WO2013062024A1 - Agent de lutte contre des maladies de plantes contenant un dérivé arylamidine ou un sel de celui-ci - Google Patents

Agent de lutte contre des maladies de plantes contenant un dérivé arylamidine ou un sel de celui-ci Download PDF

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WO2013062024A1
WO2013062024A1 PCT/JP2012/077536 JP2012077536W WO2013062024A1 WO 2013062024 A1 WO2013062024 A1 WO 2013062024A1 JP 2012077536 W JP2012077536 W JP 2012077536W WO 2013062024 A1 WO2013062024 A1 WO 2013062024A1
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optionally substituted
substituted
alkylene
atom
imino
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PCT/JP2012/077536
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English (en)
Japanese (ja)
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小柳　徹
晋太朗 佃
行男 中村
孝祐 常松
清水　学
岩本　拓也
ゆずか 河合
将也 大野
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石原産業株式会社
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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
    • A01N43/34—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
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/52—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing groups, e.g. carboxylic acid amidines
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom not containing sulfur-to-oxygen bonds, e.g. polysulfides
    • 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
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • 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
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C311/04—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms

Definitions

  • the present invention relates to a plant disease control agent comprising an arylamidine derivative or a salt thereof as an active ingredient, and a novel arylamidine derivative or a salt thereof.
  • Patent Documents 1 and 2 describe an arylamidine derivative useful as a medical antifungal agent and its pharmaceutical use, but does not describe that the derivative is useful for controlling plant diseases.
  • the present inventors have studied to solve the above-mentioned problems, and as a result, by using the compound represented by the formula (I) or a salt thereof as an active ingredient, an excellent control effect against various plant diseases.
  • the present invention was completed by obtaining the knowledge that the compound also has useful properties as a plant disease control agent.
  • a 1 and A 2 are each independently amidino which may be protected;
  • X 1 and X 2 are each independently an alkylene which may be substituted with a halogen atom (methylene in the alkylene may be replaced with an oxygen atom, a sulfur atom or an optionally substituted imino);
  • Z is an optionally substituted imino or an optionally substituted nitrogen-containing heterocycle;
  • R 1 and R 2 are each independently a halogen atom, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted alkylthio, nitro, or optionally substituted.
  • the present invention is based on the formula (I) among the active ingredients of the plant disease control agent:
  • a 1 and A 2 are each independently amidino which may be protected;
  • X 1 and X 2 are each independently an alkylene which may be substituted with a halogen atom (methylene in the alkylene may be replaced with an oxygen atom, a sulfur atom or an optionally substituted imino);
  • Z is an optionally substituted imino or an optionally substituted nitrogen-containing heterocycle;
  • R 1 and R 2 are each independently a halogen atom, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted alkylthio, nitro, or optionally substituted.
  • l and m are each independently an integer of 0 to 4; (1) (i) both A 1 and A 2 are bonded to the para position relative to X 1 and X 2 , and (a) both X 1 and X 2 are alkylenes replaced with oxygen atoms The oxygen atom is bonded to the benzene ring, and Z may be substituted (the imino substituent may be substituted alkyl, cycloalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxythiocarbonyl, alkylthiocarbonyl).
  • An alkylene having a sulfur atom, an oxygen atom or an optionally substituted imino bonded to a benzene ring, and Z may be substituted (the imino substituent is an optionally substituted alkyl) , Cycloalkyl, alkylcarbonyl, alkoxycarbonyl, alkoxythiocarbonyl, alkylthiocarbonyl and alkyldithiocarbonyl) (ii) A 1 is bonded to X 1 in the para position
  • the carbon atom constituting the heterocycle is bonded to X 2 ; (3) A 1 is bonded to the para position with respect to X 1 , X 2 is alkylene, the alkylene is bonded to the benzene ring through a carbon atom, and Z may be substituted In the case of a nitrogen-containing heterocycle, the carbon atom constituting the heterocycle is bonded to X 1 ] And a novel compound or a salt thereof.
  • the plant disease control agent of the present invention has a high control effect against a wide range of plant pathogens and also has high safety.
  • the plant disease control agent of the present invention has a so-called residual effect that maintains the plant disease control effect for a long time after spraying the drug, and also exhibits an excellent effect even when the crop is subjected to rain after spraying the drug. Yes, it has excellent so-called rain resistance. Since the plant disease control agent of the present invention has useful properties as such a plant disease control agent, the number of times the drug is used or the amount used is increased in consideration of rainfall after the spraying of the drug and the duration of the control effect. It is not necessary and can protect crops from plant diseases at lower cost and less effort.
  • —C ( ⁇ O) R ′ R ′ may be an optionally substituted alkyl, which may be substituted.
  • Arylalkyl, optionally substituted aryl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted arylalkoxy, optionally substituted arylalkylthio, optionally substituted aryloxy or substituted May represent arylthio), —C ( ⁇ S) R ′ (R ′ is as defined above), —OH, —OC ( ⁇ O) R ′′ (R ′′ represents an optionally substituted alkyl) , Represents an optionally substituted arylalkyl or an optionally substituted aryl), —OC ( ⁇ S) R ′′ (where R ′′ is the same as described above), or —OR ′′ (where R ′′ is as defined above). Amidino protected by the same
  • substitution position of the amidino which may be protected represented by A 1 or A 2 is not particularly limited, it is preferably substituted at the meta position or para position with respect to X 1 and X 2 .
  • Examples of the alkylene in X 1 or X 2 include C 1 -1 such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, undecamethylene, and dodecamethylene. There are 12 examples.
  • the alkylene may be substituted with one or more halogen atoms which are the same or different.
  • one or more methylenes in the alkylene may be replaced with an oxygen atom, a sulfur atom or an imino which may be substituted, and the position and number of the substitution are not particularly limited.
  • the imino replaced with methylene may be substituted with a substituent represented by R 3 .
  • the imino in Z may be substituted with a substituent represented by R 3 .
  • a 3 is an amidino which may be protected, and X 3 is an alkylene which may be substituted with a halogen atom (methylene in the alkylene is an oxygen atom, a sulfur atom or an imino which may be substituted)
  • R A may be a halogen atom, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkoxy, optionally substituted alkylthio, nitro, optionally substituted.
  • alkyl group which may be substituted in R 3 does not include the group represented by the formula (B).
  • the protected may be amidino represented by A 3, are the same as those of the exemplified protected may be an amidino as the A 1 or A 2.
  • Examples of the alkylene that may be substituted with a halogen atom represented by X 3 include the same alkylenes exemplified as X 1 or X 2 .
  • the nitrogen-containing heterocycle in Z contains one or more non-aromatic nitrogen atoms, and in some cases contains one or more heteroatoms other than nitrogen atoms (for example, oxygen atoms, sulfur atoms, etc.).
  • Saturated or unsaturated 3- to 7-membered or polycyclic heterocyclic ring may be mentioned.
  • the heterocyclic ring may be monocyclic or polycyclic, and may be substituted with an oxo group ( ⁇ O).
