Indian Patents
Title of Invention

"SUBSTITUTED PHENYLKETOENOLS COMPOUNDS OF THE FORMULA (I)"
Abstract Substituted phenylketoenols compounds of the formula (I) wherein V represents hydrogen, halogen, alkyl or alkoxy, W represents cyano, nitro, halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenoalkyl, halogenoalkoxy, respectively optionally substituted phenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio, X represents hydrogen, halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano, nitro or respectively optionally substituted phenyl, phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio, Y represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano or nitro, Z represents halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, hydroxyl, cyano, nitro or respectively optionally substituted phenoxy, phenylthio, 5- to 6-membered hetaryloxy, 5- to 6-membered hetarylthio, phenylalkyloxy or phenylalkylthio, Y and Z represent together with the carbon atoms that they are attached to an optionally substituted cycle which is optionally interrupted by one or more heteroatoms, V, X and W having one of the above- mentioned meanings, or W and Z represent together with the carbon atoms that they are attached to an optionally substituted cycle which is optionally interrupted by one or more heteroatoms, V, X and Y having one of the above- mentioned meanings.
Full Text The present invention relates to substituted phenylketoenols compounds of the formula (I).
The invention relates to novel phenyl-substituted cyclic ketoenols, a plurality of processes and intermediates for their preparation and their use as pesticides and herbicides.
It has already been disclosed that certain phenyl-substituted cyclic ketoenols are active as insecticides, acaricides and/or herbicides.
Pharmaceutical properties of 3-acyl-pyrrolidine-2,4-diones have previously been described (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)). Further¬more, N-phenylpyrrolidine-2,4-diones have been synthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985, 1095). Biological activity has not been disclosed for these compounds.
EP-A-0 262 399 and GB-A-2 266 888 disclose compounds (3-aryl-pyrrolidine-2,4-diones) of a similar structure, for which, however, no herbicidal, insecticidal or acaricidal activity has been disclosed. Unsubstituted, bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-355 599 and EP-A-415 211) and substituted mono¬cyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077) with herbicidal, insecticidal or acaricidal activity are known.
Polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-442 073) and lH-aryl-pyrrolidine-dione derivatives (EP-A-456 063, EP-A-521 334, EP-A-596 298, EP-A-613 884, EP-A-613 885, DE 44 40 594, WO 94/01 997, WO 95/01 358, WO 95/20 572, EP-A-668 267 and WO 95/26 954) are also known.
It is known that certain substituted Δ3-dihydrofuran-2-one derivatives have herbicidal properties (cf. DE-A-4 014 420). The synthesis of the tetronic acid derivatives used as starting materials (such as, for example, 3-(2-methyl-phenyl)-4-hydroxy-5-(4-fluorophenyl)-Δ3 -dihydrofuran-2-one) is likewise described in DE-A-4 014 420. Compounds of similar structure without details of an insecticidal and/or acaricidal activity are known from the publication Campbell et al., J. Chem. Soc, Perkin Trans. 1, 1985, (8) 1567-76. Furthermore, 3-aryl-Δ3-dihydrofuranone derivatives having herbicidal, acaricidal and insecticidal properties are disclosed in EP-A-528 156 and EP-A-0 647 637. 3-Aryl-Δ3-dihydrothiophen-one derivatives are known (WO 95/26 345).

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Certain phenyl-pyrone derivatives unsubstituted in the phenyl ring have already been disclosed (cf. A.M. Chirazi, T. Kappe and E. Ziegler, Arch. Pharm. 309, 558 (1976) and K.-H. Boltze and K. Heidenbluth, Chem. Ber. 9J_, 2849), a possible utility for these compounds as pesticides not being indicated. Phenyl-pyrone derivatives substituted in the phenyl ring and having herbicidal, acaricidal and in-secticidal properties are described in EP-A-588 137.
Certain 5-phenyl-l,3-thiazine derivatives unsubstituted in the phenyl ring have already been described (cf. E. Ziegler and E. Steiner, Monatsh. 95, 147 (1964), R. Ketcham, T. Kappe and E. Ziegler, J. Heterocycl. Chem. 10, 223 (1973)), a possible utility as pesticides not being indicated for these compounds. 5-Phenyl-1,3-thiazine derivatives substituted in the phenyl ring and having herbicidal, acaricidal and insecticidal activity are described in WO 94/14 785.
However, the acaricidal and insecticidal activity and/or spectrum of action, and/or the toleration of these compounds by plants, in particular by crops, is not always satisfactory.
There have now been found a novel compounds of the (Formula Removed)


in which
V represents hydrogen, halogen, alkyl or alkoxy,
W represents cyano, nitro, halogen, alkyl, alkenyl, alkinyl, alkoxy, halogeno-alkyl, halogenoalkoxy, respectively optionally substituted phenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio,
X represents hydrogen, halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano, nitro or respectively optionally substituted phenyl, phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio,

Lg_A_3.1.661 -Foreign Countries
Y represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano or nitro,
Z represents halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, hydroxyl, cyano, nitro or respectively optionally substituted phenoxy, phenylthio, 5- to 6-membered hetaryloxy, 5- to 6-membered hetarylthio, phenylalkyloxy or phenylalkylthio, or
Y and Z represent together with the carbon atoms that they are attached to an
optionally substituted cycle which is optionally interrupted by one or more hetero atoms, V, X and W having one of the abovementioned meanings, or
W and Z represent together with the carbon atoms that they are attached to an
optionally substituted cycle which is optionally interrupted by one or more heteroatoms, V, X and Y having one of the abovementioned meanings,
Het represents one of the groups
A represents hydrogen, respectively optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, respectively saturated or unsaturated and optionally substituted cycloalkyl or hetero-cyclyl or respectively optionally halogen-, alkyl-, halogenoalkyl-, alk-oxy-, halogenoalkoxy-, cyano- or nitro- substituted aryl, arylalkyl or hetaryl,
B represents hydrogen, alkyl or alkoxyalkyl, or
A and B represent together with the carbon atom that they are attached to a saturated or unsaturated optionally substituted carbocycle or hetero-cycle,
D represents hydrogen or an optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl, saturated or unsaturated heterocyclyl, arylalkyl, aryl, hetarylalkyl or hetaryl, or
A and D represent together with the atoms that they are attached to a respectively optionally substituted carbocycle or heterocycle,
G represents hydrogen (a) or one of the groups
in which,
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulphur,
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M represents oxygen or sulphur,
R1 represents respectively optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioaikyl or polyalkoxyalkyl or respectively optionally halogen-, alkyl- or alkoxy- substituted cycloalkyl or heterocyclyl or respectively optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R2 represents respectively optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl or respectively optionally substituted cycloalkyl, phenyl or benzyl,
R\ R4 and R3 each represent independently of one another respectively
optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylarnino, alkylthio, alkenylthio or cycloalkylthio or respectively optionally substituted phenyl, benzyl, phenoxy or phenylthio,
R'1 and R7 each represent independently of one another hydrogen, respectively optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl or respectively optionally substituted phenyl or benzyl, or represent together with the N-atom that they are attached to an optionally oxygen- or sulphur- containing and optionally substituted cycle,
excluding the following compounds

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The compounds of the formula (I) can also be present, depending on the nature of the substituents, as geometric and/or optical isomers or isomer mixtures of differing composition which, if appropriate, can be separated in a customary manner. Both the pure isomers and the isomer mixtures, their preparation and use, and compositions containing them are part of the subject matter of the present invention. In the following, for simplicity, however, compounds of the formula (I) are always referred to, although both pure compounds and, if appropriate, mixtures having different proportions of isomer compounds are intended.
Including the meanings (1) to (5) of the group Het, the following principal structures (1-1) to (1-5) result:
Lg-A..^ll-661-Foreign Countries
A, B, D, G, V, W, X, Y and Z are each as defined above
Including the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following principal structures (I-l-a) to (I-l-g) result if Het represents the group (I)
(Formula Removed) A J I 661-Foreign Countries
(Y, Z, R1, R2, R\ R4, R5, R6 and R7 are each as defined
above
Including the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following principal structures (I-2-a) to (I-2-g) result if Het represents the group (2)
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Le A 31 661-Foreign Countries
A, B, E, L, M, V, W, X, Y Z, R1, R2, R\ R4, R5, R6 and R7 are each as defined above
Including the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following principal structures (1-3-a) to (1-3-g) result if Het represents the group (3)




Lg_A_3J_66-bF.preign Countries
A, B, E, L, M, V, W, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 are each as defined above. d to be expressed by the dashed line in the formula (1-4).
The compounds of the formulae (I-4)a and (I-4)h can be present both as mixtures and in the form of their pure isomers. Mixtures of the compounds of the formulae (l-4)a and (1-4),, can, if desired, be separated by physical methods in a manner known per se, for example by chromatographic methods.

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For better clarity, in the following in each case only one of the possible isomers is shown This does not exclude the possibility that the compounds can optionally be present in the form of the isomer mixtures or in the other respective isomer form.
Including the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following principal structures (I-4-a) to (I-4-g) result if Het represents the group (4)
(Formula Removed)




-

in which
A, D, E, L, M, V, W, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 are each as defined above
Including the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G, the following principal structures (I-5-a) to (I-5-g) result if Het represents the group (5)

in which
A, E, L, M, V, W, X, Y, Z, R1, R2, R3, R4, R5, R6 and R7 are each as defined above
Furthermore, it has been found that the novel compounds of the formula (I) are obtained by one of the processes described below:
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(A) Compounds of the(Formula Removed)


n which
A, B, V, W, X, Y and Z are each as defined above.
are obtained by the intramolecular condensation of
compounds of the formula (II)

W
Y
in which,
A, B, V, W, X, Y and Z are each as defined above
and
Rx represents alkyl (preferably C|-C6-alkyl)
in the presence of a diluent and in the presence of a base.

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(B) Furthermore, it was found that compounds of the formula (I-2-a)

in which
A, B, V, W, X, Y and Z are each as defined above
are obtained by the intramolecular condensation of
compounds of the formula (III)

W
A, B, V, W, X, Y, Z and R8 are each as defined above
in the presence of a diluent and in the presence of a base.
(C) Furthermore, it was found that compounds of the formula (I-3-a)
A, B, V, W, X, Y and Z are each as defined above
are obtained by the intramolecular cyclization of
compounds of formula (IV)


T R
in which
A, B, V, W, X, Y, Z and R are each as defined above and
T represents hydrogen, halogen, alkyl (preferably C^-C^alkyl) or alkoxy (preferably C,-C8-alkoxy),
if appropriate in the presence of a diluent and in the presence of an acid. (D) Furthermore, it was found that compounds of the formula (I-4-a)
L Z in which
A, D, V, W, X, Y and Z are each as defined above are obtained by reacting compounds of the formula (V) O

D-C-CH2-A
in which
A and D are each as defined above or their silyl enol ethers of the formula (Va) D-C=CH-A

(V)

in which
A and D are each as defined above and R's represents alkyl (preferably methyl) with compounds of the formula (VI)

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X, Y and Z are each as defined above and
Hal represents halogen (preferably chlorine or bromine),
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
(E) Furthermore, it was found that compounds of the formula (I-5-a)

in which
A, V, W, X, Y and Z are each as defined above
are obtained by reacting compounds of the(Formula Removed) 661 -Foreign Countries
(Formula Removed)ith compounds of th formula (VI)
Hal, V, W, X, Y and Z are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
In addition, it has been found
(F) that the compounds of the formulae (I-l-b) to (I-5-b) shown above in which A, B, D, R1, V, W, X, Y and Z are each as defined above are obtained by reacting compounds of the formulae (I-l-a) to (I-5-a) shown above in which A, B, D, V, W, X, Y and Z are each as defined above
a) with acid halides of the formula (VIII)
R1 is as defined above and
Hal represents halogen (in particular chlorine or bromine)
Le A .1.1 66J -Foreign Countries
P) with carboxylic anhydrides of the formula (IX)
R'-CO-O-CO-R1 (IX)
in which R1 is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent;
(G) that the compounds of the formulae (I-l-c) to (I-5-c) shown above in which A, B, D, R2, V, W, M, X, Y and Z are each as defined above and L represents oxygen are obtained by reacting compounds of the formulae (I-l-a) to (I-5-a) shown above in which A, B, D, V, W, X, Y and Z are each as defined above in each case
with chloroformic esters or chloroformic thioesters of the formula (X)
R2-M-CO-C1 (X)
in which R2 and M are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent;
(H) that compounds of the formulae (I-l-c) to (I-5-c) shown above in which A, B, I), R", V, W, M, X, Y and Z are each as defined above and L represents sulphur are obtained by reacting compounds of the formulae (I-l-a) to (1-5-a) shown above in which A, B, D, V, W, X, Y and Z are each as defined above in each case
a) with chloromonothioformic esters or chlorodithioformic esters of the formula
(XI)

Le A 31 661 -Foreign Countries
M and R" are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent
or
p) with carbon disulphide and subsequently with compounds of the formula (XII)
R2-Hal (XII)
in which
R." is as defined above and Hal represents chlorine, bromine or iodine,
if appropriate in the presence of a diluent and if appropriate in the presence of a base,
(I) that compounds of the formulae (I-l-d) to (I-5-d) shown above in which A, B, D, R\ V, W, X, Y and Z are each as defined above are obtained by reacting compounds of the formulae (I-l-a) to (I-5-a) shown above in which A, B, D, V, W, X, Y and Z are each as defined above in each case
with sulphonyl chlorides of the formula (XIII)
Le A 31 661-Foreign Countries
in which
R1 is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent,
(J) that compounds of the formulae (I-l-e) to (I-5-e) shown above in which A, B, D, L, R4, R5, V, W, X, Y and Z are each as defined above are obtained by reacting compounds of the formulae (I-l-a) to (I-4-a) shown above in which A, B, D, V, W, X, Y and Z are each as defined above in each case
with phosphorus compounds of the formula (XIV)
L, R4 and R5 are each as defined above and
Hal represents halogen (in particular chlorine or bromine),
if appropriate in the presence of a diluent and if appropriate in the presence of acid-binding agent,
(K) that compounds of the formulae (I-l-f) to (I-5-f) shown above in which A, B, D, E, V, W, X, Y and Z are each as defined above are obtained by reacting compounds of the formulae (I-l-a) to (I-5-a) in which A, B, D, V, W, X, Y and Z are each as defined above in each case
with metal compounds or amines of the formulae (XV) or (XVI)
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Me represents a mono- or divalent metal (preferably an alkali metal or an alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium),
t represents the number 1 or 2 and
Rl(l, R", R12 each represent independently of one another hydrogen or alkyl (preferably C,-C8-alkyl),
if appropriate in the presence of a diluent,
(L) that compounds of the formulae (I-l-g) to (I-5-g) shown above, in which A, B, D, L, R6, R7, V, W, X, Y and Z are each as defined above, are obtained by reacting compounds of the formulae (I-l-a) to (I-5-a) shown above, in which A, B, D, V, W, X, Y and Z are each as defined above, in each case
a) with isocyanates or isothiocyanates of the formula (XVII)
R('-N=OL (XVII)
in which Rh and L are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or
P) with carbamoyl chlorides or thiocarbamoyl chlorides of the formula (XVIII)
Le A 31 661-Foreign Countries
and R are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent.
Furthermore, it has surprisingly been found that the novel compounds of the formula (1) have very good activity as pesticides, preferably as insecticides, acaricides and, as herbicides, and that they additionally are very well tolerated by plants, in particular by crops.
Formula (1) provides a general definition of the compounds according to the invention. Preferred substituents or ranges of the radicals shown in the formulae mentioned heremabove and hereinbelow are illustrated below:

V

preferably represents hydrogen, halogen, C,-Cr)-alkyl or C,-C6-alkoxy.

W preferably represents cyano, nitro, halogen, C,-C6-alkyl, CVC6-alkenyl, CV C6-alkinyl, CpC^-alkoxy, C]-C4-halogenoalkyl, C,-C4-halogenoalkoxy or respectively optionally halogen-, C,-C6-alkyl-, C|-C6-alkoxy-, C|-C4-halo-genoalkyl-, C|-C4-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phen-oxy, phenylthio, phenyl-C,-C4-alkoxy or phenyl-C,-C4-alkylthio,

X

preferably represents hydrogen, halogen, C,-C6-alkyl, C9-C6-alkenyl, C0-C6-alkinyl, r|-C6-alkoxy, C|-C4-halogenoalkyl, C,-C4-halogenoalkoxy, cyano, nitro or respectively optionally halogen-, C)-C6-alkyl-, C,-C6-alkoxy-, C,-C4-halogenoalkyl-, CpCz-halogenoalkoxy-, nitro- or cyano- substituted phenyl, phenoxy, phenylthio, phenyl-C]-C4-alkoxy or phenyl-Ct-C4-alkyl-

