WO2017110864A1 - Composition de lutte contre des maladies végétales et son application - Google Patents

Composition de lutte contre des maladies végétales et son application Download PDF

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WO2017110864A1
WO2017110864A1 PCT/JP2016/088078 JP2016088078W WO2017110864A1 WO 2017110864 A1 WO2017110864 A1 WO 2017110864A1 JP 2016088078 W JP2016088078 W JP 2016088078W WO 2017110864 A1 WO2017110864 A1 WO 2017110864A1
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compound
disease control
oxadiazole
plant disease
formula
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PCT/JP2016/088078
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English (en)
Japanese (ja)
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雄一 松崎
孝明 中野
井上　拓也
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住友化学株式会社
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Publication of WO2017110864A1 publication Critical patent/WO2017110864A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • 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
    • A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • 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
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero 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
    • A01N43/72—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
    • A01N43/88—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 six-membered rings with three ring hetero 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Definitions

  • the present invention relates to a plant disease control composition and its use.
  • Patent Documents 1 and 2 Conventionally, many compounds have been developed and put into practical use for controlling plant diseases (see, for example, Patent Documents 1 and 2).
  • An object of the present invention is to provide a composition having an excellent control effect against plant diseases.
  • the present inventor has found one or more kinds selected from the oxadiazole compound represented by the following formula (1) and the following group (A). It has been found that a plant disease control composition containing a bactericidal compound has an excellent control effect against plant diseases.
  • R 1 represents a halogen atom, a C1-C4 alkoxy group, or a nitro group
  • n represents an integer of 0-2 (when n is 2, R 2 may be the same or different)
  • R 2 represents a C1-C9 alkyl group, a C1-C4 alkoxy group, a C2-C4 alkenyl group, or a phenyl group that may be substituted with the same or different groups P 1 as described above
  • R 3 represents a hydrogen atom or a C1-C4 alkyl group
  • R 4 and R 5 represent a C1-C15 alkyl group, a C2-C4
  • Group P 1 A group consisting of a halogen atom, a C1-C4 alkyl group which may be substituted with a halogen atom, a C1-C4 alkoxy group which may be substituted with a halogen atom, a cyano group, and a nitro group.
  • a plant disease control composition comprising an oxadiazole compound represented by the formula (1) and one or more fungicidal compounds selected from the groups (A) to (E).
  • QoI fungicides Qo inhibitors
  • C Bixafen, benzovindiflupyr, fluxapyroxad, penthiopyrad, pyraziflumid, isofetamid, isoprazam, boscalid, flupiram , Sedaxane, penflufen, flutolanil, mepronil, carboxin, thifluxamide, furametpyr, pydiflumetofen, CAS registry number 1228284-64 -7), N-cyclopropyl-3- (difluoromethyl) -5-fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide (CAS Registry Number 1255734- 28-1), 3-difluoromethyl -1-methyl-N- (1,1,3-trimethylindan-4-yl) pyrazole-4-carboxamide (CAS registration number 141573-94-6), 3-difluoromethyl-1-methyl-N-[( 3R) -1
  • the content ratio of the oxadiazole compound represented by the formula (1) to one or more fungicidal compounds selected from the groups (A) to (E) is 0.1: 1 to 10 by weight.
  • the oxadiazole compound represented by the formula (1) according to [1] and one or more bactericidal compounds selected from the groups (A) to (E) are used in a weight ratio of 0.1: 1 to 10:
  • a plant disease control method comprising a step of treating a plant in the range of 1.
  • the plant disease control method according to [3] or [4], wherein the plant is soybean or wheat.
  • plant diseases can be controlled.
  • the plant disease control composition of the present invention (hereinafter referred to as the present composition) is represented by the formula (1). [Wherein R 1 , Z and n represent the same meaning as described above. ]
  • An oxadiazole compound represented by the following (hereinafter referred to as the present oxadiazole compound) and one or more bactericidal compounds selected from the groups (A) to (E) (hereinafter referred to as the present bactericidal compound). To do.
  • halogen atoms means that when two or more halogen atoms are present, these halogen atoms may be the same or different from each other.
  • C1-C3 means having 1 to 3 carbon atoms.
  • the halogen atom represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • An oxadiazole compound represented by formula (1), wherein Z is OC ( X) NR 2 R 3 .
  • An oxadiazole compound represented by formula (1), wherein Z is OC ( O) R 5 .
  • An oxadiazole compound represented by formula (1), wherein Z is NHC ( X) NR 6 R 7 .
  • An oxadiazole compound represented by formula (1), wherein Z is NHC ( O) R 9 .
  • Z is OC ( ⁇ O) XR 4 , and Z is an oxadiazole compound substituted at a position para to the oxadiazole ring of the benzene ring.
  • Z is OC ( ⁇ O) R 5 , and Z is an oxadiazole compound substituted at a position para to the oxadiazole ring of the benzene ring.
