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WO2017213137A1 - Nouveau composé et produit chimique agricole/horticole l'utilisant comme ingrédient actif - Google Patents

Nouveau composé et produit chimique agricole/horticole l'utilisant comme ingrédient actif Download PDF

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Publication number
WO2017213137A1
WO2017213137A1 PCT/JP2017/020971 JP2017020971W WO2017213137A1 WO 2017213137 A1 WO2017213137 A1 WO 2017213137A1 JP 2017020971 W JP2017020971 W JP 2017020971W WO 2017213137 A1 WO2017213137 A1 WO 2017213137A1
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group
alkoxy
alkyl
compound
agricultural
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PCT/JP2017/020971
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Japanese (ja)
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信弥 逸見
秀一 薄井
正浩 畠本
福地　俊樹
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アグロカネショウ株式会社
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Priority to JP2018521733A priority Critical patent/JPWO2017213137A1/ja
Publication of WO2017213137A1 publication Critical patent/WO2017213137A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—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
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-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
    • A01N43/60—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
    • A01N43/72—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
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
    • C07C235/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton

Definitions

  • the present invention relates to a novel compound, an intermediate thereof, an agricultural and horticultural drug containing the compound as an active ingredient, and a method for using the same.
  • pesticides that have been widely used in the past do not necessarily satisfy the requirements such as the effect, spectrum, residual effect, etc., and further, the number of application times and the reduction of the applied dose.
  • appearance of pests that have developed resistance to conventional general pesticides is also a problem.
  • triazole agents imidazole agents, pyrimidine agents, benzimidazole agents, dicarboximide agents, phenylamide agents.
  • pathogens that have developed resistance to various types of fungicides such as strobilurins and SDHI have emerged in various places, and the control of these resistant bacteria has become difficult year by year.
  • organophosphorus insecticides pyrethroid insecticides, benzoylurea insecticides, diamide insecticides, organotin acaricides, etc. have been put on the market.
  • resistant pests and ticks have emerged shortly after launch, and the decline in effectiveness has become a problem. Therefore, the emergence of new pesticides that exhibit sufficient control effects at low doses and have little adverse environmental impact on various pests that have developed resistance to conventional general agricultural and horticultural agents is always desired. It is rare.
  • Patent Documents 1 to 20 and Non-Patent Document 1 disclose carboxamide derivatives having the following structure having herbicidal activity or bactericidal activity (refer to CAS number).
  • Patent Document 1 Compound No. 48
  • Patent Document 2
  • Patent Document 3
  • Patent Document 4
  • Patent Document 5
  • Patent Document 6
  • Patent Document 7
  • Patent Document 8
  • Patent Document 9
  • Patent Document 10
  • Patent Document 11
  • Patent Document 12
  • Patent Document 13
  • Patent Document 14
  • Patent Document 15
  • Patent Document 16
  • Patent Document 17
  • Patent Document 19
  • Patent Document 20
  • Non-patent document 1
  • Patent Documents 2 to 3 and 5 to 20 and Non-Patent Document 1 do not disclose a group represented by the following formula as a substituent of the aniline part of the compound.
  • Patent Documents 1 and 4 do not disclose a phenyl group having a substituent represented by the above formula as a substituent bonded to the nitrogen atom of the amide portion of the compound.
  • the present inventors have found that the compound represented by the following formula (1), which is a novel compound, is useful as an agricultural and horticultural drug, It has been completed. That is, the present invention relates to the following [1] to [14].
  • R 1 is hydrogen, C 1-12 alkyl group, C 1-12 haloalkyl group, C 3-6 alkenyl group, C 3-6 haloalkenyl group, C 3-6 alkynyl group, C 3-6 haloalkynyl group, C 3-8 cycloalkyl group, C 3-8 halocycloalkyl group, C 3-8 cycloalkyl-C 1-6 alkyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 Alkoxy C 1-6 alkyl group, C 1-6 alkylcarbonyl group, C 1-6 haloalkylcarbonyl group, C 1-6 alkoxycarbonyl group, C 1-6 haloalkoxycarbonyl group, C 1-6 alkoxy C 1-6 Alkylcarbonyl group, C 1-6 alkoxycarbonyl-carbonyl group, mono (di) C 1-6 alkylaminocarbonyl group, mono (di) C 1-6 alkyla
  • X may be the same or different, and may be hydrogen, halogen, C 1-12 alkyl group, C 1-12 haloalkyl group, C 3-8 cycloalkyl group, C 1-6 alkoxy group, C 3-6 alkenyloxy group, C 3-6 alkynyloxy group, C 1-6 haloalkoxy group, C 3-6 haloalkenyloxy group, C 3-6 haloalkynyloxy group, C 1-6 alkylthio group, C 1-6 alkylsulfinyl group, C 1-6 alkylsulfonyl group, C 1-6 haloalkylthio group, C 1-6 haloalkylsulfinyl group, C 1-6 haloalkylsulfonyl group, a nitro group or a cyano group, Y represents a (Y 1 ) n 3 -hetero
  • V is 4-substituted The compound according to the above [1], its N-oxide or a salt thereof.
  • the manufacturing method including making the compound represented by these react.
  • a method for controlling plant pests comprising a step of treating pests and / or their habitats and / or seeds and / or plant propagation materials with the agricultural and horticultural agent according to [6]. .
  • a plant pest comprising a step in which a useful crop is grown, or a place where the useful crop is grown or a growing crop is treated with the agricultural and horticultural agent according to [6]. How to prevent.
  • a method for preparing an agrochemical composition comprising a step of mixing the agricultural and horticultural chemical according to [6] above with a bulking agent and / or a surfactant.
  • the compound of the present invention has an excellent effect as an agricultural and horticultural agent.
  • halogen represents a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
  • C 1-12 alkyl group means, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n- Pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, isohexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decyl group A linear or branched alkyl group having 1 to 12 carbon atoms
  • the “C 3-8 cycloalkyl group” refers to a cyclic cycloalkyl group having 3 to 8 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like.
  • the “C 3-8 halocycloalkyl group” is the same as, for example, 1-chlorocyclopropyl, 2,2-difluorocyclopropyl, 2,2-dichloro-1-methylcyclopropyl, 4,4-difluorocyclohexyl, etc.
  • a cyclic cycloalkyl group having 3 to 8 carbon atoms substituted with one or more halogen atoms which may be different is shown.
  • the “C 3-8 cycloalkyl-C 1-6 alkyl group” means a cyclic carbon atom having 3 to 8 carbon atoms such as cyclopropylmethyl, 1-cyclopropylethyl, cyclobutylmethyl, 2-cyclooctylpropyl, etc.
  • Examples of the C 1-6 haloalkyl group include a fluoromethyl group, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, 2 -Fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-iodoethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 1-fluoroisopropyl Group, 3-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, heptafluoropropyl group, 4-fluorobutyl group, 4-chlorobutyl, nonafluorobutyl group, 5,5,
  • Examples of the C 1-12 haloalkyl group include, in addition to the groups exemplified for the C 1-6 haloalkyl group, for example, 1-fluoroheptyl group, 1-fluorooctyl group, 1-fluoroundecyl group, 1-fluorododecyl group. And a linear or branched alkyl group having 1 to 12 carbon atoms and substituted with 1 to 13, preferably 1 to 9 halogen atoms.
  • Examples of the C 1-6 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, a cyclopropyloxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, and an n-pentoxy group. And a linear or branched alkoxy group having 1 to 6 carbon atoms such as an n-hexyloxy group.
  • Examples of the C 1-6 haloalkoxy group include a fluoromethoxy group, a dichloromethoxy group, a trichloromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a dichlorofluoromethoxy group, 1- Fluoroethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-iodoethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, penta Fluoroethoxy group, 1-fluoroisopropoxy group, 3-fluoropropoxy group, 3-chloropropoxy group, 3-bromopropoxy group, 4-fluorobutoxy group, 4-chlorobutoxy group, etc., preferably 1-9 Linear or branched having 1 to 6 carbon atoms substituted with
  • Examples of the C 2-6 alkenyl group include a vinyl group, 1-propenyl group, allyl group, isopropenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1,1-dimethyl-2-propenyl group, 1-ethyl-2-propenyl group, 1-methyl-2-butenyl group, 1-methyl-3-butenyl group, 2- At least one double at any position such as hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, etc.
  • Examples thereof include a linear or branched alkenyl group having 3 to 6 carbon atoms having a bond.
  • Examples of the C 3-6 haloalkenyl group include a 3-chloro-2-propenyl group, a 3,3-difluoro-2-allyl group, a 3,3-dichloro-2-allyl group, a 4,4,4-trimethyl group, and the like.
  • At least one double bond at any position such as fluoro-2-butenyl group, 4,4,4-trifluoro-3-butenyl group, 5-chloro-3-pentenyl group, 6-fluoro-2-hexenyl group And a straight-chain or branched alkenyl group having 3 to 6 carbon atoms and having 1 to 13, preferably 1 to 7 halogen atoms.
  • Examples of the C 2-6 alkynyl group include ethynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 1-butynyl group, 2-butynyl group, 3 -Butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 1,1-dimethyl-2- 3 to 6 carbon atoms having at least one triple bond at any position such as butynyl group, 1,1-dimethyl-3-butynyl group, 1-methyl-3-pentynyl group, 1-methyl-4-pentynyl group, etc.
  • C 3-6 haloalkynyl groups include 4,4,4-trifluoro-2-butynyl group, 5,5,5-trifluoro-3-pentynyl group, 1-methyl-3,3,3-trifluoro Linear or branched alkynyl having 3 to 6 carbon atoms and having at least one triple bond at an arbitrary position such as -2-butynyl group, 1-methyl-5,5,5-trifluoro-2-pentynyl group, etc. And an alkynyl group substituted with 1 to 9, preferably 1 to 6, halogen atoms.
