Compositions and methods for controlling insects which damage rice and other crops

Abstract

Compositions and methods for controlling insect populations, in particular, insects which attack rice crops, are disclosed. The compositions include one or more compounds from the Formula 1A and one or more compounds from the formulas 1B-G described in the specification, and optionally but preferably include a suitable carrier.

We claim:  
     
         1 . An insecticidal composition which comprises synergistically insecticidal effective amounts of one or more compounds of the following Formula 1A and one or more compounds of the following Formulas 1B-G:  
       
         
           
           
               
               
           
         
       
       wherein: 
 E is selected from the group H and C 1 -C 3  alkyl; or Y is selected from the group H; C 1 -C 6  alkyl, benzyl; C 2 -C 6  alkoxyalkyl; C 2 -C 6  alkenyl; C 2 -C 6  alkynyl; C 1 -C 6  alkyl optionally substituted by halogen, C 1 -C 3  alkoxy, C 1 -C 3  haloalkoxy, —CN, —NO 2 , —S(O) r R 32 , —COR 32 , —CO 2 R 32 , phenyl optionally substituted by halogen, —CN, —C 1 -C 2  haloalkyl and/or C 1 -C 2  haloalkoxy; C 3 -C 6  cycloalkyl; C 3 -C 6  cyclohaloalkyl; C 3 -C 6  cycloalkylalkyl; —CHO; —C 2 -C 6  alkylcarbonyl; —C 2 -C 6  alkoxycarbonyl; —C 2 -C 6  haloalkylcarbonyl; —COR 36 ; —CO 2 R 36 ; —C 1 -C 6  alkylthio; —C 1 -C 6  haloalkylthio; phenylthio; R 12 OC(O)N(R 13 )S— and R 14  (R 15 )NS—;  
 R 1  and R 2  are independently selected from the group H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, C 2 -C 6  haloalkenyl, C 2 -C 6  alkynyl, C 3 -C 6  haloalkynyl, C 2 -C 6  alkoxyalkyl, C 2 -C 6  alkylthioalkyl, C 1 -C 6  nitroalkyl, C 2 -C 6  cyanoalkyl, C 3 -C 8  alkoxycarbonylalkyl, C 3 -C 6  cycloalkyl, C 3 -C 6  halocycloalkyl, halogen, —CN, —N 3 , —SCN, —NO 2 , —OR, —SR 17 , —S(O)R 17 , —S(O) 2 R 17 , —OC(O)R 17 , —OS(O) 2 R 17 , —CO 2 R 17 , —C(O)R 17 , —C(O)NR 17 R 18 , —SO 2 NR 17 R 18 , —NR 17 R 18 , —NR 18 C(O)R 17 , —OC(O)NHR 17 , —NR 18 C(O)NHR 17 , —NR 18 SO 2 R 17 , phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or when m or n is 2, (R 1 ) 2  can be taken together, or (R 2 ) 2  can be taken together as —OCH 2 O—, —OCF 2 O—, —OCH 2 CH 2 O—, —CH 2 C(CH 3 ) 2 O—, —CF 2 CF 2 O or —OCF 2 CF 2 O— to form a cyclic bridge; provided that when R 1  or R 2  is —S(O)R 17 , —S(O) 2 R 17 , —OC(O)R 17  or —OS(O) 2 R 17  then R 17  is other than H;  
 R 3 is selected from the group H, J, —N 3 , —NO 2 , halogen, —N( 22 )R 23 , —C(R 34 )═N—O—R 35 , C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, C 2 -C 6  haloalkenyl, C 2 -C 6  alkynyl, C 2 -C 6  alkoxylalkyl, C 3 -C 8  alkoxycarbonylalkyl, —CO 2 R 17 , —OR 19 , —C(O)R 17 , —C(O)NR 17 R 18 , —C(S)NR 17 R 18 , —C(S)R 17 , —C(S)SR 17 , —CN, —Si( 28 )(R 29 )R 27 , —SR 27 , —S(O)R 27 , —SO 2 R 27 , —P(O)(OR 27 ) 2 , phenyl, phenyl substituted with (R 16 ) p , benzyl and benzyl substituted with 1 to 3 substituents independently selected from W; or R 3  is —C 2 -C 6  epoxyalkyl optionally substituted with a group selected from —C 1 -C 3  alkyl, —CN, —C(O)R 24 , —CO 2 R 24  and phenyl optionally substituted with W; or R 3  is C 1 -C 6  alkyl substituted with a group selected from —C(O)N(R 25 )R 26 , C(O)R 25 , —SR 27 , —S(O)R 27 , —SO 2 R 27 , —SCN, —CN, —C 1 -C 2  haloalkoxy, —Si(R 28 )R 29 )R 30 , —N( 22 )R 23 , —NO 2 —OC(O)R 25 —P(O)(OR ) 2  and J;  
 J is selected from the group saturated, partially unsaturated or aromatic 5- or 6-membered heterocyclic rings, bonded through carbon or nitrogen, containing 1-4 heteroatoms independently selected from the group consisting of 0-2 oxygen, 0-2 sulfur and 0-4 nitrogen, this substituent optionally containing one carbonyl and optionally substituted with one or more members selected from W;  
 R 4  is selected from the group H, C 1 -C 4  alkyl, —COR 20  and C 2 -C 4  alkoxycarbonyl; or  
 R 12  is C 1 -C 6  alkyl;  
 R 13  is C 1 -C 4  alkyl;  
 R 14  and R 15  are independently C 1 -C 4  alkyl; or  
 R 14  and R 15  can be taken together as —CH 2 CH 2 CH 2 CH 2 CH 2 — or —CH 2 CH 2 OCH 2 CH 2 —;  
