WO2002006243A1 - Tetrahydropyrimidines tenant lieu de pesticides - Google Patents

Tetrahydropyrimidines tenant lieu de pesticides Download PDF

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Publication number
WO2002006243A1
WO2002006243A1 PCT/EP2001/008254 EP0108254W WO0206243A1 WO 2002006243 A1 WO2002006243 A1 WO 2002006243A1 EP 0108254 W EP0108254 W EP 0108254W WO 0206243 A1 WO0206243 A1 WO 0206243A1
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Prior art keywords
crc
alkyl
spp
substituted
unsubstituted
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PCT/EP2001/008254
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English (en)
Inventor
Martin Eberle
André Jeanguenat
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Syngenta Participations Ag
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Priority to AU2001289673A priority Critical patent/AU2001289673A1/en
Publication of WO2002006243A1 publication Critical patent/WO2002006243A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member

Definitions

  • the invention relates to a compound of formula
  • ⁇ is unsubstituted or mono- to penta-substituted aryl, the substituents being selected from the group consisting of
  • R 2 is H, OH, halogen, CN, NO 2 , d-C ⁇ alkyl, C C 6 alkoxy, CrC 6 alkoxy-CrC 6 alkyl,
  • R is CrC 4 alkyl or C 3 -C 6 cycloalkyl;
  • R 5 each independently of the other is H, CrC 6 alkyl, C 3 -C 8 cycloalkyl, CrCehaloalkyl,
  • R 6 is H, CrC 6 alkyl, C 3 -C 8 cycloalkyl, CrCehaloalkyl, CrC 6 alkoxy, -N(R 7 ) 2 or CrC 6 alkoxy-
  • R 7 each independently of the other is H, CrC 6 alkyl, C 3 -C 8 cycloalkyl, CrCehaloalkyl or aryl-CrC 6 alkyl;
  • X 2 and X 3 are each independently of the other H or R 8 ;
  • R 8 is halogen, CN, NO 2> CrC 6 alkyl, d-Cehaloalkyl, CrC 6 alkoxy, C 3 -C 8 cycloalkoxy, C C 6 - haloalkoxy, C 3 -C 8 halocycloalkoxy, CrC 6 alkylthio, C 3 -C 8 cycloalkylthio, CrC 6 halo- alkylthio or C 3 -C 8 halocycloalkylthio;
  • Y is O or S;
  • n is 0, 1 or 2;
  • W is a single bond, O, S, NH or N(C C 4 alkyl);
  • R 9 is hydrogen, CrC 6 alkyl, CrCehaloalkyl, C ⁇ -C 6 cycloalkyl, CrC 6 halocycloalkyl, phenyl or phenyl-CrC 6 alkyl;
  • the literature proposes certain tetrahydropyrimidine derivatives in pesticidal compositions.
  • the biological properties of those known compounds are not, however, fully satisfactory in the area of pest control and there is accordingly a need to provide further compounds having pesticidal properties, especially for the control of insects, that problem being solved according to the invention by the provision of the present compounds of formula (I).
  • Some of the compounds of formula (I) may also be present in the form of isomers. This is the case, for example, when, in the compound of formula (I), R 2 is not hydrogen; or when R 2 is hydrogen and R-i is not in the 5-position on the pyrimidine ring, for example
  • R 1 ; R 3 , X-,, X 2 and X 3 are as defined for formula (I).
  • the prepared compounds therefore often comprise mixtures of isomers and tautomers thereof, in free form or in salt form.
  • the compounds of formula (I) and, where appropriate, the tautomers thereof can form salts, e.g. acid addition salts.
  • Those salts are formed, for example, with strong inorganic acids, such as mineral acids, e.g. sulfuric acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as unsubstituted or substituted, for example halo-substituted, CrC 4 alkanecarboxylic acids, e.g acetic acid, or saturated or unsaturated dicarboxylic acids, e.g. oxalic, malonic, maleic, fumaric or phthalic acid, or hydroxycarboxylic acids, e.g.
  • strong inorganic acids such as mineral acids, e.g. sulfuric acid, a phosphoric acid or a hydrohalic acid
  • strong organic carboxylic acids such as unsubstituted or substituted, for example halo-substituted, CrC
  • compounds of formula (I) having at least one acidic group are capable of forming salts with bases.
  • Suitable salts with bases are, for example, metal salts, such as alkali metal or alkaline earth metal salts, e.g.
  • sodium, potassium or magnesium salts or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, e.g. ethylamine, diethylamine, triethylamine or dimethylpropylamine, or a mono-, di- or tri- hydroxy-lower alkylamine, e.g. mono-, di- or tri-ethanolamine.
  • corresponding internal salts may also be formed. Preference is given to the free form.
  • preference is given to agrochemically advantageous salts.
  • Carbon-containing groups and compounds each contain from 1 up to and including 6 carbon atoms, preferably from 1 up to and including 4 carbon atoms, especially 1 or 2 carbon atoms.
  • Aryl is phenyl or naphthyl.
  • Halogen - as a group perse and as a structural element of other groups and compounds, such as of haloalkyl, haloalkoxy and haloalkylthio - is fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, more especially fluorine or chlorine.
  • Alkyl - as a group perse and as a structural element of other groups and compounds, such as of haloalkyl, alkoxy and alkylthio, - is, in each case giving due consideration to the number of carbon atoms present in the group or compound in question, either straight-chain, e.g. methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, or branched, e.g. isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl or isohexyl.
