Title of Invention | PESTICIDAL 1-ARYL-3-AMIDOXIME-PYRAZOLE DERIVATIVES |
---|---|
Abstract | 1-Arylpyrazole-3-substituted-amidoxime derivatives of formula (Ia) or (Ib), or salts thereof: (Ia) (Ib) wherein the various symbols are as defined in the description, and pesticidal compositions thereof, processes for their preparation, and their use for the control of arthropods (including insects and arachnids) and helminths (including nematodes). |
Full Text | Description PESTICIDAL 1-ARYL-3-AMIDOXIWJE-PYRA20LE DERIVATIVES The invention relates to 1-arylpyrazote-3-SLibstttuied-amidoxime derivatives, processes for their preparation, to compositions thereof, and to their use for the control of pests, such as harmful" arthropods (including insects and arachnids) and helminths (including nematodes). The control of insects, arachnids or helminths with 1-arylpyrazoie compounds has been described in, for example, patent publication numbers WO 93/06089, WO 94/21606, WO 87/03781, EP 0295117, EP 659745, EP 679650, EP 201852 and U.S. 5,232,940, The control of parasites in animals filth 1-arylpyrazole compounds has also been described in patent publication numbers WO 00/35884, EP 0846686, WO 98/24769 and WO 97/28126. In particular WO 98/28278 and WO 97/28126 describe certain l-arylpyrazole-3-substituted-amidoxime derivatives as we!) as other related compounds, however benzyl substituted and heterocyclic are not specifically mentioned therein, nor is it suggested that they might also be useful as pesticides. However, the level of action and/or duration of action of these prior-art compounds is not entirely satisfactory in alt fields of application, in particular against certain organisms or when low concentrations are applied. Since modern pesticides must meet a wide range of demands, for example regarding level, duration and spectrum of action, use spectrum, toxicity, combination Vflth other active substances, combination with formulation auxiliaries 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 knovm compounds, at least as far as some aspects are concerned. The present invention provides a compound which is a l-arylpyrazole-S-substituted- amidoxime derivative of formula (la) or (lb): R" is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, {Ci-C6)-alkyl, (CrCej-haioalkyl, (Ci-C6)-alko)cy, (Ci-Cs)- haloalkoxy, CN, NO2, S(0}pR"^ and NR^R"; R* Is H, {CrC6)-atkyl, (CrCel-haloalkyl. (Cs-CjVcycloatkyl, -(Ci-C4)-alkyKC3-C7)- cycloalkyl. -(CH3)„R^ or -{CHz}^^^: R^ and R^are each independently H, {C,-Cs)-alkyl, {Ci-Cej-haloalkyl. (C3-C7)- cydoalkyl or -(CrC4)-alkyl-(C3-C7)-cycloalkyl; or R^ ^nd R^ together with the attached N atom form a five- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from 0. S and N, frie ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (CrC6)-alkyl, (Ci-Ce)-haloalkyl and halogen; R^° is heterocyciyi unsubstituted or substituted by one or more radicals selected from the group consisting of halc^en. (Ci-C4)-alkyl, (CrC4)-ha!oa!kyl, (Ci-C4)-a!koxy, S{0)pR^^ OH and 0x0; R" is halogen, (Ci-C6)-alkoxy, (CrCsj-haloalkoxy, (C3-C7)-cycloalkyl. S(0)pR", - C0r{Ci-C6)-alky!, -0(C=0)-{Ci-C6)-alkyl, C0-{C,-C6)-aikyl, CO-(Ci-C6}-haloalkyl, NR^R^ CONRV, SOaNR^R^ OH, CN, NO2, OR^ NR^COR^*, NR^SOzR^^ or OR^"; R^^ is (C3-C7)-cycloaikyl, (Cz-C6)-alkenyt, (C2-C6)-hatoalkenyl or R^°; or phenyl unsubstituted or substituted by one or more radicals selected from R"; or is (CI-IJE)- alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (Ci-C6)-alkoxy,{C!-CB)-haloaikoxy, (C3-Ce}-alkenyloxy, (Cr Co haloalkenyloxy, (C3-C6)-alkynyloxy, (C3-C6}-ha)oalkynyloxy, (C3-C7)-cycloalkyl, S{0}pR^ S{0)pR"°, S(0)pR"^ CN, NO2, OH, C0R^ NR^COR", NR^SOJR", CONR^R^ NRV, OR^ 0R^°, R^^ R^" and COiR^; R^* is halogen, (Ci-C6)-aikyl. {Ci-C6)-haloalkyl, (CrC6)-alkoxy, (Ci-Cej-haloalkoxy, CN. NOj, S{0)pR", NR^R^ COR", C0R^ CONRV, SO^NR*R^ R^ SF5, OH, 0RR"*, 0R^^ SO3H or (CrC6)-alkylldeneimino; R^^ is pher!yl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (Ci-C6)-aIkyl, (Ci-CeVhaloalkyI, (C)-C6)-alkoxy, (CI-CB)- haloalkoxy, CN, NO3. S(0)pR", NRV, COR". COR^ CONR^R^ S02NR""R^ OH. SO3H and (Ci-Ce)-alkylideneimlno; R" is {C:-C6)-alkyl which is substituted by (Ci-C6)-aIkoxy, S(0}p-(Ci-C6)"alkyl or S(0)p-(C,-C6)-haloalky!; R^^ is a heteroaromatic radical selected from the group consisting of pyridyl, pyrimidinyi, pyridazinyl, pyrazinyl. triazinyl, thienyl, thiazolyl, thiadiazolyl, oxazoly! isoxazoiyi, furyl, pyrrolyl, pyrazolyl, imidazolyl and iriazolyl, which groups are unsut)stituted or substituted by one or more radicals selected from the group consisting of halogen, {Ci-Cgj-alkyl, (Ci-CgVhaloalkyi and (Ci-C6)-aikoxy; R"^ "i a heteroaromatic radical selected from the group consisling of pyridyl, pyrimidinyi, pyridazinyl, pyrazinyl, triazinyl, thieny!, thiazolyl, thiadiazolyl. oxazolyi, isoxazoiyi, furyl, pyrrolyl, pyrazolyl, imidazolyl and triazolyl, which is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (Ci-C6)-a!kyl, (Ci-Cg^haloalkyl and (Ci-C6)-alkoxy, and wdiich hetenaaromatic radical is substituted by R^ R^^ or OR"; m is 1 or 2; n and p are each independently zero, one or two; q is zero or one; and each heterocyclyl in the above-mentioned radicals is independently a hetefocyciic radical having 3 to 6 ring atoms and 1,2 or 3 hetera atoms in the ring selected from the group consisting of N, O and S; or a pesticidally acceptable salt thereof. These compounds possess valuable pesticidal properties. The hvention aiso encompasses any stereoisomer, enantiomer or geometric isomer, and mixtures thereof. Compounds of fomiula (la) and (lb) wherein Y is H may exist in tautomeric forms as shown below: -0(CH,),R" 0(CH2)^R^ H. N 1 "S(O) ;N .-^ ^-. RV J It R S^ > M R3 R3 (la) (lb) Such tautomerism is well known and is described in SPatai (The Chemistry of Functional Groups: Amidines and Imidates, Voi 2, 1991, pages 276-277). It will be understood that all such tautomeric forms are embraced by the present invention. By i\-3 term "pesticidally acceptable salts" is meant salts the anions or cations 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 carboxylic acid group, include alkali metal (e.g. sodium and potassium), alkaline earth metal (e.g. calcium and magnesium), ammonium and amine (e.g. diethanolamine, trJethanolamine, octyiamine, morpholine and dioctylmethyJamine) sails. Suttabie acid addition salts, e.g. formed by compounds of formula (I) containing an amino group, include salts viflth inorganic acids, for example hydrochlorides, sulphates, phosphates and nitrates and salts with organic acids for example acetic acid. It is to be understood thai the above mentioned provisos are included only for reasons of chemical instability for the particular cxduded moieties, and not for reasons of prior art. In t".5 present patent specification, including the accompanying claims, the aforementioned substituenls have the following meanings: Halogen atom means fluorine, chtorine, bromine or iodine. The term "halo" before the name of a radical means that this radical is partially or completely halogenaled, that is to say, substituted by F, CI, Br. or i. in any combination, preferably by F or Cl. Alkyi groups and portions thereof (unless otherwise defined} may be straight- or branched-chain. The expression "(Ci-C6)-aikyr 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, Vbutyl, 2-butyl, 2-mettiytpropyl or tert- buti; radical. Alky! radicals and also in composite groups, unless othenwse defined, preferably have 1 to 4 carbon atoms. "(Ci-CejHaloalkyl" means an alkyl group mentioned under the expression "(Cr Cejalkyr in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms, such as monohaloaikyl, perhaloalkyi, CF3, CHF2. CH2F, CHFCHj, CFaCH;, CFaCFz, CHFaCFj, CH2FCHC!, CHjCl, CCIj, CHClj or CH2CH2CI. The expression ""(CrCi2)-alkylenB" is to be understood as meaning an unbranched or branched saturated carbon chain having from 1 to12 carbon atoms. The expression "(Ci-Ci2)-haloalkylene" is to be understood as meaning an unbranched or branched saturated carbon chain having from 1 to 12 carton atoms, in which one or more hydrogen atoms are replaced by the same number of identical or different halogen atoms. The expression "(CrCuj-alken^ene" is to be understood as meaning an un""" anched or branched saturated carbon chain having from 2 to 12 carbon atoms, and which contains at least one double bond which can be located in any position of the respective unsaturated radical. "(CrC6)Alkoxy" means an alkoxy group whose carbon chain has the meaning given under the expression "(Ci-CeJalkyf". "Haloatkoxy" is, for example, OCF3, OCHFj, OCH2F, CF3CF2O, OCHaCFa or OCHsCHjCI. "(C2-CE)Alkenyr means an unbranched or brandied non-cyclic carbon chain having a number of carbon atoms which corresponds to this stated range and which contains at least one double bonij which can be located in any position of the respective unsaturated radical, "(C2-C6)Alkenyr accordingly denotes, for example, the vinyl, allyl, 2-methy[-2-propenyl, 2-bufenyl, penteny!, 2-methylpentenyi or the hexenyl group. "(C2-C6}Alkyny!" means an unbranched or branched non-cyclic carbon chain having a number of carbon atoms which corresponds to this stated range and which contains one triple bond which can be located in any position of the respective unsaturated radical. ■"(C2"C6)Alkynyr accordingly denotes, for example, the propargyl, 1-methyl-2-propynyl, 2-butynyl or3-butynyl group. CycloaikyI groups preferably have from three to seven carbon atoms in the ring and are optionally substituted by