Indian Patents
Title of Invention

PYRIDYLCARBOXAMIDE DERIVATIVE AND PROCESS FOR PREPARING THE SAME
Abstract The invention relates to a 3-pyridylcarboxamide derivative of formula (I) wherein the various symbols are as defined in the description, compositions thereof, their use for the control of pests, and to processes for their preparation.
Full Text

The invention relates to 3-pyridylcarboxamide derivatives and their use for the control of pests, in particular arthropods such as insects and acarids, and helminths (including nematodes); to compositions containing them, and to processes and Intennediates for their preparation.
The control of insects, nematodes or helminths with 3-pyridylcarboxamide compounds has been described in many patents such as EP 580374, JP 10101648, JP 10182625, WO 200109104, WO 200114340, JP 6321903, JP 10195072 and JP 11180957.
However, the level of action and/or duration of action of these prior-art compounds is not entirely satisfactory in all fields of apphcation, in particular against certain organisms or when low concentrations are apphed.
Since modern pesticides must meet a wide range of demands, for example regarding level, duration and spectrum of action, use spectrum, toxicity, combination with other active substances, combination with formulation auxiharies or synthesis, and since the occurrence of resistances is possible, the development of such substances can never be regarded as concluded, and there is constantly a high demand for novel compounds which are advantageous over the known compounds, at least as far as some aspects are concerned.
It is an object of the present invention to provide compounds which widen the spectrum of the pesticides in various aspects.
The present invention provides a compound which is a 3-pyridylcarboxamide derivative of formula (I):


wherein;
R1 is -C(=U)NR2R4 or-C(=V)OR3a
R1 is H, (C1-C6)alkyl or R1
R1 is R1, OH or NH2; or is (C1-C6)all or R1 and R1 together with the interconnecting atoms form a Ineterocychc ring
selected from (A), (B), (C), (D) and (E);

R1^ is (C3-CB)cycloall R4 is H or R1; or is (C1-C6)alkyl unsubstituted or substituted by one or more R1 groups;

or R1 and R4 together with the adjacent N atom form a 3 to 8-membered unsaturated, partially saturated or saturated heterocychc ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R1 or R14a groups (preferred examples of such ring systems include pyrrol id in-1-yl, pyrrohn-1-yl, piperidin-1-yl, morphohn-1-yi (or its N-oxide), thiomorphohn-1-yl (or its S-oxide orS, S-dioxide), 4,5-dihydropyrazol-1-yl or pyrazol-1-yl);
R1 is (C3-C6)a!kenyl, (C3-C6)alkynyl, (C3-C8)cycloalkyl, (C1-C6)alkoxy, (C3-C6)alkenyloxy, (C3-C6)alkynyloxy, (C1-C6)alkylamino, di-(C1-C6)alkylamino, C0(C1-C6)alkyl, NHC0(C1-C6)alkyl, NHS02(C1-C6)a[kyl or S02(C1-C6)alkyl which last 12 mentioned groups are unsubstituted or substituted by one or more R1 groups; or is (C3-C8)cycloalkyl-(C1-C6)alkyl which cycloalkyi group is unsubstituted or substituted by one or more R6 groups; or is NH(CHR14)saryl, -(CR15R16)paryl, 0(R1^R1%aryl, NHCOaryl, CO(CH2)taryl, NHS02aryl, S02(CH2)uaryl or N=C(aryl)2, -(CR15R16)pheterocyclyl or 0(R15R16)rheterocyclyl, which last ten mentioned aryl or heterocyclyl groups are unsubstituted or substituted by one or more R17' groups; or is 0(CR1^R1^)p(C3-C8)cycloalkyl or N=C[(C1-C6)alkyl]2;
R1 is halogen, (C1-C6)a!koxy, (C1-C6)haloalkoxy, S(0)nR14a CN, C02(C1-C6)alkyl, CO2H, NO2, OH, amino, (C1-C6)alkylamino, di-(C1-C6)alkylamino, carbamoyl, (C1-C6)-a!kylcarban:ioyl, di-(C1-C6)-alkylGarbamoyl or CH[0(C1-C6)alkyl]2; or is phenoxy unsubstituted or substituted by one or more R14a or halogen groups; R17 is R1 R14a or CH2OH; U is S, O or NR18;
V is O or S;
W is (CHR19)q. CO or NR20; XisCR21 orN;
Y is CR22 or N;
Z is O, CO or NR23;
R7 R8 R9 R12 R19 R21 and R22 are each independently H; or (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C8)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyloxy or (C2-C6)alkynyloxy, which last seven mentioned groups are unsubstituted or substituted by one or more R1 groups; or is -(CH2)paryl or heterocyclyl, which aryl or

heterocycly! groups are unsubstituted or substituted by one or more R1 groups; or
(C3- C8)cycloalkyl-(C1-C6)alkyl which cycloaikyi group is unsubstituted or substituted
by one or more R6 groups;
or R7' and R6 together with the attached carbon atom may represent C=0;
R1°, R1°and R1^ are each independently H; or (C1-C6)alkyl. (C3-C6)alkenyl, (C3-
C6)alkynyl or (C3-C8)cycloalkyl, which last four mentioned groups are unsubstituted
or substituted by one or more R1 groups; or is (C3-C8)cycloalkyl-(C1-C6)alkyl which
cycloaikyi group is unsubstituted or substituted by one or more R1 groups; or is
-(CH2)paryl or heterocyclyl which aryl or heterocyclyl groups are unsubstituted or
substituted by one or more R6 groups; .
R4 is R1 halogen, CN, C02(C1-C6)alkyl, NO2 or S(0)nR14; or is (C1-C6)alkylamino or
di-(C1-C6)alkylamino, which groups are unsubstituted or substituted by one or more
R1 groups;
R4 is R1 or OH;
R14 R15 and R16 are each independently H, (C1-C6)alkyl or (C1-C6)haloalkyl;
R14a is (C1-C6)alkyl or (C1-C6)haloalkyl;
R18 is R1 or OH; or is (C1-C6)alkylamino or di-(C1-C6)alkylamino, which groups are
unsubstituted or substituted by one or more R1 groups;
m is zero or one;
n, p, r, s, t and u are each independently zero, one or two;
q is one, two or three; and each heterocyclyl in the above mentioned radicals is
independently a heterocychc radical having 3 to 7 ring atoms and 1 to 4 hetero
atoms selected from N, O and S;
or a pesticidally acceptable salt thereof;
with the exclusion of the compound wherein R1 is -C(=U)NR1R'; U is O; R1 is H; m is
zero; R4 is H and R1 is 2,4-dichlorophenyl.
These compounds possess valuable pesticidal properties.
The invention also encompasses any stereoisomer, enantiomer or geometric isomer, and mixtures thereof.

By the term "pesticidally acceptable salts" is meant salts the cations or anions of which are known and accepted in the art for the formation of salts for pesticidal use. Suitable salts with bases, e.g. formed by compounds of formula (I) containing a carboxy or OH group, include alkah metal (e.g. sodium and potassium), alkahne earth metal (e.g. calcium and magnesium), ammonium and amine (e.g. diethanolamine, triethanolamine, octylamine, morphohne and dioctylmethylamine) salts. Suitable acid addition salts, e.g. formed by compounds of formula (I) containing an amino group, include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates and nitrates and salts with organic acids for example acetic acid.
The term pests means arthropod pests (including insects and acarids), and helminths (including nematodes).
In the present patent'specification, including the accompanying claims, the
aforementioned substituents have the following meanings:
halogen atom means fluorine, chlorine, bromine or iodine;
alkyl groups and portions thereof (unless otherwise defined) may be straight- or
branched-chaln;
cycloaikyi groups preferably have from three to six carbon atoms in the ring and are
optionally substituted by halogen or alkyl.
The haloalkyl and haloalkoxy groups can bear one or more halogen atoms; preferred
groups of this type include -CF3 and -OCF3.
The term "halo" before the name of a radical means that this radical is partially or
completely halogenated, that is to say, substituted by F, CI, Br, or I, in any
combination, preferably by F or CI.
The expression "(C1-C6)-alkyl' is to be understood as meaning an unbranched or
branched hydrocarbon radical having 1, 2, 3, 4, 5 or 6 carbon atoms, such as, for
example a methyl, ethyl, propyl, isopropyl, 1-butyi, 2-butyl, 2-methylpropyl ortert-
butyl radical.

"(C1-C6)-Haloall "(C1-C6VAlkoxy" is to be understood as meaning an alkoxy group whose hydrocarbon radical has the meaning given under the expression "(C1-C6)-alkyl".
The terms "alkenyl" and "alkynyl" with a range of carbon atoms stated as prefix denote a straight-chain or branched hydrocarbon radical having a number of carbon atoms which corresponds to this stated range and which contains at least one multiple bond which can be located in any position of the respective unsaturated radical. "(C2-C6)-Alkenyl" accordingly denotes, for example, the vinyl, allyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or the hexenyl group. "(C2-C6)-Alkynyl" denotes, for example, the ethynyl, propargyl, 2-methyI-2-propynyl; 2-butynyl; 2-pentynyl or the 2-hexynyl group.
"(C3-C8)-Cycloalkyl" denotes monocychc alkyl radicals, such as the cyclopropyl, cyclobutyi, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl radical, and denotes bicychc alkyl radicals, such as the norbornyl radical.
The expression "(C3-C8)-cycloalkyl-(C1-C6)-alkyl" is to be understood as meaning, for example the cyclopropyl methyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylbutyl, 1-methylcyclopropyl, 1-methylcyclopentyl, 1-methylcyc!ohexyl, 3-hexylcyclobuty) or the 4-tert-butylcyclohexyl radical.
"(C1-C6Mlkylamino" denotes a nitrogen atom which is substituted by an alkyl radical of the above definition. "Di-(C1-C6)-alkyiamino" denotes a nitrogen atom which is substituted by two alkyl radical of the above definition.

The expression "(C1-C6)-alkylcarbamoyl" denotes a carbamoyl group having one hydrocarbon radical which has the meaning given under the expression "(C1-C6)-alkyl"; and "di-(C1-C6)-alkylcarbamoyl" denotes a carbamoyl group having two hydrocarbon radicals which can be identical or different.
The expression "aryl" is to be understood as meaning a carbocychc, i.e. constructed of carbon atoms, aromatic radical having preferably 6 to 14, in particular 6 to 12, carbon atoms, such as, for example, phenyl, naphthyl or biphenylyl, preferably phenyl.
The expression "heterocyclyl" preferably denotes a cychc radical which can be completely saturated, partially unsaturated or completely unsaturated and which contains in the ring one or more identical or different atoms selected from the group consisting of nitrogen, sulfur and oxygen, where, however, two oxygen atoms may not be directly adjacent and at least one carbon atom has to be present in the ring, such as, for example, a thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazoie, 1,3,4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo[b]thiophene, benzo[b]furan, indole, benzo[c]thiophene, benzo[c]furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,3,5-triazine, 1,2,4-triazine, 1,2,4,5-tetrazine, quinohne, isoquinohne, quinoxahne, quinazohne, cinnohne, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, phthalazine, pyridopyrimidine, purine, pteridine, 4H-quinohzine, piperidine, pyrrohdine, oxazollne, tetrahydrofuran, tetrahydropyran, isoxazohdine, thiazohdine, oxirane or oxetane radical.
Heterocyclyl preferably denotes a saturated, partially saturated or aromatic ring system having 3 to 7 ring members and 1 to 4 heteroatoms selected from the group consisting of O, S and N, where at least one carbon atom has to be present in the ring.

