United States Patent (10) Patent No.: US 7,288,554 B2 Finkelstein Et Al
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USOO7288554B2 (12) United States Patent (10) Patent No.: US 7,288,554 B2 Finkelstein et al. (45) Date of Patent: Oct. 30, 2007 (54) ORTHO-SUBSTITUTED ARYL AMIDES FOR 6,548,512 B1 4/2003 Pinto et al. CONTROLLING INVERTEBRATE PESTS 6,602,895 B2 8/2003 Galemmo, Jr. et al. 6,747,047 B2 * 6/2004 Lahm et al. ................ 514,341 (75) Inventors: Bruce Lawrence Finkelstein, Newark, 2004.0102324 A1 5/2004 Annis et al. DE (US); George Philip Lahm, 2004/O110777 A1 6/2004 Annis et al. Wilmington, DE (US); Tom Paul 2004/O138450 A1 7, 2004 Clark Selby, Wilmington, DE (US); Thomas 2004/O142984 A1 T/2004 Lahm et al. Martin Stevenson, Newark, DE (US) 2004/0171649 A1 9, 2004 Annis et al. s s 2004/O198984 A1 10, 2004 Lahm et al. (73) Assignee: E.I. du Pont de Nemours and 2004/0198987 A1 10/2004 Freudenberger et al. Company, Wilmington, DE (US) 2004/0209923 A1 10/2004 Berger et al. s s 2004/02599.13 A1 12, 2004 Clark (*) Notice: Subject to any disclaimer, the term of this SOE. A. ck 3. hy s - - - - - - - - - - - - - - - - 514,341 patent is extended or adjusted under 35 ak ( a. U.S.C. 154(b) by 0 days. 2005, 0147633 A1 7/2005 Stevenson (21) Appl. No.: 10/483,118 FOREIGN PATENT DOCUMENTS (22) PCT Filed: Aug. 13, 2002 DE 1543 332 8, 1969 DE 1543 332.6 8, 1969 (86). PCT No.: PCT/USO2/26959 DE 27.10382 9, 1978 DE 44.28380 A 8, 1994 S 371 (c)(1), DE 1984.0322 A1 9, 1998 (2), (4) Date: Jan. 7, 2004 EP 0289879. A 11, 1988 EP O919.542 A2 6, 1999 (87) PCT Pub. No.: WO03/016300 EP O 946 508 A1 10, 1999 EP 1193254 A1 1, 2001 PCT Pub. Date: Feb. 27, 2003 (65) Prior Publication Data (Continued) US 2004/0192731 A1 Sep. 30, 2004 OTHER PUBLICATIONS O O Ca 135:92626, “Synthesis of isoxazolylsulfonamides derivs. that Related U.S. Application Data modulate the activity of endothelin'. Wu et al.* (60) Eyal application No. 60/312,423, filed on Aug. (Continued) s Primary Examiner Bernard Dentz (51) Int. Cl. Assistant Examiner Binta Robinson A6 IK 3/44 (2006.01) A6 IK 3L/45 (2006.01) (57) ABSTRACT CO7D 40/04 (2006.01) CO7D 23/00 (2006.01) Disclosed are compounds of Formula I, their N-oxides and (52) U.S. Cl. ................... 514/341; 514/406; 548/374.1; agriculturally Suitable salts (I) wherein J is a phenyl ring, a 548,274.1 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9 (58) Field of Classification Search ............. 546/268.1, or 10-membered fused carbobicyclic O heterobicyclic ring 546/275.4, 275.7, 276.1, 274.1: 548/374.1, system wherein each ring or ring system is Substituted with 548/376.1, 366.4, 366.7, 371.7, 275.4, 360.5, from one to four substituents independently selected from 548/370.1; 514/341, 406; 504/141, 142, R; and A, B, G. R. R. R. R. R. Rand n are as defined 504/143, 144, 145, 146, 148, 149 in the disclosure. Also disclosed are methods for controlling See application file for complete search history. invertebrate pests comprising contacting the pests or their (56) References Cited environment with a biologically effective amount of a com pound of Formula (I) and compositions containing the U.S. PATENT DOCUMENTS compounds of Formula (I) 3,840,541 A 10, 1974 Collin et al. 4,137,325 A 1/1979 Sellstedt et al. (I) 4,175,184 A 11/1979 Merkle et al. 4.321,371 A 3/1982 Parget al. 4,565,875 A 1, 1986 Cavender 5,602,126 A 2f1997 Barnette et al. 5,728,693. A 3, 1998 Stevenson 5.998.424. A 12/1999 Galemmo, Jr. et al. 6,020,357 A 2/2000 Pinto et al. 6.297,195 B1 10/2001 Gesing et al. 6,403,620 B1 6/2002 Galemmo, Jr. et al. 18 Claims, No Drawings US 7,288,554 B2 Page 2 FOREIGN PATENT DOCUMENTS WO WO 03/016284 2, 2003 WO WO O3,106427 12/2003 EP O991 625 B1 6, 2005 WO WO 04/O11447 2, 2004 GB 1178322 1, 1970 WO WO 04/O11453 2, 2004 IT 869213 7, 1970 WO WO 04/033468 4/2004 NL 6603319 9, 1967 WO WO 04/046129 6, 2004 NL 92O2O78 A 11, 1992 WO WO 04/067528 9, 2004 WO WO96,0517O A 2, 1996 WO WO96,384.19 12/1996 WO WO97/47589 A 12/1997 OTHER PUBLICATIONS WO WO98,03508 A 1, 1998 Peter H. Gore, et al., “Friedel-Crafts Reactions. Part XXV. Acetyla WO WO98.28269 7, 1998 tion and Benzoylation of lodobenzene and of o-, m-, and WO WO98,57937 12/1998 p-iodotoluenes”, J.C.S. Perkin I, 1973, pp. 2940-2948. WO WO O1/O2354 A1 1, 2001 Milton J. Kornet, “Synthesis and Anticonvulsant Activity of 3-alkyl WO WO O1/32628 A1 5, 2001 3,4-dihydro-2(1H)-quinazolinones”. J. Heterocyclic Chem., 1992, WO WOO 1/70671 A2 9, 2001 pp. 103-105, 29. WO WO O2,32856 A2 4/2002 WO WO O2/48115 A2 6, 2002 * cited by examiner US 7,288,554 B2 1. 