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WO1996038419A1 - Derives de 5-pyrazolecarboxamide et agent de lutte contre les maladies des plantes - Google Patents

Derives de 5-pyrazolecarboxamide et agent de lutte contre les maladies des plantes Download PDF

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Publication number
WO1996038419A1
WO1996038419A1 PCT/JP1996/001466 JP9601466W WO9638419A1 WO 1996038419 A1 WO1996038419 A1 WO 1996038419A1 JP 9601466 W JP9601466 W JP 9601466W WO 9638419 A1 WO9638419 A1 WO 9638419A1
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Prior art keywords
group
methyl
pyrazolecarbonyl
chloro
atom
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PCT/JP1996/001466
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English (en)
Japanese (ja)
Inventor
Shigeaki Akiyama
Hiroyuki Suzuki
Yoshiaki Yasumi
Toshiaki Takeyama
Takamasa Kikuchi
Junichi Watanabe
Hiroshi Ohya
Masanori Nishioka
Takashi Furusato
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Nissan Chemical Industries, Ltd.
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Application filed by Nissan Chemical Industries, Ltd. filed Critical Nissan Chemical Industries, Ltd.
Priority to AU58450/96A priority Critical patent/AU5845096A/en
Publication of WO1996038419A1 publication Critical patent/WO1996038419A1/fr

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    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D231/16—Halogen atoms or nitro radicals

Definitions

  • the present invention relates to a novel 5-virazole carboxylic acid amide derivative, and a plant disease controlling agent, particularly a rice blast controlling agent, containing a 5-virazole carboxylic acid amide derivative as an active ingredient.
  • the compound which has a bactericidal activity shown by this is disclosed.
  • X is a halogen atom
  • R 1 is a d-C 4 alkyl group
  • W is an oxygen atom or a sulfur atom
  • R 2 and R s each independently represent a hydrogen atom, a Ci-C 10 alkyl group,
  • -N (R 8 ) (R 8 ) group C (R ⁇ XR 11 ) group or —OR 12 group, or R 2 and R 8 together with the nitrogen atom to which they are attached That is, to form a 3- to 11-membered nitrogen-containing heterocycle, or to form a 3- to 7-membered heterocycle containing one or more additional, sulfur and Z or nitrogen atoms as ring members; heterocycle may be substituted by one or more D ⁇ C 6 alkyl or d ⁇ C4 alkoxy force Ruponiru group,
  • p is 0 or an integer from 1 to 8
  • n 0 or 1
  • n 0, 1 or 2;
  • R 4 and R 6 are each independently a hydrogen atom, a halogen atom, Ci ⁇ C e alkyl le group, C 2 -C 6 alkenyl group, C 2 -C 6 alkynyl group, Ci ⁇ C e Haroa alkyl group, C 2 -C e haloalkenyl, C 2 -C 6 haloalkynyl group, C 8 -C 6 consequent ⁇ alkyl group, Ci ⁇ C e alkoxy group, Ci ⁇ C e Haroarukoki shea group, an optionally substituted Ariru group, to an optionally substituted Teroari group, base may be substituted Njiru group, Ci ⁇ C 4 alkylcarbonyl group,
  • Cl ⁇ C 6 alkoxycarbonyl group, hydroxycarbonyl group, Cl ⁇ C4 ⁇ alkylthio D ⁇ C 4 alkyl group, Ci ⁇ C 4 alkylsulfinyl Ci ⁇ C 4 alkyl group, Ci ⁇ C 4 alkylsulfonyl 0! ⁇ is a C 4 alkyl group or Ci ⁇ C 4 Arukiruokishi D ⁇ C 4 alkyl group,
  • R 4 and R 5 may be taken together to form a C 3 -C 6 alkylene group.
  • R 6 is a hydrogen atom, a halogen atom, a Ci- 10 alkyl group, C 2 -d. Alkenyl group, C 2 ⁇ ⁇ ! . Alkynyl group, Cl. Haloalkyl group, C 2 ⁇ d. C ⁇ alkenyl, C 2 -C 10 haloalkynyl group, C s -C 10 cycloalkyl group, O 9
  • Ci ⁇ C 10 alkoxy group I ⁇ C 6 Nono n alkoxy group, c 2 -C e Haroaru Keniruokishi group, C 2 ⁇ C e Nono b alkynyl O carboxy groups, C 8 -C e a cycloalkyl Kiruokishi groups, substituted Aryl group, optionally substituted heteroaryl group, optionally substituted heterocyclyl group, optionally substituted aryloxy group, optionally substituted heteroaryloxy group, hydroxyl group, Ci ⁇ C 6 alkylcarbonyl O alkoxy group, optionally substituted Ariru carbonyl be the O alkoxy group, -S (0) "one R 18 group, Ci ⁇ C e alkoxycarbonyl two group, hydroxy radical Poni group, -CON (R 14 ) (R 15 ) group or
  • R 7 is a hydrogen atom, a Ci-C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C e alkynyl group, a Ci-C 6 ha ⁇ alkyl group, —N (R 14 ) (R 18 ) group, An aryl group which may be substituted, a benzyl group which may be substituted or a heteroaryl group which may be substituted;
  • R 8 a hydrogen atom, Ci ⁇ C 10 alkyl group, C 2 ⁇ C 10 alkenyl group, C 2 -C 10 alkynyl group, Cs ⁇ C 10 consequent opening alkyl group, Ci ⁇ Ci. Ha port alkyl group, C 2 ⁇ Ci. Haloalkenyl, C 2 ⁇ Ci. Haroa Rukiniru group, an optionally substituted Ariru group, base may be substituted Nji group, heteroaryl group which may be substituted, D ⁇ C e alkyl carbonylation group, Ci ⁇ C e haloalkylcarbonyl An optionally substituted arylcarbonyl group, an optionally substituted heteroarylcarbonyl group, d-
  • R 8 and R 8 are taken together with the nitrogen atom to which they are attached to form a 4- to 11-membered heterocycle or as a ring member one or more additional oxygen, sulfur and Z or Form a 3- to 7-membered heterocycle containing a nitrogen atom,
  • R 10 and R 11 are each independently a 7j elementary atom, a Ci-C 6 alkyl group, d- A C e c n alkyl, C s -C 8 cycloalkyl group or an optionally substituted good I Ariru group,
  • R 12 is a ⁇ element, a Ci-C 10 alkyl group, C 2 -d. Alkenyl group, C 2 ⁇ Ci. Alkynyl group, Ci ⁇ C l () haloalkyl group, C 2 to d.
