WO2024034565A1 - Imidazolylazole compound and pest control agent - Google Patents
Imidazolylazole compound and pest control agent Download PDFInfo
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- WO2024034565A1 WO2024034565A1 PCT/JP2023/028758 JP2023028758W WO2024034565A1 WO 2024034565 A1 WO2024034565 A1 WO 2024034565A1 JP 2023028758 W JP2023028758 W JP 2023028758W WO 2024034565 A1 WO2024034565 A1 WO 2024034565A1
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- JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-UHFFFAOYSA-N 0.000 description 1
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- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- DBHVHTPMRCXCIY-UHFFFAOYSA-N tyclopyrazoflor Chemical compound N1=C(Cl)C(N(C(=O)CCSCCC(F)(F)F)CC)=CN1C1=CC=CN=C1 DBHVHTPMRCXCIY-UHFFFAOYSA-N 0.000 description 1
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- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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- 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
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Definitions
- the present invention relates to imidazolylazole compounds and pest control agents. More specifically, the present invention provides an imidazolylazole compound that has excellent insecticidal and/or acaricidal activity, is highly safe, and can be synthesized industrially advantageously, and a pest control method containing the same as an active ingredient. Regarding drugs.
- This application claims priority based on Japanese Patent Application No. 2022-127442 filed in Japan on August 9, 2022, the contents of which are incorporated herein.
- Patent Document 1 discloses compounds represented by formula (A), formula (B), etc.
- An object of the present invention is to provide an imidazolylazole compound that has excellent pest control activity, particularly insecticidal and/or acaricidal activity, is excellent in safety, and can be industrially advantageously synthesized.
- 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 extermination agent containing the above imidazolylazole compound as an active ingredient.
- a compound represented by formula (I) or a salt thereof is a group represented by formula (A1) or a group represented by formula (A2), In formulas (A1) and (A2), * indicates the binding site with B, R 1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted phenyl group, R 2 is a substituted or unsubstituted C1-6 alkyl group, R 3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, an amino group, a cyano group, or a halogeno group, In formula (I), B is a group represented by formula (B1) or a group represented by formula (B2), In formulas (B1) and (B2)
- a pest control agent containing as an active ingredient at least one selected from the group consisting of the compound described in [1] above and its salt.
- An insecticide or acaricide containing as an active ingredient at least one selected from the group consisting of the compounds described in [1] above and salts thereof.
- An ectoparasite control agent containing as an active ingredient at least one selected from the group consisting of the compounds described in [1] above and salts thereof.
- An endoparasite control or extermination agent containing as an active ingredient at least one selected from the group consisting of the compound described in [1] above and its salt.
- the imidazolylazole compound (compound represented by formula (I) or a salt thereof) of the present invention can control pests that cause problems in agricultural crops and hygiene.
- the imidazolylazole compound of the present invention can effectively control agricultural pests and mites, especially at lower concentrations.
- the imidazolylazole compound of the present invention can further effectively control ectoparasites and endoparasites that harm humans and livestock.
- the imidazolylazole compound of the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) or a salt of compound (I).
- the imidazolylazole compound of the present invention includes a compound represented by formula (I-1) (hereinafter sometimes referred to as compound (I-1)), a salt of compound (I-1), and a compound represented by formula (I-1).
- the compound represented by (I-2) (hereinafter sometimes referred to as compound (I-2)), the salt of compound (I-2), the compound represented by formula (I-3) (hereinafter referred to as compound (I-2)) , may be written as compound (I-3)), salt of compound (I-3), compound represented by formula (I-4) (hereinafter may be written as compound (I-4)) ) or a salt of compound (I-4).
- the imidazolylazole compound of the present invention is preferably Compound (I-1), a salt of Compound (I-1), Compound (I-2) or a salt of Compound (I-2); ) or a salt of compound (I-1) is more preferable.
- the term "unsubstituted” means only the core group. When “substituted” is not mentioned and only the name of the core group is listed, it means “unsubstituted” unless otherwise specified.
- substituted means that any hydrogen atom of a group serving as a core is substituted with a group (substituent) having the same or different structure from the core. Therefore, a “substituent” is another group bonded to the core group.
- the number of substituents may be one, or two or more. Two or more substituents may be the same or different.
- a term such as "C1-6" indicates that the number of carbon atoms in the group serving as a core is 1 to 6.
- This number of carbon atoms does not include the number of carbon atoms present in substituents.
- a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.
- the "substituent” is not particularly limited as long as it is chemically permissible and has the effects of the present invention.
- 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 group 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; Phenyl C1-6 alkyl groups such as benzyl group and phenethyl group; 3-6 membered heterocyclyl group; 3-6 membered heterocyclyl C1-6 alkyl group;
- Hydroxyl 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 group and pyridyloxy group; 5- to 6-membered heteroaryl C1-6 alkyloxy group such as thiazolylmethyloxy group and pyridylmethyloxy group;
- Formyl group C1-6 alkylcarbonyl groups such as acetyl group and propionyl group; 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 group, chloro group, bromo group, iodo 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; C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 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-chloropropeny
- Amino group C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group, diethylamino group; Anilino group, naphthylamino group; Phenyl C1-6 alkylamino groups such as benzylamino group and 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; unsubstituted or substituted aminocarbonyl groups such as aminocarbonyl group, dimethylaminocarbonyl group, phenylaminocarbonyl group, N-phenyl-
- 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 and 2,2,2-trifluoroethylthio group; Phenylthio group, naphthylthio group; 5- to 6-membered heteroarylthio groups such as thiazolylthio group and pyridylthio group;
- C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group; Phenylsulfinyl group; 5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl groups and pyridylsulfinyl groups;
- C1-6 alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group; C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group; phenylsulfonyl group; 5- to 6-membered heteroarylsulfonyl groups such as thiazolylsulfonyl group and pyridylsulfonyl group; C1-6 alkylsulfonyloxy groups such as methylsulfonyloxy group, ethylsulfonyloxy group, t-butylsulfonyloxy group; C1-6 haloalkylsulfonyloxy groups such as trifluoromethylsulfonyloxy group and 2,2,2-trifluoroethy
- TriC1-6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group; triphenylsilyl group; Cyano group; Nitro group.
- any hydrogen atom in the substituents may be substituted with a group having a different structure.
- substituents in this case include a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, a nitro group, and the like.
- the above-mentioned "3- to 6-membered heterocyclyl group” contains 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms as ring constituent atoms.
- the heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, as long as at least one ring is a heterocycle, the remaining rings may be any of a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring.
- Examples of the "3- to 6-membered heterocyclyl group” include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups.
- Examples of the "3- to 6-membered saturated heterocyclyl group” include aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group, etc.
- Examples of the "5-membered heteroaryl group” 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. can be mentioned.
- Examples of the "6-membered heteroaryl group” include a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, and triazinyl group.
- Examples of "5- to 6-membered partially unsaturated heterocyclyl group” include pyrrolinyl group, dihydrofuranyl group, dihydrothiophenyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group, thiazolinyl group, isothiazolinyl group, etc.
- a 5-membered partially unsaturated heterocyclyl group; a 6-membered partially unsaturated heterocyclyl group such as a dihydropyranyl group can be mentioned.
