Classifications

• • 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
  • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
  • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K31/00—Medicinal preparations containing organic active ingredients
  • A61K31/33—Heterocyclic compounds
  • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
  • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
  • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
  • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
  • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
  • A61P33/10—Anthelmintics
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
  • A61P33/14—Ectoparasiticides, e.g. scabicides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
  • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
  • C07D491/10—Spiro-condensed systems
  • C07D491/113—Spiro-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring

Definitions

• the present invention relates to an agricultural and horticultural insecticide that contains a benzimidazole compound or a salt thereof as an active ingredient, and a method of using the same.
• benzimidazole compounds have been reported to be useful as insecticides (see, for example, Patent Documents 1 and 2).
• a specific N-sulfonyl group such as an N-alkylsulfonyl group is located at the 1-position.
• No benzimidazole compounds having groups are disclosed.
• a benzimidazole compound having a pyridyl group bonded to the 2-position is disclosed, but in this document, any compound having a specific N-sulfonyl group such as an alkylsulfonyl group at the 1-position and a description of insecticidal effects are also disclosed. (For example, refer nonpatent literatures 1 and 2).
• the present inventors have found that a benzimidazole compound having a pyridyl group bonded to the 2-position represented by the general formula (1) and having a specific N-sulfonyl group at the 1-position or The present inventors have found that the salts can not only have an excellent control effect against agricultural and horticultural pests, but can also solve the above-mentioned problems, leading to the present invention.
• R represents (a1) (C 1 -C 8 ) alkyl group; (a2) (C 3 -C 8 ) cycloalkyl group; (a3) (C 3 -C 8 ) cycloalkyl (C 1- C 8) alkyl group; (a4) halo (C 1 -C 8) alkyl group; (a5) (C 2 -C 8) alkenyl groups; (a6) (C 2 -C 8) alkynyl groups; (a7) aryl A group; or (a8) which may be the same or different, (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) ( C 1 -C 6) alkoxy groups, (e) halo (C 1 -C 6) alkoxy groups, (f) (C 1 -C 6) alkoxy groups, (f) (C 1 -
• R 1 represents (b1) (C 1 -C 8 ) alkyl group; (b2) halo (C 1 -C 8 ) alkyl group; (b3) (C 3 -C 8 ) cycloalkyl group; (b4) halo ( C 3 -C 8 ) cycloalkyl group; (b5) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl group; (b6) halo (C 3 -C 8 ) cycloalkyl (C 1 -C 8) alkyl group; (b7) (C 2 -C 8) alkenyl groups; (b8) halo (C 2 -C 8) alkenyl groups; (b9) (C 2 -C 8) alkynyl groups; (b10) halo ( C 2 -C 8) alkynyl groups; (b11) an aryl group; (b12) may be the same or different, (a) a halogen
• Aromatic heterocyclic group having 1 to 3 substituents selected from; (b17) (C 1 -C 8) alkoxy (C 1 -C 8) alkyl group; (b18) (C 1 -C 8) An alkylthio (C 1 -C 8 ) alkyl group; (b19) (C 1 -C 8 ) alkylsulfinyl (C 1 -C 8 ) alkyl group; or (b20) (C 1 -C 8 ) alkylsulfonyl (C 1- C 8 ) represents an alkyl group.
• X is O, S, SO, SO 2 or NR 2 (where R 2 is a hydrogen atom, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group, (C 1- C 6 ) represents an alkoxycarbonyl group, (C 1 -C 6 ) alkylsulfonyl group, or halo (C 1 -C 6 ) alkylsulfonyl group, or R 2 is bonded to R 1 and R 2 is bonded.
• R 2 is a hydrogen atom, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group, (C 1- C 6 ) represents an alkoxycarbonyl group, (C 1 -C 6 ) alkylsulfonyl group, or halo (C 1 -C 6 ) alkylsulfonyl group, or R 2 is bonded to R 1 and R 2 is bonded.
• Y may be the same or different and represents (c1) a halogen atom; or (c2) (C 1 -C 8 ) alkyl group.
• m represents 0, 1, 2, or 3.
• Z may be the same or different, and (d1) a halogen atom; (d2) (C 1 -C 8 ) alkyl group; (d3) (C 3 -C 8 ) cycloalkyl group; (d4) (C 3- C 8) cycloalkyl group (C 1 -C 8) alkyl group; (d5) halo (C 3 -C 8) cycloalkyl (C 1 -C 8) alkyl group; (d6) halo (C 1 -C 8) (D7) a halo (C 1 -C 8 ) alkoxy group; (d8) a halo (C 1 -C 8 ) alkylthio group; (d9) a halo (C 1 -C 8 ) alkylsulfin
• R is (a1) (C 1 -C 8 ) alkyl group; (a2) (C 3 -C 8 ) cycloalkyl group; (a3) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl group; (a4) halo (C 1 -C 8 ) alkyl group; (a5) (C 2 -C 8 ) alkenyl group; (a6) (C 2 -C 8 ) alkynyl group; (a7) aryl group Or (a8) may be the same or different, (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) (C 1- C 6 ) alkoxy group, (e) halo (C 1 -C 6 ) alkoxy group, (f) (C 1 -C 6 ) alkylthio group,
• R is (a1) (C 1 -C 8 ) alkyl group; (a2) (C 3 -C 8 ) cycloalkyl group; (a4) halo (C 1 -C 8 ) alkyl group; (a7) An aryl group; or (a8) which may be the same or different, (a) a halogen atom, (b) a (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) (C 1 -C 6 ) alkoxy group, (e) halo (C 1 -C 6 ) alkoxy group, (f) (C 1 -C 6 ) alkylthio group, (g) halo (C 1 -C 6 ) alkylthio group (H) (C 1 -C 6 ) alkylsulfinyl group, (i) halo (C 1 -C 6 ) alkylsulfin
• R 2 alkyl sulfonyl group. or combines R 2 is as R 1, together with the nitrogen atom to which R 2 is attached, from 1 to 5 substituents of a optionally saturated also be 5-8 membered (Wherein the substituents are (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group, (C 1 -C 6 ) alkoxycarbonyl).
• the two oxy groups of the group (C 1 -C 6 ) alkylsulfonyl group, halo (C 1 -C 6 ) alkylsulfonyl group, and (C 1 -C 6 ) alkylenedioxy group (alkylenedioxy group) It may be bonded to the same carbon atom of the nitrogen aliphatic heterocycle or may be bonded to different carbon atoms.
• Y may be the same or different and (c1) represents a halogen atom; m represents 0 or 1, Z may be the same or different and represents (d1) a halogen atom; or (d2) (C 1 -C 8 ) alkyl group, benzimidazole compound or a salt thereof according to [1], wherein n is 0, 1, or 2;
• R represents a (a1) (C 1 -C 8 ) alkyl group
• R 1 represents a (b1) halo (C 1 -C 8 ) alkyl group
• m represents 0, and n represents ,
• An agricultural and horticultural insecticidal acaricide comprising the benzimidazole compound or a salt thereof according to any one of [1] to [4] as an active ingredient
• a method for using an agricultural and horticultural insecticide which comprises treating a plant or soil with an effective amount of the benzimidazole compound or salt thereof according to any one of [1] to [4]
• An ectoparasite control agent for animals comprising an effective amount of the benzimidazole compound or salt thereof according to any one of [1] to [4] as an active ingredient
• An animal endoparasite control agent or the like comprising an effective amount of the benzimidazole compound or a salt thereof according to any one of [1] to [4] as an active ingredient.
• the benzimidazole compound or a salt thereof having a pyridyl group bonded to the 2-position and having a specific N-sulfonyl group at the 1-position of the present invention not only has an excellent effect as an insecticide for agricultural and horticultural use, but also dogs and cats. It is also effective against such pests as parasites such as pet animals or livestock such as cattle and sheep.