halogen or alkyl. In compounds of formula (!) the followring examples of radicate are provided: An example of alkyi substituted by cycloaikyi is cyclopropylmethyi; an example of alkyl substituted by alkoxy is methoxymethyl (CHsOCHr); and an example of alkyl substituted by alkylthio is methylthiomethyl {CH3SCH2-). Aryl is a mono- or bicylic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl and the like, preferably phenyl. A "heterocyclyr group can be saturated, unsaturated or heteroarwriatic; it preferably contains one or more, in particular 1.2 or 3. heiero atorr^s in the heterocyclfc ring. preferably selected from the group consisting of N, O and S; it is preferably an aliphatic heterocyclyt radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms. The heterocyclic radical can be, for example, a heteroaromatic radical or ring (heteroaryl) such as, for example, a mono-, bi- or poiycyclic aromatic system in which at least 1 ring contains one or more hetero atoms, for example pyridyl, pyrimidinyt, pyridazinyl, pyrazinyl. triazinyl, thienyl, thiazotyl, thiadiazolyl, oxazoiyi, isoxazolyl, furyl, pyrrolyl, pyrazolyl, innidazolyl and triazolyl, or it is a partially or fully hydrogenated radical such as oxiranyl, oxetanyl, oxolany! (= tetrahydrofuryl), oxanyl, pyrrolidyl, piperidyl. piperazinyi, dioxolanyl, oxazolinyl. isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl. The "heterocyclyr group may be unsubstituted or substituted by one or radicals (preferably 1,2 or 3 radicals) selected from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, cartioxyl, cyano. alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl. substituted amino such as aciriamino, mono- and dialkylamino, and alkylsulfinyl, haioalkylsulfinyl, aikylsuifonyl, haloalkylsulforiyl, alkyl and haloalkyl, and additionally also oxo. The oxo group can also be present at those hetero ring atoms where various oxidation numbers are possible, for example in the case of N and S. The tenm pests means arthropod pests {including insects and arachnids), and helminths (including nematodes). Compounds of formula (lb) are pretend. Preferably R"" is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (Ci-C6)-a!kyt, {CrC6)-haloaikyl, {Ci-C6)-alkoxy, (C,-C6)-ha!oalkoxy. CN, NO;, S(0)pR^^ NR^R^, COR^* and CONR^R^ {more preferably R" is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (Ci-C3)-alkyt, (Ci-Caj-haloalkyI, (Ci-C3)-alkoxy, (Ci-C3)-halDatkoxy, CN, N02, S(0)pR" and NR^R^; and in which preferably R^ and R^ are each independently H or {Ci-C6)-alkyl, or R^ and R" together with the attached N atom form a five- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from 0, S and N, the ring being unsubstituted or substituted by one or more (Ci-C3)-atkyl radicals; and R^^ is (C,-C3)-alkyl or {CrC3)-ha[oalkyt. Preferably X and Y are each independently H, {CrCej-aikyI or C0(Ci-C6)-alkyl, Preferably W is C-CI. Preferably R^ is CI. Preferably R^ is CF3 or 0CF3{mDre preferably R^ is CF3). Preferably R* is H. (C,-Cs)-alkyl, {C3-CB}-alkenyl. (C3-C6)-alkynyl. (Ca-CTj-cycloalkyI, ■ C0r(CrC6)-alkyl, -(Ci-C6)-alkyl-{CrC7)-cycloalkyl, COCHzO{C,-C4)-alkyl, -(CrCg)- alkyf-S(0)p-(Ci-Ce}-a{kyl or -CH^R^ in which R"" is phenyl unsubsttuted or substituted fay one or more radicals selected from halogen, (Ci-CaVatkyl. (Cips)- haloalkyi, (Ci-C3)-alkoxy. (CrCsj-haloalkoxy, CN, N02 and S(0)pR", and R" is {d- C3)-alkyl or(Ci-C3)-haloalkyl, Preferably R^is H, (CrCej-alkyl. {CrC6)-alkenyl, (C3-CB)-alkynyl, (C3-C7)-cycloalkyl. C02-(C,-C6)-alkyl or -(Ci-CB)"alkyKC3-C7)-cycloalkyl. Preferably R^ is CF3. Preferably m is 1. Preferably heferocyclyl in the above-mentioned radicals is independently a heteroaromatic radical having 3 to 6 ring atoms and 1, 2 or 3 hetero atoms in ttie ring selected from the group consisting of N, 0 and S, unsubstituted or substiftjted by one or more radicals selected from the group consisting of halogen, {Ct-C4)ralkyl. (Ci-C4)-haloalkyl and {CrC4)-aikoxy (more preferably each heterocyciyi in the above-mentioned radicals is independently a heteroaromatic radical having 5 or 6 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, O and S, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (CrC4)-alkyl, {Ci-C4)-haloalkyl and {Ci-C4)-alkoxy}. A preferred class of compounds of formula (ib) are those in vi/hich: R^ is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (CrCej-alkyl, (Ci-C6)-haloa!kyl, (CrCej-alkoxy. S(0}p- (CrC6)-alkyl or S(0)p-(CTC6)-haloalkyl; or is pyridyl, pyrimidinyl. thienyl, thiazolyl, furyl, tetrahydrofuryl, pyrrolyl, pyrazolyl, imidazolyl, triazoiyl, tetrahydrothienyl or tetrazolyl which groups are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (CrC3)-alkyl or (CrC3)-haloalkyl; X is H. (CrC6)-a!kyl. (CrC6)-alkenyl, (C3-C6)-alkynyl, (CrC7)-cycloalkyl, -(C,-C4)- a!ky!-(C3-C7)-cycloalkyl, -C02-{C,-C6}-alkyl. C0(Ci-C6)-alkyl, -CH20-{Ci-Cs)-alkyf - (Ci-C6)-alkyl-S(0)p- W is C-Ci; R^ is CI; R^and R^ are each CF3; R" is H, (Ci-C6)-alkyl, C0CH;0(C,-C4)-alkyl. -(CrC6)-alkyl-S(0}p-(Ci-C6)-aIkyl or - CHephenyl; R^ is H, {Ci-C6)-alkyl, (Ca-Cej-alkenyl, (C3-C6)-alkynyl, (Cs-Crhcycloalkyl. -(C1-C4)- alkyl-(C3-C7)-cycloalkyl, -C02-(CrC6)-alkyl, C0(Ci-C6)-atkyl. -CH20-{Ci-C6)-a!kyl. - (Ci-C6}-alkylS(0}p-(C,-Ce)-alkyl, S02(C,-C6)-alkyl, S02{C,-C5)-haloatkyl or S02CH2phen^; and m is 1 or 2. A preferred class of compounds of formula (la) are those in which: R" is phenyl; Y is H. (Ci-C6)-alky!, (Ca-Cej-aikenyl, (C3-C6)-alkynyl, (C3-C7)-cycloalkyl, -(Ci-C«}- alkyl-(C3-C7)-cycloa!kyl, -C02-(Ci-C6)-aikyl, C0 S02CHzphenyl; XisH: W is C-Ci; R^ is Ci; R^ and R^ are each CF3; R* is H. (CrC6)-aikyi. -{Ci-C6)-alkyl-S(0)p-(C,-C6)-alkyl or -CHzphenyl; R^ is H. (CrC6)-alkyl, {C3"C6)"alkenyl, (C3-C6)-alkynyl, (C3-C7)-cycloalkyl. -(0,-0^)- alkyi-(C3-C7}-cycloa!kyl, -C02-(CrC6}-a!kyl, C0(C,-C6)-alkyl, -CH20-(CrC6)-alkyI, - (CrCG)-aikylS{0)p-(CrC6)-alkyl, S0;(Ci-C6}-alkyl, SOztCrCeVhaloalkyI or S02CH2phenyl; and m is 1. A further preferred class of compounds of formula (la) are those in which: R^ is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (CrC6)-alkyl, (Ci-C5)-haloalkyl, (CrCej-alkoxy, S[01^- . (CrC6)-alkyl and S{0)p-{CrC6)-haloalkyl; X is H. (C-Csl-alkyl, (C3-C6)-atkenyl, (C3-C6)-alkynyl. (C3-C7)-cycloalkyl. -(CrC4)" al)(y)-{C3-C7)-cydoa!kyi, -C02-(C,-C6)-a)ky), CO(CrCa)-a)kyl. CON[{CrCfi)-a!ky!J?, - Ch20^(Ci-C6)-alkyl. -(CrC6)-alkyl-S(0)p-(CrC5)-aIkyl or -CHzpheny! unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (Ci-C3).alkyl or {Ci-C3)-alkoxy; Y is {CrC6}-alkyl; W is C-CI; R^ is CI; R^ and R^ are each CF3; R" is (Ci-C6)-alkyi or -(CrC4)-alkyl-S{0)p-(Ci-C4)-alkyl; R^isHorCH3;and mis 1, A most preferred class of compounds of formula (la) or (lb) are those in which: R"" is phenyl; X and Y are each independently H, methyl or acetyl; W is C-C!; R" is CI; R^ and R^ are each CF3; R"* and R* are each independently H, methyl, efhyJ, d}lyl propargyi, cyciopropyl, benzyJ, cyclopropylmethyl, methylthkiethyl, ethoxyacetyi or ethoxycarbonyl; and m is 1. The compounds of general formufa (I) can be prepared by the application or adaptation of known methods (i.e. methods heretofore used or described in the chemical literature), it will be understood that in certain cases the use of protecting agents well known in the art may be necessary in onder to obtain satisfactory yields. In the following description of processes when symbols appearing in fonmulae 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 (la) wherein X is H, m and R^ are as defined above, and Y is as defined above with the exclusion of H, and the other symbols are as defined above, may be prepared by the reaction of a compound of formula (11): R^S{0}„\ ^CN wherein R^, R^, R*, R^, R^, W and n are as defined above, with a compound of formula (III): Y-NH-0(CH2),„R" (110 wherein R" and m are as defined above and Y is as defined above with the exclusion of H. The reaction is generally performed in the presence of a base such as a trialkylamine for example triethyiamine, in a solvent such as methanol, at a temperature of from O" to lOO"C (preferably 0" to SO^C), According to a further feature of the invention compounds of formula (la) wherein X is H, m and R" are as defined above, Y is as defined above with the exclusion of H, and the other symbols are as defined above, may also be prepared by the reaction of a compound of fomiula (IV): (IV) wherein the various symbols are as defined above, vifith a compound of fomiula (V): LKCH2),„R^ (V) wherein R and m are as defined above and L is a leaving group such as halogen, preferably chlorine, or sutfonyloxy. The reaction is generally performed in the presence of a base such as sodium hydride, in a solvent such as teUahydrofuran or N,N-dimethylformamide. at a temperature of from 0° to 100°C (preferably 0° to 5D°C}. According to a further feature of the invention compounds offormula (la) wherein X is as defined above with the exclusion of H. and the other symbols are as defined above, may be prepared by the alkylation, acylation or sulfonylation of the corresponding compound of fonnula (la) wherein X is H, using a compound of forr.jla(VI); X-L" (VI) wherein X is as defined above with the exclusion of H and L" is a leaving group sudi as halogen, preferably chlorine, or suifonyloxy. The alkylation reaction {when X Is (Cs-Cej-alkenyl, {C3-C6)-haloaikenyl, (Cs-Ce)-alkynyl, (C3-Ce)-haloalkynyl. {C3-C7)-cyclDalkyl, -(Ci-C4)-alkyl-(CrC7)-cycloalkyl, or (Ct-Cs)-aJkyl unsubstftuted or subst/fuied by one or more R"^ radicals: or where X is -{CH2)qR", -{CH2)qR"° and