More preferably, heterocyclyl denotes a pyridine, pyrimidine, (1,2,4)-oxadiazole, (1,3,4)-oxadiazole, (1,3,4)-thiadiazoie, (1,2,4)-thiadiazole, pyrrole, furan, thiophene, oxazole, thiazole, benzothiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazole, tetrazole, pyrimidine, pyrazine, pyridazine, oxazohne, thiazohne, tetrahydrofuran, tetrahydropyran, morphohne, piperidine, piperazine, pyrrohne, pyrrohdine, oxazohdine orthiazohdine radical (particularly a pyridine, pyrimidine, (1,2,4)-oxadiazole, (1,3,4)-oxadiazoie, (1,3,4)-thiadiazole, 1,2,4-thiadiazole, thiazole, pyrazole, pyrrole, isoxazole, benzothiazole, 1,2,4-triazole, pyrazine, pyridazine, oxirane or oxetane radical).
Preferred substituents for the various ahphatic, aromatic and heterocychc ring systems include halogen, nitro, cyano, (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C1-C4)-alkoxy, (C1-C4)-aikylthio, (C1-C4)-alkylsulfinyl, (C1-C4)-alkylsulfonyl, phenyl, benzyl or phenoxy, where in the alkyl radicals and the radicals derived therefrom one or more - and in the case of fluorine up to the maximum number of - hydrogen atoms can be replaced by halogen, preferably chlorine or fluorine.
More preferred substituents include halogen, nitro, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C3-C6)-cycloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio or (C1-C4)-haloalkylthio.
Most preferred substituents include halogen, nitro, cyano, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio or (C1-C4)-haloalkylthio.
It is to be generally understood, unless otherwise stated, that the term "unsubstituted or substituted by one or more groups" or "unsubstituted or substituted by one or more groups selected from" means that such groups (or preferred groups) may be the same or different.
R1 is preferably -C(=U)NR2R1
R1 is preferably H or R1 (more preferably R1 is H);

R1 is preferably R1 or OH; or is (C1-C6)alkyl substituted by one or more R1 groups; or preferably R1 and R8 together with the interconnecting atoms form a heterocychc ring selected from (A) and (C):

R4 is preferably H or R1, or is (C1-C6)alkyl unsubstituted or substituted by one or more R1 groups;
or R1 and R4 together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocychc ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R1 or R14a groups (particularly preferred examples of such ring systems include pyrrohdin-1-yl, piperidin-1-yl, morphohn-1-yl, thiomorphohn-1-yl or its S-oxide or S, S-dioxide); R1 is preferably (C3-C6)alkenyl, (C3-C6)alkynyl, (C3-C8)cycloalkyl, (C3-CB)cycloalkyl-(C1-C6)alkyl, (C1-C6)alkoxy, (C3-C6)alkenyloxy, (C3-C6)alkynyloxy or 0(CR15R16)p(C3-C8)cycloalkyl; or is -(CR1^R1%phenyl, -(CR1^R1^)pheterocyclyl, 0(CR15R16)rphenyl or 0(CR1^R1^)rheterocyclyl, which last four mentioned phenyl or heterocyclyl groups are unsubstituted or substituted by one or more R4 groups; (more preferably R1 is (C3-C6)alkeny!, (C3-C6)alkynyl, (C1-C6)alkoxy, (C3-C6)alkenyloxy, (C3-C6)alkynyloxy or 0(CR1^R1®)p(C3-C8)cycloalky!; or is -(CR1^R1^)pphenyl, -(CR1^R1^heterocyclyl, 0(CR1^R1^)rphenyl or 0(CR'^R1%heterocyclyl, which last four mentioned phenyl or heterocyclyl groups are unsubstituted or substituted by one or more R1"" groups);
R1 is preferably halogen, (C1-C6)alkoxy, (C1-C6)haloalkoxy, S(0)nR''*^ CN, NO2 or OH; (more preferably R1 is halogen or CN); R1^ is preferably R1 R1'*^ or CH2OH; U is preferably S or O; W is preferably (CHR1^)q or CO;

Z is preferably O;
R7 R8 R9, R10 and R19 are each preferably H; or (C1-C6)alkyl unsubstituted or
substituted by one or more R1 groups;
or R7 and R8 together with the attached carbon atom represent C=0;
R14 R15 and R16 are each preferably H or (C1-C6)alkyl;
R14a is preferably (C1-C6)alkyl or (C1-C6)haloaikyl;
m is preferably zero;
n, r, s, t and u are preferably zero or one;
q is preferably one; and
heterocyclyl preferably denotes a pyridine, pyrimidine, (1,2,4)-oxadiazole, (1,3,4)-
oxadiazole, (1,2,4)-thiadia2ole, (1,3,4)-thiadiazole, benzothiazoie, pyrrole, furan,
thiophene, oxazole, thiazole, imidazole, pyrazole, isoxazole, 1,2,4-triazo)e, tetrazole,
pyrimidine, pyrazine, pyridazine, oxazohne, thiazohne, tetrahydrofuran,
tetrahydropyran, morphohne, piperidine, piperazine, pyrrohne, pyrrohdine,
oxazohdine, thiazohdine, oxirane oroxetane radical.
A preferred class of compounds of formula (I) are those in which:
R1 is -C(=U)NR3R4 or-C(=V)OR3a;
R1^ is (C3-C8)cycloalkyl or (C3-C8)cycloalkyl-(C1-C6)alkyl, which cycloalkyi groups are
unsubstituted or substituted by one or more (C1-C6)alkyl, (C1-C6)haloalkyl or R1
groups; or Is (C1-C6)alkyl, (C3-C6)alkenyl or (C3-C6)alkynyl which last three
mentioned groups are substituted by one or more R1^ groups; or is (Cr
C6)alkylamino; or is NH(CHR14)saryl which aryl group is unsubstituted or substituted
by one or more R6 groups;
R1' is (C1-C6)alkoxy, (C1-C6)haloalkoxy, S(O)nR14a C02(C1-C6)alkyl, CO2H, amino,
(C1-C6)alkylamino, carbamoyl, (C1-C6)-alkylcarbamoyl, di-(C1-C6)-alkylcarbamoyl or
CH[0(C1-C6)alkyl]2; or is phenoxy unsubstituted or substituted by one or more R14a
or halogen groups;
and the other values are as defined in formula (I).
A further preferred class of compounds of formula (1) are those in which: R1 is -C(=U)NR3R1;

R1 is H;
R1 is R1 or OiH; or is {C1-C6)alkyl substituted by one or more R1 groups;
or R1 and R4 together with the interconnecting atoms may form a heterocychc ring
selected from (A) and (C):

R4 is H or R1, or is (C1-C6)alkyl unsubstituted or substituted by one or more R1
groups;
or R1 and R4 together with the adjacent N atom may form a pyrrohdin-1-yl, piperidin-
1-yl, morphohn-1-yi orthiomorphohn-1-yl (or its S-oxide or S, S-dioxide) ring;
R1 is (C3-C6)alkeny!, (C3-C6)all (C1-C6)alkoxy, (C3-C6)alkenyloxy, (C3-C6)alkynyloxy or 0(CR15R16)p(C3-C8)cycloalkyl;
or-(CR15R16)phenyl, -(CR15R16)pheterocyclyl, 0(CR15R16),phenyl or
0(CR15 R16)rheterocyclyl, which last four mentioned phenyl or heterocyclyl groups are
unsubstituted or substituted by one or more R17 groups;
R1 is halogen, (C1-C6)aikoxy. (C1-C6)haloalkoxy, S(0)nR14a CN, NO2 or OH;
R1^ is R1 R14a or CH2OH;
U is S or O;
W is (CHR1^)q or CO;
ZisO;
R7 R8 R9 R10 and R19 are each H; or (C1-C6)alkyl unsubstituted or substituted by
one or more R1 groups;
or R7 and R8 together with the attached carbon atom represent C=0;
R14 R15 and R16 are each H or (C1-C6)alkyl;
R14a is (C1-C6)alkyl or (C1-C6)haloalkyl;
m is zero;
n, r, s, t and u are zero, one or two;

q is one; and wherein heterocyciyl denotes a pyndine, pyrimidine, (1,2,4)-oxadiazole, (1,3,4)-oxadiazoie, (1,2,4)-thiadia2ole, (1,3,4)-thiadia2ole, pyrrole, furan, thiophene, oxazole, thiazole, benzothiazoie, imidazole, pyrazole, isoxazoie, 1,2,4-tria2ole, tetrazole, pyrazine, pyridazine, oxazohne, thiazohne, tetrahydrofuran, tetrahydropyran, morphohne, piperidine, piperazine, pyrrohne, pyrrohdine, oxazohdine, thiazohdine, oxirane or oxetane radical.
A further preferred class of compounds of formula (!) are those in which:
R1 is -C(=U)NR3R4•
R1isH;
U is O or S;
R1 is (C1-C6)haloalkyl, (C3-C6)alkenyl, (C3-C6)aikynyl, (C3-C8)cycloaikyl, (C3-
CB)cycioalkyl(C1-C6)alky!, (C3-C6)alkenyloxy. (C3-C6)alkynyloxy, NH2, (Ci-
C6)aIkylamino, OH, Ophenyl, pyrimidyl, benzothiazoiyi, thiazolyi, thiadiazolyl,
-(CH2)2pyrrohdin-1-yl, NHS02phenyI, NHC0(C1-C6)alkyi, NHS02{C1-C6)alkyt,
NHCOphenyl or N=C(phenyl)2; or is pyridyl unsubstituted or substituted by one or
more groups selected from halogen, (C1-C6)alkyl, (C1-C6)alkoxy, CN and NO2; or is
0CH2phenyl which phenyl is unsubstituted or substituted by one or more groups
selected from halogen, (C1-C6)alkyl, CN and NO2; or is (C1-C6)alkoxy unsubstituted
or substituted by a C02(C1-C6)alkyl group;
or is -(CHR1^)pphenyl wherein p is 0,1 or 2, R15 is H or (C1-C6)alkyl, and phenyl is
unsubstituted or substituted by one or more groups selected from halogen, (C1-
C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkoxy, (C1-C6)haloalkoxy, CN, NO2, OH, CH2OH,
C02(C1-C6)alkyl and phenoxy which phenoxy is unsubstituted or substituted by one
or more groups selected from halogen and (C1-C6)haloalkyl;
or is (C1-C6)alkyl unsubstituted or substituted by one or more groups selected from
(C1-C6)alkoxy, CN, OH, C02(C1-C6)alkyl and CH[0(C1-C6)alkyl]2;
or is NH(CH2)sPhenyl wherein s is zero or 1;
R4 is H, (C1-C6)alkyl, (C3-C6)alkenyl, (C3-C6)alkynyl, (C3-C8)cycloa!kyl, -(CH2)pPhenyl
wherein p is 0 or 1, or N=C[(C1-C6)alkyI]2;-
or R1 and R' together with the adjacent N atom may form a pyrrohdin-1-yi, piperidin-
1-yI, morphohn-1-yl, thiomorphohn-1-yl which groups are unsubstituted or substituted

by one or more groups selected from halogen, (C1-C6)alkyl and OH; or form a 4,5-dihydropyrazol-1-yl ring; and m is zero.
A further preferred class of compounds of formula (1) are those in which:
R1 is -C(=U)NR1R4;
UisO;
R1 is (C1-C6)alkyl, (C3-C6)alkenyl, (C3-C6)alkynyl orCHaphenyl; or is (C1-C6)alkyl
substituted by C02(C1-C6)alkyl or CH[0(C1-C6)alkyl]2;
R1 is (C3-C6)alkenyloxy, (C3-C6)alkynyloxy, CHaphenyl or 0CH2phenyl; or is (Cr
C6)alkoxy unsubstituted or substituted by one or two C02(C1-C6)aIkyl groups;
R4 is H or (C1-C6)alkyl; and
m is zero.
A further preferred class of compounds of formula (I) are those in which;
R1 is -C(=U)NR1R';
R1 and R1 together with the interconnecting atoms form a heterocychc ring selected
from (A) and (C):

wherein U is O or S;
and in (A):
W is CH2, CO or CHR1^ wherein R19 is H, (C1-C6)alkyl or phenyl;
R4 is H, (C1-C6)alkyl, phenyl, CHzphenyl or OCHiphenyl;
R1 is H, (C1-C6)alkyl, (C1-C6)alkoxy or phenyl; and
R1 is H or (C1-C6)alkyl;
and in (C):
ZisO;
R4 is (C1-C6)alkyl, (C3-C8)cycloalkyl or CH2phenyl; and

