US2009221424A1PendingUtilityA1

Pesticides

67
Assignee: DOW AGROSCIENCES LLCPriority: Mar 3, 2008Filed: Feb 27, 2009Published: Sep 3, 2009
Est. expiryMar 3, 2028(~1.6 yrs left)· nominal 20-yr term from priority
C07D 213/75C07C 381/10C07C 2603/18A01N 43/40C07C 2601/14C07C 2601/02C07D 405/12A01N 47/44A01N 47/36A01N 47/34C07D 401/12C07D 413/12C07D 213/32
67
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Claims

Abstract

Compounds having the following generic formula are disclosed.

Claims

exact text as granted — not AI-modified
1 . A compound having the following formula (I) 
     
       
         
         
             
             
         
       
     
     wherein:
 (a) R1 is C 2 -C 8  alkenyl, C 2 -C 8  alkenyloxy, C 2 -C 8  alkenylthio, C 1 -C 8  alkoxy, C 1 -C 8  alkyl, C 1 -C 8  alkylthio, C 2 -C 8  alkynyl, C 2 -C 8  alkynyloxy, C 2 -C 8  alkynylthio, aryl, C 3 -C 8  cycloalkenyl, C 3 -C 8  cycloalkenyloxy, C 3 -C 8  cycloalkenylthio, C 3 -C 8  cycloalkyl, C 3 -C 8  cycloalkoxy, C 3 -C 8  cycloalkylthio, heterocyclyl, or C 0 -C 8  alkyl-C(═O)OR8, wherein each of which may be independently substituted with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, S(═O) n1 C 1 -C 6  alkyl (where n1=0-2), S(═O) n1 C 1 -C 6  haloalkyl (where n1=0-2), OSO 2 C 1 -C 6  haloalkyl, C(═O)OC 1 -C 6  alkyl, C(═O)C 1 -C 6  alkyl, C(═O)C 1 -C 6  haloalkyl, aryl, C 1 -C 6  hydroxyalkyl, NR9R10, and heterocyclyl; 
 (b) R2 is C 2 -C 8  alkenyl, C 2 -C 8  alkenyloxy, C 2 -C 8  alkenylthio, C 1 -C 8  alkoxy, C 1 -C 8  alkyl, C 1 -C 8  alkylthio, C 2 -C 8  alkynyl, C 2 -C 8  alkynyloxy, C 2 -C 8  alkynylthio, aryl, C 3 -C 8  cycloalkenyl, C 3 -C 8  cycloalkenyloxy, C 3 -C 8  cycloalkenylthio, C 3 -C 8  cycloalkyl, C 3 -C 8  cycloalkoxy, C 3 -C 8  cycloalkylthio, heterocyclyl, or C 0 -C 8  alkyl-C(═O)OR8, wherein each of which may be independently substituted with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, S(═O) n1 C 1 -C 6  alkyl (where n1=0-2), S(═O) n1 C 1 -C 6  haloalkyl (where n1=0-2), OSO 2 C 1 -C 6  haloalkyl, C(═O)OC 1 -C 6  alkyl, C(═O)C 1 -C 6  alkyl, C(═O)C 1 -C 6  haloalkyl, aryl, C 1 -C 6  hydroxyalkyl, NR9R10, and heterocyclyl, and wherein R2 and R5 may also form a 4, 5, or 6 membered ring; 
 (c) R3 is F, Cl, Br, I, C 2 -C 8  alkenyl, C 2 -C 8  alkenyloxy, C 2 -C 8  alkenylthio, C 1 -C 8  alkoxy, C 1 -C 8  alkyl, C 1 -C 8  alkylthio, C 2 -C 8  alkynyl, C 2 -C 8  alkynyloxy, C 2 -C 8  alkynylthio, aryl, C 3 -C 8  cycloalkenyl, C 3 -C 8  cycloalkenyloxy, C 3 -C 8  cycloalkenylthio, C 3 -C 8  cycloalkyl, C 3 -C 8  cycloalkoxy, C 3 -C 8  cycloalkylthio, H, heterocyclyl, C(═O)C 1 -C 6  alkyl, C(═O)C 1 -C 6  aryl, or C 0 -C 8  alkyl-C(═O)OR8, wherein each of which may be independently substituted (except for H, F, Cl, Br, I) with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, S(═O) n1 C 1 -C 6  alkyl (where n1=0-2), S(═O) n1 C 1 -C 6  haloalkyl (where n1=0-2), OSO 2 C 1 -C 6  haloalkyl, C(═O)OC 1 -C 6  alkyl, C(═O)C 1 -C 6  alkyl, C(═O)C 1 -C 6  haloalkyl, aryl (wherein said aryl may be substituted with one or more substituents selected from F, Cl, Br, I, or C 1 -C 8  alkoxy) C 1 -C 6  hydroxyalkyl, NR9R10, and heterocyclyl, and wherein R3 and R4 may also form a 4, 5, or 6 membered ring; 