  • straight-chain e.g. methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, or branched, e.g. isopropyl, isobutyl, sec-
  • Cycloalkyl - as a group perse and as a structural element of other groups and compounds, such as of halocycloalkyl, cycloalkoxy and cycloalkylthio, - is, in each case giving due consideration to the number of carbon atoms present in the group or compound in question, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
  • Alkenyl - as a group perse and as a structural element of other groups and compounds - is, in each case giving due consideration to the number of carbon atoms and conjugated or isolated double bonds present in the group or compound in question, either straight-chain, e.g. allyl, 2-butenyl, 3-pentenyl, 1-hexenyl, 1-heptenyl, 1 ,3-hexadienyl or 1 ,3-octadienyl, or branched, e.g. isopropenyl, isobutenyl, isoprenyl, tert-pentenyl, isohexenyl, isoheptenyl or isooctenyl.
  • straight-chain e.g. allyl, 2-butenyl, 3-pentenyl, 1-hexenyl, 1-heptenyl, 1 ,3-hexadienyl or 1 ,3-octadieny
  • Alkynyl - as a group perse and as a structural element of other groups and compounds - is, in each case giving due consideration to the number of carbon atoms and conjugated or isolated double bonds present in the group or compound in question, either straight-chain, e.g. propargyl, 2-butynyl, 3-pentynyl, 1 -hexynyl, 1-heptynyl, 3-hexen-1 -ynyl or 1 ,5-hepta- dien-3-ynyl, or branched, e.g. 3-methylbut-1-ynyl, 4-ethylpent-1-ynyl, 4-methylhex-2-ynyl or 2-methylhept-3-ynyl.
  • straight-chain e.g. propargyl, 2-butynyl, 3-pentynyl, 1 -hexynyl, 1-heptynyl, 3-hexen-1 -ynyl or 1
  • Halo-substituted carbon-containing groups and compounds such as haloalkyl, haloalkoxy or haloalkylthio, may be partially halogenated or per-halogenated, the halogen substituents in the case of poly-halogenation being the same or different.
  • haloalkyl - as a group perse and as a structural element of other groups and compounds, such as of haloalkoxy or haloalkylthio - are methyl substituted from one to three times by fluorine, chlorine and/or by bromine, such as CHF 2 or CF 3 ; ethyl substituted from one to five times by fluorine, chlorine and/or by bromine, such as CH 2 CF 3 , CF 2 CF 3 , CF 2 CCI 3 , CF 2 CHCI 2 , CF 2 CHF 2 , CF 2 CFCI 2 , CF 2 CHBr 2 , CF 2 CHCIF, CF 2 CHBrF or CCIFCHCIF; propyl or isopropyl, each substituted from one to seven times by fluorine, chlorine and/or by bromine, such as CH 2 CHBrCH 2 Br, CF 2 CHFCF 3 , CH 2 CF 2 CF 3 or CH(CF 3 ) 2
  • halogen CN, NO 2 , C C 4 alkyl, C 3 -C 8 cycloalkyl, CH 2 -C 3 -C 6 cycloalkyl, C r C 4 haloalkyl, C 3 -C 6 halocycloalkyl, C C 4 alkoxy, CrC 4 haloalkoxy, C C 4 alkylthio, CrC 4 haloalkylthio, CrC 4 alkylsulfinyl, CrC 4 haloalkylsulfinyl, CrC alkylsulfonyl, CrC 4 haloalkylsulfonyl, C 3 -C 6 - alkenyl, C 3 -C 6 alkynyl; unsubstituted or mono- or di-substituted phenyl, the substituents being selected from the group consisting of halogen, CN, NO 2 , CrC 4 alkyl, C 3 -C 8 cycl
  • Ri is especially unsubstituted or mono- or di-substituted phenyl, the substituents being selected from the group consisting of halogen, CN, NO 2 , C C 2 alkyl, C 3 -C 6 cycloalkyl, CrC 2 haloalkyl, CrC 2 alkoxy, CrC 2 haloalkoxy, C C 2 alkylthio, C C 2 haloalkylthio, CrC 2 alkylsulfinyl, CrC 2 haloalkylsulfinyl, CrC 2 alkyl- sulfonyl, CrC 2 haloalkylsulfonyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl; unsubstituted or mono- or di-substituted phenyl, the substituents being selected from the group consisting of fluorine, chlorine, CN, NO 2 , C C 2 alkyl, C
  • R T is very especially mono- or di-substituted phenyl substituted by mono- or di-substituted phenyl, the substituents being selected from the group consisting of fluorine, chlorine, methyl, cyclopropyl, trifluoromethyl, methoxy, trifluoromethoxy, methylthio and trifluoromethylthio; more especially wherein R T is phenyl substituted in the p-position by mono- or di-substituted phenyl; more especially wherein Ri is in the 5-position on the tetrahydropyrimidine ring;
  • R 2 is H, OH, halogen, CN, NO 2 , C r C 4 alkyl, CrC 4 alkoxy, C C 4 alkylthio, C 3 -C 6 cycloalkyl, CrC haloalkyl, CrC cyanoalkyl or C r C 4 nitroalkyl; especially H, OH, chlorine, CN or methyl; more especially H;
  • each R 5 independently of the other is H or C C 4 alkyl; especially H, methyl or ethyl;
  • the invention relates also to a process for the preparation of compounds of formula (I) and, where appropriate, their tautomers, in each case in free form or in salt form, wherein a) for the preparation of a compound of formula
  • A-(C Y) n -W-R 9 (III), which is known or can be prepared according to methods known perse, and wherein Y, n and W are as defined for formula (l) and A is a leaving group; or c) for the preparation of a compound of formula (I) a compound of formula
  • reaction described hereinbefore and hereinafter are carried out in a manner known per se, e.g. in the absence or, customarily, in the presence of a suitable solvent or diluent or a mixture thereof, the reaction being carried out, as required, with cooling, at room temperature or with heating, e.g. in a temperature range of from about -80°C to the boiling temperature of the reaction medium, preferably from about 0°C to about +150°C, and, if necessary, in a sealed container, under pressure, in an inert gas atmosphere and/or under anhydrous conditions.