  • Haloalkenyl group, C 3 -C 10 consequent ⁇ alkyl group, base may be substituted Njiru group, optionally substituted Ariru C 2 -C 4 alkyl group, optionally substituted Ari le C 2 -C 4 alkenyl group, an optionally substituted Ariru group, Ci ⁇ C e ⁇ alkoxy 0 ⁇ -C 6 alkyl group, Ci ⁇ C 6 dialkylamino ⁇ to c 6 Al kill group, Ci ⁇ C 6 alkylthio d ⁇ C 6 alkyl group, Ci ⁇ C 6 alkoxy Shikarubo nil ⁇ ! ⁇ C 6 alkyl group, optionally substituted phenyloxy!
  • R 18 is a d-C e alkyl group, a d-C e ha ⁇ alkyl group or an optionally substituted aryl group;
  • R "and R 16 are each independently, 7j atom, Ci ⁇ C e alkyl group, C 2 -C e alkenyl group, C 2 -C e alkynyl group, an optionally substituted Ariru group, substituted A benzyl group or a heteroaryl group which may be substituted,
  • R 14 and R 16 may be taken together with the nitrogen atom to which they are attached to form a 4- or 9-membered nitrogen-containing heterocycle
  • Expression "optionally substituted” includes, in addition to a halogen atom as a substituent 7j atom, Shiano group, a nitro group, Ci ⁇ C 4 alkyl group, D ⁇ C 4 alkoxy, Ci ⁇ C 4 c ⁇ alkyl group, Ci ⁇ _4 haloalkoxy group, Ariru group, ⁇ Li Ruokishi group, Benjiruokishi group, C 3 -C 6 cycloalkyl group, Cl ⁇ (: 4 alkoxycarbonyl group, Cj ⁇ C 4 alkylthio group, Ci ⁇ C 4 c ⁇ alkyl thio group, Ci ⁇ C 4 Ryo Ruki Rusuru alkylsulfonyl group, Ci ⁇ C 4 alkyl sulfonyl Group, means a styryl group, an amino group, C i ⁇ C 4 alkoxycarbonyl ⁇ amino group, C i ⁇ C 4 alkoxycarbonyl O alkoxy group, ⁇ amino carbon
  • aryl refers to an aromatic group of fuunil or naphthyl
  • heteroaryl (group) means an aromatic heterocyclic group of a 5-membered ring, a 6-membered ring or a fused ring thereof or an aromatic heterocyclic group fused to a benzene ring,
  • heterocyclyl (group) means a 3- to 6-membered non-aromatic heterocyclic group.
  • a plant disease controlling agent containing a conductor as an active ingredient.
  • Examples of the ⁇ -gen atom of X include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a chlorine atom or a bromine atom is particularly preferable.
  • a fluorine atom a chlorine atom, a bromine atom and an iodine atom
  • a chlorine atom or a bromine atom is particularly preferable.
  • W represents an oxygen atom or a sulfur atom, preferably an oxygen atom.
  • R 2 is a 7-element atom, C i-d.
  • 7i elemental atom methyl group, ethyl group, propyl group, i-propyl group, n-, i- or s-butyl group, methoxy group, ethoxy group, benzyl group, Acetyl, propionyl, optionally substituted benzoyl, substituted Preferred are a pyrazole carboxy group, an optionally substituted thiazole carboxy group and a methoxycarbonyl group.
  • R 8 is not particularly limited, but particularly, R 8 is
  • R 4 and R 6 are a hydrogen atom, a methyl group, an i-propyl group, a methylthioethyl group, a methylsulfonylethyl group or A benzyl group, wherein R e is an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted heterocyclyl group, a d-C 6 alkoxy group, an acid group or D ⁇ C 6 alkoxycarbonyl group, p is 0 to 2, R 7 is D ⁇ C 6 alkyl group,
  • n is 0 to 2
  • R 8 and R 8 are hydrogen atoms, d to C 10 alkyl group, optionally substituted Ariru group, a substituted terrorism to good though Ariru group or D ⁇ C e alkylcarbonyl group,
  • R 8 may be taken together with the nitrogen atom to which they are attached to form a 4- or 11-membered nitrogen-containing heterocycle
  • R 12 is d to Ct. Alkyl group, C 2 ⁇ Ci. Alkenyl group, C 2 ⁇ C ,. It is a haloalkenyl group, a benzyl group which may be substituted or a phenylethyl group which may be substituted, and R 14 and R 16 are preferably d-C 4 alkyl groups. ) 0
  • the definitions of the substituents of R 2 and R 8 have the following meanings.