 (d) R4 is F, Cl, Br, I, C 2 -C 8  alkenyl, C 2 -C 8  alkenyloxy, C 2 -C 8  alkenylthio, C 1 -C 8  alkoxy, C 1 -C 8  alkyl, C 1 -C 8  alkylthio, C 2 -C 8  alkynyl, C 2 -C 8  alkynyloxy, C 2 -C 8  alkynylthio, aryl, C 3 -C 8  cycloalkenyl, C 3 -C 8  cycloalkenyloxy, C 3 -C 8  cycloalkenylthio, C 3 -C 8  cycloalkyl, C 3 -C 8  cycloalkoxy, C 3 -C 8  cycloalkylthio, H, heterocyclyl, C(═O)C 1 -C 6  alkyl, C(═O)C 1 -C 6  aryl, or C 0 -C 8  alkyl-C(═O)OR8, wherein each of which may be independently substituted (except for H, F, Cl, Br, I) with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, S(═O) n1 C 1 -C 6  alkyl (where n1=0-2), S(═O) n1 C 1 -C 6  haloalkyl (where n1=0-2), OSO 2 C 1 -C 6  haloalkyl, C(═O)OC 1 -C 6  alkyl, C(═O)C 1 -C 6  alkyl, C(═O)C 1 -C 6  haloalkyl, aryl (wherein said aryl may be substituted with one or more substituents selected from F, Cl, Br, I, or C1-C 8  alkoxy) C 1 -C 6  hydroxyalkyl, NR9R10, and heterocyclyl, and wherein R3 and R4 may also form a 4, 5, or 6 membered ring; 
 (e) R5 is C 2 -C 8  alkenyl, C 2 -C 8  alkenyloxy, C 2 -C 8  alkenylthio, C 1 -C 8  alkoxy, C 1 -C 8  alkyl, C 1 -C 8  alkylthio, C 2 -C 8  alkynyl, C 2 -C 8  alkynyloxy, C 2 -C 8  alkynylthio, aryl, C 3 -C 8  cycloalkenyl, C 3 -C 8  cycloalkenyloxy, C 3 -C 8  cycloalkenylthio, C 3 -C 8  cycloalkyl, C 3 -C 8  cycloalkoxy, C 3 -C 8  cycloalkylthio, H, heterocyclyl, or C 0 -C 8  alkyl-C(═O)OR8, wherein each of which may be independently substituted (except for H) with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, S(═O) n1 C 1 -C 6  alkyl (where n1=0-2), S(═O) n1 C 1 -C 6  haloalkyl (where n1=0-2), OSO 2 C 1 -C 6  haloalkyl, C(═O)OC 1 -C 6  alkyl, C(═O)C 1 -C 6  alkyl, C(═O)C 1 -C 6  haloalkyl, aryl, C 3 -C 8  cycloalkyl, C 1 -C 6  hydroxyalkyl, NR9R10, and heterocyclyl, and wherein R2 and R5 may also form a 4, 5, or 6 membered ring, and wherein R5 and R6 may also form a 3, 4, 5, or 6 membered ring; 
 (f) R6 is C 2 -C 8  alkenyl, C 2 -C 8  alkenyloxy, C 2 -C 8  alkenylthio, C 1 -C 8  alkoxy, C 1 -C 8  alkyl, C 1 -C 8  alkylthio, C 2 -C 8  alkynyl, C 2 -C 8  alkynyloxy, C 2 -C 8  alkynylthio, aryl, C 3 -C 8  cycloalkenyl, C 3 -C 8  cycloalkenyloxy, C 3 -C 8  cycloalkenylthio, C 3 -C 8  cycloalkyl, C 3 -C 8  cycloalkoxy, C 3 -C 8  cycloalkylthio, H, heterocyclyl, or C 0 -C 8  alkyl-C(═O)OR8, wherein each of which may be independently substituted (except for H) with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, S(═O) n1 C 1 -C 6  alkyl (where n1=0-2), S(═O) n1 C 1 -C 6  haloalkyl (where n1=0-2), OSO 2 C 1 -C 6  haloalkyl, C(═O)OC 1 -C 6  alkyl, C(═O)C 1 -C 6  alkyl, C(═O)C 1 -C 6  haloalkyl, aryl, C 3 -C 8  cycloalkyl, C 1 -C 6  hydroxyalkyl, NR9R10, and heterocyclyl, and wherein R2 and R5 may also form a 4, 5, or 6 membered ring, and wherein R5 and R6 may also form a 3, 4, 5, or 6 membered ring; 
 (g) n is 0 to 4; 
 (h) X is NR8, O, or S; 
 (i) J is N or CR7; 
