Title of Invention

PYRAZOLE DERIVATIVES AS PESTICIDES

Abstract Disclosed are compounds of formula (I) or pesticidally acceptable salts thereof wherein, for example, W is =CR8- or =C(NR9R10)-, R8 is halogen, R9 and R10 are independently of one another Hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, aralkyl or heterocyclylalk-yl, R1 is cyano, methyl, tfifluoromethyl or -CS-NH2, R2 is C1C6-alkyl, C1-C6 C1-C6haloalkyl, R3 is hydrogen, alkyl or cycloalkyl, R4 and R5 are alkenyl, alkynyl or cycloalkyl, R6 is haloalkyl, haloalkoxy, halogen or - SF5l R7 is halogen or alkyl, and n is 0, 1 or 2.These compounds can be used for controlling pests, especially by treatment of domestic animals.
Full Text Chemical comopounds, process for their preparation and use thereof Description
The invention relates to novel phenylpyrazole-oximcarbamate derivatives, processes for their preparation; to compositions thereof, and to their use for the control of pests (including arthropods and helminths).
The control of insects, arachnids and helminths with 5-alkoxycarbonylamino- and 5-haloalkoxycarbonylaminopyrazole compounds has been described in, for example, in EP-A-295,117, WO-A-2000/35,884 and WO-A-2003/74,493.
Furthermore, WO-A-87/03,781and WO-A-2003/74,492 disclose 1-aryl-pyrazol derivatives and their use asj pesticidal agents.
However, since modem 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 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 known compound!, at least as far as some aspects are concerned.
It is an object of the present invention to provide new pesticides which may be used in domestic companion animals.
It is advantageous to apply pesticides to animals in oral form so as to prevent the possible contamination of humans or the surrounding environment.
Another o|ject of the invention is to provide new pesticides which may be used in lower dose than existing pesticides.
Another ofject of the invention is to provide new pesticides which are substantially non-emetic.
Another object of the invention is to provide new pesticides which are safer to the user and the environment
Another object of the invention is to provide new pesticides which show improved activity against ectoparasites in terms of application rate and long lasting activity as systemic ectoparasiticides.

These objects are met in whole or in part by the present invention.
The 5-aminopyrazole carbamate derivatives of the present invention are characterized by a ketone-oxime groups in the carbamate group.
The present invention provides a compound which is a 5-oximecarbonyl-aminopyrazole derivative of formula | or a pesticidally acceptable salt thereof; wherein

(Formula Removed)

