Drug – bio-affecting and body treating compositions – Nonspecific immunoeffector – per se ; or nonspecific... – Bacterium or component thereof or substance produced by said...
Patent
1981-07-09
1983-02-08
Ford, John M.
Drug, bio-affecting and body treating compositions
Nonspecific immunoeffector, per se ; or nonspecific...
Bacterium or component thereof or substance produced by said...
424258, 424274, 424275, 424283, 424285, 546166, 548510, 549 58, 549407, 549433, 549466, 549471, C07D30778, A01N 4308
Patent
active
043729703
DESCRIPTION:
BRIEF SUMMARY
This invention relates to pesticides and in particular to certain substituted acetic acid esters as compounds, to pesticidal compositions containing them and to methods of killing pests especially insects and arachnids using the compounds of the invention or compositions containing them.
It is well known that certain esters of chrysanthemumic and related acids have potent insecticidal properties. Such insecticides are known as pyrethroid insecticides. The naturally occurring pyrethroid insecticides are esters of derivatives of cyclopropanecarboxylic acid. Attention in recent years has been focussed on this general class of pesticides because they do not suffer from the disadvantages which have become increasingly associated with the use of organohalogen and organophosphorous pesticides.
Apart from the development of closely similar analogues to the naturally occurring pyrethroids and in particular to compounds based on cyclopropanecarboxylic acid, compounds not containing a cyclopropane ring have been investigated and it has been found that certain classes of substituted acetic acid esters and in particular substituted phenylacetic acid esters have insecticidal properties similar to those of the naturally occurring pyrethroids. Such materials are conventionally included under the classification of "synthetic pyrethroids". British Pat. No. 1,439,615, for example, describes certain classes of substituted acetic acid esters having pesticidal properties. Of the compounds within the claims of this Sumitomo patent we are aware that .alpha.-cyano-3-phenoxy-benzyl 2-(4-chlorophenyl)-3-methylbutyrate, known by the trivial name Fenvalerate has come into commercial use.
The present invention is based on the discovery that certain classes of fused bicyclic derivatives of substituted acetic acid form esters which have marked insecticidal properties.
The present invention accordingly provides compounds of the general formula (I): ##STR1## where: R.sub.1 and R.sub.2 together represent a residue of any one of the general formulae: ##STR2## where
X is an oxygen or a sulphur atom, or a --NH-- group;
R.sub.6, R.sub.7 and R.sub.8 are each independently a hydrogen, or halogen (preferably chlorine or bromine) atom, or a lower alkyl, aralkyl, aryl, lower alkoxy, or lower alkenyl or trifluoromethyl group, or R.sub.6 and R.sub.7 may be together a methylenedioxy, or R.sub.7 and R.sub.8 may be together a methylenedioxy group;
R.sub.3 is a hydrogen, or halogen (preferably chlorine, bromine or fluorine) atom, or a lower alkyl or lower alkoxy group;
R.sub.4 is a lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, cyano, halogen-substituted lower alkyl, halogen-substituted lower alkenyl group, or a C.sub.3 to C.sub.5 alicylic group; and ##STR3## where:
A is a hydrogen atom, or a cyano group, or a --C.tbd.CH group, or a ##STR4##
R.sub.9 and R.sub.10 are each independently a hydrogen atom, or a lower alkyl or lower alkenyl group;
Z is an oxygen or a sulphur atom, or a --CH.sub.2 -- or --CO-- group; and
Y is a hydrogen atom, or a lower alkyl, lower alkenyl, lower alkynyl or an aryl or furyl group which is either unsubstituted, or is substituted by one or more lower alkyl, lower alkenyl or lower alkoxy groups or halogen atoms; ##STR5## where:
R.sub.11 is a hydrogen atom, or a methyl group; and
R.sub.12 and R.sub.13 are each independently a hydrogen atom, or a lower alkyl group; ##STR6## where: ##STR7## is a benzene ring, or a dihydro- or tetrahydro-benzene ring; and
B.sub.1, B.sub.2, B.sub.3, B.sub.4 are each independently a hydrogen, or halogen atom, or a methyl group; ##STR8## where:
D.sub.1 and D.sub.2 are each independently a halogen atom (preferably fluorine or chlorine) or a methyl group;
each n is independently 0, 1 or 2; and ##STR9##
Alcohols of the formula R.sub.5 OH, where R.sub.5 is as defined above, are generally known and have been suggested or used as the alcohol radical in synthetic pyrethroids and substituted acetate esters having pesticidal activity. In the compounds of the present invention we have found that particul
REFERENCES:
patent: 4091111 (1978-05-01), Ohno et al.
patent: 4224330 (1980-09-01), Henrick et al.
Godfrey Andrew A.
Hadler Malcolm R.
Woodward David R.
Dentz Bernard
Ford John M.
Shell Internationale Research Maatschappij B.V.
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