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Fused Heterocyclic Compound Or Salt Thereof

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Fused Heterocyclic Compound Or Salt Thereof (19) TZZ Z¥_T (11) EP 2 975 039 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07D 487/04 (2006.01) A01N 43/90 (2006.01) 15.08.2018 Bulletin 2018/33 A01P 7/04 (2006.01) A61K 31/5025 (2006.01) A61P 33/14 (2006.01) (21) Application number: 14762737.6 (86) International application number: (22) Date of filing: 14.03.2014 PCT/JP2014/056832 (87) International publication number: WO 2014/142292 (18.09.2014 Gazette 2014/38) (54) FUSED HETEROCYCLIC COMPOUND OR SALT THEREOF, AGRICULTURAL AND HORTICULTURAL INSECTICIDE CONTAINING FUSED HETEROCYCLIC COMPOUND, AND METHOD FOR USING AGRICULTURAL AND HORTICULTURAL INSECTICIDE KONDENSIERTE HETEROCYCLISCHE VERBINDUNG ODER SALZ DAVON, INSEKTIZID FÜR LANDWIRTSCHAFT UND GARTENBAU MIT EINER KONDENSIERTEN HETEROCYCLISCHEN VERBINDUNG UND VERFAHREN ZUR VERWENDUNG DES INSEKTIZIDS FÜR LANDWIRTSCHAFT UND GARTENBAU COMPOSÉ HÉTÉROCYCLIQUE CONDENSÉ OU SEL DE CELUI-CI, INSECTICIDE AGRICOLE ET HORTICOLE CONTENANT LE COMPOSÉ HÉTÉROCYCLIQUE CONDENSÉ ET PROCÉDÉ D’UTILISATION DE L’INSECTICIDE AGRICOLE ET HORTICOLE (84) Designated Contracting States: • FURUYA, Takashi AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Kawachinagano-shi GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO Osaka 586-0094 (JP) PL PT RO RS SE SI SK SM TR • SUWA, Akiyuki Kawachinagano-shi (30) Priority: 15.03.2013 JP 2013053201 Osaka 586-0094 (JP) 22.05.2013 JP 2013107592 25.07.2013 JP 2013155074 (74) Representative: Witte, Weller & Partner 07.11.2013 JP 2013231582 Patentanwälte mbB Postfach 10 54 62 (43) Date of publication of application: 70047 Stuttgart (DE) 20.01.2016 Bulletin 2016/03 (56) References cited: (73) Proprietor: Nihon Nohyaku Co., Ltd. WO-A1-2012/086848 WO-A1-2013/018928 Tokyo 104-8386 (JP) JP-A- 2012 092 049 JP-A- 2012 092 050 JP-A- 2012 092 051 JP-A- 2012 092 052 (72) Inventors: JP-A- 2012 092 053 JP-A- 2012 092 054 • YONEMURA, Ikki JP-A- 2012 092 055 JP-A- 2012 092 056 Kawachinagano-shi JP-A- 2012 092 057 JP-A- 2012 092 058 Osaka 586-0094 (JP) JP-A- 2012 092 059 JP-A- 2012 092 060 • FUKATSU, Kosuke JP-A- 2012 092 061 JP-A- 2012 131 780 Kawachinagano-shi Osaka 586-0094 (JP) 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 2 975 039 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 975 039 B1 Description TECHNICAL FIELD 5 [0001] The present invention relates to an agricultural and horticultural insecticide comprising a certain kind of con- densed heterocyclic compound or a salt thereof as an active ingredient; and the method for using the insecticide. BACKGROUND ART 10 [0002] Various compounds have been examined for their potential as an agricultural and horticultural insecticide, and among them, certain kinds of condensed heterocyclic compounds have been reported to be useful as an insecticide (for example, see Patent Literature 1 to 6). None of these references disclose any condensed heterocyclic compound containing a pyridazine ring. 15 CITATION LIST Patent Literature [0003] 20 Patent Literature 1: JP-A 2009-280574 Patent Literature 2: JP-A 2010-275301 Patent