Mesoionic pesticides

Patent metadata

Field	Value
Publication number	US-9210932-B2
Application number	US-201414219079-A
Country	US
Kind code	B2
Filing date	Mar 19, 2014
Priority date	Aug 5, 2009
Publication date	Dec 15, 2015
Grant date	Dec 15, 2015

Abstract

Disclosed are compounds of Formula 1, N-oxides, and salts thereof,

wherein
X is O or S; Y is O or S; A is O, S, NR 3e or C(R 3c )═C(R 3d ); Z is a direct bond, O, S(O) n , NR 6 , C(R 7 ) 2 O, OC(R 7 ) 2 , C(═X 1 ), C(═X 1 )E, EC(═X 1 ), C(═NOR 8 ) or C(═NN(R 6 ) 2 ); a is 1, 2 or 3; and R 1 , R 2 , R 3a -R 3e , R 4 , R 5 , R 6 , R 7 , R 8 , X 1 and E are as defined in the disclosure.

Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or a composition of the invention.

First claim

What is claimed is:

1. A composition comprising a compound of Formula 1 or salt thereof,

wherein
X is O or S;
Y is O or S;
A is C(R 3c )═C(R 3d ), provided that the C(R 3c )═C(R 3d ) moiety is oriented so the carbon atom bonded to R 3d is connected directly to the pyrimidinium ring of Formula 1;
Z is a direct bond, O, S(O) n , NR 6 , C(R 7 ) 2 O, OC(R 7 ) 2 , C(═X 1 ), C(═X 1 )E, EC(═X 1 ), C(═NOR 8 ) or C(═NN(R 6 ) 2 );
X 1 is O, S or NR 9 ;
E is O, S or NR 9a ;
R 1 is a 3- to 10-membered ring or a 7- to 11-membered ring system, each ring or ring system containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N, wherein up to 3 carbon atom ring members are independently selected from C(═O) and C(═S) and the sulfur atom ring members are independently selected from S(═O) u (═NR 24 ) z , each ring or ring system optionally substituted with up to 5 substituents independently selected from R 14 ;
R 2 is H, halogen, cyano, hydroxy, amino, nitro, OCN, SCN, CHO, C(═O)OH, C(═O)NH 2 , C(═S)NH 2 , SO 2 NH 2 , C(═O)R 18 , C(═O)OR 18 , NHR 18 , NR 18 R 19 , C(═O)NR 21 R 19 , C(═S)NR 21 R 19 , SO 2 NR 21 R 19 , OC(═O)R 21 , OC(═O)OR 18 , OC(═O)NR 21 R 19 , N(R 21 )C(═O)R 21 , N(R 21 )C(═O)OR 19 , N(R 21 )C(═O)NR 21 R 22 , OSO 2 R 18 , OSO 2 NR 21 R 22 , NR 21 SO 2 R 18 , NR 21 SO 2 NR 21 R 22 or Si(R 18 R 19 R 20 ); or C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 10 cycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 5 -C 10 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 1 -C 8 alkoxy, C 3 -C 8 cycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 8 alkenyloxy, C 2 -C 8 alkynyloxy, C 1 -C 8 alkylthio, C 1 -C 8 alkylsulfinyl, C 1 -C 8 alkylsulfonyl, C 3 -C 8 cycloalkylthio, C 3 -C 8 cycloalkylsulfinyl, C 3 -C 8 cycloalkylsulfonyl, C 4 -C 10 cycloalkylalkylthio, C 4 -C 10 cycloalkylalkylsulfinyl, C 4 -C 10 cycloalkylalkylsulfonyl, C 2 -C 8 alkenylthio, C 2 -C 8 alkenylsulfinyl, C 2 -C 8 alkenylsulfonyl, C 2 -C 8 alkynylthio, C 2 -C 8 alkynylsulfinyl or C 2 -C 8 alkynylsulfonyl, each unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH 2 , C(═O)R 10 , C(═O)OR 11 , C(═O)NR 12 R 13 , OR 11 , S(O) n R 10 SO 2 NR 12 R 13 and Si(R 10 ) 3 ; or a 3- to 10-membered ring or a 7- to 11-membered ring system, each ring or ring system containing ring members selected from carbon atoms and up to 4 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 4 N, wherein up to 3 carbon atom ring members are independently selected from C(═O) and C(═S) and the sulfur atom ring members are independently selected from S(═O) u (═NR 24 ) z , each ring or ring system optionally substituted with up to 5 substituents independently selected from R 15 ;
R 3a , R 3b , R 3c and R 3d are independently H, halogen, cyano, hydroxy, amino, nitro, SF 5 , OCN, SCN, CHO, C(═O)OH, C(═O)NH 2 , C(═S)NH 2 , SO 2 NH 2 , C(═O)R 18 , C(═O)OR 18 , NHR 18 , NR 18 R 19 , C(═O)NR 21 R 19 , C(═S)NR 21 R 19 , SO 2 NR 21 R 19 OC(═O)R 21 , OC(═O)OR 18 , OC(═O)NR 21 R 19 , N(R 21 )C(═O)R 21 , N(R 21 )C(═O)OR 19 , N(R 21 )C(═O)NR 21 R 22 , OSO 2 R 18 , OSO 2 NR 21 R 22 , NR 21 SO 2 R 18 , NR 21 SO 2 NR 21 R 22 , Si(R 18 R 19 R 20 ) or Z 1 Q t ; or C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 10 cycloalkyl, C 4 -C 10 alkylcycloalkyl, C 4 -C 10 cycloalkylalkyl, C 6 -C 14 cycloalkylcycloalkyl, C 5 -C 10 alkylcycloalkylalkyl, C 3 -C 8 cycloalkenyl, C 1 -C 8 alkoxy, C 3 -C 8 cycloalkoxy, C 