Indian Patents. 224490:''NAPHTHYRIDINE DERIVATIVES AND THEIR USE AS FUNGICIDES''

Title of Invention	''NAPHTHYRIDINE DERIVATIVES AND THEIR USE AS FUNGICIDES''
Abstract	The present invention relates to derivatives of general formula I Wherein the substituents are as herein described and to a process for preparing the same.

Full Text	FUNGICIDES This invention relates to novel derivatives of naphthyridines. to processes for preparing them, to certain intermediate chemicals used in their manufacture, to compositions containing them and to methods of using them to combat fungi, especially fungal infections of plants. Derivatives of the nitrogen-containing 5,6 ring system S-l,2,4-triazolo[l,5-a]pyri-Ynidine are known from the patent literature as being useful for controlling phytopathogenic fungi. Examples of recent patent publications include EP-A-1249452, WO 02/051845, WO 02/083676, WO 02/083677, WO 02/088125, WO 02/088126, WO 02/088127. The plant fungicidal activity of certain derivatives of naphthyridines is described in EP-A-0410762 and US 4801592. Other naphthyridine derivatives are described, for example, in WO 92/07468 and US 525S356 as herbicides and in WO 93/13097 and WO 92/22533 for pharmaceutical applications. Naphthyridine derivatives are also known in the general chemical literature, for example, from Synthetic Communications (2003), 33(1), 73; Indian Journal of Chemistry, Section B (2002), 4IB(10), 2194; Fannaco (2002), 57(8), 631; Farmaco (2001), 56(4), 311; Farmaco (2000), 55(9-10), 603; Arch. Pharm. (1957), 290, 136; Farmaco, Edizione Scientifica (1979), 34(2), 165; Journal of the Chemical Society', Chemical Communications (1974), (4), 134; Journal of the Chemical Sociey, 1 (1996), (12), 1359; Journal of Organic Chemistry (1972), 37(20), 3101; Journal of Medicinal Chemistry (1973), 16(7), 849; Journal of the Chemical Society, Chemical Communications (1974), (4), 134; and the European Journal of Medicinal Chemistry (200), 35(11), 1021-1035. The present invention is concerned with the provision of alternative, novel naphthyridines for combating phytopathogenic diseases on plants and harvested food crops. Thus, according to the present invention, there is provided a compound of the general formula (1): wherein R is H, halo, C1-4 alkyl, C1-4 alkoxy or ha!o(C1-4)alkyI, provided that when X is CH, Z is N R is NHNH2, R1 is phenyl and R2 is CI, W and Y are not both CCH3; one of Rand RL isNR-R and the other is halo, C1-8 alkyl, C1-8 alkoxy, C1-8 alkylthio, C2-8 alkenyl, C2-8 alkynyl or cyano; R is aryl, heteroaryl, morpholino, piperidino or pyrrolidino; R3 and R4 are independently H, C1-8 alkyl, C2-8 alkenyl, C2-3 alkynyl, aryl, aryl(CNS)aIkyI, C3-scycloaIkyl, C3-8cycloaIkyl()alkyl, heteroaryl, heteroaryl(C1-8)alkyi, NR5R6, provided that not both R3 and R4 are H or NR5R6, or R and R together foR"" a C3.7 alkylene or-C3-C7 alkenylene chain optionally substituted with one or more C1-4 alkyl or C1-4 alkoxy groups, or, together with the nitrogen atom to which they are attached, R3 and R4 foR"" a morpholine, thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring or a piperazine or piperazine Ar-(C1-4)alkyl (especiallyN-methyl) ring; and R5 and R6 are independently H, C1-8alkyl, C2-8 alkenyl,C2-8 alkynyl, aryl, aryl(C1-8)alkyl, C3-8 cycloalkyl, C3-8cycloaikyl(C1-6)alkyl, heteroaryl or heteroaryl(C1-8)aIkyI; any of the foregoing alkyl, alkenyl, alkynyl or cycloalkyl groups or moieties (other than for R8) being optionally substituted with halogen, cyano, C1-6 alkoxy, C1-6alkylcarbonyl, C1-6 alkoxycarbonyl, haloalkoxy, C1-6 alkylthio, tri(C1-4)alkylsilyl, C1-4 alkylamino or C1-6 dialkylamino, any of the foregoing morpholine, thiomorpholine, piperidine, piperazine and pyrrolidine rings being optionally substituted with C1-4 alkyl (especially methyl), and any of the foregoing aryl or heteroaryl groups or moieties being optionally substituted with one or more substituents selected from halo, hydroxy, mercapto, C1-4 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-4 alkoxy, C2-6 alkenyloxy, C2-6 alkynyloxy, halo()alkyl, haIo(C1-6)alkoxy, C1-6 alkylthio, haIo()alkyIthio, hydroxy(C1-6)alkyl, C1-4alkoxy(C1-6)alkyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyI, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, iso- thiocyanato, nitre, -NR'"R"", -NHCOR'", -NHCONR""R"", -CONR-'R"", -S02R"", -OS02R"", -COR"", -CR""=NR""" or -N=CR'"R"",in which R"" and R"" are independently hydrogen, C1-4 alkyl, halo(C1-4)aIkyl, C1-4 alkoxy, halo(C1-4)alkoxy, C1-4 alkylthio, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)a!kyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl or C1-4 alkoxy. and R"; C7 alkylene and C3.7 alkenylene are excluded as chains foR""ed by R3 and R4; the C3_6 chain that R and R may foR"" may only be optionally substituted with one or more methyl groups; thiomorpholine, thiomorpholine S-oxide, thiomorphoiine S-dioxide and piperazine are excluded as rings that R and R""may foR""; tri(C].4)a!kylsiIyI is excluded as a substituent of any alkyl, alkenyl, alkynyl or cycloalkyl group or moiety and any morphoiine. piperidine or pyrrolidine ring is unsubstituted. The compounds of the invention may contain one or more asymmetric carbon atoms and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such. They may also exist as diastereoisomers by virtue of restricted rotation about a bond. However, mixtures of enantiomers or diastereoisomers may be separated into individual isomers or isomer pairs, and this invention embraces such isomers and mixtures thereof in all proportions. -It is to be expected that for any given compound, one isomer may be more fungicidally active than another. Except where otherwise stated, alkyl groups and alkyl moieties of alkoxy, alkylthio, etc., contain from 1 to 8, suitably from 1 to 6 and typically from 1 to 4, carbon atoms-in the foR"" of straight or branched chains. Examples are methyl, ethyl, n- and iso-propyl, n-, sec--; iso- and tert-butyl, /7-pentyl and /z-hexyl. Cycloalkyl groups contain from 3 to 8, typically from 3 to 6, carbon atoms and include bicycloalkyl groups such as the bicyclo[2.2.1]heptyl group. Haloalkyl groups or moieties are typically trichloromethyl or trifluoromethyl or contain a trichloromethyl or trifluoromethyl teR""inal group. Except where otherwise stated, alkenyl and alkynyl moieties also contain from 2 to S, suitably from 2 to 6 and typically from 2 to 4, carbon atoms in the foR"" of straight or branched chains. Examples are allyl, 2-methylallyl and propargyl. Optional substituents include halo, typically fluoro. An example of halo-substituted alkenyl is 3,4,4-trifluoro-n-butenyl. Halo includes fluoro, chloro, bromo and iodo. Most commonly it is fluoro, chloro or bromo and usually fluoro or chloro. Aryl is usually phenyl but also includes naphthyl, anthryl and phenanthryl. Heteroaryl is typically a 5- or 6-membered aromatic ring containing one or more O, N or S heteroatoms, which maybe fused to one or more other aromatic or heteroaromatic rings, such as a benzene ring. Examples are thienyl, furyl, pyrrolyl, isoxazolyl, oxazoM, benzothiazolyl, benzoxazolyl, benzimidazolyl, indolyl, quinolinyl and quinoxalinyl groups and, where appropriate, N-oxides thereof. The 6,6-ring systems embraced by the general foR""ula (1) are 1,8-naphthyridines (where W, X and Y are all CR8 and Z is N), 1,7-naphthyridines (where W, X and Z are all CRS and Y is N), 1,6-naphthyridines (where W, Y and Z are all CRS and X is N) and 1,5-naphthyridines (where X,Y and Z are all CRS and W is N). Of partiC1-6lar interest are 1,8-naphthyridines. R8, which may be the same or different for the three CR5 values of W, X, Y and Z is H, halo (for example bromo), C1-4 alkyl (for example methyl), C1-4 alkoxy (for example methoxy) or halo(Ci.4)alkyl (for example trifluoromethyl). Usually R8 will be H. However, of partiC1-6lar interest are compounds containing a 3-bromo-l,8-naphthyridine ring (i.e. where W and Y are CH, X is CBr and Z is N). One of R and R2, preferably R2, is NR3R4. The other is typically halo, especially chloro or fluoro. In the case of thel,S-naphthyridine ring system, the more active compounds are those where R is NR R . R is typically C1-8 alkyl (for example ethyl, /t-propyl, n-butyl, sec-bbuty,(the S- or R-isomer or the racemate) and tert-butyl), haIo(Ci.s)aIkyl (for example 2,2,2-trifluoroethyl, 2,2,2-trifluoro-l-methyIethyI (the S- or R-isomer or the racemate), 3,3,3-trifluoropropyl and 4,4,4-trifluorobutyl), hydroxy(C1-8)alkyl (for example hydroxyethyl), C1-4 alkoxy(C1-8)alkyl (for example methoxymethyl and methoxy-/so-butyI), C1-4 alkoxyhalo-(Cl.8)alkyl (for example 2-methoxy-2-trifluromethylethyl), tri(C1-4)alkylsilyI(C1-6)alkyl (for example trimethylsilylmethyl), C1-4 alkylcarbonyl(C1-8)alkyl (for example 1-acetylethyl and l-terr-butylcarbonylethyl), C1-4 alkylcarbonylhalo(C1-8)alkyl (for example l-acetyl-2,2,2-trifluoroethyl), phenyI(M)alkyl (for example benzyl), C2-8 alkenyl (for example allyl and methylallyl), halo(C2-8)alkenyl (for example 3-methyl-4,4-difluorobut-3-enyl), C2-8 alkynyl (for example propargyl), C3-8 cycloalkyl (for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl) optionally substituted with chloro, fluoro or methyl, C3-8 cycloalkyl(C1-4)-aLkyl (for example cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl and cyclohexylmethyl), phenylamino, piperidino or morpholino, the phenyl ring of phenylalkyl or phenylamino befng optionally substituted with one, two or three substituents selected from halo (typically fluoro, chloro or bromo), C1-4 alkyl (typically methyl), halo(C1-4)alkyl (typically trifluoromethyl), C1-4 alkoxy (typically methoxy) and halo(C1-4aIkoxv (typically C4-6 alkylene chain optionally substituted with methyl, for example 3-methylpentyIene, or, together with the nitrogen atom to which they are attached, R3 and R4 foR"" a morpholine, thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring or a piperazine or piperazine iV-(Ci.4)alkyl (especially ;V-methyl) ring, in which the morpholine or piperazine rings are optionally substituted with methyl. Typically R1 is phenyl optionally substituted with from one to five halogen atoms, partiC1-6larly fluorine and chlorine atoms and especially fluorine atoms or with from one to three substituents selected from halo (for example fluoro and chloro), C1-4 alkyl (for example methyl), halo(Ci.4)aIkyl (for example trifluoromethyl), C1-4 alkoxy (for example methoxy) or halo(Ci.4)alkoxy (for example trifluoromethoxy). Examples are 2,6-difluorophenyL 2-fluoro-6-chlorophenyl, 2,5,6-trifluorophenyl, 2,4,6-trifluorophenyl, 2,6-difluoro-4-methoxyphenyl, pentafluorophenyl, 2-fluorophenyI, 2,3,5,6-tetrafluorophenyl, 2-chloro-4,6-difluorophenyI, 2-chIorophenyl, 2,6-dichIorophenyI, 2,4-dichIorophenyl, 2,4,6-trichlorophenyI, 2,3.6-tri-chlorophenyl, pentachlorophenyl, 2-fluoro-4,6-dichIorophenyI, 4-fluoro-2.6-dichIoropheixyl, 2-bromophenyl, 2-fluoro-6-bromophenyl, 2-brorno-4,6-difluorophenyl, 2-fluoro-6-methyl-phenyl, 2-chloro-6-methyIphenyl, 2-methoxyphenyl, 2,6-dimethoxyphenyI, 2-fluoro-6-methoxyphenyl, 2-trifIuoromethylphenyI, 2-fluoro-6-trifluoromethylphenyI, 2,6-di-(trifluoro-methyl)phenyl, 2-chloro-6-trifluoromethylphenyl, 2,4-difluoro-6-trifluoromethylphenyI, 2,4-difluoro-6-methoxyphenyI and 2,4-difluoro-6-methylphenyl. Also of partiC1-6lar interest are compounds where R1 is pyridyl optionally substituted with from one to four halogen atoms or with from one to three substituents selected from halo (for example fluoro and chloro), C1-4 alkyl (for example methyl), halo(C1-6t)alkyl (for example trifluoromethyl), C1-4 alkoxy (for example methoxy) or halo(C1-6)alkoxy (for example trifluoromethoxy). Examples are 2,4-difluoropyrid-3-yl, 3,5-difluoropyrid-4-yl, tetrafluoropyrid-4-yI, 3-fluoropyrid-2-yl, 4-fluoropyrid-3-yl, 3-fluoropyrid-4-yl, 2-fluoro-pyrid-3-yl, 2,4,6-trifluoropyrid-3-yl, 3,5-difluoropyrid-2-yl, 2,6-difluoropyrid-3-yl, 2,4-difluoro-6-methoxypyrid-3-yl, 2-fluoro-4-chloropyrid-3-yl, 3-fluoro-5-chloropyrid-4-yl, 2-chloro-4-fluoropyrid-3-yl, 2,4~dichloropyrid-3-yl, 3-chloropyrid-2-yl I, 4-chlorop>Tid-3-yl, 3-chloropyrid-4-yI, 2-chloropyrid-3-yl, 3-trifIuoromethylpyrid-2-yI, 4-trifluoromethylpyrid-3-yI, 3,5-dichloropyrid-2-yl, 4,6-dichloropyrid-3-yl, 3-trifluoromethylpyrid-4-yl, 2-trifluoro-methylpyrid-3-yI, 2-fluoro-4-trifluoromethylpyrid-3-yl, 3-fluoro-5-trifiuoromethy]pyrid-4-yl, chloro-6-trifluoromethy!pyrid-2-yl, 3-fluoro-6-trifluoromethyIpyrid-2-yI, pyrid-2-yl, pyrid-3-yl and pyrid-4-yl. Also of partiC1-6lar interest are compounds where R1 is 2- or 3-thienyl optionally substituted with from one to three halogen atoms or with from one to three substituents selected from halo (for example fluoro and chloro), C1-4 alkyl (for example methyl), halo-(C1-4)aIkyl (for example trifluoromethyl), C1-4 alkoxy (for example methoxy) or ha!o(C1-4). alkoxy (for example trifluoromethoxy). Examples are 3-fluorothien-2-yI, 3-chlorothien-2-yl, 2,4-difluorothien-3-yl. 2,4-dichlorothien-3-yl and 2,4,5-trichlorothien-3-yl. Examples of other values o fR'of especial interest are unsubstituted piperidino and morpholino, 2-methylpiperidino, 2,6-dimethyIpiperidino and 2,6-dimethylmorpholino. In one aspect the invention provides a compound of the general foR""ula (1) wherein . one of W, X, Y and Z is N and the others are CRS; R8 is H, halo, C1-4 alkyl, C1-4 alkoxy or halo(C1-4)alkyl, provided that when X is CH, Z is N, R is NHNH2, R1 is phenyl and R2 is CI, W and Y are not both CCH3; one of R and R" (preferably R ) is NR R and the other is halo; R1 is aryl, heteroaryl, morpholine, piperidino or pyrrolidino; R3 and R4 are independently H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, aryl, aryI(Cj-8)alkyl, C3-8cycloalkyC'C3-8cycloaIkyI(C1-6)alkyl, heteroaryl, heteroaryl(C1-8)alkyl, NRDR6, provided that not both R3 and R4 are H or NR5R6, or R3 and R4 together foR"" a C3.7 alkylene or C3.7 alkenylene chain optionally substituted with one or more C1-4 alkyl or C1-4 alkoxy groups, or, together with the nitrogen atom to which they are attached, R3 and R4 foR"" a morpholine, thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring or a piperazine or piperazine A^-(Ci-4)alkyl (especially TV-methyl) ring; and R5 and R6 are independently H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, aryl, aryl(C1-8)aIkyl, C3-scycloalkyl, C3.gcycloaIkyl()alkyI, heteroaryl orheteroaryl(C1-8)alkyl; any of the foregoing alkyl, alkenyl, alkynyl or cycloalkyl groups or moieties (other than for R8) being optionally substituted with halogen, cyano, alkoxy, C1-6 alkylcarbonyl, alkoxycarbonyl, C1-4 haloalkoxy, alkylthio, tri(C1-6)alkyIsiIyI, alkylamino or dialkylamino, any of the foregoing morpholine, thiomorpholine, piperidine, piperazine and pyrrolidine substituted with one or more substituents selected from halo, hydroxy, mercapto, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyk C1-6 alkoxy. C2-6 alkenyloxy, C2-6 alkynyloxy, halo()aIkyl, haIo(C1-6)alkoxy, C1-6 alkylthio, ha!o(C1-6)alkyIthio, hydroxy(C1-6)aIkyL C1-4aIkoxy(C1-6)-alkyl, C3-6 cycloalkyl, C3-6 cycIoaIkyl(C1-4)aIky!, phenoxy, benzyloxy, benzoyloxy, cyano, isocvC1-6no, thiocyanato, isothiocyanaio, nitro, -NR"'R"",-NHCOR"', -NHCONR""R"",-CONRH,R"", -S02R"", -OS02R",-COR'", -CR"'=NR'm or -N=CR'"R"f,in which R"' and R"" are independently hydrogen, C1-4 alkyl, haIo(C1-4)alkyI, C1-4alkoxy, halo(C1-4)aIkoxy,C1-4 alkylthio, C3-6 cycloalkyl. C3-6 cycloalkyl(Ci„:)alkyI, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl or C1-4alkoxy. Of partiC1-6lar interest are compounds where W, X and Y are CH and Z is N. The invention includes a compound of the general foR""ula (1) as defined immediately above except that: C7 alkylene and C3-7 alkenylene are excluded as chains foR""ed by R and R ; the C3-6 chain that R3 and R4 may foR"" may only be optionally substituted with one or more methyl groups; thiomorpholine, thiomorpholine S-oxide, thiomorpholine S-dioxide and piperazine are excluded as rings that RJ and R4 may foR""; tri(C1-4)alkylsilyl is excluded as a substituent of any alkyl, alkenyl, alkynyl or cycloalkyl group or moiety, and any morpholine, piperidine or pyrrolidine ring is unsubstituted. In another aspect the invention provides a compound of the general foR""ula (I) wherein one of W, X, Y and Z is N and the others are CR8; R8 is H, halo, C1-4 alkyl, C1-4 alkoxy or halo(C[-4)alkyl, provided that when X is CH, Z is N, R is NHNH2, R1 is phenyl and R2 is CI, W and Y are not both CCH3; one of R and R2 (preferably R2) is NR3R4 and the other is halo; R1 is aryl, heteroaryl, morpholino, piperidino orpyrrolidino; R3 is C1-4 alkyl, halo(C1-4)aIkyl, C2-4 alkenyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl or phenylamino in which the phenyl ring is optionally substituted with one, two or three substituents selected from halo, C1-4 alkyl, ha!o(C1-4)alkyI, C1-4 alkoxy and halo(C1-4)alkoxy; and R4 is H, C1-4 alkyl or amino, or R3 and R4 together foR"" a C4-6 alkylene chain optionally substituted with C1-4 alkyl or C1-4 alkoxy, or, together with the nitrogen atom to which they are attached, R and R foR"" a morpholine. any of the foregoing alkyl. alkenyl, alkynyl orcycloalkyl groups or moieties (other than for R3) being optionally substituted with halogen, cyano, C1-6 alkoxy, C1-6alkylcarbonyl, C1-6 alkoxycarbony], C].0 haloalkoxy, C1-6 alkylthio, tri(C1-4)alkyIsilyI, C1-6 alkylamino or C1-6 dialkylamino, any of the foregoing morpholine, thiomorpholine, piperidine. piperazine and pyrrolidine rings being optionally substituted with C1-4 alkyl (especially methyl), and any of the foregoing aryl or heteroaryl groups or moieties being optionally substituted with one or more substituents selected from halo, hydroxy, mercapto, C1-6alkyl, C1-6 alkenyl, C1-6 alkynyl, alkoxy, C2-6 alkenyloxy, C2-6 alkynyloxy, haIo(Ci-o)aIkyI, halo(C1-6)alkoxy, C].6 alkylthio, halo(Cj.6)a!kylthio, hydroxy()aIkyl, C1-4alkoxy()alkyI, C1-6cycloalkyl, C3-6 cycloa!kyl(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, iso-thiocyanato, nitro, -NR"'R"", -NHCOR",-NHCONR,,,R,",-CONR"'R""", -SO:R"", -OS02R",-COR"', -CR'"=NR"" or -N-CR'-'R"", in which R"" and R""r are independently hydrogen, C1-4 alkyl, halo(C1-4)aIkyl, C1-4alkoxy, halo(C(_4)alkoxy, C1-4 alkylthio, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyI, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl or C1-4 alkoxy. Of partiC1-6lar interest are compounds where W, X and Y are CH and Z is N. ... The invention includes a compound of the general foR""ula (1) as defined immediately above except that; the C4-6 chain that R3 and R4 may foR"" may only be optionally substituted with methyl; thiomorpholine, thiomorpholine S-oxide, thiomorpholine S-dioxide and piperazine are excluded as rings that R3 and R4 may foR""; tri(C1-4)alkyIsilyI is excluded as a substituent of any alkyl, alkenyl, alkynyl or cycloalkyl group or moiety, and any morpholine, piperidine or pyrrolidine ring is unsubstituted In yet another aspect the invention provides a compound of the general foR""ula (1) wherein one of W, X, Y and Z is N and the others are CR8; R8 is H, halo, C1-4 alkyl, C1-4 alkoxy or halo(C1-4)aIkyl, provided that when X is CH, Z is N, R is NHNH2, R1 is phenyl and R2 is CI, W and Y are not both CCH3; one of R and R2 is NR3R4 and the other is halo, C1-8 alkyl, C1-8alkoxy, C1-4 alkylthio, C2-8 alkenyl, C2-8 alkynyl or cyano; R1 is optionally substituted phenyl; that not both R3 and R4 are H or NR5R6, or R and R together foR"" a C3.7 alkylene or C3.7 alkenylene chain optionally substituted with one or more C1-4alkyl or C1-4 alkoxy groups, or, together with the nitrogen atom to which they are attached, RJ and R4 foR"" a morpholine, thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring or a piperazine or piperazine;V-(C1-4)aIkyI (especially yV-methyl) ring; and R5 and R6 are independently}-!, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, aryl, aryI(C]„s)alkyl, C3-8 cycloalkyl, C3-8 cycIoalkyI()alkyI, heteroaryl orheteroaryl(C1-8)alkyl; any of the foregoing alkyl, alkenyl, alkynyl or cycloalkyl groups or moieties (other than for R8) being optionally substituted with halogen, cyano, C1-6 alkoxy, C1-6alkylcarbonyl, C1-6 alkoxycarbonyl, C1-6 haloalkoxy, C1-6 alkylthio, tri(C1-4)aIkyIsilyl, C1-6 alkylamino or C1-6dialkylamino, any of the foregoing morpholine, thiomorpholine, piperidine, piperazine and pyrrolidine rings being optionally substituted with C1-4 alkyl (especially methyl), and any of the foregoing aryl or heteroaryl groups or moieties, including the phenyl group of R1, being optionally substituted with one or more substituents selected from halo, hydroxy, mercapto, C1-6alkyl, C2-6 alkenyl, C2-6 alkynyl, alkoxy, C2-6 alkenyloxy, C2-6 'alkynyloxy, halo()alkyl, haIo(C1-6)alkoxy, alkylthio, halo()alkylthio, hydroxy-()alkyl, C1-4 alkoxy()alkyl, C3-6 cycloalkyl, C3-6 cycloalkyI(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, -NR'"R"", -NHCOR", -NHCONR""R""", -CONR""R"", -S02R",-OS02R", -COR",-CR,H=NR"" or -N=CR'"R"", in which R"" and R"" are independently hydrogen, C1-4 alkyl, haIo(C1-4)alkyI, C1-4 alkoxy, halo(C1-4)alkoxy, C1-4 alkylthio, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl or C1-4 alkoxy. Of partiC1-6lar interest are compounds where W, X and Y are CH and Z is N. The invention includes a compound of the general foR""ula (1) as defined immediately above except that: C1-8 alkoxy and C1-8 alkylthio are excluded as values of R and R2; C7 alkylene and C3.7 alkenylene are excluded as chains foR""ed by R3 and R4; the C3-6 chain that R3 and R4 may foR"" may only be optionally substituted with one or more methyl groups; thiomorpholine, thiomorpholine S-oxide, thiomorpholine S-dioxide and piperazine of any alkyl, alkenyl, alkynyl orcycloalkyl group or moiety, and the morphoiine ring that R3 and FT may foR"" is unsubstituted. In still yet another aspect the invention provides a compound of the general foR""ula (1) wherein one of W, X, Y and Z is N and the others are CRS; R8 is H, halo (e.g. fluoro, chloro or bromo), C1-4 alkyl (e.g. methyl). C1-4 alkoxy (e.g. methoxy) or halo(C1-4)alkyl (e.g. trifluoromethyl), provided that when X is CH, Z is N, R is NHNH2, R1 is phenyl and R2 is CI, W and Y are not both CCH3; R is halo (e.g. fluoro, chloro or bromo), C1-4alkyl (e.g. methyl), C1-4 alkoxy (e.g. methoxy) orcyano; R1 is phenyl optionally substituted with from one to five halogen atoms or with from one to three substituents selected from halo, C1-4 alkyl, halo(C1-4)alkyl, C1-4 alkoxy or Kalo(C1-4)-alkoxy, pyridyl optionally substituted with from one to four halogen atoms or with from one to three substituents selected from halo, C1-4 alkyl, halo(C1-4)alkyI, C1-4 alkoxy or halo(C1-4)-alkoxy, 2- or 3-thienyl optionally substituted with from one to three halogen atoms or with from one to three substituents selected from halo, C1-4 alkyl, halo(C1-4)aIkyl, C1-4alkoxy or halo(C1-4)alkoxy, or piperidino or morpholino both optionally substituted with one or two methyl groups; R2 is NR3R4; R3 is C1-8 alkyl, halo(C].g)alkyl, hydroxy(Ci_g)alkyl, C1-4 aIkoxy(C1-8)alkyl, C1-4 alkoxyhalo-(C1-8)alkyl, tri(C1-4)alkylsilyl()alkyl, C1-4 alkylcarbonyl(C1-8)aIkyl, C1-4alkylcarbonyl-halo(C1-8)alkyl, phenyl(i.4)alkyl, C2-8 alkenyl, haIo(C2-8)alkenyl, C2-8 alkynyl, C3-8 cycloalkyl optionally substituted with chloro, fluoro or methyl, C3-8 cycloalkyl(C1-4)alkyl, phenylamino, piperidino or morpholino, the phenyl ring of phenylalkyl or phenylamino being optionally substituted with one, two or three substituents selected from halo, C1-4alkyl, halo(C1-4)alkyl, C1-4 alkoxy and halo(C1-6alkoxy; and R is H, C1-4 alkyl, halo(C1-4)alkyl or amino, or R3 and R4 together foR"" a C3.7 alkylene or C3.7 alkenylene chain optionally substituted with methyl, or, together with the nitrogen atom to which they are attached, R3 and R foR"" a morphoiine, t rings are optionally substituted with methyl. Of partiC1-6lar interest are compounds where W, X and Y are CH and Z is N. In still yet another aspect the invention provides a compound of the general formula (1) wherein one of W, X, Y and Z is N and the others are CRS; Rs is H, halo, C1-4 alkyl C1-4 alkoxy or haIo(C:.j)aIkyl; R is halo; R1 is phenyl optionally substituted with from one to five halogen atoms or with from one to three substituents selected from halo, C1-4alkyl, haIo(C1-4)alkyI, C1-4 alkoxy or halo(C1-6)-alkoxy; R2 is NR3R4; R3 is C1-4 alkyl, haIo((C1-4)alkyl, C2-4 alkenyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alky! or phenylamino in which the phenyl ring is optionally substituted with one, two or three substituents selected from halo, C1-4 alkyl haIo(C1-4)alkyl, C1-4 alkoxy and halo(C1-4)alkoxy; and R4 is H, C1-4 alkyl or amino, or R3 and R4 together form a C4-6 alkylene chain optionally substituted with methyl, or, together with the nitrogen atom to which they are attached, RJ and R4 form a morpholine ring. Of partiC1-6lar interest are compounds where W, X and Y are CH and Z is N. Compounds that form part of the invention are illustrated in Tables 1 to 126 below. Characterising data are given later in the Examples and in Table 132 In Table 1 the compounds have the general formula (1 A), where W, X and Y are CH, Z is N, R is CI, R1 is 2,4,6-trifluorophenyl and R3 and R4 are as shown in the table. Table 3 Table 3 consists of 662 compounds of the general foR""ula (1 A), where W, X and Y are CH and Z is N, R is CI, R1 is 2,3,4,5,6-pentafluorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound I of Table 3 is the same as compound 1 of Table 1 except that in compound 1 of Table 3, R1 is 2.3,4,5,6-pentailuorophenyI. Similarly. compounds 2 to 662 of Table 3 are the same as compounds 2 to 662 of Table 1 except that in the compounds of Table 3, R' is 2,3,4,5,6-pentafluorophenyl. Table 4 - Table 4 consists of 662 compounds of the general foR""ula (1 A), where W, X and Y are CH and Z is N, R is CI, R1 is 2",6-dif!uoro-4-methoxyphenyl, and the values of RJ and R4 are as listed in Table 1. Thus, compound 1 of Table 4 is the same as compound 1 of Table 1 except that in compound 1 of Table 4, R1 is 2,6-difluoro-4-methoxyphenyl. Similarly, compounds 2 to 662 of Table 4 are the same as compounds 2 to 662 of Table 1 except that in the compounds of Table 4, R1 is 2,6-difluoro-4-methoxyphenyl. Table 5 Table 5 consists of 662 compounds of the general foR""ula (1A), where W, X and Y are CH and Z is N, R is CI, R1 is 2-fluoro-6-chIorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 5 is the same as compound 1 of Table 1 except that in compound 1 of Table 5, R1 is 2-fluoro-6-chlorophenyl. Similarly, compounds 2 to 662 of Table 5 are the same as compounds 2 to 662 of Table 1 except that in the compounds of Table 5, R1 is 2-fluoro-6-chlorophenyI. Table 6 Table 6 consists of 662 compounds of the general foR""ula (IB), where W, X and Y are CH and Z is N, R is CI, R1 is 2.4,6-trifluorophenyI, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 6 is the same as compound 1 of Table 1 except that in compound 1 of Table 6, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 6 are the same as compounds 2 to 662 of Table 1 except that in the compounds of Table 6, the compounds have the general foR""ula (IB). Table 7 Table 7 consists of 662 compounds of the general foR""ula (IB), where W, X and Y are CH and Z is N, R is CI, R1 is.2?5,6-trifluorophenyI, and the values of R3 and R4 are as listed in Table I. Thus, compound 1 of Table 7 is the same as compound 1 of Table 2 except that in compound 1 of Table 7, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 7 are the same as compounds 2 to 662 of Table 2 except that in the compounds of Table 7, the compounds have the general foR""ula (IB). Table 8 Table 8 consists of 662 compounds of the general foR""ula (IB), where W, X and Y are CH and Z is N, R is CI, R1 is 2,3,4,5,6-pentafluorophenyI, and the values of R3 and R4 are as listed in Table 3. Thus, compound 1 of Table 8 is the same as compound 1 of Table 3 except that in compound 1 of Table S, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 8 are the same as compounds 2 to 662 of Table 3 except that in the compounds of Table S, the compounds have the general foR""ula (IB). Table 9 Table 9 consists of 662 compounds of the general foR""ula (IB), where W, X and Y are CH and Z is N, R is CI, R1 is 2,6-difIuoro-4-methoxyphenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 9 is the same as compound 1 of Table 4 except that in compound 1 of Table 9, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 9 are the same as compounds 2 to 662 of Table 4 except that in the compounds of Table 9, the compounds have the general foR""ula (IB). Table 10 Table 10 consists of 662 compounds of the general foR""ula (IB), where W, X and Y are CH and Z is N, R is CI, R1 is 2-fluoro-6-chlorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 10 is the same as compound 1 of Table 5 except that in compound 1 of Table 10, the compound has the general foR""ula (IB). Table 11 Table 11 consists of 662 compounds of the general foR""ula (1A). where W is N and X, Y and Z are CH, R is CI, R1 is 2,4,6-trifluorophenyI, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 11 is the same as compound 1 of Table 1 except that in compound 1 of Table 11, the compound has the general foR""ula (1 A) where \V is N and X, Y and Z are CH. Similarly, compounds 2 to 662 of Table 11 are the same as compounds 2 to 662 of Table 1 except that in the compounds of Table 11, the compounds have the general foR""ula (1 A) where W is N and X, Y and Z are CH. Table 12 Table 12 consists of 662 compounds of the general foR""ula (1 A), where W is N and X,Y and Z are CH, R is CI, R1 is 2,5,6-trifluorophenyI, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 12 is the same as compound 1 of Table 2 except that in compound 1 of Table 12, the compound has the general- foR""ula (1A) where W is N and X, Y and Z are CH. Similarly, compounds 2 to 662 of Table 12 are the same as compounds 2 to 662 of Table 2 except that in the compounds of Table 12, the compounds have the general foR""ula (1 A) where W is N and X, Y and Z are CH. Table 13 Table 13 consists of 662 compounds of the general foR""ula (1A), where W is N and X, Y and Z are CH, R is CI, R1 is 2,3,4,5,6-pentafluorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 13 is the same as compound 1 of Table 3 except that in compound 1 of Table 13, the compound has the general foR""ula (1 A) where W is N and X, Y and Z are CH. Similarly, compounds 2 to 662 of Table 13 are the same as compounds 2 to 662 of Table 3 except that in the compounds of Table 13, the compounds have the general foR""ula (1 A) where W is N and X, Y and Z are CH. Table 14 Table 14 consists of 662 compounds of the general foR""ula (1A), where W is N and X, Y and Z are CH, R is CI, R1 is 2,6-difluoro-4-methoxyphenyl, and the values of R3 andR4 are as listed in Table I. Thus, compound 1 of Table 14 is the same as compound 1 of Table 4 , except that in compound 1 of Table 14, the compound has the general foR""ula (1A) where W is N and X, Y and Z are CH. Similarly, compounds 2 to 662 of Table 14 are the same as compounds 2 to 662 of Table 4 except that in the compounds of Table 14, the comooumis Table 15 consists of 662 compounds of the general foR""ula (1 A), where W is N and X,Yand Z are CH, R is CI, R1 is 2-fluoro~6-chlorophenyl, and the values of RJ and R4 are as listed in Table 1. Thus, compound 1 of Table 15 is ihe same as compound 1 of Table 5 except that in compound 1 of Table 15, the compound has the general foR""ula (I A) where W is N and X, Y and Z are CH. Similarly, compounds 2 to 662 of Table 15 are the same as compounds 2 to 662 of Table 5 except that in the compounds of Table 15, the compounds have the general foR""ula (1A) where W is N and X, Y and Z are CH. Table 16 Table 16 consists'of 662 compounds of the general foR""ula (IB), where W is N and X, Y and Z are CH, R is CI, R1 is 2,4.6-trifluorophenyl, and the values of R- and R" are as listed'in Table 1. Thus, compound 1 of Table 16 is the same as compound 1 of Table 11 except that in compound 1 of Table 16, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 16 are the same as compounds 2 to 662 of Table 11 except that in the compounds of Table 16, the compounds have the general foR""ula (IB). Table 17 Table 17 consists of 662 compounds of the general foR""ula (IB), where W is N and i ** * X, Y and Z are CH, R is CI, R is 2,5,6-trifluorophenyl, and the values of RJ and K* are as listed in Table 1. Thus, compound 1 of Table 17 is the same as compound 1 of Table 12 except that in compound 1 of Table 17, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 17 are the same as compounds 2 to 662 of Table 12 except that in the compounds of Table 17, the compounds have the general foR""ula (IB). Table 18 Table 18 consists of 662 compounds of the general foR""ula (IB), where W is N and X, Y and Z are CH, R is CI, R1 is 2,3,4,5,6-pentafluorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 18 is the same as compound 1 of Table 13 except that in compound 1 of Table 18, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 18 are the same as compounds 2 to 662 of Table 13 * except-that in the compounds of Table 18, the compounds have the general foR""ula (IB). Table 19 Table 19 consists of 662 compounds of the general foR""ula (IB), where W is N and X. Y and Z are CH, R is CI. Rl is 2.6-difluoro-4-methoxvt>henvl. and the values of R3 and R4 Similarly, compounds 2 to 662 of Table 19 are the same as compounds 2 to 662 of Table 14 except that in the compounds of Table 19, the compounds have the senera! foR""ula OB) Table 20 Table 20 consists of 662 compounds of the general foR""ula (IB), where W is N and X, Y and Z are CH, R is CI, R1 is 2-fluoro-6-chloropheny!, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 20 is the same as compound 1 of Table 15 except that in compound 1 of Table 20, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 20 are the same as compounds 2 to 662 of Table 15 except that in the compounds of Table 20, the compounds have the general foR""ula (IB) Table 21 Table 21 consists of 662 compounds of the general foR""ula (1 A), where W, X and Z are CH and Y is N, R is CI, R1 is 2,4,6-tnfluorophenyl, and the values of R3 and R4' are as listed in Table 1. Thus, compound 1 of Table 21 is the same as compound 1 of Table 1 except that i„ compound 1 of Table 21, the compound has the general foR""ula (1 A) where W, X and Z are CH and Y is N. Similarly, compounds 2 to 662 of Table 21 are the same as compounds 2 to 662 of Table 1 except that i„ the compounds of Table 21, the compounds have the general foR""ula (i'A) where W, X and Z are CH and Y is N. Table 22 Table 22 consists of 662 compounds of the general foR""ula (IA), where W, X and Z are CH and Y is N, R is CI, R1 is 2,5,6-trifluorophenyl, and the values of R3 and R4' are as listed in Table 1. Thus, compound 1 of Table 22 is the same as compound 1 of Table 2 except that in compound 1 of Table 22, the compound has the general foR""ula (1 A) where W, X and Z are CH and Y is N. Similarly, compounds 2 to 662 of Table 22 are the same as compounds 2 to 662 of Table 2 except that in the compounds of Table 22, the compounds have the general foR""ula (1 A) where W, X and Z are CH and Y is N. Table 23 Table 23 consists of 662 compounds of the general foR""ula (1 A), where W, X and Z are CH and Y is N, R is CI, R1 is 2,3,4,5,6-pentafluorophenyl, and the values of R3 and R4 are as listed in.fable 1. Thus," compound 1 of Table 23 is the same as compound 1 of Table 3 except that in compound 1 of Table 23, the compound has the general foR""ula (1 A) where W, X and Z are CH and Y is N. Similarly, compounds 2 to 662 of Table 23 are the same as Table 24 Table 24 consists of 662 compounds of the general foR""ula (1 A), where \Y, X and Z are CH and Y is N, R is CI, R1 is 2,6-difluoro-4-methoxyphenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound I of Table 24 is the same as compound 1 of Table 4 except that in compound 1 of Table 24, the compound has the general foR""ula (1 A) where W, X and Z are CH and Y is N. Similarly, compounds 2 to 662 of Table 24 are the same as compounds 2 to 662 of Table 4 except that in the compounds of Table 24, the compounds have the general foR""ula (1 A) where W, X and Z are CH and Y is N. Table 25 Table 25 consists of 662 compounds of the general foR""ula (1 A), where \\,X and Z are CH and Y is N, R is CI, R1 is 2-fluoro-6-chlorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 25 is the same as compound 1 of Table 5 except that in compound 1 of Table 25, the compound has the general foR""ula (1 A) where W, X and Z are CH and Y is N. Similarly, compounds 2 to 662 of Table 25 are the same as compounds 2 to 662 of Table 5 except that in the compounds of Table 25, the compounds have the general foR""ula (1 A) where W, X and Z are CH and Y is N. Table 26 Table 26 consists of 662 compounds of the general foR""ula (1 A), where W, Y and Z are CH and X is N, R is CI, R1 is 2,4,6-trifluorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 26 is the same as compound 1 of Table 1 except that in compound 1 of Table 26, the compound has the general foR""ula (1 A) where W, Y and Z are CH and X is N. Similarly, compounds 2 to 662 of Table 26 are the same as compounds 2 to 662 of Table 1 except that in the compounds of Table 26, the compounds have the general foR""ula (1 A) where W, Y and Z are CH and X is N. Table 27 Table 27 consists of 662 compounds of the general foR""ula (1A), where W, Y and Z are CH and X is N, R is CI, R1 is 2,5,6-trifluorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 27 is the same as compound 1 of Table 2 ' except that in compound 1 of Table 27, the compound has the general foR""ula (1 A) where W, Y and Z are CH and X is N. Similarly, compounds 2 to 662 of Table 27 are the same as Table 28 Table 28 consists of 662 compounds of the general foR""ula (1 A), where W. Y and Z are CH and X isN, R is CI, R1 is 2.3A5,6-pentafluorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 28 is the same as compound 1 of Table 3 except that in compound 1 of Table 28, the compound has the general foR""ula (1 A) where W, Y and Z are CH and X is N. Similarly, compounds 2 to 662 of Table 2S are the same as compounds 2 to 662 of Table 3 except that in the compounds of Table 28, the compounds have the general foR""ula (1A) where W, Y and Z are CH and X is N. Table 29 Table 29 consists of 662 compounds of the general foR""ula (1 A), where YY,Y and Z are CH and X is N, R is CI, R1 is 2,6-difluoro-4-methoxyphenyI, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 29 is the same as compound 1 of Table 4 except that in compound 1 of Table 29, the compound has the general foR""ula (1 A) where W, Y and Z are CH and X is N. Similarly, compounds 2 to 662 of Table 29 are the same as compounds 2 to 662 of Table 4 except that in the compounds of Table 29, the compounds have the general foR""ula (1 A) where W, Y and Z are CH and X is N.