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Y preferably represents hydrogen, halogen, C,-C6-alkyl, C,-C6-alkoxy, C,-C4-halogenoalkyl, C,-C4-halogenoalkoxy, cyano or nitro,
Z preferably represents halogen, Cj-C^alkyl, C|-C6-alkoxy, C,-C4-halogeno-alkyl, CpC4-halogenoalkoxy, hydroxyl, cyano, nitro or respectively optionally halogen-, C,-C4-alkyl-, C,-C4-alkoxy-, C,-C4-halogenoalkyl-, C,-C4-halo-genoalkoxy-, nitro- or cyano-substituted phenoxy, phenylthio, thiazolyloxy, pyridinyloxy, pyrimidyloxy, pyrazolyloxy, phenyl-C,-C4-alkyloxy or phenyl-C,-C-alkylthio, or,
Y and Z together preferably represent respectively optionally halogen-, Cj-C6-alkyi-, C,-C6-alkoxy- or C,-C4-halogenoalkyl-substituted C3-C5-alkanediyl or C,-C5-alkenediyl in which one to three members can be optionally replaced independently of one another by oxygen, sulphur, nitrogen or a carbonyl group, or
W and Z together preferably represent respectively optionally halogen-, C,-C6-alkyl-, C|-Cf]-alkoxy- or C|-C4-halogenoalkyl-substituted C3-C5-alkanediyl or C^-C^-alkenediyl in which one to three members can be optionally replaced independently of one another by oxygen, sulphur, nitrogen or a carbonyl group.
Het preferably represents one of the groups
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n, respectively optionally halogen-substituted C,-Cp-alkyl, C-,-C8-alkenyl, C1-C10-alkoxy-C]-Cs-alkyl, poly-Cj-C8-alkoxy-C,-C8-alkyl or CpCuj-alkylthio-CpCfi-alkyl, optionally halogen-, C,-C6-alkyl- or C|-C6-alkoxy-substituted Cs-C8-cycloalkyl in which optionally one or two not directly adjacent methylene groups are replaced by oxygen and/or sulphur, or preferably represents respectively optionally halogen-, C,-C6-alkyl-, CrC6-halogenoalkyl-, C|-C6-alkoxy-, Cj-C6-halogenoalkoxy-, cyano-or nitro-substituted phenyl, naphthyl, phenyl-C,-C6-alkyl, naphthyl-C,-C6-alkyl or hetaryl having 5 or 6 ring atoms and one to three heteroatoms from the group consisting of oxygen, sulphur and nitrogen.
B preferably represents hydrogen, Cj-Cp-alkyl or C,-CK-alkoxy-C,-C6-alkyl or
A, B and the carbon atom that they are attached to preferably represent C3-C10-cycloalkyl or C5-C,0-cycloalkenyl where in each case one methylene group is optionally replaced by oxygen or sulphur and which are optionally substituted by r,-C8-alkyl, C\-C|()-cycloalkyl, C,-Cx-halogenoalkyl, C,-G C",-('s-alkvlthio, halogen or phenyl, or
Le A .31 661-Foreign Countries
A, B and the carbon atom that they are attached to preferably represent C5-C6-cycloalkyl which is substituted by an alkylenediyl group optionally containing one or two oxygen and/or sulphur atoms, or by an alkylenedioxy group or alkylenedithioyl group forming a further five- to eight-membered ring with the carbon atom that it is attached to, or
A, B and the carbon atom that they are attached to preferably represent C-^-Cg-cycloalkyl or C5-Cs-cycloalkenyl in which two carbon atoms are connected by respectively optionally C,-C6-alkyl-, C,-C6-alkoxy- or halogen-substituted CrC6-alkanediyl, CrC6-alkenediyl or C4-Cfi-alkanedienediyl where in each case one methyiene group is optionally replaced by oxygen or sulphur.
D preferably represents hydrogen, respectively optionally halogen-substituted C,-C12~alkyl, C^-C8-alkenyl, (\-C8-alkinyl, C,-C]0-alkoxy-C7-C8-alkyl, poly-C,-C8-alkoxy-C,-C8-alkyl or CpCm-alkylthio-Ci-Cjj-alkyl, optionally halogen-, CrC4-alkyl-, CrC4-alkoxy- or CpChaiogenoalkyl-substituted CrCs-cycloalkyl in which optionally one or two not directly adjacent methyiene groups are replaced by oxygen and/or sulphur, or preferably represents respectively optionally halogen-, C|-C6-alkyl-, C|-C6-halogenoalkyl-, C,-C6-alkoxy-, C(-C6-halogenoalkoxy-, cyano- or nitro-substituted phenyl, hetaryl having 5 to 6 ring atoms and one or two heteroatoms from the group consisting of oxygen, sulphur and nitrogen, phenyl-C|-C6-alkyl or hetaryl-Cj-C()-alkyl having 5 to 6 ring atoms and one or two heteroatoms from the group consisting of oxygen, sulphur and nitrogen, or
A and D together preferably represent a C3-C6-alkanediyl, C^-C6-alkenediyl or C4-C6-alkadienediyl group in which in each case one methyiene group is optionally replaced by oxygen or sulphur and which are respectively optionally substituted by halogen or by respectively optionally halogen-substituted f ,-CKj-alkyl, C,-C6-alkoxy, C,-C6-alkylthio, CrC7-cycloalkyl, phenyl or benzyloxy or by a further CrC6-alkanediyl, C,-C6-alkenediyl or C4-Cf>-alkadienediyl group forming a fused-on ring where in each case one methyiene group is optionally replaced by oxygen or sulphur and which are optionally substituted by C,-Cf)-alkyl, or
Le A 31 661-Foreiun Countries
A and D together represent a CrC6-alkanediyl or C3-C6-alkenediyl group, each of which optionally contains one of the following groups
hydrogen (a) or one of the groups
in which
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulphur and
Le A 31 661-Foreign Countries
M represents oxygen or sulphur.
R1 preferably represents respectively optionally halogen-substituted C,-C00-alkyl, C2-C20-alkenyl, CrC8-alkoxy-C,-Cg-alkyl, C,-C8-alkylthio-C,-C8-alkyl or poly-C1-C8-alkoxy-C!-C8-alkyI or respectively halogen-, Cj-C6-alkyl- or C|-C6-alkoxy-substituted C3-C8-cycloalkyl in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and/or sulphur,
optionally halogen-, cyano-, nitro-, C|-C6-alkyl-, C,-C6-alkoxy-, C,-C6-halo-genoalkyl-, C,-C6-haIogenoalkoxy-, CrC6-alkyithio- or C,-C6-alkyl-sulphonyl-substituted phenyl,
optionally halogen-, nitro-, cyano-, C,-C6-alkyl-, C,-C6-alkoxy-, C,-C6-haio-genoalkyl- or C|-C6-halogenoalkoxy-substituted phenyl-C,-C6-alkyl,
optionally halogen- or C^C^-alkyl-substituted 5- or 6-membered hetaryl having one or two heteroatoms from the group consisting of oxygen, sulphur and nitrogen,
optionally halogen- or C,-C6-alkyl-substituted phenoxy-C|-C6-alkyl or
optionally halogen-, ami no- or C,-C6-alkyl-substituted 5- or 6-membered hetaryloxy-C,-C6-alkyl having one or two heteroatoms from the group consisting of oxygen, sulphur and nitrogen.
R~ preferably represents respectively optionally halogen-substituted C,-Co()-alkyl, (-,-C0()-alkenyl, CpC^-alkoxy-CTC^-alkyl or poly-C,-C8-alkoxy-C-,-Cx-alkyl,
optionally halogen-, C^C^-alkyl- or C,-C6-alkoxy-substituted C:,-C8-cyclo-alkyl or
respectively optionally halogen-, cyano-, nitro-, C,-C6-alkyl-, C,-C6-alkoxy-, C|-Cf)-halogenoalkyl or C|-Cri-halogenoalkoxy-substituted phenyl or benzylLe A 31 661-Foreign Countries
R/ preferably represents optionally halogen-substituted C,-C8-alkyl or respectively optionally halogen-, C,-C6-alkyl-, C,-C6-alkoxy-, C,-C4-halogeno-alkyl-, C|-C4-halogenoalkoxy-, cyano- or nitro-substituted phenyl or benzyl.
R4 and R^ each preferably represent independently of one another respectively optionally halogen-substituted C,-C8-alkyl, C,-C8-alkoxy, CpCj^-alkylamino, di-(C|-C8-alkyl)amino, C,-C8-alkylthio or C3-C8-alkenylthio, respectively optionally halogen-, nitro-, cyano-, C,-C4-alkoxy-, C,-C4-halogenoalkoxy-, C,-C4-alkylthio-, C,-C4-halogenoalkylthio-, C,-C4-alkyl- or C,-C4-halogeno-alkyl-substituted phenyl, phenoxy or phenylthio.
R/' and R7 preferably represent independently of one another hydrogen, respectively optionally halogen-substituted C,-C8-alkyl, CrC8-cycloalkyl, C,-C8-alkoxy, C3-C8-alkenyl or C,-C8-alkoxy-C0-C8-alkyl, respectively optionally halogen-, C,-C8-alkyl-, CrC8-halogenoalkyl- or CpCjj-alkoxy-substituted phenyl or benzyl or together represent an optionally C,-C6-alkyl-substituted C3-C6-alkylene radical in which one methylene group is optionally replaced by oxygen or sulphur.
R1" preferably represents hydrogen or respectively optionally halogen-substituted C,-C8-alkyl or C,-C8-alkoxy, optionally halogen-, C,-C4-alkyl- or C,-C4-alkoxy-substituted C\-C8-cycloalkyl in which one methylene group is optionally replaced by oxygen or sulphur, or respectively optionally halogen-, C,-C6-alkyl-, C,-C6-alkoxy-, C,-C4-halogenoalkyl-, C,-C4-halo-genoalkoxy-, nitro- or cyano-substituted phenyl, phenyl-C(-C4-alkyl or
R14 preferably represents hydrogen or C,-C8-alkyl or R1" and R14 together preferably represent C4-C6-alkanediyl, R1" and R16 are identical or different and preferably represent C|-C6-alkyl or
R1"1 and Ru> together preferably represent a C2-C4-alkanediyl radical which is optionally substituted by C,-C6-alkyl or by optionally halogen-, C,-C4-
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alkyl-, r,-C4-halogenoalkyK C,-C4-alkoxy-, CrC4-halogenoalkoxy-, nitro-or cyano-substituted phenyl.
R17 and R18 each preferably represent independently of one another hydrogen, optionally halogen-substituted C,-Cx-alkyl or optionally halogen-, C,-C6-alkyl-, C,-C6~alkoxy-, C,-C4-halogenoalkyl-, CrC4-halogenoalkoxy-, nitro-or cyano-substituted phenyl or
R17 and R18 preferably represent together with the carbon atom that they are attached to optionally Cj-C4-alkyl-substituted C5-C7-cycloalkyl in which one methylene group is optionally replaced by oxygen or sulphur.
R19 and R2() each preferably represent independently of one another C|-C,0-alkyl, CVC1()-alkenyl, C,-C10-alkoxy, C^-CiQ-alkylamino, C^-C1()-alkenylamino, di-(C|-C|0-alkyl)amino or di-(C3-C]()-alkenyl)amino).
V particularly preferably represents hydrogen, fluorine, chlorine, bromine, C,-C4-alkyl or C,-C4-alkoxy.
W particularly preferably represents cyano, nitro, fluorine, chlorine, bromine, C|-C4-alkyl, C,-C4-alkoxy, CptVhalogenoalkyl, Cj-C-,-halogenoalkoxy or respectively optionally fluorine-, chlorine-, bromine-, C,-C4-alkyl-, C|-C4-alkoxy-, C,-C2-halogenoalkyl-, C^Co-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy, benzyl or benzyloxy.
X particularly preferably represents hydrogen, fluorine, chlorine, bromine, C,-C,-alkyl, C|-C4-alkoxy, CpCo-halogenoalkyl, C,-C0-halogenoalkoxy, cyano, nitro or respectively optionally fluorine-, chlorine-, bromine-, C|-C4-alkyl-, C|-C4-alkoxy-, ("j-Co-halogenoalkyl-, CpCVhalogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy, benzyl or benzyloxy
Y particularly preferably represents hydrogen, fluorine, chlorine, bromine, C,-C4-alkyl, CpC.^alkoxy, Cj-C^-halogenoalkyl, CrC-,-halogenoalkoxy, cyano or nitro
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Z particularly preferably represents fluorine, chlorine, bromine, C|-C4-alkyl, C|-C4-alkoxy, CpCVhalogenoalkyl, CrC2-halogenoalkoxy, hydroxyl, cyano, nitro or respectively optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C,-C4~alkoxy-, C,-C2-halogenoalkyl-, CpC-j-halogenoalkoxy-, nitro- or cyano-substituted phenoxy or benzyioxy, or
Y and Z together particularly preferably represent respectively optionally fluorine-, chlorine-, bromine-, C,-C4-alkyl-, C,-C4-alkoxy- or C,-C2-halogenoalkyl-substituted C?-C4-alkanediyl or C3-C4-alkenediyl in which optionally one or two not directly adjacent members are replaced independently of one another by oxygen, sulphur or nitrogen, or
W and Z together particularly preferably represent respectively optionally fluorine-, chlorine-, bromine-, C,-C4-alkyl-, C|-C4-alkoxy- or C,-C,-halogenoalkyl-substituted CrC4-alkanediyl or C^-C^alkenyldiyl in which optionally one or two not directly adjacent members are replaced independently of one another by oxygen, sulphur or nitrogen.
Met particularly preferably represents one of the groups
particularly preferably represents hydrogen, respectively optionally fluorine-or chlorine-substituted C|-C1()-alkyl, C2-C6-alkenyl, C,-C
(Formula Removed) A 31 661-Foreign Countries
alkyl, poly-C,-Cri-alkoxy-C]-C6-alkyl or C,-C8-alkylthio-CrC6-alkyl or optionally fluorine-, chlorine-, C,-C4-alkyl- or C,-C4-alkoxy-substituted Cr C7-cycloalkyl in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and/or sulphur, or respectively optionally fluorine-, chlorine-, bromine-, C,-C4-alkyl-, C,-C4-halogenoalkyl-, C,-C4-alkoxy-, C,-C4-halogenoalkoxy-, cyano- or nitro-substituted phenyl, furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, indolyl, thiazolyl, thienyl or phenyl-C,-C4-alkyl.
B particularly preferably represents hydrogen, CrC10-alkyl or C,-C6-alkoxy-C,-C4-alkyl or
A, B and the carbon atom that they are attached to particularly preferably represent C,-C8-cycloalkyl or C5-C8-cycloalkenyl in which respectively optionally one methylene group is replaced by oxygen or sulphur and which are optionally substituted by C,-C6-alkyl, C^-C8-cycloalkyl, C|-C?-halogenoalkyl, C,-C6-alkoxy, C|-C6-alkylthio, fluorine, chlorine or phenyl, or
A, B and the carbon atom that they are attached to particularly preferably represent C5-Crrcydoalkyl which is substituted by an alkylenediyl group optionally containing one or two oxygen or sulphur atoms, or by an alkylenedioxy or alkylenedithiol group forming a further five- to seven-membered ring with the carbon atom that it is attached to or
A, B and the carbon atom that they are attached to particularly preferably represent C,-Cri-cycloalkyl or C5-C6-cycloalkenyl in which two carbon atoms are connected by respectively optionally C|-C4-alkyl-, C,-C4-alkoxy-, fluorine-, chlorine- or bromine-substituted C,-C5-alkanediyl, C^-C5-alkenediyl or buta-dienediyl in which respectively optionally one methylene group is replaced by oxygen or sulphur.
1) particularly preferably represents hydrogen, respectively optionally fluorine-or chlorine-substituted CpC^-alkyl, C.-C6-alkenyl, C3-C6-alkinyl, C|-C8-alkoxy-C,-('(i-alkyl, poly-CpC^-alkoxy-C-rC^alkyl or C,-C8-alkylthio-Co-C()-alkyl, optionally fluorine-, chlorine-, C,-C4-alkyl-, C|-C4-alkoxy- or C{-(o-halogenoalkvl-substituted C^-C7-cycloalkyl in which one or two not di-
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reedy adjacent methylene groups are optionally replaced by oxygen and/or sulphur, or particularly preferably represents respectively optionally fluorine-, chlorine-, bromine-, C,-C4-alkyl-, CrC4-halogenoalkyl-, C,-C4-alkoxy-, C,-C4-halogenoalkoxy-, cyano- or nitro-substituted phenyl, furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl, thienyl, tri-azolyl or phenyl-C,-C4-alkyl or
A and D together particularly preferably represent a C3-C5-alkanediyl or C^-C^-alkenediyl group in which respectively optionally one carbon atom is replaced by oxygen or sulphur and which are optionally substituted by fluorine, chlorine or respectively optionally fluorine- or chlorine-substituted C,-C6-alkyl, C,-C4-alkoxy, CrC4-alkylthio, C3-C6-cycloalkyl, phenyl or benzyloxy or
which respectively optionally contain one of the following groups:
G particularly preferably represents hydrogen (a) or one of the groups
epresents a metal ion equivalent or an ammonium ion,
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L represents oxygen or sulphur and M represents oxygen or sulphur.
R1 particularly preferably represents respectively optionally fluorine- or chlorine-substituted C,-C16-alkyl, C2-C|6-alkenyl, C,-C6-aIkoxy-C,-C6-alkyl, C|-C6-alkylthio-C,-C6-alkyl or poly-C,-C6-alkoxy-C|-C6-alkyl or optionally fluorine-, chlorine-, CrC5-alkyl- or C,-C5-alkoxy-substituted C3-C7-cyclo-alkyl in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and/or sulphur,
optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C]-C4-alkyl-, C,-C4-alkoxy-, C,-C3-halogenoalkyl-, Cj-C^-halogenoaikoxy-, C,-C4-alkylthio- or C|-C4-alkylsulphonyl-substituted phenyl,
optionally fluorine-, chlorine-, bromine-, C,-C4-alkyl-, C,-C4-alkoxy-, C,-C.-halogenoalkyl- or C,-Crhalogenoalkoxy-substituted phenyl-C1-C4-alkyl,
optionally fluorine-, chlorine-, bromine- or C,-C4-alkyl-substituted pyrazolyl, thiazolyl, pyndyl, pyrimidyl, furanyl or thienyl,
optionally fluorine-, chlorine-, bromine- or C,-C4-alkyl-substituted phenoxy-C,-C5-alkyl or
respectively optionally fluorine-, chlorine-, bromine-, amino- or C,-C4-alkyl-substituted pyridyloxy-C,-C5-alkyl, pyrimidyloxy-C,-C5-alkyl or thiazolyl-oxy-C,-C5-alkyl.
R~ particularly preferably represents respectively optionally fluorine- or chlorine-substituted C|-C]6-alkyl, C,-C16-alkenyl, Ct-C6-alkoxy-C-,-Cr)-alkyl or poly-Cj-C6-alkoxy-C->-C6-alkyl,
optionally fluorine-, chlorine-, CrC4-alkyl- or C]-C4-alkoxy-substituted C,-C7-cycloalkyl or
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respectively optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C|-C4-alkyl-, ("i-C^-alkoxy-, Cj-C^-halogenoalkyl- or C-C-halogenoalk-oxy-substituted phenyl or benzyl.
R1 particularly preferably represents optionally fluorine- or chlorine-substituted C|-C6-alkyl or respectively optionally fluorine-, chlorine-, bromine-, C|-C4-alkyl-, C|-C4-alkoxy-, C,-C2-halogenoalkoxy-, C,-C2-halogenoalkyl-, cyano-or nitro-substituted phenyl or benzyl.
R1 and R^ each particularly preferably represent independently of one another respectively optionally fluorine- or chlorine-substituted C,-C6-alkyl, Cj-C6-alkoxy, C|-C6-alkylamino, di-(C|-C6-alkyl)amino, C,-C6-alkylthio or CrC4-alkenylthio or respectively optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, C|-C3-alkoxy-, C,-Crhalogenoalkoxy-, C,-C3-alkylthio-, C,-Cr halogenoalkylthio, C,-C,-alkyl- or CpC^-halogenoalkyl-substituted phenyl, phenoxy or phenylthio.
R(> and R7 each particularly preferably represent independently of one another hydrogen, respectively optionally fluorine- or chlorine-substituted C,-C6-alkyl, CrC6-cycloalkyl, C,-Cr,-alkoxy, CrC6-alkenyl or CrC6-alkoxy-C-,-C6-alkyl, respectively optionally fluorine-, chlorine-, bromine-, C|-C5-halo-genoalkyl-, CpCj-alkyl- or C,-C5-alkoxy-substituted phenyl or benzyl, or particularly preferably represent together an optionally C,-C4-alkyl-substituted Co-C6-alkylene radical in which one methylene group is optionally replaced by oxygen or sulphur.
R1" particularly preferably represents hydrogen or respectively optionally fluorine- or chlorine-substituted C,-C6-alkyl or C,-C6-alkoxy, optionally fluorine-, C,-CValkyl- or C,-C,-alkoxy-substituted Cn-C7-cycloalkyl in which one methylene group is optionally replaced by oxygen or sulphur, or particularly preferably represents respectively optionally fluorine-, chlorine-, bromine-, CpC^-alkyl-, C,-C5-alkoxy-, Ci-CVhalogenoalkyl-, CrC-,-halo-genoalkoxy-, nitro- or cyano-substituted phenyl, phenyl-C^C^-alkyl or phenyl-f |-(Va
R1"1 particularly preferably represents hydrogen or C|-C6-alkyl or
L^ A 31 661-Foreign Countries
RM and R1'1 together particularly preferably represent C4-C6-alkanediyl.
II1 ^ and Ru> are identical or different and particularly preferably represent C,-C4-alkyl or
Rl3 and Rifl together particularly preferably represent a C-,-CraIkanediyl radical which is optionally substituted by CrC4-alkyl or optionally fluorine-, chlorine-, bromine-, C^-CValkyl-, C,-C-,-halogenoalkyl-, C,-C-,-alkoxy-, C,-(Vhalogenoalkoxy-, nitro- or cyano-substituted phenyl.
V very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, tert-butyl, methoxy, ethoxy, propoxy or isopropoxy
W very particularly preferably represents cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, phenyl or benzyloxy.
X very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, isobutyl, isopropyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano, nitro, phenyl or benzyloxy.
Y very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano or nitro
Z very particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, isobutyl, isopropyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano or nitro, or
Y and Z together very particularly preferably represent optionally fluorine-, chlorine- methyl-, ethyl-, propyl-, isopropyl-, methoxy-, ethoxy-, propoxy-, 31 661-Foreign Countries
isopropoxy- or trifluoromethyl-substituted C^-C4-alkanediyl in which two not directly adjacent members are optionally replaced by oxygen, or
W and Z together very particularly preferably represent optionally fluorine-, chlorine-, methyl-, ethyl-, propyl-, isopropyl-, methoxy-, ethoxy-, propoxy-, isopropoxy- or trifluoromethyl-substituted C3-C4-alkanediyl in which two not directly adjacent members are optionally replaced by oxygen.

