Symmetrical insecticidal bis-carbamate compounds

A compound of the formula:

• ##STR19## wherein:
• R is:
• ##STR20## wherein:
• R.sub.2 is alkyl, alkylthio, alkoxy, alkanoyl or alkoxycarbonyl, all of which may be unsubstituted or aliphatically substituted in any combination with one or more cyano, nitro, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxy or R.sub.4 R.sub.5 --NCO-- groups;
• or R.sub.2 is phenyl, R.sub.4 R.sub.5 NCO-- or R.sub.6 CON(R.sub.4)--;
• wherein:
• R.sub.4 and R.sub.5 are individually hydrogen or alkyl;
• R.sub.6 is hydrogen, alkyl or alkoxy;
• R.sub.3 is hydrogen, alkyl, alkylthio or cyano;
• provided that the total number of carbon atoms in R may not exceed eight and provided further than when R.sub.2 is alkyl substituted with alkylthio, R.sub.3 is alkyl or alkylthio;
• and
• R' is alkyl containing from one to four carbon atoms.

A pesticidal composition comprising an insecticidally or miticidally effective amount of at least one compound of the formula:

• ##STR22## wherein:
• R is:
• ##STR23## wherein:
• R.sub.2 is alkyl, alkylthio, alkoxy, alkanoyl or alkoxycarbonyl, all of which may be unsubstituted or aliphatically substituted in any combination with one or more cyano, nitro, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxy or R.sub.4 R.sub.5 --NCO--groups;
• or R.sub.2 is phenyl, R.sub.4 R.sub.5 NCO-- or R.sub.6 CON(R.sub.4)--;
• wherein:
• R.sub.4 and R.sub.5 are individually hydrogen or alkyl;
• R.sub.6 is hydrogen, alkyl or alkoxy;
• R.sub.3 is hydrogen, alkyl, alkylthio or cyano;
• A is a four or five member divalent aliphatic chain which includes one or two divalent oxygen, sulfur, sulfinyl or sulfonyl groups and which may include not more than one divalent amino, alkylamino or carbonyl groups, in any combination;
• provided that the total number of carbon atoms in R may not exceed eight and provided further that when R.sub.2 is alkyl substituted with alkylthio, R.sub.3 is alkyl or alkylthio;
• and
• R' is alkyl containing from one to four carbon atoms;
• and an acceptable carrier.

A pesticidal composition comprising an insecticidally or miticidally effective amount of at least one compound of the formula:

• ##STR26## wherein:
• R is:
• ##STR27## wherein:
• R.sub.2 is alkyl, alkylthio, alkoxy, ankanoyl or alkoxycarbonyl, all of which may be unsubstituted or aliphatically substituted in any combination with one or more cyano, nitro, alkylthio, alkylsulfonyl, alkylsulfonyl, alkoxy or R.sub.4 R.sub.5 --NCO-- groups;
• or R.sub.2 is phenyl, R.sub.4 R.sub.5 NCO-- or R.sub.6 CON(R.sub.4)--;
• wherein:
• R.sub.4 and R.sub.5 are individually hydrogen or alkyl;
• R.sub.6 is hydrogen, alkyl or alkoxy;
• R.sub.3 is hydrogen, alkyl, alkylthio or cyano;
• provided that the total number of carbon atoms in R may not exceed eight and provided further than when R.sub.2 is alkyl substituted with alkylthio, R.sub.3 is alkyl or alkylthio;
• and
• R' is alkyl containing from one to four carbon atoms;
• and an acceptable carrier.

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

• ##STR28## wherein:
• R is:
• ##STR29## wherein:
• R.sub.2 is alkyl, alkylthio, alkoxy, alkanoyl or alkoxycarbonyl, all of which may be unsubstituted or aliphatically substituted in any combination with one or more cyano, nitro, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxy or R.sub.4 R.sub.5 --NCO--groups;
• or R.sub.2 is phenyl, R.sub.4 R.sub.5 NCO-- or R.sub.6 CON(R.sub.4)--;
• wherein:
• R.sub.4 and R.sub.5 are individually hydrogen or alkyl;
• R.sub.6 is hydrogen, alkyl or alkoxy;
• R.sub.3 is hydrogen, alkyl, alkylthio or cyano;
• A is a four or five member divalent aliphatic chain which includes one or two divalent oxygen, sulfur, sulfinyl or sulfonyl groups and which may include not more than one divalent amino, alkylamino or carbonyl groups, in any combination;
• provided that the total number of carbon atoms in R may not exceed eight and provided further that when R.sub.2 is alkyl substituted with alkylthio, R.sub.3 is alkyl or alkylthio;
• and
• R' is alkyl containing from one to four carbon atoms.

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

• ##STR32## wherein:
• R is:
• ##STR33## wherein:
• R.sub.2 is alkyl, alkylthio, alkoxy, alkanoyl or alkoxycarbonyl, all of which may be unsubstituted or aliphatically substituted in any combination with one or more cyano, nitro, alkylthio, alkylsulfinyl, alkylsulfonyl, alkoxy or R.sub.4 R.sub.5 --NCO-- groups;
• or R.sub.2 is phenyl, R.sub.4 R.sub.5 NCO-- or R.sub.6 CON(R.sub.4)--;
• wherein:
• R.sub.4 and R.sub.5 are individually hydrogen or alkyl;
• R.sub.6 is hydrogen, alkyl or alkoxy;
• R.sub.3 is hydrogen, alkyl, alkylthio or cyano;
• provided that the total number of carbon atoms in R may not exceed eight and provided further than when R.sub.2 is alkyl substituted with alkylthio, R.sub.3 is alkyl or alkylthio;
• and
• R' is alkyl containing from one to four carbon atoms.