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WO2010032886A1 - Composition agricole luttant contre ou prévenant une maladie des plantes causée par une bactérie pathogène des végétaux - Google Patents

Composition agricole luttant contre ou prévenant une maladie des plantes causée par une bactérie pathogène des végétaux Download PDF

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Publication number
WO2010032886A1
WO2010032886A1 PCT/JP2009/067191 JP2009067191W WO2010032886A1 WO 2010032886 A1 WO2010032886 A1 WO 2010032886A1 JP 2009067191 W JP2009067191 W JP 2009067191W WO 2010032886 A1 WO2010032886 A1 WO 2010032886A1
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group
alkyl
substituent
phenyl
alkylamino
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Japanese (ja)
Inventor
久保田真由美
真鍋明夫
松崎雄一
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • the present invention relates to an agricultural composition for controlling or preventing plant diseases caused by plant pathogens, a method for controlling or preventing plant diseases caused by plant pathogens, and the like.
  • the present invention provides an agricultural composition for controlling or preventing plant diseases caused by plant pathogens having excellent efficacy. That is, the present invention includes the following.
  • [1] For controlling or preventing plant diseases caused by plant pathogens, Formula (1) [Where, A is the following A 1 , A 2 or A 3 (Wherein p represents any integer from 0 to 6, q represents any integer from 0 to 5, r represents any integer from 0 to 4; R 1 represents a halogen atom, a C1-C4 alkyl group or a cyano group, R 2 represents a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group or a cyano group, R 3 represents a halogen atom, a C1-C4 alkyl group, a C1-C4 alkoxy group or a cyano group.
  • each R 1 is the same or different from each other, and when q is an integer from 2 to 5, each R 2 is the same or different from each other, and r is When R is an integer from 2 to 4, each R 3 is the same as or different from each other.
  • n represents any integer from 1 to 4
  • E represents a furyl group, a thienyl group, a pyrrolyl group, a tetrazolyl group, a thiazolyl group, a pyrazolyl group or a phenyl group; Any group represented by E may have at least one group listed in the following substituent group a-1 and substituent group a-2.
  • [Substituent group a-1] ⁇ Halogen atom, amino group, hydroxyl group, mercapto group, cyano group, formyl group, carboxyl group, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl Group, 5-10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group, C3-8 cycloalkylidene C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, C6-10 aryl C2-6 Alkenyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, 5 -10 membered heterocyclic oxy group, C3-8 cycloalkyl C1-6
  • E represents a furyl group having at least one group listed in the substituent group a-1 and the substituent group a-2, the substituent group a-1 and the substituent group a.
  • the agricultural composition according to [1] which is a phenyl group having at least one group listed in the substituent group a-2.
  • E represents a furyl group having at least one group listed in the substituent group a-3 and the substituent group a-4, the substituent group a-3, and the substituent group a.
  • a thienyl group having at least one group listed in -4, a-3 and a pyrrolyl group having at least one group listed in substituent group a-4, or a substituent group a-3 and substituent group The agricultural composition according to [1], which is a phenyl group having at least one group listed in a-4.
  • [Substituent group a-3] ⁇ Halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 member Heterocyclic group, C 3-8 cycloalkyl C 1-6 alkyl group, C 3-8 cycloalkylidene C 1-6 alkyl group, C 6-10 aryl C 1-6 alkyl group, 5-10 membered heterocyclic C 1-6 alkyl group, C 1 -8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, C3-8 cycloalkyl C1-6 alkoxy group, 5-10 membered heterocycle C1-6 alkoxy group, C1-8 alkylthio group, C2
  • [Substituent group b-2] ⁇ Hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C1-6 alkyl group, C3-8 cycloalkyl group, 5-10 membered heterocyclic group, C1-6 alkoxy group, C6 -10 aryloxy group, 5-10 membered heterocyclic oxy group, C1-6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, trifluoromethyl group, trifluoromethoxy group, mono-C1-6 alkylamino group, di- C1-6 alkylamino group, mono-C6-10 arylamino group which may have one amino group or aminosulfonyl group and N-C6-10 arylC1- which may have one amino group 6 alkyl-N-C1-6 alkylamino group ⁇ [4]
  • E may have one or two substituents listed in the substituent group e-1 and
  • E represents a furyl group optionally having 1 or 2 substituents listed in the substituent group g-1 and the substituent group g-2, a substituent group g- 1 and the thienyl group which may have one or two substituents listed in the substituent group g-2, the substituents listed in the substituent group g-1 and the substituent group g-2 are 1 or [1]
  • the pyrrolyl group which may have
  • E is a phenyl group which may have one or two substituents listed in the substituent group g-1 and the substituent group g-2 [5] Agricultural composition.
  • E is a furyl group having at least one group listed in the substituent group i-1, and a thienyl group having at least one group listed in the substituent group i-1.
  • Agricultural group according to [1] which is a pyrrolyl group having at least one group listed in the substituent group i-1 or a phenyl group having at least one group listed in the substituent group i-1 Composition.
  • [Substituent group i-1] ⁇ Halogen atom, C1-8 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C6-10 aryloxy group, C6-10 aryl C1-6 alkoxy group and (C1- C2 alkoxy) C2-C5 alkoxy group ⁇
  • E is a phenyl group having at least one group listed in the substituent group i-1.
  • E is a furyl group having at least one group listed in the substituent group j-1, and a thienyl group having at least one group listed in the substituent group j-1.
  • [Substituent group j-1] ⁇ Halogen atom, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group and (C1-C2 alkoxy) C2-C5 alkoxy group ⁇ [10]
  • E is a phenyl group having at least one group listed in the substituent group j-1.
  • A is A1.
  • A is A 3 [1] ⁇ agricultural composition according to any one of [10].
  • p is an integer from 0 to 6, and the case where p is 0 is preferable.
  • q is an integer from 0 to 5, and a case where q is 0 is preferable.
  • r is an integer from 0 to 4, and a case where r is 0 is preferable.
  • n is an integer of 1 to 4, and a case where n is 1 or 2 is preferable.
  • R 1 , R 2 And R 3 examples of the halogen atom represented by: include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom,
  • Examples of the C1-C4 alkyl group include a methyl group, an ethyl group, a 1-methylethyl group, a 1,1-dimethylethyl group, a propyl group, and a 1-methylpropyl group.
  • R 2 And R 3 As the C1-C4 alkoxy group represented by methoxy group, ethoxy group, 1-methylethoxy group, 1,1-dimethylethoxy group, propoxy group, 1-methylpropoxy group, 2-methylpropoxy group, butoxy group and the like Named R 1 , R 2 And R 3 As the group represented by the formula, a fluorine atom can be preferably exemplified.
  • E in the formula (1) is a furyl group, a substituent group a-1 and a substituent which may have at least one group listed in the substituent group a-1 and the substituent group a-2.
  • a thienyl group optionally having at least one group enumerated in group a-2, at least one group enumerated in substituent group a-1 and substituent group a-2;
  • a thiazolyl group optionally having at least one group listed in the above, a pyrazolyl group optionally having at least one group listed in the substituent group a-1 and the substituent group a-2 Or at least one group listed in the substituent group a-1 and the substituent group a-2.
  • phenyl group optionally having at least one group enumerated in group a-2, at least one group enumerated in substituent group a-1 and substituent group a-2;
  • [Substituent group a-1] ⁇ Halogen atom, amino group, hydroxyl group, mercapto group, cyano group, formyl group, carboxyl group, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl Group, 5-10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group, C3-8 cycloalkylidene C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, C6-10 aryl C2-6 Alkenyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, 5 -10 membered heterocyclic oxy group, C3-8 cycloalkyl C1-6
  • Preferred examples of E include
  • a thienyl group having at least one group listed in 2 a pyrrolyl group having at least one group listed in the substituent group a-1 and the substituent group a-2, or the substituent group a- And phenyl group having at least one group listed in 1 and the substituent group a-2.
