Molecules having pesticidal utility, and intermediates, compositions, and processes, related thereto

Abstract

This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. This document discloses molecules having the following formula (“Formula One”).

1 . A molecule having the following formula 
       
         
           
           
               
               
           
         
         wherein:
 (A) R 1  is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ; 
 (B) R 2  is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ; 
 (C) R 3  is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ; 
 (D) R 4  is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ; 
 (E) R 5  is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ; 
 (F) R 6  is selected from the group consisting of H and (C 1 -C 4 )alkyl; 
 (G) R 7  is selected from the group consisting of H, F, Cl, Br, and I; 
 (H) R 8  is selected from the group consisting of F, Cl, Br, and I; 
 (I) R 9  is selected from the group consisting of H and (C 1 -C 4 )alkyl; 
 (J) R 10  is selected from the group consisting of H, (C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl(C 1 -C 4 )alkoxy, C(═O)(C 1 -C 4 )alkyl, and (C 1 -C 4 )alkoxyC(═O)(C 1 -C 4 )alkyl; 
 (K) R 11  is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ; 
 (L) R 12  is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ; 
 (M) R 13  is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ; 
 (N) R 14  is selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 4 )alkenyl, (C 3 -C 6 )cycloalkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkyl, (C 3 -C 6 )halocycloalkyl, (C 2 -C 4 )haloalkenyl, (C 3 -C 6 )halocycloalkenyl, (C 1 -C 4 )haloalkoxy, S(C 1 -C 4 )alkyl, S(O)(C 1 -C 4 )alkyl, S(O) 2 (C 1 -C 4 )alkyl, S(C 1 -C 4 )haloalkyl, S(O)(C 1 -C 4 )haloalkyl, S(O) 2 (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl-S(O) 2 NH 2 , and (C 1 -C 4 )haloalkyl-S(O) 2 NH 2 ; 
 (O) R 15  is selected from the group consisting of H, (C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkyl(C 1 -C 4 )alkoxy, C(═O)(C 1 -C 4 )alkyl, and (C 1 -C 4 )alkoxyC(═O)(C 1 -C 4 )alkyl; 
 (P) R 16  is selected from the group consisting of (C 3 -C 8 )cycloalkyl, azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinonyl, imidazolidinonyl, isoxazolidinonyl, morpholinyl, oxazolidinonyl, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetrahydropyranyl, tetra hydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinonyl, wherein each cycloalkyl, azetidinyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinonyl, imidazolidinonyl, isoxazolidinonyl, morpholinyl, oxazolidinonyl, oxetanyl, piperazinyl, piperidinyl, pyranyl, pyrrolidinyl, pyrrolidinonyl, tetrahydrofuranyl, tetra hydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, tetrahydrothiophenyl-dioxide, thietanyl, thietanyl-oxide, thietanyl-dioxide, and thioxothiazolidinonyl may be optionally substituted with one or more substituents selected from the group consisting of H, F, Cl, Br, I, CN, NH 2 , NO 2 , oxo, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, C(═O)O(C 1 -C 4 )alkyl, (C═O)NH(C 1 -C 4 )alkyl, (C═O)NH(C 1 -C 4 )haloalkyl, C(═O)(C 3 -C 6 )cyclopropyl, C(═O)(C 1 -C 4 )haloalkyl, C(═O)(C 1 -C 4 )alkyl(C 1 -C 4 )alkoxy, and (C 1 -C 4 )alkyl-morpholinyl; 
 (Q) Q 1  and Q 2  are each independently selected from the group consisting of O and S; and
 N-oxides, agriculturally acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, resolved stereoisomers, and tautomers, of the molecules of Formula One. 
 
 
       
     
     
         2 . A molecule according to  claim 1 , wherein R 1  is selected from the group consisting of H and Cl. 
     
     
         3 . A molecule according to  claim 1 , wherein R 2  is selected from the group consisting of H, Cl, Br, CH 3 , and CF 3 . 
     
     
         4 . A molecule according to  claim 1 , wherein R 3  is selected from the group consisting of H, F, Cl, CH 3 , CF 3 , and OCF 3 . 
     
