United States Patent (10) Patent No.: US 7,754,738 B2 Lahm Et Al
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USOO7754738B2 (12) United States Patent (10) Patent No.: US 7,754,738 B2 Lahm et al. (45) Date of Patent: Jul. 13, 2010 (54) PYRAZOLE AND PYRROLE CARBOXAMIDE 7,241,767 B2 7/2007 Clarket al. INSECTICDES 7,288,554 B2 * 10/2007 Finkelstein et al. ......... 514,341 2004.0102324 A1 5/2004 Annis et al. (75) Inventors: George Philip Lahm, Wilmington, DE 2.8. 8. A. 183. Rerger et al. Strans' TE: Marti 2004/0242645 A1 12/2004 Clarket al. ................. 514,340 1Im1ngton, ; nomas IV artin 2005.0075372 A1 4, 2005 Lahm et al. Stevenson, Newark, DE (US) 2006/0205748 A1* 9, 2006 Annis et al. ................. 514,275 (73) Assignee: E.I. du Pont de Nemours and FOREIGN PATENT DOCUMENTS Company, Wilmington, DE (US) EP O 946 508 A1 10, 1999 EP O991 625 B1 6, 2005 (*) Notice: Subject to any disclaimer, the term of this JP 2129.171 5, 1990 patent is extended or adjusted under 35 WO WO98.28269 7, 1998 U.S.C. 154(b) by 0 days. WO WO98,57937 12/1998 WO WOO 170671 9, 2001 (21) Appl. No.: 10/514, 183 WO WOO3016300 2, 2003 WO WOO3016304 2, 2003 (22) PCT Filed: Jun. 10, 2003 WO WOO3O26415 4/2003 WO WOO3O27099 4/2003 (86). PCT No.: PCT/USO3A18609 OTHER PUBLICATIONS S371 (c)(1), Kordiketal, Pyrazolecarboxamide human neuropeptideY5 receptor (2),2). (4) Date: Nov. 10,9 2004 ligands with in vivo antifeedant activity, Bioorganic & Medicinal Chemistry Letters, 2001, 11(17), 2287-2290.* (87) PCT Pub. No.: WO03/106427 XPO02275434 Order Nos. 5K-0011, SK-014, 2H-016, SK-020, 5K026 and “Interchim Intermediates' Jul. 9, 2002, Interchim, 231 PCT Pub. Date: Dec. 24, 2003 Avenue. * cited by examiner (65) Prior Publication Data y US 2006/0167060A1 Jul 27, 2006 Pririmary ExaminerExaminer—Allon Alton NPIN Pryor Related U.S. Application Data (57)57 ABSTRACT (60) Provisional application No. 60/388,244, filed on Jun. This invention provides compounds of Formula (I), N-oxides 13, 2002. and salts thereof wherein: A is O or S: B is a phenyl ring or a s pyridine ring, each ring optionally substituted with 1 to 5 R; (51) Int. Cl. J is a pyrazole or a pyrrole heterocyclic ring system as defined AOIN 43/40 (2006.01) herein; and; R is H; or C-C alkyl, C-C alkenyl, C-C, A6 IK 3/44 (2006.01) alkynyl or C-C cycloalkyl each optionally Substituted with (52) U.S. Cl. ....................... 514/332, 514/333, 514/341, one or more Substituents selected from the group consisting s s 514,406 of halogen, CN, NO, hydroxy, C-C alkoxy, C-C alky (58) Field of Classification Search ................. 51434. Ithio. C-C alkylsulfinyl, C1-C4 alkylsulfonyl, C2-C alkoxy 5147406. 332 333 carbonyl, C-C alkylamino, C-C dialkylamino and C-C, See application file for complete search histo s cycloalkylamino. Also disclosed are methods for controlling pp p ry. at least one invertebrate pest comprising contacting the inver (56) References Cited tebrate pest or its environment with a biologically effective amount of at least one compound of Formula I, an N-oxide or U.S. PATENT DOCUMENTS a salt thereof (e.g., as a composition described herein). This 5.998.424. A 12/1999 Galemmo, Jr. et al. invention also pertains to a composition comprising at least 6,020,357 A 2/2000 Pinto et al. one compound of Formula I, an N-oxide or a salt thereof; and 6,403,620 B1 6/2002 Galemmo, Jr. et al. at least one additional component selected from the group 6,548,512 B1 4/2003 Pinto et al. consisting of a Surfactant, a solid diluent and a liquid diluent. 6,602,895 B2 8/2003 Galemmo, Jr. et al. 6,747,047 B2 6, 2004 Lahm et al. 6,965,032 B2 11/2005 Freudenberger (I) 6,995, 178 B2 2/2006 Lahm et al. 7,038,057 B2 5, 2006 Annis et al. 7,087,598 B2 8, 2006 Clark 7,148,217 B2 12/2006 Selby 7,157,475 B2 1, 2007 Clark 7,179,824 B2 2/2007 Zimmerman 7,199,138 B2 4/2007 Finkelstein et al. 7,232,836 B2 6, 2007 Lahm et al. 8 Claims, No Drawings US 7,754,738 B2 1. PYRAZOLE AND PYRROLE CARBOXAMIDE INSECTICDES -continued J-2 BACKGROUND OF THE INVENTION 5 This invention relates to certain heterocyclic amides, their N-oxides, salts and compositions Suitable for agronomic and nonagronomic uses, including those uses listed below, and a J-3 method of their use for controlling invertebrate pests in both R8, agronomic and nonagronomic environments. 