q is 0) is generally perfomied in the presence of a base such as sodium hydride, in a solvent such as tetrahydrofuran or N,N-rfimefhylformamide. at a temperature of from 0° to lOCC (preferably 0° to 50°C). For alkylations where X is -(CH2)aR", -(CHjjqR""" and q is 1 (i.e. arylattons), L" is preferably fluorine, The sulfonylation reaction (when X is SO?R"} \^ generally performed in the presence of a base such as sodium hydride, in a solvent such as tetrahydrofuran or N,N-dimethylfonnamide, at a temperature of from 0" to 100°C {preferably 0° to 50°C). Th^. acylation reaction (when X is -C02-(Ci-C6)-alky!. CONR^R^ CONR^R^ -COr (CHajqR^, COR^ or COR") is generally performed in the presence of a base such as triethylamine, in a solvent such as tetrahydrofuran, 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 (la) wherein X. Y and the other symbols are as defined above, may be prepared by the reaction of a compound of formula (V!i): ,X wherein the various symbols are as defined above, with a compound of formula (V) as defined above. The reaction is generally performed in the presence of a base sucii as sodium hydride, in a solvent such as tefrahydrofuran or N,N-dimethyifomiamide, 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 (lb) wherein X and Y are each H, and m, R" and the other symbols are as defined above, may be prepared by the reaction of a compound of formula (II) as defined above, with a compound of fonnula (VIII): NH2-0(CH2)n,R^ (VIII) wherein R^ and m are as defined above. The reaction is generally perfomied in tho presence of a base such as a trialkylamine for example triethylamine, in a solvent such as methanol, at a temperature of from 0° to 100°C (preferably 0° to SO"C). According to a further feature of the invention compounds of formula (lb) wherein X is H. Y is as defined above with the exclusion of H, and the other symbols are as defined above, may be prepared by the alkylation, acylation or sulfonylation of the corresponding compound of formula (lb) wherein Y is H, using a compound ol formula (IX): Y-L" (IX) wherein Y is as defined above with the exclusion of H and L^ is a leaving group such as halogen, preferably chlorine, or suifonyloxy. The alkylation, acyiation and sulfonylation reactions may be performed according to the procedures described in the above process for the preparation of compounds of formula (la) from compounds of formula (VI). According to a further feahjre of the invention compounds of formula (lb) wherein X and Y are as defined above with the exclusion of H, and the other symbols are o=; defined above, may be prepared by the aikylation, acyiation or sulfonylation of the corresponding compound of fonnula (lb) wherein X is H, using a compound of formula (VI) as defined above. Tl.fc alkylation, acyiation and sulfonylation reactions may be perfonned according to the procedures described in the above process for the preparation of compounds of formula (la) from compounds of fomiula (VI), According to a further feature of the invention compounds of formula (1) wherein R^, R^ R^ R\ R^ R^ W, X, V and m are as defined above, and n is 1 or 2 may be prepared by oxidising a corresponding compound in which n is 0 or 1. The oxidation is generally performed using a peracid such as S-chJoroperbenzoic acid in a solvent such as dichloromethane or 1,2-dichloroethane, at a temperature of from O"C to the reflux temperature of the solvent. 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, fn this case, it is possible, for example, to automate the procedure of the reaction, work-up or p jiTfication of the products or of the intennediates. 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, Veriag E&txim 1997. p^es 69 to 77. A series o! commercially available apparatuses as are offered by, for example. Stem Corporation. Woodrotfe Road, Tollesbury, Essex, CU9 8SE, England or H+P Labortechnik GmbH, Bruckmanndng 28, 85764 ObetschleiBheim, Germany ot Radleys, Shirehili, Saffron Walden. Essex, England, may t>e used for the parallel procedure of the reaction and worit-up. For the parallel purification of compounds of the formula (I), or of intermediates obtained during the preparation, use may be made, inter alia, of chromatography apparatuses, for example those by tSCO, Inc., 4700 Superior Street, Lincoln, NE 6B504. USA. The apparatuses mentioned lead to a modular procedure in which the 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 automaton modules in question are operated by, for example, nabots. Such automation systems can be obtained, for example, from Zymark Corporation, Zymark Center, Hopkinton, IwSA 01748, USA. In addition to what has been described here, compounds of the formula (I) may be prepared in part or fully by solid-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. Solid-phase-supported synthesis methods are described extensively in the specialist literature, for example Barry A. Bunin in "The Combinatorial index". Academic Press, 1998. The use of solid-phase-supported synthesis methods pennits a series of protocols which are known from the literature 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 et al,. Proc. Nat!. 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 solid-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, WuHener Feld 4. 5B454 Witten, Gemiany. The preparation of the processes described herein yields compounds of the formula (i) in the form of substance coilections which are termed libraries. The present invention also relates to libraries which comprise at least two compounds of the fomiula (i). tntemiediates of formula (IS^ as defined above, may be prepared by the reaction of a compound of fomiuia (II) as defined above, with a compound of formula (X): Y-NHOH (X) wherein Y is as defined above. The reaction may be carried out using the above procedure for the preparation of a compound of formula (la) from compounds of formula (lil) and (11). Inter.iediates of formula (VII) as defined above, may be prepared by the reaction of a compound of fomiula {IV) as defined above, with a compound of formula (VI) as defined above. The reaction may be earned out using the above procedure for the preparation of compound of formula (la) by the alkylation, acylation and suifonylation of the corresponding compounds of formula (la) wherein X is H, using compounds of formula (VI). Certain compounds of formula (IV) and (Vll) are novel and as such form a further feature of the invention. Compounds of formula (I!), (ill), (V), (VI), (VIII), (fX) and (X) are known or may be prepared by known methods. The following non-limiting Examples illustrate the preparation of the compounds of fonnula (I). Chemical Examples In th i Examples which follow, quantities (also percentages) are vreight-based, unless stated otherwise. Example V. 1-(2,6-Dich!orO"4-trifluoromethylpheny])-3-(N-benzyioxy-2-amidino)-5-methylarnino-4-trifluorom6thylsulfonyipyrazole (Compound 1-49) To a solution of 1-{2,6-dic:hioro-4-tr)fluoromethyipheny))-3-cyano-5-methylamino-4-trlfluoromethylsulfonylpyrazole (0,5 g, 1.1 mmoi) in mettianol was added O-benzyihydroxylamine hydroctiloride (0.214 g, 1.34 mmol) and triethylamine (0.33 g, 3.3 mmol). The mixture was stirred at 20""C until a clear solution was obtained, and then evaporated. After adding water and ethyl acetate and extractive work up there was obtained the title product (0.387 g) as a white solid. Example 2: 1-(2,6-Dichloro4-trifIuoromethylphenyi)-3-[N-(2,6-dichloroberzyloxy)-N-methyl-2-amidino]*5-methylamino-4-trifIuoromethylsulfinylpyrazoie (Compound 4-82) To a solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-(N-hydroxy-N-methyl-2-amidrno)-5-methylamino-4-tr!fluoromethylsulfinylpyrazole (0.5 g, 1.0 mmol) in N,N-dimethyiformamide was added sodium hydride (90%, 0.029 g, 1.1 mmol). After stirring for 0,5 hour at 20°C, 2.6-dichlorobenzyl bromide (0.252 g, 1,05 mmol) was added dropwise. The mixture was stirred for an additiorial 7 hours at 20°C. After adding aqueous ammonium chloride and e)Ctractive w/orkup, the title product was isolated by chrcwatography (D.31 g) as a solid. Example 3: 1-(2,6-Djch!oro-4-trifluoromethylphenyl)-3-[N-methyl-N-(4-trifluoromethy!benzyloxy)-2-amidino]-5-methylamina4-trifluoromethylsulfonylpyrazole (Compound 4-128) By proceeding according to Example 2 but using 1-(2,6-dichloro-4-trifluorQmethylphenyl)-3-(N-hydroKy-N"methyl-2-amidrno)-5-methylamino-4-triftuoromefhylsulfonylpyrazole (0.5 g, 1.0 mmol), sodium hydride (90%. 0.029 g. 1,1 mmol) and 4-trifluoromethylbenzyl bnsmide, Itiere was obtained Hie title compound (0.57 g) as a solid. Example 4: 1-(2,6-Dichforo-4-lrffruoromethylpheny!)-3-[N-methy(-N-(4- frifluoromethoxyben2yloxy)-2-amidino]-5-methylamino-4-trifluoromethylthiopyra2ole (Compound 4-165) By proceeding according to Example 2 but using 1-(2,6-dichloro-4- trifluoromethylphenyl)--3-(N-hydroxy-N-methy!-2-amidino)-5-methylamino-4- trifluoromethylthiopyrazole (0.5 g, 1,0 mmol), sodium hydride (90%, 0.029 g, 1.1 mmol) and 4-trifluoromethoxybenzyl bromide (0.290 g. 1.05 mmoi) there was obtained the title compound (0,093 g) as a solid. Example 5: 1-(2,6-Dichforo-4"trifluoromethylphenyl)-3-lN-methy!