USOO9504250B2 (12) United States Patent (10) Patent No.: US 9,504,250 B2 Ogawa et al. (45) Date of Patent: *Nov. 29, 2016 (54) ARTHROPOD PEST CONTROL FOREIGN PATENT DOCUMENTS COMPOSITION AND METHOD FOR CN 101.073324. A 11, 2007 CONTROLLING ARTHROPOD PESTS CN 1012O3135 A 6, 2008 (71) Applicant: SUMITOMO CHEMICAL (Continued) COMPANY., LIMITED, Tokyo (JP) OTHER PUBLICATIONS (72) Inventors: Masaomi Ogawa, Kasai (JP); Yukie Machine Generated English translation for DE-102007045920-A1. Hirotomi, Kasai (JP) (Continued) (73) Assignee: SUMITOMO CHEMICAL Primary Examiner — Traviss C McIntosh, III COMPANY., LIMITED, Tokyo (JP) (74) Attorney, Agent, or Firm — Birch, Stewart, Kolasch & Birch, LLP (*) Notice: Subject to any disclaimer, the term of this (57) ABSTRACT patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. Disclosed is an arthropod pest control composition having an excellent controlling effect on arthropod pests, which This patent is Subject to a terminal dis- comprises an amide compound represented by formula (a): claimer. HC (a) (21) Appl. No.: 15/054,791 3 Y. F HC CH3, (22) Filed: Feb. 26, 2016 N^ H M N CH (65) Prior Publication Data HC 3 US 2016/O174559 A1 Jun. 23, 2016 O Related U.S. Application Data a spinosin compound represented by formula (1): (62) Division of application No. 14/232,057, filed as (1) application No. PCT/JP2012/068402 on Jul. 12, 2012, now Pat. No. 9,301,531. OCH CH3 (30) Foreign Application Priority Data O- oROCH3 Jul. 13, 2011 (JP) ................................. 2011-155104 (51) Int. Cl. AOIN 43/22 (2006.01) XI w2 R AOIN 43/56 (2006.01) X4 R AOIN 43/40 (2006.01) AOIN 43/78 (2006.01) wherein R' represents a hydrogen atom or a C1-C4 alkyl AOIN 43/50 (2006.01) group, R represents a C1-C4 alkyl group, and X" and X (Continued) each represents a hydrogen atom, or X" and X’ are taken together to form a single bond, and (52) U.S. Cl. one or more compounds selected from Group (A): CPC ............... AOIN 43/78 (2013.01); AOIN 43/22 Group (A): the group consisting of fipronil, pymetrozine, a (2013.01); A0IN 43/40 (2013.01); A0IN compound represented by formula (b): 43/50 (2013.01); A0IN 43/56 (2013.01); A0IN 43/707 (2013.01); A0IN 43/88 (b) (2013.01); A0IN 47/44 (2013.01) O (58) Field of Classification Search None O, See application file for complete search history. N N (56) References Cited 2 liest C N U.S. PATENT DOCUMENTS 4,742,060 A 5, 1988 Shiokawa et al. and a neonicotinoid compound containing a nitroguanidine 5,034.404 A 7, 1991 Uneme et al. Structure. (Continued) 9 Claims, No Drawings US 9,504,250 B2 Page 2 (51) Int. Cl. WO WO 2007/112847 A2 10, 2007 AOIN 43/707 WO WO 2007/115644 A1 10, 2007 (2006.01) WO WO 2009/O15763 A1 2, 2009 AOIN 43/88 (2006.01) WO WO 2009/043442 A1 4/2009 AOIN 47/44 (2006.01) WO WO 2010.000790 A1 1, 2010 WO WO2010/052129 * 5/2010 References Cited WO WO 2010/052129 A2 5, 2010 (56) WO WO 2010/092032 A1 8, 2010 U.S. PATENT DOCUMENTS WO WO 2010/O921.19 A1 8, 2010 5.434,181 A 7, 1995 Kodaka et al. OTHER PUBLICATIONS 5,852,012 A 12, 1998 Maienfisch et al. 6,444,667 B1 9, 2002 Andersch et al. The Extended European Search Report, dated Jan. 27, 2015, issued 9,301,531 B2 * 4/2016 Ogawa ................... AON 43,22 in the corresponding European Patent Application No. 12811430.3. 2004/0204470 A1 10, 2004 Elbe et al. 2008/0293566 A1 11, 2008 Suty-Heinze et al. The First Office Action (including an English translation), dated 2009,0253749 A1 10, 2009 Jeschke et al. Nov. 2, 2014, issued in the corresponding Chinese Patent Applica 2010/O197737 A1 8, 2010 Hungenberg et al. tion No. 201280O32593.9. 2010, O298.137 A1 11, 2010 Hungenberg et al. The International Preliminary Report on Patentability, dated Jan. 14. 2013/O123506 A1 5, 2013 Jeschke et al. 2014, issued in the International Application No. PCT/JP2012/ O68402. FOREIGN PATENT DOCUMENTS The Office Action (including an English translation), dated Feb. 17. 2015, issued in the corresponding Japanese Patent Application No. CN 101466705. A 6, 2009 2011-155104. CN 101708.000 A 5, 2010 The Pesticide Manual, 15th Edition, Published by BCPC, ISBN DE 102007045920 A1 4/2009 978-1-901396-18-8 (9 pages). EP O3753.16 A1 6, 1990 The Second Office Action (including an English translation), dated JP 61-178981 8, 1986 Jun. 2, 2015, issued in the corresponding Chinese Patent Applica JP 3-1573O8 7, 1991 tion No. 201280O32593.9. JP 6-183918 T 1994 The Written Opinion of the International Searching Authority, dated JP T-179448 7, 1995 Sep. 11, 2012, issued in the International Application No. PCT/ JP 2002-516258 6, 2002 JP2012/068402. JP 2008-539 179 11/2008 JP 2009-531352 9, 2009 XP-002734489: Database WPI Week 200828 Thomson Scientific, JP 2010-534625 11 2010 London, GB, Nov. 21, 2007; AN 2008-D86053. JP 2011-501733 1, 2011 XP-002734490: Database WPI Week 201038 Thomson Scientific, WO WO 97.00265 1, 1997 London, GB, May 19, 2010: AN 2010-F97344. WO WO 03/010149 2, 2003 WO WO 2006, 114212 11 2006 * cited by examiner US 9,504,250 B2 1. 