- R 1 in formulas (I-1), (I-2), (I-3) and (I-4) is substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted phenyl group.
- R 1 is preferably a substituted or unsubstituted C2-6 alkenyl group or a substituted or unsubstituted phenyl group, more preferably a substituted or unsubstituted phenyl group.
- the "C1-6 alkyl group” in R 1 may be linear or branched.
- Examples of “C1-6 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. , t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group, etc.
- Examples of the "C2-6 alkenyl group" in R 1 include 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, etc.
- substituents on the “phenyl group” in R 1 Halogeno group, C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group; A phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a C1-6 A 6-membered heteroaryl group substituted
- the "substituted phenyl group” in R 1 has one or more substituents on the "phenyl group", and the plurality of substituents may be bonded to each other to form a ring, and the ring is a saturated alicyclic group or It may be any unsaturated alicyclic ring.
- Examples of the "substituted phenyl group” include an indenyl group, an indanyl group, a tetrahydronaphthyl group, a dihydronaphthyl group, a tolyl group, a xylyl group, a mesityl group, and a juryl group.
- R 2 in formulas (I-1) and (I-2) is a substituted or unsubstituted C1-6 alkyl group.
- Examples of the "substituted or unsubstituted C1-6 alkyl group" for R 2 include the same ones as exemplified for R 1 above.
- R 3 in formulas (I-3) and (I-4) is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, an amino group (a group represented by -NH 3 ), a cyano group, or a halogeno group. It is the basis.
- Examples of the "substituted or unsubstituted C1-6 alkyl group" for R 3 include the same ones as exemplified for R 1 above.
- halogeno group examples include a fluoro group, a chloro group, a bromo group, an iodo group, and the like.
- a group represented by R b , a nitro group,
- Examples of the "substituted or unsubstituted C1-6 alkyl group” and “substituted or unsubstituted C2-6 alkenyl group” for R 4 include the same ones as exemplified for R 1 above.
- Examples of the "C2-6 alkynyl group" in R 4 include 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 and 1,1-dimethyl-2-butynyl group.
- C1-6 alkylcarbonyl group examples include acetyl group, propionyl, n-propylcarbonyl group, i-propylcarbonyl group, n-butylcarbonyl group, and t-butylcarbonyl group.
- Examples of the "C1-6 alkoxycarbonyl group" for R 4 include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group, etc. can.
- C3-6 cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.
- the "5- to 10-membered heterocyclyl group” in R 4 is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms as ring constituent atoms. When there are two or more heteroatoms, they may be the same or different. It may be either monocyclic or polycyclic. Examples of the "5- to 10-membered heterocyclyl group” include 5- to 10-membered saturated heterocyclyl groups, 5- to 10-membered heteroaryl groups, and 5- to 10-membered partially unsaturated heterocyclyl groups.
- Examples of the 5- to 10-membered saturated heterocyclyl group include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl 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 isoxazolyl 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 pyridazinyl group, and a triazinyl group.
- a pyridyl group examples include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
- 7-membered heteroaryl group 3-azabicyclo[3.2.0]heptane-1,4-dien-2-yl group, 3-azabicyclo[3.2.0]heptane-1,4,6-trien-6-yl Examples include groups.
- Examples of the 8-membered heteroaryl group include a 2,4,5,6-tetrahydrocyclopenta[c]pyrrol-2-yl group, a 2,4-dihydrocyclopenta[c]pyrrol-4-yl group, and the like.
- Examples of the 9-membered heteroaryl group include an indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, indazolyl group, benzimidazolyl group, benzoxazolyl group, benzisoxaozolyl group, benzothiazolyl group, benzisothiazolyl group, etc. can be mentioned.
- Examples of the 10-membered heteroaryl group include a quinolinyl group, an isoquinolinyl group, a cinnolinyl group, a phthalazinyl group, a quinazolinyl group, and a quinoxalinyl group.
- Examples of 5- to 10-membered partially unsaturated heterocyclyl groups include 5-membered partially unsaturated heterocyclyl groups such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, and isoxazolinyl group; dihydropyranyl group, etc.
- 6-membered partially unsaturated heterocyclyl group 9-membered partially unsaturated heterocyclyl group such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, 1,3-dihydrobenzofuranyl group; 1,2,3 , 10-membered partially unsaturated heterocyclyl groups such as 4-tetrahydroquinolinyl groups;
- the substituents on the "C3-6 cycloalkyl group", “phenyl group”, “naphthyl group”, or “5- to 10-membered heterocyclyl group” in R 4 include: Halogeno group, C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group; A phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; a 5-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6
- the "substituted phenyl group” or “substituted naphthyl group” in R 4 has one or more substituents on the "phenyl group” or "naphthyl group”, and the plurality of substituents are bonded to each other to form a ring.
- the ring may be either a saturated alicyclic ring or an unsaturated alicyclic ring.
- substituted phenyl group or “substituted naphthyl group” includes, for example, an indenyl group, an indanyl group, a tetrahydronaphthyl group, a dihydronaphthyl group, a tolyl group, a xylyl group, a mesityl group, a juryl group, and the like.
- the "substituted or unsubstituted amino group” in R 4 is a group represented by "-NR c R d ".
- the "substituted or unsubstituted aminocarbonyl group” in R 4 is a group represented by "-CO-NR c R d ".
- R c and R d each independently include a hydrogen atom, a C1-6 alkyl group, a formyl group, a C1-6 alkylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, and the like.
- Examples of the "substituted or unsubstituted amino group” for R 4 include an amino group, a methylamino group, an ethylamino group, a dimethylamino group, and the like.
- Examples of the "substituted or unsubstituted aminocarbonyl group” for R 4 include a methylaminocarbonyl group, an ethylaminocarbonyl group, and a dimethylaminocarbonyl group.
- Examples of the "C1-6 alkyl group" for R c and R d include the same groups as exemplified for R 1 .
- Examples of the "C1-6 alkylcarbonyl group" for R c and R d include an acetyl group and a propionyl group.
- R e and R f each independently include a hydrogen atom, a C1-6 alkyl group, a formyl group, a C1-6 alkylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, and the like.
- Examples of the "C1-6 alkyl group”, “C1-6 alkylcarbonyl group”, and “substituted or unsubstituted aminocarbonyl group” in R e and R f include the same ones as exemplified in R c and R d . be able to.
- R a and R b examples include the same ones as exemplified for R 1 .
- R 5 in formulas (I-1), (I-2), (I-3) and (I-4) is a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cyclo It is an alkyl group.
- R 5 is preferably a substituted or unsubstituted C1-6 alkyl group.
- Examples of the "substituted or unsubstituted C1-6 alkyl group" for R 5 include the same ones as exemplified for R 1 .
- Specific examples of the "substituted or unsubstituted C1-6 alkyl group” for R 5 include C3-6 cycloalkyl C1-6 alkyl groups such as cyclopropylmethyl group.
- Examples of the "substituted or unsubstituted C3-6 cycloalkyl group” for R 5 include the same ones as exemplified for R 4 .
- n in formulas (I-1), (I-2), (I-3) and (I-4) represents the number of O, and is 0, 1 or 2. That is, the group represented by R 5 --S(O) n -- is a group represented by R 5 --S-, a group represented by R 5 --SO-, or a group represented by R 5 --SO 2 --. indicates a group. It is preferable that n is 2.
