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
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/647—Triazoles; Hydrogenated triazoles
  • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P7/00—Arthropodicides
  • A01P7/04—Insecticides
• • 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
  • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
  • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
  • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
• • 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
  • C07D401/14—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 three or more hetero rings

Definitions

• the present invention relates to azinylazole compounds and pest control agents. More specifically, the present invention has excellent insecticidal activity and / or acaricidal activity, is excellent in safety, and can be synthesized industrially advantageously. Azinylazole compound and pest control containing the same as an active ingredient. Regarding agents.
• the present application claims priority based on Japanese Patent Application No. 2020-037098 filed in Japan on March 4, 2020, the contents of which are incorporated herein by reference.
• Patent Document 1 states that the compound represented by the formula (A) or the like can be used for suppressing ectoparasites in animals.
• An object of the present invention is to provide an azinylazole compound which is excellent in pest control activity, particularly insecticidal activity and / or acaricidal activity, is excellent in safety, and can be synthesized industrially advantageously.
• Another object of the present invention is to provide a pest control agent, an insecticide or acaricide, an ectoparasite control agent, or an endoparasite control or control agent containing an azinylazole compound as an active ingredient.
• X is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkyl.
• Sulfinyl group substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C3-6 cycloalkylthio Shows a group, substituted or unsubstituted C3-6 cycloalkylsulfinyl group, substituted or unsubstituted C3-6 cycloalkylsulfonyl group, nitro group, or cyano group;
• X indicates a substituted or unsubstituted C2-6 alkynyl group;
• n indicates the number of X and is an integer of 0 to 5, and when n is 2 or more, X may be the same or different from each other.
• R 1 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
• R 2 represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
• R 3 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, or a substituted or unsubstituted C1-6 alkoxycarbonyl group.
• Y 1 represents a nitrogen atom or a group represented by CR a
• Y 2 represents a group represented by a nitrogen atom or CR a
• R a each independently represent a hydrogen atom, a halogeno group or a substituted or unsubstituted C1 ⁇ 6 alkyl group
• Q indicates a substituted or unsubstituted 6-membered heteroaryl group.
• [2] The compound according to [1] or a salt thereof, wherein Q is a substituted or unsubstituted pyridyl group or a substituted or unsubstituted pyrimidinyl group.
• a pest control agent containing at least one selected from the compound according to [1] or [2] or a salt thereof as an active ingredient.
• An insecticide or acaricide containing at least one selected from the compound according to [1] or [2] or a salt thereof as an active ingredient.
• An ectoparasite control agent containing at least one selected from the compound according to [1] or [2] or a salt thereof as an active ingredient.
• An endoparasite control or extermination agent containing at least one selected from the compound according to [1] or [2] or a salt thereof as an active ingredient.
• the azinylazole compound of the present invention has a function of controlling harmful organisms that pose a problem in terms of crops and hygiene.
• the control agent containing the azinylazole compound of the present invention can effectively control pests, especially agricultural pests and mites, at a lower concentration, and further ectoparasites and endoparasites that may harm humans and animals. Insects can be effectively controlled.
• the azinylazole compound of the present invention is a compound represented by the formula (I) or a salt thereof.
• the term “unsubstituted” means that it is only a parent group. When there is no description of “substitution” and only the name of the parent group is described, it means “unsubstituted” unless otherwise specified.
• substitution means that any hydrogen atom of the parent group is substituted with a group (substituent) having the same or different structure as the mother nucleus. Therefore, a “substituent” is another group attached to the parent group.
• the substituent may be one or two or more.
• the two or more substituents may be the same or different.
• Terms such as "C1 to 6" indicate that the number of carbon atoms of the parent group is 1 to 6 or the like. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.
• the "substituent” is chemically acceptable and is not particularly limited as long as it has the effect of the present invention.
• the groups that can be “substituents” are illustrated below. C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc.
• Alkyl group Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, etc.
• C2-6 alkenyl groups C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group;
• C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; Phenyl group, naphthyl group; Benzyl group, phenethyl group; 3-6 member heterocyclyl group; 3-6 member heterocyclyl C1-6 alkyl group;
• C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group; C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group; Phenoxy group, naphthoxy group; Phenyl C1-6 alkoxy groups such as benzyloxy group and phenethyloxy group; 5- to 6-membered heteroaryloxy groups such as thiazolyloxy groups and pyridyloxy groups; 5- to 6-membered heteroaryl C1 to 6 alkyloxy groups such as thiazolylmethyloxy group and pyridylmethyloxy group;
• Formylation group C1-6 alkylcarbonyl groups such as acetyl and propionyl groups; Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy groups and propionyloxy groups; Benzoyl group; C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group; C1-6 alkoxycarbonyloxy groups such as methoxycarbonyloxy group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group, i-propoxycarbonyloxy group, n-butoxycarbonyloxy group, t-butoxycarbonyloxy group; Carboxyl group;
• Halogeno groups such as fluoro groups, chloro groups, bromo groups and iod groups; C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group; C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group, 2-fluoro-1-butenyl group; C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group; C1-6 haloalkoxy groups such as trifluoromethoxy group, 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group; C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group, 3-bromobutenyloxy group
• Amino group C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group, diethylamino group; Phenylamino groups such as anilino groups; Phenyl C1-6 alkylamino groups such as benzylamino group, phenethylamino group; Formylamino group; C1-6 alkylcarbonylamino groups such as acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group; Aminocarbonyl group having an unsubstituted or substituent such as a carbamoyl group, a dimethylaminocarbonyl group, a phenylamino
• C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group; C1-6 haloalkylthio groups such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group; Phenylthio group, naphthylthio group; 5- to 6-membered heteroarylthio groups such as thiazolylthio groups and pyridylthio groups;
• C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group; Phenylsulfinyl group; 5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl groups, pyridylsulfinyl groups;
• C1-6 alkylsulfonyl groups such as methylsulfonyl groups, ethylsulfonyl groups, t-butylsulfonyl groups; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl groups, 2,2,2-trifluoroethylsulfonyl groups; Phenylsulfonyl group; 5- to 6-membered heteroarylsulfonyl groups such as thiazolylsulfonyl groups and pyridylsulfonyl groups; C1-6 alkylsulfonyloxy groups such as methylsulfonyloxy groups, ethylsulfonyloxy groups, t-butylsulfonyloxy groups; C1-6 haloalkylsulfonyloxy groups such as trifluoromethylsulfonyloxy groups, 2,2,2-trifluoroethy
• Tri-C1-6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group; Triphenylsilyl group; Pentafluorosulfanyl group; Cyano group; Nitro group;
• any hydrogen atom in the substituent may be substituted with a group having a different structure.
