US008895.035B2 (12) United States Patent (10) Patent No.: US 8,895,035 B2 Fukumoto et al. (45) Date of Patent: Nov. 25, 2014 (54) ALKOXYIMINO DERIVATIVE AND PEST (2013.01); A0IN 43/08 (2013.01); A0IN 43/10 CONTROL AGENT (2013.01); A0IN 43/20 (2013.01); A0IN 43/40 (2013.01); A0IN 43/50 (2013.01); A0IN 43/56 (75) Inventors: Shunichirou Fukumoto, Shizuoka (JP); (2013.01); A0IN 43/653 (2013.01); A0IN Daisuke Shikama, Shizuoka (JP); Keiji 43/713 (2013.01); A0IN 43/78 (2013.01); Toriyabe, Shizuoka (JP); Toshihiro A0IN 43/82 (2013.01); C07C 259/02 Nagata, Shizuoka (JP); Masaaki (2013.01); A0IN 43/84 (2013.01); C07D Komatsu, Shizuoka (JP): Takeshi 249/10 (2013.01); C07D401/12 (2013.01); Matsuda, Shizuoka (JP); Yuki Nakano, C07D 403/12 (2013.01); C07D 413/06 Tokyo (JP) (2013.01); C07D 413/12 (2013.01); C07D (73) Assignees: Kumiai Chemical Industry Co., Ltd, 417/06 (2013.01); C07F 7/10 (2013.01); C07D 403/06 (2013.01); C07D405/12 (2013.01); Tokyo (JP); Ihara Chemical Industry C07D 417/12 (2013.01); A0IN 47/18 Co., Ltd., Tokyo (JP) (2013.01); C07F 7/0812 (2013.01) (*) Notice: Subject to any disclaimer, the term of this USPC .............................. 424/400: 514/63: 514/236 patent is extended or adjusted under 35 (58) Field of Classification Search U.S.C. 154(b) by 0 days. CPC ............................... A01N 37/50: A01N 43/56 (21) Appl. No.: 13/806,317 USPC ..................................... 424/400: 514/63, 236 See application file for complete search history. (22) PCT Filed: Jun. 21, 2011 (86). PCT No.: PCT/UP2011/OO3522 (56) References Cited S371 (c)(1), (2), (4) Date: Dec. 21, 2012 U.S. PATENT DOCUMENTS (87) PCT Pub. No.: WO2011/161945 4,358.408 A 11/1982 Kruger et al. 5,411,990 A 5/1995 Tsuji et al. PCT Pub. Date: Dec. 29, 2011 (Continued) (65) Prior Publication Data US 2013/O1 O2568 A1 Apr. 25, 2013 FOREIGN PATENT DOCUMENTS (30) Foreign Application Priority Data AU A-9 1777.82 12/1982 GB 1443555. A 7, 1976 Jun. 24, 2010 (JP) ................................. 2010-143577 (Continued) (51) Int. Cl. AOIN 43/54 (2006.01) Primary Examiner — Johann R Richter AOIN 55/00 (2006.01) Assistant Examiner — Yanzhi Zhang AOIN 37/50 (2006.01) (74) Attorney, Agent, or Firm — Bacon & Thomas, PLLC AOIN 43/08 (2006.01) AOIN 43/10 (2006.01) (57) ABSTRACT AOIN 43/20 (2006.01) AOIN 43/40 (2006.01) The present invention provides a novel alkoxyimino deriva AOIN 43/50 (2006.01) tive or a salt thereof, as well as to a pest control agent con AOIN 43/56 (2006.01) taining the derivative or salt thereofas an active ingredient, AOIN 43/653 (2006.01) which shows an excellent pest control effect on a wide range AOIN 43/73 (2006.01) of pests in the agricultural and horticultural field and is also AOIN 43/78 (2006.01) capable of controlling resistant pests. The novel alkoxyimino AOIN 43/82 (2006.01) derivative is characterized by being represented by general C07C 259/02 (2006.01) formula I AOIN 43/84 (2006.01) Chemicial formula 1 CO7D 249/10 (2006.01) CO7D 40/12 (2006.01) CO7D 403/2 (2006.01) X CO7D 413/06 (2006.01) CO7D 413/2 (2006.01) R11 O NN 2 2 No1 CO7D 417/06 (2006.01) C07F 7/10 (2006.01) CO7D 403/06 (2006.01) CO7D 405/2 (2006.01) (in the formula, X, R, R and Q are as defined in the speci C07D 417/12 (2006.01) fication) and the post control agent is characterized by con AOIN 47/8 (2006.01) taining as an active ingredient the alkoxyimino derivative or a C07F 7/08 (2006.01) salt thereof. (52) U.S. Cl. CPC ................ A0IN 55/00 (2013.01); A0IN37/50 16 Claims, No Drawings US 8,895,035 B2 Page 2 (56) References Cited JP 521361.20. A 11, 1977 JP 58110569. A T 1983 U.S. PATENT DOCUMENTS JP 6-40811 A 2, 1994 JP 11-512446. A 10, 1999 6,130,247 A 10/2000 Bayer et al. JP 2000506902 A1 6, 2000 6.225,349 B1* 5/2001 Bayer et al. ................... 514,538 JP 2001-513782. A 9, 2001 2004/0023806 A1* 2/2004 Ziegler et al. ................. 