  • An oxadiazole compound in which Z is NHC ( ⁇ X) NR 6 R 7 and Z is substituted at a position para to the oxadiazole ring of the benzene ring in formula (1) Z is NHC ( ⁇ O) XR 8 , and Z is an oxadiazole compound substituted at a para position with respect to the oxadiazole ring of the benzene ring.
  • the present oxadiazole compound can be synthesized by, for example, a synthesis method described in JP-A No. 63-162680. Specific examples of the present oxadiazole compound are shown below.
  • Formula (2) [Compound No .; R 10 , R 11 , R 12 , R 13 , R 14 ], Me is a methyl group, Et is an ethyl group, Pr is a propyl group, i-Pr is an isopropyl group, Bu represents a butyl group, t-Bu represents a tertiary butyl group, OMe represents a methoxy group, OEt represents an ethoxy group, Br represents a bromine atom, Cl represents a chlorine atom, F represents a fluorine atom, and Ph represents a phenyl group.
  • R 10 , R 11 , R 13 and R 14 are hydrogen atoms, and R 12 is OC ( ⁇ O) NHMe.
  • A1 to A83 of the oxadiazole compound are shown below.
  • the present bactericidal compound is a bactericidal compound described in groups (A) to (E), all of which are known compounds.
  • This bactericidal compound is, for example, MeisterPro Crop Protection Handbook Vol. 100 (2014), “THE PESTICIDE MANUAL-14th EDITION (BCPC) ISBN 190139396142”, International Publication No. 2013/160387, International Publication No. 2012/084812, International Publication No. 2010/0663700, International Publication No. 2011/162397 No., International Publication No. 2007/072999, International Publication No. 2005/121104, International Publication No. 2008/110313, International Publication No. 2013/162077, and the like. These compounds can be obtained from commercial preparations or synthesized by known methods.
  • Group (A) bactericidal compounds are listed in Table 1 together with compound numbers.
  • the bactericidal compounds of group (B) are listed in Table 2 together with the compound numbers.
  • Group (D) bactericidal compounds are listed in Table 4 together with compound numbers.
  • Group (E) bactericidal compounds are listed in Table 5 along with compound numbers.
  • composition of the present invention are shown below.
  • Z is a para-position relative to the oxadiazole ring of the benzene ring, and any of Compounds I to LXXX
  • Z is OC ( ⁇ O) XR 4 , wherein Z is a para-position substituted with respect to the oxadiazole ring of the benzene ring, and any one of compounds I to LXXI A plant disease control composition containing tsutsu.
  • Z is OC ( ⁇ O) R 5 , and Z is a oxadiazole compound substituted at a position para to the oxadiazole ring of the benzene ring, and any one of Compounds I to LXXI A plant disease control composition containing tsutsu.
  • Z is NHC ( ⁇ X) NR 6 R 7 , and Z is a para-position relative to the oxadiazole ring of the benzene ring, and any one of Compounds I to LXXI
  • the plant disease control composition containing one.
  • Z is NHC ( ⁇ O) XR 8 , wherein Z is a para-position relative to the oxadiazole ring of the benzene ring, and any one of compounds I to LXXI
  • Z is NHC ( ⁇ O) R 9 , and Z is an oxadiazole compound substituted at a position para to the oxadiazole ring of the benzene ring, and any one of Compounds I to LXXI A plant disease control composition containing tsutsu.
  • a plant containing compound I, wherein in formula (1), Z is OC ( X) NR 2 R 3 and Z is substituted at the position para to the oxadiazole ring of the benzene ring, and compound I Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , Z is substituted at the position of para to the oxadiazole ring of the benzene ring, and plant disease control containing Compound I Composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing Compound I Composition.
  • a plant containing compound II, wherein in formula (1), Z is OC ( X) NR 2 R 3 and Z is substituted at a position para to the oxadiazole ring of the benzene ring, and compound II Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control comprising Compound II Composition.
  • a plant containing compound II, wherein in formula (1), Z is NHC ( X) NR 6 R 7 and Z is substituted at the position para to the oxadiazole ring of the benzene ring, and compound II Disease control composition.
  • Z is NHC ( ⁇ O) R 9 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing Compound II Composition.
  • a plant containing compound III, wherein in formula (1), Z is OC ( X) NR 2 R 3 and Z is substituted at a position para to the oxadiazole ring of the benzene ring, and compound III Disease control composition.
  • Z is substituted at the position of para to the oxadiazole ring of the benzene ring, and plant disease control containing compound III Composition.
  • Z is OC ( ⁇ O) R 5 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound III Composition.
  • a plant containing compound III, wherein in formula (1), Z is NHC ( X) NR 6 R 7 and Z is substituted at the position para to the oxadiazole ring of the benzene ring, and compound III Disease control composition.
  • the oxadiazole compound Z is substituted at a position para to the oxadiazole ring of the benzene ring, a plant disease control containing Compound III Composition.