  • monocyclic nitrogen-containing heterocycles include 3-membered heterocycles such as aziridine; 4-membered heterocycles such as azetidine; pyrrolidine, pyrroline, imidazolidine, imidazoline, pyrazolidine, pyrazoline, oxazolidine, oxazoline, isoxazolidine 5-membered heterocycles such as isoxazoline, thiazolidine, thiazoline, isothiazolidine, isothiazoline; 6-membered heterocycles such as piperidine, piperazine, morpholine, thiomorpholine, perhydropyrimidine, perhydropyridazine; such as azepane and diazepane 7-membered heterocyclic ring; and the like.
  • polycyclic nitrogen-containing heterocycle examples include condensed nitrogen-containing heterocycles such as indoline and isoindoline; quinuclidine, 7-azabicyclo [2.2.1] heptane, 2,5-diazabicyclo [2.2.1] heptane, Bridged nitrogen-containing compounds such as 2,5-diazabicyclo [2.2.2] octane, 8-azabicyclo [3.2.1] octane, 3-azabicyclo [3.2.1] octane, 3,8-diazabicyclo [3.2.1] octane A heterocyclic ring; and the like.
  • the nitrogen-containing heterocycle may have 1 to 8 substituents at substitutable positions, and when there are two or more substituents, each substituent may be the same or different.
  • Alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl represented by R 1 , R 2 , R A or R B may have 1 to 7 substituents at each substitutable position. When the number of groups is 2 or more, each substituent may be the same or different.
  • the cycloalkyl represented by R 1 , R 2 or R A may have 1 to 11 substituents at substitutable positions. Examples of such substituents include the nitrogen-containing heterocycle described above. The thing similar to the substituent which it has is mentioned.
  • R 3 , R ′, R ′′ or R B and each substituent in the amino substituent represented by R 1 , R 2 or R A is substituted at a substitutable position. It may have a group.
  • substituent on the alkyl or alkyl moiety examples include halogen, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, nitro, trimethylsilyl, thiocyanato, aryloxy and the like.
  • Aryl or aryl moieties or cycloalkyl substituents include halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, nitro, trimethylsilyl, thiocyanato, aryl, alkyl Amino, dialkylamino and the like can be mentioned.
  • examples of the halogen atom or the halogen as a substituent include fluorine, chlorine, bromine and iodine atoms.
  • the number of halogen atoms as substituents may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.
  • an alkyl or an alkyl moiety includes C 1 such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl and the like. -12 and so on.
  • examples of cycloalkyl include those of C 3-6 such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
  • examples of the aryl or aryl moiety include those of C 6-10 such as phenyl and naphthyl.
  • the salt of the compound of the formula (I) includes any salt that is acceptable in the technical field.
  • a salt with an inorganic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or the like.
  • Salts with organic carboxylic acids such as tartaric acid, formic acid, acetic acid, citric acid, fumaric acid, maleic acid, trichloroacetic acid and trifluoroacetic acid; methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, mesitylenesulfonic acid and naphthalene
  • salts with sulfonic acids such as sulfonic acids.
  • the compound of the formula (I) may have isomers such as geometric isomers, tautomers, and optical isomers. In the present invention, both isomers and isomer mixtures are present. Is included. In the present specification, unless otherwise specified, isomers are described as a mixture. The present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field.
  • X 1 or X 2 in the above formula (I) is each independently an alkylene in which methylene in the alkylene may be replaced by an oxygen atom or a sulfur atom (for example, C 2-9 alkylene, in particular, C 2-8 alkylene) is preferred.
  • X 1 in the above formula (I) is specifically —O—, — (CH 2 ) 4 —, —OCH 2 —, —O (CH 2 ) 2 —, —O (CH 2 ) 3 —, —O (CH 2 ) 4 —, —O (CH 2 ) 5 —, —O (CH 2 ) 7 —, —O (CH 2 ) 9 —, —CH 2 OCH 2 —, —CH 2 O ( CH 2 ) 2 —, —O (CH 2 ) 3 O (CH 2 ) 3 —, —O (CH 2 ) 2 CH (CH 3 ) —, —O (CH 2 ) 3 CH (CH 3 ) —, —SCH 2 —, —S (CH 2 ) 3 —, —S (CH 2 ) 4 —, —CH 2 S (CH 2 ) 2 —, — (CH 2 ) 2 S (CH 2 ) 3 —, — SCH
  • X 2 in the above formula (I) is specifically —O—, — (CH 2 ) 4 —, —CH 2 O—, — (CH 2 ) 2 O—, — (CH 2 ) 3 O—, — (CH 2 ) 4 O—, — (CH 2 ) 5 O—, — (CH 2 ) 7 O—, — (CH 2 ) 9 O—, —CH 2 OCH 2 —, — (CH 2 ) 2 OCH 2 —, — (CH 2 ) 3 O (CH 2 ) 3 O—, —CH (CH 3 ) (CH 2 ) 2 O—, —CH (CH 3 ) (CH 2 ) 3 O—, — CH 2 S—, — (CH 2 ) 3 S—, — (CH 2 ) 4 S—, — (CH 2 ) 2 SCH 2 —, — (CH 2 ) 3 S (CH 2 ) 2 —, —CH 2 NH (CH 2 ) 3 O—
  • Z in the above formula (I) is preferably an imino which may be substituted or a nitrogen-containing saturated heterocyclic ring which may be substituted (particularly a 5- to 6-membered heterocyclic ring).
  • the imino substituent is preferably a group represented by the formula (B), and more preferably, X 3 is an alkylene substituted with an oxygen atom.
  • R 1 and R 2 in the formula (I) are each independently halogen, optionally substituted alkyl, optionally substituted alkoxy, optionally substituted alkylthio, optionally substituted amino or Nitro is preferred, and optionally substituted alkylthio, optionally substituted amino or nitro.
  • R 1 or R 2 in the above formula (I) specifically, —F, —Me, —OMe, —SMe, —SEt, —Si—Pr, —NH 2 , —NHMe, —N ( Me) 2 and —NO 2 are preferred.
  • l and m are each independently 0 or 1. As l and m, 1 is more preferable respectively.
  • preferred specific examples of the arylamidine derivatives include compounds obtained by appropriately combining the above preferred substituents of A 1 , A 2 , X 1 , X 2 , Z, R 1 and R 2 in the above formula (I). More preferred specific examples include various compounds described in the examples, and particularly preferred specific examples include compounds measuring physical properties among various compounds described in the examples. Can be mentioned.
  • the compound of the above formula (I) or a salt thereof (hereinafter also referred to as the compound of the present invention) can be produced according to the following production method, ordinary salt production method and usual amidino protection method. It is not limited to.
  • Z 1 is an imino optionally substituted with R 3 ;
  • Y 1 is L, Y 2 is amino or NHR 3 ;
  • Y 1 is amino or NHR 3 , Y 2 is L;
  • L is halogen (chlorine, bromine, iodine, etc.), —OSO 2 R 4 (R 4 is alkyl optionally substituted with fluorine or the like, or aryl optionally substituted with alkyl, etc.), —OP ( A leaving group such as ⁇ O) (OR 5 ) 2 (R 5 is alkyl);
  • R 1 , R 2 , R 3 , X 1 , X 2 , l and m are the same as described above.