• the "substituent” in this case include a C1 to 6 alkyl group, a C1 to 6 haloalkyl group, a C1 to 6 alkoxy group, a C1 to 6 haloalkoxy group, a halogeno group, a cyano group, a nitro group and the like.
• the above-mentioned "3 to 6-membered heterocyclyl group” is a 3-membered ring, a 4-membered ring, 5 containing 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as ring constituent atoms. It is a member ring or a 6-member ring.
• the heterocyclyl group may be monocyclic or polycyclic.
• the polycyclic heterocyclyl group may have any of a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring as long as at least one ring is a heterocyclic ring.
• Examples of the "3- to 6-membered heterocyclyl group” include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.
• Examples of the 3- to 6-membered saturated heterocyclyl group include an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group and a dioxanyl group.
• Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group. Can be done.
• 6-membered heteroaryl group examples include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, a triazinyl group and the like.
• X is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkyl.
• Sulfinyl group substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted C3-6 cycloalkyloxy group, substituted or unsubstituted C3-6 cycloalkylthio Shows a group, substituted or unsubstituted C3-6 cycloalkylsulfinyl group, substituted or unsubstituted C3-6 cycloalkylsulfonyl group, nitro group, or cyano group;
• X represents a substituted or unsubstituted C2-6 alkynyl group.
• n indicates the number of X and is an integer of 0 to 5. When n is 2 or more, X may be the same or different from each other.
• halogeno group examples include a fluoro group, a chloro group, a bromo group, an iod group and the like.
• the "C1 to 6 alkyl group” in X may be a straight chain or a branched chain.
• the "C1 to 6 alkyl groups” in X include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group and s-. Butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group and the like can be mentioned.
• Examples of the "C1 to 6 alkoxy group" in X include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, and an i-butoxy group. Examples thereof include an s-butoxy group, a t-butoxy group, and an i-hexyloxy group.
• Examples of the "C1 to 6 alkylthio group" in X include a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, and an i-propylthio group.
• Examples of the "C1 to 6 alkylsulfinyl group" in X include a methylsulfinyl group, an ethylsulfinyl group, and a t-butylsulfinyl group.
• Examples of the "C1 to 6 alkylsulfonyl group" in X include a methylsulfonyl group, an ethylsulfonyl group, and a t-butylsulfonyl group.
• Examples of the "C3 to 6 cycloalkyl group" in X include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.
• Examples of the "C3 to 6 cycloalkyloxy group” in X include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.
• Examples of the "C3 to 6 cycloalkylthio group” in X include a cyclopropylthio group, a cyclobutylthio group, a cyclopentylthio group, a cyclohexylthio group and the like.
• Examples of the "C3 to 6 cycloalkylsulfinyl group” in X include a cyclopropylsulfinyl group, a cyclobutylsulfinyl group, a cyclopentylsulfinyl group, a cyclohexylsulfinyl group and the like.
• Examples of the "C3 to 6 cycloalkylsulfonyl group" in X include a cyclopropylsulfonyl group, a cyclobutylsulfonyl group, a cyclopentylsulfonyl group, and a cyclohexylsulfonyl group.
• C3-6 cycloalkyl group "C3-6 cycloalkyloxy group”, “C3-6 cycloalkylthio group”, “C3-6 cycloalkylsulfinyl group”, or “C3-6 cycloalkylsulfonyl group” in X
• the above substituents include halogeno groups such as fluoro group, chloro group, bromo group and iodo group; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group and i.
• C1-6 alkyl groups such as -butyl group, t-butyl group, n-pentyl group, n-hexyl group; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1 C1-6 haloalkyl groups such as -fluoro-n-butyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group C1-6 alkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, C1-6 haloalkoxy groups such as trifluoromethoxy group; or cyano group; are preferable.
• a halogeno group a halogeno group substituted or unsubstituted C1 to 6 alkyl group, a halogeno group substituted or unsubstituted C1 to 6 alkoxy group, or a cyano group is preferable, and a halogeno group or a halogeno group substituted is preferable.
• a C1 to 6 alkyl group, a halogeno group substituted C1 to 6 alkoxy group, or a cyano group is preferable.
• Examples of the "halogeno-substituted C1 to 6 alkyl group" in X include a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, and a 2,2,2,1,1-pentafluoroethyl group. And so on.
• Examples of the "halogeno-substituted C1 to 6 alkoxy groups" in X include a difluoromethoxy group, a trifluoromethoxy group, a 2,2-difluoroethoxy group, a 2,2,2-trifluoroethoxy group, and 2,2,1. Examples thereof include 1-tetrafluoroethoxy group and 2,2,2,1,1-pentafluoroethoxy group.
• Examples of the "C2-6 alkynyl group" in X include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group and the like. It can be mentioned, and an ethynyl group is preferable.
• a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group
• a hydroxyl group a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, C1-6 alkoxy groups such as n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group and the like.
• C1-6 haloalkoxy group phenyl group; 4-chlorophenyl group, 4-trifluoromethylphenyl group, 4-trifluoromethoxyphenyl group, etc., "halogeno group, C1-6 haloalkyl group, or C1-6 haloalkoxy group
• a phenyl group substituted with "; a cyano group; or a tri-C1-6 alkyl-substituted silyl group; is preferred, a tri-C1-6 alkyl-substituted silyl group is more preferred, and a trimethyl-substituted silyl group is more preferred.
• R 1 represents a hydrogen atom or a substituted or unsubstituted C1 to 6 alkyl group
• R 2 represents a hydrogen atom or a substituted or unsubstituted C1 to 6 alkyl group
• R 3 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, or a substituted or unsubstituted C1-6 alkoxycarbonyl group, preferably a hydrogen atom.
• R 3 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, or a substituted or unsubstituted C1-6 alkoxycarbonyl group, preferably a hydrogen atom.
• C1 to 6 alkyl in R 1 , R 2 , and R 3 can be the same as those exemplified in X.