  • preferred E may have 1 or 2 groups listed in the substituent group (1) (preferably, may be optionally substituted) 2-furyl group, substituted A 2-thienyl group which may have 1 or 2 groups listed in the group (1) (preferably may be substituted by 1), and a group listed in the substituent group (1)
  • phenyl C1-6 alkoxy group (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, a phenoxy group, a 5-6 membered heterocyclic oxy group and a C1-6 alkyl group)
  • phenyl C1-6 alkoxy group (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, 5-6 membered heterocyclic oxy group and C1 5-6 membered heterocyclic C1-6 alkoxy group (which may have 1 to 3 groups selected from the group consisting of 6 alkyl groups), (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy)
  • a phenoxy C1-6 alkyl group (which may have 1 to 3 groups selected from the group consisting of a group, a phenoxy group and a 5-6 membered heterocyclic oxy group), and a (halogen atom, C3-5 cyclo) 5-6 member
  • a phenoxy C1-6 alkyl group (which may have 1 to 3 groups selected from the group consisting of a phenoxy group and a 5-6 membered heterocyclic oxy group), and a (halogen atom, C3-5 cycloalkyl) 5-6 membered heterocyclic oxy C1-6 alkyl group which may have 1 to 3 groups selected from the group consisting of a group and a C1-6 alkoxy group ⁇ [Substituent group (3)] ⁇ (C1-6 alkyl optionally having 1 to 3 halogen atoms, C3-5
  • Phenyl C1-6 alkyl group (having 1 to 3 halogen atoms, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, 5-6 membered heterocyclic oxy group, C1-6 alkyl group) 5-6 membered heterocyclic C1-6 alkyl group, (halogen atom, C3-5 cycloalkyl group, C1-6 alkoxy group, phenoxy group, 5-6 membered heterocyclic oxy group) A phenoxy C1-6 alkyl group (which may have 1 to 3) or a 5-6 membered heterocycle (which may have 1 to 3 halogen atoms, a C3-5 cycloalkyl group or a C1-6 alkoxy group) Oxy C1-6 alkyl group ⁇
  • E is a furyl group having at least one group listed in the substituent group a-3 and the substituent group a-4, a substituent group a-3 and a substituent group a-4.
  • [Substituent group a-3] ⁇ Halogen atom, hydroxyl group, mercapto group, cyano group, carboxyl group, C1-8 alkyl group, C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 member Heterocyclic group, C 3-8 cycloalkyl C 1-6 alkyl group, C 3-8 cycloalkylidene C 1-6 alkyl group, C 6-10 aryl C 1-6 alkyl group, 5-10 membered heterocyclic C 1-6 alkyl group, C 1 -8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy group, C3-8 cycloalkyl C1-6 alkoxy group, 5-10 membered heterocycle C1-6 alkoxy group, C1-8 alkylthio group, C2
  • C6-10 aryloxy C1-6 alkyl group and 5-10 membered heterocyclic oxy C1-6 alkyl group ⁇ [Substituent group a-4] ⁇ C2-8 alkenyl group, C2-8 alkynyl group, C3-8 cycloalkyl group, C6-10 aryl group, 5-10 membered heterocyclic group, C3-8 cycloalkyl C1-6 alkyl group, C6-10 aryl C1-6 alkyl group, 5-10 membered heterocyclic C1-6 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C3-8 cycloalkoxy group, C6-10 aryloxy Group, C3-8 cycloalkyl C1-6 alkoxy group, C6-10 aryl C1-6 alkoxy group, 5-10 membered heterocyclic C1-6 alkoxy group, C1-8 alkylthio group, C2-8 alkenylthio group, C2- 8
  • [Substituent group b-2] ⁇ Hydroxyl group, mercapto group, cyano group, carboxyl group, amino group, carbamoyl group, nitro group, C1-6 alkyl group, C3-8 cycloalkyl group, 5-10 membered heterocyclic group, C1-6 alkoxy group, C6 -10 aryloxy group, 5-10 membered heterocyclic oxy group, C1-6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, trifluoromethyl group, trifluoromethoxy group, mono-C1-6 alkylamino group, di- C1-6 alkylamino group, mono-C6-10 arylamino group which may have one amino group or aminosulfonyl group and N-C6-10 arylC1- which may have one amino group 6 alkyl-N-C1-6 alkylamino group ⁇
  • E is a furyl group which may have one or two substituents listed in the substituent group
  • -2 may have one or two substituents listed in the group -2 may have one or two substituents listed in the substituent group e-1 and the substituent group e-2.
  • Examples include a pyrrolyl group or a phenyl group that may have one or two substituents listed in the substituent group e-1 and the substituent group e-2.
  • [Substituent group f] ⁇ Halogen atom, hydroxyl group, cyano group, amino group, nitro group, C3-8 cycloalkyl group, C1-6 alkoxy group, C1-6 alkylthio group, C6-10 aryloxy group, 5-10 membered heterocyclic oxy group, C1-6 alkoxycarbonyl group, C1-6 alkylsulfonyl group, mono-C6-10 arylamino group, trifluoromethyl group, trifluoromethoxy group and C1-6 alkyl group ⁇
  • E is a furyl group optionally having one or two substituents listed in the substituent group g-1 and the substituent group g-2, the substituent group g-1 and the substituent group.
  • It has one or two thienyl groups which may have one or two substituents listed in g-2, one or two substituents listed in substituent group g-1 and substituent group g-2.
  • An pyrrolyl group which may be substituted, or a phenyl group which may have one or two substituents listed in the substituent group g-1 and the substituent group g-2 can be exemplified.
  • E is a furyl group having at least one group listed in the substituent group i-1, a thienyl group having at least one group listed in the substituent group i-1, and a substituent.
  • a pyrrolyl group having at least one group listed in group i-1 or a phenyl group having at least one group listed in substituent group i-1 can be mentioned.
  • [Substituent group i-1] ⁇ Halogen atom, C1-8 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C6-10 aryloxy group, C6-10 aryl C1-6 alkoxy group and (C1- C2 alkoxy) C2-C5 alkoxy group ⁇
  • E is a furyl group having at least one group listed in the substituent group j-1, a thienyl group having at least one group listed in the substituent group j-1, and a substituent.
  • pyrrolyl groups having at least one group listed in group j-1 or phenyl groups having at least one group listed in j-1.
  • [Substituent group j-1] ⁇ Halogen atom, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group and (C1-C2 alkoxy) C2-C5 alkoxy group ⁇
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and the like
  • examples of the C1-8 alkyl group include a methyl group, an ethyl group, an n-propyl group, and an iso-propyl group.
  • N-butyl group iso-butyl group, n-pentyl group, iso-pentyl group, n-hexyl group, 4-methylpentyl group, 3-methylpentyl group and the like.
  • Is vinyl group, allyl group, 2-butenyl group, 3-butenyl group, 2-pentenyl group, 3-pentenyl group, prenyl group, 3-methyl-3-butenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 4-methyl-4-pentenyl group, 4-methyl-3-pentenyl group and the like can be mentioned.
  • C2-8 alkynyl group examples include ethynyl group, propyl group, and the like. Pargyl group, 2-butynyl group, 3-butynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 2-hexynyl group, 3-hexynyl group, 4-hexynyl group, 5-hexynyl group, etc.
  • Examples of the C3-8 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like.
  • a C6-10 aryl group includes a phenyl group.