- the salt of compound (I) is not particularly limited as long as it is an agriculturally and horticulturally acceptable salt.
- salts of compound (I) include 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; alkaline earths such as calcium and magnesium.
- Examples include salts of similar metals; salts of transition metals such as iron and copper; ammonia; salts of organic bases such as triethylamine, tributylamine, pyridine and hydrazine.
- the method for producing compound (I) or a salt of compound (I) is not particularly limited.
- compound (I) or a salt of compound (I) can be obtained by a known production method described in Examples and the like.
- the salt of compound (I) can be obtained from compound (I) by a known method.
- a compound in which the B moiety in formula (1) is B2 and n is 2 ((P-1) in the formula in the figure below) is produced by the reaction as follows. can do.
- a and R 5 in compound (IM-1) in the figure below have the same meanings as those in formula (1).
- a and R 5 in compound (P-3) have the same meanings as in formula (1).
- a and R 5 in compound (P-2) have the same meanings as in formula (1).
- A, R 4 and R 5 in compound (P-1) have the same meanings as in formula (1).
- R 4 in compound (IM-2) has the same meaning as those in formula (1), and
- X 1 represents a halogeno group.
- Compound (IM-1) is known or can be produced according to the method described in International Publication No. 2018/052035, International Publication No. 2023/090345, etc.
- Compound (P-3) can be produced by reacting compound (IM-1) with N,N-dimethylformamide dimethyl acetal (abbreviation: DMF-DMA).
- the reaction is usually carried out in a solvent.
- the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of these.
- DMF-DMA is usually used in a ratio of 1 to 10 mol per 1 mol of compound (IM-1).
- the reaction temperature is usually in the range of 0°C to 120°C. Reaction times usually range from 0.5 to 24 hours.
- compound (P-3) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
- Compound (P-2) can be produced by reacting compound (P-3) with hydrazine.
- the reaction is carried out in the presence of an organic acid, usually in a solvent.
- An example of the organic acid used in the reaction is acetic acid.
- Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, alcohols, and mixtures of two or more of these.
- hydrazine is usually used in a ratio of 1 to 5 mol per 1 mol of compound (P-3).
- the reaction temperature is usually in the range of -20°C to 120°C. Reaction times usually range from 0.1 to 24 hours.
- compound (P-2) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
- Compound (P-1) can be produced by reacting compound (P-2) and compound (IM-2) in the presence of a base.
- the reaction is usually carried out in a solvent.
- the solvent used in the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, and mixtures of two or more of these.
- Bases used in the reaction include organic bases, alkali metal hydrides, and alkali metal carbonates.
- compound (IM-2) is usually used in a proportion of 1 to 10 moles and a base is used in a proportion of usually 0.1 to 5 moles per mole of compound (P-2).
- the reaction temperature is usually in the range of -20°C to 120°C. Reaction times usually range from 0.1 to 24 hours.
- compound (P-1) After completion of the reaction, compound (P-1) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
- Compound (IM-2) is a commercially available compound or can be produced using known methods.
- a compound in which the B moiety in formula (1) is B1 and n is 2 ((T-1) in the formula in the figure below) can be reacted as follows. It can be manufactured in A and R 5 in compound (IM-3) in the figure below have the same meanings as those in formula (1). A and R 5 in compound (T-3) have the same meanings as those in formula (1), and X 2 represents a halogeno group. A, R 4 and R 5 in compound (T-2) have the same meanings as in formula (1). R 4 in compound (IM-4) has the same meaning as in formula (1). A, R 4 and R 5 in compound (T-1) have the same meanings as in formula (1).
- Compound (IM-3) is known or can be produced according to the method described in International Publication No. 2018/052035, International Publication No. 2023/090345, etc.
- Compound (T-3) can be produced by reacting compound (IM-3) with a chlorinating agent or a brominating agent.
- the reaction is usually carried out in the presence of a solvent.
- the solvent include halogenated hydrocarbons, alcohols, ethers, aprotic polar solvents such as DMF, NMP, DMI, and DMSO, acetic acid, water, and mixtures thereof.
- Chlorinating agents include, for example, chlorine and N-chlorosuccinimide
- brominating agents include, for example, bromine and N-bromosuccinimide.
- a chlorinating agent or a brominating agent is usually used in a ratio of 0.9 to 1.2 mol per 1 mol of compound (IM-3).
- Compound (T-2) can be produced by reacting compound (T-3) and compound (IM-4).
- the reaction is usually carried out in a solvent.
- the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, alcohols, and mixtures of two or more of these.
- compound (IM-4) is usually used in a ratio of 1 to 5 mol per 1 mol of compound (T-3).
- the reaction temperature is usually in the range of room temperature to 100°C. Reaction times usually range from 0.1 to 24 hours.
- compound (T-2) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
- Compound (IM-4) is a commercially available compound or can be produced using known methods.
- Compound (T-3) can be produced by reacting compound (T-2) with an oxidizing agent.
- the reaction is usually carried out in a solvent.
- the solvent used in the reaction include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more thereof.
- the oxidizing agent used in the reaction include mCPBA and hydrogen peroxide.
- a base or a catalyst may be used as necessary.
- the base include sodium carbonate.
- the catalyst include sodium tungstate.
- a catalyst When a catalyst is used in the reaction, it is usually used in a ratio of 0.01 to 0.5 mol per 1 mol of compound (T-2).
- the oxidizing agent In the reaction, the oxidizing agent is usually used in a ratio of 2 to 5 mol per 1 mol of compound (T-2).
- the reaction temperature is usually in the range of -20 to 60°C. Reaction times usually range from 0.1 to 12 hours.
- water is added to the reaction mixture, extracted with an organic solvent, and the organic layer is optionally treated with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (e.g., sodium bicarbonate). Wash.
- Compound (T-3) can be obtained by drying and concentrating this organic layer.
- the imidazolylazole compound of the present invention (hereinafter referred to as "the compound of the present invention") has an excellent control effect on pests such as various agricultural pests and mites that affect the growth of plants. Furthermore, the compound of the present invention has low phytotoxicity to crops and low toxicity to fish and warm-blooded animals, so it is a highly safe substance. Therefore, it is useful as an active ingredient in insecticides or acaricides. Furthermore, in recent years, many insect pests such as diamondback moths, planthoppers, leafhoppers, and aphids have developed resistance to various existing pesticides, resulting in the lack of efficacy of these drugs.Therefore, there is a need for drugs that are effective against resistant insect pests. ing. The compounds of the present invention exhibit excellent control effects not only on susceptible strains, but also on various resistant strains of insect pests, and furthermore against acaricide-resistant strains of mites.
- the compound of the present invention has an excellent control effect on ectoparasites and endoparasites that are harmful to humans and animals. It is also a highly safe substance as it has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient in agents for controlling ectoparasites and endoparasites.
- the compounds of the present invention exhibit efficacy at all developmental stages of organisms to be controlled, and exhibit excellent control effects against eggs, nymphs, larvae, pupae, and adults of mites and insects, for example.
- Pest control agent 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 pest control agent of the present invention is not particularly limited as long as it exhibits a pest control effect.
- Pest control agents are agents for controlling harmful organisms, and include insecticides or acaricides, ectoparasite control agents, endoparasite control or exterminators, and the like.