  • a suitable solvent or diluent or a mixture thereof the reaction being carried out, as required, with cooling, at room temperature or with heating, e.g. in a temperature range of from about -80°C to the boiling temperature of the reaction medium, preferably from about 0°C to about +150°C, and, if necessary, in a sealed container, under pressure, in an inert gas atmosphere and/or under anhydrous conditions
  • reaction time is not critical; preference is given to a reaction time of from about 0.1 to about 24 hours, especially from about 0.5 to about 10 hours.
  • the product is isolated according to customary methods, e.g. by filtration, crystallisation, distillation or chromatography or any suitable combination of those procedures.
  • Suitable catalysts are especially transition metal catalysts, especially iron, palladium, ruthenium, rhodium, nickel, zinc or platinum catalysts.
  • Especially suitable catalysts include nickel(O), platinum and palladium(O) catalysts, especially Raney nickel, platinum on carbon and palladium on carbon.
  • Suitable acids for facilitating the reaction are, for example, carboxylic acids, such as acetic acid or oxalic acid; or mineral acids, such as hydrochloric acid.
  • solvents or diluents examples include: esters, such as ethyl acetate; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether (dimethoxyethane), dimethoxydiethyl ether, tetrahydrofuran and dioxane; ketones, such as acetone, methyl ethyl ketone and methyl isobutyl ketone; alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol and glycerol.
  • esters such as ethyl acetate
  • ethers such as diethyl ether, dipropyl ether, diisopropyl ether, di
  • the reaction is carried out advantageously in a temperature range of from about room temperature to about 80°C, preferably at room temperature and especially at normal pressure up to about 50 atm, preferably at normal pressure.
  • Example P1 Especially preferred conditions for the reaction are described in Example P1.
  • the reactants can be reacted with one another as such, that is to say without the addition of a solvent or diluent, e.g. in the molten state. It is generally advantageous, however, to add an inert solvent or diluent or a mixture thereof.
  • solvents or diluents examples include: aromatic, aliphatic and alicyclic hydrocarbons and halogenated hydrocarbons, such as benzene, toluene, xylene, mesitylene, Tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, tetrachloromethane, dichloroethane, trichloroethene or tetrachloro-ethene; ethers, such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydro
  • Suitable leaving groups A in the compounds of formula (III) are, for example, CrC 8 alkoxy, halo-d-C 8 alkoxy, CrC 8 alkanoyloxy, C C 8 alkylthio, halo-C C 8 alkylthio, d-C 8 alkane- sulfonyloxy, halo-C C 8 alkanesulfonyloxy, benzenesulfonyloxy, toluenesulfonyloxy and halogen, preferably toluenesulfonyloxy, trifluoromethanesulfonyloxy or halogen, especially halogen, more especially bromine or chlorine.
  • the reaction can be carried out in the absence or presence of a catalyst.
  • Suitable catalysts are especially copper acetate, zinc acetate, or an acid, such as hydrochloric acid or toluene- sulfonic acid.
  • the reaction is advantageously carried out in a temperature range of from about room temperature to about 200°C, preferably from 80 to 180°C.
  • Salts of compounds of formula (I) can be prepared in a manner known perse. For example, acid addition salts of compounds of formula (I) are obtained by treatment with a suitable acid or a suitable ion-exchange reagent, and salts with bases are obtained by treatment with a suitable base or a suitable ion-exchange reagent.
  • Salts of compounds of formula (I) can be converted into the free compounds of formula (I) in customary manner: acid addition salts, for example by treatment with a suitable basic agent or a suitable ion-exchange reagent, and salts with bases, for example, by treatment with a suitable acid or a suitable ion-exchange reagent.
  • Salts of compounds of formula (I) can be converted into different salts of compounds of formula (I) in a manner known perse: acid addition salts, for example, can be converted into different acid addition salts, e.g. by treatment of a salt of an inorganic acid, such as a hydrochloride, with a suitable metal salt, such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt being formed, e.g. silver chloride, is insoluble and therefore separates out from the reaction mixture.
  • a salt of an inorganic acid such as a hydrochloride
  • a suitable metal salt such as a sodium, barium or silver salt
  • the compounds of formula (I) having salt-forming properties can be obtained in free form or in the form of salts.
  • the compounds of formula (I) may be in the form of one of the possible isomers or in the form of a mixture thereof, in the form of pure isomers or in the form of mixtures of isomers, that is to say in the form of a racemic mixture; the invention relates both to the pure isomers and to the racemic mixtures, and this is to be understood hereinbefore and hereinafter, even if stereochemical details are not specifically mentioned in each case.
  • racemates can be separated into the optical antipodes according to known methods, for example by recrystallisation from an optically active solvent, by chromatography on chiral adsorbents, e.g. high-pressure liquid chromatography (HPLC) on acetyl cellulose, with the aid of suitable microorganisms, by cleavage with specific immobilised enzymes, via the formation of inclusion compounds, e.g. using chiral crown ethers, in which case only one isomer is complexed.
  • HPLC high-pressure liquid chromatography
  • the compounds of formula (I) can also be obtained in the form of their hydrates and/or may include other solvents, for example solvents which may have been used for the crystallisation of compounds in solid form.
  • the invention relates to all those forms of the process according to which a compound obtainable as starting material or intermediate at any stage of the process is used as starting material and all or some of the remaining steps are carried out, or a starting material is used in the form of a derivative or a salt and/or its racemates or antipodes or, especially, is formed under the reaction conditions.
  • the invention relates especially to the preparation processes described in Examples P1 and P2.
