Imperial Chemical Industries Limited

Robin A Carr

Michael J Bushell

Alan J Whittle

Lyn Powell

Donn W Moseley

Nan C Sillars

This invention relates to novel fluorinated ethers, useful as insecticides and acaricides, to processes and intermediates for their preparation, to insecticidal and acaricidal compositions thereof and to methods of combating and controlling insect and acarine pests therewith.

Insecticidal ethers

A compound of formula: ##STR1## wherein W represents one or two substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy, or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Z represents a fluoroalkyl group of up to two carbon atoms; Y represents a substituted aryl group where such substituent is selected from halo, alkyl, aryl, aralkyl, aryloxy and arylamino; and either X' is hydrogen and X is selected from hydrogen, halo, hydroxy, alkoxy and aryloxy, or X and X' together represent a second bond between the adjacent carbon atoms. The compounds have useful insecticidal properties.

The invention provides insecticidally active compounds of formula (I): ##STR1## wherein X is nitrogen or carbon bearing a hydrogen atom; R.sup.1 is a group of formula --S(O).sub.n --Y, wherein Y is an optionally substituted heterocyclic ring containing at least one nitrogen atom, the point of attachment of the group Y being at a ring nitrogen atom, and n is 0, 1 or 2; R.sup.2 is a group of formula --OSO.sub.2 R.sup.3 wherein R.sup.3 is selected from C.sub.1-8 alkyl, C.sub.1-4 alkyl substituted by an optionally substituted phenyl or heterocyclic ring, C.sub.1-8 haloalkyl, C.sub.2-6 alkenyl, C.sub.2-4 alkenyl substituted by an optionally substituted phenyl or heterocyclic ring, C.sub.2-4 alkynyl, C.sub.2-4 alkynyl substituted by an optionally substituted phenyl or heterocyclic ring, optionally substituted aryl, and a group of formula --N(R.sup.4)(R.sup.5) wherein R.sup.4 and R.sup.5 are independently selected from hydrogen and C.sub.1-6 alkyl or wherein R.sup.4 and R.sup.5 together represent --(CH.sub.2).sub.p -- wherein p is 2, 3, 4 or 5; and wherein the groups R.sup.2 and R.sup.1 occupy either a 1,3 configuration relative to each other on the ring when X is carbon bearing a hydrogen, or a 2,4 or 2,6 configuration relative to the group X when X is nitrogen. The invention also provides compositions comprising the compounds of formula (I) and methods of their use in combating insect pests, and novel intermediates and chemical processes for their preparation.

Insecticidal compounds

The invention provides insecticidally active compounds of formula I: ##STR1## wherein A is selected from oxygen and a group of formula S(O).sub.n, where n represents 0, 1 or 2; W represents one or two substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy, or W represents a bidentate group linking adjacent carbon atoms, selected from alkylene and alkylenedioxy; Y represents a substituted aryl group where each substituent is selected from halo, alkyl, aryl, aralkyl, aryloxy and arylamino; Z represents a fluoroalkyl group of up to two carbon atoms; and either X' represents hydrogen and X is selected from hydrogen, halo, hydroxy, alkoxy and acyloxy, or X and X' together represent a second bond between the adjacent carbon atoms. The invention also provides processes and intermediates useful for the preparation of the compounds of formula I, insecticidal compositions comprising the compounds of formula I, and methods of combating and controlling pests therewith.

The invention provides novel arylalkene compounds of formula I, a process for their preparation and their use as intermediates for insecticidal compounds, comprising, ##STR1## wherein W represents 1 to 4 substituents selected from halo, alkyl, alkoxy, haloalkyl, haloalkoxy and alkoxyalkyl, or W represents a bidentate alkylene or alkylenedioxy group linking adjacent carbon atoms, X represents fluoroalkyl, and Y is selected from chlorine, bromine and alkoxy; and a process for preparing said ethers. The compounds of formula I are prepared by reacting a ketone of formula: ##STR2## with a phosphonium salt of formula Hal.sup.- (Q).sub.3 P.sup.+ --CH.sub.2 --Y, where Hal.sup.- represents a halide ion and Q represents alkyl or aryl.

Process for intermediates for insecticidal compounds

The invention provides insecticidally active compounds of formula: ##STR1## wherein X is N or CH; R.sup.a is the group (R.sup.1)(R.sup.2)NS(O).sub.n --wherein R.sup.1 and R.sup.2 are independently selected from H, alkyl, haloalkyl, alkoxy, alkoxyalkyl, formyl, alkanoyl, alkenyl, alkynyl, optionally substituted cycloalkyl, optionally substituted cycloalkylmethyl, optionally substituted benzyl and optionally substituted phenyl, and n is 0, 1 or 2; R.sup.b is the group --OSO.sub.2 R.sup.3 wherein R.sup.3 is alkyl optionally substituted by an optionally substituted phenyl group, haloalkyl, alkenyl optionally substituted by an optionally substituted phenyl group, optionally substituted aryl or N(R.sup.4)(R.sup.5), wherein R.sup.4 and R.sup.5 are independently selected from H and alkyl; and wherein the groups R.sup.a and R.sup.b occupy either a 1,3 configuration relative to each other when X is CH, or a 2,4 or 2,6 configuration relative to X when X is N. The invention provides insecticidal compositions comprising these compounds and methods of their use in controlling insects and also provides processes and intermediates for preparing the compounds.

Insecticidal compounds and compositions

The invention provides novel arylalkene compounds of formula I, a process for their preparation and their use as intermediates for insecticidal compounds, comprising, ##STR1## wherein W represents 1 to 4 substituents selected from halo, alkyl, alkoxy, haloalkyl, haloalkoxy and alkoxyalkyl, or W represents a bidentate alkylene or alkylenedioxy group linking adjacent carbon atoms, X represents fluoroalkyl, and Y is selected from chlorine, bromine and alkoxy; and a process for preparing said ethers. The compounds of formula I are prepared by reacting a ketone of formula: ##STR2## with a phosphonium salt of formula Hal.sup.- (Q).sub.3 P.sup.+ -CH.sub.2 -Y, where Hal.sup.- represents a halide ion and Q represents alkyl or aryl.

A compound of formula: ##STR1## wherein W represents one or more substituents selected from halo, alkyl, alkoxy, alkoxyalkyl, haloalkyl and haloalkoxy or W represents a bidentate group linking adjacent carbon atoms selected from alkylene and alkylenedioxy; Y is a group of formula ##STR2## wherein X is a group of formula --(CF.sub.2).sub.n R.sup.3, where R.sup.3 is selected from hydrogen, chloro and fluoro, and n is one or two, R.sup.1 is selected from hydrogen, chloro, fluoro and hydroxy and R.sup.2 is selected from methyl, cyano, ethynyl and hydrogen; Q is selected from carbon bearing a hydrogen atom and nitrogen; and Z represents one or more substituents selected from fluoro, benzyl, phenoxy, chlorophenoxy, fluorophenoxy and bromophenoxy, or any isomer thereof. Processes for preparing these compounds and intermediates for use therein, insecticidal compositions containing these compounds and the use thereof are also disclosed.

Growing community of inventors

Camberley, United Kingdom

Robin A Carr