- the 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 compound of the present invention contained in the insecticidal or acaricidal agent of the present invention is not particularly limited as long as it exhibits an insecticidal or acaricidal effect.
- the pest control agent, insecticide or acaricide of the present invention can be applied to cereals; vegetables; root vegetables; tubers; flowers; fruit trees; ornamental plants, trees such as tea, coffee and cacao; grasses; Turf; preferably used for plants such as cotton.
- the pest control agent, insecticide or acaricide of the present invention can be applied to any plant such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, cuttings, etc. It may be used in the following areas.
- 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, cultivated varieties, mutants, hybrids, and genetically modified plants (GMO).
- 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.
- Lepidoptera butterflies or moths (a) Arctiidae moths, such as Hyphantria cunea, Lemyra imparilis; (b) moths of the Bucculatricidae family, such as Bucculatrix pyrivorella; (c) moths of the Carposinidae family, such as Carposina sasakii; (d) Moths of the Crambidae family, such as Diaphania spp., Diaphania indica, Diaphania nitidalis; for example, Ostrinia spp.
- Agrotis ipsilon, Agrotis segetum For example, Helicoverpa armigera, Helicoverpa assulta, cotton ball worm (Helicoverpa zea) of the Helicoverpa spp.; Heliothis armigera, of the Heliothis spp.
- Thysanoptera pests (a) Phlaeothripidae, for example, Ponticulothrips diospyrosi; (b) Thripidae, for example, Frankliniella spp., Frankliniella intonsa, Frankliniella occidentalis; for example, Thrips spp., Southern yellow thrips; Thrips palmi, Thrips tabaci; others, Heliothrips haemorrhoidalis, Scirtothrips dorsalis.
- Phlaeothripidae for example, Ponticulothrips diospyrosi
- Thripidae for example, Frankliniella spp., Frankliniella intonsa, Frankliniella occidentalis
- Thrips spp. Southern yellow thrips
- Thrips palmi Thrips tabaci
- others Heliothrips haemorrhoidalis, Scirtothrips dorsalis.
- B Clypeorrhyncha
- a Empoasca fabae, Empoasca nipponica, Empoasca onukii, Empoasca onukii, Empoasca spp. of the family Cicadellidae, for example Empoasca spp. Empoasca sakaii; Other leafhoppers: Arboridia apicalis, Balclutha saltuella, Epicanthus stramineus, Macrosteles striifrons, Nephotettix cinctinceps ).
- C Heteroptera
- Alydidae for example, Riptortus clavatus
- Coreidae for example Cletus punctiger, Leptocorisa chinensis
- Lygaeidae such as Blissus leucopterus, Cavelerius saccharivorus, Togo hemipterus
- Members of the Miridae family such as Halticus insularis, Lygus lineolaris, Cotton Free Hopper (Psuedatomoscelis seriatus), Stenodema sibiricum, and Stenotus rubrovitttatus. ), Trigonotylus caelestialium;
- Pentatomidae such as Nezara spp., Nezara antennata, Nezara viridula; for example, Eysarcoris spp. , Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, others, Dolycoris baccarum, Eurydema rugosum, Glaucias subpunctatus, and Eysarcoris ventralis.
- Halyomorpha halys Piezodorus hybneri, Plautia crossota, Scotinophora lurida;
- Pyrrhocoridae for example, Dysdercus cingulatus;
- Rhopalus musculatus of the family Rhopalidae for example;
- Scutelleridae for example, Eurygaster integriceps;
- Tingidae for example Stephanitis nashi.
- (D) Sternorrhyncha (a) Adelgidae, for example, the larch aphid (Adelges laricis); (b) Bemisia argentifolii, Bemisia tabaci of the family Aleyrodidae, such as Bemisia spp.; other, Aleurocanthus spiniferus, citrus whitefly; (Dialeurodes citri), whitefly (Trialeurodes vaporariorum); (c) Aphis craccivora, Aphis fabae, Aphis forbesi, and Aphis gossypii of the Aphidae family, such as Aphis spp.
- Aphids Macrosiphum euphorbiae
- Myzus spp. Myzus cerasi, Myzus persicae, Myzus varians; other aphids (Macrosiphum euphorbiae); Acyrthosiphon pisum), Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, Chaetosiphon fragaefolii, Hyalopterus pruni, Hyperomyzus lactuc ae ), Japanese radish aphid (Lipaphis erysimi), broad bean aphid (Megoura viciae), wheat aphid (Metopolophium dirhodum), lettuce aphid (Nasonovia ribis-nigri), hop aphid (Phorodon humuli), wheat aphid (Schizaphis graminum) ), wheat aphid (Sitobion a
- Unaspis euonymi Unaspis yanonensis; others, Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, Pseudaonidia paeoniae ); (f) family Margarodidae, such as Drosicha diverenta, Icerya purchasi; (g) of the family Phylloxeridae, for example Viteus vitifolii; (h) Planococcus citri, Planococcus kuraunhiae of the Pseudococcidae family, such as Planococcus spp.; other Phenacoccus solani , Pseudococcus comstocki; (i) Psylla mali, Psylla pyrisuga of the family Psyllidae, such as Psylla spp.; and other, Diaphorina citri.
- Pests of the suborder Polyphaga (a) of the family Anobiidae, for example, the tobacco beetle (Lasioderma serricorne); (b) family Attelabidae, such as Byctiscus betulae, Rhynchites heros; (c) Bostrichidae, for example, Lyctus brunneus; (d) of the family Brentidae, for example, Cylas formicarius; (e) Buprestidae, for example, Agrilus sinuatus; (f) Cerambycidae, such as Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, and Xylotrechus pyrrhoderus; (g) Chrysomelidae, e.g.
- Bruchus spp. pea weevil (Bruchus pisorum), broad bean weevil (Bruchus rufimanus); e.g. Diabrotica spp., northern corn; rootworm (Diabrotica barberi), southern corn rootworm (Diabrotica undecimpunctata), western corn rootworm (Diabrotica virgifera); e.g., Phyllotreta spp.
- Coccinellidae for example, Epilachna spp., Epilachna varivestis, Epilachna vigintioctopunctata;
- Curculionidae e.g. Anthonomus spp., boll weevil (Anthonomus grandis), pear weevil (Anthonomus pomorum); e.g. of Sitophilus spp.
- Pests of Diptera Brachycera
- a family Agromyzidae, for example, Liriomyza spp., Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, Liriomyza trifolii; Others, Chromatomyia horticola, Agromyza oryzae;
- Anthomyiidae such as Delia spp., Delia platura, and Delia radicum; other Pegomya cunicularia;
- Ephydridae for example, Hydrellia griseola;
- Psilidae for example, Psila rosae;
- Bactrocera cucurbitae Bactrocera dors
- Bactrocera spp. Bactrocera dorsalis; European fruit fly (Rhagoletis spp.); Rhagoletis cerasi), Rhagoletis pomonella; others, Ceratitis capitata, Dacus oleae.
- Nematocera (a) Family Cecidomyiidae, such as Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor, and Sitodiplosis mosellana.