  • Z is NHC ( ⁇ O) R 9 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control comprising compound III Composition.
  • a plant containing compound IV, wherein in formula (1), Z is OC ( X) NR 2 R 3 and Z is substituted at the position para to the oxadiazole ring of the benzene ring, and compound IV Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , and Z is substituted at the position of para to the oxadiazole ring of the benzene ring, and a plant disease control comprising compound IV Composition.
  • Z is OC ( ⁇ O) R 5 , Z is substituted at the position of para to the oxadiazole ring of the benzene ring, and the plant disease control containing Compound IV Composition.
  • a plant containing compound IV, wherein in formula (1), Z is NHC ( X) NR 6 R 7 and Z is substituted at the para position relative to the oxadiazole ring of the benzene ring, and compound IV Disease control composition.
  • Z is NHC ( ⁇ O) R 9 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control comprising the compound IV Composition.
  • a plant containing compound V, wherein Z is OC ( X) NR 2 R 3 in formula (1), Z is substituted at the para position relative to the oxadiazole ring of the benzene ring, and compound V Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , Z is substituted at the position of para to the oxadiazole ring of the benzene ring, and plant disease control containing compound V Composition.
  • Z is OC ( ⁇ O) R 5 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound V Composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound V Composition.
  • Z is OC ( ⁇ O) XR 4 , and Z is substituted at the position para to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound VI Composition.
  • Z is OC ( ⁇ O) R 5 , Z is substituted at the position of para to the oxadiazole ring of the benzene ring, and the plant disease control containing the compound VI Composition.
  • Z is NHC ( ⁇ O) XR 8 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound VI Composition.
  • Z is NHC ( ⁇ O) R 9 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound VI Composition.
  • a plant containing compound XVII, wherein Z is OC ( X) NR 2 R 3 in formula (1) and Z is substituted at the position para to the oxadiazole ring of the benzene ring, and compound XVII Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound XVII Composition.
  • Z is OC ( ⁇ O) R 5 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound XVII Composition.
  • Z is NHC ( ⁇ O) XR 8 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound XVII Composition.
  • Z is NHC ( ⁇ O) R 9 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XVII Composition.
  • a plant containing compound XVIII, wherein Z is OC ( X) NR 2 R 3 in formula (1) and Z is substituted at the para position relative to the oxadiazole ring of the benzene ring, and compound XVIII Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XVIII Composition.
  • Z is OC ( ⁇ O) R 5 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control comprising compound XVIII Composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XVIII Composition.
  • Z is NHC ( ⁇ O) R 9 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XVIII Composition.
  • a plant containing compound XIX, wherein in formula (1), Z is OC ( X) NR 2 R 3 and Z is substituted at the position para to the oxadiazole ring of the benzene ring, and compound XIX Disease control composition.
  • Z is OC ( ⁇ O) R 5 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control comprising the compound XIX Composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound XIX Composition.
  • Z is NHC ( ⁇ O) R 9 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound XIX Composition.
  • a plant containing compound XX, wherein in formula (1), Z is OC ( X) NR 2 R 3 and Z is substituted at the para position relative to the oxadiazole ring of the benzene ring, and compound XX Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound XX Composition.
  • Z is OC ( ⁇ O) R 5 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XX Composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound XX Composition.
  • a plant containing, in the formula (1), Z is OC ( X) NR 2 R 3 and Z is substituted at the position para to the oxadiazole ring of the benzene ring, and the compound XXI Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , and Z is substituted at the position para to the oxadiazole ring of the benzene ring, and a plant disease control comprising the compound XXI Composition.
  • Z is OC ( ⁇ O) R 5 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XXI Composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XXI Composition.
  • Z is NHC ( ⁇ O) R 9 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound XXI Composition.
  • a plant containing compound XXII, wherein in formula (1), Z is OC ( X) NR 2 R 3 and Z is substituted at the position para to the oxadiazole ring of the benzene ring, and compound XXII Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound XXII Composition.
  • Z is OC ( ⁇ O) R 5 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound XXII Composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing compound XXII Composition.
  • Z is NHC ( ⁇ O) R 9 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XXII Composition.
  • a plant containing, in formula (1), an oxadiazole compound in which Z is OC ( X) NR 2 R 3 and Z is substituted at a position para to the oxadiazole ring of the benzene ring, and compound XXXIII Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound XXXIII Composition.
  • Z is OC ( ⁇ O) R 5 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing compound XXXIII Composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XXXIII Composition.
  • Z is NHC ( ⁇ O) R 9 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XXXIII Composition.
  • a plant containing compound XXXIV, wherein in formula (1), Z is OC ( X) NR 2 R 3 , and Z is substituted at the para position relative to the oxadiazole ring of the benzene ring, and compound XXXIV Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound XXXIV Composition.
  • Z is OC ( ⁇ O) R 5 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XXXIV Composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XXXIV Composition.