R9 and R10 are each H; and m is zero.
A further preferred class of compounds of formula (I) are those in which:
R1 is -C(=U)NR3R4;
wherein U is NR18
R1 is H;
R1 is (C1-C6)aikyl, (C3-C6)alkenyl, (C3-C8)cycloalkyl; or is (C1-C6)alkyl substituted by
one or two (C1-C6)all R4 and R18are each the same or different H or (C1-C6)alkyl;
or R1 and R4 together with the adjacent N atom form a morphohn-l-yl or pyrazol-1-yl
ring; and
m is zero.
A further preferred class of compounds of formula (I) are those in which:
R1 is -C(=V)OR3a
wherein Vis O or S;
R1 is H, (C3-C8)cycloalkyl-(C1-C6)alkyl, NHCHaphenyl; or is (C1-C6)alkyl substituted
by a group selected from (C1-C6)alkoxy, CN, OH and S(O)nR14a;
R3a is (C3-C8)cycloalkyl or (C3-C8)cycloalkyl-(C1-C6)alkyl, which cycloalkyi groups are
unsubstituted or substituted by one or more R6 groups; or is (C1-C6)alkyl, (C3-
C6)alkenyl or (C3-C6)alkynyl which last three mentioned groups are substituted by
one or more R6 groups; or is (C1-C6)alkylamino; or is NH(CHR14)saryI which aryl
group is unsubstituted or substituted by one or more R1 groups; and
m is zero.
A more preferred class of compounds of formula (I) are those in which:
R1is-C(=U)NR3R4';
R1 is H;
U is O or S;
R1 is (C1-C6)alkoxy, C1-C6)haloalkoxy, (C3-C6)alkenyloxy, (C3-C6)alkynyloxy,
CH2phenyl or 0CH2phenyl, phenyl or 2-pyridyl which last four mentioned phenyl or

pyridyl groups are unsubstituted or substituted by one or more groups selected from
halogen, (C1-C6)alkyl, (C1-C6)alkoxy, CN and N02;
R4 is H, (C1-C6)alkyl, (C3-C6)alkenyl, (C3-C6)alkynyl or CH2phenyl; and
m is zero.
A further more preferred class of compounds of formula (I) are those in which:
R1 is -C(=U)NR3R4
R2 is H;
U is O;
R1 is (C1-C6)alkoxy;
R4 is (C1-C6)alkyl; and
m Is zero.
The compounds of general formula (I) can be prepared by the apphcation or adaptation of known methods (i.e. methods heretofore used or described in the chemical hterature.
In the following description of processes when symbols appearing in formulae are not specifically defined, it is understood that they are "as defined above" in accordance with the first definition of each symbol in the specification.
According to a feature of the invention compounds of formula (I) wherein R1 is -C(=U)NR1R4, m is zero, and R1, U, R1and R4^ are as defined above; or R1 and R1 together with the interconnecting atoms form a heterocychc ring selected from (A), (B), (C), (D) and (E);


wherein R4 R7 R8 R9 R10, R11 R12 R13 W, X, Y and Z are as defined above, may be prepared by the reaction of a compound of formula (11):

wherein L is a leaving group, generally halogen and preferably chlorine, with a compound of formula (Ih):
HNR1-C(=U)NR3R4 (ill) wherein R1, U, R1and R4 are as defined above, or with a compound of formula (IV), (V), (VI); (Vh) or (VIh):


wherein R4, R7 R8 R9 R10, R11 R12 R13 W, X, Y and Z are as defined above. The reaction is generally performed in tine presence of an organic base such as a tertiary amine for example trietlnylamine, or pyridine, or an inorganic base such as an ail According to a further feature of the present invention compounds of formula (I) wherein R' is -C(=U)NR1R4, m is zero, R1 is H, U is O, and R1and R4* are as defined above, may be prepared by the reaction of a compound of formula (IX):

with oxalyl chloride ortriphosgene, in an inert solvent such as dichloroethane at a temperature of from 0°C to the reflux temperature of the solvent, followed by removal of the solvent to give the corresponding acyhsocyanate intermediate which is generally not isolated, and which is directly reacted with an amine of formula (X):
HNR1R4 (X)

wherein R1 and R4 are as defined above. The reaction is generally performed in an inert solvent such as dichloroethane or tetrahydrofuran at a temperature of from 0° to
60°C.
According to a further feature of the present invention compounds of formula (I) wherein R' is -C(=V)OR1^, m is zero, R1 is H, V is O, and R1® is as defined above, may be prepared by the reaction of a compound of formula (IX) as defined above, with oxalyl chloride to give an acyhsocyanate intermediate above which is generally not isolated, and which is directly reacted with an alcohol of formula (XI):
HOR13a (XI)
wherein R1 is as defined above. The reaction is generally performed in an inert solvent such as dichloroethane or tetrahydrofuran at a temperature of from 0° to 60°C.
According to a further feature of the present invention compounds of formula (I) wherein R' is -C(=U)NR1R4, m is zero, R1 is H, U is O or S, and R1 and R4 are as defined above, may be prepared by the reaction of a compound of formula (Xh).

wherein U is O or S, with a compound of formula (X) as defined above. The reaction is generally performed in an inert solvent such as dichloroethane or tetrahydrofuran at a temperature of from 0° to 60°C.
According to a further feature of the present invention compounds of formula (I) wherein R1 is -C(=V)OR1^, m is zero, R1 is H, V is O or S, and R1^ is as defined above, may be prepared by the reaction of a compound of formula (XIh).


wherein V is O or S, with a compound of formula (XI) as defined above. The reaction is generally performed in an inert solvent such as dichloroethane or tetrahydrofuran at a temperature of from 0° to 60°C.
According to a further feature of the present invention compounds of formula (1) wherein R1 is -C(=U)NR1R4, m is zero, R1 is H, R4 is H, U is O or S, and R1 is as defined above, may be prepared by the reaction of a compound of formula (IX) as defined above, with a strong base such as sodium hydride to form the corresponding salt, which is then reacted with a compound of formula (XIV):
R1N=C=U (XIV)
wherein R1 is as defined above. The reaction is generally performed In an inert solvent such as N,N-dimethylformamide at a temperature of from 0° to 60°C.
According to a further feature of the present invention compounds of formula (1) wherein R1 Is -C(=U)NR1R' or -C(=V)OR1^, m is zero, R1 is H, U and V are each S, and R1, R1^ and R4* are as defined above, may be prepared in a 1-pot process by the reaction of 4-trifluoromethylnicotinic acid with a suitable halogenating agent, preferably oxalyl chloride, in a solvent such as dichloroethane, optionally in the presence of N,N-dimethylformamide, at a temperature of from 0°C to the reflux temperature of the solvent, to give the corresponding acid chloride, followed by removal of the solvent, and reaction with an alkah metal thiocyanate or ammonium thiocyanate or a tetraalkylammonium thiocyanate for example tetrabutylammonium thiocyanate, generally in the presence of a base, such as an alkah metal carbonate for example potassium carbonate, in an inert solvent such as toluene or acetone, at a temperature of from 0° to 60°C, to give 4-trifluoromethyi-3-pyridylcarbonyl isothiocyanate, followed by reaction with an amine of formula (X) above or an alcohol of formula (XI) above, at a temperature of from 0° to 60°C.

According to a further feature of the invention compounds of formula (1) wherein R1 is -C(=U)NR3R4 m is zero, U, R3 and R4 are as defined above, and R2 is (C1-C6)all R2-L1 (XV)
wherein L' is a leaving group generally halogen and preferably chlorine. The reaction is generally performed in the presence of an organic base such as a tertiary amine for example ti'iethylamine, or pyridine, or an inorganic base such as an alkah metal carbonate, for example potassium carbonate, or an alkah metal alkoxide such as sodium ethoxide, or sodium hydride, in a solvent such as dioxan, tetrahydrofuran or N,N-dimethylformamide, at a temperature of from 0° to 100°C (preferably 0° to 50°C).
According to a further feature of the invention compounds of formula (I) wherein R1,
and R2 are as defined above, and m is 1 may be prepared by oxidising a corresponding compound in which m is 0. The oxidation is generally performed using hydrogen peroxide in a solvent such as acetic acid, or a peracid such as 3-chloroperbenzoic acid in a solvent such as dichloromethane or 1,2-dichloroethane, at a temperature of from 0°C to the reflux temperature of the solvent.
Intermediates of formula (h) wherein L is chlorine, may be prepared according to known procedures, for example by the reaction of the corresponding carboxyhc acid of formula (h) wherein L is replaced by OH, with a suitable halogenating agent, preferably oxalyl chloride orthionyl chloride, in a solvent such as dichloroethane, optionally in the presence of N,N-dimethylformamide, at a temperature of from 0°C to the reflux temperature of the solvent.

Intermediates of formula (Xh) wherein U is S, and (XIh) wherein V is O, may be prepared according to known procedures, for example by the reaction of a compound of formula (11) as defined above, with an alkah metal thiocyanate or ammonium thiocyanate or a tetraalkylammonium thiocyanate for example tetrabutylammonium thiocyanate, generally in the presence of a base such as an alkah metal carbonate for example potassium carbonate, in an inert solvent solvent such as toluene or acetone, at a temperature of from 0° to 100°C.
Intermediate of formula (Xh) wherein U is O, may be prepared according to known procedures, for example by the reaction of a compound of formula (11) as defined above, with an alkah metal cyanate or ammonium cyanate or a tetraalkylammonium cyanate for example tetrabutylammonium cyanate, generally in the presence of a base such as an alkah metal carbonate for example potassium carbonate, in an inert solvent solvent such as toluene, at a temperature of from 0° to 100°C.
Collections of compounds of the formula (I) which can be synthesized by the above mentioned process may also be prepared in a parallel manner, and this may be effected manually or in a semiautomated or fully automated manner. In this case, it is possible, for example, to automate the procedure of the reaction, work-up or purification of the products or of the intermediates. In total, this is to be understood as meaning a procedure as is described, for example, by S.H. DeWitt in "Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis", Volume 1, Verlag Escom 1997, pages 69 to 77.
A series of commercially available apparatuses as are offered by, for example. Stem Corporation, Woodrolfe Road, Tollesbury, Essex, CM9 8SE, England or H+P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleihheim, Germany or Radleys, Shirehill, Saffron Walden, Essex, England, may be used for the parallel procedure of the reaction and work-up. For the parallel purification of compounds of the formula (I), or of intermediates obtained during the preparation, use may be made, inter aha, of chromatography apparatuses, for example those by ISCO, Inc., 4700 Superior Street, hncoln, NE 68504, USA.

The apparatuses mentioned lead to a modular procedure in which tine individual process steps are automated, but manual operations must be performed between the process steps. This can be prevented by employing semi-integrated or fully integrated automation systems where the automation modules in question are operated by, for example, robots. Such automation systems can be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, MA 01748, USA.
In addition to what has been described here, compounds of the formula (I) may be prepared in part or fully by sohd-phase-supported methods. For this purpose, individual intermediate steps or all intermediate steps of the synthesis or of a synthesis adapted to suit the procedure in question are bound to a synthetic resin. Sohd-phase-supported synthesis methods are described extensively in the speciahst hterature, for example Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998.
The use of sohd-phase-supported synthesis methods permits a series of protocols which are known from the hterature and which, in turn, can be performed manually or in an automated manner. For example, the "tea-bag method" (Houghten, US 4,631,211; Houghten etal., Proc. Natl. Acad. Sci, 1985, 82, 5131-5135), in which products by iRORl, 11149 North Torrey Pines Road, La Jolla, CA 92037, USA, are employed, may be semiautomated. The automation of sohd-phase-supported parallel syntheses is performed successfully, for example, by apparatuses by Argonaut Technologies, Inc., 887 industrial Road, San Carlos, CA 94070, USA or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Germany.
The preparation of the processes described herein yields compounds of the formula (1) in the form of substance collections which are termed hbraries. The present invention also relates to hbraries which comprise at least two compounds of the formula (I).
Compounds of fomnula (11), (111), (IV), (V), (VI), (Vh), (VIh), (IX), (X), (XI), (XIV) and (XV) are known or may be prepared by known methods.

The following non-hmiting Examples illustrate the preparation of the compounds of formula (I). Chemical Examples
NMR spectra were run in deuterochloroform unless stated otherwise.
In the Examples which follow, quantities (also percentages) are weight-based,
unless stated otherwise.
Example 1
Oxalyl chloride (0.15ml) was added to a suspension of 4-trifluoromethyl-3-pyridinecarboxamide (0.25g) in 1,2-dichloroethane at 20°C and then heated to reflux for 2 hours. The mixture was cooled, evaporated and the residue containing 4-trifluoromethyl-3-pyridylcarbonyI isocyanate was dissolved in tetrahydrofuran. Benzylamine (0.15ml) was added and the mixture stin-ed at 20'C for 2 hours and evaporated. The residue was purified by sihca-gel column chromatography, eiuting with n-hexane/ethyl acetate (3:2), to give 1-benzyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.30g, Compound A-37).
By proceeding In a similar manner there was prepared 1-benzyl-1-(2-hydroxyethyl)-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (Compound A-862).
Example 2
Oxalyl chloride (1.50ml) was added to a suspension of 4-trifluoromethyl-3-pyridinecarboxamlde (2.0g) in 1,2-dichloroethane at 20°C, and stirred under reflux for 2 hours. The mixture was evaporated and dichloromethane added to the residue containing 4-trifluoromethyl-3-pyridylcarbonyl isocyanate. To this was added at 20°C a suspension of N,0-dimethylhydroxylamine hydrochloride(2.05g) and triethylamine (3,0ml) in dichloromethane, which had been prepared in advance. The mixture was stirred for 30 minutes, then water added and the organic layer dried (magnesium sulfate) and evaporated, to give after trituration with ethanol, 1-methyl-1-methoxy-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (2.2g) (Compound A-313).