  • the C 3-6 alkenyloxy group can be mentioned those with group to those exemplified in the C 3-6 alkenyl group.
  • the C 3-6 haloalkenyloxy group can be mentioned those with group to those exemplified in the C 3-6 haloalkenyl group.
  • the C 3-6 alkynyloxy group can be mentioned those with group to those exemplified in the C 3-6 haloalkenyl group.
  • the C 3-6 haloalkynyl group include those attached group to those exemplified in the C 3-6 haloalkenyl group.
  • Examples of the C 1-6 alkylthio group include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, a cyclopropylthio group, an n-butylthio group, a sec-butylthio group, a tert-butylthio group, and an n-pentylthio group.
  • a linear or branched alkylthio group having 1 to 6 carbon atoms such as an n-hexylthio group.
  • Examples of the C 1-6 alkylsulfinyl group include a methylsulfinyl group, an ethylsulfinyl group, an n-propylsulfinyl group, an isoprosulfinyl group, a cyclopropylsulfinyl group, an n-butylsulfinyl group, a sec-butylsulfinyl group, and a tert-butyl.
  • Examples thereof include a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms such as a sulfinyl group, an n-pentylsulfinyl group, and an n-hexylsulfinyl group.
  • Examples of the C 1-6 alkylsulfonyl group include methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isoprosulfonyl group, cyclopropylsulfonyl group, n-butylsulfonyl group, sec-butylsulfonyl group, tert-butyl. Examples thereof include a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms such as a sulfonyl group, an n-pentylsulfonyl group, and an n-hexylsulfonyl group.
  • Examples of the C 1-6 haloalkylthio group include a difluoromethylthio group, a trifluoromethylthio group, a monochloromethylthio group, a dichloromethylthio group, a trichloromethylthio group, a monobromomethylthio group, a dibromomethylthio group, a tribromomethylthio group, and a 1-fluoro group.
  • C 1-6 haloalkylsulfinyl group includes difluoromethylsulfinyl group, trifluoromethylsulfinyl group, dichloromethylsulfinyl group, trichloromethylsulfinyl group, monobromomethylsulfinyl group, dibromomethylsulfinyl group, tribromomethylsulfinyl group, 1- Fluoroethylsulfinyl group, 2-fluoroethylsulfinyl group, 2,2-difluoroethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 2-chloro-2,2-difluoroethylsulfinyl group, 1-chloroethyl Sulfinyl group, 2-chloroethylsulfinyl group, 2,2, -dichloroethylsulfinyl group,
  • Examples of the C 1-6 haloalkylsulfonyl group include a difluoromethylsulfonyl group, a trifluoromethylsulfonyl group, a dichloromethylsulfonyl group, a trichloromethylsulfsulfonyl group, a monobromomethylsulfonyl group, a dibromomethylsulfonyl group, and a tribromomethylsulfonyl group.
  • Examples of the C 1-6 alkoxy C 1-6 alkyl group include 1 to 6 carbon atoms such as methoxymethyl group, methoxy-2-ethyl group, ethoxymethyl group, isopropoxymethyl group, tert-butoxy-1-ethyl group, and the like.
  • Examples of the C 1-6 alkylcarbonyl group include linear or branched alkylcarbonyl groups having 1 to 6 carbon atoms such as a methylcarbonyl group, an ethylcarbonyl group, an isopropylcarbonyl group, and a tert-butylcarbonyl group.
  • Examples of the C 1-6 haloalkylcarbonyl group for example, a trifluoromethylcarbonyl group, a chloromethylcarbonyl group, a 3-bromopropylcarbonyl group, etc., preferably having 1 to 6 carbon atoms substituted with 1 to 9 halogen atoms A linear or branched alkoxy group is mentioned.
  • Examples of the C 1-6 alkoxycarbonyl group include linear or branched alkoxycarbonyl groups having 1 to 6 carbon atoms such as a methoxycarbonyl group, an ethoxycarbonyl group, a 1-fluoroisopropoxycarbonyl group, and a tert-butoxycarbonyl group. Is mentioned.
  • As the C 1-6 haloalkoxycarbonyl group for example, 1 to 13, such as trifluoromethoxycarbonyl group, 2-chloroethoxycarbonyl group, isopropoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, etc. are preferable.
  • Examples of the C 1-6 alkoxy C 1-6 alkylcarbonyl group include a methoxymethylcarbonyl group, a methoxy-2-ethylcarbonyl group, an ethoxymethylcarbonyl group, an isopropoxymethylcarbonyl group, and a tert-butoxy-1-ethyl group. Examples thereof include straight-chain or branched alkoxy having 1 to 6 carbon atoms and straight-chain or branched alkyl groups having 1 to 6 carbon atoms.
  • a mono (di) C 1-6 alkylamino group represents a mono C 1-6 alkylamino group or a diC 1-6 alkylamino group;
  • the mono C 1-6 alkylamino group include linear or branched alkylamino groups having 1 to 6 carbon atoms such as a methylamino group, an ethylamino group, and a tert-butylamino group.
  • the di-C 1-6 alkylamino group include linear or branched dialkylamino groups having 1 to 6 carbon atoms such as dimethylamino group, N-methyl-N-ethylamino group, and diethylamino group. .
  • Examples of the mono C 1-6 alkylaminocarbonyl group include linear or branched alkylaminocarbonyl groups having 1 to 6 carbon atoms such as a methylaminocarbonyl group, an ethylaminocarbonyl group, and a tert-butylaminocarbonyl group. It is done.
  • Examples of the di-C 1-6 alkylaminocarbonyl group include linear or branched dialkylaminocarbonyl having 1 to 6 carbon atoms such as dimethylaminocarbonyl group, Nmethyl-N-ethylaminocarbonyl group, and diethylaminocarbonyl group. Groups.
  • Examples of the C 1-6 hydroxyalkyl group include hydroxymethyl group, dihydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1,2-dihydroxyethyl group, 1-hydroxyisopropyl group, 3-hydroxypropyl group, Examples thereof include a 4-hydroxybutyl group, a 6-hydroxyhexyl group, and preferably a linear or branched alkyl group having 1 to 6 carbon atoms substituted with 1 to 2 hydroxy groups.
  • examples of the “aryl group” include phenyl group, 1-naphthyl group, 2-naphthyl group, anthracenyl group, phenanthrenyl group, acenaphthylenyl group and the like.
  • the “heteroaryl” may be monocyclic or polycyclic, and a heterocyclic group containing one or two or more of the same or different ring-constituting heteroatoms can be used.
  • the kind of hetero atom is not specifically limited, For example, a nitrogen atom, an oxygen atom, a sulfur atom etc. can be illustrated.
  • heterocyclic group examples include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, dihydroisoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, thiadiazolyl, triazolyl , Tetrazolyl group, pyrrolidinyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, azepinyl group, oxazepinyl group, piperidinyl group, morpholinyl group and the like.
  • polycyclic heterocyclic group examples include benzofuranyl group, isobenzofuranyl group, benzothienyl group, indolyl group, isoindolyl group, indazolyl group, benzoxazolyl group, benzoisoxazolyl group, benzothiazolyl group, benzoisothiazo group.
  • Ryl group benzooxadiazolyl group, benzothiadiazolyl group, benzotriazolyl group, quinolyl group, isoquinolyl group, cinnolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, naphthyridinyl group, purinyl group, pteridinyl group, carbazolyl group And 8- to 14-membered polycyclic heterocyclic groups such as carbolinyl group, acridinyl group, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, phenoxazinyl group, phenothiazinyl group and phenazinyl group.
  • Y represents a (Y 1 ) n 3 -heteroaryl-A- group or a (Y 1 ) n 4 -aryl-A- group, and preferred substituents include (Y 1 ) n 3 -pyridyloxy group or ( Y 1 ) n 4 -phenoxy group.
  • n 3 and n 4 each independently represents an arbitrary integer of 1 or more, preferably an integer of 1 to 10, more preferably an integer of 1 to 5.
  • Examples of (Y 1 ) n 3 -pyridyloxy group include 5-trifluoromethyl-2-pyridyloxy group, 3-chloro-5-iodo-2-pyridyloxy group, 5-iodo-2-pyridyloxy group, 3-fluoro-5-trifluoromethyl-2-pyridyloxy group, 3,5-dichloro-2-pyridyloxy group, 6-chloro-3-pyridyloxy group, 6-trifluoromethyl-3-pyridyloxy group, 4-pyridyloxy group can be mentioned.
  • Examples of the (Y 1 ) n 4 -phenoxy group include a 4-trifluorophenoxy group, a 4-iodophenoxy group, a 2-fluoro-4-trifluoromethylphenoxy group, and a 2,4-dichlorophenoxy group.
  • two Ws are substituted with two adjacent carbon atoms on the phenyl ring, these Ws are bonded to each other, and each W is bonded.
  • a saturated or unsaturated 5- or 6-membered ring may be formed together with the carbon atoms present, but for example, condensed with a phenyl ring to form an indane ring, a tetrahydronaphthalene ring, or a naphthalene ring, respectively.
  • Examples of the salt of the compound of the present invention represented by the formula (1) include inorganic acid salts such as hydrochloride, sulfate, nitrate, and phosphate, acetate, fumarate, maleate, oxalate, Examples thereof include organic acid salts such as methanesulfonate, benzenesulfonate, and p-toluenesulfonate.
  • the compound of the present invention represented by the formula (1) may contain one or more asymmetric centers in the structural formula, and there are two or more optical isomers and diastereomers.
