WO2002088086A1 - Derive de n-(3-quinolyl)amide - Google Patents

Derive de n-(3-quinolyl)amide Download PDF

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Publication number
WO2002088086A1
WO2002088086A1 PCT/JP2002/004031 JP0204031W WO02088086A1 WO 2002088086 A1 WO2002088086 A1 WO 2002088086A1 JP 0204031 W JP0204031 W JP 0204031W WO 02088086 A1 WO02088086 A1 WO 02088086A1
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WO
WIPO (PCT)
Prior art keywords
group
meo
compound
ipr
methyl
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Application number
PCT/JP2002/004031
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English (en)
Japanese (ja)
Inventor
Hiroyuki Ito
Hisako Tanaka
Hiroshi Ohta
Tohru Ohnishi
Chiaki Imai
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Sankyo Company, Limited
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Application filed by Sankyo Company, Limited filed Critical Sankyo Company, Limited
Publication of WO2002088086A1 publication Critical patent/WO2002088086A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings

Definitions

  • the present invention relates to an N- (3-quinolyl) amide derivative or a salt thereof, and an agricultural chemical containing the same as an active ingredient.
  • the present inventors have conducted intensive studies on ⁇ - (3-quinolyl) amide derivatives, and as a result, have found that cyclohexancarboxylic acid or cyclohexenecarboxylic acid having a substituent at the ⁇ -position in the 3-aminoquinolyl group can be obtained.
  • the bound ⁇ - (3-quinolyl) amide derivative has excellent bactericidal activity against various plant diseases and is useful as an active ingredient of pesticides.
  • the present invention has been found to be able to control rice blast (Pyricularia oryzae), which often causes serious damage to rice, and Botrytis cinerea, a tomato, cucumber and kidney bean, with a low dose.
  • the present invention has the general formula [Wherein, ...... represents a single bond or a double bond,
  • R is an optionally substituted alkyl group (the substituents may be the same or different, and may have 1 to 4 halogen atoms, 1 C 3 -C 6 cycloalkyl group, or 1 C 1 -C 6 alkoxy group; is a group.), represents C 3 -C 6 cycloalkyl group, C 2 -C 6 alkenyl or C 3 -C 6 alkynyl group,
  • X is a halogen atom, which may be substituted ⁇ 6 alkyl group (the substituent is the same or different 1 to 3 halogen atoms.) Or which may be substituted ⁇ ⁇ ⁇ ⁇ alkoxy group (said alkoxy The groups are the same or different and are 1 to 3 halogen atoms.
  • n an integer of 0 to 6
  • n an integer of 0 to 6
  • n 2 or more, a plurality of Zs may be the same or different, and any two Z forces together form an alkylene group. Or a salt thereof.
  • " ⁇ ⁇ 8 alkyl group” for example, a methyl group, Echiru group, a propyl group, an isopropyl group, heptyl group, isobutyl group, s - butyl group, t-Bed butyl group, a pentyl group, an isopentyl group , 2-methylbutynole, neopentyl, 1-ethylpropyl, hexyl, 4-methylpentynole, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 3,3-dimethylbutyl , 2,2-dimethylbutyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylmethylmethylbuty
  • it is a linear or branched alkyl group having 1 to 5 carbon atoms (to alkyl group), and still more preferably, a linear or branched alkyl group having 1 to 4 carbon atoms.
  • the “halogen atom” is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom, a chlorine atom or a bromine atom, more preferably a fluorine atom or a chlorine atom. And most preferably a fluorine atom.
  • the “C 3 -C 6 cycloalkyl group” is a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group, preferably a cyclopropyl group or a cyclobutyl group, more preferably Is a cyclopropyl group.
  • the "rCiCe alkoxy group” is, for example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, an s-butoxy group, a t-butoxy group, a pentyloxy group , Isopentyloxy, 2-methylbutoxy, neopentyloxy, 1-ethylpropoxy, hexyloxy, (4-methylpentyl) oxy, (3-methylpentyl) oxy,
  • It is a straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms such as 3-dimethylbutoxy group, 2,3-dimethylbutoxy group or 2-ethylbutoxy group, and preferably has 1 to 4 carbon atoms.
