Chevron Research Company

Irene C Huang

William L Schinski

David C Chan

Gustave K Kohn

William G Toland

Novel N-haloacetylphenylamino carbonyl oximes represented by the formula ##STR1## wherein Ar is phenyl or substituted phenyl; R.sup.1 is halomethyl; R.sup.2 and R.sup.3 are each independently hydrogen, alkyl, phenyl, benzyl, substituted phenyl or benzyl, haloalkyl, cyanoalkyl, alkoxyalkyl, alkylthioalkyl or thiocyanoalkyl; R.sup.4 is hydrogen or alkyl; n is 0 or 1; m is 0 or 1; R is hydrogen, alkyl, alkenyl, alkynyl, alkylthioalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, phenyl, benzyl, substituted phenyl or benzyl, or R is acyl of the formula ##STR2## wherein R.sup.5 is hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, acetonyl, or the group --NR'R' wherein R' and R' are independently hydrogen, alkyl or phenyl; with the proviso that R.sup.2 and R.sup.3 may be joined together to form a carbocyclic ring or a heterocyclic ring; or R and R.sup.2 may be joined together to form a heterocyclic ring; or R and R.sup.3 may be joined together to form a heterocyclic ring.

N-Haloacetylphenylamino carbonyl cyclic intermediates

Novel N-haloacetylphenylamino carbonyl oximes represented by the formula ##STR1## wherein Ar is phenyl or substituted phenyl; R.sup.1 is halomethyl; R.sup.2 and R.sup.3 are each independently hydrogen, alkyl, phenyl, benzyl, substituted phenyl or benzyl, haloalkyl, cyanoalkyl, alkoxyalkyl, alkylthioalkyl or thiocyanoalkyl; R.sup.4 is hydrogen or alkyl; n is 0 or 1; m is 0 or 1; R is hydrogen, alkyl, alkenyl, alkynyl, alkylthioalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, phenyl, benzyl, substituted phenyl or benzyl, or R is acyl of the formula ##STR2## wherein R.sup.5 is hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, acetonyl, or the group -NR'R' wherein R' and R' are independently hydrogen, alkyl or phenyl; with the proviso that R.sup.2 and R.sup.3 may be joined together to form a carbocyclic ring or a heterocyclic ring; or R and R.sup.2 may be joined together to form a heterocyclic ring; or R and R.sup.3 may be joined together to form a heterocyclic ring.

Herbicidal and plant-growth-regulating N-haloacetylphenylamino carbonyl

Novel N-haloacetylphenylamino carbonyl oximes represented by the formula ##STR1## wherein Ar is aryl, R.sup.1 is halomethyl, R.sup.2 is hydrogen, alkyl or aryl, R.sup.3 is hydrogen, alkyl or aryl, n is 0 or 1 and R is hydrogen, aryl, alkyl, alkenyl or alkynyl, with the proviso that R.sup.2 and R.sup.3 may be joined together to form a carbocyclic ring of 5 to 6 carbon atoms or a heterocyclic ring of one N, O or S hetero atom and 4 to 5 carbon atoms. The oxime compounds are useful as herbicides and plant growth regulators.

Herbicidal and plant-growth regulating N-haloacetylphenylamino carbonyl

O,S-dimethyl phosphoroamidothioates are prepared by reacting in the liquid phase methyl phosphorodichloridite with methyl sulfenyl chloride in the presence of a lower alkanoic acid to produce O,S-dimethyl phosphorochloridothioate and subsequently reacting in the liquid phase the O,S-dimethyl phosphorochloridothioate with ammonia or an amine.

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Huntington Beach, CA, United States of America

Irene C Huang