• Specific examples of the "C1 ⁇ 6 alkyl group” in R 3 may be exemplified such as acetyl group, propionyl group.
• Specific examples of the "C1 ⁇ 6 alkoxycarbonyl group” in R 3 is methoxycarbonyl group, an ethoxycarbonyl group, n- propoxycarbonyl group, i- propoxycarbonyl group, n- butoxycarbonyl group, and the like t- butoxycarbonyl group Can be mentioned.
• R 1 examples of R 2 or R 3 definitive "C1 ⁇ 6 alkyl group", the substituent on the "C1 ⁇ 6 alkyl group” or "C1 ⁇ 6 alkoxycarbonyl group", fluoro, chloro, bromo Halogeno groups such as groups and iodo groups; hydroxyl groups; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and other C1 to 6 alkoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; phenyl group; 4-chlorophenyl group, 4-trifluoromethylphenyl group, A "phenyl group substituted with a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group”
• examples of the substituent on the "C1 ⁇ 6 alkyl group" in R 3 cyclopropyl group, cyclobutyl group, cyclopentyl group, C3 ⁇ 6 cycloalkyl group such as cyclohexyl group; C2 ⁇ 6 alkenyl, such as vinyl group Group; or ethynyl group is preferred.
• Y 1 represents a nitrogen atom or a group represented by CR a, preferably a nitrogen atom.
• Y 2 represents a nitrogen atom or a group represented by CR a.
• R a is, independently, a hydrogen atom, a halogeno group or a substituted or unsubstituted C1 ⁇ 6 alkyl group, preferably denotes a hydrogen atom or an unsubstituted C1 ⁇ 6 alkyl group.
• Specific examples of the "halogeno group" or "C1-6 alkyl” in Ra can be the same as those exemplified in X.
• [Q] Q indicates a substituted or unsubstituted 6-membered heteroaryl group.
• the "6-membered heteroaryl group" in Q is an aromatic 6-membered ring containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as ring constituent atoms. It is a monovalent group. When there are two or more heteroatoms, they may be the same or different.
• the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, a triazinyl group and the like.
• Q is preferably a pyridyl group, a pyrimidinyl group, or a pyridadinyl group, and more preferably a pyridyl group or a pyrimidinyl group.
• a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group
• a methyl group, an ethyl group, an n-propyl group, an i-propyl group and an n- C1-6 alkyl groups such as butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group
• hydroxyl group methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy C1-6 alkoxy groups
• the azinylazole compound of the present invention is not particularly limited depending on the production method thereof.
• the azinylazole compound of the present invention (hereinafter, may be referred to as “the compound of the present invention”) can be obtained by a procedure described in Examples and the like using a known reaction. It can be obtained by using the reaction described in the reaction scheme shown below in addition to the method described in Examples and the like.
• reaction scheme 1 The outline of the method for preparing the compound represented by the formula (I) is shown in the following reaction scheme 1.
• the symbols in formula (I) have the same meanings as those above.
• the symbols in formula (2) have the same meaning as those in formula (I).
• X and n in the formula (3) have the same meanings as those in the formula (I).
• Z represents a halogeno group.
• the compound of formula (I) can be prepared by reacting the compound of formula (2) with the compound of formula (3) in the presence of an appropriate base.
• organic bases such as triethylamine and N, N-diisopyrethylamine are preferable.
• reaction scheme 2 The outline of the method for preparing the compound represented by the formula (2) is shown in the following reaction scheme 2.
• the symbols in formula (4) have the same meaning as those in formula (I). Z'indicates a halogeno group.
• R 3 in the formula (5) shows the same meaning as R 3 in formula (I).
• the compound of the formula (2) can be prepared by reacting the compound of the formula (4) with the amine compound of the formula (5).
• reaction scheme 3 Among the compounds represented by the formula (4), the compound represented by the formula (4') in which Y 1 is a nitrogen atom and Y 2 is a group represented by CR a is described in the following reaction scheme 3. It can be prepared by the method shown.
• reaction scheme 4 Among the compounds represented by the formula (3), the compound represented by the formula (3') in which the 2-position of the quinazoline ring is hydrogen can be prepared by the method shown in the following reaction scheme 4.
• X in the formula (3') has the same meaning as X in the formula (I), m represents an integer of 0 to 4, and Z'represents a halogeno group.
• X in the formula (10) has the same meaning as X in the formula (I), and m represents an integer of 0 to 4.
• the compound of formula (3') can be prepared by condensing the compound of formula (10) and formamide under heating conditions and then reacting with a halogenating agent such as thionyl chloride.
• the compound of the present invention is excellent in controlling harmful organisms such as various agricultural pests and mites that affect the growth of plants.
• the compound of the present invention is a highly safe substance because it causes less phytotoxicity to crops and has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of insecticides or acaricides.
• resistance to various existing drugs has developed in many pests such as diamondback moth, planthopper, leafhopper, and aphid, causing a problem of insufficient efficacy of these drugs, and a drug effective against pests of resistant strains is desired. ing.
• the compound of the present invention exhibits an excellent control effect not only on sensitive strains but also on pests of various resistant strains and mites of acaricide-resistant strains.
• the compound of the present invention is excellent in controlling ectoparasites and endoparasites that are harmful to humans and animals. In addition, it is a highly safe substance because it has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of a control agent for ectoparasites and endoparasites.
• the compound of the present invention is effective at all developmental stages of the organism to be controlled, and exhibits an excellent control effect on, for example, eggs such as mites and insects, larvae, larvae, pupae, and adults.
• the pest control agent, or insecticide or acaricide of the present invention contains at least one selected from the compounds of the present invention as an active ingredient.
• the amount of the pest control agent of the present invention, or the compound of the present invention contained in the insecticide or acaricide is not particularly limited as long as it shows the control effect of pests, agricultural pests or mites.
• the pest control agent, insecticide or acaricide of the present invention includes grains; vegetables; root vegetables; potatoes; flowers; fruit trees; foliage plants, tea, coffee, cacao and other trees; grasses; Turbs; preferably used for plants such as cotton.
• the pest control agent, or insecticide or acaricide of the present invention can be any of leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tubers, shoots, cuttings, etc. It may be used for the site of.