  • -C 4 alkoxy group more preferably, main butoxy group, an ethoxy group or isopropoxy group, still preferably more, main butoxy or ethoxy And most preferably a methoxy group.
  • “-alkyl group the substituents are the same or different 1 to 4 logen atoms, 1 C 3 -C 6 cycloalkyl group or 1 alkoxy group”. In addition to the above “C, to C.
  • alkyl group for example, Noremethyl group, trichloromethyl group, difluoromethyl group, dichloromethyl group, dimethyl methinole group, fluoromethyl group, chloromethyl group, bromomethyl group, chloromethyl group, 2,2,2-trichloromethylethyl group, 2,2,2 —Trifluoroethyl group, 2-bromoethyl group, 2-chloroethyl group, 2-funoleoethyl group, 3-cyclopropyl group, 3,3,3-trifluoropropyl group, 4-fluorobutynole group, 3— The same or different, such as fluoro-2-methylpropyl, 3,3,3 ⁇ trifluoro-2-methylpropyl, 6,6,6-trichlorohexyl, 3,3,4,4-tetrafluorobutyl
  • Neck alkyl is bonded " ⁇ 8 alkyl group", or, main Tokishimechiru group, ethoxymethyl group,
  • ⁇ C 1, C 8 -alkyl group '' to which one ⁇ dialkoxy group '' such as a propoxymethyl group, a methoxyethyl group, a methoxypropyl group, a methoxybutoxy group, a pentyloxymethyl group is bonded preferably, the same or different 1-3 amino wherein "halogen atom", Ri by the one of the "C 3 -C 6 cycloalkyl group” or one of the " ⁇ ⁇ ⁇ alkoxy group” substituted And more preferably 1 to 3 of the same or different “halogen atoms”, 1 of the “C 4 -C 6 cycloalkyl group” or 1
  • the “C 2 -C 6 alkenyl group” is, for example, a vinyl group, an aryl group, a 1-propenyl group, a 2-methyl-1-propenyl group, a 2-methylino-2-propyl group.
  • a straight or branched chain having 2 to 6 carbon atoms such as a ole group, 3-butenyl group, 2-methyl-2-butenyl group, 2-pentenyl group, 4-pentenyl group, 3-methyl-2-butenyl group
  • An alkenyl group preferably a linear or branched alkenyl group having 2 to 5 carbon atoms, more preferably a vinyl group, an aryl group, a 4-pentenyl group or a 3-methyl-2- It is a butenyl group, and even more preferably an aryl group.
  • the “C 3 -C 6 alkynyl group” is, for example, a straight chain or branched having 3 to 6 carbon atoms such as a propargyl group, a 2-pentynyl group, a 3-pentynyl group and a 2-butynyl group.
  • a chain alkynyl group preferably an alkynyl group having 3 or 4 carbon atoms, still more preferably a propargyl group or a 2-pentynyl group, and particularly preferably a 2-pentynyl group.
  • ⁇ ⁇ 6 alkyl group (the substituent is the same or different 1 to 3 halogen atoms.)
  • Alkyl group '' more preferably, the above-mentioned ⁇ -alkyl group '' which may be substituted by the same or different 1 to 3 ⁇ fluorine atoms or chlorine atoms '', and even more preferably, a methyl group, It is an ethyl group, a propyl group, a chloromethyl group or a trifluoromethyl group, particularly preferably a methyl group, an ethyl group or a trifluoromethyl group.
  • "- ⁇ alkoxy group the substituents are the same or different;!
  • -3 halogen atoms) is, for example, trifluoromethoxy in addition to the above-mentioned " ⁇ - ⁇ alkoxy group”.
  • the ⁇ FC i C alkylene group '' is, for example, a linear or branched alkylene group having 1 to 4 carbon atoms such as a methylene group, an ethylene group, a trimethylene group, a propylene group, and a tetramethylene group.
  • R is preferably an optionally substituted alkyl group (the substituents may be the same or different from one to four fluorine or chlorine atoms, and one C 4 to C 6 cycloalkyl group Or one C 1 -C 4 alkoxy group.), A C 3 -C 4 cycloalkyl group, a C 3 -C 5 alkenyl group or a C 3 -C 5 alkynyl group, and more preferably a substituted good Te ⁇ ⁇ alkyl group (the substituent is from 1 to three fluorine atoms, is one of the cyclohexyl groups or one main butoxy group cyclohexylene.), C 3 ⁇ C 5 alkenyl group or A C 3 -C 5 alkynyl group, and even more preferably, an optionally substituted c, -c 4 alkyl group (the substituent is 1-3 fluorine atoms), and C 3 -C 4 alkenyl group or C 4 -C 5 alkyl