 R 16  is selected from the group C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, C 2 -C 6  haloalkenyl, C 2 -C 6  alkynyl, C 3 -C 6  haloalkynyl, C 2 -C 6  alkoxyalkyl, C 2 -C 6  alkylthioalkyl, C 1 -C 6  nitroalkyl, C 2 -C 6  cyanoalkyl, C 3 -C 8  alkoxycarbonylalkyl, C 3 -C 6  cycloalkyl, C 3 -C 6  halocycloalkyl, halogen, —CN, —N 3 , —SCN, —NO 2 , —OR 17 , —SR 17 , —S(O)R 17 , —S(O) 2 R 17 , —OC(O)R 17 , —OS(O) 2 R 17 , —CO 2 R 17 , —C(O)R 17 , —C(O)NR 17 R 18 , —SO 2 NR 17 R 18 , —NR 17 R 18 , —NR 18 C(O)R 17 , —OC(O)NHR 17 , NR 18 C(O)NHR 17 , —NR 18 SO 2 R 17 , phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or when p is 2, (R 16 ) 2  can be taken together as —OCH 2 O—, —OCF 2 O—, —OCH 2 CH 2 O—, —CH 2 C(CH 3 ) 2 O—, —CF 2 CF 2 O or —OCF 2 CF 2 O— to form a cyclic bridge; provided that when R 16  is —S(O)R 17 , —S(O) 2 R 17 , —OC(O)R 17  or —OS(O) 2 R 17  then R 17  is other than H;  
 R 17  is selected from the group H, C 1 -C 6  alkyl, C 1 -C 6  haloalkyl, C 2 -C 6  alkenyl, C 2 -C 6  haloalkenyl, C 2 -C 6  alkynyl, C 3 -C 6  haloalkynyl, C 2 -C 6  alkoxyalkyl, C 2 -C 6  alkylthioalkyl, C 1 -C 6  nitroalkyl, C 2 -C 6  cyanoalkyl, C 3 -C 8  alkoxycarbonylalkyl, C 3 -C 6  cycloalkyl, C 3 -C 6  halocycloalkyl, and optionally substituted phenyl and benzyl wherein the substituents are 1 to 3 substituents independently selected from W;  
 R 18  is selected from the group H and C 1 -C 4  alkyl; or  
 R 17  and R 18 , when attached to the same atom, can be taken together as —(CH 2 ) 4 —, —(CH 2 ) 5 —, or —CH 2 CH 2 OCH 2 CH 2 —;  
 R 19  is selected from the group H, C 1 -C 4  alkyl, C 2 -C 4  alkenyl, C 2 -C 4  alkynyl, C 2 -C 4  alkylcarbonyl, C 2 -C 4  alkoxycarbonyl and C 1 -C 4  alkylsulfonyl;  
 R 20  is C 1 -C 3  alkyl;  
 R 21  is selected from the group H, C 1 -C 4  alkyl, C 2 -C 4  alkenyl and C 2 -C 4  alkynyl;  
 R 22  is selected from the group H, C 2 -C 7  alkylcarbonyl, C 2 -C 7  alkoxycarbonyl, optionally substituted C 1 -C 4  alkyl, optionally substituted C 2 -C 4  alkenyl, and optionally substituted C 2 -C 4  alkynyl, the substituents selected from C 1 -C 2  alkoxy, —CN, —C(O)R 30  and —C(O) 2 R 27 ;  
 R 23  is selected from the group H, C 1 -C 3  alkyl, phenyl, phenyl substituted with W, benzyl and benzyl substituted with W;  
 R 24  is selected from the group H, C 1 -C 4  alkyl, C 2 -C 4  alkenyl and C 2 -C 4  alkynyl;  
 R 25  and R 26  are independently selected from the group H and C 1 -C 2  alkyl;  
 R 27  is selected from the group C 1 -C 3  alkyl, phenyl and phenyl substituted with W;  
 R 28  is C 1 -C 3  alkyl;  
 R 29  is C 1 -C 3  alkyl;  
 R 30  is selected from the group H, C 1 -C 3  alkyl, phenyl and phenyl substituted by W;  
 R 32  is selected from the group C 1 -C 3  alkyl;  
 R 34  is selected from the group H, Cl, C 1 -C 4  alkyl, C 1 -C 4  alkoxy, C 1 -C 2  thioalkyl and —CN;  
 R 35  is selected from the group H, C 1 -C 4  alkyl, C 2 -C 3  alkylcarbonyl and C 2 -C 3  alkoxycarbonyl;  
 R 36  is selected from the group phenyl and phenyl substituted with W;  
 W is selected from the group halogen, —CN, —NO 2 , C 1 -C 2  alkyl, C 1 -C 2  haloalkyl, C 1 -C 2  alkoxy, C 1 -C 2  haloalkoxy, C 1 -C 2  alkylthio, C 1 -C 2  haloalkylthio, C 1 -C 2  alkylsulfonyl and C 1 -C 2  haloalkylsulfonyl;  
 m is 1 to 3;  
 n is 1 to 3;  
 p is 1 to 3;  
 r is 0, 1 or 2;  
 t is 2 or 3;  
 u is 1 or 2;  
 R 1′  is —S(O) m′ R 5 ;  
 R 2′  is selected from a hydrogen atom, a halogen atom, —NR 6′ R 7′ , —S(O) n′ R 8′ , —C(O)R 8 , —C(O)OR 9′ , alkyl, haloalkyl, —OR 9′ , or —N═C(R 10′ )(R 11′ );  
 R 3′  is selected from a halogen atom or the hydrogen atom;  
 R 4′  is selected from a halogen atom, haloalkyl, haloalkoxy, —S(O) p′ CF 3 , or —SF 5 ;  
 R 5′  is alkyl or haloalkyl;  
 R 6′  and R 7′  are independently selected from a hydrogen atom, alkyl, haloalkyl, —C(O) R 8′ , —C(O)OR 8′ , —S(O) q′ CF 3 ; the alkyl portions of which are optionally substituted by one or more R 12′ ; or R 6′  and R 7′  are joined so as together form a divalent radical having 4 to 6 atoms in the chain, this divalent radical being alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene, preferably to form a morpholine, pyrrolidine, piperidine or piperazine ring;  
 R 8′  is alkyl or haloalkyl;  
 R 9′  is selected from alkyl, haloalkyl or the hydrogen atom;  
 R 10′  is selected from R 9′  or alkoxy;  
 R 11′  is alkyl or haloalkyl; or is selected from phenyl or heteroaryl that is optionally substituted by one or more groups selected from hydroxy, halogen, alkoxy, —S(O) r′ R 8′ , cyano, R 8′  or combinations thereof;  
 R 12′  is selected from cyano, nitro, alkoxy, haloalkoxy, —S(O) s′ -alkyl, —S(O) s′ -haloalkyl, —C(O)-alkyl, —C(O)-haloalkyl, —C(O)O-alkyl, —C(O)O-haloalkyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;  
 X′ is selected from the nitrogen atom, or the radical C—R 13′ ;  
 R 13′  is a halogen atom;  
 R 14′  is—C(O)CH 3  or —CN; and  
 m′, n′, p′, q′, r′ and s′ represent, independently of one another, the values zero, one or two;  
 