-N-(4-trifluorDmethylbenzyloyvV 2-amidino]"5-methylamino-4-trif!uoromethy!sulfinylpyrazole (Compound 4-93) By pnaceeding according to Example 2 but using 1-(2,6-dichloro-4-trif)uoromethy!phenyl)-3-{N-hydroxy-N-methyl-2-amidino)-5-methylamino-4-friflLoromelhylsulfinylpyrazole (D.5 g, 1.0 mmol). sodium hydride 90% (0.029 g, 1,1 mmol) and 4-trifluoromethyibenzy] bromide (0,251 g, 1.05 mmol), and subsequent purification by chromatography there was obtained 1-{2,6-dichloro-4-trifIuoromethylphenyl)-3-[N-methyl-N-(4-trifluoromethylbenzylGxy)-2-amidino]-5-methyiamino-4-trifluoromethylsulfinylpyrazole (0.018 g) as a solid. Examples: 1-(2,6-Dichlpro-4-trifluoromethylphenyi)-3-(N-(4-fIuorobenzyloxy-N-methyl)-N"-(4- fluorobenzyl)-2-amidinol-5-methylamino-4-trifiuoromethylsuifonylpyra2ole (Compound 4-159) By proceeding according to Example 2 but using 1-(2,6-dichlorO"4- trifluoromethylphenyl)-3-(N-methyl-N-hydroxy-2-amidino)-5-methylamino-4- trifluoromethylsulfonylpyrazole (0.5 g, 1.0 mmol), sodium hydride {90%, 0.029 g, 1.1 mmol) and 4-fluorobenzyl bromide (0.202 g, 1.05 mmol) there was obtained the title compound (0.309 g) as a solid. The following Reference Examples illustrate the preparation of intemiediales used in the synthesis of the above Examples. intermediate Example 1: 1-{2,6-Dichloro-4-trJfluQromethylphenyl)-3--(N-hydroxy-N-methyl-2-amidinD)-5-methytamino-4-tr(fiuoromethy!sulf]nylpyra2oie To , solution of 1-(2,6-dichtoro-4-trifluoromethylphenyl}-3-cyano-5-methylamino-4-trifluoromethylsuifinylpyrazole (2.0 g, 4.0 mmol) in methanol was added N-methyihydroxylamine hydrochloride (3.45 g, 41.55 mmoi} and triethylamine (10.05 g, 13.9 ml, 99.0 mmol). The mixture was stirred for 8 hours at 20""C, evaporated and the resulting solid washed with water, filtered and dried to yield the title product (14,73 g) as a pate white solid. Intermediate Example 2: 1-(2,6-Dichloro-4-trifluoromethylphenyl)-3-(N-ben2yl-N-hydroxy-2-amtdino)-5- methylaminD-4-trifluoromethyisulfiny[pyrazole By proceeding according to Intemiediate Example 1 but using 1-(2,6-dichlor0"4- trifluoromethy!phenyl)-3-cyano-5-methylamino-4-trifluoromethyisulfinylpyrazole{0.5 g, 1.1 mmof), N-benzylhydroxylamine hydrochloride (0,22 g, 1.34 mmol), there was obtained the title compound (0.450 g) as white solid. Int?miediate Example 3: 3-{N-Benzyl-N-hydro)cy-2-amidino)-1-(2,6-dichloro-4-trifluoromethylphenyl)-5- methylamino-4-trifluoromethylthiopyrazoie By proceeding according to Intermediate Example 1 but using 1-(2,6-dichloro-4- trif|yoromethy!pheny))-3-cyano-5-methyIamino-4-tr!fluoromethyithiopyrazole(0.5g, 1.1 mmol) and N-benzylhydroxylamine hydrochloride (0,22 g, 1.34 mmol) there was obtained the title compound (0.435 g) as a white solid. tntenmediate Example 4: 3-(N-Benzyl-N-hydroxy-2-amidino)-1-(2.6-dichloro-4-trifluoromethylpheny!)-5- methylamino-4"trifluoromethylsulfonylpyrazole By proceeding according to Intermediate Example 1 but using 1-{2,6-dr(^loro-4- trifiuoromethylphenyl)-3-cyano-5-methy(amino-4-trifluoromettiy!suifonylpyrazole ",0,5 the invention may therefore be applied 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 pesticidally active compounds and methods of use of said compounds for the control of a number of pest species v^"hich includes: arthropods, especially insects or arachnids, such as mites, or helminths, such as 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 livestock husbandry, or in public health. The compounds ofthe invention riiay be used for example in the following applications and on the foltowing pests: For the control of soil insects, such as corn rootw/orm, temiites (especially for protection of structures), root maggots, wirev/orms, root vreevils, stalkborers, cutwoms, root aphids, or gmbs. They may also be used to provide activity against plant pathogenic nematodes, such as root-knot, cyst, dagger, lesion, or stem or L jib nematodes, or against mites. For the control of soil pests, for example com rootvi"orm, the compounds are advantageously applied to or incorporated at an effective rate into the soil in v/hich crops are planted or to be planted or to the seeds or grow/ing plant roots. In the area of public health, the compounds are especially useful in the control of many insects, especially filth flies or other Dipteran pests, such as housefiies, stablefiies, soldJerfiies, hornflies, deerflies. horseflies, midges, punkies. blackflies, 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 vreevils, moths or mites, for exampte Ephestia spp. {flour moths). Anthrenus spp. (carpet beetles). Tribolium spp. {flour beetles), Sitophilus spp. (grain weevils) or Acarus spp. (mites). In the control of cockroaches, ants or termites or similar arthropod pests in infe^"sd domestic or industrial premises or in the control of mosquito larvae in watenways, wells, reservoirs or other running, or standing water. For the treatment of foundations, structures or soil in the prevention of the attack c , building by termites, for example, ReticulitenT^es spp., Heterotermes spp., Coptotermesspp-, tn agriculture against adults, larvae and eggs of Lepidoptera (butterflies and mofris), e.g. Heliothis spp, such as Heliothis virescens (tobacco budworm), Heliothis armigera and Heliotfiis zea. Against adults and larvae of Coleoptera (beetles) e.g. Anthonomus spp. e.g. grandis (cotton boll weevil), Leptinotarsa decemiineata (Colorado potato beetle), Diabrotica spp, (corn rootworms). Against Heteroptera (Hemiptera and Homoptera) e.g. Ps^^la spp,, Bemisia spp., Trialeurodes spp., Aphis spp., Myzus spp,, Megoura viciae. Phylloxera spp,. Nephotettix spp. (rice leaf hoppers), Nilaparvata spp.. Against Diptera e.g. ^Ausca spp.. Against Thysatioptera sud\ as Thrips tabaci. Against Orthoptera such as Locusta and Schistocerca spp., (locusts and crickets) e.g. Gryllus spp,, and Acheta spp. for example, Blatta orientalis, Periplaneta americana, Blatella germanica, Locusta mlgratoria 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. Tetranychus spp., and Panonychus spp.. Against nematodes which attack plants or trees of importance to agriculture, forestry or hurticulture either directly or by spreading bacterial, viral, mycoplasma or fungal diseases of the plants. For example root-knot nematodes such as Meloidogyne spp. (e.g. M, incognita). In the field of veterinary medicine or livestock husbandry or in the maintenance of public health against arthropods which are parasitic infernally 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. sot-bodied ticks including Argasidae spp. e.g. Argas spp. and Omithodorus spp. (e.g. Omithodorus moubata); hard-bodied ticks including Ixodidae spp., e.g. Boophilus spp. e.g. Boophilus microplus, Rhipicephalus spp. e.g. Rhipicephalus append iculatus and Rhipicephalus sanguineus; mites (e.g. Damalinia spp.); fleas (e.g. Ctenocephalides spp. e.g. Ctenacephalides felts (cat flea) and Cfenocephalides canis (dog flea)); lice e.g. Menopon spp.; Diptera (e.g. Aedes spp.. Anopheles spp,, Musca spp., Hypoderma spp.); Hemiptera.; Dictyoptera (e.g. Periplaneta spp,, Blateila spp.); Hymenoptera; for example against infections of the gastro-intestinal tract caused by parasitic nematode worms, for example members of the family Trichostrongylidae- in a preferred aspect of the invention the compounds of formula (I) are used for the control of parasites of animals. Preferably the animal to be treated is a domestic companion animal such as a dog or a cat. In a further aspect of the invention Vne compounds of formula (I) or salts or compositions thereof are used for the preparation of a veterinary medicament. In practical use for the control of arthropods, especially insects or arachnids, such as mites, or helminths, such as 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 applied to the focus in v4iich the arthropod or nematode infestation is to be controlled af an effective rate in the range of about 2g to about 1kg vf the active compound perhectareof 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 rov/ spacing or also the method of application. Preferably an effective rate range of the active compound is from about 10g/ba to about 400g/ha, more preferably from about SOgflia to about 200 g/ha. \Mien a pest is soil-borne, the active compound, generally in a fonnulated composition, is distributed evenly over the area to be treated (for example broadcast or band treatment) in any convenient manner and is applied at rates from about 10g/ha to about 400g ai/ha, preferably from about 50g/ha to about 200 g ai/ha, V".tien applied as a root dip to seedlings or drip irrigation to plants the liquid solution or suspension contains from about 0.075 to about 1000 mg al/l, preferably from about 25 to about 200 mg ai/l. Application 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 fror^ attack. The compound of the rnuention 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 application, the formulated compound can, if desired, be distributed mechanically in the soil, for example by ploughing, disking, or use of drag chains. Application 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 (^ 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 fmit or citrus), ornamental plants,.flowers or vegetables or shrubs under glass or in gardens or parks, or foicst trees (both deciduous and evergreen) in forests, plantations or nurseries. They are also valuable in the protection of timber (standing, felled, converted, stored or. stnjclural) from attack, for example, by sawrflies or beetles or temjites. They have applications 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, mifes, lice, fleas, midges, or biting, nuisance or myiasis flies. The compounds of the invention are particularly useful in controlling arthropods or helminths which are present insic-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, parenterady, percutaneousiy or topically. The compositions hereinafter described for application 