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
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
• • 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
  • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
  • A61K31/4355—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
• • 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
• • 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
  • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/62—Oxygen or sulfur atoms
  • C07D213/63—One oxygen atom
  • C07D213/68—One oxygen atom attached in position 4
• • 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
  • C07D401/12—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 linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • 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
  • C07D491/04—Ortho-condensed systems
  • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
  • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered

Definitions

• the present invention relates to an amide compound and a pest control agent. More specifically, the present invention relates to an amide compound which has excellent acaricidal activity and / or insecticidal activity, is excellent in safety, and can be synthesized industrially advantageously, and a pest control agent containing this as an active ingredient About.
• This application claims priority based on Japanese Patent Application No. 2015-207080 filed in Japan on October 21, 2015, the contents of which are incorporated herein by reference.
• Patent Literature 1 disclose aryloxyureas and aryloxyacetic acid amides as compounds structurally related to the amide compound of the present invention.
• An object of the present invention is to provide an amide compound having excellent pesticidal activity, in particular, acaricidal activity and / or insecticidal activity, excellent safety, and industrially advantageous synthesis, and harmful substances containing this as an active ingredient. It is to provide a biocontrol agent.
• Z is an oxygen atom or a sulfur atom.
• A is a group represented by the formula (A-1) or a group represented by the formula (A-2).
• B is a group represented by the formula (B-1) when A is a group represented by the formula (A-1), and B is a group represented by the formula (A-2) It is a group represented by B-2).
• W is a nitrogen atom or CH.
• * represents a bonding position.
• X is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy Group, amino group, substituted or unsubstituted C1-6 alkylamino group, formyl group, substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted C1-6 alkylaminocarbonyl group, substituted or unsubstituted C1-6 alkoxyimino C1-6 alkyl group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alky
• n represents the number of substitutions of X and is an integer from 0 to 3. When n is 2 or 3, Xs may be the same or different.
• R 1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, or a phenyl group.
• R 2 and R 3 are each independently a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group.
• R 4 and R 5 are each independently a hydrogen atom or an unsubstituted C 1-6 alkyl group. R 4 and R 5 may be joined together to form a ring together with the carbon atom to which they are attached.
• R 6 is a substituted or unsubstituted aminocarbonyl group, or a substituted or unsubstituted aminothiocarbonyl group.
• R 7 is a substituted or unsubstituted aminocarbonyl group, or a substituted or unsubstituted heteroaryl group.
• a pest control agent comprising at least one selected from the group consisting of the compound according to [1] or [2] and a salt thereof as an active ingredient.
• An acaricide or insecticide containing as an active ingredient at least one selected from the group consisting of the compound according to [1] or [2] and a salt thereof.
• An endoparasite control or control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to [1] or [2] and a salt thereof.
• the amide compound of the present invention can control pests that are problematic in crops and hygiene. In particular, mites and pests can be effectively controlled.
• the amide compound of the present invention is a compound represented by formula (1) (hereinafter sometimes referred to as compound (1)) or a salt of compound (1).
• the term “unsubstituted” means that only the group serving as a mother nucleus. When only the name of a group serving as a mother nucleus is described, it means “unsubstituted” unless otherwise specified.
• the term “substituted” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having the same or different structure from the mother nucleus. Accordingly, the “substituent” is another group bonded to a group serving as a mother nucleus.
• the number of substituents may be one, or two or more. Two or more substituents may be the same or different.
• the “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
• Specific examples of the group that can be a “substituent” include the following groups. Halogeno groups such as fluoro, chloro, bromo and iodo groups; 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.
• An alkyl group Vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4 A C2-6 alkenyl group such as a hexenyl group, a 5-hexenyl group;
• Ethynyl 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-pentynyl 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group, etc.
• a C2-6 alkynyl group of A C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cubanyl group;
• a C3-8 cycloalkenyl group such as a 2-cyclopropenyl group, a 2-cyclopentenyl group, a 3-cyclohexenyl group, a 4-cyclooctenyl group;
• a C6-10 aryl group such as a phenyl group or a naphthyl group; 5-membered heteroaryl groups such as pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadia
• Hydroxyl group oxo 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; C6-10 aryloxy groups such as phenoxy group and naphthoxy group; 5- to 6-membered heteroaryloxy group such as thiazolyloxy group and pyridyloxy group;
• Carboxyl group A formyl group; a C1-6 alkylcarbonyl group such as an acetyl group or a propionyl group; Formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy group and propionyloxy group; A C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group;
• C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group;
• a C2-6 haloalkenyl group such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group;
• a C2-6 haloalkynyl group such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group;
• a C3-6 halocycloalkyl group such as a 3,3-difluorocyclobutyl group;
• C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-
• a aminocarbonyl group such as a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylaminocarbonyl group, an i-propylaminocarbonyl group;
• Imino C1-6 alkyl groups such as an iminomethyl group, a (1-imino) ethyl group, a (1-imino) -n-propyl group;
• Hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group;
• a C1-6 alkoxyimino C1-6 alkyl group such as a methoxyiminomethyl group and a (1-methoxyimino) ethyl group;
• a mercapto group such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group;
• a C1-6 haloalkylthio group such as a trifluoromethylthio group or a 2,2,2-trifluoroethylthio group;
• C2-6 alkenylthio groups such as vinylthio group and allylthio group;
• a C2-6 alkynylthio group such as an ethynylthio group or a propargylthio group;
• a C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group;
• a tri-C1-6 alkylsilyl group such as a trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
• a tri-C6-10 arylsilyl group such as a triphenylsilyl group; In these “substituents”, any hydrogen atom in the substituent may be substituted with a group having a different structure.
• “Terms such as“ C1-6 ” indicate that the number of carbon atoms of the group serving as the mother nucleus is 1-6. This number of carbon atoms does not include the number of carbon atoms present in the substituent.
• an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because a group serving as a mother nucleus is a butyl group and a substituent is an ethoxy group.
• Z is an oxygen atom or a sulfur atom.
• Z is an oxygen atom
• it may be called acid amides
• Z when Z is a sulfur atom, it may be called thioamides.
• Thioamides in which Z in formula (1) is a sulfur atom have low water solubility compared to acid amides, and therefore have a low mobility in the environment and animal organisms, and are preferable from the viewpoint of safety. Have.
• A represents a substituted or unsubstituted N-[(pyridin-4-yl) oxy] amino group, a substituted or unsubstituted [(pyridin-4-yl) oxy] methyl group, or a substituted or unsubstituted An unsubstituted 2,3-dihydrofuro [3,2-c] pyridin-2-yl group.
• the substituted or unsubstituted N-[(pyridin-4-yl) oxy] amino group and [(pyridin-4-yl) oxy] methyl group in A are preferably groups represented by the formula (A-1) It is.
• the substituted or unsubstituted 2,3-dihydrofuro [3,2-c] pyridin-2-yl group in A is preferably a group represented by the formula (A-2).
• X represents a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2 ⁇ 6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, amino group, substituted or unsubstituted C1-6 alkylamino group, formyl group, substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted Substituted C1-6 alkylaminocarbonyl group, substituted or unsubstituted C1-6 alkoxyimino C1-6 alkyl group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsul
• halogeno group examples include a fluoro group, a chloro group, a bromo group, and an iodo group.
• the “C1-6 alkyl group” in X may be a straight chain or a branched chain.
• Examples of the alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group and t-butyl group.
• Examples of the “C2-6 alkenyl group” in X include a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2 -Methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
• the “C2-6 alkynyl group” in X is an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2 -Methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group 1,1-dimethyl-2-butynyl group and the like.
• C1-6 alkoxy group 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, an i-butoxy group, Examples thereof include an s-butoxy group, a t-butoxy group, and an i-hexyloxy group.
• Examples of the “C1-6 alkylamino group” in X include a methylamino group, a dimethylamino group, and a diethylamino group.
• Examples of the “C1-6 alkylcarbonyl group” in X include an acetyl group and a propionyl group.
• Examples of the “C1-6 alkylaminocarbonyl group” in X include a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylaminocarbonyl group, and an i-propylaminocarbonyl group.
• Examples of the “C1-6 alkoxyimino C1-6 alkyl group” in X include a methoxyiminomethyl group and a (1-methoxyimino) ethyl group.