  • the present invention includes all the optical isomers and mixtures containing them in an arbitrary ratio.
  • the compound represented by the said Formula (1) of this invention may contain a geometric isomer and a rotational isomer.
  • there may be two kinds of geometric isomers derived from carbon-carbon double bonds, but the present invention provides each geometric isomer, rotamer and a mixture containing them in an arbitrary ratio. Is also included.
  • R 1 and R 3 are hydrogen atoms
  • R 2 is hydrogen atom, halogen atom, C 1-3 alkyl group, C 1-3 alkoxy, C 1-3 haloalkoxy, C 1-3 alkoxy
  • a compound showing a C 1-3 alkyl group is preferred, and a compound wherein R 2 is a methyl group, an ethyl group or a propyl group is particularly preferred.
  • compounds in which Y represents a hydrogen atom are preferred.
  • reaction represented by the above reaction formula 1 can be carried out in the presence of a condensing agent and in the presence of a solvent and a base, or in the presence of a condensing agent and in the absence of a solvent and a base.
  • Solvents include aromatic hydrocarbons such as benzene, toluene, and xylene; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; halogenated hydrocarbons such as chloroform and methylene chloride; water; methyl acetate, Esters such as ethyl acetate; or ethers such as tetrahydrofuran, dioxane, diethyl ether, 1,2-dimethoxyethane; water; acetonitrile, N, N-dimethylformamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, etc. Polar solvents; alcohols such as methanol, ethanol and isopropanol, or mixed solvents of the above solvents.
  • Bases include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine; sodium hydroxide, potassium hydroxide, etc.
  • Examples of the condensing agent used in the reaction include 1,3-dicyclohexylcarbodiimide (DCC), 2-chloro-1-methylpyridinium iodide, carbonyldiimidazole (CDI), and trifluoroacetic anhydride. .
  • the reaction temperature is, for example, ⁇ 30 ° C. to 150 ° C., preferably ⁇ 5 ° C. to 80 ° C.
  • the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification by washing with a solvent, recrystallization, column chromatography or the like.
  • reaction represented by the above reaction formula 2 can be carried out in the presence or absence of a solvent and a base.
  • the solvent is not particularly limited as long as it does not directly participate in this reaction, and for example, aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform and Halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; or ethers such as tetrahydrofuran, dioxane, diethyl ether, and 1,2-dimethoxyethane; water; acetonitrile and N, N Examples thereof include polar solvents such as dimethylformamide, N-methyl-2-pyrrolidone, and dimethyl sulfoxide, or mixed solvents of the above solvents.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • ketones such as acetone, methyl ethyl ketone and methyl iso
  • Bases include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine; sodium hydroxide, potassium hydroxide, etc.
  • the reaction temperature is, for example, ⁇ 30 ° C. to 150 ° C., preferably ⁇ 5 ° C. to 80 ° C.
  • the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification by washing with a solvent, recrystallization, column chromatography or the like.
  • the compound represented by the formula (4) or the compound represented by the formula (3) can be produced according to the method described in Patent Document 1.
  • R 6 is a C 1-12 alkyl group, a C 1-6 haloalkyl group, a C 3-6 alkenyl, a C 3-6 haloalkenyl, a C 3-6 alkynyl group, C 3-6 haloalkynyl group, C 3-8 cycloalkyl group, C 3-8 halocycloalkyl group, C 3-8 cycloalkyl-C 1-6 alkyl group, C 1-6 alkoxy C 1-6 alkyl group C 1-6 alkylcarbonyl group, C 1-6 haloalkylcarbonyl group, C 1-6 alkoxycarbonyl group, C 1-6 haloalkoxycarbonyl group, C 1-6 alkoxy C 1-6 alkylcarbonyl group, C 1- 6 represents an alkylsulfonyl group, a C 1-6 haloalkylsulfonyl group, or a cyano group.
  • the solvent is not particularly limited as long as it does not directly participate in this reaction, and for example, aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform and Halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; or ethers such as tetrahydrofuran, dioxane, diethyl ether, and 1,2-dimethoxyethane; water; acetonitrile and N, N Examples thereof include polar solvents such as dimethylformamide, N-methyl-2-pyrrolidone, and dimethyl sulfoxide, or mixed solvents of the above solvents.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • ketones such as acetone, methyl ethyl ketone and methyl iso
  • Bases include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine; sodium hydroxide, potassium hydroxide, etc.
  • the reaction temperature is, for example, ⁇ 30 ° C. to 150 ° C., preferably ⁇ 5 ° C. to 80 ° C.
  • the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification by washing with a solvent, recrystallization, column chromatography or the like.
  • Reaction formula 4 [Wherein R 1 , R 2 , R 3 , V, W, X, Y, Z 1 , Z 2 , n 1 and n 2 are as defined in the above formula (1)]
  • reaction to obtain (7) can be carried out in the presence or absence of a solvent and a base.
  • the solvent is not particularly limited as long as it does not directly participate in this reaction, and for example, aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform and Halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; or ethers such as tetrahydrofuran, dioxane, diethyl ether, and 1,2-dimethoxyethane; water; acetonitrile and N, N Examples thereof include polar solvents such as dimethylformamide, N-methyl-2-pyrrolidone, and dimethyl sulfoxide, or mixed solvents of the above solvents.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • ketones such as acetone, methyl ethyl ketone and methyl iso
  • Bases include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine; sodium hydroxide, potassium hydroxide, etc.
  • the reaction temperature is, for example, ⁇ 30 ° C. to 150 ° C., preferably ⁇ 5 ° C. to 80 ° C.
  • the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification by washing with a solvent, recrystallization, column chromatography or the like.
  • reaction to obtain (1) can be carried out in the presence of a solvent and a base.
  • the solvent is not particularly limited as long as it does not directly participate in this reaction, and for example, aromatic hydrocarbons such as benzene, toluene and xylene; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; chloroform and Halogenated hydrocarbons such as methylene chloride; esters such as methyl acetate and ethyl acetate; or ethers such as tetrahydrofuran, dioxane, diethyl ether, and 1,2-dimethoxyethane; water; acetonitrile and N, N Examples thereof include polar solvents such as dimethylformamide, N-methyl-2-pyrrolidone, and dimethyl sulfoxide, or mixed solvents of the above solvents.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • ketones such as acetone, methyl ethyl ketone and methyl iso
  • Bases include organic bases such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), 4-dimethylaminopyridine; sodium hydroxide, potassium hydroxide, etc.
  • the reaction temperature is, for example, ⁇ 30 ° C. to 150 ° C., preferably ⁇ 5 ° C. to 80 ° C.
  • the target product may be isolated from the reaction system by a conventional method. If necessary, the target product can be produced by purification by washing with a solvent, recrystallization, column chromatography or the like.
  • the agricultural and horticultural agent according to the present invention contains, as an active ingredient, at least one selected from the group consisting of the compound of formula (1) or an N-oxide or a salt thereof.
  • the amount of the active ingredient contained in the agricultural and horticultural agent of the present invention is preferably 0.01 to 90% by mass, more preferably 0.05 to 85% by mass, still more preferably 0.00%, based on the entire preparation. It is about 05 to 80% by mass.
  • Formulations comprising the compound of formula (1) of the present invention or an N-oxide or salt thereof as an active ingredient are one or more fungicides, insecticides, acaricides, repellents, synergists, or plant growth regulators. It can be mixed or used together with an agent. The mixture thus obtained has a broad activity spectrum.
  • bactericides examples include those that can be mixed or used in combination with a preparation comprising the compound of formula (1) of the present invention or an N-oxide or salt thereof as an active ingredient are shown below. It is not limited to this.
  • bactericides that inhibit nucleic acid synthesis include, for example, benalaxyl, benalaxyl M, furalaxyl, metalaxyl, metalaxyl M, oxadixyl oxaxyl (Bupirimate), dimethylirimol, ethirimol, hydroxyisoxazole, hymexazole, octylinone, oxolinic acid and the like.
  • Bactericides that inhibit mitosis and cell division include, for example, benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate methyl, and thiophanate methyl. ), Zoxamide, zaralamid, ethaboxam, pencycuron, fluopicolide and the like.
  • fungicides that inhibit respiration include diflumetorim, tolfenpyrad, tebufenpyrad, fenazaquin, pyridaben, fenpyroximate, fenpyroximate benodanil, flutolanil, mepronil, isofetamide, fluopyram, fenfuram, carboxin, oxycarboxin, oxycarboxin, oxycarboxin Thifluzamide, benzovindiflupyr, bixafen, flixapyroxad, furamethpyr, iopyrafen, p , Boscalid, pyraziflumide, pydiflumethofen, isoflucipram, azoxystrobin, coxoxystrobin, coxoxystrobin tropin, fluphenoxystrobin, picoxystrobin, pyroxystrobin, pyracrostrobin, pyramethostrobin, triclopyrmethyl kresoxi
  • Bactericides that inhibit amino acid and protein synthesis include, for example, andoprim, cyprodinil, mepanipyrim, pyrimethanil, blasticidin S, kasugamyctomomycin ), Oxytetracycline, mildiomycin and the like.
  • Bactericides that inhibit signal transduction include, for example, quinoxyfen, proquinazid, fenpiclonil, fludioxonil, clozolinate, iprodion, crodinone Is mentioned.
  • Bactericides that inhibit lipid and cell membrane synthesis include, for example, edifenphos, iprobenfos, pyrazophos, isoprothiolane, biphenyl, chloroneb, techtozane, Examples thereof include methyl (tolclofos-methyl), ecromezole, iodocarb, propamocarb, and prothiocarb.