  • Indenyl group, naphthyl group and the like, and examples of the 5- to 10-membered heterocyclic group include a furyl group, a thienyl group, a thiazolyl group, a pyrazolyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, and a benzofuranyl group.
  • Examples of the C3-8 cycloalkyl C1-6 alkyl group include a cyclopropylmethyl group, a cyclopropylethyl group, a cyclopropylpropyl group, a cyclopropylbutyl group, and a cyclopropyl group.
  • Pentyl group cyclopropylhexyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclobutylpropyl group, cyclobutylbutyl group, cyclobutylpentyl group, cyclopentylethyl group, cyclopentylpropyl group, cyclopentylbutyl group, cyclohexylethyl group, cyclohexyl A propyl group etc.
  • a C3-8 cycloalkylidene C1-6 alkyl group a cyclopropylidenemethyl group, a cyclopropylideneethyl group, a cyclopropylidenepropyl group, cyclo Propylidenebutyl group, cyclopropylidenepentyl group, cyclopropylidenehexyl group, cyclobutylidenemethyl group, cyclobutylideneethyl group, cyclobutylidenepropyl group, cyclobutylidenebutyl group, cyclobutylidenepentyl group, cyclopentylidene Examples thereof include an ethyl group, a cyclopentylidenepropyl group, a cyclopentylidenebutyl group, a cyclohexylideneethyl group, a cyclohexylidenepropyl
  • the 0-membered heterocyclic C1-6 alkyl group includes a furylmethyl group, a furylethyl group, a furylpropyl group, a furylbutyl group, a furylpentyl group, a furylhexyl group, a thienylmethyl group, a thienylethyl group, a thienylpropyl group, and a thienylbutyl group.
  • Examples of the C3-8 alkenyloxy group include a Ruoxy group, 1-methyl-2-propenyloxy group, 2-butenyloxy group, 3-butenyloxy group, 2-pentenyloxy group, 3-pentenyloxy group, prenyloxy group, 3-methyl-3-butenyloxy group, 2- A hexenyloxy group, a 3-hexenyloxy group, a 4-hexenyloxy group, a 4-methyl-4-pentenyloxy group, a 4-methyl-3-pentenyloxy group, and the like can be given.
  • Examples of the C3-8 alkynyloxy group include , Propargyloxy group, 2-butynyloxy group, 3-butynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, 2-hexynyloxy group, 3-hexynyloxy group, 4-hexynyloxy group , 5-hexynyloxy group and the like, and C3-8 cycloalco
  • Examples of the xy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy group, and the like
  • examples of the C6-10 aryloxy group include a phenoxy group.
  • C3-8 cycloalkyl C1-6 alkoxy group a cyclopropylmethoxy group, a cyclopropylethoxy group, a cyclopropylpropoxy group, a cyclopropylbutoxy group, a cyclopropylpentyloxy group, a cyclopropyl group, Propylhexyloxy group, cyclobutylmethoxy group, cyclobutylethoxy group, cyclobutylpropoxy group, cyclobutylbutoxy group, cyclobutylpentyloxy group, cyclopentylethoxy group, cyclopentylpropoxy group, A clopentyl butoxy group, a cyclohexyl ethoxy group, a cyclohexyl propoxy group, etc.
  • a C6-10 aryl C1-6 alkoxy group a benzyloxy group, a phenethyloxy group, a phenylpropyloxy group, a phenylbutyloxy group, a phenyl
  • Examples include pentyloxy group, 2-methyl-4-phenylbutyloxy group, 2-methyl-5-phenylpentyloxy group, 3-methyl-5-phenylpentyloxy group, (2-naphthyl) ethyloxy group, and the like.
  • a 5-10 membered heterocyclic C1-6 alkoxy group includes a furylmethoxy group, a furylethoxy group, a furylpropyloxy group, a furylbutyloxy group, a furylpentyloxy group, a furylhexyloxy group, a thienylmethoxy group, a thienylethoxy group , Thienylp A pyroxy group, a thienylbutyloxy group, a thienylpentyloxy group, a thienylhexyloxy group, and the like can be given.
  • allylthio group 1-methyl-2-propenylthio group, 2-butenylthio group, 3-butenylthio group, 2-pentenylthio group, 3-pentenylthio group, prenylthio group, 3-methyl-3-butenylthio group, 2 -Hexenylthio group, 3-hexenylthio group, 4-hexenylthio group Group, 4-methyl-4-pentenylthio group, 4-methyl-3-pentenylthio group and the like, and as C2-8 alkynylthio group, propargylthio group, 2-butynylthio group, 3-butynylthio group , 2-pentynylthio group, 3-pentynylthio group, 4-pentynylthio group, 2-hexynylthio group, 3-hexynylthio group, 4-hexynylthio group, 5-hexynylthio group
  • Examples of the C6-10 arylthio group include a phenylthio group, a naphthylthio group, and the like.
  • C3-8 cycloalkyl C1-6a As the thio group, cyclopropylmethylthio group, cyclopropylethylthio group, cyclopropylpropylthio group, cyclopropylbutylthio group, cyclopropylpentylthio group, cyclopropylhexylthio group, cyclobutylmethylthio group, cyclobutylethylthio group , Cyclobutylpropylthio group, cyclobutylbutylthio group, cyclobutylpentylthio group, cyclopentylethylthio group, cyclopentylpropylthio group, cyclopentylbutylthio group, cyclohexylethylthio group,
  • C6-10 aryl C1-6 alkylthio groups include benzylthio group, phenethylthio group, phenylpropylthio group, phenylbutylthio group, phenylpentylthio group, 2-methyl-4-phenyl group, And nylbutylthio group, 2-methyl-5-phenylpentylthio group, 3-methyl-5-phenylpentylthio group, and the like.
  • Examples of the 5-10 membered heterocyclic C1-6 alkylthio group include a furylmethylthio group and furyl.
  • n-pentylamino group iso-pentylamino group, n -Hexylamino group, 4-methylpentylamino group, 3-methylpentylamino group and the like can be mentioned.
  • mono-C2-6 alkenylamino group allylamino group, 2-butenylamino group, 3-butenylamino group, 2 -Pentenylamino group, 3-pentenylamino group, prenylamino group, 3-methyl-3-butenylamino group, 2-hexenylamino group, 3-hexenylamino group, 4-hexenylamino group, 4-methyl-4-pentenylamino Group, 4-methyl-3-pentenylamino group and the like.
  • mono-C2-6 alkynylamino group propargylamino group, 2-butynylamino group, 3-butynylamino group, 2-pentynylamino group , 3-pentynylamino group, 4-pentynylamino group, 2-hexynylamino group, -Hexynylamino group, 4-hexynylamino group, 5-hexynylamino group and the like, and as mono-C3-8 cycloalkylamino group, cyclopropylamino group, cyclobutylamino group, cyclopentylamino group, cyclohexylamino group, A cycloheptylamino group, a cyclooctylamino group, etc.
  • Mono-C3-8 cycloalkyl C1- 6 Alkylamino groups include cyclopropylmethylamino, cyclopropylethylamino, cyclopropylpropylamino, cyclopropylbutylamino, cyclopropylpentylamino, cyclopropylhexylamino, cyclobutylmethylamino Group, cyclobutylethylamino group, cyclobutylpropylamino group, cyclobutylbutylamino group, cyclobutylpentylamino group, cyclopentylethylamino group, cyclopentylpropylamino group, cyclopentylbutylamino group, cyclohexylethyla
  • the ring C1-6 alkylamino group examples include a furylmethylamino group, a furylethylamino group, a furylpropylamino group, a furylbutylamino group, a furylpentylamino group, a furylhexylamide group, a thienylethylamino group, a thienylmethylamino group, Thienylpropyla Mino group, thienylbutylamino group, thienylpentylamino group, thienylhexylamino group and the like.