  • Z is NHC ( ⁇ O) R 9 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound XXXIV Composition.
  • a plant containing an oxadiazole compound in which Z is OC ( X) NR 2 R 3 in formula (1) and Z is substituted at a position para to the oxadiazole ring of the benzene ring, and a compound XXXV Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound XXXV Composition.
  • Z is OC ( ⁇ O) R 5 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XXXV Composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound XXXV Composition.
  • Z is NHC ( ⁇ O) R 9 and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound XXXV Composition.
  • a plant containing compound L, wherein Z is OC ( X) NR 2 R 3 in formula (1) and Z is substituted at the para position relative to the oxadiazole ring of the benzene ring, and compound L Disease control composition.
  • Z is OC ( ⁇ O) XR 4
  • Z is a oxadiazole compound substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound L Composition.
  • Z is OC ( ⁇ O) R 5
  • Z is an oxadiazole compound substituted at the position para to the oxadiazole ring of the benzene ring, and a plant disease control comprising the compound L Composition.
  • a plant containing compound L, wherein Z is NHC ( X) NR 6 R 7 in formula (1), and Z is substituted at the para position relative to the oxadiazole ring of the benzene ring, and compound L Disease control composition.
  • Z is NHC ( ⁇ O) XR 8
  • Z is substituted at the position of para to the oxadiazole ring of the benzene ring, and plant disease control containing the compound L Composition.
  • a plant containing, in formula (1), an oxadiazole compound in which Z is OC ( X) NR 2 R 3 and Z is substituted at a position para to the oxadiazole ring of the benzene ring, and compound LII Disease control composition.
  • Z is OC ( ⁇ O) XR 4
  • Z is a oxadiazole compound substituted at the para position with respect to the oxadiazole ring of the benzene ring
  • plant disease control containing compound LII Composition
  • Z is OC ( ⁇ O) R 5 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound LII Composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound LII Composition.
  • Z is NHC ( ⁇ O) R 9 , and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control comprising the compound LII Composition.
  • a plant containing, in formula (1), an oxadiazole compound in which Z is OC ( X) NR 2 R 3 and Z is substituted at a position para to the oxadiazole ring of the benzene ring, and compound LIII Disease control composition.
  • Z is OC ( ⁇ O) XR 4
  • Z is an oxadiazole compound substituted at the position para to the oxadiazole ring of the benzene ring, and a plant disease control containing the compound LIII Composition.
  • Z is OC ( ⁇ O) R 5
  • Z is an oxadiazole compound substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control comprising the compound LIII Composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the position of para to the oxadiazole ring of the benzene ring, and plant disease control containing compound LIII Composition.
  • Z is NHC ( ⁇ O) R 9 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound LIII Composition.
  • a plant containing the compound LVII, wherein in formula (1), Z is OC ( X) NR 2 R 3 and Z is substituted at the para position relative to the oxadiazole ring of the benzene ring, and compound LVII Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound LVII Composition.
  • Z is OC ( ⁇ O) R 5 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound LVII Composition.
  • a plant containing compound LVII, wherein in formula (1), Z is NHC ( X) NR 6 R 7 and Z is substituted at the para position relative to the oxadiazole ring of the benzene ring, and compound LVII Disease control composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound LVII Composition.
  • Z is NHC ( ⁇ O) R 9 and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control comprising the compound LVII Composition.
  • a plant containing the compound LXIII, wherein in formula (1), Z is OC ( X) NR 2 R 3 , and Z is substituted at the para position relative to the oxadiazole ring of the benzene ring Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control comprising the compound LXIII Composition.
  • a plant containing, in formula (1), an oxadiazole compound in which Z is NHC ( X) NR 6 R 7 and Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and compound LXIII Disease control composition.
  • Z is NHC ( ⁇ O) XR 8 , and Z is substituted at the position para to the oxadiazole ring of the benzene ring, and a plant disease control comprising the compound LXIII Composition.
  • Z is NHC ( ⁇ O) R 9 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound LXIII Composition.
  • a plant containing the compound LXV, wherein in formula (1), Z is OC ( X) NR 2 R 3 and Z is substituted at a position para to the oxadiazole ring of the benzene ring, and the compound LXV Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , and Z is an oxadiazole compound substituted at the para position with respect to the oxadiazole ring of the benzene ring, and a plant disease control comprising the compound LXV Composition.
  • Z is OC ( ⁇ O) R 5
  • Z is a oxadiazole compound substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound LXV Composition.
  • a plant containing, in formula (1), an oxadiazole compound in which Z is NHC ( X) NR 6 R 7 and Z is substituted at a position para to the oxadiazole ring of the benzene ring, and a compound LXV Disease control composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound LXV Composition.
  • Z is NHC ( ⁇ O) R 9 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound LXV Composition.