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 foliar sprays (for example as an in-furrow spray), dusts, granules, fogs or foams or also as suspensions of finely divided or encapsulated compositions as soil or root treatments by liquid drenches, dusts, granules, smokes or foams; to seeds of crops via application as seed dressings by liquid slurries or dusts; to animals infested by or exposed to infestation by arthropods or helminths, by parenteral, oral or topical applicafion 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 pharmaceuticai formulations, edible baits, salt licks, dietary supplements, pour-on formulations, sprays, baths, dips, showers, jets, dusts, greases, shampoos, creams, wax smears or livestock self-treatment systems; 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 trickiefeeds to waterways, wells, reservoirs or other running or standing water. The compounds of formula (I) are particularly useful for the control of parasites of animals when applied orally, and in a further preferred aspect of the invention the compounds of formula (i) are used for the control of parasites of animals by oral application. The compounds of the formula (1) or salts thereof may be administered before, during or after meals. The compounds of the formula (I) or salts thereof may be mixed with a carrier and/or foodstuff. The compound of the formula (1) or salt thereof is administered orally in a dose+■-> the animal in a dose range generally from 0.1 to 500 mg/kg of the compound of the fonnula (1) or salt thereof per kilogram of animal body vi/eight (mg/kg). The frequency of treatment of the animal, preferably the domestic animal to be treated by the compound of the formula (1) or salt thereof is generally from about once per week to about once per year, preferably from about once every two weeks to once every three months. The compounds of the invention may be administered most advantageously with another parasiticidally effective material, sudi as an endoparasitlcide, and/or an ector^rasiticide, and/or an endectoparasiticide. For example, such compounds include macrocyclic lactones such as avemiectins or milbemycins e.g., ivermectin, pyratel or an insect growth regulator such as lufenuron or methoprene. The compounds of the formula (1) can also be empioyed for controiltng pests 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 han/ested material with regard to quantity, quality, storage properties, composition and specific constituents. Thus, transgenic plants are known where the starch content is increased, or the starch quality is altered, or where the harvested materia! 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 pests to be observed in other crops, which are specific for application in tfie transgenic crop in question, for example an altered or specifically wridened spectrum of pests which can be controlled, or altered application rates which may be employed for application. The invention therefore also relates to the use of compounds of the formula (1> for controlling pests in transgenic crop plants- According to a further feature of the present invention there is provided a pesticida! 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 earners 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 fonrs parts of compositions. These compositions can be employed to control arthropods, especially insects and arachnids, such as mites, or helminths, such as plant nemathodes. The compositions may be of any type known in the art suitable for application to the desired pest in any premises or indoor or outdoor area. These compositions contiiln at least one compound of the invention as the active ingredient in combination or association with one or more ottier compatible components which are for example, solid or liquid carriers or diluents, adjuvants, surface-active-agents, or the like 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, likewise form a part of this invention. The compounds of the invention, in their commercially available formulations and in the use forms prepared from these fomiulations may be present in mixtures with other active substances such as insecticides, attractants, sterilants, acarictdes, nematicides, fungicides, growth regulatory substances or herbicides. The pesticides include, for example, phosphoric esters, carbamates, carboxylic esters, fomnamidines, tin compounds and materials produced by microorganisms. Preferred components in mixtures are: 1. from the group of the phosphorus compounds acephate, azamethiphos, azinphos-ethyl. azinphos-methyl, bromophos, bromophD"> ethyl, cadusafos (F-67825), chiorethoxyphos, chbrfenvinphos, chlormephos, chlorpyrifos, chloTpyrifos^rvethyi, demeton, tiemeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, EPN, e\hiun, ethoprophos, etrimfos, famphur, fenamiphos, teniiriolhion, fensuifothion, fenthion, flupyrazofos, fonofos, formothion, fosfhiazate, heptenophos, isazophos, isothioale, isoxatViion, malath"ion. methacritos, melhamidophos, methidathion, saiithion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paralhion, pafatbion-meUryl, phenthoate, phorate, phosalone, phosfolan, phosphocarb (BAS-301), phosmel, phosphamidon, phoxim, pirimiphos, pirimiphos-elhyl, pirimiphos-melhyl, profenofos, propaphos, proelamphos, prothiofos, pyraclofos, pyridapenthion, quinaiphos, sulprofos, temephos, terbufos, tebupirimfos, letrachloFvinphos, thiometon, triazophos, Irichlorphon, vamidothion; 2. from the group of the cartjamates alanycarb (OK-135), aldicarb, 2-sec-bufylphenyl melhylcarbamate (BPMC), carba. /I, carbofuran, carbosulfan, cbethocarb, benfuracart). ethiofencaiti, furathiocarb, HCN-801. isoprocarb, mefhomyl, S-methyl-m-cumenylbutyry! (methyl}carbamale, oxamyl, plrimicarb, propoxur, thiodicarb, thiofanox, 1-methylthJo{ethylideneamino)-N-methyl-N-{r.iurpholinothio}carbamate (liC 51717), triazamafe; 3. from the group of the caitoxylic esters acrinafhrin, aliethrin, alphamefrin, 5-benzyl-3-fury!methyl (E)- (1 R)-cts-2,2-dimethyl-3--(2-oxothiolan-3-ylidenemethyl)cycloprDpanecart)Oxylate, beta-cyfluthrin, alpha-cypermethrin, beta-cypermethrin, bioailethrin, bioallethrin ((S)-cyciopentylisonr>er), bioresmethrin, bifen^rin, (RS)-1-cyano-1-(6-phenoxy-2-pyridyl)methyl (1RS)-trans-3-(4-tert-butylphenyl)-2,2-dimethylcyclopropanecarboxylate {NCI 85193), cycloprothrin. cyfluthrin, cyhaloltirin, cythithrin, cypemfiethrin, cyphenothrin, dettamethrin, empenthrin, esfenvalerate, fenftuthrin, fenpropaOirin. fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin (S-41311), lambda-cyhatothrin, permethrin, phenothrin (® isomer), praliethrin, pyrethrins (natural products), resmethrin, tefluthrin, tetramethrin, theta-cypermethrin, trabmethrin, transfiuthrin, zeta-cypermethrin (F-56701); 4. from the group of the amidines arri"raz, chlordimeform; 5. from the group of ttie tin compounds cyhexatin, fenbutatin oxide; 6. others abamectin, ABG-9008, acetamiprid, acequinocyl, Anagrapha falcitera, AKD-1022, AKD-3059, ANS-118, azadirachtin, Bacillus thuringiensis, Beauveria bassianea, bensuitap, brfenazate, binapacryl, BJL-932, bromopropylate, BTG-504, BTG-505, buprofezin, camphechior, cartap, chlorobenzilate, chlorfenapyr, chlorfluazuron, 2-(4-chlorophenyt)-4,5-diphenyithiophene (UBi-T 930), chlorfentezine, chlcrproxyfen, chromafenozide, dothianidine, 2-naphthylmethyl cyclopropanecarboxylate (Ro12-0470), cyromazin, diacloden (thiamethoxan), diafenthiufDft, DBI-3204, ethyl 2-chloro-N-{3,5-dichloro-4-(l,1,2,3,3,3-hexafluoro-1-propyloxy)pheny!)carbamoyi)-2-carboximidate, DDT, dJcofol, dlflubenzuron, N-(2,3-dihydrD*3-methy!-1,3-thjazo!-2-ylHene)-2,4-xyltdine, dihydroxymethyidihydroxypyrrolidine, dirrobuton. dinocap, diofenolan, emamectin benzoate, endosulfan, ethiprole (sulfethiprole), efhofenprox, etoxazole, fenazaquin, fenoxycarb, fipronil, fluazuron, flumite (flufenzine, S2M21), 2-fluoro-5-{4-(4-ethoxyphenyl)-4-methy)-1-penty!)diphenyl ether (MTi 800), granulosis and nuclear polyhedrosis vimses, fenpyroximate, fenthiocarb, fluacrypyrim, flubenzimine, fiubrocythrlnate, flucycloxuron, flufenoxuron, flufenzine, flufenprox, ftuprpxyfen, gamma-HCH, halfenozide, hafofenprox, hexaflumuron (DE_473), hexythiazox, HOI-9004, hydramethylnon (AC 217300), IKI-220, indoxacarb, ivermectin, L-14165, imidactoprid, indoxacarb (DPX-MP062), kanemite (AKD-2023), lufenuron, M-020, M-020, methoxyfenoztde, milbemectin, NC-196, neemgard, nidinoterfuran. nltenpyram, 2-nitrornethyI-4,5-dthydro>6H-thiazine (DS 52618), 2-nitromelhyl-3,4-dihydrothia20le (SD 35651}, 2-nitromethyIene-1,2-thiazinan-3-ylcarbamaidehyde {WL 108477), novaluron, pirydaryl, propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen, pyriproxyfen, NC-196, NC-1111, NNI-9768. novaluron (MCW-275), OK-9701, OK-9S01, OK-9602. OK-9802, R-195, RH"0345, RH-2485. RYI-210, S-1283, S-1833, SU8601. silafluofen, silomadine (CG-177), spinosad, spirodiclofen, SU-911B, tebufenozide, tebufenpyrad, teflubenzuron, tetiadifon. ietrasui, thiadoprid, thiocyclam, thiamethoxam, totfenpyrad, triazamate, triethoxyspinosyn A, triflumuron. verbutin, vertaiec (m^otal), 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 limits, particularly depending on the nature of the pest to be elifninated or degree of infestation, for example, of crops with these pests. In generaf, 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 solid or liquid carriers and, optionally, about 0.1 to about 50^o of one or more other compatible components, such as surface-active agents or the like. In the present account, the term "carrier" denotes an organic