Patent EA-000468-B1 (EA)
Title: Bicyclic amines and their use as insecticides
Inventor: URCH CHRISTEPHER JOHN
IPC: C07D401/04
Filed: 1996-05-13
Abstract: 1. A compound of formula (I):   wherein R<1> represents a group of formula (A)   where each of W, X, Y and Z represents either a group CR or the nitrogen atom, provided that not more than two of W, X, Y and Z represent the nitrogen atom and where each R present is independently selected from hydrogen and halogen atoms and cyano, amino, hydrazino, acylamino, hydroxy, alkyl, hydroxyalkyl, alkoxy, haloalkyl, haloalkoxy, alkenyl, alkenyloxy, alkoxyalkenyl, alkynyl, carboxylic acyl, alkoxycarbonyl, aryl and heterocyclyl groups, said groups comprising up to 6 carbon atoms, and wherein R<2> represents hydrogen or cyano or a group selected from alkyl, aryl, heteroaryl, aralkyl, hetcroarylalkyl, alkenyl, aralkenyl, alkynyl, alkoxycarbonyl, alkanesulfonyl, arenesulfonyl, alkanyloxycarbonyl, aralkyloxycarbonyl, aryloxycarbonyl, heterocyclylalkyl, carbamyl or dithiocarboxyl groups, said groups comprising from 1 to 15 carbon atoms, said groups being optionally substituted with one or more substituents selected from, halogen, cyano, carboxyl, carboxylic acyl, carbamyl, alkoxycarbonyl, alkoxy, alkylenedioxy. hydroxy, nitro, haloalkyil alkyl, amino, acylamino, imidate and phosphonato groups; and acid addition salts, quaternary ammonium salts and N-oxides derived therefrom., and wherein R<1> represents 5-chloropyride-3-yl, then R<2> can represent acetyl, trifluoroacetyl, 4-chlorobenzoyl, 4-fluorobenzoyl, formyl, fluorocarbonyl, N-methyl-N-phenyl carbamyl, 4-morpholynocarbonyl, N-(3-choro-4-fluirophenul)carbamyl, 4-allyl-2,3,5,6-tetrafluorobenzyl, 3-trifluorometoxybenzyl, 2-N-succinimido)benzyl, 4-(1,2,3-thiadiazole-4-yl)benzyl, 3-(4-fluorophenoxy)benzyl, 2-phenoxyethyl, cyclogexymethyl, metoxy or methylmercaptothiocarbonyl; provided that R<1> is not substituted phenyl, when R<2> is not substituted benzyl or tozyl. 2. A compound according to Claim 1 wherein R' represents a halo-substituted phenyl, pyridyl or diazinyl group. 3. A compound according to Claim 1 where R<1> represents an optionally halogen substituted phenyl group or an optionally halogen substituted pyridyl, pyridazinyl or pyrazinyl group and R<2> represents hydrogen or a C1-6 alkyl, alkenyl, alkynyl, phenyl, benzyl, pyridylmethyl, thienylmethyl, thiazolylmethyl group which may be optionally substituted with one or more alkyl, alkoxy, alkoxycarbonyl, cyano, optionally substituted alkane sulphonyl groups or halogen atoms; and acid addition salts thereof. 4. A compound according to Claim 1 wherein R<1> is a halo-substituted pyridyl group. 5. A compound according to Claim 1 wherein R<2> is a hydrogen or haloalkyl, haloalkenyl or haloaralkyl group. 6. A compound according to Claim 4 wherein R<2> is a haloalkyl or haloalkenyl group. 7. A compound according to Claim 6 wherein R<2> is a fluoroalkyi or fluoroalkenyl group. 8. A compound according to Claim 4 where R<1> is a 5-halopyrid-3-yl group. 9. A compound according to Claim 8 wherein R<2> is fluoroethyl, difluoroethyl or trifluoroethyl. 10. An insecdcidal acaricidal and nematicidal composition comprising an insecucidally, acaricidally or nemadcidally effective amount of a compound according to Claim 1. 11. A method of combating and controlling ticks, acerine or nematode pests at a locus which comprises treating the pests or the locus of the pests with an effective amount of a composition according to Claim 10. 12. A method according to Claim 11 wherein the pests are insect pests of growing plants. 13. A method of preparing a compound of formula (I) where R<2> is not hydrogen which comprises reacting a compound of formula (II):   with a compound of formula R<2>L where L is a leaving group in the presence of a base. 14. A process according to Claim 13 wherein L represents halide or triflate. 15. A process of preparing a compound of formula (I) which comprises reacting a compound of formula (VI):   with a compound of formula R<1>Hal where Hal is a halide in the presence of a base. 16. A process of preparing a compound of formula (VI):   which comprises reacting a compound of formula (YII):   with a compound of formula R<2>L where L is a leaving group in the presence of a base. 17. A compound of formula (VI):   wherein R<2> represents hydrogen or cyano or a group selected from alkyl, aryl, heteroaryl, aralkyl, hetcroarylalkyl, alkenyl, aralkenyl, alkynyl, alkoxycarbonyl, alkanesulfonyl, arenesulfonyl, alkanyloxycarbonyl, aralkyloxycarbonyl, aryloxycarbonyl, heterocyclylalkyl, carbamyl or dithiocarboxyl groups, said groups comprising from 1 to 15 carbon atoms, said groups being optionally substituted with one or more substituents selected from, halogen, cyano, carboxyl, carboxylic acyl, carbamyl, alkoxycarbonyl, alkoxy, alkylenedioxy. hydroxy, nitro, haloalkyil alkyl, amino, acylamino, imidate and phosphonato groups; and acid addition salts, quaternary ammonium salts and N-oxides provided that R<2> is not methyl, 3-methylbutyl, H-hexyl, cyclogexylmethyl, benzyl 4-chlorobenzyl, 4-methylbenzyl, 4-metoxybenzyl, 3,4-dichlorobenzyl, 3-trifluoromethylbenzyl, 2-phenetyl, 2-thienyl or trichloroethyl.