• C1-6 alkyl group C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C1-6 alkylamino group”, “C1-6 alkylcarbonyl group” in X , “C1-6 alkylaminocarbonyl group”, and “C1-6 alkoxyimino C1-6 alkyl group”, preferably a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo 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; 2-chloro-n-propoxy Groups, C1-6 haloalkoxy groups such as 2,3-dichlorobutoxy group, trifluoromethoxy group, etc .; C6-10 groups such as phenyl group, naphthyl group
• Examples of the “C1-6 alkylthio group” in X include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group and the like.
• Examples of the “C1-6 alkylsulfinyl group” in X include a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group, and the like.
• Examples of the “C1-6 alkylsulfonyl group” in X include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group, and the like.
• Examples of the “C1-6 alkoxysulfonyl group” in X include a methoxysulfonyl group, an ethoxysulfonyl group, a t-butoxysulfonyl group, and the like.
• C1-6 alkylthio group preferably a fluoro group, a chloro group
• Halogeno groups such as bromo group, iodo group
• C1 ⁇ 6 alkoxy groups preferably a fluoro group
• C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group
• cyano group preferably a fluoro group, a chloro group
• Halogeno groups such as bromo group, iodo group
• C1 ⁇ 6 alkoxy groups preferably a fluoro group
• C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group
• cyano group preferably a fluoro group, a chloro group
• Halogeno groups such as bromo group, iodo group
• C1 ⁇ 6 alkoxy groups
• Examples of the “C3-8 cycloalkyl group” in X include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
• Examples of the “C6-10 aryl group” in X include a phenyl group and a naphthyl group.
• heteroaryl group in X, pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group (for details, [1,2,3] Triazolyl group or [1,2,4] triazolyl group), oxadiazolyl group (specifically, [1,2,3] oxadiazolyl group, [1,2,4] oxadiazolyl group, [1,2,5] oxadiazolyl group Or a [1,3,4] oxadiazolyl group), a thiadiazolyl group, a tetrazolyl group or the like; a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group
• Examples of the “C6-10 aryloxy group” in X include a phenoxy group and a naphthoxy group.
• heteroaryloxy group examples include 5- to 6-membered heteroaryloxy groups such as thiazolyloxy group and pyridyloxy group.
• Substituents on the “C3-8 cycloalkyl group”, “C6-10 aryl group”, “heteroaryl group”, “C6-10 aryloxy group”, and “heteroaryloxy group” in X are preferably fluoro Group, chloro group, bromo group, iodo group and other halogeno groups; methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group C1-6 alkyl groups such as n-pentyl group and n-hexyl group; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, C1-6 haloalkyl groups such as perfluoro-n-pentyl group; methoxy group, ethoxy
• X represents a halogeno group, a C1-6 alkyl group, a C1-6 haloalkyl group, a C2-6 alkynyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group C1-6 alkylamino group, C1-6 alkylaminocarbonyl group, C1-6 haloalkylaminocarbonyl group, C1-6 alkoxyimino C1-6 alkyl group, C6-10 aryl C1-6 alkoxyimino C1-6 alkyl group, A C1-6 alkylthio group, a C1-6 alkylsulfonyl group, a C6-10 aryl group, a heteroaryl group, a nitro group, or a cyano group is preferable, a halogeno group, a C1-6 haloalkyl group, a C1-6 haloalkoxy group More preferably a C1-6 alkylamino group, a
• R 1 represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group Or a phenyl group.
• Specific examples of the “C1-6 alkyl group”, “C2-6 alkenyl group”, and “C2-6 alkynyl group” in R 1 are the same as those exemplified for X.
• the substituent on the “C1-6 alkyl group”, “C2-6 alkenyl group”, or “C2-6 alkynyl group” in R 1 is preferably a halogeno group.
• R 1 is preferably a C1-6 alkyl group, a C1-6 haloalkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, or a phenyl group, More preferred is a C1-6 alkyl group.
• W is a nitrogen atom or CH.
• R 2 and R 3 are each independently a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. Specific examples of the “C1-6 alkyl group” for R 2 and R 3 include the same as those exemplified for X. The substituent on the “C1-6 alkyl group” in R 2 and R 3 is preferably a halogeno group. In formula (A-2), R 2 or R 3 is preferably a hydrogen atom.
• B is a group represented by Formula (B-1) when A is a group represented by Formula (A-1), and A is represented by Formula (A-2).
• the compound (1) composed of a combination of A and B in the formula (1) is a compound represented by the formula (2) or the formula (3).
• Formula (2) is expressed by Formula (2-1) or Formula (2-2).
• R 4 and R 5 are each independently a hydrogen atom or a C1-6 alkyl group. Examples of the C1-6 alkyl group for R 4 and R 5 are the same as those exemplified for X.
• R 4 and R 5 are preferably methyl groups.
• R 4 and R 5 may be connected to form a ring together with the carbon atom to which they are bonded.
• Examples of the ring formed by connecting R 4 and R 5 include alicyclic rings having 3 to 6 carbon atoms such as a cyclopropane ring, a cyclobutane ring, and a cyclohexane ring, and a cyclopropane ring is preferable.
• R 6 represents a substituted or unsubstituted aminocarbonyl group, or a substituted or unsubstituted aminothiocarbonyl group.
• R 7 is a substituted or unsubstituted aminocarbonyl group or a substituted or unsubstituted heteroaryl group.
• Examples of the substituent on the “aminocarbonyl group” in R 6 or R 7 include a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C1-6 alkoxy.
• the “substituted aminocarbonyl group” in R 6 or R 7 is a substituted or unsubstituted mono C1-6 alkylaminocarbonyl group, a substituted or unsubstituted diC1-6 alkylaminocarbonyl group, a substituted Or an unsubstituted C3-6 cycloalkylaminocarbonyl group, a substituted or unsubstituted cyclic aminocarbonyl group, a substituted or unsubstituted C1-6 alkoxyaminocarbonyl group, a substituted or unsubstituted N- (C1-6 alkyl)- N- (C1-6 alkoxy) aminocarbonyl group, 2-mono C1-6 alkylhydrazine-1-carbonyl group, 2,2-diC1-6 alkylhydrazine-1-carbonyl group, substituted or unsubstituted ((C1 -6 alkoxyimino) methyl) aminocarbonyl group and the like.
• R 6 or R 7 a methylaminocarbonyl group, an ethylaminocarbonyl group, an n-propylaminocarbonyl group, an i-propylaminocarbonyl group, an n-butylaminocarbonyl group, Examples thereof include s-butylaminocarbonyl group, t-butylaminocarbonyl group, i-butylaminocarbonyl group, n-pentylaminocarbonyl group, i-pentylaminocarbonyl group, n-hexylaminocarbonyl group and the like.
• Examples of the “di-C1-6 alkylaminocarbonyl group” in R 6 or R 7 include a dimethylaminocarbonyl group, a methylethylaminocarbonyl group, a diethylaminocarbonyl group and the like.
• Examples of the “C3-6 cycloalkylaminocarbonyl group” in R 6 or R 7 include a cyclopropylaminocarbonyl group, a cyclobutylaminocarbonyl group, a cyclopentylaminocarbonyl group, a cyclohexylaminocarbonyl group and the like.
• the “cyclic aminocarbonyl group” in R 6 or R 7 is a group in which a cyclic amino group such as an aziridinyl group, pyrrolidinyl group, piperidyl group, piperazinyl group, morpholinyl group or the like is bonded to a carbonyl group, specifically piperidine-1 And -carbonyl group, piperazine-1-carbonyl group, and pyrrolidine-1-carbonyl group.
• Examples of the “C1-6 alkoxyaminocarbonyl group” in R 6 or R 7 include methoxyaminocarbonyl group, ethoxyaminocarbonyl group, n-propoxyaminocarbonyl group and the like.
• N- (C1-6 alkyl) -N- (C1-6 alkoxy) aminocarbonyl group in R 6 or R 7 has a C1-6 alkyl group and a C1-6 alkoxy group as substituents of the aminocarbonyl group. Specific examples thereof include N-methyl-N-methoxyaminocarbonyl group and N-methyl-N-ethoxyaminocarbonyl group.
• the “2-mono C1-6 alkylhydrazine-1-carbonyl group” in R 6 or R 7 has a mono C1-6 alkylamino group as a substituent for the aminocarbonyl group. Examples thereof include a methyl hydrazine-1-carbonyl group and a 2-ethylhydrazine-1-carbonyl group.