  • Bactericides that inhibit cell membrane sterol biosynthesis include, for example, triforine, pyrifenox, pyrisoxazole, fenarimol, nuarimol, imazaril, oxpoconazole, oxpoconazole Pefurazoate, prochloraz, triflumizole, azaconazole, bitteranol, zylconol, ciproconazole, ciproconazole, ciproconazole diniconazole, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, fluconazole, flusilazole, flusilazole, flusilazole, flusilazole, flusilazole, flusilazole, flusilazole (fluconazole), fluconazole (fluconazole), fluconazole (fluconazole), fluconazole (fluconazole), fluconazole (fluconazole), fluconazole
  • Bactericides that inhibit cell wall biosynthesis include, for example, validamycin, polyoxin, dimethomorph, flumorph, pyrimorph, bentiavalical, iprovalic, iproval, (Variiferate), mandipropamide, and the like.
  • fungicides include, for example, cymoxanil, fosetyl, phosphorous acid, phosphite, teclophthalam, triazoxide, flusulfamide (flusulfamide), flusulfamide (flusulfamide) dicolomezine, metasulfocarb, cyflufenamide, metraphenone, pyriophenone, dodine, fluthiain p, felimone p ), Torquerocarb (picolbutrazox), machine oil (petroleum oil), organic oil (organic oil), potassium hydrogencarbonate (carbonic acid), sodium hydrogen carbonate (sodium hydrogen) Sodium hypochlorite, calcium carbonate, benthiazole, diclobutrazol, flumetover, thiadiazin, loor di-tin in), shiitake mycelium extract, extract quinofumelin, quinoline compound described in WO 2011/081174 pamphlet, pyridazin
  • Examples of the compound (generic name) having insecticidal activity, acaricidal activity or nematicidal activity that can be mixed or used in combination with a preparation comprising the compound of the formula (1) of the present invention or an N-oxide or salt thereof as an active ingredient are shown below.
  • the insecticide, acaricide or nematicide which can be mixed or used together is not necessarily limited thereto.
  • organic phosphorus agent examples include acephate, azinephos-methyl, chlorpyrifos, diazinon, dichlorvos, dimethon-S-methyl (dimethon-S-methyl), Dimethylvinphos, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidothio (methathidothio) ion), monocrotophos, nared, oxydeprofos, parathion, phensoate, fosalone, pirimiphos-methyl, feihion profenofos, prothiofos, propopafos, pyraclofos, salithion, sulprofos, thiomethon, tetrachlorvinphos (tetrochlorv) richlorphon), mention may be made of Bamidochin (vamidothion) and the like.
  • carbamate agents examples include alanicalcarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, etiofencarb, ethofencarb. (Furathiocarb), isoprocarb, mesomyl, metolcarb, pirimicarb, propoxur, thiodicarb, and the like.
  • organic chlorine agent examples include aldrin, chlordane, DDT (p, p'-DDT), endosulfan, lindane and the like.
  • pyrethroid agents include acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cythothrin, cyphenthrin, and phenothrin.
  • neonicotinoids examples include acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, and thiaclopridum.
  • diamide agent examples include chlorantraniprole, cyantraniprore, cyclaniliprore, tetraniliprole, and fulbenedia.
  • insect growth control agents such as benzoyl urea agents include bistrifluron, chlorofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumulon ), Lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, cyromazine (in), cyromazine (in), cyromazine, etc.
  • phenylpyrazole agent examples include etiprole, fipronil, acetoprole, pyrafluoprol, pyriprole and the like.
  • nereistoxin agents examples include bensultap, cartap, thiocyclam, thiosultap, and the like.
  • diacylhydrazone agent examples include chromafenozide, halofenozide, methoxyphenozide, tebufenozide and the like.
  • juvenile hormone agents include diophenolan, phenoxycarb, hydroprene, methoprene, and pyriproxyfen.
  • insecticidal substances produced by microorganisms include, for example, abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin, nemadectin and nemadectin. , Polyoxin complex (polyoxin), spinetram, spinosad, BT agent (Bacillus thuringiensis and insecticidal protein product) and the like.
  • insecticidal substances derived from natural products include anabasine, azadirachtin, deguelin, fatty acid glycerides, hydroxypropyl starch, soybean starch, and soybean. ), Nornicotine, sodium oleate (orecic acid sodium salt), machine oil (petrolium oil), propylene glycol monofatty acid ester (propylene glycol monolaurate), rape oil (rope oil), rotenone roten (on) Rubitan fatty acid esters (Sorbitan fattyacid ester), mention may be made of starch (starch) and the like.
  • insecticides include, for example, afidopyropen, brofuranilide, chlorfenapyr, diafenthiuron, didichloromezothiaz, dichromezothiaz, dichromezothiaz (Flonicamid), flometoquin, flufenerim, fluhexafone, flupyradifurone, hydramethylnon ), Indoxacarb, metaflumizone, metaldehyde, nicotine sulfate, pymetrozine, pyridalyl, spiridrofluidyl (Sulfuramid), sulfoxafluor, triflumezopyrim, tolfenpyrad, triazamate, and the like.
  • acaricides include acequinocyl, acinonapyr, amidoflumet, amitraz, azocyclotin, benzomate, benzomate, benzomate. Bromopropyrate, quinomethionate, clofentezine, cienopyrafen, cyflumetofen, tricyclohexyltin hydroxide, diolformi Le (dienochlor), Jifurobidajin (diflovidazin), etoxazole (ethoxazole), Fenazafuroru (fenazaflor), fenazaquin (fenazaquin), fenbutatin oxide (fenbutatin oxide), fenothiocarb (fenothiocarb), fenpyroximate (fenpyroximate), fluacrypyrim (fluacrypyrim), hexythiazox (Hexythiazox ), Pyrimidifene, poly
  • nematicides for example, aluminum phosphide, benclothiaz, cadusafos, etoprofos, fluensulfone, fluopyram, fluopyram, fluopyram, fluopyram , Imiciafos, levamisole hydrochloride, mesulfenfos, methamfenfos, methyl isothiocyanate, mortar of tartaric acid e), oxamyl (oxamyl), thifluzamide (thifluzamide), mention may be made of Chiokisazafen (thioxazafen) and the like.
  • poison baits include chlorofacinone, coumatetralyl, diphacin, difluoroacetate, warfarin and the like.
  • composition provided by the present invention can be used for prevention and extermination of harmful pests in agriculture, indoors, forests, livestock, sanitation, and other scenes. Specific use scenes, target pests, and usage methods are shown below, but the contents of the present invention are not limited to these.
  • the agricultural and horticultural pharmaceutical composition of the present invention includes agricultural crops such as food crops (rice, barley, wheat, rye, oats and other wheat, potatoes, sweet potatoes, taro, potatoes such as potatoes, soybeans, red beans, Beans such as broad beans, green beans, green beans, peanuts, corn, persimmons, buckwheat, etc., vegetables (cabbage, Chinese cabbage, radish, persimmon, broccoli, cauliflower, komatsuna), cruciferous crops, pumpkin, cucumber, watermelon, ma Cucumber, melon, zucchini, cucumber, cucumber, cucumber, aubergine, eggplant, tomato, pepper, red pepper, mushrooms, mushrooms, mushrooms, spinach, red pepper, etc.
  • agricultural crops such as food crops (rice, barley, wheat, rye, oats and other wheat, potatoes, sweet potatoes, taro, potatoes such as potatoes, soybeans, red beans, Beans such as broad beans, green beans, green beans, peanuts, corn, persimmons, buckwhe
  • the pests targeted by the agricultural and horticultural pharmaceutical composition of the present invention include fungi such as Mycota, Myxomycota, Bacteriomycota, Actinomycota, and the like. And can be used to control the diseases they cause.
  • diseases include rice blast (Piculararia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), brown rot (Panteoanaanatis), idiophyllia eu Seedling blight (Pythium graminicum), Brown streak (Acidovorax avene subsp. Avenae), Leaf sheath browning (Pseudomonas fuscovaginae), Bacterial blight (Xanthomonas oryzae v.
  • Reezae p. Of powdery mildew (Erysiphe graminis), red mold (Gi) berella zeae), red rust (Puccinia striformis, P. graminis, P. recondita, P. hordei), snow rot (Typhula sp., Micronella nivalis), black scab (U. (Tilletia caries), eye spot disease (Pseudocercosporella herpotrichoides), cloud disease (Rhynhosporum secoris), leaf blight (Septoria territory disease) tum Ikata), black spot disease (Pseudomonas syringae pv.
  • citrus black spot disease (Diaporthe citria), common scab (Elsinoe fawceti), brown rot (Penicillium rot). citrophthora ,, P. nicotianae), black scab (Phyllostictina citricarpa), etc .
  • pirina powdery mildew (Phyllactinia mary), black spot disease (Alternaria kikuchiana), erythematosis (Gimnosporium haraenum), erythema disease (monilia fructigena) Monilinia fracticola, anthrax (Glomerella cingula), larvae of larvae (Monilinia fukuticola), black scab (Cladosporium carposis) Disease (Xanthomonas camp) estris pv.
  • Grapes black rot (Elsinoe ampelina), late rot (Colletotrichum acutatum), Glomerella cinulata, powdery mildew (Uncinula necator), rust pso , Downy mildew (Plasmopara viticola), Black star disease (Cladosporium viticolum), basidiomycete bacterial disease (Agrobacterium vitis), etc .
  • oyster anthracnose (Gloeosporium kakicola), powdery mildew (Phyllactinia kakicola), deciduous leaf disease (Cercosporicus kakicola) Horn spot disease (Phomopsis sp.), Anthracnose (Colletotrichum gloeosporioids), white leaf blight (Rosellinia necatoroid erystocerosis) Anthracnose (Colletotrichum lagenariaum), powdery mildew (Sphaer
  • Cabbage Rot (Pseudomonas syringae pv marginalis), black rot (Xanthomonas campestris pv campestris Lettuce downy mildew (Rhizoctonia solani), rot disease (Pseudomonas viridiflava), spot bacterial disease (Xantampon rastropon.