• the pest control agent, insecticide or acaricide of the present invention is not particularly limited depending on the species of the plant to which it is applied. Examples of plant species include original species, varieties, improved varieties, cultivars, mutants, hybrids, genetically modified organisms (GMOs) and the like.
• the pest control agent of the present invention can be used for seed treatment, foliage spraying, soil application, water surface application, etc. in order to control various agricultural pests and mites.
• (1) Lepidoptera butterflies or moths Arctiidae moths, such as the fall webworm (Hyphantria cunea) and morus alba (Lemyra imparilis); (B) Bucculatricidae moths, such as Bucculatrix pyrivorella; (C) Moths of the family Carposinidae, such as Carposina sasakii; (D) Moths of the Crambidae family, such as the genus Diaphania spp., Diaphania indica, Diaphania nitidalis; for example, the genus Ostrinia (Ostrinia spp.).
• Awanomeiga (Ostrinia furnacalis), European cornballer (Ostrinia nubilalis), Azukinomeiga (Ostrinia scapulalis); Diatraea grandiosella), Kwanomeiga (Glyphodes pyloalis), Hymadalanomeiga (Hellula undalis), Shibatuga (Parapediasia teterrella);
• Noctuidae (Agrotis ipsilon), Noctuidae (Agrotis segetum); For example, Helicoverpa spp., Helicoverpa armigera, Helicoverpa assulta, Cotton ball worm (Helicoverpa zea); Heliothis spp., Heliothis armigera, Heliothis virescens; Others, Aedia leucomelas, Ctenoplusia agnata, Eudocima tyran Mamestra brassicae), Awayoto (Mythimna separata), Futaobikoyaga (Naranga aenescens), Matsukiriga (Panolis japonica), Nisetama nayaga (Peridroma saucia), Soibean looper (Pseudoplusia includens), Irakusagin uwaba (Tricho) (M) Moths of the Tuft moth family
• Plutellidae moths such as the Acrolepiopsis spp., Acrolepiopsis sapporensis, Acrolepiopsis suzukiella; and other diamondback moths (Plutella xylostella);
• P) Pyralidae moths such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Greater wax moth;
• Q Moths of the family Sphingidae, such as the Manduca spp. Tomato hornworm (Manduca quinquemaculata), Tobacco hornworm (Manduca sexta);
• Ringomonhamaki (Archips breviplicanus), Midarekakumonhamaki (Archips fuscocupreanus); ), Chahamaki (Homona magnanima), Mameshiniga (Leguminivora glycinivorella), Hosobahimehamaki (Lobesia botrana), Mamehimesayamushiga (Matsumuraeses phaseoli), Tobihamaki (Pandemis heparana), Tenguhamaki (Sparganothis pill) (U) Moths of the Ermine moth family (Yponomeutidae), such as the apple fruit moth (Argyresthia conjugella).
• Thripidae Thysanoptera pests
• Thripidae Thripidae
• Thripidae Pieris-associated pests
• Thripidae Thripidae
• Thripidae Pieris-associated pests
• B Thripidae, for example Frankliniella spp., Thripidae thripidae, Thripidae thripidae, Frankliniella occidentalis
• Thrips spp. Thrips palmi, Thrips tabaci Others, Thripidae (Heliothrips haemorrhoidalis), Western flower thrips (Scirtothrips dorsalis).
• A Leafhoppers (Cicadellidae), for example, Empoasca spp., Leafhoppers (Empoasca fabae), Leafhoppers (Empoasca nipponica), Chanomidorihimeyokobai (Empoasca onukii), Maeno Leafhopper (Empoasca sakaii); Others, Leafhopper (Arboridia apicalis), Empoasca (Balclutha saltuella), Leafhopper (Epiacanthus stramineus), Leafhopper (Macrosteles striifrons) ..
• Stink bugs for example, Nezara spp., Stink bug (Nezara antennata), Southern green stink bug (Nezara viridula); for example, Stink bug genus (Eysarcoris spp.) , Stink bug (Eysarcoris aeneus), Stink bug (Eysarcoris lewisi), Stink bug (Eysarcoris ventralis), Others, Stink bug (Dolycoris baccarum), Stink bug (Dolycoris baccarum) Halyomorpha halys), stink bug (Piezodorus hybneri), stink bug (Plautia crossota), stink bug (Scotinophora lurida); (F) Of the red bug family (Pyrrhocoridae), for example, the red bug (Dysdercus cingulatus); (G) Of the leaf-footed bug family (Rhopalidae),
• (D) Sternorrhyncha A) Adelgidae, for example, Larch aphid (Adelges laricis);
• (B) Whitefly family Aleyrodidae) For example, Silverleaf whitefly (Bemisia argentifolii), Tobacco whitefly (Bemisia tabaci) of Bemisia species (Bemisia spp.); Other whitefly (Aleurocanthus spiniferus), Whitefly (Di) citri), whitefly (Trialeurodes vaporariorum);
• Aphididae for example, Aphis spp., Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii.
• European apple aphid (Aphis pomi), chicken aphid (Aphis sambuci), snowy aphid (Aphis spiraecola); for example, corn aphid (Rhopalosiphum maidis), wheat aphid (Rhopalosiphum maidis)
• the genus Aphididae (Dysaphis spp.), Aphididae (Dysaphis plantaginea), Aphididae (Dysaphis radicola); for example, the genus Macrosiphum spp.
