Imperial Chemical Industries Limited

Alan J Whittle

Trevor R Perrior

Roger Salmon

David J Tapolczay

Edward McDonald

Michael J Bushell

Robin A Carr

Raymond L Sunley

Alfred Glyn Williams

Michael G Hutchings

Donn W Moseley

Maureen Smith

Nicola J Bettesworth

Peter Doyle

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.

Phenyl substituted heterocyclic compounds having insecticidal activity have the formula (I): ##STR1## wherein R.sup.1 is an optionally substituted pyridone, thiopyridone, pyrimidinthione, pyrimidinone, pyrazole, imidazole or triazole group; R.sup.2 is hydrogen, halogen, haloalkyl, nitro, cyano or a group --CX--NY.sup.1 Y.sup.2 ; R.sup.3 and R.sup.5 are hydrogen, halogen, alkyl or cycloalkyl; R.sup.4 is halogen, haloalkyl, haloalkoxy or S(O).sub.n R.sup.6 ; and Y.sup.1 and Y.sup.2 are independently selected from hydrogen, nitro, amino or optionally substituted alkyl or Y.sup.1 and Y.sup.2 together with the nitrogen to which they are attached form an aliphatic heterocyclic group or form the group .dbd.CHY.sup.3 or Y.sup.1 is hydrogen and Y.sup.2 is alkoxycarbonyl, alkylcarbonyl, optionally substituted aralkyl or --S(O).sub.n R.sup.6.

1-phenyl substituted pyrimidone derivatives

A pyrimidinone compound of formula (IIIA) or (VA): ##STR1## wherein R.sup.13 is hydrogen, halogen or cyano and R.sup.14 is halo or haloalkyl with the proviso that (a) when R.sup.13 is cyano, R.sup.14 is other than chlorine; (b) R.sup.13 and R.sup.14 are not both halo; (c) when R.sup.13 is halo R.sup.14 is other than monofluoromethyl; and (d) when R.sup.13 is hydrogen R.sup.14 is not halo or a halomethyl group; ##STR2## wherein R.sup.10 is hydrogen or C.sub.1-4 alkyl; R.sup.15 is cyano and R.sup.16 is R.sup.6 is defined in relation to formula (V) or R.sup.15 is hydrogen or halogen other than fluorine and R.sup.16 is pentafluoroethyl or difluoromethyl. These compounds are useful as intermediates in the preparation of insecticidal compounds.

Pyrimidine compounds

A phenyl substituted heterocyclic compound of formula (I): ##STR1## wherein R.sup.1 is optionally substituted pyridone, thiopyridone, pyrimidinthione, pyrimidinone, pyrazole, imidazole or triazole group; R.sup.2 is hydrogen, halogen, haloalkyl, nitro or cyano; R.sup.3 and R.sup.5 are independently selected from hydrogen, halogen, alkyl or cycloalkyl; R.sup.4 is halogen, haloalkyl, haloalkoxy or S(O).sub.n R.sup.6 where R.sup.6 is alkyl, haloalkyl or cycloalkyl and n is 0, 1 or 2; having insecticidal activity.

Pyrimidine

A compound of formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently selected from hydrogen, halogen, haloalkyl, alkoxy or nitro, provided that R.sup.1 and R.sup.2 are not both nitro; R.sup.3 and R.sup.4 are independently selected from hydrogen, halogen, alkyl or cycloalkyl; R.sup.5 is halogen, nitro, haloalkyl, haloalkoxy or --S(O).sub.n R.sup.10 ; R.sup.6 is halogen, nitro, haloalkyl, haloalkoxy or --S(O).sub.n R.sup.10 ; R.sup.7 is hydrogen, halogen, hydroxyalkyl, cyano, nitro, alkoxy, --S(O).sub.n R.sup.10, NR.sup.11 R.sup.12, haloalkyl or formyl; R.sup.8 is hydrogen, halogen, NR.sup.11 R.sup.12, alkyl, cycloalkyl or S(O).sub.n R.sup.10 ; and R.sup.9 is oxygen or sulphur; where n is 0, 1 or 2; and R.sup.10 is alkyl, haloalkyl or cycloalkyl; and R.sup.11 and R.sup.12 are independently selected from hydrogen, alkyl or cycloalkyl or R.sup.11 and R.sup.12 together with the nitrogen to which they are attached form a heterocyclic group; provided that when R.sup.5 is trifluoromethyl at least one of the following applies:

