Arthropodicidal and nematocidal phosphoramidates

Abstract

This invention relates to novel phosphoramidates of the formula: ##STR1## wherein R 1 is (C 6 -C 10 ) aryl optionally substituted with alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, dialkylamino, haloalkyl, hydroxyalkyl, cyano, nitro, hydroxy, or halogen; R 2 is hydrogen.[., alkyl, cycloalkyl, alkenyl, or optionally substituted aralkyl or aryl.]. R 3 is (C 1 -C 6 ) alkyl; R 4 is (C 3 -C 4 ) alkyl; .Iadd.X is sulfur; .Iaddend.and .[.X,.]. Y and Z are independently oxygen or sulfur; and the agronomically acceptable metal salts and metal salt complexes thereof; to compositions containing them; and to methods of using them to control certain harmful pests, e.g. arthropods and nematodes.

We claim: 
     
       1. A method of controlling pests which comprises applying directly to the pests or to the loci to be freed of or protected from attack by such pests, a pesticidally effective amount of a compound of the formula ##STR9## wherein R 1  is a (C 6  -C 10 ) aryl group, optionally substituted with up to five (C 1  -C 4 ) alkyl groups, (C 1  -C 4 ) alkoxyl groups, (C 1  -C 4 ) alkylthio groups; (C 1  -C 4 ) alkylsulfonyl groups, (C 1  -C 4 ) hydroxyalkyl groups, (C 1  -C 4 ) haloalkyl groups, cyano groups, nitro groups, hydroxyl groups, or halogen atoms; R 3  is a (C 1  -C 6 ) alkyl group;   R 4  is a (C 3  -C 4 ) alkyl group;   X is .[.an oxygen or.]. .Iadd.a .Iaddend.sulfur atom;   Y is an oxygen or sulfur atom; and   Z is an oxygen or sulfur atom and the agronomically acceptable metal sales and metal salt complexes thereof.   
     
     
       2. A compound of the formula: ##STR10## wherein A is independently (a) a (C 1  -C 4 ) alkyl group;   (b) a (C 1  -C 4 ) alkoxy group;   (c) a (C 1  -C 4 ) alkylthio group;   (d) a trihalomethyl group; or   (e) a halogen atom;   R 5  is a (C 1  -C 4 ) alkylthio group or a (C 1  -C 4 ) alkoxy group;   R 6  is a (C 3  -C 4 ) alkyl group;   X is .[.an oxygen or.]. .Iadd.a .Iaddend.sulfur atom; and   n is an integer from 0 to 3 and the agronomically acceptable metal salts and metal salt complexes thereof.   
     
     
       3. A compound according to claim 2 wherein A is independently (a) a methyl group;   (b) a methoxy group;   (d) a trifluoromethyl group; or   (e) a chlorine atom;     R 5  is a propylthio group or an ethoxy group;   R 6  is a n-propyl, isobutyl, or sec-butyl group;   X' is .[.an oxygen or.]. .Iadd.a .Iaddend.sulfur atom; and   n is an integer of 0 to 2.   
     
     
       4. A compound according to claim 3 wherein R 5  is an ethoxy group and R 6  is an isobutyl group or a sec-butyl group. .[.5. A compound according to claim 4 having the formula: ##STR11## 
     
     
        .[.6.  A compound according to claim 4 having the formula: ##STR12## 
     
     
        7. A compound according to claim 4 having the formula: ##STR13## 
     
     
         .[.8.  A compound according to claim 5 having the formula: ##STR14## 
     
     
        .[.9.  A compound according to claim 5 having the formula: ##STR15## 
     
     
        10. A pesticidal composition comprising a compound according to claim 1 
     
     
        and an agronomically acceptable carrier. 11. A method of controlling pests which comprises applying directly to the pests or to the loci to be freed of or protected from attack by such pests, a pesticidally effective amount 
     
     
        of the composition of claim 10. 12. A method according to claim 11 wherein 
     
     
        the pests are arthropods. 13. A method according to claim 12 wherein the 
     
     
        arthropods are insects or acarids. 14. A method according to claim 11 wherein the pests are nematodes.