fluorine- or chlorine-substituted C,-CK-alkyl, C0-C4-alkenyl, C|-C6-alkoxy-C|-C4-alkyl, poly-C|-C4-alkoxy-C|-C4-alkyl or C]-C6-alkylthio-C]-C4-alkyl or optionally fluorine-, chlorine-, methyl- or methoxy-substituted C^-C6-cycloalkyl in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and/or sulphur, or very particularly preferably represents respectively optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, isopropyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoro-methoxy-, cyano- or nitro-substituted phenyl, pyridyl or benzyl.
LeL_ A J -L.6-61 -Foreign Countries
B very particularly preferably represents hydrogen, C,-Cx-alkyl or C,-C4-alkoxy-Cj-CValkyl or
A, B and the carbon atom that they are attached to very particularly preferably represent CrC8-cycloalkyI or C5-Cx-cycloalkenyl where in each case one methylene group is optionally replaced by oxygen or sulphur and which are optionally substituted by methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, fluorine, chlorine or phenyl or
A, B and the carbon atom that they are attached to very particularly preferably represent C5-C6-cycloalkyl which is substituted by an alkylenediyl group optionally containing an oxygen or sulphur atom, or by an alkylenedioxy group forming a further five- or six-membered ring with the carbon atom that it is attached to or
A, B and the carbon atom that they are attached to very particularly preferably represent C,-C6-cycIoalkyl or C5-C6-cycloalkenyl in which two carbon atoms are connected by CrC4-alkanediyl, C3-C4-alkenediyl or butadienediyl.
D very particularly preferably represents hydrogen, respectively optionally fluorine-- or chlorine-substituted Cj-Cg-alkyl, C?-C4-alkenyl, CrC4-alkinyl, C,-C()-alkoxy-C2-C4-alkyl, poly-C1-C4-alkoxy-C2-C4-alkyl, CrC4-alkyUhio-(VC4-alkyl or C,-C6-cycloalkyl in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and/or sulphur, or very particularly preferably represents respectively optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, isopropyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl, furanyl, pyridyl, thienyl or benzyl,
or
A and D together very particularly preferably represent a CrC5-alkanediyl or Cr (.\-alkenediyt group where in each case one methylene group is optionally replaced by oxygen or sulphur and which are optionally substituted by
Le A 31 661-Foreign Countries
- 41 -
fluorine, chlorine or respectively optionally fluorine- or chlorine-substituted C|-("f,-alkyl or C,-C4-alkoxy.
G very particularly preferably represents hydrogen (a) or one of the groups
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulphur and
M represents oxygen or sulphur.
R1 very particularly preferably represents respectively optionally fluorine- or chlorine-substituted C,-C14-alkyl, G,-C,4-alkenyl, C,-C4-alkoxy-C,-Cfi-alkyl, C|-C.,-alkylthio-C,-C6-alkyl, poly-C1-C4-alkoxy-C1-C4-alkyl or optionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, i-propyl-, n-butyl-, i-butyl-, tert-butyl-, methoxy-, ethoxy-, n-propoxy- or isopropoxy-substituted C3-C6-cycloalkyl in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and/or sulphur,
optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, methylthio-, ethylthio-, methylsulphonyl- or ethylsulphonyl-substituted phenyl,
optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy-substituted benzyl,
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respectively optionally fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted furanyl, thienyl or pyridyl,
optionally fluorine-, chlorine-, methyl- or ethyl-substituted phenoxy-C|-C4-alkyl or
respectively optionally fluorine-, chlorine-, amino-, methyl- or ethyl-substituted pyridyloxy-C,-C4-alkyl, pyrimidyloxy-C|-C4-alkyl or thiazolyloxy-C,-C4-alkyl.
R2 veiy particularly preferably represents respectively optionally fluorine- or chlorine-substituted C,-C]4-alkyl, C2-C,4-alkenyl, CrC4-alkoxy-C0-C6-alkyl or poly-CpQj-alkoxy-C-j-C^alkyl,
optionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, isopropyl- or meth-oxy-substituted CrC6-cycloalkyl,
or respectively optionally fluorine-, chlorine-, cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl or benzyl.
II1 very particularly preferably represents optionally fluorine- or chlorine-substituted methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, or respectively optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, isopropyl-, tert-butyl-, methoxy-, ethoxy-, isopropoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl or benzyl.
R4 and R^ each very particularly preferably represent independently of one another respectively optionally fluorine- or chlorine-substituted C,-C4-alkyl, C,-C4-alkoxy, C,-C4-alkylamino, di-(C,-C4-alkyl)amino or C,-C4-alkylthio or respectively optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, methyl-, methoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl, phenoxy or phenylthio.
R(> and R each very particularly preferably represent independently of one another hydrogen, respectively optionally fluorine- or chlorine-substituted C,-C4-

Le A .•> I 661 -Foreign. Countries
C4-alkoxy, C-^-C^-alkenyl or C|-C4-alkoxy-C0-C4-alkyl, respectively optionally fluorine-, chlorine-, bromine-, methyl-, methoxy- or trifluoromethyl-substituted phenyl or benzyl or together represent an optionally methyl- or ethyl-substituted C5-C6-alkylene radical in which one m ethyl en e group is optionally replaced by oxygen or sulphur.
Excluded are in each case the following compounds (disclosed in EP-0 528 156):

661-Foreign Countries

If, in the compounds of the formula (1-2), only the substituent V of the substitu-ents X, V, Y, Z and W represents hydrogen and X, Y, Z and W have a meaning different from hydrogen, then preference is given to such compounds of the formula (1-2) in which Z does not represent halogen.
The abovementioned definitions or illustrations of radicals mentioned generally or in preferred ranges can be combined with each other as desired, i.e. also between the respective ranges and preferred ranges. They apply correspondingly to the final products and to the precursors and intermediates.
For the purpose of the invention, preference is given to compounds of the formula (I) in which there exists a combination of the meanings mentioned above as preferred (preferable)
For the purpose of the invention, particular preference is given to compounds of the formula (I) in which there exists a combination of the meanings mentioned above as particularly preferred.
For the purpose of the invention, very particular preference is given to the compounds of the formula (I) in which there exists a combination of the meanings mentioned above as very particularly preferred.

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Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl can, as far as possible, in each case be straight-chain or branched, also in combination with heteroatoms, e.g. in alkoxy.
Optionally substituted radicals can be mono- or polysubstituted, it being possible in the case of poly substitution for the substituents to be identical or different.
Particular preference is given to compounds of the formula 1-1 to 1-3 in which
a) A, B and the carbon atom that they are attached to have the meanings
mentioned as very particularly preferred and V represents hydrogen,
b) A, B and the carbon atom that they are attached to have the meanings
mentioned as very particularly preferred and V and Y represent hydrogen.
In addition to the compounds mentioned in the Preparation Examples, the following compounds of the formula (I-l-a) may be specifically mentioned:
1-Foreign Countries
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ethyl)-phenyl]-5,5-pentamethylene-pyrrolidine-2,4-dione and ethoxyethyl chloroform ate are used as starting materials,

Le A 3 I 661-Foreign Countries
the course of the process according to the invention can be represented by the fo
If according to the process (H), (variant a) 3-[(2,6-dibromo-3,4-dimethyl)-phenyl]-4-hydroxy-6-(3-pyridyl)-pyrone and methyl chloromonothioformate are used as starting materials, the course of the reaction can be represented in the following


If according to process (H), (variant B) 5-[(3-chloro-2,6-dimethyl)-phenyl]-6-hydroxy-2-(4-chlorophenyl)-thiazin-4-one, carbon disulphide and methyl iodide are used as starting materials, the course of the reaction can be represented as follows:


phenyl]-5,5-[(3-methyl)penta-methylene|-pyi rolidine-2,4-dione and methanesulphonyl chloride are used as starting materials, the course of the reaction can be represented by the following reaction scheme
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(Formula Removed)f according to process (J) 2-[(2-chloro-5,6-dimethyl)-phenyl]-4-hydroxy-5-methyl-6-(2-pyridyl)-pyrone and 2,2,2-trifluoroethyl chloromethanethio-phosphonate are used as starting materials, the course of the reaction can be represented by the following reaction scheme:



CH,
(Formula Removed) according to process (L) (variant a) 3-[(2,6-dichloro-4-bromo-3-methyl)-phenyl]~ 4-hydroxy-5,5~tetramethylene-A1-dihydro-furan-2-one and ethyl isocyanate are used as starting materials, the course of the reaction can be represented by the follow-in» reaction scheme:

ethyl-pyrrolidine-2,4-dione and dimethylcarbamoyl chloride are used as starting materials, the course of the reaction can be represented by the following scheme:





The compounds of the formula (II)
A, B, V, W, X, Y, Z and RH have the meanings given above,
Le A 3 1 661-Foreign Countries
needed as starting substances in process (A) according to the invention are novel.
The acylamino acid esters of the formula (II) are obtained, for example, when ami no acid derivatives of the formula (XIX)
h
A, B and Rs are each as defined above, are acylated using substituted phenylacetyl halides of the formula (XX)
in which
V, W, X, Y and Z are each as defined above and
Hal icpresents chlorine or bromine,
(Chem. Reviews 52, 237-416 (1953); Bhattacharya, Indian J. Chem. 6, 341-5, 1968)
or when acylamino acids of the formula (XXI)
Le A 31 661-Foreign Countries


H
O
W
in which
A, B, V, W, X, Y and Z are each as defined above.
are esterified (Chem. Ind. (London) 1568 (1968)).
The compounds of the formula (XXI)


,C02H
H
O
W
Y
in which
A, B, V, W, X, Y and Z are each as defined above,
are novel.
The compounds of the formula (XXI) are obtained when amino acids of the formula (XXII)
Le A 31 661-Foreign Countries
A and B are each defined as above,
are acylated using substituted phenylacetyl halides of the formula (XX)
in which
V, W, X, Y and Z are each as defined above and
Hal represents chlorine or bromine,
according to Schotten-Baumann (Organikum, VEB Deutscher Verlag der Wissenschaften, Berlin 1977, p. 505).
Some of the compounds of the formula (XX) are novel and can be prepared by known methods
The compounds of the formula (XX) are obtained, for example, by reacting substituted phenylacetic acids of the formula (XXIII)
V, W, X, Y and Z are each as defined above,
with halogenating agents (e.g. thionyl chloride, thionyl bromide, oxalyl chloride, phosgene, phosphorus trichloride, phosphorus tribromide or phosphorus penta-

Le A 31 661-Foreign Countries
chloride), if appropriate in the presence of a diluent (e.g. optionally chlorinated aliphatic or aromatic hydrocarbons such as toluene or methylene chloride) at temperatures from -20°C to 150°C, preferably from-lO°C to 100°C.
Some of the compounds of the formula (XXIII ) are novel, they can be prepared by methods known from the literature (Organikum 15th edition, p. 533, VEB Deutscher Veriag der Wissenschaften, Berlin 1977). The compounds of the formula (XXIII) are obtained, for example, by hydrolysing substituted phenylacetic acid esters of the formula (XXIV)
V, W, X, Y, Z and R8 are each as defined above,
at temperatures between 0°C and 150°C, preferably between 20°C and 100°C, in the presence of an acid (e.g. of an inorganic acid such as hydrochloric acid) or of a base (e.g. of an alkali metal hydroxide such as sodium or potassium hydroxide) and, if appropriate, of a diluent (e.g. of an aqueous alcohol such as methanol or ethanol).
Some of the compounds of the formula (XXIV) are novel, they can be prepared by methods known in principle.
The compounds of the formula (XXIV) are obtained, for example, by reacting substituted l,l,l-trichloro-2-phenylethanes of the formula (XXV)
0ove,
first with alkoxides (e.g. alkali rnetal alkoxides such as sodium methoxide or sodium ethoxide) in the presence of a diluent (e.g. the alcohol derived from the alkoxide) at temperatures between 0°C and 150°C, preferably between 20°C and !20°C, and then reacting with an acid (preferably an inorganic acid, e.g. sulphuric acid) at temperatures between -20°C and 150°C, preferably 0°C and 100°C (cf. DE-33 14 249).
Some of the compounds of the formula (XXV) are novel, they can be prepared by methods known in principle.
The compounds of the formula (XXV) are obtained, for example, when anilines of the formula (XXVI)
V, W, X, Y and Z are each as defined above,
are reacted with vinylidene chloride (CH-,=CC12) in the presence of an alkyl nitrite of the formula (XXVII)
R21-ONO (XXVII)
in which
R-1 represents alkyl, preferably C,-C6-alkyl,
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in the presence of copper(II) chloride and if appropriate in the presence of a diluent (e.g. of an aliphatic nitrile such as acetonitrile) at a temperature of -20°C to 8()"C, preferably 0°C to 60°C.
Some of the compounds of the formula (XXVI) are known compounds, or they can be prepared by methods known in principle. The compounds of the formula (XXV11) are known compounds of organic chemistry. Copper(II) chloride and vinylidene chloride have long been known and are commercially available.
The compounds of the formulae (XIX) and (XXII) are known in some cases and/or can be prepared by known processes (see, for example, Compagnon, Miocque, Ann Chim. (Paris) [14] 5, p. 11-22, 23-27 (1970)).
The substituted cyclic aminocarboxylic acids of the formula (XXIIa), in which A and B form a ring, are in general obtainable by the Bucherer-Bergs synthesis or by the Strecker synthesis and are in each case obtained here in different isomeric forms. Thus, according to the conditions of the Bucherer-Bergs synthesis mainly the isomers (in the following designated as P for the sake of simplicity) in which the radicals R and the carboxyl group are equatorial are obtained, while according to the conditions of the Strecker synthesis mainly the isomers (in the following designated as a for the sake of simplicity) are obtained in which the amino group and the radicals R are equatorial.