  • a plant containing the compound LXIX, wherein in formula (1), Z is OC ( X) NR 2 R 3 and Z is substituted at the para position relative to the oxadiazole ring of the benzene ring, and the compound LXIX Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound LXIX Composition.
  • Z is OC ( ⁇ O) R 5 , and Z is an oxadiazole compound substituted at the position para to the oxadiazole ring of the benzene ring, and a plant disease control comprising the compound LXIX Composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound LXIX Composition.
  • Z is NHC ( ⁇ O) R 9 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound LXIX Composition.
  • a plant containing the compound LXX, wherein Z is OC ( X) NR 2 R 3 in formula (1) and Z is substituted at the para position relative to the oxadiazole ring of the benzene ring, and the compound LXX Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound LXX Composition.
  • a plant containing the compound LXX, wherein Z is NHC ( X) NR 6 R 7 and Z is substituted at the para position relative to the oxadiazole ring of the benzene ring, and the compound LXX in the formula (1) Disease control composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound LXX Composition.
  • Z is NHC ( ⁇ O) R 9 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound LXX Composition.
  • a plant containing the compound LXXI, wherein in formula (1), Z is OC ( X) NR 2 R 3 and Z is substituted at the para position relative to the oxadiazole ring of the benzene ring Disease control composition.
  • Z is OC ( ⁇ O) XR 4 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound LXXI Composition.
  • Z is OC ( ⁇ O) R 5 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound LXXI Composition.
  • a plant containing the compound LXXI, wherein in formula (1), Z is NHC ( X) NR 6 R 7 and Z is substituted at a position para to the oxadiazole ring of the benzene ring Disease control composition.
  • Z is NHC ( ⁇ O) XR 8 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing compound LXXI Composition.
  • Z is NHC ( ⁇ O) R 9 , Z is substituted at the para position with respect to the oxadiazole ring of the benzene ring, and plant disease control containing the compound LXXI Composition.
  • the content ratio of the present oxadiazole compound and the present bactericidal compound in the composition of the present invention is not particularly limited, but the ratio of the content of the present oxadiazole compound and the present bactericidal compound is by weight.
  • a range of 0.01: 1 to 500: 1 is preferred, a range of 0.1: 1 to 10: 1 is more preferred, and a range of 0.3: 1 to 3: 1 is particularly preferred.
  • the composition of the present invention may be a mixture of the present oxadiazole compound and the present bactericidal compound, but usually the present oxadiazole compound, the present bactericidal compound, and an inert carrier are mixed, and if necessary, an interface is used. It is formulated into oils, emulsions, flowables, wettable powders, granular wettable powders, powders, granules, and the like by adding active agents and other formulation adjuvants. Such a preparation can be used as a plant disease control agent as it is or with addition of other inactive ingredients.
  • the total amount of the present oxadiazole compound and the present bactericidal compound is usually 0.1 to 99% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80% by weight. .
  • inert carriers used in formulation include solid carriers and liquid carriers.
  • the solid carrier include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fubasamic clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon).
  • liquid carrier examples include water, alcohols (eg, methanol, ethanol), ketones (eg, acetone, methyl ethyl ketone), Aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (eg, n-hexane, cyclohexanone, kerosene), esters (eg, ethyl acetate, butyl acetate), nitriles (Eg acetonitrile, isobutyronitrile), ethers (eg , Dioxane, diisopropyl d - ether), acid amides (e.g., DMF, dimethylacetamide), halogenated hydrocarbons (e.g., dichloroethane, trichlorethylene, carbon te
  • Aromatic hydrocarbons eg, benzene, tol
  • surfactant examples include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. Is mentioned.
  • formulation adjuvants include, for example, fixing agents, dispersants, and stabilizers.
  • casein gelatin, polysaccharides (eg, starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, Bentonite, saccharides, synthetic water-soluble polymers (eg, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (Mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, fatty acid or ester thereof, and the like.
  • polysaccharides eg, starch, arabic gum, cellulose derivatives, alginic acid
  • lignin derivatives Bentonite
  • saccharides synthetic water-soluble polymers (eg, polyvinyl alcohol, polyvinyl
  • composition of the present invention can also be formulated into a preparation containing the present oxadiazole compound and the present oxadiazole compound and the present bactericidal compound, each prepared by the above-described method, diluted with water as necessary. It can also be prepared by mixing a preparation containing a bactericidal compound, or a diluent thereof.
  • composition of the present invention can be used to protect plants from plant diseases.
  • the control method of the present invention is obtained by treating the composition of the present invention on the soil where the plant or plant is cultivated, or treating the present oxadiazole compound and the present bactericidal compound separately on the soil where the plant or plant is cultivated, Can control plant diseases
  • the method of applying the composition of the present invention is not particularly limited as long as the composition of the present invention can be applied substantially, but for example, treatment of plants such as foliage spraying, plants such as soil treatment, etc. To seeds such as seed sterilization and so on.