  • the compounds of formula (I) according to the invention are valuable preventive and/or curative active ingredients having a very advantageous very broad biocidal spectrum even at low rates of concentration, while being well tolerated by warm-blooded animals, fish and plants. They are surprisingly equally suitable for controlling plant pests as for controlling ecto- and endo-parasites in humans and especially in productive livestock, domestic animals and pets. They are effective against all or individual development stages of normally sensitive animal pests, but also of resistant animal pests, such as insects and representatives of the order Acarina, nematodes, cestodes, trematodes and gastropodes, whilst simultaneously sparing useful organisms.
  • the insecticidal or acaricidal action of the compounds according to the invention may manifest itself directly, i.e. in the death of the pests, which occurs immediately or only after some time, for example during moulting, or indirectly, for example in reduced oviposition and/or hatching rate, good activity corresponding to a mortality of at least 50 to 60%.
  • the action of the compounds according to the invention and of compositions comprising them against animal pests can be substantially broadened and adapted to prevailing circumstances by the addition of other insecticides and/or acaricides.
  • additives there come into consideration, for example, representatives of the following classes of compound: organophosphorus compounds, nitrophenols and derivatives, formamidines, ureas, carbamates, pyrethroids, chlorinated hydrocarbons, and Bacillus thuringiensis preparations.
  • mixing partners include: azamethiphos; chlorfenvinphos; cypermethrin, cypermethrin high-cis; cyromazine; diafenthiuron; diazinon; dichlorvos; dicrotophos; dicyclanil; fenoxycarb; fluazuron; furathiocarb; isazofos; iodofenphos; kinoprene; lufenuron; methacrifos; methidathion; monocrotophos; phosphamidon; profenofos; diofenolan; a substance obtainable from Bacillus thuringiensis strain GC91 or from NCTC11821 ; pymetrozine; bromopropylate; methoprene; disulfoton; quinalphos; tau- fluvalinate; thiocyclam; thiometon; aldicarb; azinphos-methyl; ben
  • the mentioned animal pests include, for example, representatives of the classes Insecta, Arachnida, Nematoda and Gastropoda.
  • the class insecta they are preferably representatives of the order Lepidoptera, for example
  • Curculio spp. Dermestes spp., Diabrotica spp., Epilachna spp., Eremnus spp., Leptinotarsa decemlineata, Lissorhoptrus spp., Melolontha spp., Orycaephilus spp., Otiorhynchus spp.,
  • Blatta spp. Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Periplaneta spp. and Schistocerca spp.; of the order Psocoptera, for example Liposcelis spp.; of the order Anoplura, for example
  • Haematopinus spp. Linognathus spp., Pediculus spp., Pemphigus spp. und Phylloxera spp.; of the order Mallophaga, for example Damalinea spp. and Trichodectes spp.; of the order Thysanoptera, for example Frankliniella spp., Hercinothrips spp., Taeniothrips spp., Thrips palmi, Thrips tabaci and Scirtothrips aurantii; of the order Heteroptera, for example Cimex spp., Distantiella theobroma, Dysdercus spp.,
  • Aonidiella spp. Aphididae, Aphis spp., Aspidiotus spp., Bemisia tabaci, Ceroplaster spp.,
  • Paratoria spp. Pemphigus spp., Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Rhopalosiphum spp.,
  • Saissetia spp. Scaphoideus spp., Schizaphis spp., Sitobion spp., Trialeurodes vaporariorum, Trioza erytreae and Unaspis citri; of the order Hymenoptera, for example Acromyrmex, Atta spp., Cephus spp., Diprion spp.,
  • Neodiprion spp. Solenopsis spp. and Vespa spp.; of the order Diptera, for example Aedes spp., Antherigona soccata, Bibio hortulanus,
  • Dacus spp. Drosophila melanogaster, Fannia spp., Gastrophilus spp., Glossina spp.,
  • Thysanura for example Lepisma saccharina
  • Isoptera longites
  • the families Hodotermitidae, Kalotermitidae, Rhinotermitidae and Termitidae are especially Allondothermes ssp., e.g. A. giffardi and A. tenax; ; Ancistrotermes ssp:, e.g. A. cavithorax, A. guineensis, A. latinotus and A.
  • Amitermes ssp. e.g. A. evuncifer
  • Heterotermes ssp. e.g. H. indicola uhd H. tenuis
  • Hodotermes ssp. e.g. H. mossambicus
  • Macrotermes ssp. e.g. M. michaelseni, M. falcifager, M. bellicosus, M. subhyalinus and M. natalensis
  • Microtermes ssp. e.g. M. albopartitus, . redenianus, . lepidus, M-. traghardi and M.
  • Nasutitermes ssp. e.g. N. costalis
  • Neotermes ssp. e.g. N. gestroi
  • Odontotermes ssp. e.g. O. bruneus, O. classicus, O. smeathmani, O. lathericius and O. badius
  • Pseudacantho- termes ssp. e.g. P. militaris and P. spiniger
  • Reticulitermes ssp. e.g. R. flavides, R. santonensis and R. hesperus
  • Termes ssp. e.g. T. fatalis
  • Trinervitermes ssp. e.g. T. trinervius
  • wood-boring insects such as representatives of the family Lyctidae, the family Apidae, for example Xylocopa virginica, and of the family Anobiidae, such as Anobium punctatum.
  • the said pests are preferably representatives of the order Acarina, for example
  • a further preferred subject according to the invention is the control of representatives of the class Nematoda, such as root knot nematodes, stem eelworms and foliar nematodes; especially Heterodera spp., for example Heterodera schachtii, Heterodora avenae and Heterodora trifolii; Globodera spp., for example Globodera rostochiensis; Meloidogyne spp., for example Meloidogyne incognita and Meloidogyne javanica; Radopholus spp., for example Radopholus similis; Pratylenchus, for example Pratylenchus neglectans and Pratylenchus penetrans; Tylenchulus, for example Tylenchulus semipenetrans; Longidorus, Trichodorus, Xiphinema, Ditylenchus, Aphelenchoides and
  • a further preferred subject according to the invention is the control of representatives of the class of the Gastropoda.