 (j) R7 is H, F, Cl, Br, I, C 2 -C 8  alkenyl, C 2 -C 8  alkenyloxy, C 2 -C 8  alkenylthio, C 1 -C 8  alkoxy, C 1 -C 8  alkyl, C 1 -C 8  alkylthio, C 2 -C 8  alkynyl, C 2 -C 8  alkynyloxy, C 2 -C 8  alkynylthio, aryl, C 3 -C 8  cycloalkenyl, C 3 -C 8  cycloalkenyloxy, C 3 -C 8  cycloalkenylthio, C 3 -C 8  cycloalkyl, C 3 -C 8  cycloalkoxy, C 3 -C 8  cycloalkylthio, heterocyclyl, or C 0 -C 8  alkyl-C(═O)OR8, wherein each of which may be independently substituted (except for H, F, Cl, Br, I) with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, S(═O) n1 C 1 -C 6  alkyl (where n1=0-2), S(═O) n1 C 1 -C 6  haloalkyl (where n1=0-2), OSO 2 C 1 -C 6  haloalkyl, C(═O)OC 1 -C 6  alkyl, C(═O)C 1 -C 6  alkyl, C(═O)C 1 -C 6  haloalkyl, aryl, C 1 -C 6  hydroxyalkyl, NR9R10 and heterocyclyl; 
 (k) R8 is H, OH, OC(═O)C 1 -C 6  alkyl, C 2 -C 8  alkenyl, C 2 -C 8  alkenyloxy, C 2 -C 8  alkenylthio, C 1 -C 8  alkoxy, C 1 -C 8  alkyl, C 1 -C 8  alkylthio, C 2 -C 8  alkynyl, C 2 -C 8  alkynyloxy, C 2 -C 8  alkynylthio, aryl, C 3 -C 8  cycloalkenyl, C 3 -C 8  cycloalkenyloxy, C 3 -C 8  cycloalkenylthio, C 3 -C 8  cycloalkyl, C 3 -C 8  cycloalkoxy, C 3 -C 8  cycloalkylthio, or heterocyclyl, wherein each of which may be independently substituted with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 1 -C 6  alkoxy, C 3 -C 8  cycloalkyl, C 3 -C 8  halocycloalkyl, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, S(═O) n1 C 1 -C 6  alkyl (where n1=0-2), S(═O) n1 C 1 -C 6  haloalkyl (where n1=0-2), OSO 2 C 1 -C 6  haloalkyl, C(═O)OC 1 -C 6  alkyl, C(═O)C 1 -C 6  alkyl, C(═O)C 1 -C 6  haloalkyl, aryl (wherein said aryl may be substituted with one or more substituents selected from F, Cl, Br, I, or C 1 -C 8  alkoxy), C 1 -C 6  hydroxyalkyl, and heterocyclyl; 
 (l) R9 is C 2 -C 8  alkenyl, C 2 -C 8  alkenyloxy, C 2 -C 8  alkenylthio, C 1 -C 8  alkoxy, C 1 -C 8  alkyl, C 1 -C 8  alkylthio, C 2 -C 8  alkynyl, C 2 -C 8  alkynyloxy, C 2 -C 8  alkynylthio, aryl, C 3 -C 8  cycloalkenyl, C 3 -C 8  cycloalkenyloxy, C 3 -C 8  cycloalkenylthio, C 3 -C 8  cycloalkyl, C 3 -C 8  cycloalkoxy, C 3 -C 8  cycloalkylthio, or heterocyclyl, wherein each of which may be independently substituted with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, S(═O) n1 C 1 -C 6  alkyl (where n1=0-2), S(═O) n1 C 1 -C 6  haloalkyl (where n1=0-2), OSO 2 C 1 -C 6  haloalkyl, C(═O)OC 1 -C 6  alkyl, C(═O)C 1 -C 6  alkyl, C(═O)C 1 -C 6  haloalkyl, aryl, C 1 -C 6  hydroxyalkyl, and heterocyclyl, and wherein R9 and R10 may also form a 4, 5, or 6 membered ring; and 
 (m) R10 is C 2 -C 8  alkenyl, C 2 -C 8  alkenyloxy, C 2 -C 8  alkenylthio, C 1 -C 8  alkoxy, C 1 -C 8  alkyl, C 1 -C 8  alkylthio, C 2 -C 8  alkynyl, C 2 -C 8  alkynyloxy, C 2 -C 8  alkynylthio, aryl, C 3 -C 8  cycloalkenyl, C 3 -C 8  cycloalkenyloxy, C 3 -C 8  cycloalkenylthio, C 3 -C 8  cycloalkyl, C 3 -C 8  cycloalkoxy, C 3 -C 8  cycloalkylthio, or heterocyclyl, wherein each of which may be independently substituted with one or more of the following substituents, F, Cl, Br, I, CN, NO 2 , C 1 -C 6  alkyl, C 2 -C 6  alkenyl, C 2 -C 6  alkynyl, C 1 -C 6  alkoxy, C 1 -C 6  haloalkyl, C 1 -C 6  haloalkoxy, C 1 -C 6  haloalkylthio, S(═O) n1 C 1 -C 6  alkyl (where n1=0-2), S(═O) n1 C 1 -C 6  haloalkyl (where n=0-2), OSO 2 C1-C 6  haloalkyl, C(═O)OC 1 -C 6  alkyl, C(═O)C 1 -C 6  alkyl, C(═O)C 1 -C 6  haloalkyl, aryl, C 1 -C 6  hydroxyalkyl, and heterocyclyl, and wherein R9 and R10 may also form a 4, 5, or 6 membered ring. 
 