W is =CR8 or =C(NR9RJO)->
R8 is halogpn, alkyl or haloalkyl,
R9 and RIO!are independently of one another hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
which groups R9 and R10 independently of one another are optionally substituted by one or more halogen, C3-C7-cycloalkyl, aryl, heteroaryl, C1-C6-alkoxy and/or C1-C6-haloalkoxy,
R1 is cyant), methyl, trifluoromethyl, -CS-NH2 or -C(=NR11)S(O)I1RUS R11 is hydrogen, alkyl or aryl, R12 is alky or aryl,
which groups Rnand/or R12 are optionally substituted by one or more halogen, hydroxyl, oxo, nitro, cyano, amino, alkyl, alkoxy, alkylthio, cycloalkyl, aryl, heterocyclyl and/or aralkyl groups,
R2 is C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl or C2-C6-haloalkynyl,
R3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, heterocyclyl, aralkyl or heterocyclylalkyl, which group R3 is optionally substituted by one or more halogen, hydroxyl, cyano, nitfo, carboxy, carboxylic acid ester, oxo, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcar-bonyl, alkylcycloalkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclylcarbonyl, heterocycly-lalkylcarbonyl, amino, alkyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloal-kynyloxy, alkylthio, haloalkylthio, cycloalkylthio, alkylcycloalkylthio, arylthio, aralkylthio, hetero-cyclylthio, heterocyclylalkylthio, alkylsulphoxidyl, haloalkylsulphoxidyl, cycloalkylsulphoxidyl, alkylcycloalkylsulphoxjdyl, arylsulphoxidyl, aralkylsulphoxidyl, heterocyclylsulphoxidyl, hetero-cyclylalkylsulphoxidyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcycloalkyl-sulphonyl, arylsulphonyl, aralkylsulphonyl, heterocyclylsulphonyl, heterocyclylalkylsulphonyl, cycloalkylk cycloalkyloxy, aryl, aryl substituted by one or more halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano, nitro, alkylthio, haloalkylthio, cycloalkylthlo, alkylcycloalkylthio, arylthio, aralkylthio, heterocyclylthio, heterocyclylalkylthio, alkylsulphoxidyl, haloalkylsulphoxidyl, cycloalkyligulphoxidyl, alkylcycloalkylsulphoxidyl, arylsulphoxidyl, aralkylsulphoxidyl, heterocy-clylsulphoixidyl, heterocyclylalkylsulphoxidyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, aljkylcycloalkylsulphonyl, arylsulphonyl, aralkylsulphonyl, heterocyclylsulphonyl, hetero-cyclylalkyllsulphonyl, and/or amino groups, heterocyclyl, heterocyclyl substituted by one or more halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkylcycloalkylthio, arylthio, aralkylthio,_heterocyclylthio, heterocyclyl-alkylthio, alkylsulphoxidyl, haloalkylsiilphoxidyl, cycloalkylsulphoxidyl, alkylcycloalkylsulphoxidyl, arylsulphoxidyl, aralkylsulphoxidyl, heterocyclylsulphoxidyl, heterocyclylalkylsulphoxidyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcycloalkyl-sulphonyl, arylsulphonyl, aralkylsulphonyl, hetero-cyclylsulpihonyl, heterocyclylalkylsulphonyl, hydroxy and/or oxo groups, aralkyl and/or heterocy-clylalkyl group,
R4 and R! are independently of one another hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloal-kylalkyl, aryl, heterocyclyl, aralkyl or heterocyclylalkyl or R4 and R5 together with the attached C-atom form a four- to seven-membered saturated or unsaturated ring which optionally contains oxy-gen, sulfur and/or nitrogen atoms in the ring and/or which is fused to one or more saturated or un-saturated carbocyclic or heterocyclic ring, which groups R4 and/or R5 or which ring formed by R4 and R5 are optionally substituted by one or more halogen, hydroxyl, cyano, nitro, carboxy, carbox-ylic acid fster, oxo, alkylcarbonyl, haloalkylcarbonyl, cycloalkylcarbonyl, alkylcycloalkylcarbonyl, arylcarbopyl, aralkylcarbonyl, heterocyclylcarbonyl, heterocyclylalkylcarbonyl, amino, alkyl, alkoxy, cycloalkyloxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, al-kylthio, haloalkylthio, cycloalkylthio, alkylcycloalkylthio, arylthio, aralkylthio, heterocyclylthio, heterocyclylalkylthio, alkylsulphoxidyl, haloalkylsulphoxidyl, cycloalkylsulphoxidyl, alkylcy-
cloalkylsujphoxidyl, arylsulphoxidyl, aralkylsulphoxidyl, heterocyclylsulphoxidyl, heterocyclylal-kylsulphoxidyl, alkylsulphonyl, haloaikylsulphonyl, cycloalkylsulphonyl, alkylcycloalkyl-sulphonyl, arylsulphonyl, aralkylsulphonyl, heterocyclylsulphonyl, heterocyclylalkylsulphonyl, cycloalkylj aryl, aryl substituted by one or more halogen, alkyl, haloalkyl, alkpxy, haloalkoxy, cyano, nitlib, alkylthio, haloalkylthio, cycloalkylthio, alkylcycloalkylthio, arylthio, aralkylthio, het-erocyclylthio, heterocyclylalkylthio, alkylsulphoxidyl, haloalkylsulphoxidyl, cycloalkyl-sulphoxidyl, alkylcycloalkylsulphoxidyl, arylsulphoxidyl, aralkylsulphoxidyl, heterocyclyl-sulphoxidyl, heterocyclylalkylsulphoxidyl, alkylsulphonyl, haloaikylsulphonyl, cycloalkylsul-phonyl, aljtylcycloalkylsulphonyl, arylsulphonyl, aralkylsulphonyl, heterocyclylsulphonyl, hetero-cyclylalkylsulphonyl, and/or amino groups, heterocyclyl, heterocyclyl substituted by one or more halogen,alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkylcy-cloalkylthijo, arylthio, aralkylthio, heterocyclylthio, heterocyclyl-alkylthio, alkylsulphoxidyl, haloalkylsfilphoxidyl, cycloalkylsulphoxidyl, alkylcycloalkylsulphoxidyl, arylsulphoxidyl, aralkyl-sulphoxidyj, heterocyclylsulphoxidyl, heterocyclylalkylsulphoxidyl, alkylsulphonyl, haloaikylsulphonyl, cycloalkylsulphonyl, alkylcycloalkyl-sulphonyl, arylsulphonyl, aralkylsulphonyl, hetero-cyclylsulpfionyl, heterocyclylalkylsulphonyl, hydroxy and/or oxo groups, aralkyl and/or heterocy-clylalkyl group,
R6 is halosflkyl, haloalkoxy, halogen or -SF5, R7 is halogen, alkyl or -NR17R18,
R17 and R18 are independently of one another hydrogen, C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, which groups R17 and/or R18 are optionally substituted by one or more halogen, C3-C7-cycloalkyli, aryl, heteroaryl, C1-C6-alkoxy or C1-C6-haloalkoxy, and
nisO, I,or2.
In the present specification, including the accompanying claims, the aforementioned groups have the following meanings:
The term ,,halogen" shall mean fluorine, chlorine, bromine or iodine.
The term 'halo" before the name of a radical shall mean that this radical is partially or completely halogenatsd, that is to say, substituted by F, Cl, Br, or I, in any combination, preferably by F or Cl.
The term ,,alkyl" shall mean a straight-chain or branched chain saturated aliphatic hydrocarbon group. In general alkyl groups possess one to ten carbon atoms, preferably one to eight carbon at-
orns. Examples of alky I groups are methyl, ethyl, propyl, isopropyl, 2-methylpropyl, 1-butyl, 2-butyl, isobWyl, tert-butyl, 2-methylbutyl, 1,1-dimethylpropyl, n-pentyl, n-hexyl, n-heptyl, 2-ethylhexyl Or octyl.
The term "C1-C6-alkyl" is to be understood as meaning an unbranched or branched hydrocarbon radical haviftg one to six carbon atoms.
Alkyl radicals preferably have 1 to 4 carbon atoms.
The term "haloalkyl" shall mean an alkyl group wherein one or more hydrogen atoms are replaced by identicallor different halogen atoms, preferably by fluorine and/or chlorine.
Examples for haloalkyl groups are trifluoromethyl, difluoromethyl, monofluoromethyl, 1- or 2-
fluoroethylj 2,2,2-trifluoroethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, mono-, di- or tri-
chlorometh$'l, l-fluoro-2-chloro-ethyl, l-chloro-2-fluoro-ethyl or 1- or 2-chloroethyl.
Haloalkyl radicals preferably have 1 to 2 carbon atoms.
The term ,,|ilkoxy" shall mean a straight-chain or branched chain saturated aliphatic hydrocarbon group whic|h is connected via an oxygen atom to another group. In general alkoxy groups possess one to ten icarbon atoms, preferably one to eight carbon atoms. Examples of alkoxy groups are methoxy, ethoxy, propyloxy, isopropyloxy, 1-butyloxy, 2-butyloxy, isobutyloxy, tert-butyloxy, 2-methylbutyloxy, 1,1-dimethyIpropyloxy, n-pentyloxy, n-hexyloxy, n-heptyloxy, 2-ethylhexyloxy or octyloxy.
The term "(C1-C6)alkoxy" shall mean an alkoxy group whose carbon chain has the meaning given under the expression "(C1-C6)-alkyl".
The term "haloalkoxy" shall mean an alkoxy group wherein one or more hydrogen atoms are replaced by lalogen atoms, preferably by fluorine and/or chlorine. Examples for haloalkoxy groups are trifluoromethoxy, difluoromethoxy, monofluoromethoxy, pentafluoroethoxy, 1- or 2-fluoroethoiy, 2,2,2-trifluoroethoxy, chloromethoxy, 2-chloroethoxy or 1,1,2,2-tetrafluoro-ethoxy.
The term alkcylthio" shall mean a straight-chain or branched chain saturated aliphatic hydrocarbon group which is connected via a sulfur atom to another group. In general alkylthio groups possess one to ten carbon atoms, preferably one to eight carbon atoms. Examples of alkylthio groups are methylthio, ethylthio, propylthio, isopropylthio, l-butylylthio, 2-butylthio, isobutylthio, tert-butylthio, 2-methylbutylthio, 1,1-dimethylpropylthio, n-pentylthio, n-hexylthio, n-heptylthio, 2-ethylhexyljthio or octylthio.
The term .alkenyl" shall mean a straight-chain or branched chain unsaturated aliphatic hydrocarbon group possessing one or more non-conjugated double bonds. In general alkenyl groups possess one to ten?carbon atoms, preferably one to eight carbon atoms. Examples of alkenyl groups are vinyl, allyl, 2-methyl-2-propenyl, 1- or 2-butenyl, pentenyl, 2-methylpentenyl, hexenyl, heptenyl or octenyl.
The term "(C1-C6)-alkenyl" shall mean an unbranched or branched non-cyclic carbon chain having a number $f carbon atoms which corresponds to this stated range and which contains at least one double borid which can be located in any position of the respective unsaturated radical.
The term alkynyl" shall mean a straight-chain or branched chain unsaturated aliphatic hydrocarbon group jpossessing one or more non-conjugated triple bonds. In general alkynyl groups possess one to ten; carbon atoms, preferably one to eight carbon atoms. Examples of alkynyl groups are ethynyl, propargyl, 2-methyl-2-propynyl, l-methyl-2-propynyl, 2-butynyl, 3-butynyl, pentynyl-, 2-methylpentynyl, hexynyl, heptynyl and octynyl.
The term 'teycloalkyl" shall mean a monocyclic and saturated alkyl group having preferably three to seven rjng carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctylj or cyclodecyl; or a bicyclic and saturated alkyl group, such as norbornyl or bicy-clo[2.2.2]octyl; or condensed and saturated system, such as decahydronaphthalene. Monocyclic cycloalkyli groups with five- or six-membered rings are preferred.
Cycloalkyl groups preferably are optionally substituted by halogen or alkyl.
The term ,,aryl" shall mean a carbocyclic aromatic group formed from ring-carbon atoms, preferably six to fourteen, especially six to twelfe ring carbon atoms. Examples for aryl groups are phenyl, naphthyl or biphenylyl, preferably phenyl.
The term,,heterocyclyl" shall mean a cyclic group being fully saturated, partially unsaturated or fully unsaturated which possesses besides at least one ring carbon atom one or more ring heteroa-toms selected from the group of oxygen, sulfur and nitrogen. Different ring heteroatoms are possible with the exception of two adjacent ring oxygen atoms. Heterocyclyl groups preferably contain one two or three hetero atoms in the heterocyclic ring, preferably selected from the group consisting of N, O and S (including the oxidized forms of S). Hetero-cyclyl groups are preferably aliphatic heterocyclyl radicals having three to seven ring atoms or heteroaromatic radicals having five to seven ring atoms. Heteroaromatic groups can be mono-, bi- or polycyclic aromatic systems in which at least one ring contains one or more hetero atoms.
Examples of heterooyclyl groups axe thiophenyl, furyl, pyrrolyl, thiazolyl, oxazolyl, imidazolyl, isothiazolyl,; isoxazolyl, pyrazolyl, 1,3,4-oxadiazolyI, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, 1,2,4-oxadiaizofyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazoIyl, 1,2,3,4-tetrazolyl, -benzotblthiqphenyl, benzo[b]furanyl, indolyl, benzo[c]thiophenyl, benzo[c]furanyl, isoindolyl, benzoxazoljll, benzothiazolyl, benzimidazolyl, benzisoxazolyl, benzisothiazolyl, benzopyrazolyl, benzothiadi4zolyl, benzotriazolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, pyridyl, pyraz-inyl, pyrimifinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,4,5-tetrazinyl, quinolinyl, isoqui-nolinyl, chinoxalinyl, chinazolinyl, cinnolinyl, 1,8-naphthyridinyl, 1,5-naphthyridinyl, 1,6-naphthyjfidinyl, 1,7-naphthyridinyl, phthalazinyl, pyridopyrimidinyl, purinyl, pteridinyl, 4H-quinoliz|nyl, piperidinyl, pyrrolidinyl, oxazolinyl, tetrahydrofuranyl, tetrahydropyranyl, isoxa-zolidinyl, thiazolidmyl, thienyl, oxiranyl, oxetanyl,_oxolanyl (= tetrahydrofuryl), oxanyl, pyrrolidyl, piporidyl, pfperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and mor-pholinyl.
The term "fketeroaromatic group" or "heteroaryl group" is a subgroup of the term ,,heterocyclyl group" and encompasses the in the above list mentioned fully unsaturated aromatic heterocyclic componds.
Heterocycly groups may be unsubstituted or substituted, preferably by one or more radicals, very preferably by one to three radicals selected from the group consisting of halogen, alkoxy, haloalkoxy,; alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino such as acylamino, mono-and dialkylftmino, and alkylsulfinyl, haloalkylsulflnyl, alkylsulfonyl, haloalkylsulfonyl, 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.
Heterocyclyl shall preferably mean an unsaturated, partially saturated or aromatic ring system with three to six ring carbon atoms and one to four ring hetero atoms selected from the group oxygen, sulfur and nitrogen or their combinations.
Two groupjs together with an. attached C-atom may form a four- to seven-membered carbocyclic ring saturated or unsaturated ring including an aromatic ring. They may form one ring or a ring system wherein one ring is fused to one or more saturated or unsaturated carbocyclic or heterocyclic rings, preferably to a benzene ring. Examples of such fused systems are indanone, tetralone or chromanonte.The term ..pycloalkylalkyl" shall mean a cycloalkyl group which is connected via an alkylene group to another group. The alkylene portion is a saturated straight-chain or branched-chain hydrocarbon portion possessing in general one to six carbon atoms.
The term ,,cycloalkyloxy " shall mean a cycloalkyl group which is connected via an oxygen atom to another group.
The term arralkyl" shall mean an aryl group which is connected via an alkylene group to another group. The alkylene portion is a saturated straight-chain or_branohed-chain hydrocarbon portion possessing jn general one to six carbon atoms. Preferred aralkyl group is benzyl.
The term ,heterocyclylalkyl" shall mean a heterocyclyl group which is connected via an alkylene group to anjother group. The alkylene portion is a saturated straight-chain or branched-chain hydrocarbon port|on possessing in general one to six carbon atoms.
Preferred 4e compounds of formula I wherein W is =C(halogen)-,
Preferred afe compounds of formula I, wherein R8 is chlorine or fluorine.
Preferred ate compounds of formula I, wherein R1 is cyano, methyl, trifluoromethyl or -CS-NH2.
Very preferably R1 is -CN or -CSNH2 and most preferred R1 is -CN.
Preferred ajre compounds of formula I, wherein R2 is (C1-C3)-haloalkyl and most preferred -CF3.
Preferred are compounds of formula I, wherein R3 is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyi! or haloalkynyl.
Preferably !R3 is hydrogen or (C1-C6)-alkyl unsubstituted or substituted by one or more radicals selected ffom the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C3-C6)-alkenyloxjj, (C1-C6)-haloalkenyloxy, (C3-C6)-alkynyloxy, (C3-C6)-haloallcynyloxy, (C3-C7) cycloalkylj S(O)pR19, CN, NO2, OH, R20, R21, COR19, NR^R23, OR19, COOH and CO2R19, wherein R19, R20, R*1, R22, R23 and p are as hereinafter defined.
More preferably R3 is hydrogen or (C1-C3)-alkyl. ,
Preferred We compounds of formula I, wherein R4 and R5 independently of one another are alkenyl, alkynyl, haloalkenyi or haloalkynyl.
Preferably R4 and R5 are each independently of one another (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl (C2-C6)-haloalkynyl, (C3-C7)-cycloalkyl, (C3-C7)-cycIoalkyl-(C1-C4)-alkyl, or are indepjendently of one another phenyl, heterocyclyl which are unsubstituted or substituted by one or moije radicals selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-haloalkenyloxy, (C3-C6)-alkynyloxy, (C3-C6)-haloalkynylfxy, (C3-C7)-oycIoalkyl, (C3-C7)-cycloalkyloxy, S(O)pR19, CN, NO* OH, R20, R21, COR19, NRfR23, OR19, COOH and CO2R19,
or are each j independently (C1-C6)-alkyl unsubstituted or substituted by one or more radicals selected froni the group consisting of halogen, (Ci-C6)-alkoxy, (C]-C6)-haloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-haloalkenyloxy, (C3-C6)-alkynyloxy, (C3-C6)-haloalkynyloxy, (C3-C7)-cycloalkyl, {C3-C7)-cycloalkyloxy, S(0),,R19, CN, NO2, OH, R20, R21, COR19, NR22R23, COOH and CO2R19, or
R4 and R5 together with the attached C atom can form a four- to seven-membered saturated ring or a five- to seven-membered unsaturated ring, which optionally contains one or more hetero atoms in the ring whfch are selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl and oxo, and whjen present any additional ringN atom is unsubstituted or substituted by a (C1-C6)-alkyl, CO- (C1-C6)fralkyl or CHaR20 radical; or which is condensed with a benzene ring, wherein R19, R20, R21, R22, R2J and p are as hereinafter defined.
R6 is very preferably halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl or -SF5 most preferred chlorine or -CF3.
Preferred are compounds of formula I, wherein R7 and R8 are halogen or R7 is -NR17R18.
Very preferred are compounds of formula I, wherein
R1 is -CN,
R7 is halogdn, -CH3or -NR17R18,
R6 is (C1-C3)-haIoalkyl, (C1-C3)-haloalkoxy or -SF5,
R3 is hydrigen, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-
C7)-cycloalkyl, (C3-C7)-cycloalkyl- (C1-C6)-alkyl, or (C1-C6)-alkyl unsubstituted or substituted by
one or mofe radicals selected from the group consisting of halogen, (C1-C6)alkoxy, (C1-C6)-
haloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-haloalkenyloxy, (C3-C6)-alkynyloxy(C3-C6)-halpalkynyloxy, (C3-C7)-cycloalkyl, (C3-C7)cycloalkyloxy, -S(O)pR19, -CN, -NO3, -OH, -R20, R21, -CDR19, -NR22R23, -OR19, -COOH and -CO2R19,
R2 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl> (C2-C6)-alkynyl or (CrC6)-haloalkynyi,
R4 and R5 ire each independently (C2-Cs)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyf, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkyl-(C1-C4)-alkyl, or are each independently phenyl, hetferocyclyl which are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen,(C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-haloalkenyjbxy, (C3-C6)-alkynyloxy, (C3-C6)-haloalkynyloxy, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkylqxy, S(O)PR19, CN, NO2s OH, R20, R21, COR19, NR22R23, OR19 , COOH and CO2R19, or are each independently (Ci-Cfi)-alkyl unsubstituted or substituted by one or more radicals selected from the gjroup consisting of halogen, (Ci-C6)-alkoxy, (C1-C6)haloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-haljoalkenyloxy, (C3-C6)-alkynyloxy, (C3-C6)-haloalkynyloxy, (C3-C7)-cycloalkyl, '(C3-C7)-cycloalkylcfxy, S(O)PR19, CN, NO2, OH, R20, R21, COR19, NR^R23, COOH and CO2R19, or
R4 and R5 together with the attached C atom can form a four- to seven-membered saturated ring or a five- to seven-membered unsaturated ring, which optionally contains one or more hetero atoms in the ring which are selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl and oxo, and when present any additional ring N atom is unsubstituted or substituted by a (C1-C6)-alkyl, CO-(CrC6|-alkyl or CHjR20 radical; or which is condensed with a benzene ring,
R19 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C7)-cycloalkyl, (C1-C4)-alkyl-(C3-C7)-cycloalkyl, -(CH2)qR20»r~-(CH2)qR21,
R20 is pherjyl unsubstituted or substituted by one or more radicals selected from the group consist-ing of halbgen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, CN, NO2, S(O)pRl9apdNR22R23,
R21 is hetorocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting Of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, S(O)PR19, OH and oxo,
R22 and R?3 are each independently hydrogen, (C1-C6-alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynyl, which lastithree mentioned groups are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C3-C7)-cycloalkyl, R20, R21, (CrC6)-alkoxy, (Cr C6)-haloal)toxy, and
n and p andjq are each independently zero, one or two.
Most preferred are compounds of formula I, wherein:
R1 is CN,
R7 and R8 ale Cl,
R6isCF3lR3 is hydrogen or (C1-C3)-alkyl, and
R2 is CF3.
Most prefeiired are compounds of formula I, wherein:
R4 and R5 are each independently (C2-C6-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-Cfi)-haloalkynyj, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkyl-(C1-C4)-alkyl,or are each independently R20, R21, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, ((n-C6)-alkoxy, (C1-C6)-haloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-haloalkenyloxy, (C3-C6)-alkynylioxy, (C3-Cs)-haloalkynyloxy, (C3-C7)-cycloalkyl, S(O)pR19, CN, NO2, OH, R20, R21, COR19, NRpR'VOR19, COOH and CO2R19,or are each independently (C1-C6)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6) alkoxy, (C1-C6)haloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-haloalkenyloxy, (C3-C6)-alkynyloxy, (C3-C6)-haloalkjynyloxy, (C3-C7)-cycloalkyl, S(O)pR19, CN, NO2, OH, R20, R21, COR19, NR22R23, OR19, COOH and; Co2R19,
R4 and R5 together with the attached C atom can form a four- to seven-membered saturated ring or a five- to siven-membered unsaturated ring, which optionally contains one or more additional het-ero atoms ki the ring which are selected from O, S and N, the ring being unsubstituted or substituted by onje or more radicals selected from the group consisting of halogen, (C1-C6)-alkyl,(C1-C6)-haloalkyl ajid oxo, and when present any additional ring N atom is unsubstituted or substituted by a (C1-C6)-alkll, CO-(C1-C6)-alkyl or CH2R20 radical;' or which is condensed with a benzene ring.
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 anions or cations of which are known and accepted in the art for the formation of salts for pesticidal use.
Suitable sa|ts 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, triethanolamine, octylamine, morpholine and dioctyljnethylainme) salts. Suitable acid addition salts, e.g. formed by compounds of formula I containing jan ammo group, include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates and nitrates and salts with organic acids for example acetic acid.
The expression "one or more radicals selected from the group consisting of in the definition is to be understood as meaning in each case one or more identical or different radicals selected from the stated group of radicals, unless specific limitations are defined expressly.
The term pests means arthropod pests (including insects and arachnids), and helminths (including nematodes)
The compounds of formula I can be prepared by the application or adaptation of known methods (i.e. methods heretofore used or described in the chemical literature).
In the following description of processes when symbols appearing in formulae are not specifically defined, it |s understood that they are "as defined above" in accordance with the first definition of each symbol in the specification.
According to a further feature of the invention compounds of formula I wherein R1 is cyano, halogen, alkyl or haloalkyl and R2, R3, R4, R5, R6, R7, W and n are as defined above, may be prepared by the reaction of a compound of formula II:
(Formula Removed)
wherein R1 Is cyano, halogen, alkyl or haloalkyl and the other values are as defined above, with an oxime of formula 011):
R4R5C=N-OH (III) and phosgene COCl2 (or a phosgene precursor like diphosgene or triphosgene) and a base.
The reaction is generally carried out using a solvent such as tetrahydrofuran, dioxan, dichloro-methan or tcetonitrile, at a temperature of from 0°C to 100°C. The base is preferably an organic base such is a tertiary amine, for example triethylamine or ethyldiisopropylamine, or an alkali metal hydride such as sodium hydride, or an alkali metal carbonate such as potassium carbonate or sodium carbonate, or an alkali metal phosphate such as potassium phosphate.
According to a feature of the invention compounds of formula I, wherein Rl of is -CSNHa, and the other values are as defined above, may be prepared by the reaction of the corresponding compound of formula :I, wherein R1 is CN, with alkali metal or alkaline earth metal or hydro sulphides, such as sodium jw lithium, potassium, calcium preferably hydro sulphides, in at inert solvent for example N,N-dimethylformamide, pyridine, dioxan, tetrahydrofuran, sulfolane, dimethyl sulfoxide, methanol ar ethanol at a temperature from -35°C to 50°C preferably 0°C to 30°C. Optionally the hydrosulphides may be generated in situ by treatment with H2S in the presence of at organic base, such as a metal alkoxide or trialkylamine or an inorganic base, such as metal alkaline at alkaline or earth hydroxide or a carbonate, such as carbonate for sodium, potassium or ammonium. The use of a metal complexing agent, such as a crown ether, can be of benefit in accelerating the reaction.
The reaction of hydrosulphide salt with the compound of formula I can therefore be conducted in a two-phase iwater/organic solvent system using a phase transfer catalyst selected from a crown ether or a tetraajlkylammonium salt or benzyltrimethylammonium chloride or tetra-n-butylammonium bromide. Organic solvents suitable for use in a two-phase system with water include benzene, tolu-ene, dichlpromethane, 1-chlorobutane and methyl tertiary-butyl ether.
According to a feature of the invention compounds of formula I, wherein R1 is -CS-NH2, and the other values are as defined above may be prepared by the reaction of the corresponding compound of formula I, wherein R1 is -CN, with a bis(trialkylsilyl)sulfide, preferably bis(trimethylsilyl)sulfide, in the presence of a base generally an alkali metal alkoxide, for example sodium monoxide, in a solvent such as N,N-dimethylformamide, at a temperature of from 0°C to 60°C. The procedure is generally described by Lin, Ku of and Shiao in Synthesis 1219(1992).