• halo means “halogen atom” And a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
• (C 1 -C 8 ) alkyl group means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group Tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group, normal heptyl group, 2-heptyl group, 3-heptyl group, 2-methylhexyl group , 3-methylhexyl group, 4-methylhexyl group, is
• (C 2 -C 8) alkenyl group include vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2 -Butenyl group, 2-methyl-2-propenyl group, 1-methyl-2-propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, A straight-chain or branched alkenyl group having 2 to 8 carbon atoms such as a heptenyl group and an octenyl group is shown, and “(C 2 -C 8 ) alkynyl group” means, for example, an ethynyl group, a 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl-1-propyn
• (C 1 -C 6 ) alkyl group means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group Tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, A linear or branched alkyl group having 1 to 6 carbon atoms such as 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group, etc.
• the "(C 2 -C 6) alkenyl group” include vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2 Butenyl group, 2-methyl-2-propenyl group, 1-methyl-2-propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, etc.
• a linear or branched alkenyl group having 2 to 6 carbon atoms, and “(C 2 -C 6 ) alkynyl group” means, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1- Butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl-1-propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, 3,
• a linear or branched alkynyl group having 2 to 6 carbon atoms such as a 3-dimethyl-1-butynyl group.
• (C 3 -C 8 ) cycloalkyl means a cyclic alkyl having 3 to 8 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.
• Examples of the “(C 1 -C 8 ) alkoxy group” include a methoxy group, an ethoxy group, a normal propoxy group, an isopropoxy group, a normal butoxy group, a secondary butoxy group, a tertiary butoxy group, and a normal pentyloxy group.
• (C 3 -C 6 ) cycloalkyl group means a cyclic alkyl group having 3 to 6 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc.
• “C 1- Examples of the “C 6 ) alkoxy group” include a methoxy group, an ethoxy group, a normal propoxy group, an isopropoxy group, a normal butoxy group, a secondary butoxy group, a tertiary butoxy group, a normal pentyloxy group, an isopentyloxy group, and a tertiary group.
• Pentyloxy group neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group, 1,1,2-trimethylpropyl group Alkoxy having 1 to 6 carbon atoms such as straight or branched chain such as oxy group A group.
• Examples of the “(C 1 -C 8 ) alkylthio group” include, for example, methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, and normal pentylthio group.
• Alkylsulfinyl group includes, for example, methylsulfinyl group, ethylsulfinyl group, Malpropylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tert
• alkylsulfinyl group a straight or branched chain having 1 to 8 carbon atoms alkylsulfinyl group, a "(C 1 -C 8) alkylsulfonyl group”
• Examples of the “(C 1 -C 6 ) alkylthio group” include methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, and normal pentylthio group.
• alkyl sulfinyl group and the "(C 1 -C 6) alkylsulfonyl group", for example, methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylsulfonyl group, Rumulbutylsulfonyl, secondary butylsulfonyl, tertiary butylsulfonyl, normal pentylsulfonyl, isopentylsulfonyl, tertiary pentylsulfonyl, neopentylsulfonyl, 2,3-dimethylpropylsulfonyl, 1-ethylpropyl Linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms such as sulfonyl group, 1-methylbutylsulfonyl group, normal he
• “(C 1 -C 8 ) alkyl group”, “(C 2 -C 8 ) alkenyl group”, “(C 2 -C 8 ) alkynyl group”, “(C 3 -C 8 ) cycloalkyl group”, “(C 1 -C 8 ) alkoxy”, “(C 1 -C 8 ) alkylthio”, “(C 1 -C 8 ) alkylsulfinyl” or “(C 1 -C 8 ) alkylsulfonyl” 1 or 2 or more halogen atoms may be substituted at the substitutable position, and when two or more halogen atoms are substituted, the halogen atoms may be the same or different.
• Halo (C 1 -C 8 ) alkyl group “halo (C 2 -C 8 ) alkenyl group”, “halo (C 2 -C 8 ) alkynyl group”, “halo (C 3 -C 8 )”, respectively “Cycloalkyl group”, “halo (C 1 -C 8 ) alkoxy group”, “halo (C 1 -C 8 ) alkylthio group”, “halo (C 1 -C 8 ) alkylsulfinyl group”, or “halo (C shows the 1 -C 8) alkylsulfonyl group ".
• halogen atoms may be substituted at substitutable positions. When two or more halogen atoms are substituted, the halogen atoms may be the same or different.
• Halo (C 1 -C 6 ) alkyl “Halo (C 2 -C 6 ) alkenyl”, “Halo (C 2 -C 6 ) alkynyl”, “Halo (C 3 -C 6 )” “Cycloalkyl group”, “halo (C 1 -C 6 ) alkoxy group”, “halo (C 1 -C 6 ) alkylthio group”, “halo (C 1 -C 6 ) alkylsulfinyl group”, or “halo (C shows the 1 -C 6) alkylsulfonyl group ".
• aryl group refers to an aromatic hydrocarbon group having 6 to 10 carbon atoms such as a phenyl group, 1-naphthyl group, 2-naphthyl group and the like.
• Aromatic heterocyclic group '' means, for example, oxygen such as furyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, triazinyl 5- to 6-membered monocyclic aromatic heterocyclic groups having 1 to 5 heteroatoms such as atoms, nitrogen atoms and sulfur atoms; quinolyl, isoquinolyl, quinazolyl, quinoxalyl, benzofuranyl, benzothienyl, benzoxazolyl, benz Isoxazolyl, benzothiazolyl, benzimidazolyl, benzotriazolyl, indolyl, inf
• “Saturated nitrogen-containing aliphatic heterocycle” means having at least one nitrogen atom such as pyrrolidine, piperidine, morpholine, piperazine (preferably 1 to 2), and further containing heteroatoms such as oxygen atom and sulfur atom.
• a 5- to 8-membered saturated nitrogen-containing aliphatic heterocycle optionally having 1 or 2 is shown.
• (C 1 -C 6 ) alkylcarbonyl group means, for example, acetyl group, propionyl group, butyryl group, isobutyryl group, normal butylcarbonyl group, isobutylcarbonyl group, secondary butylcarbonyl group, tertiary butylcarbonyl group, normal pentyl group Carbonyl group, isopentylcarbonyl group, tertiary pentylcarbonyl group, neopentylcarbonyl group, 2,3-dimethylpropylcarbonyl group, 1-ethylpropylcarbonyl group, 1-methylbutylcarbonyl group, 2-methylbutylcarbonyl group, normal Detectivexylcarbonyl group, isohexylcarbonyl group, 2-hexylcarbonyl group, 3-hexylcarbonyl group, 2-methylpentylcarbonyl group, 3-methylpentylcarbonyl group, 1,1,2-trimethylpro Le carbonyl
• Examples of the “(C 1 -C 6 ) alkoxycarbonyl group” include a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, a secondary butoxycarbonyl group, and a tertiary butoxycarbonyl group.
• tri (C 1 -C 6 ) alkylsilyl group examples include trimethylsilyl group, triethylsilyl group, tertiary butyldimethylsilyl group, ethyldimethylsilyl group, isopropyldimethylsilyl group, n-propyldimethylsilyl group, etc.
• a straight or branched trialkylsilyl group having 1 to 6 carbon atoms is shown. In this case, the three alkyl groups may be the same or different.
• Examples of the “(C 1 -C 6 ) alkylenedioxy group” include a methylenedioxy group and an ethylenedioxy group.
• the two oxy groups of the alkylenedioxy group may be bonded to the same carbon atom of the nitrogen-containing aliphatic heterocyclic ring or may be bonded to different carbon atoms.
