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 3 -C 6 )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 3 -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 (Q), 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 (Q), (C 1 -C 8 )alkyl, (C 1 -C 8 )alkyl-O—(C 1 -C 8 )alkyl, (C 1 -C 8 )alkyl(C 3 -C 8 )cycloalkyl, (C 1 -C 8 )alkylphenyl, (C 2 -C 8 )alkenyl, (C 2 -C 8 )alkynyl, (C 1 -C 8 )haloalkyl, (C 1 -C 8 )alkyl-S—(C 1 -C 8 )alkyl, (C 1 -C 8 )alkyl-S(O)—(C 1 -C 8 )alkyl, (C 1 -C 8 )alkyl-S(O) 2 —(C 1 -C 8 )alkyl, O-phenyl, O—(C 2 -C 5 )alkenyl, O—(C 1 -C 8 )alkyl(C 3 -C 8 )cycloalkyl, O—(C 1 -C 8 )alkylphenyl, (C 1 -C 8 )alkyl-O—(C 1 -C 8 )alkyl(C 3 -C 8 )cycloalkyl, (C 1 -C 8 )alkyl-O—(C 1 -C 8 )haloalkyl, (C 1 -C 8 )alkyl-C(═O)NH—(C 1 -C 8 )haloalkyl, (C 1 -C 8 )alkyl-NHC(O)—(C 1 -C 8 )alkyl, (C 1 -C 8 )alkyl-S—(C 1 -C 8 )haloalkyl, (C 1 -C 8 )alkyl-S(O)—(C 1 -C 8 )haloalkyl, (C 1 -C 8 )alkyl-S(O) 2 —(C 1 -C 8 )haloalkyl, and (C 1 -C 8 )alkyl-S(O) 2 —NH 2 ,
 wherein each alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, and phenyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH 2 , NO 2 , (C 1 -C 8 )alkyl, (C 1 -C 8 )alkoxy, (C 1 -C 8 )haloalkyl, N((C 1 -C 8 )alkyl) 2 , C(O)O(C 1 -C 8 )alkyl, benzothioenyl, 2,3-dihydro-1H-imidazolonyl, furanyl, pyrazolyl, pyridinyl, thiazolyl, and triazolyl; 
 
 (Q) R 15  and R 16  together can optionally form a 2- to 5-membered saturated or unsaturated, hydrocarbyl link, which may contain one or more heteroatoms selected from the group consisting of nitrogen, sulfur, and oxygen,
 wherein said hydrocarbyl link may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, NH 2 , and NO 2 ; 
 
 (R) 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 2  is selected from the group consisting of H, F, and Cl. 
     
     
         3 . A molecule according to  claim 1 , wherein R 3  is selected from the group consisting of H, F, and Cl. 
     
     
         4 . A molecule according to  claim 1 , wherein R 4  is F or Cl. 
     
     
         5 . A molecule according to  claim 1 , wherein R 1 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , and R 14  are each independently H. 
     
     
         6 . A molecule according to  claim 1 , wherein R 7  is selected from the group consisting of Cl and Br. 
     
     
         7 . A molecule according to  claim 1 , wherein R 8  is selected from the group consisting of Cl and Br. 
     
     
         8 . A molecule according to  claim 1 , wherein R 13  is selected from the group consisting of H, Cl, and CF 3 . 
     
     
         9 . A molecule according to  claim 1 , wherein R 15  is selected from the group consisting of H and CH 3 . 
     