-Table 30 Table 30 consists of 662 compounds of the general foR""ula (1 A), where W, Y and Z are CH and X is N, R is CI, R1 is 2-fluoro-6-chlorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 30 is the same as compound 1 of Table 5 except that in compound 1 of Table 30, the compound has the general foR""ula (1 A) where W, Y and Z are CH and X is N. Similarly, compounds 2 to 662 of Table 30 are the same as compounds 2 to 662 of Table 5 except that in the compounds of Table 30, the compounds have the general foR""ula (1 A) where W, Y and Z are CH and X is N. Table 31 Table 31 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds.1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly Table 32 Table-32 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds I9S7 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 32 R is 2-fluorophenyl instead of 2-fluoro-6-chlorophenyl. Table 33 Table 33 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 33 R is 2,3,5,6-tetrafluorophenyl instead of 2-fluoro-6-chlorophenyI. Table 34 Table 34 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 34 Rl is 2-chloro-4,6-difluorophenyl instead of 2-fluoro-6-chloro- phenyl same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 35 R is 2-chloropheny] instead of 2-fIuoro-6-chIorophenyl. Table 36 Table 36 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds I to 662 of Table 30 respectively, except that in all of the compounds of Table 36 R3 is 2,6-dichlorophenyl instead of 2-fluoro-6-chIorophenyL Table 37 - - i Table 37 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectivelyrcompounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds I to 662 of Table 30 respectively, except that in all of the compounds of Table 37 R1 is 2,4-dichlorophenyl instead of 2-fluoro-6-chlorophenyl. Table 38 Table 38 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly - . the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the Table 39 Table 39 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 axe exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 39 R is 2,3,6-trichlorophenyl instead of 2-fluoro-6-chlorophenyl. Table 40 Table 40 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are .exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 40 R1 is pentachlorophenyl instead of 2-fluoro-6-chlorophenyL Table 41 Table 41 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 41 R1 is 2-fluoro-4,6-dichlorophenyl instead of 2-fluoro-6-chloro- phenyl. Table 42. Table 42 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactiv the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 42 R1 is 4-fluoro-2,6-dichIorophenyl instead of 2-fluoro-6-chloro-phenyl. Table 43 Table 43 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 43 R is 2-bromophenyl instead of 2-fluoro-6-chlorophenyl. Table 44 -Table 44 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 44 Rl is 2-fluoro-6-bromophenyI instead of 2-fluoro-6-chlorophenyl. Table 45 Table 45 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the Table 46 Table 46 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the 'same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 46 R is 2-fluoro-.6-methylphenyl instead of 2-fluoro-6-chlorophenyl. Table 47 Table 47 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds I to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 47 R1 is 2-chloro-6-methylphenyl instead of 2-fluoro-6-chlorophenyl. Table 48 Table 48 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds I to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 48 R1 is 2-methoxyphenyl instead of 2-fluoro-6-chlorophenyl. Table 49 Table 49 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 49 R1 is 2,6-dimethoxyphenyl instead of 2-fluoro-6-chIorophenyl Table 50 Table 50 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 50 R is 2-fluoro-6-methoxyphenyl instead of 2-fluoro-6-chIorophenyI. Table 51 Table 51 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds "1 to 662 of Table 5 respectively, compounds"663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325"to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 51 R is 2-trifluoromethylphenyl instead of 2-fluoro-6-chlorophenyl. Table 52 Table 52 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 52 R1 is 2-fluoro-6-trifluoromethylphenyl instead of 2-fluoro-6-chloro-ohenyl. Table 53 Table 53 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 53 R is 2,6-di- Table 54 consists of 3972 compounds. Compounds! to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 54 R1 is 2-chIoro-6-trifIuoromethylphenyl instead of 2-fluoro-6-chlorophenyl. Table 55 Table 55 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 55 R1 is 2,4-difluoro-6-trifluoromethylphenyl instead of 2-fluoro-6-chlorophenyl. TableJ>6 compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 56 R! is 2,4-difluoro-6-rnethoxyphenyl instead of 2-ftuoro-6-chloro-phenyl. Table 57 Table 57 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same -} .as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are ' exactly the same as compounds 1 to 662 of Table 30 respectively, except-that in all of the compounds of Table 57 R1 is 2,4-difluoro-6-methylphenyl instead of 2-fluoro-6-chloro-phenyl. Table 58 Table 58 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 58 R! is 2,4-difluoropyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 59 Table 59 consists of 3972 compounds. Compounds 1 to 662. are exactlv the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 59 R1 is 3,5-difluoropyrid-4-yI instead of 2-fluoro-6-chlorophenyl. Table 60 Table 60 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 60 Rl is tetrafluoropyrid-4-yl instead of 2-fluoro-6-chlorophenyI. Table 61 Table 61 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds I to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662-of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 61 R! is 3-fluoropyrid-2-yl instead of 2-fluoro-6-chlorophenyl. Table 62 Table 62 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the n . ... compounds of Table 62 R1 is 4-fluoropyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 63 Table 63 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that m all of the compounds of Table 63 R is 3-fluoropyrid-4-yl instead of 2-fluoro-6-chIorophenyl. Table 64 Table 64 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 64 R1 is 2-fluoropyrid-3-yl instead of 2-fluoro-6-chloropheny!. Table 65 Table 65 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to. 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 65 R1 is 2,4,6-trifluoropyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 66 Table 66 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactiy the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, exceot that in all of the Table 67 Table 67 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 io 662 of Table 20 respectively, compounds 2649 to 3310 axe exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 67 R is2.6-difiuoropyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 6S Table 68 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds I to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 68 R1 is 2,4-difluoro-6-methoxypyrid-3-yl instead of 2-fluoro-6-chIoro-phenyl. Table 69 Table 69 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 69 Rl is 2-fluoro-4-chloropyrid-3-yI instead of 2-fluoro-6-chlorophenyl. Table 70 Table 70 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds I to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds I to 662 of Table 30 respectively, except that in all of the compounds of Table 70 R1 is 3-fluoro-5-chloropyrid-4-yl instead of 2-fiuoro-6-chlorophenyI. Table 71 Table 71 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 71 R1 is 2-chloro-4-fluoropyrid-3-yl instead of 2-fluoro-6-chIorophenyl/ Table 72 Table 72 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 6.62 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds I to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 72 R is 2,4-dichloropyrid-3-yl instead of 2-fluoro-6-chIorophenyl. Table 73 Table 73 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 73 Rl is 3-chloropyrid-2-yl instead of 2-fluoro-6-chloroohenv!. Table 74 Table 74 consists of 3972 compounds. Compounds I to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table-25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 74 R is 4-chlo:opyrid-3-yl instead of 2-fluoro-6-chlorophenyI. Table 75 Table 75 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Tattle 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 75 R1 is 3-chloropyrid-4-yl instead of 2-fluoro-6-chlorophenyl. Table 76 Table 76 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 76 R! is 2-chloropyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 77 Table 77 consists of 3972 compounds. Compounds 1 to662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 77 R1 is 3-trifluoromethyipyrid-2-yl instead of 2-fluoro-6-chlorophenvl. Table 78 Table 7S consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 78 R1 is 4-trifluoromethyIpyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 79 Table 79 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds I to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 79 R1 is 3,5-dichloropyrid-2-yl instead of 2-fluoro-6-chlorophenyl. Table 80 Table 80 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 80 R1 is 4,6-dichloropyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table.3_l compounds 1 to 662 of Table 10 respectively, compounds 1325 to I9S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 6o2 of Table 30 respectively, except that in all of the compounds of Table 81 R'is 3-tritluoromethyipyrid-4-yI instead of 2-fluoro-6-chlorophenyl. Table 82 Table 82 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 82 R1 is 2-trifIuoromethy!pyrid-3-yl instead of 2-fluoro-6-chlorophenyL Table 83 Table 83 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 83 R1 is 2-fluoro-4-trifluoromethylpyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 84 Table 84 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly compounds of Table S4 R1 is 3-fluoro-5-tnfluoromethyipyrid-4-yl instead of 2-fluoro-6-chlorophenyl. Table 85 Table 85 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 85 R1 is 4-fluoro-2-trifIuoromethylpyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 86 Table 86 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the satne as compounds I to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 86 R1 is 2,6-dichloropyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 87 Table 87 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds I to 662 of Table 25 respectively, and compounds S3 IT to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 87 R1 is 3,5-dichloropyrid-4-yl instead of 2-fluoro-6-chlorophenyl. Table 88 compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2643 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in ail of the compounds of Table SS R1 is 3-chIoro-6-trifluoromethylpyrid-2-yl instead of 2-fluoro-6-chlorophenyl. Table 89 Table S9 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same^ as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are -exactly'the.same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 89 R1 is 3-fIuoro-6-trifIuoromethylpyrid-2-yl instead of 2-fluoro-6-chlorophenyl. Table 90 Table 90 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649. to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 90 Rl is pyrid-2-yl instead of 2-fluoro-6-chlorophenyI. Table 91 Table 91 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 91 R1 is pyrid-3-yl instead of 2-fluoro-6-chlorophenyI. Table 92 Table 92 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 92 R1 is pyrid-4-yl instead of 2-fluoro-6-chIorophenyl. Table 93 Table 93 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 93 R1 is 3-fluorothien-2-yl instead of 2-fluoro-6-chlorophenyl. Table 94 Table 94 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all oftfie compounds of Table 94 R1 is 3-chlorothien-2-yl instead of 2-fluoro-6-chIorophenyl. Table 95 as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 95 R1 is 2,4-difIuorothien-3-yl instead of 2-fluoro-6-chlorophenyl. Table 96 Table 96 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 96 R1 is 2,4-dichlorothien-3-yl instead of 2-fluoro-6-chlorophenyl. . Table 97 Table 97 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 97 R1 is 2,4,5-trichlorothien-3-yl instead of 2-fluoro-6-chlorophenyl. Table 98 Table 98 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the Table 99 Table 99 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 ore exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 99 R1 is 2-methylpiperidino instead of 2-fluoro-6-chlorophenyI. Table 100 Table 100 consists of 3972 compounds. Compounds 1 to 662Are exactly the same aS compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 100 R1 is 2,6-dimethyIpiperidino instead of 2-fluoro-6-chIorophenyl. Table 101 Table 101 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 101 R1 is morpholino instead of 2-fluoro-6-chlorophenyl. Table 102 Table 102 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 the same as compounds 1 to 662 of Table ?5 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 102 R1 is 2,6-dimethyImorpholino instead of 2-fluoro-6-chlorophenyl. Table 103 Table 103 consists of 305,844 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 102 (thus, for-example. compound I of Table 103 is the same as compound 1 of Table 1, compound 663 of Table 103 is the same as compound 1 of Table 2, compound 19,861 of Table 103 is the same as compound 1 of Table 31, compound 305,844 of Table 103 is the same as compound 3.972 of Table 102) except that in all of the compounds of Table 103 R is F instead of CI. Table 104 Table 104 consists of 305,844 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 102 (thus, for example, compound 1 of Table 104 is the same as compound 1 of Table 1, compound 663 of Table 104 is the same as compound 1 of Table 2, compound 19,8(51 of Table 104 is the same as compound 1 of Table - 31, compound 305,844 of Table 104 is the same as compound 3,972 of Table 102) except ... that in all of the compounds of Table 104 R is Br instead of CI. Table 105 Table 105 consists of 305,844 compounds. Each of these compounds is exactly the' same as the corresponding compound in Tables 1 to 102 (thus, for example, compound 1 of Table 105 is the same as compound 1 of Table 1, compound 663 of Table 105 is the same as compound 1 of Table 2, compound 19,861 of Table 105 is the same as compound 1 of Table 31, compound 305,844 of Table 105 is the same as compound 3,972 of Table 102) except that in all of the compounds of Table 105 R is methyl instead of CI. Table 106 Table 106 consists of 305,844 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 102 (thus, for example, compound 1 of Table 106 is the same as compound 1 of Table.1, compound 663 of Table 106 is the same as compound 1 of Table 2, compound 19,861 of Table 106 is the same as compound 1 of Table 31, compound 305,844 of Table 106 is the same as compound 3,972 of Table 102) except that in all of the compounds of Table 106 R is ethyl instead of CI. Table 107 Table 107 consists of 305,844 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 102 (thus, for example, compound 1 of Table 107 is the same as compound 1 of Table 1, compound 663 of Table 107 is the same as compound 1 of Table 2, compound I9.S61 of Table 107 is the same as compound I of Table 31, compound 305,844 of Table 107 is the same as compound 3,972 of Table 102) except that in all of the compounds of Table 107 R is cyano instead of CI. Table 108 Table 108 consists of 305,844 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 102 (thus, for example, compound 1 of Table 108 is the same as compound 1 of Table 1, compound 663 of Table 108 is the same as compound 1 of Table 2, compound 19,861 of Table 10S is the same as compound 1 of Table 31, compound 305,844 of Table 108 is the same as compound 3,972 of Table 102) except that in all of the compounds of Table 108 R is methoxy instead of CI. Table 109 Table 109 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table 109 is the same as compound 1 of Table 1, compound 663 of Table 109 is the same as compound 1 of Table 2, etc.) except that in all of the compounds of Table 109 X is CF instead of CH. Table 110 Table 110 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table 110 is the same as compound 1 of Table 1, compound 663 of Table 110 is the same as compound 1 of Table 2, etc.) except that in all of the compounds of Table 110 X is CC1 instead of CH. Table 111 Table 111 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table 111 is the same as compound 1 of Table 1, compound 663 of Table 111 is the same as compound 1 of Table 2, etc.) except that in all of the Table 112 Table 112 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table 112 is the same as compound 1 of Table 1, compound 663 of Table 112 is the same as compound 1 of Table 2, etc.) except that in all of the compounds of Table 112 X is CCH3 instead of CH. Table 113 Table 113 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table 113 is the same as compound 1 of Table 1, compound 663 of Table 113 is the same as compound 1 of Table 2, etc.) except that in all of the compounds of Table 113 Y is CF instead of CH. Table 114 Table 114 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table 114 is the same as compound 1 of Table I, compound 663 of Table 114 is the same as compound 1 of Table 2, etc.) except that in all of the compounds of Table 114 Y is CC1 instead of CH. Table 115 Table 115 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table 115 is the same as compound 1 of Table 1, compound 663 of Table 115 is the same as compound 1 of Table 2, etc.) except that in all of the compounds of Table 115 Y is CBr instead of CH. Table 116 Table 116 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table 116 is the same as compound 1 of Table 1, compound jj£3,o£ Table 116 is the same as compound 1 of Table 2, etc.) except that in all of the compounds of Table 116 Y is CCH3 instead ofCH. listed in Table 1. Thus, compound I of Table ! 17 is the same as compound 1 of Table 21 except that in compound 1 of Table 117. the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 117 are the same as compounds 2 to 662 of Table 21 except that in the compounds of Table 117, the compounds have the general foR""ula (IB). Table 118 Table 1 IS consists of 662 compounds of the general foR""ula (IB), where W, X and Z are CH and Y is N, R is CI, R1 is 2,5,6-trifluorophenyI, and the values of R3 and R4 are as listed in Table I. Thus, compound I of Table 1 IS is the same as compound 1 of Table 22 except that in compound ] of Table 118, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 118 are the same as compounds 2 to 662 of Table 22 except that in the compounds of Table 1 IS, the compounds have the general foR""ula (IB). Table 119 Table 119 consists of 662 compounds of the general foR""ula (IB), where W, X and Z are CH and Y is N, R is CI, R! is 2,3,4,5,6-pentafluorophenyl, and the values of R3 and R4 areas listed in Table 1. Thus, compound 1 of Table 119 is the same as compound 1 of Table 23 except that in compound 1 of Table 119, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 119 are the same as compounds 2 to 662 of Table 23 except that in the compounds of Table 1-19, the compounds have the general foR""ula (IB). Table 120 Table 120 consists of 662 compounds of the general foR""ula (IB), where W, X and Z are CH and Y is N, R is CI, R] is 2,6-difluoro-4-methoxyphenyI, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 120 is the same as compound 1 of Table 24 except that in compound 1 of Table 120, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 120 are the same as compounds 2 to 662 of Table 24 except that in the compounds of Table 120, the compounds have the general foR""ula (IB). Table 121 Table 121 consists of 662 compounds of the general foR""ula (IB), where W, X and Z are CH and Y is N, R is CI, R1 is 2-fluoro-6-chlorophenyl, and the values of R3 and R are as listed in Table 1. Thus, compound 1 of Table 121 is the same as compound I of Table J25 . . except that in compound 1 of Table 121, the compound1 has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 121 are the same as compounds 2 to 662 of Table 25 except that in the compounds of Table 121, the compounds have the general foR""ula (IB). Table 122 Table 122 consists of 662 compounds of the general foR""ula (IB), where W, Y and Z are CH and X is N, R is CI, R1 is 2,4.6-trifluorophenyI, and the values of R3 and R4 are as listed in Table !. Thus, compound 1 of Table 122 is the same as compound 1 of Table 26 except that in compound 1 of Table 122, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 122 are the same as compounds 2 to 662 of Table 26 except that in the compounds of Table 122, the compounds have the general foR""ula (IB). Table 123 Table 123 consists of 662 compounds of the general foR""ula (IB), where \V, Y and Z are CH and X is N, R is CI, R1 is 2,4.5-trifluorophenyl, and the values of R3 and R4 are as listed in Table I. Thus, compound 1 of Table 123 is the same as compound 1 of Table 27 except that in compound 1 of Table 123, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 123 are the same as compounds 2 to 662 of Table 27 except that in the compounds of Table 123, the compounds have the general foR""ula (IB). Table 124 Table 124 consists of 662 compounds of the general foR""ula (IB), where W, Y and Z are CH and X is N, R is CI, R1 is 2,3,4,5,'6-pentafluorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound'1 of Table 124 is the same as compound 1 of Table 28 except that in compound 1 of Table 124, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 124 are the same as compounds 2 to 662 of Table 23 except that in the compounds of Table 124, the compounds have the general foR""ula (IB). Table 125 Table 125 consists of 662 compounds of the general foR""ula (IB), where W, Y and Z are CH and X is N, R is CI, R1 is 2,6-difluoro-4-methoxyphenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table-125 is the same as compound 1 of Table 29 except that in compound 1 of Table 125, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 125 are the same as compounds 2 to 662 of Table 29 except that in the compounds of Table 125, the compounds have the general foR""ula (IB). Table 126 Table 126 consists of 662 compounds of the general foR""ula (IB), where W, Y and Z are CH and X is N, R is CI, Rl is 2-fluoro-6-ch!orophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 126 is the same as compound 1 of Table 30 except that in compound 1 of Table 126, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Tabie 126 are the same as compounds 2 to 662 of Table 30 except that in the compounds of Table 126, the compounds have the general foR""ula (IB). Compounds of foR""ula (7) or (S). which are examples of compounds of general foR""ula (1) where one of R and R2 is N-R3R-,can be made as shown in Scheme 1, in which W, X, Y, Z, R , R" and R have the meanings given above and R is C1-4 alkyl. Compounds of general foR""ula (4) can be prepared from compounds of general foR""ula (2), which are either commercially available or made by methods known in the literature, by reaction with acids of general foR""ula (3), using standard coupling methods, for example by conversion to the acid chloride using a chlorinating agent such as thionyl chloride, followed by reaction of the resultant acid chloride optionally in the presence of a - base such-as triethylamine, in a suitable solvent such as dichloromethane or toluene. Compounds of general foR""ula (5) can be prepared by treating compounds of general foR""ula (4) with a base such as sodium hydride, optionally in the presence of a Lewis acid general foR""ula (6) can be prepared by reaction of compounds of general foR""ula (5) with a chlorination reagent such as phosphorus oxychloride, either neat or in a suitable solvent such as toluene, at between 50 and 150°C. but preferably between SO and 110°C, or in a microwave reactor at between 150 and 300°C, but preferably between 200 and 250°C. Compounds of foR""ula (7) and (S) can be prepared by reaction of compounds of general foR""ula (6) with an amine R3RaNH, either neat, or in a suitable solvent such as DMF, between room temperature and 150°C, but preferably between 50 and 80°C. If compounds (7) and (S) are produced as a mixture they can be separated by suitable means such as crystallisation or chromatography under noR""al or reverse phase conditions. Compounds of the general foR""ulae (5), (6), (7) and (8) may be derivatised, via the chloro or hydroxy substituents, using routine chemical techniques to foR"" other compounds of the general foR""ula (1). Alternatively, other compounds of the general foR""ula (1) may be prepared using a similar methodology to that described for preparing the compounds (5) to (8) and employing preparative techniques known from the chemical literature. Compounds of foR""ula (7) can also be made as shown in scheme 2. Compounds of general foR""ula (10) can be prepared from compounds of general foR""ula (9), which are either commercially available or made by methods known in the literature, by reaction with acids of general foR""ula (3), using standard coupling methods, for chloride, followed by reaction of the resultant acid chloride optionally in the presence of a base such as triethylamine, in a suitable solvent such as dichioromethane or toluene. Compounds of general foR""ula (11) can be prepared by treating compounds of general foR""ula (10) with a base such as sodium hydride, optionally in the presence of a Lewis acid such as magnesium oxide, in a suitable solvent such as NN-dimethylfoR""amide (DMF) or toluene, at between room temperature and 150°C, but preferably at 60-9O°C. Compounds of general foR""ula (12) can be prepared by reaction of compounds of general foR""ula (11) with a chlorination reagent such as phosphorus oxychloride, either neat or in a suitable solvent such as toluene, at between- 50 and 150°C, but preferably between SO and 110°C, or in a microwave reactor at between 150 and 300°C, but preferably between 200 and 250°C. Compounds of foR""ula (7) can be prepared from compounds of foR""ula (12) by reductive amination, for example by reaction with a ketone or aldehyde in a suitable solvent such as ethanol or toluene, at between room temperature and reflux, optionally in the presence of an acid catalyst such as para-toluenesulphonic acid or a drying agent such as moleC1-6lar sieves, followed by treatment with a suitable reducing agent such as sodium borohydride, at between -20°C and 40°C, but preferably at room temperature. The aldehyde or ketone is chosen so that the desired groups R3 and R4 are foR""ed after reduction of the product of reaction with the amine (12). For example if compounds of foR""ula (12) are reacted with one equivalent of propionaldehyde and then sodium borohydride, compounds of foR""ula (7) where RJ is n- propyl, and R is hydrogen are foR""ed. If required, the reaction can be repeated with a different aldehyde or ketone. For example, if acetone is used for the second reaction, then compounds of foR""ula (7) where R3 is N-propyl and R4 is zs-o-propyl, are foR""ed. Alternatively compounds of foR""ula (7) can be foR""ed from compounds of foR""ula (12) by alkylation with a group R3LG, where LG is a leaving group, by treatment with a suitable base such as sodium hydride in a solvent such as DMF, or a base such as potassium carbonate in a solvent such as acetone or DMF, at between -78°C and 100°C, but preferably between room temperature and 60°C, followed by treatment with R4LG in a second step under the same conditions if required. - - Compounds of foR""ula (13) can be prepared as shown in Scheme 3 from compounds of foR""ula (6) by reaction with a source of fluoride ion, such as potassium fluoride, in a suitable solvent such as sulpholane, at a temperature between 50°C and 200°C7 but preferably at 80-150°C. Compounds of foR""ula (14) and/or compounds of foR""ula (15) can be prepared from difluoro compounds of foR""ula (13) by reaction with an amine of foR""ula R3R4NH in a suitable solvent such as DMF or CH2Q2, at a temperature of 0°C-100°C, but preferably at room temperature. Compounds of general foR""ula (16), where Hal1 is chlorine or fluorine, can be converted into compounds of foR""ula (17), (18), (19), (20), (21), (22) or (23) as shown in Scheme 4. Compounds of general foR""ula (17) where Hal2 is bromine or iodine can be foR""ed by reacting compounds of general foR""ula (16) with a metal halide, for example C1-6prous bromide, in a suitable solvent, for example DMF, at between room temperature and 155°C, but preferably between 70°C and 155°C Compounds of general foR""ula (18) where V is oxygen or sulphur and R is C1-8 alkyl, can be foR""ed by reacting compounds of general foR""ula (16) with a metal alkoxide or thioalkoxide MVR9 in a suitable solvent, for example sodium methoxide in methanol, at room temperature to 65°C Compounds of general foR""ula R is C1-8alkyl. can be foR""ed by reacting compounds of general foR""ula (16) with an alkyl metal derivative in a suitable solvent, for example methyl magnesium bromide in THF, optionally in the presence of catalyst such as C1-6prous bromide or Pd(Ph)4, between -40°C and 50°C. Compounds of general foR""ula (21) can be foR""ed by reduction of compounds of general foR""ula (16), where Hal1 is chlorine, for example by hydrogenolysis with hydrogen gas and a metal catalyst such as palladium on carbon in a suitable solvent such as ethanol, at room temperature. Compounds of general foR""ula (22) where R11 is hydrogen or C1-6 alkyl, can be foR""ed by reaction of compounds of general foR""ula (16) with an alkyl acetylene under the Sonogashira conditions, for example with 1-propyne in triethylamine in the presence of a C1-6prous salt such as C1-6prous iodide and a palladium catalyst such as Pd(Ph)4, between room temperature and 70°C Compounds of general foR""ula (23) where R12 is hydrogen or C1-6alkyl, can be foR""ed by reaction of compounds of general foR""ula (16) with an alkenyl metal derivative in a suitable solvent, such as ethenylboronic acid in THF, in the presence of a palladium catalyst such as Pd(Ph)4 and a base such as caesium carbonate, between room temperature and 65°C. In Scheme 5 compounds of general foR""ula (24), where the two R R N groups are identical, can be made from compounds of general foR""ula (13) by reaction with a large excess of amine R3R4NH in a suitable solvent such as DMF, at a temperature between 0°C and 150°C, but preferably between room temperature and 100°C Further assistance in the preparation of the compounds of foR""ula (1) may be derived from the following publications: Emilio, Toja, et. al.7J. Heterocyclic Chem., 23, 1955 CI 9.86), H. Schafer, et. al.,J.f.prakt. Chemie, 321(4), 695 (1970) and H.Bredereck et. a/., Chem. Ber. 96, 1868-1872 (1993). The inteR""ediate chemicals having the general foR""ulae (4), (5), (6) and (13): wherein W, X, Y, Z, R and R are as define above, are believed to be novel compounds and foR"" a further part of this invention. It should be noted that the inteR""ediate of general foR""ula (5) may exist in the tautomeric foR""s (a), (b) and (c) as well as in the foR"" shown in foR""ula (5): The invention as defined by the'general foR""ula (5) embraces all such tautomers; Of partiC1-6lar interest are the inteR""ediates listed in Tables 127 to 134 below. In Tabl-127 the compounds have the general foR""ula (4) where R7 is methyl and W, X, Y, Z and R1 have the values shown in the table. Table 128 Table 128 consists of 48 compounds of the general foR""ula (5), where \V,X, Y, Z and R1 have the values given in Table 127. Thus, compound 1 of Table 12S has the same W, X, Y, Z and R! values as compound 1 of Table 127, etc. Table 129 Table 129 consists of 48 compounds of the general foR""ula (6), where W, X, Y, Z and R1 have the values given in Table 127. Thus, compound 1 of Table 129 has the same W, X, Y, Z and R1 values as compound 1 of Table 127, etc. Table 130 Table 130 consists of 48 compounds of the general foR""ula (13), "where W, X, Y, Z and Rl have the values given in Table 127. Thus, compound 1 of Table 130 has the same W. " X, Y, Z and R1 values as compound 1 of Table 127, etc. Table 131 Table 131 consists of 48 compounds of the general foR""ula (4), where W, X, Y, Z and R1 have the values given in Table 127 and R7 is ethyl. Thus, compound 1 of Table 131 is the same as compound 1 of Table 127 except that in compound 1 of Table 131, R' is ethyl instead of methyl. Similarly, compounds 2 to 48 of Table 131 are the same as compounds 2 to 48 of Table 127 except that in the compounds of Table 131, R is ethyl. The compounds of foR""ula (1) are active fungicides and may be used to control one or more of the following pathogens: PyriC1-6laria oryzae. (Magnaporthe grisea) on rice and wheat and other PyriC1-6laria spp. on other hosts; Puccinia triticina (or recondita), Puccinia striifoR""is and other rusts on wheat, Puccinia hordei, Puccinia striifoR""is and other rusts on barley, and rusts on other hosts (for example turf, rye, coffee, pears, apples, peanuts, sugar beet, vegetables and ornamental plants); Erysiphe dehoracearum on C1-6C1-6rbits (for example melon); Blumeria (or Erysiphe) graminis (powdery mildew) on barley, wheat, rye and turf and other powdery mildews on various hosts, such as Sphaerotheca maC1-6laris or. hops, apples and Uncinula necator on vines; Cochliobolus spp., Helminihosporium spp., Drechslera spp. (Pyrenophora spp.)* Rhynchosporium spp., Mycosphaerella graminicola (Septoria tritici) and Phaeosphaeria nodonim (Stagonospora nodorwn or Septoria nodorum). Pseudocercosporella herpotrichoides and Caeumannomyces gramirus on cerenls (for example wheat. barley, rye), turf and other hosts; Cercospora arachidicola and Cercosporidium personatum on peanuts and other Cercospora spp. on other hosts, for example sugar beet, bananas, soya beans and rice; Botrytis cinerea (grey mould) on tomatoes, strawberries, vegetables, vines and other hosts and other Botrytis spp. on other hosts; Alternaria spp. on vegetables (for example carrots), oil-seed rape, apples, tomatoes, potatoes, cereals (for example wheat) and other hosts; Venturia spp. (including Venturia inaequalis (scab)) on apples, pears, stone fruit, Jree nuts and other hosts; Cladosporium spp. on a range of hosts including cereals (for example wheat) and tomatoes; Monilinia spp. on stone fruit, tree nuts and other hosts; Didymella spp. on tomatoes, turf, wheat, C1-6C1-6rbits and other hosts; Phoma spp. on oil-seed rape, turf, rice, potatoes, wheat and other hosts; Aspergillus spp. and Aureobasidium spp. on wheat, lumber and other hosts; Ascochyta spp. -on peas, wheat, barley and other hosts; Stemphyliwn spp. (Pleospora spp.) on apples, pears, onions and other hosts; summer diseases (for example bitter rot (Gbmerella cingulata), black rot or frogeye leaf spot {Botryosphaeria obtiisa), Brooks fruit spot (Mycosphaerella pomi), Cedar apple rust (Gymnosporangiumjuniperi-virginianae), sooty blotch (Gloeodes pomigena), flyspeck (Schizothyrium pomi) and white rot (Botryosphaeria dothidea)) on apples and pears; Plasmopara viticola on vines; other downy mildews, such as Bremia lactucae on lettuce, Peronospora spp. on soybeans, tobacco, onions and other hosts, Pseudoperonospora humuli on hops and Pseudoperonospora C1-6bensis on C1-6C1-6rbits; Pythium spp. (including Pythium ultimum) on turf and other hosts; Phytophthora infestans on potatoes and tomatoes and other Phytophthora spp. on vegetables, strawberries, avocado, pepper, ornamentals, tobacco, cocoa and other hosts; Thanatephorus C1-6C1-6meris on rice and turf and other Rhizoctonia spp. on various hosts such as wheat and barley, peanuts, vegetables, cotton and turf; Sclerotinia spp. on turf, peanuts, potatoes, oil-seed rape and other hosts; Sclerotium spp. on turf, peanuts and other hosts; Gibberella fujikuroi on rice; Colletotrichum spp. on a range of hosts including turf, coffee and vegetables; Laetisaria fucifoR""is on turf; Mycosphaerella spp. on bananas, peanuts, citrus, pecans, papaya and other hosts; Diaporthe spp. on citrus, soybean, melon, pears, lupin and other hosts; Elsinoe spp. on citrus, vines, potatoes and tomatoes; Pyrenopeziza spp. on oil-seed rape and other hosts; Oncobasidium theobromae on cocoa causing vasC1-6lar streak dieback; Fusarium spp., Typhula spp., Microdochium nivale, Usiilago spp., Urocystis spp., Tilletia spp. and Claviceps purpurea on a variety of hosts but partiC1-6larly wheat, barley, turf and maize; Ramulana spp. on sugar beet, barley and other hosts; post-harvest diseases partiC1-6larly of fruit (for example Penicillium digitatum, Penicillium italicwn and ThchodeR""a viride on oranges, Colletotrichum musae and Gloeosporiwn musarum on bananas and Botrytis cinerea on grapes); other pathogens on vines, notably Eniypa lata, Gnignardia bidwelliL Phellinus igniarus, Phomopsis viticola, Pseudopeziza tracheiphila and Stereum hirsutum,other pathogens on trees (for example LophodeR""ium seditiosum) or lumber, notably CephaloasC1-6s fragrans, Ceratocyslis spp., Ophiostomapiceae, Penicillium spp., -" TrichodeR""a pseudokoningii, TrichodeR""a viride, TrichodeR""a harzianwn, Aspergillus niger, Leptographium lindbergi and Aureobasidium pulhdans,and fungal vectors of viral diseases (for example Polymyxa gramims on cereals as the vector of barley yellow mosaic virus (BYMV) and Polymyxa betae on sugar beet as the vector of rhizomania). A compound of foR""ula (1) may move acropetally, basipetally or locally in plant tissue to be active against one or more fungi. Moreover, a compound of foR""ula (l)Tnay be volatile enough to be active in the vapour phase against one or more fungi on the plant. The invention therefore provides a method of combating or controlling phytopatho-genic fungi which comprises applying a fungicidally effective amount of a compound of foR""ula (1), or a composition containing a compound of foR""ula (1), to a plant, to a seed of a plant, to the loC1-6s of the plant or seed or to soil or any other plant growth medium, e.g. nutrient solution. The teR"" "plant" as used herein includes seedlings; bushes and trees. FurtheR""ore, the fungicidal method of the invention includes protectant, C1-6rative, systemic, eradicant and antisporulant treatments. The compounds of foR""ula (1) are preferably used for agriC1-6ltural, hortiC1-6ltural and turfgrass purposes in the foR"" of a composition. - - In order to apply a compound of foR""ula (1) to a plant, to a seed of a plant, to the loC1-6s of the plant or seed or to soil or any other growth medium, a compound of foR""ula (1) is usually foR""ulated into a composition which includes, in addition to the compound of liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting). It is preferred that all compositions (both solid and liquid foR""ulations) comprise, by weight, 0.0001 to 95%, more preferably I to 85%, for example 5 to 60%, of a compound of foR""ula (1). The composition is generally used for the control of fungi such that a compound of foR""ula (1) is applied at a rate of from 0.1 g to 10kg per hectare, preferably from Ig to 6kg per hectare, more preferably from lg to 1kg per hectare. When used in a seed dressing, a compound of foR""ula (1) is used at a rate of O.OOOlg to lOg (for example 0.00lg or 0.05g), preferably 0.005g to lOg, more preferably 0.005g to 4g, per kilogram of seed. In another aspect the present invention provides a fungicidal composition comprising a fungicidally effective amount of a compound of foR""ula (1) and a suitable carrier or diluent therefor. In a still further aspect the invention provides a method of combating and controlling fungi at a loC1-6s, which comprises treating the fungi, or the loC1-6s of the fangi with a fungicidally effective amount of a composition comprising a compound of foR""ula (1). The compositions can be chosen from a number of foR""ulation types, including dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke foR""ulations, capsule suspensions (CS) and seed treatment foR""ulations. The foR""ulation type chosen in any instance will depend upon the partiC1-6lar purpose envisaged and the physical, chemical and biological properties of the compound of foR""ula (1). Dustable powders (DP) may be prepared by mixing a compound of foR""ula (1) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder. Soluble powders (SP) may be prepared by mixing a compound of foR""ula (1) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water dispersibiiity/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to foR"" water soluble granules (SG). Wettable powders (WP) may be prepared by mixing a compound of foR""ula (1) with one or more solid diluents or earners, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate the dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions may also be granulated to foR"" water dispersible granules (WG). Granules (GR) may be foR""ed either by granulating a mixture of a compound of foR""ula (1) and one or more powdered solid diluents or carriers, or from pre-foR""ed blank granules by absorbing a compound of foR""ula (1) (or a solution thereof, in a suitable agent) in "a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of foR""ula (1) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulphates or phosphates) and drying if necessary. Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketonesand esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent). Dispersible Concentrates (DC) may be prepared by dissolving a compound of foR""ula (1) in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surface active agent (for example to improve water dilution or prevent crystallisation in a spray tank). Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may be prepared by dissolving a compound of foR""ula (1) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). Suitable organic solvents for use in-ECs include aromatic hydrocarbons (such as alkylbenzenes or alkyinaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclo-hexanone), alcohols (such as product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment. Preparation of an EW involves obtaining a compound of foR""ula (1) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion. Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents that have a low solubility in water. Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a theR""odynamically stable ^ isotropic liquid foR""ulation. A compound of foR""ula (1) is present initially in either the water or the solvent/SFA blend. Suitable solvents for use in MEs include those hereinbefore described for use in in ECs or in EWs. An ME may be either an oil-in-water or a watej-in-oil system (which system is present may be deteR""ined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same foR""ulation. An ME is suitable for dilution into water, either remaining as a microemulsion or foR""ing a conventional oil-in-water emulsion. Suspension concentrates (SC) may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of foR""ula (1). SCs may be prepared by bail or bead milling the solid compound of foR""ula (I) in a suitable medium, optionally with c ne or more dispersing agents, to produce a fine particle suspension of the compound. One c; more wetting agents may be included in the composition and a suspending agent may be inc ;ded to reduce the rate at which the particles settle. Alternatively, a compound of foR""u . (1) may be dry milled and added to water, containing agents hereinbefore described, to pre :ce the desired end product. \erosol foR""ulations comprise a compound of foR""ula (1) and a suitable propellant (for e: nple /z-butane). A compound of foR""ula (1) may also be dissolved or dispersed in a suitab medium (for example water or a water miscible liquid, such as /i-propanol) to provi .ompositions for use in non-pressurised, hand-actuated spray pumps. . compound of foR""ula (1) may be mixed in the dry state with a pyrotechnic mixture to fo composition suitable for generating, in an enclosed space, a smoke containing the Capsule suspensions (CS) may be prepared in a manner similar to the preparation of EW foR""ulations but with an additional polymerisation stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of foR""ula ;!) and, optionally, a carrier or diluent therefor. The polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure. The compositions may provide for controlled release of the compound of foR""ula (1) and they may be used for seed treatment. A compound of foR""ula (1) may also be foR""ulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound. A composition may include one or more additives to improve the biological perfoR""ance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of foR""ula (1)). Such additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the ^ action of a compound of foR""ula (1)). A compound of foR""ula (1) may also be foR""ulated for use as a seed treatment, for example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS). The preparations of DS,SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above. Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-foR""ing barrier). Wetting agents, dispersing agents and emulsifying agents may be SFAs of the cationic, anionic, amphoteric or non-ionic type. Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts. Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds sodium laureth-3-sulphate), ether carboxylates (for example sodium lauretho-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally these products may be ethoxylated), sulphosuccinamates, paraffin or define sulphonates, taurates and lignosulphonates. Suitable SFAs of the amphoteric type include betaines, propionates and glycinates. Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenoL nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins. Suitable suspending agents include hydrophrlic colloids (such-as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcelltriose) and swelling clays (such as bentonite or attapulgite). A compound of foR""ula (1) may be applied by any of the known means of applying fungicidal compounds. For example, it may be applied, foR""ulated or unfoR""ulated, to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic C1-6lture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste foR""ulation, applied as a vapour or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water-soluble bag) in soil or an aqueous environment, A compound of foR""ula (1) may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems. Compositions for use as aqueous preparations (aqueous solutions or dispersions) are generally supplied in the foR"" of a concentrate containing a high proportion withstand storage for prolonged periods and, after such storage, to be capable of addition to water to foR"" aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment. Such aqueous preparations may contain varying amounts of a compound of foR""ula (1) (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used. A compound of foR""ula (1) may be used in mixtures with fertilisers (for example nitrogen-, potassium- or phosphorus-containing fertilisers). Suitable foR""ulation types include granules of fertiliser. The mixtures suitably contain up to 25% by weight-of the compound of foR""ula (1). The invention therefore also provides a fertiliser composition comprising a fertiliser and a compound of foR""ula (1). The compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having'similar or complementary fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, .. nematicidal or acaricidal activity. By including another fungicide, the resulting composition may have a broader spectrum of activity or a greater level of intrinsic activity than the compound of foR""ula (1) alone. Further the other fungicide may have a synergistic effect on the fungicidal activity of the compound of foR""ula (1). The compound of foR""ula (1) may be the sole active ingredient of the composition o it maybe admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate. An additional active ingredient may: provide a composition having a broader spectrum of activity or increased persistence at a loC1-6s; synergise the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of foR""ula (1); or help to overcome or prevent the development of resistance to individual components. The partiC1-6lar additional active ingredient will depend upon the intended utility of the composition. Examples of fungicidal compounds which may be included in the composition of the invention are AC 382042 trifloxystrobim triflumizole, trifonne, triticonazole. validamycin A, vapam, vinclozolin, XRJD-563, zineb, ziram, zoxamide and compounds of the foR""ulae: The compounds of foR""ula (1) may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases. Some mixtures may comprise active ingredients, which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional foR""ulation type. In these cirC1-6mstances other foR""ulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a" water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resultant composition is a suspoemulsion (SE) foR""ulation. Step I 2-Aminonicotinic acid ethyl ester (2.4 g) was suspended in dry toluene (50 ml). To the stirred suspension, 2,4,6-trifluorophenylacetyl chloride (3.0 g) in dry toluene (20 ml) was added. The resulting suspension was heated to reflux for 8 hours. The reaction mixture was cooled to ambient temperature, diluted with diethyl ether (100 ml), washed with water and brine, and the organic layer was dried over magnesium sulphate. The solvent was evaporated... to give 2-[2-(2,4,6-trifluorophenyl)-acetylamino]-nicotinic acid ethyl ester as a yellow solid (4.5 g, 93%). 'H NMR (CDCh) 5 ppm: 133 (t,3H), 4.00 (s,2H), 4.31 (q,2H), 6.63 (m,2H); 7.00 (dd,lH), 3.25 (dd,lH), 8.50 (dd,lH), 10.86 (s,lH). Step 2 The product of Step 1 (3.0 g) was dissolved in toluene (100 ml) and sodium hydride (1.0 g of an 60% dispersion in mineral oil) was added portion-wise. There was an immediate reaction, and the mixture was stirred at room temperature for 2 hours, and at 70°C for 5 hours. The reaction mixture was cooled and evaporated to give a white solid (3 g), which was then acidified with dilute hydrochloric acid. The resultant white suspension was filtered and collected, washed with ether and dried to give 3-(2>4?6-trifluorophenyl)- lH[l,8]naphthyridine-2,4-dione (1.6 g, 62%). 1H NMR (d6-DMSO) 5 ppm: 7.26 (m,3H), 8.35 (dd,lH), S.59 (dd,lH),l 1.21 (s,l H), 11 -97 (s,lH). Step 3 The product from Step 2 (1.0 g) was added portion-wise to phosphorus oxychloride (18 ml) with stining. The reaction was exotheR""ic. The mixture became yellow with a fine suspension, and was then refluxed for 3 hours. Excess phosphorus oxychloride was evaporated, the mixture was diluted with diethyl ether, and then washed with, ice water and brine, and the organic layer was dried over magnesium sulphate. The solvent was evaporated to give 2,4-dichloro-3-(2,4,6-trifluorophenyI)-[l,S]naphthyridine as a yellow solid (1.0 g, 88%). 1H NMR (CDCI3) 6 ppm: 6.81 (m?2H), 7.61 (dd,lH), 8.60 (dd.lH), 9.17 (dd.lH). Step 4 The product from Step 3 (0.12 g). isopropylamine (0.3 ml) and .V-ethyl-di/jo- propylamine (0.10 g) were refluxed in DMF (8 ml) in a sealed tube at 50°C for 17 hours. The dark coloured reaction mixture was evaporated to give an oil, which was puritled by flash column chromatography on silica gel (40-60, ethyl acetate/hexane 1/3) to give [2-chloro-3- (2,4,6-trif]uorophenyl)-[l,8]naphthyridin-4-yl]-isopropylamine as white crystals (0.059.g, 46%), m.p. 193°C. 'H NMR(CDCb) 5 ppm: 1.06 (d,6H), 3.68 (m.lH), 4.04 (m,lH), 6.80 (m,2H), 7.36 (dd,lH), 8.28 (dd,lH), 9.00 (dd,lH) and [4-chloro-3-(2,4,6-trifluorophenyl)-[l,S]naphthyridin-2-yl]-isopropylamine as yellow crystals, (0.039g, 30%), m.p. 202°C. 'H NMR (CDC13) 5 ppm: 1.24 (d,6H), 4.35 (m,lH), 4.70 (m,lH), 6.93 (m52H), 7.70 (dd,lH), 8.38 (dd,lH), 8.67 (dd,lH). » 2,4-DichIoro-3-(2,4,6-trifluoro-phenyl)-[l,8}naphthyridine (0.12 g, the product from Example 1, step 3) and morpholine (0.01 ml) were refluxed in DMF (Sml) in a sealed tube at 'H NMR (CDCh) 5 ppm: 3.34 (m.2H), 3.62 (m,2H), 6.90 (m.2H), 7.43 (dd,lH), 8.51 (ddJH), 9.05 (dd,lH). Starting with 2-amino-5-bromo-nicotinic acid ethyl ester using a process analogous to that described in Example 1, steps 1 to 4, the title compound was synthesized (41%), as yellow crystals, m.p. 202°C. lH NMR (CDC13) 5 ppm: 1.36 (d,6H), 3.94 (m,lH), 4.25 (m,lH), 7.06 (m,2H), 8.64 (dJH), 9.25 (d,lH). Step 1 3-Amino-4-pyridinecarboxylic acid (5.52 g) was suspended in ethanol (300ml) at room temperature, with stirring. One equivalent ofDMAP (10.0 g) was added initially and the mixture stirred for 1 hour at room temperature to produce a suspension. A second equivalent ofDMAP was added and the suspension disappeared. EDC (8.0 g) was then added and the reaction stirred at room temperature for 17 hours. The solvent was removed give yellow oil, which was water-soluble. The aqueous fraction was extracted with ethyl acetate, washed with brine and dried over magnesium sulphate. After evaporation of the solvent a sludge (16.2 g) was obtained which was passed through a plug of si lira gel (40-60) eluting with ethyl acetate, giving a yellow liquid (4.5 g), which by NMR was the desired product ethyl 3-amino-4-pyridinecarboxylate in a ratio of 2:1 with DMAP, and which was used for the next reaction without further purification. lH NMR (CDC13) 6 ppm: 1.4 (t,3H), 4.4 £q,2h), 5.8 (bs,2H), 7.6 (d,lH), 7.95 (d,lH), 8.2 (s,lH). Step 2 The crude ester from Step I (4.5 g) was dissolved in dry DC1-4 (30 ml), and then pyridine (5.0 ml) added to give a dark brown solution. The stirred solution was cooled in an ice bath, and 2,4,6-trifluorophenylacetyI chloride (3.1 g) in dry DC1-4 (20 ml) added - -dropwise. The reaction mixture was stirred for 6 hours and stood over night. The solvent was removed to give an orange sludge, water added and the solid was dissolved in ethyl acetate. The organic fraction was washed with sodium bicarbonate solution, followed by a small amount of 1M hydrochloric acid solution, then water and dried magnesium sulphate." The ethyl acetate was evaporated to yield a solid (6.5 g), which was purified by flash column chromatography on silica gel (40-60), eluting with ethyl acetate to give ethyl 3-[2-(2,4,6-trifluorophenyl)-acetyIamino]-pyridine-4-carboxylate as a yellow solid (3.2 g). lH NMR (CDCb) 5 ppm: 1.45 (t,3H), 3.8 (fd,2H), 4.45 (q,2H) 6.75 (t,2H), 7.8 (d,2H), 8.45 (d,2H), 10.0 (s,lH), 11.0 (s,lH). Step 3 The product from Step 2 (3.0 g) and potassium carbonate (1.6 g) were stirred in dry DMF (100 ml) at 100°C for 3 hours. The reaction was cooled and the excess DMF evaporated to give a black oil. Water (100ml) was added and then washed with ethyl acetate. The aqueous fraction was filtered and acidified with 2M aqueous hydrochloric acid to neutral pH, and the water was evaporated to give a solid, which was then extracted with methanol. The methanol extract was evaporated to give the crude 3-(2,4,6-trifluorophenyl)-liZ-... [l,7]naphthyridine-2,4-dione as a dark brown crystalline solid (2.0 g), which was used for the next reaction without further purification. 'H NMR (CDCI3) 5 ppm: 6.8 (t, 2H), 7.95 (m:2H), 8.2 (d,lH). Step 4 phosphorus oxychloride was evaporated to give a brown oil, which was dissolved in diethyl ether (100 ml) and washed with cold water. The ether layer was separated, dried over magnesium sulphate and evaporated to give a sludge (0.150 g),which was purified by flash column chromatography on silica gel (40-60), eluting with diethyl ether, to give 2.4-dichIoro-3-(2.4,6-trifluorophenyI)-[I,7]naphthyndine as an oil (0.10 g) which solidified on standing. 'H NMR (CDC13) 5 pom: 6.9 (t,2H), S.05 (dJH), 8.8 (d,iH), 9.5 (s,lH), .\f 329 Step 5 The product of Step 4 (0.09 g) was dissolved in DC1-4 (3.0 ml) and transferred to a sealed tube containing isopropylamine (I.OmI), N-ethyl-dizsopropylarnine (0.07 g) and dimethylacetamide (1.0ml). The vessel was sealed and gently waR""ed to 60°C for 10 hours. The reaction was cooled and evaporated to give an oil, which was purified by flash column chromatography on silica gel (40-60) eluting with diethyl ether. Two isomers were obtained: [2-chloro-3-(2,4,6-trifIuoro-phenyl)-[l,7]naphthyridin-4-yl]-isopropylamine as an oil (0.028 - g) 1HNMR (CDC13) 5 ppm: 1.1 (d, 6H), 3.75 (m,lH), 4.3 (bd,lH), 6.9 (t,2H), 7.7.5(d,lH), 8.6 (d,lH), 9.35(s,lH). The second isomer, [4-chloro-3-(2,4J6-trifluoro-phenyl)-[l,7]naphthyridin-2-yl]- isopropylamine, was obtained as a mixture with the starting dichloro compound, and was reacted again and purified by chromatography as described above to give the compound as an oil. 1H NMR (CDC13) 5 ppm: 1.1 (d,6H), 4.25 (bd,lH), 4.5 (m,lH), 6.9 (t,2H), 7.75 (d,lH), S.4 Step 1 Ethyl 4-aminopyridine-3-carboxyIate (1.5 g) was dissolved in dry toluene (50 ml) to give a pale yellow solution, and 2-chloro-6-fluorophenylacetyl chloride (1.S7 g) in dry DC1-4 (13 ml) was added. The bright yellow reaction mixture was heated at 95°C for 4 hours. The brownish solution was cooled to ambient temperature, ethyl acetate was added and the mixture was washed with water, brine, and then dilute hydrochloric acid, and the organic layer was dried over magnesium sulphate. The solvent was evaporated to yield a brown solid, which was purified by flash column chromatography on silica gel (40-60) eluting with hexane:ethyl acetate 1:1, to yield pure ethyl 4-(2-(2-chloro-6-fluorophenyl)acetamido)-pyridine-3-carboxylate as a yellow solid (1.4 g), m.p. 114-116 QC 'HNMRfCDCWSppm: 1.32 (t,3H), 3.91 (s,2H), 4.28 (q,2H), 7.02 (m,lH), 7.21 (m,2H), 3.51 (m,2H), 9.07 (s,lH), 11.2 (s,lH). . Step 2 The product from Step 1 (1.0 g) was dissolved in DMF (15 ml) and solid potassium carbonate (0.S g) was added. The resulting pale yellow solution was heated at 100°C for 4 hours. The reaction mixture was cooled and evaporated to give a yellow solid (3 g), which was then acidified with dilute hydrochloric acid. The resulting white suspension was filtered and collected, washed with ether and dried to give 3-(2-chloro-6-fluorophenyl)-l/f-[l,6] naphthyridine-2,4-dione (0.8 g), m.p. 249 °C. 1H NMR (d6-DMSO) 5 ppm: 6.80 (d,lH), 7.00 (m,lH), 7.13 (m,2H), 8.10 (d,IH), 8.62 (d,lH), 12.11 (s,lH). Step 3 The product from Step 2 (0.70 g) was dissolved in 1,2-dichloroethane (15 ml). DMF (2 ml) and phosphorus oxychloride (2 ml) were added with stirring. The pale yellow-suspension was then refluxed for 4 hours. The reaction mixture was cooled to ambient temperature, diluted with diethyl ether,.and then washed with water to give 2>4-dichIoro-3-(2-chloro-6-fluorophenyl)-l,6-naphthyridine as a light yellow solid (0.38 g). H NMR (CDC13) S ppm: 7.12 (td,lH), 7.32 (d,lH), 7.4.1 (dd,lH), 7.S7 (bs,lH), 8.88 (bs,l£). 9.40(bs,lH). Step 4 The product from Step 3 (0.10 g) was dissolved in DMF (2 ml). Sec-butylamine (0.2 chromatography on silica gel (40-60) in ethyl acetaterhexane 1:1 to give N-sec-butyl-4-chloro-3-(2-chloro-6-fIuorophenyl)-l,6-naphthyridin-2-amineas a light yellow gum (0.0 8g). 'H NMR (CDCI3) 5 ppm: 0.08 (m,3H), 1.10 (t,3H), 1.4S (m,2H). 4.18 (m,lH), 4.28 (m,lH). 7.10 (m,lH), 7.36 (UH), 7.40 (m,lH), 8.52 (d,lH), 9.20 (s,lH). 9.30 (s,lH). Step 1 2,4-Dichloro-3-(2-chloro-6-fluorophenyl)-l,6-naphthyridine (0.20 g) was dissolved in sulpholane (2 ml). Potassium fluoride (0.11 g) was added and the mixture was heated in a sealed tube at 120°C for 14 hours. The honey coloured reaction mixture was,.cooled to ambient temperature, diluted with diethyl ether, and then washed extensively with water. After evaporation of the solvent the resulting light yellow oil was purified by flash column chromatography on silica gel (40-60) eluting with ethyl acetate:hexane 1:4, to give 3-(2-chloro-6-fluorophenyl)-2,4-difluoro-l,6-naphthyridine as a light yellow solid (0.10 g). 1H NMR (CDCb) 5 ppm: 7.06 (m,lH), 7.20 (m,IH), 7.31 (m,IH), 8.53 (d,lH), 9.20 (d,lH). Step 6 The product from Step 1 (0.10 g) was dissolved in DMF (2 ml). Sec-butylamine (0.1 ml) and DMAP (0.001 g) were added and the mixture was stirred in a sealed tube at ambient temperature for 18 hours. The brown reaction mixture was diluted with diethyl ether, washed with brine and dried over sodium sulphate. After evaporation of the solvent the resulting yellow gum was purified by flash column chromatography on silica gel (40-60) in ethyl acetate:hexane 1:3 to give N-sec-butyl-3-(2-chloro-6-fluorophenyl)-2-fluoro-l,6- naphthyridin-4-amine as a darlc yellow solid (0.06 g). 1H NMR (CDCb) 5 ppm: 0.082 (m,3H), 1.20 (m,3H), 1.34 (m,2H), 3.02 (m,IH), 5.0S (m,lH), 7.10 (d,lH), 7.28 (m,lH), 7.38 (m,lH), 8.58 (d,lH), 9.20 (s,lH), 9.30 (s1H). Step 1 3-Amino-2-picoIinic acid (4.14 g) was suspended in ethanol (100 ml) at room temperature with stirring. DMAP (3.7 g) was added and the reaction was stirred for 1 hour at room temperature. A further equivalent of E5MAP (3.7 g) was added and the suspension disappeared, and then EDC (5.80 g) was added and the reaction was stirred at room temperature for 17 hours. The ethanol was evaporated to give a dark oil, water was added and the mixture was extracted with ethyl acetate, washed with brine and dried over magnesium sulphate. Evaporation of the solvent gave ethyl 3-amino-2-picolinate as a solid (6.5 g), mixed in a 2:1 ratio with DMAP. 1H NMR (CDC13) Sppm: 1.4 (t,3H), 4.45 (q,2h), 5.S (bs,2H), 7.05 (d,iH), 7.2 (dd,lH), 8.05 (fd,lH). Step 2 The crude product from Step 1 (6.5 g) was dissolved in dry DC1-4 (150 ml), and triethylamine (5.0 ml) was added to give a dark brown solution. The reaction was stirred in an ice bath, and 2,4,6-trifluorophenylacetyl chloride (8.0 g) in dry DC1-4 (20 ml) was added dropwise. The mixture was stirred for 6 hours and stood for 18 hours. The solvent was evaporated to give an orange sludge, water was added, and the solid was dissolved in ethyl acetate, which was washed with sodium bicarbonate solution and water, and then dried over magnesium sulphate. The ethyl acetate was evaporated to yield a solid (8.5 g), which was purified by flash column chromatography on silica gel (40-60), eluting with ethyl acetate to give Ksolid which was triturated with diethyl ether to give ethyl 3-[2-(2,4,6-trifIuorophenyI)-acetylamino]-pyridine-2-carboxylic acid ethyl ester as a white solid (3.0 g). lH NMR (CDCI3) 5 ppm: 1.45 (t,3H), 3.85 (d,2H), 4.5 (q,2H) 6.75 (t,2H), 7.5 (m,lH), 8.45 Step 3 The product from Step 2 (0.80 g) and potassium carbonate (0.40 g) were stirred in dry DMF (10 ml) at 100°C for 6 hours. The reaction mixture was cooled, stood for 18 hours and the DMF was evaporated to give a solid. This was diluted with water (1 ml), acidified to neutrality and the water was evaporated to give a solid, which was then extracted with methanol. The methanol was evaporated to give 3-(2,4,6-trifluorophenyl)-lH'-[l,5]naphthyridine-2,4-dione as a peach coloured solid (0.15g), which was used without further purification. 'H NMR (CD3OD) 5 ppm: 6.88 (m,2H), 7.45 (m,lH), 7.72 (m,lH), 8.10 (d,lH). Step 4 The product from Step 3 (0.20 g) was added to phosphorus oxychloride (5.0 ml) and the suspension stirred and brought to S5QC for 5 hours. The phosphorus oxychloride was evaporated to give a brown oil which was dissolved in DC1-4 (100 ml) and washed with cold water. The DC1-4 layer was separated, dried over magnesium sulphate and the solvent was evaporated to give 2,4-dichloro-3-(2,4,6-trifluorophenyl)-[l35]naphthyridine as a solid (0.070 8)- lH NMR (CDCh) 5 ppm: 6.9 (t,2H), 7.9 (m,lH), 8.5 (d.IH), 9.2 (bs,lH). Step 5 The product from Step 4 (0.070 g) was dissolved in propylamine (1.0 ml) and waR""ed in a sealed tube to 60°C for 2 hours. Thepropylamine was evaporated and the residue was purified by flash column chromatography on silica gel (40-60) eluting with diethyl ether to give [2-chloro-3-(2,4,6-trifluorophenyl)-[l,5]naphthyridin-4-yl]-isopropylamine as a yellow gum (0.009 g). 1H NMR (CDCh) 5 ppm: 1.1 (d,6H), 3.25 (m,lH), 6.8 (t,2H), 7.6 (dd,lH), 8.35 (d,lH), 8.7 (d,lH). Compounds were tested in a leaf disk assay, with methods described below. Test compounds were dissolved in DMSO, and diluted into water to 200 ppm. Erysiphe graminisf.sp. hordei (barley powdery mildew): barley leaf segments were placed on agar in a 24-weIl place and sprayed with a solution of the test compound. After allowiftg' -to dry completely, for between 12 and 24 hours, the leaf disks were inoC1-6lated with a spore suspension of the fungus. After appropriate inC1-6bation the activity of a compound was 1. W, X and Y are all CH and Z is N; R is halo; R1 is an/I, heteroaryl, morphciino, piperidino or pyrrolidine; R2 is NR3RR3 and R4 are independently H, C1-8alkyl, C2-9alkenyl, C2-8 alkynyl, aryl, aryl(Ci.8)alkyl, C3-8 cycloalkyl, C3-9cycloalkyl(C1-6)alkyl, heteroaryl, hetero- aryl(Ci.8)alkyl, NR5Re, provided that not both R3 and R4 are H or NR5R6, or R3 and R4 together form a C3-7 alkylene or C3-7 alkenylene chain optionally substituted with one or more C,.4 alkyl or C1-4 alkoxy groups, or, together with the nitrogen atom to which they are attached, R3 and R4 form a morpholine, thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring or a piperazine or piperazine /V-(C1-4)alkyl (especially N-methy) ring; and R5 and R6 are independently H, C1-8alkyl, C2-8alkenyl, C2-3 alkynyl, aryl, aryl(Cva)alkylt C3-8cycl6alkyl, C3-8cycioalkyl(CV5)alkyl, heteroaryl or hetero-aryl(Ci.3)alkyl; any of the foregoing alkyl, alkanyl, alkynyl or cycloalkyl groups or moieties (other than for R8) being optionally substituted with halogen, cyano, C1-6 alkoxy, C1-6al- kylcarbonyl, C1-6alkoxycarbonyl, C1-6 haloalkoxy, C1-6alkylthio, tri(C1-4)alkylsilyl, C1-6alkylamino or C1-6 dialkylamino, any of the foregoing morpholine, thiomorpholine, piperidine, piperazine and pyrrolidine rings being optionally substituted with C1-4 alkyl (especially methyl), and any of the foregoing aryl or heteroan/l groups or moieties being optionally substituted with one or more substituents selected from halo, hydroxy, mercapto, C1-6 alkyl, C2-6alkenyl, C2-6alkynyl, C1-6 alkoxy, C2-6alkenyloxy, C2-6 alkynyloxy, halo(C1-6)aIkyl, halo(C1-6)alkoxy, C1-6 alkylthio, halo(C1.5)alkylthio, hydroxy(C1.5)alkyl, C1-4alkoxy(C1-6)alk'yl, C3-6 cycloalkyl, C3-6-cyc!oalkyl(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, -NR'"R"", -NHCOR",-NHCONR'"R",-CONR"'Rm,-S02R",-OS02R",-COR",-CR"'=NR"" or -N=CR"'R"", in which R'" and R,m are independently hydrogen, C,.4 alkyl, halo- (Ci-a)alkyl, C1-6aikoxy, halo(C1-4)alkoxy, C1-4alkylthio, C3-6 cycloalkyl, C3-5 cycloalkyl- (C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being opt;enally substituted with halogen, C1-4aikyl or C1-4 alkoxy. A compound according claim 1 wherein R3 is C1-8 alky! haIo(C1-8)alkyl, hycroxyfC1-8alkyl, C1-6 alkoxy(C1-8)alky:. C1-4alkoxy- ha!o(C1-8)alkyi. tri(C1-4)alkylsilyl(C1-8)alkyl, C1-4alkylcarbcnyl(C1-8)alkyi. C1-4 alkyl- carbonylhalo(C1-8)alkyl, phenylC1-4alkyl, C2-8 aikenyl, ha!o(C2.8)alkenyl. C2-8alkynyl, C3-8 cycioalkyl optionally substituted with chloro, fluoro or methyl, C3-8 cycloal- kyl-(C1-6)alkyl, phenylamino, piperidino or morpholino, the phenyl ring ex phenyfalkyl or phenylamino being optionally substituted with one, two or three substituents selected from halo, C1-6 alkyl, haio(C1-4)alkyl, C1-4 alkoxy and halo(C1-4)alkoxy; and R4 is H, C1-4aikyl, halo(C1-4)alkyl or amino, or R3 and R4 together form a C3-7 alkylene or C3-7 alkenylene chain optionally substituted with methyl, or, together with the nitrogen atom to which they are attached, R3 and R4 form a morpholine, thiomorphoiine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring or a piperazine or piperazine N-(C1-4)alkyl (especially N-methyl) ring, in which the morpholine or piperazine rings are optionally substituted with methyl. A compound according to claiml or 2 claims wherein R1 is phenyl optionally substituted with from one to five halogen atoms or with from one to three substituents selected from halo, C1-4alkyl, halo(C1-4)alkyl, C1-6 alkoxy or halo(C1-4)alkoxy, pyridyl optionally substituted with from one to four halogen atoms or with from one to three substituents selected from halo, C1-4alkyl, halo(C1-4)aIkyl, C1-4alkoxy or halo(C1-4)alkoxy, 2- or 3-thienyl optionally substituted with from one to three halogen atoms or with from one to three substituents selected from halo, C1-4alkyl, halo(C1-4)alkyl,C1-4alkoxy or halo(C1-4)alkoxy, or piperidino or morpholino both optionally substituted with one or two methyl groups. A compound according to claim 3 wherein R1 is 2,6-difluorophenyl, 2-fiuoro-6-chloro-phenyl, 2,5,6-trifluorophenyl, 2,4,6-trifIuorophenyl, 2,6-difluoro-4-methoxyphenyl or pentafluorophenyl. A compound according to claim 1 wherein W, X and Y are all CH and Z is N; R is halo, R1 is aryl, heteroaryl, morpholino, piperidino or pyrrolidino; R2 is NR3R4; R3 and R4are independently H, C1-8aikyl,C2-8 aikenyl,C2-8 alkynyl, an/l, ar/KC1-8aikyl, C3-8cycloalkyl, C3-8cycloalkyl(C1-6)alkyl. heteroaryl, hetero-aryC1-8alkyl, NR5R6, provided that not both R3 and R4 are H or NR5R6. or R3 and R4 together foR"" a C3_7 alkylene or C3-7 alkenylene chain optionally substituted with one or more C1-4aikyl or C1-4 alkoxy groups, or, together with the nitrogen atom to which they are attached, R° and R4 r'oR"" a morpholine, thiomorpholine, thiomorpholine S-oxide or thiomcrphoiine S-dioxide ring or a piperazine or piperazine N-(C1-4)aikyl (especially N-methy!) ring; and R5 and R6 are independently H, C1-8aikyl, C2-8 alkenyl,C2-8 aikynyl, aryl(Ci:8)alkyl, C3-8 cycloalkyl, C3-8cycloalkyl(C1-6)alkyl, heteroaryl orhetero-aryC1-8alkyl; any of the foregoing aikyl, alkenyl, aikynyl or cycloalkyl groups or moieties being optionally substituted with halogen, cyano, C1-6alkoxy, C1-4alkylcarbonyl, C1-6alkoxy-carbonyl, C1-6 haloalkoxy, C1-6 alkylthio, tri(C1-4)alkylsilyl, C1-6alkyfamino or C1-6alkylamino, any of the foregoing morpholine, thiomorpholine, piperidine, piperazine and pyrrolidine rings being optionally substituted with C1-4 aikyl (especially methyl), and any of the foregoing aryl, heteroaryl, aryloxy or heteroan/l groups being optionally substituted with one or more substituents selected from halo, hydroxy, mercapto, C1-6 aikyl, C2-6 alkenyl, C2.5alkynyl, C1-6 alkoxy, C2-6 afkenyloxy, C2-6alkynyloxy, halo(C1-6)alky(, halo(C1-6)alkoxy, C1-6 alkylthio, halo(d-s)a!kyithio, hydroxy(C1-6)alkyl, C1-4alkoxy(C1-6)aikyl, C3-6cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, -NFTR"", -NHCOR"', -NHCONR'"R"", -CONR""R'",-S02R",-OS02R"", -COR"", -CR"'=NR"" or -N=CR'"R'",in which R'" and R"" are independently hydrogen, C1-4alkyl, halo(C1-4)alkylT C1-4 alkoxy, halo(C1-4)alkoxy, C1-4 alkylthio, C3.5 cycloalkyl, C3-6 cydoalkyl(d-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4aikyl or C1-4 alkoxy. A compound according to claim 1 wherein W, X and Y are all CH and Z is N; R is halo; R1 is aryl, heteroaryl, morphofino, piperidino or pyrrolidine; R2 is NR3R4, R3 is C1-4aLkyl, halo(C1-4)alkyl, C2-4alkenyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl or phenylamino in which the phenyl ring is optionally substituted with one, two or three substituents selected from halo, C1-4 aikyl, halo(C1-4)alky(, C1-4 alkoxy and - halo(C1-4)alkoxy; and R4 is H,C1-4aikyl or amino, or R3 and R4 together foR"" a C4-6 alkylene chain optionally substituted with C1-4 aikyl or C1-4 alkoxy, or together with the nitrogen atom to which they are attached, R3 and R4 foR"" a morpholine, thiomorpholine, thiomorphofine S-oxide or thiomorpholine S-dioxide ring or a piperazine or piperazine N-(C1-4)alkyl (esoecially /V-methyl) ring; any of the foregoing alkyl, alkenyl, alkynyl or cycloalkyl groups or moieties being optionally substituted with halogen, cyano, C1-6 atkoxy, C1-6alkyfcarbcnyl, C1-6alkoxy-carbcnyl, C1-6 haloalkoxy, C1-6 alkylthio, tri(C1-4)alkylsilyl. C1-6 alkylamino or C1-6dialkylamino, any of the foregoing morphciine, thiomorpholine, piceridine, piperazine and pyrrolidine rings being optionally substituted with C1-6 alkyl (especially methyl), and any of the foregoing an/I or heteroan/f groups or moieties oeing optionally substituted with one or more substituents selected from halo, hydroxy, mercapto, C1-8 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C2-6 alkenyloxy, C2-6alkynyloxy, halo(C1-6)alky(, halo(C1-6)alkoxy,C1-6alkylthio, halc(C1-4;alkylthio, hydroxy(C1-6)alkyl, C1-4alkoxy(C1-6)alkyl, C3_6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, -NR'"R"", -NHCOR'", -NHCONR'"R'",-CONR'"R""', -S02R",-OS02R"', -COR"', -CR'"=NR"" or -N=CR""R'",in which R'" and R"" are independently hydrogen, C1-4alkyl, halo(Ci-j)alkyl, C1-4alkoxy, halo(C1-4)alkoxy, C1-4 alkylthio, C1-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl'or C1-4 alkoxy. A compound according to claim 1 wherein one of W, X and Y are all CH and Z is N; R is halo; Rl is optionally substituted phenyl; R2 is NR3R4, R3 and R4 are independently H, C1-8alkyl, C2-8 alkenyl,C2-8 alkynyl, an/l, aryl(C1-8)alkylf C1-6 cycloalkyl, C3-8cycloalkyl(C1-4)alkylf heteroaryl, heterc- aryl(C1-8)alkyl, NR5R6, provided that not both R3 and R4 are H or NR5R5, or R3 and R4 together foR"" a C3-7 alkylene or C3-7 alkenylene chain optionally substituted with one or more C1-4 alkyl or C1-4 alkoxy groups, or, together with the nitrogen atom to which they are attached, R3 and R4 foR"" a morpholine, thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-cioxide ring or a piperazine or piperazine N-(C1-4)alkyl (especially N-methyl) ring; and R5 and R6 are independently H, C1-8alkyl, C2-8 alkenyl, C2-3 alkynyl, an/l, aryl(C1-8)alkyl, C3-8 cycloalkyl, C3-8cycloalkyl(C1-6)alkyl, heteroaryl or hetero- aryf(C1-8)alkyl; any of the foregoing alkyl, alkenyl, alkynyl or cycloalkyl groups or moieties being optionally substituted with halogen, cyano, C1-6 alkoxy, C1-6alkylcarbonyl, C1-6al- koxycarbonyl, C1-6 haloalkoxy, C1-6 alkylthio, tri(C1-4)alkylsilyl, C1-6 alkylamino or C1-6dialkylamino; any of the foregoing morpholine, thiomorpholine, piperidine, piperazine and pyrrolidine rings being optionally substituted withC1-4aikyl (especially methyl), and any of the foregoing ar/I or heteroaryl groups or moieties, including the phenyl group of R,being ootionally substituted with one or more substituents selected from halo, hydroxy, mercapto, d-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-8alkoxy, C2-6 alkenyloxy, C2-6 alkynyloxy, halo(C1-6)alkyi, halo(C1-8)aikoxy, C1-8aikylthio, halo(C1-6)alkylthio, hydroxy(C1-8)alkyl, C1-4alkoxy(C1-6)alkyl, C3-6cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, -NR'"R"", -NHCOR'", -NHCONR""R"", -CONRn,R'",-S02R",-OS02R",-COR'", -CR",=NR"or-N=CR""R", in which R"" and R"" are independently hydrogen,C1-4alkyl, halo(C1-6)alkyl,C1-4alkoxy, halo(C1-4)alkoxyf C1-4 alkylthio, C3-6 cycloalkyl, d-6 cycloalkyl(C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4alkyl orC1-4alkoxy. A compound according to claim 1 wherein W, X and Y are all CH and Z is N; R is halo; R1 is phenyl optionally substituted with from one to five halogen atoms or with from one to three substituents selected from halo, C1-4 alkyl, halo(C1-4)alkyl, C1-4alkoxy or haIo(C1-4)alkoxy, pyridyl optionally substituted with from one to four halogen atoms or with from one to three substituents selected from halo,C1-4alkyl, halo(C1-4)alkyl, C1-4alkoxy or halo(C1-4)alkoxy, 2- or 3-thienyl optionally substituted with from one to three halogen atoms or with from one to three substituents selected from halo, C1-4alkyl, ha!o(C1-4)alkyl,C1-4alkoxy or halo(C1-4)alkoxy, or piperidino or morpholino both optionally substituted with one or two methyl groups; R2 is NR3R4; R3 is C1-8 alkyl, halo(C1-8)alkyl, hydroxy(C1-8)aIkyl,C1-4aIkoxy(C1-8)alkyl,C1-4alkoxy-halo(C1-8)alkylt tri(C1-4)alkylsilyl(d-6)alkyl,C1-4alkyicarbonyl(C1-8)alkyl, C1-4 alkyl-carbonylhalo(C1-4)alkyl, pheny!(C1-4)a!kyf, C2-8 alkenyl, haIo(C2_8)alkenyl, C2-8 alkynyl, C3-8 cycloalkyl optionally substituted with chloro, fluoro or methyl, C3.3 cycloalkyl-(C1-4)alkyl, phenylamino, piperidino or morpholino, the phenyl ring of phenylalkyl or phenylamino being optionally substituted with one, two or three substituents selected from halo,C1-4alkyl, ha!o(C1-4)alkyl,C1-4alkoxy and halo(C1-4)alkoxy; and R4 is H,C1-4alkyl, halo(C1-4)alkyl or amino, or v R3 and R4 together foR"" a C3-7 alkylene or C3-7 alkenylene chain optionally substituted with methyl, or, together with the nitrogen atom to which they are attached, R3 and R4 foR"" a morpholine, thiomorpholine, thiomorphcline S-oxide or thiomorpholine S-dioxide ring or a piperasne or piperaan© N-(C1-4)alkyl (especially N-methyl) ring, in which the morpholine or piperazine rings ara optionally substituted with methyl. A compound according to claim 1 wherein one of W, X and Y are all CH and Z is N; R is halo; R1 is phenyl optionally substituted with from one to five halogen atoms cr with from one to three substituents selected from halo,C1-4aJkyi, halo(C1-4)alkyi, C1-6alkcxy cr hafo(C1-6)alkoxy; R2 is NR3R3; R3 is C1-4alkyl. halo(C1-6)aryI, C1-6alkenyl, C3-8 cycloalkyl, C1-6 cydoalkyl(C1-4)alkyl or phenylamino in which the phenyl ring is optionally substituted with one, two or three substituents selected from halo, C1-4 alkyl, halo(C1-4)alky\|, C1-4 alkoxy and haIo(C1-4)alkoxy; and R4 is H, r amino, or R3 and Rd together foR"" a C4-6alkylene cnain optionally substituted with methyl, or, together with the nitrogen atom to which they are attached, R3 and R4 foR"" a morpholine ring. A process for preparing a compound of the general foR""ula (T)-according to claim 1 whsrein one of R is chloro orfluoro and R2 is NR3R4 and W, X, Y, Z, R,R3 and R4 are as defined in claim 1, which comprises reacting an amine of the general foR""ula NR3R4 with a compound of the general foR""ula (6) or (13): wherein W, X, Y, Z and R1 are as defined in dafml. A plant fungicidal composition comprising a fungicidally effective amount of a compound as defined in claim 1 and a suitable carrier or diluent therefor. A method cf combating or controlling phytcpathogenic fungi which comprises applying to a plant, to a saed of a plant to t'no loC1-4s of ths plant or ssad or to soil or to any other plant growth medium, a fungicidally effective amount of a compound according to claim 1 or a composition according to claim 12.