1-phenyl-6-one-pyrimidine derivatives

Insecticidal compounds of formula (I) ##STR1## wherein R.sup.1 and R.sup.2 are independently selected from halogen or nitro; R.sup.3 and R.sup.4 are independently selected from hydrogen or halogen; R.sup.5 is hydrogen, halogen or cyano; and R.sup.6 is halogen or haloalkyl; provided that R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are not all fluorine.

Novel compounds

This invention provides novel insecticidally and acaricidally active pyrimidine derivatives of formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is selected from alkyl; alkenyl; alkynyl; haloalkyl; haloalkenyl; and cycloalkyl optionally substituted by alkyl or halogen;

Pyrimidine derivatives

An insecticidal compound of formula (I): ##STR1## wherein R.sup.1 and R.sup.3 are independently selected from hydrogen; halogen; nitro; cyano; or alkyl, alkoxy, alkylthio or cycloalkyl any of which can be optionally substituted by halogen; R.sup.2 is hydrogen; halogen; nitro; cyano; alkyl, alkoxy or alkylthio any of which may be optionally substituted with halogen; or S(O).sub.n R.sup.8, where R.sup.8 is alkyl, haloalkyl or cycloalkyl and n is 0, 1 or 2; R.sup.4 is hydrogen; halogen; nitro; cyano; or alkyl, alkoxy or alkythio any of which may be optionally substituted with halogen; R.sup.5 is hydrogen; halogen; nitro; cyano; alkyl, alkoxy alkylthio any of which can be optionally substituted with halogen; or NR.sup.9 R.sup.10 where R.sup.9 and R.sup.10 are independently selected from hydrogen, alkyl or cycloalkyl; R.sup.6 is hydrogen; halogen; nitro; cyano; alkyl, alkoxy or alkylthio any of which can be optionally substituted with halogen; or S(O).sub.n R.sup.8 ; R.sup.7 is hydrogen; halogen; nitro; cyano; alkyl; alkoxy or alkythio any of which is optionally substituted with halogen; S(O).sub.n R.sup.8 ; or NR.sup.9 R.sup.10 ; and Z is oxygen or sulphur.

Pyridyl-pyrimidones

Insecticidally and acaricidally active pyrimidine esters and

Certain phenoxy- or benzyl substituted pyridylmethyloxy-alkenes having

A compound of formula: ##STR1## wherein R is selected from hydrogen, cyano, methyl, and ethynyl, and X represents the residue of any carboxylic acid of formula X-COOH which forms an insecticidally active ester with a 3-phenoxybenzyl alcohol. The compounds are useful as insecticides and acaricides.

Fluorobenzyl esters

Compounds of the formula: ##STR1## wherein X is selected from bromine and chlorine useful as intermediates in the preparation of insecticidal compounds.

Trihalobenzene compounds

Insecticidal alkenes

Insecticidally active compounds of the formula (I): ##STR1## wherein R.sup.4 represents a group selected from those groups represented by R.sup.5 in insecticidally active compounds of formula: ##STR2## R.sup.3 is selected from fluoromethyl and difluoromethyl, and either (a) R.sup.1 and R.sup.2 represent alkyl of one, two, three or four carbon atoms, or (b) R.sup.1 and R.sup.2 taken together with the adjacent carbon atom form a cycloalkyl ring of four, five or six carbon atoms.

Growing community of inventors

Twyford, United Kingdom

Alan J Whittle