• the “2,2-diC1-6 alkylhydrazine-1-carbonyl group” in R 6 or R 7 has a diC1-6 alkylamino group as a substituent of the aminocarbonyl group.
• Examples include 2,2-dimethylhydrazine-1-carbonyl group, 2,2-diethylhydrazine-1-carbonyl group, and the like.
• Examples of the “(((C1-6 alkoxyimino) methyl) aminocarbonyl group” in R 6 or R 7 include a ((methoxyimino) methyl) aminocarbonyl group or a ((ethoxyimino) methyl) aminocarbonyl group.
• the “substituted or unsubstituted aminocarbonyl group” in R 6 or R 7 is a substituted or unsubstituted mono C1-6 alkylaminocarbonyl group, a substituted or unsubstituted C3-6 cycloalkylaminocarbonyl group, substituted or unsubstituted.
• a C1-6 alkylaminocarbonyl group or a substituted or unsubstituted C3-6 cycloalkylaminocarbonyl group is preferred.
• Examples of the “C2-6 haloalkenyl group” for G 1 include a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group.
• Examples of the “C2-6 haloalkynyl group” in G 1 include a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, a 5-bromo-2-pentynyl group, and the like.
• Examples of the “C1-6 haloalkoxy group” in G 1 include 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, and the like. Can do.
• Examples of the “C1-6 haloalkylthio group” for G 1 include a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group.
• Examples of the “C1-6 haloalkylsulfinyl group” in G 1 include a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group.
• Examples of the “C1-6 haloalkylsulfonyl group” for G 1 include a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group.
• C2-6 alkenyl group “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C3-6 cycloalkyl group”, “C1-6 alkylthio group”, “C1-6 alkylsulfinyl” in G 1 Group, C1-6 alkylsulfonyl group, C6-10 aryl group, 5-membered heteroaryl group, 6-membered heteroaryl group, condensed heteroaryl group,
• Examples of the “halogeno group” include the same as those exemplified for X.
• C6-10 aryl group “5-membered heteroaryl group”, “6-membered heteroaryl group”, and “fused-ring heteroaryl group” in G 1 may be substituted with “halogeno group” Good.
• G 1 includes a C2-6 alkenyl group, a C2-6 haloalkenyl group, a C2-6 alkynyl group, a C2-6 haloalkynyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C3-6 cycloalkyl group.
• Particularly preferred “substituted or unsubstituted aminocarbonyl group” for R 6 or R 7 is a substituted or unsubstituted mono C1-6 alkylaminocarbonyl group
• substituent G 1 is a C2-6 alkenyl group, C2-6 Haloalkenyl group, C2-6 alkynyl group, C2-6 haloalkynyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, C3-6 halocycloalkyl group, C1-6 alkylthio group , C1-6 haloalkylthio group, C1-6 alkylsulfinyl group, C1-6 haloalkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylsulfonyl group, optionally substituted with a halogeno group, C6-10 Aryl group, 6-membered heteroaryl group (option
• Examples of the substituent on the “thioaminocarbonyl group” in R 6 include a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C3-6 cycloalkyl group, a substituted or unsubstituted C1-6 alkoxy group, Examples thereof include a substituted or unsubstituted mono C1-6 alkylamino group, a substituted or unsubstituted diC1-6 alkylamino group, a substituted or unsubstituted (C1-6 alkoxyimino) methyl group, or an oxetanyl group. .
• the “substituted aminothiocarbonyl group” in R 6 includes a substituted or unsubstituted mono C1-6 alkylaminothiocarbonyl group, a substituted or unsubstituted diC1-6 alkylaminothiocarbonyl group, a substituted or unsubstituted C3 to C3— 6 cycloalkylaminothiocarbonyl group, substituted or unsubstituted cyclic aminothiocarbonyl group, substituted or unsubstituted C1-6 alkoxyaminothiocarbonyl group, substituted or unsubstituted N- (C1-6 alkyl) -N- ( C1-6 alkoxy) aminothiocarbonyl group, 2-mono C1-6 alkylhydrazine-1-thiocarbonyl group, 2,2-diC1-6 alkylhydrazine-1-thiocarbonyl group, substituted or unsubstituted ((C1 -6 alkoxyimino) methyl) amino
• Examples of the “mono C1-6 alkylaminothiocarbonyl group” in R 6 include a methylaminothiocarbonyl group, an ethylaminothiocarbonyl group, an n-propylaminothiocarbonyl group, an i-propylaminothiocarbonyl group, an n-butylaminothio group.
• Examples of the “di-C1-6 alkylaminothiocarbonyl group” in R 6 include dimethylaminothiocarbonyl group, methylethylaminothiocarbonyl group, diethylaminothiocarbonyl group and the like.
• Examples of the “C3-6 cycloalkylaminothiocarbonyl group” for R 6 include a cyclopropylaminothiocarbonyl group, a cyclobutylaminothiocarbonyl group, a cyclopentylaminothiocarbonyl group, a cyclohexylaminothiocarbonyl group, and the like.
• the “cyclic aminothiocarbonyl group” in R 6 is a group in which a cyclic amino group such as aziridinyl group, pyrrolidinyl group, piperidyl group, piperazinyl group, morpholinyl group or the like is bonded to a thiocarbonyl group, specifically piperidine-1- A thiocarbonyl group, a piperazine-1-thiocarbonyl group, and a pyrrolidine-1-thiocarbonyl group can be mentioned.
• Examples of the “C1-6 alkoxyaminothiocarbonyl group” for R 6 include a methoxyaminothiocarbonyl group, an ethoxyaminothiocarbonyl group, an n-propoxyaminothiocarbonyl group, and the like.
• N— (C1-6 alkyl) -N— (C1-6 alkoxy) aminothiocarbonyl group in R 6 has a C1-6 alkyl group and a C1-6 alkoxy group as substituents for the aminothiocarbonyl group. Specific examples thereof include N-methyl-N-methoxyaminothiocarbonyl group and N-methyl-N-ethoxyaminothiocarbonyl group.
• the “2-mono C1-6 alkylhydrazine-1-thiocarbonyl group” in R 6 has a mono C1-6 alkylamino group as a substituent of the aminothiocarbonyl group, specifically 2-methyl Examples thereof include a hydrazine-1-thiocarbonyl group and a 2-ethylhydrazine-1-thiocarbonyl group.
• the “2,2-diC1-6 alkylhydrazine-1-thiocarbonyl group” in R 6 has a diC1-6 alkylamino group as a substituent of the aminothiocarbonyl group. 2,2-dimethylhydrazine-1-thiocarbonyl group, 2,2-diethylhydrazine-1-thiocarbonyl group, and the like.
• Examples of the “((C1-6 alkoxyimino) methyl) aminothiocarbonyl group” for R 6 include a ((methoxyimino) methyl) aminothiocarbonyl group or a ((ethoxyimino) methyl) aminothiocarbonyl group.
• the “substituted or unsubstituted aminothiocarbonyl group” in R 6 is a substituted or unsubstituted mono C1-6 alkylaminothiocarbonyl group, a substituted or unsubstituted C3-6 cycloalkylaminothiocarbonyl group, substituted or unsubstituted.
• a cyclic aminothiocarbonyl group a substituted or unsubstituted C1-6 alkoxyaminothiocarbonyl group, a substituted or unsubstituted ((C1-6 alkoxyimino) methyl) aminothiocarbonyl group, and more preferably a substituted or unsubstituted group.
• a substituted mono C1-6 alkylaminothiocarbonyl group or a substituted or unsubstituted C3-6 cycloalkylaminothiocarbonyl group is preferred.
• G 1 Specific examples of these groups include the same ones as those exemplified in G 1. Further, the C6-10 aryl group, the 5-membered heteroaryl group, the 6-membered heteroaryl group, and the condensed heteroaryl group may be further substituted with a halogeno group.
• Preferred G 2 is the same as described in G 1 .
• R 6 include "substituted or unsubstituted amino thiocarbonyl group” is substituted or unsubstituted mono- C1 ⁇ 6 alkylaminothiocarbonyl group (preferred substituents G 2 are, C2 ⁇ 6 alkenyl group, C2 ⁇ 6 halo Alkenyl group, C2-6 alkynyl group, C2-6 haloalkynyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, C3-6 halocycloalkyl group, C1-6 alkylthio group, C1-6 haloalkylthio group, C1-6 alkylsulfinyl group, C1-6 haloalkylsulfinyl group, C1-6 alkylsulfonyl group, C1-6 haloalkylsulfonyl group, C6-10 aryl (which may be substituted with a halogeno group)
• heteroaryl group examples include pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc.