According to a feature of the invention compounds of formula I, wherein n is 1 or 2 and R1, R2, R3, R4 , R5, R 6, Z and W are as defined above, 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 3-chloroperbenzoic acid in a solvent, such as dichloromethane or in 1,2-dichloroethane, at a tem-perature of from 0°C to the reflux temperature of the solvent.
Intermediates of formula II may be prepared as described in EP-A-295,117.
Collections! of compounds of the formula I which can be synthesized by the above mentioned process may therefore be prepared in a parallel manner, and this may be effected manually or in a semi-automated or fully automated manner. In this case, it is possible, for example, to automate the procedure of t|e reaction, work-up or purificadon of the products or of the intermediates. In total, this is to be understood ace meaning a procedure as is described, for example, by S.H. Dewitt in "Annual report! in Combinatorial Chemistry of and Molecular Diversity: Automated Synthesis", Volume 1, pubjishing house Escom 1997, pages 69 to 77.
A series of commercially available apparatuses are offered by, for example, Stem Corporation, Woodrolfe Road, Tollesfaury, Essex, CM9 8SE, England of or H+P laboratory technology Ltd., Bruckmannring 28, 85764 Oberschleiflheim, Germany of 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 of be made, inter alia, of chromatography apparatuses, for example those by ISCO, Inc.,, 4700 superiors Street, Lincoln, NE 68504, USA.
The apparatuses mentioned lead to a modular procedure in which the .individual process steps are automated,! but manual operation must be performed between the process steps. This can be prevented by Employing semi-integrated or fully integrated automation of system of where the automation modules in question are operated by, for example, robots. Look automation of system of can be obtained, for example, from Zymark Corporation, Zymark Center, of Hopkinton, MA 01748, for 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, 199$.
The use of solid-phase-supported synthesis methods permits a series of protocols which are known from the literature and which, in does gymnastics, can be performed manually or in at automated manner. Far example, the "tea-bag method" (Houghten) U.S. 4,631,211; Houghten et al., Proc. Natl. Acadj.Sci, 1985, 82, 5131-5135, in which products by IRORI, 11149 North-Torrey Pines Road, La Jolla CA 92037 USA, are employed, May be semiautomated. The_automation of solid-phase-supp|>rted, parallel syntheses is performed successfully, for example, by apparatuses by Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, CA 94070, USA or MultiSynTech Ltd., Wullejner field 4, 58454 Witten, Germany.
The preparation of the processes described herein yields compounds of the formula I in the form of substance collections which are termed libraries. The present invention therefore relates to libraries which comprise at least of two compounds of the formula I.
Compounds of formula III are known or may be prepared by known methods.
The following non-limiting 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, therefore percentages, are weight based, unless stated otherwise. Ratios of solvents are volume based.
Example 11 Compound number 3-02
l-[2,6-dichloro-4-(triiluoromethyl)phenyl]-5-[methyl({[(l-phenylethylidene)amino]oxy}carbonyl) amino]-4-f|trifluoromethyl)sulfinyl]-lH-pyrazole-3-carbonitrile
To a mixture of l-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-methylamino-4-trifluoro-methylsulfinylpyrazole (0.5 g, 1.1 mmol), acetophenone-oxime (0.165 g, 1.2 mmol), diisopro-pylethylanjine (0.43 g, 3.3 mmol) and 4-dimethylaminopyridine (41 mg, 0.3 mmol) in tetrahydro-furan (15 ml) was added a toluene solution of phosgene (0.66 g, 20%, 1.2 mmol) at 0-5°C. The mixture wfts stirred at reflux for 2 hours. Extractive workup (heptane-ethyl acetate, water) and chromatogj-aphy gave the title product (Compound 3-02, 0,14 g) as a solid; 1H-NMR: 2,25 (3H), 3,21 (3H), 7,42 and 7,68 (5H), 7,82 (2H); 19F-NMR: -64,3 (PhCF3); -72,9 (SO-CF3).
Example 2: Compound number 4-08
To a mixture of l-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-methylamino-4-trifluoro-methylsulfufylpyrazole (0.5 g, 1.1 mmol), cyclohexanone-oxime (0.138 g, 1.2 mmol), diisopro-pylethylamine (0.43 g, 3.3 mmol) and 4-dimethylaminopyridine (41 mg, 0.3 mmol) in tetrahydro-furan (15 n|l) was added a toluene solution of phosgene (0.66 g, 20%, 1.2 mmol) at 0-5°C. The mixture waf stirred at reflux for 2 hours. Extractive workup (heptane-ethyl acetate, water) and chromatogrtphy gave the title product (Compound 4-08, 0.12 g) as an oil; 1H-NMR: 1,62 and 1,74 (6H), 2,34 (jffl), 3.1 1 (3H), 7.81 (2H); 19F-NMR: -63,8 (Ph-CF3); -72,4 (SOCF3).
Tables:
The following preferred compounds shown in Tables 1 to 4 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 4 or the above-described general methods.
Where subscripts are omitted they are intended, for example CH2 means CH2.
In the Tablf s Me means methyl, Et means ethyl, Pr means propyl, Bu means butyl, C5H1 1 means n-pentyl, C6513 means n-hexyl, C2H4 means ethylene, (-CH2CH2-), cC3H5 means cyclopropyl, NHC3H6 njeans propyleneamino, (-CH2CH2CH2NH-), and Ph means phenyl.
19F-NMR spectra shift values are given in ppm.
"Cpd No" rtieans Compound Number.
Compound mumbers are given for reference purposes only.
Table 1 : Compounds of Formula I in which the substituents have the following meanings:
R1 is CN; R7and R8 are Cl; R6 and R2 are each CF3; R3 is Me
R4 and R5 are each independently (C1-C6)-alkyl or (C1-C6)-haloalkyl
(Table Removed)

Table 2: Compounds of Formula I in which the substituents have the following meanings:
R1 is CN; K7 and R8 are Cl; R6 and R2 are each CF3; R3 is Me;
R4 is (C1-C6)-alkyl and R5 is (C3-C7)-cycloalkyl or (C3-C7)-cycloalkyl-(C1-C4)-alkyl
(Table Removed)

Table 3: Co|npounds of Formula I in which the substituents have the following meanings:
R1 is CN; RJ and R8 are Cl; R6 and R2 are each CF3; R3 is Me;
R4 is (C1-C6)alkyl or R20 and R3 is R20 or R10 or (C1-C6)-alkyl substituted by R20
(Table Removed)



Table 4: Compounds of Formula (I) in which the substituents have the following meanings: R1 is CN; R7 and R8 are Cl; R6and R2 are each CF3; R3 is Me;
R4 and R5 are connected to form together with G of the C=NO unit a four- to seven-membered saturated ring ojf a five- to seven-membered unsaturated ring
(Table Removed)

Table 5: (Compounds of Formula I in which the substituents have the following meanings:
R1 is CN; Rf and R8 are Cl; R6 and R2 are each CF3; R3 is H;
R4 and R5 are each independently(C1-C6)-alky] unsubstituted or substituted
(Table Removed)

Table 6: Compounds of Fonnula I in which the substituents have the following meanings:
R1 is CN; R7 and R8 are Cl; R6 and R2 are each CF3; R3 is H;
R4 is (C1-C6)-alkyl and R5 is (C3-C7)-cycloalkyl or (C3-C7)-cycloalkyl-(C1-C4)-alkyl
(Table Removed)
Table 7: Cojmpounds of Fonnula I in which the substituents have the following meanings:
R1 is CM; R7 and R8 are Cl; R6 and R2 are each CF3; R3 is H;
R4 is (C1-C6)-alkyl or R20 and R5 is R20 or R21 or(C1-C6)-alkyl substituted by R20
(Table Removed)