  • Examples of the di-C1-6 alkylamino group include dimethylamino group, methylethylamino group, diethylamino group, methylpropylamino group.
  • a N-C2-6 alkenyl-N-C1-6 alkylamino group includes an N-allyl-N-methylamino group and N- (2-butenyl) -N.
  • -Methylamino group, N- (3-butenyl) -N-methylamino group and the like can be mentioned, and N-C2-6 alkynyl-N-C1-6 alkylamino group includes N-methyl-N-propargyl.
  • N-C3-8 cycloalkyl-N-C1-6 alkylamino group includes N-cyclopropyl-N-methylamino group, N-cyclobutyl-N-methylamino group, N-cyclopentyl-N-methylamino group, etc.
  • Examples of the N-C6-10 aryl-N-C1-6 alkylamino group include an N-methylanilino group, and the like includes an N-C3-8 cycloalkyl C1-6 alkyl-N-C1.
  • N-cyclopropylmethyl-N-methylamino group N-cyclopropylethyl-N-methylamino group, N-cyclopropylpropyl-N-methylamino group, N-cyclobutylmethyl- N-methylamino group, N-cyclobutylethyl-N-methylamino group, N-cyclobutylpropyl-N-methylamino group, etc.
  • N-C6-10 aryl C1-6 alkyl-N-C1-6 alkylamino group includes N-benzyl-N-methylamino group, N-phenethyl-N-methylamino group, N-phenylpropoxy group.
  • -C1-6 alkylamino group includes N-furylmethyl-N-methylamino group, N-furylethyl-N-methylamino group, N-furylpropyl-N-methylamino group, N-furylbutyl-N-methyl Amino group, N-furylpentyl-N-methylamino group, N-thienyl-N-methylamino group, N-thienylethyl-N-methylamino group, N-thieni Examples include a rupropyl-N-methylamino group, an N-thienylbutyl-N-methylamino group, an N-thienylpentyl-N-methylamino group, and the C1-6 alkylcarbonyl group
  • n-propylcarbonyl group iso-propylcarbonyl group, n-butylcarbonyl group, iso-butylcarbonyl group, sec-butylcarbonyl group, n-pentylcarbonyl group, iso-pentylcarbonyl group, sec-pentylcarbonyl group, An n-hexylcarbonyl group, an iso-hexylcarbonyl group, a sec-hexylcarbonyl group, and the like can be mentioned.
  • Examples of the C1-6 alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propyloxycarbonyl group, an iso- Propoxy Rubonyl group, n-butoxycarbonyl group, iso-butoxycarbonyl group, sec-butoxycarbonyl group, n-pentyloxycarbonyl group, iso-pentyloxycarbonyl group, sec-pentyloxycarbonyl group, n-hexyloxycarbonyl group, iso -Hexyloxycarbonyl group, sec-hexyloxycarbonyl group and the like can be mentioned, and as C1-6 alkylsulfonyl group, methanesulfonyl group, ethanesulfonyl group, propanesulfonyl group, butanesulfonyl group, pentanesulfonyl group, hexanesulfonyl A group of formula -
  • Examples thereof include benzyloxymethyl group, benzyloxyethyl group, benzyloxypropyl group, benzyloxybutyl group, benzyloxypentyl group, (2-naphthyl) oxymethyl group and the like.
  • C1-6 alkyl groups include furyloxymethyl, furyloxyethyl, furyloxypropyl, furyloxybutyl, furyloxypentyl, thienyloxymethyl, thienyloxyethyl, thienyloxypropyl, thienyloxy Butyl group, Thieni An oxypentyl group, a pyridyloxymethyl group, a pyridyloxyethyl group, a benzofuranyloxymethyl group, a benzothienyloxymethyl group, and the like can be mentioned.
  • Examples of the C6-10 aryl C2-6 alkenyl group include a styryl group and a phenylpropenyl group.
  • Examples of the 5-10 membered heterocyclic oxy group include a furyloxy group, a thienyloxy group, a pyridyloxy group, a benzofuranyloxy group, and the like, and examples of the C6-10 arylcarbonyl group include phenyl. Examples thereof include a carbonyl group, a (2-naphthyl) carbonyl group, etc.
  • C1-6 alkylsulfinyl group a methylsulfinyl group, an ethylsulfinyl group, an n-propylsulfinyl group, an iso-propylsulfinyl group, an n-butylsulfinyl group , Iso-bu Rulsulfinyl group, n-pentylsulfinyl group, iso-pentylsulfinyl group, n-hexylsulfinyl group, 4-methylpentylsulfinyl group, 3-methylpentylsulfinyl group and the like can be mentioned, and C1-3 trialkylsilyl C2- As 8-alkynyl group, 2-trimethylsilyl-1-ethynyl group, 3-trimethylsilyl-2-propynyl group, 4-trimethylsilyl-3-butynyl group, 5-trimethylsilyl-4
  • the group represented by E may have at least one group listed in the substituent group m-1.
  • [Substituent group i-1] ⁇ Halogen atom, C1-8 alkyl group, C1-8 alkoxy group, C3-8 alkenyloxy group, C3-8 alkynyloxy group, C6-10 aryloxy group, C6-10 aryl C1-6 alkoxy group and (C1- C2 alkoxy) C2-C5 alkoxy group ⁇ ;
  • the group represented by E may have at least one group listed in the substituent group j-1.
  • A is A 1 An ether compound which is In Formula (1), A is A 2 An ether compound which is In Formula (1), A is A 3 An ether compound which is In Formula (1), A is A 1 , A 2 Or A 3 An ether compound in which p, q or r is 0; In Formula (1), A is A 1 An ether compound wherein p is 0; In Formula (1), A is A 2 An ether compound in which q is 0; In Formula (1), A is A 3 An ether compound wherein r is 0; An ether compound in which n is 1 in formula (1); An ether compound in which n is 1 or 2 in formula (1); An ether compound in which n is 2 in formula (1); An ether compound in which n is 2 in formula (1); An ether compound in which n is an ether compound in which n is an ether compound in which n is 2 in formula (1); An ether compound in which n is in which n is an ether compound in which n is 2 in formula (1); An ether compound in
  • An ether compound represented by In formula (2) E represents a furyl group optionally having at least one group listed in the substituent group m-1, and at least one group listed in the substituent group m-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group i-1, and at least one group listed in the substituent group i-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group j-1, and at least one group listed in the substituent group j-1.
  • An ether compound represented by In Formula (3) E represents a furyl group optionally having at least one group listed in the substituent group m-1, and at least one group listed in the substituent group m-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group i-1, and at least one group listed in the substituent group i-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group j-1, and at least one group listed in the substituent group j-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group m-1, and at least one group listed in the substituent group m-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group i-1, and at least one group listed in the substituent group i-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group j-1, and at least one group listed in the substituent group j-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group m-1, and at least one group listed in the substituent group m-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group i-1, and at least one group listed in the substituent group i-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group j-1, and at least one group listed in the substituent group j-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group m-1, and at least one group listed in the substituent group m-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group i-1, and at least one group listed in the substituent group i-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group j-1, and at least one group listed in the substituent group j-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group m-1, and at least one group listed in the substituent group m-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group i-1, and at least one group listed in the substituent group i-1.
  • E represents a furyl group optionally having at least one group listed in the substituent group j-1, and at least one group listed in the substituent group j-1.
  • the present compound can be produced by the production method described in the international patent application WO2005 / 033079 pamphlet (Patent Document 1) or the production examples described later.
  • This compound can also be produced, for example, by the following (Production Method 1) to (Production Method 3).