• Examples of the salt of the benzimidazole compound represented by the general formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, acetate, fumarate, maleate and oxalic acid.
• examples include salts, organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium. .
• the benzimidazole compound represented by the general formula (1) and salts thereof of the present invention may have one asymmetric center in the structural formula thereof, and the present invention includes each optical isomer and any proportion thereof. All mixtures included are also included.
• R is (a1) (C 1 -C 8 ) alkyl group; (a2) (C 3 -C 8 ) cycloalkyl group; (a4) halo (C 1 -C 8 ) alkyl group; (a7) aryl group; Or (a8) may be the same or different, (a) a halogen atom, (b) (C 1 -C 6 ) alkyl group, (c) a halo (C 1 -C 6 ) alkyl group, (d) (C 1 -C 6 ) alkoxy group, (e) halo (C 1 -C 6 ) alkoxy group, (f) (C 1 -C 6 ) alkylthio group, (g) halo (C 1 -C 6 ) alkylthio group, (h ) (C 1 -C 6 ) alkylsulfiny
• R 2 alkyl sulfonyl group. or combines R 2 is as R 1, together with the nitrogen atom to which R 2 is attached, from 1 to 5 substituents of a optionally saturated also be 5-8 membered (Wherein the substituents are (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkylcarbonyl group, (C 1 -C 6 ) alkoxycarbonyl).
• the two oxy groups of the group (C 1 -C 6 ) alkylsulfonyl group, halo (C 1 -C 6 ) alkylsulfonyl group, and (C 1 -C 6 ) alkylenedioxy group (alkylenedioxy group) It may be bonded to the same carbon atom of the nitrogen aliphatic heterocycle or may be bonded to different carbon atoms.
• Y may be the same or different and is (c1) a halogen atom; m is 0 or 1, Z may be the same or different and is (d1) a halogen atom; or (d2) (C 1 -C 8 ) alkyl group; n is 0, 1, or 2; More preferably, R is a (a1) (C 1 -C 6 ) alkyl group, R 1 is a (b1) halo (C 1 -C 6 ) alkyl group, and m and n are 0. .
• the benzimidazole compound or a salt thereof represented by the general formula (1) of the present invention can be produced by, for example, the following production method, but the present invention is not limited to these.
• the nitrile compound represented by the general formula (2-2) is obtained by combining a compound represented by the general formula (2-3) and a compound represented by the general formula (4) with a base and an amine. It can manufacture by reacting in presence of an active solvent.
• Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate, acetates such as sodium acetate and potassium acetate, potassium t Alkali metal alkoxides such as butoxide, sodium methoxide, sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, pyridine, dimethyl Nitrogen-containing aromatic compounds such as aminopyridine can be mentioned, and the amount used is usually in the range of 1 to 10 moles compared to the compound represented by the general formula (4).
• inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate
• acetates such as sodium acetate and potassium acetate
• potassium t Alkali metal alkoxides such
• the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
• aromatic hydrocarbons such as benzene, toluene and xylene
• halogens such as methylene chloride, chloroform and carbon tetrachloride.
• Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, linear or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, dimethylformamide, dimethyl
• amides such as acetamide, ketones such as acetone and methyl ethyl ketone
• inert solvents such as polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone (NMP). These inert solvents are In or as a mixture of two or more thereof may be used.
• each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
• the reaction temperature can be from room temperature to the boiling range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be in the range of several minutes to 48 hours.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Further, the next step may be performed without isolating the intermediate from the reaction system.
• step [B] The carboxylic acid compound represented by the general formula (2-1) is obtained by reacting the nitrile compound represented by the general formula (2-2) in the presence of a base and an inert solvent. Can be manufactured.
• Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate and potassium hydrogen carbonate, and acetates such as sodium acetate and potassium acetate.
• the amount used is usually in the range of 1-fold to 10-fold moles with respect to the compound represented by the general formula (2-2).
• the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
• aromatic hydrocarbons such as benzene, toluene and xylene
• halogenated aromatic carbonization such as chlorobenzene and dichlorobenzene.
• Hydrogen, diethyl ether, methyl tertiary butyl ether, chain or cyclic ethers such as dioxane and tetrahydrofuran, amides such as dimethylformamide and dimethylacetamide, ketones such as acetone and methyl ethyl ketone, dimethyl sulfoxide, 1,3-dimethyl- Examples thereof include polar solvents such as 2-imidazolidinone, inert solvents such as alcohols such as methanol, ethanol, propanol and isopropyl alcohol, and water. These inert solvents may be used alone or in combination of two or more. Can be used Kill.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
• the amide compound represented by the general formula (2) comprises a carboxylic acid compound represented by the general formula (2-1) and a diamino compound represented by the general formula (3) as a condensing agent.
• Examples of the condensing agent used in this reaction include diethyl cyanophosphate (DEPC), carbonyldiimidazole (CDI), 1,3-dicyclohexylcarbodiimide (DCC), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide ( EDC) or its hydrochloride, chlorocarbonates, 2-chloro-1-methylpyridinium iodide, etc., and the amount used is one time the compound represented by the general formula (2-1) It may be appropriately selected from the range of mol to 1.5 times mol.
• DEPC diethyl cyanophosphate
• CDI carbonyldiimidazole
• DCC 1,3-dicyclohexylcarbodiimide
• EDC 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide
• the amount used is one time the compound represented by the general formula (2-1) It may be appropriately selected from the range of mol
• Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate, acetates such as sodium acetate and potassium acetate, potassium t Alkali metal alkoxides such as butoxide, sodium methoxide, sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene, pyridine, dimethyl
• Examples thereof include nitrogen-containing aromatic compounds such as aminopyridine (DMAP), and the amount used is usually in the range of 0.1-fold to 10-fold mol with respect to the compound represented by formula (2-1). Used in.
• the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
• aromatic hydrocarbons such as benzene, toluene and xylene
• halogens such as methylene chloride, chloroform and carbon tetrachloride.
• Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, linear or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, dimethylformamide, dimethyl
• amides such as acetamide, ketones such as acetone and methyl ethyl ketone
• polar solvents such as dimethyl sulfoxide and 1,3-dimethyl-2-imidazolidinone
• inert solvents such as nitrogen-containing aromatic compounds such as pyridine. These inert solvents are simple In or as a mixture of two or more thereof may be used.
• each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
• the reaction temperature can be from room temperature to the boiling range of the inert solvent used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but it may be in the range of several minutes to 48 hours.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Further, the next step may be performed without isolating the intermediate from the reaction system.
• step [D] The benzimidazole compound represented by the general formula (1-1) is produced by reacting the amide compound represented by the general formula (2) in the presence of an acid and an inert solvent. be able to.
• Examples of the acid used in the reaction include inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid, organic acids such as formic acid, acetic acid, propionic acid, trifluoroacetic acid and benzoic acid, methanesulfonic acid, trifluoromethanesulfonic acid and paratoluenesulfone.
• examples thereof include sulfonic acids such as acids, phosphoric acids and the like, and the amount used is appropriately selected from the range of 0.01-fold to 10-fold moles relative to the amide compound represented by the general formula (1-1). And use it.
• the inert solvent used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
• aromatic hydrocarbons such as benzene, toluene and xylene
• halogens such as methylene chloride, chloroform and carbon tetrachloride.
• Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, linear or cyclic ethers such as diethyl ether, methyl tertiary butyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, dimethylformamide, dimethyl
• amides such as acetamide, ketones such as acetone and methyl ethyl ketone
• inert solvents such as polar solvents such as dimethyl sulfoxide, 1,3-dimethyl-2-imidazolidinone, and N-methylpyrrolidone (NMP). These inert solvents are In or as a mixture of two or more thereof may be used.