Table 8: Compounds of Formula I in which the substituents have the following meanings: R1 is CN; R7 and R8 are Cl; Rs and R2 are each CF3; R3 is H;
R4 and R3 are connected to form together with C of the C=NO unit a four- to seven-membered satu-5 rated ring or a five- to seven-membered unsaturated ring
(Table Removed)
According to a further feature of the present invention there is provided a method for the control of pests at a locus which comprises applying thereto an effective amount of a compound of formula I or a salt thf reof. 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 polar 5-aminopyrazole car-bamate derivative of formula I 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 like) where the pest resides or feeds, or a place susceptible to future infestation by the pest. The compound of 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 compound! 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 livestock husbandry, or in public health.
The compounds of the invention may be used for example in the following applications 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, stalkborers, cutworms, root aphids, or grubs. They may also be used to provide activity against plant pathogenic nematodes, such as root-knot, cyst, dagger, lesion, or stem or bulb nematodes, or against mites. For the control of soil pests, for exam-
ple corn rootworm, the compounds are advantageously applied to or incorporated at an effective rate into the Soil in which crops are planted or to be planted or to the seeds or growing 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 houseflies, stableflies, soldierflies, homflies, 5 deerflies, horseflies, midges, punkies, blackflies, or mosquitoes.
In the protection of stored products, for example cereals, including grain or flour, groundnuts, ani-mal 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), Tribolium spp, (flour bee-tles), Sitophllus spp. (grain weevils) or Acarus spp. (mites).
In the contrjol 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, Reticulitermes spp., Heterotermes spp., Coptotermes spp..
Moreover it has been found that the compounds of the invention exhibit high insecticidal action against inseicts that destroy technical materials.
As example and preferably - but not limiting - the following insects are named:
Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovil-losum, Ptiljnus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brun-neus, Lyctus afiicanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rujgicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostlychus brunneus, Sinoxylon spec. Dinoderus minutus;
Hymenoptfra such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticuliter-mes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zo-otermopsis nevadensis, Coptotermes formosanus;
Silverfish such as Lepisma saccharina.
Within the present context technical materials are understood to mean non-living materials such as preferably plastics, adhesives, glues, paper and cardboard, leather, wood, wood fabrication products and paints.
At the same time the compounds of the invention can be used for protection against fouling of objects, especially ships' hulls, screens, nets, buildings, wharfs and signal installations that come into contact with sea or brackish water.
Moreover, the compounds of the invention can be used in combination with other active com-pounds as anti-fouling agents.
The active compounds are suitable for the control of zoopests in household, hygiene and storage protection, especially insects, arachnids and mites that appear in enclosed spaces such as apart-ments, factory halls, offices, vehicle cabins, etc. They can be used alone or in combination with other active compounds and auxiliaries hi household insecticidal products for the control of these pests. They are active against sensitive and resistant species as well as against all development stages. These pests include:
The order Scorpionidea e.g. Buthus occitanus.
The order Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyci-phagus dofmesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombifula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
The order ^raneae e.g Aviculariidae, Araneidae.
The order JDpiliones e.g Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones pha-langium.
The order Isopoda e.g Oniscus asellus, Porcellio scaber.
The order Diplopodae.g.. Blaniulus guttulatus, Polydesmus spp..
The order Chilopoda e.g. Geophilus spp..
The order Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
The order der Blattaria e.g. Blatta orientalies, Blattella gennanica, Blattella asahinai, Leucophaea maderae, panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Pe-riplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.
The order Saltatoria e.g. Acheta domesticus.
The order Derermaptera e.g. Forficula auricularia.
The order Isoptera e.g. Kalotermes spp., Reticulitermes spp.
The order Ppocoptera e.g. Lepinatus spp., Liposcelis spp.
The order Coleoptera e.g. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Ne-crobia spp.j Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, St0gobium paniceum.
The order piptera e.g. Aedes aegypti, Aedes albopiotus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Dr^sophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga car-naria, Simujium spp., Stomoxys calcitrans, Tipula paludosa.
The order Lepidoptera e.g.. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, TJinea pellionella, Tineola bisselliella.
The order Siphonaptera e.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
The order Hymenaptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus ,Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
The order j^noplura e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera vjastatrix, Phthirus pubis.
The order Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodbus prolixus, Triatoma infestans. ;
The use injthe household insecticidal sector is carried out alone or in combination with other suitable active (compounds such as phosphates, carbarnates, pyrethroids, neonicotinoids, growth regulators or active compounds from other known classes of insecticides.
Use is carried out with aerosols, non-pressurised spray agents, e.g. pump and dusting sprays, nebu-lisers, misters, foamers, gels, evaporation products with evaporation platelets of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, non-energy or
passive evaporation systems, fly papers, fly traps, and fly gels, as granulates or dusts, in scatter bait or bait stations.
In agricultures against adults, larvae and eggs of Lepidoptera (butterflies and moths), e.g. Heliothis spp. such as Heliothis virescens (tobacco budworm), Heliothis armigera and Heliothis zea. Against adults and larvae of Coleoptera (beetles) e.g. Anthonomus spp. e.g. grandis (cotton boll weevil), Leptinotarsa decemlinata (Colorado potato beetle), Diabrotica spp. (corn rootworms). Against Heteroptera {Hemiptera and Homoptera) e.g. Psylla spp., Bemisia spp., Trialeurodes spp., Aphis spp., Myzus ispp., Megoura viciae, Phylloxera spp., Nephotettix spp. (rice leaf hoppers), Nilapar-vata 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 orientalis, Periplaneta americana, Blatella germanica, Locusta migratoria migrato-rioides, and I Schistocerca gregaria. Against Collembola e.g. Periplaneta spp. and Blatella spp. (roaches).
Against arthropods of agricultural significance such as Acari (mites) e.g. Tetranychus spp., and Panonychuslspp..
Against nemjatodes 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. For example root-knot nematodes such as Meloidogyne spp. (e.g. M. incognita).
In the field pf veterinary medicine or livestock husbandry or in the maintenance of public health against arthropods which are parasitic internally or externally upon vertebrates, particularly warmblooded verfebrates, for example domestic animals, e.g. cattle, sheep, goats, equines, swine, poultry, dogs orjcats, for example Acarina, including ticks (e.g. soft-bodied ticks including Argasidae spp. e.g. Argas spp. and Omithodorus spp. (e.g. Ornithodorus moubata); hard-bodied ticks including Ixodidae spp., e.g. Boophilus spp. e.g. Boophilus microplus, Rhipicephalus spp. e.g. Rhipicephal|us appendiculatus and Rhipicephalus sanguineus; mites (e.g. Damalinia spp.); fleas (e.g. Cteno4ephalides spp. e.g. Ctenocephalides felis (cat flea) and Ctenocephalides canis (dog flea)); lice 0.g. Menopon spp.; 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 off the family Trichostrongylidae.
In a preferred aspect of the invention the compounds of formula I are used for the control of para-
i sites of animals. Preferably the animal to be treated is a domestic companion animal such as a dog
or a cat.
The parasites! to be controlled include for example:
The order Ahoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., So-lenopotes spp.
The order Mallophagida and the suborders Amblycerina and Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectea; spp., Felicola spp.
The order Diptera and the suborders Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp,, Tabanus spp., Haematopota spp., Philipomyia spp., Braulai spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp.Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sar-cophaga sppj., Oestrus spp., Hypoderma spp,, Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagusj spp.
The order Siiphonapterida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
The order Heteropterida e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp. The order Blattarida e.g Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.
The subclass Acari (Acarina) and the order Meta- and Mesostigmata e.g. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophy-salis spp., ijyalomma spp., Rhipicephalus spp., Dermahyssus spp., Raillietia spp., Pneumonyssus spp., Sternoptoma spp., Varroa spp.
The order Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornitrjocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Lis-trophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes sjip., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The compounds of the invention of structure (I) are also suitable for the control of arthropods that affect agricultural animals such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other domestic animals such as dogs, cats, cage birds, aquarium fish as well as so-called experimental animals such as hamsters, guinea pigs, rats and mice. By control of these arthropods death rates and performance loss (in meat, milk, wool, hides, eggs, honey.etc.) will be reduced so that a more economic and simpler animal husbandry is possible by the usje of the compounds of the invention.
The use of the active compounds in veterinary sector and animal husbandry is carried out by known means by enteric administration in the form of, for example, tablets, capsules, drinks, drenches, granulates, pastes, boli, the feed-through process, suppositories, by parenteral administration by, for example! injection (intramuscular, subcutaneous, intravenous, interperitoneal, among others), implants, by nasal application, by dermal administration in the form of, for example, dipping, spraying, pour-on and spot-on, washing, powdering and with the help of appliances containing the active compound such as collars, ear markers, tail markers, limb bands, halters, marking devices, etc.
During use }n cattle, poultry, domestic animals, etc., the active compounds of structure (I) can be used as formulations (for example, powder, emulsions, flowable agents) that contain the active compounds (in an amount of 1 to 80 wt.%, directly or after 100 to 10,000 times dilution or as a chemical bath.
In a further aspect of the invention the compounds of formula (I) or salts or compositions thereof are used for the preparation of a veterinary medicament.
A further feature of the invention thus relates to the use of a compound of formula I or a salt thereof, or of a composition thereof, for the control of pests.
The above r|amed pests include for example:
the order Anoplura (Phthiraptera) e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pedi-culus spp., Trichodectes spp.
The class of Arachm'da e.g. Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Derma-nyssus galljnae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemi-tarsonemusj spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oli-gonychus spp., Omithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsone-

mus latus, psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsoriemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.
The class of Bivalva e.g. Dreissena spp.
The order Chilopoda e.g. Geophilus spp,, Scutigera spp.
The orderColeoptera e.g. Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp,, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp,, Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Ceutho-rhynchus sp|p,, Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Cur-culio spp., tryptorhynohus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cu-bae, Gibbii|m psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilusj, Lixus spp., Lyotus spp., Meligethes aeneus, Melolontha melolontha, Migdohis spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Popillia japjoniea, Premnotrypes spp., Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio mjilitor, Tribolium spp,, Trogodenna spp., Tychius spp., Xylotrechus spp., Zabrus spp.
The order Collembola e.g. Onychiurus armatus. The order Dermaptera e.g. Forficula auricularia. The order Diplopoda e.g. Blaniulus guttulatus.
The order liptera e.g. Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fannia spp., Gastrophilus spp., Hylemyia sppp., Hyppobosca spp., Hypoderma spp., Liriomyza spp.. Lucilia spp., Musca spp., Nezara spp, Oestrus spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanus spf., Tannia spp., Tipula paludosa, Wohlfahrtia spp.
The class Gastropoda e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.
The class of Helminths e.g. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma bra-ziliensis, Ancylostoma spp,, Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori,

Bunostomurh spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocular|s, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymeno-lepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthor-chis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosoraen spp, Strongy-loides fuelliborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudop-siralis, Tricrfostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.
In addition protozoa such as Eimeria may be controlled.
The order Heteroptera e.g. Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campy-lomma lividja, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furca-? tus, Diconojioris hewetti, Dysdercus spp., Euschistus spp., .Eurygaster spp., Heliopeltis spp., Hor-cias nobileljus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miri-dae, Nezaraj spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacyst4 persea, Rhodnius spp., Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp Triatoraa spp.
The order ijlomoptera e.g. Acyrthosipon spp., Aeneolamia spp., Agonoscena spp,, Aleurodes spp., Aleurolobu|i barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigjna piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthu|n solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne bras-sicae, Calligypona marginata, Caraeocephala fulgida, Ceratovacuna lanigera, Cercopidae, Cero-plastes spp Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis jug-landicola, (jlhrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbijilus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilo-batus, Geofcoccus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscjopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphfm spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Meto-polophiumldirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myri-cae, Paratfioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzjus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriforrais, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp.,

Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopa-losiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella fiircifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocybajspp., Unaspis spp., Viteus vitifolii.
The order Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. :
The order Isopoda e.g. Armadillidium vulgare, Oniscus asellus, Porcellio scaber. The order Ispptera e.g. Reticulitermes spp., Odontotermes spp..
The order Lepidoptera e.g. Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticnlana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumi-ferana, Clysia ambiguella, Cnaphaloceras spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoefe, Euxoa spp,, Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hof-mannophila! pseudospretella, Homona magnanima, Hyponomeuta padella, Laphygma spp., Litho-colletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria spp., Malacosoma
f
neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae, Pano-lis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., Phrtella xylostella, Prode-nia spp., Psjeudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis| Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp.
The order Orthoptera e.g. Aoheta domestious, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
The order Siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis. The order Symphyla e.g. Soutigerella immaculata.
The order Thysanoptera e.g. Baliothrips biformis, Ermeothrips flavens, Frankliniella spp,, Helio-thrips spp Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taen|othrips cardamoni, Thrips spp.
The order Thysanura e.g. Lepisma saccharina.