  • Carrotorumum Carrotorumum
  • strawberry powdery mildew Sphaerothecium umuli
  • anthrax Phytophthora nicotianae Dendroboma obscurans
  • Bacterial blight Bacterial blight (Pseudomonas marginalis pv. Marginalis), etc .
  • Brown brown streak of tea Pseudocercosporathee's disease, Pseudocercosporathee's disease) theae
  • Pestaliopsis longiseta net blast (Exobasidium reticulatum), rice blast (Exobasidium vexans), white scab (Elsinoe leucospila), red burning (Pseudomonas sapiens.
  • scab Xanthomonas campestris pv. theicola
  • tobacco red rot Alternaria longipes
  • powdery mildew Erysiphaticobacter's disease
  • Nicotianae Blight disease (Ralstonia solaacearum)
  • Cavity disease Pectobacterium carotovorum subsp.
  • Powdery mildew (Uncinula sp.). , White spot disease (Phomatospora albomaculans), powdery mildew (Uncinula sp., Microsphaera alphitoides), Erysiphe gracilis, Armillariamellius disease Spot disease (Septoria chinensis), blight (D aporthe melanocarpa, Diaporthe alleghaniensis), Kusunoki of anthracnose (Glomerella cingulata), gardenia of Susukabi disease (Passalora okinawaensis), leaf spot (Phaeosphaerella gardeniae), brown spot disease of Zelkova (Pseudocercospora zelkovae), if bamboo disease (Armillaria mellea) , Fistula powdery mildew (Phyllactinia magnoliae), spotted disease (Phyllostica concentrica), cherry blossoms (N
  • pests include Lepidoptera, Coleoptera, Hemoptera, Hemoptera, Thomoptera, and Thysanoptera (Hymenoptera), fly order (Diptera), grasshopper order (Orthooptera), termite order (Isoptera), earworm (Dermaptera), Arthropoda side insect class Collembola, Arthropoda crustacea, etc.
  • Legs Isopada
  • Arthropoda spider mite Acari
  • Mollusc antiogastropod primitive string tongue (Architaenioglossa)
  • Linear animal genus genus Tyrenx T lenchida
  • a pest is not limited to these.
  • Lepidoptera of the Arthropoda elegans examples include Lepidoptera (Helicoverpa armigera), Heliothis spp., Agrotis segetum, and Managinographia. ), Yeoga (Mamestra brassicae), Shirochimodojiyoto (Spodoptera exigua), Spodoptera atracha saga (Plutella xylostella), and the like Echinaceae (Adoxophyes honmai), Midarekae Umumakigi (Archips fusucupureanus), Chamonaki (Homona magnima) et al.
  • Coleoptera for example, Anomala cupurea, Populus japonica, Oxycetonia jucunda, Akamula genus, etc. , Memanotus fortumi, etc., Epilachna vigintioctopuncta, etc., Anomalophalis, Anopalophora rrhoderus, potato beetle (Alacophora femoralis), rootworm species (Diabrotica spp.), killer whale beetle (Phylotretta striola), beetle potato beetle (Cassida nebulosa).
  • Hemoptera Heteroptera examples include, for example, Eurydema rugosum, Eysarcoris lewisi, Esarsarvous, Eysarvoris Stink bugs (Platia stali), Ragwort bugs (Harymorpha mista), Relative bugs (Urochela luteovoria), Rabbit bugs, Rabbitaceae (River) , Hosoharika Mussel (Cletus puntigger), etc., Leptocorisa chinensis, etc .; Streptomyceae (Apolygus spinolai), Akajikasumi turtle (Stenothus rubrovittalus), Trichonotylus coelestialium, etc .; Insects, larvae and eggs, and the like can be given.
  • Homoptera examples include Homoptera, such as Platypleura kaempferi, Arboridia apicoli, and N. cerevisiae. , Nephotettix virescens, etc., Lamindelfax striatellus, Japanese green planta (Nilaparvata lugens), White-spotted planta (Sokatella furomofera) nctissima) and other species, Psylla pyrisuga, various citrus leafworms (Diaphorina citrii), and other species such as Bifolia citrus species.
  • Homoptera such as Platypleura kaempferi, Arboridia apicoli, and N. cerevisiae. , Nephotettix virescens, etc., Lamindelfax striatellus, Japanese green planta (Nilaparvata lugens), White-spotted planta (Sokatella furomofera) nctissima) and other species, Psylla pyrisuga
  • Citrus whitefly (Dialeurodes citri), Onitsu whitefly (Trialeurodes vapariorirum), etc., phyllocera family grape aphids (Viteus vitifoliii), etc., Aphidaceae Yuukiyanagiburamushi (Aicalis aphid) craccivora), cotton aphid (Aphis gossypii), potato aphid (Aulacorthum solani), radish aphid (Brevicoryne brassicae), Komi can aphid (Toxoptera aurantii), mandarin orange black aphid (Toxoptera citricidus), elder aphid (Aulacorthum magnoliae), pear Aphids (Schizophis piricola), Nasimidori aphids (Nippolachnus piri), Nisedaikon aphids (Liphaphis erysimi),
  • Thysanoptera and to, for example, yellow tea thrips thrips family (Scirtothrips dorsalis), southern thrips (Thrips palmi), green onion thrips (Thrips tabaci), soybean mouse thrips (Thrips setosus), Hirazuhanaazamiuma (Frankliniella intonsa), mandarin orange Yellow thrips (Frankliniella occidentalis), Croton thrips (Heliotrips haemorrhoidalis), etc., Phyto thrips (Ponticothrips diospyropis) culeatus) adult, etc., it can be mentioned the larvae and eggs and the like.
  • bees include, for example, the bee of the waspaceae (Athalia rosae ruficornis), the horn bee (Arge pagana), and the like. Examples include adults, larvae, eggs, and the like, such as Megachile nipponica nipponica, and other ants of the ant family, Formica japonica.
  • flies examples include, for example, the soybean flies of the family Frostaceae (Asphondylia yushimai), the fruit flies of the family Frogidae (Rhacochlaena japonica), the flies of the fruit flies (Bactrocera ciraceae). Drosophila suzukii, etc., Limemya trifolii, etc., and Nabae Department of seedcorn maggot (Delia platura), onion maggot (Delia antiqua) adults such as, mention may be made of the larvae and eggs and the like.
  • orthoptera examples include, for example, the grasshopper (Rusporia lineosa) of the family Krygudidae, the pine weevil (Truljalia hibinonis), etc., the moth of the family Kela (Glylottalpa orientis), etc. Examples include larvae and eggs.
  • Examples of the termites include adults, larvae and eggs, such as the termite family Odontotermes formosanus.
  • Examples of the order Dermaptera include adults, larvae, eggs, and the like, such as Labidaura riparia.
  • Collembola of the Arthropoda side insect class include adults such as larvae such as Stomthulus viridis, pine moth, and larvae such as Onchiurus matsusumotoi.
  • Examples of the isopoda of the arthropod phylum Crustacea include adults, larvae, eggs and the like, such as Armadillium vulgare of the family Gillidae.
  • mites of the arthropod arachnid include, for example, the mite mites (Polyphagotaronemus latus), the cyclamen mite mite (Phytonemus pallidus), the mite mites (Penthaleus mahida), Brevipalpus lewisi, Brewipalpus phoenicis, etc., Mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite spider mite
  • Grape ticks (Colomerus vitis), moss mite (Aculus fockeii), chanosabi mite (Calacarus carinatus), and the like, Tyraphagus putrescentiae, Robinne tick (Rhizogiri) us robini) adults such as, mention may be made of the larvae and eggs and the like.
  • the archaeenioglossa of the mollusc anterogastronomy for example, Pomacea canalicula, such as the mosquito family, such as Plumonata, for example, the Achatina falica of the family Amythidae, (Migiumium bilineatum), Niwako urchinaceae (Milax gagates), Aurora amphiidae (Lehmannina valentiana), Species sect.
  • Pomacea canalicula such as the mosquito family
  • Plumonata for example, the Achatina falica of the family Amythidae, (Migiumium bilineatum), Niwako urchinaceae (Milax gagates), Aurora amphiidae (Lehmannina valentiana), Species sect.
  • Tylenchidae of the linear genital genital class examples include, for example, the Anguinaceae Imogusaresenchu (Ditylenchus destructor), the Tyrencorhynus pylaenus Pylenaceae, ), Nymphaea nematode (Pratylenchus coffeae), etc., Namila nechu (Helocotylenchus dihystera), etc., potato cyst nematode (Globodera rostochiensis), etc.
  • the long-tailed nematode Xifinema sp.
  • the pharmaceutical composition for agricultural and horticultural use of the present invention is highly safe for crops and useful organisms, and has low toxicity to various organisms such as fish and warm-blooded animals.
  • the pharmaceutical composition for agricultural and horticultural use of the present invention is resistant to existing agents such as benzimidazole agents, dicarboximide agents, anilinopyrimidine agents, strobilurin agents, SDHI agents, and fluazinam agents. Excellent bactericidal activity against resistant bacteria.
  • the pharmaceutical composition for agricultural and horticultural use of the present invention can also be used for the prevention and treatment of diseases of organs such as the skin, digestive system and respiratory system of humans, livestock and pets.