By proceeding in a similar manner there was prepared 1-hydroxyi-1-isopropyl-3-(4-trifluoromethyl-3-pyridylcarbonyi)urea (Compound A-540).
Example 3
Sodium hydride (O.OQOg, 60% dispersion in mineral oil) was added to a solution of 4-trifluoromethyI-3-pyridinecarboxamide (0.40g) in N,N-dimethylformamide at 20°C, and stirred for 1 hour. Benzyl isocyanate (0.31 ml) was added and the mixture stirred at 20°C for 2 hours, then methyl bromoacetate (0.30 ml) added and stirring continued for 5 hours. Ethyl acetate and water were added to the solution and the organic phase dried (magnesium sulfate), evaporated and the residue purified by column chromatography on sihca gel, eluting with n-hexane/ethyl acetate (2:1), to give 3-benzyl-1-(4-trifluoromethyl-3-pyridylcarbony!)hydantoin (0.50g, Compound S-132).
Example 4
Methanesulfonyl chloride (0.17ml) was added to an ice-cooled mixture of 1-benzyl-1-(2-hydroxyethyl)-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.70g), and triethylamine (0,64ml) in dichloromethane, then stirred for 3 hours at 20°C. The mixture was washed (water), dried (magnesium sulfate), evaporated and the residue purified by sihca-gel chromatography, eluting with n-hexane/ethyl acetate (3:2), to give 1 -benzyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)-2-imidazohdinone (0.63g, Compound S-15).
Example 5
1,2-Dibromoethane (0.06ml) was added to a suspension of 1-hydroxyl-1-isopropyl-3-(4-trlfluoromethyl-3-pyridylcarbonyl)urea (0.20g) and potassium carbonate (0.20g) in N,N-dimethylformamide at 20°C, and stirred for 3 hours. Ethyl acetate and water were added and the organic phase dried (magnesium sulfate), evaporated and the residue purified by column chromatography on sihca gel, eluting with n-hexane/ethyl acetate (2:1), to give 2-isopropyl-4-(4-trifluoromethyl-3-pyridylcarbonyI)-perhydro-1,2,4-oxadiazin-3-one (0.25g, Compound U-3).

Example 6
Oxalyl chloride (3.2 ml, 2M) was added to a suspension of 4-trifluoromethylnicotinic acid (1g) and a catalytic amount of N,N-dimethylformamide in dichloromethane, and stirred at 20°C for 1 hour. After evaporation, the residue was dissolved in acetone and potassium thiocyanate (1g) added with ice bath coohng to give 4-trifluoromethyl-3-pyridylcarbonyl isothiocyanate, then N-methylanihne (0.65g) was added and the mixture stirred at 20'C for 1 hour. Ethyl acetate was added and the mixture washed with water, dried (magnesium sulfate), evaporated and the residue purified by sihca-gel chromatography, eluting with n-hexane/ethyl acetate = 2/1, to give 1-methyl-1-phenyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)thiourea (0.96g, Compound B-349).
Example 7
Oxalyl chloride (6.4ml, 2M) was added to a suspension of 4-trifluoromethylnicotinic acid (2g) and a catalytic amount of N,N-dimethylformamlde in dichloromethane, and stirred at 20°C for 1 Hour to give a solution of 4-trifluoromethylnicotinic acid chloride. N, N-Ethylenethiourea (2.23g) was added to sodium hydride (0.82g, 60% dispersion in mineral oil) in tetrahydrofuran, and the mixture was stirred at 20°C for 1 hour, and then added to the above solution of 4-trifluoromethylnicotinic acid chloride with ice bath coohng, then stirred at 20°C for 1 hour. Ethyl acetate was added and the mixture washed with water, dried (magnesium sulfate), evaporated and the residue crystalhzed (ethanol) to give N-(4-trifluoromethyl-3-pyridylcarbonyl)-imidazohn-2-thione (1.35 g, Compound S-356).
Example 8
Oxalyl chloride (9.6 ml, 2i\/l) was added to a suspension 4-trifluoromethylnicotinic acid (3g) and a catalytic amount of N, N-dimethylformamide in dichloromethane, and stirred at 20°C for 1 hour. The mixture was evaporated, the residue dissolved in toluene and tetrabutylammonium thiocyanate (3g) and potassium carbonate (1.5g) added, then stirred at 20°C for 30 minutes to give 4-trifluoromethyl-3-pyridylcarbonyl isothiocyanate 2,2,2-trifluoroethanol (3.15g) was then added, and the mixture stirred at 20°C for 1 hour. Ethyl acetate was added and the mixture washed with water, hydrochloric acid 1(M), saturated sodium bicarbonate and brine, dried (magnesium

sulfate), evaporated and recrystalhsed from ethanol to give 2,2,2-trifluoroethyl N-(4-trifluoromethyl-3-pyridylcarbonyi) thiocarbamate (1.2g, Compound X-45).
Example 9
Ally! bromide (0.10ml) was added to a suspension of 1-methyl-1-methoxy-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.25g) and potassium carbonate (0.16g) in N,N-dimethylformamide at 20 °C, and stirred for 2 hours. Ethyl acetate and water were added and tine organic phase dried (magnesium sulfate), evaporated and the residue purified by column chromatography on sihca gel, eiuting with n-hexane/ethyl acetate (2:1) to give 1-methyl-1-methoxy-3-allyl-3-(4-trifluoromethyl-3-pyridylcarbonyl)urea (0.26g, Compound E-85).
Tile following preferred compounds shown in Tables 1 to 9 also form part of the present invention, and were or may be prepared in accordance with, or analogously to, the above-mentioned Examples 1 to 9 or the above-described general methods. In the Tables Ph means phenyl. Where subscripts are omitted after atoms it will be understood that they are intended, for example CH3 means CH3.
Compound numbers are given for reference purposes only.
Table I
Compounds of formula (I) in which R1 is -C(=U)NR1R4; R1 is H and m is zero. In Table 1 compounds A-1 to A-881 represent individual compounds in which U is O, whilst compounds B-1 to B-881 represent individual compounds in which U is S.











































Table 2
Compounds of formula (I) in which R' is -C{=U)NR1R4; U is O, m is zero and R1 is as defined hereafter. In Table 2 compounds C-1 to C-151 represent individual compounds in which R1is methyl; compounds D-1 to D-151 represent individual compounds in which R1is ethyl; compounds E-1 to E-151 represent individual compounds in which R1is allyl; compounds F-1 to F-151 represent individual compounds in which R1is propargyl; compounds G-1 to G-151 represent individual compounds in which R1is benzyl; compounds H-1 to H-151 represent individual compounds in which R1is -CH2CO2CH3; compounds 1-1 to 1-151 represent
individual compounds in which R1is -CH(CH3)C02CH3; compounds J-1 to J-151
represent individual compounds in which R1is -CH2CH(OCH3)2.













Table 3
Compounds of formula (I) in which R1 is -C(=U)NR1R'; U is S and m is zero. In Table 3 compounds K-1 to K-151 represent individual compounds in which R1is methyl; compounds L-1 to L-151 represent individual compounds in which R1is ethyl; compounds M-1 to M-151 represent individual compounds in which R1is allyl; compounds N-1 to N-151 represent individual compounds in which R1is propargyl; compounds 0-1 to 0-151 represent individual compounds in which R1is benzyl; compounds P-1 to P-151 represent individual compounds in which R1is -CH2CO2CH3; compounds Q-1 to Q-151 represent individual compounds in which R1is -CH(CH3)C02CH3; compounds R-1 to R-151 represent individual compounds in which R1 is -CH2CH(OCH3)2.













































































Table 10
1H-NMR spectral details for representative Examples from the above Tables.
Nmr spectra were measured in deuterochloroform unless otherwise stated.

































According to a further feature of the present invention there is provided a method for the control of pests at a locus which comprises the apphcation of an effective amount of a compound of formula (I) or a salt thereof. For this purpose, the said compound is normally used in the form of a pesticidal composition (i.e. in association with compatible diluents or carriers and/or surface active agents suitable for use in pesticidal compositions), for example as hereinafter described.
The term "compound of the invention" as used hereinafter embraces a 3-pyhdylcarboxamide of formula (!) as defined above and a pesticidally acceptable salt thereof.
One aspect of the present invention as defined above is a method for the control of pests at a locus. The locus Includes, for example, the pest itself, the place (plant, field, forest, orchard, waterway, soil, plant product, or the hke) where the pest resides or feeds, or a place susceptible to future infestation by the pest. The compound of the invention may therefore be apphed directly to the pest, to the place where the pest resides or feeds, or to the place susceptible to future infestation by the pest.

As is evident from the foregoing pesticidal uses, the present invention provides pesticidaily active compounds and methods of use of said compounds for the control of a number of pest species which includes: arthropods, especially insects or mites, or plant nematodes. The compound of the invention may thus be advantageously employed in practical uses, for example, in agricultural or horticultural crops, in forestry, in veterinary medicine or hvestock husbandry, or in pubhc health. The compounds of the invention may be used for example in the following apphcations and on the following pests:
For the control of soil insects, such as corn rootworm, termites (especially for protection of structures), root maggots, wireworms, root weevils, stall In the area of pubhc health, the compounds are especially useful in the control of many insects, especially filth fhes or other Dipteran pests, such as housefhes, stablefhes, soldierfhes, hornfhes, deerfhes, horsefhes, midges, punkies, blackfhes, or mosquitoes.
In the protection of stored products, for example cereals, including grain or flour, groundnuts, animal feedstuffs, timber or household goods, e.g. carpets and textiles, compounds of the invention are useful against attack by arthropods, more especially beetles, including weevils, moths or mites, for example Ephestia spp. (flour moths), Anthrenus spp. (carpet beetles), Tribohum spp. (flour beetles), Sitophilus spp. (grain weevils) or Acarus spp. (mites).
In the control of cockroaches, ants or termites or similar arthropod pests in infested domestic or industrial premises or in the control of mosquito larvae in waterways, wells, reservoirs or other running or standing water.
For the treatment of foundations, structures or soil in the prevention of the attack on building by termites, for example, Reticuhtermes spp., Heterotermes spp., Coptotermes spp..

In agriculture against adults, larvae and eggs of Lepidoptera (butterfhes and moths), e.g. Hehothis spp. such as Hehothis virescens (tobacco budworm), Hehothis armigera and Hehothis zea. Against adults and larvae of Coleoptera (beetles) e.g. Anthonomus spp. e.g. grandis (cotton boll weevil), Leptinotarsa decemhneata (Colorado potato beetle), Diabrotica spp. (corn rootworms). Against Heteroptera (Hemiptera and Homoptera) e.g. Psylla spp., Bemisia spp., Trialeurodes spp., Aphis spp., Myzus spp., Megoura viciae, Phylloxera spp., Nephotettix spp. (rice leaf hoppers), Nilaparvata spp..
Against Diptera e.g. Musca spp.. Against Thysanoptera such as Thrips tabaci. Against Orthoptera such as Locusta and Schistocerca spp., (locusts and crickets) e.g. Gryllus spp,, and Acheta spp. for example, Blatta orientahs, Peripianeta americana, Blatella germanica, Locusta migratoria migratorioides, and Schistocerca gregaria. Against Collembola e.g. Peripianeta spp. and Blatella spp. (roaches). Against arthropods of agricultural significance such as Acari (mites) e.g, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus galhnae, 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., Tetranychus spp., Eotetranychus spp., Ohgonychus spp., Eutetranychus spp. From the order of the Isopoda, for example, Oniscus aselus, Armadium vulgare, Porcelho scaber.
Against nematodes which attack plants or trees of importance to agriculture, forestry or horticulture either directly or by spreading bacterial, viral, mycoplasma or fungal diseases of the plants. The plant-parasitic nematodes which can be controlled in accordance with the invention include, for example, the root-parasitic soil-dwelhng nematodes such as, for example, those of the genera Meloidogyne (root knot nematodes, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera palhda, Heterodera trifohi) and of the genera Radopholus, such as Radopholus simihs, Pratylenchus such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus;

Tylenchulus such as Tylenchulus semipenetrans, Tylenchorhynchus, such as Tylenchorhynchus dubius and Tylenchorhynchus claytoni, Rotylenchus such as Rotylenchus robustus, Hehocotylenchus such as Hahocotylenchus multicinctus, Belonoaimus such as Belonoaimus longicaudatus, Longidorus such as Longidorus elongatus, Trichodorus such as Trichodorus primitivus and Xiphinema such as Xiphinema index.
Other nematode genera which can be controlled using the compounds according to the invention are Ditylenchus (stem parasites, such as Dityienchus dipsaci and Ditylenchus destructor), Aphelenchoides (fohar nematodes, such as Aphelenchoides ritzemabosi) and Anguina (seed nematodes, such as Anguina tritici). In the field of veterinary medicine or hvestock husbandry or in the maintenance of pubhc health against arthropods which are parasitic internally or externally upon vertebrates, particularly warm-blooded vertebrates, for example domestic animals, e.g. cattle, sheep, goats, equines, swine, poultry, dogs or cats, for example Acarina, including ticks (e.g. Ixodes spp., Boophilus spp. e.g. Boophilus microplus, Rhipicephalus spp. e.g. Rhipicephalus appendiculatus Ornithodorus spp, (e.g. Ornithodorus moubata) and mites (e.g. Damahnia spp.); fleas; Diptera (e.g. Aedes spp., Anopheles spp., Musca spp., Hypoderma spp.); Hemiptera.; Dictyoptera (e.g. Periplaneta spp., Blatella spp.); Hymenoptera; for example against infections of the gastro-intestinal tract caused by parasitic nematode worms, for example members of the family Trichostrongyhdae.
From the class of the helminths, for example, Haemonchus, Trichostrongulus, Ostertagia, Cooperia, Chabertia, Strongyloides, Oesophagostomum, Hyostrongulus, Ancylostoma, Ascaris and Heterakis and also Fasciola.
From the class of the Gastropoda, for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Buhnus spp., Oncomelania spp. From the class of the Bivalva, for example, Dreissena spp.