• the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
• step [E] The benzimidazole compound represented by the general formula (1) is reacted with the corresponding sulfonyl chloride in the presence of an inert solvent and a base. Can be manufactured.
• Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and sodium hydride, and acetic acid such as sodium acetate and potassium acetate.
• inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and sodium hydride
• acetic acid such as sodium acetate and potassium acetate.
• alkali metal alkoxides such as potassium t-butoxide, sodium methoxide, sodium ethoxide; tertiary amines such as triethylamine, diisopropylethylamine, 1,8-diazabicyclo [5.4.0] undec-7-ene
• Nitrogen-containing aromatic compounds such as pyridine, dimethylaminopyridine and the like, and the amount used is usually in the range of 1 to 10 moles compared to the compound represented by the general formula (1-1). used.
• the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction.
• aromatic hydrocarbons such as benzene, toluene, and xylene
• halogenated compounds such as methylene chloride, chloroform, and carbon tetrachloride.
• hydrocarbons halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene
• chain or cyclic ethers such as diethyl ether, tetrahydrofuran (THF) and dioxane.
• the sulfonyl chloride used in the present invention is not particularly limited as long as it is a sulfonyl chloride represented by the formula: RSO 2 Cl (R is the same as described above). Since this reaction is an equimolar reaction, each reactant may be used in an equimolar amount, but any of the reactants can be used in excess.
• the reaction temperature in this reaction may usually be in the range of about 0 ° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., and is not constant, but it is suitably in the range of several minutes to 48 hours Just choose.
• the target product may be isolated by a conventional method, and the target product can be produced by purification by recrystallization, distillation, column chromatography or the like, if necessary.
• Me is a methyl group
• Et is an ethyl group
• n-Pr is a normal propyl group
• i-Pr is an isopropyl group
• n-Bu is a normal butyl group
• t-Bu is a tertiary butyl group
• n-Pen is shown below.
• n-Hex is normal hexyl group
• c-Pr is cyclopropyl group
• c-Pen is cyclopentyl group
• c-Hex is cyclohexyl group
• c-Hep is cycloheptyl group
• Ac is acetyl group
• pTol is p-Tolyl group
• Ph represents a phenyl group
• Bn represents a benzyl group
• TMS represents a trimethylsilyl group.
• the physical properties indicate melting point (° C.) or H 1 -NMR.
• the H 1 -NMR data is shown in Table 8.
• the agricultural and horticultural insecticidal acaricide containing the benzimidazole compound represented by the general formula (1) or a salt thereof of the present invention as an active ingredient is various agricultural and forestry that harms paddy rice, fruit trees, vegetables, other crops and florets, Suitable for horticulture, pests of stored grains, sanitary pests, nematodes, and mites.
• Examples of the pests or nematodes include the following. Lepidoptera (Lepidoptera) pests such as Parasa consocia, Redwood (Anomis mesogona), Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, African exotic empties (Spod) (Hyphantria cunea), Awanoiga (Ostrinia furnacalis), Ayayotou (Pseudaletia separata), Iga (Tinea translucens), Igusashinmushiga (Bactra furfuryla), Ichinomoseisari (Parnara guttata), Ina Temui inferens), Brachimia triannulella, Monema flavescens, Iraqusinu Waiba (Trichoplusia ni), Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Male
• Hemiptera pests, for example, Nezara antennata, red beetle (Stenotus rubrovittatus), red beetle (Graphosoma rubrolineatum), red beetle (Trigonotylus coelestialium), Aeschynteles maculatus), red beetle (Creontiades pallidifer), red beetle bug (Dysdercus cingulatus), red beetle (Chrysomphalus ficus), red beetle (Aonidiella aurantii), red crab beetle (Graptops) Scale insects (Icerya purchasi), Japanese beetle (Piezodorus hybneri), Japanese beetle (Lagynotomus elongatus), Japanese white-winged beetle (Thaia subrufa), Japanese black beetle (Scotinophara luridaito
• Coleoptera (Coleoptera) pests include, for example, Xystrocera globosa, Aobaarie-hane-kakushi (Paederus fuscipes), Akhanamuri (Eucetonia roelofsi), Azuki beetle (Callosobruchus chinensis), Arimodosium (Hypera postica), rice weevil (Echinocnemus squameus), rice beetle (Oulema oryzae), rice beetle (Oulema oryzae), rice beetle (Donacia provosti), weevil weevil (Epilachna varivestis), bean weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), beetle weevil (Involvulus cupreus), cucumber beetle (Aulacophora femoralis), Peas we
• Diptera pests, for example, Culex pipiens len pallens, red winged fly (Pegomya hyoscyami), red winged fly flies (Liriomyza huidobrensis), house fly (Musca domestica), rice moth (Chlo) Flies Fruit flies (Rhacochlaena japonica), fruit flies (Muscina stabulans), fruit flies such as fruit flies (Megaselia spiracularis), butterfly flies (Clogmia albipunctata), mung fly moth (Tipula aino), hormone moth (Pipula) rhynchus), Anopheles sinensis, Japanese flies (Hylemya brassicae), Soybean fly (Asphondylia sp.), Panax fly (Delia platqua), Onion fly (Delia antiqua) asiR
• Hymenoptera Pristomyrmex ponnes
• Arbatidae Arbatidae
• Moneorumium pharaohnis Pheidole noda
• Athalia rosae Crispae (Dryocosmus purioh)
• Hornets black bee (Athalia infumata ata infumata), horned bee (Arge pagana), Japanese bee (Athalia japonica), cricket (Acromyrmex spp.), Fire ant (Solenopsis spp.), Apple honey bee (Arlen beli) (Ochetellus glaber) and the like.
• insects of the order Diptera Hortocoryphus lineosus
• Kera Gryllotalpa sp.
• Coago Oxya hyla intricata
• Oxya ⁇ ⁇ yezoensis Oxya ⁇ ⁇ yezoensis
• Tonosama locust Locusta migrago
• Oneya Homorocoryphus jezoensis
• emma cricket Teogryllus emma
• Thrips examples of thrips of the order Thrips (Selenothrips rubrocinctus), Thrips (Stenchaetothrips biformis), Thrips thrips (Haplothrips aculeatus), Thrips , Lithrips floridensis, Thrips simplex, Thrips nigropilosus, Black thrips, dominos Leeuwenia pasanii), Shiritakuthamis (Litotetothrips pasaniae), Citrus srips (Scirtothrips citri), Hempothrips chinensis, Soybean thrips (Mycterothrips glycines), Da Thrips setosus, Scirtothrips dorsalis, Dendrothrips niwai Thrips hawaiiensis, Haplothrips kurdjumovi, Thrips coloratus , Lilyripa vaneeckei, and
• pests examples include Leptotrombidium akamushi, Tetranychus ⁇ ludeni, American dock ticks (Dermacentor variabilis), Tetranychus truncatus, Mite (Ornithonyssus bacoti), Mite Tetranychus viennensis), ticks (Tetranychus kanzawai), ticks (Rhipicephalus sanguineus), etc.