  • This compound can be produced by reacting compound (8) with compound (9) in the presence of a base.
  • A, E and n represent the same meaning as described above, and L represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group or a p-toluenesulfonyloxy group.
  • the reaction is usually performed in the presence of a solvent.
  • ethers such as tetrahydrofuran (hereinafter sometimes referred to as THF), ethylene glycol dimethyl ether, tert-butyl methyl ether (hereinafter sometimes referred to as MTBE), toluene, Aromatic hydrocarbons such as xylene, halogenated hydrocarbons such as chlorobenzene, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide (hereinafter sometimes referred to as DMF), dimethyl sulfoxide, etc.
  • THF tetrahydrofuran
  • MTBE tert-butyl methyl ether
  • DMF dimethyl sulfoxide
  • the reaction temperature is usually ⁇ 20 to 100 ° C., and the reaction time is usually 0.1 to 24 hours.
  • reaction method 2 This compound can be produced by reacting the compound (8) and the alcohol compound represented by the compound (10) in the presence of a condensing agent. [Wherein, A, E and n represent the same meaning as described above. ] The reaction is usually performed in the presence of a solvent.
  • the solvent examples include hydrocarbons such as toluene and hexane, ethers such as THF and MTBE, halogenated hydrocarbons such as chlorobenzene, acid amides such as DMF, and mixtures thereof.
  • the condensing agent examples include a reagent comprising diethyl azodicarboxylate (hereinafter sometimes referred to as DEAD) and triphenylphosphine.
  • DEAD diethyl azodicarboxylate
  • triphenylphosphine triphenylphosphine.
  • the amount of compound (8) to be used is generally 0.5 mol to excess, preferably 1 to 1.5 mol per 1 mol of compound (10), and the condensing agent comprises DEAD and triphenylphosphine.
  • the amount of DEAD used is usually 0.8 to 2 mol, preferably 1 to 2 mol
  • the amount of triphenylphosphine used is usually 0.8 to 2 mol, relative to 1 mol of compound (10).
  • the reaction temperature is usually from ⁇ 20 ° C. to the boiling point of the solvent used for the reaction or 100 ° C.
  • the reaction time is usually from 5 minutes to 24 hours.
  • this compound can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated present compound can be further purified by chromatography, recrystallization and the like.
  • compound (II) can be produced by reacting compound (11) in which E is a phenyl group having a hydroxyl group with compound (12) in the presence of a base.
  • A, L and n represent the same meaning as described above, and R 4 Is a C1-8 alkyl group, a C3-8 alkenyl group, a C3-8 alkynyl group, a C6-10 aryl C1-6 alkyl group, a C1-6 alkoxy C1-8 alkyl group, a C3-8 cycloalkyl C1-6 alkyl group, Phenyl C1-6 alkyl group, furyl C1-6 alkyl group, thienyl C1-6 alkyl group, pyridyl C1-6 alkyl group, phenoxy C1-6 alkyl group, pyridyloxy C1-6 alkyl group, C1-8 haloalkoxy group, C1-6 alkylthio C1-8 alkyl group, C
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, nitriles such as acetonitrile, and acid amides such as DMF. , Sulfoxides such as dimethyl sulfoxide, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, water, and mixtures thereof.
  • Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate, alkali metal hydroxides such as sodium hydroxide, alkali metal hydrides such as sodium hydride, and the like. .
  • the amount of compound (12) used is usually 1 to 10 moles and the amount of base used is usually 1 to 5 moles relative to 1 mole of compound (11).
  • the reaction temperature is usually ⁇ 20 to 100 ° C., and the reaction time is usually 0.1 to 24 hours. After completion of the reaction, after adding water to the reaction mixture, if a solid is precipitated, the compound (II) can be isolated by filtration. If no solid is precipitated, the reaction mixture is organically mixed.
  • Compound (II) can be isolated by performing post-treatment operations such as extraction with a solvent and drying and concentration of an organic layer.
  • the isolated compound (II) can be further purified by chromatography, recrystallization and the like.
  • this compound is usually mixed with a liquid carrier, solid carrier, gas carrier, surfactant and the like, and if necessary, an auxiliary for formulation such as a binder and a thickener is added, It is formulated into wettable powder, wettable powder, flowable powder, granule, dry flowable powder, emulsion, aqueous liquid, oil, smoke, aerosol, microcapsule and the like.
  • Solid carriers used for formulation include vegetable powders (eg, soybean powder, tobacco powder, wheat flour, wood powder, etc.), mineral powders (eg, kaolin, bentonite, acid clay, clays such as clay) Talc such as talc powder and wax stone powder, silica such as diatomaceous earth and mica powder), alumina, sulfur powder, activated carbon, saccharides (eg lactose, glucose etc.), inorganic salts (eg calcium carbonate, sodium bicarbonate) Etc.), hollow glass bodies (obtained by firing natural glass and enclosing bubbles therein), and the like. Two or more kinds of these solid carriers can be mixed and used at an appropriate ratio.
  • vegetable powders eg, soybean powder, tobacco powder, wheat flour, wood powder, etc.
  • mineral powders eg, kaolin, bentonite, acid clay, clays such as clay
  • Talc such as talc powder and wax stone powder
  • silica such as diatomaceous earth and mica powder
  • alumina
  • the liquid carrier or solid carrier is usually used in an amount of 1 to 99% by weight, preferably about 10 to 99% by weight, based on the entire preparation.
  • a surfactant is usually used as an emulsifier, a dispersant, a spreading agent, a penetrating agent, a wetting agent and the like used for formulation.
  • surfactants include anions such as alkyl sulfate ester salts, alkyl aryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphate esters, lignin sulfonates, and naphthalene sulfonate formaldehyde polycondensates.
  • Nonionic surfactants such as surfactants and polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters and the like can be mentioned. Two or more kinds of these surfactants can be used.
  • the surfactant is usually used in a proportion of 0.1 to 50% by weight, preferably about 0.1 to 25% by weight, based on the whole preparation.
  • binder or thickener examples include dextrin, sodium salt of carboxymethyl cellulose, polycarboxylic acid polymer compound, polyvinyl pyrrolidone, polyvinyl alcohol, sodium lignin sulfonate, calcium lignin sulfonate, sodium polyacrylate, gum arabic Sodium alginate, mannitol, sorbitol, bentonite minerals, polyacrylic acid and its derivatives, sodium salt of carboxymethyl cellulose, white carbon, natural sugar derivatives (for example, xanthan gum, guar gum, etc.), and the like.
  • the agricultural composition of the present invention may be mixed with or without mixing with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers or soil conditioners. It can also be used.
  • Such other fungicides include, for example, propiconazole, prothioconazole, triazimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumi Azole fungicides such as sol, tetraconazole, microbutanyl, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, viteltanol, imazalil, flutriahol, cimeconazole, ipconazole; fenpropimorph,
  • Such other insecticides include, for example, (1) Organophosphorus compounds Acephate, aluminum phosphide, butathiofos, cadusafos, chlorethoxyphos, chlorfenvinphos, chlorpyriphos, chloropyriphos , Cyanophos (CYAP), diazinon, DCIP (dichloropropionic ether), diclofenthion (ECP), dichlorvos (DDVP), dimethoate (dimethoa) e), dimethylvinphos, disulfoton, EPN, ethion, etiophos, etrimfos, fenthion (MPP), fenitrothion (M) , Formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathione monochromate, DM rotophos, naled (BRP), oxydeprof
  • acaricides include, for example, acequinocyl, amitraz, benzoximate, biphenate, phenisobromolate, quinomethionate, and quinomethionate.