or inorganic ingredient. Ht^itiral or synthetic, with which the active ingredient is combined to facilitate its application, 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, parficufarly to the treated plant). The carrier may be a solid, for example, days, natural or synthetic silicates, silica, resins, waxes, solid fertilizers (for example ammonium salts), ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmoritionite, bentonite or diatomaceous earth, or ground synthetic minerals, such as silica, alumina, or silicates espedally aluminium or magnesium silicates. As solid carriers for granules the following are suitable: crushed or fractionated natural rocks such as calcite, marble, pumice, sepioIJte and dolomte; synthetic granules of inorganic or organic meals; granules of organic material such as sawdust, coconut shells, corn cobs, com husks or tobacco stalks; kiese/guhr, tricatclum phosphate, powdered cork, or absorbent carbon black; water soluble polymers, resins, waxes; or solid fertilizers. Such solid compositions may, if desired, contain nne or more compatible wetting, dispersing, emulsifying or colouring agents which, when solid, may also serve as a diluent. The carrier may also be liquid, for exampie: water, alcohols, pariicuiariy butanoi or glycol, as well as their ethers or esters, particularly methylglyco! acetate; ketones, particularly acetone, cyciohexanone, methylethyl ketone, methylisobutylketone, or isophorone; petroleum fractions such as paraifinic or aromatic hydrocarbons, particularly xylenes or alkyl naphthalenes; mineral or vegetable oils; aliphatic chlorinated hydrocarbons, particularly trichloroethane or methylene chloride; aromatic chlorinated hydrocarbons, particularly chlorobenzenes; water-soluble or strongly polar solvents such as dimethytfomiamide, dimethyl sulphoxide, or N-methylpyrrolidone; liquefied gases; or the like 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 polyacrylic acids, salts of lignosulphonic acids, salts of phenolsulphonic or naphtha lenesuiphonic acids, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty esters or fatty amines, substituted phenols (particularly atkyfphenols orarylphenols), salts of sulphosuccinic acid esters, la" ;"ine 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 earner are only slightly water soluble or are not water soluble and the carrier agent of the compositron for application is water. Compositions of the invention may further contain other additives such as adhesives or colorants- Adhesives such as carboxymethylcellulose or natural or synthetic poiiwiers in the form of powders, granules or lattices, such as arable gum, polyvinyl alcohol or polyvinyl acetate, natural phospholipids, such as cephalins or lecithins, or synthetic phospholipids 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 alizarin 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 application, the compounds of the invention are therefore generally in the form of compositions, which are in various solid or liquid fonms. Solid forms of compositions v/hich can be used are dusting powders (with a content of tl--. compound of the invention, ranging up to 80%), wettabie powders or granules (including water dispersiblegranules), 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 wettabie powders or granules being between about 0,5 and about 80%). Solid 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. Liquid compositions, for example, include aqueous or non-aqueous solutions or suspensions (such as emulsifiabte concentrates, ervuls"ions, flowabJes, dispersions, or solutions) or aerosols. Liquid compositions also indude, in particular, emuteifiable concentrates, dispersions, emulsions, flowables. aerosols, wettabie powders {or powder for spraying), dry flowables or pastes as fomis of compositions which are liquid or intended to fomi liquid compositions when applied, for example as aqueous spr.-ys (including low and ultra-low volume) or as fogs or aerosols. Liquid compositions, for example, in the fonn 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 application 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, ab"out 2 to about 50% of suitable additives, such as stabilizers, surface-active agents, penetrating agents, corrosion inhibitors, colorants or adhesives. Emulsions of any required concentration, which are particularly suitable for application, for example, to plants, may be obtained from these concentrates by dilution with water. These compositions are included within the scope of the compositions which may be employed in the present invention. The emulsions may be in the form of vi"ater-in-oil or oil-jn-water type and they may have a thick consistency. The liquid compositions of this invention may, in addition to normai agriculturai ust.-applications be used for example to treat substrates or sites infested or liable to infestation by arthropods (oi other pests controiled by compounds of this invention) incl"iding premises, outdoor or indoor storage or processing areas, containers or equipment or standing or mnniiig water. All these aqueous dispersions or emulsions or spraying mixtures can be applied, for example, to crops by any suitable means, chiefly by spraying, at rates vMch are generally of the order of about 100 to about 1,200 liters of spraying mixture per hectare, but may be higher or lower (eg, low or ultra-low volume) depending upon the need or application technique. The compound or compositions according to the invention are conveniently applied to vegetation and in particular to roots or leaves having pests to be eliminated. Another method of application of the compounds or compositions according to the invention is by chemigation, that is to say, the addition of a formuiation containing the active ingredient to irrigation water. This irrigation may be sprinkler irrigation for foliar pesticides or it can be ground irrigation or underground irrigation for soil or for systemic pesticides. The concentrated suspensions, wfhich can be applied 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, stabilizers, penetrating agents, adhesives and, as the carrier, v/ater or an organic liquid in which the active ingredient is poorly soluble or insoluble Some organic solids or inorganic salts may be dissolved in the carrier to help prevent settling or as antifreezes for water. The wettable powers (or powder for graying) 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 solid 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 atjout 0 to about 80% of one or more stabilizers and/or other additives, such as penetrating agents, adhesives, anti-caking agents, colorants, or the like. To obtain these wettable powders, the active ingredient is thoroughly mixed in a suitabie blender with additional substances which may be impregnated on the porous filler and is ground using a mill or other suitable grinder. This produces wettabie powders, the ■wettability and the suspendabtlity of vMch are advantageous. They may be suspended in water to give any desired concentration and this suspension can be employed very advantageously in particular for application io plant foliage. Tt^e "water dispersible gtanySes (WG)" (granules which are readily dispersible in water) have compositions which are substantially close to that of the vi^ttable 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 little water, e.g. 1 to 20% by weight, or with an aqueous solution of 3 dispersing agent or binder, followed by drying and screening), or by a dry route (compacting foliowed by grinding and screening). The rates and concentrations of the formulated compositions may vary according to the method of application or the nature of the compositions or use thereof. Generally speaking, the compositions for application to control arthropod or plant nematode pests usually contain from about 0.00001% to about 95%, more particularly from about 0.0005% io 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 wit! > other substances toxic to arthropods or plant nematodes, synergists, trace elements or stabiiizers). The actual compositions employed and their rate of application will be selected to achieve the desired ef}ec:t{s) by the farmer, livestock producer, medical or veterinary practitioner, pest control operator or other person skilled in the art. Solid or liquid compositions for application topically to animals, timber, stored products or household goods usually contain frorr abcmf 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 solid or liquid 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 saltlicks 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 liquid compositions for application to livestock, goods, premises or outdoor areas may contain ft"om about 0.0001% to about 15%, more especially from about 0.005% to about 2.0%, by weight, of one or more compounds of ttie 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 fanning with appropriate exposure times. Edible bails 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 ot 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 b° combined and administered to animals on a single occasion. The following composition EXAMPLES 2A - 2fyi illustrate compositions for use against arthropods, espedaily mites or insects, or 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 Hie following percentages are in weight percent), used in the composition EXAMPLES 2A - 2M exemplified below, are as follows: Trade Name Chemical Description Ethyfan BCP Nonylphenol ethylene oxide conderisate Soprophor BSU Tristyrylphenol ethylene oxide condensate Arylan CA A 70% w/v solution of calcium dodecylbenzenesulfonate Solvesso 150 Light Cio aromatic sofvent Arylan S Sodium dodecylbenzenesulfonate Darvan NOj Sodium lignosulphonate Celrte PF Synthetic magnesium silicate carrier Sopropon T36 Sodium salts of polycarboxylic acids Rhodigel 23 Polysaccharide xanthan gum Bentone 38 Organic derivative ot magnesium montmoriUonite Aerosi! Microfine silicon dioxide EXAMPLE 2A A water soluble concentrate is prepared with the composition as follows: Active ingredient 7% Ethylan BCP 10% N-methyipyrrolidone 83% To a solution of Ethylan BCP dissolved in a portion of N-methylpyrrolidone is added the -"ctive ingredient with heating and stirring until dissolved. The resulting solution is made up to volume 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-methylpyrrolidone 50% Solvesso150 10% The first three components are dissolved in N-raefhylpyrrolidone and to this is then added the Sotvesso 150 to give the final volume. EXAMPLE 2C A w/ettable powder (WP) is prepared with the composition as follovre: Active ingredient 40% Afylan S 2% Darvan NO2 5% Celite PF 53% The ingredients are mixed and ground in a bammer-miil 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% Ethyian BCP 1.00% Sopropon T360. 