Full Text

FUNGICIDES
This invention relates to novel derivatives of naphthyridines. to processes for preparing them, to certain intermediate chemicals used in their manufacture, to compositions containing them and to methods of using them to combat fungi, especially fungal infections of plants.
Derivatives of the nitrogen-containing 5,6 ring system S-l,2,4-triazolo[l,5-a]pyri-Ynidine are known from the patent literature as being useful for controlling phytopathogenic fungi. Examples of recent patent publications include EP-A-1249452, WO 02/051845, WO 02/083676, WO 02/083677, WO 02/088125, WO 02/088126, WO 02/088127. The plant fungicidal activity of certain derivatives of naphthyridines is described in EP-A-0410762 and US 4801592. Other naphthyridine derivatives are described, for example, in WO 92/07468 and US 525S356 as herbicides and in WO 93/13097 and WO 92/22533 for pharmaceutical applications. Naphthyridine derivatives are also known in the general chemical literature, for example, from Synthetic Communications (2003), 33(1), 73; Indian Journal of Chemistry, Section B (2002), 4IB(10), 2194; Fannaco (2002), 57(8), 631; Farmaco (2001), 56(4), 311; Farmaco (2000), 55(9-10), 603; Arch. Pharm. (1957), 290, 136; Farmaco, Edizione Scientifica (1979), 34(2), 165; Journal of the Chemical Society', Chemical Communications (1974), (4), 134; Journal of the Chemical Sociey, 1 (1996), (12), 1359; Journal of Organic Chemistry (1972), 37(20), 3101; Journal of Medicinal Chemistry (1973), 16(7), 849; Journal of the Chemical Society, Chemical Communications (1974), (4), 134; and the European Journal of Medicinal Chemistry (200), 35(11), 1021-1035.
The present invention is concerned with the provision of alternative, novel naphthyridines for combating phytopathogenic diseases on plants and harvested food crops.
Thus, according to the present invention, there is provided a compound of the general formula (1):
wherein

R is H, halo, C1-4 alkyl, C1-4 alkoxy or ha!o(C1-4)alkyI, provided that when X is CH, Z is N
R is NHNH2, R1 is phenyl and R2 is CI, W and Y are not both CCH3;
one of Rand RL isNR-R and the other is halo, C1-8 alkyl, C1-8 alkoxy, C1-8 alkylthio, C2-8
alkenyl, C2-8 alkynyl or cyano;
R is aryl, heteroaryl, morpholino, piperidino or pyrrolidino;
R3 and R4 are independently H, C1-8 alkyl, C2-8 alkenyl, C2-3 alkynyl, aryl, aryl(CNS)aIkyI,
C3-scycloaIkyl, C3-8cycloaIkyl()alkyl, heteroaryl, heteroaryl(C1-8)alkyi, NR5R6, provided
that not both R3 and R4 are H or NR5R6, or
R and R together foR"" a C3.7 alkylene or-C3-C7 alkenylene chain optionally substituted with
one or more C1-4 alkyl or C1-4 alkoxy groups, or,
together with the nitrogen atom to which they are attached, R3 and R4 foR"" a morpholine,
thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring or a piperazine or
piperazine Ar-(C1-4)alkyl (especiallyN-methyl) ring; and
R5 and R6 are independently H, C1-8alkyl, C2-8 alkenyl,C2-8 alkynyl, aryl, aryl(C1-8)alkyl,
C3-8 cycloalkyl, C3-8cycloaikyl(C1-6)alkyl, heteroaryl or heteroaryl(C1-8)aIkyI;
any of the foregoing alkyl, alkenyl, alkynyl or cycloalkyl groups or moieties (other than for
R8) being optionally substituted with halogen, cyano, C1-6 alkoxy, C1-6alkylcarbonyl, C1-6
alkoxycarbonyl, haloalkoxy, C1-6 alkylthio, tri(C1-4)alkylsilyl, C1-4 alkylamino or C1-6
dialkylamino,
any of the foregoing morpholine, thiomorpholine, piperidine, piperazine and pyrrolidine
rings being optionally substituted with C1-4 alkyl (especially methyl), and
any of the foregoing aryl or heteroaryl groups or moieties being optionally substituted with
one or more substituents selected from halo, hydroxy, mercapto, C1-4 alkyl, C2-6 alkenyl, C2-6
alkynyl, C1-4 alkoxy, C2-6 alkenyloxy, C2-6 alkynyloxy, halo()alkyl, haIo(C1-6)alkoxy, C1-6
alkylthio, haIo()alkyIthio, hydroxy(C1-6)alkyl, C1-4alkoxy(C1-6)alkyl, C3-6 cycloalkyl, C3-6
cycloalkyl(C1-4)alkyI, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, iso-
thiocyanato, nitre, -NR'"R"", -NHCOR'", -NHCONR""R"", -CONR-'R"", -S02R"", -OS02R"",
-COR"", -CR""=NR""" or -N=CR'"R"",in which R"" and R"" are independently hydrogen, C1-4
alkyl, halo(C1-4)aIkyl, C1-4 alkoxy, halo(C1-4)alkoxy, C1-4 alkylthio, C3-6 cycloalkyl, C3-6
cycloalkyl(C1-4)a!kyl, phenyl or benzyl, the phenyl and benzyl groups being optionally
substituted with halogen, C1-4 alkyl or C1-4 alkoxy.