In practical use for the control of arthropods, especially insects or acarids, or nematode pests of plants, a method, for example, comprises applying to the plants or to the medium in which they grow an effective amount of a compound of the invention. For such a method, the compound of the invention is generally apphed to the locus in which the arthropod or nematode infestation is to be controlled at an effective rate in the range of about 2g to about 1 kg of the active compound per hectare of locus treated. Under ideal conditions, depending on the pest to be controlled, a lower rate may offer adequate protection. On the other hand, adverse weather conditions, resistance of the pest or other factors may require that the active ingredient be used at higher rates. The optimum rate depends usually upon a number of factors, for example, the type of pest being controlled, the type or the growth stage of the infested plant, the row spacing or also the method of apphcation. Preferably an effective rate range of the active compound is from about lOg/ha to about 400g/ha, more preferably from about 50g/ha to about 200 g/ha. When a pest is soil-borne, the active compound generally in a formulated composition, is distributed evenly over the area to be treated (ie, for example broadcast or band treatment) in any convenient manner and is apphed at rates from about 10g/ha to about 400g ai/ha, preferably from about 50g/ha to about 200 g ai/ha. When apphed as a root dip to seedhngs or drip irrigation to plants the hquid solution or suspension contains from about 0.075 to about 1000 mg ai/1, preferably from about 25 to about 200 mg ai/1. Apphcation may be made, if desired, to the field or crop-growing area generally or in close proximity to the seed or plant to be protected from attack. The compound of the invention can be washed into the soil by spraying with water over the area or can be left to the natural action of rainfall. During or after apphcation, the formulated compound can, if desired, be distributed mechanically in the soil, for example by ploughing, disking, or use of drag chains. Apphcation can be prior to planting, at planting, after planting but before sprouting has taken place, or after sprouting.
The compound of the invention and methods of control of pests therewith are of particular value in the protection of field, forage, plantation, glasshouse, orchard or vineyard crops, of ornamentals, or of plantation or forest trees, for example: cereals (such as wheat or rice), cotton, vegetables (such as peppers), field crops (such as

sugar beets, soybeans or oil seed rape), grassland or forage crops (such as maize or sorghum), orchards or groves (such as of stone or pit fruit or citrus), ornamental plants, flowers or vegetables or shrubs under glass or in gardens or parks, or forest trees (both deciduous and evergreen) in forests, plantations or nurseries. They are also valuable in the protection of timber (standing, felled, converted, stored or structural) from attack, for example, by sawflies or beetles or termites. They have apphcations in the protection of stored products such as grains, fruits, nuts, spices or tobacco, whether whole, milled or compounded into products, from moth, beetle, mite or grain weevil attack. Also protected are stored animal products such as skins, hair, wool or feathers in natural or converted form (e.g. as carpets or textiles) from moth or beetle attack as well as stored meat, fish or grains from beetle, mite or fly attack.
Additionally, the compound of the invention and methods of use thereof are of particular value in the control of arthropods or helminths which are injurious to, or spread or act as vectors of diseases domestic animals, for example those hereinbefore mentioned, and more especially in the control of ticks, mites, hce, fleas, midges, or biting, nuisance or myiasis fhes. The compounds of the invention are particularly useful in controlhng arthropods or helminths which are present inside domestic host animals or which feed in or on the skin or suck the blood of the animal, for which purpose they may be administered orally, parenterally, percutaneously or topically.
The compositions hereinafter described for apphcation to growing crops or crop growing loci or as a seed dressing may, in general, alternatively be employed in the protection of stored products, household goods, property or areas of the general environment. Suitable means of applying the compounds of the invention include: to growing crops as fohar sprays (for example as an in-fun-ow spray), dusts, granules, fogs or foams or also as suspensions of finely divided or encapsulated compositions as soil or root treatments by hquid drenches, dusts, granules, smokes or foams; to seeds of crops via apphcation as seed dressings by hquid slurries or dusts;
to animals infested by or exposed to infestation by arthropods or helminths, by parenteral, oral or topical apphcation of compositions in which the active ingredient

exhibits an immediate and/or prolonged action over a period of time against the arthropods or helminths, for example by incorporation in feed or suitable orally-ingestible pharmaceutical formulations, edible baits, salt hcks, dietary supplements, pour-on formulations, sprays, baths, dips, showers, jets, dusts, greases, shampoos, creams, wax smears or hvestocl to the environment in general or to specific locations where pests may lurk, including stored products, timber, household goods, or domestic or industrial premises, as sprays, fogs, dusts, smokes, wax-smears, lacquers, granules or baits, or in tricklefeeds to waterways, wells, reservoirs or other running or standing water.
The compounds of the formula (I) can also be employed for controlhng harmful organisms in crops of known genetically engineered plants or genetically engineered plants yet to be developed. As a rule, the transgenic plants are distinguished by especially advantageous properties, for example by resistances to particular crop protection agents, resistances to plant diseases or pathogens of plant diseases, such as particular insects or microorganisms such as fungi, bacteria or viruses. Other particular properties concern, for example, the harvested material with regard to quantity, quahty, storage properties, composition and specific constituents. Thus, transgenic plants are known where the starch content is increased, or the starch quahty is altered, or where the harvested material has a different fatty acid composition.
The use in economically important transgenic crops of useful plants and ornamentals is preferred, for example of cereals such as wheat, barley, rye, oats, millet, rice, cassava and maize or else crops of sugar beet, cotton, soya, oilseed rape, potatoes, tomatoes, peas and other types of vegetables.
When used in transgenic crops, in particular those which have resistances to insects, effects are frequently observed, in addition to the effects against harmful organisms to be observed in other crops, which are specific for apphcation in the transgenic crop in question, for example an altered or specifically widened spectrum of pests

which can be controlled, or altered apphcation rates which may be ennployed for
apphcation.
The invention therefore also relates to the use of compounds of the formula (1) for controlhng harmful organisms in transgenic crop plants.
According to a further feature of the present invention there is provided a pesticidal composition comprising one or more compounds of the invention as defined above, in association with, and preferably homogeneously dispersed in one or more compatible pesticidally acceptable diluents or carriers and/or surface active agents [i.e. diluents or carriers and/or surface active agents of the type generally accepted in the art as being suitable for use in pesticidal compositions and which are compatible with compounds of the invention].
in practice, the compounds of the invention most frequently form parts of compositions. These compositions can be employed to control arthropods, especially insects and acarids, or helminths such as plant nematodes. The compositions may be of any type known in the art suitable for apphcation to the desired pest in any premises or indoor or outdoor area. These compositions contain at least one compound of the invention as the active ingredient in combination or association with one or more other compatible components which are for example, sohd or hquid carriers or diluents, adjuvants, surface-active-agents, or the hke appropriate for the intended use and which are agronomically or medicinally acceptable. These compositions, which may be prepared by any manner known in the art, hkewise form a part of this invention.
The compounds of the invention, in their commercially available formulations and in the use forms prepared from these formulations may be present in mixtures with other active substances such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth regulatory substances or herbicides.
The pesticides include, for example, phosphoric esters, carbamates, carboxyhc esters, formamidines, tin compounds and materials produced by microorganisms.

Preferred components in mixtures are:
1. from the group of the phosphorus compounds
acephate, azamethiphos, azinphos-ethyi, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos (F-67825), ctilorethoxyphos, cthorfenvinphos, chlormeplnos, chlorpyrifos, chlorpyrifos-mettiyj, demeton, demeton-S-methyl, demeton-S-mettiyl suifone, diahfos, diazinon, dictilorvos, dicrotophos, dimethoate, disulfoton, EPN, ethion, ettioprophos, etrinnfos, famphur, fenamiphos, fenitriothion, fensulfothion, fentthon, flupyrazofos, fonofos, formotlnion, fosthiazate, ineptenoptios, isazophos, isothioate, isoxatihon, malathion, methacrifos, methamidophos, methidathion, sahtihon, mevinptios, monocrotophos, naied, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosaione, pinosfoian, phosphocarb (BAS-301), phiosmet, phosphamidon, pfioxim, pirimiphos, pirinniphos-etinyl, pirimiplnos-methyl, profenofos, propaphos, proetamplnos, protihofos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thiometon, triazoptios, tricthorpficn, vamidotinion;
2. from ttie group of tine carbamates
alanycarb (OK-135), aldicarb, 2-sec-butylphenyl methylcarbamate (BPIVIC), carbaryl, carbofuran, carbosulfan, cloettiocarb, benfuracarb, etihofencarb, furathiocarb, HCN-801, isoprocarb, metfiomyl, 5-mettnyl-m-cumenylbutyryl (mettnyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, 1-methylthio(ethyhdeneamino)-N-methyl-N-(morphohnothio)carbamate (UC 51717), triazamate;
3. from the group of the carboxyhc esters
acrinatfirin, allethrin, alphametrln, 5-ben2yl-3-furylmettiyl (E)- (1R)-cis-2,2-dimettiyl-3-(2-oxottniolan-3-yhdenemethyl)cyclopropanecarboxylate, beta-cyfluttirin, alpha-cypermethrln, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyhsomer), bioresmethrin, bifenthrin, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl (1RS)-trans-3-(4-tert-butylphenyl)-2,2-dimethylcyciopropanecarboxylate (NCI 85193), cycloprothrin, cyfluthrin, cyhalothrin, cythithrin, cypermethrin, cyphienothrin, deltamethrin, empentinrin, esfenvalerate, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate,

flumethrin, fluvahnate (D isomer), imiprothrin (S-41311), lambda-cyhalothrin, permethrin, phenothrin (® isomer), prallethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin, traiomethrin, transfluthrin, zeta-cypermethrin (F-56701);
4. from the group of the amidines amitraz, chlordimeform;
5. from the group of the tin compounds cyhexatin, fenbutatin oxide;
6. others
abamectin, ABG-9008, acetamiprld, acequinocyl, Anagrapha falcitera, AKD-1022, AKD-3059, ANS-118, azadirachtin, Bacillus thuringiensis, Beauveria bassianea, bensultap, bifenazate, binapacryl, BJL-932, bromopropylate, BTG-504, BTG-505. buprofezin, camphechlor, cartap, chlorobenzilate, chlorfenapyr, chlorfluazuron, 2-(4-chlorophenyl)-4,5-diphenylthlophene (UBI-T 930), chlorfentezine, chlorproxyfen, chromafenozide, ciothianidine, 2-naphthylmethyl cyclopropanecarboxylate (Ro12-0470), cyromazin, diacloden (thiamethoxam), diafenthiuron, DBI-3204, ethyl 2-chloro-N-(3,5-dichloro-4-(1,1,2,3,3,3-hexafluoro-1-propyloxy)phenyl)carbamoyI)-2-carboximidate, DDT, dicofol, difiubenzuron, N-(2,3-dihydro-3-methyl-1,3-thiazol-2-yhdene)-2,4-xyhdine, dihydroxymethyldihydroxypyrrohdine, dinobuton, dinocap, diofenolan, emamectin benzoate, endosulfan, ethiprole (sulfethiprole), ethofenprox, etoxazole, fenazaquin, fenoxycarb, fipronil, fluazuron, flumlte (flufenzine, SZI-121), 2-fluoro-5-(4-(4-ethoxypheny[)-4-methyl-1-pentyl)dlphenyl ether (MTi 800), granulosis and nuclear polyhedrosis viruses, fenpyroximate, fenthiocarb, fluacrypyrim, flubenzlmine, flubrocythrinate, flucycloxuron, flufenoxuron, flufenzine, flufenprox, fluproxyfen, gamma-HCH, halfenozide, halofenprox, hexaflumuron (DE_473), hexythiazox, HOI-9004, hydramethylnon (AC 217300), IKI-220, indoxacarb, ivermectin, L-14165, imidacioprid, indoxacarb (DPX-MP062), kanemite (AKD-2023), lufenuron, M-020, M-020, methoxyfenozide, milbemectin, NC-196, neemgard, nidinoterfuran, nitenpyram, 2-nitromethyi-4,5-dihydro-6H-thiazine (DS