0.20% Ethylene glycol 5,00% Rhodigei 230- 0.15% Water 53.65% The ingredients are intimately mixed and are ground in a bead mift until a mean pamcle size of less than 3 microns is obtained. EXAMPLE 2E An emulsifiable suspension concentrate is prepared with the composition as follow/s: Active ingredient 30.0% EthylanBCP 10.0% BentoneSS 0.5% SolvessolSO 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 A water dispersible granule is prepared with the composition as follows; Active ingredient 30% DarvanNo2 15% Arylan S 8% Celite PF 47% Tht 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 vAlh the composition as follows; Active ingredient 1 to 10% Taic powder-superfine 99 to 90% The ingredients are intimately mixed and further ground as necessary to achieve a fine powder. This powder may be appplied to a locus of arthropod infestation, for example refuse dumps, stored products or household goods or animals infested by, or af risk of infestatfon by, arthropods to control the arthropods by oral ingestion. Suitable means for distributing the dusting powfl^er to the locus of arthropod Infestation include mechanical blowers, handshakers or livestock self treatment devices, EXAMPLE 2H An edible bail is prepared with the composition as follovre; 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 fomn. 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 flies, to control the arttiropods by oral ingestion. EXAMPLE 21 A solution formuiation is prepared Vi"ith a composition as follows; Active ingredient 15% Dimethyl sulfoxide 85% The active ingredient is dissolved in dimethyl sulfoxide wilti mixing and or heating as required. This solution may be applied percutaneously as a pour-on application to domestic animals infested by arthropods or, after sterilization by filtration through a polytetrafluoroethytene membrane (0.22 micrometer pore size), by parenteral injection, at a rate of application of from 1-2 to 12 m! of solution per 100 kg of animal body v/eight, EXAMPLE 2J A wettable powder is prepared with the composition as follows: Active ingredient 50% Ethyian BCP 5% Aerosil 5% Celite PF 40% The Ethyian BCP is absorfcied onto the Aerosil which is then mixed with the othei ingredients and ground in a hammer-mill to give a wettable pov/der, which may be diluted with water to a concentration of from 0.001 % to 2% by weight of the active comoound and applied 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 run.ifiant domestic animals for retention within the reticufo-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, peliets, brickettes or the like can be prepared with compositions as follows: Active ingredient 0.5 to 25% Polyvinyl chloride 75 to 99.5% DiocSyl 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 info 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 follov/s; Active ingredient 85%(max) Polyvinylpyrrolidone 5% Attapulgite clay 6% Sodium laury! sulfate 2% Glycerine 2% The ingredients are mixed as a 45% slurry with wafer and wet milled to a particle size of 4 microns, then spray-dried to remove wafer. METHODS OF PESTiClDAL USE The following representative test procedures, using compounds of the invention, were conducted to determine the parasiticidal and pesticidal activity of compounds of the invention. METHOD A: Screening method to test systemicity of compounds against Ctenocephalides felis (Cat flea) A test container was filled with 10 aduits of Ctenocephalides felis. A glass cylinder was closed on one end with parafilm and placed on top of the test container. The test compound solution was then pipetted into bovine blood and added to the glass cylinder. The treated Ctenocephalides felis were held in this artificial dog test (blood 37 "C, 40-60 % relative humidity; Ctenocephalides felts 20-22""C, 40-60 % relative humidity) and assessment performed at 24 and 48 hours after application. Active compounds gave at least 90% control of Ctenocephalides felis at a test concentration of 5ppm or less. METHOD 8: Diabrotica undecimpunctata (southern corn rootworm) screen Two days before application, seeds of maize v/ere soaked in vrater under warm conditions to elicit fast germination. One day before application, eggs of Diabrotica undecimpunctata were transferred to one half of a Japanese filter paper placed in a plastic petri dish. Afterwards, a sprouted maize seed was placed on a moistened pad beside the filler paper. Three drops of 200 microlitres of test compound solution were carefuily pipetted onto the egg. The remainder of the solution was placed on the maize and then the Petri dish was closed. The treated eggs in the Petri dishes were held in a climate chamber for 6 days. The compound efficacy (percentage of dead eggs and/or larvae in comparison to untreated control) was assessed 6 days after application using a binocular microscope. Active compounds gave at least 90% control of Diabrotica undecimpunctata at a test concentration of 10ppm. METHOD C: Nephotettrx Cinciceps (rice leafhopper) screen The leaves of 12 rice plants having a stem length of 8 cm were dipped for 5 seconds into an aqueous soiution of the formulated test compound. After the solution had mn off, the rice plants treated in this manner were placed in a Petri dish and populated with about 20 larvae (L3 stage) of Nephotettrx cincticeps. The Petri dish was CIOSLJ and then stored in a climate chamber (16 hours of light/day, 25°C, 40-60% relative humidity). After 6 days storage, the percentage mortality of leafhopper lawae was determined. Active compounds gave at least 98% mortality of Nephotettix cinciceps larvae at a test concentration of 100 ppm. METHOD D: Screening method to test contad activity against Ctenocephalides felts (Cat flea) Solutions of the test compounds were dropped onto filter paper, dried and ftie filter paper placed into test tubes and infested with 10 adults of Ctenocephalides felis. The treated Ctenocephalides felis were held in a climate chamber (26""C, 80% RH) and the percentage efficacy assessed 24 hours and 48 hours after application in comparison with the untreated control. Active compounds gave at least 70% contact control of Ctenocephalides felis a! a test concentration of 1000 ppm. METHOD E: Screening method to test contact activity against Rhipicephalus sanguineus (Brown dog tick) Solutions of the test compounds were dropped onto filter paper, dried and the filter paper placed into test tubes and infested with 20-30 larvae {LI) of Rhipicephalus sanguineus and the tubes closed with a clip. The treated Rhipicephalus sanguineus were held in a climate chamber (25°C. 90% RH) and the percentage efficacy assessed 24 hours after application in comparison with the untreated control. Active compounds gave at least 70% contact control of Rhiptcephalus sanguineus at a test concentration of 100 ppm. The following Compound numbers were active in one or more of the above tests: WE CLAIM: 1. A compound of formula (la) or (!b): wherein: R"" is ary! unsubstituted or substituted by one or more R"1 radicals; or is R1° or R""1; X and Y are each independently H. (C3-C6)- (C3-Ce)- , (Cs-Cs)- alkynyl, (C3-C6)-halo3lkynyi, (C3-C7)-cydoalkyl. -(CrC4)-all(yi-(C3-C7)-cycloalkyl, - C02KCvC6)-a!kyl, CONR1R1 CONR1R1 -COHCHjjqR1 -(CH2}qR1 -(CHz) COR1 SOjR"1 or COR"; or (Ci-C6)-alkyl unsubstituted or substituted by one or more R11 radicals; W is N, C-CH3 or C-halogen; R1 is hydrogen, CH3 or halogen; R1 is halo. (Ci-Csj-aikyI, (Ci-Cjj-haloalkyI, (Cf-C3)-haloalkoxy, S{0)p-(C,-C3)- haioalkyl or SFs; R" is H, (C3-C6)-aikenyl, (Ca-Ce1haloalkenyl, {C3-C6)-a!kynyl, (Ca-Ce1haloalkynyl, (C3-C7)-cyc!oalkyl, -C02-{CrC6)-alkyl, -COr(C3"CT)"Cycloa(kyl, -COrfCrC1HIkyl- {C3-C7}-cycioalkyl, -C02-(C3-C6}-alkenyl, -CO1-{CH1)qR1 CONR""R1 -C0r(CH2)qR1°, -{CH2)qR1 -(CH3}qR1° COR1 or COCH20-(CrC4)-atkyl; or {Ci-C6)-a!kyl unsubstituted or substituted by one or more R""1 radicals; R* is H, (Cj-Cel-alkynyl, -C02-(CrC6)-aIkyl, (C3-C7)-cycloalkyl or -SOjR11; or (Ci-Ce)- alkyl, (C2-C6}-alkenyl or C0-(C,-C6)-alkyl which last three mentioned groups are unsiibstitut*"f1 t1i" «;iiheitifiitpfi hv nnH nr mnrp R rarfirj1ls" R1 and R1are each independently (C,-C6)-alkyi, {CrCel-haloalkyl. {CrCej-alkenyl, (Cj-Csj-haloalkenyl, (Cj-Csj-alkynyl, {CrCs}-halDalkynyt or (C3-C7)-cycloaikyl; R1 ij phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (CrC6)-aikyl, (CrC6)-haloalkyl, (CfCeValkoxy, {d-Ce}- haloalkQ>cy, CN, NO;, S(0)pR" and NR1R""; R" is H, (C,-C6)-3lky!. (C,-C6)-haloalkyl, (C3"C7)-cycloaIkyl, -(Ci-C4)-alkyKC3-C7}" cycloalkyi, -{CH2)flR1 or -(CH2)qR""; R1 and R11are each independently H, (Ci-C5)-alkyl, (Ci-Cs)-haloalkyl, (CrC?)