Novel oxime-phosphate compounds

Compounds of the formula:

• ##STR14## wherein:
• X is either oxygen or sulfur;
• R.sub.1 is alkyl, cycloalkyl or phenyl, all of which may be unsubstituted or substituted with one or more alkyl, halogen, alkoxy or alkylthio substituents;
• provided that the total number of aliphatic carbon atoms in any alkyl, alkoxy or alkylthio substituent may not exceed eight;
• and provided further that the total number of aliphatic carbon atoms in R.sub.1 may not exceed sixteen;
• and provided further that when R.sub.1 is cycloalkyl, the total number of aliphatic carbon atoms in said cycloalkyl ring structure may be no less than three and may not exceed six;
• R.sub.2 is alkyl, provided that the total number of aliphatic carbon atoms in R.sub.2 does not exceed eight;
• R.sub.3 and R.sub.4 are individually alkyl.

Compounds of the formula:

• ##STR15## wherein:
• X is oxygen or sulfur;
• R.sub.3 and R.sub.4 are individually alkyl;
• A is a three or four-membered divalent aliphatic chain, which may be optionally substituted by one or more alkyl groups each containing no more than six carbon atoms, and which may include in said chain one or more divalent:
• sulfur, sulfinyl, sulfonyl, oxygen, carbonyl, thiono or dicyanomethylidene moieties;
• or
• amino moieties, which may be optionally substituted with alkyl, alkenyl, alkoxyalkyl, or acyl groups having no more than six carbon atoms;
• or
• imino moieties of the formula:
• ##STR16## wherein Y is alkyl, alkenyl, alkynyl, dialkylamino, cyano, alkylsulfonyl, aryl or arysulfonyl groups, said aryl groups being optionally substituted with halogen or alkyl substituents having no more than ten carbon atoms.

An insecticidal, miticidal and nematocidal composition comprising an acceptable carrier and as the active toxicant a pesticidally effective amount of a compound of the formula:

• ##STR17## wherein:
• X is oxygen or sulfur;
• R.sub.3 and R.sub.4 are individually alkyl;
• provided that the total number of aliphatic carbon atoms in each of R.sub.3 and R.sub.4 does not exceed six;
• R is:
• ##STR18## wherein:
• R.sub.1 is alkyl, cycloalkyl or phenyl, all of which may be unsubstituted or substituted with one or more alkyl, halogen, alkoxy or alkylthio substituents;
• provided that the total number of aliphatic carbon atoms in any alkyl, alkoxy or alkylthio substituent may not exceed eight;
• and provided further that the total number of aliphatic carbon atoms in R.sub.1 may not exceed sixteen;
• and provided further that when R.sub.1 is cycloalkyl, the total number of aliphatic carbon atoms in said cycloalkyl ring structure may be no less than three and may not exceed six;
• R.sub.2 is alkyl, provided that the total number of aliphatic carbon atoms in R.sub.2 does not exceed eight;
• or ##STR19## wherein:
• A is a three- or four-membered divalent aliphatic chain, which may be optionally substituted on one or more alkyl groups each containing no more than six carbon atoms, and which may include in said chain one or more divalent;
• sulfur, sulfinyl, sulfonyl, oxygen, carbonyl, thiono or dicyanomethylidene moieties;
• or
• amino moieties, which may be optionally substituted with alkyl, alkenyl, alkoxyalkyl, or acyl groups having no more than six carbon atoms;
• or imino moieties of the formula:
• ##STR20## wherein Y is alkyl, alkenyl, alkynyl, dialkylamino, cyano, alkylsulfonyl, aryl or arysulfonyl groups, said aryl groups being optionally substituted with halogen or alkyl substituents having no more than ten carbon atoms.

An insecticidal, miticidal and nematocidal composition comprising an acceptable carrier and as the active toxicant an insecticidally, miticidally or nematocidally effective amount of a compound of the formula:

• ##STR21## wherein:
• X is either oxygen or sulfur;
• R.sub.1 is alkyl, cycloalkyl or phenyl, all of which may be unsubstituted or substituted with one or more alkyl, halogen, alkoxy or alkylthio substituents;
• provided that the total number of aliphatic carbon atoms in any alkyl, alkoxy or alkylthio substituent may not exceed eight;
• and provided further that the total number of aliphatic carbon atoms in R.sub.1 may not exceed sixteen;
• and provided further than when R.sub.1 is cycloalkyl, the total number of aliphatic carbon atoms in said cycloalkyl ring structure may be no less than three and may not exceed six;
• R is alkyl, provided that the total number of aliphatic carbon atoms in R.sub.2 does not exceed eight.
• R.sub.3 and R.sub.4 are individually alkyl.