  • Compound (IV) can be produced by reacting compound (II) with compound (III) in the presence of a base and a solvent.
  • any solvent can be used as the solvent used in this reaction as long as it does not adversely influence the reaction.
  • N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone examples include polar aprotic solvents such as acetonitrile and dimethyl sulfoxide; ethers such as tetrahydrofuran, dioxane and ethylene glycol diethyl ether; and the like.
  • Bases used in this reaction include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal carbonates such as sodium carbonate and potassium carbonate; alkali metals such as sodium hydrogen carbonate and potassium hydrogen carbonate.
  • Bicarbonates alkyl lithiums such as n-butyl lithium and t-butyl lithium; organic bases such as triethylamine, diisopropylethylamine and pyridine;
  • the amount of the base used is equimolar or more, preferably 1.1 to 2.2 times the molar amount of the compound (II) or compound (III).
  • the reaction temperature is usually about 0 to 150 ° C., preferably about 10 to 100 ° C., and the reaction time is usually about 1 to 2 hours.
  • Compound (II) and Compound (III) can be produced by the methods described in WO96 / 16947, WO03 / 74476 and the like.
  • R 6 is C 1-8 alkyl, or benzyl optionally substituted with alkyl, alkoxy, etc .; R 1 , R 2 , X 1 , X 2 , Z 1 , l and m are the same as described above.
  • Compound (V) can be produced by reacting compound (IV) with R 6 OH in the presence of an acid.
  • R 6 OH methanol and ethanol are usually used, but propanol, butanol, isobutanol, octanol, benzyl alcohol and the like can also be used.
  • R 6 OH is usually used, but ethers such as diethyl ether, tetrahydrofuran and dioxane; halogenated hydrocarbons such as methylene chloride and chloroform; aromatic hydrocarbons such as benzene and toluene. Etc. can also be used alone or in combination.
  • hydrogen chloride and hydrogen bromide are usually used, but perchloric acid, sulfonic acids such as methanesulfonic acid, p-toluenesulfonic acid, and the like can also be used.
  • the reaction temperature is usually about ⁇ 20 to 50 ° C., preferably about ⁇ 10 to 20 ° C., and the reaction time is usually about 1 to 24 hours, preferably about 2 to 12 hours.
  • Compound (Ia) can be produced by reacting compound (V) with ammonia or an ammonium salt in a solvent.
  • ammonia ammonia water or ammonia gas can be used as appropriate.
  • ammonium salts include ammonium chloride, ammonium bromide, and ammonium acetate.
  • alcohols such as methanol, ethanol and propanol are usually used, but ethers such as diethyl ether, tetrahydrofuran and dioxane; halogenated hydrocarbons such as methylene chloride and chloroform; N, N— Polar aprotic solvents such as dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, acetonitrile, dimethyl sulfoxide; and the like can be used alone or in admixture.
  • ethers such as diethyl ether, tetrahydrofuran and dioxane
  • halogenated hydrocarbons such as methylene chloride and chloroform
  • N, N— Polar aprotic solvents such as dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, acetonitrile, dimethyl sulfoxide; and the like can be used alone or in admixture.
  • the reaction temperature is usually about ⁇ 20 to 100 ° C., preferably about ⁇ 10 to 80 ° C., and the reaction time is usually about 1 to 48 hours, preferably about 2 to 24 hours.
  • R 7 is C 1-4 alkyl
  • R 1 , R 2 , X 1 , X 2 , Z 1 , l and m are the same as described above.
  • Compound (VI) can be produced by reacting compound (IV) with hydrogen sulfide in the presence of a base and a solvent.
  • Examples of the base include ammonia, triethylamine, diisopropylethylamine, pyridine, 2-picoline and the like.
  • alcohols such as methanol, ethanol and isopropanol
  • bases such as pyridine and 2-picoline can also be used as the solvent.
  • the reaction temperature is usually about 0 to 120 ° C., preferably about 20 to 100 ° C.
  • the reaction time is usually about 1 to 48 hours, preferably about 2 to 24 hours.
  • Compound (VII) can be produced by alkylating compound (VI) with an alkylating agent in a solvent.
  • alkylating agent examples include alkyl halides such as methyl iodide, ethyl iodide, and ethyl bromide; dialkyl sulfates such as dimethyl sulfate and diethyl sulfate.
  • the solvent examples include ketones such as acetone and 2-butanone; halogenated hydrocarbons such as methylene chloride and chloroform; and the like can be used alone or as a mixture.
  • the reaction temperature is usually about 0 to 100 ° C., preferably about 10 to 80 ° C., and the reaction time is usually about 1 to 48 hours, preferably about 2 to 24 hours.
  • Compound (Ia) can be produced by reacting compound (VII) with ammonia or an ammonium salt in a solvent.
  • ammonia ammonia water or ammonia gas can be used as appropriate.
  • ammonium salts include ammonium chloride, ammonium bromide, and ammonium acetate.
  • alcohols such as methanol, ethanol and propanol are usually used, but ethers such as diethyl ether, tetrahydrofuran and dioxane; halogenated hydrocarbons such as methylene chloride and chloroform; N, N— Polar aprotic solvents such as dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, acetonitrile, dimethyl sulfoxide; and the like can be used alone or in admixture.
  • ethers such as diethyl ether, tetrahydrofuran and dioxane
  • halogenated hydrocarbons such as methylene chloride and chloroform
  • N, N— Polar aprotic solvents such as dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone, acetonitrile, dimethyl sulfoxide; and the like can be used alone or in admixture.
  • the reaction temperature is usually about ⁇ 20 to 100 ° C., preferably about ⁇ 10 to 80 ° C., and the reaction time is usually about 1 to 24 hours, preferably about 2 to 12 hours.
  • Compound (Ia) can be produced from compound (IV) via compound (Ia-1) in which amidino is protected.
  • R 1 , R 2 , X 1 , X 2 , Z 1 , l and m are the same as described above.
  • Compound (Ia-1) can be produced by reacting compound (IV) with hydroxylamine or a hydroxylamine salt in a solvent.
  • Hydroxylamine salts include hydrochloride, sulfate and the like.
  • the solvent examples include alcohols such as methanol, ethanol and isopropanol; polar aprotic solvents such as dimethyl sulfoxide and N, N-dimethylformamide; and the like can be used alone or in combination.
  • an inorganic base such as sodium acetate, potassium acetate, sodium carbonate or potassium carbonate or an organic base such as triethylamine, diisopropylethylamine or pyridine is used to adjust the pH of the reaction solution. Is usually used.
  • the reaction temperature is usually about 0 to 120 ° C., preferably about 20 to 80 ° C.
  • the reaction time is usually about 1 to 24 hours, preferably about 2 to 12 hours.
  • Compound (Ia-1) can be converted to Compound (Ia) by a hydrogenation reaction using a metal catalyst such as Raney nickel, palladium, rhodium or the like in a solvent, or a reduction reaction with zinc in acetic acid.
  • a metal catalyst such as Raney nickel, palladium, rhodium or the like in a solvent, or a reduction reaction with zinc in acetic acid.