• Macrosiphum euphorbiae for example, from the genus Myzus spp., Myzus cerasi, Myzus persicae, Myzus varians; pisum), potato aphid (Aulacorthum solani), wheat aphid (Brachycaudus helichrysi), daikon aphid (Brevicoryne brassicae), strawberry aphid (Chaetosiphon fragaefolii), peach aphid (Chaetosiphon fragaefolii) , Fake aphid (Lipaphis erysimi), Aphididae (Megoura viciae), Aphididae (Metopolophium dirhodum), Lettuce aphid (Nasonovia ribis-nigri), Hot Phorodon humuli, Schizaphis graminum, Sitobion avenae, Toxoptera aurantii;
• Pests of the suborder Polyphaga (a) Anobiidae, for example, Lasioderma serricorne; (B) Attelabidae, for example, Byctiscus betulae, Rhynchites heros; (C) Lyctus brunneus of the family Lyctus brunneus; (D) Of the family Curculionidae (Brentidae), for example, Cylas formicarius; (E) Of the jewel beetle family (Buprestidae), for example, the jewel beetle (Agrilus sinuatus); (F) Cerambycidae, for example, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus; (G) Chrysomelidae, eg, Bruchus spp., Pea weevil (Bruchus pisorum), Broad bean weevil (Bruchus s
• Root worm (Diabrotica barberi), Southern corn root worm (Diabrotica undecimpunctata), Western corn root worm (Diabrotica virgifera); ); Others, Aulacophora femoralis, Callosobruchus chinensis, Cassida nebulosa, Chaetocnema concinna, Colorado leaf beetle (Leptinotarsa decemlineata), Inekubihosohamushi (Leptinotarsa decemlineata) Nagasnetobi beetle (Psylliodes angusticollis);
• Agromyzidae for example, Agromyzidae (Liriomyza spp.), Agromyzidae (Liriomyza bryoniae), Agromyzidae (Liriomyza chinensis), Tomato leafminer (Liriomyza sativae), Agromyzidae (Liriomyza sativae), Agromyzidae (Liriomyza sativae) Others, Agromyzidae (Chromatomyia horticola), Agromyzidae (Agromyza oryzae); (B) Anthomyiidae, eg, Delia spp., Delia platura, Delia radicum; and other sugar beet, Pegomya cunicularia; (C) Drosophilidae, for example, Drosophil
• Nematocera (A) Cecidomyiidae, for example, Soybean Cecidomyiidae, Sorghum sorghicola, Hessian fly (Mayetiola destructor), Mugia caterpillar (Sitodiplosis mosellana).
• Orthoptera pests Grasshoppers (Acrididae), for example, the genus Schistocerca spp., American locusts (Schistocerca americana), desert locusts (Schistocerca gregaria); Australia Tobibatta (Chortoicetes terminifera), Sydney Inago (Dociostaurus maroccanus), Tonosamabatta (Locusta migratoria), Brown Inago (Locustana pardalina), Akatobibatta (Nomadacris septemfasciata), Kobaneinago (Oxya yezoensis) (B) Cricket family (Gryllidae), such as European house cricket (Acheta domestica), cricket (Teleogryllus emma); (C) Mole cricket (Gryllotalpidae), for example, mole cricket (Gryllotalpa orientalis); (D) Of the Bush cricket family (Tettigoniidae), for example
• Mites (Acari) (A) Acaridida of the order Astigmata (A) Acaridae mites, such as Rhizoglyphus spp., Rhizoglyphus echinopus, Rhizoglyphus robini; for example, Tyrophagus spp. (Tyrophagus neiswanderi), Tyrophagus putrescenti, Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis;
• B Prostigmata prostigmata (Actinedida)
• A Spider mite (Tetranychidae) mites, such as Bryobia spp., Clover mite (Bryobia praetiosa), fake clover mite (Bryobia rubrioculus); for example, Eotetranychus spp.
• Eotetranychus asiaticus Anzu spider mite (Eotetranychus boreus), Eotetranychus celtis, Michinoku spider mite (Eotetranychus geniculatus), Miyake spider mite (Eotetranychus geniculatus), Miyake spider mite (Eotetranychus kankitus) (Eotetranychus smithi), Suginami spider mite (Eotetranychus suginamensis), walnut spider mite (Eotetranychus uncatus); Mango spider mite (Oligonychus mangiferus), sugar cane spider mite (Oligonychus orthius), avocado spider mite (Oligonychus perseae), Ezosugi spider mite (Oligonychus pustulosus), rice spider mite (Oligonychus shinkajii), rice spider mite (Oligonychus shinkajii) , Mikan spider mit
• Tenuipalpus spp. Tenuipalpus pacificus
• Tenuipalpus zhizhilashviliae Other, pineapple zhizhilashviliae
• Eriophyidae mites such as Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, carnation.
• Aceria paradianthi Aceria tiyingi, Aceria tulipae, Aceria zoysiea; for example, Eriophyes spp., Eriophyes chibaensis, Eriophyes chibaensis emarginatae); for example, Aceria spp., Tomato sabi mite (Aculops lycopersici), Mikan sabi mite (Aculops pelekassi); for example, Aculus spp.
• the pest control agents of the present invention are other active ingredients such as fungicides, insecticides / acaricides, nematode pesticides, soil pesticides; plant growth regulators, synergists, fertilizers, soil conditioners, for animals. It may be mixed or used in combination with feed or the like.
• the combination of the compound of the present invention and another active ingredient can be expected to have a synergistic effect on insecticidal, acaricidal, and nematode activity.
• the synergistic effect can be confirmed by Colby's formula (Colby.SR; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, pp. 20-22, 1967) according to a conventional method.
• insecticides / acaricides, nematodes, soil pesticides, anthelmintics, etc. that can be mixed or used in combination with the pest control agent of the present invention are shown below.
• Acetylcholinesterase inhibitor (A) Carbamate: Aranicarb, Aldicarb, Bengiocarb, Benfracarb, Butocarboxim, Butoxycarboxym, Carbaryl, Carbofuran, Carbosulfan, Ethiophenacarb, Phenoccarb, Formetanate, Frathiocarb, Isoprocarb, Methiocarb, Methomyl, Oxamil, Pyrimicarb, Propoxal.
• Nicotinic acetylcholine receptor agonists acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradiflon, flupyrimin.
• Nicotinic acetylcholine receptor allosteric modulator spinetram, spinosad.
• Chloride channel activator abamectin, emamectin benzoate, repimectin, milbemectin, ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, nemadetin.
• Juvenile hormone-like substances hydroprene, quinoprene, methoprene, phenoxycarb, pyriproxyfen, diophenolan, epophenonan, triprene.
• Other non-specific inhibitors methyl bromide, chloropicrin, sulfuryl fluoride, borax, antimony stone.
• Hemiptera selective feeding inhibitors Fronicamid, Pymetrodin, Pyrifluquinazone.
• Mite growth inhibitors clofentezine, difluorovidazine, hexitiazox, etoxazole.
• Microbial-derived insect mid-intestinal membrane-destroying agent Bacillus thuringiensis subspecies Isla Elenshi, Bacillus thuringiensis subspecies Isla Elenshi, Bacillus thuringiensis subspecies Isawai, Bacillus thuringiensis subspecies Kurstaki, Bacillus thuringiensis subspecies Teneblionis, Bt Crop protein, Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.
