Patent EA-001422-B1 (EA)
Title: Bicyclic amines as insecticides
Inventor: SALMON ROGER
IPC: C07D451/02
Filed: 1997-05-09
Abstract: 1. A compound of formula (I) or formula (II)   wherein R<1> represents a group of formula (A)   where each of W, X, Y and Z 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 a group X'R<3> where X' represents oxygen or a group NR<4> where R<3> and R<4> are individually selected from hydrogen or a group selected from alkyl, aryl, heteroaryl, aralkyl, heteroarylalkyl, alkenyl, aralkenyl, alkynyl, heterocyclylalkyl, alkoxycarbonyl, and carboxylic acyl 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, haloalkyl and alkyl groups; said groups comprising up to carbon atoms; and heterocyclyl comprises one non-aromatic ring and heteroaryl comprises one aromatic ring, each of which comprises 5, 6 or 7 atoms, comprising one or two heteroatoms selected from O, S and N; and acid addition salts and quaternary ammonium salts and N-oxides derived therefrom. 2. A compound according to claim 1 wherein R<1> 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, pyridazin yl or pyrazinyl group and X' represents oxygen and R<3> represents hydrogen or a C1-6 alkyl, C1-6 alkenyl, C1-6 alkynyl, phenyl, benzyl, acetyl or benzoyl group which may be optionall y substituted with one or more C1-6 alkyl, C1-6 alkoxy, C1-6 alkoxycarbonyl or cyano 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, X' is oxygen and R<3> is a C1-6 alkyl group. 5. An insecticidal acaricidal and nematicidal composition comprising an insecticidally, acaricidally or nematicidally effective amount of a compound according to claim 1. 6. A method of combating and controlling 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 5. 7. A method according to claim 11 wherein the pests are insect pests of growing plants. 8. 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. 9. A compound of formula (VI)   wherein R<2> has any of the meanings given in claim 1. 10. A process for preparing a compound of formula (VI) which comprises the steps  of:  (a) reacting cyclohepta-2,6-dienone with a compound of formula R<2>NH2, where R<2> is as defined in claim 1, to obtain a compound of formula (VIII)   and (b) reacting t he compound of formula (VIII) with an arene sulphonyl methyl isocyanide.