  • R and Rogen means fluorine, chlorine, bromine and iodine
  • Ci -C 4 alkyl group Ci ⁇ C 6 alkyl group and D ⁇ d.
  • alkyl group examples include methyl, ethyl, n- or i-propyl, n-, s-, i- or t-butyl, pentyl, hexyl, heptyl, nonyl, octyl and the like.
  • d-C 6 alkylcarbonyl group include acetyl And propionyl.
  • Aryl groups include phenyl and naphthyl.
  • Examples of the heteroaryl group include furyl, phenyl, pyrazolyl, thiazolyl, imidazolyl, pyridyl, pyrimidinyl, triazinyl, benzofuranyl, and indolyl.
  • Examples of the C i -C 6 alkoxycarbonyl group include methoxycarbonyl, ethoxycarbonyl, n-propylcarbonyl, i-propylcarbonyl, n-butylcarbonyl and the like.
  • Examples of the C 2 -C 10 alkenyl group include vinyl, ⁇ -penyl, butenyl, hexenyl and the like.
  • Haloalkenyl groups include 1-chloro-1-probenyl and 1-bromo-1-propenyl.
  • the C 8 -C 8 cycloalkyl group, cyclopropyl, cycloheptyl cyclohexane, cyclohexyl and the like cyclohexane is ⁇ up.
  • heterocyclyl group examples include oxilanyl, oxetanyl, tetrahydrofuranyl, dioxolanyl, tetrahydroviranyl, dioxanyl, tetrahydrophenyl, pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, and thiomorpholinyl.
  • Group A a compound in which X is a chlorine atom or a bromine atom, R 1 is a methyl group, and W is an oxygen atom or a sulfur atom.
  • Group B wherein, is a chlorine atom or a bromine atom, R 1 is a methyl group, W is an oxygen atom, R 2 is a hydrogen atom, C i -d.
  • Group C wherein, is a chlorine atom or a bromine atom; R 1 is a methyl group; W is an oxygen atom; R 2 is a hydrogen atom; Alkyl group, Ci
  • Alkoxy group, base may be substituted Njiru group, a formyl group, Ci ⁇ Ce alkylcarbonyl group, an optionally substituted ⁇ reel carbonyl group, substitution which may have been the good hetero arylcarbonyl group, or -C e An alkoxycarbonyl group, wherein R 3 is one of [C (R 4 ) (R 5 )] p one R 6
  • Group D wherein X is a chlorine atom, R 1 is a methyl group, W is an oxygen atom, R 2 is a hydrogen atom, Ci-d. Alkyl group, Ci-d. An alkoxy group or a benzyl group, wherein R 3 is a Ci-C 10 alkyl group,
  • R 4 (R &)] p - a group R e, R 4, R 5 is a 7j atom, Ci -C 4 alkyl or downy Njiru group, R 6 is substituted A phenyl group, an optionally substituted heteroaryl group or an optionally substituted heterocyclyl group, wherein p is 0, 1 or 2.
  • Group E wherein X is a chlorine atom, R 1 is a methyl group, W is an oxygen atom, R 2 is a hydrogen atom, d to C !.
  • Group F wherein, is a chlorine atom, R 1 is a methyl group, W is an oxygen atom, R 2 is a hydrogen atom, d ⁇ .
  • R 7 is, Ci ⁇ C e alkyl group, an optionally substituted Fuweniru group or be - N (R 14) (R 16) group
  • R 14 and R 15 are d to C 4 alkyl groups;
  • n is 2;
  • R 8 and R 8 are each independently a hydrogen atom, an optionally substituted Hue group, base may be substituted Njiru group, Teroari Lumpur group to an optionally substituted, Ci ⁇ C e alkylcarbonyl group, an optionally substituted Benzoiru group or D ⁇ C 6 alkoxycarbonyl group, or, R 8 and R 8 Waso those such together with the nitrogen atom to which they are attached connexion, from 4 11 A nitrogen-containing heterocyclic ring of
  • R 12 is a hydrogen atom, Ci to Ct. Alkyl group, C 2 to d. Alkenyl group, C 2
  • Group G wherein X is a chlorine atom, R 1 is a methyl group, carbon dioxide, an oxygen atom, or R 2 and R 3 together with the nitrogen atom to which they are bonded becomes, the 3 to form a nitrogen-containing heterocycle 11- and their heterocycle Yo Rere compounds substituted Ri by the one or more D ⁇ C e alkyl or D ⁇ C 4 alkoxycarbonyl group .
  • Group H wherein X is a chlorine atom, is a methyl group, and W is an oxygen atom
  • R 2 is a hydrogen atom and R 3 is a d to C 10 alkyl group.
  • Group I wherein X is a chlorine atom, is a methyl group, W is an oxygen atom, R 2 is a hydrogen atom, and R 8 is a C 10 alkoxy group or C 2 to
  • a compound that is a C 10 alkenyloxy group is a compound that is a C 10 alkenyloxy group.