• Mitochondrial ATP biosynthetic enzyme inhibitor diafentiurone, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradiphon.
• Oxidative phosphorylation decoupling agent chlorfenapyr, sulfurlamin, DNOC, binapacryl, dinobutone, dinocup.
• Nicotinic Acetylcholine Receptor Channel Blocker Bensultap, Cartap Hydrochloride, Neristoxin, Thiosultap-Sodium Salt, Nereistoxin.
• Chitin synthesis inhibitors bistrifluron, chlorflubenzuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumron, lufenuron, novalron, nobiflumron, teflubenzuron, triflubenzuron, buprofezin, fluazuron.
• Diptera molting disturber Cyromazine.
• Moulting hormone receptor agonists chromaphenozide, halophenozide, methoxyphenozide, tebufenozide.
• Octopamine receptor agonists Amitraz, Demiditraz, Chlordimeform.
• Mitochondrial electron transport chain complex III inhibitor acequinosyl, fluacripirim, hydramethylnon, biphenazate.
• Mitochondrial electron transport chain complex I inhibitor phenazakin, phenpyroximate, pyrimidiphen, pyridaben, tebufenpyrado, tolfenpyrad, rotenone.
• Voltage-gated sodium channel blockers indoxacarb, metaflumisone.
• Acetyl-CoA carboxylase inhibitors spirodiclophen, spiromesiphen, spirotetramato, spiropidion.
• Mitochondrial electron transport chain complex IV inhibitor aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide.
• Mitochondrial electron transport chain complex II inhibitor sienopyraphen, siflumethofen, piflubumid.
• Ryanodine receptor modulators chloranthraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, tetraniliprole.
• Mixed Function Oxidase Inhibitor Compound Piperonyl butoxide.
• Latrophilin receptor agonists depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, modepside.
• Anthelmintic (A) Benzimidazole system: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole, fevantel, netobimin, thiophanate, thiabendazole, cambendazole; (B) Salicylanilide system: closantel, oxyclozanide, lafoxanide, niclosamide; (C) Substituted phenolic system: nitroxynyl, nitroscanate; (D) Pyrimidines: Pyrantel, Morantel; (E) Imidazothiazole type: levamisole, tetramisole; (F) Tetrahydropyrimidines: Praziquantel, Epsiprantel; (G) Other anthelmintics: cyclodiene, liania, chlorthrone, metronidazole,
• fungicide that can be mixed or used in combination with the pest control agent of the present invention are shown below.
• A Nucleic Acid Synthesis and Metabolism Inhibitors
• DNA topoisomerase type II inhibitor oxolinic acid RNA Polymerase I Inhibitors Benalaxil, Benalaxil M, Flaluxil, Metalaxil, Metalaxil M; Oxadixil; Ofrace.
• Cytoskeleton and motor protein inhibitors (1) ⁇ -tubulin polymerization inhibitors benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, dietophencarb, zoxamide, Etaboxam. (2) Other inhibitors Pencyclon. Full opicoride. Fenamacril, Metraphenone, Periodophenone.
• Complex I NADH Oxidoreductase Inhibitor Diflumetrim, Torphenpyrado, Fenazakin.
• Complex II Inhibitors of succinate dehydrogenase Benodanyl, flutranyl, mepronil; isofetamide; fluopyram; fenfram; carboxyne, oxycarboxin; tifluzamide; benzobindiflupill, bixaphen, fluindapyl, fluxapyroxado, Flametopill, impilfluxam, isopyrazam, penflufen, penthiopyrado, sedaxan; isoflusiplum; pidiflumethophene; boscalide; pyraziflumid.
• Oxidative phosphorylation decoupling agent Binapacryl, Dinocup, Meptyldinocup; Fluazinum.
• Inhibitors of oxidative phosphorylation and ATP synthase Triphenyltin acetate, triphenyltin chloride, triphenyltin hydroxide.
• Complex III Amethoctrazine, an inhibitor of ubiquinone reductase (Qo site, stigmaterin-binding subsite).
• plant growth regulators that can be mixed or used in combination with the pest control agent of the present invention are shown below.
• the ectoparasite control agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient.
• the amount of the compound of the present invention contained in the ectoparasite control agent of the present invention is not particularly limited as long as it exhibits the ectoparasite control effect.
• Examples of host animals to be treated with the ectoparasite control agent of the present invention include pet animals such as dogs and cats; pet birds; domestic animals such as cows, horses, pigs and sheep; poultry; and other warm-blooded animals. be able to. Other examples include bees, stag beetles, and beetles.
• the ectoparasite control agent of the present invention can be applied by a known veterinary method (topical, oral, parenteral or subcutaneous administration).
• a method of orally administering to an animal by mixing tablets, capsules, feed, etc . a method of administering to an animal by an immersion liquid, a suppository, an injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); oily or A method of locally administering an aqueous solution by spraying, pore-on, spot-on, etc .; A method of wearing and locally administering; etc. can be mentioned.
• Ectoparasites parasitize in and on host animals, especially warm-blooded animals. Specifically, it parasitizes the back, armpits, lower abdomen, inner crotch, etc. of the host animal and inhabits by obtaining nutrient sources such as blood and dandruff from the animal. Examples of ectoparasites include mites, lice, fleas, mosquitoes, stable flies, and flesh flies. Specific examples of ectoparasites that can be controlled by the ectoparasite control agent of the present invention are shown below.
• Mites Dermanyssidae mites, Macronyssidae mites, Laelapidae mites, Varroidae mites, Argasidae mites, Ixodidae mites, cucumber mites Insect-parasitic mites such as Psoroptidae mites, Sarcoptidae mites, Knemidokoptidae mites, Demodixidae Demodixidae mites, Trombiculidae mites, and mulberry mites. ..
• Flea eyes Semiptera
• Human flea (Pulicidae) fleas such as dog fleas (Ctenocephalides spp.), Dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis); Fleas of the family Ceratophyllidae, fleas of the family Ceratophyllidae, fleas of the family Ceratophyllidae (Leptopsyllidae).
• Hemiptera Hemiptera.