Bucherer-Bergs synthesis Strecker synthesis
(fi-isomer) (a-isomer)
(L Munday, J Chetn. Soc. 4372 (1961); J.T. Eward, C. Jitrangeri, Can J. Chem.
53, 3339 (1975))
I'urlhetniore. the starting materials of the formula (II)
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O
W
Y
in which
A, B, V, W X, Y, Z and R8 are each as defined above,
used in the above process (A) can be prepared by reacting aminonitriles of the formula (XXVIII)



(XXVIII)

in which
A and B are as defined above,
with substituted phenylacetyl halides of the formula (XX)

V, W, X, Y, Z and Hal are each as defined above,
to give compounds of the formula (XXIX)

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in which
A, B, V, W X, Y and Z are each as defined above, and these are then subjected to an acidic alcoholysis. The compounds of the formula (XXIX) are also novel. The compounds of the formula (III)

in which
A, B, V, W, X, Y, Z and Rx are each as defined above,
needed as starting materials in process (B) according to the invention are novel.
They can be prepared in a simple manner by methods known in principle.
The compounds of the formula (III) are obtained, for example, when
2-hydroxycarboxylic acid esters of the formula (XXX)
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in which
A, B and Rs are each as defined above, are acylated using substituted phenylacetyl halides of the formula (XX)
in which
V, W, X, Y, Z and Hal are each as defined above,
(Chetn. Reviews 52, 237-416 (1953)).
Furthermore, compounds of the formula (III) are obtained when
substituted phenylacetic acids of the formula (XXIII)
V, W, X, Y and Z are each as defined above, are alkylated using a-halogenocarboxylic acid esters of the formula (XXXI)
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in which
A, B and Rs are each as defined above and
Hal represents chlorine or bromine.
The compounds of the formula (XXXI) are commercially available.
The compounds of the formula (IV)


in which
A, B, T, V, W, X, Y, Z and RH are each as defined above,
needed as starting substances in the above process (C) are novel. They can be prepared by methods known in principle. The compounds of the formula (IV) are obtained, for example, when substituted phenylacetic acid esters of the formula (XXIV)
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V, W, X, Y, Rx and Z are each as defined above,
are acylated using 2-benzylthio-carbonyl halides of the formula (XXXII)
in which
A, B and T are each as defined above and
Hal represents halogen (in particular chlorine or bromine),
in the presence of strong bases (see, for example, M.S. Chambers, E.J. Thomas, D..I Williams, J Chem. Soc. Chem. Commun., (1987), 1228).
The benzylthio-carbonyl halides of the formula (XXXII) are known in some cases and/or can be prepared by known methods (J. Antibiotics (1983), 26, 1589).
The halogenocarbonylketenes of the formula (VI) needed as starting materials in process (D) are novel. They can be prepared in a simple manner by methods known in principle (cf, for example, Org. Prep. Proced. Int., 7, (4), 155-158, 1975 and DE 1 945 703). The compounds of the formula (VI)
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in which
V, W, X, Y and Z are each as defined above and

Hal

represents chlorine or bromine,

are obtained when
substituted phenylmalonic acids of the formula (XXXIII)


V, W, X, Y and Z are each as defined above,
are reacted with acid halides, for example thionyl chloride, phosphorus(V) chloride, phosphorus(III) chloride, oxalyl chloride, phosgene or thionyl bromide, if appropriate in the presence of catalysts, for example diethylformatnide, methyl-sterylformamide or triphenylphosphine and if appropriate in the presence of bases, e.g. pyridine or triethylamine, at a temperature between -20°C and 200°C, preferably between 0°C and 150°C.
The substituted phenylmalonic acids of the formula (XXXIII) are novel. However, they can be prepared by known processes in a simple manner (cf, for example Organikum, VKB Deutscher Verlag der Wissenschaften, Berlin 1977, p. 517 ff),
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lor example by saponification of substituted phenylmalonic esters of the formula (XXXIV)

in which
V, W, X, Y, Z and R8 are each as defined above.
The carbonyl compounds of the formula (V) or their silyl enol ethers of the formula (Va)

in which

A, D and Rs are each as defined above,
needed as starting materials for process (E) according to the invention are compounds which are commercially available, generally known or accessible by
known processes
The preparation of the ketene acid chlorides of the formula (VI) needed as starting materials for carrying out process (E) according to the invention has already been described for process (D) according to the invention. The thioamides of the formula (VII)

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in which
A is as defined above,
needed for carrying out process (E) according to the invention are compounds which are generally known in organic chemistry.
The malonic acid esters of the formula (XXXIV)


CO2R
in which
Rs, V, W, X, Y and Z are each as defined above,
are novel and can be prepared by generally known methods of organic chemistry (cf., for example. Tetrahedron Lett. 27, 2763 (1986) and Organikum VEB Deutscher Verlag der Wissenschaften, Berlin 1977, p. 587 ff.).
The acid halides of the formula (VIII), carboxylic anhydrides of the formula (IX), chloroformic acid esters or chloroformic acid thioesters of the formula (X), chloro-monothioformic acid esters or chlorodithioformic acid esters of the formula (XI), alkyl halides of the formula (XII), sulphonyl chlorides of the formula (XIII), phosphorus compounds of the formula (XIV) and metal hydroxides, metal alkoxides or amines of the formula (XV) and (XVI) and isocyanates of the formula (XVII) and carbamoyl chlorides of the formula (XVIII) additionally needed as starting substances for carrying out processes (F), (G), (H), (I), (J), (K) and (L) according to the invention are generally known compounds of organic or inorganic chemistry
The compounds of the formulae (V), (VII) to (XVIII), (XIX), (XXII), (XXVIII), (XXX), (XXXI), (XXXII), (XXXIII) and (XXXIV) are moreover disclosed in the patent applications cited at the outset and/or can be prepared by the methods given
there

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Process (A) is characterized in that compounds of the formula (II), in which A, B, V, W, X, Y, 7. and R8 are each as defined above, are subjected to an intramolecular condensation in the presence of a diluent and in the presence of a base.
Diluents employed in process (A) according to the invention can be all organic solvents which are inert to the reaction participants. Those preferably utilizable are hydrocarbons, such as toluene and xylene, further ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, additionally polar solvents, such as dimethyl sulphoxide, sulpholane, dimethyl-formamide and N-methyl-pyrrolidone, and also alcohols such as methanol, ethanol, propanol, iso-propanol, butanol, iso-butanol and tert-butanol.
Suitable bases (deprotonating agents) employed in carrying out process (A) according to the invention can be all customary proton acceptors. Those preferably utilizable are alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, each of which can also be employed in the presence of phase-transfer catalysts, e.g. triethylbenzylarnmonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltnalkyl(C8-C10)ammonium chloride) or TDA 1 (= tris-(methoxyethoxy-ethyl)-amme). Alkali metals such as sodium or potassium can furthermore be used. Alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and additionally also alkali metal alkoxides, such as sodium methoxide, sodium ethoxide and potassium tert-butoxide can further be employed.
When carrying out process (A) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between -50°C and 250°C, preferably between -30°C and 150'T.
Process (A) according to the invention is in general carried out under atmospheric pressure
When carrying out process (A) according to the invention, the reaction component of the formula (II) and the deprotonating base are in general employed in

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equirnolar to approximately double equimolar amounts. However, it is also possible to use one component or the other in a relatively large excess (up to 3 mol).
Process (B) is characterized in that compounds of the formula (III), in which A, B, V, W, X, Y, Z and R8 are each as defined above, are condensed intramolecularly in the presence of a diluent and in the presence of a base.
The diluents employed in process (B) according to the invention can be all organic solvents which are inert to the reaction participants. Those preferably utilizable are hydrocarbons, such as toluene and xylene, furthermore ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and additionally polar solvents, such as dimethyl sulphoxide, sulpholane, dimethyl-formamide and N-rnethyl-pyrrolidone. Alcohols such as methanol, ethanol, propanol, iso-propanol, butanol, iso-butanol and tert-butanol can furthermore be employed
The bases (deprotonating agents) employed in carrying out process (B) according to the invention can be all customary proton acceptors. Those preferably utilizable are alkali metal and alkaline earth metal oxides, hydroxides and carbonates, such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, each of which can also be employed in the presence of phase-transfer catalysts, e.g. tri ethyl benzyl-ammonium chloride, tetrabutylammonium bromide, Adogen 464 (= methyltri-alkyl(Cs-C,())ammoniurn chloride) or TDA 1 (= tris-(methoxyethoxyethyl)-amine). Alkali metals such as sodium or potassium can furthermore be used. Alkali metal and alkaline earth metal amides and hydrides, such as sodium amide, sodium hydride and calcium hydride, and additionally also alkali metal alkoxides, such as sodium methoxide, sodium ethoxide and potassium tert-butoxide can additionally also be employed
When carrying out process (B) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between -50°C and 250°C, preferably between -30°C and 150°C.

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Process (B) according to the invention is in general carried out under atmospheric pressure.
When carrying out process (B) according to the invention, the reaction components of the formula (III) and the deprotonating bases are in general employed in approximately equimolar amounts. However, it is also possible to use one component or the other in a relatively large excess (up to 3 mol).
Process (C) is characterized in that compounds of the formula (IV), in which A, B, T, V, W, X, Y, Z and R8 are each as defined above, are cyclized intra-molecularly in the presence of an acid and if appropriate in the presence of a diluent.
Diluents which can be employed in process (C) according to the invention are all organic solvents which are inert to the reaction participants. Those preferably utilizable are hydrocarbons, such as toluene and xylene, further halogenated hydrocarbons such as dichloromethane, chloroform, ethylene chloride, chlorobenzene, dichlorobenzene, additionally polar solvents, such as dimethyl sulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone. Alcohols such as methanol, ethanol, propanol, iso-propanol, butanol, isobutanol, tert-butanol can furthermore be employed.
The acid employed can optionally also be used as a diluent.
Acids which can be employed in process (C) according to the invention are all customary inorganic and organic acids, e.g. hydrohalic acids, sulphuric acid, alkyl-, aryl- and haloalkylsulphonic acids; halogenated alkylcarboxylic acids, e.g. trifluoroacetic acid, are used in particular.
When carrying out process (C) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between -30°C and 250°C, preferably between 0°C and 150°C.
Process (C) according to the invention is in general carried out under atmospheric
pressure.

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When carrying out process (C) according to the invention, the reaction components of the formulae (IV) and the acid are employed, for example, in equimolar amounts. However, it is optionally also possible to employ the acid in catalytic amounts.
Process (D) according to the invention is characterized in that carbonyl compounds of the formula (V) or their silyl enol ethers of the formula (Va) in which A and B are each as defined above are reacted with ketene acid halides of the formula (VI) in which V, W, X, Y and Z are each as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
Diluents which can be employed in process (D) according to the invention are all organic solvents which are inert to the reaction participants. Those preferably utilizable are hydrocarbons, such as o-dichlorobenzene, tetralin, toluene and xylene, furthermore ethers, such as dibutyl ether, glycol dimethyl ether and di-glycol dimethyl ether, and additionally polar solvents, such as dimethyl sulphoxide, sulpholane, dimethylformamide or N-methyl-pyrrolidone.
Acid acceptors which can be used when carrying out process (D) according to the invention are all customary acid acceptors.
Those preferably utilizable are tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclononene (DBN), Hiinig base or N,N-dimethyl-aniline.
When carrying out process (D) according to the invention, the reaction temperature can be varied within a relatively wide range. The reaction is expediently carried out at temperatures between 0°C and 250°C, preferably between 50°C and
220°C
Process (D) according to the invention is preferably carried out under atmospheric pressure.
When carrying out process (D) according to the invention, the reaction components of the formulae (V) and (VI) and, if appropriate, the acid acceptor are m general employed in approximately equimolar amounts. However, it is also

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possible to use one component or the other in a relatively large excess (up to
> mol)
Process (E) according to the invention is characterized in that thioamides of the formula (VII) in which A is as defined above are reacted with ketene acid halides of the formula (VI), in which V, W, X, Y and Z are as defined above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.
Diluents which can be employed in process variant (E) according to the invention are all inert organic solvents. Those preferably utilizable are hydrocarbons, such as o-dichlorobenzene, tetralin, toluene and xylene, furthermore ethers, such as dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, and additionally polar solvents, such as dimethyl sulphoxide, sulpholane, dimethylformamide and N-methy I -pyrrol idone.
Acid acceptors which can be used in carrying out process (E) according to the invention are all customary acid acceptors.
Those preferably utilizable are tertiary amines, such as tri ethyl am ine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecane (DBU), diazabicyclononene (DBN), Hiinig base and N,N-dimethyl-aniline.
When carrying out process (E) according to the invention, the reaction temperature can be varied within a relatively wide range. The reaction is expediently carried out at temperatures between 0°C and 250°C, preferably between 20°C and 220°C.
Process (E) according to the invention is expediently carried out under atmospheric pressure.
When carrying out process (E) according to the invention, the reaction components of the formulae (VII) and (VI) and, if appropriate, the acid acceptors are in general employed in approximately equimolar amounts. However, it is also possible to use one component or the other in a relatively large excess (up to ^ mol)

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Process (Fa) is characterized in that compounds of the formulae (I-l-a) to (I-5-a) are in each case reacted with carboxylic acid halides of the formula (VIII), if appropriate in the presence of a diluent and if appropriate in the presence of an
acid-binding agent.
Diluents which can be employed in process (Fa) according to the invention are all solvents inert to the acid halides. Those preferably utilizable are hydrocarbons, such as benzine, benzene, toluene, xylene and tetralin, furthermore halogen ohydro-carbons, such as methylene chloride, chloroform, carbon tetrachloride, chloro-benzene and o-dichlorobenzene, additionally ketones, such as acetone and methyl isopropyl ketone, furthermore ethers, such as diethyl ether, tetrahydrofuran and dioxane, moreover carboxylic acid esters, such as ethyl acetate, and also strongly polar solvents, such as dimethylformamide, dimethyl sulphoxide and sulpholane. If the stability to hydrolysis of the acid halide permits, the reaction can also be carried out in the presence of water.
In the reaction by process (Fa) according to the invention, suitable acid-binding agents are all customary acid acceptors. Those preferably utilizable are tertiary amines, such as triethylamine, pyridine, diazabicyclooctane (DABCO), diaza-bicycloundecene (DBU), diazabicyclononene (DBN), Hiinig base and N,N-dimeth-yl-aniline, furthermore alkaline earth metal oxides, such as magnesium and calcium oxide, additionally alkali metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate and also alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
In process (Fa) according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between -20°C and +150°C, preferably between 0°C and 100°C
When carrying out process (Fa) according to the invention, the starting substances of the formulae (1-1-a) to (1-5-a) and the carboxylic acid halide of the formula (VIII) are in general each used in approximately equivalent amounts. However, it is also possible to employ the carboxylic acid halide in a relatively large excess (up to *> mol). Work-up is carried out according to customary methods.

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Process (F(3) is characterized in that compounds of the formulae (I-1-a) to (I-5-a) are each reacted with carboxylic anhydrides of the formula (IX), if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding
agent.
Diluents which can be used in process (FP) according to the invention are preferably those diluents which are also suitable when using acid halides. Otherwise, a carboxylic anhydride employed in excess can also simultaneously function as diluent.
Possible acid-binding agents optionally added in process (F(3) are preferably those acid-binding agents which are also suitable when using acid halides.
The reaction temperature in process (F(3) according to the invention can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between -20°C and + 150°C, preferably between 0°C and 100°C.
When carrying out process (F(3) according to the invention, the starting substances of the formulae (1-1-a) to (I-5-a) and the carboxylic anhydride of the formula (XI) are in general used in approximately equivalent amounts in each case. However, it is also possible to employ the carboxylic anhydride in a relatively large excess (up to 5 mol). Work-up is carried out according to customary methods.
In general, a procedure is used in which diluent and carboxylic anhydride present in excess and also the resulting carboxylic acid are removed by distillation or by washing with an organic solvent or with water.
Process (G) is characterized in that compounds of the formulae (I-l-a) to (I-5-a) are each reacted with chloroformic acid esters or chloroformic acid thioesters of the formula (X), if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent.
Possible acid-binding agents in process (G) according to the invention are all customary acid acceptors. Those preferably utilizable are tertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBA, Hunig base and N,N-dimethyl-aniline, furthermore alkaline earth metal oxides, such as magnesium and calcium

L_e_A_3> J_6£>jkForeign Countries
oxide, additionally alkali metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate and also alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.
Diluents which can be employed in process (G) according to the invention are all solvents which are inert to the chloroformic acid esters or chloroformic acid thio-esters. Those preferably utilizable are hydrocarbons, such as benzine, benzene, toluene, xylene and tetralin, further halogenohydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichloroben/ene, additionally ketones, such as acetone and methyl isopropyl ketone, furthermore ethers, such as diethyl ether, tetrahydrofuran and dioxane, moreover carboxylic acid esters, such as ethyl acetate, furthermore nitriles, such as acetonitrile, and also strongly polar solvents, such as dimethylformamide, dimethyl sulphoxide and sulpholane.
When carrying out process (G) according to the invention, the reaction tempera-lure can be varied within a relatively wide range. The reaction temperature is in general between -20°C and +100°C, preferably between 0°C and 50°C.
Process (G) according to the invention is in general carried out under atmospheric
pressure
When carrying out process (G) according to the invention, the starting substances of the formulae (I-l-a) to (1-5-a) and the approporiate chloroformic acid esters or chloroformic acid thioesters of the formula (X) are in general each used in approximately equivalent amounts. However, it is also possible to employ one component or the other in a relatively large excess (up to 2 mol). Work-up is carried out according to customary methods. In general, a procedure is used in which precipitated salts which are deposited are removed and the reaction mixture which remains is concentrated by stripping off the diluent.
Process (H) according to the invention is characterized in that compounds of the formulae (l-l-a) to (I-5-a) are each reacted with (Ha) compounds of the formula (XI) in the presence of a diluent and if appropriate in the presence of an acid-binding agent or (H(5) carbon disulphide and then with alkyl halides of the