• the “heteroaryl group” for R 7 is preferably a 6-membered heteroaryl group such as a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, more preferably a pyridyl group or a pyrimidinyl group, and pyridin-2-yl More preferred is a group or a pyrimidin-2-yl group.
• the “heteroaryl group” for R 7 preferably has 1 to 4 substituents, more preferably 1 to 2 substituents. When having two or more substituents, the substituents may be the same or different. When R 7 is a pyridin-2-yl group or a pyrimidin-2-yl group, the substituent is preferably at the 4-position.
• Examples of the substituent (hereinafter referred to as Y) on the “heteroaryl group” in R 7 include a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, hydroxyl group, substituted or unsubstituted C1-6 alkoxy group, amino group, substituted or unsubstituted C1-6 alkylamino group, carboxyl group, formyl group, substituted or unsubstituted C1-6 alkyl Carbonyl group, substituted or unsubstituted C1-6 alkoxycarbonyl group, substituted or unsubstituted C1-6 alkylaminocarbonyl group, substituted or unsubstituted C1-6 alkoxyimino C1-6 alkyl group, substituted or unsubstituted C1 -6 alkylthio group, substituted
• Halogeno group in Y substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, substituted or unsubstituted C1-6 alkoxy group, substituted Or an unsubstituted C1-6 alkylamino group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkylaminocarbonyl group, a substituted or unsubstituted C1-6 alkoxyimino C1-6 alkyl Group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C1-6 alkoxysulfonyl group, substituted Or an un
• Examples of the “C1-6 alkoxycarbonyl group” in Y include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, and a t-butoxycarbonyl group.
• the substituent on the “C1-6 alkoxycarbonyl group” in Y is preferably a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group Group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and other C1-6 alkoxy groups; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group C1-6 haloalkoxy groups such as: C6-10 aryl groups such as phenyl groups and naphthyl groups; cyano groups;
• Examples of the substituent on the “heteroaryl group” for R 7 include a C1-6 haloalkoxy group, a C1-6 alkylsulfoxyimino group, a C1-6 alkylthio group, a C1-6 alkylsulfinyl group, and a C1-6 alkylsulfonyl group. Is preferred.
• the amide compound of the present invention is preferably a compound represented by formula (2) (hereinafter sometimes referred to as compound (2)) or a salt thereof.
• Z represents the same as that in the formula (1).
• R 1 , W, X, and n are the same as those in formula (A-1).
• R 4 , R 5 and R 6 are the same as those in the formula (B-1).
• the salt of the compound (1) of the present invention is not particularly limited as long as it is an agro-horticulturally acceptable salt.
• salts of inorganic acids such as hydrochloric acid and sulfuric acid
• salts of organic acids such as acetic acid and lactic acid
• salts of alkali metals such as lithium, sodium and potassium
• salts of alkaline earth metals such as calcium and magnesium
• iron and copper and salts of organic metals such as ammonia, triethylamine, tributylamine, pyridine, hydrazine, and the like.
• the amide compound of the present invention can be obtained by a known method.
• the salt of compound (1) can be produced from compound (1) by a known method.
• the 4-halopyridine compound is reacted with a 2-hydroxycarboxylic acid ester compound in the presence of a base to obtain a 2-[(pyridin-4-yl) oxy] carboxylic acid ester compound, which is then hydrolyzed to give 2 A — [(pyridin-4-yl) oxy] carboxylic acid compound is obtained, and this is reacted with an N-substituted amine compound to obtain a compound represented by the formula (2-2).
• Hal is a halogeno group.
• R 1a is not particularly limited, and is, for example, a C1-6 alkyl group.
• a compound represented by the formula (2-1) can be obtained by using an N-hydroxycarbamic acid ester compound instead of the 2-hydroxycarboxylic acid ester compound.
• R 1a is not particularly limited, but is, for example, a C1-6 alkyl group.
• the amide compound of the present invention is excellent in controlling pests such as various mites that affect plant growth.
• the amide compound of the present invention is a highly safe compound because it has no phytotoxicity to crops and has low toxicity to fish and warm-blooded animals.
• the amide compound of the present invention is useful as an active ingredient of an acaricide.
• the amide compound of the present invention exhibits an excellent control effect not only on mites of sensitive strains but also on mite-resistant mites which have recently become a problem.
• the amide compound of the present invention is excellent in the control effect of endoparasites that are harmful to humans and animals. In addition, it is a highly safe compound due to its low phytotoxicity and low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of an endoparasite control agent.
• the amide compound of the present invention exhibits efficacy at all stages of development of organisms to be controlled, and exhibits excellent control effects on, for example, eggs, nymphs, larvae, pupae and adults such as mites and insects. .
• the pest control agent or acaricide or insecticide of the present invention contains, as an active ingredient, at least one selected from the amide compounds of the present invention, that is, the compound (1) and the salt of the compound (1).
• the amount of the amide compound contained in the pest control agent or the acaricide or insecticide of the present invention is not particularly limited as long as it exhibits a pest control effect.
• the pest control agent or acaricide or insecticide of the present invention includes cereals, vegetables, root vegetables, potatoes, flowering plants, fruit trees, foliage plants, trees such as tea, coffee, cacao, grasses, turf Kind: It is preferably used for plants such as cotton.
• the pest control agent or acaricide or insecticide of the present invention may be any of leaves, stems, stalks, flowers, buds, fruits, seeds, sprout, roots, tubers, tuberous roots, shoots, cuttings, etc. It may be used for the part.
• the pest control agent or acaricide or insecticide of the present invention is not particularly limited depending on the species of the plant to be applied. Examples of plant seeds include original species, varieties, improved varieties, cultivars, mutants, hybrids, and genetically modified organisms (GMO).
• the pest control agent or acaricide or insecticide of the present invention can be used for seed treatment, foliage application, soil application, water surface application, etc. to control various mites.
• Lepidoptera butterfly or moth (a) moths of the Arctiidae family, eg Hyphantria cunea, Lemyra imparilis; (b) moths of the family Bucculatricidae, for example, Bucculatrix pyrivorella; (c) moths of Carposinidae, for example, Carposina sasakii; (d) moths of the family Craambidae, for example, Diaphania spp., Diaphania indica, Diaphania nitidalis; for example, Ostrinia spp.
• Astragalus Ostrinia furnacalis
• European corn borer Ostrinia nubilalis
• Azuki bean Ostrinia scapulalis
• Others Diatraea grandiosella
• Glyphodes pyloalis, Hellula undalis, Parapediasia teterrella
• Gelechiidae moths for example, Helcystogramma triannulella, Pectinophora gossypiella, Phthhorimaea operculella, Sitotroga cerealella
• Geometridae moths for example Ascotis selenaria
• moths from the family Gracillariidae for example, Caloptilia theivora, citrus leafworm (Phyllocnistis citrella), phleglonorycter ringoniella
• Hesperiidae butterflies such as Parnara
• (k) moths of the family Lyonetiidae for example, Lyonetia clerkella, Lyonetia prunifoliella malinella, from the genus Lyonetia spp .;
• (l) Noctuidae moths for example, Spodoptera depravata, Southern army worm (Spodoptera eridania), Spodoptera exigua, Spodoptera exigua, Spodoptera exigua, Spodoptera exigua, ), African Spodoptera littoralis, Spodoptera litura; eg, Autographa spp., Autographa gamma, Autographa nigrisigna; eg, Agrotis sp.
• Agrotis ipsilon, Agrotis segetum for example, Helicoverpa spp., Helicoverpa armigera, Tobacco moth (Helicoverpa assulta), Cotton ball worm (Helicoverpa zea); Of the species (Heliothis spp.), Heliothis armigera, Heliothis virescens; Others, Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, Mythimna separata, Naranga aenis jacen Peridroma saucia), soy bean looper (Pseudoplusia includens), nettle wain (Trichoplusia ni); (m) Nolidae moths, such as Misaria Olingsa (Earias insulana); (n) Pieridae butterflies, for example, Pieris sp., Pieris brassicae, Pieris
• Thysanoptera pest (a) from the Phlaeothripidae family, for example, Ponticulothrips diospyrosi; (b) from the Thripidae family, for example, Frankliniella intonsa, Frankliniella occidentalis; for example, Frankliniella occidentalis; Thrips palmi, Thrips tabaci; other, Croton thrips (Heliothrips haemorrhoidalis), Scirtothrips dorsalis.