  • Group J wherein X is a chlorine atom, is a methyl group, W is an oxygen atom, R 2 is a hydrogen atom or an optionally substituted benzyl group, and R 8 is (R 4 ) (R 5 )] p is an R 6 group, p is 1 or 2,
  • R 4 is a hydrogen atom, a methyl group or an ethyl group
  • R 5 is a hydrogen atom, a methyl group, an i-propyl group, a benzyl group or a methylthioethyl group
  • R e is a methoxycarbonyl group, an ethoxycarbonyl group, Compounds that are a propyloxycarbonyl group or a t-butoxycarbonyl group.
  • Group K wherein X is a chlorine atom, R 1 is a methyl group, W is an oxygen atom, and R 2 is a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, an aryl group, or a t-group.
  • R 3 is a —N (R 8 ) (R 8 ) group, and R 8 is a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, an aryl group, a t-butyl group, a formyl group, and an acetyl group.
  • R 9 is a hydrogen atom or a methyl group, or R 8 together with the nitrogen atom to which they are attached, 5 A compound which may form a membered nitrogen-containing heterocycle.
  • Group L wherein X is a chlorine atom, R 1 is a methyl group, W is an oxygen atom, and R 2 is a hydrogen atom, a methyl group, an ethyl group, a propyl group, a cyclopropyl group, a methoxy group or A compound in which R 3 is an S (0) felicitR 7 group, n is 2, and R 7 is a methyl group or a dimethylamino group.
  • Group M wherein X is a chlorine atom, R 1 is a methyl group, W is an oxygen atom, and R 2 is a 5-membered member together with the nitrogen atom to which they are attached.
  • Compounds which form a nitrogen-containing heterocycle and which heterocycle may be substituted by one or more d ⁇ (: 4 alkoxyl groups.
  • Group N a compound selected from the following (1) to (7):
  • Group Q Compounds selected from the following (1) to (16):
  • the compound according to the present invention has little or no antibacterial activity against rice blast in a petri dish test. However, sprayed directly on rice In addition, it shows excellent rice blast control effect when applied to the water surface. That is, it is thought that the compound according to the present invention promotes the production of antibacterial substances in the rice body and imparts resistance to disease, thereby preventing the infection of blast fungus and preventing the onset of the disease. Can be
  • Me is a methyl group
  • Et is an ethyl group
  • Pr is a propyl group
  • Bu is a butyl group
  • Pen is a pentyl group
  • Hex is a hexyl group
  • n is normal, i is iso, s is secondary, c is cyclo, t is tertiary
  • Ph represents a fluorine group
  • Y 1 to Y 48 represent the structures described on the following pages c
  • Jiazo of step is usually hydrochloric acid, in a mineral acid sulfuric acid, properly good carried out at 0 ° C desired in the range of one 10 e Celsius to room temperature.
  • the reaction with copper halide it is possible to directly add to the diazonium solution.However, usually, the copper salt is suspended in an inert solvent such as chloroform and the diazonium solution is added. desirable.
  • the reaction is preferably carried out at 0 to 100 or at the reflux temperature of the solvent.
  • the carboxylic acid introduction step following the lithiation is usually carried out in an inert solvent such as getyl ether / tetrahydrofuran at a temperature of ⁇ 120 to room temperature, preferably 180 to 0. Is good. After the completion of the reaction, a carboxylic acid is obtained by performing a usual post-treatment.
  • an inert solvent such as getyl ether / tetrahydrofuran
  • the desired compound (1a) can be synthesized by converting 5-pyrazolecarboxylic acid (4) into a carboxylic acid halide (5) according to a conventional method, and then reacting with various amines (6).
  • the amidation step can be performed in a suitable inert solvent.
  • the solvent include aromatic hydrocarbons such as toluene, xylene and chlorobenzene, halogenated hydrocarbons such as chloroform and dichloromethane, ethers such as diisopropyl ether and dioxane, nitriles such as acetonitrile, and dimethyl.
  • Polar solvents such as sulfoxide and dimethylformamide are exemplified.
  • an organic base pyridine, triethylamine, etc.
  • an inorganic base lanese, sodium hydride, etc.
  • the reaction temperature is usually preferably from 0 to 50 ° C.
  • the solvent examples include aromatic hydrocarbons such as toluene and xylene, and halogenated hydrocarbons such as chloroform and dichloroethane.
  • the reaction can be carried out at a temperature between the temperature and the boiling point of the solvent, and preferably the reflux of the solvent is good.
  • 3-hachigeno 1-alkylpyrazole (3) is lithiated at the 5-position using a lithium compound such as LDA (lithium diisopropylamide) and reacted with chloroethyl or getyl carbonate.
  • LDA lithium diisopropylamide
  • 5-pyrazolecarboxylic acid ethyl ester (7) can be synthesized.
  • the lithiation followed by the introduction of the ethyl ester group is usually carried out in an inert solvent such as getyl ether tetrahydrofuran at a temperature of ⁇ 120 ° C. to room temperature, preferably at ⁇ 80 ° C. After the completion of the reaction, an ordinary post-treatment is performed to obtain an ethyl ester.
  • an inert solvent such as getyl ether tetrahydrofuran
  • the desired product (1a) can be synthesized by reacting the 5-pyrazolecarboxylic acid ethyl ester (7) with various amines (6).