  • X is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, an optionally substituted alkyl group (the substituents may be the same or different one to three fluorine atoms or It is a chlorine atom.) Or may be substituted A xyl group (the substituents are the same or different 1 to 3 fluorine atoms or chlorine atoms), m is 0, 1 or 2, more preferably X is fluorine Atom, chlorine atom, C!
  • m is 0 or 1, even more preferably, X is a fluorine atom or a methyl group, m is 0 or 1, Particularly preferably, m is 0,
  • Z n is preferably, Z is a C 1 -C 4 alkyl group, n is 0, 1 or 2, when n is 2, two Z, together becomes, the ⁇ ⁇ Ji may form 2 alkylene group, and more preferably, Z is a C i Cs alkyl radical, n is 0 or 1, more preferably more, Z is, A methyl group, n is 0 or 1, particularly preferably n is 0;
  • Nini is preferably a single bond [the cyclohexylcarbonyl group in which the acyl group of the compound (I) of the present invention is substituted with R at the 1-position. ].
  • the compound (I) of the present invention preferably,
  • R is, which may be substituted ⁇ 6 alkyl group (said substituent is 1 to 4 fluorine atoms or chlorine atoms became identical or different, one ⁇ 4 ⁇ 6 cycloalkyl group or 1 and C, a -C 4 alkoxy group.), a C 3 -C 4 cycloalkyl group, C 3 -C 5 alkenyl or C 3 -C 5 alkynyl group,
  • X is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and may be substituted ⁇ To ⁇ 4 alkyl group (the substituents may be the same or different 1 to 3 fluorine atoms or chlorine atoms) or may be substituted to alkoxy groups (the substituents may be the same or different 1 to 3 fluorine atoms or chlorine atoms.) Wherein m is 0, 1 or 2;
  • R is an optionally substituted ⁇ to 5- alkyl group (the substituent is 1-3 fluorine atoms, one cyclohexyl group or one methoxy group), a C 3 -C 5 alkenyl or C 3 -C 5 alkynyl group,
  • X is a fluorine atom, a chlorine atom, a ⁇ alkyl group or a ⁇ ⁇ ⁇ alkoxy group, m is 0 or 1,
  • (b 3) Z is a Ci Cs alkyl group, n is 0 or 1,
  • (c 1) is an optionally substituted ⁇ alkyl group (the substituent is 1-3 fluorine atoms), a C 3 -C 4 alkenyl group or a C 4 -C 5 alkynyl group, (c 2) X is a fluorine atom or a methyl group, m is 0 or 1,
  • (c 3) 2 is a methyl group, n is 0 or 1,
  • R is methyl, ethyl, propyl, butyl, isobutyl, pentyl, trifluoromethyl, vinyl, aryl, 4-pentenyl, 3-methyl-2-butenyl Group, propargyl group or 2-pentynyl group,
  • (d 4) is a single bond or a double bond
  • the compound (I) of the present invention can be made into a salt such as, for example, sulfate, hydrochloride, nitrate, phosphate. These salts are included in the present invention as long as they can be used as fungicides for agricultural and horticultural use.
  • the compound (I) of the present invention can be solvated, and these solvates are also included in the present invention.
  • a solvate is preferably a hydrate.
  • the present invention includes a mixture of one kind of optically active substance and several kinds of optically active substances at an arbitrary ratio.
  • Representative compounds of the present invention are illustrated in the following table, but the present invention is not limited to these compounds.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un dérivé de N-(3-quinolyl)amide, représenté par la formule générale (1), ou un sel de ce dérivé. Dans la formule (1), ?????? représente une simple liaison ou une double liaison, R est un groupe alkyle C1-8, un groupe cycloalkyle C3-6, un groupe alcényle C2-6 ou un groupe alcynyle C3-6 éventuellement substitués, X est un groupe halogéno, un groupe alkyle C1-6 éventuellement substitué ou un groupe alkoxy C1-6 éventuellement substitué, m est un nombre entier compris entre 0 et 6, Z est un groupe alkyle C1-6, n est un nombre entier compris entre 0 et 6, et si n est supérieur ou égal à 2, l'une quelconque des combinaisons de deux Z peut être un groupe alkylène C1-4. L'invention concerne également un produit chimique agricole contenant comme ingrédient actif ce dérivé ou un sel de ce dérivé.
PCT/JP2002/004031 2001-04-24 2002-04-23 Derive de n-(3-quinolyl)amide WO2002088086A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2001-125661 2001-04-24
JP2001125661 2001-04-24