  • pathogenic bacteria that cause disease include Trichophyton rubrum and Trichophyton mentagrophytes such as trichophytic fungi, Candida albicans such as Candida fungi, Aspergillus E. coli fungi such as Candida albicans, Gram negative bacteria such as Pseudomonas aeruginosa, Gram positive bacteria such as Staphylococcus aureus, and the like.
  • the compound represented by the formula (1) of the agricultural and horticultural agent of the present invention includes a compound having insecticidal activity, acaricidal activity or nematicidal activity in addition to a compound having fungicidal activity, and other active compounds other than these compounds. It can also be present as a mixture. In order to control diseases and / or weeds that occur at the same time of use, it can be used in combination with a compound having fungicidal activity, herbicidal activity, or plant growth regulating activity, thereby reducing the control effort and reducing the dosage. Synergistic effects can be expected. Moreover, more effective control effects, such as a synergistic effect, can be expected by using a mixture with a repellent or a synergist.
  • the agricultural and horticultural chemicals of the present invention can be used as they are or in general as a pesticide. It can be used in dosage forms such as flowable agents such as agents, capsules, powders, granules, fine granules, baits, tablets, sprays, fumes, aerosols and the like.
  • the agricultural and horticultural medicine of the present invention contains 0.1 to 99.9% by mass, preferably 0.2 to 80% by mass of the active ingredients in total.
  • various agricultural chemical adjuvants conventionally used in the technical field of agricultural and horticultural medicine can be used as appropriate.
  • Such agrochemical adjuvants can be used for the purpose of, for example, improving the effects, stabilizing, and improving dispersibility of agricultural and horticultural chemicals.
  • the agricultural chemical adjuvant include a carrier (diluent), a spreading agent, an emulsifier, a wetting agent, a dispersing agent, a disintegrating agent, and the like.
  • Liquid carriers include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, methyl Mention may be made of naphthalene, cyclohexane, animal and vegetable oils, fatty acids and the like.
  • solid carrier clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like can be used.
  • a normal surfactant can be used as the emulsifier and the dispersant.
  • anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine, etc.
  • Cationic surfactants, nonionic surfactants, amphoteric surfactants, and the like can be used.
  • spreading agents wetting agents such as dialkyl sulfosuccinate; fixing agents such as carboxymethyl cellulose and polyvinyl alcohol; disintegrating agents such as sodium lignin sulfonate and sodium lauryl sulfate can be used.
  • soil All layers mixed cropping application, side strip application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface treatment, etc. Can also be used. It can also be used by soaking seeds in chemicals, seed dressing, seed treatment such as calper treatment, application to nutrient solution in nutrient solution (hydroponic) cultivation, smoke, or trunk injection.
  • the preparation is diluted or diluted with water.
  • spraying granules to plant seedling or seedling nursery, etc., before sowing or transplanting powder, wettable powder, granule Method of spraying wettable powder, granule, etc. and mixing with the whole soil, before sowing or planting plant, powder, wettable powder, wettable granule powder, fine powder, fine powder on planting holes, crops etc. And the like.
  • wettable powders For wettable powders, granular wettable powders, aqueous solvents, emulsions, liquids, flowables such as aqueous suspensions and emulsions, dilute with water, generally 5 to 500 liters per 10 ares Then, it may be sprayed on the soil surface or irrigated into the soil so as to be uniform over the entire area to be treated. Powders, granules, fine granules, baits and the like may be sprayed on the soil surface so that they are evenly distributed over the entire area to be treated. Spraying or irrigation may be around the seeds, crops or trees that you want to protect from harm. Further, the active ingredient can be mechanically dispersed by tilling during or after spraying.
  • the total amount of active ingredients per 10 ares is generally 0.01, although it varies depending on the type and amount of pests and the target crop / tree type, cultivation form / growth state or soil type. -1000 g, preferably 0.1-500 g are applied.
  • the method of application to the seedling box of paddy rice may vary depending on the application time such as application at seeding, application at the greening period, application at the time of transplantation, etc.
  • the wettable powder, granular wettable powder, aqueous solvent, emulsion, liquid, flowable preparation such as aqueous suspension and aqueous emulsion, capsules and the like may be used after diluted with water. It can also be applied by mixing with cultivated soil, and can be mixed with cultivated soil and powder or granules, for example, mixed with floor soil, mixed with cover soil, mixed into the entire cultivated soil, and the like. Alternatively, the culture medium and various preparations may be applied alternately in layers.
  • solid preparations such as jumbo agents, pack agents, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields.
  • an appropriate preparation can be sprayed and injected into the soil as it is or mixed with fertilizer.
  • chemicals such as wettable powder, emulsion, flowable, etc. as the source of water flowing into the paddy field such as a water mouth or an irrigation device, it can be applied labor-saving along with the supply of water.
  • Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted to immerse the seed in a liquid state to attach and permeate the drug, a solid preparation or liquid preparation is mixed with the seed, Examples thereof include a method of dressing and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as resin and polymer, and a method of spraying around the seed simultaneously with planting.
  • the “seed” for performing the seed treatment means a plant body at an early stage of cultivation used for plant propagation. For example, in addition to seeds, nutrition for bulbs, tubers, seed buds, buds, baskets, bulbs or cuttings cultivation Mention may be made of plants for breeding.
  • the “soil” or “cultivation carrier” of a plant when applied refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. Any material can be used as long as it can grow, so-called soil, seedling mat, water, etc. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel material, polymer material, rock Examples include wool, glass wool, wood chips, and bark. When used, the total amount of active ingredients per kilogram of seed is 0.001 to 50 g, preferably 0.01 to 10 g.
  • the irrigation treatment of the liquid drug or the granule spraying treatment to the seedling nursery is preferable.
  • the agricultural and horticultural pharmaceutical composition of the present invention is intended to prevent and treat the occurrence and spread of diseases of organs such as the skin, digestive system and respiratory system that are parasitic on the body surface of humans, livestock and pets, or in the body.
  • the compound of the present invention is mixed in a small meal or feed, a suitable pharmaceutical composition that can be taken orally, such as tablets, pills containing pharmaceutically acceptable carriers and coating substances, Capsules, pastes, gels, beverages, medicinal feeds, medicinal drinking water, medicinal supplements, sustained-release large pills, other sustained-release devices designed to be retained in the gastrointestinal tract, sprays, powders, It can be administered transdermally as grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo and the like.
  • 0.0001 to 0.1%, preferably 0.001 to 0.01% by weight is contained as a total amount of the active ingredient compounds.
  • the melting point of the obtained compound was 90-100 ° C.
  • FIG. 2- [4-[[5- (Trifluoromethyl) -2-pyridyl] oxy] phenoxy] -N-methoxymethylcarbonyl-N-[(2-chloro-4-heptafluoroisopropyl-6-methyl) phenyl ] Synthesis of propanamide (Compound No.
  • the obtained organic layer was washed with water and saturated aqueous sodium hydrogen carbonate.
  • the extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • the melting point of the obtained compound was 112-114 ° C.
  • Table 1 below shows the 1 H-NMR data of compounds produced in the same manner as in the above Examples.
  • Emulsion Compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts), Solpol 3005X (mixture of nonionic surfactant and anionic surfactant, Toho Chemical Industry Co., Ltd. (trade name) (10 parts) was uniformly mixed and dissolved to obtain an emulsion.
  • Formulation Example 5 Aqueous solvent-1 The compound of the present invention (20 parts), Lunox P-65L (alkyl allyl sulfonate, Toho Chemical Industry Co., Ltd., trade name) (3 parts), water-soluble carrier potassium chloride (77 parts) were mixed and ground uniformly. A water solvent was obtained.
  • Lunox P-65L alkyl allyl sulfonate, Toho Chemical Industry Co., Ltd., trade name
  • water-soluble carrier potassium chloride 77 parts
  • Formulation Example 6 Aqueous solvent-2 The compound of the present invention (50 parts), Newkalgen BX-C (Na alkylnaphthalene sulfonate, Takemoto Yushi Co., Ltd., trade name) (5 parts), water-soluble carrier potassium chloride (45 parts) are uniformly mixed and pulverized. Thus, an aqueous solvent was obtained.
  • Newkalgen BX-C Na alkylnaphthalene sulfonate, Takemoto Yushi Co., Ltd., trade name
  • water-soluble carrier potassium chloride 45 parts
  • Formulation Example 7 Flowable Agent-1 Premixed propylene glycol (5 parts), Solpol 7933 (anionic surfactant, Toho Chemical Co., Ltd., trade name) (5 parts), water (50 parts) and compound of the present invention (20 parts) was dispersed into a slurry mixture, and this slurry mixture was then wet pulverized, and then xanthan gum (Kelzan, Sanki Co., Ltd., trade name) (0.2 parts) was previously added to water (19.8 parts). What was well mixed and dispersed was added to obtain a flowable agent.
  • xanthan gum Kelzan, Sanki Co., Ltd., trade name
  • Formulation Example 8 Flowable Agent-2 Compound of the present invention (20 parts), Newkalgen FS-26 (mixture of dioctyl sulfosuccinate and polyoxyethylene tristyryl phenyl ether, Takemoto Yushi Co., Ltd., trade name) (5 parts), propylene glycol (8 parts), Water (50 parts) was mixed in advance, and the slurry mixture was wet pulverized. Next, xanthan gum (0.2 parts) was thoroughly mixed and dispersed in water (16.8 parts) to prepare a gel-like material, which was thoroughly mixed with the pulverized slurry to obtain a flowable agent.