• Tick (Dermacentor taiwanicus), Chinese cabbage mite (Acaphylla theavagrans), Chinese dust mite (Polyphagotarsonemus latus), Tomato mite (Aculops lycopersici), Trichoid mite (Ornithonyssus sylvairum), Nami spider mite (Tetranychus) icae), red spider mite (Eriophyesbachibaensis), hymenid tick (Sarcoptes scabiei), black tick (Haemaphysalis longicornis), black-legged tick (Ixodes scapularis), spinach prickly tick (Tyrophagus similis, tick , Southern ticks (Cheyletus moorei), southern ticks (Brevipalpus phoenicis), earthworm ticks (Octodectes cynotis), mushroom mites (Dermatophagoides ptrenyss
• termite insect pests include the ant termite (Reticulitermes miyatakei), the American ant termite (Incisitermes minor), the termite (Coptotermes formosanus), the termite (Hodotermopsis japonica), the common termite (Reticulitermes termtermes eticmite), , Glyptotermes , Nakajima termite (Glyptotermes nakajimai), Nitobe termite (Pericapritermes nitobei), Yamato termite (Reticulitermes speratus) and the like.
• cockroach Periplaneta fuliginosa
• German cockroach Blattella germanica
• Great cockroach Blatta orientalis
• Greater cockroach Periplaneta brunnea
• Greater cockroach Blattella lituriplanet (Periplaneta americana) and the like.
• fleas examples include human fleas (Pulex irritans), cat fleas (Ctenocephalides felis), and fleas (Ceratophyllus gallinae).
• Nematodes such as strawberry nematode (Nothotylenchus acris), rice scallop nematode (Aphelenchoides besseyi), red beetle nematode (Pratylenchus penetrans), red fox nematode (Meloidogyne hapla), sweet potato nematode (Meloidogyne moth geraod) rostochiensis), Javaloid nematode (Meloidogyne javanica), Soybean cyst nematode (Heterodera glycines), Southern nematode nematode (Pratylenchus coffeae), Munenegusa nematode (Pratylenchus neglectus), and Tenetrans sem
• molluscs examples include Pomacea canaliculata, Achatina fulica, slugs (Meghimatium bilineatum), Lehmannina valentiana, Limax flavus, and Acusta despecta Is mentioned.
• the agricultural and horticultural insecticide of the present invention has a strong insecticidal effect against tomato kibaga (Tuta absoluta) as other pests.
• animal parasite ticks Boophilus microplus
• black tick ticks Rastericephalus sanguineus
• white tick ticks Haemaphysalis longicornis
• yellow ticks Haemaphysalis flava
• tsurigane talis scab Haemaphysali ticks
• Tick Haemaphysalis concinna
• tick Haemaphysalis japonica
• tuna Haemaphysalis kitaokai
• tick Haemaphysalis ias
• tick Ixodes ovatus
• tick desmite Ticks Dermanyssus, ticks such as Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis gallinae
• avian mite Ornithonyssus sy
• fleas to be controlled include, for example, ectoparasite worms belonging to the order Flea (Siphonaptera), more specifically fleas belonging to the family Flea (Pulicidae), Cleaphyllus (Ceratephyllus), etc. .
• fleas belonging to the family flea family include, for example, dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis), fleas (Pulex irritans), elephant fleas (Echidnophaga gallinacea), keops mouse fleas (Xenopsylla cheopis), Leptopsylla segnis), European mouse minnow (Nosopsyllus fasciatus), and Yamato mouse minnow (Monopsyllus anisus).
• dog fleas Ctenocephalides canis
• cat fleas Ctenocephalides felis
• fleas Pulex irritans
• elephant fleas Eudnophaga gallinacea
• keops mouse fleas Xenopsylla cheopis
• Leptopsylla segnis European mouse minnow (Nosopsyllus fasciatus), and Yamato mouse minnow (Monopsyllus anisus).
• ectoparasites to be controlled include, for example, cattle lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), cattle white lice (Linognathus vituli), pig lice (Haematopinus ⁇ pubis), And lice such as head lice (Pediculus capitis), and white lice like dog lice (Trichodectes canis), blood-sucking moths such as the cattle fly (Tabanus trigonus), the water mosquito (Culicoides schultzei), and the dipteran moth (Simulium ornatum) Examples include pests.
• endoparasites include nematodes such as pneumoniae, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms, manson cleft worms, broad-headed crest worms, berries Tapeworms such as tapeworms, multi-headed tapeworms, single-banded tapeworms, and multi-banded tapeworms, flukes such as Schistosoma japonicum, and liver fluke, and coccidium, malaria parasites, intestinal granulocysts, toxoplasma And protozoa such as Cryptosporidium.
• nematodes such as pneumoniae, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms, manson cleft worms, broad-headed crest worms, berries Tapeworms such as tapeworms, multi-headed tapeworms, single-banded tapeworms, and multi-banded tapeworms,
• Enoprida parasites Trichris spp., Capillaria spp., Trichomosides spp., Trichinella sp. Genus (Trichinella spp.), Rhabditia, for example, Micronema spp., Strongyloides spp., Strungylida, for example, Stronylida (Stomach beetle) (Stronylus spp.), Tridontophorus spp., Esophagodondons spp.
• Lung insects (Metastromylus spp.), Dictyocaurus spp., Muellerius spp., Protostrongillus spp., Neostrongulus sp. Subgenus (Cytocaurus spp.), Pneumothrongillus spp ), Spicocaurus spp., Elahostrongillus spp., Parerahostrongillus spp., Clenosopulo sp., Crenosoma spp. .), Angiostrongillus spp., Erurostungylus spp., Filaroides spp., Parafiloides esparafiloid.
• Trichostrongillus subgenus (Ciliate elegans) pp.), Haemonchus spp., Ostertagia spp., Marshallia spp., Cooperia spp., Nematodil (Nematodirus spp.), Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Orlnus subsp.
• Oxyurida parasites Oxyuris subsp. (Oxyuris spp.), Enterobius subsp. (Enterobius spp.), Passalurus spp., Sphacia subsp. , Subsp. Aspiculis spp., Heterakis spp. And the like;
• Ascaridia parasites Ascaris subsp. (Ascaris spp.), Toxocarpus subsp. (Toxascaris spp.), Toxocara subsp. (Toxocara spp.), Parascalis subsp.
• Filariida Stefanophilia subsp., Parafilaria subsp., Setaria subsp., Loa spp., Loa spp. (Dirofilaria spp.), Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerc sp., Etc.
• Gigentorhynchida Filicolis spp., Moniliformis spp., Macracanthrhynchus spp., Prostenth sp. It is done.
• the endoparasite control agent comprising the benzimidazole compound represented by the general formula (1) or a salt thereof of the present invention as an active ingredient is not only a parasite that inhabits the intermediate host and the end host, but also an insect host It is also effective for parasites in the body.
• the benzimidazole compound represented by the general formula (1) of the present invention or a salt thereof exhibits an effect at all stages of development of the parasite.
• protozoa include cysts, precapsular, vegetative or asexual reproductive divisions, amoebic bodies, sexual reproductive maternal bodies, genital bodies, fusions, and spores.
• Nematodes are eggs, larvae, and adults.
• the compounds according to the present invention not only control parasites in the living body, but also prevent the infection of parasites prophylactically by applying them to the environment serving as an infection route.
• soil-borne infection from fields, park soils, transdermal infections from rivers, lakes, wetlands, paddy fields and other water systems oral infections from feces of animals such as dogs and cats, saltwater fish, freshwater fish, crustaceans
• oral infection from shellfish and live meat of livestock infection from mosquitoes, flies, flies, cockroaches, ticks, fleas, lice, sand turtles, tsutsugamushi and the like.
• an effective amount of the compound of the present invention is orally administered and injected (intramuscular, subcutaneous, intravenous, intraperitoneal) together with a pharmaceutical additive.
• Parenteral administration such as); transdermal administration such as immersion, spraying, bathing, washing, pouring-on and spotting-on and dusting; and nasal administration.
• the compounds of the present invention can also be administered by molded products using strips, plates, bands, collars, ear marks, rim bands, labeling devices and the like.
• the compound of the present invention can be in any dosage form suitable for the administration route.
