(12) United States Patent (10) Patent No.: US 8.487,115 B2 Matsuo (45) Date of Patent: Jul
Total Page:16
File Type:pdf, Size:1020Kb
US008487115B2 (12) United States Patent (10) Patent No.: US 8.487,115 B2 Matsuo (45) Date of Patent: Jul. 16, 2013 (54) HYDANTOIN DERIVATIVES OF (56) References Cited CYANO-SUBSTITUTED CHRYSANTHEMIC ACD ESTERS AND THEIR USE IN PEST U.S. PATENT DOCUMENTS CONTROL 4,176,189 A * 1 1/1979 Itaya et al. .................... 514/389 (75) Inventor: Noritada Matsuo, Amagasaki (JP) FOREIGN PATENT DOCUMENTS JP 57-158765 A 9, 1982 (73) Assignee: Sumitomo Chemical Company, W. 3. A. 3. Limited, Tokyo (JP) WO WO 2010O87419 A2 * 8, 2010 OTHER PUBLICATIONS (*) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 Int'l Search Report and Written Opinion issued Jun. 17, 2011 in Int’l U.S.C. 154(b) by 0 days. Application No. PCT/JP2011/057504. Tomlin, “473 imiprothrin'. The e-Pesticide Manual, Version 4.0, pp. 1-2 (Jul. 1, 2006). (21) Appl. No.: 13/637,788 Int’l Preliminary Report on Patentability issued Oct. 2, 2012 in Int’l Application No. PCT/JP2011/057504. (22) PCT Filed: Mar. 18, 2011 * cited by examiner (86). PCT No.: PCT/UP2011/057504 Primary Examiner — Joseph K. McKane S371 (c)(1), Assistant Examiner — Amanda L. Aguirre (2), (4) Date: Dec. 12, 2012 (74) Attorney, Agent, or Firm — Panitch Schwarze Belisario & Nadel LLP (87) PCT Pub. No.: WO2011/122509 (57) ABSTRACT PCT Pub. Date: Oct. 6, 2011 An ester compound represented by formula (1): wherein R represents hydrogen or methyl, R' represents hydrogen or (65) Prior Publication Data C1-C4 alkyl, andR represents hydrogen or C1-C4 alkyl; has US 2013/0090363 A1 Apr. 11, 2013 an excellent pest control effect and is therefore useful as an active ingredient of a pest control agent. (30) Foreign Application Priority Data Mar. 31, 2010 (JP) ................................. 2010-08 1657 O H3C CH3 R3 R4 (51) Int. Cl. AOIN 53/00 (2006.01) l 5 C07D 233/72 (2006.01) e1) \ CHEC R (52) U.S. Cl. USPC ...................... 548/319.5: 548/318.5: 514/389 is, O O YN (58) Field of Classification Search USPC ............................................ 548/3001: 334.5 See application file for complete search history. 30 Claims, No Drawings US 8,487,115 B2 1. 2 HYDANTON DERVATIVES OF 5 The ester compound according to 1, wherein a relative CYANO-SUBSTITUTED CHRYSANTHEMIC configuration of the Substituent of the 1'-position existing on ACDESTERS AND THEIR USE IN PEST the Substituent at the 3-position of the cyclopropane ring is CONTROL Z-configuration in formula (1): 6The ester compound according to 1, wherein an absolute CROSS-REFERENCE TO RELATED configuration of the 1-position of the cyclopropane ring is an APPLICATION R configuration and a relative configuration of the Substituent of the 1'-position existing on the substituent at the 3-position This application is a Section 371 of International Applica of the cyclopropane ring is Z-configuration in formula (1): tion No. PCT/JP2011/057504, filed Mar 18, 2011, which was 10 7The ester compound according to 1, wherein an absolute published in the English language on Oct. 6, 2011, under configuration of the 1-position of the cyclopropane ring is an International Publication No. WO 2011/122509 A1, and the R configuration, a relative configuration of the Substituent at disclosure of which is incorporated herein by reference. the 1-position of the cyclopropane ring and the Substituent at 15 the 3-position of the cyclopropane ring is a trans configura TECHNICAL FIELD tion, and a relative configuration of the substituent of the 1'-position existing on the substituent at the 3-position of the The present invention relates to an ester compound and use cyclopropane ring is Z-configuration in formula (1): thereof. 8. The ester compound according to any one of 1 to 7. wherein R is hydrogen in formula (1): BACKGROUND ART 9. The ester compound according to any one of 1 to 7. wherein R is hydrogen or methyl in formula (1): Heretofore, various compounds have been synthesized so 10 The ester compound according to any one of 1 to 7. as to control pests. For example, a certain ester compound is wherein R is hydrogen in formula (1): described in JP-A-57-158765. 25 11 The ester compound according to any one of 1 to 7. wherein R is methyl in formula (1): DISCLOSURE OF INVENTION 12 The ester compound according to any one of 1 to 7. wherein R is hydrogen in formula (1): An object of the present invention is to provide a novel 13 The ester compound according to any one of 1 to 7. compound having an excellent pest control effect. 30 wherein R is hydrogen and R is hydrogen or methyl in The present inventors have intensively studied and found formula (1): that an ester compound represented by formula (1) shown 14 The ester compound according to any one of 1 to 7. below has an excellent pest control effect, and led to the wherein R is hydrogen and R is hydrogen in formula (1): present invention. 