- Pests of the order Orthoptera (a) Acrididae, such as Schistocerca spp., Schistocerca americana, Schistocerca gregaria; other, Australian locust (Chortoicetes terminifera),ixie locust (Dociostaurus maroccanus), brown locust (Locusta migratoria), brown locust (Locustana pardalina), red kite locust (Nomadacris septemfasciata), brown locust (Oxya yezoensis); (b) Gryllidae, for example, European house cricket (Acheta domestica), Enma cricket (Teleogryllus emma); (c) Molecular family (Gryllotalpidae), for example, Molecular mole (Gryllotalpa orientalis); (d) Members of the family Tettigoniidae, such as Tachycines asynamorus.
- Acrididae such as Schisto
- Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus ludeni of Tetranychus spp. Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Tetranychus viennensis, Tetranychus evansi; for example, Aponychus corpuzae, Aponychus spp.
- Aponychus firmianae for example, Sasanychus akitanus, Sasanychus pusillus, of the genus Sasanychus spp.; for example, Aponychus firmianae, of the genus Shizotetranychus spp. Shizotetranychus celarius), Shizotetranychus longus, Shizotetranychus miscanthi, Shizotetranychus recki, Willow spider mite (Shizotetranychus schizopus); Others, Tetranychina harti, Tuckerella pavoniformis ), Caeus spider mite (Yezonychus sapporensis);
- Aceria paradianthi Aceria tiyingi, tulip rust mite, Aceria zoysiea; for example, Eriophyes spp., Eriophyes chibaensis, Eriophyes emarginatae); e.g., Aculops spp., tomato rust mite (Aculops lycopersici), orange rust mite (Aculops pelekassi); e.g., Aculus spp., peach rust mite (Aculus fockeui), apple rust mite (Aculus) convincedendali; others: Acaphylla theavagrans, Calacarus carinatus, Colomerus vitis, Calepitrimerus vitis, Epitrimerus pyri, Paraphytoptus kikus, Paracalacarus podocarpi), Ryukyu citrus rust mite (Phyllocotruta citri); (d) Mites of the family Transonemidae
- the pest control agent of the present invention may contain other active ingredients such as fungicides, insecticides/acaricides, nematicides, and soil insecticides; plant regulators, synergists, fertilizers, soil conditioners, and animals. It may be mixed or used in combination with feed etc.
- the combination of the compound of the present invention and other active ingredients can be expected to have a synergistic effect with respect to insecticidal, acaricidal, and nematocidal activities.
- 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 standard method.
- Acetylcholinesterase (AChE) inhibitor organophosphorus
- Acephate Azamethiphos
- Azinphos-ethyl Azinphosmethyl
- Cadusafos Chlorethoxyfos
- Chlorfenvinphos Chlormephos
- Chlorpyrifos Chlorpyrifos-methyl
- Coumaphos Cyanophos
- Cyanophos Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoate ( Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate Fosthiazate), Heptenophos, Imicyafos, Isofenphos, Is
- GABAergic chloride ion (chloride ion) channel blockers Chlordane, Endosulfan; Ethiprole, Fipronil. Acetoprole, Camphechlor, Dienochlor, Heptachlor, Pyrafluprole, Pyriprole; Flufiprole.
- Kappa-Bifenthrin Biopermethrin, Chloroprallethrin, Dimefluthrin, Fenfluthrin, Fenpirithrin, Flufenprox, Heptaflu Heptafluthrin, Meperfluthrin, epsilon-Metofluthrin, Momfluorothrin, epsilon-Momfluorothrin, trans-Permethrin, Profluthrin , Protrifenbute, kappa-Tefluthrin, Terallethrin, Tetramethylfluthrin; Bioethanomethrin. (3B) Sodium channel modulators (DDTs) DDT, Methoxychlor.
- Nicotinic acetylcholine receptor (nAChR) competitive modulators Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam; Nicotine (Nicotine); Sulfoxaflor; Flupyradifurone; Triflumezopyrim. Nithiazine; Dicloromezotiaz, Flupyrimin.
- Nicotinic acetylcholine receptor (nAChR) allosteric modulators Spinetoram, Spinosad.
- Glutamatergic chloride ion (chloride ion) channel (GluCl) allosteric modulator Abamectin, Emamectin, Emamectin-benzoate, Lepimectin, Milbemectin. Doramectin, Eprinomectin, Ivermectin, Moxidectin, Selamectin.
- Other non-specific (multisite) inhibitors Methyl bromide, alkyl halides; Chloropicrin; Sodium aluminum fluoride, sulfuryl fluoride ( Sulfuryl fluoride; Borax, Boric acid, Disodium octaborate, Sodium borate, Sodium metaborate; Tartar Dazomet, Metam, Metam Sodium, Metam Potassium.
- chordotonal organ TRPV channel modulators Pymetrozine, Pyrifluquinazon; Afidopyropene; (10) Mite growth inhibitors Clofentezine, Diflovidazin, Hexythiazox; Etoxazole.
- Bt crop proteins Microbial-derived insect midgut lining disrupting agent Bt subsp. israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, Bt subsp. tenebrionis; Proteins contained in Bt crops (Bt crop proteins): Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1; Bacillus sphaericus.
- Chitin biosynthesis inhibitor type 0 Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron ), Noviflumuron, Teflubenzuron, Triflumuron. Fluazuron.
- Chitin biosynthesis inhibitor type 1 Buprofezin.
- Cyromazine an ecdysis inhibitor.
- anthelmintic agents that can be used in combination or in combination with the pest control agent of the present invention are shown below.
- Salicylanilide series closantel, oxyclozanide, lafoxanide, niclosamide;
- fungicides that can be mixed or used in combination with the pest control agent of the present invention are shown below.
- A) Inhibitor of nucleic acid synthesis metabolism A1) RNA polymerase I inhibitor benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M; oxadixyl ); ofurace.
- DNA/RNA biosynthesis inhibitors hymexazole and octhilinone A4) DNA topoisomerase type II inhibitor oxolinic acid.
- B Agents that act on the cytoskeleton and motor proteins B1) to B3) ⁇ -tubulin polymerization inhibition benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate methyl (thiophanate-methyl), diethofencarb, zoxamide, Ethaboxam. Chlorfenazole, debacarb, trichlamide, zarilamid. B4) Cell division (point of action unknown) pencycuron. B5) Delocalization of spectrin-like proteins fluopicolide, fluopimomide. B6) Actin/myosin/fimbrin function phenamacryl, metrafenone, pyriofenone.
- C1 Respiratory inhibitor C1
- Complex I NADH oxidoreductase diflumetorim, tolfenpyrad, fenazaquin.
- Complex II Succinate dehydrogenase benodanil, flutolanil, mepronil; isofetamid; fluopyram; cyclobutrifluram; fenfuram; carboxy carboxin, oxycarboxin; thifluzamide; benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, impyr inpyrfluxam, isopyrazam, penflufen, penthiopyrad, sedaxane; isoflucypram; pydiflumetofen; boscalid; pyraziflumid .
- Furmecyclox. C3) Complex III Cytochrome bc1 (ubiquinol oxidase) Qo site (cyt b gene) azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin; mandestrobin (mandestrobin); pyraclostrobin, pyrametostrobin, triclopyricarb; kresoxim-methyl, trifloxystrobin; dimoxystrobin, phenaminest fenaminstrobin, metominostrobin, orysastrobin; famoxadone; fluoxastrobin; fenamidone; pyribencarb; methyltetraprole.
