Patent EA-002064-B1 (EA)
Title: Pesticide compounds, compositions and process for the preparation thereof
Inventor: ARVAI GEZA
IPC: C07C43/166
Filed: 1996-11-19
Abstract: 1 .Compounds of the general formula I,    their optically active isomers and salts, wherein Ar = C3-C6 alycylic, aromatic or 5- heterocyclic moiety, containing one or two nitrogen atoms and/or one or two oxygen atoms optionally substituted by one or more C1-C4 alkoxy-, methylenedioxy-, C1-C6 alkyl-, C1-C6 haloalkyl-, or a nitro-group, a halo atom and/or condensed with a benzene ring; R<1>, R<2> - independently H, C1-C6 alkyl, C1-C6 alkenyl, C1-C6 haloalkyl, phenyl, C3-C6 cycloalkyl, R<3>, R<4> = independently H, C1-C6 alkyl, C1-C6 alkenyl, C1-C6 haloalky, phenyl, C1-C6 cycloalkyl, or R<3>, R<4> are together = O; Y = C or YR<3>R<4> form together a   X=-O-;-NR<10>-; R<9> = H, C1-C6 alkyl, phenyl; R<10>=H, C1-C6 alkyl; R<5>, R<6>, R<7>, R<8> are independently H, C1-C6 alkyl, C1-C6 alkenyl, C1-C6 haloalkyl; E = H, methyl; m=0,1,2; n=0,1; o=0,1,2; p=0,1,2; with the proviso that the sum of the atoms or groups of the - (CR<1> R<2>)m - (CR<3>R<4>)n - X - (CR<5>R<6>)o - (CR<7>R<8>)p bridge sceleton is 3 and the -C  [triple bond]  C - E sceleton forms with the atoms of the bridge a linear chain, consisting of 6 atoms ending favourably in a methyl group, furthermore with the proviso, that if Ar stands for a naphthyl group, Y means C-atom, X means O-atoms, R<3> and R<4> together cannot mean = O,  or if Ar stands for a phthalimide group, R<1> means methyl, m = 0, n = 0, o = 1, R<5> and R<6> are H atoms, E is not H, or if Ar is naphthyl, m is 0, n is 0, X is O, R<5>, R<6>, R<6>, R<7> and R<8> are H atoms, E is not H, or if Ar is phenyl or which may be substituted or naphthyl, m is 0, n is 1, X is O-atom, Y is C-atom, R<3> and R<4> are each H or R<3> and R<4> are together O atom, or YR<3>R<4> are together R<9> --C.dbd.N, where R<9> is H or alkyl, E is not H. 2. Compounds of the general formula IA    and their optically active isomers,where Ar, R<1>, R<2>, R<5>, R<6>, R<7>, R<8>, Y, E, m, o, and p have the same meanings as defined in claim 1. 3. Compounds of the general formula IB    and their optically active isomers, where Ar, R<1>, R<2>, R<5>, R<6>, R<7>, R<8>, R<10>, Y, E, m, o, and p have the same meanings as defined in claim 1. 4. Compounds of the general formula IC    and their optically active isomers, where Ar, R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7>, R<8>, E, m, n, o, and p have the same meanings as defined in claim 1. 5. Compounds of the general formula ID    where Ar, R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7>, R<8>, R<10>, E, m, n, o, and p have the same meanings as defined in claim 1. 6. Compounds of the general formula IE   and their optically active isomers, where Ar, R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7>, R<8>, R<10>, E, m, n, o, and p have the same meanings as defined in claim 1. 7. Compounds of the general formula IF    and their optically active isomers,where Ar, R<1>, R<2>, R<5>, R<6>, R<7>, R<8>, R<9>, E, m, o, and p have the same meanings as defined in claim 1. 8. Compounds according to claim 1, 1-naphthyl-methyl-2-butynyl ether, 2-propynyl-1,3-benzodioxol-5-carboxylate, 1-[(2-butynyloxy)-ethyl]-3,4-dimethoxybenzene, 2,6-dichloro-1-(2-butynyloxy-methyl)benzene, 1-[1-(2-butynyloxy)propyl]naphthalene, R-(+)-2-[1-(2-butynyloxy)ethyl]naphthalene, 5-[(but-2-ynyloxy)methyl]-1,3-benzodioxole, 5-[2-methyl-1-(2-butynyloxy)propyl]-1,3-benzodioxole, 5-[(but-2-ynyloxy)phenylmethyl]-1,3-benzodioxole, 2-[2-butynyloxy)methyl]-1,4-benzodioxane, 2,3-dihydro-2,2-dimethyl-7-(3-pentyloxy)benzofurane. 