(19) TZZ _Z_T (11) EP 2 186 804 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A01N 43/90 (2006.01) A01N 47/12 (2006.01) 17.06.2015 Bulletin 2015/25 A01N 47/18 (2006.01) A01N 47/28 (2006.01) A01N 47/36 (2006.01) C07D 413/10 (2006.01) (2006.01) (2006.01) (21) Application number: 08792510.3 C07D 413/14 C07D 417/04 C07D 471/04 (2006.01) (22) Date of filing: 11.08.2008 (86) International application number: PCT/JP2008/064664 (87) International publication number: WO 2009/022746 (19.02.2009 Gazette 2009/08) (54) NITROGEN-CONTAINING HETEROCYCLIC COMPOUND AND PEST CONTROL AGENT STICKSTOFFHALTIGE HETEROCYCLISCHE VERBINDUNG UND SCHÄDLINGSBEKÄMPFUNGSMITTEL COMPOSÉ HÉTÉROCYCLIQUE CONTENANT DE L’AZOTE ET AGENT DE LUTTE CONTRE LES ANIMAUX NUISIBLES (84) Designated Contracting States: WO-A1-2009/066009 WO-A1-2009/112275 AT BE BG CH CY CZ DE DK EE ES FI FR GB GR WO-A2-2006/129158 JP-A- 04 224 577 HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT RO SE SI SK TR • JESSICA D. TOWNSEND ET AL.: SYNTHETIC COMMUNICATIONS, vol. 30, no. 12, 2000, (30) Priority: 10.08.2007 JP 2007208855 XP002655398, 26.12.2007 JP 2007333470 • TUAN THANH DANG ET AL.: "Synthesis of Isoxazole-5-carboxylatesby Cyclization of Oxime (43) Date of publication of application: 1,4-Dianions with Diethyl Oxalate", SYNTHESIS, 19.05.2010 Bulletin 2010/20 vol. 15, 2006, pages 2515-2522, XP002655399, • HIROKI FUKUI ET AL: "NMR Determination of the (73) Proprietor: Nippon Soda Co., Ltd. Absolute Configuration of an .ALPHA.-Exo- Tokyo 100-8165 (JP) methylene-.GAMMA.-lactone.", BIOSCIENCE, BIOTECHNOLOGY, AND BIOCHEMISTRY, vol. (72) Inventors: 64, no. 7, 1 January 2000 (2000-01-01), pages • IWATA, Jyun 1345-1351, XP55003995, ISSN: 0916-8451, DOI: Odawara-shi 10.1271/bbb.64.1345 Kanagawa 250-0280 (JP) • DATABASE CAPLUS [Online] CHEMICAL • KAWAGUCHI, Masahiro ABSTRACTS SERVICE, COLUMBUS, OHIO, US; Odawara-shi 1994, XP002655401, retrieved from STN Database Kanagawa 250-0280 (JP) accession no. 1994:483129 & DE MATTOS, MARCIO CONTRUCCI S.; KOVER, W. BRUCE: (74) Representative: Cabinet Plasseraud "Cycloaddition of nitrile oxides to limonene: 52, rue de la Victoire chemo- and regiospecific synthesis of 3- 75440 Paris Cedex 09 (FR) substituted 2- isoxazolines", QUIMICA NOVA, vol. 17, no. 2, 1994, page 11-123, (56) References cited: • SHINOHARA ET AL.: "Synthesis and character of EP-A1- 0 455 052 EP-A1- 1 731 512 new bis(isoxazoline) ligands character", WO-A1-2005/021516 WO-A1-2005/085216 HETEROCYCLES, vol. 59, no. 2, 2003, page WO-A1-2006/090234 WO-A1-2007/029077 587-593, XP002655402, Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 186 804 B1 Printed by Jouve, 75001 PARIS (FR) (Cont. next page) EP 2 186 804 B1 • KENSUKE NABETA ET AL: "Absolute • WALTERSMJ ET AL:’The preparationof ...acetyl Configuration of Kelsoene and Prespatane.", ketones’SYNTHETIC COMMUNICATIONS vol. 33, BIOSCIENCE, BIOTECHNOLOGY, AND no. 23, 2003, pages 4163 - 4171, XP009116765 BIOCHEMISTRY, vol. 63, no. 10, 1 January 1999 • DATABASE REGISTRY [Online] 29 May 2006 ’5- (1999-01-01), pages 1772-1776, XP55003996, Isoxazolol, 5-(difluoromethyl) -4,5-dihydro-3-(6- ISSN: 0916-8451, DOI: 10.1271/bbb.63.1772 hydroxy-4,7-dimethoxy-5-b enzofuranyl)-’, • DATABASE REGISTRY [Online] CHEMICAL XP008138182 Retrieved from stn Database ABSTRACTS SERVICE, COLUMBUS, OHIO, US; accession no. RN 885890-19-7 21 March 2001 (2001-03-21), XP002655404, • DATABASE REGISTRY [Online] 29 May 2006 ’5- retrieved from STN Database accession no. Isoxazolol,4,5-dihydro-3-(6-hydroxy-4,7- 328285-44-5 dimethoxy-5-benzofuranyl)-5-(1,1,2,2-tetraf • JASSBI, AMIR REZA; FUKUSHI, YUKIHARU; luoroethyl)’, XP008138183 Retrieved from stn TAHARA,SATOSHI: HELVETICA CHIMICA ACTA, Database accession no. RN 885890-13-1 vol. 85, no. 5, 2002, pages 1706-1713, • DATABASE REGISTRY [Online] 29 March 2006 ’5- XP002655405, isoxazolol,4,5-dihydro-3-(6-hydroxy-4,7- • PARMAR VS ET AL: ’Synthesis dimethoxy-5-benzofuranyl)-5-(trifluoromethy l)’, Characterization ... Heterocyclic compounds’ XP008138204 Retrieved from stn Database BIOORGANIC & MEDICAL CHEMISTRY vol. 11, accession no. RN 878436-08-9 no. 6, 2003, pages 913 - 929, XP002348797 • DATABASE REGISTRY [Online] 21 March 2001 ’5- • JANUSZ JM ET AL: ’New Cyclooxygenase-2/5- isoxazolol,4,5-dihydro-3-(2-naphthalenyl )- Lipoxygenase Inhibitors.3.7-tert-Butyl-2,3- 5-(trifluoromethyl)’,XP008138184 Retrieved from dihydro-3,3-dimethylbenzofuran Derivatives as stn Database accession no. RN 328285-44-5 Gastrointestinal Safe Antiinflammatory and Analgesic Agents: Variations at the 5 Position’ JOURNAL OF MEDICINAL CHEMISTRY vol. 41, no. 18, 1998, pages 3515 - 3529, XP002223203 2 EP 2 186 804 B1 Description TECHNICAL FIELD 5 [0001] The present invention relates to a novel nitrogen-containing heterocyclic compound or salt thereof, and to a pest control agent containing as an active ingredient thereof at least one type of these compounds. [0002] The present application claims priority on Japanese Patent Application No. 2007-208855 filed in Japan on August 10, 2007, and on Japanese Patent Application No. 2007-333470 filed in Japan on December 26, 2007. 