• Pests of the Hemiptera (A) Cervical antrum (Archaeorrhyncha) (a) From the Delphacidae family, for example, the green planthopper (Laodelphax striatella), the green planthopper (Nilaparvata lugens), the black planthopper (Perkinsiella saccharicida), and the white planthopper (Sogatella furcifera).
• Clypeorrhyncha (a) From the family of Cicadellidae, for example, Empoasca spp., Empoasca fabae, Empoasca nipponica, Empoasca onukii, Empoasca sakaii, Others ).
• C Stink bug (Heteroptera) (a) from the family Alydidae, for example, Riptortus clavatus; (b) from the family Coridae, for example, Cletus punctiger, Leptocorisa chinensis; (c) From the family of the family Lygaeidae, for example, the American leaf beetle (Blissus leucopterus), the leaf beetle (Cavelerius saccharivorus), the leaf beetle (Togo hemipterus); (d) From the Miridae family, for example, the black beetle turtle (Halticus insularis), the red-bellied turtle (Lygus lineolaris), the cotton-free hopper (Psuedatomoscelis seriatus), the long-nosed turtle (Stenodema sibiricum), the Stellata tus rutus ), Trigonotylus caelestialium;
• (D) Sternorrhyncha (a) from the family Adelgidae, for example, Adelges laricis; (b) Aleyrodidae, for example, Bemisia spp., Silver leaf whiteflies (Bemisia argentifolii), Tobacco whiteflies (Bemisia tabaci); Others citri), Trialeurodes vaporariorum; (c) Aphididae, for example, from Aphis spp., Aphis craccivora, bean aphid (Aphis fabae), strawberry aphid (Aphis forbesi), cotton aphid (Aphis gossypii) , European apple aphids (Aphis pomi), elder-core aphids (Aphis sambuci), Aphis spiraecola; for example, Rhopalosiphum spp.
• Aphididae for example, from Aphis spp., Aphi
• Dysaphis spp. from the genus Dysaphis spp., Dysaphis plantaginea, Dysaphis radicola; for example, Macrosiphum spp., Macrosiphum avenae, aphid (Macrosiphum euphorbiae); e.g. Myzus spp.
• Mussels (Myzus cerasi), peach aphids (Myzus persicae), myrtle aphids (Myzus varians); other, pea beetle aphids (Acyrthosiphon pisum), potato beetles Aphids (Brevicoryne brassicae), strawberry aphids (Chaetosiphon fragaefolii), peach beetles (Hyalopterus pruni), Hyperomyzus lactucae, black-headed aphids (Lipaphis erysimi), ura aphids Aphids (Metopolophium dirhodum), lettuce aphids (Nasonovia ribis-nigri), hops aphids (Phorodon humuli), barley aphids (Schizaphis graminum), barley aphids (Sitobion avenae), comican aphids
• Polyphaga pests (a) from the family Anobiidae, for example, the tobacco beetle (Lasioderma serricorne); (b) from the family Attelabidae, for example, Byctiscus betulae, Rhynchites heros; (c) from the Bostrichidae family, for example, Lyctus brunneus; (d) from the Brentidae family, for example, Cylas formicarius; (e) from the Buprestidae family, for example, Agrilus sinuatus; (f) From the Cerambycidae family, for example, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoder; (g) Northern corn of the Chrysomelidae family, for example, Bruchus spp., Bruchus pisorum, Bruchus rufimanus; eg, Diabrotica
• Rootworm (Diabrotica barberi), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm (Diabrotica virgifera); for example, Phyllotreta nemorum, Phyllotreta nemorum, ); Others, Aulicophora femoralis, Adzuki beetle (Callosobruchus chinensis), Tortoise beetle (Cassida nebulosa), Tentobi potato beetle (Chaetocnema concinna), Colorado potato beetle (Leptinotarsa decemlineata), Inkubihoso yzae (Oule) Psylliodes angusticollis;
• Flies (Diptera) pests A) Brachycera (a) From the family Agromyzidae, for example, from the genus Liriomyza spp., from Liriomyza bryoniae, from Liriomyza chinensis, from tomato leaf (Liriomyza sativae), from rio myza trifoli; Others, Chromatomyia horticola, Agromyza oryzae; (b) From the family Anthomyiidae, for example, Delia spp., Dela platura, Cabbage fly (Delia radicum); Other, Pegomya cunicularia; (c) Drosophila suzukii from the Drosophilidae family, for example, from Drosophila spp., Drosophila melanogaster, Drosophila suzukii; (d) from the Ephydridae family, for example, Hydrellia griseola;
• Nematocera From the family Cecidomyiidae, for example, the soybean fly (Asphondylia yushimai), the sorghum fly (Contarinia sorghicola), the fly fly (Mayetiola destructor), the mud fly (Sitodiplosis mosellana).
• Grasshopper (Orthoptera) pests (a) From the Acrididae family, for example, Schistocerca spp., Schistocerca americana, Schistocerca gregaria; (Dociostaurus maroccanus), grasshopper (Locusta migratoria), brown locust (Locustana pardalina), red locust (Nomadacris septemfasciata), cobaneago (Oxya yezoensis); (b) From the family of crickets (Gryllidae), for example, European cricket (Acheta domestica), Teleogryllus emma; (c) from the family Gryllotalpidae, for example, Gryllotalpa orientalis; (d) From the Tettigoniidae family, for example, Tachycines asynamorus.
• Acrididae family for example, Schistocerca spp., Schistocerca americana, Schistocer
• Tick (Acari) (A) Astigmata (Acaridida) (a) Acaridae ticks, for example, Rhizoglyphus echinopus, Rhizoglyphus robini; Rhizoglyphus robini; for example, Tyrophagus spp. Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; Other, Acetus tick
• B Prostigmata mite (Actinedida)
• (a) Tetranychidae ticks for example, Bryobia spp., Clover spider mites (Bryobia praetiosa), Fowl spider mites (Bryobia rubrioculus); , White spider mite (Eotetranychus kankitus), tick mite (Eotetranychus kankitus) (Eotetranychus smithi), Sugimen spider mite (Eotetranychus suginamensis), Walnut spider mite (Eotetranychus uncatus); for example, Oligonis spp.
• Mango spider mite (Oligonychus mangiferus), sugar cane spider mite (Oligonychu s orthius), Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii, Oligonychus ununguis; tick, Pony Panonychus mori), apple spider mites (Panonychus ulmi); for example, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus vorni, Tetranychus tranni (Tetranychus phaselus), nite spider mite (Tetranychus urticae), mite spider mite (Tetranychus viennensis); for example, Aponicchus spp.
• Sasanychus akitanus Spider mites (Sasanychus pusillus); for example, Shizotetranychus celarius, Shizotetranychus longus, Shizotetranychus miscanzo, chus Willow spider mites (Shizotetranychus schizopus); Others, Tetranychina harti, Tuckerella pavoniformis, Kew spider mite (Yezonychus sapporensis);
• Tenuipalpidae ticks for example, Brevipalpus spp., Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Cactus russulus), for example, Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; other, Tenuipalpus zhizhilashviliae;
• Eriophyidae mites such as Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, carnation Rust mites (Aceria paradianthi), Black spider mites (Aceria tiyingi), Tulip spider mites (Aceria tulipae), Shibahamakifushi mite (Aceria zoysiea); for example, Eriophyes spp.
• the pest control agent or acaricide or insecticide of the present invention may contain components other than the amide compound of the present invention.
• examples of other components include known carriers used for formulation.
• conventionally known fungicides, insecticides / acaricides, nematicides, soil insecticides, plant regulators, synergists, fertilizers, soil improvers, animal feeds, etc. be able to. By containing such other components, there may be a synergistic effect.
• insecticide / acaricide, nematicide, soil insecticide, anthelmintic and the like that can be mixed or used in combination with the pest control agent of the present invention are shown below.
• Acetylcholinesterase inhibitor (a) Carbamate series: Alanicarb, Aldicarb, Bengiocarb, Benfuracarb, Butcarboxyme, Butoxycarboxyme, Carbaryl, Carbofuran, Carbosulfan, Ethiophenecarb, Fenobucarb, Formethanate, Furatiocarb, Isoprocarb, Methiocarb, Mesomil, Oxamyl, Pirimicarb, Propoxyl Thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb, phenothiocarb, MIPC, MPMC, MTMC, aldoxicarb, alixicarb, aminocarb, bufencarb, cloetocarb, metam sodium, promecarb;
• GABA-agonist chloride channel antagonists acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole; camfechlor, heptachlor, dienochlor.
