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EP-3694852-B1 - IMIDAZOLIDINE PYRIMIDINIUM COMPOUNDS FOR COMBATING ANIMAL PESTS

EP3694852B1EP 3694852 B1EP3694852 B1EP 3694852B1EP-3694852-B1

Inventors

  • DICKHAUT, JOACHIM
  • KUZMINA, Olesya
  • ADISECHAN, ASHOKKUMAR
  • DATTA, Gopal Krishna

Dates

Publication Date
20260506
Application Date
20181010

Claims (9)

  1. Compounds of formula (I): wherein Z is a direct bond; R 1 is C 1 -C 4 -alkyl or -CH 2 -phenyl; R 2 phenyl, -CH 2 -phenyl, -CH(CH 3 )-phenyl, or -O-CH 2 -phenyl, wherein the phenyl ring is unsubstituted, partially or fully substituted with halogen, CN, C 1 -C 3 -alkyl, C 1 -C 3 -haloalkyl, C 1 -C 3 -alkoxy, or C 1 -C 3 -haloalkoxy, preferably phenyl, 3,5-dichlorophenyl, 3-trifluoromethylphenyl, 3-difluoromethylphenyl, or 4-methoxyphenyl; R 3 is C 1 -C 3 -alkyl or C(=O)O-C 1 -C 4 -alkyl; Het is D-1, D-2, D-9, or D-27, wherein the index n is 1; R a is each independently halogen, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, or phenyl.
  2. Compounds of formula (I) according to claims 1, having the following stereochemistry of formula I-R
  3. Pesticidal mixtures comprising a compound of formula (I) as defined in any of claims 1 to 2, and another agrochemically active ingredient, preferably a pesticide, more preferably an insecticide and/or fungicide.
  4. An agrochemical or veterinary composition comprising a compound of formula(I), as defined in any of claims 1 to 2, or a pesticidal mixture as defined in claim 3, and a liquid or solid carrier.
  5. A method for controlling invertebrate pests, infestation, or infection by invertebrate pests, comprising contacting the pests, their food supply, habitat, breeding grounds or their locus with a compound of formula (I) as defined in any of claims 1 to 2 or a pesticidal mixture as defined in claim 3 in pesticidally effective amounts, where the method does not encompass the therapeutic treatment of the human or animal body.
  6. A method of protecting plants from attack or infestation by invertebrate pests comprising contacting the plant, or the soil or water in which the plant is growing, with a pesticidally effective amount of a compound of formula (I) as defined in any of claims 1 to 2 or a pesticidal mixture as defined in claim 3.
  7. A method for protection of plant propagation material comprising contacting the plant propagation material with a compound of formula (I) as defined in any of claims 1 to 2 or a pesticidal mixture as defined in claim 3 in pesticidally effective amounts.
  8. Seed, comprising a compound of formula (I) as defined in any of claims 1 to 2, or a pesticidal mixture as defined in claim 3 in an amount of from 0.1 g to 10 kg per 100 kg of seeds.
  9. The use of compounds of formula (I) as defined in any of claims 1 to 2, or of a pesticidal mixture as defined in claim 3, for combating invertebrate pests, where the use does not encompass the therapeutic treatment of the human or animal body.