10 BACKGROUND ART [0003] Although numerous insecticides, miticides and other pest control agents have been used in the past, since their efficacy has been inadequate, their use has been limited due to problems with drug resistance, or they have caused damage or contamination of plant bodies or demonstrated potent toxicity against human beings, livestock or fish, there 15 have been more than a few cases in which these conventional pest control agents were hardly considered to be satis- factory control agents. Thus, there has been a desire for the development of a chemical having few of these disadvantages that can also be used safely. [0004] Patent Document 1 relating to the present invention describes the following compound having a backbone that resembles that of the compound according to the present invention. 20 [0005] However, the compound according to the present invention is not described in this document. 25 30 [0006] In the above formula, W’ represents an oxygen atom or sulfur atom, A a, A b and A c respectively and independently represent a carbon atom or nitrogen atom, Y’ represents a halogen atom or the like, n’ represents an integer of 0 to 4, Rd and Re respectively and independently represent a hydrogen atom or C1 to C12 alkyl group or the like, R f represents 35 a halogen atom or the like, and Z’ represents a phenyl group or the like. [0007] In addition, Patent Document 2 describes a compound represented by the following general formula. However, this compound was not considered to always demonstrate adequate control effects. 40 45 2 2 [0008] In the above formula, in the case R and Y are present at adjacent locations, R may form -CH2-, -CH2CH2-, 6 6 -CH2O- -CH2S- or -CH2N(R )- (wherein, R represents a C1 to C6 alkyl group or the like) together with Y, or may form a 5-membered or 6-membered ring together with atoms respectively bonded thereto. 50 Patent Document 1: WO 2005/085216 Patent Document 2: WO 2007/105814 DISCLOSURE OF THE INVENTION 55 PROBLEMS TO BE SOLVED BY THE INVENTION [0009] An object of the present invention is to provide a novel nitrogen-containing heterocyclic compound or salt 3 EP 2 186 804 B1 thereof, which can be advantageously synthesized industrially and can function as an active ingredient of a pest control agent that has reliable effects and can be used safely, and a pest control agent that contains as an active ingredient thereof at least one type of these compounds. 5 MEANS FOR SOLVING THE PROBLEMS [0010] In order to solve the aforementioned problems, a first aspect of the present invention relates to a nitrogen- containing heterocyclic compound represented by the following formula (I), or salt thereof as defined in claim 1. 10 15 [0011] A second aspect of the present invention relates to an insecticide containing as an active ingredient thereof at least one type of the nitrogen-containing heterocyclic compound of the first aspect of the present invention, or salt thereof. [0012] A third aspect of the present invention relates to a miticide containing as an active ingredient thereof at least one type of the nitrogen-containing heterocyclic compound of the first aspect of the present invention, or salt thereof. [0013] A fourth aspect of the present invention relates to a pest control agent containing as an active ingredient thereof 20 at least one type of the nitrogen-containing heterocyclic compound of the first aspect of the present invention, or salt thereof. EFFECTS OF THE INVENTION 25 [0014] According to the present invention, a novel nitrogen- containing heterocyclic compound or salt thereof, which can be advantageously synthesized industrially and can function as an active ingredient of a pest control agent that has reliable effects and can be used safely, as well as an insecticide, miticide and pest control agent, which contain as an active ingredient thereof at least one type of the compound, are provided. 30 BEST MODE FOR CARRYING OUT THE INVENTION [0015] The following provides a detailed explanation of the present invention. 1) Nitrogen-Containing Heterocyclic Compound Represented by Formula (I) or Salt Thereof 35 [0016] A first aspect of the present invention relates to a nitrogen-containing heterocyclic compound represented by the following formula (I) (hereinafter to be referred to as the "nitrogen-containing heterocyclic compound according to the present invention") and a salt thereof as defined in claim 1.