- Cytochrome bc1 ubiquinol oxidase
- Qo site cyt b gene
- D Inhibitor of amino acid and protein synthesis
- Methionine biosynthesis cgs gene
- Cyprodinil mepanipyrim
- pyrimethanil cgs gene
- D2 Protein synthesis (ribosome translation termination stage) Blasticidin-S.
- D3 D4
- Protein synthesis ribosome translation initiation stage
- Kasugamycin kasugamycin hydrochloride
- streptomycin D5
- Protein synthesis ribosome polypeptide elongation stage
- E Signal transduction inhibitor
- E1 Signal transduction (mechanism of action unknown) Quinoxyfen, proquinazid.
- E2) MAP/histidine kinase (os-2, HOG1) in osmotic signal transduction
- E3) MAP/histidine kinases (os-1, Daf1) in osmotic signal transduction chlozolinate, dimethachlone, iprodione, procymidone, vinclozolin.
- F Agents that inhibit lipid biosynthesis or transport/cell membrane structure or function
- F2 Phospholipid biosynthesis, methyltransferases edifenphos, iprobenfos, pyrazophos; isoprothiolane.
- F3) Cellular biphenyl peroxide, chloroneb, dicloran, quintozene, tecnazene, tolclofos-methyl; etridiazole.
- F4 Cell membrane permeability, fatty acids iodocarb, propamocarb, propamocarb hydrochloride, prothiocarb.
- (G) Inhibitor of sterol biosynthesis in cell membrane G1) Demethylase at position C14 of sterol biosynthesis (erg11/cyp51) triforine; pyrifenox, pyrisoxazole; fenarimol, nuarimol; imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole; azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, etaconazole ( etaconazole), fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, mefen trifluconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole
- H Inhibitor of cell wall biosynthesis H4) Chitin synthase polyoxin. Polyoxorim. H5) Cellulose synthase dimethomorph, flumorph, pyrimorph; Benthiavalicarb, iprovalicarb, valifenalate; mandipropamid.
- I Inhibitor of cell wall melanin synthesis
- I1 Melanin biosynthesis reductase fthalide; pyroquilon; tricyclazole.
- I2) Melanin biosynthesis dehydratase carpropamid; diclocymet; fenoxanil.
- P Agents that induce host plant resistance P1 to P3) Salicylic acid signal transduction acibenzolar-S-methyl; probenazole; tiadinil, isotianil. P4) Polysaccharide elicitor laminarin. P5) Anthraquinone elicitor extract from Reynoutria sachalinensis. P6) Microorganism elicitor Bacillus mycoides isolate J; cell walls of Saccharomyces cerevisiae strain LAS117. P7) Phosphonate fosetyl-Al; phosphorous acid and salts; fosetyl-K, fosetyl-Na. P8) Salicylic acid-related dichlobentiazox.
- (M) Agents that exhibit multi-site contact activity Copper (different salts), basic copper sulfate, Bordeaux mixture, copper hydroxide, copper Copper naphthenate, copper oxychloride, copper sulfate, cuprous oxide, oxine-copper; sulphur, lime sulfur; amobam, ferbam, mancozeb, maneb, metiram, propineb, thiram, zinc thiazole, zineb, ziram ); captan, captafol, folpet; chlorothalonil; dichlofluanid, tolylfluanid; guazatine, guazatine acetates, iminoctadine (iminoctadine), iminoctadine triacetate, iminoctadine trialbesilate; anilazine; dithianon; chinomethionat; fluorimide; methasulfocarb. dazomet, cufraneb, mancopper, polycarba
- BM01 Biopesticides with multiple mechanisms of action/Biologically derived pesticides Extract from the cotyledons of lupine plantlets; Extract from Swinglea glutinosa; Gosei Kayupte ( extract from Melaleuca alternifolia (tea treeoil); plant oils (mixtures): eugenol, geraniol, thymol.
- BM02 Biological pesticides with multiple mechanisms of action/Biologically derived pesticides Trichoderma atroviride strain I-1237, Trichoderma atroviride strain LU132, Trichoderma atroviride strain SC1 ( Trichoderma atroviride strain SC1), Trichoderma atroviride strain SKT-1, Trichoderma atroviride strain 77B; Trichoderma asperellum strain T34, Trichoderma asperellum strain kd; Trichoderma harzianum strain T-22; Trichoderma virens strain G-41; Gliocladium catenulatum strain J1446; Clonostachys rosea strain CR-7; Coniothyrium minitans strain CON/M/91-08; Talaromyces flavus strain SAY-Y-94-01; Saccharomyces cerevisae strain LAS02; Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens strain FZ
- plant regulators that can be mixed or used 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 aviglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothiol, 1 -Naphthylacetamide, ethiclozate, cloxyphonac, maleic hydrazide, 2,3,5-triiodobenzoic acid,
- the ectoparasite control agent of the present invention contains at least one compound 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 an ectoparasite control effect.
- Host animals to be treated with the ectoparasite control agent of the present invention include humans, livestock mammals (e.g., cows, horses, pigs, sheep, goats, etc.), experimental animals (e.g., mice, rats, gerbils, etc.). ), companion animals (e.g.
- hamsters guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.
- wild and zoo mammals monkeys, foxes, deer, buffalo, etc.
- poultry turkeys, ducks, chickens, etc.
- warm-blooded animals such as quail, geese, etc.
- pet birds pigeons, parrots, mynahs, sparrows, parakeets, Japanese pine, canaries, etc.
- fish such as salmon, trout, and carp.
- Other examples include bees, stag beetles, and rhinoceros beetles.
- the ectoparasite control agent of the present invention can be applied by known veterinary techniques (topically, orally, parenterally, or subcutaneously).
- Methods of administration include oral administration to animals using tablets, capsules, and feed mixtures; administration to animals via immersion solutions, suppositories, and injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); oil-based or A method of locally administering an aqueous solution by spraying, pour-on, spot-on, etc.; kneading an ectoparasiticide into a resin, molding the kneaded product into a suitable shape such as a collar or ear tag, and applying it to an animal.
- Method of wearing and local administration; etc. can be mentioned.
- Ectoparasites live in and on host animals, especially warm-blooded animals. Specifically, they live by parasitizing the back, armpits, lower abdomen, inner thighs, etc. of host animals, and obtain nutrients such as blood and dander from the animals. Examples of external parasites include mites, lice, fleas, mosquitoes, stable flies, and black flies. Specific examples of ectoparasites that can be controlled by the ectoparasiticide of the present invention are shown below.
- Siphonaptera fleas of the family Pulicidae such as Ctenocephalides spp., dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis); Fleas of the family Tungidae, fleas of the family Ceratophyllidae, and fleas of the family Leptopsyllidae.
- Hemiptera Hemiptera.
- Pests of the order Diptera mosquitoes of the family Culicidae; blackflies of the family Simuliidae; midges of the family Ceratopogonidae; horseflies of the family Tabanidae; flies of the family Muscidae; Sheshe flies of the family Glossinidae, flies of the family Hippoboscidae, flies of the family Hippoboscidae, flies of the family Calliphoridae, and flies of the family Oestridae.
- the endoparasite controlling or exterminating agent of the present invention contains at least one compound 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 exhibits an endoparasite control effect.