52618), 2-nitromethyl-3,4-dihydrothia2ole (SD 35651), 2-nitromethylene-1,2-thiazinan-3-ylcarbamaldehyde (WL 108477), novaluron, pirydaryl, propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen, pyriproxyfen, NC-196, NC-1111, NNI-9768, novaluron (MCW-275), OK-9701, OK-9601, OK-9602, OK-9802, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, Sl-8601, silafluofen, silomadine (CG-177), spinosad, spirodiclofen, SU-9118, tebufenozide, tebufenpyrad, teflubenzuron, tetradifon, tetrasul, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosyn A, triflumuron, verbutin, vertalec (mykotal), YI-5301.
The abovementioned components for combinations are known active substances, many of which are described in Ch.R Worthing, S.B. Walker, The Pesticide Manual, 12* Edition, British Crop Protection Council, Farnham 2000.
The effective use doses of the compounds employed in the invention can vary within wide hmits, particularly depending on the nature of the pest to be ehminated or degree of infestation, for example, of crops with these pests. In general, the compositions according to the invention usually contain about 0.05 to about 95% (by weight) of one or more active ingredients according to the invention, about 1 to about 95% of one or more sohd or hquid carriers and, optionally, about 0.1 to about 50% of one or more other compatible components, such as surface-active agents or the hke. In the present account, the term "carrieR4 denotes an organic or inorganic ingredient, natural or synthetic, with which the active ingredient is combined to facihtate its apphcation, for example, to the plant, to seeds or to the soil. This carrier is therefore generally inert and it must be acceptable (for example, agronomically acceptable, particularly to the treated plant).
The carrier may be a sohd, for example, clays, natural or synthetic sihcates, sihca, resins, waxes, sohd fertihzers (for example ammonium salts), ground natural minerals, such as kaohns, clays, talc, chalk, quartz, attapulgite, montmorillonite, bentonite or diatomaceous earth, or ground synthetic minerals, such as sihca, alumina, or sihcates especially aluminium or magnesium sihcates. As sohd carriers for granules the following are suitable: crushed or fractionated natural rocks such as calcite, marble, pumice, sepiohte and dolomite; synthetic granules of inorganic or

organic meals; granules of organic material such as sawdust, coconut shells, corn cobs, corn husks or tobacco stalks; kieselguhr, tricalcium phosphate, powdered cork, or absorbent carbon black; water soluble polymers, resins, waxes; or sohd fertihzers. Such sohd compositions may, if desired, contain one or more compatible wetting, dispersing, emulsifying or colouring agents which, when sohd, may also serve as a diluent.
The carrier may also be hquid, for example: water, alcohols, particularly butanol or glycol, as well as their ethers or esters, particularly methylglycol acetate; ketones, particularly acetone, cyclohexanone, methylethyl ketone, methyhsobutylketone, or isophorone; petroleum fractions such as paraffinic or aromatic hydrocarbons, particularly xylenes or alkyl naphthalenes; mineral or vegetable oils; ahphatic chlorinated hydrocarbons, particularly trichloroethane or methylene chloride; aromatic chlorinated hydrocarbons, particularly chlorobenzenes; water-soluble or strongly polar solvents such as dimethylformamide, dimethyl sulphoxide, or N-methylpyrrohdone; hquefied gases; or the hke or a mixture thereof. The surface-active agent may be an emulsifying agent, dispersing agent or wetting agent of the ionic or non-ionic type or a mixture of such surface-active agents. Amongst these are e.g., salts of polyacryhc acids, salts of hgnosulphonic acids, salts of phenolsulphonic or naphthalenesulphonic acids, polycondensates of ethylene oxide with fatty alcohols orfatty acids or fatty esters or fatty amines, substituted phenols (particularly alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (particularly alkyltaurates), phosphoric esters of alcohols or of polycondensates of ethylene oxide with phenols, esters of fatty acids with polyols, or sulphate, sulphonate or phosphate functional derivatives of the above compounds. The presence of at least one surface-active agent is generally essential when the active ingredient and/or the inert carrier are only shghtly water soluble or are not water soluble and the carrier agent of the composition for apphcation is water. Compositions of the invention may further contain other additives such as adhesives or colorants. Adhesives such as carboxymethylcellulose or natural or synthetic polymers in the form of powders, granules or lattices, such as arable gum, polyvinyl alcohol or polyvinyl acetate, natural phosphohpids, such as cephahns or lecithins, or synthetic phosphohpids can be used in the formulations. It is possible to use

colorants such as inorganic pigments, for example: iron oxides, titanium oxides or Prussian Blue; organic dyestuffs, such as ahzarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs; or trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum or zinc.
For their agricultural apphcation, the compounds of the invention are therefore generally in the form of compositions, which are in various sohd or hquid forms. Sohd forms of compositions which can be used are dusting powders (with a content of the compound of the invention, ranging up to 80%), wettable powders or granules (including water dispersible granules), particularly those obtained by extrusion, compacting, impregnation of a granular carrier, or granulation starting from a powder (the content of the compound of the invention, in these wettable powders or granules being between about 0.5 and about 80%). Sohd homogenous or heterogenous compositions containing one or more compounds of the invention, for example granules, pellets, briquettes or capsules, may be used to treat standing or running water over a period of time. A similar effect may be achieved using trickle or intermittent feeds of water dispersible concentrates as described herein. hquid compositions, for example, include aqueous or non-aqueous solutions or suspensions (such as emulsifiable concentrates, emulsions, flowables, dispersions, or solutions) or aerosols. hquid compositions also include, in particular, emulsifiable concentrates, dispersions, emulsions, flowables, aerosols, wettable powders (or powder for spraying), dry flowables or pastes as forms of compositions which are hquid or intended to form hquid compositions when apphed, for example as aqueous sprays (including low and ultra-low volume) or as fogs or aerosols. hquid compositions, for example, in the form of emulsifiable or soluble concentrates most frequently comprise about 5 to about 80% by weight of the active ingredient, while the emulsions or solutions which are ready for apphcation contain, in their case, about 0.01 to about 20% of the active ingredient. Besides the solvent, the emulsifiable or soluble concentrates may contain, when required, about 2 to about 50% of suitable additives, such as stabihzers, surface-active agents, penetrating agents, corrosion inhibitors, colorants or adhesives. Emulsions of any required concentration, which are particularly suitable for apphcation, for example, to plants, may be obtained from these concentrates by dilution with water. These

compositions are included within the scope of the connpositions which may be employed in the present invention. The emulsions may be in the form of water-in-oil or oil-in-water type and they may have a thick consistency. The hquid compositions of this invention may, in addition to normal agricultural use apphcations be used for example to treat substrates or sites infested or hable to infestation by arthropods (or other pests controlled by compounds of this invention) including premises, outdoor or indoor storage or processing areas, containers or equipment or standing or running water.
All these aqueous dispersions or emulsions or spraying mixtures can be apphed, for example, to crops by any suitable means, chiefly by spraying, at rates which are generally of the order of about 100 to about 1,200 hters of spraying mixture per hectare, but may be higher or lower (eg. low or ultra-low volume) depending upon the need or apphcation technique. The compound or compositions according to the invention are conveniently apphed to vegetation and in particular to roots or leaves having pests to be ehminated. Another method of apphcation of the compounds or compositions according to the invention is by chemigation, that is to say, the addition of a formulation containing the active ingredient to irrigation water. This irrigation may be sprinl The concentrated suspensions, which can be apphed by spraying, are prepared so as to produce a stable fluid product which does not settle (fine grinding) and usually contain from about 10 to about 75% by weight of active ingredient, from about 0.5 to about 30% of surface-active agents, from about 0.1 to about 10% of thixotropic agents, from about 0 to about 30% of suitable additives, such as anti-foaming agents, corrosion inhibitors, stabihzers, penetrating agents, adhesives and, as the carrier, water or an organic hquid in which the active ingredient is poorly soluble or insoluble Some organic sohds or inorganic salts may be dissolved in the carrier to help prevent setthng or as antifreezes for water.
The wettable powers (or powder for spraying) are usually prepared so that they contain from about 10 to about 80% by weight of active ingredient, from about 20 to about 90% of a sohd carrier, from about 0 to about 5% of a wetting agent, from about 3 to about 10% of a dispersing agent and, when necessary, from about 0 to about

80% of one or more stabihzers and/or other additives, such as penetrating agents, adhesives, anti-caking agents, colorants, or the hke. To obtain these wettable powders, the active ingredient is thoroughly mixed in a suitable blender with additional substances which may be impregnated on the porous filler and is ground using a mill or other suitable grinder. This produces wettable powders, the wettabihty and the suspendabihty of which are advantageous. They may be suspended in water to give any desired concentration and this suspension can be employed very advantageously in particular for apphcation to plant fohage. The "water dispersible granules (WG)" (granules which are readily dispersible in water) have compositions which are substantially close to that of the wettable powders. They may be prepared by granulation of formulations described for the wettable powders, either by a wet route (contacting finely divided active ingredient with the inert filler and a httle water, e.g. 1 to 20% by weight, or with an aqueous solution of a dispersing agent or binder, followed by drying and screening), or by a dry route (compacting followed by grinding and screening).
The rates and concentrations of the formulated compositions may vary according to the method of apphcation or the nature of the compositions or use thereof. Generally speaking, the compositions for apphcation to control arthropod or helminth pests usually contain from about 0.00001 % to about 95%, more particularly from about 0.0005% to about 50% by weight of one or more compounds of the invention, or of total active ingredients (that is to say the compounds of the invention, together with other substances toxic to arthropods or helminths, synergists, trace elements or stabihzers). The actual compositions employed and their rate of apphcation will be selected to achieve the desired effect(s) by the farmer, hvestock producer, medical or veterinary practitioner, pest control operator or other person skilled in the art. Sohd or hquid compositions for apphcation topically to animals, timber, stored products or houslehold goods usually contain from about 0.00005% to about 90%, more particularly from about 0.001 % to about 10%, by weight of one or more compounds of the invention. For administration to animals orally or parenterally, including percutaneously sohd or hquid compositions, these normally contain from about 0.1 % to about 90% by weight of one or more compounds of the invention. Medicated feedstuffs normally contain from about 0.001% to about 3% by weight of

one or more compounds of the invention. Concentrates or supplements for mixing with feedstuffs normally contain from about 5% to about 90%, preferably from about 5% to about 50%, by weight of one or more compounds of the invention. Mineral salt hcks normally contain from about 0.1 % to about 10% by weight of one or more compounds of formula (I) or pesticidally acceptable salts thereof. Dusts or hquid compositions for apphcation to hvestock, goods, premises or outdoor areas may contain from about 0.0001% to about 15%, more especially from about 0.005% to about 2.0%, by weight, of one or more compounds of the invention. Suitable concentrations in treated waters are between about 0.0001 ppm and about 20 ppm, more particularly about 0.001 ppm to about 5.0 ppm. of one or more compounds of the invention, and may be used therapeutically in fish farming with appropriate exposure times. Edible baits may contain from about 0.01% to about 5%, preferably from about 0.01 % to about 1.0%, by weight, of one or more compounds of the invention.
When administered to vertebrates parenterally, orally or by percutaneous or other means, the dosage of compounds of the invention, will depend upon the species, age, or health of the vertebrate and upon the nature and degree of its actual or potential infestation by arthropod or helminth pests. A single dose of about 0.1 to about 100 mg, preferably about 2.0 to about 20.0 mg, per kg body weight of the animal or doses of about 0.01 to about 20.0 mg, preferably about 0.1 to about 5.0 mg, per kg body weight of the animal per day, for sustained medication, are generally suitable by oral or parenteral administration. By use of sustained release formulations or devices, the daily doses required over a period of months may be combined and administered to animals on a single occasion. The following composition EXAMPLES 2A - 2M illustrate compositions for use against arthropods, especially insects or acarids, or helminths such as plant nematodes, which comprise, as active ingredient, compounds of the invention, such as those described in preparative examples. The compositions described in EXAMPLES 2A - 2M can each be diluted to give a sprayable compositon at concentrations suitable for use in the field. Generic chemical descriptions of the ingredients (for which all of the following percentages are in weight percent), used in the composition EXAMPLES 2A - 2M exemphfied below, are as follows:

Ethylan BCP Nonylphenol ethylene oxide condensate
Soprophor BSU Tristyrylphenol ethylene oxide condensate
Arylan CA A 70% w/v solution of calcium dodecylbenzenesulfonate
Solvesso 150 hght CIQ aromatic solvent
Arylan S Sodium dodecyjbenzenesulfonate
Darvan NO2 Sodium hgnosulphonate
Cehte PF Synthetic magnesium sihcate can-ier
Sopropon T36 Sodium salts of polycarboxyhc acids
Rhodigel 23 Polysaccharide xanthan gum
Bentone 38 Organic derivative of magnesium montmorhlonite
Aerosil Microfine sihcon dioxide
EXAMPLE 2A
A water soluble concentrate Is prepared with the composition as follows:
Active ingredient 7%
Ethylan BCP 10%
N-methylpyrrohdone 83%
To a solution of Ethylan BCP dissolved in a portion of N-methylpyrrohdone is added
the active ingredient with heating and stirring until dissolved. The resulting solution
is made up to volunne with the remainder of the solvent.
EXAMPLE 2B
An emulsifiable concentrate (EC) is prepared with the composition as follows:
Active ingredient 25%(max)
Soprophor BSU 10%
Arylan CA 5%
N-methylpyn-ohdone 50%
Solvesso 150 10%
The first three components are dissolved in N-methylpyrrohdone and to this is then added the Solvesso 150 to give the final volume.