     
         10 . A molecule according to  claim 1 , wherein R 16  is selected from the group consisting of CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 OCH 2 CH 2 , CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 , CH 2 CH(CH 3 ) 2 , CH 2 cyclopropyl, CH 2 CH 2 cyclopropyl, CH 2 cyclobutyl, CH 2 phenyl, CH 2 CH 2 phenyl, CH 2 C═CH, CH 2 C═CH, CH 2 CF 3 , CH 2 CHF 2 , CH 2 CH 2 CF 3 , CH 2 CF 2 CF 3 , CH 2 CH 2 CH 2 CF 3 , CH 2 CH 2 CF 2 CF 3 , CH 2 CF 2 CF 2 CF 3 , CH 2 CH 2 CH 2 CH 2 F, CH 2 CH 2 SCH 3 , CH 2 CH 2 S(O)CH 3 , CH 2 CH 2 S(O) 2 CH 3 , C(CH 3 ) 2 CH 2 S(O) 2 CH 3 , Ophenyl, OCH 2 CH═CH 2 , OCH 2 cyclopropyl, OCH 2 phenyl, CH 2 CH 2 OCH 2 cyclopropyl, CH 2 CH 2 CH 2 OCH 2 CF 3 , CH 2 C(═O)NHCH 2 CF 3 , or CH 2 CH 2 NHC(═O)CH 3 ,
 wherein each CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , cyclopropyl, cyclobutyl, and phenyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, CN, C(CH 3 ) 3 , CF 3 , OCH 3 , OCH 2 CH 3 , N(CH 3 ) 2 , and pyridinyl. 
 
     
     
         11 . A molecule according to  claim 1 , wherein R 15  and R 16  together are —CH 2 CH 2 CF 2 CH 2 —. 
     
     
         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 H;   (B) R 2  is selected from the group consisting of H and Cl;   (C) R 3  is selected from the group consisting of H and Cl;   (D) R 4  is Cl;   (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 6  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, 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 CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 OCH 2 CH 2 , CH 3 , CH 2 CH 3 , CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 2 CH 3 , CH 2 CH 2 CH 2 CH 2 CH 2 CH 3 , CH 2 CH(CH 3 ) 2 , CH 2 cyclopropyl, CH 2 CH 2 cyclopropyl, CH 2 cyclobutyl, CH 2 phenyl, CH 2 CH 2 phenyl, CH 2 C═CH, CH 2 C═CH, CH 2 CF 3 , CH 2 CHF 2 , CH 2 CH 2 CF 3 , CH 2 CF 2 CF 3 , CH 2 CH 2 CH 2 CF 3 , CH 2 CH 2 CF 2 CF 3 , CH 2 CF 2 CF 2 CF 3 , CH 2 CH 2 CH 2 CH 2 F, CH 2 CH 2 SCH 3 , CH 2 CH 2 S(O)CH 3 , CH 2 CH 2 S(O) 2 CH 3 , C(CH 3 ) 2 CH 2 S(O) 2 CH 3 , Ophenyl, OCH 2 CH═CH 2 , OCH 2 cyclopropyl, OCH 2 phenyl, CH 2 CH 2 OCH 2 cyclopropyl, CH 2 CH 2 CH 2 OCH 2 CF 3 , CH 2 C(═O)NHCH 2 CF 3 , and CH 2 CH 2 NHC(═O)CH 3 ,
 wherein each CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 , cyclopropyl, cyclobutyl, and phenyl, may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, CN, C(CH 3 ) 3 , CF 3 , OCH 3 , OCH 2 CH 3 , N(CH 3 ) 2 , and pyridinyl; and 
   (Q) R 15  and R 16  together are preferably a 4-membered saturated, hydrocarbyl link,   wherein said hydrocarbyl link is substituted with one or more F.   (R) Q 1  and Q 2  are O.   
     
     
         14 . A molecule according to  claim 1  wherein said molecule is selected from the group consisting of F1 through F75, F78, F79, F84 through F88, F91 through F100, F102 through F109, F111 through F135, PF1 through PF7, and PF10 through PF16. 
     
     
         15 . A molecule according to  claim 1  wherein said molecule is selected from the group consisting of F4, F15, F28, F30, F35, F38, F39, F40, F44, F45, F46, F47, F49, and P16. 
     
     
         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 process to control a pest said process comprising applying to a locus, a pesticidally effective amount of a molecule according to  claim 1 . 
     
     
         19 . A process according to  claim 18  wherein said pest is a chewing pest. 
     
     
         20 . A process according to  claim 18  wherein said pest is a sap-feeding pest.