  • These molluscs include, for example, Ampullariidae; Arion (A. ater, A. circumscriptus, A. hortensis, A. rufus); Bradybaenidae (Bradybaena fruticum); Cepaea (C. hortensis, C. nemoralis); Cochlodina; Deroceras (D. agrestis, D. empiricorum, D. laeve, D. reticulatum); Discus (D. rotundatus); Euomphalia; Galba (G. trunculata); Helicella (H.
  • H. obvia Helicidae (Helicigona arbustorum); Helicodiscus; Helix (H. aperta); Umax (L. cinereoniger, L. flavus, L. marginatus, L. maximus, L. tenellus); Lymnaea; Milax (M. gagates, M. marginatus, M. sowerbyi); Opeas; Pomacea (P. canaticulata); Vallonia and Zanitoides.
  • the present invention places special emphasis on the use of the compounds of formula (I) according to the invention in the protection of plants against parasitic feeding pests.
  • Target crops are especially cereals, such as wheat, barley, rye, oats, rice, maize and sorghum; beet, such as sugar beet and fodder beet; fruit, such as pomes, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries, or berries, for example strawberries, raspberries or blackberries; leguminous plants, such as beans, lentils, peas and soybeans; oil plants, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans and groundnuts; cucurbitaceae, such as marrows, cucumbers and melons; fibre plants, such as cotton, flax, hemp and jute; citrus fruit, such as oranges, lemons, grapefruit and mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes and paprika; lauraceae, such as avocados, cinnamon and camphor; and tobacco, nuts,
  • the invention accordingly relates also to pesticides, such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, wettable powders, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymer substances, comprising - at least - one of the compounds of the invention, the type of formulation being chosen in accordance with the intended objectives and prevailing circumstances.
  • pesticides such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsions, wettable powders, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymer substances, comprising - at least - one of the compounds of the invention, the type of formulation being chosen in accordance with the intended objectives and prevailing circumstances.
  • the active ingredient is used in those compositions in pure form, a solid active ingredient, for example, in a specific particle size, or preferably together with - at least - one of the adjuvants customary in formulation technology, such as extenders, for example solvents or solid carriers, or surface-active compounds (surfactants).
  • extenders for example solvents or solid carriers, or surface-active compounds (surfactants).
  • surfactants surface-active compounds
  • formulation adjuvants for example, solid carriers, solvents, stabilisers, "slow release” adjuvants, colorants and, where appropriate, surface-active substances (surfactants).
  • carriers and adjuvants there come into consideration all the substances customarily used, such as solvents, solid carriers, surface-active compounds, nonionic surfactants, cationic surfactants, anionic surfactants and further adjuvants known in the art.
  • solvents which are suitable are: unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably the fractions C 8 to C 12 of alkylbenzenes, such as xylene mixtures, alkylated naphthalene or tetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such as paraffins or cyclohexane, alcohols, such as ethanol, propanol or butanol, glycols and their ethers and esters, such as propylene glycol, dipropylene glycol ether, ethylene glycol, ethylene glycol monomethyl ether or ethylene glycol monoethyl ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents, such as N-methylpyrrolid-2-one, dimethyl sulfoxide or N,N-dimethylformamide, water, unepoxidized or epoxidized vegetable oils, such as unepoxidized or
  • Solid carriers which are used for example for dusts and dispersable powders are, as a rule, ground natural minerals, such as calcite, talc, kaolin, montmorillonite or attapulgite. Highly- disperse silicas or highly-disperse absorptive polymers may also be used to improve the physical properties.
  • Suitable particulate, adsorptive carriers for granules are porous types, such as pumice, brick grit, sepiolite or bentonite, and suitable non-absorptive carrier materials are calcite or sand.
  • a large number of granulated materials of inorganic or organic nature, in particular dolomite or comminuted plant residues may be used.
  • Suitable surface-active compounds are, depending on the nature of the active ingredient to be formulated, non-ionic, cationic and/or anionic surfactants or surfactant mixtures have good emulsifying, dispersing and wetting properties.
  • the surfactants listed below are only given by way of example; a large number of other surfactants conventionally used in the art of formulation and suitable according to the invention are described in the relevant literature.
  • Suitable non-ionic surfactants are mainly polyglycol ether derivatives of aliphatic or cyclo- liphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can have 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols. Also suitable are water-soluble polyethylene oxide adducts with polypropylene glycol, ethylene diaminoolypropylene glycol and alkyl polypropylene glycol having 1 to 10 carbon atoms in the alkyl chain and comprising 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups.
  • the abovementioned compounds conventionally have 1 to 5 ethylene glycol units per propylene glycol unit.
  • examples which may be mentioned are nonylphenol polyethoxyethanols, castor oil polyglycol ether, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxy- ethanol, polyethylene glycol and octylphenoxypolyethoxyethanol.
  • fatty acid esters or polyoxyethylene sorbitan such as polyoxyethylene sorbitan trioleate.
  • the cationic surfactants are mainly quaternary ammonium salts which have, as substituents, at least one alkyl radical having 8 to 22 carbon atoms and as further substituents lower, halogenated or unhalogenated alkyl, benzyl or lower hydroxyalkyl radicals.
  • the salts are preferably in the form of halides, methylsulfates or ethylsulfates. Examples are stearyl- trimethyl-ammonium chloride and benzyl di-(2-chloroethyl)ethylammonium bromide.
  • Suitable anionic surfactants can be water-soluble soaps and also water-soluble synthetic surface-active compounds.