- the parasites targeted by the endoparasite control or extermination agent of the present invention parasitize host animals, particularly warm-blooded animals and fish (endoparasites).
- Host animals for which the endoparasite control or extermination agent of the present invention is effective include humans, livestock mammals (e.g., cows, horses, pigs, sheep, goats, etc.), and laboratory animals (e.g., mice, rats, gerbils, etc.).
- companion animals e.g.
- hamsters guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.
- wild and zoo mammals monkeys, foxes, deer, buffaloes, etc.
- poultry turkeys, ducks, chickens, quails, etc.
- warm-blooded animals such as pet birds (pigeons, parrots, mynahs, sparrows, parakeets, Japanese pine, canaries, etc.); and fish such as salmon, trout, and carp.
- Parasites to be controlled or exterminated include the following: (1) Nematodes of the order Dioctophymatida (a) Kidney worms of the family Dioctophymatidae, for example, Dioctophyma renale of the genus Dioctophyma spp.; (b) Kidney insects of the family Soboliphymatidae, such as Soboliphyme abei, Soboliphyme baturini of the Soboliphyme spp.
- Trichocephalida (a) Trichinella of the family Trichinellidae, for example, Trichinella spiralis of the Trichinella spp.; (b) Whipworms of the family Trichuridae, such as Capillaria spp., Capillaria annulata, Capillaria contorta, hepatic capillary nematodes ( Capillaria hepatica), Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris spp., Trichuris vulpis, cattle Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris suis.
- Capillaria spp. Capillaria annulata, Capillaria contorta, hepatic capillary nematodes ( Capillaria hepatica), Capillaria perforans, Capillaria plica, Capillaria suis; Trichuri
- Nematodes of the order Rhabditida Strongyloididae of the family Strongyloididae such as Strongyloides papillosus of the genus Strongyloides spp., cat feces Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, Strongyloides ratti .
- Nematodes of the order Strongylida Hookworms of the family Ancylostomatidae such as Ancylostoma braziliense, Ancylostoma caninum, and Zubini hookworm of the Ancylostoma spp.
- Ancylostoma duodenale Ancylostoma tubaeforme
- Uncinaria stenocephala Uncinaria stenocephala
- Bunostomum spp. Bunostomum phlebotomum, sheep hookworm ( Bunostomum trigonocephalum).
- Nematodes of the order Strongylida (a) Nematodes of the family Angiostrongylidae, for example Aelurostrongylus abstrusus of the genus Aelurostrongylus spp.; Angiostrongylus vasorum, Angiostrongylus cantonesis of the genus Angiostrongylus spp.; (b) Nematodes of the family Crenosomatidae, such as Crenosoma spp., Crenosoma aerophila, Crenosoma vulpis; (c) nematodes of the family Filaroididae, such as Filaroides spp., canine lungworm (Filaroides hirthi), Filaroidesosleri; (d) Lungworms of the family Metastrongylidae, such as Metastrongylus spp., Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus pudendotec
- Nematodes of the order Strongylida (a) Nematodes of the family Molineidae, such as Nematodirus filicollis, Nematodirus spp. Tigger (Nematodirus spathiger); (b) Nematodes of the family Dictyocauridae, such as Dictyocaulus spp., filamentous lungworm (Dictyocaulus filaria), bovine lungworm (Dictyocaulus viviparus); (c) Nematodes of the family Haemonchidae, such as Haemonchus contortus of the genus Haemonchus spp.; bovine contortus of the genus Mecistocirrus spp.
- Nematodes of the order Strongylida (a) Nematodes of the family Chabertiidae, such as Chabertia ovina of Chabertia spp.; intestinal nodules Oesophagostomum brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum, Oesophagostomum georgianum, of the genus Oesophagostomum spp.
- Intestinal noduleworm (Oesophagostomum maplestonei), Intestinal noduleworm (pig) (Oesophagostomum quadrispinulatum), Bovine intestinal noduleworm (Oesophagostomum radiatum), Goat intestinal noduleworm (Oesophagostomum venulosum), Intestinal noduleworm (boar) (Oesophagostomum watanabei); (b) nematodes of the Stephanuridae family, such as Stephanurus dentatus of the Stephanurus spp.; (c) Nematodes of the strongyle family (Strongylidae), such as Strongylus spp., Strongylus asini, Strongylus edentatus, Strongylusequinus, Strongylus vulgaris.
- Nematodes of the order Oxyurida Nematodes of the family Oxyuridae, such as Enterobius spp., chimpanzee pinworms (Enterobius anthropopitheci), pinworms (Enterobius vermicularis); Oxyuris equi, of the genus Oxyuris; Passalurus ambiguus, of the genus Passalurus spp.
- Nematodes of the order Ascaridida (a) Nematodes of the family Ascaridiidae, such as Ascaridia galli of the Ascaridia spp.; (b) Nematodes of the family Heterakidae, such as Heterakis spp., Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum; , Heterakis pusilla, Heterakis putaustralis; (c) nematodes of the family Anisakidae, such as Anisakis simplex of the genus Anisakis spp.; (d) Nematodes of the Ascarididae family, such as Ascaris lumbricoides of the Ascaris spp., Ascaris suum; horse roundworms of the Parascaris spp.
- Nematodes of the family Toxocaridae such as Toxocara spp., Toxocara canis, Toxocara leonina, Toxocarasuum, Toxocara vitulorum; ), Toxocara cati.
- Nematodes of the order Spirurida (a) Nematodes of the family Onchocercidae, such as Brugia spp., Brugia malayi, Brugia pahangii (Brugia pahangi), Brugia patei; Dipetalonema spp., Dipetalonema reconditum; Dirofilaria spp., Dirofilaria Filaria oculi; Onchocerca spp.; Cervical threadworm (Onchocerca cervicalis); Onchocerca gibsoni; Pharyngeal threadworm Insect (Onchocerca gutturosa); (b) Nematodes of the Setariidae family, such as Setaria digitata, Setaria equina, Setaria labiatopapillosa, of the Setaria spp.
- Nematodes of the family Filariidae such as Parafilaria multipapillosa of the genus Parafilaria spp.; Stephanofilaria assumum of the genus Stephanofilaria spp. Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.
- Nematodes of the order Spirurida (a) Nematodes of the family Gnathostomatidae, such as Gnathostoma doloresi of the genus Gnathostoma spp.
- Nematodes of the family Habronematidae such as Habronema majus, Habronema microstoma, Habronema muscae of the genus Habronema spp.; Draschia Draschia megastoma of the genus and species (Draschia spp.);
- Nematodes of the family Physalopteridae such as Physaloptera spp., Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera spp.
- Physaloptera felidis Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaloptera rara), Physaloptera sibirica, Physaloptera vulpineus
- nematodes of the family Gongylonematidae such as Gongylonema pulchrum of the genus Gongylonema spp.
- nematodes of the Spirocercidae family such as Ascarops spp., Ascarops strongylina
- Nematodes of the family Thelaziidae such as Thelazia spp., Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Rhodesian eye; worm (Thelazia rhodesi), Scria
- the compounds of the present invention can also be applied to pests that have poisonous stingers and venom and cause damage to humans and animals, pests that transmit various pathogens and germs, and pests that cause discomfort to humans (toxic pests, sanitary pests, unpleasant pests). etc.) has excellent control effects.