     
         5 . A molecule according to  claim 1 , wherein R 4  is selected from the group consisting of H, F, Cl, Br, CH 3 , and CF 3 . 
     
     
         6 . A molecule according to  claim 1 , wherein R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , and R 14  are H. 
     
     
         7 . A molecule according to  claim 1 , wherein R 7  is Cl. 
     
     
         8 . A molecule according to  claim 1 , wherein R 6  is Cl. 
     
     
         9 . A molecule according to  claim 1 , wherein R 13  is selected from the group consisting of H, Cl, and CF 3 . 
     
     
         10 . A molecule according to  claim 1 , wherein R 15  is selected from the group consisting of H and CH 3 . 
     
     
         11 . A molecule according to  claim 1 , wherein R 16  is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, azetidinyl, morpholinyl, oxetanyl, pyranyl, tetrahydrothiophenyl, thietanyl, thietanyl-oxide, and thietanyl-dioxide,
 wherein each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, azetidinyl, morpholinyl, oxetanyl, pyranyl, tetrahydrothiophenyl, thietanyl, thietanyl-oxide, and thietanyl-dioxide, may be optionally substituted with one or more substituents selected from the group consisting of H, F, CN, C(═O)OC(CH 3 ) 3 , and C(═O)CF 3 .   
     
     
         12 . A molecule according to  claim 1 , wherein Q 1  and Q 2  are O. 
     
     
         13 . A molecule according to  claim 1 , wherein:
 (A) R 1  is selected from the group consisting of H, F, and Cl;   (B) R 2  is selected from the group consisting of H, F, Cl, Br, CH 3 , and CF 3 ;   (C) R 3  is selected from the group consisting of H, F, Cl, CH 3 , and CF 3 , OCF 3 ;   (D) R 4  is selected from the group consisting of H, F, Cl, Br, CH 3 , and CF 3 ;   (E) R 5  is H;   (F) R 6  is H;   (G) R 7  is selected from the group consisting of Cl and Br;   (H) R 8  is selected from the group consisting of Cl and Br;   (I) R 9  is H;   (J) R 10  is H;   (K) R 11  is H;   (L) R 12  is H;   (M) R 13  is selected from the group consisting of H, F, Cl, and CF 3 ;   (N) R 14  is H;   (O) R 15  is selected from the group consisting of H and CH 3 ;   (P) R 16  is selected from the group consisting of (C 3 -C 8 )cycloalkyl, azetidinyl, morpholinyl, oxetanyl, pyranyl, tetrahydrothiophenyl, thietanyl, thietanyl-oxide, and thietanyl-dioxide, wherein each cycloalkyl, azetidinyl, morpholinyl, oxetanyl, pyranyl, tetrahydrothiophenyl, thietanyl, thietanyl-oxide, and thietanyl-dioxide, may be optionally substituted with one or more substituents selected from the group consisting of H, F, CN, C(═O)O(C 1 -C 4 )alkyl, C(═O)(C 3 -C 6 )cyclopropyl, C(═O)(C 1 -C 4 )haloalkyl, and C(═O)(C 1 -C 4 )alkyl(C 1 -C 4 )alkoxy; and   (Q) Q 1  and Q 2  are O.   
     
     
         14 . A molecule according to  claim 1  wherein said molecule is selected from one of the following molecules F1 through F92, PF1 through PF9, PF12, PF14, PF18 through PF23, PF28 through PF 34, PF36, PF37, and PF41 through PF45. 
     
     
         15 . A molecule according to  claim 1  wherein said molecule is selected from the group consisting of molecules F4, F5, F9, F10, F11, F15, F16, and F17. 
     
     
         16 . A composition comprising:
 (a) a molecule according to  claim 1 : and   (b) an active ingredient.   
     
     
         17 . A composition comprising:
 (a) a molecule according to  claim 13 : and   (b) an active ingredient.   
     
     
         18 . A composition comprising:
 (a) a molecule according to  claim 15 : and   (b) an active ingredient.   
     
     
         19 . A process to control a pest, said process comprising, applying to a locus, a pesticidally effective amount of a molecule according to  claim 1 . 
     
     
         20 . A process according to  claim 19  wherein said pest is a chewing pest.