• Nicotinic acetylcholine receptor agonists acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxafurol, nicotine, flupiradiflon.
• Nicotinic acetylcholine receptor allosteric modulator spinetoram, spinosad.
• Juvenile hormone-like substances hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen; diophenolan, epofenonane, triprene.
• Non-specific inhibitors methyl bromide, chloropicrin, sulfuryl fluoride, borax, tartar.
• Homogeneous selective feeding inhibitors flonicamid, pymetrozine, pyrifluquinazone.
• Tick growth inhibitor clofentezin, difluvidazine, hexythiazox, etoxazole.
• Microbial-derived insect midgut lining destroyer Bacillus thuringiensis subsp. Isla elensis, Bacillus sphaericus, Bacillus thuringiensis subsp. Aisawai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp.
• Crop proteins Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.
• Mitochondrial ATP biosynthetic enzyme inhibitors diafenthiuron, azocyclotin, cyhexatin, fenbutasine oxide, propargite, tetradiphone.
• Oxidative phosphorylation uncouplers chlorfenapyr, sulframide, DNOC; binapacryl, dinobutone, dinocup.
• Nicotinic acetylcholine receptor channel blocker bensultap, cartap hydrochloride; nereistoxin; thiosultap monosodium salt, thiocyclam.
• Chitin synthesis inhibitor bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novallon, nobiflumuron, teflubenzuron, triflumuron, buprofezin, fluazuron.
• Diptera molting agent cyromazine.
• Molting hormone receptor agonists Chromafenozide, halofenozide, methoxyphenozide, tebufenozide.
• Octopamine receptor agonist Amitraz, demiditraz, chlordimeform.
• Mitochondrial electron transport system complex III inhibitor acequinosyl, fluacrylpyrim, hydramethylnon.
• Mitochondrial electron transport system complex I inhibitor phenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone.
• Anthelmintic (a) benzimidazole series: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, fulbendazole; fevantel, netobimine, thiophanate; thiabendazole, canbendazole; (b) Salicylanilide series: closantel, oxyclozanide, rafoxanide, niclosamide; (c) substituted phenols: nitroxinyl, nitroskanate; (d) Pyrimidine series: Pirantel, Morantel; (e) Imidazothiazole series: levamisole, tetramisol; (f) Tetrahydropyrimidine series: praziquantel, epsiprantel; (g) Other anthelmintic drugs: cyclodiene, riania, chlorthrone, metronidazo
• Nucleic acid biosynthesis inhibitors (a) RNA polymerase I inhibitor: benalaxyl, benalaxyl-M, furaxyl, metalaxyl, metalaxyl-M; oxadixil; cloziracone, off-race; (b) adenosine deaminase inhibitor: bupilimate, dimethylylmol, ethylimol; (c) DNA / RNA synthesis inhibitors: Himexazole, octirinone; (d) DNA topoisomerase II inhibitor: Oxophosphate.
• Mitotic fission inhibitor and cell division inhibitor (a) ⁇ -tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate methyl; dietofencarb; zoxamide; ethaboxam; (b) Cell division inhibitor: Pencyclon; (c) Delocalization inhibitor of spectrin-like protein: fluopicolide.
• Respiratory inhibitor (a) Complex I NADH oxidoreductase inhibitor: diflumetrim; tolfenpyrad; (b) Complex II succinate dehydrogenase inhibitors: benodanyl, flutolanil, mepronil; isophetamide; fluopyram; fenfram, flumeciclos; carboxin, oxycarboxin; tifluzamide; , Furametopyr, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid; (c) Complex III ubiquinol oxidase Qo inhibitor: azoxystrobin, cumoxystrobin, cumethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyroxystrobin; pyraclostrobin, Piramethostrobin, triclopyricarb; Cresoxime-methyl, trifloxystrobin; Dimoxystrobin, Phenaminestrobin, Met
• Signaling inhibitor (a) Signaling inhibitor: quinoxyphene, proquinazide; (b) MAP / histidine kinase inhibitor in osmotic signal transduction: fenpiclonil, fludioxonil; clozolinate, iprodione, procymidone, vinclozolin.
• Lipid and cell membrane synthesis inhibitors (a) Phospholipid biosynthesis, methyltransferase inhibitor: Edifenphos, iprobenphos, pyrazophos; isoprothiolane; (b) lipid peroxidants: biphenyl, chloroneb, dichlorane, kinden, technazene, tolcrofosmethyl; etridiazole; (c) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarbfocetylate, prothiocarb; (d) Microorganisms that disrupt the pathogen cell membrane: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis strain D747 strain; (e) Agent that disturbs the cell membrane: An extract of Goseika Yupte (Tea Tree).
• Cell membrane sterol biosynthesis inhibitors (a) Demethylation inhibitor at the C14 position in sterol biosynthesis: Triphorine; Pyrifenox, Pyrioxazole; Phenarimol, Flurprimidol, Nuarimol; Imazalyl, Imazaryl Sulfate, Oxpoconazole, Pefrazoate, Prochloraz, Triflumizole Azaconazole, viteltanol, bromconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriazole, fluconazole, Fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole
• Melanin biosynthesis inhibitor (a) Reductase inhibitor of melanin biosynthesis: Fusaride; Pyroxylone; Tricyclazole; (b) Dehydrase inhibitor of melanin biosynthesis: carpropamide; diclocimet; phenoxanyl.
• Host plant resistance inducer (a) Agents acting on the salicylic acid synthesis pathway: Acibenzoral-S-methyl; (b) Others: Probenazole; thiazinyl; isotianil; laminarin;
• Agents with multiple action points copper (copper salt), Bordeaux liquid, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; farbum, mancozeb, maneb, Mankappa, methylam, polycarbamate, propineb, thiram, dineb, ziram; captan, captahol, phorpet; chlorothalonil; diclofluuride, tolylfluanid; guazatine, iminoctadine acetate, iminoctadine albecate (iminoctadine trialbesilate); anilazine; dithianon; quinomethionate;
• plant regulators that can be used in combination or in combination with the pest control agent of the present invention are shown below. Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichloroprop, phenothiol, 1 -Naphtylacetamide, Ethiclozate, Cloxiphonac, Maleic acid hydrazide, 2,3,5-Triiodobenzoic acid
• the endoparasite control agent or pesticide of the present invention contains at least one selected from the amide compounds of the present invention as an active ingredient.
• the compound of the present invention can be used in an amount (pharmacologically effective amount) of 0.01 to 1000 mg per 1 kg of the host animal.
• the endoparasite control agent or pesticide of the present invention is not particularly limited by the dosage form. Dosage forms include powders, granules, tablets, capsules, pour-on formulations, spot-on formulations, emulsions, sprays, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal injections, etc.), wafers , Biscuits, minced meat and the like.
• the endoparasite control or control agent of the present invention may contain only the amide compound of the present invention, a carrier such as a liquid carrier, a gaseous carrier, a solid carrier, a surfactant as necessary, Other adjuvants may be further contained. Further, the endoparasite control or control agent of the present invention may be obtained by impregnating a base material such as a porous ceramic plate or a nonwoven fabric with the amide compound of the present invention.
• Parasites that are targets of the endoparasite control or pesticide of the present invention parasitize in host animals, particularly warm-blooded animals and fish (endoparasites).
• a host animal in which the parasite control or control agent of the present invention is effective include humans, livestock mammals (e.g., cows, horses, pigs, sheep, goats), laboratory animals (e.g., mice, rats, gerbils, etc.) Pets (e.g., hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, buffalos, etc.), poultry (turkeys, ducks, chickens, quails, Warm-blooded animals such as geese and pet birds (eggs, parrots, nine-birds, wild birds, parakeets, juvenile pine, canaries, etc.); and fishes such as salmon, trout, and swordfish.
• Parasites to be controlled or controlled include the following: (1) Nematodes of Dioctophymatida (a) nematodes of the family Dioctophymatidae, for example, Dioctophyma renale of the genus Dioctophyma spp .; (b) Nematodes of the family Soboliphymatidae, for example, Soboliphyme abei, Soboliphyme baturini, of the species Soboliphyme spp.