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004005261A1 (fr) * 2002-07-08 2004-01-15 Sankyo Agro Company, Limited Derive de 1-aralkyl-n-(3-quinolyl)-1-cyclohexanecarboxamide
WO2004039783A1 (fr) * 2002-10-21 2004-05-13 Sankyo Agro Company, Limited Compose a base de quinoline-3-carboxamide
WO2004069792A3 (fr) * 2003-02-03 2005-01-20 Janssen Pharmaceutica Nv Amides derives quinoliniques modulant le recepteur vr1 vanilloide
JP2005206517A (ja) * 2004-01-22 2005-08-04 Sankyo Agro Kk １−アラルキルシクロヘキサン化合物
WO2019053027A1 (fr) * 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
US11584740B2 (en) 2017-09-13 2023-02-21 Syngenta Participations Ag Microbiocidal quinoline (thio)carboxamide derivatives

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61126071A (ja) * 1984-11-22 1986-06-13 Hokko Chem Ind Co Ltd 農園芸用殺菌剤
WO1993004580A1 (fr) * 1991-09-03 1993-03-18 Dowelanco Pesticides a base d'arylacetamides n-(4-pyridyle ou 4-quinoleinyle)

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61126071A (ja) * 1984-11-22 1986-06-13 Hokko Chem Ind Co Ltd 農園芸用殺菌剤
WO1993004580A1 (fr) * 1991-09-03 1993-03-18 Dowelanco Pesticides a base d'arylacetamides n-(4-pyridyle ou 4-quinoleinyle)

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DIADONE G. ET AL.: "Salicylanilide and its heterocyclic analogs. A Comparative study of their antimicrobial activity", PHARMAZIE, vol. 45, no. 6, 1990, pages 441 - 442, XP002955020 *
KIM K. ET AL.: "Two efficient N-acylation methods mediated by solid-supported reagents for weakly nucleophilic heterocyclic amines", SYNLETT, no. 12, 1999, pages 1957 - 1959, XP002955019 *

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004005261A1 (fr) * 2002-07-08 2004-01-15 Sankyo Agro Company, Limited Derive de 1-aralkyl-n-(3-quinolyl)-1-cyclohexanecarboxamide
WO2004039783A1 (fr) * 2002-10-21 2004-05-13 Sankyo Agro Company, Limited Compose a base de quinoline-3-carboxamide
JPWO2004039783A1 (ja) * 2002-10-21 2006-03-02 三共アグロ株式会社 キノリン−３−カルボキサミド化合物
JP4511362B2 (ja) * 2002-10-21 2010-07-28 三井化学アグロ株式会社 キノリン−３−カルボキサミド化合物
EP2308848A1 (fr) * 2003-02-03 2011-04-13 Janssen Pharmaceutica NV Amides derives quinoliniques modulant le recepteur VR1 vanilloide
WO2004069792A3 (fr) * 2003-02-03 2005-01-20 Janssen Pharmaceutica Nv Amides derives quinoliniques modulant le recepteur vr1 vanilloide
US8394828B2 (en) 2003-02-03 2013-03-12 Janssen Pharmaceutica, Nv Quinoline-derived amide modulators of vanilloid VR1 receptor
JP2005206517A (ja) * 2004-01-22 2005-08-04 Sankyo Agro Kk １−アラルキルシクロヘキサン化合物
JP4511201B2 (ja) * 2004-01-22 2010-07-28 三井化学アグロ株式会社 １−アラルキルシクロヘキサン化合物
WO2019053027A1 (fr) * 2017-09-13 2019-03-21 Syngenta Participations Ag Dérivés microbiocides de quinoléine (thio)carboxamide
JP2020533389A (ja) * 2017-09-13 2020-11-19 シンジェンタ パーティシペーションズ アーゲー 殺微生物性キノリン（チオ）カルボキサミド誘導体
US11241011B2 (en) 2017-09-13 2022-02-08 Syngenta Participations Ag Microbiocidal quinoline (thio)carboxamide derivatives
JP7202366B2 (ja) 2017-09-13 2023-01-11 シンジェンタ パーティシペーションズ アーゲー 殺微生物性キノリン（チオ）カルボキサミド誘導体
US11584740B2 (en) 2017-09-13 2023-02-21 Syngenta Participations Ag Microbiocidal quinoline (thio)carboxamide derivatives

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