  • the application amount of the composition of the present invention varies depending on weather conditions, formulation form, application time, application method, application location, target disease, target crop, etc., but is usually 1 to 500 g, preferably 2 to 200 g per 1000 m 2. is there.
  • Emulsions, wettable powders, suspensions and the like are usually diluted with water and applied.
  • the concentration of the composition of the present invention after dilution is usually 0.0005 to 2% by weight, preferably 0.005 to It is 1% by weight, and powders, granules and the like are usually applied as they are without dilution.
  • the amount of the composition of the present invention per 1 kg seed is usually applied in the range of 0.001 to 100 g, preferably 0.01 to 50 g.
  • Examples of the places where plant diseases occur in the present invention include paddy fields, fields, tea gardens, orchards, non-agricultural land, houses, seedling trays and seedling boxes, seedling culture soil, and seedling mats.
  • composition of the present invention can be used as a plant disease control agent in agricultural land such as fields, paddy fields, lawns, orchards.
  • the composition of the present invention can control plant diseases that occur in the cultivated land or the like where the “plant” or the like listed below is 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, chili peppers) Cucumber, pumpkin, zucchini, watermelon, melon, etc., cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae Vegetables (burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (green onion, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, American burdock etc.), red crustacean vegetables (spinach, chard, etc.) , Lamiaceae vegetables (Perilla, mint, basil ), Strawberry, sweet potato, yam, taro, etc., Bridegroom, Fol
  • 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).
  • plants include genetically modified crops.
  • Rice diseases rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiotic seedling (Gibberella fujikuruoi).
  • Wheat diseases powdery mildew (Erysiphe graminis), red mold disease (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivare), rust (Puccinia striformi.
  • Ustilago nuda cloud disease (Rhynchosporium secalis), reticular disease (Pyrenophora teres), spot disease (Cochliobolus sativus), leafy leaf disease (Pyrenophora graminea), and Rhizonia a.
  • Oyster diseases Anthracnose (Gloeosporium kaki), deciduous leaf disease (Cercospora kaki, Mycosphaerella nawae). Diseases of cucurbits: Anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca furiginea), vine blight (Mycosphaerella meloniis), vine scab (Fusarium oxysporum), por disease (fusarium oxysporum) ), Seedling blight (Pythium sp.); Diseases of tomato: Alternaria solani, leaf mold (Cladosporium fulvum), plague (Phytophthora infestans).
  • Peanut disease black astringency (Cercospora personata), brown spot (Cercospora arachidicola), white silkworm (Sclerotium rolfsii).
  • Pea disease powdery mildew (Erysiphe pisi). Diseases of potato: Alternaria solani, Phytophthora infestans, Phytophthora erythropeptica, Spongospora subteranean f.
  • Strawberry disease powdery mildew (Sphaerotheca humuli), anthracnose (Glomerella singulata).
  • Tea diseases net blast (Exobasidium reticulatum), white scab (Elsinoe leucospila), ring spot disease (Pestarotropis sp.), Anthracnose (Colletotrichum theae-sinensis).
  • Tobacco disease Alternaria longipes, powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), epidemic (Phytophyti. Rapeseed diseases: Sclerotinia sclerotiorum, Rhizoctonia solani, and Rhizoctonia solani.
  • Banana disease Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola). Sunflower disease: downy mildew (Plasmopara halstedii). Aspergillus genus, Penicillium genus, Fusarium genus, Gibberella genus, Tricoderder genus, Thielaviopsis genus, Rhizopus genus, Mucor genus, Corticium genus, Phoma genus, Rhizoctonia genus Disease. Viral diseases of various crops mediated by Polymixa genus or Olpidium genus.
  • the composition of the present invention is obtained by mixing the present oxadiazole compound and the present bactericidal compound in the following weight ratio.
  • a plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and Compound I in a ratio of 0.1: 1;
  • a plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and Compound I in a ratio of 1: 1;
  • a plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and Compound I in a ratio of 10: 1;
  • a plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and Compound II in a ratio of 0.1: 1;
  • a plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and Compound II in a ratio of 1: 1;
  • a plant disease control composition comprising any one of the present oxadiazole compounds A1
  • a plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound XVII in a ratio of 0.1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound XVII in a ratio of 1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound XVII in a ratio of 10: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound XVIII in a ratio of 0.1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound XVIII in a ratio of 1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound XVIII in a ratio of 10: 1; A plant disease control composition comprising any one of the present oxadiazole
  • a plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound XXXIII in a ratio of 0.1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound XXXIII in a ratio of 1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound XXXIII in a ratio of 10: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound XXXIV in a ratio of 0.1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound XXXIV in a ratio of 1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound XXXIV in a ratio of 1: 1; A plant disease control composition comprising any one of the present
  • a plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound LV in a ratio of 0.1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and the compound LV in a ratio of 1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound LV in a ratio of 10: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound LVI in a ratio of 0.1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and the compound LVI in a ratio of 1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound LVI in a ratio of 10: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound LVI
  • a plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and compound LXIV in a ratio of 0.1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and the compound LXIV in a ratio of 1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and the compound LXIV in a ratio of 10: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and the compound LXV in a ratio of 0.1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and the compound LXV in a ratio of 1: 1; A plant disease control composition comprising any one of the present oxadiazole compounds A1 to A83 and the compound LXV in a ratio of 10: 1; A plant disease control composition comprising any one of the present oxadiazole compounds
  • Formulation Example 1 A composition is obtained by thoroughly pulverizing and mixing 50 parts of any one of the compositions of the present invention, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic silicon hydroxide.