  • the amidation step can be performed in a suitable inert solvent.
  • the solvent include aromatic hydrocarbons such as toluene, xylene, and chlorobenzene; halogenated hydrocarbons such as chloroform and dik ⁇ ethane; ethers such as diisopropyl ether and dioxane; nitriles such as acetonitrile; Examples include polar solvents such as dimethyl sulfoxide and dimethylformamide.
  • an organic base pyridine, triethylamine, etc.
  • an inorganic base latitude, etc.
  • the reaction is preferably carried out at 0 to 120 or at reflux of the solvent.
  • 5-pyrazolecarboxylic acid chloride (5) or 5-pyrazolecarboxylic acid amide (9) synthesized from 5-pyrazolecarboxylic acid ethyl ester (7) is converted into a compound having a leaving group such as halogen.
  • the desired product (1a) can be synthesized by reacting with the above reagent. The reaction with various reagents can be carried out in a suitable inert solvent.
  • toluene for example, toluene, xylene Aromatic hydrocarbons such as chlorobenzene, chlorobenzene, halogenated hydrocarbons such as chloroform and dichloroethane, ethers such as diisopropyl ether and dioxane, nitriles such as acetonitrile, dimethyl sulfoxide, dimethylform amide and the like Polar solvents.
  • an organic base pyridine, triethylamine, etc.
  • an inorganic base carbonated lime, sodium hydride, etc.
  • plant diseases to be controlled by the present compound include:
  • Grape downy mildew P 1 a smo paraitico 1 a
  • black rot Els inoe ampe 1 ina
  • disease Glomer ellac ingul ata
  • powdery mildew Un c inul a necator
  • rust Disease PhaKops or a ampe l ops idis
  • Anthracnose of ikiki (Gl ocospor i um kaki), deciduous disease (Cer eospora ka i, Mycosphaer ella nawae), downy mildew of Pari (Ps eudoper enospor a cubens is), anthracnose (Co lle tot) ri ch um 1 agenari um), rice scab (Sphaerotheca fuli ginea), vine blight (y cosphaer ella me l on is),
  • Tomato blight (Phytophthor a inf es t ans), ring (Alt ernar i a so l an i), leaf mold (Cl adospor i um f ul vum),
  • Eggplant brown 3 ⁇ 4 ⁇ (? 1 01110 isvex: s), powdery mildew (E rysi ph ecichoracar um), black spot of azirana family vegetables (A 1 ternariajapor ca), white spot (Cerocospor ella br as si cae) Leek Rust (Pu cciniaallii),
  • Soybean purpura (Cer cospor a kikuchi i), black rot (Els inoe g 1 y c i n e s), black spot (D i a p o r t h e p h a s e o 1 o 1 um),
  • Angen anthracnose (Colle totrichum 1 indemuthi anum),
  • a suitable carrier for example, a solid carrier such as clay, talc, bentonant, diatomaceous earth or 7, an alcohol (methanol, ethanol, etc.), an aromatic hydrocarbon (Eg, benzene, toluene, methylnaphthalene, etc.), chlorinated hydrocarbons, ethers, ketones, esters (ethyl acetates), and acid amides (dimethylformamide, etc.)
  • emulsifiers, dispersants, suspending agents, mk spreading agents, stabilizers, etc. into liquids, emulsions, wettable powders, powders, granules, flowables And can be put to practical
  • the formulation may be mixed and applied with other kinds of herbicides, various agents, fungicides, plant growth regulators, synergists and the like at the time of formulation or spraying.
  • the application dose of the compound of the present invention varies depending on the application scene, application timing, application method, target disease, cultivated crops, and the like. is there.
  • examples of the preparation of a fungicide containing the compound of the present invention as an active ingredient are shown, but the invention is not limited thereto.
  • “parts” means parts by weight.
  • the above components are uniformly mixed to form an emulsion.
  • the above emulsion is diluted 50 to 20000-fold and dispersed so that the amount of the active ingredient is 0.005 to 50 kg per hectare.
  • Formulation Example 2 wettable powder
  • the above-mentioned components except for the active ingredient are uniformly dissolved, and then the compound of the present invention is added and stirred well, and then wet-milled with a sand mill to obtain a flowable agent.
  • the above-mentioned flowables are diluted 50 to 200 times to be effective Spray so that the amount of ingredients is between 0.005 and 50 kg per hectare.
  • Triethylamine was added to a mixed solution of 0.66 g of 3-methyl-1-methyl-5-pyrazolecarboxylic acid chloride, 0.72 g of 0-ethylhydroxylamine hydrochloride and 40 ml of chloroform at ice-cooling, and 5 g of the mixture was added dropwise. did. After stirring at room temperature for 1 day, 2 Oml of water was added, the form layer was separated, the ⁇ layer was extracted twice with 10 ml of ⁇ -form, and the chloroform layers were combined and dried over anhydrous sodium sulfate.
  • Dissolve 65 g of 3-amino-1-methylvirazole in 550 ml of concentrated hydrochloric acid A solution prepared by dissolving 62 g of sodium nitrite in 120 ml of water was added dropwise to this solution while maintaining the temperature at 0 to 5 under ice cooling. After completion of the dropping, stirring was further continued for 1 hour.