Description

The present invention relates to insecticidal substituted imidazolidine pyrimidinium compounds and/or to the compositions comprising such compounds for combating invertebrate pests. The invention also relates to pesticidal methods, to uses and to applications of substituted imidazolidine pyrimidinium compounds as described in the present invention and the stereoisomers, salts, tautomers and N-oxides thereof as well as compositions comprising them. Invertebrate pests and in particular insects, arthropods and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, thereby causing large economic loss to the food supply and to property. While a large number of pesticidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an ongoing need for new agents for combating invertebrate pests such as insects, arachnids and nematodes. It is therefore an object of the present invention to provide compounds having a good pesticidal activity and showing a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control insects, arachnids and nematodes. It has been found that these objectives can be achieved by substituted imidazolidine pyrimidinium compounds of formula (I), as defined below, including their stereoisomers, their salts, in particular their agriculturally or veterinary acceptable salts, their tautomers and their N-oxides. The invention provides substituted imidazolidine-pyrimidinium compounds of formula (I) wherein Zis a direct bond, O S(O)m, NRb, C(RaRaa)O, C(=X1), C(=X1)Y1, or Y1C(=X1);X1is O, S, or NRb;Y1is O, S, or NRc;Hetis a three- to ten-membered heterocyclic ring, or a seven- to eleven-membered heterocyclic ring system, wherein the ring or ring system contains up to four ring members independently selected from O, S, and N(Rc)p with the proviso that up to two ring members are O, up to two ring members are S, and up to four ring members are N(Rc)p, and wherein up to 3 carbon atom ring members are independently replaced by C(=O) and C(=S), wherein the S-ring members are independently replaced by S(=O)o(=NRb)q, and wherein each ring or ring system is unsubstituted or substituted with up to five Ra; o, q are each independently 0, 1 or 2, provided that the sum (o + q) is 0, 1 or 2 for each ring;R1, R3are independently H; C1-C8-alkyl, C2-C8-alkenyl, C2-C8-alkynyl, C3-C10-cycloalkyl, C4-C10-cycloalkenyl, C5-C14-cycloalkylcycloalkyl, which groups are unsubstituted, or partially, or fully substituted with Ra; or a three- to eleven-membered saturated,partially unsaturated, or aromatic carbo-, or heterocyclic ring or ring system, which ring or ring system is unsubstituted, partially, or fully substituted with Ra, and wherein the heterocyclic ring or ring system contains 1 to 4 ring members independently selected from N(Rc)p, O, and S, wherein S is non-oxidized or oxidized; orC(=O)Rb, C(=O)ORe, NRbRc, C(=O)NRbRc, C(=S)NRbRc, SO2NRbRc, OC(=O)Rc, OC(=O)ORe, OC(=O)NRbRe, N(Rc)C(=O)Rc, N(Rc)C(=O)ORe, N(Rc)C(=O)NRbRc, NRcSO2Rb, NRcSO2NRbRc, Si(Rd)3, C(=NRc)Rc, C(=NORc)Rc,, C(=NNRbRc)Rc, C(=NN(C(=O)Rb)Rc)Rc, C(=NN(C=O)ORc)(Rc)2, S(=O)o(=NRb)qRc or N=CRbRc; Ra is each independently halogen, CN, ORc, NRbRc, NO2, C(=O)(O)pRc, OC(=O)(O)pRe, C(=O)NRbRc, OC(=O)NRbRe, NRbC(=O)(O)pRe , NRbC(=O)NRbRc, C(=S)NRbRc, S(O)mRb, SO2NRbRc, OSO2Rc, OSO2NRbRe, NRbSO2Rc, NRbSO2NRbRc, N=S(=O)pRcRc, S(=O)o(=NRb)qRc, SF5, OCN, SCN, Si(Rd)3;C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C4-alkenyl, C2-C4-alkynyl, C3-C6-cycloalkyl, which groups are unsubstituted, partially or fully substituted with Raa;a three- to six-membered saturated, or partially unsaturated or aromatic carbo-or heterocyclic ring, which ring is unsubstituted, partially, or fully substituted with Raa, wherein the heterocyclic ring contains 1 to 3 ring members independently selected from N(Rc)p, O, and S, wherein S is unoxidized or oxidized; ortwo geminally bound groups Ra together may form a group selected from =O, =S, =CRbRc, =NRc, =NORc, and =NNRcRc; Raa is each independently halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy; Rb is each independently H; C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, which groups are unsubstituted, partially or fully substituted with Raa; ora three- to six-membered saturated, or partially unsaturated or aromatic carbo-or heterocyclic ring, which ring is unsubstituted, partially, or fully substituted with Raa, wherein the heterocyclic ring contains 1 to 3 ring members independently selected from N(Rc)p, O, and S, wherein S is non-oxidized or oxidized; Rc is each independently H; C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkylcarbonyl, or C1-C6 cycloalkyl; or a three- to six-membered saturated, partially unsaturated or aromatic carbo- or heterocyclic ring, which ring is unsubstituted, partially, or fully substituted with Raa, wherein the heteroc