  • nematicidal active ingredients include, for example, DCIP, fostiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartarate, iciafos Etc.
  • the weight ratio of the active ingredient to the agricultural composition of the present invention combined with or used in combination with the agricultural composition is usually in the range of 1: 0.01 to 1: 100, preferably 1: 0.1 to 1:10.
  • the weight ratio of the active ingredient to the agricultural composition of the present invention and the insecticide used in combination or in combination is usually in the range of 1: 0.01 to 1: 100, preferably 1: 0.1 to 1:10.
  • the weight ratio of the active ingredient to the acaricide used together with or in combination with the agricultural composition of the present invention is usually in the range of 1: 0.01 to 1: 100, preferably 1: 0.1 to 1:10.
  • the weight ratio of the active ingredient to the nematicide used together with or in combination with the agricultural composition of the present invention is usually in the range of 1: 0.01 to 1: 100, preferably 1: 0.1 to 1:10. .
  • the weight ratio of the active ingredient to the herbicide mixed or used in combination with the agricultural composition of the present invention is usually in the range of 1: 0.01 to 1: 100, preferably 1: 0.1 to 1:10.
  • the weight ratio of the active ingredient to the plant growth regulator used in combination with or in combination with the agricultural composition of the present invention is usually in the range of 1: 0.00001 to 1: 100, preferably 1: 0.0001 to 1: 1.
  • the ratio of the fertilizer or soil improver used in combination with or in combination with the agricultural composition of the present invention is usually in the range of 1: 0.1 to 1: 1000, preferably 1: 1 to 1: 200, by weight.
  • the method of applying the agricultural composition of the present invention is not particularly limited as long as the agricultural composition of the present invention can be applied substantially.
  • a plant of a useful plant crop such as foliage spraying.
  • Treatment of cultivated land such as planted or planted soil of useful crop plants, treatment of seeds such as seed disinfection, and the like.
  • the application amount of the agricultural composition of the present invention varies depending on weather conditions, formulation form, application time, application method, application location, target disease, target crop, etc., but it is based on the weight of the present compound in the agricultural composition of the present invention. It is usually 1 to 500 g, preferably 2 to 200 g per 10 ares.
  • Emulsions, wettable powders, suspensions and the like are usually diluted with water before use. In this case, the concentration of the present compound after dilution is usually 0.0005 to 2% by weight, preferably 0.005 to 1.
  • the powder, granules and the like are usually applied as they are without dilution.
  • the weight of the present compound in the agricultural composition of the present invention is usually 0.001 to 100 g, preferably 0.01 to 50 g per 1 kg seed.
  • the agricultural composition of the present invention can be used as a plant disease control agent due to phytopathogenic fungi in agricultural land such as fields, paddy fields, lawns, orchards.
  • the agricultural composition of the present invention can control plant diseases caused by phytopathogenic fungi in the cultivated land in the cultivated land and the like where the following “crop” and the like are cultivated.
  • Agricultural crops corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, vegetables, solanaceous vegetables (eggplants, tomatoes, peppers, peppers, potatoes) Cucumber, pumpkin, zucchini, watermelon, melon, etc., cruciferous vegetables (radish, turnip, horseradish, kohlrabi, cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae (burdock, Shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celeryaceae vegetables (carrot, parsley, celery, red pepper, etc.), red crustacean vegetables (spinach, chard, etc.) (Perilla, mint, basil ), Strawberry, sweet potato, yam, taro, etc., Flower buds; Foliage plant; Fruit trees; pears
  • Trees other than fruit trees Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.
  • Biofuel plants Jatropha curcas, safflower, Amanas, switchgrass, Miss Kansas, Kusanoshi, Danchiku, Kenaf, cassava, willow, algae, etc.
  • HPPD inhibitors such as isoxaflutol
  • ALS inhibitors such as imazetapyr and thifensulfuron methyl
  • EPSP synthase inhibitors such as imazetapyr and thifensulfuron methyl
  • EPSP synthase inhibitors glutamine synthase inhibitors
  • herbicides such as bromoxynil
  • imidazoline non-herbicide-resistant Clearfield canola
  • imazetapir imidazoline non-herbicide-resistant Clearfield
  • sulfonylurea-type ALS-inhibiting herbicide-resistant such as thifensulfuron methyl
  • STS soybeans Examples of “crop” to which tolerance has been imparted by genetic recombination technology include glyphosate and glufosinate-resistant corn varieties, which are already sold under trade names such as RoundupReady (registered trademark) and LibertyLink (registered trademark). Has been.
  • the “crop” includes, for example, a crop that can synthesize selective toxins known in the genus Bacillus by using genetic recombination technology.
  • Toxins expressed in such genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus popirie; Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis Insecticidal proteins such as ⁇ -endotoxin, VIP1, VIP2, VIP3 or VIP3A; nematode-derived insecticidal proteins; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plants Lectin; agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; ly
  • Ribosome inactivating protein RIP
  • steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-COA reductase; sodium channel, calcium channel inhibitor, etc. Ion channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.
  • toxins expressed in such genetically modified crops hybrids of insecticidal proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, and the like, ⁇ -endotoxin proteins, VIP1, VIP2, VIP3 or VIP3A Toxins, partially defective toxins, modified toxins are also included.
  • Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques.
  • Cry1Ab lacking a part Cry1Ab lacking a part of the amino acid sequence is known.
  • the modified toxin one or more amino acids of the natural toxin are substituted.
  • Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073, and the like.
  • the toxins contained in these recombinant plants particularly confer resistance to Coleoptera pests, Diptera pests, and Lepidoptera pests.
  • genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known and some are commercially available.
  • transgenic plants examples include YieldGard® (a corn variety that expresses Cry1Ab toxin), YieldGuard Rootworm® (a corn variety that expresses Cry3Bb1 toxin), YieldGard Plus® (Cry1Ab and Cry3Bb1) Corn varieties that express toxin), Herculex I® (corn varieties that express phosphinotricin N-astilyltransferase (PAT) to confer resistance to Cry1Fa2 toxin and glufosinate), NuCOTN33B (Cry1Ac toxin) Cotton varieties that express), Bollgard I (registered trademark) (cotton varieties that express Cry1Ac toxin), Bollgard II (registered trademark) (Cry1Ac and cotton varieties expressing ry2Ab toxin), VIPCOT® (cotton varieties expressing VIP toxin), NewLeaf® (potato varieties expressing Cry3A toxin), NatureGard® Agriure® Examples include GT Advantage (GA
  • the above “crop” includes those given the ability to produce an anti-pathogenic substance having a selective action using genetic recombination technology.
  • PR proteins and the like are known as examples of anti-pathogenic substances (PRPs, EP-A-0 392 225).
  • anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0 392 225, WO 95/33818, EP-A-0 353 191 and the like.
  • anti-pathogenic substances expressed in such genetically modified plants include, for example, sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.).
  • Ion channel inhibitor Ion channel inhibitor
  • stilbene synthase bibenzyl synthase
  • chitinase glucanase
  • PR protein Antibacterial substances produced by microorganisms such as antibiotics, protein factors involved in plant disease resistance (referred to as plant disease resistance gene and described in WO 03/000906), and the like.
  • plant diseases that can be controlled by the present invention include plant diseases caused by phytopathogenic filamentous fungi, and more specifically, the following diseases can be mentioned, but are not limited thereto. .
  • Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiotic seedling (Gibberella fujikuroi) or yellow rot Erysiphe graminis), Fusarium graminearum, F. avenacerum, F. culmorum, Microchiuminumivale, rust disease (Puccinia striformis, P. graminis, P. graminis, P. graminis, P. graminis, P. graminis, P. nivalis), Bare scab (Ustilago tritici, U.