15 The ester compound according to any one of 1 to 7. That is, the present invention is directed to the following 35 wherein R is hydrogen and R is methyl in formula (1): invention: 16. The ester compound according to any one of 1 to 7. 1. An ester compound represented by formula (1): wherein R is hydrogen and R is hydrogen in formula (1): 17 The ester compound according to any one of 1 to 7. 40 wherein R is hydrogen or methyl, and R is hydrogen in formula (1): 18 The ester compound according to any one of 1 to 7. wherein R is hydrogen and R is hydrogen in formula (1): 19. The ester compound according to any one of 1 to 7. 45 wherein R is methyl and R is hydrogen in formula (1): e1) - \ 3 ci 20. The ester compound according to any one of 1 to 7. N.Y. O wherein R is hydrogen, R is hydrogen or methyl, and R is hydrogen in formula (1): 21. The ester compound according to any one of 1 to 7. wherein R represents hydrogen or methyl, R' represents 50 wherein R is hydrogen, Rishydrogen, and Rishydrogenin hydrogen or C1-C4 alkyl, and R represents hydrogen or formula (1): C1-C4 alkyl 22 The ester compound according to any one of 1 to 7. (hereinafter referred to as the compound of the present inven wherein R is hydrogen, R is methyl; and R is hydrogen in tion); formula (1): 2 The ester compound according to 1, wherein a relative 55 23 A pest control agent comprising the ester compound configuration of the Substituent at the 1-position of the cyclo according to any one of 1 to 22 and an inert barrier; propane ring and the Substituent at the 3-position of the cyclo 24A method of controlling pests, which comprises a step of propane ring is a trans configuration in formula (1); applying an effective amount of the ester compound accord 3 The ester compound according to 1, wherein an absolute ing to any one of 1 to 22 to pests or a place where pests configuration of the 1-position of the cyclopropane ring is an 60 habitat; R configuration in formula (1): 25 A method of controlling pests, which comprises the step 4The ester compound according to 1, wherein an absolute of applying an effective amount of the ester compound configuration of the 1-position of the cyclopropane ring is an according to any one of 1 to 22 to cockroaches or a place R configuration, and a relative configuration of the Substitu where cockroaches inhabits: ent at the 1-position of the cyclopropane ring and the Sub 65 26. The method of controlling pests according to 25. stituent at the 3-position of the cyclopropane ring is a trans wherein the cockroach is American cockroach (Periplaneta configuration in formula (1): Americana); US 8,487,115 B2 3 4 27 The method of controlling pests according to 25, Substituent at the 1-position of the cyclopropane ring and the wherein the cockroach is German cockroach (Blattella ger Substituent at the 3-position of the cyclopropane ring is a trans manica); configuration, and a relative configuration of the Substituent 28 A method of controlling pests, which comprises a step of of the 1'-position existing on the substituent at the 3-position spraying an effective amount of the ester compound accord 5 of the cyclopropane ring is Z-configuration. ing to any one of 1 to 22 to cockroaches or a place where Anester compound represented by formula (1) in which R is cockroaches inhabit; hydrogen. 29. The method of controlling pests according to 28. An ester compound represented by formula (1) in which a wherein the cockroach is American cockroach (Periplaneta relative configuration of the substituent at the 1-position of 10 the cyclopropane ring and the Substituent at the 3-position of Americana); the cyclopropane ring is a trans configuration, and R is 30 The method of controlling pests according to 28. hydrogen. wherein the cockroach is German cockroach (Blattella ger An ester compound represented by formula (1) in which an manica). absolute configuration of the 1-position of the cyclopropane The compound of the present invention has an excellent 15 ring is an R configuration, and R is hydrogen. pest control effect and is therefore useful as an active ingre An ester compound represented by formula (1) in which an dient of a pest control agent. absolute configuration of the 1-position of the cyclopropane In the compound of the present invention, there are isomers ring is an R configuration, a relative configuration of the derived from two asymmetric carbon atoms at the 1-position Substituent at the 1-position of the cyclopropane ring and the and the 3-position on the cyclopropane ring, and isomers Substituent at the 3-position of the cyclopropane ring is a trans derived from the double bond present in the substituent at the configuration, and R is hydrogen.