  • solvent used in the hydrogenation reaction examples include carboxylic acids such as formic acid and acetic acid; ethers such as tetrahydrofuran and dioxane; alcohols such as methanol and ethanol;
  • the reaction temperature of the hydrogenation reaction is usually about 0 to 120 ° C., preferably about 20 to 80 ° C., and the reaction time is usually about 1 to 24 hours, preferably about 2 to 12 hours.
  • the reaction temperature for the reduction with zinc in acetic acid is usually about 10 to 110 ° C., preferably about 30 to 80 ° C., and the reaction time is usually about 1 to 24 hours, preferably about 2 to 12 hours. It is.
  • Compound (Ia) can also be produced from compound (Ia-1) via compound (Ia-2) in which amidino is protected.
  • R 8 is alkyl optionally substituted with halogen, etc .; arylalkyl optionally substituted with alkyl, alkoxy, etc .; or aryl optionally substituted with alkyl, alkoxy, etc .; R 1 , R 2 , X 1 , X 2 , Z 1 , l and m are the same as described above.
  • Compound (Ia-2) can be produced by reacting compound (Ia-1) with an acid halide or acid anhydride in the presence of an acid or a base catalyst in a solvent.
  • the acid catalyst examples include carboxylic acids such as acetic acid and trifluoroacetic acid; inorganic acids such as hydrochloric acid and sulfuric acid; sulfonic acids such as methanesulfonic acid and p-toluenesulfonic acid; and the like.
  • the base catalyst examples include organic bases such as triethylamine, diisopropylethylamine, and pyridine.
  • Examples of the acid halide include acetyl chloride, propionyl chloride, butyryl chloride, phenylacetic acid chloride and the like.
  • Examples of the acid anhydride include acetic anhydride and propionic anhydride.
  • solvent examples include ethers such as diethyl ether, tetrahydrofuran and dioxane; halogenated hydrocarbons such as methylene chloride and chloroform, and these can be used alone or as a mixture.
  • the reaction temperature is usually about 0 to 100 ° C., preferably about 10 to 60 ° C., and the reaction time is usually about 1 to 24 hours, preferably about 2 to 12 hours.
  • Compound (Ia-2) can be converted to Compound (Ia) by a hydrogenation reaction using a metal catalyst such as Raney nickel, palladium, or rhodium in a solvent.
  • a metal catalyst such as Raney nickel, palladium, or rhodium in a solvent.
  • solvent examples include carboxylic acids such as formic acid and acetic acid; ethers such as tetrahydrofuran and dioxane; alcohols such as methanol and ethanol;
  • the reaction temperature is usually about 0 to 120 ° C., preferably about 20 to 80 ° C.
  • the reaction time is usually about 1 to 24 hours, preferably about 2 to 12 hours.
  • Compound (Ia) can also be produced by reacting compound (IV) with lithium bis (trimethylsilyl) amide in a solvent.
  • R 1 , R 2 , X 1 , X 2 , Z 1 , l and m are the same as described above.
  • the solvent examples include ethers such as diethyl ether and tetrahydrofuran; polar aprotic solvents such as N, N-dimethylformamide and hexamethylphosphoric triamide; and the like can be used alone or in combination. .
  • the reaction temperature is usually about ⁇ 78 to 50 ° C., preferably about ⁇ 30 to 30 ° C., and the reaction time is usually about 1 to 24 hours, preferably about 2 to 12 hours.
  • Z 2 is a nitrogen-containing heterocycle, and a nitrogen atom constituting the heterocycle is bonded to X 1 or R 9 ;
  • R 9 is an amino protecting group;
  • R 1 , R 2 , X 1 , X 2 , L, l and m are the same as described above.
  • Examples of the amino protecting group represented by R 9 include t-butoxycarbonyl, benzyloxycarbonyl, benzyl and the like.
  • Compound (VIII) can be produced by the method described in WO 03/74476 or WO 06/3881.
  • the solvent examples include halogenated hydrocarbons such as methylene chloride and chloroform; ethers such as tetrahydrofuran and dioxane; alcohols such as methanol and ethanol; polar aprotic solvents such as acetonitrile and dimethylformamide; Or can be used in combination.
  • halogenated hydrocarbons such as methylene chloride and chloroform
  • ethers such as tetrahydrofuran and dioxane
  • alcohols such as methanol and ethanol
  • polar aprotic solvents such as acetonitrile and dimethylformamide
  • the reaction temperature is usually about ⁇ 20 to 120 ° C., preferably about 0 to 100 ° C., and the reaction time is usually about 1 to 24 hours, preferably about 2 to 12 hours.
  • Compound (VIII) in which R 9 is a benzyloxycarbonyl group or a benzyl group can be converted to compound (IX) by catalytic hydrogenation in a solvent using a catalyst such as palladium, palladium chloride, Raney nickel or the like.
  • the solvent examples include alcohols such as methanol and ethanol; carboxylic acids such as formic acid and acetic acid; ethers such as tetrahydrofuran and dioxane; and the like. These can be used alone or in combination.
  • the reaction temperature is usually about ⁇ 20 to 120 ° C., preferably about 0 to 100 ° C., and the reaction time is usually about 1 to 24 hours, preferably about 2 to 12 hours.
  • Compound (XI) can be obtained by reacting Compound (IX) with Compound (X) under the same reaction conditions as the reaction between Compound (II) and Compound (III) in Production Method 1.
  • the method for converting compound (XI) to compound (Ib-1) can be appropriately selected from the methods for converting compound (IV) in production method 2 to production method 6 to compound (Ia). .
  • a compound (Ib-2) in which Z is a nitrogen-containing heterocyclic ring and X 1 ′ and X 2 ′ are bonded to a carbon atom of the heterocyclic ring can be produced by the following production method 8.
  • X 1 ′ and X 2 ′ are each independently alkylene which may be substituted with a halogen atom (provided that methylene to which L in the alkylene is not bonded represents an oxygen atom or a sulfur atom) May be substituted);
  • Each W is independently an oxygen atom or a sulfur atom;
  • Z 3 is a nitrogen-containing heterocycle, and the carbon atom constituting the heterocycle is bonded to X 1 ′ and X 2 ′;
  • R 1 , L, l and R 3 are the same as described above.
  • Compound (XII) can be produced according to the method described in WO09 / 61879, WO05 / 26165, Chemistry Letters, 1996, 747 and the like.
  • Compound (XIV) can be obtained by reacting compound (XII) with compound (XIII) under the same reaction conditions as the reaction between compound (II) and compound (III) in Production Method 1.
  • the method for converting compound (XIV) to compound (Ib-2) can be appropriately selected from the methods for converting compound (IV) in production method 2 to production method 6 to compound (Ia). .
  • R 10 is C 1-4 alkyl optionally substituted with halogen or the like, or C 7-10 arylalkyl optionally substituted with alkyl, alkoxy or the like;
  • R 1 , R 2 , X 1 , X 2 , Z 1 , l and m are the same as described above.
  • Compound (Ia-3) can be produced by reacting compound (Ia-1) with an alkylating agent in the presence of a base, if necessary, in a solvent.
  • the base examples include organic bases such as triethylamine, diisopropylethylamine and pyridine; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydroxide and hydroxide Alkali metal hydroxides such as lithium; and the like.