  • Formulation Example 2 20 parts of any one of the compositions of the present invention 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.
  • a formulation is obtained by adding 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate, and further adding 10 parts of propylene glycol and stirring.
  • Formulation Example 3 A formulation is obtained by thoroughly pulverizing and mixing 2 parts of any one of the compositions of the present invention, 88 parts of kaolin clay and 10 parts of talc.
  • Formulation Example 4 A formulation is obtained by thoroughly mixing 5 parts of any one of the compositions of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.
  • Formulation Example 5 2 parts of the composition of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are mixed and mixed well with water. The formulation is obtained by granulating and drying.
  • Formulation Example 6 Formulation by mixing 10 parts of any one of the compositions of the present invention; 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt; and 55 parts of water and processing using a pulverizer Get.
  • Test Example 1 Control test against Septoria tritici
  • the final concentration of the present oxadiazole compound and the present bactericidal compound in a potato broth liquid medium (PDB medium) is described in [Table 7] to [Table 11].
  • a solution obtained by diluting and mixing the present oxadiazole compound and the present bactericidal compound with DMSO (dimethyl sulfoxide) to a concentration is dispensed to a titer plate (96-well), conidia spores of wheat leaf blight fungus in advance.
  • 150 ⁇ l of the PDB medium inoculated with 1 was dispensed. This plate was shaken and cultured at 18 ° C.
  • Test Example 2 Control test against soybean anthracnose fungus (Colletotrichum truncatum)
  • the final concentrations of the present oxadiazole compound and the present bactericidal compound in the potato broth liquid medium (PDB medium) are the concentrations described in Table 12 to Table 16.
  • 1 ⁇ l of a solution prepared by diluting the oxadiazole compound and the bactericidal compound with DMSO (dimethyl sulfoxide) and mixing them in a titer plate (96-well) 150 ⁇ l of the inoculated PDB medium was dispensed. This plate was cultured with shaking at 18 ° C.
  • Test Example 3 Control test against tomato leaf mold fungus (Cladosporium fulvum) The final concentrations of the present oxadiazole compound and the present bactericidal compound in the potato broth liquid medium (PDB medium) are described in [Table 17] to [Table 20].
  • Test example 4 A plastic pot is filled with soil, seeded with wheat (variety: Apogee), and grown in a greenhouse for 14 days.
  • the composition is formulated according to Formulation Example 6, diluted with water to a predetermined concentration, and sprayed so that the diluted solution adheres sufficiently to the leaf surface of the wheat. After spraying, the plants are air-dried, and after 2 days, sprayed with a water suspension (about 1,000,000 cells / ml) of conidia of wheat leaf blight fungus (Septoria tritici).
  • a water suspension about 1,000,000 cells / ml
  • conidia of wheat leaf blight fungus Septoria tritici
  • the lesion area of wheat leaf blight is investigated.
  • wheat is cultivated in the same manner as the treated area except that the diluted solution of the present composition is not sprayed on the foliage (this is referred to as the untreated area).
  • the lesion area of wheat leaf blight is investigated as in the treatment area.
  • a marked reduction in the lesion area of wheat treated with the disease control composition containing the present oxadiazole compound and the present bactericidal active compound is recognized as compared with the lesion area in the untreated area.
  • Test Example 5 The plastic pot is filled with soil, soybean (variety: Kurosengoku) is sown and grown in a greenhouse for 14 days. This composition is made into a preparation according to Preparation Example 6, and then diluted with water to a predetermined concentration, and the diluted solution is sprayed so as to adhere sufficiently to the leaves of the soybean. After spraying, the plants are air-dried, and after 2 days, spray-inoculated with an aqueous suspension (about 10,000 / ml) of a summer spore of soybean rust fungus (Phakopsora pachyrhizi). First, after inoculation, place under high humidity at 23 ° C. for 1 day, take out from high humidity and cultivate in a 23 ° C.
  • soybeans are cultivated in the same manner as the treated group except that the diluted solution of the present composition is not sprayed on the foliage (this is referred to as an untreated group). Then, the lesion area of soybean rust is investigated as in the treatment area. As a result, the lesion area of soybean treated with the disease control composition containing the present oxadiazole compound and the present bactericidal active compound is significantly reduced as compared with the lesion area in the untreated area.