4 -C 10 cycloalkylalkoxy, C 2 -C 8 alkenyloxy, C 2 -C 8 alkynyloxy, C 1 -C 8 alkylthio, C 1 -C 8 alkylsulfinyl, C 1 -C 8 alkylsulfonyl, C 3 -C 8 cycloalkylthio, C 3 -C 8 cycloalkylsulfinyl, C 3 -C 8 cycloalkylsulfonyl, C 4 -C 10 cycloalkylalkylthio, C 4 -C 10 cycloalkylalkylsulfinyl, C 4 -C 10 cycloalkylalkylsulfonyl, C 2 -C 8 alkenylthio, C 2 -C 8 alkenylsulfinyl, C 2 -C 8 alkenylsulfonyl, C 2 -C 8 alkynylthio, C 2 -C 8 alkynylsulfinyl or C 2 -C 8 alkynylsulfonyl, each unsubstituted or substituted with at least one substituent independently selected from R 17 ; or R 3a and R 3b , or R 3b and R 3c , or R 3c and R 3d are taken together with the adjacent carbon atoms to which they are attached to form a 5- to 7-membered carbocyclic or heterocyclic ring, each ring containing ring members selected from carbon atoms and up to 3 heteroatoms independently selected from up to 2 O, up to 2 S, and up to 3 N, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and the sulfur atom ring members are independently selected from S(═O) n , each ring optionally substituted with up to 3 substituents independently selected from the group consisting of halogen, cyano, hydroxy, amino, nitro, C(═O)OH, C(═O)NH 2 , SO 2 NH 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, C 3 -C 7 cycloalkyl, C 3 -C 7 halocycloalkyl, C 4 -C 8 alkylcycloalkyl, C 4 -C 8 haloalkylcycloalkyl, C 4 -C 8 cycloalkylalkyl, C 4 -C 8 halocycloalkylalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 haloalkoxycarbonyl, C 2 -C 6 alkylcarbonyl and C 2 -C 6 haloalkylcarbonyl;
each R 4 and R 5 is independently H, halogen, cyano, hydroxy, amino, nitro, OCN, SCN, CHO, C(═O)OH, C(═O)NH 2 , C(═S)NH 2 or SO 2 NH 2 ; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 4 -C 8 alkylcycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 12 cycloalkylcycloalkyl, C 5 -C 8 alkylcycloalkylalkyl, C 3 -C 6 cycloalkenyl, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkoxy, C 4 -C 8 cycloalkylalkoxy, C 2 -C 6 alkenyloxy or C 2 -C 6 alkynyloxy, each unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH 2 , C(═O)R 10 , C(═O)OR 11 , C(═O)NR 12 R 13 , OR 11 , S(O) n R 10 , SO 2 NR 12 R 13 and Si(R 10 ) 3 ; or
R 4 and R 5 are taken together with the carbon atom to which they are attached to form a 3- to 7-membered ring containing ring members selected from carbon atoms and up to 2 heteroatoms independently selected from one O, one S, and up to 2 N, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and the sulfur atom ring member is selected from S, S(O) or S(O) 2 , said ring optionally substituted with up to 4 substituents independently selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl;
each R 6 is independently H; or C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 4 -C 8 alkylcycloalkyl, C 4 -C 8 cycloalkylalkyl, C 6 -C 10 cycloalkylcycloalkyl, C 5 -C 10 alkylcycloalkylalkyl, C 3 -C 6 cycloalkenyl, C 2 -C 6 alkylcarbonyl or C 2 -C 6 alkoxycarbonyl, each unsubstituted or substituted with at least one substituent independently selected from the group consisting of halogen, cyano, nitro, CHO, C(═O)OH, C(═O)NH 2 , C(═O)R 10 , C(═O)OR 11 , C(═O)NR 12 R 13 , OR 11 , S(O) n R 10 , SO 2 NR 12 R 13 and Si(R 10 ) 3 ; or
two R 6 substituents are taken together with the nitrogen atom to which they are attached to form a 3- to 7-membered ring containing ring members selected from carbon atoms and up to 2 heteroatoms independently selected from one O, one S, and up to 2 N, wherein up to 2 carbon atom ring members are independently selected from C(═O) and C(═S) and the sulfur atom ring member is selected from S, S(O) or S(O) 2 , said ring optionally substituted with up to 4 substituents independently selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl;
each R 7

Assignees

• Du Pont

Inventors

• Zhang Wenming
• Holyoke Jr Caleb William
• Hughes Kenneth Andrew
• Lahm George Philip
• Pahutski Jr Thomas Francis
• Tong My-Hanh Thi
• Xu Ming

Classifications

• A61P33/10

  Anthelmintics · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• C07D239/54

  as doubly bound oxygen atoms or as unsubstituted hydroxy radicals · CPC title