• Diptera pests Culicidae mosquitoes, gnats Simuliidae gnats, Ceratopogonidae mosquitoes, Tabanidae mosquitoes, Muscidae flies, Glossinidae flies, Gnat flies, Hipboscidae flies, Calliphoridae flies, Oestridae flies.
• the endoparasite control or extermination agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient.
• the amount of the compound of the present invention contained in the endoparasite control or extermination agent of the present invention is not particularly limited as long as it shows the effect of controlling endoparasites.
• the parasite that is the target of the endoparasite control or extermination agent of the present invention parasitizes in host animals, especially warm-blooded animals and fish (endoparasites).
• host animals for which the endoparasite control or extermination agent of the present invention is effective include humans, domestic mammals (eg, cows, horses, pigs, sheep, goats, etc.), and experimental animals (eg, mice, rats, snails, etc.).
• Pet animals eg hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.
• wild and zoo mammals monkeys, foxes, deer, buffalo, etc.
• poultry shichimenchou, ducks, chickens, quail, etc.
• Gacho etc.
• warm-blooded animals such as pet birds (pigeons, parrots, nine official birds, literary birds, inco, juushi pine, canary, etc.); or fish such as salmon, trout, and Nishikigoi.
• Examples of parasites to be controlled or exterminated include the following.
• Nematodes of the order Dioctophymatida (a) Nematodes of the family Dioctophymatidae, for example, Dioctophyma renale of the genus Dioctophyma spp. (B) Kidneyworms of the Soboliphymatidae family, such as Soboliphyme abei and Soboliphyme baturini of the Soboliphyme spp.
• Trichocephalida Trichinella spiralis of the Trichinellidae family, for example, Trichinella spiralis of the Trichinella spp. Species;
• Trichuridae trichuridae for example, Trichuridae species, Capillaria annulata, Capillaria contorta, Liver hair nematodes (Capillaria contorta) Capillaria hepatica, Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris spp., Trichuris vulpis, cattle Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris suis.
• Nematodes (Strongyloides planiceps), Pig manure nematodes (Strongyloides ransomi), Pig manure nematodes (Strongyloides suis), Feces nematodes (Strongyloides stercoralis), American cat manure nematodes (Strongyloides tumefaciens), Mouse manure nematodes (Strongyloides ratti) .
• Ancylostomatidae hookworms such as Ancylostoma spp., Brazilian hookworm (Ancylostoma braziliense), dog hookworm (Ancylostoma caninum), and Zubini hookworm.
• Ancylostoma duodenale cat hookworm (Ancylostoma tubaeforme); Uncinaria stenocephala, narrow-headed hookworm (Uncinaria stenocephala); Bunostomum trigonocephalum).
• C. elegans of the order Strongylida (a) C. elegans of the family Angiostrongylidae, for example, Aelurostrongylus abstrusus of the genus Aelurostrongylus spp.; Angiostrongylus vasorum of the genus Angiostrongylus spp., Angiostrongylus cantonesis; (B) Crenosomatidae nematodes, such as Crenosoma spp., Crenosoma aerophila, Crenosoma vulpis; (C) C.
• C. elegans of the order Strongylida (a) C. elegans of the family Molineidae, for example, Nematodirus spp., Nematodirus filicollis, Nematodirus spa Tiger (Nematodirus spathiger); (B) Nematodes of the family Dictyocaulidae (Dictyocaulus spp.), Dictyocaulus filaria, Dictyocaulus viviparus; (C) Haemonchidae nematodes, such as Haemonchus contortus, Haemonchus contortus; Mecistocirrus spp., Mecistocirrus spp.
• C. elegans of the order Strongylida (a) C. elegans of the family Chabertiidae, for example, Chabertia ovina of the genus Chabertia spp.; Intestinal nodules.
• Insect genus (Oesophagostomum spp.), Intestinal nodule (pig) (Oesophagostomum brevicaudatum), Colombian intestinal nodule (Oesophagostomum columbianum), Oesophagostomum dentatum, intestinal nodule (pig) (Oesophagostomum georgianum) Oesophagostomum maplestonei, Oesophagostomum quadrispinulatum, Oesophagostomum radiatum, Oesophagostomum venulosum, Oesophagostomum venulosum, Oesophagostomum venulosum, Oesophagostomum venulosum (B) Nematodes of the family Stephanuridae, eg, Stephanurus dentatus of the genus Stephanurus spp.; (C) Strongylus vulgaris
• Oxyurida nematodes Oxyuridae nematodes, such as the Enterobius spp., Enterobius anthropopitheci, Enterobius vermicularis; Oxyuris. Oxyuris equi of spp.); Passalurus ambiguus of the genus Passalurus spp.
• Ascaridida nematodes (a) Ascaridiidae nematodes, such as chicken roundworm species (Ascaridia spp.), Chicken roundworm (Ascaridia galli); (B) Heterakidae nematodes, such as the Heterakis spp., Heterakis beramporia, Heterakis brevispiculum, and Heterakis gallinarum.
• Anisakidae nematodes such as Anisakis simplex from the genus Anisakidae (Anisakis spp.);
• Ascarididae nematodes such as roundworm species (Ascaris spp.), Human roundworms (Ascaris lumbricoides), ascaris suum; Parascaria species (Parascaris spp.), Horse roundworms.
• Nematodes of the order Spirurida Nematodes of the order Spirurida
• a Nematodes of the Onchocercidae family, for example, Brugia malayi and Brugia malayi of the genus Brugia spp. (Brugia pahangi), Brugia patei; Dipetalonema spp., Dipetalonema reconditum; Dirofilaria spp., Dirofilaria spp.
• Nematodes of the order Spirurida (a) Gnathostomiasis (Gnathostomatidae) nematodes, for example, Gnathostoma doloresi of the genus Gnathostoma spp.
• Habronematidae nematodes such as Haemonema spp., Haemonema majus, Habronema microstoma, Haemonchus muscae; Draschia Draschia megastoma of the genus (Draschia spp.);
• C Physalopteridae nematodes, such as Physaloptera spp., Physaloptera canis, Physaloptera cesticillata, Physaloptera erdociona, Physaloptera erdoc.