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formula (Xil), if appropriate in the presence of a diluent and if appropriate in the presence of a base.
In preparation process (Ha), about 1 mol of chloromonothioformic acid ester or chlorodithioformic acid ester of the formula (XI) is reacted at 0 to 120°C, preferably at 20 to 60°C, per mole of starting compound of the formulae (I-l-a) to
(I-5-a).
Possible diluents optionally added are all inert polar organic solvents, such as ethers, amides, sulphones, sulphoxides, but also halogenoalkanes.
Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably employed.
If, in a preferred embodiment, the enolate salt of the compounds (I-l-a) to (I-5-a) is prepared by addition of strong deprotonating agents, e.g. sodium hydride or potassium tertiary butoxide, the further addition of acid-binding agents can be dispensed with.
If acid-binding agents are employed, customary inorganic or organic bases are suitable; sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine may be mentioned by way of example.
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The reaction can be carried out at atmospheric pressure or at elevated pressure; it is preferably carried out at normal pressure. Work-up takes place according to customary methods.
In preparation process (HP), the equimolar amount or an excess of carbon di-sulphide is in each case added per mole of starting compounds of the formulae (I-1-a) to (I-5-a). The reaction is in this case preferably carried out at temperatures from 0 to 50°C and in particular at 20 to 30°C.
Often it is expedient first to prepare the corresponding salt from the compounds of the formulae (1-1-a) to (I-5-a) by addition of a base (e.g. potassium tertiary butoxide or sodium hydride). The compounds (I-l-a) to (I-5-a) are each reacted with carbon disulphide until the formation of the intermediate compound is complete, e.g. after stirring at room temperature for several hours.
Bases which can be employed in process (HP) are all customary proton acceptors. Those preferably utilizable are alkali metal hydrides, alkali metal alkoxides, alkali metal or alkaline earth metal carbonates or hydrogen carbonates or nitrogen bases. Those which may be mentioned, for example, are sodium hydride, sodium meth-oxide, sodium hydroxide, calcium hydroxide, potassium carbonate, sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclononene (DBN) and diazabicyclo-undecene (DBU).
Diluents which can be used in this process are all customary solvents.
Those preferably utilizable are aromatic hydrocarbons such as benzene or toluene, alcohols such as methanol, ethanol, isopropanol or ethylene glycol, nitriles such as acetonitnle, ethers such as tetrahydrofuran or dioxane, amides such as dimethyl-formamide or other polar solvents such as dimethyl sulphoxide or sulpholane.
Further reaction with the alkyl halide of the formula (XII) is preferably carried out at 0 to 70°C and in particular at 20 to 50°C. In this case, at least the equimolar amount of alkyl halide is employed.
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The reaction is carried out at atmospheric pressure or at elevated pressure, preferably at atmospheric pressure.
Work-up is in turn carried out according to customary methods.
Process (1) according to the invention is characterized in that compounds of the formulae (I-l-a) to (I-5-a) are each reacted with sulphonyl chlorides of the formula (XIII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent.
In preparation process (I), about 1 mol of sulphonyl chloride of the formula (XIII) is reacted at -20 to 150°C, preferably at 0 to 70°C, per mole of starting compound of the formula (I-l-a to I-5-a).
Process (1) is preferably carried out in the presence of a diluent.
Possible diluents are all inert polar organic solvents, such as ethers, amides, ketones, carboxylic acid esters, nitriles, sulphones, sulphoxides or halogenated hydrocarbons such as methylene chloride.
Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide and methylene chloride are preferably employed.
If, in a preferred embodiment, the enolate salt of the compounds (I-l-a) to (I-5-a) is prepared by addition of strong deprotonating agents (e.g. sodium hydride or potassium tertiary butoxide), the further addition of acid-binding agents can be dispensed with.
If acid-binding agents are employed, customary inorganic or organic bases are suitable; those which may be mentioned by way of example are sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
The reaction can be carried out at atmospheric pressure or at elevated pressure, preferably it is carried out at atmospheric pressure. Work-up takes place according, to customary methods.
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Process (.1) according to the invention is characterized in that compounds of the formulae (1-1-a) to (I-5-a) are each reacted with phosphorus compounds of the formula (XIV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent.
In preparation process (J), to obtain compounds of the formulae (I-l-e) to (I-5-e), I to 2, preferably 1 to 1.3, mol of the phosphorus compound of the formula (XIV) are reacted at temperatures between -40°C and 150°C, preferably between -10 and 110°C, relative to 1 mol of the compounds (I-l-a) to (I-5-a).
Process (J) is preferably carried out in the presence of a diluent.
Possible diluents are all inert, polar organic solvents, such as ethers, carboxylic acid esters, halogenated hydrocarbons, ketones, amides, nitriles, sulphones, sulph-oxides etc
Acetonitrile, dimethyl sulphoxide, tetrahydrofuran, dimethyiformamide and methyl ene chloride are preferably employed.
Possible acid-binding agents optionally added are customary inorganic or organic bases such as hydroxides, carbonates or amines. Those which may be mentioned by way of example are sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine.
The reaction can be carried out at atmospheric pressure or at elevated pressure, preferably at atmospheric pressure. Work-up takes place according to customary methods of organic chemistry. The final products are preferably purified by crystallization, chromatographic purification or by so-called "incipient distillation", i.e. removal of the volatile constituents in vacuo.
Process (K) is characterized in that compounds of the formulae (I-l-a) to (I-5-a) are each reacted with metal hydroxides or metal alkoxides of the formula (XV) or amines of the formula (XVI), if appropriate in the presence of a diluent.
Diluents which can be employed in process (K) according to the invention are preferably ethers such as tetrahydrofuran, dioxane, diethyl ether or else alcohols such
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as methanol, ethanol, isopropanol, but also water. Process (K) according to the invention is in general carried out under atmospheric pressure. The reaction temperature is in general between -20°C and 100°C, preferably between 0°C and 50°C.
Process (L) according to the invention is characterized in that compounds of the formulae (I-l-a) to (I-5-a) are each reacted with (La) compounds of the formula (XVII), if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst, or (Lp) with compounds of the formula (XVIII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent.
In preparation process (La), about 1 mol of isocyanate of the formula (XVII) is reacted at 0 to IOO°C, preferably at 20 to 50°C, per mole of starting compound of the formulae (I-l-a) to (I-5-a).
Process (La) is preferably carried out in the presence of a diluent.
Possible diluents are all inert organic solvents, such as aromatic hydrocarbons, halogenated hydrocarbons, ethers, amides, nitriles, sulphones or sulphoxides.
Catalysts can optionally be added to accelerate the reaction. The catalysts employed can very advantageously be organotin compounds, e.g. dibutyltin dilau-
rate.
The reaction is preferably carried out at atmospheric pressure.
In preparation process (LP), about 1 mol of carbamoyl chloride of the formula (XVIII) is reacted at 0 to 150°C, preferably at 20 to 70°C, per mole of starting compound of the formulae (I-l-a) to (I-5-a).
Possible diluents optionally added are all inert polar organic solvents, such as ethers, carboxylic acid esters, nitriles, ketones, amides, sulphones, sulphoxides or
halogenated hydrocarbons.
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Dimethyl sulphoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably employed.
If, in a preferred embodiment, the enolate salt of the compound (I-l-a) to (I-5-a) is prepared by addition of strong deprotonating agents (e.g. sodium hydride or potassium tertiary butoxide), the further addition of acid-binding agents can be dispensed with.
If acid-binding agents are employed, customary inorganic or organic bases are suitable; those which may be mentioned by way of example are sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.
The reaction can be carried out at atmospheric pressure or at elevated pressure, preferably at atmospheric pressure. Work-up takes place according to customary methods
The active compounds are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnida, which are encountered in agriculture, in forestry, in the protection of stored products and of materials, and in the hygiene field. They are active against normally sensitive and resistant species and against all or some stages of development. The above-mentioned pests include:
From the order of the Isopoda, for example, Oniscus asellus, Armadillidium vulgare and Porcellio scaber.
From the order of the Diplopoda, for example, Blaniulus guttulatus.
From the order of the Chilopoda, for example, Geophilus carpophagus and
Scutigera spec
From the order of the Symphyla, for example, Scutigerella immaculata.
From the order of the Thysanura, for example, Lepisma saccharina.
From the order of the Collembola. for example, Onychiurus armatus.
From the order of the Orthoptera, for example, Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus,

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Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Schistocerca gregaria.
From the order of the Dermaptera, for example, Forficula auricularia. From the order of the Isoptera, for example, Reticulitermes spp..
From the order of the Anoplura, for example, Phylloxera vastatrix, Pemphigus
spp., Pediculus humanus corporis, Haematopinus spp. and Linognathus spp.
From the order of the Mallophaga, for example, Trichodectes spp. and Damalinea
spp.
From the order of the Thysanoptera, for example, Hercinothrips femoralis and
Thrips tabaci.
From the order of the Heteroptera, for example, Eurygaster spp., Dysdercus inter-
medius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp.
From the order of the Homoptera, for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis. Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psylla spp.
From the order of the Lepidoptera, for example, Pectinophora gossypiella, Bupalus pinianus, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp , Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana.
From the order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni,

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Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis and Costelytra zealandica.
From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa spp.
From the order of the Diptera, for example, Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hoitulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and Tipula paludosa.
From the order of the Siphonaptera, for example, Xenopsylla cheopis and
Ceratophyllus spp.
From the order of the Arachnida, for example, Scorpio maurus and Latrodectus
mactans.
From the order of the Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp, Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.
The active compounds according to the invention are distinguished by a high in-secticidal and acancidal activity.
They can be used to particularly good effect for controlling insects which are injurious to plants, such as, for example, against the larvae of the mustard beetle

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leaf hopper (Nephotettix cincticeps) or against the caterpillars of the cabbage moth (Plutella maculipennis).
The active compounds according to the invention can furthermore be used as defoliants, desiccants, agents for destroying broad-leaved plants and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
The dosages of the active compounds according to the invention necessary for controlling weeds are betweeen 0.001 and 10 kg/ha, preferably between 0.005 and 5 kg/ha.
The active compounds according to the invention can be used, for example, in connection with the following plants:
Dicotyledon weeds of the genera: Sinapis, Lepidium, Galiutn, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
Dicotyledon crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Bras-sica, Lactuca, Cucumis and Cucurbita.
Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cycnodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.
Monocotyledon crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

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However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
The compounds are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for controlling weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, on lawns, turf and pasture-land, and for the selective control of weeds in annual cultures.
The active compounds according to the invention are very highly suitable for the selective control of monocotyledon weeds in dicotyledon crops pre- and post-emergence. They can be employed to very good effect for the control of grass weeds, for example in cotton or sugar beet.
The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.
In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aro-matics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloro-elhylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly

Le A 31 661-Foreiun Countries
polar solvents, such as dimethyl form amide and dimethyl sulphoxide, as well as
water.
As solid carriers there are suitable:
for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as albumen hydrolysis products; as dispersing agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
The active compound according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations, as a mixture with other active compounds, such as insecticides, attractants, sterilizing agents, acaricides, nematicides, fungicides, growth-regulating

Le A 3 1 661-Foreimi Countries
substances or herbicides. The insecticides include, for example, phosphates, carb-amates, carboxylates, chlorinated hydrocarbons, phenylureas and substances produced by microorganisms.
Examples of particularly advantageous mixture components are the following compounds:
Fungicides:
2-aminobutane, 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2',6'-dibromo-2-
methyl- 4'-trifluoromethoxy-4'-trifluoro-methyl-l,3-thiazole-5-carboxanilide; 2,6-di-
chloro-N- (4-trifluoromethylbenzyl)benzamide; (E)-2-methoxyimino-N-methyl-2-(2-
phenoxy-phenyl)-acetamide; 8-hydroxyquinoline sulphate; methyl (E)-2-{2-[6-(2-
cyanophenoxy)-pyrimidin-4-yloxy]-phenyl }-3-methoxyacrylate; methyl (E)-
methoximino[alpha-(o-tolyloxy)-o-tolyl]acetate; 2-phenylphenol (OPP), aldimorph,
ampropylfos, anilazine, azaconazole,
benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol, blasticidin-S,
bromuconazole, bupirimate, buthiobate,
calcium polysulphide, captafol, captan, carbendazim, carboxin, quinomethionate,
chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cypro-
conazole, cyprofuram,
dichlorophen, diclobutrazol, diclofluanid, diclomezin, dicloran, diethofencarb,
difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap,
diphenylamine, dipyrithion, ditalimfos, dithianon, dodine, drazoxolon,
edifenphos, epoxyconazole, ethirimol, etridiazole,
fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fen-
propimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam,
fludioxonil, fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil,
flutriafol, folpet, fosetyl-aluminum, fthalide, fuberidazole, furalaxyl, furmecyclox,
guazatine,
hexachlorobenzene, hexaconazole, hymexazol,
irnazalil, imibenconazole, iminoctadine, iprobenfos (IBP), iprodione, iso-
prothiolane,
kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate,
copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux
mixture, mancopper, mancozeb, maneb, mepanipyrim, mepronil, metalaxyl,
metconazole, methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutanil,

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nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,
ofurace, oxadixyl, oxamocarb, oxycarboxin,
pefurazoate, penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin,
polycarbamate, polyoxin, probenazole, prochloraz, procymidone, propamocarb,
propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,
quintozene (PCNB),
sulfur and sulfur preparations,
tebuconazole, teclottalam, tecnazene, tetraconazole, thiabendazole, thicyofen, thio-
phanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol,
triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforine,
triticonazole,
validamycin A, vinclozolin,
zineb, ziram
Bactericides:
bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphate and other copper preparations.
Insecticides/Acaricides/Nematicides:
abamectin, abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb,
alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos
M, azocyclotin.
Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap, beta-cyfluthrin,
bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin,
butocarboxim, butylpyridaben,
cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,
CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos,
chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, cis-resmethrin,
clocythrin, clofentezine, cyanophos, cycloprothrin, cyfluthrin, cyhalothrin,
cyhexatin, cypermethrin, cyromazine,
deltamethrin, demeton-M, demeton-S, demeton-S-methyl, diafenthiuron, diazinon,
dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron, di-
methoate, dimethylvinphos, dioxathion, disulfoton,
edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox, etho-
prophos, etrimphos,

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fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb,
fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvaierate, fipronil,
fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvaiinate,
fbnophos, formothion, fosthiazate, fubfenprox, furathiocarb,
HCH, heptenophos, hexaflumuron, hexythiazox,
imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion, ivermectin,
lambda-cyhalothrin, lufenuron,
malathion, mecarbam, mevinphos, mesulfenphos, metaldehyde, methacrifos,
methamidophos, methidathion, methiocarb, methomyl, metolcarb, milbemectin,
monocrotophos, moxidectin,
naled, NC 184, NI 25, nitenpyram,
omethoate, oxamyl, oxydemethon M, oxydeprofos,
parathion A, parathion M, permethrin, phenthoate, phorate, phosalone, phosmet,
phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, profenofos,
promecarb, propaphos, propoxur, prothiofos, prothoate, pymetrozin, pyrachlophos,
pyridaphenthion, pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen,
quinalphos,
RH 5992,
salithion, sebufos, silafluofen, sulfotep, sulprofos,
tebufenozid, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, temephos,
terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb, thiofanox, thiomethon,
thionazin, thuringiensin, tralomethrin, triarathen, tnazophos, triazuron, trichlorfon,
triflumuron, trimethacarb,
vamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin.
Herbicides:
for example anilides such as, for example, diflufenican and propanil; arylcarb-oxylic acids such as, for example, dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids such as, for example, 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones such as, for example, chloridazon and norflurazon; carbamates such as, for example, chlorpropham, desmedipham, phenmedipham and propham; chloroacetanilides such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor, dinitroanilines such as, for

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example, oryzalin, pendimethalin and trifluralin; diphenyl ethers such as, for example, acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as, for example, chlortoluron, diuron, fluometuron, iso-proturon, linuron and methabenzthiazuron; hydroxylamines such as, for example, alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones such as, for example, imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles such as, for example, bromoxynil, dichlobenil and ioxynil; oxyacetamides such as, for example, mefenacet; sulfonylureas such as, for example, amido-sulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, met-sulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates such as, for example, butylate, cycloate, di-allate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and tri-allate; triazines such as, for example, atrazine, cyanazine, simazine, sime-tryn, terbutryn and terbutylazine; triazinones such as, for example, hexazinone, metamitron and metribuzin; others such as, for example, aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.
The active compound according to the invention can furthermore be present in its commercially available formulations and in the use forms prepared from these formulations, as a mixture with synergistic agents. Synergistic agents are compounds which increase the action of the active compounds, without it being necessary for the synergistic agent added to be active itself.
The active compound content of the use forms prepared from the commercially available formulations can vary within wide limits. The active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
The compounds are employed in a customary manner appropriate for the use
forms.
When used against hygiene pests and pests of stored products, the active compounds are distinguished by an excellent residual action on wood and clay as well as a good stability to alkali on limed substrates.

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The active compounds according to the invention are not only active against plant, hygiene and stored-product pests, but also, in the veterinary medicine sector, against animal parasites (ectoparasites), such as ixodid ticks, argasid ticks, scab mites, trombiculid mites, flies (stinging and sucking), parasitic fly larvae, lice, hair lice, bird lice and fleas. These parasites include:
From the order of the Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
From the order of the Mallophagida and the sub-orders Amblycerina and Isochnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp..
From the order of the Diptera and the sub-orders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp, Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp , Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp..
From the order of the Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Xenopsylla spp and Ceratophyllus spp..
From the order of the Heteropterida, for example, Cimex spp., Triatoma spp., Khodnius spp and Panstrongylus spp..
From the order of the Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattela gennanica and Supella spp..
From the sub-class of the Acaria (Acarida) and the orders of the Meta- and Mesostigmata, for example Argas spp., Ornithodorus spp., Otabius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemaphysalis spp..

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Ilyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp , Sternostoma spp. and Varroa spp..
From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp. and Laminosioptes spp..
For example, they show an outstanding activity against Boophilus microplus and Lucilia cuprina
The active compounds of the formula (I) according to the invention are also suitable for combating arthropods which attack agricultural livestock, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, honey bees, other domestic animals, such as, for example, dogs, cats, cage birds, aquarium fish, and so-called experimental animals, such as, for example, hamsters, guinea-pigs, rats and mice. By combating these arthropods, it is intended to reduce mortality and decreased performance (in meat, milk, wool, hides, eggs, honey and the like), so that more economical and simpler animal keeping is made possible by using the active compounds according to the invention
In the veterinary sector, the active compounds according to the invention are used in a known manner by enteral administration, for example in the form of tablets, capsules, drinks, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, such as, for example, by means of injections (intramolecular, subcutaneous, intravenous, intraperitoneal and the like), implants, by nasal application, by dermal administration, for example in the form of dipping or bathing, spraying, pouring-on and spotting-on, washing, dusting, and with the aid of shaped articles which comprise active compound, such as collars, ear tags, tail marks, limb bands, halters, marking devices and the like.
When administered to livestock, poultry, domestic animals and the like, the active compounds of the formula (I) can be used as formulations (for example powders,

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emulsions, flowables) which comprise the active compounds in an amount of 1 to 80% by weight, either directly or after dilution by a factor of 100 to 10,000, or they may be used in the form of a chemical bath.
Furthermore, it has been found that the compounds of the formula (I) according to the invention have a potent insecticidal action against insects which destroy industrial materials
The following insects may be mentioned by way of example and as being preferred, but without any limitation:
Beetles, such as
Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Pulinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec., Tryptodendron spec, Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec., Dinoderus minutus.
Dermapterans, such as
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
Termites, scuh as
Kalotermes tlavicollis, Cryptotermes brevis, Heterotermes indicola, Recticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevdensis, Coptotermes formosanus.
Bristletails, such as Lepisma saccharina.
Industrial materials are to be understood as meaning, in the present context, non-live materials, such as, preferably, synthetic materials, glues, sizes, paper and board, leather, wood and timber products, and paint.
The materials lo be very particularly protected against attack by insects are wood and timber products

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Wood and timber products which can be protected by the composition according to the invention or mixtures comprising such a composition are to be understood as meaning, for example, construction timber, wooden beams, railway sleepers, bridge components, jetties, wooden vehicles, boxes, pallets, containers, telephone poles, wood lagging, windows and doors made of wood, plywood, particle board, joiner's articles, or wood products which, quite generally, are used in the construction of houses or in joinery.
The active compounds can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes.
The formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersant and/or binder or fixative, water repellent, if appropriate desiccants and UV stabilizers and, if appropriate, colorants and pigments and other processing auxiliaries.
The insecticidal compositions or concentrates used for the protection of wood and wooden materials comprise the active compound according to the invention at a concentration of 00001 to 95% by weight, in particular 0.001 to 60% by weight.
The amount of the compositions or concentrates employed depends on the species and the occurrence of the insects and on the medium. The optimum rate of application can be determined upon use in each case by test series. However, in general, it suffices to employ 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
The solvent and/or diluent used is an organochemical solvent or solvent mixture and/or an oily or oil-type organochemical solvent or solvent mixture of low volatility and/or a polar organochemical solvent or solvent mixture and/or water and, if appropriate, an emulsifier and/or wetting agent.
Organochemical solvents which are preferably employed are oily or oil-type solvents having an evaporation number of above 35 and a flashpoint of above .iO°(\ preferably above 45°C Substances which are used as such oily and oil-type

Le A 31 66l-F"oreign Countries
solvents which have low volatility and are insoluble in water are suitable mineral oils or their aromatic fractions, or mineral-oil-containing solvent mixtures, preferably white spirit, petroleum and/or alkylbenzene.
Substances which are advantageously used are mineral oils with a boiling range of 170 to 220°C, white spirit with a boiling range of 170 to 220°C, spindle oil with a boiling range of 250 to 350°C, petroleum or aromatics of boiling range 160 to 280°C, essence of terpentine and the like.
In a preferred embodiment, liquid aliphatic hydrocarbons with a boiling range of 180 to 210°C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range of 180 to 220°C and/or spindle oil and/or monochloro-naphthalene, preferably a-monochloronaphthalene, are used.
The organic oily or oil-type solvents of low volatility having an evaporation number of above 35 and a flashpoint of above 30°C, preferably above 45°C, can be partially replaced by organochemical solvents of high or medium volatility, with the proviso that the solvent mixture also has an evaporation number of above 35 and a flashpoint of above 30°C, preferably above 45°C, and that the in-sectide/fungicule mixture is soluble or emulsifiable in this solvent mixture.
In a preferred embodiment, part of the organochemical solvent or solvent mixture is replaced by an aliphatic polar organochemical solvent or solvent mixture. Substances which are preferably used are aliphatic organochemical solvents having hydroxyl and/or ester and/or ether groups, such as, for example, glycol ether, esters and the like.
The organochemical binders used within the scope of the present invention are the synthetic resins and/or binding drying oils which are known per se and can be diluted with water and/or are soluble or dispersible or emulsifiable in the organochemical solvents employed, in particular binders composed of, or comprising, an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, poly-condensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenol resin, hydrocarbon resin, such as indene/coumarone resin, silicone resin, drying vegetable and/or drying oils and/or physically drying binders based on a natural and/or synthetic resin.