  • plant diseases can be effectively controlled.

Abstract

L'invention concerne une composition de lutte contre des maladies végétales, contenant un composé d'oxadiazole représenté par la formule (1) [dans la formule, Z représente OC(=X)NR2R3, OC(=O)XR4 ou analogue, R1 représente un atome d'halogène, un groupe alcoxy en C1-4 ou analogue, n représente un entier de 0 à 2, R2 représente un groupe alkyle en C1-9, un groupe alcoxy en C1-4 ou analogue, R3 représente un atome d'hydrogène ou un groupe alkyle en C1-4, R4 et R5 représentent un groupe alkyle en C1-15, un groupe alcényle en C2-4 ou analogue, R7 représente un atome d'hydrogène ou un groupe alkyle en C1-4, R8 et R9 représentent un groupe alkyle en C1-9, un groupe halogénoalkyle en C1-4 ou analogue, et X représente un atome d'oxygène ou un atome de soufre], et un composé microbicide présente un excellent effet de lutte contre des maladies végétales.
PCT/JP2016/088078 2015-12-25 2016-12-21 Composition de lutte contre des maladies végétales et son application WO2017110864A1 (fr)

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WO2019002151A1 (fr) * 2017-06-28 2019-01-03 Syngenta Participations Ag Compositions fongicides
WO2019150219A2 (fr) 2018-01-30 2019-08-08 Pi Industries Ltd. Nouveaux oxadiazoles
WO2019171234A1 (fr) 2018-03-09 2019-09-12 Pi Industries Ltd. Composés hétérocycliques en tant que fongicides
US10501425B2 (en) 2015-10-02 2019-12-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2020070610A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd. Nouveaux oxadiazoles
WO2020070611A1 (fr) 2018-10-01 2020-04-09 Pi Industries Ltd Oxadiazoles utilisés comme fongicides
US10640497B2 (en) 2015-12-02 2020-05-05 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10757941B2 (en) 2016-07-22 2020-09-01 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10798941B2 (en) 2016-01-08 2020-10-13 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2020208511A1 (fr) 2019-04-08 2020-10-15 Pi Industries Limited Nouveaux composés d'oxadiazole pour la lutte ou la prévention contre des champignons phytopathogènes
WO2020208510A1 (fr) 2019-04-08 2020-10-15 Pi Industries Limited Nouveaux composés d'oxadiazole pour la lutte contre ou la prévention contre des champignons phytopathogènes
WO2020208509A1 (fr) 2019-04-08 2020-10-15 Pi Industries Limited Nouveaux composés d'oxadiazole pour la lutte ou la prévention contre des champignons phytopathogènes
US10899724B2 (en) 2015-10-02 2021-01-26 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11083196B2 (en) 2016-03-24 2021-08-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11192867B2 (en) 2016-06-03 2021-12-07 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
WO2022038500A1 (fr) 2020-08-18 2022-02-24 Pi Industries Limited Nouveaux composés hétérocycliques pour lutter contre des champignons phytopathogènes
WO2022234470A1 (fr) 2021-05-05 2022-11-10 Pi Industries Ltd. Nouveaux composés hétérocycliques condensés pour lutter contre des champignons phytopathogènes
EP4091451A1 (fr) 2021-05-17 2022-11-23 BASF Agro B.V. Compositions comprenant du méfentrifluconazole
US11653650B2 (en) 2017-09-06 2023-05-23 Ishihara Sangyo Kaisha, Ltd. Fungicide composition and method for controlling disease of crop

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US11180462B2 (en) 2015-10-02 2021-11-23 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11066375B2 (en) 2015-10-02 2021-07-20 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10899724B2 (en) 2015-10-02 2021-01-26 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10501425B2 (en) 2015-10-02 2019-12-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10640497B2 (en) 2015-12-02 2020-05-05 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10798941B2 (en) 2016-01-08 2020-10-13 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11259524B2 (en) 2016-01-08 2022-03-01 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11083196B2 (en) 2016-03-24 2021-08-10 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US11192867B2 (en) 2016-06-03 2021-12-07 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
US10757941B2 (en) 2016-07-22 2020-09-01 Syngenta Participations Ag Microbiocidal oxadiazole derivatives
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US11653650B2 (en) 2017-09-06 2023-05-23 Ishihara Sangyo Kaisha, Ltd. Fungicide composition and method for controlling disease of crop
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WO2022038500A1 (fr) 2020-08-18 2022-02-24 Pi Industries Limited Nouveaux composés hétérocycliques pour lutter contre des champignons phytopathogènes
WO2022234470A1 (fr) 2021-05-05 2022-11-10 Pi Industries Ltd. Nouveaux composés hétérocycliques condensés pour lutter contre des champignons phytopathogènes
EP4091451A1 (fr) 2021-05-17 2022-11-23 BASF Agro B.V. Compositions comprenant du méfentrifluconazole

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