  • Newkalgen FS-26 mixture of dioctyl sulfosuccinate and polyoxyethylene tristyryl phenyl ether, Takemoto Yushi Co., Ltd., trade name
  • propylene glycol 8 parts
  • Water 50 parts
  • xanthan gum 0.2 parts was thoroughly mixed and dispersed in water (16.8 parts) to
  • Antifoaming agent Antihome E-20 (emulsion-type modified silicone, Kao Corporation, trade name) (0.1 part) was added to the obtained dispersion, and xanthan gum dispersed in propylene glycol (5.0 parts) (Kelzan, Sanki Co., Ltd., trade name) (0.2 parts) was added to obtain an emulsion formulation (phase inversion emulsification method).
  • Formulation Example 10 EW-2 The compound of the present invention (10 parts) was dissolved in xylene (10 parts) and mixed with the surfactant Rheidol 430V (polyoxyethylene sorbite tetraoleate, Kao Corporation, trade name) (24 parts). Liquid obtained in water (50.6 parts), antifoaming agent Antihome E-20 (emulsion-type modified silicone, Kao Corporation, trade name) (0.1 part), preservative Proxel GX-L (Lonza) Japan Co., Ltd.
  • Rheidol 430V polyoxyethylene sorbite tetraoleate, Kao Corporation, trade name
  • Liquid obtained in water (50.6 parts), antifoaming agent Antihome E-20 (emulsion-type modified silicone, Kao Corporation, trade name) (0.1 part), preservative Proxel GX-L (Lonza) Japan Co., Ltd.
  • Formulation Example 11 ME Agent-1
  • the compound of the present invention (0.01 part) and Solpol CA-42 (nonionic activator, Toho Chemical Co., Ltd., trade name) (0.1 part) were mixed and homogenized, and then gradually mixed with stirring. (99.79 parts) was added.
  • Preservative Proxel GX-L Lionza Japan Co., Ltd., trade name
  • Formulation Example 14 Granule-1 Compound of the present invention (15 parts), Sun extract P-252 (sodium lignin sulfonate, Nippon Paper Industries Co., Ltd., trade name) (5 parts), Lunox P-65L (alkyl allyl sulfonate, Toho Chemical Co., Ltd.) (Product name) (2 parts), Sado bentonite (Kanto bentonite industry Co., Ltd.) (20 parts) and kaolin clay (Kaolinite, Takehara Chemical Co., Ltd., trade name) (58 parts) were uniformly mixed and ground in an air mill. . Water was added to this mixture and kneaded well, followed by extrusion granulation and dry sizing to obtain granules.
  • Sun extract P-252 sodium lignin sulfonate, Nippon Paper Industries Co., Ltd., trade name
  • Lunox P-65L alkyl allyl sulfonate, Toho Chemical Co., Ltd.
  • Formulation Example 15 Granule-2 Silica sand (90 parts) was placed in a rolling granulator and allowed to contain water, and then the compound of the present invention (5 parts) and sun extract P-252 (sodium lignin sulfonate, Nippon Paper Industries Co., Ltd.) previously pulverized and mixed. , Trade name) (4 parts), GOHSENOL GL05 (polyvinyl alcohol, Nippon Synthetic Chemical Industry Co., Ltd., trade name) (0.5 parts) and nip seal NS-K (white carbon, Tosoh Silica Corporation, trade name) ( 0.5 parts), and after coating, dry sized to obtain granules.
  • sun extract P-252 sodium lignin sulfonate, Nippon Paper Industries Co., Ltd.
  • trade name 4 parts
  • GOHSENOL GL05 polyvinyl alcohol, Nippon Synthetic Chemical Industry Co., Ltd., trade name
  • nip seal NS-K white carbon, Toso
  • Formulation Example 16 Granule-3 Ishikawa Light (Ishikawa Light Industry Co., Ltd., trade name) (89 parts) was placed in a rolling granulator, and after adding water, the compound of the present invention (5 parts), Sun Extract P- 252 (sodium lignin sulfonate, Nippon Paper Industries Co., Ltd., trade name) (3 parts), Aerol CT-1L (dioctyl sulfosuccinate, Toho Chemical Co., Ltd., trade name) (0.5 parts), Solpol 5276 Ion activator, Toho Chemical Industry Co., Ltd., trade name) (2 parts) and Gohsenol GL05 (polyvinyl alcohol, Nippon Synthetic Chemical Industry Co., Ltd., trade name) (0.5 parts) are coated, dried and sized. To obtain granules.
  • Sun Extract P- 252 sodium lignin sulfonate, Nippon Paper Industries Co., Ltd., trade name
  • Formulation Example 17 Fine granules-1
  • the compound of the present invention (2 parts) was diluted with a solvent, and mixed with Ishikawa Light (Ishikawa Light Industry Co., Ltd., trade name) (98 parts) while spraying the diluted solution.
  • the obtained granular composition was dried and sieved to obtain a fine granule.
  • Fine granules-2 The compound of the present invention (5 parts) is subjected to air mill grinding or mechanochemical grinding as required.
  • Toxanone GR-31A polycarboxylic acid type anionic surface active agent
  • No. 6 silica sand Ube Sand Industry Co., Ltd., trade name
  • Formulation Example 19 Powder A compound of the present invention (2 parts), Nipseal NS-K (white carbon, Tosoh Silica Co., Ltd., trade name) (10 parts) and Kaolin clay (Kaolinite, Takehara Chemical Co., Ltd., trade name) (88 parts) was uniformly mixed and ground with an air mill to obtain a powder.
  • Nipseal NS-K white carbon, Tosoh Silica Co., Ltd., trade name
  • Kaolin clay Kaolin clay
  • Formulation Example 20 DL Powder Compound (5 parts) of the present invention, propylene glycol (0.5 part) and DL clay (Showa KDE Co., Ltd., trade name) (94.5 parts) are uniformly mixed and pulverized. Obtained.
  • Seed coating powder Compound of the present invention (10 parts), Sun extract P-252 (sodium lignin sulfonate, Nippon Paper Industries Co., Ltd., trade name) (6 parts), Gohsenol GL05 (polyvinyl alcohol, Nippon Synthetic Chemical Industry Co., Ltd.) Company, product name) (1 part) and clay (Nippon Talc Co., Ltd. product name) (83 parts) are uniformly mixed and pulverized, and pre-moistened seeds are mixed, air-dried, and coated seeds Got.
  • Sun extract P-252 sodium lignin sulfonate, Nippon Paper Industries Co., Ltd., trade name
  • Gohsenol GL05 polyvinyl alcohol, Nippon Synthetic Chemical Industry Co., Ltd.
  • clay Naippon Talc Co., Ltd. product name
  • Oily Suspension Formulation Compound (20 parts) of the present invention Newkalgen C-120 (POE tristyryl phenyl ether, Takemoto Yushi Co., Ltd., trade name) (5 parts), Rheodor TW-O120V (POE sorbitan monoole) Eight, Kao Corporation, trade name) (10 parts), oleic acid methyl ester (Kanto Chemical Co., Reagents) (62 parts), Sven NZ (Organic Bentonite, Hojun Co., Ltd., trade name) (3 parts) The slurry dispersion was wet pulverized to obtain an oily suspension formulation.
  • Newkalgen C-120 POE tristyryl phenyl ether, Takemoto Yushi Co., Ltd., trade name
  • Rheodor TW-O120V POE sorbitan monoole
  • Kao Corporation trade name
  • oleic acid methyl ester Kanto Chemical Co., Reagents
  • Sven NZ Organic Bento
  • Comparative compound A (compound described in Patent Document 17)
  • Comparative compound B analogous compound of comparative drugs A, C, D
  • Comparative compound C (compound described in Patent Document 19)
  • Comparative compound D (compound described in Patent Document 13)
  • Comparative compound E (compound described in Patent Document 1)
  • Table 1 below shows the 1 H-NMR data of Comparative Compounds A to E.
  • Test Example Test for Cucumber Powdery Mildew A water dilution of the emulsion prepared according to Formulation Example 1 was sprayed over the entire cucumber seedling (approximately 1.5 leaf seedlings) at a rate of 5 ml / pot using a spray gun. On the next day after spraying, the leaf surface of the first true leaf was spray-inoculated with a spore suspension (1.0 ⁇ 10 5 spores / ml) having a predetermined concentration. After inoculation, it moved to the glass greenhouse, and after 12 days, the severity was investigated based on the following lesion area ratio. Based on the following formula, the control value was calculated from the severity of the untreated group and the severity of the treated group.
  • Control value (%) [1 ⁇ (Disease level of treated area / Disease level of untreated area)] ⁇ 100
  • Test Example Test for Wheat Powdery Mildew A water dilution of the emulsion prepared according to Formulation Example 1 was sprayed over the whole wheat seedling (approximately 1.5 leaf seedlings) at a rate of 5 ml / pot using a spray gun. On the next day after spraying, the seedlings after spraying were moved to a glass greenhouse and inoculated by placing seedlings with wheat powdery mildew around them. 12 days after the inoculation, the disease severity was investigated based on the following lesion area ratio. Based on the following formula, the control value was calculated from the severity of the untreated group and the severity of the treated group.
  • Control value (%) [1 ⁇ (Disease level of treated area / Disease level of untreated area)] ⁇ 100
  • compound numbers 19, 22, 24, 36, 43, 54, 68, 80, 105, 119, 122, 165, 166, 200, 201, 202, 203, 207, 208, 261 are controlled at a concentration of 400 ppm. The value was 70 or more.
  • the comparative agents A, B, C, D, and E had control values of 0, 22, 20, 25, and 25, respectively, at a concentration of 400 ppm.
  • Test example Insecticidal effect test on Japanese horseshoe moth
  • the water-diluted emulsion prepared according to Formulation Example 1 was sprayed onto the leaves of potted rice seedlings grown for two weeks after seeding using an airbrush. .
  • 5 third instar larvae were inoculated, placed in a 430 ml container in a PET cup, covered with a mesh, and then kept in a thermostatic chamber at 23 ° C.