• Physaloptera felidis Egyptian cat gastrointestinal worm (Physaloptera gemina), Physaloptera papilloradiata, cat gastrointestinal worm (Physaloptera praeputialis), Physaloptera pseudopraerutialis rara), Physaloptera sibirica, Physaloptera vulpineus;
• D Gongylonematidae nematodes, such as the Gongylonema spp., Gongylonema pulchrum;
• E Nematodes of the family Spirocercidae, such as Ascarops spp., Ascarops strongylina;
• Nematodes of the family Thelaziaidae such as Thelazia spp., Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Thelazia rhodes. Insects (Thelazia rhodes
• the compound of the present invention has pests that have poisonous needles and toxic liquids and damage human animals, pests that transmit various pathogens and pathogens, and pests that cause discomfort to humans (toxic pests, sanitary pests, and unpleasant pests). Etc.) is excellent in control effect.
• the pharmaceutical formulations for agriculture and horticulture and paddy rice are shown below.
• (Formation 1: wettable powder) 40 parts of the compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate ester, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely pulverized to obtain a wettable powder having 40% of the active ingredient.
• (Formation 2: Emulsion) 30 parts of the compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsion containing 30% of the active ingredient.
• Formation 3 Granules
• 5 parts of the compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and finely pulverized, and then granulated into granules having a diameter of 0.5 to 1.0 mm. To obtain granules having 5% of the active ingredient.
• Formation 4 Granules 5 parts of the compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate were thoroughly pulverized and mixed, water was added and kneaded well, and then granulated and dried. Obtain granules with 5% active ingredient.
• Form 5 Suspension 10 parts of the compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 part of xanthan gum, and 73.8 parts of water are mixed to reduce the particle size to 3 microns or less. Wet grind to obtain a suspension of 10% active ingredient.
• the formulation of the ectoparasite control agent or the endoparasite control or control agent is shown below.
• Formation 8 Poaon agent
• a poreon agent is obtained by uniformly mixing 5 parts of the compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol.
• Formation 9 Spot-on agent
• 10 to 15 parts of the compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol are uniformly mixed to obtain a spot-on agent.
• Forma 10 Spray
• a spray agent is obtained by uniformly mixing 1 part of the compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol.
• Step 1 Synthesis of 2-amino-5-bromo-3- (trifluoromethyl) benzoic acid [2-amino-5-bromo-3- (trifluoromethyl) benzoic acid]
• Step 5 1-(1- (pyridin-2-yl) -1H-1,2,4-triazole-5-yl) ethane-1-amine [1- (1- (pyridin-2-yl) -1H-1,2 , 4-triazol-5-yl) ethan-1-amine]
• 6-Bromo-4-chloro-8- (trifluoromethyl) quinazoline 100 mg was dissolved in N, N-dimethylformamide (3 ml).
• 1- (1- (pyridin-2-yl) 1H-1,2,4-triazole-5-yl) ethane-1-amine 87 mg
• N, N-diisopyrethylamine 124 mg
• the mixture was stirred at 150 ° C. for 0.5 hours using a microwave device.
• the obtained liquid was purified by silica gel chromatography. The fraction containing the target product was concentrated, and the obtained solid content was washed with hexane to obtain 125 mg (yield 84%) of the target product.
• Table 1 shows an example of the compound of the present invention produced by the same method as in the above-mentioned Examples.
• the physical property data of the compound was entered in the "Physical characteristics" column.
• the melting point (mp) was described.
• the efficacy test (1) on armyworm was carried out for the compound of compound number A-1.
• the compound of A-1 had an insecticidal rate of 100% and was effective.
• the insecticidal rate of emulsion (II) was 0%.
• Emulsion (I) Effectiveness test against armyworm (2) Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm by mass.
• the corn leaf pieces were immersed in the diluted solution for 30 seconds.
• the corn leaf pieces were placed in a petri dish and 5 second-instar larvae of Mythimna separata were released.
• the petri dish was left in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60% during the test period. When 6 days had passed since the insect was released, the life or death was judged and the insecticidal rate was calculated. The test was performed in two iterations.
• the efficacy test (2) on armyworm was carried out for the compounds of compound numbers A-2 and A-3. Both compounds showed an insecticidal rate of 80% or more with respect to armyworm. On the other hand, the insecticidal rate of emulsion (II) was 0%.
• Emulsion Test for Diamondback Moth Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm by mass.
• the cabbage leaves were immersed in the diluted solution for 30 seconds.
• the cabbage leaves were air-dried and placed in a petri dish, and five second-instar diamondback moth larvae were released.
• the petri dish was left in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60% during the test period. Life or death was determined when 3 days had passed since the insect was released, and the insecticidal rate was calculated. The test was performed in two iterations.
• the compounds of Compound Nos. A-2 and A-3 were tested for efficacy against diamondback moth. Both compounds showed an insecticidal rate of 80% or more with respect to diamondback moth. On the other hand, the insecticidal rate of emulsion (II) was 0%.
• Emulsion Test for Spodoptera litura Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm by mass.
• the cabbage leaves were immersed in the diluted solution for 30 seconds.
• the cabbage leaves were air-dried and placed in a petri dish, and five second-instar larvae of Spodoptera litura were released.
• the petri dish was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. When 6 days had passed since the insect was released, the life or death was judged and the insecticidal rate was calculated. The test was performed in two iterations.
• Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm by mass. This diluted solution was sprayed on the cucumber. After that, the cucumber was placed in a homeothermic chamber at a temperature of 25 ° C. and a humidity of 60%, and after 5 days, the life and death of the cotton aphid was examined, and the insecticidal rate was determined.
• the compounds of Compound Nos. A-26, A-29, A-30, A-39 and A-57 were tested for efficacy against brown planthoppers. Both compounds showed an insecticidal rate of 80% or more. On the other hand, the insecticidal rate of emulsion (II) was 0%.
• Randomly selected compounds of the present invention exert the above-mentioned effects. Therefore, the compounds of the present invention include compounds that could not be shown in the examples, and pest control, acaricide, especially insecticide, etc. It can be understood that it is a compound having the effect of.
• the azinylazole compound of the present invention has a function of controlling harmful organisms that pose a problem in terms of crops and hygiene.
• the control agent containing the azinylazole compound of the present invention can effectively control pests, especially agricultural pests and mites, at a lower concentration, and further ectoparasites and endoparasites that may harm humans and animals. Insects can be effectively controlled.

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