EXAMPLE 2C
A wettabie powder (WP) is prepared with the composition as fohows:
Active ingredient 40%
Arylan S 2%
Darvan NO2 5%
Cehte PF 53%
The ingredients are mixed and ground in a hammer-mill to a powder with a particle size of less than 50 microns.
EXAMPLE 2D
An aqueous-flowable formulation is prepared with the composition as follows:
Active ingredient 40.00%
EthylanBCP 1.00%
Sopropon T360. 0.20%
Ethylene glycol 5.00%
Rhodigel230. 0.15%
Water 53.65%
The ingredients are intimately mixed and are ground in a bead mill until a mean particle size of less than 3 microns Is obtained.
EXAMPLE 2E
An emulsifiable suspension concentrate is prepared with the composition as follows:
Active ingredient 30.0%
EthylanBCP 10.0%
Bentone 38 0.5%
Solvesso150 59.5%
The Ingredients are intimately mixed and ground in a beadmill until a mean particle size of less than 3 microns is obtained.
EXAMPLE 2F
Awaterdispersible granule is prepared with the composition as follows:

Active ingredient 30%
DarvanNo2 15%
Arylan S 8%
Cehte PF 47%
The ingredients are mixed, micronized in a fluid-energy mill and then granulated in a rotating pelletizer by spraying with water (up to 10%). The resulting granules are dried in a fluid-bed drier to remove excess water.
EXAMPLE 2G
A dusting powder is prepared with the composition as follows:
Active ingredient 1 to 10%
Talc powder-superfine 99 to 90%
The ingredients are intimately mixed and further ground as necessary to achieve a fine powder. This powder may be apphed to a locus of arthropod infestation, for example refuse dumps, stored products or household goods or animals infested by, or at risk of infestation by, arthropods to control the arthropods by oral ingestion. Suitable means for distributing the dusting powder to the locus of arthropod infestation include mechanical blowers, handshakers or hvestock self treatment devices.
EXAMPLE 2H
An edible bait is prepared with the composition as follows:
Active ingredient 0.1 to 1.0%
Wheat flour 80%
Molasses 19.9 to 19%
The ingredients are intimately mixed and formed as required into a bait form. This edible bait may be distributed at a locus, for example domestic or industrial premises, e.g. kitchens, hospitals or stores, or outdoor areas, infested by arthropods, for example ants, locusts, cockroaches or fhes, to control the arthropods by oral ingestion.

EXAMPLE 21
A solution formulation is prepared with a composition as follows:
Active ingredient 15%
Dimethyl sulfoxide - 85%
The active ingredient is dissolved in dimethyl sulfoxide with mixing and or heating as required. This solution may be apphed percutaneously as a pour-on apphcation to domestic animals infested by arthropods or, after sterihzation by filtration through a polytetrafiuoroethylene membrane (0.22 micrometer pore size), by parenteral injection, at a rate of apphcation of from 1.2 to 12 ml of solution per 100 kg of animal body weight.
EXAMPLE 2J
A wettable powder is prepared with the composition as follows:
Active ingredient 50%
Ethylan BCP 5%
Aerosil 5%
Cehte PF 40%
The Ethylan BCP is absorbed onto the Aerosil which is then mixed with the other ingredients and ground in a hammer-mill to give a wettable powder, which may be diluted with water to a concentration of from 0.001% to 2% by weight of the active compound and apphed to a locus of infestation by arthropods, for example, dipterous larvae or plant nematodes, by spraying, or to domestic animals infested by, or at risk of infection by arthropods, by spraying or dipping, or by oral administration in drinking water, to control the arthropods.
EXAMPLE 2K
A slow release bolus composition is formed from granules containing the following components in varying percentages(similar to those described for the previous compositions) depending upon need:

Active ingredient
Density agent
Slow-release agent
Binder The intimately mixed ingredients are formed into granules which are compressed into a bolus with a specific gravity of 2 or more. This can be administered orally to ruminant domestic animals for retention within the reticulo-rumen to give a continual slow release of active compound over an extended period of time to control infestation of the ruminant domestic animals by arthropods.
EXAMPLE 2L
A slow release composition in the form of granules, pellets, brickettes or the hke can
be prepared with compositions as follows:
Active ingredient 0.5 to 25%
Polyvinyl chloride 75 to 99.5%
Dioctyl phthalate (plasticizer) The components are blended and then formed into suitable shapes by melt-extrusion or molding. These composition are useful, for example, for addition to standing water or for fabrication into collars or eartags for attachment to domestic animals to control pests by slow release.
EXAMPLE 2M
A water dispersible granule is prepared with the composition as follows:
Active ingredient 85%(max)
Polyvinylpyrrohdone 5%
Attapulgite clay 6%
Sodium lauryl sulfate 2%
Glycerine 2%
The ingredients are mixed as a 45% slurry with water and wet milled to a particle size of 4 microns, then spray-dried to remove water.

METHODS OF PESTICIDAL USE
The following representative test procedures, using compounds of the invention, were conducted to determine the parasiticidai and pesticidai activity of compounds of the invention.
METHOD A:
Germinated field bean seeds (Vicia faba) with seed roots were transferred into brown glass bottles filled with tap water and then populated with about 100 black bean aphids (Aphis fabae). Plants and aphids were then dipped into an aqueous solution of the formulated preparation to be examined for 5 seconds. After they had drained, plants and animals were stored in a chmatized chamber (16 hours of hght/day, 25°C, 40-60% relative atmospheric humidity). After 3 and 6 days of storage, the effect of the preparation on the aphids was determined. At a concentration of 100 ppm (based on the content of active compound), the following Compounds caused a mortahty of at least 50% among the aphids:

METHOD B:
Germinated field bean seeds (Vicia faba) with seed roots were transferred into brown
glass bottles filled with tap water. Four milhhters of an aqueous solution of the

formulated preparation to be examined were pipetted into the brown glass bottle. The field bean was then heavily populated with about 100 black bean aphids (Aphis fabae). Plants and aphids were then stored in a chmatized chamber (16 hours of hght/day, 25°C, 40-60% relative atmospheric humidity). After 3 and 6 days of storage, the root-systemic effect of the preparation on the aphids was determined. At a concentration of 10 ppm (based on the content of active compound), the following Compounds caused a mortahty of at least 80% among the aphids, by root-systemic action:



WE CLAIM:
1. A compound of the formula (I):

wherein:
R1 is —C(=U)NR6R6;
R6isH, (C1-C6)alkylorR6;
R6 is R6 OH or NH2 ; or is (C1-C6)alkyl substituted by one or more R groups;
or R6 and R1' together with the interconnecting atoms form a heterocyclic ring selected from (A), (B), (C), (D) and (E);


R6' is (C3-C8)cycloalkyl or (C3-C8)cycloalkyl-(C,-C6)alkyl, which cycloalkyl groups are unsubstituted or substituted by one or more (C1-C6)aikyi, (C1-C6)haloaIkyI or R6 groups; or is (C1-C6)alkyl, (C3-C6)alkenyl or (C3-C6)alkynyl which last three mentioned groups are substituted by one or more R6 groups; or is (C1-C6)alkylamino; or is NH(CHR14)saryl which aryl group is unsubstituted or substituted by one or more Regroups;
R6 is H or R6 or is (C1-C6)alkyl unsubstituted or substituted by one or more R groups;
or R1^ and R1* together with the adjacent N atom form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R6orR1^" groups;
R6 is (C3-C6)alkenyl, (C3-C6)alkynyl, (C3-C8)cycloalkyl, (C,-C6)alkoxy, (C3-C6)alkenyloxy, (C3-C6)alkynyloxy, (C1-C6)alkylamino, di-(C1-C6)alkylamino, CO(Ci-C6)alkyl, NHCO(C,-C6)alkyl, NHS02(C,-C6)alkyl or S02(C,-C6)alkyl which last 12 mentioned groups are unsubstituted or substituted by one or more R6 groups; or is (C3-C8)cycloalkyl-(C1-C6)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R6 groups; or is NH(CHR1Vryl, —(CR1^R1Vryl' 0(R1^R1Vryl, NHCOaryl, C0(CH2)taryl, NHS02aryl, S02(CH2)„aryl or N=C(aryl)2, — (CR15R16)pheterocyclyl or 0(R1^R1^)rheterocyclyl, which last ten mentioned aryl or heterocyclyl groups are unsubstituted or substituted by one or more R1^ groups; or is 0(CR1^R"^)p(C3-C8)cycloalkyl or N=C[(C,-C6)alkyl]2;

R6 is halogen, (C1-C6)alkoxy, (C,-C6)haloalkoxy, S(0)nR4a CN, COJCC,-C6)alkyl, CO2H, NO2, OH, amino, (C1-C6)aIkylamino, di-(C1-C6)alkylamino, carbamoyl, (C1-C6)-alkylcarbamoyl, di-(C1-C6)-alkylcarbamoyl or CH[0(C|-C6)alkyl]2; or is phenoxy unsubstituted or substituted by one or more R1'*^ or halogen groups;

R6 R\ R6 R1^ R1^ R6' and R6^are each independently H; or (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C8)cycloalkyl, (C,-C6)alkoxy, (C2-C6)alkenyloxy or (C2-C6)alkynyloxy, which last seven mentioned groups are unsubstituted or substituted by one or more R6 groups; or is —(CH2)paryl or heterocyclyl, which aryl or heterocyclyl groups are unsubstituted or substituted by one or more R6 groups; or (C3-C8)cycloalkyl-(C1-C6)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R6 groups;
or R1 and R6 together with the attached carbon atom may represent C=0;

R10, R20 and R23are each independently H; or (C1-C6)alkyl, (C3-C6)alkenyl, (C3-C6)alkynyl or (C3-C8)cycloalkyl, which last four mentioned groups are unsubstituted or substituted by one or more R groups; or is (C3-C8)cycloalkyl-(C1-C6)aIkyl which cycloalkyl group is unsubstituted or substituted by one or more R6 groups; or is — (CH2)paryl or heterocyclyl which aryl or heterocyclyl groups are unsubstituted or substituted by one or more Regroups;
R" is R6, halogen, CN, COaCCi-CeJalkyl, NO2 or S(0)nR"*; or is (C,-C6)alkylamino or di-(C1-C6)alkylamino, which groups are unsubstituted or substituted by one or more R6 groups;
R1^ is R6 or OH;
R1^ R1^ and R1Sre each independently H, (C,-C6)alkyl or (C,-C6)haloalkyl;
R1^'is (C,-C6)alkyl or (C1-C6)haloalkyl;
R1^ is R6 or OH; or is (C]-C6)alkylamino or di-(C1-C6)alkylamino, which groups are unsubstituted or substituted by one or more R6 groups;
m is zero or one;
n, p, r, s, t and u are each independently zero, one or two;
q is one, two or three; and each heterocyclyl in the above mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1 to 4 hetero atoms selected from N, O and S;
or a pesticidally acceptable salt thereof;

with the exclusion of the compound wherein R1 is —C(=U)NR3R4; U is O; R2 is H; m is zero; R is H and R is 2,4-dichlorophenyl.
2. The compound as claimed in claim 1 wherein:
R1 is —C(=U)NR3R4
R2isH, (C,-C6)alkylorR3;
R3 is R5 OH or NH2 ; or is (C1-C6)alkyl substituted by one or more R groups;
or R and R together with the interconnecting atoms form a heterocyclic ring selected from (A), (B), (C), (D) and (E);


