((N-heterocyclyl)carbonyl)phosphoramidothioate ester insecticides
AssigneeDowElanco
InventorsWalter Reifschneider, Barat Bisabri-Ershadi, James E. Dripps, J. Brian Barron
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Abstract
O,S-Dailkyl ((nitrogen heterocyclyl)carbonyl)phosphoramidothioates are prepared by the reaction of O,S-dialkyl phosphoroisocyanatidothioates with selected five and six membered nitrogen heterocycles and found to be effective plant systemic and contact insecticides. Ethyl 1-(((methoxy(methylthio)phosphinyl)amino)carbonyl)-4-piperidinecarboxylate , for example, is prepared from O,S-dimethyl phosphoroisocyanatidothioate and ethyl 4-piperidinecarboxylate and found to control aster leafhopper when applied to rice plants.
Claims27
A compound of the formula:
- ##STR5## wherein R and R.sup.1 each independently represent C.sub.1 -C.sub.4 alkyl;
- A represents --CHX--or o-phenylene;
- X represents phenyl, C.sub.1 -C.sub.34 alkyl, CH.sub.2 CO.sub.2 R, CO.sub.2 R, or CONR.sup.3.sub.2 ;
- each R.sup.3 independently represents H or C.sub.1 -C.sub.4 alkyl;
- m represents 0, 1, or 2;
- n represents 1, 2, 3, or 4;
- and
- p represents 0 or 1
- with the proviso that the sum of m, n, and p is such that the nitrogen heterocyclic moiety described in a five or six membered ring.
A ninsecticidal composition comprising an agricultrually acceptable adjuvant or carrier and an insecticidally effective amount of a compound of the formula:
- ##STR6## wherein R and R.sup.1 each independently represent C.sub.1 -C.sub.4 alkyl;
- A represents --CHX--or o-phenylene;
- X represents phenyl, C.sub.1 -C.sub.4 alkyl, CH.sub.2 CO.sub.2 R, CO.sub.2 R, or CONR.sup.3.sub.2 ;
- each R.sup.3 independently represents H or C.sub.1 -C.sub.4 alkyl;
- m represents 0, 1, or 2;
- n represents 1, 2, 3, or 4;
- and
- p represents 0 or 1
- with the proviso that the sum of m, n, and p is such that the nitrogen heterocyclic moiety described is a five or six membered ring.
A method of controlling insects which comprises contacting the insects or the locus thereof or the plants on which the insects feed or the locus thereof with an insecticidally effective amount of a compound of the formula ##STR7## wherein R and R.sup.1 each independently represent C.sub.1 -C.sub.4 alkyl;
- A represents --CHX--or o-phenylene;
- X represents phenyl, C.sub.1 -c.sub.4 alkyl, CzH.sub.2 CO.sub.2 R, CO.sub.2 R, or CONR.sup.3.sub.2 ;
- each R.sup.3 independently represents H or C.sub.1 -c.sub.4 alkyl;
- m represents 0, 1, or 2;
- n represents 1, 2, 3, or 4;
- and
- p represents 0 or 1
- with the proviso that the sum of m, n, and p is such that the nitrogen heterocyclic moiety described is a five or six members ring.
Dependencies are inferred from the claim text.