  • alkylating agent examples include alkyl halides such as methyl iodide, ethyl bromide and benzyl bromide; dialkyl sulfates such as dimethyl sulfate and diethyl sulfate.
  • Solvents include ethers such as diethyl ether, tetrahydrofuran and dioxane; halogenated hydrocarbons such as methylene chloride and chloroform; polar aprotic solvents such as dimethyl sulfoxide and N, N-dimethylformamide; water and the like These may be used alone or in admixture.
  • the reaction temperature is usually about 0 to 120 ° C., preferably about 20 to 100 ° C.
  • the reaction time is usually about 1 to 48 hours, preferably about 2 to 24 hours.
  • R 11 is C 1-4 alkyl which may be substituted with halogen, alkoxy or the like; C 1-4 alkoxy which may be substituted with halogen, alkoxy or the like; may be substituted with halogen, alkyl, alkoxy or the like good C 6-10 aryl; halogen, alkyl, C 7-12 arylalkyl which may be substituted by an alkoxy, a halogen, alkyl, optionally C 6-10 aryloxy optionally substituted by an alkoxy, a halogen, alkyl, alkoxy C 7-12 arylalkoxy optionally substituted by, and the like; R 1 , R 2 , X 1 , X 2 , Z 1 , l and m are the same as described above.
  • Compound (Ia-4) can be produced by reacting compound (Ia) with chloroformate, dicarbonate, acid halide or acid anhydride in the presence of a base catalyst in a solvent.
  • Base catalysts include organic bases such as triethylamine, diisopropylethylamine, pyridine; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal carbonates such as sodium carbonate and potassium carbonate; sodium hydroxide, water And alkali metal hydroxides such as lithium oxide.
  • chloroformate examples include ethyl chloroformate, propyl chloroformate, isopropyl chloroformate, butyl chloroformate, phenyl chloroformate, benzyl chloroformate and the like.
  • dicarbonate examples include diethyl pyrocarbonate and dibenzyl dicarbonate.
  • acid halide examples include acetyl chloride and benzoyl chloride.
  • the acid anhydride examples include acetic anhydride and benzoic anhydride.
  • Solvents include ethers such as diethyl ether, tetrahydrofuran and dioxane; halogenated hydrocarbons such as methylene chloride and chloroform; polar aprotic solvents such as dimethyl sulfoxide and N, N-dimethylformamide; water and the like These may be used alone or in admixture.
  • the reaction temperature is usually about 0 to 120 ° C., preferably about 20 to 100 ° C.
  • the reaction time is usually about 1 to 48 hours, preferably about 2 to 24 hours.
  • the compound of the present invention can be applied to, for example, Mastigomycotina, Ascomycotina, Basidiomycotina, Deuteromycotina, Zygomycotina, etc. It can control phytopathogenic fungi belonging to them, and is particularly effective for controlling phytopathogenic fungi belonging to Ascomycotina or Deuteromycotina.
  • plant pathogenic bacteria More specific examples include the following.
  • Erysiphe genus such as wheat powdery mildew (Erysiphe graminis); Sphaerotheca humuli such as cucumber powdery mildew (Sphaerotheca fuliginea), Sphaerotheca humuli ; Uncinula genus such as Grape powdery mildew (Uncinula necator); Podosphaera genus such as Podosphaera leucotricha; Mycosphaerellaspinodes, Mycosphaerella ), Banana black sigatoka (Mycosphaerella musicola), oyster circle deciduous fungus (Mycosphaerella nawae), Mycosphaerella fragariae genus Mycosphaerella (Mycosphaerella) genus; Venturia genus such as Venturia nashicola); Pyrenophora teres, Pyrenophora graminea, Pyren
  • Rhizoctonia genus such as rice rot fungus (Rhizoctonia solani); Ustilago genus such as wheat naked smut fungus (Ustilago nuda); Oat crown rust fungus (Puccinia coronata), Puccinia recondita, Puccinia striiformis genus Puccinia, and the like.
  • Septoria nodorum Septoria tritici genus Septoria tritici
  • Botrytis cinerea genus Botrytis ;
  • Pyricularia genus such as rice blast fungus (Pyricularia oryzae); Cercospora beticola, Cercospora genus such as Cercospora beticvola; Colletotrichumbicular Colletotrichum genus such as: Alternaria alternata apple pathotype, pear black rot (Alternaria alternata Japanese pear pathotype), potato summer or tomato rot fungus (Alternaria solani), cabbage black spot fungus ( Alternaria genus such as Alternaria brassicae; Pseud genus Pseudocercosporella such as ocercosporella herpotrichoides; genus Pseudocercospora such as Pseudocercospora vitis; Rhynchosporium secali
  • zygomycetes examples include the genus Rhizopus ⁇ ⁇ ⁇ stronifer and the genus Rhizopus such as Rhizopus nigricans.
  • the compound of the present invention is useful as an active ingredient of a plant disease control agent.
  • a plant disease control agent for example, rice blast, sesame leaf blight, coat blight; wheat powdery mildew, red mold, rust, snow rot, Bare scab, eye rot, leaf blight, dry blight; citrus black spot disease, scab; apple monilia disease, powdery mildew, spotted leaf disease, black star disease, anthracnose disease, brown spot disease, circle Herb disease, soot spot disease, soot spot disease, black spot disease; pear black star disease, black spot disease, powdery mildew, plague; pear ring-shaped ring disease, powdery mildew; Rot disease; grape black rot, late rot, powdery mildew, downy mildew, gray mold, brown spot, branch swelling; oyster anthracnose, deciduous, powdery mildew, soot spot; cucumber Anthracnose, powdery mildew, vine blight, downy mildew
  • the compound of the present invention is usually prepared by mixing the compound with various agricultural adjuvants, powders, granules, granule wettable powders, wettable powders, aqueous suspensions, oily suspensions, aqueous solvents, emulsions, It can be formulated into various forms such as liquids, pastes, aerosols, microdispersions, etc., but can be made into any conventional form used in the art as long as it meets the purpose of the present invention. it can.
  • Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; water, Solvents such as toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, alcohol Fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylates, alkyl sulfate esters, alkyl sulfates, alkylaryl s
  • each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. Further, in addition to the above-mentioned adjuvants, it can also be used by appropriately selecting from those known in the art, a bulking agent, a thickener, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a safener, Various commonly used adjuvants such as antifungal agents can also be used.
  • the compounding ratio of the compound of the present invention and various adjuvants is generally 0.005: 99.995 to 95: 5, preferably 0.2: 99.8 to 90:10. Therefore, the content of the arylamidine derivative or a salt thereof in the plant disease control agent is 0.005% to 95% by weight, desirably 0.2% to 90% by weight.
  • these preparations use them as they are, or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.
  • the concentration of the compound of the present invention varies depending on the target crop, method of use, formulation, application rate, etc., and cannot be defined unconditionally, but in the case of foliage treatment, it is usually 0.1 to 10,000 ppm per active ingredient, Desirably, it is 1 to 2,000 ppm. In the case of soil treatment, it is usually 10 to 100,000 g / ha, preferably 200 to 20,000 g / ha. In the case of seed treatment, it is usually 0.01 to 100 g / Kg seed, preferably 0.02 to 20 g / Kg seed.