504,244 JP 2003-516384 A 5, 2003 WO 971 1065 A1 3, 1997 FOREIGN PATENT DOCUMENTS WO 01,36399 A1 5, 2001 JP 49-55833 5, 1974 * cited by examiner US 8,895,035 B2 1. ALKOXYMNO DERVATIVE AND PEST CONTROL AGENT Formula 1 TECHNICAL FIELD The present invention relates to a novel alkoxyimino R11 OnNN 2 2 N No1 derivative or a salt thereof, as well as to a pest control agent containing the derivative or salt thereof as an active ingredi ent. 10 in the formula, BACKGROUND ART X is a hydrogen atom, a halogen atom, a cyano group, a C-C alkyl group, a C-C alkenyl group, a C-C alkynyl For example, the following patent literature 1 or patent group, a C-C cycloalkyl group, a C-C cycloalkyl C-C, literature 2 is already known as a literature regarding com 15 alkyl group, a C-C haloalkyl group, a C-C alkylthio pounds similar to the alkoxyimino derivative of the present group, a C-C alkylsulfinyl group, a C-C alkylsulfonyl invention. group, a C-C alkylthio C-C alkyl group, a C-C alkyl The patent literature 1 discloses a hydroximoylazole sulfinyl C-C alkyl group, a C-C alkylsulfonyl C-C, derivative. However, this derivative is restricted to com alkyl group, a C-C alkoxy group, a C-C alkoxy C-C, pounds having a carbamic acid ester structure, and the litera alkyl group, a thiocarbamoyl group, a RRNC(=O) group, ture does not disclose the alkoxyimino derivative of the a R'R''N group, a C-C alkoxycarbonyl group, a carboxyl present invention. group, a RO(HN=)C group, a RON=(R')C group, a The patent literature 2 discloses a hydroximoyl derivative. R''S(O—)C group, a R'R''NSONH group, a hydroxy However, this derivative is restricted to O-acyl derivatives, 25 C-C alkyl group, a cyano C-C alkyl group, a C-C, and the literature does not disclose the alkoxyimino derivative alkylcarbonyl group, a phenyl group which may be substi of the present invention. tuted with substituent(s) selected from substituent group C. PRIOR ART LITERATURES shown later, or a heterocyclic ring group of 1 to 9 carbon 30 atoms, having 1 to 5 hetero atoms which may be the same or Patent Literatures different and which are selected from oxygen atom, sulfur atom and nitrogen atom (the group may be substituted with 1 Patent literature 1: DE-3150984 to 5 substituent(s) selected from halogenatoms, C-C alkyl Patent literature 2: JP-1995-41704 group, C-C haloalkyl group, C-C alkoxy group, oxo 35 group or cyano group), SUMMARY OF THE INVENTION R" is a C-Clo alkyl group, a C-C alkenyl group, a C-C alkynyl group, a C-C cycloalkyl group, a C-C, Task to be Achieved by the Invention cycloalkyl C-C alkyl group, a C-C haloalkyl group, a C-C haloalkenyl group, a C-C haloalkynyl group, a 40 It is desired that pest control agents such as insecticide, C-C alkylthio C-C alkyl group, a C-C alkylsulfinyl acaricide and the like, used to useful crops are safe to man and C-C alkyl group, a C-C alkylsulfonyl C-C alkyl group, livestock, are Small in influence to environment, and exhibit a a C-C alkoxy C-C alkyl group, a C-C haloalkoxy sufficient effect to pests at a low dose. Use of insecticides and C-C alkyl group, a C-C alkoxyimino C-C alkyl group, acaricides for past many years has generated resistant pests, 45 a tri (C-C alkyl)silyl C-C alkyl group, a cyano C-C, making it difficult to control pests completely with conven alkyl group, a gem-di (C-C alkoxy) C-C alkyl group, a tional chemicals. hydroxy C-C alkyl group, an amino C-C alkyl group (the The task of the present invention is to provide an excellent group may be substituted with R'' and R'), a phenyl group which may be substituted with substituent(s) selected from pest control agent which solves the above-mentioned prob 50 lems of conventional pest control agents. the Substituent group C, a phenyl C-C alkyl group which may be substituted with substituent(s) selected from the sub Means for Achieving the Task stituent group C, a phenyl C-C alkenyl group which may be substituted with substituent(s) selected from the substituent In order to develop a pest control agent having the above 55 group C, a phenoxy C-C alkyl group which may be substi mentioned advantageous features, the present inventors Syn tuted with substituent(s) selected from the substituent group thesized various alkoxyimino derivatives and studied physi C., a heterocyclic ring group of 1 to 9 carbon atoms, having 1 ological activities thereof. As a result, it was found that an to 5 hetero atoms which may be the same or different and alkoxyimino derivative represented by the general formula II which are selected from oxygen atom, Sulfur atom and shown below shows a high effect to pests and resistant pests. 60 nitrogen atom (the group may be substituted with 1 to 5 The finding has led to the completion of the present invention.