and R"; C7 alkylene and C3.7 alkenylene are excluded as chains foR""ed by R3 and R4; the C3_6 chain that R and R may foR"" may only be optionally substituted with one or more methyl groups; thiomorpholine, thiomorpholine S-oxide, thiomorphoiine S-dioxide and piperazine are excluded as rings that R and R""may foR""; tri(C].4)a!kylsiIyI is excluded as a substituent of any alkyl, alkenyl, alkynyl or cycloalkyl group or moiety and any morphoiine. piperidine or pyrrolidine ring is unsubstituted.
The compounds of the invention may contain one or more asymmetric carbon atoms and may exist as enantiomers (or as pairs of diastereoisomers) or as mixtures of such. They may also exist as diastereoisomers by virtue of restricted rotation about a bond. However, mixtures of enantiomers or diastereoisomers may be separated into individual isomers or isomer pairs, and this invention embraces such isomers and mixtures thereof in all proportions. -It is to be expected that for any given compound, one isomer may be more fungicidally active than another.
Except where otherwise stated, alkyl groups and alkyl moieties of alkoxy, alkylthio, etc., contain from 1 to 8, suitably from 1 to 6 and typically from 1 to 4, carbon atoms-in the foR"" of straight or branched chains. Examples are methyl, ethyl, n- and iso-propyl, n-, sec--; iso- and tert-butyl, /7-pentyl and /z-hexyl. Cycloalkyl groups contain from 3 to 8, typically from 3 to 6, carbon atoms and include bicycloalkyl groups such as the bicyclo[2.2.1]heptyl group. Haloalkyl groups or moieties are typically trichloromethyl or trifluoromethyl or contain a trichloromethyl or trifluoromethyl teR""inal group.
Except where otherwise stated, alkenyl and alkynyl moieties also contain from 2 to S, suitably from 2 to 6 and typically from 2 to 4, carbon atoms in the foR"" of straight or branched chains. Examples are allyl, 2-methylallyl and propargyl. Optional substituents include halo, typically fluoro. An example of halo-substituted alkenyl is 3,4,4-trifluoro-n-butenyl.
Halo includes fluoro, chloro, bromo and iodo. Most commonly it is fluoro, chloro or bromo and usually fluoro or chloro.
Aryl is usually phenyl but also includes naphthyl, anthryl and phenanthryl.
Heteroaryl is typically a 5- or 6-membered aromatic ring containing one or more O, N or S heteroatoms, which maybe fused to one or more other aromatic or heteroaromatic rings, such as a benzene ring. Examples are thienyl, furyl, pyrrolyl, isoxazolyl, oxazoM,

benzothiazolyl, benzoxazolyl, benzimidazolyl, indolyl, quinolinyl and quinoxalinyl groups and, where appropriate, N-oxides thereof.
The 6,6-ring systems embraced by the general foR""ula (1) are 1,8-naphthyridines (where W, X and Y are all CR8 and Z is N), 1,7-naphthyridines (where W, X and Z are all CRS and Y is N), 1,6-naphthyridines (where W, Y and Z are all CRS and X is N) and 1,5-naphthyridines (where X,Y and Z are all CRS and W is N). Of partiC1-6lar interest are 1,8-naphthyridines.
R8, which may be the same or different for the three CR5 values of W, X, Y and Z is H, halo (for example bromo), C1-4 alkyl (for example methyl), C1-4 alkoxy (for example methoxy) or halo(Ci.4)alkyl (for example trifluoromethyl). Usually R8 will be H. However, of partiC1-6lar interest are compounds containing a 3-bromo-l,8-naphthyridine ring (i.e. where W and Y are CH, X is CBr and Z is N).
One of R and R2, preferably R2, is NR3R4. The other is typically halo, especially chloro or fluoro. In the case of thel,S-naphthyridine ring system, the more active compounds are those where R is NR R . R is typically C1-8 alkyl (for example ethyl, /t-propyl, n-butyl, sec-bbuty,(the S- or R-isomer or the racemate) and tert-butyl), haIo(Ci.s)aIkyl (for example 2,2,2-trifluoroethyl, 2,2,2-trifluoro-l-methyIethyI (the S- or R-isomer or the racemate), 3,3,3-trifluoropropyl and 4,4,4-trifluorobutyl), hydroxy(C1-8)alkyl (for example hydroxyethyl), C1-4 alkoxy(C1-8)alkyl (for example methoxymethyl and methoxy-/so-butyI), C1-4 alkoxyhalo-(Cl.8)alkyl (for example 2-methoxy-2-trifluromethylethyl), tri(C1-4)alkylsilyI(C1-6)alkyl (for example trimethylsilylmethyl), C1-4 alkylcarbonyl(C1-8)alkyl (for example 1-acetylethyl and l-terr-butylcarbonylethyl), C1-4 alkylcarbonylhalo(C1-8)alkyl (for example l-acetyl-2,2,2-trifluoroethyl), phenyI(M)alkyl (for example benzyl), C2-8 alkenyl (for example allyl and methylallyl), halo(C2-8)alkenyl (for example 3-methyl-4,4-difluorobut-3-enyl), C2-8 alkynyl (for example propargyl), C3-8 cycloalkyl (for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl) optionally substituted with chloro, fluoro or methyl, C3-8 cycloalkyl(C1-4)-aLkyl (for example cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl and cyclohexylmethyl), phenylamino, piperidino or morpholino, the phenyl ring of phenylalkyl or phenylamino befng optionally substituted with one, two or three substituents selected from halo (typically fluoro, chloro or bromo), C1-4 alkyl (typically methyl), halo(C1-4)alkyl (typically trifluoromethyl), C1-4 alkoxy (typically methoxy) and halo(C1-4aIkoxv (typically

C4-6 alkylene chain optionally substituted with methyl, for example 3-methylpentyIene, or, together with the nitrogen atom to which they are attached, R3 and R4 foR"" a morpholine, thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring or a piperazine or piperazine iV-(Ci.4)alkyl (especially ;V-methyl) ring, in which the morpholine or piperazine rings are optionally substituted with methyl.
Typically R1 is phenyl optionally substituted with from one to five halogen atoms, partiC1-6larly fluorine and chlorine atoms and especially fluorine atoms or with from one to three substituents selected from halo (for example fluoro and chloro), C1-4 alkyl (for example methyl), halo(Ci.4)aIkyl (for example trifluoromethyl), C1-4 alkoxy (for example methoxy) or halo(Ci.4)alkoxy (for example trifluoromethoxy). Examples are 2,6-difluorophenyL 2-fluoro-6-chlorophenyl, 2,5,6-trifluorophenyl, 2,4,6-trifluorophenyl, 2,6-difluoro-4-methoxyphenyl, pentafluorophenyl, 2-fluorophenyI, 2,3,5,6-tetrafluorophenyl, 2-chloro-4,6-difluorophenyI, 2-chIorophenyl, 2,6-dichIorophenyI, 2,4-dichIorophenyl, 2,4,6-trichlorophenyI, 2,3.6-tri-chlorophenyl, pentachlorophenyl, 2-fluoro-4,6-dichIorophenyI, 4-fluoro-2.6-dichIoropheixyl, 2-bromophenyl, 2-fluoro-6-bromophenyl, 2-brorno-4,6-difluorophenyl, 2-fluoro-6-methyl-phenyl, 2-chloro-6-methyIphenyl, 2-methoxyphenyl, 2,6-dimethoxyphenyI, 2-fluoro-6-methoxyphenyl, 2-trifIuoromethylphenyI, 2-fluoro-6-trifluoromethylphenyI, 2,6-di-(trifluoro-methyl)phenyl, 2-chloro-6-trifluoromethylphenyl, 2,4-difluoro-6-trifluoromethylphenyI, 2,4-difluoro-6-methoxyphenyI and 2,4-difluoro-6-methylphenyl.
Also of partiC1-6lar interest are compounds where R1 is pyridyl optionally substituted with from one to four halogen atoms or with from one to three substituents selected from halo (for example fluoro and chloro), C1-4 alkyl (for example methyl), halo(C1-6t)alkyl (for example trifluoromethyl), C1-4 alkoxy (for example methoxy) or halo(C1-6)alkoxy (for example trifluoromethoxy). Examples are 2,4-difluoropyrid-3-yl, 3,5-difluoropyrid-4-yl, tetrafluoropyrid-4-yI, 3-fluoropyrid-2-yl, 4-fluoropyrid-3-yl, 3-fluoropyrid-4-yl, 2-fluoro-pyrid-3-yl, 2,4,6-trifluoropyrid-3-yl, 3,5-difluoropyrid-2-yl, 2,6-difluoropyrid-3-yl, 2,4-difluoro-6-methoxypyrid-3-yl, 2-fluoro-4-chloropyrid-3-yl, 3-fluoro-5-chloropyrid-4-yl, 2-chloro-4-fluoropyrid-3-yl, 2,4~dichloropyrid-3-yl, 3-chloropyrid-2-yl I, 4-chlorop>Tid-3-yl, 3-chloropyrid-4-yI, 2-chloropyrid-3-yl, 3-trifIuoromethylpyrid-2-yI, 4-trifluoromethylpyrid-3-yI, 3,5-dichloropyrid-2-yl, 4,6-dichloropyrid-3-yl, 3-trifluoromethylpyrid-4-yl, 2-trifluoro-methylpyrid-3-yI, 2-fluoro-4-trifluoromethylpyrid-3-yl, 3-fluoro-5-trifiuoromethy]pyrid-4-yl,

chloro-6-trifluoromethy!pyrid-2-yl, 3-fluoro-6-trifluoromethyIpyrid-2-yI, pyrid-2-yl, pyrid-3-yl and pyrid-4-yl.
Also of partiC1-6lar interest are compounds where R1 is 2- or 3-thienyl optionally substituted with from one to three halogen atoms or with from one to three substituents selected from halo (for example fluoro and chloro), C1-4 alkyl (for example methyl), halo-(C1-4)aIkyl (for example trifluoromethyl), C1-4 alkoxy (for example methoxy) or ha!o(C1-4). alkoxy (for example trifluoromethoxy). Examples are 3-fluorothien-2-yI, 3-chlorothien-2-yl, 2,4-difluorothien-3-yl. 2,4-dichlorothien-3-yl and 2,4,5-trichlorothien-3-yl.
Examples of other values o fR'of especial interest are unsubstituted piperidino and morpholino, 2-methylpiperidino, 2,6-dimethyIpiperidino and 2,6-dimethylmorpholino.
In one aspect the invention provides a compound of the general foR""ula (1) wherein . one of W, X, Y and Z is N and the others are CRS;
R8 is H, halo, C1-4 alkyl, C1-4 alkoxy or halo(C1-4)alkyl, provided that when X is CH, Z is N,
R is NHNH2, R1 is phenyl and R2 is CI, W and Y are not both CCH3;
one of R and R" (preferably R ) is NR R and the other is halo;
R1 is aryl, heteroaryl, morpholine, piperidino or pyrrolidino;
R3 and R4 are independently H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, aryl, aryI(Cj-8)alkyl,
C3-8cycloalkyC'C3-8cycloaIkyI(C1-6)alkyl, heteroaryl, heteroaryl(C1-8)alkyl, NRDR6, provided
that not both R3 and R4 are H or NR5R6, or
R3 and R4 together foR"" a C3.7 alkylene or C3.7 alkenylene chain optionally substituted with
one or more C1-4 alkyl or C1-4 alkoxy groups, or,
together with the nitrogen atom to which they are attached, R3 and R4 foR"" a morpholine,
thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring or a piperazine or
piperazine A^-(Ci-4)alkyl (especially TV-methyl) ring; and
R5 and R6 are independently H, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, aryl, aryl(C1-8)aIkyl,
C3-scycloalkyl, C3.gcycloaIkyl()alkyI, heteroaryl orheteroaryl(C1-8)alkyl;
any of the foregoing alkyl, alkenyl, alkynyl or cycloalkyl groups or moieties (other than for
R8) being optionally substituted with halogen, cyano, alkoxy, C1-6 alkylcarbonyl,
alkoxycarbonyl, C1-4 haloalkoxy, alkylthio, tri(C1-6)alkyIsiIyI, alkylamino or
dialkylamino,
any of the foregoing morpholine, thiomorpholine, piperidine, piperazine and pyrrolidine

substituted with one or more substituents selected from halo, hydroxy, mercapto, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyk C1-6 alkoxy. C2-6 alkenyloxy, C2-6 alkynyloxy, halo()aIkyl, haIo(C1-6)alkoxy, C1-6 alkylthio, ha!o(C1-6)alkyIthio, hydroxy(C1-6)aIkyL C1-4aIkoxy(C1-6)-alkyl, C3-6 cycloalkyl, C3-6 cycIoaIkyl(C1-4)aIky!, phenoxy, benzyloxy, benzoyloxy, cyano, isocvC1-6no, thiocyanato, isothiocyanaio, nitro, -NR"'R"",-NHCOR"', -NHCONR""R"",-CONRH,R"", -S02R"", -OS02R",-COR'", -CR"'=NR'm or -N=CR'"R"f,in which R"' and R"" are independently hydrogen, C1-4 alkyl, haIo(C1-4)alkyI, C1-4alkoxy, halo(C1-4)aIkoxy,C1-4 alkylthio, C3-6 cycloalkyl. C3-6 cycloalkyl(Ci„:)alkyI, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl or C1-4alkoxy. Of partiC1-6lar interest are compounds where W, X and Y are CH and Z is N.
The invention includes a compound of the general foR""ula (1) as defined immediately above except that: C7 alkylene and C3-7 alkenylene are excluded as chains foR""ed by R and R ; the C3-6 chain that R3 and R4 may foR"" may only be optionally substituted with one or more methyl groups; thiomorpholine, thiomorpholine S-oxide, thiomorpholine S-dioxide and piperazine are excluded as rings that RJ and R4 may foR""; tri(C1-4)alkylsilyl is excluded as a substituent of any alkyl, alkenyl, alkynyl or cycloalkyl group or moiety, and any morpholine, piperidine or pyrrolidine ring is unsubstituted.
In another aspect the invention provides a compound of the general foR""ula (I) wherein
one of W, X, Y and Z is N and the others are CR8;
R8 is H, halo, C1-4 alkyl, C1-4 alkoxy or halo(C[-4)alkyl, provided that when X is CH, Z is N, R is NHNH2, R1 is phenyl and R2 is CI, W and Y are not both CCH3; one of R and R2 (preferably R2) is NR3R4 and the other is halo; R1 is aryl, heteroaryl, morpholino, piperidino orpyrrolidino;
R3 is C1-4 alkyl, halo(C1-4)aIkyl, C2-4 alkenyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl or phenylamino in which the phenyl ring is optionally substituted with one, two or three substituents selected from halo, C1-4 alkyl, ha!o(C1-4)alkyI, C1-4 alkoxy and halo(C1-4)alkoxy; and R4 is H, C1-4 alkyl or amino, or
R3 and R4 together foR"" a C4-6 alkylene chain optionally substituted with C1-4 alkyl or C1-4 alkoxy, or, together with the nitrogen atom to which they are attached, R and R foR"" a morpholine.

any of the foregoing alkyl. alkenyl, alkynyl orcycloalkyl groups or moieties (other than for R3) being optionally substituted with halogen, cyano, C1-6 alkoxy, C1-6alkylcarbonyl, C1-6 alkoxycarbony], C].0 haloalkoxy, C1-6 alkylthio, tri(C1-4)alkyIsilyI, C1-6 alkylamino or C1-6 dialkylamino,
any of the foregoing morpholine, thiomorpholine, piperidine. piperazine and pyrrolidine rings being optionally substituted with C1-4 alkyl (especially methyl), and any of the foregoing aryl or heteroaryl groups or moieties being optionally substituted with one or more substituents selected from halo, hydroxy, mercapto, C1-6alkyl, C1-6 alkenyl, C1-6 alkynyl, alkoxy, C2-6 alkenyloxy, C2-6 alkynyloxy, haIo(Ci-o)aIkyI, halo(C1-6)alkoxy, C].6 alkylthio, halo(Cj.6)a!kylthio, hydroxy()aIkyl, C1-4alkoxy()alkyI, C1-6cycloalkyl, C3-6 cycloa!kyl(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, iso-thiocyanato, nitro, -NR"'R"", -NHCOR",-NHCONR,,,R,",-CONR"'R""", -SO:R"", -OS02R",-COR"', -CR'"=NR"" or -N-CR'-'R"", in which R"" and R""r are independently hydrogen, C1-4 alkyl, halo(C1-4)aIkyl, C1-4alkoxy, halo(C(_4)alkoxy, C1-4 alkylthio, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyI, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl or C1-4 alkoxy. Of partiC1-6lar interest are compounds where W, X and Y are CH and Z is N. ...
The invention includes a compound of the general foR""ula (1) as defined immediately above except that; the C4-6 chain that R3 and R4 may foR"" may only be optionally substituted with methyl; thiomorpholine, thiomorpholine S-oxide, thiomorpholine S-dioxide and piperazine are excluded as rings that R3 and R4 may foR""; tri(C1-4)alkyIsilyI is excluded as a substituent of any alkyl, alkenyl, alkynyl or cycloalkyl group or moiety, and any morpholine, piperidine or pyrrolidine ring is unsubstituted
In yet another aspect the invention provides a compound of the general foR""ula (1) wherein
one of W, X, Y and Z is N and the others are CR8;
R8 is H, halo, C1-4 alkyl, C1-4 alkoxy or halo(C1-4)aIkyl, provided that when X is CH, Z is N, R is NHNH2, R1 is phenyl and R2 is CI, W and Y are not both CCH3;
one of R and R2 is NR3R4 and the other is halo, C1-8 alkyl, C1-8alkoxy, C1-4 alkylthio, C2-8 alkenyl, C2-8 alkynyl or cyano; R1 is optionally substituted phenyl;

that not both R3 and R4 are H or NR5R6, or
R and R together foR"" a C3.7 alkylene or C3.7 alkenylene chain optionally substituted with one or more C1-4alkyl or C1-4 alkoxy groups, or,
together with the nitrogen atom to which they are attached, RJ and R4 foR"" a morpholine, thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring or a piperazine or piperazine;V-(C1-4)aIkyI (especially yV-methyl) ring; and
R5 and R6 are independently}-!, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, aryl, aryI(C]„s)alkyl, C3-8 cycloalkyl, C3-8 cycIoalkyI()alkyI, heteroaryl orheteroaryl(C1-8)alkyl; any of the foregoing alkyl, alkenyl, alkynyl or cycloalkyl groups or moieties (other than for R8) being optionally substituted with halogen, cyano, C1-6 alkoxy, C1-6alkylcarbonyl, C1-6 alkoxycarbonyl, C1-6 haloalkoxy, C1-6 alkylthio, tri(C1-4)aIkyIsilyl, C1-6 alkylamino or C1-6dialkylamino,
any of the foregoing morpholine, thiomorpholine, piperidine, piperazine and pyrrolidine rings being optionally substituted with C1-4 alkyl (especially methyl), and any of the foregoing aryl or heteroaryl groups or moieties, including the phenyl group of R1, being optionally substituted with one or more substituents selected from halo, hydroxy, mercapto, C1-6alkyl, C2-6 alkenyl, C2-6 alkynyl, alkoxy, C2-6 alkenyloxy, C2-6 'alkynyloxy, halo()alkyl, haIo(C1-6)alkoxy, alkylthio, halo()alkylthio, hydroxy-()alkyl, C1-4 alkoxy()alkyl, C3-6 cycloalkyl, C3-6 cycloalkyI(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, -NR'"R"", -NHCOR", -NHCONR""R""", -CONR""R"", -S02R",-OS02R", -COR",-CR,H=NR"" or -N=CR'"R"", in which R"" and R"" are independently hydrogen, C1-4 alkyl, haIo(C1-4)alkyI, C1-4 alkoxy, halo(C1-4)alkoxy, C1-4 alkylthio, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl or C1-4 alkoxy. Of partiC1-6lar interest are compounds where W, X and Y are CH and Z is N.
The invention includes a compound of the general foR""ula (1) as defined immediately above except that: C1-8 alkoxy and C1-8 alkylthio are excluded as values of R and R2; C7 alkylene and C3.7 alkenylene are excluded as chains foR""ed by R3 and R4; the C3-6 chain that R3 and R4 may foR"" may only be optionally substituted with one or more methyl groups; thiomorpholine, thiomorpholine S-oxide, thiomorpholine S-dioxide and piperazine

of any alkyl, alkenyl, alkynyl orcycloalkyl group or moiety, and the morphoiine ring that R3 and FT may foR"" is unsubstituted.
In still yet another aspect the invention provides a compound of the general foR""ula (1) wherein
one of W, X, Y and Z is N and the others are CRS;
R8 is H, halo (e.g. fluoro, chloro or bromo), C1-4 alkyl (e.g. methyl). C1-4 alkoxy (e.g. methoxy) or halo(C1-4)alkyl (e.g. trifluoromethyl), provided that when X is CH, Z is N, R is NHNH2, R1 is phenyl and R2 is CI, W and Y are not both CCH3;
R is halo (e.g. fluoro, chloro or bromo), C1-4alkyl (e.g. methyl), C1-4 alkoxy (e.g. methoxy) orcyano;
R1 is phenyl optionally substituted with from one to five halogen atoms or with from one to three substituents selected from halo, C1-4 alkyl, halo(C1-4)alkyl, C1-4 alkoxy or Kalo(C1-4)-alkoxy, pyridyl optionally substituted with from one to four halogen atoms or with from one to three substituents selected from halo, C1-4 alkyl, halo(C1-4)alkyI, C1-4 alkoxy or halo(C1-4)-alkoxy, 2- or 3-thienyl optionally substituted with from one to three halogen atoms or with from one to three substituents selected from halo, C1-4 alkyl, halo(C1-4)aIkyl, C1-4alkoxy or halo(C1-4)alkoxy, or piperidino or morpholino both optionally substituted with one or two methyl groups; R2 is NR3R4;
R3 is C1-8 alkyl, halo(C].g)alkyl, hydroxy(Ci_g)alkyl, C1-4 aIkoxy(C1-8)alkyl, C1-4 alkoxyhalo-(C1-8)alkyl, tri(C1-4)alkylsilyl()alkyl, C1-4 alkylcarbonyl(C1-8)aIkyl, C1-4alkylcarbonyl-halo(C1-8)alkyl, phenyl(i.4)alkyl, C2-8 alkenyl, haIo(C2-8)alkenyl, C2-8 alkynyl, C3-8 cycloalkyl optionally substituted with chloro, fluoro or methyl, C3-8 cycloalkyl(C1-4)alkyl, phenylamino, piperidino or morpholino, the phenyl ring of phenylalkyl or phenylamino being optionally substituted with one, two or three substituents selected from halo, C1-4alkyl, halo(C1-4)alkyl, C1-4 alkoxy and halo(C1-6alkoxy; and R is H, C1-4 alkyl, halo(C1-4)alkyl or amino, or
R3 and R4 together foR"" a C3.7 alkylene or C3.7 alkenylene chain optionally substituted with methyl, or, together with the nitrogen atom to which they are attached, R3 and R foR"" a morphoiine,

t
rings are optionally substituted with methyl. Of partiC1-6lar interest are compounds where W, X and Y are CH and Z is N.
In still yet another aspect the invention provides a compound of the general formula (1) wherein
one of W, X, Y and Z is N and the others are CRS; Rs is H, halo, C1-4 alkyl C1-4 alkoxy or haIo(C:.j)aIkyl; R is halo;
R1 is phenyl optionally substituted with from one to five halogen atoms or with from one to three substituents selected from halo, C1-4alkyl, haIo(C1-4)alkyI, C1-4 alkoxy or halo(C1-6)-alkoxy; R2 is NR3R4;
R3 is C1-4 alkyl, haIo((C1-4)alkyl, C2-4 alkenyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alky! or phenylamino in which the phenyl ring is optionally substituted with one, two or three substituents selected from halo, C1-4 alkyl haIo(C1-4)alkyl, C1-4 alkoxy and halo(C1-4)alkoxy; and
R4 is H, C1-4 alkyl or amino, or R3 and R4 together form a C4-6 alkylene chain optionally substituted with methyl, or, together with the nitrogen atom to which they are attached, RJ and R4 form a morpholine ring. Of partiC1-6lar interest are compounds where W, X and Y are CH and Z is N.
Compounds that form part of the invention are illustrated in Tables 1 to 126 below. Characterising data are given later in the Examples and in Table 132
In Table 1 the compounds have the general formula (1 A), where W, X and Y are CH, Z is N, R is CI, R1 is 2,4,6-trifluorophenyl and R3 and R4 are as shown in the table.

Table 3
Table 3 consists of 662 compounds of the general foR""ula (1 A), where W, X and Y
are CH and Z is N, R is CI, R1 is 2,3,4,5,6-pentafluorophenyl, and the values of R3 and R4 are
as listed in Table 1. Thus, compound I of Table 3 is the same as compound 1 of Table 1
except that in compound 1 of Table 3, R1 is 2.3,4,5,6-pentailuorophenyI. Similarly.
compounds 2 to 662 of Table 3 are the same as compounds 2 to 662 of Table 1 except that in
the compounds of Table 3, R' is 2,3,4,5,6-pentafluorophenyl.
Table 4 -
Table 4 consists of 662 compounds of the general foR""ula (1 A), where W, X and Y
are CH and Z is N, R is CI, R1 is 2",6-dif!uoro-4-methoxyphenyl, and the values of RJ and R4
are as listed in Table 1. Thus, compound 1 of Table 4 is the same as compound 1 of Table 1
except that in compound 1 of Table 4, R1 is 2,6-difluoro-4-methoxyphenyl. Similarly,
compounds 2 to 662 of Table 4 are the same as compounds 2 to 662 of Table 1 except that in
the compounds of Table 4, R1 is 2,6-difluoro-4-methoxyphenyl.
Table 5
Table 5 consists of 662 compounds of the general foR""ula (1A), where W, X and Y
are CH and Z is N, R is CI, R1 is 2-fluoro-6-chIorophenyl, and the values of R3 and R4 are as
listed in Table 1. Thus, compound 1 of Table 5 is the same as compound 1 of Table 1 except
that in compound 1 of Table 5, R1 is 2-fluoro-6-chlorophenyl. Similarly, compounds 2 to 662
of Table 5 are the same as compounds 2 to 662 of Table 1 except that in the compounds of
Table 5, R1 is 2-fluoro-6-chlorophenyI.
Table 6

Table 6 consists of 662 compounds of the general foR""ula (IB), where W, X and Y
are CH and Z is N, R is CI, R1 is 2.4,6-trifluorophenyI, and the values of R3 and R4 are as
listed in Table 1. Thus, compound 1 of Table 6 is the same as compound 1 of Table 1 except
that in compound 1 of Table 6, the compound has the general foR""ula (IB). Similarly,
compounds 2 to 662 of Table 6 are the same as compounds 2 to 662 of Table 1 except that in
the compounds of Table 6, the compounds have the general foR""ula (IB).
Table 7
Table 7 consists of 662 compounds of the general foR""ula (IB), where W, X and Y
are CH and Z is N, R is CI, R1 is.2?5,6-trifluorophenyI, and the values of R3 and R4 are as
listed in Table I. Thus, compound 1 of Table 7 is the same as compound 1 of Table 2 except
that in compound 1 of Table 7, the compound has the general foR""ula (IB). Similarly,
compounds 2 to 662 of Table 7 are the same as compounds 2 to 662 of Table 2 except that in
the compounds of Table 7, the compounds have the general foR""ula (IB).
Table 8
Table 8 consists of 662 compounds of the general foR""ula (IB), where W, X and Y
are CH and Z is N, R is CI, R1 is 2,3,4,5,6-pentafluorophenyI, and the values of R3 and R4 are
as listed in Table 3. Thus, compound 1 of Table 8 is the same as compound 1 of Table 3
except that in compound 1 of Table S, the compound has the general foR""ula (IB). Similarly,
compounds 2 to 662 of Table 8 are the same as compounds 2 to 662 of Table 3 except that in
the compounds of Table S, the compounds have the general foR""ula (IB).
Table 9
Table 9 consists of 662 compounds of the general foR""ula (IB), where W, X and Y
are CH and Z is N, R is CI, R1 is 2,6-difIuoro-4-methoxyphenyl, and the values of R3 and R4
are as listed in Table 1. Thus, compound 1 of Table 9 is the same as compound 1 of Table 4
except that in compound 1 of Table 9, the compound has the general foR""ula (IB). Similarly,
compounds 2 to 662 of Table 9 are the same as compounds 2 to 662 of Table 4 except that in
the compounds of Table 9, the compounds have the general foR""ula (IB).
Table 10
Table 10 consists of 662 compounds of the general foR""ula (IB), where W, X and Y
are CH and Z is N, R is CI, R1 is 2-fluoro-6-chlorophenyl, and the values of R3 and R4 are as
listed in Table 1. Thus, compound 1 of Table 10 is the same as compound 1 of Table 5
except that in compound 1 of Table 10, the compound has the general foR""ula (IB).