  • the compound of the present invention is generally applied for the application of various preparations or dilutions thereof, that is, spraying (for example, spraying, spraying, misting, atomizing, dusting, water surface application, etc.), soil It can be carried out by application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.) and the like. It can also be applied by the so-called ultra-low concentration volume application method. In this method, it is possible to contain 100% of the active ingredient.
  • the compound of the present invention may contain other agricultural chemicals as necessary, such as fungicides, insecticides, acaricides, nematicides, soil insecticides, antiviral agents, attractants, herbicides, plant growth preparations, etc. Can be mixed and used together. In this case, a more excellent effect may be exhibited.
  • bactericide for example, anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil; Tria like 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazolo [1,5-a] pyrimidine Zolopyrimidine compounds; Pyridinamine compounds such as fluazinam; Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole), tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, a bactericide, for example, Anilinopyrimidine compounds such as mepanipyrim, pyrimethanil, cyprodinil
  • Insecticides acaricides, nematicides or soil pesticides in the above-mentioned other pesticides, that is, active ingredient compounds of pesticides (generic name; including some pending applications or Japan Plant Protection Association test code) ),
  • pesticides for example, Profenofos, dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiophos, prothiophos Fosthiazate, cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate ), Sulprofos, thiometon, bamidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl, pirimiphos-methyl Propapho
  • Microbial pesticides such as: avermectin, emamectin benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin ), Antibiotics such as emamectin, spinetoram and semi-synthetic antibiotics; natural products such as azadirachtin, rotenone; repellents such as deet; Mixed with , Can be used together.
  • the plant disease control agent according to the present invention can be suitably used in a method for controlling plant diseases applied to plants.
  • a plant disease control agent comprising a compound represented by the formula (I) or a salt thereof.
  • X 1 and X 2 are each independently alkylene which may be substituted with a halogen atom (methylene in the alkylene may be replaced with an oxygen atom or a sulfur atom), [a1] Plant disease control agent.
  • Both A 1 and A 2 are bonded to the para position with respect to X 1 and X 2 , X 1 and X 2 are both alkylenes replaced with oxygen atoms, and the oxygen atoms are both bonded to the benzene ring; Z is an imino substituted with phenyloxyalkyl substituted with amidino in the para position,
  • the plant disease control agent according to any one of the above [a1] to [a3].
  • Both A 1 and A 2 are bonded to the para position with respect to X 1 and X 2 , X 1 and X 2 are both alkylenes replaced with oxygen atoms, and the oxygen atoms are both bonded to the benzene ring;
  • Z is an optionally substituted imino;
  • At least one of R 1 and R 2 is selected from the group consisting of optionally substituted alkylthio, nitro, optionally substituted amino, optionally substituted alkylsulfinyl, and optionally substituted alkylsulfonyl;
  • the plant disease control agent according to any one of the above [a1] to [a3].
  • Both A 1 and A 2 are bonded to the para position with respect to X 1 and X 2 ,
  • One of X 1 and X 2 is an alkylene substituted with a sulfur atom, the other is an alkylene substituted with an oxygen atom or a sulfur atom, and both the sulfur atom and the oxygen atom are bonded to a benzene ring;
  • Z is a nitrogen-containing heterocyclic ring which may be substituted, and carbon atoms constituting the heterocyclic ring are bonded to X 1 and X 2 ;
  • a compound represented by the formula (I) or a salt thereof (1) (i) both A 1 and A 2 are bonded to the para position relative to X 1 and X 2 , and (a) both X 1 and X 2 are alkylenes replaced with oxygen atoms And the oxygen atom is bonded to the benzene ring, and Z may be substituted (the imino substituent is an optionally substituted alkyl (provided that the optionally substituted alkyl represents the above formula (B)).
  • X 1 and X 2 are a sulfur atom or an alkylene substituted with an optionally substituted imino, the other is an oxygen atom, a sulfur atom or optionally substituted Alkylene that replaced imino,
  • the sulfur atom, oxygen atom or optionally substituted imino is bonded to a benzene ring, and Z may be substituted (the imino substituent is substituted with an optionally substituted alkyl, cycloalkyl and alkylcarbonyl).
  • a 1 is bonded to X 1 in the para position, and one of X 1 and X 2 is a sulfur atom or an alkylene substituted with an optionally substituted imino, and the other is an oxygen atom, a sulfur atom or a substituted atom.
  • the carbon atom constituting the heterocycle is bonded to X 2 ; (3) A 1 is bonded to the para position with respect to X 1 , X 2 is alkylene, the alkylene is bonded to the benzene ring through a carbon atom, and Z may be substituted When it is a nitrogen-containing heterocycle, the carbon atom constituting the heterocycle is bonded to X 1 .
  • Compound or salt thereof When it is a nitrogen-containing heterocycle, the carbon atom constituting the heterocycle is bonded to X 1 .
  • X 1 and X 2 are each independently alkylene which may be substituted with a halogen atom (methylene in the alkylene may be replaced with an oxygen atom or a sulfur atom), provided that (1) (i) both A 1 and A 2 are bonded to the para position relative to X 1 and X 2 , and (a) both X 1 and X 2 are alkylenes replaced with oxygen atoms The oxygen atom is bonded to a benzene ring, or (b) one of X 1 and X 2 is an alkylene substituted with a sulfur atom, and the other is an alkylene substituted with an oxygen atom or a sulfur atom, And the oxygen atom is bonded to the benzene ring and Z is an optionally substituted imino, (ii) A 1 is bonded to X 1 in the para position, and one of X 1 and X 2 is an alkylene substituted with a sulfur atom, and the other is an alkylene substituted with an oxygen
  • the carbon atom constituting the heterocycle is bonded to X 2 ;
  • a nitrogen-containing complex in which A 1 is bonded to X 1 in the para position, X 2 is alkylene, the alkylene is bonded to the benzene ring through a carbon atom, and Z may be substituted. If it is ring compound or a salt thereof of the [b1] the carbon atoms constituting the heterocyclic ring is bonded to X 1.
  • Both A 1 and A 2 are bonded to the para position with respect to X 1 and X 2 , X 1 and X 2 are both alkylenes replaced with oxygen atoms, and the oxygen atoms are both bonded to the benzene ring;
  • Z is an imino substituted with phenyloxyalkyl substituted with amidino in the para position, Any of the compounds [b1] to [a3] or a salt thereof.
  • Both A 1 and A 2 are bonded to the para position with respect to X 1 and X 2 , X 1 and X 2 are both alkylenes replaced with oxygen atoms, and the oxygen atoms are both bonded to the benzene ring;
  • Z is an optionally substituted imino;
  • At least one of R 1 and R 2 is selected from the group consisting of optionally substituted alkylthio, nitro, optionally substituted amino, optionally substituted alkylsulfinyl, and optionally substituted alkylsulfonyl; Any of the compounds [b1] to [a3] or a salt thereof.