• Optional dosage forms include powders, granules, wettable powders, pellets, tablets, large pills, capsules, solid preparations such as molded products containing the active compound; injectable solutions, oral solutions, on the skin or body cavities Liquid preparations used therein; Solution preparations such as drop-on agents, spot-on agents, flowable agents, and emulsions; semi-solid preparations such as ointments and gels.
• the solid preparation can be mainly used for oral administration or transdermal administration after dilution with water, or for environmental treatment.
• Solid preparations can be prepared by adding the active compound, if necessary, with auxiliaries, mixing with appropriate excipients, and converting to the desired shape. Suitable excipients include, for example, inorganic substances such as carbonates, bicarbonates, phosphates, aluminum oxides, silicas, clays, and organic substances such as sugars, celluloses, crushed grains, and starches.
• Injection solutions can be administered intravenously, intramuscularly and subcutaneously.
• Injection solutions dissolve the active compound in a suitable solvent and, if necessary, solubilizers, acids, bases, buffer salts, antioxidants. And can be prepared by adding additives such as protective agents.
• Suitable solvents include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable vegetable oils, synthetic oils suitable for injection, and the like.
• solubilizers include polyvinylpyrrolidone, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.
• Protecting agents include benzyl alcohol, trichlorobutanol, p-hydroxybenzoate and n-butanol.
• Oral solution can be administered directly or diluted. It can be prepared in the same manner as an injectable solution.
• Flowables, emulsions, etc. can be administered directly or diluted transdermally or by environmental treatment.
• the liquid used on the skin can be administered by dripping, spreading, rubbing, spraying, spraying, or applying by immersion (immersion, bathing or washing). These solutions can be prepared in the same manner as injection solutions.
• Drops and drop preparations can be prepared by dissolving, suspending or emulsifying the active ingredient in suitable skin-compatible solvents or solvent mixtures.
• auxiliary agents such as surfactants, colorants, absorption accelerators, antioxidants, light stabilizers and adhesives may be added, and solvents such as water, alkanol, glycol, polyethylene glycol, polypropylene glycol Glycerin, benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, acetone, methyl ethyl ketone, aromatic and / or aliphatic hydrocarbons, vegetable or synthetic oils, Mention may be made of DMF, liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane.
• solvents such as water, alkanol, glycol, polyethylene glycol, polypropylene glycol Glycerin, benzyl alcohol,
• Absorption enhancers include DMSO, isopropyl myristate, dipropylene glycol pelargonate, silicone oil, aliphatic esters, triglycerides and fatty alcohols.
• Antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole and tocopherol.
• the emulsion can be administered orally, transdermally or as an injection.
• the active ingredient is dissolved in a hydrophobic phase or a hydrophilic phase, and this is added with a suitable emulsifier, and if necessary, a colorant, an absorption promoting substance, a protective agent, an antioxidant, a light-shielding agent, a thickening substance, etc.
• a suitable emulsifier and if necessary, a colorant, an absorption promoting substance, a protective agent, an antioxidant, a light-shielding agent, a thickening substance, etc.
• hydrophobic phase paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglyceride, ethyl stearate, di-n-butyryl adipate, hexyl deurate, dipropylene glycol pelargonate, branched Esters of chain-like short-chain fatty acids and saturated fatty acids having a chain length of C 16 to C 18 , isopropyl myristate, isopropyl palmitate, capryl / caprate esters of saturated fatty alcohols having a chain length of C 12 to C 18 , stearic acid
• examples include isopropyl, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid ester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol,
• hydrophilic phase examples include water, propylene glycol, glycerin and sorbitol.
• Emulsifiers include nonionic interfaces such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefin acid, sorbitan monostearate, glyceryl monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether, etc.
• Activators such as disodium N-lauryl ⁇ -iminodipropionate and lecithin
• anionics such as sodium lauryl sulfate, fatty alcohol sulfate ether, monoethanolamine salt of mono / dialkyl polyglycol orthophosphate
• Cationic surfactants such as cetyltrimethylammonium chloride are listed.
• adjuvants include carboxymethyl cellulose, methyl cellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinyl pyrrolidone, polyvinyl alcohol, methyl vinyl ether, a copolymer of maleic anhydride, polyethylene glycol, wax and colloidal silica.
• Semi-solid preparations can be administered by applying on the skin or spreading or introducing into body cavities.
• Gels can be prepared by adding sufficient thickener to a solution prepared as described above for an injectable solution to produce a clear material having an ointment-like consistency.
• the optimal amount (effective amount) of the active ingredient depends on treatment or prevention, the type of infectious parasite, and the type of infection.
• the dose is in the range of about 0.0001 to 10,000 mg / kg body weight per day.
• the dose ranges from 0001 to 10,000 mg / kg body weight, and is administered in a single dose or divided doses.
• the concentration of the active ingredient in the endoparasite control agent of the present invention is generally about 0.001 to 100% by mass, preferably about 0.001 to 99%, more preferably about 0.005 to 20% by mass.
• the endoparasite control agent of the present invention may be a composition that is administered as it is, or a high-concentration composition that is used after being diluted to an appropriate concentration at the time of use.
• an existing endoparasite control agent can be used in combination for the purpose of reinforcing or complementing the effect of the endoparasite control agent of the present invention.
• a preparation in which two or more active ingredients are mixed before administration may be used, or two or more different preparations may be administered separately.
• the agricultural and horticultural insecticidal acaricide containing the benzimidazole compound represented by the general formula (1) of the present invention or a salt thereof as an active ingredient damages paddy field crops, field crops, fruit trees, vegetables, other crops, and florets.
• the desired effects of the agricultural and horticultural insecticidal acaricide of the present invention can be exerted by treating other crops, seeds such as flower buds, paddy field water, stalks and leaves, or a cultivation carrier such as soil. Among them, it is treated with seedling soil such as crops, flower buds, planting hole soil at the time of transplantation, plant origin, irrigation water, cultivated water in hydroponics, etc., and the present compound is absorbed from the root through or without soil. Application utilizing the so-called osmotic transfer property by making it a preferable form of use.
• Useful plants that can use the agricultural and horticultural insecticide of the present invention are not particularly limited, and examples thereof include cereals (eg, rice, barley, wheat, rye, oats, corn, etc.), beans ( Soy beans, red beans, broad beans, green beans, kidney beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, strawberries, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves and fruit vegetables ( Cabbage, tomato, spinach, broccoli, lettuce, onion, green onion (satsuki, parrot), bell pepper, eggplant, strawberry, pepper, ladle, leek, etc., root vegetables (carrot, potato, sweet potato, sweet potato, sweet potato, turnip, turnip, lotus root) , Burdock, garlic, raccoon, etc.), crops for processing (salmon, hemp, beet, hops, sugar cane, sugar beet, olive, rubber, coffee, tobacco, Etc.),
• Crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), flowers (kiku, rose, carnation, orchid, tulip, lily, etc.), garden trees (ginkgo, sakura, aoki, etc.), forest trees (todomatsu, And other plants such as pine, pine, hiba, cedar, cocoon, and eucalyptus.
• the “plant” includes HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, cetoxydim and the like. Also included are plants that have been rendered resistant by classical breeding methods or genetic recombination techniques to herbicides such as acetyl CoA carboxylase inhibitors, bromoxynil, dicamba, 2,4-D.
• Plants to which tolerance to an acetyl CoA carboxylase inhibitor has been imparted are Procedures of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci). USA) 87, 7175-7179 (1990).
• a mutant acetyl CoA carboxylase resistant to an acetyl CoA carboxylase inhibitor has been reported in Weed Science 53, 728-746 (2005).