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The synthetic resin used as the binder can be employed in the form of an emulsion, dispersion or solution. Up to 10% of bitumen or bituminous substances can also be used as binders. In addition, colorants, pigments, water repellents, odour-masking substances and inhibitors or anticorrosives known per se and the like can also be employed.
The composition or the concentrate preferably comprises, in accordance with the invention, at least one alkyd resin or modified alkyd resin and/or a drying vegetable oil as the organochemical binder. Preferably used according to the invention are alkyd resins with an oil content of over 45% by weight, preferably 50 to 68% by weight.
All or some of the abovementioned binder can be replaced by a fixative (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active compounds and crystallization or precipitation. They preferably replace 001 to 30% of the binder (based on 100% of binder employed).
The plasticizers are from the chemical classes of the phthalic esters, such as dibutyl phthalate, dioctyl phthalate or benzylbutyl phthalate, the phosphoric esters, such as tributyl phosphate, the adipic esters, such as di-(2-ethylhexyl) adipate, the stearates, such as butyl stearate or amyl stearate, the oleates, such as butyl oleate, the glycerol ethers or relatively high-molecular-weight glycol ethers, glycerol esters and p-toluene-sulphonic esters.
Fixatives are chemically based on polyvinyl alkyl ethers, such as, for example, polyvinyl methyl ether, or ketones, such as benzophenone or ethyl enebenzo-phenone.
Particularly suitable as a solvent or diluent is also water, if appropriate as a mixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants.
Particularly effective protection of wood is achieved by large-scale industrial impregnation processes, for example vacuum, double-vacuum or pressure processes.

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If appropriate, the ready-to-use compositions can additionally comprise other insecticides and, if appropriate, additionally one or more fungicides.
Suitable additional components which may be admixed are, preferably, the insecticides and fungicides mentioned in WO 94/29 268. The compounds mentioned in that document are expressly part of the present application.
Very particularly preferred components which may be admixed are insecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron,
and fungicides, such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlofluanid, tolylfluanid, 3-iodo-2-propinylbutyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.
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The preparation and the use of the active compounds according to the invention can be seen from the examples which follow.
Preparation Examples Example (i-l-a-1)


O
Under reflux, 29.6 g (0.0764 mol) of the compound prepared by the method of Example (II-1) in 160 ml of anhydrous toluene are added dropwise to 22.7 g (0.2 mol) of potassium tert-butoxide in 60 ml of anhydrous tetrahydrofuran (THF), and the mixture is stirred under reflux for 1.5 hours. For work-up, 230 ml of water are added, the aqueous phase is separated off, the toluene phase is extracted with 1 10 ml of water, and the aqueous phases are combined, washed with toluene and acidified at 10 to 20°C with cone. HC1 to pH 1. The product is filtered off under suction, washed, dried and washed by stirring in methyl tert-butyl ether (MTB) ether/n-hexane.
Yield 13.7 g (56% of theory), mp.: 220°C.
The compounds of the formula (I-l-a) given below were prepared analogously or in accordance with the general preparation instructions:
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0000000At 0 to 10°C, 1.2 ml (0.012 mol) of ethyl chloroformate in 5 ml of anhydrous methylene chloride are added dropwise to 3.84 g (0.012 mol) of the compound prepared by the method of Example (I-l-a-1) and 1.7 ml (0.012 mol) of triethylamine in 70 nil of anhydrous CH2C12, and the mixture is stirred at room temperature until the reaction has ended (TLC check). For work-up, the mixture is washed twice with 50 ml of 0.5 N aqueous sodium hydroxide solution, dried over magnesium sulphate and evaporated.
Yield: 3.6 g (76% of theory), mp.: >220°C.
The compounds of the formula (I-l-c) given below are obtained analogously or in accordance with the general preparation instructions:

H
O W


At 30 to 40°C, 16.7 g (0.0544 mol) of the compound prepared by the method of Example (XXIX-1) in 160 ml of anhydrous methylene chloride are added drop-wise to 26.6 g (0.257 mol) of cone, sulphuric acid, and the mixture is stirred for 2 hours at this temperature. 37 ml of absolute methanol are then added in such a way that the internal temperature is about 40°C, and stirring is continued at 40 to 70°C for a further 6 hours.
For work-up, the mixture is poured on 0.28 kg of ice, extracted with methylene chloride, washed with aqueous sodium bicarbonate solution, dried and evaporated. The residue is recrystallized from methyl tert-butyl ether/n-hexane.
Yield 16.5 g (89% of theory), mp.: 168°C.
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15.9 g (0.08 mol) of 3-chloro-2,6-dimethylphenylacetic acid and 17.7 ml (0.24 mol) of thionyl chloride are stirred for 30 minutes at room temperature and subsequently at 80°C until the evolution of gas has ceased. Excess thionyl chloride is removed at 50°C under reduced pressure. 50 ml of anhydrous toluene are then added, and the solution is evaporated once again. The residue is taken up in 100 ml of anhydrous THF (solution 1).
At 0 to 10°C, solution 1 is added dropwise to 16.8 g of methyl cis-4-methylcyclo-hexylamine-1-carboxylate and 24.6 ml (0.176 mol) of triethylamine in 160 ml of anhydrous THF, and the solution is subsequently stirred at room temperature for 1 hour. The mixture is filtered under suction, washed with anhydrous THF and evaporated. The residue is taken up in methylene chloride, washed with 0.5 N HC1, dried and evaporated. The crude product is recrystallized from methyl tert-butyl ether/n-hexane.
Yield 269 g (74% of theory), mp.: 163°C.
The compounds of the formula (II) given below are prepared analogously to Examples (11-1) and (II-2) and in accordance with the general preparation instructions.

rmula (II)



Le A J1_MI-Foreign .ilQuntnes


1 drop of dimethylformamide (DMF) and then 11.4 g (96 mmol) of thionyl chloride are added to 18 g (64 mmol) of the compound


(Formula Removed)

in 70 ml of absolute toluene. The solution is stirred for 5 minutes at room temperature and subsequently at 100°C until the gas formation has ended. The mixture is concentrated under reduced pressure, treated twice with toluene which is distilled off again in each case, and the mixture is subsequently stirred for 1 hour under high vacuum. The acid chloride obtained is dissolved in 40 ml of absolute tetrahydrofuran (THF) (solution A).
At about 0°C, 57 ml (177 mmol) of a solution of lithium diisopropylamide (LDA) in [lacuna] are initially charged in 100 ml of absolute THF. At this temperature, 22.1 g (107 mmol) of methyl 2,3,4,6-tetramethylphenylacetate dissolved in 40 ml of absolute THF are added dropwise, and stirring is continued for a further 30
minutes.

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Subsequently, again at about 0°C, solution A is added dropwise and the mixture is stirred for I hour without cooling.
The mixture is admixed with 350 ml of MTB ether and a few drops of water, washed twice with 10% strength aqueous ammonium chloride solution, and the organic phase is dried and concentrated. The crude product is stirred with petroleum ether. The product is filtered off with suction and dried.




2.4 g (10 rnmol) of 2,3,5,6-tetramethyl-phenyl-chlorocarbonyl ketene are initially charged in 20 ml of toluene (p.a.). At room temperature, 1.35 g (10 mmol) of 2-pyridyl ethyl ketone are added, and the solution is stirred under reflux for 8 hours. On cooling, the product crystallizes out. The precipitate is filtered off under suction and washed twice with cyclohexane.
Yield: 1.4 g (41% of theory), mp.: 202-205°C.
The compounds of the formula (I-4-a) given in the table below were prepared analogously to Example (I-4-a-1) or according to the general preparation instructions:
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(Formula Removed)


1.7 g (5 mmol) of the compound prepared by the method of Example I-4-a-6 are initially charged in 20 ml of ethyl acetate p.a.. At 20°C, 0.5 g (5 mmol) of triethylamine are added, and at 0°C 0.39 g (5 mmol) of C1COCH3 in 5 ml of ethyl acetate are added dropwise. The reaction is carried out with the exclusion of moisture. The mixture is stirred at 20°C for 20 hours. The precipitate is separated off and washed with ethyl acetate. The organic phase is washed with twice 25 ml of half-concentrated NaCl solution, dried over sodium sulphate and evaporated.
Yield: 1 g (53% of theory), mp.: 170 to 172°C.
The compounds of the formula (I-4-b) given below are obtained analogously or in accordance with the general preparation instructions.
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1.7 g (5 mmol) of the compound prepared by the method of Example I-4-a-6 are initially charged in 20 ml of ethyl acetate p.a.. At 20°C, 0.5 g (5 mmol) of tri-ethylamme are added, and at 0°C 0.47 g (5 mmol) of C1CO2CH3 in 5 ml of ethyl acetate are added dropwise. The reaction is carried out with the exclusion of moisture The mixture is stirred at 20°C for 20 hours. For work-up, the precipitate is separated off and washed with ethyl acetate. The organic phase is washed with twice 25 ml of half-concentrated NaCI solution, dried over sodium sulphate and evaporated.
Yield: ! 0 g (Sl% of theory), mp.: 136 to 139°C.
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are added dropwise to 15 g (63.5 mmol) of the compound prepared by the method of Example (XXXIII-1) in 20 ml of toluene, and the solution is stirred initially for 1 hour at room temperature and then at about 95°C overnight. After cooling, HC1 and SO-, are blown off at about 45°C by passing argon through the solution, and remaining volatile compounds are subsequently removed using high vacuum.
Yield: 7.4 g (52% of theory), bp.: 110-111°C/0.08 mbar. Example (VI-2)
Analogously to Example (VI-1) or according to the general preparation procedures, the compound

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At room temperature, 40 g (0.155 mol) of the compound prepared by the method of Example (XXXIV-1) are added to 28.2 g of potassium hydroxide in 37.8 g of water and 75 6 ml of methanol, and the mixture is heated under reflux for 10 hours.
After cooling, the mixture is concentrated under reduced pressure, the residue is dissolved in about 100 ml of ice water and, while cooling, acidified with half-concentrated hydrochloric acid. The phases are separated and extracted with toluene. The solid which separates off is filtered off with suction, stirred with a little toluene and filtered off under suction once more.
Yield: 35.20 g (703% of theory), mp.: 193-198°C. Example (XXXII1-2)
Analogously to Example (XXXIII-1) or according to the general preparation instructions, the compound


CO2H
of mp.: 18I°C (decomposition) is obtained.
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At room temperature, 350 g (3.5 mol) of dimethyl carbonate and then, slowly, at 85-90°C, 42.0 g (0.203 mol) of methyl 2,3,5,6-tetramethylphenylacetate are added dropwise to 7.9 g (0.264 mol) of 80% strength sodium hydride, and the mixture is stirred overnight. After cooling, a little methanol is added to the mixture which is then poured into about 1 1 of ice water and acidified with half-concentrated hydrochloric acid. The organic phase is separated off, the aqueous phase is extracted with toluene, and the combined organic phases are dried and concentrated. The residue is subsequently distilled using high vacuum
Yield: 41 9 g (82% of theory), mp.: 125-129°C.
Analogously to Example (XXXIV-1) and according to the general preparation instructions, the compound

At room temperature, 171.9 g of the compound prepared by the method of Example XXVI-1 are added dropwise to a mixture of 85.8 g (1.532 mol) of KOH in 110.2 ml of water and 224 ml of methanol, and the mixture is heated under reflux for 5 h After cooling, the mixture is diluted with 300 ml of water and washed with methyl tert-butyl ether. The aqueous phase is acidified with half-concentrated hydrochloric acid, filtered off with suction and dried, and the residue is recrystallized from toluene.
Yield: 11 1.4 g ( A 69% of theory) mp.: 128-130°C.
The compounds of the formula (XXIII) given below were obtained analogously to Example (XX11I-1) and according to the general preparation instructions:
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Le_A JLL^ALrlloreign Countries
The compounds of the formula (XXIV) given below were obtained analogously to Hxample (XX1V-1) and according to the general preparation instructions:
Table 67

These compounds were employed directly for synthesis as crude products for preparing compounds of the formula (XXIII)
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2205 g (22.8 mol) of 1,1-dichloroethylene (vinylidene chloride) are added drop-wise to a well-cooled mixture of 229.7 g (2.27 mol) of tert-butyl nitrite and 255 g (1 776 mol) of anhydrous copper-(II) chloride in 990 ml of anhydrous acetonitrile, the mixture being kept at room temperature. Then, at a temperature of below 30°C, a mixture of 232 g (1.49 mol) of 3-chloro-2,6-dimethylaniline in 1500 ml of anhydrous acetonitrile is added dropwise. At room temperature, the mixture is stirred until the formation of gas has ceased, and the mixture is then carefully poured into 6 litres of 20% strength hydrochloric acid and extracted with methylene chloride. The organic phases are combined, washed once more with 20% strength hydrochloric acid, dried and concentrated. The remaining oil is used without any further work-up for the reaction of Example (XXIV-1).
The compounds of the formula (XXV) given below were obtained analogously to Example (XXV-1) and according to the general preparation instructions:
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TThe compounds listed in Table 68 were employed as crude products in the saponification reaction leading to compounds of the formula (XXIV), and were, for that reason, not further characterized.
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Use Examples Example 1
Phaedon larvae test
Solvent: 7 parts by weight of dimethylformamide
Hmulsifier: I part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of the active compound of the desired concentration and are infested with mustard beetle larvae (Phaedon cochleariae) while the leaves are still moist.
After the specified period of time, the destruction in % is determined. 100% means that all the beetle larvae have been killed; 0% means that none of the beetle larvae have been killed.
In this test, for example the compounds of Preparation Examples (I-l-a-2), (I-l-a-3), (1-l-b-l), (l-l-b-2) and (I-l-c-1) at an exemplary active compound concentration of 1000 ppm caused a destruction of 100% after 7 days
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Tetranychus test (OP resistant/spray treatment)
Solvent: 3 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentrations.
Bean plants (Phaseolus vulgaris) heavily infected by all stages of the spider mite (Tetranychus urticae) are sprayed with a preparation of the active compound of the desired concentration
After the specified period of time, the destruction in % is determined. 100% means that all spider mites have been killed; 0% means that none of the spider mites have been killed.
In this test, an activity of 100% was shown, after 7 days, for example by the compound of Preparation Example (I-l-a-2) at an exemplary active compound concentration of 1000 ppm.

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Plutella test
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are infested with caterpillars of the diamond-back moth (Plutella maculipennis) while the leaves are still moist.
After the specified period of time, the destruction in % is determined. 100% means that all the caterpillars have been killed; 0% means that none of the caterpillars have been killed
In this test, for example the compounds of Preparation Examples (I-l-a-3), (1-1-b-1), (l-l-b-2), (l-l-b-6) and (I-l-c-1) at an exemplary active compound concentration of 0.1% caused a destruction of 100% after 7 days.
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Spodoptera test
Solvent: 7 parts by weight of dimethylformamide
Emulsifiei: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of the active compound of the desired concentration and are infested with caterpillars of the owlet moth (Spodoptera frugiperda), as long as the leaves are still moist
After the specified period of time, the destruction in % is determined. 100% means that all the caterpillars have been killed; 0% means that none of the caterpillars have been killed.
In this test, for example the compounds of Preparation Examples (I-l-a-2), (I-l-a-3) and (I-l-b-4) at an exemplary active compound concentration of 0.1% caused a destruction of at least 80% after 7 days.
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Nephotettix test
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Rice seedlings (Oryzae sativa) are treated by being dipped into the preparation of the active compound of the desired concentration and are infested with larvae of the green rice leafhopper (Nephotettix cincticeps) while the seedlings are still
moist.
After the specified period of time, the destruction in % is determined. 100% means that all the leafhoppers have been killed, 0% means that none of the leafhoppers have been killed.
In this test, for example, the compounds of Preparation Examples (I-l-a-1), (I-l-a-2), (1-1-a-3), (I-l-b-1), (I-l-b-2), (I-l-b-3), (1-1 -b-4), (I-l-b-5), (I-l-b-6) and (I-i-c-2) at an exemplary active compound concentration of 0.1% caused a destruction of 100% after 6 days.
L§A JJ_i>iil-lH>reigO....Countries
My/Ais test
Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Cabbage leaves (Brassica oleracea) which have been heavily infested with the peach aphid (Myzus persicae) are treated by being dipped into the preparation of the active compound of the desired concentration.
After the specified period of time, the destruction in % is determined. 100% means that all the aphids have been killed; 0% means that none of the aphids have been killed
In this test, for example, the compounds according to Preparation Examples (I-l-a-1), (i-l-a-2), (I-l-a-3), (I-l-b-2), (I-l-b-3) and (I-2-a-l) at an exemplary active compound concentration of 0.1% caused a destruction of at least 80% after
h days.

Example 7
'I'ctranychus test (OP resistant/dip treatment)
Solvent: 3 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
Bean plants (Phaseolus vulgaris) heavily infected by all stages of the spider mite (Tetranychus urticae) are dipped into a preparation of the active compound of the desired concentration.
After the specified period of time, the destruction in % is determined. 100% means that all spider mites have been killed; 0% means that none of the spider mites have been killed.
In this test, a destruction of 100% was caused, after 5 days, for example by the compounds of Preparation Examples (I-l-a-1), (I-l-a-2), (I-l-a-3), (I-l-b-2) and (1-2-b-l) at an exemplary active compound concentration of 0.1%.