- cycloalky! or -{Ci-C R1 and R1 together with the attached N atom form a ffve- or six-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, {Ci-C6}-alkyl, (Ci-C6}-haloalkyl and halogen; R"" is heterocyclyl unsubstituted or substituted by one or more radicals selected trom the group consisting of halogen, (Ci-C1j-alkyl, (Ci-C4)-haloalkyl, (CrC4)-3lkoxy, S(0)pR", OH and oxo; R1" is halogen, {Cf Ce1alkoxy, (Ci-C6}-haioaikoxy, {CrC/j-cycloaikyl, S{0)pR11 - C02-(CrC6)-alkyl, 10{C=0)-(Ci-C6)-al" R11 is (C3-C7)-cycloaIkyt, (C3-C6)-a}kenyl. (C2-G6)-haloalkenyl or R""; or phenyl unsubstituted or substituted by one or more radicals selected from R"1; or is (Ci-Ce)- alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (Ci-C6)"alkoxy, (Ci-Cel-haloaikoxy, (C3-C6)-alkenyloxy, {C3- C6)-haloalkenyloxy. (C3-C6)-alkynylo)cy, (C3-C6)-hatoa!kynytoxy, {Cs-CyKycloalkyI, S(0)pR\ S(0)pR1°, S(0)pR", CN, NO?, OH, COR1 NR1COR"", NR1SOJR". CONR"R1 NR*R1 OR1 0R"°, R11 R1° and COjR*; R"* is halogen, (Ci-C6)-alkyl, (Ci-Cej-haloalkyI, (Ci-C6)-alkoxy, {Ci-C6)-haloalkoxy, CN, N02, S{0)pR11 NR""R1 COR"1 COR", CONR1R1 S02NR11 R1 SF5. OH, OR", R11 0R"1 SOjH or (Ci-CgValkylideneimino; R11 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (Ci-C6)-alkyl, (Ci-Cs)-haloalkyl, (CrCej-alkoxy, (Ci-Cs)- haloaikoxy. CN. NO?, S(0)pR", NR1R1 COR"1 COR1 CONR1R1 SO;NR1R1 OH, SOaH and (CrCej-aikylideneimino; R"1 is (CrC6)-akyl which is substituted by (Ci-Cs)-aikoxy. S(0)p-(CrCs)-alkyl or S(0)p-(CrC6)-halDalkyi; R"1 is a heteroaromatic radical selected from the group consisting of pyridyl, pyhmidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazoiy!, fhiadiazolyl, oxazolyl, isoxazoiyl, furyi, pyn"oiyl, pyrazolyl, irnidazolyi and tnazolyl, which groups are unsubstftuted or substituted by one or more radicals selected from the group consisting of halogen, (Ci-C6)-alkyi. (Ci-C6)-haloaikyl and (Ci-C6)-alkoxy; R1* is a heteroaromatic radical selected from the group consisting of pyridyl, pyhmidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazoiyi, thiadiazolyl, oxazoiyi, isoxazoiyl, furyl, pyrrolyi, pyrazolyl. imidazolyl and triazolyl, which is unsubsfitufed or substituted by one or more radicals selected from the group consisting of halogen, (C,-C6)-a!ky!, (Ci-C6)-iialoalkyI and {Ci-Cej-alkoxy, and which heteroaromatic radical is substituted by R1 R11 or OR1: mis 1 or 2; n and p are each independently zero, one or two; q is zero or one; and each heterocyclyl in the above-mentioned radicals is independently a heterocyclic radical having 3 to 6 ring atoms and 1, 2 or 3 hetero atoms in the ring selected from the group consisting of N, 0 and S; or a pesticidaily acceptable salt thereof. 2. The compound as claimed in claim 1 wherein R1 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (Ci-C6)-alkyl, (Ci-C6)-haloalkyl, (C,-C6)-alkoxy. (Ci-Ce)-haloaikojfy, CN, NO;, S(0}pR11 NR1R1, COR" and CONR1R"; and in which R* and R1 are each independently H or {CrC6)-alkyl, or R1 and R1 together with tht-attached N atom fonn a frve- or slx-membered saturated ring which optionally contains an additional hetero atom in the ring which is selected from 0, S and I., the ring being unsubstituted or substituted by one or more (Ci-Csj-alky) radicals; and R" is (Ci-Cal-alkyI or (Ci-Cjj-haloalkyl. 3. The compoundas claimed in claim 1 or 2 wherein X and Y are each independently H, {Ci-Cej-alkyI orCO(Ci-C6)-alky!. 4. The compound as claimed in claim 1, 2 or 3 wherein W is C-CI. 5. The compound as claimed in any one of claims 1 to 4 wherein R1 is CI. 6. The compounds claimed in any one of claims 1 to 5 wherein R1 is CF3, 7. The compound as daimed in any one of claims 1 to 6 wherein R* is H, (C,-C6)-alkyl, {C3-C6)-alkenyl, {C3-C6}-alkynyl, (C3-C7)"Cycfoa!kyl, -C02-(Ci-Cel-alkyl, "(Ci-C6)-a!kyHC3-C7)-cycloalkyl, C0CH20(C,-C1)-alkyi. -(CrCej-alkyl-S(0)p-(CrC6)-atky! or -CH2R", in which R1 is phenyl unsubstituted or substituted by one or more radicals selected from halogen, (CrC3)-atkyl, (C,-C3)-haloalkyl, (C1-C3}-alkoxy. (Ci-C3)-haloaiK0!(y. CN. NO; and S(0)pR"1, and R" is (CrC3)-a5ky) or (Ci-C3}-haloalkyl. 8. The compoundas daimed in any one of claims 1 to 7 wherein R1 is H, (Ci-Cs)-alkyl, (C3-C6)-alkenyi, (C3-C6)-alkynyl, (C3-C7>-cycloalkyl, -C02-(Ci- C6)-alkyl or -{C,-C6)-3ikyl-(C3-C7)-cycloalkyl. 9. I he compound as claimed in any one of claims 1 to 8 wherein R1isCFa. 10. The compoundas claimed in any one of claims 1 to 9 wherein m is 1. 11. The compoundas claimed in any one of claims 1 to 10 wherein R" is phenyl; X and Y are each independently H, methyl or acetyl; W is C-CI; R1 is CI; R" pnd R1 are each CF3; R1 and R1 are each independently H, methyl, ethyl, ally!, propargyl, cyclopropyl, benzy!, cyclopropylmethyl, methyithioethyl, efhoxyacetyl or ethofycarbonyl; and m is 1, 12. A process for the preparation of a compound of fomiula (!) or a salt thereof as claimed in any one of claims 1 to 11, which process comprises: a) where (I) is a fomiula (la), X is H, m and R1 are as defined in claim 1, Y is as defined in claim 1 with the exclusion of H, and the other symbols are as defined in claim 1, reacting a compound of formula (II): R6S(0),\_ .CN (I!) wherein R1, R1, R*. R1 R1, W and n are as defined in claim 1, with a compound of formula (III): Y-NH-0(CH2)mR" (lit) vstierein R1 and m are as defined in claim 1 and Y is as defined In claim 1 with the exclusion of H; or b) where (I) is a fonnuia (la), X is H, m and R" are as defined in claim 1, Y is as defined in claim 1 with the exclusion of H, and the other symbols are as defined in claim 1, reacting a compound of fomnula (IV): ,0H {IV) wherein the various symbols are as defined in claim 1, with a compound of fomiula (V): L-{CHz)mR" (V) wherein R" and m are as defined in claim 1 and L is a leaving group; or c) where (I) is a fomiula (la), X is as defined in claim 1 with Ihe exclusion of H, and the other symbols are as defined in claim 1, the aikylation, acylation or sulfonyiation of the corresponding compound of formula (la) wherein X is H, using a compound of formula (Vi); X-L1 (VI) wherein X is as defined in claim 1 with the exclusion of H and L" is a leaving group; or d) where (I) is a formula (la). X, Y and the other symbols are as defined in claim 1, the reaction of a compound of formula (VII): ,X ,0H wherein the various symbols are as defined in claim 1, with a compound of formula (V) as defined above; or e) where (I) is a formula (lb), X and Y are each H. and m, R1 and the other symuois are as defined in claim 1, the reaction of a compound of formula (If) as defined in claim 1, with a compound of formula (VOi): NHrO{CH2),„R" (Vlil) wherein R" and m are as defined in claim 1; or f) where (I) is a formula (ib), X is H, Y is as defined in claim Iwith the exclusion of H, and the other symbols are as defined in claim 1, the alkylation, acylation or sulfonylation of the corresponding compound of formula (Ib) wherein Y is H, using a compound of formula {IX); Y-L1 (IX) wherein Y is as defined in claim 1 with the exclusion of H and L1 is a leaving group; or g) where (I) is a formula (lb), X and Y are as aefined in claim 1 with the exclusion of H, and the other symbols are as defined in claim 1, the alkylation, acylation or sulfonylation of the corresponding compound of formula (lb) wherein X is H, using a con .pound of formula (Vl) as defined in claim 1; or h) where R\ R1, R1, R*, R1, R1,W, X.Y and m are as defined in claim 1. and nis 1 or 2, oxidising a corresponding compound in which n is 0 or 1; and i) if desired, converting a resulting compound of formula (I) into a pesticidally acceptable salt thereof- 13. Apesticidal composition comprising a compound of formula (I) or a pesticidaiiy acceptable salt thereof as defined in any one of claims 1 to 11, in association with a pesticidally acceptable diluent or canier and/or surface active agent, 14, A veterinary medicament comprising acompound of fonnula (1) or a s£it thereof according to any one of claims 1 to 11 or of a composition according to claim 13, 15. A veterinary medicament for controlling pests comprising a compound or salts thereof or a composition as claimed in claim "14. |
---|
1085-chenp-2005 abstract duplicate.pdf
1085-chenp-2005 claims duplicate.pdf
1085-chenp-2005 correspondence-others.pdf
1085-chenp-2005 correspondence-po.pdf
1085-chenp-2005 description (complete) duplicate.pdf
1085-chenp-2005 description (complete).pdf
1085-chenp-2005 pct search report.pdf
Patent Number | 223486 | ||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Indian Patent Application Number | 1085/CHENP/2005 | ||||||||||||||||||
PG Journal Number | 47/2008 | ||||||||||||||||||
Publication Date | 21-Nov-2008 | ||||||||||||||||||
Grant Date | 11-Sep-2008 | ||||||||||||||||||
Date of Filing | 01-Jun-2005 | ||||||||||||||||||
Name of Patentee | BAYER CROPSCIENCE S.A | ||||||||||||||||||
Applicant Address | 55, avenue René Cassin, F-69009 Lyon, | ||||||||||||||||||
Inventors:
|
|||||||||||||||||||
PCT International Classification Number | A01N 43/56 | ||||||||||||||||||
PCT International Application Number | PCT/EP2003/012620 | ||||||||||||||||||
PCT International Filing date | 2003-11-12 | ||||||||||||||||||
PCT Conventions:
|