The plant parasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Be-lonoaimus $pp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Hetercjdera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.
The compounds of structure (I) of the invention are characterised particularly by strong action against aphds (e.g. Aphis gossypii and Myzus persicae), beetle larvae (e.g. Phaedon cochleariae), butterfly caterpillars (e.g. Plutella xylostella, Spodoptera exigua and Spodoptera frugiperda).
The compounds of the invention can optionally also be used in certain concentrations or application amounts as herbicides, safeners, growth regulators, or as agents for improving plant properties or as microbiocid.es, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as agents against MLO (Mycoplasma-like organism) and RLO (Rickettsia-like organism).they may also be optionally used as intermediates or precursors for the synthesis of further active compounds.
According to the invention all plants and plant parts can be treated. Plants are hereby understood to mean all plants and plant populations such as desirable and undesirable wild plants or cultigens (including naturally occurring cultigens). Cultigens can be plants that can be obtained by conventional breeding and optimisation methods or by biotechnology or genetic engineering methods or combinations of these methods, including transgenic plants and including plant varieties that are protectable or not protectable by plant varieties protection rights. Plant parts are understood to be all above ground and below fcround parts and organs of the plants such as scion, leaf, blossom and root, including, for example, leaves, needles, stalks, stems, blossoms, fruiting bodies, fruits and seed as well as roots, bulbs, rhizomes. Harvest crops as well as vegetative and generative reproduction material, for example cuttings, bulbs, rhizomes, shoots and seed also belong to plant parts.
In practical use for the control of arthropods, especially insects or mites, or helminths, especially 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 locus in which the arthropod or nematode infestation is to be controlled at an effective rate in the range of about 2g to about 1kg of the active compound jper 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 application.; Preferably an effective rate range of the active compound is from about l0g/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 applied at rates from about lOg ai/ha to about 400g ai/ha, preferably from about 50g ai/ha to about 200 g ai/ha (,,ai" means active ingredient). When 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 ai/1, preferably from about 25 to about 200 mg ai/1. 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 frij)m 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 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 of field, forage, plantation, glasshouse, orchard or vineyard crops, of ornamentals, or of plantatio 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 majze 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 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, mites 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 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 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 compoundsjof 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, e.g. by liquid slurries or dusts;
to animals Infested by or exposed to infestation by arthropods or helminths, by parenteral, oral or topical appjication of compositions in which the active ingredient exhibits an immediate and/or prolonged ajction 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 licks, dietary supplements, pour-on formulations, sprays, baths, dips, showers, jets, dusts, greases, shampoos, creates, 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 tricklefeeds to waterways, wells, reservoirs or other running or standing water.
The compounds of formula I are particularly useful for the control 6f 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 I or salts thereojf 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 I or salt thereof is administered orally in a dose to the animal in a dose range generally from 0.1 to 500 mg/kg of the compound of the formula I or salt thereof per kilogram of (animal body weight (mg/kg).
The frequency of treatment of the animal, preferably the domestic animal to be treated by the compound of th| formula I 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 parasiti-cidally effective material, such as an endoparasiticide, and/or an ectoparasiticide, and/or an endec-toparasiticide. For example, such compounds include macrocyclic lactones such as avermectins or milbemycins e.g., ivermectin, pyratel or an insect growth regulator such as lufenuron or metho-prene.
The compounds of the formula I can also be employed for controlling 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 bisects or microorganisms such as fungi, bacteria or viruses. Other particular properties concern, for example, the harvested 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 material has a different fatty acid composition.
All plants fhat have received by genetic engineering modification genetic material that imparts particularly! advantageous valuable properties ("traits") to these plants belong to the transgenic (obtained by genetic engineering) plants or plant varieties to be preferably treated in accordance with the indention. Examples of such properties are improved plant growth, increased tolerance toward high or low temperatures, increased tolerance toward drought or toward water or soil salt content, improved blossoming performance, simplified harvesting, accelerated ripening, increased harvest yields, improved quality and/or nutritional value of the crop, better storage life and/or processing of the crop. Further and particularly emphasised examples of such properties are increased resistance of the plants toward zoopests and microbial pests, such as toward insects, mites, pathogenic plant fungi, bacteria and/or viruses as well as an increased tolerance of the plants toward certain herbicides. Examples of such transgenic plants are the important cultigens such as cereals (wheat, rice), maize, soy, potato, sugar beet, tomato, peas, and other vegetable varieties, cotton, tobacco, rape as well as fruit plants (with the fruits apple, pear, citrus fruits and grapes), whereby

maize, soy, potato, cotton, tobacco and rape are especially emphasised. Properties ("traits") especially emphasised are the increased tolerance of the plants toward insects, arachnids, nematodes and gastropods through the toxins formed in the plants, especially those that are produced in the plants (hereinafter known as "Bt plants") by the genetic material from Bacillus thuringiensis (e.g. from the genes CrylA(a), CrylA(b), CryIA(c), CryllA, CrymA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations). Also particularly emphasised as properties ("traits") is the increasdd resistance of plants toward fungi, bacteria and viruses through systemically acquired resistance (BAR), systemin, phytoalexine, elicitors and resistance genes and correspondingly expressed profeins and toxins. Further particularly emphasised properties ("traits") are the increased tolerance ot the plants to certain active herbicidal compounds, for example imidazolinones, sul-phonylureas;, glyphosate or phosphinotricin (e.g. "PAT'-gene). The respective genes imparting the desired properties ("traits") can also occur in the transgenic plants in combination with each other. Examples of such "Bt plants" are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade marks YIELD GARD® (e.g. maize, cotton, soy), KnockOut® (e.g. maizej, StarLink® (e.g. maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide tolerant plants are maize varieties, cotton varieties and soy varieties that are marketed under the trade marks Roundup Ready® (tolerance toward glyphosate, e.g. maize, cotton, soy), Liberty Link® (tolerance toward phosphinotricin, e.g. rape), IMI® (tolerance toward imidazolinones) and STS® (tolerance toward sulphonyl ureas, e.g. maize). Also mentioned as herbicidf resistant (conventionally bred for herbicide tolerance) plants are those varieties marketed under| the name Clearfield® (e.g. maize). Naturally these statements also apply to plant varieties developed or marketed in the future with these genetic properties ("traits") or those developed in the future
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 belt, 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, whidh are specific for application in the transgenic crop in question, for example an altered or specifically widened 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 I for controlling 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/pr surface active agents [i.e. diluents or carriers and/or surface active agents of the type -5 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, or plant nematodes or mites. The compositions may be of any type known in the art suitable for application to the desired 10 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, 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, ikewise form a part of this invention.
The compounds of the invention, in their commercially available formulations and in the use forms prepared frojm 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, carboxylic esters, formamidi-nes, tin compounds and materials produced by microorganisms.
Preferred components in mixtures are:
Fungicides: Nucleic acidj synthesis inhibitors
benalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazol, metalaxyl, metalaxyl-M, ofurace, oxadixyl, oxolinic acid
Inhibitors ofjmitosis and cell division
benomyl, carbendazim, diethofencarb, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, zoxamis

Inhibitor of respiratory complex I
diflumetorim Inhibitors of respiratory complex n
bos4alid, carboxin, fenfuram, flutolanil, furametpyr, mepronil, oxycarboxin, penthiopyrad, thifliuzamide
Inhibitor of respiratory complex HI
azojxystrobin, cyazofamide, dimoxystrobin, enestrobin, famoxadone, fenamidone, fluox-astrobin, kresoxiramethyl, metominostrobin, orysastrobin, pyraclostrobin, picoxystrobin
Decouplers
dincdcap, fluazinam Inhibitors of ATP production
fentin acetate, fentin chloride, fentin hydroxide, silthiofam Inhibitor of 4mino acid and protein biosynthesis
andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, me-panipyrim, pyrimethanil
Inhibitors of signal transduction
fenpiclonil, fludioxonil, quinoxyfen Inhibitors of fat and membrane synthesis
chlozolinate, iprodione, procymidone, vinclozolin
ampjropylfos, potassium ampropylfos, edifenphos, iprobenfos (IBP), isoprothiolane, pyrazo-phos
tolc|ofos-methyl, biphenyl
iodojcarb, propamocarb, propamocarb hydrochloride

Inhibitors of ergosterol biosynthesis fenhexamide,
azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, dini-conazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusi-lazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazole, penconazole, propiconazole, prothioconazole, sicnjeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, unicona-zole, voriconazole, imazalil, imazalil sulphate, oxpoconazole, fenarimol, flurprimidol, nuari-mol, pyrifenox, triforin, peftirazoate, prochloraz, triflumizole, viniconazole,
aldlmorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, spirox-amine
naftifin, pyributicarb, terbinafin Inhibitors c(f cell wall synthesis
benthiavalicarb, bialaphos, dimethomorph, flumorph, iprovalicarb, polyoxins, polyoxorim, valldamycin A
Inhibitors oF melanin biosynthesis
capropamide, diclocymet, fenoxanil, phtalide, pyroquilon, tricyclazole Resistence induction
acij>enzolar-S-methyl, probenazole, tiadinil Multisite
captafol, captan, chlorothalonil, copper salts: copper hydroxide, copper riaphthenate, copper oxychloride, copper sulphate, copper oxide, oxine-copper and Bordeaux mixture, dichloflua-nid dithianon, dodin, dodin freie base, ferbam, fluorofolpet, guazatin, guazatin acetate, imi-no4tadin, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, propineb, sulphur and sulphur preparations containing calcium poly-sulphide, thiram, tolylfluanid, zineb, ziram
Unknown rmechanism

amjbroradol, benthiazole, bethoxazin, capsimycin, carvone, quinoline methionate, chloropic-
rin,| cufraneb, cyflufenamide, cymoxanil, dazomet, debacarb, diclomezine, dichlorophen, di-
clofan, difenzoquat, difenzoquat methyl sulphate, diphenylamine, ethaboxam, ferimzone, flu-
metover, flusulfamide, fluopicolide, fluoroimide, hexachlorobenzene, 8-hydroxyquinoline
sulphate, iramamycin, methasulphocarb, metrafenone, methyl isothiocyanate, mildiomycin,
nat|mycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb, oxy-
fenjhiin, pentachlorophenol and salts, 2-phenylphenol and salts, piperalin, propanosin -
sodjkim, proquinazid, pyrrohiitrin, qiiintozen, tecloftalam, tecnazen, triazoxido, trichlamide,
zar|lamide and 2J3,5)6-tetrachloro-4-(methylsulphonyl)pyridine, N-(4-chloro-2-nitrophenyl)-
N-^thyl4-methylbenzenesulphonamide, 2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide,
2-c|iloro-N-(2,3-dihydro-l,lJ3-trimethyl-lH-inden-4-yl)-3-pyridine carboxamide, 3-[5-(4-
chlorophenyl)-2,3-dimethylisoxazolidin-3-y l]pyridine, cis-1 -(4-chloropheny I)-2-( 1H-1,2,4-
triajtol-l-yl)cycloheptanol, 2,4-dihydro-5-methoxy-2-methyl-4-[[[tl-[3-(trifluoromethyl)-
phenyl]ethy!iden]amino]oxy]methyl]phenyl]-3H-l,23-triazol-3-one (185336-79-2), methyl 1-
(2,3-dihydro-2,2-dimetiiyl-lH-inden-l-yl)-lH-imidazole-5-carboxylate, 3,4,5-trichloro-2,6-
pyridine dicarbonitriel, methyl 2-[[[cyclopropyl[(4-methoxyphenyl) imino]methyl]thio
]methyl]-.alpha.-(methoxymethylen)-benzacetate, 4-chloro-alpha-propinyloxy-N-[2-[3-
methoxy-4-(2-propkiyloxy)phenyl]ethyl]-benzacetamide, (2S)-N-[2-[4-[[3-(4-chlorQphenyl)-
2-pjropinyl]oxy]-3-methoxyphenyl]ethyl]- 3-methyl-2-[(methylsulphonyl)amino]-butanamide,
5-chloro-7-(4-methylpiperidin-l-yl)-6-(2,4,6-trifluorophenyl)[l,2,4]triazoIo[l,5-a]pyrimidine,
5-chloro-6-(2,4)6-trifluorophenyl-N-[(lR)-l,2,2-trimefliylpropyl][l,2,4]triazolo[l,5-a]pyrimi-
dine-7-amine, 5-chloro-N-[(l R)-l ,2'dimethylpropyl]-6-(2,4,6-trifhiorophenyl) [1,2,4]triazolo
[l,5-a]pyrimidine-7-amine, N-[l-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronico-
tinamide, N-(5-bromo-3-chloropyridin-2-yl)methyl-2,4-dichloronicx3tinamide, 2-butoxy-6-
iodo-S-propylbenzopyranon-4--one, N- {(Z)-[(oyolopropylmethoxy) imino][6-(difluoro-
methoxy)-2,3-difluoraphenyl]methyl}-2-benzacetamide> N-(3-ethyl-3,5,5-trimethyl-
cyclohexyl)-3-fonnylamino-2-hydroxybenzamide, 2-[[[[l-[3(lfluoro-2-phenylethyl)
ooxy]phenyl ethylidene]amino]oxy]methyl]-alpha-(methoxyimino)-N-methyl-alphaE-benzace-tamide, N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide) N-(3',4'-dichloTO-5-fluorobiphenyl-2-yl)-3-(difluoromethyl)-l-methyl-lH-pyrazole-4-carbox-amide, N-(6-Methoxy-3-pyridinyl)-cyclopropane carboxamide, l-[(4-methoxy-phenoxy)methyl]-2,2-dimethylpropyl-lH-imidazole-l- carboxylic acid, 0-[l-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl]-lH-imidazole- 1- carbothioic acid, 2-(2-{[6-(3-chlor-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide

Bactericidos:
bronopol, djtehlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinon, fu-ran carboxylic acid, oxytetracyclin, probenazol, streptomycin, tecloftalam, copper sulphate and other copper preparations.
Insecticide / Acaricide / Nematkide:
Acetylcholinesterase (AChE) inhibitors
carbamates,
for (example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfura-carb), bufencarb, butacarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosul-fan cloethocarb, dimetilan, ethiofeucarb, fenobucarb, fenothiocarb, formetanate, furathio-carb, isoprocarb, metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate
organophosphates,
for example acephate, azamethiphos, azinphos (-methyl, -ethyl), aromophos-ethyl, arom-fenvinfos (-methyl), autathiofos, cadusafos, carbophenothion, chloremoxyfos, chlorfenvin-phos, chlormephos, chlorpyrifos (-methyl/-ethyl), coumaphos, cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphone, dialifos, diazinone, di-chlofenthione, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, dioxa-benzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, feni-trothion, fensulfothion, fenthion, flupyrazofos, fonofos, formothion, fosmethilan, fps-thijazate, heptenophos, iodofenphos, iprobenfos, isazofos, isofenphos, isopropyl O-salicylate, isoxathion, malathion, mecarbam, methacrifos, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion (-methyl/ -ethyl), phenthoate, phorate, phosalone, phosmet, phosphamidone, phosphocarb, Phoxim, pirimiphos (-methyl/-ethyl), profenofos, propaphos, propetamphos, prothiofos, prothoate, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, te-bupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon, vami-dothion
Sodium channel modulators / voltage-dependent sodium channel blockers
pyrethroids,
for example acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioal-

lethrin, bioallethrin-S-cyc!opentyl-isomer, bioethanomethrin, biopermethrin, bioresme-thrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocythrin, cyclo-prothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta), cyphenothrin, deltf|methrin, empenthrin (IR-isomer), esfenvalerate, etofenprox, fenfluthrin, fen-propjathrin, fenpyrithrin, fenvalerate, flubrocythrinate, flucythrinate, flufenprox, flumethrin, fluvalinate, fiibfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, pennethrin (cis-, trans-), phenothrin (IR-trans isomer), prallethrin, proflu-thrirj, protrifenbute, pyresmethrin, resmethrin, RU 15525, silafluofen, tau-fluvalinate, teflu-thrir, terallethrin, tetramethrin (-1R- isomer), tralomethrin, transfluthrin, ZXI 8901, pyre-thrins (pyrethrum)
DDt
oxadiazines,
for example indoxacarb
Acetylcholine receptor agonists/antagonists
chloronicotinyls,
for (example acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine,
thiacloprid, thiamethoxam
nicotine, bensultap, cartap Acetylcholihe receptor modulators
Spihosynes,
for example spinosad
GABA controlled chloride channel antagonists
Organochlorinee,
for example camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, Hndane,
mefhoxychlor
Fiproles,
for example acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole
Chloride channel activators

Mectins,
for example avermectin, emamectin, emamectin benzoate, ivermectin, milbemycin
Juvenile hormone mimetics,
for example diofenolan, epofenonane, fenoxycarb, hydroprene, kinoprene, methoprene, pyriproxifen, triprene
Ecdysone agonists/disruptors
diacylhydrazines,
for example chromafenozide, halofenozide, methoxyfenozide, tebufenozide
Inhibitors of chitin biosynthesis
Benzoylureas,
for; example bistrifluron, chlofluazuron, diflubenzuron, fluazuron, flucycloxuron, fluftnoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, te-flubjenzuron, triflumuron
buprofezin cyromazine
Inhibitors of oxidative phosphorylation, ATP disrupters diafenthiuron
org|notin compounds,
for example azocyclotin, cyhexatin, fenbutatin-oxide
Decouplers iof oxidative phosphorylation by interruption of H-proton gradients
pyrrole,
for example chlorfenapyr
dinjtrophenols,
for (example binapaoyrl, dinobuton, dinocap, DNOC
Site I electron transport inhibitors

for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad
hydramethynon
dicofol Site II electron transport inhibitors
rotenones Site III electron transport inhibitors
acecquinocyl, fluacrypyrim microbial disruptors of insect intestinal membrane
Bacillus thuringiensis strains Inhibitors of) fat synthesis
tetrqonic acids,
for example spirodiclofen, spiromesifen
tetramic acids,
for (example spirotetramat (CAS-Reg.-No.: 203313-25-1) and 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-l-azaspiro[4.5]dec-3-en-4-yl ethyl carbonate (alias: carbonic acid, 3-(2,5-dimthylphenyl)-8-methoxy-2-oxo-l-azaspiro[4.5]dec-3-en-4-yl ethyl ester, CAS-Reg.-No.i 382608-10-8)
carboxamides, for Example flonicamid octojpaminergic agonists, for example amitraz Inhibitor of magnesium-stimulated ATPase,

profargite
benzoic acid dicarboxamides,
for example flubendiamide
Nereistoxin analogous,
for example thiocyclam hydrogen oxalate, thiosultap-sodium Agonists of the ryanodin receptor,
benfcoic acid dicarboxamides,
for example flubendiamide BiologicalsJ hormones or pheromones
azadirachtin, Bacillus spec., Beauveria spec., codlemone, Metarrhizium spec., Paecilomy-ces Spec., thuringiensin, Verticillium spec.
Active compounds with unknown or non-specific mode of action
fun|igants, for example aluminium phosphide, methyl bromide, sulphuryl fluoride
feeding inhibitors, for example cryolite, flonicamid, pymetrozine
mite growth inhibitors, for example clofentezine, etoxazole, hexythiazox
amidoflumet, benclothiaz, benzoximate, bifenazate, bromopropylate, buprofezin, quinome-thionate, chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, cyflume-tofqn, dicyolanil, fenoxacrim, fentrifanil, flubenzimine, flufenerim, flutenzin, gossyplure, hydramethylnone, japonilure, metoxadiazone, petroleum, piperonyl butoxide, potassium oleate, pyridalyl, sulfluramid, tetradifon, tetrasul, triarathene,verbutin
A mixture with other known active compounds such as herbicides, fertilisers, growth regulators, safeners, semiochemicals or also with agents for improving plant properties is also possible.
The active compounds of the invention can also be present in their normal commercial formulations when used as insecticides as well as in the application forms prepared from these

formulations in admixture with synergists. Synergists are compounds through which the activity of the active compound can be increased without the added synergist itself having to be active.
The active Compounds of the invention can also be present in their normal commercial formulations when used as insecticides as well as in the application forms prepared from these formulations in admixture with inhibitors that reduce degradation of the active compound after use in the environment of the plants, on the surface of the plants or in plant tissues.
The abovementioned components for combinations are known active substances, many of which are described in Ch.R Worthing, S.B. Walker, The Pesticide Manual, 12th Edition, British Crop Protection Council, Farnham 2000,
The effective use doses of the compounds employed in the invention can vary within wide limits, particularlyjdepending on the nature of the pest to be eliminated or degree of infestation, for example, of crops with these pests. In general, the compositions according to the invention usually contain about Cj.05 to about 95% (by weight) of one or more active ingredients according to the invention, about to about 95% of one or more solid or liquid carriers and, optionally, about 0.1 to about 50% of one! or more other compatible components, such as surface-active agents or the like.
hi the present account, the term "carrier" denotes an organic or inorganic ingredient, natural 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, particularly to the treated plant).
The carrier may be a solid, for example, clays, natural or synthetic silicates, silica, resins, waxes, solid fertilisers (for example ammonium salts), ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite, bentonite or diatomaoeous earth, or ground synthetic minerals, such as silica, alumina, or silicates especially aluminium or magnesium silicates. As solid carriers for granules the following are suitable: crushed or fractionated natural rocks such as calcite, marble, pumice, sepiolite 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; kiesjelguhr, tricalcium phosphate, powdered cork, or absorbent carbon black; water soluble polymers, tesins, waxes; or solid fertilizers. Such solid compositions may, if desired, contain one or more compatible wetting, dispersing, emulsifying or colouring agents which, when solid, may also serve is a diluent.