• Trichocephalida nematodes (a) Trichinellidae Trichinella, for example, Trichinella spiralis from Trichinella spp .; (b) Trichuridae Trichuridae, for example, Capillaria spp. Capillaria annulata, Capillaria contorta, Capillary contorta Capillaria hepatica, Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris spp., Trichuris vulpis, cattle Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris suis.
• Trichinellidae Trichinella for example, Trichinella spiralis from Trichinella spp .
• Trichuridae Trichuridae for example, Capillaria spp. Capillaria annulata, Capillaria contorta, Capillary contorta Capillaria
• Rhabditida nematodes For example, Strongyloides papillosus, cat feces Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, Strongyloides ratti .
• Ancylostomatidae worms for example, Ancylostoma spp., Ancylostoma braziliense, Ancylostoma caninum, Zubini worms (Ancylostoma duodenale), cat helminth (Ancylostoma tubaeforme); Uncinaria spp., Uncinaria stenocephala; Bunostomum spp. (Bunostomum trigonocephalum).
• Strongylida nematodes (a) nematodes of the family Angiostrongylidae, for example, Aelurostrongylus spp., cat lungworm (Aelurostrongylus abstrusus); Schistosomiasis (Angiostrongylus vasorum), Cantonese schistosomiasis (Angiostrongylus cantonesis); (b) Crenosomatidae nematodes, for example, Crenosoma aerophila, Crenosoma vulpis of the genus Crenosoma spp .; (c) Filaroididae nematodes, for example, Filaroides hirthi, Filaroides osleri of Filaroides spp .; (d) Pneumoides of the family Pneumolidae (Metastrongylidae), for example, Metastrongylus aprius, Metastrongylus asymmetricus
• Strongylida nematodes (a) Nematodirus filicollis, Nematodirus spathiger from the nematodes of the Molineidae family, for example, Nematodirus spp .; (b) Nematodes of the Dictyocaulidae family, for example, Dictyocaulus spp., Dictyocaulus filaria, Bovine lungworm (Dictyocaulus viviparus); (c) Haemonchidae nematodes, for example, Haemonchus spp., Haemonchus contortus; Mexistocirrus spp.
• Strongylida nematodes (a) Nematodes of the Chabertiidae family, for example, the intestinal nodules of the Chabertia ovina; the intestinal nodules (Oesophagostomum spp.) of the genus Chabertia spp.
• elegans for example, from the species of the genus Strongylus spp., Strongylus asini, edentulous (Strongylus edentatus), Strongylus equinus , Strongylus vulgaris.
• Oxyurida nematodes Oxyuridae nematodes, for example, Enterobius anthropopitheci, Enterobius vermicularis; Oxyuris of Enterobius spp. spp.), Oxyuris equi; Passalurus spp., Passalurus ambiguus.
• Nematode of Ascaridida (a) Acaridiidae nematodes, for example, Ascaridia galli from the genus Ascaridia spp .; (b) Heterakidae nematodes such as Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum, Heterakis spp.
• Anisakidae nematodes for example, Anisakis simplex from Anisakis spp .;
• Nematodes of Ascarididae for example, Ascaris lumbricoides, Ascaris suum; Ascaris suum; Parascaris spp. (Parascaris equorum);
• Toxocaridae nematodes for example, Toxocara spp., Toxocara canis, Toxocara leonina, Toxocarasum, Toxocara vitulorum ), Toxocara cati.
• Spirurida nematodes (a) Nematodes of Onchocercidae, for example, Brugia spp., Brugia malayi, Brugia pahangi, Brugia patei; Dipetalonema Dipetalonema spp., Dipetalonema reconditum; Dirofilaria spp., Dirofilaria immitis; Filaria spp., Filaria spp.
• Nematodes of the Setariidae family for example, Setaria spp., Setaria digitata, Setaria equina, Setaria labiatopapillosa , Setaria marshalli; Wuchereria spp., Wuchereria bancrofti;
• Filariidae nematodes for example, Parafilaria spp., Parafilaria multipapillosa; Stephanofilaria spp., Stephanofilaria spp. Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.
• Spirurida nematodes (a) Nematodes of the Gnathostomatidae family, for example, Gnathostoma doloresi, Gnathostoma spinigerum of Gnathostoma spp .; (b) Nematodes of the family Habronematidae (Habronema spp.), for example, Habronema majus, Habronema microstoma, Habronema muscae; From the genus Species (Draschia spp.); (c) Nematodes of the family Physalopteridae, for example, Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera felidis,
• Thelaziidae nematodes such as Thelazia spip., Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Rhodesian eyes Insects (Thelazia rhodesi), Scriabin eyeworms (Thelazia skrjabini).
• Step 1-3 Ethyl 2-methyl-2- (3- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ ureido) propanoate: Compound 19 To a solution of compound 18 (6.04 g) in THF (40 ml) was added ethyl 2-amino-2-methylpropionate (2.93 g), and the mixture was stirred with heating under reflux for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain compound 19 (4.21 g, yield 62%).
• Step 1-4 Ethyl 2- (3-ethyl-3- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ ureido) -2-methylpropanoate: Compound 20 Compound 19 (4.21 g) was dissolved in DMF (40 ml), potassium carbonate (4.18 g) and iodoethane (1.97 g) were added, and the mixture was stirred for 5 hours under ice cooling. After completion of the reaction, ethyl acetate was added and washed with an aqueous ammonium chloride solution. The organic layer was dried over magnesium sulfate and filtered, and then the solvent was distilled off under reduced pressure.
• Step 1-6 2- (3-Ethyl-3- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ ureido) -N-isobutyl-2-methylpropanamide: Compound 22 (Compound No. 1-5) To a solution of compound 21 (0.20 g) in acetonitrile (10 ml) were added diisopropylethylamine (0.31 g), isobutylamine (0.048 g) and TBTU (0.31 g), and the mixture was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain compound 22 (0.21 g, yield 91%).
• Step 2-2 2- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ butanoic acid: Synthesis of Compound 12 Lithium hydroxide monohydrate in a THF / methanol / water (32ml / 8ml / 8ml) solution of Compound 11 (6.95g) The Japanese product (1.13 g) was added and stirred overnight. After completion of the reaction, 7% HCl (14.1 g) was added and extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure.
• Step 2-3 Methyl 2-methyl-2- (2- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ butanamido) propanoate: Synthesis of Compound 13 Compound 12 (2.50 g) in DMSO (30 ml) solution in diisopropylethylamine (7.76 g), 2-amino-2-methylpropionic acid methyl hydrochloride (1.69 g) and TBTU (5.14 g) were added, and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction solution was poured into aqueous ammonium chloride and extracted with ethyl acetate.
• Step 2-4 Methyl 2-methyl-2- (2- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ butanamido) propanoic acid: Synthesis of Compound 14 Compound 13 (8.44 g) in THF / methanol / water (60 ml / 15 ml Lithium hydroxide monohydrate (1.36 g) was added to the solution and stirred overnight. After completion of the reaction, 7% HCl (17.0 g) was added and extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer, dried and filtered, and then the solvent was distilled off under reduced pressure.
• Step 2-5) N- [1- (Isobutylamino) -2-methyl-1-oxopropan-2-yl] -2- ⁇ [2- (trifluoromethyl) pyridin-4-yl] oxy ⁇ butanamide: Synthesis of Compound 15 Compound 14 (0.20 g ) In acetonitrile (10 ml) was added diisopropylethylamine (0.31 g), isobutylamine (0.048 g) and TBTU (0.31 g), and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain Compound 15 (Compound No.
• Ethyl 4-bromo-2,3-dihydrofuro [3,2-c] pyridine-2-carboxylate Synthesis of Compound 2 2-Bromo-3-methyl-4-nitropyridine (16.5 g) is dissolved in THF (70 ml). , Ethyl glyoxyate (47% toluene solution: 24.7 g) and TBAF (1M THF solution: 190 ml) were added, and the mixture was stirred at room temperature for 2 days. After completion of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate.
• Step 3-2 Ethyl 4-bromo-2-ethyl-2,3-dihydrofuro [3,2-c] pyridine-2-carboxylate: Synthesis of Compound 3 A THF (241 ml) solution of Compound 2 (9.36 g) was cooled to -78 ° C. , HMPA (6.16 g) and EtI (6.44 g) were added, and NaHMDS (1.9 M: 21.7 ml) was added dropwise. After stirring at ⁇ 78 ° C. for 30 minutes, the mixture was stirred at room temperature for 1 hour. After completion of the reaction, an aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate.