R3a is (C3-C8)cycloalkyl or (C3-C8)cycloalkyl-(C1-C6)alkyl, which cycloalkyl groups are unsubstituted or substituted by one or more R6 groups; or is (C1-C6)alkyl, (C3-C6)alkenyl or (C3-C6)alkynyl which last three mentioned groups are substituted by one or more R groups; or is (C1-C6)aikylamino; or is NH(CHR"*)saryl which aryl group is unsubstituted or substituted by one or more R6 groups;
R4 is H or R5 or is (C1-C6)alkyl unsubstituted or substituted by one or more R groups;
or R3 and R4 together with the adjacent N atom form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N, O or S atoms and which ring is unsubstituted or substituted by one or more R6orR14a groups;
R5 is (C3-C6)alkenyl, (C3-C6jalkynyl, (C3-C8)cycloalkyl, (C1-C6)alkoxy, (C3-C6)alkenyloxy, (C3-C6)alkynyloxy, (C1-C6)alkylamino, di-(C1-C6)alkylamino, CO(Ci-C6)alkyl, NHC0(C1-C6)alkyl, NHS02(C1-C6)alkyl or S02(C1-C6)alkyl which last 12 mentioned groups are unsubstituted or substituted by one or more R6 groups; or is (C3-C8)cycloalkyl-(C1-C6)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R6 groups; or is NH(CHR1Vryl —(CR15R16)paryl, OCR15R16^aryl, NHCOaryl, COCCHjXaryl, NHSOzaryl, S02(CH2)uaryl or N=C(aryl)2, — (CR15R16)pheterocyclyl or 0(R15R16)rheterocyclyl, which last ten mentioned aryl or heterocyclyl groups are unsubstituted or substituted by one or more R1^ groups; or is 0(CR15R16(C3-C8)cycloalkyl or N=C[(C1-C6)alkyl]2;

R6 is halogen, (C,-C6)alkoxy, (C,-C6)haloalkoxy, S(0)nR14a, CN, CO2(C1-C6)alkyl, CO2H, NO2, OH, amino, (C1-C6)alkylamino, di-(C1-C6)alkylamino, carbamoyl, (C1-C6)-alkylcarbamoyl, di-(C1-C6)-alkylcarbamoyl or CH[0(Ci-C6)alkyl]2; or is phenoxy unsubstituted or substituted by one or more R1"*^ or halogen groups;

R7R8 R9 R12 R19 R21 and R22 are each independently H; or (C,-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C8)cycloalkyl, (C1-C6)alkoxy, (C2-C6)alkenyloxy or (C2-C6)alkynyioxy, which last seven mentioned groups are unsubstituted or substituted by one or more R groups; or is —(CH2)paryl or heterocyclyl, which aryl or heterocyclyl groups are unsubstituted or substituted by one or more R1' groups; or (C3-C8)cycloalkyl-(C1-C6)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R groups;
or R and R together with the attached carbon atom may represent C=0;

R10, R20 and R23 are each independently H; or (C1-C6)alkyl, (C3-C6)alkenyl, (C3-C6)alkynyl or (C3-C8)cycloalkyl, which last four mentioned groups are unsubstituted or substituted by one or more R6 groups; or is (C3-C8)cycloalkyl-(C1-C6)alkyl which cycloalkyl group is unsubstituted or substituted by one or more R6 groups; or is — (CH2)paryl or heterocyclyl which aryl or heterocyclyl groups are unsubstituted or substituted by one or more R6 groups;
R11is R7 halogen, CN, C02(C1-C6)alkyl, NO2 or S(0)„R1^ or is (C,-C6)alkylamino or di-(C1-C6)alkylamino, which groups are unsubstituted or substituted by one or more R6 groups;
R13 is R7 or OH;
R14 R15and R16are each independently H, (C,-C6)alkyl or (C1-C6)haloalkyl;
R14a is (C,-C6)alkyl or (C,-C6)haloalkyl;
R18 is R1 or OH; or is (C1-C6)alkylamino or di-(C1-C6)alkylamino, which groups are unsubstituted or substituted by one or more R6 groups;
m is zero or one; k.
n, p, r, s, t and u are each independently zero, one or two;
q is one, two or three; and each heterocyclyl in the above mentioned radicals is independently a heterocyclic radical having 3 to 7 ring atoms and 1 to 4 hetero atoms selected from N, O and S;
or a pesticidally acceptable salt thereof;

with the exclusion of the compound wherein R1 is —C(=U)NR6R4; U is O; R2 is H; m is zero; R4 is H and R3 is 2,4-dichlorophenyl.
3. The compound or a salt thereof as claimed in claim 1 or 2, wherein R2 is H or
R3
4. The compound or a salt thereof as claimed in any one of claims 1 to 3, wherein
R3 is R5 or OH; or is (C1-C6)alkyl substituted by one or more R groups;
or R2 and R3 together with the interconnecting atoms form a heterocyclic ring selected from (A) and (C):

5. The compound or a salt thereof as claimed in any one of claims 1 to 4, wherein
R4 is H or R5 or is (C1-C6)alkyl unsubstituted or substituted by one or more Rg
groups;
or R3 and R5 together with the adjacent N atom may form a 3 to 8-membered unsaturated, partially saturated or saturated heterocyclic ring which optionally contains up to three additional N. O or S atoms and which ring is unsubstituted or substituted by one or more R6 or R14A groups.

6. The compound or a salt thereof as claimed in any one of claims 1 to 5, wherein R1 is —C(=U)NR3R4
R2 is H;
R3 is R5 or OH; or is (C1-C6)alkyl substituted by one or more R groups;
or R and R together with the interconnecting atoms may form a heterocyclic ring selected from (A) and (C):

R4 is H or R5 or is (C1-C6)alkyl unsubstituted or substituted by one or more R groups;
or R3 and R4 together with the adjacent N atom may form a pyrrolidin-1-yl, piperidin-1-yl, morpholin-1-yl or thiomorpholin-1-yl (or its S-oxide or S,S-dioxide) ring;
R5 is (C3-C6)alkenyl, (C3-C6)alkynyl, (C3-C8)cycloalkyl, (C3-C8)cycloalkyl-(Ci-C6)alkyl, (CrC6)alkoxy, (C3-C6)alkenyloxy, (C3-C6)alkynyloxy or 0(CR15R16)p(C3-C8)cycloalkyl; or —(CR15R16)pphenyl, —(CR15R16)pheterocyclyl, 0(CR16R16)rphenyl or 0(CR15R16)rheterocyclyl, which last four mentioned phenyl or heterocyclyl groups are unsubstituted or substituted by one or more R17 groups;

R6 IS halogen, (C,-C6)alkoxy, (C,-C6)haloalkoxy, S(0)nR14a CN, NO2 or OH;
R17sR6R14aorCH20H;
U is S or O;
W is(CHR19)qorCO;
ZisO;
R7 R8 R9 R10 and R19 are each H; or (C1-C6)alkyl unsubstituted or substituted by one or more R groups;
or R1 and R8 together with the attached carbon atom represent C=0;
R14 R15 and R16 are each H or (C1-C6)alkyl;
R14a is (C1-C6)alkyl or (C1-C6)haloalkyl;
m is zero;
n, r, s, t and u are zero, one or two;
q is one; and wherein heterocyclyl denotes a pyridine, pyrimidine, (1,2,4)-oxadiazole, (l,3,4)-oxadiazole, (l,2,4)-thiadiazole, (l,3,4)-thiadiazole, pyrrole, furan, thiophene, oxazole, thiazole, benzothiazole, imidazole, pyrazoie, isoxazole, 1,2,4-triazole, tetrazole, pyrazine, pyridazine, oxazoline, thiazoline, tetrahydrofuran, tetrahydropyran, morpholine, piperidine, piperazine, pyrroline, pyrrolidine, oxazolidine, thiazolidine, oxirane or oxetane radical.

7. The compound or a salt thereof as claimed in claim 1, wherein R1 is —
C(=U)NR3R4;
R2 is H;
U is O or S;
R3is (C1-C6)alkoxy, (C1-C6)haloalkoxy, (C3-C6)alkenyloxy, (C3-C6)alkynyloxy, CH2phenyl or OCHaphenyl, phenyl or 2-pyridyl which last four mentioned phenyl or pyridyl groups are unsubstituted or substituted by one or more groups selected from halogen, (C1-C6)alkyl, (C1-C6)alkoxy, CN and NO2;
R4is H, (C1-C6)alkyl, (C3-C6)alkenyl, (C3-C6)alkynyl or CH2phenyl; and
m is zero.
8. A process for the preparation of a compound of formula (I) or a salt thereof as
defined in any one of claims 1 to 8, which process comprises:
a) where R1 is —C(=U)NR3R4 m is zero, and R2 U, R3 and R4 are as defined in formula (I); or R and R together with the interconnecting atoms form a heterocyclic ring selected from (A), (B), (C), (D) and (E);



wherein R4 R7, R8 R9 R10, R11, R12, R13 W, X, Y and Z are as defined in formula (I), reacting a compound of formula (II):

wherein L is a leaving group, with a compound of formula (III):
HNR2--C(=U)NR3R4 (III)
wherein R2, U, R3 and R4 are as defined in formula (I), or with a compound of formula (IV), (V), (VI); (VII) or (VIII):



wherein R4 R7 R8 R9 R10, R11 R12 R13 W, X, Y and Z are as defined in formula (I); or
b) where R1 is —C(=U)NR3R4 m is zero, R2 is H, U is O, and R3 and R4 are as defined in formula (I), reacting a compound of formula (IX):

with oxalyl chloride or triphosgene, to give the corresponding acylisocyanate intermediate followed by reacting the resultant intermediate with an amine of formula (X):
HNR3R4 (X)
wherein R3 and R4 are as defined in formula (I); or

c) where R1 is —C(=U)NR3R4, m is zero, R2 is H, U is O or S, and R3 and R4 are
as defined in formula (I), reacting a compound of formula (XII):

wherein U is O or S, with a compound of formula (X) as defined in formula (I); or
d) where R1 is —C(=U)NR3R4 m is zero, R2 is H, R4 is H, U is O or S, and R3 is
as defined in formula (I), reacting a compound of formula (IX) as defined in formula
(I), with a strong base, followed reacting with a compound of formula (XIV):
R3N=C=U (XIV)
wherein R3 is as defined in formula (I); or
e) where R1 is —C(=U)NR3R4 m is zero, R2 is H, U and V are each S, and R6 R6'
and R4 are as defined in formula (I), as a 1-pot reaction, reacting 4-
trifluoromethylnicotinic acid with a halogenating agent to give the corresponding acid
chloride, followed by reacting the acid chloride with an alkali metal thiocyanate or
ammonium thiocyanate or a tetraalkylammonium thiocyanate to give the 4-
trifluoromethyl-3-pyridylcarbonyl isothiocyanate, followed by reacting the
isothiocyanate with an amine of formula (X) above or an alcohol of formula (XI)
above; or

f) where R1 and R2 are as defined above, and m is 1 oxidizing a corresponding
compound in which m is 0; and

if desired, converting a resulting compound of formula (I) into a pesticidally acceptable salt thereof.
9. A pesticidal composition comprising a pesticidally effective amount of a compound of formula (I) or a pesticidally acceptable salt thereof as defined in any one of claims 1 to 7, in association with a pesticidally acceptable diluent or carrier and/or surface active agent.

Documents:

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Patent Number 229370
Indian Patent Application Number 2573/CHENP/2004
PG Journal Number 12/2009
Publication Date 20-Mar-2009
Grant Date 17-Feb-2009
Date of Filing 16-Nov-2004
Name of Patentee BAYER CROPSCIENCE GmbH
Applicant Address Bruningstrasse 50, D-65926 Frankfurt,
Inventors:
# Inventor's Name Inventor's Address
1 ARAKI, Koichi 2-4-39, Kamiya Ushiku, Ibaraki 300-1216,
2 MURATA, Tetsuya 1-19-10, Chuo Ushiku, Ibaraki 300-1234,
3 GUNJIMA, Koshi 4-2-3-303, Yachiyomidorigaoka, Yachiyo City, Chiba 276-0049,
4 NAKAKURA, Norihiko 3-2-7-503 Gion, Minamikawachi-machi, Tochigi 329-0434,
5 SHIMOJO, Eiichi 4-16-1 Nishijyonan, Oyama, Tochigi,
6 ARNOLD, Christian Grimmersdorfer Weg 11, 53343 Adendorf,
7 HEMPEL, Waltraud Zum Morgengraben 18, 65835 Liederbach,
8 JANS, Daniela Schone Aussicht 11, 61348 Bad Homburg v. d. H.,
9 MALSAM, Olga Berghovener Strasse 67, 53227 Bonn,
10 WAIBEL, Jutta, Maria Manderscheider Strasse 51, 60529 Frankfurt,
PCT International Classification Number C07D213/82
PCT International Application Number PCT/EP2003/004714
PCT International Filing date 2003-05-06
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 02010910.4 2002-05-16 EUROPEAN UNION