Suitable as splid carriers are:
for example ammonium salts and natural mineral powders such a kaolin, clays, talc, chalk, quartz attapulgite, montmorillonite or diatomaceous earth, and synthetic mineral powders such as highly dispersed sillca, aluminium oxide and silicates, suitable as carriers for granulates are: for example crushed and (fractionated natural minerals such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granulates of inorganic and organic flours as well as granulates from organic materials such 4s paper, sawdust, coconut shells, maize ears and tobacco stalks; suitable as emulsifiers and foaming agents are; for example non-ionogenic and anionic emulsifiers such as polyoxyethyl-ene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates and protein hydrolysates; suitable as dispersant are non-ionic; and/or ionic materials, for example from the class of alcohol-POE and/or POP ethers, acid- and/or POP or POE esters, alkyl-aryl- and/or POP or POE ethers, fat- and/or POP or POE adducts, POE- and/or POP-polyol derivates, POE- and/or POP-sorbitan or sugar adducts, alkyl or aryl sulphates, sulphonates and phosphates or the respective PO ether adducts. In addition suitable oligo- or pojymers, for example starting from vinylic monomers, of acrylic acid, from EO and/or PO alone on in combination with, for example (poly)alcohols or (poly)amines. In addition lignin and its sulp|onic acid derivatives, simple and modified celluloses, aromatic and/or aliphatic sul-phonic acids as well as their adducts with formaldehyde can be used .
Deposit builders such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate as w£ll as natural phospholipids such a cephalins and lecithins and synthetic phospholipids.
The carrier may also be liquid, for example: water; alcohols, particularly butanol or glycol, as well as their ethers or esters, particularly methylglycol acetate; ketones, particularly acetone, cyclohexa-none, methylethyl ketone, methylisobutylketone, or isophorone; petroleum fractions such as paraf-finic or aromatic hydrocarbons, particularly xylenes or alkyl naphthalenes; mineral or vegetable oils; aliphatjc chlorinated hydrocarbons, particularly trichloroethane or methylene chloride; aromatic chlorinated hydrocarbons, particularly chlorobenzenes; water-soluble or strongly polar solvents such 4s dimethylformarnide, 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 phenolsul-phonic or naphthalenesulphonic acids, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty esters or fatty amines, substituted phenols (particularly alkylphenols or arylphe-nols), 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 fulphate, sulphonate or phosphate functional derivatives of the above compounds. The presence of lat least one surface-active agent is generally essential when the active ingredient and/or the inert carrier are only slightly water soluble or are not water soluble and the carrier agent of the composition 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 polymers in the form of powders, granules or (lattices, such as arabic gum, polyvinyl alcohol or polyvinyl acetate, natural phospholip-ids, such as! cephalitis or lecithins, or synthetic phospholipids can be used in the formulations. It is possible to bse 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 corhpositions, which are in various solid or liquid forms.
20 Solid 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 dis-persible 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%). Solid homogenous or
25 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 conjipositions, for example, include aqueous or non-aqueous solutions or suspensions (such 30 as emulsiflable concentrates, emulsions, flowables, dispersions, or solutions) or aerosols. Liquid 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 liquid or intended to form liquid compositions when applied, for example as aqueous sprays (including low and ultra-low volume) or as fogs or aerosols.
Liquid 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 whfch 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, about 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 water-in-oil or oil-in-water type and they may have a thick consistency.
The liquid compositions of this invention may, in addition to normal agricultural use applications be used for example to treat substrates or sites infested or liable 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 aqjieous dispersions or emulsions or spraying mixtures can be applied, 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 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 formulation 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, which 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 (j.l 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, water or an organic liquid in which the active ingredient is poorly soluble or insoluble Some organjc solids or inorganic salts may be dissolved in the carrier to help prevent settling or as antifreezes fbr 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 solid carrier, from about 0 to ahout 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 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 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 wettability and the suspendabilrty 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 application to plant foliage.
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 little 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 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% 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 plant nematodes, synergists, trace elements or stabilizers). The actual compositions employed and their rate of application will be selected to achieve the desired effect(s) by the fanner, livestock producer, medical or veterinary practitioner, pest control operator or other person skilled in the art.
Solid or liqjuid compositions for application topically to animals, timber, stored products or household 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 prally 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 feedstuff's 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 licks 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 from (about 0.0001% to about 15%, more especially from about 0.005% to about 2.0%, by weight, of onje 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 fanning 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 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 the following percentages are in weight percent), used in the composition EXAMPLES 2A - 2M exemplified below, are as follows:
Trade Narmt Chemical Description
Ethylan BCP Nonylphenol ethylene oxide condensate
Soprophor BSU Tristyrylphenol ethylene oxide condensate
i Arylan CA A 70% w/v solution of calcium dodecylbenzenesulfonate
Solvesso 130 Light C i o aromatic solvent
Arylan S Sodium dodecylbenzenesulfonate
Darvan NO2 Sodium lignosulphonate
Celite PF Synthetic magnesium silicate carrier
Sopropon T36 Sodium salts of polycarboxylic acids
Rhodigel 23 Polysaccharide xanthan gum
Bentone 3 8 Organic derivative of magnesium montmorillonite
Aerosil Microfme silicon dioxide
EXAMPLES 2A
Active ingredient 7%
EthylanBCP 10%
N-methylpyrrolidone 83%
A water soluble concentrate is prepared with the composition as follows:
To a solution of Ethylan BCP dissolved in a portion of N-methylpyrrolidone is added the active ingredient iwith heating and stirring until dissolved. The resulting solution is made up to volume with the remainder of the solvent.
EXAMPLE2B
An emulsifiable concentrate (EC) is prepared with the composition as follows:
Active ingredient 25%(max)
Soprophor BSU 10%
Arylan CA 5%
N-methylpyrrolidone 50%
Solvesso 150 10%
The first three components are dissolved in N-methylpyrrolidone and to this is then added the Solvesso 1 50 to give the final volume.
EXAMPLEJ2C
Active ingredient 40%
Arylan S 2%
DarvanNO2 5%
Celite PF 53%
A wettable pjowder (WP) is prepared with the composition as follows:
The ingredients are mixed and ground in a hammer-mill to a powder with a particle size of less than 50 microns.
EXAMPLE 2D
Active ingredient 40.00%
EthylanBCP 1.00%
SoproponT360. 0.20%
Ethylene glycol 5.00%
; Rhodigel230. 0.15%
Water . 53.65%
An aqueous-flowable formulation is prepared with the composition as follows:
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
1 Active ingredient 30.0%
EthylanBCP 10.0%
Bentone38 0.5%
; Solvesso 150 59.5%
An emulsifiable suspension concentrate is prepared with the composition as follows:
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%
The ingredients are mixed, micronized in a fluid-energy mill and then granulated in a rotating pel-
letizer 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 appplied to a locus of arthropod infestation, for example refuse dumps, stored products oil 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 livestock self treatment devices.
EXAMPLES 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 flies, 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 applied percutaneously as a pour-on application to domestic animals infested by arthropods or, after sterilization by filtration through a polytetrafluoroethylene membrane (0.22 micrometer bore size), by parenteral injection, at a rate of application of from 1.2 to 12 ml of solution per l00ikg of animal body weight.
EXAMPLE! 2J
Active ingredient 50%
EthylanBCP 5%
Aerosil 5%
Celite PF 40%
A wettable powder is prepared with the composition as follows:
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 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
Active ingredient Density agent Slow-release agent Binder
A slow release bolus composition is formed from granules containing the following components in varying p$rcentages(similar to those described for the previous compositions) depending upon need:
The intimately mixed ingredients are formed into granules which are compressed into a bolus with 20 a specific (gravity of 2 or more. This can be administered orally to ruminant domestic animals for retention fvithin 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 like can be prepared with compositions as follows:
Actite 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 eaitags for attachment to domestic animals to control pests by slow release.
EXAMPLE 2M
A water dispfersible granule is prepared with the composition as follows:
Active ingredient 85%(max)
Polyvinylpyrrolidone 5%
Attapulgite clay 6%
Socdium 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 procedure, using compounds of the invention, was conducted to determine the parasiticidal activity of compounds of the invention.
Biological Examples
METHOD 4: Screening method to test systemicity of compounds against Ctenocephalides felis (Cat flea)
A test container was filled with 10 adults 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 felis 20-22°C, 40-60 % relative humidity) and assessment performed at 24 and 48 hours after application. Compounds 1-02, 3-02, 4-08,4-14 gave at least 80% control of Gtenocephalides felis at a test concentration of 5ppm or less.
METHOD B: 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 withi a clip. The treated Rhipicephalus sanguineus were held in a climate chamber (2S°C, 90% RH) and the percentage efficacy assessed 24 hours after application in comparison with the untreated control.
Compound jnumbers 1-02 gave at least 70% contact control of Rhipicephalus sanguineus at a test concentration of 100 ppm.



WE CLAIM
1. A compound of formula I or a pesticidally acceptable salt thereof, wherein
(Formula Removed)
W is =CR8- or =C(NR9R10>,
R8 is halogen, alkyl or haloalkyl,
R9 and R10 are independently of one another hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl,
which groups R9 and R10 independently of one another are optionally substituted by one or more halpgen, C3-C7-cycloalkyl, aryl, heteroaryl, C1-C6-alkoxy and/orC1-C6-haloalkoxy,
R1 is cyafio, methyl, trifluoromethyl, -CS-NH2 or -C(=NRn)S(O)nR12, R" is hydrogen, alkyl or aryl, R12 is alkfyl or aryl,
which groups Rnand/or R12 are optionally substituted by one or more halogen, hydroxyl, oxo, nitro, cyano, amino, alkyl, alkoxy, alkylthio, cycloalkyl, aryl, heterocyclyl and/or aralkyl groups,
R2 is C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl or C2-C6-haloalkynyl,
R3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, ary], heterocyclyl, arallcyl or hetefocyclylalkyl, which group R3 is optionally substituted by one or more halogen, hy-droxyl, cyano, nitro, carboxy, carboxylic acid ester, oxo, alkylcarbonyl, haloalkylcarbonyl, cycloalfcylcarbonyl, alkylcycloalkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclylcar-bonyl, heterocyclylalkylcarbonyl, amino, alkyl, alkoxy, haloalkoxy, alkenyloxy, haloalkeny-loxy, ajlkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, cycloalkylthio, alkylcycloalkyl-thio, aeylthio, aralkylthio, heterocyclylthio, heterocyclyl-alkylthio, alkylsulphoxidyl, haloal-kylsulphoxidyl, cycloalkylsulphoxidyl, alkylcycloalkylsulphoxidyl, arylsulphoxidyl, aralkyl-sulpho^idyl, heterocyclylsulphoxidyl, heterocyclylalkylsulphoxidyl, alkylsulphonyl, haloal-kylsulpjhonyl, cycloalkylsulphonyl, alkylcycloalkyl-sulphonyl, arylsulphonyl, aralkylsul-phonylj heterocyclylsulphonyl, heterocyclylalkylsulphonyl, cycloalkyl, cycloalkyloxy, aryl, aryl substituted by one or more halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano, nitro, al-kylthioi, haloalkylthio, cycloalkylthio, alkylcycloalkylthio, arylthio, aralkylthio, heterocyclyl-thio, h(|terocyclylalkylthio, alkylsulphoxidyl, haloalkylsulphoxidyl, cycloalkylsulphoxidyl, a-ky Icycjoalkylsulphoxidyl, arylsulphoxidyl, aralkylsulphoxidyl, heterocyclylsulphoxidyl, het-erocycjylalkylsulphoxidyl,_alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alfcylcy-cloalkyilsulphonyl, arylsulphonyl, aralkylsulphonyl, heterocyclylsulphonyl, heterocyclylalkyl-sulphohyl, and/or amino groups, heterocyclyl, heterocyclyl substituted by one or more halo-gen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkylcy-cloalkyllthio, arylthio, aralkylthio, heterocyclylthio, heterocyclyl-alkylthio, alkylsulphoxidyl, haloalkylsulphoxidyl, cycloalkylsulphoxidyl, alkylcycloalkylsulphoxidyl, arylsulphoxidyl, aralkylsulphoxidyl, heterocyclylsulphoxidyl, heterocyclylalkylsulphoxidyl, alkylsulphonyl, haloallfylsulphonyl, cycloalkylsulphonyl, alkylcycloalkyl-sulphonyl, arylsulphonyl, aralkyl-sulphohyl, heterocyclylsulphonyl, heterocyclylalkylsulphonyl, hydroxy and/or oxo groups, aralkyl and/or heterocyclylalkyl group,
R4 and R5 are independently of one another hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, heterocyclyl, aralkyl or heterocyclylalkyl or R4 and R5 together with the attached C-atom form a four- to seven-membered saturated or unsaturated ring which optionally contains oxygen, sulfur and/or nitrogen atoms in the ring and/or which is fused to one or more saturated or unsaturated carbocyclic or heterocyclic ring, which groups R4 and/or R5 or which ring formed by R4 and R3 are optionally substituted by one or more halogen, hydroxyl, cyano, nitro, carboxy, carboxylic acid ester, oxo, alkylcarbonyl, haloalkylcarbonyl, cycloal-kylcarbonyl, alkylcycloalkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclylcarbonyl, heterocyclylalkylcarbonyl, amino, alkyl, alkoxy, cycloalkyloxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, cycloalkylthio, alkylcy-
cloalkylthio, arylthio, aralkylthio, heterocyclylthio, heterooyclyl-alkylthio, alkylsulphoxidyl, haloalkylsulphoxidyl, cycloalkylsulphoxidyl, alkylcycloalkylsulphoxidy!, arylsulphoxidyl, aralkylsulphoxidyl, heterocyclylsulphoxidyl, heterocyclylalkylsulphoxidyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcycloalkyl-sulphonyl, arylsulphonyl,_aralkyl-sulphoiiyl, heterocyclylsulphonyl, heterocyclylalkylsulphonyl, cycloalkyl, aryl, aryl substi-tuted by one or more halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, cyano, nitro, alkylthio, haloalkylthio, cycloalkylthio, alkylcycloalkylthio, arylthio, aralkylthio, heterocyclylthio, het-erocyclylalkylthio, alkylsulphoxidyl, haloalkylsulphoxidyl, cycloalkylsulphoxidyl, alkylcy-cloalkylsulphoxidyl, arylsulphoxidyl, aralkylsulphoxidyl, heterocyclylsulphoxidyl, heterocy-clylalkylsulphoxidyl, alkylsulphonyl, haloalkylsulphonyl, cycloalkylsulphonyl, alkylcycloal-kylsulphonyl, arylsulphonyl, aralkylsulphonyl, heterocyclylsulphonyl, heterocyclylalkylsul-phonyl and/or amino groups, heterocyclyl, heterocyclyl substituted by one or more halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, cycloalkylthio, alkylcycloalkyl-thio, arylthio, aralkylthio, heterocyclylthio, heterocyclyl-alkylthio, alkylsulphoxidyl, haloal-kylsulphoxidyl, cycloalkylsulphoxidyl, alkylcycloalkylsulphoxidyl, arylsulphoxidyl, aralkyl-sulphoxidyl, heterocyclylsulphoxidyl, heterocyclylalkylsulphoxidyl, alkylsulphonyl, haloal-kylsulflhonyl, cycloalkylsulphonyl, alkylcycloalkyl-sulphonyl, arylsulphonyl, aralkylsul-phonyl| heterocyclylsulphonyl, heterocyclylalkylsulphonyl, hydroxy and/or oxo groups, aral-kyl and/or heterocyclylalkyl group,
R6 is haloalkyl, haloalkoxy, halogen or -SF5, R7 is halogen, alkyl or -NR17R18,
R17 and R18 are independently of one another hydrogen,C1-C6-alkyI, C2-C6-alkenyl or C2-C6-alkynyl, which groups R17 and/or R18 are optionally substituted by one or more halogen, C3-C7-tycloalkyl, aryl, heteroaryl, C1-C6-alkoxy or C1-C6-haloalkoxy, and
n is 0,1, or 2.
2. A compound as claimed in claim I, wherein W is =C(R8)- and R8 is halogen or haloalkyl or a
pesticidally acceptable salt thereof.
3. A compound as claimed in claim 2, wherein R8 is chlorine or fluorine or a pesticidally accept-
able salt thereof.
4. A compound as claimed in claim 1, wherein R1 is cyano, methyl, trifluoromethyl or -CS-NH2
or a pegticidally acceptable salt thereof.
5. A compound as claimed in claim 4, wherein R1 is -CN or -CS-NH2 or a pesticidally accept-
able salt thereof.
6. A compound as claimed in claim 1, wherein R2 is (C1-C3-haloalkyl, preferably chlorine and -
CF3 or n pesticidally acceptable salt thereof.
7. A compound as claimed in claim 1, wherein R3 is hydrogen, alkyl, alkenyl, alkynyl, haloalkyl,
haloalkpnyl or haloalkynyl or a pesticidally acceptable salt thereof.
8. A compound as claimed in claim 1 or a pesticidally acceptable salt thereof, wherein R3 is hy
drogen or (C1-C6)-alkyl unsubstituted or substituted by one or more radicals selected from the
group donsisting of halogen, C1-C6-alkoxy,(C1-C6)-haloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-
haloalkenyloxy, (C3-C6)-alkynyloxy, (C3-C6)-haloalkynyloxy, (C3-C7)-cycloalkyl, S(O)pR19,
CN, N02, OH, R20, R21, COR19, NR22R23, OR19, COOH and CO2R19, wherein R19, R20, R21, R22,
R23 and; p are as defined in claim 14.
9. A compound as claimed in claim 8, wherein R3 is hydrogen or (C1-C3)-alkyl or a pesticidally
acceptable salt thereof.
10. A compound as claimed in claim 1, wherein R4 and R5 independently of one another are al-
kenyl, alkynyl, haloalkenyl or haloalkynyl or a pesticidally acceptable salt thereof.
11. A compound as claimed in claim 1, wherein R4 and R5 are independently of one another (C2-
C6)-alkjenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C7)-cycloalkyl,
(C3-C7}-cycloalkyl(C1-C,4)-alkyl, or are independently of one another phenyl, heterocyclyl
which fere unsubstituted or substituted by one or more radicals selected from the group consist
ing of halogen, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C1-C6)-alkenyloxy, (C3-C6)-
haloalkenyloxy, (C3-C6)-alkynyloxy, (C3-C6)-haloalkynyloxy, (C3-C7)-cycloalkyl, (C3-C7)-
cycloalkyloxy, S(O)PR19, CN, NO2, OH, R20, R21, COR19, NR22R23, OR19, COOH and CO2R19,
or are each independently (C1-C6)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen,(C1-C6)-alkoxy,(C1-C6)-haloalkoxy, (C3-C6)-alkenyjloxy, (C3-C6)-haloalkenyloxy, (C3-C6)-alkynyloxy, (C3-C6)-haloalkynyloxy, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkyloxy, S(O)PR19, CN, NO2, OH, R20, R21, COR19, NR22R23, COOH and CO2R19, or
R4 and, R5 together with the attached C atom can form a four- to seven-membered saturated ring or a five- to seven-membered unsaturated ring, which optionally contains one or more hetero atoms in the ring which are selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6) -alk!yl,(C1-C6)-haloalkyl and oxo, and when present any additional ring N atom is unsubstituted or substituted by a (C1-C6)-alkyl, CO-(C1-C6)-aIkyI or CH2R20 radical; or which is condensed" with a benzene ring, wherein R19, R20, R21, R22, R23 and p are as defined in claim 14 or a pestioidally acceptable salt thereof.
12. A compound as claimed in claim 1, wherein R6 is halogen, (C1-C3)-alkyl, (C1-C3)-haloalkyl or
-SF5, preferably chlorine or -CF3 or a pesticidally acceptable salt thereof.
13. A compound as claimed in claim 1, wherein R7 and R8 are halogen or R7 is -NR17R18 or a pes
ticidally acceptable salt thereof.
14. A compound as claimed in claim 1, wherein
R1 is -CN
R7 is hllogen, -CH3 or -NR17R18,
R6 is (C1-C3)-haloalkyl,(C1-C3)-haloalkoxy or -SF5)
R3 is hydrogen, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-haloalkynyl, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkyl-(C1-C6)-alkyl, or (C1-C6)-alkyl unsubstituted or substi-tuted b^ one or more radicals selected from the group consisting of halogen, (C1-C6)-alkoxy, (C3-C6)-alkenyloxy, (C3-C7)-haloalkenyloxy, (C3-C6)-alkynyloxy, , (C3-C7)-cycloalkyl, (C3-C7)-cycloalkyloxy, -S(O)PR19, -CN, -NO2, -OH, -R20, R21, -COR19, -NR22R23, -OR19, -COOH and -CO2R19, R2 is (C1-C6)-alkyl, (C1-C6)-haloalkjyl, (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl or (C2-C6)-haloalkynyl,
R4 and R5 are each independently (C2-C6)-alkenyl, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-halbalkynyl, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkyl-(C1-C4)-alkyI, or are each independently phenyl, heterocyclyl which are unsubstituted or substituted by one or more radicals se-lected ifrom the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C3-C6)-alkenyjoxy, (C3-C6)-haloalkenyloxy, (C3-C6)-alkynyloxy, (C3-C6)-haloalkynyloxy, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkyloxy) S(O)PR19, CN, NO2, OH, R20, R21, COR19, NR22R23, OR19 , COOH, and CO2R19, or are each independently(C1-C6)-alkyl unsubstituted or substituted by
one or more radicals selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-haloalkenyloxy, (C3-C6)-alkynyloxy, (C3-C6)-haloalkjnyloxy, (CrC^-cycloalkyl, (C3-C7)-cycIoalkyloxy, S(0)pR19, CN, NO2, OH, R20 R21, COR19, NR22R23, COOH and CO2R19, or
R4 and R5 together with the attached C atom can form a four- to seven-membered saturated ring or a five- to seven-membered unsaturated ring, which optionally contains one or more hetero atoms in the ring which are selected from O, S and N, the ring being unsubstituted or substituted by one or more radicals selected from the group consisting of halogen,(C1-C6) -alkyl,(C1-C6)-haloalkyl and oxo, and when present any additional ring N atom is unsubstituted on substituted by a (C1-C6)-alkyl, CO-(C1-C6)-alkyl or CH2R20 radical; or which is condensed ivith a benzene ring,
R19 is (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C7)-cycloalkyl, (C1-C4)-alkyl-(C3-C7)-cycloalkyl, -(CH2),R20or-(CH2)(1R21,
R20 is phenyl unsubstituted or substituted by one or more radicals selected from the group consisting R21 is heeterocyclyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, S(O)PR19, OH and oxo,
R22 an4 R23 are each independently hydrogen, (C1-C6)alkyl, (C2-C6)-alkenyl or (C2-C6)-alkynylj which last three mentioned groups are unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C3-C7)-cycloalkyl, R20, R21, (C1-C6)-alkoxy,; (C1-C6)-haloalkoxy, and
n and psand q are each independently zero, one or two. 15. A compound as claimed in claim 1, wherein: R1 is CN, R7andR8areCl, R6 is CF3,
R3 is hydrogen or (Ci-C3)-alkyl, and R2 is CP3.
16. A compound as claimed in claim 1, wherein:
R4 and*5 are each independently (C1-C6)-alkenyI, (C2-C6)-haloalkenyl, (C2-C6)-alkynyl, (C2-C6)-halbalkynyl, (C3-C7)cycloalkyl, (C3-C7)-cycloalkyl-(C1-C4)-alkyl,or are each independently R20, R21, unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-aIkoxy, (Ci-C6)-haloalkoxy, (C3-Cs)-alkenyloxy, (C3-C6)-haloalkenyloxy, (C3-C6)-alkynyloxy, (C3-C6)-haIoalkynyloxy, (C3-C7)-cycloalkyl, S(O)PR19, CN, N02, OH, R20, R21, COR19, NR22R23, OR19, COOH and CO2R19,or are each independently (Ci-C6)-alkyl unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C1-C6)-alkoxy, (C1-C6)-haloalkoxy, (C3-C6)-alkenyloxy, (C3-C6)-haloalkjenyloxy, (C3-C6)-alkynyloxy, (C3-C6)-haloalkynyloxy, (C3-C7)-cycloalkyl, S(O)PR19, CN, NO2, OH, R20, R21, COR19, NR22R23, OR19, COOH and CO2R19,
R4 and R5 together with the attached C atom can form a four- to seven-membered saturated ring or a five- to seven-membered unsaturated ring, which optionally contains one or more additional hetero atoms in the ring which are selected from O, S and N, the ring being unsubstituted or substituted by one or more, radicals selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl and oxo, and when present any additional ring N atom is un-substitftted or substituted by a (C1-C6)-alkyl, CO- (C1-C6)-alkyl or CH2R20 radical; or which is condensed with a benzene ring, wherein R19, R20, R21, R22, R23 and p are as defined in claim 14.
17. A process for preparation of a compound of formula I as claimed in claim 1, wherein R1 is
cyano, halogen, alkyl or haloalkyl and R2, R3, R*, R5, R6, R7, W and n are as defined in claim
1, comprising reacting a compound of formula II:
(Formula Removed)