An insecticidal and miticidal composition comprising an acceptable carrier and as the active toxicant an insecticidally or miticidally effective amount of a compound of the formula:

• ##STR22## wherein:
• X is oxygen or sulfur;
• R.sub.3 and R.sub.4 are individually alkyl;
• A is a three- or four-membered divalent aliphatic chain, which may be optionally substituted by one or more alkyl groups each containing no more than six carbon atoms, and which may include in said chain one or more divalent:
• sulfur, sulfinyl, sulfonyl, oxygen, carbonyl, thiono or dicyanomethylidene moieties;
• or
• amino moieties which may be optionally substituted with alkyl, alkenyl, alkoxyalkyl or acyl groups having no more than six carbon atoms;
• or imino moieties of the formula:
• ##STR23## wherein Y is alkyl, alkenyl, alkynyl, dialkylamino, cyano, alkylsulfonyl, aryl or arysulfonyl groups, said aryl groups being optionally substituted with halogen or alkyl substituents having no more than ten carbon atoms.

A method of controlling insects, mites or nematodes which comprises subjecting them to an insecticidally, miticidally or nematocidally effective amount of a compound of the formula:

• ##STR24## wherein:
• X is oxygen or sulfur;
• R.sub.3 and R.sub.4 are individually alkyl;
• provided that the total number of aliphatic carbon atoms in each of R.sub.3 and R.sub.4 does not exceed six;
• R is:
• ##STR25## wherein:
• R.sub.1 is alkyl, cycloalkyl or phenyl, all of which may be unsubstituted or substituted with one or more alkyl, halogen, alkoxy or alkylthio substituents;
• provided that the total number of aliphatic carbon atoms in any alkyl, alkoxy or alkylthio substituent may not exceed eight;
• and provided further that the total number of aliphatic carbon atoms in R may not exceed sixteen;
• and provided further that when R.sub.1 is cycloalkyl, the total number of aliphatic carbon atoms in said cycloalkyl ring structure may be no less than three and may not exceed six;
• R.sub.2 is alkyl, provided that the total number of aliphatic carbon atoms in R.sub.2 does not exceed eight;
• or ##STR26## wherein:
• A is a three- or four-membered divalent aliphatic chain, which may be optionally substituted by one or more alkyl groups each containing no more than six carbon atoms, and which may include in said chain one or more divalent:
• sulfur, sulfinyl, sulfonyl, oxygen, carbonyl, thiono or dicyanomethylidene moieties;
• or
• amino moieties, which may be optionally substituted with with alkyl, alkenyl, alkoxyalkyl or acyl groups having no more than six carbon atoms;
• or
• imino moieties of the formula:
• ##STR27## wherein Y is alkyl, alkenyl, alkynyl, dialkylamino, cyano, alkylsulfonyl, aryl or arylsulfonyl groups, said aryl groups being optionally substituted with halogen or alkyl substituents having no more than ten carbon atoms.

A method of controlling insects, mites and nematodes which comprises subjecting them to an insecticidally, miticidally or nematocidally effective amount of a compound of the formula:

• ##STR28## wherein:
• X is either oxygen or sulfur;
• R.sub.1 is alkyl, cycloalkyl or phenyl, all of which may be unsubstituted or substituted with one or more alkyl, halogen, alkoxy or alkylthio substituents;
• provided that the total number of aliphatic carbon atoms in any alkyl, alkoxy or alkylthio substituent may not exceed eight;
• and provided further that the total number of aliphatic carbon atoms in R.sub.1 may not exceed sixteen;
• and provided further that when R.sub.1 is cycloalkyl, the total number of aliphatic carbon atoms in said cycloalkyl ring structure may be no less than three and may not exceed six;
• R.sub.2 is alkyl, provided that the total number of aliphatic carbon atoms in R.sub.2 does not exceed eight;
• R.sub.3 and R.sub.4 are individually alkyl.

A method of controlling insects, mites and nematodes which comprises subjecting them to an insecticidally, miticidally or nematocidally effective amount of a compound of the formula:

• ##STR29## wherein:
• X is oxygen or sulfur;
• R.sub.3 and R.sub.4 are individually alkyl;
• A is a three- or four-membered divalent aliphatic chain, which may be optionally substituted by one or more alkyl groups each containing no more than six carbon atoms, and which may include in said chain one or more divalent:
• sulfur, sulfinyl, sulfonyl, oxygen, carbonyl, thiono or dicyanomethylidene moieties;
• or
• amino moieties, which may be optionally substituted with alkyl, alkenyl, alkoxyalkyl or acyl groups having no more than six carbon atoms;
• or
• imino moieties of the formula:
• ##STR30## wherein Y is alkyl, alkenyl, alkynyl, dialkylamino, cyano, alkylsulfonyl, aryl or arysulfonyl groups, said aryl groups being optionally substituted with halogen or alkyl moieties having no more than ten carbon atoms.