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We Claim:
1. Substituted phenylketoenols compounds of the formula (I)
(Formula Removed)
wherein
Y represents hydrogen, halogen, alkyl or alkoxy,
W represents cyano, nitro, halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenoalkyl, halogenoalkoxy, respectively optionally substituted phenyl, phenoxy, phenylthio, phenylalkoxy or phenylalkylthio,
X represents hydrogen, halogen, alkyl, alkenyl, alkinyl, alkoxy, halogenoalkyl, halogenoalkoxy, cyano, nitro or respectively optionally substituted phenyl, phenoxy, phenylthio, phenylalkyloxy or phenylalkylthio,
Y represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,
halogenoalkoxy, cyano or nitro,
Z represents halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy, hydroxyl, cyano, nitro or respectively optionally substituted phenoxy, phenylthio, 5- to 6-membered hetaryloxy, 5- to 6-membered hetarylthio, phenylalkyloxy or phenylalkylthio,
Y and Z represent together with the carbon atoms that they are attached
to an optionally substituted cycle which is optionally interrupted by one or more heteroatoms, V, X and W having one of the above-mentioned meanings, or
W and Z represent together with the carbon atoms that they are attached to an optionally substituted cycle which is optionally interrupted

by one or more heteroatoms, V, X and Y having one of the above-mentioned meanings,
Het represents one of the groups

(Formula Removed)
in which
A represents hydrogen, respectively optionally halogen-sub¬stituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, respectively saturated or unsaturated and optionally substituted cycloalkyl or heterocyclyl or respectively optionally halogen-, alkyl-, halogenoalkyl-, alkoxy-, halogenoalkoxy-, cyano- or nitro- substituted aryl, arylalkyl or hetaryl,
B represents hydrogen, alkyl or alkoxyalkyl, or
A and B represent together with the carbon atom that they are attached to a saturated or unsaturated optionally substituted carbocycle or heterocycle,

D represents hydrogen or an optionally substituted radical from the group consisting of alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl, saturated or unsaturated heterocyclyl, arylalkyl, aryl, hetarylalkyl or hetaryl, or
A and D represent together with the atoms that they are attached to a respectively optionally substituted carbocycle or heterocycle,
G represents hydrogen (a) or one of the groups

(Formula Removed)

in which,
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulphur,
M represents oxygen or sulphur,
R1 represents respectively optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl or respectively optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl or heterocyclyl or respectively optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxy alkyl,
R2 represents respectively optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl or respectively optionally substituted cycloalkyl, phenyl or benzyl,

R3, R4and R5 each represent independently of one another respectively optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkyl thio, alkenylthio or cycloalkylthio or respectively optionally substituted phenyl, benzyl, phenoxy or phenylthio,
R6 and R7 each represent independently of one another hydrogen, respectively optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl or respectively optionally substituted phenyl or benzyl, or represent together with the N-atom that they are attached to an optionally oxygen- or sulphur-containing and optionally substituted cycle,
provided that in case of Het = group (2), V is substituted by hydrogen, alkyl or alkoxy.
2. Process for preparing compounds of the formula (I) as claimed in claim 1, wherein
(A) compounds of the formula (I- 1-a)

(Formula Removed)
in which
A, B, V, W, X, Y and Z are each as defined above, are obtained by the intramolecular condensation of
compounds of the formula (II)

(Formula Removed)
in which,
A, B, V, W, X, Y and Z are each as defined above
and
R8 represents alkyl (preferably C1-C6-alkyl)
in the presence of a diluent and in the presence of a base,
(B) compounds of the formula (I-2-a)

(Formula Removed)
in which
A, B, V, W, X, Y and Z are each as defined above
are obtained by the intramolecular condensation of
compounds of the formula (III)

(Formula Removed)
in which
A, B, V, W, X, Y, Z and R8 are each as defined above
in the presence of a diluent and in the presence of a base,
(C) compounds of the formula (I-3-a)

(Formula Removed)
in which
A, B, V, W, X, Y and Z are each as defined above
are obtained by the intramolecular cyclization of
compounds of formula (IV)

(Formula Removed)

in which
A, B, V, W, X, Y, Z and R8 are each as defined above and
T represents hydrogen, halogen, alky (preferably C1-C6-alkyl) or alkoxy (preferably C1-C8-alkoxy),
if appropriate in the presence of a diluent and in the presence of an acid,
(D) compounds of the formula (I-4-a)

(Formula Removed)
in which
A, D, V, W, X, Y and Z are each as defined above
are obtained by reacting
compounds of the formula (V)
(Formula Removed)
in which
A and D are each as defined above
or their silyl enol ethers of the formula (Va)

(Formula Removed)
in which
A and D are each as defined above and R8 represents alkyl (preferably methyl) with compounds of the formula (VI)

(Formula Removed)
in which
V, W, X, Y and Z are each as defined above and
Hal represents halogen (preferably chlorine or bromine),
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor,
(E) compounds of the formula (I-5-a)

(Formula Removed)
in which

A, V, W, X, Y and Z are each as defined above
are obtained by reacting compounds of the formula (VII)

(Formula Removed)
in which
A is as defined above
with compounds of the formula (VI)

(Formula Removed)
in which
Hal, V, W, X, Y and Z are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor, and by optionally subsequently reacting the compounds of the formulae (I-l-a) to (I-5-a) obtained in this manner
(Fα) with acid halides of the formula (VIII)
(Formula Removed)
in which
R1 is as defined above and

Hal represents halogen (in particular chlorine or bromine)
or (Fß) with carboxylic anhydrides of the formula (IX)
(Formula Removed)
in which
R1 is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent;
or
(G) with chloroformic esters or chloroformic thioesters of the formula (X)
(Formula Removed)
in which
R2 and M are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent;
or
(Hα) with chloromonothioformic esters or chlorodithioformic esters of the formula (XI)
(Formula Removed)

in which
M and R2 are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent
or
(Hα) with carbon disulphide and subsequently with compounds of the formula (XII)
(Formula Removed)
in which
R2 is as defined above and
Hal represents chlorine, bromine or iodine,
if appropriate in the presence of a diluent and if appropriate in the presence of a base,
or
(I) with sulphonyl chlorides of the formula (XIII)
(Formula Removed)
in which
R3 is as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent,
or
(J) with phosphorus compounds of the formula (XIV)
(Formula Removed)
in which
L, R4 and R5 are each as defined above and
Hal represents halogen (in particular chlorine or bromine),
if appropriate in the presence of a diluent and if appropriate in the presence of acid-binding agent,
or
(K) with metal compounds or amines of the formulae (XV) or (XVI)

(Formula Removed)

in which
Me represents a mono- or divalent metal (preferably an alkali metal or an alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium),
t represents the number 1 or 2 and
R10, R11, R12 each independently of one another represent hydrogen or alkyl (preferably C1-C8-alkyl),
if appropriate in the presence of a diluent,
or
(Lα) with isocyanates or isothiocyanates of the formula (XVII)

(Formula Removed)
in which
R6 and L are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or
(Lß) with carbamoyl chlorides or thiocarbamoyl chlorides of the formula (XVIII)
(Formula Removed)
in which
L, R6 and R7 are each as defined above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent.
3. Compounds of the formula (I) as claimed in claim 1 wherein
V represents hydrogen, halogen, C1-C6-alkyl or C1-C6-alkoxy,
W represents cyano, nitro, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C1-C6-alkoxy, C1-C4-halogenoalkyl, C1-C4-halogenoalkoxy or respectively optionally halogen-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C4-halogenoalkyl-, C1-C4-halogenoalkoxy-, nitro- or cyano substitute phenyl, phenoxy, phenylthio, phenyl-C1-C4-alkoxy or phenyl-C1-C4-alkylthio,
X represents hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, C1-C6-alkoxy, C1-C4-halogenoalkyl, C1-C4-halogenoalkoxy, cyano, nitro or respectively optionally halogen-, V-C6-alkyl-, C1-

C6-alkoxy-, C1-C4-halogenoalkyl-, C1-C4-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenoxy, phenylthio, phenyl-C1-C4-alkoxy or phenyl-C1-C4-alkylthio,
Y represents hydrogen, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-
halogenoalkyl, C1-C4-halogenoalkoxy, cyano or nitro,
Z represents halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-halogenoalkyl, C1-C4-halogenoalkoxy, hydroxyl, cyano, nitro or respectively optionally halogen-, C1-C4-alkyl-, C1-C4-alkoxy-, C1-C4-halogenoalkyl-, C1-C4-halogenoalkoxy-, nitro- or cyano-substituted phenoxy, phenylthio, thiazolyloxy, pyridinyloxy, pyrimidyloxy, pyrazolyloxy, phenyl-C1-C4-alkyloxy or phenyl-C1-C4-alkylthio, or,
Y and Z together represent respectively optionally halogen-, C1-C6-alkyl-,
C1-C6-alkoxy- or C1-C4-halogenoalkyl-substituted C3-C5-alkanediyl or C3-C5-alkenediyl in which one to three members can be optionally replaced independently of one another by oxygen, sulphur, nitrogen or a carbonyl group, or
W and Z together represent respectively optionally halogen-, C1-C6-alkyl-, C1-C6-alkoxy- orC1-C4-halogenoalkyl-substituted C3-C5-alkanediyl or C3-C5-alkenediyl in which one to three members can be optionally replaced independently of one another by oxygen, sulphur, nitrogen or a carbonyl group,
Het represents one of the groups




(Formula Removed)
A represents hydrogen, respectively optionally halogen-substituted C1-C12-alkyl, C2-C8-alkenyl, C1-C10-alkoxy-C1-C8-alkyl, poly-C1-C8-alkoxy-C1-C8-alkyl or C1-C10-alkylthio-C1-C6-alkyl, optionally halogen-, C1-C6-alkyl- or C1-C6-alkoxy-substituted C3-C8-cycloalkyl in which optionally one or two not directly adjacent methylene groups are replaced by oxygen and/or sulphur, or represents respectively optionally halogen-, C1-C6-alkyl-, C1-C6-halogenoalkyl-, C1-C6-alkoxy-, C1-C6-halogenoalkoxy-, cyano- or nitro-substituted phenyl, naphthyl, phenyl-C1-C6-alkyl, naphthyl-C1-C6-alkyl or hetaryl having 5 or 6 ring atoms and one to three heteroatoms from the group consisting of oxygen, sulphur and nitrogen,
B represents hydrogen, C1-C12-alkyl or C1-C8-alkoxy-C1-C6-alkyl or
A, B and the carbon atom that they are attached to represent C3-C10-cycloalkyl or C5-C10-cycloalkenyl where in each case one methylene group is optionally replaced by oxygen or sulphur and which are optionally substituted by C1-C8-alkyl, C3-C10-cycloalkyl, C1-C8-halogenoalkyl, C1-C8-alkoxy, C1-C8-alkylthio, halogen or phenyl, or
A, B and the carbon atom that they are attached to represent C5-C6-cycloalkyl which is substituted by an alkylenediyl group optionally

containing one or two oxygen and/or sulphur atoms, or by an alkylenedioxy group or alkylenedithioyl group forming a further five- to eight-membered ring with the carbon atom that it is attached to, or
A, B and the carbon atom that they are attached to represent C3-C8-karin cycloalkyl or C5-C3-cycloalkenyl in which two carbon atoms are connected by respectively optionally C1-C6-alkyl-, C1-C6-alkoxy-or halogen-substituted C3-C6-alkanediyl, C3-C6-alkenediyl or C4-C6-alkanedienediyl where in each case one methylene group is optionally replaced by oxygen or sulphur,
D represents hydrogen, respectively optionally halogen-substituted
C1-C12-alkyl, C3-C8-alkenyl, C3-C8-alkinyl, C1-C10-alkoxy-C2-C8-
alkyl, poly-C1-C8-alkoxy-C2-C8-alkyl or C1-C10-alkylthio-C2-C8-alkyl,
optionally halogen-, C1-C4-alkyl-, C1-C4-alkoxy- or C1-C4-halogeno-
alkyl-substituted C3-C8-cycloalkyl in which optionally one or two
not directly adjacent methylene groups are replaced by oxygen
and/or sulphur, or represents respectively optionally halogen-, C1-
C6-alkyl-, C1-C6-halogenoalkyl-, C1-C6-alkoxy-, C1-C6-
halogenoalkoxy-, cyano- or nitro-substituted phenyl, hetaryl having 5 to 6 ring atoms and one or two heteroatoms from the group consisting of oxygen, sulphur and nitrogen, phenyl-C1-C6-alkyl or hetaryl-C1-C6-alkyl having 5 to 6 ring atoms and one or two heteroatoms from the group consisting of oxygen, sulphur and nitrogen, or
A and D together represent a C3-C6-alkanediyl, C3-C6-alkenediyl or C4-C6-alkadienediyl group in which in each case one methylene group is optionally replaced by oxygen or sulphur and which are respectively optionally substituted by halogen or by respectively optionally halogen-substituted C1-C10-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, C3-C7-cycloalkyl, phenyl or benzyloxy or by a further C3-C6-alkanediyl, C3-C6-alkenediyl or C4-C6-alkadienediyl group forming a fused-on ring where in each case one methylene group is optionally replaced

by oxygen or sulphur and which are optionally substituted by C1-C6-alkyl, or
A andD together represent a C3-C6-alkanediyl or C3-C6-alkenediyl group, each of which optionally contains one of the following groups
(Formula Removed)
G represents hydrogen (a) or one of the groups
(Formula Removed)
in which
E represents a metal ion equivalent or an ammonium ion,

L represents oxygen or sulphur and
M represents oxygen or sulphur,
R1 represents respectively optionally halogen-substituted C1-C20-alkyl, C2-C20-alkenyl, C1-C8-alkoxy-C1-C8-alkyl, C1-C8-alkylthio-C1-C8-alkyl or poly-C1-C8-alkoxy-C1-C8-alkyl or respectively halogen-, C1-C6-alkyl- or C1-C6-alkoxy-substituted C3-C8-cycloalkyl in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and/or sulphur,
optionally halogen-, cyano-, nitro-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-halogenoalkyl-, C1-C6-halogenoalkoxy-, C1-C6-alkylthio- or C1-C6-alkylsulphonyl-substituted phenyl,
optionally halogen-, nitro-, cyano-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-halogenoalkyl- or C1-C6-halogenoalkoxy-substituted phenyl-C1-C6-alkyl,
optionally halogen- or C1-C6-alkyl-substituted 5- or 6-membered hetaryl having one or two heteroatoms from the group consisting of oxygen, sulphur and nitrogen,
optionally halogen- or C1-C6-alkyl-substituted phenoxy-C1-C6-alkyl or
optionally halogen-, amino- or C1-C6-alkyl-substituted 5- or 6-membered hetaryloxy-C1-C6-alkyl having one or two heteroatoms from the group consisting of oxygen, sulphur and nitrogen,
R2 represents respectively optionally halogen-substituted C1-C2o-alkyl, C2-C20-alkenyl, C1-C8-alkoxy-C2-C8-alkyl or poly-C1-C8-alkoxy-C2-C8-alkyl,
optionally halogen-, C1-C6-alkyl- or C1-C6-alkoxy-substituted C3-C8-cycloalkyl or

respectively optionally halogen-, cyano-, nitro-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-halogenoalkyl or C1-C6-halogenoalkoxy-substituted phenyl or benzyl,
R3 represents optionally halogen-substituted C1-C8-alkyl or respectively optionally halogen-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C4-halogeno-alkyl-, C1-C4-halogenoalkoxy-, cyano- or nitro-substituted phenyl or benzyl,
R4 and R5 each represent independently of one another respectively optionally halogen-substituted C1-C8-alkyl, C1-C8-alkoxy, C1-C8-alkylamino, di-(C1-C8-alkyl)amino, C1-C8-alkylthio or C3-C8-alkenylthio, respectively optionally halogen-, nitro-, cyano-, C1-C4-alkoxy-, C1-C4-halogenoalkoxy-, C1-C4-alkylthio-, C1-C4-halogeno-alkylthio-, C1-C4-alkyl- or C1-C4-halogenoalkyl-substituted phenyl, phenoxy or phenylthio,
R6 and R7 represent independently of one another hydrogen, respectively optionally halogen-substituted C1-C8-alkyl, C3-C8-cycloalkyl, C1-C8-alkoxy, C3-C8-alkenyl or C1-C8-alkoxy-C2-C8-alkyl, respectively optionally halogen-, C1-C8-alkyl-, C1-C8-halogenoalkyl- or C1-C8-alkoxy-substituted phenyl or benzyl or together represent an optionally C1-C6-alkyl-substituted C3-C6-alkylene radical in which one methylene group is optionally replaced by oxygen or sulphur,
R13 represents hydrogen or respectively optionally halogen-substituted C1-C8-alkyl or C1-C8-alkoxy, optionally halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted C3-C8-cycloalkyl in which one methylene group is optionally replaced by oxygen or sulphur, or respectively optionally halogen-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C4-halogeno-alkyl-, C1-C4-halogenoalkoxy-, nitro- or cyano-substituted phenyl, phenyl-C1-C4-alkyl or phenyl-C1-C4-alkoxy,
R14 represents hydrogen or C1-C8-alkyl or
R13 and R14 together represent C4-C6-alkanediyl,

R15 and R16 are identical or different and represent C1-C6-alkyl or
R15 and R16 together represent a C2-C4-alkanediyl radical which is optionally substituted by C1-C6-alkyl or by optionally halogen-, C1-C4-alkyl-, C1-C4-halogenoalkyl-, C1-C4-alkoxy-, C1-C4-halogeno-alkoxy-, nitro- or cyano-substituted phenyl,
R17 and R18 each represent independently of one another hydrogen, optionally halogen-substituted C1-C8-alkyl or optionally halogen-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C4-halogenoalkyl-, C1-C4-halogenoalkoxy-, nitro- or cyano-substituted phenyl or
R17 and R18 represent together with the carbon atom that they are attached to optionally C1-C4-alkyl-substituted C5-C7-cycloalkyl in which one methylene group is optionally replaced by oxygen or sulphur and
R19 and R20 each represent independently of one another C1-C10-alkyl, C2-C10-alkenyl, C1-C10-alkoxy, C1-C10-alkylamino, C3-C10-alkenyl-amino, di-(C1-C10-alkyl)amino or di-(C3-C10-alkenyl)amino),
provided that in case of Het = group (2), V is substituted by hydrogen, alkyl or alkoxy.
4. Compounds of the formula (I) as claimed in claim 1 wherein
V represents hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl or C1-C4-alkoxy,
W represents cyano, nitro, fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-halogenoalkyl, C1-C2-halogenoalkoxy or respectively optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-alkoxy-, C1-C2-halogenoalkyl-, C1-C2-halogenoalkoxy-, nitro-or cyano-substituted phenyl, phenoxy, benzyl or benzyloxy,
X represents hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-halogenoalkyl,C1-C2-halogenoalkoxy, cyano,

nitro or respectively optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-alkoxy-, C1-C2-halogenoalkyl-, C1-C2-halogenoalk-oxy-, nitro- or cyano-substituted phenyl, phenoxy, benzyl or ben2yl-oxy,
Y represents hydrogen, fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-halogenoalkyl, C1-C2-halogenoalkoxy, cyano or nitro,
Z represents fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C1-C2-halogenoalkyl, C1-C2-halogenoalkoxy, hydroxyl, cyano, nitro or respectively optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-alkoxy-, C1-C2-halogenoalkyl-, C1-C2-halogenoalk-oxy-, nitro- or cyano-substituted phenoxy or benzyloxy, or
YandZ together represent respectively optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-alkoxy- or C1-C2-halogenoalkyl-substituted C3-C4-alkanediyl or C3-C4-alkenediyl in which optionally one or two not directly adjacent members are replaced independently of one another by oxygen, sulphur or nitrogen, or
W and Z together represent respectively optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-alkoxy- or C1-C2-halogenoalkyl-sub-stituted C3-C4-alkanediyl or C3-C4-alkenyldiyl in which optionally one or two not directly adjacent members are replaced independently of one another by oxygen, sulphur or nitrogen,
Het represents one of the groups