  • apple Monilia mary rot (Valsa ceratosperma), powdery mildew (Podosperaera leucotricha), leaf spot (Alternaria alteratapap) Diseases (Glomerella cingula); Pear black spot disease (Venturia nashicola, V. pirina); Black spot disease (Alternaria alternata Japan pathotype); Red star disease (Gymnosporum); Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.
  • Grapes black rot (Elsinoeamelina), late rot (Glomerella cinulata), powdery mildew (Uncinula necatoria), rust (Phakopsora amploidis), black lot illness (Guinardiabilid) Anthracnose of oysters (Gloeosporium kaki), deciduous leaf (Cercospora kaki, Mycosphaerella nawae); Anthracnose of cucurbits (Colletotrichum lagenarium), powdery mildew (Sphaerothegul) (Fusarium ox sporum, downy mildew (Pseudoperonospora cubensis), plague (Phytophthora sp.), seedling blight (Phythium sp.); tomato ring rot (Alternaria phalanthrum fuld disease) Brown leaf blight of eggplant (Phomopsis vexans), powdery mildew (Erys
  • Sojae Sojae
  • rust Phakopsoraporinto
  • Black astringent disease Cercospora personata
  • brown spot disease Cercospora arachidicola
  • white silkworm Sclerotium rolfsii
  • pea powdery mildew Edrysiphe phisii
  • potato summer plague Alternaria foliage disease
  • Wilting Disease Verticillium albo-arum, V.
  • Production Example 1 To a mixture of 0.096 g of 55% sodium hydride (oil) and 3 ml of N, N-dimethylformamide (hereinafter sometimes referred to as DMF) was added 0.29 g of quinolin-6-ol under ice cooling, and then A mixed solution of 0.28 g of 2-fluorobenzyl chloride and 2 ml of DMF was added. Water was added to the reaction mixture stirred overnight at room temperature, and this was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure.
  • DMF N-dimethylformamide
  • Production Example 24 Add 0.25 g of 3- (quinolin-6-yloxymethyl) phenol, 0.18 g of 4-methoxybutyl methanesulfonate and 0.39 g of cesium carbonate to 3 ml of DMF, stir at room temperature overnight, and then stir at 80 ° C. for 4 hours. did. A 4% aqueous sodium hydroxide solution was added to the reaction mixture cooled to room temperature, and this was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure.
  • Reference production example 2 10 ml of concentrated hydrochloric acid was added to a mixed solution of 12.0 g of ⁇ [3- (3-methoxymethoxy) phenyl] methyl ⁇ (quinolin-6-yl) ether and 100 ml of ethanol, followed by stirring at room temperature overnight. Saturated aqueous sodium hydrogen carbonate solution was added to the concentrated reaction mixture, and the precipitated solid was collected by filtration, washed successively with water and hexane, dried and crude 3- (quinolin-6-yloxymethyl) phenol 3- (quinoline- 7.0 g of 6-yloxymethyl) phenol was obtained.
  • the reaction mixture was cooled to room temperature, water was added, and ethanol was distilled off under reduced pressure.
  • the pH of the mixture obtained with 5% hydrochloric acid was adjusted to 2, and the precipitated solid was collected by filtration.
  • the obtained solid was washed with water and then dried under reduced pressure to obtain 4.3 g of 3- (3-phenoxyphenyl) propionic acid.
  • Formulation Example 2 20 parts of each of the present compounds 1 to 55 and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol and finely pulverized by a wet pulverization method. 40 parts of an aqueous solution containing 0.05 part and 0.1 part of aluminum magnesium silicate are added, and further 10 parts of propylene glycol are added and stirred and mixed to obtain each flowable preparation.
  • Formulation Example 3 2 parts of each of the present compounds 1 to 55, 88 parts of kaolin clay and 10 parts of talc are thoroughly pulverized and mixed to obtain each powder.
  • Formulation Example 4 Each of the compounds 1 to 55, 5 parts of each, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene are mixed well to obtain each emulsion.
  • Formulation Example 5 2 parts of each of the present compounds 1 to 55, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are thoroughly pulverized and mixed, and then well kneaded and granulated and dried. Thus, each granule is obtained.
  • Formulation Example 6 10 parts of each of the present compounds 1 to 55; 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt; and 55 parts of water are mixed and finely pulverized by a wet pulverization method to obtain each flowable preparation.
  • test examples show that the present invention is useful for controlling plant diseases.
  • the control effect is to visually observe the area of the lesion on the test plant at the time of the survey, and to compare the area of the lesion on the plant treated with the present control agent and the area of the lesion on the untreated plant. It was evaluated by.
  • Test example 1 Cucumber powdery mildew prevention effect test (Sphaerotheca furiginea) A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. Thereafter, the present compounds 13 to 16, 25, 31, 33 and 34 were made into flowable preparations according to Preparation Example 6 and then diluted with water to give a predetermined concentration (500 ppm) so that they sufficiently adhere to the cucumber leaf surface. The foliage was sprayed. After spraying, the plants were air-dried and sprinkled with spores of pathogenic bacteria. After inoculation, it was placed in a 23 ° C. greenhouse for 10 days, and then the lesion area was examined.
  • Test example 2 Wheat leaf blight prevention effect test (Septoria tritici) A plastic pot was filled with sandy loam, wheat (cultivar: Apogee) was sown and grown in a greenhouse for 10 days. The compounds 1, 3, 6, 8, 13-16, 18, 20, 28, 40 and 52 were made into flowable preparations according to Preparation Example 6 and then diluted with water to a predetermined concentration (500 ppm). The foliage was sprayed so as to adhere well to the leaf surface.
  • the present compounds 32, 40, 41 and 52 were made into flowable formulations according to Formulation Example 6, diluted with water to a predetermined concentration (500 ppm), and sprayed on the foliage so as to adhere well to the cucumber leaves. After spraying, the plants were air-dried, and a PDA medium containing spores of cucumber gray mold was placed on the cucumber leaf surface. After inoculation for 4 days at 12 ° C. and high humidity, the lesion area was examined. As a result, the lesion area on the plant treated with the present compounds 32, 40, 41 and 52 was 30% or less of the lesion area on the untreated plant.
  • Test example 4 Cucumber nuclear disease prevention effect test (Sclerotinia sclerotiorum) A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. The compounds 1, 3, 6-8, 11, 13-22, 24-28, 30-33, 40, 41, 54 and 55 were made into flowable preparations according to Preparation Example 6 and then diluted with water to a predetermined concentration. (500 ppm) was sprayed on the foliage so that it adhered sufficiently to the cucumber leaf surface. After spraying, the plants were air-dried, and a mycelia-containing PDA medium containing mycorrhizal fungi was placed on the cucumber leaf surface.
  • Sclerotinia sclerotiorum Cucumber nuclear disease prevention effect test
  • the present compounds 1, 6, 29 and 55 were made into flowable formulations according to Formulation Example 6, diluted with water to a predetermined concentration (500 ppm), and sprayed on the foliage so as to adhere well to the radish leaves. After spraying, the plants were air-dried and spray-inoculated with an aqueous suspension of radish black spot fungus spores. After inoculation, it was first placed at 24 ° C. under high humidity for 1 day and then placed in a greenhouse for 3 days, and then the lesion area was examined. As a result, the lesion area on the plant treated with the present compounds 1, 6, 29 and 55 was 30% or less of the lesion area on the untreated plant.
