The Dow Chemical Company

Dowelanco

Barat Bisabri-Ershadi

Walter Reifschneider

James E Dripps

J Brian Barron

Raymond H Rigterink

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.

((N-heterocyclyl)carbonyl)phosphoramidothioate ester insecticides

O,S-Dialkyl ((nitrogen heterocyclyl)carbonyl)-phosphoramidothioates are prepared by the reaction of O,S-dialkyl phosphoroisocyanatidothioates with selected 5 and 6 membered nitrogen heterocycles, such as thiomorpholine and tetrahydroquinoline, and found to be effective plant systemic and contact insecticides. O,S-dimethyl ((4-thiomorpholinyl)carbonyl)phosphoramidothioate, for example, is prepared from O,S-dimethyl phosphoroisocyanatidothioate and thiomorpholine and found to control aster leafhopper when applied to rice plants.

Ester and amide derivatives of N-(((alkoxy-(alkylthio)phosphinyl)amino)carbonyl)amino)alkanecarboxylic acids of the formula: ##STR1## (wherein R.sup.2 represents an alkyl group containing a carboxylic acid ester or amide moiety) were prepared by the reaction of O,S-dialkyl phosphoroisocyanatidothioates and ester and amide derivatives of naturally occurring and synthetic aminoacids and were found to be effective plant systemic and contact insecticides. Ethyl N-(((methoxy(methylthio)phosphinyl)amino)-carbonyl)methioninate, for example, were prepared from O,S-dimethyl phosphoroisocyanatidothioate and ethyl methioninate and found to control aster leafhoppers when applied to rice plants.

N-(((alkoxy(alkylthio)phosphinyl)amino)carbonyl)-aminoalkanoate ester

Novel aniline compounds that are useful in preparing N-aroyl N'-phenyl ureas having alkyl substituents in the 2-, 3-, 5- and 6-positions and haloalkoxy in the 4-position of the N'-phenyl which are more active and have a broader spectrum of effectiveness than the known benzoylurea insecticides.

Substituted aniline compounds

O,S-Dialkyl ((piperazinyl)carbonyl)phosphoramidothioates are prepared by the reaction of O,S-dialkyl phosphoroisocyanatidothioates with substituted piperazines and found to be effective plant systemic and contact insecticides. ((4-(1,1-Dimethylethyl)-1-piperazinyl)carbonyl)phosphoramidothioate, for example, is prepared from O,S-dimethyl phosphoroisocyanatidothioate and 4-(1,1-dimethylethyl)piperazine and found to control aster leafhoppers when applied to rice plants.

((1-piperazinyl)carbonyl)phosphoramidothioate ester insecticides

N-aroyl N'-phenyl ureas having the formula ##STR1## wherein: Ar is a substituted phenyl, pyridyl or pyrimidinyl radical wherein the substituents are chloro, bromo, fluoro C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxy, with the proviso that at least one substituent is positioned ortho to the carbonyl group; R.sub.3 and R.sub.4 are individually H or C.sub.1 -C.sub.4 alkyl or together they form the group ##STR2## Y is O or S; X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are individually H, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, alkylcarbonyl, alkoxycarbonyl, C.sub.1 -C.sub.3 alkylthio, NO.sub.2, CN or NR.sub.5 R.sub.6 wherein R.sub.5 and R.sub.6 are H or C.sub.1 -C.sub.3 alkyl with the provisos that at least one of X.sub.1, X.sub.2, X.sub.3 or X.sub.4 is other than H and (a) when three of X.sub.1, X.sub.2, X.sub.3 or X.sub.4 are H, the fourth substitution cannot be halogen or alkyl, (b) when X.sub.1 and X.sub.3 are H, X.sub.2 and X.sub.4 cannot both be halogen, (c) when X.sub.2 and X.sub.3 are H, X.sub.1 and X.sub.4 cannot be both halogen, (d) when X.sub.1 and X.sub.4 are hydrogen, X.sub.2 and X.sub.3 cannot both be halogen and R is a C.sub.1 -C.sub.4 haloalkyl, haloalkoxy or haloalkylthio group which possess insecticidal properties.

Substituted N-aroyl N'-phenyl urea compounds

Novel N-aroyl N'-phenyl urea compounds having halogen substituents in the 2- and 5-position of the phenyl radical possess exceptional insecticidal activity.

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Davis, CA, United States of America

Barat Bisabri-Ershadi