2 ARTHROPOD PEST CONTROL a spinosin compound represented by formula (1): COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS (1) CROSS-REFERENCE TO RELATED APPLICATIONS OCH This application is a Divisional of co-pending application oROCH3 Ser. No. 14/232,057 filed on Jan. 10, 2014, which is a 10 National Phase of PCT International Application No. PCT/ JP2012/068402 filed on Jul. 12, 2012, which claims priority under 35 U.S.C. S 119(a) to Patent Application No. 2011 155104 filed in Japan on Jul. 13, 2011. All of the above applications are hereby expressly incorporated by reference X X2 RI into the present application. 15 wherein R' represents a hydrogen atom or a C1-C4 alkyl group, R represents a C1-C4 alkyl group, and X" and X TECHNICAL FIELD each represents a hydrogen atom, or X" and X’ are taken together to form a single bond, and The present invention relates to an arthropod pest control one or more compounds selected from Group (A): composition and a method for controlling arthropod pests. Group (A): the group consisting of fipronil, pymetrozine, a compound represented by formula (b): BACKGROUND ART 25 (b) Heretofore, various compounds are known as active ingredients in arthropod pest control compositions (see, for example, The Pesticide Manual-15th edition (published by BCPC): ISBN 978-1-901396-18-8). 30 SUMMARY OF INVENTION NS 2 CHCF2H C N Technical Problem 35 and a neonicotinoid compound containing a nitroguanidine An object of the present invention is to provide an Structure. arthropod pest control composition having an excellent 2 The arthropod pest control composition according to the above 1, wherein the weight ratio of the amide compound control effect on arthropod pests. to the spinosin compound is from 50:1 to 1:50. 3 The arthropod pest control composition according to the Solution to Problem 40 above 2, wherein the weight ratio of the amide compound to the one or more compounds selected from Group (A) is The present inventors have intensively studied for pro from 50:1 to 1:100. viding an arthropod pest control composition having an 4 The arthropod pest control composition according to any excellent control effect on arthropod pests, and finally found one of the above 1 to 3, wherein the neonicotinoid that a composition comprising an amide compound repre 45 compound is a compound represented by formula (2): sented by the following formula (a), a spinosin compound represented by the following formula (1) and one or more compounds selected from Group (A) has an excellent con (2) trol effect on arthropod pests, thereby attaining the present 50 invention. Namely, the present invention includes the followings 1 -N-N- to 10: NNO 1 An arthropod pest control composition comprising an amide compound represented by formula (a): 55 wherein R represents a hydrogen atom or a methyl group, A and E each represents a hydrogen atom, or A and E are taken together to form CH, CH, or CH, O CH, (a) Z represents a 2-chloro-5-thiazolyl group, a 6-chloro-3- H3 C pyridyl group or a 3-tetrahydrofuryl group. Y F HC CH3, 60 5 The arthropod pest control composition according to any M one of the above 1 to 3, wherein the neonicotinoid NN CH3 compound is clothianidin, imidacloprid, thiamethoxam or dinotefuran. HC 6. The arthropod pest control composition according to any 65 one of the above 1 to 3, wherein the one or more compounds selected from Group (A) is pymetrozine, dinote furan or the compound represented by formula (b). US 9,504,250 B2 3 4 7. The arthropod pest control composition according to any wherein R', R, X' and X’ are defined as above, and one of the above 1 to 6, wherein the spinosin compound one or more compounds (hereinafter sometimes referred to is spinosad or spinetoram. as “the present compound (A)') selected from the following 8. A method for controlling an arthropod pest, which Group (A): comprises applying an effective amount of the arthropod 5 pest control composition according to any one of the above Group (A): the group consisting of fipronil, pymetrozine, a 1 to 7 to a plant or an area in which a plant is grown.