   
   
       2 . A compound that is a pesticidally acceptable acid addition salt of a compound according to  claim 1 . 
   
   
       3 . A solvate comprising compound according to  claim 1 . 
   
   
       4 . A process comprising applying a compound according to  claim 1  to a locus to control pests. 
   
   
       5 . A process comprising applying a compound according to  claim 1  to a locus to control pests of Phylum Nematoda or Phylum Arthropoda. 
   
   
       6 . A composition comprising a mixture of a compound according to  claim 1  with at least one other pesticide. 
   
   
       7 . A composition comprising a mixture of a compound according to  claim 1  with at least one herbicide, at least one fungicide, or at least one herbicide and fungicide. 
   
   
       8 . A composition comprising a compound according to  claim 1  with at least one of the following items: acetyl choline esterase inhibitor; sodium channel modulator; chitin biosynthesis inhibitor; GABA-gated chloride channel antagonist; GABA and glutamate-gated chloride channel agonist; acetyl choline receptor agonist; MET I inhibitor; Mg-stimulated ATPase inhibitor; nicotinic acetylcholine receptor; Midgut membrane disrupter; or oxidative phosphorylation disrupter. 
   
   
       9 . A process of applying a compound of  claim 1  to a seed. 
   
   
       10 . A process of applying a compound of  claim 1  to a seed that has been genetically transformed to express one or more specialized traits. 
   
   
       11 . A process of applying a compound of  claim 1  to a genetically transformed plant that has been genetically transformed to express one or more specialized traits. 
   
   
       12 . A process of orally administering or applying a compound of  claim 1  to an animal. 
   
   
       13 . A process comprising reacting 
     
       
         
         
             
             
         
       
     
     to yield a compound according to  claim 1 , wherein R1, R2, R3, R4, R5, and R6 are as specified in  claim 1 . 
   
   
       14 . A compound having the following formula

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