10 The control of invertebrate pests is extremely important in -N achieving high crop efficiency. Damage by invertebrate pests to growing and stored agronomic crops can cause significant / - reduction in productivity and thereby resultin increased costs 3 to the consumer. The control of invertebrate pests in forestry, 15 R5 J-4 greenhouse crops, ornamentals, nursery crops, stored food 3 4 and fiber products, livestock, household, and public and ani W A-R7 mal health is also important. Many products are commer 2 y cially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, N environmentally safer or have different modes of action. R5 J-5 JP02129171 discloses pyrazolecarboxanilide derivatives 4 5 of Formula i as insecticides N 25 N NRs and 2 R5 J-6 R8. NH X3 A 30 N wherein, R' through R and X' through R are as defined 35 therein. R" is H; or C-C alkyl, C-C alkenyl, C-C alkynyl or C-C cycloalkyl each optionally substituted with one or SUMMARY OF THE INVENTION more Substituents selected from the group consisting of halogen, CN, NO, hydroxy, C-C alkoxy, C-C alky This invention pertains to compounds of Formula I, and 40 lthio, C-C alkylsulfinyl, C-C alkylsulfonyl, C-C N-oxides or salts thereof alkoxycarbonyl, C-C alkylamino, C-C dialkylamino and C-C cycloalkylamino; or R" is C-C alkylcarbonyl, C-C alkoxycarbonyl, C-C, 45 alkylaminocarbonyl, or C-C dialkylaminocarbonyl: each R is independently selected from the group consist ing of H. C-C alkyl, C-C alkenyl, C-C alkynyl, C-C cycloalkyl, C-C haloalkyl, C-C haloalkenyl, C-C haloalkynyl, C-C halocycloalkyl, C-C 50 cyanoalkyl, halogen, CN, NO, piperidine, C-C wherein alkoxy, C-Chaloalkoxy, C-C alkylthio, C-C alkyl A is O or S: Sulfinyl, C-C alkylsulfonyl, C-C haloalkylthio. B is a phenyl ring or a pyridine ring, each ring Substituted C-C haloalkylsulfinyl, C-C haloalkylsulfonyl, with 1 to 5 R: C-C alkylamino, C-C dialkylamino, and C-C, J is a pyrazole or a pyrrole heterocyclic ring system 55 cycloalkylamino; or Selected from the group consisting of J-1, J-2, J-3, J-4. each R is independently selected from the group consist J-5 and J-6: ing of a phenyl, benzyl or phenoxy ring, each ring optionally substituted with one or more substituents Selected from the group consisting of C-C alkyl, C-C J-1 60 alkenyl, C-C alkynyl, C-C cycloalkyl, C-C haloalkyl, C-Chaloalkenyl, C-Chaloalkynyl, C-C, halocycloalkyl, halogen, CN, NO, C-C alkoxy, C-C, haloalkoxy, C-C alkylthio, C-C alkylsulfinyl, C-C, alkylsulfonyl, C-C alkylamino, C-Cs dialkylamino, 65 C-C cycloalkylamino, Ca-C, (alkyl)cycloalkylamino, C-C alkoxycarbonyl, C-C alkylaminocarbonyl, and C-Cs dialkylaminocarbonyl: US 7,754,738 B2 4 R is mers. “Cyanoalkyl denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH NCCHCH and CHCH(CN)CH. “Alkylamio”, “dialky lamino', and the like, are defined analogously to the above examples. "Cycloalkyl includes, for example, cyclopropyl. cyclobutyl, cyclopentyl, and cyclohexyl. The term “cycloalkylamino' includes the same groups linked through a nitrogen atom Such as cyclopentylamino and cyclohexy lamino. 10 The term "hetero” in connection with rings or ring systems refers to a ring or ring system in which at least one ring atom is not carbon and which can contain 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, each R. R* and R7 is independently selected from the oxygen and Sulfur, provided that each ring contains no more group consisting of H. C-C alkyl, C-C cycloalkyl, 15 than 4 nitrogens, no more than 2 oxygens and no more than 2 C-C haloalkyl, halogen, CN, C-C alkoxy, C-C, Sulfurs. The terms "heteroaromatic ring or ring system” and alkylthio, C-C haloalkoxy and C-C haloalkylthio; “aromatic fused heterobicyclic ring system’ includes fully and aromatic heterocycles and heterocycles in which at least one R is H. C-C alkyl, C-C haloalkyl, C-C alkenyl, ring of a polycyclic ring system is aromatic (where aromatic C-C haloalkenyl, C-C alkynyl, C-C haloalkynyl, indicates that the Hickel rule is satisfied). The heterocyclic or C-Chaloalkoxy. ring or ring system can be attached through any available This invention also pertains to a method for controlling at carbon or nitrogen by replacement of a hydrogen on said least one invertebrate pest comprising contacting the inverte carbon or nitrogen. brate pest or its environment with a biologically effective The term “halogen, either alone or in compound words amount of at least one compound of Formula I, an N-oxide or 25 such as “haloalkyl, includes fluorine, chlorine, bromine or a salt thereof (e.g., as a composition described herein). This iodine. Further, when used in compound words such as invention also relates to such a method wherein the inverte “haloalkyl or “halocycloalkyl, said alkyl or cycloalkyl may brate pest or its environment is contacted with a biologically be partially or fully substituted with halogen atoms which effective amount of at least one compound of Formula I, an may be the same or different.