  • Both A 1 and A 2 are bonded to the para position with respect to X 1 and X 2 ,
  • One of X 1 and X 2 is an alkylene substituted with a sulfur atom, the other is an alkylene substituted with an oxygen atom or a sulfur atom, and both the sulfur atom and the oxygen atom are bonded to a benzene ring;
  • Z is a nitrogen-containing heterocyclic ring which may be substituted, and carbon atoms constituting the heterocyclic ring are bonded to X 1 and X 2 ;
  • Synthesis example 1 Synthesis of 4- ⁇ 4- [4- (4-amidinophenoxy) butylamino] butoxy ⁇ -3-nitrophenylcarboxamidine (Compound No. 2) (1) 4- (4-Bromobutoxy) -3-nitro Synthesis of benzonitrile A 40 mL N, N-dimethylformamide solution of 7.5 g of 4-hydroxy-3-nitrobenzonitrile and 6.66 g of potassium carbonate was stirred at room temperature for 30 minutes in a nitrogen atmosphere, and then 18.9 g of 1,4-dibromobutane. And reacted at 35-40 ° C. for 12 hours.
  • reaction solution was allowed to react for 12 hours while gradually returning to room temperature.
  • the mixture was acidified with 25% hydrochloric acid under ice-cooling, washed with ethyl acetate, the aqueous layer was made alkaline with 10% aqueous sodium hydroxide solution, and allowed to stand at room temperature.
  • the precipitate was dissolved in a solution of hydrogen chloride in ethanol (5.4 mol / l), and the solvent was concentrated under reduced pressure and then solidified to obtain 0.46 g of the desired product (hydrochloride) having a melting point of 208.0 ° C.
  • Synthesis example 2 Synthesis of 4- (3- ⁇ 4- [3- (4-amidinophenoxy) propyl] -1-piperidinyl ⁇ propoxy) -3-methylthiophenylcarboxamidine (Compound No. 8) (1) 4- (3- Synthesis of bromopropyloxy) -3-methylthiobenzonitrile After adding 1.93 g of potassium carbonate to 20 mL N, N-dimethylformamide solution of 2.1 g of 4-hydroxy-3-methylthiobenzonitrile and stirring for 30 minutes under nitrogen atmosphere, 6 g of 1,3-dibromopropane was added and stirred at 40 ° C. for 48 hours.
  • the reaction was continued for 12 hours while gradually returning the liquid temperature to room temperature.
  • the reaction solution was ice-cooled and acidified with 25% hydrochloric acid.
  • the aqueous layer was made alkaline with 10% aqueous sodium hydroxide under ice-cooling, and allowed to stand at room temperature, and the precipitated solid was collected by filtration.
  • a solution of hydrogen chloride in ethanol (5.4 mol / l) was added to the collected solid and stirred, and then the ethanol solution was concentrated to obtain 1.07 g of the desired product (melting point: 273.0 ° C.).
  • the reaction was continued for 12 hours while gradually returning the liquid temperature to room temperature.
  • the reaction solution was ice-cooled and acidified with 25% hydrochloric acid.
  • the aqueous layer was made alkaline with a 10% aqueous sodium hydroxide solution under ice cooling and allowed to stand at room temperature, and the precipitated solid was collected by filtration.
  • a solution of hydrogen chloride in ethanol (5.4 mol / l) was added to the collected solid and stirred, and then the ethanol solution was concentrated to obtain 0.4 g of a yellow amorphous solid target product.
  • Leprosy spot area, number of lesions or spore formation area is less than 10% of untreated area.
  • Leprosy spot area, number of lesions or spore formation area is less than 40% of the untreated area.
  • Leprosy spot area, number of lesions or spore formation area is less than 70% of untreated area.
  • the area of gonorrhea, the number of lesions or the area of spore formation is 70% or more of the untreated area.
  • Germination rate or germ tube elongation is less than 20% in the untreated area.
  • Germination rate or germ tube elongation is less than 40% in the untreated area.
  • the bud germination rate or germ tube elongation is less than 70% of the untreated area.
  • Germination rate or germ tube elongation is 70% or more of the untreated area.
  • Test example 1 (wheat blight prevention effect test) Wheat (variety: Norin 61) was cultivated in a plastic pot with a diameter of 7.5 cm, and when the 1.5 leaf stage was reached, a sufficient amount of a chemical solution prepared by adjusting the compound of the present invention to a predetermined concentration was sprayed with a spray gun. . After the drug solution is dried (on the day of treatment), a conidial spore suspension of a blight fungus (Septoria nodorum) is spray-inoculated and kept in an inoculation box at 20 ° C for about 1 day, and then kept in a constant temperature room at 20 ° C. . The number of lesions was investigated 8 to 13 days after the inoculation, and the control index was determined according to the evaluation criteria.
  • Test Example 2 Cucumber downy mildew prevention effect test
  • Cucumber (variety: Sagamihanjiro) was cultivated in a plastic pot with a diameter of 7.5 cm, and when the 1.5 leaf stage was reached, a sufficient amount of chemical solution adjusted to a predetermined concentration of the compound of the present invention was sprayed with a spray gun. .
  • a zoosporangium suspension of downy mildew (Pseudoperonospora cubensis) was spray-inoculated and kept in a constant temperature room at 20 ° C. The lesion area was examined 5 to 6 days after the inoculation, and the control index was determined according to the evaluation criteria.
  • Test Example 3 (Test for preventing bean gray mold disease) Green beans (variety: Taishokin) were cultivated in a plastic pot with a diameter of 12 cm, and when the 3 to 4 leaf stage was reached, a sufficient amount of a chemical solution of the present compound adjusted to a predetermined concentration was sprayed with a spray gun. After the chemical solution was dried (on the day of treatment or the next day), a conidial spore suspension of Botrytis cinerea was soaked in a paper disk having a diameter of 8 mm, inoculated on the floor, and kept in a constant temperature room at 20 ° C. Three days after the inoculation, the lesion area was examined, and the control index was determined according to the evaluation criteria.
  • Test Example 4 Tomato ring mold fungus spore germination inhibition test
  • a conidial spore suspension of Alternaria solani to which a chemical compound of the present invention was added to a predetermined concentration in a 96-well microplate was dispensed and kept in a constant temperature room at 20 ° C.
  • One day after the culture the degree of spore germination and germ tube elongation was examined with a microscope, and a control index was determined according to the above evaluation criteria.
  • Test Example 5 (Swheat mold fungus spores germination inhibition test) A conidial spore suspension of Fusarium graminearum to which a compound of the present invention was added to a predetermined concentration in a 96-well microplate was dispensed and kept in a constant temperature room at 20 ° C. One day after the culture, the degree of spore germination and germ tube elongation was examined with a microscope, and a control index was determined according to the above evaluation criteria.
  • Test Example 6 (Action characteristic test) (Rain resistance) Cucumber (variety: Sagamihanjiro) is cultivated in a plastic pot with a diameter of 7.5 cm, and when the 1.5 leaf stage is reached, a sufficient amount of medicinal solution prepared by adjusting the concentration of the compound of the present invention to a predetermined concentration is obtained with a spray gun. Processed. After the chemical solution was dried, 10 mm / hr of rain was treated with a rain apparatus for 1 hour, and a conidial spore suspension of cucumber gray mold (Botrytis cinerea) was inoculated. After inoculation, it was kept in a constant temperature room at 20 ° C. Three days after the inoculation, the lesion area was examined and the rain resistance of the compound of the present invention was evaluated.