• Introducing a plant resistant to an acetyl-CoA carboxylase inhibitor by introducing a mutation associated with imparting resistance to a plant or introducing a mutation associated with imparting resistance into a plant acetyl-CoA carboxylase, and further, chimeric plastic technology (Gura T. et al. 1999.
• toxins expressed in transgenic plants insecticidal proteins derived from Bacillus cereus and Bacillus popirie; ⁇ - such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis Endotoxins, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; nematicidal insecticidal proteins; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; lysine, corn-RIP, abrin, ruffin, saporin, bryodin, etc.
• ⁇ - such as Cry1Ab, Cry1Ac, Cry1F,
• Bosome inactivating protein RIP
• steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-CoA reductase; sodium channel, calcium channel inhibitor, etc. Ion channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.
• toxins expressed in such transgenic plants Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, Cry35Ab and other ⁇ -endotoxin proteins such as VIP1, VIP2, VIP3 or VIP3A
• insecticidal protein hybrid toxins partially defective toxins, and modified toxins.
• Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant technology.
• Cry1Ab lacking a part Cry1Ab lacking a part of the amino acid sequence is known.
• the modified toxin one or more amino acids of the natural toxin are substituted.
• Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera pests, Diptera pests, Lepidoptera pests and nematodes.
• the agricultural and horticultural insecticides according to the present invention can be used in combination with these techniques or systematically.
• the agricultural and horticultural insecticidal and acaricidal agents of the present invention are used for controlling pests or nematodes in the form of neat or appropriately diluted or suspended in order to control various pests.
• pests and nematodes occurring in fruit trees, cereals, vegetables, etc.
• seed immersion in seeds, seed dressing, Treat to soil, etc. such as seed treatment such as calper treatment, soil all layer mixing, crop application, floor soil mixing, cell seedling treatment, planting hole treatment, plant root treatment, top dress, rice box treatment, water surface application, etc. It can also be absorbed from the roots.
• the agrochemical for agricultural and horticultural use according to the present invention is used as it is, appropriately diluted with water or the like, or used in a place where the occurrence of the pest is predicted in an amount effective for pest control.
• agrochemical for agricultural and horticultural use according to the present invention is used as it is, appropriately diluted with water or the like, or used in a place where the occurrence of the pest is predicted in an amount effective for pest control.
• they can also be used as application to house building materials, smoke, bait and the like.
• Seed treatment methods include, for example, a method of immersing seeds in a liquid state by diluting or not diluting a liquid or solid preparation, and infiltrating the drug, mixing a solid preparation or liquid preparation with seeds, Examples thereof include a method of treating 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, bulbs, tubers, seed buds, stock buds, baskets, bulbs, or cuttings Mention may be made of plants for vegetative propagation.
• the “soil” or “cultivation carrier” of the plant when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, any material that can grow plants may be used, and so-called soil, seedling mats, water, etc. may be used. It may be a molecular substance, rock wool, glass wool, wood chip, bark or the like.
• a spraying method for crop foliage stored grain pests, house pests, hygiene pests, forest pests, etc., dilute liquid preparations such as emulsions and flowables or solid preparations such as wettable powders or granular wettable powders with water.
• Examples of application methods to soil include, for example, a method in which a liquid preparation is diluted or not diluted with water and applied to a plant stock or a seedling nursery, etc.
• a method of spraying to a nursery, etc. a method of spraying powder, wettable powder, granule wettable powder, granule, etc. before sowing or transplanting and mixing with the whole soil, a planting hole, making before planting or planting a plant body
• Examples thereof include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.
• the dosage form may vary depending on the time of application such as application at seeding, greening period, application at transplanting, etc. Apply by mold. It can also be applied by mixing with cultivating soil, and it can be mixed with cultivating soil and powder, granulated wettable powder or granules, for example, mixed with floor soil, mixed with covering soil, mixed into the entire cultivated soil and the like. Simply, the soil 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.
• a chemical solution such as emulsion or flowable as a source of water flowing into a paddy field such as a water inlet or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.
• a field crop In a field crop, it can be processed to a seed or a cultivation carrier close to a plant body from sowing to raising seedling.
• treatment on a plant source of a plant being cultivated is suitable. It is possible to perform spraying treatment using a granule or irrigation treatment in a liquid of a drug diluted or not diluted in water. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow.
• the irrigation treatment of the liquid drug or the granule spraying treatment to the seedling nursery is preferable.
• the agricultural and horticultural insecticidal and acaricidal agents of the present invention are generally used in a form convenient for use according to a conventional method for agricultural chemical preparations. That is, the benzimidazole compound represented by the general formula (1) of the present invention or a salt thereof is dissolved and separated by blending them in a suitable inert carrier or, if necessary, with an auxiliary agent in a suitable ratio.
• Suspended, mixed, impregnated, adsorbed or adhered, and formulated into appropriate dosage forms such as suspensions, emulsions, solutions, wettable powders, wettable granules, granules, powders, tablets, packs, etc. Use it.
• the composition of the present invention may contain, in addition to the active ingredient, an additive component usually used for an agricultural chemical preparation or an animal parasite control agent as necessary.
• an additive component usually used for an agricultural chemical preparation or an animal parasite control agent as necessary.
• the additive component include a carrier such as a solid carrier and a liquid carrier, a surfactant, a dispersant, a wetting agent, a binder, a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, and an antifreezing agent. , Anti-caking agents, disintegrants, decomposition inhibitors and the like. In addition, you may use a preservative, a plant piece, etc. for an additional component as needed.
• These additive components may be used alone or in combination of two or more.
• the solid support examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride.
• liquid carrier examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
• monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol
• polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
• Alcohols such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
• ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
• Ethers normal paraffins, naphthenes, isoparaffins, kerosene, mineral oils and other aliphatic hydrocarbons
• Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, etc.
• Esters lactones such as ⁇ -butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, soybean oil, rapeseed oil, Examples thereof include vegetable oils such as cottonseed oil and castor oil, and water. These may be used alone or in combination of two or more.
• surfactants used as dispersants and wetting agents include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxye Lenalkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene dio
• binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000 to 20000.
• Polyethylene glycol polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipid (for example, cephalin, lecithin, etc.) cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, cross-linked polyvinylpyrrolidone, maleic acid and styrenes Polymers, (meth) acrylic acid copolymers, half-esters of polycarboxylic alcohol polymers and dicarboxylic acid anhydrides, water soluble salts of polystyrene sulfonic acid, para Fin, terpene, polyamide resins, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, synthetic resin emulsions, and the like.
• phospholipid for example, cephalin, lecithin, etc.
• cellulose powder dextrin
• polyaminocarboxylic acid chelate compound cross-linked polyviny
• thickener examples include xanthan gum, guar gum, diyutane gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compound, water-soluble polymer such as polysaccharide, high-purity bentonite, fumed silica (fumed Inorganic fine powders such as silica and white carbon.
• the colorant examples include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.
• antifreezing agent examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
• Adjuvants for preventing caking and promoting disintegration include, for example, polysaccharides such as starch, alginic acid, mannose, galactose, polyvinylpyrrolidone, fumed silica (fumed silica), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride copolymer, starch / polyacrylonitrile graft copolymer A polymer etc. are mentioned.
• the decomposition inhibitor examples include desiccants such as zeolite, quicklime and magnesium oxide, antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
• desiccants such as zeolite, quicklime and magnesium oxide
• antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds
• ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
• preservative examples include potassium sorbate, 1,2-benzothiazolin-3-one, and the like.
• functional aids such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, UV absorbers and other supplements as necessary Agents can also be used.
• the blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide of the present invention.