  • Soaps which are suitable are the alkali metal salts, alkaline earth metal salts and substituted or unsubstituted ammonium salts of higher fatty acids (C 10 -C 22 ), such as the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained, for example, from coconut or tall oil; fatty acid methyl- taurinates should furthermore be mentioned.
  • so-called synthetic surfactants are used more frequently, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates.
  • the fatty sulfonates and fatty sulfates are, as a rule, in the form of alkali metal salts, alkaline earth metal salts or substituted or unsubstituted ammonium salts and have, as a rule, an alkyl radical of 8 to 22 carbon atoms, alkyl also including the alkyl moiety of acyl radicals, for example the sodium salt or calcium salt of lignosulfonic acid, of the dodecylsulfuric ester or of a fatty alcohol sulfate mixture prepared from natural fatty acids.
  • This group also includes the salts of the sulfuric esters and sulfonic acids of fatty alcohol/ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives comprise preferably 2 sulfonyl groups and a fatty acid radical having approximately 8-22 carbon atoms.
  • Alkylarylsulfonates are, for example, the sodium salts, calcium salts or triethanolammonium salts of dodecylbenzenesulfonic acid or of a naphthalenesulfonic acid/formaldehyde condensate.
  • Suitable phosphates for example salts of the phosphoric ester of a p-nonylphenol/(4-14)-ethylene oxide adduct, or phospholipids, are also suitable.
  • compositions for use in crop protection and in humans, domestic animals, productive livestock and pets generally contain from 0.1 to 99 %, especially from 0.1 to 95 %, of active ingredient and from 1 to 99.9 %, especially from 5 to 99.9 %, of - at least - one solid or liquid adjuvant, it generally being possible for the compositions to contain from 0 to 25 %, especially from 0.1 to 20 %, surfactants (in each case percentages are by weight). Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations which have considerably lower active ingredient concentrations.
  • Preferred crop protection compositions have especially the following composition (throughout, percentages are by weight):
  • Emulsifiable concentrates active ingredient: from 1 to 90 %, preferably from 5 to 20 % surfactant: from 1 to 30 %, preferably from 10 to 20 % solvent: from 5 to 98 %, preferably from 70 to 85 %
  • Dusts active ingredient: from 0.1 to 10 %, preferably from 0.1 to 1 % solid carrier: from 99.9 to 90 %, preferably from 99.9 to 99 %
  • Suspension concentrates active ingredient: from 5 to 75 %, preferably from 10 to 50 % water: from 94 to 24 %, preferably from 88 to 30 % surfactant: from 1 to 40 %, preferably from 2 to 30 %
  • Wettable powders active ingredient: from 0.5 to 90 %, preferably from 1 to 80 % surfactant: from 0.5 to 20 %, preferably from 1 to 15 % solid carrier: from 5 to 99 %, preferably from 15 to 98 %
  • Granules active ingredient: from 0.5 to 30 %, preferably from 3 to 15 % solid carrier: from 99.5 to 70 %, preferably from 97 to 85 %
  • compositions according to the invention may also comprise further solid or liquid adjuvants, such as stabilisers, e.g. vegetable oils or epoxidised vegetable oils (e.g. epoxidised coconut oil, rapeseed oil or soybean oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, as well as fertilisers or other active ingredients for obtaining special effects, for example acaricides, bactericides, fungicides, nematicides, molluscicides or selective herbicides.
  • stabilisers e.g. vegetable oils or epoxidised vegetable oils (e.g. epoxidised coconut oil, rapeseed oil or soybean oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, as well as fertilisers or other active ingredients for obtaining special effects, for example acaricides, bactericide
  • the crop protection compositions according to the invention are prepared in known manner, in the absence of adjuvants, for example by grinding, sieving and/or compressing a solid active ingredient or mixture of active ingredients, for example to a specific particle size, and in the presence of at least one adjuvant, for example by intimately mixing and/or grinding the active ingredient or mixture of active ingredients with the adjuvant(s).
  • the invention relates also to those processes for the preparation of the compositions according to the invention and to the use of the compounds of formula (I) in the preparation of those compositions.
  • the invention relates also to the methods of application of the crop protection compositions, i.e. the methods of controlling pests of the mentioned type, such as spraying, atomising, dusting, coating, dressing, scattering and pouring, which are selected in accordance with the intended objectives and prevailing circumstances, and to the use of the compositions for controlling pests of the mentioned type.
  • Typical rates of concentration are from 0.1 to 1000 ppm, preferably from 0.1 to 500 ppm, of active ingredient.
  • the rates of application per hectare are generally from 1 to 2000 g of active ingredient per hectare, especially from 10 to 1000 g/ha, preferably from 20 to 600 g/ha.
  • a preferred method of application in the area of crop protection is application to the foliage of the plants (foliar application), the number of applications and the rate of application depending on the risk of infestation by the pest in question.
  • the active ingredient can also penetrate the plants through the roots (systemic action) if the locus of the plants is impregnated with a liquid formulation or if the active ingredient is incorporated in solid form, e.g. in granular form, into the locus of the plants, for example into the soil (soil application).
  • granules may be applied in metered amounts to the flooded rice field.
  • the crop protection compositions according to the invention are also suitable for protecting plant propagation material, e.g. seed material, such as fruit, tubers or grains, or plant cuttings, against animal pests.
  • the propagation material can be treated with the formulation before planting: seed, for example, can be dressed before being sown.
  • the compounds of the invention can also be applied to grains (coating), either by impregnating the grains with a liquid formulation or by coating them with a solid formulation.
  • the formulation can also be applied to the planting site when the propagation material is being planted, for example to the seed furrow during sowing.
  • the invention relates also to those methods of treating plant propagation material and to the plant propagation material thus treated.