2 ORTHO-SUBSTITUTED ARYL AMIDES FOR cyclic or heterobicyclic ring system wherein each ring CONTROLLING INVERTEBRATE PESTS or ring system is substituted with from one to four substituents independently selected from R: CROSS-REFERENCE TO RELATED K is NRC(=A) , N=C(GR) or NRSO : APPLICATIONS L is C(=B)NR C(GR)=N , SONR , - C(=B)O or - C(=B)–: This application is a national filing under 35 U.S.C. 371 A and B are independently O, S, NR, NOR, NN(R), of International Application No. PCT/US02/26959, filed 13 S=O, N. CN or N NO; Aug. 2002, which claims priority of U.S. provisional appli each G is independently O, S or NR; cation No. 60/312,423, filed 15 Aug. 2001. 10 R" is H; or C-C alkyl, C-C alkenyl, C-C alkynyl or C-C cycloalkyl each optionally Substituted with one BACKGROUND OF THE INVENTION or more substituents independently selected from the group consisting of halogen, CN, NO, hydroxy, C–C This invention relates to certain ortho-substituted aryl alkoxy, C-C alkylthio. C-C alkylsulfinyl, C-C, amides, their N-oxides, salts and compositions Suitable for 15 alkylsulfonyl, C-C alkoxycarbonyl, C-C alky agronomic and nonagronomic uses, including those listed lamino, C-C dialkylamino and C-C cycloalky below, and methods of their use for controlling invertebrate lamino; or pests in both agronomic and nonagronomic environments. R" is C-C alkylcarbonyl, C-C alkoxycarbonyl, C-C, The control of invertebrate pests is extremely important in alkylaminocarbonyl or C-C dialkylaminocarbonyl: achieving high crop efficiency. Damage by invertebrate pests R is H. C-C alkyl, C-C alkenyl, C-C alkynyl, to growing and stored agronomic crops can cause significant C-C cycloalkyl, C-C alkoxy, C-C alkylamino, reduction in productivity and thereby result in increased C-C dialkylamino, C-C cycloalkylamino, C-C, costs to the consumer. The control of invertebrate pests in alkoxycarbonyl or C-C alkylcarbonyl: forestry, greenhouse crops, ornamentals, nursery crops, R is H; C1-C4 alkoxy; C1-C4 alkylamino; C–Cs dialky stored food and fiber products, livestock, household, and 25 lamino: C-C cycloalkylamino: C-C alkoxycarbo public and animal health is also important. Many products nyl or C-C alkylcarbonyl: or C-C alkyl, C-C, are commercially available for these purposes, but the need alkenyl, C-C alkynyl or C-C cycloalkyl, each continues for new compounds that are more effective, less optionally substituted with one or more substituents costly, less toxic, environmentally safer or have different independently selected from the group consisting of modes of action. 30 halogen, CN, NO, hydroxy, C-C alkoxy, C-C, NL 9202078 discloses N-acyl anthranilic acid derivatives haloalkoxy, C-C alkylthio, C-C alkylsulfinyl, of Formula i as insecticides C-C alkylsulfonyl, C-C alkoxycarbonyl, C-C, alkylcarbonyl, C-C trialkylsilyl, and a phenyl, phe noxy or 5- or 6-membered heteroaromatic ring, each 35 ring optionally substituted with from one to three R5 R6 substituents independently selected from R. or RandR can be taken together with the nitrogen to which O X R7 they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom selected R4 N 40 from the group consisting of nitrogen, Sulfur and oxy R3 N Ny R9 R8 gen, said ring optionally substituted with from one to four Substituents independently selected from the group O consisting of C-C alkyl, halogen, CN, NO, and R2 C-C alkoxy, 45 each R is independently C1-C alkyl, C-C alkenyl, RI Z C-C alkynyl, C-C cycloalkyl, C-C haloalkyl, C-C haloalkenyl, C-C haloalkynyl, C-C halocy wherein, interalia, X is a direct bond; Y is H or C-C alkyl: cloalkyl, halogen, CN, NO, hydroxy, C-C alkoxy, Z is NH2, NH(C-C alkyl) or N(C-C alkyl); and R' C-C haloalkoxy, C-C alkylthio. C-C alkylsulfi through R are independently H, halogen, C-C alkyl, 50 nyl, C-C alkylsulfonyl, C-C haloalkylthio, C-C phenyl, hydroxy, C-C alkoxy or C-C, acyloxy. haloalkylsulfinyl, C-C haloalkylsulfonyl, C-C, alkylamino, C-C dialkylamino, C-C cycloalky SUMMARY OF THE INVENTION lamino, or C-C trialkylsilyl; or This invention pertains to compounds of Formula I, and each R is independently a phenyl, benzyl or phenoxy 55 ring, each ring optionally Substituted with from one to N-oxides and salts thereof three substituents independently selected from R: each R is independently H, C-C alkyl, C.