  • Test Example 6 Rice blast prevention effect test (Magnaporthe grisea) A plastic pot was filled with soil, rice (cultivar; Nihonbare) was sown and grown in a greenhouse for 12 days. The present compounds 1, 2, 4 to 22, 25 to 27, 29, 30, 32 to 41 and 48 to 55 were made into flowable preparations according to Preparation Example 6 and then diluted with water to a predetermined concentration (500 ppm). The foliage was sprayed so as to adhere well to the leaf surface of rice. After spraying, the plants were air-dried, and a pot having rice blast-affected leaves was left around the sprayed plants. All rice was left under high humidity only at night, and the lesion area was examined 5 days after inoculation.
  • the lesion area in the plant treated with the present compounds 1, 2, 4 to 22, 25 to 27, 29, 30, 32 to 41 and 48 to 55 is 30% or less of the lesion area in the untreated plant.
  • Met. Test Example 7 Tomato plague prevention effect test (Phytophthora infestans) A plastic pot was filled with sand loam, seeded with tomato (variety: patio), and grown in a greenhouse for 20 days. Each of the present compounds 6 and 28 was made into a flowable formulation according to Formulation Example 6, diluted with water to a predetermined concentration (500 ppm), and sprayed with foliage so as to adhere well to the leaf surface of the tomato seedling.
  • the suspension was spray-inoculated with an aqueous suspension of tomato plague fungus spores. After inoculation, it was first placed at 23 ° C. under high humidity for 1 day and further cultivated in a greenhouse for 4 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the present compounds 6 and 28 was 30% or less of the lesion area in the untreated plant.
  • Test Example 8 Tomato wilt soil treatment test (irrigation) Tomato wilt (Fusarium oxysporum) contaminated soil is filled in a plastic pot, tomato (variety: patio) is sown, this compound is made into a flowable formulation according to Formulation Example 6, and then diluted with water. A soil irrigation treatment is carried out with an amount of the water-diluted solution of 10 mg of the present compound. After cultivating in a greenhouse for 1 month, investigate the growth of plants. As a result, the plants cultivated in the soil (treated area) treated with soil irrigation of this compound are compared with the plants cultivated in the same manner as the treated area in soil (untreated area) where this compound is not irrigated with soil.
  • Test Example 9 Potato half body wilt soil treatment test (irrigation) A plastic pot is filled with soil contaminated with potato half body wilt (Verticillium albo-atrum, v. Dahlliae, v. Nigrescens), potatoes (variety: baron) are planted, and the compound is made into a flowable formulation according to Formulation Example 6, followed by water. Then, the water diluted solution in an amount of 10 mg of the present compound per one pot of the plastic pot is subjected to soil irrigation treatment. After cultivating in a greenhouse for 2 months, investigate the growth of plants.
  • Test Example 10 Rice idiot seed treatment This compound is made into a flowable formulation according to Formulation Example 6, and then diluted to 2000 ppm with water, and seeds of Gibberella fujikuroi-contaminated pods are treated with a dipping method. Thereafter, the seedling box filled with soil is sown with the above-mentioned contaminated pods and cultivated in a greenhouse for one month, and then the growth state of the plant is investigated.

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

Abstract

Cette invention concerne une composition agricole comprenant un composé éther de formule (1) [A représente A1, A2 ou A3 (les symboles R1, R2, R3, p, q, r et autres étant tels que définis dans la description) ; n représente un nombre entier compris entre 1 et 4 ; et E représente un groupe furyle, un groupe thiényle, un groupe pyrrolyle, un groupe tétrazolyle, un groupe thiazolyle, un groupe pyrazolyle ou un groupe phényle, chacun d'eux pouvant avoir un substituant], un sel du composé éther, ou un hydrate du composé éther ou du sel. La composition agricole peut lutter contre ou prévenir une maladie des plantes causée par une bactérie pathogène des végétaux.
PCT/JP2009/067191 2008-09-19 2009-09-18 Composition agricole luttant contre ou prévenant une maladie des plantes causée par une bactérie pathogène des végétaux Ceased WO2010032886A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012062302A (ja) * 2010-08-20 2012-03-29 Sumitomo Chemical Co Ltd 有害節足動物防除組成物及び有害節足動物の防除方法
WO2016077240A3 (fr) * 2014-11-10 2016-08-18 Forge Life Science, Llc Compositions anti-hcmv et procédés
CN119799724A (zh) * 2024-12-26 2025-04-11 南京农业大学 TaJDR1基因及其在提高植物抗赤霉病和干旱抗性中的应用

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US2152047A (en) * 1939-03-28 Preserving and disinfecting media
US2777852A (en) * 1957-01-15 Z-lower-alkylsulfinyl
JPS63139149A (ja) * 1986-12-02 1988-06-10 Tokuyama Soda Co Ltd α−置換フエニル酢酸誘導体
JPH061778A (ja) * 1992-06-18 1994-01-11 Asahi Chem Ind Co Ltd 新規なアゾール化合物
JPH11504928A (ja) * 1995-05-12 1999-05-11 ドクトル カルル トーマエ ゲゼルシャフト ミット ベシュレンクテル ハフツング ベンゾチアゾール及びベンゾオキサゾール、これらの化合物を含む医薬組成物並びにそれらの使用及びそれらの調製方法
WO2005033079A1 (fr) * 2003-09-30 2005-04-14 Eisai Co., Ltd. Agent antifongique a compose heterocyclique
WO2007088978A1 (fr) * 2006-02-03 2007-08-09 Meiji Seika Kaisha, Ltd. Nouveau derive de quinoleine et pesticide destine a des applications agricoles et horticoles comprenant le derive en tant que principe actif
WO2008142384A1 (fr) * 2007-05-17 2008-11-27 Helperby Therapeutics Limited Utilisation de composés de 4-(pyrrolidine-1-yl)quinoléine pour tuer des micro-organismes cliniquement latents

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Publication number Priority date Publication date Assignee Title
US2152047A (en) * 1939-03-28 Preserving and disinfecting media
US2777852A (en) * 1957-01-15 Z-lower-alkylsulfinyl
JPS63139149A (ja) * 1986-12-02 1988-06-10 Tokuyama Soda Co Ltd α−置換フエニル酢酸誘導体
JPH061778A (ja) * 1992-06-18 1994-01-11 Asahi Chem Ind Co Ltd 新規なアゾール化合物
JPH11504928A (ja) * 1995-05-12 1999-05-11 ドクトル カルル トーマエ ゲゼルシャフト ミット ベシュレンクテル ハフツング ベンゾチアゾール及びベンゾオキサゾール、これらの化合物を含む医薬組成物並びにそれらの使用及びそれらの調製方法
WO2005033079A1 (fr) * 2003-09-30 2005-04-14 Eisai Co., Ltd. Agent antifongique a compose heterocyclique
WO2007088978A1 (fr) * 2006-02-03 2007-08-09 Meiji Seika Kaisha, Ltd. Nouveau derive de quinoleine et pesticide destine a des applications agricoles et horticoles comprenant le derive en tant que principe actif
WO2008142384A1 (fr) * 2007-05-17 2008-11-27 Helperby Therapeutics Limited Utilisation de composés de 4-(pyrrolidine-1-yl)quinoléine pour tuer des micro-organismes cliniquement latents

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012062302A (ja) * 2010-08-20 2012-03-29 Sumitomo Chemical Co Ltd 有害節足動物防除組成物及び有害節足動物の防除方法
WO2016077240A3 (fr) * 2014-11-10 2016-08-18 Forge Life Science, Llc Compositions anti-hcmv et procédés
CN119799724A (zh) * 2024-12-26 2025-04-11 南京农业大学 TaJDR1基因及其在提高植物抗赤霉病和干旱抗性中的应用
CN119799724B (zh) * 2024-12-26 2025-10-31 南京农业大学 TaJDR1基因及其在提高植物抗赤霉病和干旱抗性中的应用

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