  • Example P2 The other compounds of formula (I) can be prepared in a manner analogous to Example P1.
  • Table 2 Compounds of the general formula (lb) wherein R is 4-OCF 3 and the combination of the substituents X ⁇ X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 3 Compounds of the general formula (lb) wherein R b is 4-CF 3 and the combination of the substituents Xi . , X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 4 Compounds of the general formula (lb) wherein R b is 3,5-CI 2 and the combination of the substituents X 1 ; X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 5 Compounds of the general formula (lb) wherein R b is 3-CI and the combination of the substituents X 1 ; X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 6 Compounds of the general formula (lb) wherein R is 3-CI, 4-F and the combination of the substituents X 1 ( X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 7 Compounds of the general formula (lb) wherein R is 4-SCH 3 and the combination of the substituents X ⁇ X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 8 Compounds of the general formula (lb) wherein R b is 3-CF 3 and the combination of the substituents X 1 ; X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 9 Compounds of the general formula (lb) wherein R is 2,4-CI 2 and the combination of the substituents X 1 ( X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 10 Compounds of the general formula (lb) wherein R is 4-CI and the combination of the substituents X ⁇ X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 11 Compounds of the general formula (lb) wherein R b is 4-SCF 3 and the combination of the substituents Xi, X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 12 Compounds of the general formula (Ic) wherein R b is H and the combination of the substituents X 1 t X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 13 Compounds of the general formula (Ic) wherein R b is 4-OCF 3 and the combination of the substituents X-i, X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 14 Compounds of the general formula (Ic) wherein R is 4-CF 3 and the combination of the substituents X 1 ; X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 15 Compounds of the general formula (Ic) wherein R b is 3,5-CI 2 and the combination of the substituents X 1 t X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 16 Compounds of the general formula (Ic) wherein R is 3-CI and the combination of the substituents X 1 ? X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 17 Compounds of the general formula (Ic) wherein R b is 3-CI, 4-F and the combination of the substituents X 1 ? X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 18 Compounds of the general formula (Ic) wherein R b is 4-SCH 3 and the combination of the substituents X ⁇ X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 19 Compounds of the general formula (Ic) wherein R b is 3-CF 3 and the combination of the substituents X-i, X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 20 Compounds of the general formula (Ic) wherein R is 2,4-CI 2 and the combination of the substituents X ⁇ X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 21 Compounds of the general formula (Ic) wherein R b is 4-CI and the combination of the substituents X ⁇ X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Table 22 Compounds of the general formula (Ic) wherein R b is 4-SCF 3 and the combination of the substituents X 1 f X 2 , X 3 , R 2 and R 3 for each compound corresponds to a line A.1 to A.140 of Table A.
  • Example F1 Emulsifiable concentrates a) b) c) active ingredient 25% 40% 50% calcium dodecylbenzenesulfonate 5% 8% 6% castor oil polyethylene glycol ether (36 mol EO) 5% - - tributylphenol polyethylene glycol ether (30 mol EO) - 12% 4% cyclohexanone - 15% 20% xylene mixture 65% 25% 20%
  • Example F2 Solutions a) b) c) d) active ingredient 80% 10% 5% 95% ethylene glycol monomethyl ether 20% - - - polyethylene glycol (MW 400) - 70% - -
  • N-methylpyrrolid-2-one 20% - - epoxidised coconut oil - - 1 % 5% benzine (boiling range: 160-190°) - - 94% -
  • the finely ground active ingredient and adjuvants are mixed to yield a solution suitable for use in the form of microdrops.
  • Example F3 Granules a) b) c) d) active ingredient 5% 10% 8% 21 % kaolin 94% 79% 54% highly dispersed silicic acid 1% 13% 7% attapulgite - 90% - 18%
  • the active ingredient is dissolved in dichloromethane, the solution is sprayed onto the carrier mixture and the solvent is removed by evaporation in vacuo.
  • Example F4 Dusts a) b) active ingredient 2% 5% highly dispersed silicic acid 1 % 5% talcum 97% - kaolin - 90%
  • the active ingredient and carriers are mixed to yield ready-for-use dusts.
  • Example F5 Wettable powders a) b) c) active ingredient 25% 50% 75% sodium lignosulfonate 5% 5% - sodium lauryl sulfate 3% - 5% sodium diisobutylnaphthalenesulfonate - 6% 10% octylphenol polyethylene glycol ether (7-8 mol EO) - 2% - highly dispersed silicic acid 5% 10% 10% kaolin 62% 27% - The active ingredient and adjuvants are mixed and the mixture is ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of any desired concentration.
  • Example F6 Emulsifiable concentrate active ingredient 10% octylphenol polyethylene glycol ether (4-5 mol EO) 3% calcium dodecylbenzenesulfonate 3% castor oil polyethylene glycol ether (36 mol EO) 4% cyclohexanone 30% xylene mixture 50%
  • the finely ground active ingredient and adjuvants are mixed to yield an emulsifiable concentrate which gives emulsions of any desired concentration when diluted with water.
  • Example F7 Dusts a) b) active ingredient 5% 8% talcum 95% - kaolin - 92%
  • a ready-for-use dust is obtained by mixing the active ingredient and carrier and grinding the mixture in a suitable mill.
  • Example F8 Extruder granules active ingredient 10% sodium lignosulfonate 2% carboxymethylcellulose 1 % kaolin 87%
  • the active ingredient and adjuvants are mixed, the mixture is ground, moistened with water, extruded and granulated, and the granules are dried in a stream of air.