  • the above diazonium solution was added dropwise to a solution of 70 g of chloride in 500 ml of chloroform. On the way, 20 g of chloride was added twice. After completion of the dropwise addition, the mixture was reacted at 50 for 5 hours, followed by stirring at room temperature for 15 hours. After the solution was filtered through celite, sodium carbonate was added to neutralize the solution.
  • the black-mouthed form layer was separated, and the aqueous layer was further extracted twice with 300 mL of ⁇ -mouthed form.
  • the combined black-mouthed form solution was washed with saturated saline and dried over anhydrous sodium sulfate.
  • the solvent was concentrated under reduced pressure, and vacuum distillation was performed to obtain 52 g of 3-chloro-1-methylbiazole as a yellow oil. (Boiling point: 88-93 CZ 35 mmHg) Next, 45 g of this compound was dissolved in 100 ml of tetrahydrofuran.
  • Table 4 shows the physical property values and the like of the compound of the formula (1) according to these methods.
  • the numbers in the tables represent the compound numbers shown in Tables 1 to 3.
  • compound No. 1-1 (a) is compound No. 1-1 of the compound represented by formula (a) shown in Table 1.
  • Table 4 (1) Table 4 (2) Compound No Physical properties Compound No Physical properties Compound No Physical properties g 1 (a) mp 120-121 ° C l-35 (a) mp

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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne des composés représentés par la formule générale (1) dans laquelle X représente un atome d'halogène, W un atome d'oxygène ou de soufre, R1 un groupe alkyle C¿1?-C4, R?2 et R3¿ représentent chacun, de façon indépendante, un atome d'hydrogène ou un alkyle C¿1?-C10, un alcényle C2-C6, un alcynyle C2-C10, un cycloalkyle C3-C10, un aryle-alcényle C2-C4 éventuellement substitué, un groupe -[C(R?4)(R5)]p-R6¿, -CO-(O)m-[C(R?4)(R5)]p-R7¿, -S(O)n-R7, -CON(R?8)(R9), -N(R8)(R9¿), -N=C(R10)(R11) ou -OR12; l'invention concerne aussi un agent de lutte contre les maladies des plantes, comprenant le composé en question comme constituant actif. Cet agent possède une excellente efficacité de lutte contre les maladies des plantes et n'est pas toxique pour les récoltes utiles.
PCT/JP1996/001466 1995-05-31 1996-05-30 Derives de 5-pyrazolecarboxamide et agent de lutte contre les maladies des plantes WO1996038419A1 (fr)

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AU58450/96A AU5845096A (en) 1995-05-31 1996-05-30 5-pyrazolecarboxamide derivatives and plant disease control agent

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JP7/133902 1995-05-31
JP13390295 1995-05-31
JP27749195 1995-10-25
JP7/277491 1995-10-25

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WO1996038419A1 true WO1996038419A1 (fr) 1996-12-05

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Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999009013A1 (fr) * 1997-08-15 1999-02-25 Basf Aktiengesellschaft Fluorpyrazole-biphenylamides fongicides
WO1999062335A1 (fr) * 1998-06-02 1999-12-09 Nissan Chemical Industries, Ltd. Derive de phenylhydrazine, agent antibacterien et antifongique, algicide industriel et agent de prevention de la fixation d'organismes, comprenant ledit derive
EP1020447A4 (fr) * 1997-09-11 2000-11-15 Nissan Chemical Ind Ltd Composes a base de pyrazole et agent de lutte contre les maladies vegetales
WO2002100846A1 (fr) * 2001-06-11 2002-12-19 Shire Biochem Inc. Composes et methodes de traitement ou de prevention d'infections a flavivirus
US6747047B2 (en) 2000-03-22 2004-06-08 E.I. Du Pont De Nemours And Company Insecticidal anthranilamides
US7148217B2 (en) 2001-10-15 2006-12-12 E. I. Du Pont De Nemours And Company Iminobenzoxazines, iminobenzthiazines and iminoquinazolines for controlling invertebrate pests
US7179824B2 (en) 2001-09-21 2007-02-20 E. I. Du Pont De Nemours And Company Arthropodicidal anthranilamides
US7199138B2 (en) 2001-08-16 2007-04-03 E. I. Du Pont De Nemours And Company Substituted anthranilamides for controlling invertebrate pests
EP1772449A1 (fr) * 2005-10-05 2007-04-11 Bayer CropScience S.A. Derives de carboxamides N-alkyl-heterocycliques
WO2007060164A1 (fr) * 2005-11-22 2007-05-31 Bayer Cropscience Sa Nouveaux derives de n-(1-alkyl-2-phenylethyl)carboxamide