Table 11
Table 11 consists of 662 compounds of the general foR""ula (1A). where W is N and X, Y and Z are CH, R is CI, R1 is 2,4,6-trifluorophenyI, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 11 is the same as compound 1 of Table 1 except that in compound 1 of Table 11, the compound has the general foR""ula (1 A) where \V is N and X, Y and Z are CH. Similarly, compounds 2 to 662 of Table 11 are the same as compounds 2 to 662 of Table 1 except that in the compounds of Table 11, the compounds have the general foR""ula (1 A) where W is N and X, Y and Z are CH. Table 12
Table 12 consists of 662 compounds of the general foR""ula (1 A), where W is N and X,Y and Z are CH, R is CI, R1 is 2,5,6-trifluorophenyI, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 12 is the same as compound 1 of Table 2 except that in compound 1 of Table 12, the compound has the general- foR""ula (1A) where W is N and X, Y and Z are CH. Similarly, compounds 2 to 662 of Table 12 are the same as compounds 2 to 662 of Table 2 except that in the compounds of Table 12, the compounds have the general foR""ula (1 A) where W is N and X, Y and Z are CH. Table 13
Table 13 consists of 662 compounds of the general foR""ula (1A), where W is N and X, Y and Z are CH, R is CI, R1 is 2,3,4,5,6-pentafluorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 13 is the same as compound 1 of Table 3 except that in compound 1 of Table 13, the compound has the general foR""ula (1 A) where W is N and X, Y and Z are CH. Similarly, compounds 2 to 662 of Table 13 are the same as compounds 2 to 662 of Table 3 except that in the compounds of Table 13, the compounds have the general foR""ula (1 A) where W is N and X, Y and Z are CH. Table 14
Table 14 consists of 662 compounds of the general foR""ula (1A), where W is N and X, Y and Z are CH, R is CI, R1 is 2,6-difluoro-4-methoxyphenyl, and the values of R3 andR4 are as listed in Table I. Thus, compound 1 of Table 14 is the same as compound 1 of Table 4 , except that in compound 1 of Table 14, the compound has the general foR""ula (1A) where W is N and X, Y and Z are CH. Similarly, compounds 2 to 662 of Table 14 are the same as compounds 2 to 662 of Table 4 except that in the compounds of Table 14, the comooumis

Table 15 consists of 662 compounds of the general foR""ula (1 A), where W is N and X,Yand Z are CH, R is CI, R1 is 2-fluoro~6-chlorophenyl, and the values of RJ and R4 are as listed in Table 1. Thus, compound 1 of Table 15 is ihe same as compound 1 of Table 5 except that in compound 1 of Table 15, the compound has the general foR""ula (I A) where W is N and X, Y and Z are CH. Similarly, compounds 2 to 662 of Table 15 are the same as compounds 2 to 662 of Table 5 except that in the compounds of Table 15, the compounds have the general foR""ula (1A) where W is N and X, Y and Z are CH. Table 16
Table 16 consists'of 662 compounds of the general foR""ula (IB), where W is N and
X, Y and Z are CH, R is CI, R1 is 2,4.6-trifluorophenyl, and the values of R- and R" are as
listed'in Table 1. Thus, compound 1 of Table 16 is the same as compound 1 of Table 11
except that in compound 1 of Table 16, the compound has the general foR""ula (IB).
Similarly, compounds 2 to 662 of Table 16 are the same as compounds 2 to 662 of Table 11
except that in the compounds of Table 16, the compounds have the general foR""ula (IB).
Table 17
Table 17 consists of 662 compounds of the general foR""ula (IB), where W is N and
i ** *
X, Y and Z are CH, R is CI, R is 2,5,6-trifluorophenyl, and the values of RJ and K* are as
listed in Table 1. Thus, compound 1 of Table 17 is the same as compound 1 of Table 12
except that in compound 1 of Table 17, the compound has the general foR""ula (IB).
Similarly, compounds 2 to 662 of Table 17 are the same as compounds 2 to 662 of Table 12
except that in the compounds of Table 17, the compounds have the general foR""ula (IB).
Table 18
Table 18 consists of 662 compounds of the general foR""ula (IB), where W is N and
X, Y and Z are CH, R is CI, R1 is 2,3,4,5,6-pentafluorophenyl, and the values of R3 and R4
are as listed in Table 1. Thus, compound 1 of Table 18 is the same as compound 1 of Table
13 except that in compound 1 of Table 18, the compound has the general foR""ula (IB).
Similarly, compounds 2 to 662 of Table 18 are the same as compounds 2 to 662 of Table 13
* except-that in the compounds of Table 18, the compounds have the general foR""ula (IB).
Table 19
Table 19 consists of 662 compounds of the general foR""ula (IB), where W is N and
X. Y and Z are CH, R is CI. Rl is 2.6-difluoro-4-methoxvt>henvl. and the values of R3 and R4

Similarly, compounds 2 to 662 of Table 19 are the same as compounds 2 to 662 of Table 14
except that in the compounds of Table 19, the compounds have the senera! foR""ula OB)
Table 20
Table 20 consists of 662 compounds of the general foR""ula (IB), where W is N and X, Y and Z are CH, R is CI, R1 is 2-fluoro-6-chloropheny!, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 20 is the same as compound 1 of Table 15 except that in compound 1 of Table 20, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 20 are the same as compounds 2 to 662 of Table 15 except that in the compounds of Table 20, the compounds have the general foR""ula (IB) Table 21
Table 21 consists of 662 compounds of the general foR""ula (1 A), where W, X and Z are CH and Y is N, R is CI, R1 is 2,4,6-tnfluorophenyl, and the values of R3 and R4' are as listed in Table 1. Thus, compound 1 of Table 21 is the same as compound 1 of Table 1 except that i„ compound 1 of Table 21, the compound has the general foR""ula (1 A) where W, X and Z are CH and Y is N. Similarly, compounds 2 to 662 of Table 21 are the same as compounds 2 to 662 of Table 1 except that i„ the compounds of Table 21, the compounds have the general foR""ula (i'A) where W, X and Z are CH and Y is N. Table 22
Table 22 consists of 662 compounds of the general foR""ula (IA), where W, X and Z are CH and Y is N, R is CI, R1 is 2,5,6-trifluorophenyl, and the values of R3 and R4' are as listed in Table 1. Thus, compound 1 of Table 22 is the same as compound 1 of Table 2 except that in compound 1 of Table 22, the compound has the general foR""ula (1 A) where W, X and Z are CH and Y is N. Similarly, compounds 2 to 662 of Table 22 are the same as compounds 2 to 662 of Table 2 except that in the compounds of Table 22, the compounds have the general foR""ula (1 A) where W, X and Z are CH and Y is N. Table 23
Table 23 consists of 662 compounds of the general foR""ula (1 A), where W, X and Z are CH and Y is N, R is CI, R1 is 2,3,4,5,6-pentafluorophenyl, and the values of R3 and R4 are as listed in.fable 1. Thus," compound 1 of Table 23 is the same as compound 1 of Table 3 except that in compound 1 of Table 23, the compound has the general foR""ula (1 A) where W, X and Z are CH and Y is N. Similarly, compounds 2 to 662 of Table 23 are the same as

Table 24
Table 24 consists of 662 compounds of the general foR""ula (1 A), where \Y, X and Z are CH and Y is N, R is CI, R1 is 2,6-difluoro-4-methoxyphenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound I of Table 24 is the same as compound 1 of Table 4 except that in compound 1 of Table 24, the compound has the general foR""ula (1 A) where W, X and Z are CH and Y is N. Similarly, compounds 2 to 662 of Table 24 are the same as compounds 2 to 662 of Table 4 except that in the compounds of Table 24, the compounds have the general foR""ula (1 A) where W, X and Z are CH and Y is N. Table 25
Table 25 consists of 662 compounds of the general foR""ula (1 A), where \\,X and Z are CH and Y is N, R is CI, R1 is 2-fluoro-6-chlorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 25 is the same as compound 1 of Table 5 except that in compound 1 of Table 25, the compound has the general foR""ula (1 A) where W, X and Z are CH and Y is N. Similarly, compounds 2 to 662 of Table 25 are the same as compounds 2 to 662 of Table 5 except that in the compounds of Table 25, the compounds have the general foR""ula (1 A) where W, X and Z are CH and Y is N. Table 26
Table 26 consists of 662 compounds of the general foR""ula (1 A), where W, Y and Z are CH and X is N, R is CI, R1 is 2,4,6-trifluorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 26 is the same as compound 1 of Table 1 except that in compound 1 of Table 26, the compound has the general foR""ula (1 A) where W, Y and Z are CH and X is N. Similarly, compounds 2 to 662 of Table 26 are the same as compounds 2 to 662 of Table 1 except that in the compounds of Table 26, the compounds have the general foR""ula (1 A) where W, Y and Z are CH and X is N. Table 27
Table 27 consists of 662 compounds of the general foR""ula (1A), where W, Y and Z are CH and X is N, R is CI, R1 is 2,5,6-trifluorophenyl, and the values of R3 and R4 are as
listed in Table 1. Thus, compound 1 of Table 27 is the same as compound 1 of Table 2

' except that in compound 1 of Table 27, the compound has the general foR""ula (1 A) where W, Y and Z are CH and X is N. Similarly, compounds 2 to 662 of Table 27 are the same as

Table 28
Table 28 consists of 662 compounds of the general foR""ula (1 A), where W. Y and Z are CH and X isN, R is CI, R1 is 2.3A5,6-pentafluorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 28 is the same as compound 1 of Table 3 except that in compound 1 of Table 28, the compound has the general foR""ula (1 A) where W, Y and Z are CH and X is N. Similarly, compounds 2 to 662 of Table 2S are the same as compounds 2 to 662 of Table 3 except that in the compounds of Table 28, the compounds have the general foR""ula (1A) where W, Y and Z are CH and X is N. Table 29
Table 29 consists of 662 compounds of the general foR""ula (1 A), where YY,Y and Z are CH and X is N, R is CI, R1 is 2,6-difluoro-4-methoxyphenyI, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 29 is the same as compound 1 of Table 4 except that in compound 1 of Table 29, the compound has the general foR""ula (1 A) where W, Y and Z are CH and X is N. Similarly, compounds 2 to 662 of Table 29 are the same as compounds 2 to 662 of Table 4 except that in the compounds of Table 29, the compounds have the general foR""ula (1 A) where W, Y and Z are CH and X is N.-Table 30
Table 30 consists of 662 compounds of the general foR""ula (1 A), where W, Y and Z are CH and X is N, R is CI, R1 is 2-fluoro-6-chlorophenyl, and the values of R3 and R4 are as listed in Table 1. Thus, compound 1 of Table 30 is the same as compound 1 of Table 5 except that in compound 1 of Table 30, the compound has the general foR""ula (1 A) where W, Y and Z are CH and X is N. Similarly, compounds 2 to 662 of Table 30 are the same as compounds 2 to 662 of Table 5 except that in the compounds of Table 30, the compounds have the general foR""ula (1 A) where W, Y and Z are CH and X is N. Table 31
Table 31 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds.1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly

Table 32
Table-32 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds I9S7 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 32 R is 2-fluorophenyl instead of 2-fluoro-6-chlorophenyl. Table 33
Table 33 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 33 R is 2,3,5,6-tetrafluorophenyl instead of 2-fluoro-6-chlorophenyI. Table 34
Table 34 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as
compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as
compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same
as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the
same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly
the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are
exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the
compounds of Table 34 Rl is 2-chloro-4,6-difluorophenyl instead of 2-fluoro-6-chloro-
phenyl

same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 35 R is 2-chloropheny] instead of 2-fIuoro-6-chIorophenyl. Table 36
Table 36 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds I to 662 of Table 30 respectively, except that in all of the compounds of Table 36 R3 is 2,6-dichlorophenyl instead of 2-fluoro-6-chIorophenyL
Table 37 -
- i
Table 37 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectivelyrcompounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds I to 662 of Table 30 respectively, except that in all of the compounds of Table 37 R1 is 2,4-dichlorophenyl instead of 2-fluoro-6-chlorophenyl. Table 38
Table 38 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly - . the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the

Table 39
Table 39 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 axe exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 39 R is 2,3,6-trichlorophenyl instead of 2-fluoro-6-chlorophenyl. Table 40
Table 40 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are .exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 40 R1 is pentachlorophenyl instead of 2-fluoro-6-chlorophenyL Table 41
Table 41 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as
compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as
compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same
as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the
same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly
the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are
exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the
compounds of Table 41 R1 is 2-fluoro-4,6-dichlorophenyl instead of 2-fluoro-6-chloro-
phenyl.
Table 42.
Table 42 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as

same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactiv the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 42 R1 is 4-fluoro-2,6-dichIorophenyl instead of 2-fluoro-6-chloro-phenyl. Table 43
Table 43 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 43 R is 2-bromophenyl instead of 2-fluoro-6-chlorophenyl. Table 44
-Table 44 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 44 Rl is 2-fluoro-6-bromophenyI instead of 2-fluoro-6-chlorophenyl. Table 45
Table 45 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the

Table 46
Table 46 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the 'same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 46 R is 2-fluoro-.6-methylphenyl instead of 2-fluoro-6-chlorophenyl. Table 47
Table 47 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds I to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 47 R1 is 2-chloro-6-methylphenyl instead of 2-fluoro-6-chlorophenyl. Table 48
Table 48 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds I to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 48 R1 is 2-methoxyphenyl instead of 2-fluoro-6-chlorophenyl. Table 49
Table 49 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as

the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 49 R1 is 2,6-dimethoxyphenyl instead of 2-fluoro-6-chIorophenyl Table 50
Table 50 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 50 R is 2-fluoro-6-methoxyphenyl instead of 2-fluoro-6-chIorophenyI. Table 51
Table 51 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds "1 to 662 of Table 5 respectively, compounds"663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325"to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 51 R is 2-trifluoromethylphenyl instead of 2-fluoro-6-chlorophenyl. Table 52
Table 52 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 52 R1 is 2-fluoro-6-trifluoromethylphenyl instead of 2-fluoro-6-chloro-ohenyl.

Table 53
Table 53 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 53 R is 2,6-di- Table 54 consists of 3972 compounds. Compounds*! to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 54 R1 is 2-chIoro-6-trifIuoromethylphenyl instead of 2-fluoro-6-chlorophenyl. Table 55
Table 55 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 55 R1 is 2,4-difluoro-6-trifluoromethylphenyl instead of 2-fluoro-6-chlorophenyl. TableJ>6

compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 56 R! is 2,4-difluoro-6-rnethoxyphenyl instead of 2-ftuoro-6-chloro-phenyl. Table 57
Table 57 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same -} .as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are ' exactly the same as compounds 1 to 662 of Table 30 respectively, except-that in all of the compounds of Table 57 R1 is 2,4-difluoro-6-methylphenyl instead of 2-fluoro-6-chloro-phenyl. Table 58
Table 58 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 58 R! is 2,4-difluoropyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 59
Table 59 consists of 3972 compounds. Compounds 1 to 662. are exactlv the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648

exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 59 R1 is 3,5-difluoropyrid-4-yI instead of 2-fluoro-6-chlorophenyl. Table 60
Table 60 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 60 Rl is tetrafluoropyrid-4-yl instead of 2-fluoro-6-chlorophenyI. Table 61
Table 61 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds I to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662-of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 61 R! is 3-fluoropyrid-2-yl instead of 2-fluoro-6-chlorophenyl. Table 62
Table 62 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are
exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the
n . ...
compounds of Table 62 R1 is 4-fluoropyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 63
Table 63 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as

as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that m all of the compounds of Table 63 R is 3-fluoropyrid-4-yl instead of 2-fluoro-6-chIorophenyl. Table 64
Table 64 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 64 R1 is 2-fluoropyrid-3-yl instead of 2-fluoro-6-chloropheny!. Table 65
Table 65 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to. 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 65 R1 is 2,4,6-trifluoropyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 66
Table 66 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactiy the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, exceot that in all of the

Table 67
Table 67 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 io 662 of Table 20 respectively, compounds 2649 to 3310 axe exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 67 R is2.6-difiuoropyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 6S
Table 68 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds I to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 68 R1 is 2,4-difluoro-6-methoxypyrid-3-yl instead of 2-fluoro-6-chIoro-phenyl. Table 69
Table 69 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as
compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as
compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same
as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the
same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly
the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are
exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the
compounds of Table 69 Rl is 2-fluoro-4-chloropyrid-3-yI instead of 2-fluoro-6-chlorophenyl.
Table 70
Table 70 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as

same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly
the same as compounds I to 662 of Table 25 respectively, and compounds 3311 to 3972 are
exactly the same as compounds I to 662 of Table 30 respectively, except that in all of the
compounds of Table 70 R1 is 3-fluoro-5-chloropyrid-4-yl instead of 2-fiuoro-6-chlorophenyI. Table 71
Table 71 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 71 R1 is 2-chloro-4-fluoropyrid-3-yl instead of 2-fluoro-6-chIorophenyl/ Table 72
Table 72 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 6.62 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds I to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 72 R* is 2,4-dichloropyrid-3-yl instead of 2-fluoro-6-chIorophenyl. Table 73
Table 73 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 73 Rl is 3-chloropyrid-2-yl instead of 2-fluoro-6-chloroohenv!.

Table 74
Table 74 consists of 3972 compounds. Compounds I to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table-25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 74 R is 4-chlo:opyrid-3-yl instead of 2-fluoro-6-chlorophenyI. Table 75
Table 75 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Tattle 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 75 R1 is 3-chloropyrid-4-yl instead of 2-fluoro-6-chlorophenyl. Table 76
Table 76 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 76 R! is 2-chloropyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 77
Table 77 consists of 3972 compounds. Compounds 1 to*662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same

the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 77 R1 is 3-trifluoromethyipyrid-2-yl instead of 2-fluoro-6-chlorophenvl. Table 78
Table 7S consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 78 R1 is 4-trifluoromethyIpyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 79
Table 79 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds I to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 79 R1 is 3,5-dichloropyrid-2-yl instead of 2-fluoro-6-chlorophenyl. Table 80
Table 80 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 80 R1 is 4,6-dichloropyrid-3-yl instead of 2-fluoro-6-chlorophenyl.
Table.3_l

compounds 1 to 662 of Table 10 respectively, compounds 1325 to I9S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 6o2 of Table 30 respectively, except that in all of the compounds of Table 81 R'is 3-tritluoromethyipyrid-4-yI instead of 2-fluoro-6-chlorophenyl. Table 82
Table 82 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 82 R1 is 2-trifIuoromethy!pyrid-3-yl instead of 2-fluoro-6-chlorophenyL Table 83
Table 83 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 83 R1 is 2-fluoro-4-trifluoromethylpyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 84
Table 84 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly

compounds of Table S4 R1 is 3-fluoro-5-tnfluoromethyipyrid-4-yl instead of 2-fluoro-6-chlorophenyl.
Table 85
Table 85 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 85 R1 is 4-fluoro-2-trifIuoromethylpyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 86
Table 86 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the satne as compounds I to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 86 R1 is 2,6-dichloropyrid-3-yl instead of 2-fluoro-6-chlorophenyl. Table 87
Table 87 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds I to 662 of Table 25 respectively, and compounds S3 IT to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 87 R1 is 3,5-dichloropyrid-4-yl instead of 2-fluoro-6-chlorophenyl. Table 88

compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2643 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in ail of the compounds of Table SS R1 is 3-chIoro-6-trifluoromethylpyrid-2-yl instead of 2-fluoro-6-chlorophenyl. Table 89
Table S9 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same^ as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are -exactly'the.same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 89 R1 is 3-fIuoro-6-trifIuoromethylpyrid-2-yl instead of 2-fluoro-6-chlorophenyl. Table 90
Table 90 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649. to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 90 Rl is pyrid-2-yl instead of 2-fluoro-6-chlorophenyI. Table 91
Table 91 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the

exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 91 R1 is pyrid-3-yl instead of 2-fluoro-6-chlorophenyI. Table 92
Table 92 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 92 R1 is pyrid-4-yl instead of 2-fluoro-6-chIorophenyl. Table 93
Table 93 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 93 R1 is 3-fluorothien-2-yl instead of 2-fluoro-6-chlorophenyl. Table 94
Table 94 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all oftfie compounds of Table 94 R1 is 3-chlorothien-2-yl instead of 2-fluoro-6-chIorophenyl. Table 95

as compounds 1 to 662 of Table 15 respectively, compounds 19S7 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 95 R1 is 2,4-difIuorothien-3-yl instead of 2-fluoro-6-chlorophenyl. Table 96
Table 96 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 96 R1 is 2,4-dichlorothien-3-yl instead of 2-fluoro-6-chlorophenyl. . Table 97
Table 97 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 97 R1 is 2,4,5-trichlorothien-3-yl instead of 2-fluoro-6-chlorophenyl. Table 98
Table 98 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the

Table 99
Table 99 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 ore exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 264S are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 99 R1 is 2-methylpiperidino instead of 2-fluoro-6-chlorophenyI. Table 100
Table 100 consists of 3972 compounds. Compounds 1 to 662Are exactly the same aS compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 19S6 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the * compounds of Table 100 R1 is 2,6-dimethyIpiperidino instead of 2-fluoro-6-chIorophenyl. Table 101
Table 101 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10 respectively, compounds 1325 to 1986 are exactly the same as compounds 1 to 662 of Table 15 respectively, compounds 1987 to 2648 are exactly the same as compounds 1 to 662 of Table 20 respectively, compounds 2649 to 3310 are exactly the same as compounds 1 to 662 of Table 25 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 101 R1 is morpholino instead of 2-fluoro-6-chlorophenyl. Table 102
Table 102 consists of 3972 compounds. Compounds 1 to 662 are exactly the same as compounds 1 to 662 of Table 5 respectively, compounds 663 to 1324 are exactly the same as compounds 1 to 662 of Table 10

the same as compounds 1 to 662 of Table ?5 respectively, and compounds 3311 to 3972 are exactly the same as compounds 1 to 662 of Table 30 respectively, except that in all of the compounds of Table 102 R1 is 2,6-dimethyImorpholino instead of 2-fluoro-6-chlorophenyl. Table 103
Table 103 consists of 305,844 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 102 (thus, for-example. compound I of Table 103 is the same as compound 1 of Table 1, compound 663 of Table 103 is the same as compound 1 of Table 2, compound 19,861 of Table 103 is the same as compound 1 of Table 31, compound 305,844 of Table 103 is the same as compound 3.972 of Table 102) except that in all of the compounds of Table 103 R is F instead of CI. Table 104
Table 104 consists of 305,844 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 102 (thus, for example, compound 1 of Table 104 is the same as compound 1 of Table 1, compound 663 of Table 104 is the same as compound 1 of Table 2, compound 19,8(51 of Table 104 is the same as compound 1 of Table - 31, compound 305,844 of Table 104 is the same as compound 3,972 of Table 102) except ... that in all of the compounds of Table 104 R is Br instead of CI. Table 105
Table 105 consists of 305,844 compounds. Each of these compounds is exactly the' same as the corresponding compound in Tables 1 to 102 (thus, for example, compound 1 of Table 105 is the same as compound 1 of Table 1, compound 663 of Table 105 is the same as compound 1 of Table 2, compound 19,861 of Table 105 is the same as compound 1 of Table 31, compound 305,844 of Table 105 is the same as compound 3,972 of Table 102) except that in all of the compounds of Table 105 R is methyl instead of CI. Table 106
Table 106 consists of 305,844 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 102 (thus, for example, compound 1 of
Table 106 is the same as compound 1 of Table.1, compound 663 of Table 106 is the same as
compound 1 of Table 2, compound 19,861 of Table 106 is the same as compound 1 of Table 31, compound 305,844 of Table 106 is the same as compound 3,972 of Table 102) except that in all of the compounds of Table 106 R is ethyl instead of CI.

Table 107
Table 107 consists of 305,844 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 102 (thus, for example, compound 1 of Table 107 is the same as compound 1 of Table 1, compound 663 of Table 107 is the same as compound 1 of Table 2, compound I9.S61 of Table 107 is the same as compound I of Table 31, compound 305,844 of Table 107 is the same as compound 3,972 of Table 102) except that in all of the compounds of Table 107 R is cyano instead of CI. Table 108
Table 108 consists of 305,844 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 102 (thus, for example, compound 1 of Table 108 is the same as compound 1 of Table 1, compound 663 of Table 108 is the same as compound 1 of Table 2, compound 19,861 of Table 10S is the same as compound 1 of Table 31, compound 305,844 of Table 108 is the same as compound 3,972 of Table 102) except that in all of the compounds of Table 108 R is methoxy instead of CI. Table 109
Table 109 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table
109 is the same as compound 1 of Table 1, compound 663 of Table 109 is the same as
compound 1 of Table 2, etc.) except that in all of the compounds of Table 109 X is CF
instead of CH.
Table 110
Table 110 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table
110 is the same as compound 1 of Table 1, compound 663 of Table 110 is the same as
compound 1 of Table 2, etc.) except that in all of the compounds of Table 110 X is CC1
instead of CH.
Table 111
Table 111 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table
111 is the same as compound 1 of Table 1, compound 663 of Table 111 is the same as
compound 1 of Table 2, etc.) except that in all of the

Table 112
Table 112 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table
112 is the same as compound 1 of Table 1, compound 663 of Table 112 is the same as
compound 1 of Table 2, etc.) except that in all of the compounds of Table 112 X is CCH3
instead of CH.
Table 113
Table 113 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table
113 is the same as compound 1 of Table 1, compound 663 of Table 113 is the same as
compound 1 of Table 2, etc.) except that in all of the compounds of Table 113 Y is CF
instead of CH.
Table 114
Table 114 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table
114 is the same as compound 1 of Table I, compound 663 of Table 114 is the same as
compound 1 of Table 2, etc.) except that in all of the compounds of Table 114 Y is CC1
instead of CH.
Table 115
Table 115 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table
115 is the same as compound 1 of Table 1, compound 663 of Table 115 is the same as
compound 1 of Table 2, etc.) except that in all of the compounds of Table 115 Y is CBr
instead of CH.
Table 116
Table 116 consists of 6620 compounds. Each of these compounds is exactly the same as the corresponding compound in Tables 1 to 10 (thus, for example, compound 1 of Table
116 is the same as compound 1 of Table 1, compound jj£3,o£ Table 116 is the same as
compound 1 of Table 2, etc.) except that in all of the compounds of Table 116 Y is CCH3
instead ofCH.

listed in Table 1. Thus, compound I of Table ! 17 is the same as compound 1 of Table 21 except that in compound 1 of Table 117. the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 117 are the same as compounds 2 to 662 of Table 21 except that in the compounds of Table 117, the compounds have the general foR""ula (IB).
Table 118
Table 1 IS consists of 662 compounds of the general foR""ula (IB), where W, X and Z
are CH and Y is N, R is CI, R1 is 2,5,6-trifluorophenyI, and the values of R3 and R4 are as
listed in Table I. Thus, compound I of Table 1 IS is the same as compound 1 of Table 22
except that in compound ] of Table 118, the compound has the general foR""ula (IB).
Similarly, compounds 2 to 662 of Table 118 are the same as compounds 2 to 662 of Table 22
except that in the compounds of Table 1 IS, the compounds have the general foR""ula (IB).
Table 119
Table 119 consists of 662 compounds of the general foR""ula (IB), where W, X and Z
are CH and Y is N, R is CI, R! is 2,3,4,5,6-pentafluorophenyl, and the values of R3 and R4
areas listed in Table 1. Thus, compound 1 of Table 119 is the same as compound 1 of Table
23 except that in compound 1 of Table 119, the compound has the general foR""ula (IB).
Similarly, compounds 2 to 662 of Table 119 are the same as compounds 2 to 662 of Table 23
except that in the compounds of Table 1-19, the compounds have the general foR""ula (IB).
Table 120
Table 120 consists of 662 compounds of the general foR""ula (IB), where W, X and Z
are CH and Y is N, R is CI, R] is 2,6-difluoro-4-methoxyphenyI, and the values of R3 and R4
are as listed in Table 1. Thus, compound 1 of Table 120 is the same as compound 1 of Table
24 except that in compound 1 of Table 120, the compound has the general foR""ula (IB).
Similarly, compounds 2 to 662 of Table 120 are the same as compounds 2 to 662 of Table 24
except that in the compounds of Table 120, the compounds have the general foR""ula (IB).
Table 121
Table 121 consists of 662 compounds of the general foR""ula (IB), where W, X and Z
are CH and Y is N, R is CI, R1 is 2-fluoro-6-chlorophenyl, and the values of R3 and R are as
listed in Table 1. Thus, compound 1 of Table 121 is the same as compound I of Table J25 . .
except that in compound 1 of Table 121, the compound1 has the general foR""ula (IB).
Similarly, compounds 2 to 662 of Table 121 are the same as compounds 2 to 662 of Table 25
except that in the compounds of Table 121, the compounds have the general foR""ula (IB).

Table 122
Table 122 consists of 662 compounds of the general foR""ula (IB), where W, Y and Z are CH and X is N, R is CI, R1 is 2,4.6-trifluorophenyI, and the values of R3 and R4 are as listed in Table !. Thus, compound 1 of Table 122 is the same as compound 1 of Table 26 except that in compound 1 of Table 122, the compound has the general foR""ula (IB). Similarly, compounds 2 to 662 of Table 122 are the same as compounds 2 to 662 of Table 26 except that in the compounds of Table 122, the compounds have the general foR""ula (IB).
Table 123
Table 123 consists of 662 compounds of the general foR""ula (IB), where \V, Y and Z
are CH and X is N, R is CI, R1 is 2,4.5-trifluorophenyl, and the values of R3 and R4 are as
listed in Table I. Thus, compound 1 of Table 123 is the same as compound 1 of Table 27
except that in compound 1 of Table 123, the compound has the general foR""ula (IB).
Similarly, compounds 2 to 662 of Table 123 are the same as compounds 2 to 662 of Table 27
except that in the compounds of Table 123, the compounds have the general foR""ula (IB).
Table 124
Table 124 consists of 662 compounds of the general foR""ula (IB), where W, Y and Z
are CH and X is N, R is CI, R1 is 2,3,4,5,'6-pentafluorophenyl, and the values of R3 and R4
are as listed in Table 1. Thus, compound'1 of Table 124 is the same as compound 1 of Table
28 except that in compound 1 of Table 124, the compound has the general foR""ula (IB).
Similarly, compounds 2 to 662 of Table 124 are the same as compounds 2 to 662 of Table 23
except that in the compounds of Table 124, the compounds have the general foR""ula (IB).
Table 125
Table 125 consists of 662 compounds of the general foR""ula (IB), where W, Y and Z
are CH and X is N, R is CI, R1 is 2,6-difluoro-4-methoxyphenyl, and the values of R3 and R4
are as listed in Table 1. Thus, compound 1 of Table-125 is the same as compound 1 of Table
29 except that in compound 1 of Table 125, the compound has the general foR""ula (IB).
Similarly, compounds 2 to 662 of Table 125 are the same as compounds 2 to 662 of Table 29
except that in the compounds of Table 125, the compounds have the general foR""ula (IB).
Table 126
Table 126 consists of 662 compounds of the general foR""ula (IB), where W, Y and Z
are CH and X is N, R is CI, Rl is 2-fluoro-6-ch!orophenyl, and the values of R3 and R4 are as
listed in Table 1. Thus, compound 1 of Table 126 is the same as compound 1 of Table 30
except that in compound 1 of Table 126, the compound has the general foR""ula (IB).

Similarly, compounds 2 to 662 of Tabie 126 are the same as compounds 2 to 662 of Table 30 except that in the compounds of Table 126, the compounds have the general foR""ula (IB).
Compounds of foR""ula (7) or (S). which are examples of compounds of general foR""ula (1) where one of R and R2 is N-R3R-,can be made as shown in Scheme 1, in which W, X, Y, Z, R , R" and R have the meanings given above and R is C1-4 alkyl.

Compounds of general foR""ula (4) can be prepared from compounds of general foR""ula (2), which are either commercially available or made by methods known in the literature, by reaction with acids of general foR""ula (3), using standard coupling methods, for example by conversion to the acid chloride using a chlorinating agent such as thionyl chloride, followed by reaction of the resultant acid chloride optionally in the presence of a - base such-as triethylamine, in a suitable solvent such as dichloromethane or toluene. Compounds of general foR""ula (5) can be prepared by treating compounds of general foR""ula (4) with a base such as sodium hydride, optionally in the presence of a Lewis acid

general foR""ula (6) can be prepared by reaction of compounds of general foR""ula (5) with a chlorination reagent such as phosphorus oxychloride, either neat or in a suitable solvent such as toluene, at between 50 and 150°C. but preferably between SO and 110°C, or in a microwave reactor at between 150 and 300°C, but preferably between 200 and 250°C. Compounds of foR""ula (7) and (S) can be prepared by reaction of compounds of general foR""ula (6) with an amine R3RaNH, either neat, or in a suitable solvent such as DMF, between room temperature and 150°C, but preferably between 50 and 80°C. If compounds
(7) and (S) are produced as a mixture they can be separated by suitable means such as
crystallisation or chromatography under noR""al or reverse phase conditions.
Compounds of the general foR""ulae (5), (6), (7) and (8) may be derivatised, via the chloro or hydroxy substituents, using routine chemical techniques to foR"" other compounds of the general foR""ula (1). Alternatively, other compounds of the general foR""ula (1) may be prepared using a similar methodology to that described for preparing the compounds (5) to
(8) and employing preparative techniques known from the chemical literature.
Compounds of foR""ula (7) can also be made as shown in scheme 2.