(Formula Removed)
A represents hydrogen, respectively optionally fluorine- or chlorine-substituted C1-C10-alkyl, C2-C6-alkenyl, C1-C8-alkoxy-C1-C6-alkyl, poly-C1-C6-alkoxy-C1-C6-alkyl or C1-C8-alkylthio-C1-C6-alkyl or optionally fluorine-, chlorine-, C1-C4-alkyl or C1-C4-alkoxy-substituted C3-C7-cycloalkyl in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and/or sulphur, or respectively optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-halogenoalkyl-, C1-C4-alkoxy-, C1-C4-halogeno-alkoxy-, cyano- or nitro-substituted phenyl, furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, indolyl, thiazolyl, thienyl or phenyl-C1-C4-alkyl,
B represents hydrogen, C1-C10-alkyl or C1-C6-alkoxy-Ci-C4-alkyl or
A, B and the carbon atom that they are attached to represent C3-C8-cycloalkyl or C5-C8-cycloalkenyl in which respectively optionally one methylene group is replaced by oxygen or sulphur and which are optionally substituted by C1-C6-alkyl, C3-C8-cycloalkyl, C1-C3-halogenoalkyl, C1-C6-alkoxy, C1-C6-alkylthio, fluorine, chlorine or phenyl, or

A, B and the carbon atom that they are attached to represent C5-C6-cycloalkyl which is substituted by an alkylenediyl group optionally containing one or two oxygen or sulphur atoms, or by an alkylenedioxy or alkylenedithiol group forming a further five- to seven-membered ring with the carbon atom that it is attached to or
A, B and the carbon atom that they are attached to represent C3-C6-cycloalkyl or C5-C6-cycloalkenyl in which two carbon atoms are connected by optionally C1-C4-alkyl-, C1-C4-alkoxy-, fluorine-, chlorine- or bromine-substituted C3-C5-alkanediyl, C3-C5-alkenediyl or butadienediyl in which respectively optionally one methylene group is replaced by oxygen or sulphur,
D represents hydrogen, respectively optionally fluorine- or chlorine-substituted C1-C10-alkyl, C3-C6-alkenyl, C3-C6-alkinyl, C1-C8-alkoxy-C2-C6-alkyl, poly-C1-C6-alkoxy-C2-C6-alkyl or C1-C8-alkylthio-C2-C6-alkyl, optionally fluorine-, chlorine-, C1-C4-alkyl-, C1-C4-alkoxy- or C1-C2-halogenoalkyl-substituted C3-C7-cycloalkyl in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and/or sulphur, or represents respectively optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-halogenoalkyl-, C1-C4-alkoxy-, C1-C4-halogenoalkoxy-, cyano- or nitro-substituted phenyl, furanyl, imidazolyl, pyridyl, thiazolyl, pyrazolyl, pyrimidyl, pyrrolyl, thienyl, triazolyl or phenyl-C1-C4-alkyl or
A and D represent a C3-C5-alkanediyl or C3-C5-alkenediyl group in which respectively optionally one carbon atom is replaced by oxygen or sulphur and which are optionally substituted by fluorine, chlorine or respectively optionally fluorine- or chlorine-substituted C1-C6-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C3-C6-cycloalkyl, phenyl or benzyloxy or
which respectively optionally contain one of the following groups:

(Formula Removed)
G represents hydrogen (a) or one of the groups
(Formula Removed)
in which
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulphur and
M represents oxygen or sulphur
R1 represents respectively optionally fluorine- or chlorine-substituted C1-C16-alkyl, C2-C16-alkenyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkyl-thio-C1-C6-alkyl or poly-C1-C6-alkoxy-C1-C6-alkyl or optionally fluorine-, chlorine-, C1-C5-alkyl- or C1-C5-alkoxy-substituted C3-C7-cycloalkyl in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and/or sulphur,
optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, C1-C4-alkoxy-, C1-C3-halogenoalkyl-, C1-C3-halogeno-alkoxy-, C1-C4-alkylthio- or C1-C4-alkylsulphonyl-substituted phenyl,

optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-alkoxy-, C1-C3-halogenoalkyl- or C1-C3-halogenoalkoxy-substituted phenyl-C1-C4-alkyl,
optionally fluorine-, chlorine-, bromine- or C1-C4-alkyl-substituted pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl,
optionally fluorine-, chlorine-, bromine- or C1-C4-alkyl-substituted phenoxy-C1-C5-alkyl or
respectively optionally fluorine-, chlorine-, bromine-, amino- or C1-C4-alkyl-substituted pyridyloxy-C1-C5-alkyl, pyrimidyloxy-C1-C5-alkyl or thiazolyloxy-C1-C5-alkyl,
R2 represents respectively optionally fluorine- or chlorine-substituted C1-C16-alkyl, C2-C16-alkenyl, C1-C6-alkoxy-C2-C6-alkyl or poly-C1-C6-alkoxy-C2-C6-alkyl,
optionally fluorine-, chlorine-, C1-C4-alkyl- or C1-C4-alkoxy-substituted C3-C7-cycloalkyl or
respectively optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, C1-C3-alkoxy-, C1-C3-halogenoalkyl- or C1-C3-halo-genoalkoxy-substituted phenyl or benzyl,
R3 represents optionally fluorine- or chlorine-substituted C1-C6-alkyl or respectively optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-alkoxy-, C1-C2-halogenoalkoxy-, C1-C2-halogenoalkyl-, cyano- or nitro-substituted phenyl or benzyl,
R4 and R5 each represent independently of one another respectively optionally fluorine- or chlorine-substituted C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylamino, di-(C1-C6-alkyl)amino, C1-C6-alkylthio or C3-C4-alkenylthio or respectively optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, C1-C3-alkoxy-, C1-C3-halogenoalkoxy-, C1-C3-alkylthio-, C1-C3-halogenoalkylthio, C1-C3-alkyl- or C1-C3-halo-genoalkyl-substituted phenyl, phenoxy or phenylthio,

R6 and R7 each represent independently of one another hydrogen, respectively optionally fluorine- or chlorine-substituted C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-alkenyl or C1-C6-alkoxy-C2-C6-alkyl, respectively optionally fluorine-, chlorine-, bromine-, C1-C5-halogenoalkyl-, C1-C5-alkyl- or C1-C5-alkoxy substituted phenyl or benzyl, or represent together an optionally C1-C4-alkyl-substituted C3-C6-alkylene radical in which one methylene group is optionally replaced by oxygen or sulphur,
R13 represents hydrogen or respectively optionally fluorine- or chlorine-substituted C1-C6-alkyl or C1-C6-alkoxy, optionally fluorine-, C1-C2-alkyl- or C1-C2-alkoxy-substituted C3-C7-cycloalkyl in which one methylene group is optionally replaced by oxygen or sulphur, or represents respectively optionally fluorine-, chlorine-, bromine-, C1-C5-alkyl-, Ci-Cs-alkoxy-, C1-C2-halogenoalkyl-, C1-C2-halogeno-alkoxy-, nitro- or cyano-substituted phenyl, phenyl-C1-C3-alkyl or phenyl-C1-C2-alkyloxy,
R14 represents hydrogen or C1-C6-alkyl or
R13 and R14 together represent C4-C6-alkanediyl,
R15 and R16 are identical or different and represent C1-C4-alkyl or
R15 and R16 together represent a C2-C3-alkanediyl radical which is optionally substituted by C1-C4-alkyl or optionally fluorine-, chlorine-, bromine-, C1-C2-alkyl-, C1-C2-halogenoalkyl-, C1-C2-alkoxy-, C1-C2-halogenoalkoxy-, nitro- or cyano-substituted phenyl,
provided that in case of Het = group (2), V is substituted by hydrogen, alkyl or alkoxy.
5. Compounds of the formula (I) as claimed in claim 1 wherein

Y represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,
propyl, isopropyl, tert-butyl, methoxy, ethoxy, propoxy or iso
propoxy,
W represents cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl,
propyl, butyl, isopropyl, isobutyl, tert-butyl, methoxy, ethoxy,
propoxy, isopropoxy, trifluoromethyl, difluoromethoxy,
trifluoromethoxy, phenyl or benzyloxy,
X represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, isobutyl, isopropyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, difluoro¬methoxy cyano, nitro, phenyl or benzyloxy,
Y represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,
propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy,
propoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, difluoro¬
methoxy cyano or nitro,
Z represents fluorine, chlorine, bromine, methyl, ethyl, propyl, butyl, isobutyl, isopropyl, tert-butyl, methoxy, ethoxy, propoxy, iso¬propoxy trifluoromethyl, trifluoromethoxy, difluoromethoxy, cyano or nitro, or
Y and Z together represent optionally fluorine-, chlorine-, methyl-, ethyl-,
propyl-, isopropyl-, methoxy-, ethoxy-, propoxy-, isopropoxy- or trifluoromethyl-substituted C3-C4-alkanediyl in which two not directly adjacent members are optionally replaced by oxygen, or
W and Z together represent optionally fluorine-, chlorine-, methyl-, ethyl -, propyl-, isopropyl-, methoxy-, ethoxy-, propoxy-, isopropoxy- or tri-fluoromethyl-substituted C3-C4-alkanediyl in which two not directly adjacent members are optionally replaced by oxygen,
Het represents one of the groups

(Formula Removed)
A represents hydrogen, respectively optionally fluorine- or chlorine-substituted C1-C8-alkyl, C2-C4-alkenyl, C1-C6-alkoxy-C1-C4-alkyl, poly-C1-C4-alkoxy-C1-C4-alkyl or C1-C6-alkylthio-C1-C4-alkyl or optionally fluorine-, chlorine-, methyl- or methoxy-substituted C3-C6-cycloalkyl in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and/or sulphur, or represents respectively optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, isopropyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl, pyridyl or benzyl,
B represents hydrogen, C1-C8-alkyl or C1-C4-alkoxy-C1-C2-alkyl or
A, B and the carbon atom that they are attached to represent C3-C8-cycloalkyl or C5-C8-cycloalkenyl where in each case one methylene group is optionally replaced by oxygen or sulphur and which are optionally substituted by methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, fluorine, chlorine or phenyl or

A, B and the carbon atom that they are attached to represent C5-C6-cyclo-alkyl which is substituted by an alkylenediyl group optionally containing an oxygen or sulphur atom, or by an alkylenedioxy group forming a further five- or six-membered ring with the carbon atom that it is attached to or
A, B and the carbon atom that they are attached to represent C3-C6-cyclo-alkyl or C5-C6-cycloalkenyl in which two carbon atoms are connected by C3-C4-alkanediyl, C3-C4-alkenediyl or butadienediyl,
D represents hydrogen, respectively optionally fluorine- or chlorine-substituted C1-C8-alkyl, C3-C4-alkenyl, C3-C4-alkinyl, C1-C6-alkoxy-C2-C4-alkyl, poly-C1-C4-alkoxy-C2-C4-alkyl, C1-C4-alkylthio-C2-C4-alkyl or C3-C6-cycloalkyl in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and/or sulphur, or represents respectively optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, isopropyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl, furanyl, pyridyl, thienyl or benzyl,
or

A and D together represent a C3-C5-alkanediyl or C3-C5-alkenediyl group where in each case one methylene group is optionally replaced by oxygen or sulphur and which are optionally substituted by fluorine, chlorine or respectively optionally fluorine- or chlorine-substituted C1-C6-alkyl or C1-C4-alkoxy,
G represents hydrogen (a) or one of the groups
(Formula Removed)

in which
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulphur and
M represents oxygen or sulphur
R1 represents respectively optionally fluorine- or chlorine-substituted C1-C14-alkyl, C2-C14-alkenyl, C1-C4-alkoxy-C1-C6-alkyl, C1-C4-alkylthio-C1-C6-alkyl, poly-C1-C4-alkoxy-C1-C4-alkyl or optionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, i-propyl-, n-butyl-, i-butyl-, tert-butyl-, methoxy-, ethoxy-, n-propoxy- or isopropoxy-substituted C3-C6-cycloalkyl in which one or two not directly adjacent methylene groups are optionally replaced by oxygen and/or sulphur,
optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl-, tri-fluoromethoxy-, methylthio-, ethylthio-, methylsulphonyl- or ethyl -sulphonyl-substituted phenyl,
optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl- or trifluoromethoxy-substituted benzyl,
respectively optionally fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted furanyl, thienyl or pyridyl,
optionally fluorine-, chlorine-, methyl- or ethyl-substituted phenoxy- C1-C4-alkyl or
respectively optionally fluorine-, chlorine-, amino-, methyl- or ethyl- substituted pyridyloxy-C1-C4-alkyl, pyrimidyloxy-C1-C4-alkyl or thiazolyloxy-C1-C4-alkyl,

R2 represents respectively optionally fluorine- or chlorine-substituted C1-C14-alkyl, C2-C14-alkenyl, C1-C4-alkoxy-C2-C6-alkyl or poly-C1-C4-alkoxy-C2-C6-alkyl,
optionally fluorine-, chlorine-, methyl-, ethyl-, n-propyl-, isopropyl-or methoxy-substituted C3-C6-cycloalkyl,
or respectively optionally fluorine-, chlorine-, cyano-, nitro-, methyl-, ethyl-, n-propyl-, i-propyl-, methoxy-, ethoxy-, triflu-oromethyl- or trifluoromethoxy-substituted phenyl or benzyl,
R3 represents optionally fluorine- or chlorine-substituted methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, or respectively optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, isopropyl-, tert-butyl-, methoxy-, ethoxy-, isopropoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl or benzyl,
R4 and R5 each represent independently of one another respectively optionally fluorine- or chlorine-substituted C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylamino, di-(C1-C4-alkyl)amino or C1-C4-alkylthio or respectively optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, methyl-, methoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl, phenoxy or phenylthio,
R6 and R7 each represent independently of one another hydrogen, respectively optionally fluorine- or chlorine-substituted C1-C4-alkyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C3-C4-alkenyl or C1-C4-alkoxy-C2-C4-alkyl, respectively optionally fluorine-, chlorine-, bromine-, methyl-, methoxy- or trifluoromethyl-substituted phenyl or benzyl or together represent an optionally methyl- or ethyl-substituted C5-C6-alkylene radical in which one methylene group is optionally replaced by oxygen or sulphur,
provided that in case of Het = group (2), V is substituted by hydrogen, alkyl or alkoxy.

6. Pesticides or herbicides, wherein they comprise a compound of the formula (I) as claimed in claim 1.
7. Method for controlling pests and weeds, wherein the compounds of the formula (I) as claimed in claim 1 are allowed to act on pests and weeds and/or their habitat.
8. Process for preparing pesticides and herbicides, wherein compounds of the formula (I) as claimed in claim 1 are mixed with extenders and/or surface-active agents.
9. Compounds of formula I substantially as herein described with
reference to the foregoing examples.
10. Process for preparing the compounds of formula I substantially as herein described with reference to the foregoing examples.
11. Process for preparing pesticides and herbicides substantially as hereinbefore described with reference to the foregoing examples.

Documents:

0661-del-1997-abstract.pdf

0661-del-1997-claims.pdf

0661-del-1997-correspondence-others.pdf

0661-del-1997-description (complete)-26-06-2008.pdf

0661-del-1997-description (complete).pdf

0661-del-1997-form-1.pdf

0661-del-1997-form-18.pdf

0661-del-1997-form-2.pdf

0661-del-1997-form-4.pdf

0661-del-1997-form-6.pdf

0661-del-1997-gpa.pdf

661-DEL-1997-Abstract-(26-06-2008).pdf

661-DEL-1997-Claims-(26-06-2008).pdf

661-DEL-1997-Correspondence-Others-(01-07-2008).pdf

661-DEL-1997-Correspondence-Others-(26-06-2008).pdf

661-DEL-1997-Form-2-(26-06-2008).pdf

661-DEL-1997-Form-3-(01-07-2008).pdf

661-DEL-1997-GPA-(26-06-2008).pdf

661-DEL-1997-Petition-138-(01-07-2008).pdf

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Patent Number 228930
Indian Patent Application Number 0661/DEL/1997
PG Journal Number 09/2009
Publication Date 27-Feb-2009
Grant Date 13-Feb-2009
Date of Filing 17-Mar-1997
Name of Patentee BAYER AKTIENGESELLSCHAFT
Applicant Address D-51368 LEVERKUSEN, GERMANY
Inventors:
# Inventor's Name Inventor's Address
1 CHRISTOPH ERDELEN UNTERBUESCHERHOF 15, 42799 LEICHLINGEN, GERMANY
2 ALAN GRAFF GERSTENKAMP 19, 51061 KOLN, GERMANY
3 ULRIKE WACHENDORFF-NEUMANN OBERER MARKENWEG 85, 56566 NEUWIED, GERMANY
4 FOLKER LIEB ALFRED-KUBIN-STR.1, 51375 LEVERKUSEN, GERMANY.
5 HERMANN HAGEMANN KANDINSKYSTR.52, 51375 LEVERKUSEN, GERMANY
6 ARNO WIDDIG EIFGENSTR.8, 51519 ODENTHAL, GERMANY.
7 MICHAEL RUTHER GRABENSTR.23, 40789 MONHEIM, GERMANY
8 REINER FISCHER NELLY-SACHS-STR.23, 40789 MONHEIM, GERMANY
9 THOMAS BRETSCHNEIDER TALSTR.29B, 53797 LOHMAR, GERMANY
PCT International Classification Number A01N43/90
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 196 13 171.5 1996-04-02 Germany
2 196 49 665.9 1996-11-29 Germany