  • Cucumber (variety: Sagamihanjiro) is cultivated in a 7.5 cm diameter plastic pot, and when the 1.5 leaf stage is reached, a sufficient amount of the medicinal solution prepared by adjusting the compound of the present invention to a predetermined concentration is treated with cucumber cotyledons, The specimen was left in the greenhouse for 1 week. Thereafter, a conidial spore suspension of Botrytis cinerea was inoculated and kept in a constant temperature room at 20 ° C. Three days after the inoculation, the lesion area was examined to evaluate the residual effect of the drug.
  • Formulation Example 1 Compound of the present invention 20 parts by weight (2) 72 parts by weight of clay (3) Sodium lignin sulfonate 8 parts by weight The above is uniformly mixed to obtain a wettable powder.
  • Formulation Example 2 (1) Compound of the present invention 5 parts by weight (2) 95 parts by weight of talc The above components are uniformly mixed to form a powder.
  • Formulation Example 3 (1) 20 parts by weight of the compound of the present invention (2) 20 parts by weight of N, N-dimethylacetamide (3) 10 parts by weight of polyoxyethylene alkylphenyl ether (4) 50 parts by weight of xylene To make an emulsion.
  • Formulation Example 4 (1) Clay 68 parts by weight (2) Lignin sulfonic acid soda 2 parts by weight (3) Polyoxyethylene alkylaryl ether sulfate 5 parts by weight (4) Fine silica 25 parts by weight Are mixed at a weight ratio of 4: 1 to obtain a wettable powder.
  • Formulation Example 5 (1) Compound of the present invention 50 parts by weight (2) Oxidated polyalkylphenyl phosphate triethanolamine 2 parts by weight (3) Silicone 0.2 parts by weight (4) Water 47.8 parts by weight (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are further added to the mixed and crushed stock solution, and the mixture is uniformly mixed, granulated and dried to obtain a granulated wettable powder.
  • Formulation Example 6 (1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene phosphate ester 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1) to (3) is mixed uniformly in advance and diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove acetone and form granules.
  • Formulation Example 7 (1) 2.5 parts by weight of the compound of the present invention (2) 2.5 parts by weight of N-methyl-2-pyrrolidone (3) 95.0 parts by weight of soybean oil (Ultra low volume formulation).
  • Formulation Example 8 (1) Compound of the present invention 20 parts by weight (2) Oxidated polyalkylphenyl phosphate triethanolamine 2 parts by weight (3) Silicone 0.2 parts by weight (4) Xanthan gum 0.1 part by weight (5) Ethylene glycol 5 Part by weight (6) Water 72.7 parts by weight The above is uniformly mixed and pulverized to obtain an aqueous suspension.
  • the plant disease control agent of the present invention has a high control effect against a wide range of plant pathogens and also has high safety. Furthermore, the plant disease control agent of the present invention has a so-called residual effect that maintains the plant disease control effect for a long time after spraying the drug, and also exhibits an excellent effect even when the crop is subjected to rainfall after spraying the drug. Yes, it has excellent so-called rain resistance. Since the plant disease control agent of the present invention has useful properties as such a plant disease control agent, the number of times the drug is used or the amount used is increased in consideration of rainfall after the spraying of the drug and the duration of the control effect. It is not necessary and can protect crops from plant diseases at lower cost and less effort.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrrole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention propose un agent de lutte contre des maladies de plantes qui, indépendamment de là où il est employé, lutte efficacement contre une large gamme d'agents pathogènes des plantes. Cet agent de lutte contre des maladies de plantes contient, comme composant actif, un composé représenté par la formule (I) ou un sel de celui-ci [dans la formule, A1 et A2 représentent indépendamment des amidinos qui peuvent être protégés ; X1 et X2 représentent indépendamment des alkylènes substituables par des atomes d'halogène (des méthylènes parmi les alkylènes peuvent être remplacés par un atome d'oxygène, un atome de soufre ou un imino facultativement substitué) ; Z représente un imino substituable ou un cycle hétérocyclique substituable contenant de l'azote ; R1 et R2 représentent indépendamment un atome d'halogène, un alkyle substituable, un cycloalkyle substituable, un alcoxy substituable, un alkylthio substituable, nitro, un amino substituable, alkylsulfinyle substituable ou un alkylsulfonyle substituable ; et l et m sont indépendamment des entiers entre 0 et 4].
PCT/JP2012/077536 2011-10-28 2012-10-25 Agent de lutte contre des maladies de plantes contenant un dérivé arylamidine ou un sel de celui-ci WO2013062024A1 (fr)

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Cited By (5)

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Publication number Priority date Publication date Assignee Title
WO2015087857A1 (fr) * 2013-12-10 2015-06-18 日本曹達株式会社 Composé d'arylamidine et agent bactéricide
WO2016047550A1 (fr) * 2014-09-24 2016-03-31 日本曹達株式会社 Fongicide agricole et horticole contenant un composé d'arylamidine
WO2016195077A1 (fr) * 2015-06-03 2016-12-08 日本曹達株式会社 Composé guanidine et bactéricide
JP2016222655A (ja) * 2015-06-03 2016-12-28 日本曹達株式会社 アミジン化合物および殺菌剤
WO2018097126A1 (fr) * 2016-11-25 2018-05-31 日本曹達株式会社 Composé guanidine, et bactéricide

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JP2002543163A (ja) * 1999-04-30 2002-12-17 スリル バイオメディカル コーポレイション 癌および前立腺疾患のための治療としての結合体
WO2003074476A1 (fr) * 2002-03-06 2003-09-12 Toyama Chemical Co., Ltd. Nouveau derive d'arylamidine ou sel de celui-ci
JP2005097298A (ja) * 2003-09-05 2005-04-14 Toyama Chem Co Ltd 新規なアリールアミジン誘導体またはその塩

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JP2002543163A (ja) * 1999-04-30 2002-12-17 スリル バイオメディカル コーポレイション 癌および前立腺疾患のための治療としての結合体
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Cited By (8)

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Publication number Priority date Publication date Assignee Title
WO2015087857A1 (fr) * 2013-12-10 2015-06-18 日本曹達株式会社 Composé d'arylamidine et agent bactéricide
JPWO2015087857A1 (ja) * 2013-12-10 2017-03-16 日本曹達株式会社 アリールアミジン化合物および殺菌剤
WO2016047550A1 (fr) * 2014-09-24 2016-03-31 日本曹達株式会社 Fongicide agricole et horticole contenant un composé d'arylamidine
WO2016195077A1 (fr) * 2015-06-03 2016-12-08 日本曹達株式会社 Composé guanidine et bactéricide
JP2016222655A (ja) * 2015-06-03 2016-12-28 日本曹達株式会社 アミジン化合物および殺菌剤
TWI632127B (zh) * 2015-06-03 2018-08-11 日本曹達股份有限公司 胍化合物及殺菌劑
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WO2018097126A1 (fr) * 2016-11-25 2018-05-31 日本曹達株式会社 Composé guanidine, et bactéricide

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