Compounds of general foR""ula (10) can be prepared from compounds of general foR""ula (9), which are either commercially available or made by methods known in the literature, by reaction with acids of general foR""ula (3), using standard coupling methods, for

chloride, followed by reaction of the resultant acid chloride optionally in the presence of a
base such as triethylamine, in a suitable solvent such as dichioromethane or toluene.
Compounds of general foR""ula (11) can be prepared by treating compounds of general
foR""ula (10) with a base such as sodium hydride, optionally in the presence of a Lewis acid
such as magnesium oxide, in a suitable solvent such as NN-dimethylfoR""amide (DMF) or
toluene, at between room temperature and 150°C, but preferably at 60-9O°C. Compounds of
general foR""ula (12) can be prepared by reaction of compounds of general foR""ula (11) with
a chlorination reagent such as phosphorus oxychloride, either neat or in a suitable solvent
such as toluene, at between- 50 and 150°C, but preferably between SO and 110°C, or in a
microwave reactor at between 150 and 300°C, but preferably between 200 and 250°C.
Compounds of foR""ula (7) can be prepared from compounds of foR""ula (12) by reductive
amination, for example by reaction with a ketone or aldehyde in a suitable solvent such as
ethanol or toluene, at between room temperature and reflux, optionally in the presence of an
acid catalyst such as para-toluenesulphonic acid or a drying agent such as moleC1-6lar sieves,
followed by treatment with a suitable reducing agent such as sodium borohydride, at between
-20°C and 40°C, but preferably at room temperature. The aldehyde or ketone is chosen so
that the desired groups R3 and R4 are foR""ed after reduction of the product of reaction with
the amine (12). For example if compounds of foR""ula (12) are reacted with one equivalent of
propionaldehyde and then sodium borohydride, compounds of foR""ula (7) where RJ is n-
propyl, and R is hydrogen are foR""ed. If required, the reaction can be repeated with a
different aldehyde or ketone. For example, if acetone is used for the second reaction, then
compounds of foR""ula (7) where R3 is N-propyl and R4 is zs-o-propyl, are foR""ed.
Alternatively compounds of foR""ula (7) can be foR""ed from compounds of foR""ula (12) by
alkylation with a group R3LG, where LG is a leaving group, by treatment with a suitable
base such as sodium hydride in a solvent such as DMF, or a base such as potassium
carbonate in a solvent such as acetone or DMF, at between -78°C and 100°C, but preferably
between room temperature and 60°C, followed by treatment with R4LG in a second step
under the same conditions if required. - -

Compounds of foR""ula (13) can be prepared as shown in Scheme 3 from compounds of foR""ula (6) by reaction with a source of fluoride ion, such as potassium fluoride, in a suitable solvent such as sulpholane, at a temperature between 50°C and 200°C7 but preferably at 80-150°C. Compounds of foR""ula (14) and/or compounds of foR""ula (15) can be prepared from difluoro compounds of foR""ula (13) by reaction with an amine of foR""ula R3R4NH in a suitable solvent such as DMF or CH2Q2, at a temperature of 0°C-100°C, but preferably at room temperature.

Compounds of general foR""ula (16), where Hal1 is chlorine or fluorine, can be converted into compounds of foR""ula (17), (18), (19), (20), (21), (22) or (23) as shown in Scheme 4. Compounds of general foR""ula (17) where Hal2 is bromine or iodine can be foR""ed by reacting compounds of general foR""ula (16) with a metal halide, for example C1-6prous bromide, in a suitable solvent, for example DMF, at between room temperature and 155°C, but preferably between 70°C and 155°C Compounds of general foR""ula (18) where V is oxygen or sulphur and R is C1-8 alkyl, can be foR""ed by reacting compounds of general foR""ula (16) with a metal alkoxide or thioalkoxide MVR9 in a suitable solvent, for example sodium methoxide in methanol, at room temperature to 65°C Compounds of general foR""ula

R is C1-8alkyl. can be foR""ed by reacting compounds of general foR""ula (16) with an alkyl metal derivative in a suitable solvent, for example methyl magnesium bromide in THF, optionally in the presence of catalyst such as C1-6prous bromide or Pd(Ph)4, between -40°C and 50°C. Compounds of general foR""ula (21) can be foR""ed by reduction of compounds of general foR""ula (16), where Hal1 is chlorine, for example by hydrogenolysis with hydrogen gas and a metal catalyst such as palladium on carbon in a suitable solvent such as ethanol, at room temperature. Compounds of general foR""ula (22) where R11 is hydrogen or C1-6 alkyl, can be foR""ed by reaction of compounds of general foR""ula (16) with an alkyl acetylene under the Sonogashira conditions, for example with 1-propyne in triethylamine in the presence of a C1-6prous salt such as C1-6prous iodide and a palladium catalyst such as Pd(Ph)4, between room temperature and 70°C Compounds of general foR""ula (23) where R12 is hydrogen or C1-6alkyl, can be foR""ed by reaction of compounds of general foR""ula (16) with an alkenyl metal derivative in a suitable solvent, such as ethenylboronic acid in THF, in the presence of a palladium catalyst such as Pd(Ph)4 and a base such as caesium carbonate, between room temperature and 65°C.

In Scheme 5 compounds of general foR""ula (24), where the two R R N groups are identical, can be made from compounds of general foR""ula (13) by reaction with a large excess of amine R3R4NH in a suitable solvent such as DMF, at a temperature between 0°C and 150°C, but preferably between room temperature and 100°C
Further assistance in the preparation of the compounds of foR""ula (1) may be derived
from the following publications: Emilio, Toja, et. al.7J. Heterocyclic Chem., 23, 1955
CI 9.86), H. Schafer, et. al.,J.f.prakt. Chemie, 321(4), 695 (1970) and H.Bredereck et. a/., Chem. Ber. 96, 1868-1872 (1993).
The inteR""ediate chemicals having the general foR""ulae (4), (5), (6) and (13):

wherein W, X, Y, Z, R and R are as define above, are believed to be novel compounds and foR"" a further part of this invention.
It should be noted that the inteR""ediate of general foR""ula (5) may exist in the tautomeric foR""s (a), (b) and (c) as well as in the foR"" shown in foR""ula (5):

The invention as defined by the'general foR""ula (5) embraces all such tautomers;
Of partiC1-6lar interest are the inteR""ediates listed in Tables 127 to 134 below. In Tabl-127 the compounds have the general foR""ula (4) where R7 is methyl and W, X, Y, Z and R1 have the values shown in the table.

Table 128
Table 128 consists of 48 compounds of the general foR""ula (5), where \V,X, Y, Z and R1 have the values given in Table 127. Thus, compound 1 of Table 12S has the same W, X, Y, Z and R! values as compound 1 of Table 127, etc. Table 129
Table 129 consists of 48 compounds of the general foR""ula (6), where W, X, Y, Z and R1 have the values given in Table 127. Thus, compound 1 of Table 129 has the same W, X, Y, Z and R1 values as compound 1 of Table 127, etc. Table 130
Table 130 consists of 48 compounds of the general foR""ula (13), "where W, X, Y, Z and Rl have the values given in Table 127. Thus, compound 1 of Table 130 has the same W. " X, Y, Z and R1 values as compound 1 of Table 127, etc. Table 131
Table 131 consists of 48 compounds of the general foR""ula (4), where W, X, Y, Z and R1 have the values given in Table 127 and R7 is ethyl. Thus, compound 1 of Table 131 is the same as compound 1 of Table 127 except that in compound 1 of Table 131, R' is ethyl instead of methyl. Similarly, compounds 2 to 48 of Table 131 are the same as compounds 2 to 48 of Table 127 except that in the compounds of Table 131, R is ethyl.
The compounds of foR""ula (1) are active fungicides and may be used to control one or more of the following pathogens: PyriC1-6laria oryzae. (Magnaporthe grisea) on rice and wheat and other PyriC1-6laria spp. on other hosts; Puccinia triticina (or recondita), Puccinia striifoR""is and other rusts on wheat, Puccinia hordei, Puccinia striifoR""is and other rusts on barley, and rusts on other hosts (for example turf, rye, coffee, pears, apples, peanuts, sugar beet, vegetables and ornamental plants); Erysiphe dehoracearum on C1-6C1-6rbits (for example melon); Blumeria (or Erysiphe) graminis (powdery mildew) on barley, wheat, rye and turf and other powdery mildews on various hosts, such as Sphaerotheca maC1-6laris or. hops,

apples and Uncinula necator on vines; Cochliobolus spp., Helminihosporium spp., Drechslera spp. (Pyrenophora spp.)* Rhynchosporium spp., Mycosphaerella graminicola (Septoria tritici) and Phaeosphaeria nodonim (Stagonospora nodorwn or Septoria nodorum). Pseudocercosporella herpotrichoides and Caeumannomyces gramirus on cerenls (for example wheat. barley, rye), turf and other hosts; Cercospora arachidicola and Cercosporidium personatum on peanuts and other Cercospora spp. on other hosts, for example sugar beet, bananas, soya beans and rice; Botrytis cinerea (grey mould) on tomatoes, strawberries, vegetables, vines and other hosts and other Botrytis spp. on other hosts; Alternaria spp. on vegetables (for example carrots), oil-seed rape, apples, tomatoes, potatoes, cereals (for example wheat) and other hosts; Venturia spp. (including Venturia inaequalis (scab)) on apples, pears, stone fruit, Jree nuts and other hosts; Cladosporium spp. on a range of hosts including cereals (for example wheat) and tomatoes; Monilinia spp. on stone fruit, tree nuts and other hosts; Didymella spp. on tomatoes, turf, wheat, C1-6C1-6rbits and other hosts; Phoma spp. on oil-seed rape, turf, rice, potatoes, wheat and other hosts; Aspergillus spp. and Aureobasidium spp. on wheat, lumber and other hosts; Ascochyta spp. -on peas, wheat, barley and other hosts; Stemphyliwn spp. (Pleospora spp.) on apples, pears, onions and other hosts; summer diseases (for example bitter rot (Gbmerella cingulata), black rot or frogeye leaf spot {Botryosphaeria obtiisa), Brooks fruit spot (Mycosphaerella pomi), Cedar apple rust (Gymnosporangiumjuniperi-virginianae), sooty blotch (Gloeodes pomigena), flyspeck (Schizothyrium pomi) and white rot (Botryosphaeria dothidea)) on apples and pears; Plasmopara viticola on vines; other downy mildews, such as Bremia lactucae on lettuce, Peronospora spp. on soybeans, tobacco, onions and other hosts, Pseudoperonospora humuli on hops and Pseudoperonospora C1-6bensis on C1-6C1-6rbits; Pythium spp. (including Pythium ultimum) on turf and other hosts; Phytophthora infestans on potatoes and tomatoes and other Phytophthora spp. on vegetables, strawberries, avocado, pepper, ornamentals, tobacco, cocoa and other hosts; Thanatephorus C1-6C1-6meris on rice and turf and other Rhizoctonia spp. on various hosts such as wheat and barley, peanuts, vegetables, cotton and turf; Sclerotinia spp. on turf, peanuts, potatoes, oil-seed rape and other hosts; Sclerotium spp. on turf, peanuts and other hosts; Gibberella fujikuroi on rice; Colletotrichum spp. on a range of hosts including turf, coffee and vegetables; Laetisaria fucifoR""is on turf; Mycosphaerella spp. on bananas, peanuts, citrus, pecans, papaya and other hosts; Diaporthe spp. on citrus, soybean, melon, pears, lupin and other hosts; Elsinoe spp. on citrus, vines,

potatoes and tomatoes; Pyrenopeziza spp. on oil-seed rape and other hosts; Oncobasidium
theobromae on cocoa causing vasC1-6lar streak dieback; Fusarium spp., Typhula spp.,
Microdochium nivale, Usiilago spp., Urocystis spp., Tilletia spp. and Claviceps purpurea on
a variety of hosts but partiC1-6larly wheat, barley, turf and maize; Ramulana spp. on sugar
beet, barley and other hosts; post-harvest diseases partiC1-6larly of fruit (for example
Penicillium digitatum, Penicillium italicwn and ThchodeR""a viride on oranges,
Colletotrichum musae and Gloeosporiwn musarum on bananas and Botrytis cinerea on
grapes); other pathogens on vines, notably Eniypa lata, Gnignardia bidwelliL Phellinus
igniarus, Phomopsis viticola, Pseudopeziza tracheiphila and Stereum hirsutum,other
pathogens on trees (for example LophodeR""ium seditiosum) or lumber, notably
CephaloasC1-6s fragrans, Ceratocyslis spp., Ophiostomapiceae, Penicillium spp., -"
TrichodeR""a pseudokoningii, TrichodeR""a viride, TrichodeR""a harzianwn, Aspergillus niger, Leptographium lindbergi and Aureobasidium pulhdans,and fungal vectors of viral diseases (for example Polymyxa gramims on cereals as the vector of barley yellow mosaic virus (BYMV) and Polymyxa betae on sugar beet as the vector of rhizomania).
A compound of foR""ula (1) may move acropetally, basipetally or locally in plant tissue to be active against one or more fungi. Moreover, a compound of foR""ula (l)Tnay be volatile enough to be active in the vapour phase against one or more fungi on the plant.
The invention therefore provides a method of combating or controlling phytopatho-genic fungi which comprises applying a fungicidally effective amount of a compound of foR""ula (1), or a composition containing a compound of foR""ula (1), to a plant, to a seed of a plant, to the loC1-6s of the plant or seed or to soil or any other plant growth medium, e.g. nutrient solution.
The teR"" "plant" as used herein includes seedlings; bushes and trees. FurtheR""ore, the fungicidal method of the invention includes protectant, C1-6rative, systemic, eradicant and antisporulant treatments.
The compounds of foR""ula (1) are preferably used for agriC1-6ltural, hortiC1-6ltural and
turfgrass purposes in the foR"" of a composition. - -
In order to apply a compound of foR""ula (1) to a plant, to a seed of a plant, to the loC1-6s of the plant or seed or to soil or any other growth medium, a compound of foR""ula (1) is usually foR""ulated into a composition which includes, in addition to the compound of

liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting). It is preferred that all compositions (both solid and liquid foR""ulations) comprise, by weight, 0.0001 to 95%, more preferably I to 85%, for example 5 to 60%, of a compound of foR""ula (1). The composition is generally used for the control of fungi such that a compound of foR""ula (1) is applied at a rate of from 0.1 g to 10kg per hectare, preferably from Ig to 6kg per hectare, more preferably from lg to 1kg per hectare.
When used in a seed dressing, a compound of foR""ula (1) is used at a rate of O.OOOlg to lOg (for example 0.00lg or 0.05g), preferably 0.005g to lOg, more preferably 0.005g to 4g, per kilogram of seed.
In another aspect the present invention provides a fungicidal composition comprising a fungicidally effective amount of a compound of foR""ula (1) and a suitable carrier or diluent therefor.
In a still further aspect the invention provides a method of combating and controlling fungi at a loC1-6s, which comprises treating the fungi, or the loC1-6s of the fangi with a fungicidally effective amount of a composition comprising a compound of foR""ula (1).
The compositions can be chosen from a number of foR""ulation types, including dustable powders (DP), soluble powders (SP), water soluble granules (SG), water dispersible granules (WG), wettable powders (WP), granules (GR) (slow or fast release), soluble concentrates (SL), oil miscible liquids (OL), ultra low volume liquids (UL), emulsifiable concentrates (EC), dispersible concentrates (DC), emulsions (both oil in water (EW) and water in oil (EO)), micro-emulsions (ME), suspension concentrates (SC), aerosols, fogging/smoke foR""ulations, capsule suspensions (CS) and seed treatment foR""ulations. The foR""ulation type chosen in any instance will depend upon the partiC1-6lar purpose envisaged and the physical, chemical and biological properties of the compound of foR""ula (1).
Dustable powders (DP) may be prepared by mixing a compound of foR""ula (1) with one or more solid diluents (for example natural clays, kaolin, pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk, diatomaceous earths, calcium phosphates, calcium and magnesium carbonates, sulphur, lime, flours, talc and other organic and inorganic solid carriers) and mechanically grinding the mixture to a fine powder.
Soluble powders (SP) may be prepared by mixing a compound of foR""ula (1) with one or more water-soluble inorganic salts (such as sodium bicarbonate, sodium carbonate or

and, optionally, one or more wetting agents, one or more dispersing agents or a mixture of said agents to improve water dispersibiiity/solubility. The mixture is then ground to a fine powder. Similar compositions may also be granulated to foR"" water soluble granules (SG).
Wettable powders (WP) may be prepared by mixing a compound of foR""ula (1) with one or more solid diluents or earners, one or more wetting agents and, preferably, one or more dispersing agents and, optionally, one or more suspending agents to facilitate the dispersion in liquids. The mixture is then ground to a fine powder. Similar compositions may also be granulated to foR"" water dispersible granules (WG).
Granules (GR) may be foR""ed either by granulating a mixture of a compound of foR""ula (1) and one or more powdered solid diluents or carriers, or from pre-foR""ed blank granules by absorbing a compound of foR""ula (1) (or a solution thereof, in a suitable agent) in "a porous granular material (such as pumice, attapulgite clays, fuller's earth, kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing a compound of foR""ula (1) (or a solution thereof, in a suitable agent) on to a hard core material (such as sands, silicates, mineral carbonates, sulphates or phosphates) and drying if necessary. Agents which are commonly used to aid absorption or adsorption include solvents (such as aliphatic and aromatic petroleum solvents, alcohols, ethers, ketonesand esters) and sticking agents (such as polyvinyl acetates, polyvinyl alcohols, dextrins, sugars and vegetable oils). One or more other additives may also be included in granules (for example an emulsifying agent, wetting agent or dispersing agent).
Dispersible Concentrates (DC) may be prepared by dissolving a compound of foR""ula (1) in water or an organic solvent, such as a ketone, alcohol or glycol ether. These solutions may contain a surface active agent (for example to improve water dilution or prevent crystallisation in a spray tank).
Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may be prepared by dissolving a compound of foR""ula (1) in an organic solvent (optionally containing one or more wetting agents, one or more emulsifying agents or a mixture of said agents). Suitable organic solvents for use in-ECs include aromatic hydrocarbons (such as alkylbenzenes or alkyinaphthalenes, exemplified by SOLVESSO 100, SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark), ketones (such as cyclohexanone or methylcyclo-hexanone), alcohols (such as

product may spontaneously emulsify on addition to water, to produce an emulsion with sufficient stability to allow spray application through appropriate equipment. Preparation of an EW involves obtaining a compound of foR""ula (1) either as a liquid (if it is not a liquid at room temperature, it may be melted at a reasonable temperature, typically below 70°C) or in solution (by dissolving it in an appropriate solvent) and then emulsifying the resultant liquid or solution into water containing one or more SFAs, under high shear, to produce an emulsion. Suitable solvents for use in EWs include vegetable oils, chlorinated hydrocarbons (such as chlorobenzenes), aromatic solvents (such as alkylbenzenes or alkylnaphthalenes) and other appropriate organic solvents that have a low solubility in water.
Microemulsions (ME) may be prepared by mixing water with a blend of one or more solvents with one or more SFAs, to produce spontaneously a theR""odynamically stable ^ isotropic liquid foR""ulation. A compound of foR""ula (1) is present initially in either the water or the solvent/SFA blend. Suitable solvents for use in MEs include those hereinbefore described for use in in ECs or in EWs. An ME may be either an oil-in-water or a watej-in-oil system (which system is present may be deteR""ined by conductivity measurements) and may be suitable for mixing water-soluble and oil-soluble pesticides in the same foR""ulation. An ME is suitable for dilution into water, either remaining as a microemulsion or foR""ing a conventional oil-in-water emulsion.
Suspension concentrates (SC) may comprise aqueous or non-aqueous suspensions of finely divided insoluble solid particles of a compound of foR""ula (1). SCs may be prepared by bail or bead milling the solid compound of foR""ula (I) in a suitable medium, optionally with c ne or more dispersing agents, to produce a fine particle suspension of the compound. One c; more wetting agents may be included in the composition and a suspending agent may be inc ;ded to reduce the rate at which the particles settle. Alternatively, a compound of foR""u . (1) may be dry milled and added to water, containing agents hereinbefore described, to pre :ce the desired end product.
\erosol foR""ulations comprise a compound of foR""ula (1) and a suitable propellant (for e: nple /z-butane). A compound of foR""ula (1) may also be dissolved or dispersed in a suitab medium (for example water or a water miscible liquid, such as /i-propanol) to provi .ompositions for use in non-pressurised, hand-actuated spray pumps.
. compound of foR""ula (1) may be mixed in the dry state with a pyrotechnic mixture to fo composition suitable for generating, in an enclosed space, a smoke containing the

Capsule suspensions (CS) may be prepared in a manner similar to the preparation of EW foR""ulations but with an additional polymerisation stage such that an aqueous dispersion of oil droplets is obtained, in which each oil droplet is encapsulated by a polymeric shell and contains a compound of foR""ula ;!) and, optionally, a carrier or diluent therefor. The polymeric shell may be produced by either an interfacial polycondensation reaction or by a coacervation procedure. The compositions may provide for controlled release of the compound of foR""ula (1) and they may be used for seed treatment. A compound of foR""ula (1) may also be foR""ulated in a biodegradable polymeric matrix to provide a slow, controlled release of the compound.
A composition may include one or more additives to improve the biological perfoR""ance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of a compound of foR""ula (1)). Such additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the ^ action of a compound of foR""ula (1)).
A compound of foR""ula (1) may also be foR""ulated for use as a seed treatment, for
example as a powder composition, including a powder for dry seed treatment (DS), a water soluble powder (SS) or a water dispersible powder for slurry treatment (WS), or as a liquid composition, including a flowable concentrate (FS), a solution (LS) or a capsule suspension (CS). The preparations of DS,SS, WS, FS and LS compositions are very similar to those of, respectively, DP, SP, WP, SC and DC compositions described above. Compositions for treating seed may include an agent for assisting the adhesion of the composition to the seed (for example a mineral oil or a film-foR""ing barrier).
Wetting agents, dispersing agents and emulsifying agents may be SFAs of the cationic, anionic, amphoteric or non-ionic type.
Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltrimethyl ammonium bromide), imidazolines and amine salts. Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds

sodium laureth-3-sulphate), ether carboxylates (for example sodium lauretho-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally these products may be ethoxylated), sulphosuccinamates, paraffin or define sulphonates, taurates and lignosulphonates.
Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.
Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenoL nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
Suitable suspending agents include hydrophrlic colloids (such-as polysaccharides, polyvinylpyrrolidone or sodium carboxymethylcelltriose) and swelling clays (such as bentonite or attapulgite).
A compound of foR""ula (1) may be applied by any of the known means of applying fungicidal compounds. For example, it may be applied, foR""ulated or unfoR""ulated, to any part of the plant, including the foliage, stems, branches or roots, to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic C1-6lture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste foR""ulation, applied as a vapour or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water-soluble bag) in soil or an aqueous environment,
A compound of foR""ula (1) may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.
Compositions for use as aqueous preparations (aqueous solutions or dispersions) are generally supplied in the foR"" of a concentrate containing a high proportion

withstand storage for prolonged periods and, after such storage, to be capable of addition to water to foR"" aqueous preparations which remain homogeneous for a sufficient time to enable them to be applied by conventional spray equipment. Such aqueous preparations may contain varying amounts of a compound of foR""ula (1) (for example 0.0001 to 10%, by weight) depending upon the purpose for which they are to be used.
A compound of foR""ula (1) may be used in mixtures with fertilisers (for example nitrogen-, potassium- or phosphorus-containing fertilisers). Suitable foR""ulation types include granules of fertiliser. The mixtures suitably contain up to 25% by weight-of the compound of foR""ula (1).
The invention therefore also provides a fertiliser composition comprising a fertiliser and a compound of foR""ula (1).
The compositions of this invention may contain other compounds having biological activity, for example micronutrients or compounds having'similar or complementary fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, .. nematicidal or acaricidal activity.
By including another fungicide, the resulting composition may have a broader spectrum of activity or a greater level of intrinsic activity than the compound of foR""ula (1) alone. Further the other fungicide may have a synergistic effect on the fungicidal activity of the compound of foR""ula (1).
The compound of foR""ula (1) may be the sole active ingredient of the composition o it maybe admixed with one or more additional active ingredients such as a pesticide, fungicide, synergist, herbicide or plant growth regulator where appropriate. An additional active ingredient may: provide a composition having a broader spectrum of activity or increased persistence at a loC1-6s; synergise the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the compound of foR""ula (1); or help to overcome or prevent the development of resistance to individual components. The partiC1-6lar additional active ingredient will depend upon the intended utility of the composition.
Examples of fungicidal compounds which may be included in the composition of the invention are AC 382042

trifloxystrobim triflumizole, trifonne, triticonazole. validamycin A, vapam, vinclozolin, XRJD-563, zineb, ziram, zoxamide and compounds of the foR""ulae:

The compounds of foR""ula (1) may be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.
Some mixtures may comprise active ingredients, which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional foR""ulation type. In these cirC1-6mstances other foR""ulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a" water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resultant composition is a suspoemulsion (SE) foR""ulation.

Step I
2-Aminonicotinic acid ethyl ester (2.4 g) was suspended in dry toluene (50 ml). To the stirred suspension, 2,4,6-trifluorophenylacetyl chloride (3.0 g) in dry toluene (20 ml) was added. The resulting suspension was heated to reflux for 8 hours. The reaction mixture was cooled to ambient temperature, diluted with diethyl ether (100 ml), washed with water and brine, and the organic layer was dried over magnesium sulphate. The solvent was evaporated... to give 2-[2-(2,4,6-trifluorophenyl)-acetylamino]-nicotinic acid ethyl ester as a yellow solid (4.5 g, 93%).
'H NMR (CDCh) 5 ppm: 133 (t,3H), 4.00 (s,2H), 4.31 (q,2H), 6.63 (m,2H); 7.00 (dd,lH), 3.25 (dd,lH), 8.50 (dd,lH), 10.86 (s,lH). Step 2
The product of Step 1 (3.0 g) was dissolved in toluene (100 ml) and sodium hydride (1.0 g of an 60% dispersion in mineral oil) was added portion-wise. There was an immediate reaction, and the mixture was stirred at room temperature for 2 hours, and at 70°C for 5 hours. The reaction mixture was cooled and evaporated to give a white solid (3 g), which was then acidified with dilute hydrochloric acid. The resultant white suspension was filtered and collected, washed with ether and dried to give 3-(2>4?6-trifluorophenyl)-
lH[l,8]naphthyridine-2,4-dione (1.6 g, 62%). 1H NMR (d6-DMSO) 5 ppm: 7.26 (m,3H), 8.35 (dd,lH), S.59 (dd,lH),l 1.21 (s,l H), 11 -97
(s,lH).
Step 3

The product from Step 2 (1.0 g) was added portion-wise to phosphorus oxychloride (18 ml) with stining. The reaction was exotheR""ic. The mixture became yellow with a fine suspension, and was then refluxed for 3 hours. Excess phosphorus oxychloride was evaporated, the mixture was diluted with diethyl ether, and then washed with, ice water and brine, and the organic layer was dried over magnesium sulphate. The solvent was evaporated to give 2,4-dichloro-3-(2,4,6-trifluorophenyI)-[l,S]naphthyridine as a yellow solid (1.0 g, 88%).
1H NMR (CDCI3) 6 ppm: 6.81 (m?2H), 7.61 (dd,lH), 8.60 (dd.lH), 9.17 (dd.lH).
Step 4
The product from Step 3 (0.12 g). isopropylamine (0.3 ml) and .V-ethyl-di/jo-
propylamine (0.10 g) were refluxed in DMF (8 ml) in a sealed tube at 50°C for 17 hours. The
dark coloured reaction mixture was evaporated to give an oil, which was puritled by flash
column chromatography on silica gel (40-60, ethyl acetate/hexane 1/3) to give [2-chloro-3-
(2,4,6-trif]uorophenyl)-[l,8]naphthyridin-4-yl]-isopropylamine as white crystals (0.059.g,
46%), m.p. 193°C.
'H NMR(CDCb) 5 ppm: 1.06 (d,6H), 3.68 (m.lH), 4.04 (m,lH), 6.80 (m,2H), 7.36 (dd,lH),
8.28 (dd,lH), 9.00 (dd,lH)

and [4-chloro-3-(2,4,6-trifluorophenyl)-[l,S]naphthyridin-2-yl]-isopropylamine as yellow crystals, (0.039g, 30%), m.p. 202°C.
'H NMR (CDC13) 5 ppm: 1.24 (d,6H), 4.35 (m,lH), 4.70 (m,lH), 6.93 (m52H), 7.70 (dd,lH), 8.38 (dd,lH), 8.67 (dd,lH).
»
2,4-DichIoro-3-(2,4,6-trifluoro-phenyl)-[l,8}naphthyridine (0.12 g, the product from Example 1, step 3) and morpholine (0.01 ml) were refluxed in DMF (Sml) in a sealed tube at

'H NMR (CDCh) 5 ppm: 3.34 (m.2H), 3.62 (m,2H), 6.90 (m.2H), 7.43 (dd,lH), 8.51 (ddJH), 9.05 (dd,lH).

Starting with 2-amino-5-bromo-nicotinic acid ethyl ester using a process analogous to that described in Example 1, steps 1 to 4, the title compound was synthesized (41%), as yellow crystals, m.p. 202°C.
lH NMR (CDC13) 5 ppm: 1.36 (d,6H), 3.94 (m,lH), 4.25 (m,lH), 7.06 (m,2H), 8.64 (dJH), 9.25 (d,lH).