wherein R1 is cyano, halogen, alkyl or haloalkyl and R2, R3, R6, R7, W and n are as defined in claim 1 with an oxime of formula III, wherein R4 and R5 are as defined in claim 1
R4R5C=N-OH (HI)
and phosgene or a phosgene precursor in the presence of a base.
18. A process for preparation of a compound of formula I as claimed in claim 1, wherein R1 is -
CSNH2, and R2, R3, R4, R5, R6, R7, W and n are as defined in claim 1, comprising reacting a
compound of formula I, wherein R1 is CN, with alkali or alkaline earth metal hydro sulphides
in at inart solvent at a temperature from -35°C to 50°C.
19. A procass for preparation of a compound of formula I as claimed in claim 1, wherein R1, R2,
R3, R4, R5, R6, R7 and W are as defined in claim 1, and n is 1 or 2 comprising oxidation of a
compound of formula I, in which n is 0 or 1.
20. A pesticidal composition comprising as an active ingredient at least one compound of formula
I according to claim 1 or a pesticidial acceptable salt thereof.
21. A pesticidal composition according to claim 20 comprising diluents and/or carriers and/or
surface active agents which a compatible with said active ingredient.
22. A pesticidal composition according to claim 20 which is a veterinary medicament and which is
adapted! for oral administration.
23. Use of ft compound of formula I according to claim 1 or a pesticidial acceptable salt thereof
for the control of the number of arthropods, especially insects or mites, or of plant nematodes.
24. Use of 41 compound of formula I according to claim 1 or a pesticidial salt thereof for the prepa
ration off a pest control agent, preferably of an insecticide and/or miticide.
25. Use of acompound of formula I according to claim 1 or of a pesticidial acceptable salt thereof
for the protection of transgenic plants against pests.
26. Use ofa compound of formula I according to claim 1 or of a pesticidial acceptable salt thereof
in the treatment of vertebrates, preferable of domestic animals, for the control of arthropods
and/or helminths.
27. A method for controlling pests at a locus which comprises applying thereto an effective amount of a compound of formula I or a pesticidally acceptable salt thereof as claimed in any of claims 1 to 16.

Documents:

4537-delnp-2007-abstract.pdf

4537-delnp-2007-Assignment-(08-10-2014).pdf

4537-delnp-2007-assignment.pdf

4537-delnp-2007-Claims-(06-03-2014).pdf

4537-delnp-2007-Claims-(08-10-2014).pdf

4537-delnp-2007-claims.pdf

4537-delnp-2007-Correspondence Others-(01-05-2013).pdf

4537-delnp-2007-Correspondence Others-(08-10-2014).pdf

4537-delnp-2007-Correspondence Others-(15-09-2014).pdf

4537-delnp-2007-correspondence others.pdf

4537-delnp-2007-Correspondence-Others-(06-03-2014).pdf

4537-delnp-2007-description (complete).pdf

4537-delnp-2007-form-1.pdf

4537-delnp-2007-Form-13-(06-03-2014).pdf

4537-delnp-2007-Form-13-(08-10-2014).pdf

4537-delnp-2007-form-2.pdf

4537-delnp-2007-Form-3-(01-05-2013).pdf

4537-delnp-2007-form-3.pdf

4537-delnp-2007-Form-5-(06-03-2014).pdf

4537-delnp-2007-form-5.pdf

4537-delnp-2007-pct-304.pdf

4537-delnp-2007-pct-306.pdf

4537-delnp-2007-Petition-137-(06-03-2014).pdf

abstract.jpg


Patent Number 265872
Indian Patent Application Number 4537/DELNP/2007
PG Journal Number 13/2015
Publication Date 27-Mar-2015
Grant Date 20-Mar-2015
Date of Filing 13-Jun-2007
Name of Patentee MERIAL LIMITED
Applicant Address 33239 SATELLITE BLVD DULUTH, GA 30096-4640 USA
Inventors:
# Inventor's Name Inventor's Address
1 SCHNATTERER,STEFAN SCHILLERRING 10 65795 HATTERSHEIM GERMANY
2 MAIER,MICHAEL NEU ZEILSHEIM 78 65931 FRANKFURT GERMANY
3 LOCHHAAS, FRIEDERIKE AM FLURRASEN 33 36341 LAUTERBACH GERMANY
4 KNAUF, WERNER FLICHTMAYER STR. 76646 BRUCHSAL GERMANY
5 SEEGER, KARL SCHWALBENWEG 9 65719 HOFHEIM GERMANY
PCT International Classification Number C07D 401/04
PCT International Application Number PCT/EP2006/000355
PCT International Filing date 2006-01-17
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 05001182.4 2005-01-21 EUROPEAN UNION