US7232836B2 (en) 2001-08-13 2007-06-19 E. I. Du Pont De Nemours And Company Arthropodicidal anthranilamides
US7288554B2 (en) 2001-08-15 2007-10-30 E.I. Du Pont De Nemours And Company Ortho-substituted aryl amides for controlling invertebrate pests
US7354944B2 (en) 2004-10-18 2008-04-08 Amgen Inc. Thiadiazole compounds and methods of use
US7375232B2 (en) 2001-08-15 2008-05-20 E.I. Du Pont De Nemours And Company Ortho-heterocyclic substituted aryl amides for controlling invertebrate pests
WO2009016219A1 (fr) 2007-07-31 2009-02-05 Bayer Cropscience Sa Dérivés fongicides de 2-pyridyl-méthylène-thio carboxamide ou de 2-pyridyl-méthylène- carboximidamide-n-substitué
WO2009127718A3 (fr) * 2008-04-18 2010-02-04 Syngenta Participations Ag Nouveaux microbiocides
US7696233B2 (en) 2001-08-13 2010-04-13 E. I. Du Pont De Nemours And Company Method for controlling particular insect pests by applying anthranilamide compounds
US7696232B2 (en) 2001-09-21 2010-04-13 E. I. Du Pont De Nemours And Company Anthranilamide arthropodicide treatment
US7897619B2 (en) 2007-07-17 2011-03-01 Amgen Inc. Heterocyclic modulators of PKB
US7919504B2 (en) 2007-07-17 2011-04-05 Amgen Inc. Thiadiazole modulators of PKB
US8410157B2 (en) 2007-07-31 2013-04-02 Bayer Cropscience Ag Fungicidal N-cycloalkyl-benzyl-thiocarboxamides or N-cycloalkyl-benzyl-N′-substituted-amidine derivatives
CN107033083A (zh) * 2017-04-30 2017-08-11 浙江工业大学 一种含1‑甲基‑3‑三氟甲基‑1h‑吡唑结构的酰基脲类化合物及其制备方法和应用
WO2020002911A1 (fr) * 2018-06-26 2020-01-02 Imperial College Of Science, Technology And Medicine Cellules tueuses naturelles
CN116589430A (zh) * 2023-05-26 2023-08-15 青岛科技大学 一种含氟酰胺噻唑烷酯类化合物及其用途
WO2023243678A1 (fr) 2022-06-15 2023-12-21 日産化学株式会社 Composé pyrazole, son intermédiaire de production et agent antiparasitaire
WO2024204842A1 (fr) * 2023-03-31 2024-10-03 日産化学株式会社 Composé pyrazole et agent de lutte contre les organismes nuisibles

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WO1999009013A1 (fr) * 1997-08-15 1999-02-25 Basf Aktiengesellschaft Fluorpyrazole-biphenylamides fongicides
EP1020447A4 (fr) * 1997-09-11 2000-11-15 Nissan Chemical Ind Ltd Composes a base de pyrazole et agent de lutte contre les maladies vegetales
WO1999062335A1 (fr) * 1998-06-02 1999-12-09 Nissan Chemical Industries, Ltd. Derive de phenylhydrazine, agent antibacterien et antifongique, algicide industriel et agent de prevention de la fixation d'organismes, comprenant ledit derive
US6995178B2 (en) 2000-03-22 2006-02-07 E. I. Du Pont De Nemours And Company Insecticidal anthranilamides
US7338978B2 (en) 2000-03-22 2008-03-04 E.I. Du Pont De Nemours And Company Insecticidal anthranilamides
US6747047B2 (en) 2000-03-22 2004-06-08 E.I. Du Pont De Nemours And Company Insecticidal anthranilamides
WO2002100846A1 (fr) * 2001-06-11 2002-12-19 Shire Biochem Inc. Composes et methodes de traitement ou de prevention d'infections a flavivirus
US6887877B2 (en) 2001-06-11 2005-05-03 Virochem Pharma Inc. Compounds and methods for the treatment or prevention of Flavivirus infections
US7232836B2 (en) 2001-08-13 2007-06-19 E. I. Du Pont De Nemours And Company Arthropodicidal anthranilamides
US9049862B2 (en) 2001-08-13 2015-06-09 E I Du Pont De Nemours And Company Arthropodicidal anthranilamides
US8158802B2 (en) 2001-08-13 2012-04-17 E.I. Du Pont De Nemours And Company Arthropodicidal anthranilamides
US8148521B2 (en) 2001-08-13 2012-04-03 E.I. Du Pont De Nemours And Company Arthropodicidal anthranilamides
US9029365B2 (en) 2001-08-13 2015-05-12 E I Du Pont De Nemours And Company Arthropodicidal anthranilamides
US9445593B1 (en) 2001-08-13 2016-09-20 E I Du Pont De Nemours And Company Arthropodicidal anthranilamides
US8921400B2 (en) 2001-08-13 2014-12-30 E I Du Pont De Nemours And Company Arthropodicidal anthranilamides
US7696233B2 (en) 2001-08-13 2010-04-13 E. I. Du Pont De Nemours And Company Method for controlling particular insect pests by applying anthranilamide compounds
US9049861B2 (en) 2001-08-13 2015-06-09 E I Du Pont De Nemours And Company Arthropodicidal anthranilamides
US9084422B2 (en) 2001-08-13 2015-07-21 E I Du Pont De Nemours And Company Anthranilamides compositions
US8697734B2 (en) 2001-08-13 2014-04-15 E I Du Pont De Nemours And Company Method for controlling particular insect pests by applying anthranilamide compounds