• 0.01 to 50 parts by weight 0.01 to 50% by weight based on the total weight of the agricultural and horticultural insecticide
• 0.01 to 50 parts by weight 0.01 to 50% by weight based on the total weight of the agricultural and horticultural insecticide
• the amount of the agricultural and horticultural insecticide used in the present invention is various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time.
• the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg as the active ingredient compound according to the purpose.
• Agricultural and horticultural insecticides and acaricides according to the present invention include other pesticides, acaricides, and nematicides for agricultural and horticultural purposes for the purpose of controlling pests to be controlled, the expansion of the appropriate period of control, or reducing the dose. It can also be used by mixing with fungicides, biological pesticides, etc., and can also be used by mixing with herbicides, plant growth regulators, fertilizers, etc., depending on the situation of use.
• XMC 3,5-xylyl methylcarbamate
• Bacillus thuringienses aizawai Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses kurstaki, Bacillus thuringienses tenebrionis, Bacillus thuringienses produced crystal protein toxin, BPMC, Bt toxin CPC chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1, 3-dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropy
• Examples of agricultural and horticultural fungicides used for similar purposes include aureofungin, azaconazole, azithiram, acipetacs, acibenzolar, acibenzolar-S-methyl. ), Azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam, isothianyl (Isotianil), isovaledione, isopyrazam, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenfos, imazalil Iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, uniconazole, uniconazole-P, eclomeole, echlomez Edifenphos, etaconazole, ethaboxam, e
• herbicides for example, 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2, 4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, aclonifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, aslam, acetochlor, Atrazine, atraton, anisuron, anilofos, abiglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole, amino Cyclopyrachlor (aminocyclopyrachlor), aminopyralid (aminopyralid), Amibu Gin (amibuzin), amiprophos-methyl,
• biological pesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CV), insect pox virus (Entomopoxivirus, EPV) ) And other virus preparations, Monocrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasturia ⁇ pene insecticides, and Pasturia pene insecticides Sterilization of microbial pesticides, Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc.
• microbial pesticide to be used by using mixed such as biological pesticides utilized as herbicides, such as Xanthomonas campestris (Xanthomonas campestris), the same effect can be expected.
• Formulation Example 1 Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixing of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above is uniformly mixed and dissolved to prepare an emulsion.
• Formulation Example 2 Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above is mixed and ground uniformly to form a powder.
• Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts lignin sulfonate 5 parts The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules.
• Formulation Example 4 Compound of the present invention 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts The above is uniformly mixed and ground to obtain a wettable powder.
• Formulation Example 6 Compound of the present invention 2 parts Dimethyl sulfoxide 10 parts 2-propanol 35 parts Acetone 53 parts The above mixture is uniformly mixed and dissolved to obtain a spray solution.
• Formulation Example 7 Compound of the present invention 5 parts Hexylene glycol 50 parts Isopropanol 45 parts The above is uniformly mixed and dissolved to give a solution for transdermal administration.
• Formulation Example 8 Compound of the present invention 5 parts Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts The above is mixed and dissolved uniformly to give a solution for transdermal administration.
• Formulation Example 9 Compound of the present invention 2 parts Light liquid paraffin 98 parts The above is mixed and dissolved uniformly to prepare a solution for transdermal administration (dropping).
• Formulation Example 10 Compound of the present invention 2 parts Light liquid paraffin 58 parts Olive oil 30 parts ODO-H 9 parts Shin-Etsu silicone 1 part The above is mixed and dissolved uniformly to give a solution for transdermal administration (dropping).
• Control value test against peach aphid (Myzus persicae) Chinese cabbage was planted in a plastic pot having a diameter of 8 cm and a height of 8 cm to breed a peach aphid, and the number of parasites in each pot was investigated.
• the benzimidazole compound represented by the general formula (1) of the present invention or a salt thereof is dispersed in water and diluted to 500 ppm of a chemical solution.
• the number of parasites of the peach aphid parasitizing each Chinese cabbage on the sixth day after spraying the drug was investigated, the control value was calculated from the following formula, and the determination was made according to the following criteria.
• Ta Number of parasites before spraying in the treated area
• Ca Number of parasites before spraying in the untreated area
• C Number of parasites after spraying in the untreated area
• the compounds 1-3, 1-9, 1-10, 1-20, 1-24, 1-41, 1-42, 5-15, 5-17 and 5-24 of the compound of the present invention are A activity was shown.
• Test Example 2 Insecticidal test against Japanese brown planthopper (Laodelphax striatella)
• the benzimidazole compound represented by the general formula (1) of the present invention or a salt thereof is dispersed in water and diluted to 500 ppm, and rice seedlings (variety: Nipponbare) are added to the chemical. Immerse for 30 seconds, air dry, put in a glass test tube, inoculate 10 each of the 3 Japanese beetles, inoculate cotton plugs, and investigate the survival rate from the number of live and dead insects 8 days after the inoculation. And was determined according to the following criteria.
• the compounds 1-7, 1-10, 1-12, 1-13, and 5-15 of the compound of the present invention showed the activity of A.
• Test Example 3 Insecticidal test against Plutella xylostella Benzimidazoles represented by the general formula (1) of the present invention are prepared by releasing adult moths from the Chinese cabbage seedlings and laying eggs after two days of release.
• the drug containing a compound or a salt thereof as an active ingredient was immersed in a chemical solution diluted to 500 ppm for about 30 seconds, air-dried and then left in a thermostatic chamber at 25 ° C.
• Six days after immersion in the chemical solution the number of hatching insects was investigated, the corrected death rate was calculated according to the following formula, and the determination was made according to the criterion of Test Example 2. 1 ward, 10 heads, 3 systems.
• the compounds of the present invention 1-2, 1-3, 1-4, 1-6, 1-7, 1-9, 1-10, 1-12, 1-13, 1-14, 1-15 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-40, 1-41, 1-42, 1-44, 1 Compounds of ⁇ 45, 3-1, 5-2, 5-10, 5-12, 5-15, 5-18, 5-19, or 5-24 showed A activity.
• Test Example 4 Acaricidal test against urticae (Tetranychus urticae).
• a leaf disk having a diameter of 2 cm is made of green beans, placed on wet filter paper, inoculated with female adults, and then the benzimidazole compound represented by the general formula (1) of the present invention or a salt thereof is used as an active ingredient.
• 50 ml of a chemical solution diluted to 500 ppm was sprayed uniformly on the turntable, and after spraying, it was left in a constant temperature room at 25 ° C.
• Two days after the drug treatment the number of dead insects was investigated, the corrected death rate was calculated according to the following formula, and the determination was made according to the criteria of Test Example 2. 2 units in 10 wards in 1 ward.
• Test Example 5 Test for evaluating the effect of Haemonchus contourus on larval movement
• a DMSO-diluted solution of a benzimidazole compound represented by the general formula (1) of the present invention or a salt thereof The final concentration was 50 ppm.
• Twenty L-1 stage larvae of Hemonx elegans were released and allowed to stand for 4 days, after which their motility was investigated.
• the inhibition rate of movement in each treatment section was corrected and calculated based on the inhibitory power of only the DMSO solution, and judged according to the following criteria.
• Test Example 6 Test for evaluating the effect of Dirofilaria immitis on larval movement Inoculate 500 L-1 stage larvae of dog filamentous worms diluted in a predetermined preparation solution per 96-well plate, and the general formula (1 The final concentration was adjusted to 50 ppm by adding a DMSO diluted solution of a benzimidazole compound or a salt thereof. Then, it left still for 3 days and investigated the exercise ability. The inhibition rate of movement in each treatment section was corrected and calculated based on the inhibitory power of only the DMSO solution, and judged according to the following criteria.
• the compound according to the present invention has an excellent control effect against a wide range of agricultural and horticultural pests and mites, and is useful.

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