Step 1
3-Amino-4-pyridinecarboxylic acid (5.52 g) was suspended in ethanol (300ml) at room temperature, with stirring. One equivalent ofDMAP (10.0 g) was added initially and the mixture stirred for 1 hour at room temperature to produce a suspension. A second equivalent ofDMAP was added and the suspension disappeared. EDC (8.0 g) was then added and the reaction stirred at room temperature for 17 hours. The solvent was removed give yellow oil, which was water-soluble. The aqueous fraction was extracted with ethyl

acetate, washed with brine and dried over magnesium sulphate. After evaporation of the solvent a sludge (16.2 g) was obtained which was passed through a plug of si lira gel (40-60) eluting with ethyl acetate, giving a yellow liquid (4.5 g), which by NMR was the desired product ethyl 3-amino-4-pyridinecarboxylate in a ratio of 2:1 with DMAP, and which was used for the next reaction without further purification.
lH NMR (CDC13) 6 ppm: 1.4 (t,3H), 4.4 £q,2h), 5.8 (bs,2H), 7.6 (d,lH), 7.95 (d,lH), 8.2 (s,lH). Step 2
The crude ester from Step I (4.5 g) was dissolved in dry DC1-4 (30 ml), and then pyridine (5.0 ml) added to give a dark brown solution. The stirred solution was cooled in an ice bath, and 2,4,6-trifluorophenylacetyI chloride (3.1 g) in dry DC1-4 (20 ml) added - -dropwise. The reaction mixture was stirred for 6 hours and stood over night. The solvent was removed to give an orange sludge, water added and the solid was dissolved in ethyl acetate. The organic fraction was washed with sodium bicarbonate solution, followed by a small amount of 1M hydrochloric acid solution, then water and dried magnesium sulphate." The ethyl acetate was evaporated to yield a solid (6.5 g), which was purified by flash column chromatography on silica gel (40-60), eluting with ethyl acetate to give ethyl 3-[2-(2,4,6-trifluorophenyl)-acetyIamino]-pyridine-4-carboxylate as a yellow solid (3.2 g). lH NMR (CDCb) 5 ppm: 1.45 (t,3H), 3.8 (fd,2H), 4.45 (q,2H) 6.75 (t,2H), 7.8 (d,2H), 8.45 (d,2H), 10.0 (s,lH), 11.0 (s,lH). Step 3
The product from Step 2 (3.0 g) and potassium carbonate (1.6 g) were stirred in dry DMF (100 ml) at 100°C for 3 hours. The reaction was cooled and the excess DMF evaporated to give a black oil. Water (100ml) was added and then washed with ethyl acetate. The aqueous fraction was filtered and acidified with 2M aqueous hydrochloric acid to neutral pH, and the water was evaporated to give a solid, which was then extracted with methanol. The methanol extract was evaporated to give the crude 3-(2,4,6-trifluorophenyl)-liZ-... [l,7]naphthyridine-2,4-dione as a dark brown crystalline solid (2.0 g), which was used for the next reaction without further purification. 'H NMR (CDCI3) 5 ppm: 6.8 (t, 2H), 7.95 (m:2H), 8.2 (d,lH). Step 4

phosphorus oxychloride was evaporated to give a brown oil, which was dissolved in diethyl ether (100 ml) and washed with cold water. The ether layer was separated, dried over magnesium sulphate and evaporated to give a sludge (0.150 g),which was purified by flash column chromatography on silica gel (40-60), eluting with diethyl ether, to give 2.4-dichIoro-3-(2.4,6-trifluorophenyI)-[I,7]naphthyndine as an oil (0.10 g) which solidified on standing.
'H NMR (CDC13) 5 pom: 6.9 (t,2H), S.05 (dJH), 8.8 (d,iH), 9.5 (s,lH), .\f 329 Step 5
The product of Step 4 (0.09 g) was dissolved in DC1-4 (3.0 ml) and transferred to a sealed tube containing isopropylamine (I.OmI), N-ethyl-dizsopropylarnine (0.07 g) and dimethylacetamide (1.0ml). The vessel was sealed and gently waR""ed to 60°C for 10 hours. The reaction was cooled and evaporated to give an oil, which was purified by flash column chromatography on silica gel (40-60) eluting with diethyl ether. Two isomers were obtained: [2-chloro-3-(2,4,6-trifIuoro-phenyl)-[l,7]naphthyridin-4-yl]-isopropylamine as an oil (0.028 -
g)
1HNMR (CDC13) 5 ppm: 1.1 (d, 6H), 3.75 (m,lH), 4.3 (bd,lH), 6.9 (t,2H), 7.7.5(d,lH), 8.6
(d,lH), 9.35(s,lH).
The second isomer, [4-chloro-3-(2,4J6-trifluoro-phenyl)-[l,7]naphthyridin-2-yl]-
isopropylamine, was obtained as a mixture with the starting dichloro compound, and was
reacted again and purified by chromatography as described above to give the compound as
an oil.
1H NMR (CDC13) 5 ppm: 1.1 (d,6H), 4.25 (bd,lH), 4.5 (m,lH), 6.9 (t,2H), 7.75 (d,lH), S.4

Step 1
Ethyl 4-aminopyridine-3-carboxyIate (1.5 g) was dissolved in dry toluene (50 ml) to give a pale yellow solution, and 2-chloro-6-fluorophenylacetyl chloride (1.S7 g) in dry DC1-4 (13 ml) was added. The bright yellow reaction mixture was heated at 95°C for 4 hours. The brownish solution was cooled to ambient temperature, ethyl acetate was added and the mixture was washed with water, brine, and then dilute hydrochloric acid, and the organic layer was dried over magnesium sulphate. The solvent was evaporated to yield a brown solid, which was purified by flash column chromatography on silica gel (40-60) eluting with hexane:ethyl acetate 1:1, to yield pure ethyl 4-(2-(2-chloro-6-fluorophenyl)acetamido)-pyridine-3-carboxylate as a yellow solid (1.4 g), m.p. 114-116 QC
'HNMRfCDCWSppm: 1.32 (t,3H), 3.91 (s,2H), 4.28 (q,2H), 7.02 (m,lH), 7.21 (m,2H), 3.51 (m,2H), 9.07 (s,lH), 11.2 (s,lH). . Step 2
The product from Step 1 (1.0 g) was dissolved in DMF (15 ml) and solid potassium carbonate (0.S g) was added. The resulting pale yellow solution was heated at 100°C for 4 hours. The reaction mixture was cooled and evaporated to give a yellow solid (3 g), which was then acidified with dilute hydrochloric acid. The resulting white suspension was filtered and collected, washed with ether and dried to give 3-(2-chloro-6-fluorophenyl)-l/f-[l,6] naphthyridine-2,4-dione (0.8 g), m.p. 249 °C.
1H NMR (d6-DMSO) 5 ppm: 6.80 (d,lH), 7.00 (m,lH), 7.13 (m,2H), 8.10 (d,IH), 8.62 (d,lH), 12.11 (s,lH). Step 3
The product from Step 2 (0.70 g) was dissolved in 1,2-dichloroethane (15 ml). DMF (2 ml) and phosphorus oxychloride (2 ml) were added with stirring. The pale yellow-suspension was then refluxed for 4 hours. The reaction mixture was cooled to ambient temperature, diluted with diethyl ether,.and then washed with water to give 2>4-dichIoro-3-(2-chloro-6-fluorophenyl)-l,6-naphthyridine as a light yellow solid (0.38 g). H NMR (CDC13) S ppm: 7.12 (td,lH), 7.32 (d,lH), 7.4.1 (dd,lH), 7.S7 (bs,lH), 8.88 (bs,l£). 9.40(bs,lH).
Step 4
The product from Step 3 (0.10 g) was dissolved in DMF (2 ml). Sec-butylamine (0.2

chromatography on silica gel (40-60) in ethyl acetaterhexane 1:1 to give N-sec-butyl-4-chloro-3-(2-chloro-6-fIuorophenyl)-l,6-naphthyridin-2-amineas a light yellow gum (0.0 8g). 'H NMR (CDCI3) 5 ppm: 0.08 (m,3H), 1.10 (t,3H), 1.4S (m,2H). 4.18 (m,lH), 4.28 (m,lH). 7.10 (m,lH), 7.36 (UH), 7.40 (m,lH), 8.52 (d,lH), 9.20 (s,lH). 9.30 (s,lH).

Step 1
2,4-Dichloro-3-(2-chloro-6-fluorophenyl)-l,6-naphthyridine (0.20 g) was dissolved in sulpholane (2 ml). Potassium fluoride (0.11 g) was added and the mixture was heated in a sealed tube at 120°C for 14 hours. The honey coloured reaction mixture was,.cooled to ambient temperature, diluted with diethyl ether, and then washed extensively with water. After evaporation of the solvent the resulting light yellow oil was purified by flash column chromatography on silica gel (40-60) eluting with ethyl acetate:hexane 1:4, to give 3-(2-chloro-6-fluorophenyl)-2,4-difluoro-l,6-naphthyridine as a light yellow solid (0.10 g). 1H NMR (CDCb) 5 ppm: 7.06 (m,lH), 7.20 (m,IH), 7.31 (m,IH), 8.53 (d,lH), 9.20 (d,lH). Step 6
The product from Step 1 (0.10 g) was dissolved in DMF (2 ml). Sec-butylamine (0.1
ml) and DMAP (0.001 g) were added and the mixture was stirred in a sealed tube at ambient
temperature for 18 hours. The brown reaction mixture was diluted with diethyl ether, washed
with brine and dried over sodium sulphate. After evaporation of the solvent the resulting
yellow gum was purified by flash column chromatography on silica gel (40-60) in ethyl
acetate:hexane 1:3 to give N-sec-butyl-3-(2-chloro-6-fluorophenyl)-2-fluoro-l,6-
naphthyridin-4-amine as a darlc yellow solid (0.06 g).
1H NMR (CDCb) 5 ppm: 0.082 (m,3H), 1.20 (m,3H), 1.34 (m,2H), 3.02 (m,IH), 5.0S (m,lH), 7.10 (d,lH), 7.28 (m,lH), 7.38 (m,lH), 8.58 (d,lH), 9.20 (s,lH), 9.30 (s1H).

Step 1
3-Amino-2-picoIinic acid (4.14 g) was suspended in ethanol (100 ml) at room temperature with stirring. DMAP (3.7 g) was added and the reaction was stirred for 1 hour at room temperature. A further equivalent of E5MAP (3.7 g) was added and the suspension
disappeared, and then EDC (5.80 g) was added and the reaction was stirred at room temperature for 17 hours. The ethanol was evaporated to give a dark oil, water was added and the mixture was extracted with ethyl acetate, washed with brine and dried over magnesium sulphate. Evaporation of the solvent gave ethyl 3-amino-2-picolinate as a solid (6.5 g), mixed in a 2:1 ratio with DMAP.
1H NMR (CDC13) Sppm: 1.4 (t,3H), 4.45 (q,2h), 5.S (bs,2H), 7.05 (d,iH), 7.2 (dd,lH), 8.05 (fd,lH). Step 2
The crude product from Step 1 (6.5 g) was dissolved in dry DC1-4 (150 ml), and triethylamine (5.0 ml) was added to give a dark brown solution. The reaction was stirred in an ice bath, and 2,4,6-trifluorophenylacetyl chloride (8.0 g) in dry DC1-4 (20 ml) was added dropwise. The mixture was stirred for 6 hours and stood for 18 hours. The solvent was evaporated to give an orange sludge, water was added, and the solid was dissolved in ethyl acetate, which was washed with sodium bicarbonate solution and water, and then dried over magnesium sulphate. The ethyl acetate was evaporated to yield a solid (8.5 g), which was purified by flash column chromatography on silica gel (40-60), eluting with ethyl acetate to give Ksolid which was triturated with diethyl ether to give ethyl 3-[2-(2,4,6-trifIuorophenyI)-acetylamino]-pyridine-2-carboxylic acid ethyl ester as a white solid (3.0 g). lH NMR (CDCI3) 5 ppm: 1.45 (t,3H), 3.85 (d,2H), 4.5 (q,2H) 6.75 (t,2H), 7.5 (m,lH), 8.45

Step 3
The product from Step 2 (0.80 g) and potassium carbonate (0.40 g) were stirred in dry DMF (10 ml) at 100°C for 6 hours. The reaction mixture was cooled, stood for 18 hours and the DMF was evaporated to give a solid. This was diluted with water (1 ml), acidified to neutrality and the water was evaporated to give a solid, which was then extracted with methanol. The methanol was evaporated to give 3-(2,4,6-trifluorophenyl)-lH'-[l,5]naphthyridine-2,4-dione as a peach coloured solid (0.15g), which was used without further purification.
'H NMR (CD3OD) 5 ppm: 6.88 (m,2H), 7.45 (m,lH), 7.72 (m,lH), 8.10 (d,lH). Step 4
The product from Step 3 (0.20 g) was added to phosphorus oxychloride (5.0 ml) and the suspension stirred and brought to S5QC for 5 hours. The phosphorus oxychloride was evaporated to give a brown oil which was dissolved in DC1-4 (100 ml) and washed with cold water. The DC1-4 layer was separated, dried over magnesium sulphate and the solvent was evaporated to give 2,4-dichloro-3-(2,4,6-trifluorophenyl)-[l35]naphthyridine as a solid (0.070
8)- lH NMR (CDCh) 5 ppm: 6.9 (t,2H), 7.9 (m,lH), 8.5 (d.IH), 9.2 (bs,lH).
Step 5
The product from Step 4 (0.070 g) was dissolved in propylamine (1.0 ml) and waR""ed in a sealed tube to 60°C for 2 hours. Thepropylamine was evaporated and the residue was purified by flash column chromatography on silica gel (40-60) eluting with diethyl ether to give [2-chloro-3-(2,4,6-trifluorophenyl)-[l,5]naphthyridin-4-yl]-isopropylamine as a yellow gum (0.009 g).
1H NMR (CDCh) 5 ppm: 1.1 (d,6H), 3.25 (m,lH), 6.8 (t,2H), 7.6 (dd,lH), 8.35 (d,lH), 8.7 (d,lH).

Compounds were tested in a leaf disk assay, with methods described below. Test compounds were dissolved in DMSO, and diluted into water to 200 ppm. Erysiphe graminisf.sp. hordei (barley powdery mildew): barley leaf segments were placed on agar in a 24-weIl place and sprayed with a solution of the test compound. After allowiftg' -to dry completely, for between 12 and 24 hours, the leaf disks were inoC1-6lated with a spore suspension of the fungus. After appropriate inC1-6bation the activity of a compound was

1.
W, X and Y are all CH and Z is N; R is halo;
R1 is an/I, heteroaryl, morphciino, piperidino or pyrrolidine; R2 is NR3RR3 and R4 are independently H, C1-8alkyl, C2-9alkenyl, C2-8 alkynyl, aryl,
aryl(Ci.8)alkyl, C3-8 cycloalkyl, C3-9cycloalkyl(C1-6)alkyl, heteroaryl, hetero-
aryl(Ci.8)alkyl, NR5Re, provided that not both R3 and R4 are H or NR5R6, or
R3 and R4 together form a C3-7 alkylene or C3-7 alkenylene chain optionally
substituted with one or more C,.4 alkyl or C1-4 alkoxy groups, or,
together with the nitrogen atom to which they are attached, R3 and R4 form a
morpholine, thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring
or a piperazine or piperazine /V-(C1-4)alkyl (especially N-methy) ring; and
R5 and R6 are independently H, C1-8alkyl, C2-8alkenyl, C2-3 alkynyl, aryl,
aryl(Cva)alkylt C3-8cycl6alkyl, C3-8cycioalkyl(CV5)alkyl, heteroaryl or
hetero-aryl(Ci.3)alkyl;
any of the foregoing alkyl, alkanyl, alkynyl or cycloalkyl groups or moieties (other
than for R8) being optionally substituted with halogen, cyano, C1-6 alkoxy, C1-6al-
kylcarbonyl, C1-6alkoxycarbonyl, C1-6 haloalkoxy, C1-6alkylthio, tri(C1-4)alkylsilyl,
C1-6alkylamino or C1-6 dialkylamino,
any of the foregoing morpholine, thiomorpholine, piperidine, piperazine and
pyrrolidine rings being optionally substituted with C1-4 alkyl (especially methyl), and
any of the foregoing aryl or heteroan/l groups or moieties being optionally substituted
with one or more substituents selected from halo, hydroxy, mercapto, C1-6 alkyl,
C2-6alkenyl, C2-6alkynyl, C1-6 alkoxy, C2-6alkenyloxy, C2-6 alkynyloxy, halo(C1-6)aIkyl,
halo(C1-6)alkoxy, C1-6 alkylthio, halo(C1.5)alkylthio, hydroxy(C1.5)alkyl,
C1-4alkoxy(C1-6)alk'yl, C3-6 cycloalkyl, C3-6-cyc!oalkyl(C1-4)alkyl, phenoxy, benzyloxy,
benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, -NR'"R"",
-NHCOR",-NHCONR'"R",-CONR"'Rm,-S02R",-OS02R",-COR",-CR"'=NR"" or
-N=CR"'R"", in which R'" and R,m are independently hydrogen, C,.4 alkyl, halo-
(Ci-a)alkyl, C1-6aikoxy, halo(C1-4)alkoxy, C1-4alkylthio, C3-6 cycloalkyl, C3-5 cycloalkyl-

(C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being opt;enally substituted with halogen, C1-4aikyl or C1-4 alkoxy.
A compound according claim 1 wherein
R3 is C1-8 alky! haIo(C1-8)alkyl, hycroxyfC1-8alkyl, C1-6 alkoxy(C1-8)alky:. C1-4alkoxy-
ha!o(C1-8)alkyi. tri(C1-4)alkylsilyl(C1-8)alkyl, C1-4alkylcarbcnyl(C1-8)alkyi. C1-4 alkyl-
carbonylhalo(C1-8)alkyl, phenylC1-4alkyl, C2-8 aikenyl, ha!o(C2.8)alkenyl. C2-8alkynyl,
C3-8 cycioalkyl optionally substituted with chloro, fluoro or methyl, C3-8 cycloal-
kyl-(C1-6)alkyl, phenylamino, piperidino or morpholino, the phenyl ring ex phenyfalkyl
or phenylamino being optionally substituted with one, two or three substituents
selected from halo, C1-6 alkyl, haio(C1-4)alkyl, C1-4 alkoxy and halo(C1-4)alkoxy; and
R4 is H, C1-4aikyl, halo(C1-4)alkyl or amino, or
R3 and R4 together form a C3-7 alkylene or C3-7 alkenylene chain optionally
substituted with methyl, or,
together with the nitrogen atom to which they are attached, R3 and R4 form a
morpholine, thiomorphoiine, thiomorpholine S-oxide or thiomorpholine S-dioxide ring
or a piperazine or piperazine N-(C1-4)alkyl (especially N-methyl) ring, in which the
morpholine or piperazine rings are optionally substituted with methyl.
A compound according to claiml or 2 claims wherein
R1 is phenyl optionally substituted with from one to five halogen atoms or with from one to three substituents selected from halo, C1-4alkyl, halo(C1-4)alkyl, C1-6 alkoxy or halo(C1-4)alkoxy, pyridyl optionally substituted with from one to four halogen atoms or with from one to three substituents selected from halo, C1-4alkyl, halo(C1-4)aIkyl, C1-4alkoxy or halo(C1-4)alkoxy, 2- or 3-thienyl optionally substituted with from one to three halogen atoms or with from one to three substituents selected from halo, C1-4alkyl, halo(C1-4)alkyl,C1-4alkoxy or halo(C1-4)alkoxy, or piperidino or morpholino both optionally substituted with one or two methyl groups.
A compound according to claim 3 wherein R1 is 2,6-difluorophenyl, 2-fiuoro-6-chloro-phenyl, 2,5,6-trifluorophenyl, 2,4,6-trifIuorophenyl, 2,6-difluoro-4-methoxyphenyl or pentafluorophenyl.
A compound according to claim 1 wherein W, X and Y are all CH and Z is N;
R is halo, R1 is aryl, heteroaryl, morpholino, piperidino or pyrrolidino; R2 is NR3R4;
R3 and R4are independently H, C1-8aikyl,C2-8 aikenyl,C2-8 alkynyl, an/l,

ar/KC1-8aikyl, C3-8cycloalkyl, C3-8cycloalkyl(C1-6)alkyl. heteroaryl, hetero-aryC1-8alkyl, NR5R6, provided that not both R3 and R4 are H or NR5R6. or R3 and R4 together foR"" a C3_7 alkylene or C3-7 alkenylene chain optionally substituted with one or more C1-4aikyl or C1-4 alkoxy groups, or, together with the nitrogen atom to which they are attached, R° and R4 r'oR"" a morpholine, thiomorpholine, thiomorpholine S-oxide or thiomcrphoiine S-dioxide ring or a piperazine or piperazine N-(C1-4)aikyl (especially N-methy!) ring; and R5 and R6 are independently H, C1-8aikyl, C2-8 alkenyl,C2-8 aikynyl, aryl(Ci:8)alkyl, C3-8 cycloalkyl, C3-8cycloalkyl(C1-6)alkyl, heteroaryl orhetero-aryC1-8alkyl;
any of the foregoing aikyl, alkenyl, aikynyl or cycloalkyl groups or moieties being optionally substituted with halogen, cyano, C1-6alkoxy, C1-4alkylcarbonyl, C1-6alkoxy-carbonyl, C1-6 haloalkoxy, C1-6 alkylthio, tri(C1-4)alkylsilyl, C1-6alkyfamino or C1-6alkylamino, any of the foregoing morpholine, thiomorpholine, piperidine, piperazine and pyrrolidine rings being optionally substituted with C1-4 aikyl (especially methyl), and any of the foregoing aryl, heteroaryl, aryloxy or heteroan/l groups being optionally substituted with one or more substituents selected from halo, hydroxy, mercapto, C1-6 aikyl, C2-6 alkenyl, C2.5alkynyl, C1-6 alkoxy, C2-6 afkenyloxy, C2-6alkynyloxy, halo(C1-6)alky(, halo(C1-6)alkoxy, C1-6 alkylthio, halo(d-s)a!kyithio, hydroxy(C1-6)alkyl, C1-4alkoxy(C1-6)aikyl, C3-6cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, -NFTR"", -NHCOR"', -NHCONR'"R"", -CONR""R'",-S02R",-OS02R"", -COR"", -CR"'=NR"" or -N=CR'"R'",in which R'" and R"" are independently hydrogen, C1-4alkyl, halo(C1-4)alkylT C1-4 alkoxy, halo(C1-4)alkoxy, C1-4 alkylthio, C3.5 cycloalkyl, C3-6 cydoalkyl(d-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4aikyl or C1-4 alkoxy.
A compound according to claim 1 wherein W, X and Y are all CH and Z is N;
R is halo; R1 is aryl, heteroaryl, morphofino, piperidino or pyrrolidine; R2 is NR3R4,
R3 is C1-4aLkyl, halo(C1-4)alkyl, C2-4alkenyl, C3-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl
or phenylamino in which the phenyl ring is optionally substituted with one, two or
three substituents selected from halo, C1-4 aikyl, halo(C1-4)alky(, C1-4 alkoxy and -
halo(C1-4)alkoxy; and R4 is H,C1-4aikyl or amino, or
R3 and R4 together foR"" a C4-6 alkylene chain optionally substituted with C1-4 aikyl or
C1-4 alkoxy, or
together with the nitrogen atom to which they are attached, R3 and R4 foR"" a

morpholine, thiomorpholine, thiomorphofine S-oxide or thiomorpholine S-dioxide ring or a piperazine or piperazine N-(C1-4)alkyl (esoecially /V-methyl) ring; any of the foregoing alkyl, alkenyl, alkynyl or cycloalkyl groups or moieties being optionally substituted with halogen, cyano, C1-6 atkoxy, C1-6alkyfcarbcnyl, C1-6alkoxy-carbcnyl, C1-6 haloalkoxy, C1-6 alkylthio, tri(C1-4)alkylsilyl. C1-6 alkylamino or C1-6dialkylamino, any of the foregoing morphciine, thiomorpholine, piceridine, piperazine and pyrrolidine rings being optionally substituted with C1-6 alkyl (especially methyl), and any of the foregoing an/I or heteroan/f groups or moieties oeing optionally substituted with one or more substituents selected from halo, hydroxy, mercapto, C1-8 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C2-6 alkenyloxy, C2-6alkynyloxy, halo(C1-6)alky(, halo(C1-6)alkoxy,C1-6alkylthio, halc(C1-4;alkylthio, hydroxy(C1-6)alkyl, C1-4alkoxy(C1-6)alkyl, C3_6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, -NR'"R"", -NHCOR'", -NHCONR'"R'",-CONR'"R""', -S02R",-OS02R"', -COR"', -CR'"=NR"" or -N=CR""R'",in which R'" and R"" are independently hydrogen, C1-4alkyl, halo(Ci-j)alkyl, C1-4alkoxy, halo(C1-4)alkoxy, C1-4 alkylthio, C1-6 cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4 alkyl'or C1-4 alkoxy.
A compound according to claim 1 wherein one of W, X and Y are all CH and Z is N;
R is halo; Rl is optionally substituted phenyl; R2 is NR3R4,
R3 and R4 are independently H, C1-8alkyl, C2-8 alkenyl,C2-8 alkynyl, an/l,
aryl(C1-8)alkylf C1-6 cycloalkyl, C3-8cycloalkyl(C1-4)alkylf heteroaryl, heterc-
aryl(C1-8)alkyl, NR5R6, provided that not both R3 and R4 are H or NR5R5, or
R3 and R4 together foR"" a C3-7 alkylene or C3-7 alkenylene chain optionally
substituted with one or more C1-4 alkyl or C1-4 alkoxy groups, or,
together with the nitrogen atom to which they are attached, R3 and R4 foR"" a
morpholine, thiomorpholine, thiomorpholine S-oxide or thiomorpholine S-cioxide ring
or a piperazine or piperazine N-(C1-4)alkyl (especially N-methyl) ring; and
R5 and R6 are independently H, C1-8alkyl, C2-8 alkenyl, C2-3 alkynyl, an/l,
aryl(C1-8)alkyl, C3-8 cycloalkyl, C3-8cycloalkyl(C1-6)alkyl, heteroaryl or hetero-
aryf(C1-8)alkyl;
any of the foregoing alkyl, alkenyl, alkynyl or cycloalkyl groups or moieties being
optionally substituted with halogen, cyano, C1-6 alkoxy, C1-6alkylcarbonyl, C1-6al-
koxycarbonyl, C1-6 haloalkoxy, C1-6 alkylthio, tri(C1-4)alkylsilyl, C1-6 alkylamino or
C1-6dialkylamino; any of the foregoing morpholine, thiomorpholine, piperidine,

piperazine and pyrrolidine rings being optionally substituted withC1-4aikyl (especially methyl), and any of the foregoing ar/I or heteroaryl groups or moieties, including the phenyl group of R,being ootionally substituted with one or more substituents selected from halo, hydroxy, mercapto, d-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-8alkoxy, C2-6 alkenyloxy, C2-6 alkynyloxy, halo(C1-6)alkyi, halo(C1-8)aikoxy, C1-8aikylthio, halo(C1-6)alkylthio, hydroxy(C1-8)alkyl, C1-4alkoxy(C1-6)alkyl, C3-6cycloalkyl, C3-6 cycloalkyl(C1-4)alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, nitro, -NR'"R"", -NHCOR'", -NHCONR""R"", -CONRn,R'",-S02R",-OS02R",-COR'", -CR",=NR"or-N=CR""R", in which R"" and R"" are independently hydrogen,C1-4alkyl, halo(C1-6)alkyl,C1-4alkoxy, halo(C1-4)alkoxyf C1-4 alkylthio, C3-6 cycloalkyl, d-6 cycloalkyl(C1-4)alkyl, phenyl or benzyl, the phenyl and benzyl groups being optionally substituted with halogen, C1-4alkyl orC1-4alkoxy.
A compound according to claim 1 wherein W, X and Y are all CH and Z is N; R is halo; R1 is phenyl optionally substituted with from one to five halogen atoms or with from one to three substituents selected from halo, C1-4 alkyl, halo(C1-4)alkyl, C1-4alkoxy or haIo(C1-4)alkoxy, pyridyl optionally substituted with from one to four halogen atoms or with from one to three substituents selected from halo,C1-4alkyl, halo(C1-4)alkyl, C1-4alkoxy or halo(C1-4)alkoxy, 2- or 3-thienyl optionally substituted with from one to three halogen atoms or with from one to three substituents selected from halo, C1-4alkyl, ha!o(C1-4)alkyl,C1-4alkoxy or halo(C1-4)alkoxy, or piperidino or morpholino both optionally substituted with one or two methyl groups; R2 is NR3R4; R3 is C1-8 alkyl, halo(C1-8)alkyl, hydroxy(C1-8)aIkyl,C1-4aIkoxy(C1-8)alkyl,C1-4alkoxy-halo(C1-8)alkylt tri(C1-4)alkylsilyl(d-6)alkyl,C1-4alkyicarbonyl(C1-8)alkyl, C1-4 alkyl-carbonylhalo(C1-4)alkyl, pheny!(C1-4)a!kyf, C2-8 alkenyl, haIo(C2_8)alkenyl, C2-8 alkynyl, C3-8 cycloalkyl optionally substituted with chloro, fluoro or methyl, C3.3 cycloalkyl-(C1-4)alkyl, phenylamino, piperidino or morpholino, the phenyl ring of phenylalkyl or phenylamino being optionally substituted with one, two or three substituents selected from halo,C1-4alkyl, ha!o(C1-4)alkyl,C1-4alkoxy and halo(C1-4)alkoxy; and R4 is H,C1-4alkyl, halo(C1-4)alkyl or amino, or v R3 and R4 together foR"" a C3-7 alkylene or C3-7 alkenylene chain optionally substituted with methyl, or,
together with the nitrogen atom to which they are attached, R3 and R4 foR"" a morpholine, thiomorpholine, thiomorphcline S-oxide or thiomorpholine S-dioxide ring

or a piperasne or piperaan© N-(C1-4)alkyl (especially N-methyl) ring, in which the morpholine or piperazine rings ara optionally substituted with methyl.
A compound according to claim 1 wherein one of W, X and Y are all CH and Z is N; R is halo; R1 is phenyl optionally substituted with from one to five halogen atoms cr with from one to three substituents selected from halo,C1-4aJkyi, halo(C1-4)alkyi, C1-6alkcxy cr hafo(C1-6)alkoxy; R2 is NR3R3; R3 is C1-4alkyl. halo(C1-6)aryI, C1-6alkenyl, C3-8 cycloalkyl, C1-6 cydoalkyl(C1-4)alkyl or phenylamino in which the phenyl ring is optionally substituted with one, two or three substituents selected from halo, C1-4 alkyl, halo(C1-4)alky|, C1-4 alkoxy and haIo(C1-4)alkoxy; and R4 is H, r amino, or R3 and Rd together foR"" a C4-6alkylene cnain optionally substituted with methyl, or, together with the nitrogen atom to which they are attached, R3 and R4 foR"" a morpholine ring.
A process for preparing a compound of the general foR""ula (T)-according to claim 1 whsrein one of R is chloro orfluoro and R2 is NR3R4 and W, X, Y, Z, R,R3 and R4 are as defined in claim 1, which comprises reacting an amine of the general foR""ula NR3R4 with a compound of the general foR""ula (6) or (13):

wherein W, X, Y, Z and R1 are as defined in dafml.
A plant fungicidal composition comprising a fungicidally effective amount of a compound as defined in claim 1 and a suitable carrier or diluent therefor.

A method cf combating or controlling phytcpathogenic fungi which comprises
applying to a plant, to a saed of a plant to t'no loC1-4s of ths plant or ssad or to soil or
to any other plant growth medium, a fungicidally effective amount of a compound
according to claim 1 or a composition according to claim 12.

Documents:

1355-chenp-2005 abstract duplicate.pdf

1355-chenp-2005 claims duplicate.pdf

1355-chenp-2005 description (complete) duplicate-1.pdf

1355-chenp-2005 description (complete) duplicate.pdf

1355-chenp-2005-abstract.pdf

1355-chenp-2005-claims.pdf

1355-chenp-2005-correspondnece-others.pdf

1355-chenp-2005-correspondnece-po.pdf

1355-chenp-2005-description(complete).pdf

1355-chenp-2005-form 1.pdf

1355-chenp-2005-form 3.pdf

1355-chenp-2005-form 5.pdf

1355-chenp-2005-form18.pdf

1355-chenp-2005-pct.pdf

1355-chenp.rtf

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Patent Number

224490

Indian Patent Application Number

1355/CHENP/2005

PG Journal Number

49/2008

Publication Date

05-Dec-2008

Grant Date

16-Oct-2008

Date of Filing

21-Jun-2005

Name of Patentee

SYNGENTA LIMITED

Applicant Address

EUROPEAN REGIONAL CENTRE, PRIESTLEY ROAD, SURREY RESEARCH PARK GUILDFORD, SURREY GU2 7YH,

Inventors:

#	Inventor's Name	Inventor's Address
1	WILLIAMS, JOHN	SYNGENTA LIMITED, JEALOTTS HILL INTERNATIONAL RESEARCH CENTRE, BRACKNELL, BERKS RG42 6EY,
2	CROWLEY, PATRICK, JELF	SYNGENTA LIMITED, JEALOTTS HILL INTERNATIONAL RESEARCH CENTRE, BRACKNELL, BERTS RG42 6EY,
3	DOBLER, MARKUS	NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH INC., 250 MASSACHUSETTS AVENUE, CAMBRIDGE, MA 02139,
4	MUELLER, URS	SYNGENTA CROP PROTECTION AG, SCHWARZWALDALLEE 215, CH-4058 BASEL,

PCT International Classification Number

C07D471/04

PCT International Application Number

PCT/GB03/05248

PCT International Filing date

2003-12-03

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	0230018.4	2002-12-23	U.K.