Imperial Chemical Industries Limited

Michael J Robson

Mark A Spinney

John C Williams

Paul A Worthington

David J Milner

Peter J Cleare

Fungicidal compounds having the formula (I): ##STR1## wherein R.sup.1 is an optionally substituted phenyl group, C.sub.3-6 cycloalkyl optionally substituted by alkyl or alkyl; R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 are independently hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or N'R'; Z is a linking group and is --C.tbd.C--, --CR.sup.8 .dbd.CR.sup.10 -- or --CR.sup.8 R.sup.9 --CR.sup.10 R.sup.11 --; R.sup.8, R.sup.9, R.sup.10, R.sup.11, R' and R' are independently hydrogen or C.sub.1-4 alkyl; provided that when R is alkyl Z is not --CR.sup.8 R.sup.9 --CR.sup.10 R.sup.11 --; and acid addition salts or metal complexes thereof; and processes for preparing then, compositions comprising them and methods of using them to combat fungi.

Fungicidal pyridinylpyrimidine compounds

4-Haloalkenyl-2,3,5,6-tetrafluorobenzyl alcohols of formula (III): ##STR1## are intermediates to insecticidally active fluorobenzyl esters of formula (I): ##STR2## wherein X represents the residue of any carboxylic acid of formula X-COOH which forms an insecticidally active ester with a 3-phenoxybenzyl alcohol, and R, R.sup.6 and R.sup.7 are each selected from hydrogen, halogen and alkyl of up to four carbon atoms, provided that at least one of R, R.sup.6 and R.sup.7 represents halogen, and further provided that R and R.sup.6 are not both bromine when R.sup.7 is hydrogen.

Fluorobenzyl esters

The invention provides compounds of formula: ##STR1## wherein R.sup.1 represents hydrogen or halogen and R.sup.2 represents C.sub.1-8 alkyl or C.sub.1-8 haloalkyl, useful as insecticides and knockdown agents. The invention also provides compositions comprising them, methods of their use in controlling insects, and processes for their preparation.

Insecticidal compounds

Insecticidal compounds with effective knockdown activity against public health pests and having the general formula: ##STR1## wherein Z is selected from 3-allyl-2-methyl-4-oxocyclopent-2-en-1-yl; 3-propargyl-2-methyl-4-oxocyclopent-2-en-1-yl; 1-ethynyl-2-methylpent-2-en-1-yl; 3,4,5,6-tetrahydrophthalimidomethyl; (6-phenoxypyrid-2-yl)methyl; 1-cyano-1-(6-phenoxypyrid-2-yl)methyl; 1-propargylimidazolin-2,4-dione-3-ylmethyl; 5-benzylfur-3-ylmethyl; and a group of formula: ##STR2## wherein X represents hydrogen, hydroxy, methoxy or ethynyl. The invention also provides processes for the preparation of, and insecticidal compositions comprising, the compounds of formula (I).

Certain 3,3-bis-(difluoro methyl)2,2-dimethyl-cyclopropane carboxylates

Fluorobenzyl esters of the formula: ##STR1## wherein X represents the residue of any carboxylic acid of formula X-COOH which forms an insecticidally active ester with a 3-phenoxybenzyl alcohol, and R, R.sup.6 and R.sup.7 are each selected from hydrogen, halogen and alkyl of up to four carbon atoms, provided that at least one of R, R.sup.6 and R.sup.7 represents halogen, and further provided that R and R.sup.6 are not both bromine when R.sup.7 is hydrogen. The compounds are useful for combatting insect and acarine pests.

The invention provides insecticidal compositions exhibiting excellent knockdown activity against public health pests, in particular cockroach species, comprising compounds of formula (I): ##STR1## wherein X represents a group of formula: ##STR2## where (i) R.sup.1 and R.sup.2 are each selected from hydrogen, halo and C.sub.1-4 alkyl, or (ii) R.sup.1 is hydrogen and R.sup.2 represents either R.sup.3 (R.sup.4)C.dbd.CH-- or R.sup.3 (R.sup.4)(R.sup.5)C--CH(R.sup.5)--, where R.sup.3 and R.sup.4 are selected from hydrogen, methyl, halo and C.sub.1-2 haloalkyl and R.sup.5 is selected from chloro and bromo. The invention also provides methods of use of the compositions, novel compounds of formula (I) and processes for their preparation.

Insecticidal compounds characterized by enhanced knockdown effect

The compound 2-chloro-3,6-difluorobenzyl 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylate in any of its isomeric forms and mixture of these isomeric forms including racemates. Insecticidal compositions containing this compound and methods of using the compound against insect pests are also disclosed.

2-chloro-3,6-difluoro-benzyl halide

Compounds of formula (I), useful as insecticides and knockdown agents: ##STR1## where Y is C.sub.1-6 alkoxy, Z is halo or C.sub.1-6 alkoxy; R is --(CH.sub.2).sub.p --(O).sub.m --R.sup.3 where m and p may be 0 or 1; R.sup.3 is C.sub.1-6 alkyl, phenyl or benzyl, or when m is 0, R.sup.3 is C.sub.1-6 alkenyl, haloalkenyl, alkynyl or haloalkynyl, and either (a) A and B are both C.sub.1-4 alkyl or (b) A is hydrogen and B is (R.sup.1)(R.sup.2)C.dbd.CH-- where R.sup.1 and R.sup.2 are selected from methyl, chloro, bromo, fluoro and trifluoromethyl.

Halogenated esters

The invention relates to a method of combating soil-dwelling root worms of the genus Diabrotica which comprises treating the soil in which said root worms dwell with the compound 2-chloro-3, 6-difluorobenzyl (.+-.)-cis-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)- 2,2-dimethylcyclopropane carboxylate.

Insecticidally active ester

A process is described by which the pair of isomers represented by (R)-.alpha.-cyano-4-fluoro-3-phenoxybenzyl (1R,cis)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate and its enantiomer is converted by base catalyzed epimerization in solution into the insecticidally more useful isomer pair represented by (S)-.alpha.-cyano-4-fluoro-3-phenoxybenzyl (1R,cis)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate and its enantiomer, which may then be caused to crystallize out from the solution.

Process for the preparation of an enantiomeric pair of isomers of

A process is described by which the pair of cyhalothrin isomers represented by (R)-.alpha.-cyano-3-phenoxybenzyl (1R,cis)-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopro pane carboxylate and its enantiomer is converted by base catalyzed epimerization in solution into the insecticidally more useful isomer pair represented by (S)-.alpha.-cyano-3-phenoxybenzyl (1R,cis)-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopro pane carboxylate and its enantiomer, which may be caused to crystallize out from the solution.

Insecticidal product and preparation thereof

A novel crystalline material consisting of a enantiomeric pair of cyhalothrin isomers in the form of the racemic mixture and having greater insecticidal activity than cyhalothrin itself is described, together with a process for obtaining the enantiomeric pair of isomers by crystallization from concentrated cyhalothrin solutions in lower alkanols or liquid alkanes.

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Bracknell, United Kingdom

Michael J Robson