  • Five days after the treatment the state of the larvae was observed in three parts: survival, abnormality, and death, and the larval mortality (%) was determined by the following formula based on the observation results. The test was conducted using 1 seedling in each group.
  • Larval mortality rate (%) (number of dead insects + number of abnormal insects) / number of test insects x 100
  • compound numbers 19, 22, 38, 39, 41, 47, 48, 52, 57, 59, 60, 61, 63, 79, 87, 102, 103, 104, 105, 117, 127, 129, 130 146, 147, 173, 192, 193, 195, 196, 200, 201, 202, 203, 221, 4-3, 6-5, 6-7 show 100% insecticidal rate at a concentration of 500 ppm It was.
  • the comparative agents A, B, C, D and E had an insecticidal rate of 0% at a concentration of 500 ppm.
  • Test Example Insecticidal effect test against tomato rust mites Water was put into a 430 ml capacity PET cup, and a lid with a hole (diameter: about 5 mm) was formed in the center. Absorbent cotton having a width of about 1 cm and a length of about 14 cm was inserted so as to be immersed in the water in the cup through the hole of the lid, and about 8 cm square of absorbent cotton was placed thereon so that the water in the cup was constantly replenished. Place three leaf discs (1cm x 1cm) made from small leaves in the initial stage of tomato leaf development on absorbent cotton so that the back of the leaf is on top. Vaccinated.
  • this cup was placed in an acrylic cylinder having a height of 45 cm and a diameter of 12 cm, and an aqueous dilution of an emulsion prepared according to Formulation Example 1 was sprayed with 2.0 ml per cup using an air brush. (1 concentration, 1 repetition). After spraying, it was kept in a constant temperature room at 25 ° C. Seven days after the treatment, the number of surviving larvae was divided into four levels: 100 (density suppression rate: 100%), 80 (same: 99-80%), 50 (same: 79-50%), 0 (same: less than 50%) The control value was calculated by the following formula based on the evaluation.
  • Control value (A ⁇ 100 + B ⁇ 80 + C ⁇ 50) / (A + B + C + D)
  • compound numbers 20, 36, 37, 43, 47, 52, 53, 54, 61, 65, 66, 68, 71, 77, 78, 79, 85, 87, 94, 95, 147, 168, 169 , 180, 181, 182, 183, 185, 190, 192, 2-1, 3-1 exhibited a control value of 100% at a concentration of 500 ppm.
  • the comparative agents A, B, C, D and E had a control value of 0 at a concentration of 500 ppm.
  • novel compound of the present invention can be preferably used as an active ingredient of agricultural and horticultural agents.

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Abstract

La présente invention concerne un nouveau produit chimique agricole/horticole destiné à la régulation des ravageurs dans la production de culture telle que l'agriculture et l'horticulture. Un composé anilide ou un composé thioamide d'une structure spécifique présentant un substituant présenté par la formule (dans la formule, R4 et R5 représentent chacun indépendamment un atome d'hydrogène, un atome d'halogène, un groupe alkyle en C1-3, un groupe halogénoalkyle en C1-3, un groupe alcoxy en C1-3, un groupe halogénoalcoxy en C1-3, ou un groupe hydroxyle) est utilisé comme ingrédient actif.
PCT/JP2017/020971 2016-06-09 2017-06-06 Nouveau composé et produit chimique agricole/horticole l'utilisant comme ingrédient actif WO2017213137A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110468053A (zh) * 2018-05-15 2019-11-19 北京市园林科学研究院 一种毡状地丝霉菌菌株及其在生物防治中的应用
CN112538029A (zh) * 2020-12-15 2021-03-23 利民化学有限责任公司 一种高产率制备肟菌酯的绿色合成方法
US11299456B2 (en) 2016-12-05 2022-04-12 Lead Pharma Holding B.V. ROR gamma (RORγ) modulators
US11596612B1 (en) 2022-03-08 2023-03-07 PTC Innovations, LLC Topical anesthetics

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1982000400A1 (fr) * 1980-07-30 1982-02-18 Smith L Procede de desherbage selectif sur les mauvaises herbes poussant avec le riz
US4750931A (en) * 1983-11-10 1988-06-14 The Dow Chemical Company Certain 3,5-disubstituted-2-pyridyloxy-fluorophenoxy-alkanoic acids, derivatives thereof and herbicidal properties
US4968343A (en) * 1985-09-16 1990-11-06 The Dow Chemical Company Fluoroalkyl anilide derivatives of 2-(4-aryloxyphenoxy)alkanoic or alkenoic acids as selective herbicides
JP2010037311A (ja) * 2008-08-08 2010-02-18 Bayer Cropscience Ag 新規殺虫性アシルアミノベンズアミド誘導体
CN101747263A (zh) * 2008-11-28 2010-06-23 中国中化集团公司 吡啶氧基苯氧羧酸类化合物与应用
CN101941917A (zh) * 2009-07-06 2011-01-12 中国中化股份有限公司 一种酰胺类化合物及其用途
JP2012526065A (ja) * 2009-05-06 2012-10-25 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 害虫駆除における使用のための４‐シアノ‐３−ベンゾイルアミノ‐ｎ‐フェニル‐ベンズアミド
WO2015000392A1 (fr) * 2013-07-02 2015-01-08 湖南化工研究院有限公司 Composé amide de l'acide n-(aryle alkyle) aryloxy phénoxy carboxylique et procédé de préparation et application associée
WO2015097091A1 (fr) * 2013-12-23 2015-07-02 Syngenta Participations Ag Composés insecticides
CN104876922A (zh) * 2014-02-27 2015-09-02 南京工业大学 一类芳氧苯氧丙酸酰胺类除草剂
WO2015195423A1 (fr) * 2014-06-17 2015-12-23 Novartis Tiergesundheit Ag Nouveaux composés sulfonylaminobenzamide

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1982000400A1 (fr) * 1980-07-30 1982-02-18 Smith L Procede de desherbage selectif sur les mauvaises herbes poussant avec le riz
US4750931A (en) * 1983-11-10 1988-06-14 The Dow Chemical Company Certain 3,5-disubstituted-2-pyridyloxy-fluorophenoxy-alkanoic acids, derivatives thereof and herbicidal properties
US4968343A (en) * 1985-09-16 1990-11-06 The Dow Chemical Company Fluoroalkyl anilide derivatives of 2-(4-aryloxyphenoxy)alkanoic or alkenoic acids as selective herbicides
JP2010037311A (ja) * 2008-08-08 2010-02-18 Bayer Cropscience Ag 新規殺虫性アシルアミノベンズアミド誘導体
CN101747263A (zh) * 2008-11-28 2010-06-23 中国中化集团公司 吡啶氧基苯氧羧酸类化合物与应用
JP2012526065A (ja) * 2009-05-06 2012-10-25 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 害虫駆除における使用のための４‐シアノ‐３−ベンゾイルアミノ‐ｎ‐フェニル‐ベンズアミド
CN101941917A (zh) * 2009-07-06 2011-01-12 中国中化股份有限公司 一种酰胺类化合物及其用途
WO2015000392A1 (fr) * 2013-07-02 2015-01-08 湖南化工研究院有限公司 Composé amide de l'acide n-(aryle alkyle) aryloxy phénoxy carboxylique et procédé de préparation et application associée
WO2015097091A1 (fr) * 2013-12-23 2015-07-02 Syngenta Participations Ag Composés insecticides
CN104876922A (zh) * 2014-02-27 2015-09-02 南京工业大学 一类芳氧苯氧丙酸酰胺类除草剂
WO2015195423A1 (fr) * 2014-06-17 2015-12-23 Novartis Tiergesundheit Ag Nouveaux composés sulfonylaminobenzamide

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11299456B2 (en) 2016-12-05 2022-04-12 Lead Pharma Holding B.V. ROR gamma (RORγ) modulators
CN110468053A (zh) * 2018-05-15 2019-11-19 北京市园林科学研究院 一种毡状地丝霉菌菌株及其在生物防治中的应用
CN110468053B (zh) * 2018-05-15 2021-05-07 北京市园林科学研究院 一种毡状地丝霉菌菌株及其在生物防治中的应用
CN112538029A (zh) * 2020-12-15 2021-03-23 利民化学有限责任公司 一种高产率制备肟菌酯的绿色合成方法
US11806323B2 (en) 2022-03-08 2023-11-07 PTC Innovations, LLC Topical anesthetics
US11786493B2 (en) 2022-03-08 2023-10-17 PTC Innovations, LLC Anesthetic compounds and methods of making and using same to treat or prevent pain symptoms
US11596612B1 (en) 2022-03-08 2023-03-07 PTC Innovations, LLC Topical anesthetics
US11814335B1 (en) 2022-03-08 2023-11-14 PTC Innovations, LLC Anesthetic compounds and methods of making and using same to treat or prevent pain symptoms
US11845709B2 (en) 2022-03-08 2023-12-19 PTC Innovations, LLC Anesthetic compounds and methods of making and using same to treat or prevent pain symptoms
US11866390B2 (en) 2022-03-08 2024-01-09 PTC Innovations, LLC Anesthetic compounds and methods of making and using same to treat or prevent pain symptoms
US11866391B2 (en) 2022-03-08 2024-01-09 PTC Innovations, LLC Anesthetic compounds and methods of making and using same to treat or prevent pain symptoms
US11866392B2 (en) 2022-03-08 2024-01-09 PTC Innovations, LLC Anesthetic compounds and methods of making and using same to treat or prevent pain symptoms
US11980599B2 (en) 2022-03-08 2024-05-14 PTC Innovations, LLC Anesthetic compounds and methods of making and using same to treat or prevent pain symptoms

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