• Step 3-3) 4-Bromo-2-ethyl-2,3-dihydrofuro [3,2-c] pyridine-2-carboxylic acid: Synthesis of Compound 4 Compound 3 (2.99 g) in THF / MeOH / H 2 O (32 ml / 8 ml / 8 ml) Lithium hydroxide monohydrate (0.46 g) was added to the solution and stirred overnight. After completion of the reaction, 7% HCl (5.74 g) was added and extracted with ethyl acetate. Magnesium sulfate was added to the obtained organic layer for drying and filtration, and then the solvent was distilled off under reduced pressure to obtain Compound 4 (2.99 g).
• Step 3-5 4-Bromo-2-ethyl-N- ⁇ 2- [4- (ethylsulfonyl) pyridin-2-yl] propan-2-yl ⁇ -2,3-dihydrofuro [3,2-c] pyridine-2-carboxamide: Synthesis of Compound 6 Compound 5 was dissolved in 60 ml of dichloromethane, mCPBA (3.85 g) was added under ice cooling, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, an aqueous sodium hydrogen carbonate solution was added and extracted with dichloromethane.
• Table 1 represents substituents in the compound represented by the formula (2-1) wherein Z is an oxygen atom and R 4 and R 5 are methyl groups.
• Table 2 shows the substituents in the compound in which Z is an oxygen atom and R 4 and R 5 together form a ring in formula (2-1).
• Table 3 shows the substituents in the compounds represented by formula (2-2) wherein Z is an oxygen atom or sulfur atom, R 1 is an ethyl group, and R 4 and R 5 are methyl groups.
• Table 4 shows the substituents in the compound in which Z is an oxygen atom in formula (3).
• n D melting point
• Et is an ethyl group
• n Pr is a normal propyl group
• i Pr is an isopropyl group
• c Pr is a cyclopropyl group
• n Bu is a normal butyl group
• s Bu is a secondary butyl group
• t Bu is tertiary butyl.
• c Bu represents a cyclobutyl group
• n Pen represents a normal pentyl group
• i Pen represents an isopentyl group
• c Hex represents a cyclohexyl group.
• Formulation Example 1 (wettable powder) 40 parts of amide compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate and 3 parts of alkylnaphthalene sulfonate were uniformly mixed and finely pulverized to obtain a wettable powder of 40% active ingredient. .
• Formulation Example 2 (Emulsion) 30 parts of the amide compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkylallyl ether were mixed and dissolved to obtain an emulsion of 30% active ingredient.
• Formulation Example 3 (Emulsion) 5 parts of the amide compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkylaryl ether were mixed and dissolved to obtain an emulsion containing 5% active ingredient.
• Formulation Example 4 5 parts of the amide 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 As a result, granules having an active ingredient content of 5% were obtained.
• Formulation Example 5 (Granule) After 5 parts of the amide compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctylsulfosuccinate sodium salt and 1 part of potassium phosphate are thoroughly pulverized and mixed, water is added and kneaded well, followed by granulation drying As a result, granules having an active ingredient content of 5% were obtained.
• Formulation Example 6 (Suspension) Mix 10 parts of the amide 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 to reduce the particle size to 3 ⁇ m A wet pulverizing agent was obtained until the suspension became 10% active ingredient.
• Formulation Example 7 (Granule) 5 parts of the amide compound of the present invention was dissolved in an organic solvent to obtain a solution. The solution was sprayed on 94 parts of kaolin and 1 part of white carbon, and then the solvent was evaporated under reduced pressure to obtain granules. This type of granule can also be used in admixture with animal food.
• Formulation Example 8 (Injection) 0.1 to 1 part of the amide compound of the present invention and 99 to 99.9 parts of peanut oil were uniformly mixed, and then sterilized by filtration through a sterilizing filter to obtain an injection.
• Formulation Example 11 (Spray agent) A spray agent was obtained by uniformly mixing 1 part of the amide compound of the present invention, 10 parts of propylene glycol and 89 parts of isopropanol.
• test examples show that the compound of the present invention is useful as an active ingredient of an acaricide or an endoparasite control agent.
• ppm indicates weight ppm.
• Test Example 2 Efficacy test against nymph spider mites Kidney seedlings were bred in 3 inch pots, and 8 adult nymph mite from Aomori Prefecture were inoculated on primary leaves. The emulsion of Formulation Example 3 was then diluted with water to a compound concentration of 125 ppm to obtain a drug. This drug was sprayed on the kidney beans. The green beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. The life and death of ticks were examined when 10 days had elapsed since the application of the drug. The test was performed in duplicate.
• the compounds shown in Table 8 were tested for potency against citrus red mite. All the compounds showed an insecticidal rate of 90% or more against citrus red mite.
• Test Example 4 Efficacy test 2 against citrus mite Eight female citrus red spider mites from Kanagawa Prefecture were inoculated on the mandarin orange leaves placed in the petri dish. The emulsion of Formulation Example 3 was then diluted with water to a compound concentration of 125 ppm to obtain a drug. This drug was sprayed on the tangerine leaves in a rotary spray tower. The tangerine leaf was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 65%. When 10 days had elapsed since the application of the drug, the life and death of ticks were examined. The test was performed in duplicate.
• Test Example 5 Efficacy test against apple spider mite Eight female spider mites from Aomori Prefecture were inoculated on apple leaves placed in a petri dish. The emulsion of Formulation Example 3 was then diluted with water to a compound concentration of 125 ppm to obtain a drug. This medicine was sprayed on the apple leaves in a rotary spray tower. The apple leaves were placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 65%. When 10 days had elapsed since the application of the drug, the life and death of ticks were examined. The test was performed in duplicate.
• the compounds shown in Table 10 were tested for efficacy against apple spider mites. All the compounds showed an insecticidal rate of 90% or more against apple spider mites.
• Test Example 6 Efficacy test against urticae (seed treatment test) 0.1 g of each of the compounds of the present invention was dissolved in 2 mL of acetone to prepare a test chemical solution. 10 g of soybean seeds were added to the test chemical solution, air-dried, and 20 seeds were sown in a planter. After being kept in a greenhouse at 25 ° C. for 7 days, the planter was inoculated with 10 females / strain of female spider mite (Tetranychus urticae). 14 days after the inoculation, the number of spider mite parasites was investigated, and the control rate was determined by the following formula. The test was performed in duplicate.
• Control rate (%) 100- ⁇ (Nt) / (Nc) ⁇ 100 ⁇
• Nc Number of surviving mites in the untreated group
• Nt Number of surviving mites in the treated group
• the compounds Nos. 1-6 and 3-28 were tested for efficacy against the spider mite. All the compounds showed a control rate of 90% or more against the spider mite.
• Test Example 7 Efficacy test against urticae (soil irrigation test)
• the emulsion of Formulation Example 3 was diluted with tap water to prepare a chemical solution having a concentration of 100 ppm.
• a plastic potted kidney bean seedling (primary leaf stage) was irrigated with 25 ml of chemical solution and placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%.
• Control rate (%) 100- ⁇ (Nt) / (Nc) ⁇ 100 ⁇
• Nc Number of surviving mites in the untreated group
• Nt Number of surviving mites in the treated group
• the compounds Nos. 3-28 and 3-53 were tested for efficacy against the spider mite. All the compounds showed a control rate of 90% or more against the spider mite.
• Control rate (%) 100- ⁇ (Nt) / (Nc) ⁇ 100 ⁇
• Nc Number of surviving ticks in untreated group
• Nt Number of surviving ticks in treated group
• Compound Nos. 1-6, 1-15, 3-27, 3-28, 3-53, 3-71 went. All the compounds showed a control rate of 90% or more against the spider mite.
• Microscopic examination includes assessment of mortality, injury, motility, progression of development and neutral red uptake by larvae compared to DMSO controls.
• Biological activity was defined by the minimum effective concentration (“MEC”), the concentration at which at least one of the larvae exhibited death, injury, changes in motility, changes in developmental progression or no neutral red uptake.
• MEC minimum effective concentration
• the compounds shown in Table 11 were subjected to in vitro efficacy tests against Ascaridia galli and Oesophagostomum dentatum. All of the compounds showed activity against one or more target parasites at an MEC of 25 ⁇ M or less.
• the amide compound of the present invention has no phytotoxicity to crops and can effectively control pests that are problematic in crops and sanitation, especially mites and pests.

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