9. Process for the preparation of compounds of the general formula I as herein defined where Ar, R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7>, R<8>, R<10>, X, Y, E, m, n, o, and p have the same meanings as defined in claim 1, characterized by, that a.) for the preparation of compounds of the general formula IA as herein defined, where Ar, R<1>, R<2>, R<5>, R<6>, R<7>, R<8>, Y,E, m, o, and p, have the same meanings as defined in claim 1, compounds of the general formula II and III are reacted.   where Ar, R<1>, R<2>, R<5>, R<6>, R<7>, R<8>, Y, E, m, o, and p, have the same meanings as defined in claim 1, A and B are groups suitable to form ester bond. b.) to prepare compounds of formula IB as herein defined, wherein Ar, R<1>, R<2>, R<5>, R<6>, R<7>, R<8>, R<10>, Y, E, m, o, and p, have the same meaning as defined in claim 1, compounds of general formula IV and V are reacted.   wherein Ar, R<1>, R<2>, R<5>, R<6>, R<7>, R<8>, Y, E, m, o, and p, have the same meaning as defined in claim 1, and C and D stand for groups suitable to form amide bond. c.) to prepare compounds of general formula IC as herein defined, wherein Ar, R<1>, R<2>, R<5>, R<6>, R<7>, R<8>, E, m, n, o, and p, have the same meaning as defined in claim 1, R<3> and R<4> independently mean H, alkyl, alkenyl, haloalkyl, phenyl, substituted phenyl, compounds of general formula VI and VII are reacted.   wherein Ar, R<1>, R<2>, R<5>, R<6>, R<7>, R<8>, Y, E, m, n, o, and p, have the same meaning as defined in claim 1. R<3> and R<4> independently mean H, alkyl, alkenyl, haloalkyl, phenyl, substituted phenyl, F and G stand for groups, suitable to form ether bond. d.) to prepare compounds of general formula ID as herein defined, wherein Ar-(CR<1>R<2>)m-(CR<2>R<4>)n-N- stands for carboximide groups R<5>, R<6>, R<7>, R<8>, E, o, and p, have the same meaning as defined in claim 1, the carboximide of general formula Vin is reacted with the compounds of general formula IX.   wherein R<5>, R<6>, R<7>, R<8>, E, o, and p, have the same meaning as defined above and Lg stands for a leaving group. e.) to prepare compounds of general formula IE as herein defined, wherein Ar, R<1>, R<2>, R<5>, R<6>, R<7>, R<8>, R<10>, E, m, n, o, and p, have the same meaning as defined in claim 1, compound of general formula X and XI are reacted.   wherein Ar, R<1>, R<2>, R<5>, R<6>, R<7>, R<8>, E, m, n, o, and p, have the same meaning as defined in claim 1. H and I stand for a group, suitable to form a   group, wherein Rio has the same meaning as defined in claim 1. f.) to prepare compounds of general formula IF as herein defined, wherein Ar, R<1>, R<2>, R<5>, R<6> R<7>, RS, R<9>, E, m, o, and p, have the same meaning as defined in claim 1, compound of general formula XII and IX as herein defined are reacted.   wherein Ar, R<1>, R<2>, R<5>. R<6>, R<7>, R<8>, R<9>, E, m, n, o, and p, have the same meaning as defined in claim 1, and Lg stands for a leaving group, and if desired, the compound of the general formula I as herein defined can be transformed into its salts, or liberated from its salts and, if desired, the optically active isomers can be separated. 