Literature 3: JP-A 2011-79774 Patent Literature 4: JP-A 2012-131780 25 Patent Literature 5: WO 2012/086848 Patent Literature 6: WO 2013/018928 SUMMARY OF INVENTION 30 TECHNICAL PROBLEM [0004] In crop production in the fields of agriculture, horticulture and the like, the damage caused by insect pests etc. is still immense, and insect pests resistant to existing insecticides have emerged. Under such circumstances, the de- velopment of novel agricultural and horticultural insecticides is desired. 35 SOLUTION TO PROBLEM [0005] The present inventors conducted extensive research to solve the above-described problems. As a result, the present inventors found that a condensed heterocyclic compound represented by the general formula (I) or a salt thereof 40 has an excellent control effect on agricultural and horticultural insect pests, and reached the completion of the present invention. [0006] That is, the present invention relates to the following. [1] A condensed heterocyclic compound represented by the general formula (I): 45 50 55 {wherein R1 represents 2 EP 2 975 039 B1 (a1) a (C1-C6) alkyl group; (a2) a (C3-C6) cycloalkyl group; (a3) a (C2-C6) alkenyl group; (a4) a (C2-C6) alkynyl group; 5 (a5) a halo (C1-C6) alkyl group; (a6) a halo (C3-C6) cycloalkyl group; (a7) a halo (C2-C6) alkenyl group; (a8) a halo (C2-C6) alkynyl group; (a9) a (C1-C6) alkoxy (C1-C6) alkyl group; 10 (a10) a halo (C1-C6) alkoxy (C1-C6) alkyl group; (a11) a (C3-C6) cycloalkyl (C1-C6) alkyl group; (a12) a halo (C3-C6) cycloalkyl (C1-C6) alkyl group; (a13) a (C1-C6) alkoxy halo (C1-C6) alkyl group; (a14) a halo (C1-C6) alkoxy halo (C1-C6) alkyl group; 15 (a15) a (C1-C6) alkylthio (C1-C6) alkyl group; (a16) a (C1-C6) alkylsulfinyl (C1-C6) alkyl group; (a17) a (C1-C6) alkylsulfonyl (C1-C6) alkyl group; (a18) a cyano (C1-C6) alkyl group; (a19) a (C1-C6) alkoxycarbonyloxy (C1-C6) alkyl group; 20 (a20) a di-(C1-C6) alkylamino (C1-C6) alkyl group (wherein the alkyl groups of the di-(C1-C6) alkylamino moiety may be the same or different); (a21) a phenyl (C1-C6) alkyl group; or (a22) a phenyl (C1-C6) alkyl group having, on the ring, 1 to 5 substituting groups selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C 1-C6) alkyl group, (e) a (C 1-C6) 25 alkoxy group, (f) a halo (C1-C6) alkyl group and (g) a halo (C1-C6) alkoxy group, R2 represents (b1) a halogen atom; 30 (b2) a cyano group; (b3) a nitro group; (b4) a (C1-C6) alkyl group; (b5) a (C3-C6) cycloalkyl group; (b6) a (C2-C6) alkenyl group; 35 (b7) a (C2-C6) alkynyl group; (b8) a halo (C1-C6) alkyl group; (b9) a halo (C3-C6) cycloalkyl group; (b10) a halo (C2-C6) alkenyl group; (b11) a halo (C2-C6) alkynyl group; 40 (b12) a (C1-C6) alkylthio group; (b13) a (C1-C6) alkylsulfinyl group; (b14) a (C1-C6) alkylsulfonyl group; (b15) a halo (C1-C6) alkylthio group; (b16) a halo (C1-C6) alkylsulfinyl group; 45 (b17) a halo (C1-C6) alkylsulfonyl group; (b18) a (C1-C6) alkoxy (C1-C6) alkyl group; (b19) a halo (C1-C6) alkoxy (C1-C6) alkyl group; (b20) a (C3-C6) cycloalkyl (C1-C6) alkyl group; (b21) a halo (C3-C6) cycloalkyl (C1-C6) alkyl group; 50 (b22) a (C1-C6) alkoxy halo (C1-C6) alkyl group; (b23) a halo (C1-C6) alkoxy halo (C1-C6) alkyl group; (b24) a hydrogen atom; (b25) a (C1-C6) alkoxy group; (b26) a halo (C1-C6) alkoxy group; 55 (b27) an amino group; (b28) a (C1-C6) alkylamino group; (b29) a di-(C1-C6) alkylamino group (wherein the alkyl groups of the di-(C1-C6) alkyl moiety may be the same or different); 3 EP 2 975 039 B1 (b30) a (C1-C6) alkylcarbonylamino group; (b31) a (C1-C6) alkylsulfonylamino group; (b32) a (C1-C6) alkylsulfonyl ((C1-C6) alkyl) amino group; (b33) a (C1-C6) alkoxycarbonyl group; or (b34) a tri-(C 1-C6) alkylsilyl (C 2-C6) alkynyl group (wherein the alkyl groups of the tri-(C 1-C6) alkylsilyl moiety 5 may be the same or different), R3 represents (c1) a hydrogen atom; 10 (c2) a halogen atom; (c3) a cyano group; (c4) a nitro group; (c5) a (C1-C6) alkyl group; (c6) a (C1-C6) alkoxy group; 15 (c7) a (C2-C6) alkenyloxy group; (c8) a (C2-C6) alkynyloxy group; (c9) a halo (C1-C6) alkyl group; (c10) a halo (C1-C6) alkoxy group; (c11) a halo (C2-C6) alkenyloxy group; 20 (c12) a halo (C2-C6) alkynyloxy group; (c13) a (C1-C6) alkoxy (C1-C6) alkyl group; (c14) a halo (C1-C6) alkoxy (C1-C6) alkyl group; (c15) a (C3-C6) cycloalkyl (C1-C6) alkyl group; (c16) a halo (C3-C6) cycloalkyl (C1-C6) alkyl group; 25 (c17) a (C1-C6) alkoxy halo (C1-C6) alkyl group; or (c18) a halo (C1-C6) alkoxy halo (C1-C6) alkyl group, R4 represents 30 (d1) a hydrogen atom; (d2) a halogen atom; (d3) a cyano group; (d4) a nitro group; (d5) a (C1-C6) alkyl group; 35 (d6) a (C1-C6) alkoxy group; (d7) a (C2-C6) alkenyloxy group; (d8) a (C2-C6) alkynyloxy group; (d9) a halo (C1-C6) alkyl group; (d10) a halo (C1-C6) alkoxy group; 40 (d11) a halo (C2-C6) alkenyloxy group; (d12) a halo (C2-C6) alkynyloxy group; (d13) a (C1-C6) alkoxy (C1-C6) alkyl group; (d14) a halo (C1-C6) alkoxy (C1-C6) alkyl group; (d15) a (C3-C6) cycloalkyl (C1-C6) alkyl group; 45 (d16) a halo (C3-C6) cycloalkyl (C1-C6) alkyl group; (d17) a (C1-C6) alkoxy halo (C1-C6) alkyl group; (d18) a halo (C1-C6) alkoxy halo (C1-C6) alkyl group; (d19) a mercapto group; (d20) a (C1-C6) alkylthio group; 50 (d21) a (C1-C6) alkylcarbonylthio group; (d22) a halo (C1-C6) alkylthio group; (d23) a phenyl group; (d24) a phenyl group having, on the ring, 1 to 5 substituting groups selected from the group consisting of (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a (C1-C6) alkyl group, (e) a (C1-C6) alkoxy 55 group, (f) a halo (C1-C6) alkyl group and (g) a halo (C 1-C6) alkoxy group; (d25) a (C1-C6) alkylsulfinyl group; (d26) a (C1-C6) alkylsulfonyl group; (d27) a halo (C1-C6) alkylsulfinyl group; or 4 EP 2 975 039 B1 (d28) a halo (C1-C6) alkylsulfonyl group, R5 represents 5 (el) a hydrogen atom; (e2) a formyl group; (e3) a (C1-C6) alkyl group; (e4) a (C3-C6) cycloalkyl group; (e5) a halo (C1-C6) alkyl group; 10 (e6) a halo (C3-C6) cycloalkyl group; (e7) a (C1-C6) alkylsulfonyl group; (e8) a halo (C1-C6) alkylsulfonyl group; (e9) a (C1-C6) alkoxy (C1-C6) alkyl group; (e10) a halo (C1-C6) alkoxy (C1-C6) alkyl group; 15 (e11) a (C1-C6) alkoxy halo (C1-C6) alkyl group; (e12) a halo (C1-C6) alkoxy halo (C1-C6) alkyl group; (e13) an amino group; or (e14) a (C1-C6) alkoxy group, 20 A1and A2 each are CH, and A3 is CH or N, and m represents 0, 1 or 2}, and a salt thereof.
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