  • Example F9 Coated granules active ingredient 3% polyethylene glycol (MW 200) 3% kaolin 94%
  • Example F10 Suspension concentrate active ingredient 40% ethylene glycol 10% nonylphenol polyethylene glycol ether (15 mol EO) 6% sodium lignosulfonate 10% carboxymethyicellulose 1 % aqueous formaldehyde solution (37%) 0.2% aqueous silicone oil emulsion (75%) 0.8% water 32%
  • the finely ground active ingredient and adjuvants are mixed, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.
  • Example B1 Action against Aphis craccivora
  • Pea seedlings are infested with Aphis craccivora, subsequently sprayed with a spray mixture comprising 100 ppm of active ingredient and then incubated at 20°C. 3 and 6 days later the percentage reduction in population (% activity) is determined by comparing the number of dead aphids on the treated plants with that on untreated plants.
  • Maize seedlings are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of active ingredient. After the spray-coating has dried, the maize seedlings are populated with 10 Diabrotica balteata larvae in the second stage and then placed in a plastics container. 6 days later, the percentage reduction in population (% activity) is determined by comparing the number of dead larvae on the treated plants with that on untreated plants.
  • Example B3 Action against Heliothis virescens
  • Young soybean plants are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of active ingredient. After the spray-coating has dried, the plants are populated with 10 caterpillars of Heliothis virescens in the first stage and then placed in a plastics container. 6 days later, the percentage reduction in population and in feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage on the treated plants with that on untreated plants.
  • Compounds of the Tables exhibit good activity in this test.
  • compound B.1 in particular, exhibits a reduction in the pest population of more than 80 %.
  • Example B4 Action against Spodoptera littoralis
  • Young soybean plants are sprayed with an aqueous emulsion spray mixture comprising 100 ppm of active ingredient. After the spray-coating has dried, the plants are populated with 10 caterpillars of Spodoptera littoralis in the third stage and then placed in a plastics container. 3 days later, the percentage reduction in population and the percentage reduction in feeding damage (% activity) are determined by comparing the number of dead caterpillars and the feeding damage on the treated plants with that on untreated plants.
  • Example B5 Action against Nilaparvata lugens
  • Rice plants are treated with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient. After the spray-coating has dried, the rice plants are populated with cicada larvae in the 2nd and 3rd stages. The evaluation is carried out 21 days later. The percentage reduction in population (% activity) is determined by comparing the number of surviving cicadas on the treated plants with that on untreated plants.
  • Example B6 Action against Tetranychus urticae
  • Young bean plants are populated with a mixed population of Tetranychus urticae and sprayed one day later with an aqueous emulsion spray mixture comprising 100 ppm of active ingredient. The plants are then incubated for 6 days at 25°C and subsequently evaluated. The percentage reduction in population (% activity) is determined by comparing the number of dead eggs, larvae and adults on the treated plants with that on untreated plants.

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Abstract

L'invention concerne des composés de formule (I). Dans cette formule, R1 est aryle substitué ou non, les substituants pouvant être par exemple OH, halogène, CN, NO2, alkyle C1-C6, cycloalkyle C3-C8 et alkyle C1-C6-cycloalkyle-C3-C8; phényle substitué ou non, les substituants pouvant être par exemple OH, halogène, CN, NO2, alkyle C1-C6, cycloalkyle C3-C8 et cycloalcényle-C3-C8; phénoxy, phénylthio, phénylamino et phényle-(alkyle C1-C6)-amino substitué ou non; R2 est, par exemple, H, OH, halogène, CN, NO2 ou alkyle C1-C6; R3 est -(C=Y)n-W-R9; X1 est R8; X2 et X3 sont chacun indépendamment H ou R8; R8 est, par exemple, halogène, CN, NO2, alkyle C1-C6 ou haloalkyle C1-C6; Y est O ou S; n vaut O, 1 ou 2; W est une liaison unique, O, S, NH ou N(alkyle C1-C4); et R9 est, for exemple, hydrogène, alkyle C1-C6 ou haloalkyle C1-C6. Selon le cas, l'invention concerne également des isomères E/Z, des mélanges d'isomères E/Z et/ou des tautomères appropriés, toujours sous forme libre ou sous forme de sel, et le cas échéant, elle concerne les tautomères éventuels des composés considérés, toujours sous forme libre ou sous forme de sel . L'invention concerne également un procédé relatif à l'élaboration des composés et de leurs tautomères, ainsi qu'à leur utilisation. L'invention concerne en outre des compositions pesticides, dont le principe actif est choisi dans le groupe des composés considérés et de leurs tautomères. L'invention concerne enfin un procédé relatif à l'élaboration des compositions visées et à leur utilisation, et des intermédiaires, sous forme libre ou sous forme de sel, entrant dans la préparation des composés, et le cas échéant leurs tautomères, sous forme libre ou sous forme de sel.
PCT/EP2001/008254 2000-07-19 2001-07-17 Tetrahydropyrimidines tenant lieu de pesticides WO2002006243A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1013441A (en) * 1961-10-19 1965-12-15 Shell Res Ltd Novel 2,6-dihalophenyl heterocyclic compounds and compositions containing them
FR2007450A1 (fr) * 1968-04-13 1970-01-09 Hoechst Ag Tetrahydro-pyrimidines et medicaments qui en renferment
EP0469685A1 (fr) * 1990-07-31 1992-02-05 Shell Internationale Researchmaatschappij B.V. Dérivés de tétrahydropyrimidine

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1013441A (en) * 1961-10-19 1965-12-15 Shell Res Ltd Novel 2,6-dihalophenyl heterocyclic compounds and compositions containing them
FR2007450A1 (fr) * 1968-04-13 1970-01-09 Hoechst Ag Tetrahydro-pyrimidines et medicaments qui en renferment
EP0469685A1 (fr) * 1990-07-31 1992-02-05 Shell Internationale Researchmaatschappij B.V. Dérivés de tétrahydropyrimidine

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