     
     
         2 . The composition of  claim 1 , wherein the compound of Formula 1A is ethiprole and the compound of Formulas 1B-G is indoxacarb.  
     
     
         3 . The composition of  claim 1 , further comprising a carrier.  
     
     
         4 . The composition of  claim 1 , further comprising an additional insecticide.  
     
     
         5 . The composition of  claim 1 , wherein the ratio by weight of the compound(s) of Formula 1A to the compound(s) of Formulas 1B-G is between 1/32 and 32/1.  
     
     
         6 . The composition of  claim 5 , wherein the compound of Formula 1A is ethiprole and the compound of Formulas 1B-G is indoxacarb.  
     
     
         7 . The composition of  claim 1 , wherein the composition is in the form of a conventional crop protection product formulation selected from the group consisting of wettable powders, emulsifiable concentrates, aqueous solutions, emulsions, sprayable solutions, oil-or-water-based dispersions, suspoemulsions, dusts, seed treatment products, granules for soil application or spreading, water-dispersible granules, ULV formulations, microcapsules and waxes.  
     
     
         8 . The composition as claimed in  claim 7 , wherein the crop is rice.  
     
     
         9 . A synergistic insecticidal composition for controlling insects in rice plants which comprises 10 to 80% by weight of ethiprole and indoxacarb.  
     
     
         10 . The composition of  claim 9 , wherein the composition comprises between 10 and 50% by weight of ethiprole and indoxacarb.  
     
     
         11 . A method of controlling insect pests, which comprises applying a synergistically insecticidal effective amount of the composition as claimed in  claim 9  to the insect pests to the rice plants, areas or substrates infested with them.