CA1166652A - Benzyloxime ethers - Google Patents

Abstract

A B S T R A C T
Insecticidally-active compounds of the following general formula:- wherein Rl is an optionally-substituted aryl or alkyl group;
R2 is an optionally-substituted cycloalkyl group;
X is an oxygen atom or a methylene group;
Y is a hydrogen or halogen atom, or alkyl or alkoxy group;
and n is an integer of 1 to 5.

Claims (14)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. A compound of general formula I:

(I) wherein R1 represents a naphthyl group, an optionally substituted phenyl group of general formula II:

(II) wherein Z is a hydrogen or halogen atom, or an alkyl or alkoxy group, and m is an integer of 1 to 5, or an optionally-substituted alkyl group of up to 10 carbon atoms, the substituents being one or more halogen atoms, or alkoxy or aryl groups;
R2 represents cyclobutyl or an optionally substituted cyclopropyl group of general formula III:

(III) wherein Ra and Rb both represent hydrogen atoms, alkyl groups having from 1 to 6 carbon atoms, or halogen atoms, or Ra and Rb together represent an alkylene group having from 2 to 6 carbon atoms; or Ra represents a hydrogen atom and Rb represents an alkenyl group having from 2 to 6 carbon atoms, or a haloalkenyl group having from 2 to 6 carbon atoms and from 1 to 3 chlorine or bromine atoms; Rc and Rd both represent hydrogen atoms, alkyl groups having 1 to 6 carbon atoms, or RC is hydrogen and Rd is an alkenyl group having from 2 to 6 carbon atoms, or a haloalkenyl group having from 2 to 6 carbon atoms and from 1 to 3 chlorine or bromine atoms; or Rc and Rd together represent an alkylene group having from 2 to 6 carbon atoms;

X is an oxygen atom or a methylene group;
Y is a hydrogen or halogen atom, or alkyl or alkoxy group;
and n is an integer of 1 to 5.

2. A compound according to claim 1 wherein Y represents a hydrogen atom or an alkyl or alkoxy group of 1 to 4 carbon atoms or a halogen atom.

3. A compound according to claim 1 having the following general formula:

(IV) wherein R1 is phenyl, chlorophenyl, dichlorophenyl, bromophenyl, dibromophenyl, fluorophenyl, difluorophenyl, methylphenyl, dimethyl-phenyl, methoxyphenyl, butylphenyl, ethylphenyl, or naphthyl; and Y is hydrogen, chlorine, fluorine or bromine.

4. A compound according to claim 1,2 or 3 which is in the form of its E-isomer or a mixture of the E- and Z-isomers in which the E-isomer predominates.

5. A process for the preparation of a compound of formula I as defined in claim 1, wherein the alkali metal salt of a ketoxime of formula:
(V) wherein R1 and R2 are as defined in claim 1, is reacted with a substituted benzyl halide of formula:

(VI) wherein X, Y and n are as defined in claim 1 and Q is a halogen atom.

6. A process according to claim 5 wherein the alkali metal salt of the ketoxime is prepared by the reaction of an alkali metal hydride with the ketoxime or by the reaction of aqueous potassium or sodium hydroxide with the ketoxime.

7. A process according to claim 5 or 6 wherein the alkali metal salt of the ketoxime is prepared in situ.

8. A method of combating insect, tick and/or acarid pests at a locus which comprises applying to the locus a pesticidally effective amount of a benzyl oxime ether according to claim 1,2 or 3.

9. A compound according to claim 1 having the following general formula (IV) wherein R1 is 4-fluorophenyl, 4-chlorophenyl or 4-bromophenyl.

10. A method of combatting Spodoptera littoralis pests at a locus which comprises applying to the locus where Spodoptera littoralis is present a pesticidally effective amount of a compound of claim 9.

11. A method of combatting Heliothis zea pests at a locus which comprises applying to the locus where Heliothis zea is present a pesti-cidally effective amount of a compound of claim 9.

12. A compound of the formula wherein A is naphthyl or a phenyl of the formula B is cyclopropyl, halo substituted cyclopropyl, or cyclobutyl D is -CH2- or -O-E and G are separately hydrogen, halogen, alkyl or alkoxy and a is an integer from 1 to 5.

13. A process for preparing a compound of the formula wherein A, B, D, E and a are as defined in claim 12 which comprises reacting an alkyl metal salt of a ketoxime of the formula = N - OH

with a benzyl halide of the formula wherein K is a halogen atom.

14. A method for combatting insects which comprises contacting them with an insecticidally effective amount of a compound of claim 12.