10. Pesticide composition comprising as active ingredient 0.0001-99-9% by mass of a compound of the general formula I as defined in claim 1, where Ar, R<1>, R<2>, R<3>, R<4> R<5>, R<6>, R<7>, RS, R<9>, RIO, m, n, o, and p, have the same meanings as defined in claim 1, and optionally other pesticide active ingredient(s), beside carriers and other auxiliary materials. 11. Arthropodicide composition comprising as active ingredient 0.0001-99.9% by mass of a compound of the general formula I as defined in claim 1, where Ar, R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7>, RS, R<9>, RIO, m, n, o, and p, have the same meanings as defined in claim 1, and optionally other arthropodicide active ingredient(s) beside carriers and other auxiliary materials. 12. Composition according to claim 11, characterized in that it contains as other active ingredient: Acetamide derivatives: e.g. oxamyl; Benzoylurea compounds: e.g. flucycloxuron, hexaflumuron, teflubenzuron, triflumuron; Benzoylurea like IGR compounds; Bicycloheptadien compounds: e.g. heptenophos; Cross-bridged diphenyl compounds: e.g. etofenprox, bromopropylate, methoxycholor, temephos, tetradifon; Carbamates: e.g. aminocarb, aldicarb, aldoxycarb, asulam, bendiocarb, benfuracarb, carbaryl, carbetamide, carbofuran, carbosulfan, diethofencarb, dioxacarb, ethiofencarb, fenobucarb, fenoxycarb, furathiocarb, isoprocarb, methornyl, oxamyl, pirimicarb (pirimor), propoxur, thiodicarb, thiofanox, xylylcarb; Carbamoyloxime derivatives: e.g. alanycarb, butocarboxim; Cyclodienes: e.g. aldrin, chlordane, endosulfan, heptachlor; Diazoles: tipronil; Hydrazides: RH 5992, RH 5849, CGA 215'944; Nereistoxm analogues: pi. bensultap; Nitroimidazolidynylenamines: e.g. imidacloprid; Organophosphor compounds: e.g. quinalphos, diazinon, phosalone, dimethoate, azinphos-methyl; Organotin compounds: e.g. azocyclotin, cyhexatin, fenbutatin oxide SSI-121; Phenoxy compounds: e.g. diafenthiuron; Pyrazoles: e.g. pyrazophos; Pyrethroides: e.g. allethrin, bioallethrin (esbol), acrinathrin, fenvalerate, empenthrin, prallethrin, resmethrin, MTI-800, flufenprox, permethrin, tetramethrin, cypermethrin and their isomers and isomer-combinations; Pyridazinones: e.g. pyridaben; Pyridine derivatives: e.g. chlorpyriphos; Pyrimidine derivatives: e.g. pyrimiphos-ethyl, pyrimiphos-methyl; Pyrroles: e.g. AC 303-t, 630; Quinazolines: e.g. fenazaquin; Terpenoid derivatives: e.g. methoprene; Tetrazines: e.g. clofentezine, Szl-121 (flufenzin); Thiadiazines: e.g. buprofezin; Thiazolidin: pi. hexythiazox; Triazoles: pi. isazophos. RH 7988; Chlorinated hydrocarbons: lindane; Macrocyclic lactones; Tebufenpyrad; Fenpyroxymate; Triazamate. 13. Compositions according to claims 11 and 12, comprising as active ingredient of general formula I as defined in claim 1, one or more of the following compounds: 1-naphthyl-methyl 2-butynyl ether, 2-propynyl-1,3-benzodioxol-5-carboxylate, 1-[(2-butynyloxy)-ethyl]-3,4-dimethoxybenzene, 2,6-dichloro-1-(2-butynyloxy-methyl)benzene, 1-[1-(2-butynyloxy)propyl]naphthalene, R-(+)-2-[1-(2-butynyloxy)ethyl]naphthalene, 5-[(but-2-ynyloxy)methyl]-1,3-benzodioxole, 5-[2-methyl-1-(2-butynyloxy)propyl]-1,3-benzodioxole, 5-[(but-2-ynyloxy)phenylmethyl]-1,3-benzodioxole, 2-[2-butynyloxy)methyl]-1,4-benzodioxane, 2,3-dihydro-2,2-dimethyl-7-(3-pentyloxy)benzofurane. 14. Composition according to claims 11 to 13, comprising as active ingredient 0.0001-99.9%