US9113630B2 (en) 2001-08-13 2015-08-25 E I Du Pont De Nemours And Company Method of controlling particular insect pests by applying anthranilamide compounds
US7902231B2 (en) 2001-08-13 2011-03-08 E.I. Du Pont De Nemours And Company Anthropodicidal anthranilamides
US9078437B2 (en) 2001-08-13 2015-07-14 E I Du Pont De Nemours And Company Arthropodicidal anthranilamides
US7375232B2 (en) 2001-08-15 2008-05-20 E.I. Du Pont De Nemours And Company Ortho-heterocyclic substituted aryl amides for controlling invertebrate pests
US7288554B2 (en) 2001-08-15 2007-10-30 E.I. Du Pont De Nemours And Company Ortho-substituted aryl amides for controlling invertebrate pests
US7199138B2 (en) 2001-08-16 2007-04-03 E. I. Du Pont De Nemours And Company Substituted anthranilamides for controlling invertebrate pests
US7541377B2 (en) 2001-08-16 2009-06-02 E.I. Du Pont De Nemours And Company Substituted anthranilamides for controlling invertebrate pests
US7179824B2 (en) 2001-09-21 2007-02-20 E. I. Du Pont De Nemours And Company Arthropodicidal anthranilamides
US7696232B2 (en) 2001-09-21 2010-04-13 E. I. Du Pont De Nemours And Company Anthranilamide arthropodicide treatment
US9173400B2 (en) 2001-09-21 2015-11-03 E I Du Pont De Nemours And Company Anthranilamide arthropodicide treatment
US8637552B2 (en) 2001-09-21 2014-01-28 E I Du Pont De Nemours And Company Anthranilamide arthropodicide treatment
US7326704B2 (en) 2001-10-15 2008-02-05 E.I. Dupont De Nemours And Company Iminobenzoxazines, iminobenzthiazines and iminoquinazolines for controlling invertebrate pests
US7148217B2 (en) 2001-10-15 2006-12-12 E. I. Du Pont De Nemours And Company Iminobenzoxazines, iminobenzthiazines and iminoquinazolines for controlling invertebrate pests
US7919514B2 (en) 2004-10-18 2011-04-05 Amgen Inc. Thiadiazole compounds and methods of use
US7354944B2 (en) 2004-10-18 2008-04-08 Amgen Inc. Thiadiazole compounds and methods of use
US7700636B2 (en) 2004-10-18 2010-04-20 Amgen Inc. Thiadiazole compounds and methods of use
US8148538B2 (en) 2005-10-05 2012-04-03 Bayer Cropscience Ag N-alkyl-heterocyclyl carboxamide derivatives
EP1772449A1 (fr) * 2005-10-05 2007-04-11 Bayer CropScience S.A. Derives de carboxamides N-alkyl-heterocycliques
WO2007039615A1 (fr) * 2005-10-05 2007-04-12 Bayer Cropscience Sa Nouveaux dérivés de n-alkyl-héterocyclylcarboxamide
WO2007060164A1 (fr) * 2005-11-22 2007-05-31 Bayer Cropscience Sa Nouveaux derives de n-(1-alkyl-2-phenylethyl)carboxamide
EP1792901A1 (fr) * 2005-11-22 2007-06-06 Bayer CropScience S.A. Derives de n-(1-alkyl-2-phenylethyl)-carboxamide et leur utilisation en tant que fongicide
US8148419B2 (en) 2005-11-22 2012-04-03 Bayer Cropscience Ag N-(1-alkyl-2-phenylethyl)-carboxamide derivatives and use thereof as fungicides
US7919504B2 (en) 2007-07-17 2011-04-05 Amgen Inc. Thiadiazole modulators of PKB
US7897619B2 (en) 2007-07-17 2011-03-01 Amgen Inc. Heterocyclic modulators of PKB
CN101772495B (zh) * 2007-07-31 2012-08-29 拜尔农科股份公司 杀真菌剂2-吡啶基-亚甲基-硫-羧酰胺或2-吡啶基-亚甲基-n-取代-甲脒衍生物
JP2010534714A (ja) * 2007-07-31 2010-11-11 バイエル・クロツプサイエンス・エス・アー 殺真菌剤２−ピリジル−メチレン−チオカルボキサミド又は２−ピリジル−メチレン−ｎ−置換カルボキシイミドアミド誘導体
US8410157B2 (en) 2007-07-31 2013-04-02 Bayer Cropscience Ag Fungicidal N-cycloalkyl-benzyl-thiocarboxamides or N-cycloalkyl-benzyl-N′-substituted-amidine derivatives
WO2009016219A1 (fr) 2007-07-31 2009-02-05 Bayer Cropscience Sa Dérivés fongicides de 2-pyridyl-méthylène-thio carboxamide ou de 2-pyridyl-méthylène- carboximidamide-n-substitué
WO2009127718A3 (fr) * 2008-04-18 2010-02-04 Syngenta Participations Ag Nouveaux microbiocides
CN107033083A (zh) * 2017-04-30 2017-08-11 浙江工业大学 一种含1‑甲基‑3‑三氟甲基‑1h‑吡唑结构的酰基脲类化合物及其制备方法和应用
WO2020002911A1 (fr) * 2018-06-26 2020-01-02 Imperial College Of Science, Technology And Medicine Cellules tueuses naturelles
WO2023243678A1 (fr) 2022-06-15 2023-12-21 日産化学株式会社 Composé pyrazole, son intermédiaire de production et agent antiparasitaire
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WO2024204842A1 (fr) * 2023-03-31 2024-10-03 日産化学株式会社 Composé pyrazole et agent de lutte contre les organismes nuisibles
CN116589430A (zh) * 2023-05-26 2023-08-15 青岛科技大学 一种含氟酰胺噻唑烷酯类化合物及其用途

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