Pesticidal carbamates

Details Pesticidal carbamates Pesticidal carbamates

1986-07-21

1988-11-29

Lee, Mary C.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

544153, 549470, A01N 4710, C07D30786

Patent

active

047882174

DESCRIPTION:

BRIEF SUMMARY
This invention relates to new benzofurane derivatives, a process for the preparation thereof, pesticidal compositions comprising the same and the use of the said compositions for combating pests--particularly insects--and for inhibiting the growth thereof.
In the body of the specification and the set of claims the general symbols have the following definition: --(CH.sub.2).sub.n --, wherein general Formula II, and --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --.
It is known that the 2,3-dihydro-2,2-dimethyl-benzofurane-7-yl-methyl-carbamate (German Federal Republic patent No. 1 493 646) useful as a general soil disinfectant is a very toxic compound. In rats the acute toxicity amounts to LD.sub.50 =8-10 mg/kg p.o. For this reason the use of this compound is authorized only on industrial scale application.
It is the object of the present invention to provide new compounds which maintain the activity of the known derivatives but are less toxic.
It has been found that the new compounds of the Formula I ##STR3## and salts thereof exhibit outstanding pesticidal--particularly insecticidal, acaricidal and nematodical--effect either per se or in combination with other compounds. The toxicity of the said new compounds is generally lower than that of chemically related known compounds. Moreover the compounds of the Formula I have a more simple structure, are less expensive and can be more readily prepared than the known derivatives having a satisfactory toxicity.
According to the present invention there are provided new compounds of the Formula I and salts thereof (wherein R.sup.2 and R.sup.3 are as stated above).
Preferable representatives of the compounds of the Formula I are the following derivatives: carbamate and salts thereof; a.-carbethoxyethyl)-amino-methyl]-carbamate and salts thereof; henyl-ethyl)-amino-methyl]-carbamate and salts thereof; zino)-methyl]-carbamate and salts thereof.
According to a further aspect of the present invention there is provided a process for the preparation of compounds of the Formula I and salts thereof, which comprises
(a) reacting a compound of the Formula III ##STR4## with a reactive derivative of an acid of the Formula IV; or ##STR5##
(b) reacting a compound of the Formula V ##STR6## with a compound of the Formula VI, VII and/or VIII; ##STR7## or
(c) reacting a compound of the Formula IX ##STR8## with an amino of the Formula X ##STR9## and if desired converting the compound of the Formula I into a salt thereof.
According to method (a) of the process of the present invention a compound of the Formula III is reacted with a reactive derivative of an acid of the Formula IV. As reactive acid derivative an acid halide of the Formula XI ##STR10## or an anhydride of the Formula (XII ##STR11## or an active ester--preferably an ester of the Formula XIII-- ##STR12## may be used.
The reaction may be preferably carried out in the presence of an aprotic solvent (e.g. benzene or toluene) and a tertiary base. As tertiary base e.g. a trialkyl amine may be used. The reaction may be accomplished preferably at a temperature between 10.degree. C. and 30.degree. C.
Method (b) of the process of the present invention may be preferably carried out under the same reaction conditions as method (a).
According to method (c) of the process of the present invention it is preferred to use as starting material a compound of the Formula IX, which is prepared by reacting 2,3-dihydro-2,2-dimethyl-7-benzofuranyl-methyl-carbamate with thionyl chloride and paraformaldehyde, preferably in the presence of an aprotic organic solvent. The 2,3-dihydro-2,2-dimethyl-7-benzofuranyl-methyl-carbamate may be prepared from benzofuranol of the Formula III by known methods, e.g. by reacting with methyl isocyanate.
The reaction according to method (c) may be preferably carried out in the presence of an aprotic organic solvent (e.g. benzene) at a temperature between 10.degree. C. and 40.degree. C. It is preferred to add a tertiary base to the reaction mixture.
The compounds of the Formula I may be converted into the salts thereof. Sal

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