- Pests of the order Hymenoptera wasps of the family Argidae, wasps of the family Cynipidae, wasps of the family Diprionidae, ants of the family Formicidae, wasps of the family Mutillidae, A wasp of the family Vespidae.
- Formulation 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 mixed uniformly, pulverized finely, and then granulated into particles with a diameter of 0.5 to 1.0 mm. Granules with 5% active ingredient are obtained.
- Formulation 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 the mixture was thoroughly kneaded, and then granulated and dried. Granules with 5% active ingredient are obtained.
- Formulation 5 Suspension agent 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 parts of xanthan gum, and 73.8 parts of water are mixed to obtain a particle size of 3 microns or less. Wet milling to obtain a suspension containing 10% of the active ingredient.
- the formulation of the ectoparasite control agent or the internal parasite control or extermination agent is shown below.
- (Formulation 8: pour-on agent) A pour-on 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.
- (Formulation 9: Spot-on agent) A spot-on agent is obtained by uniformly mixing 10 to 15 parts of the compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol.
- (Formulation 10: Spray) A spray 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 1-(5-((Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-3-(dimethyl Amino)-2-(ethylsulfonyl)prop-2-en-1-one [1-(5-((Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)- Synthesis of 1-methyl-1H-imidazol-2-yl)-3-(dimethylamino)-2-(ethylsulfonyl)prop-2-en-1-one]
- Step 2 (Z)-3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethyl sulfonyl)-1H-pyrazole [(Z)-3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl) Synthesis of -4-(ethylsulfonyl)-1H-pyrazole
- Step 3 (Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4 -(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine [(Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)- Synthesis of 1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine]
- Step 1 2-chloro-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethane-1-one [2-chloro-1-(1-methyl-5 -(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one]
- Step 2 2-(ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethane-1-one [2-(ethylthio)-1-(1 -methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one]
- Step 4 5-(ethylthio)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole )-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole]
- the compound of the present invention was synthesized in the same manner as in Example 1. Some of them are shown in Table 1. The melting point (mp) is listed in the physical properties column. NMR data is recorded for compounds with amorphous physical properties.
- Compounds with physical properties of AMORPHOUS were analyzed by 1 H-NMR.
- Compound number A-7 1 H NMR (400MHz, CDCl 3 ) ⁇ 7.46 - 7.39 (m, 2H), 7.28 (d, 2H), 7.23 (s, 1H), 3.73 (s, 3H), 3.03 (q, 2H), 1.56 (s, 18H), 1.35 (t, 3H).
- Compound number A-18 1 H-NMR (CDCl 3 ) ⁇ : 8.92(2H, d), 8.11(1H, s), 7.45(1H,dd), 7.12(1H,s), 4.03(2H, q) , 3.87(3H, s), 1.46(3H, t).
- emulsion (I) 5 parts of the compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkylaryl ether were mixed to obtain an emulsion (I) containing 5% active ingredient.
- emulsion (II) was obtained by mixing 98.5 parts of dimethylformamide and 1.5 parts of polyoxyethylene alkylaryl ether.
- Emulsion (I) was diluted with water so that the compound of the present invention was 125 ppm to prepare a test drug solution.
- the test chemical solution was sprayed on bok choy seedlings (7th true leaf development stage) planted in 3-inch pots. Bok choy seedlings were air-dried and then placed in plastic cups. To this, 10 adult beetles were released.
- the insects were stored in a thermostatic chamber at a temperature of 25° C. and a humidity of 65%, and the adult insects were determined to be alive or dead after 7 days from release, and the killing rate was calculated. This was repeated twice.
- Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm to obtain a test drug solution.
- Emulsion (II) was diluted with water to the same ratio as emulsion (I) to obtain a control drug solution.
- the test chemical solution or control chemical solution was sprayed on cucumber seedlings and air-dried.
- Adults were removed 2 days after spraying.
- Eggs were laid on cucumber seedlings. Parasitic larvae that hatched from eggs were counted 7 days after spraying. The control rate was calculated. This was repeated twice.
- Test Example 7 Efficacy test against cat fleas
- the compound of the present invention was dissolved in isopropanol to prepare a drug solution with a concentration of 20 ppm. 100 ⁇ L of this chemical solution was applied to the inner surface of the bottom of a glass vial ( ⁇ 330 mm) and air-dried to form a thin film of the compound of the present invention.
- Four adult cat fleas (Ctenocephalides felis) (mixed sexes) (mixed sexes) (mixed sexes) were released into a vial. It was covered and placed in a constant temperature room at 25°C. Four days after the release of the insects, the cat fleas were determined to be alive or dead, and the insecticidal rate was calculated. This was repeated twice.
- Test Example 7 Efficacy test against Ixodes ticks
- the compound of the present invention was dissolved in isopropanol to prepare a drug solution with a concentration of 20 ppm. 20 ⁇ L of this chemical solution was applied to the inner surface of the bottom of a glass test tube ( ⁇ 12 mm) and air-dried to form a thin film of the compound of the present invention.
- Four nymphs of Haemophysalis longicornis were released into a test tube. It was covered and placed in a constant temperature room at 25°C. After 4 days had elapsed from the release of the insects, the survival of the ticks was determined, and the killing rate was calculated. This was repeated twice.
- the imidazolylazole compounds of the present invention can be used for pest control, It can be understood that it is a compound that has particularly acaricidal and insecticidal effects. It can also be understood that the compound is effective against parasites that are harmful to humans and animals, such as ectoparasites.
- imidazolylazole compound that has excellent insecticidal and/or acaricidal activity, is highly safe, and can be industrially advantageously synthesized, and a pest control agent containing this as an active ingredient.
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Abstract
Provided is a compound represented by formula (I-1a) or the like, or a salt thereof. [In formula (I-1a), R1 represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or the like; R2 represents a substituted or unsubstituted C1-6 alkyl group; and R4 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2 to 6 alkenyl group, or the like.]
Description
本発明は、イミダゾリルアゾール化合物および有害生物防除剤に関する。より詳細に、本発明は、優れた殺虫活性および/または殺ダニ活性を有し、安全性に優れ、且つ工業的に有利に合成できるイミダゾリルアゾール化合物、ならびにこれを有効成分として含有する有害生物防除剤に関する。
本願は、2022年8月9日に、日本に出願された特願2022-127442号に基づき優先権を主張し、その内容をここに援用する。 The present invention relates to imidazolylazole compounds and pest control agents. More specifically, the present invention provides an imidazolylazole compound that has excellent insecticidal and/or acaricidal activity, is highly safe, and can be synthesized industrially advantageously, and a pest control method containing the same as an active ingredient. Regarding drugs.
This application claims priority based on Japanese Patent Application No. 2022-127442 filed in Japan on August 9, 2022, the contents of which are incorporated herein.
本願は、2022年8月9日に、日本に出願された特願2022-127442号に基づき優先権を主張し、その内容をここに援用する。 The present invention relates to imidazolylazole compounds and pest control agents. More specifically, the present invention provides an imidazolylazole compound that has excellent insecticidal and/or acaricidal activity, is highly safe, and can be synthesized industrially advantageously, and a pest control method containing the same as an active ingredient. Regarding drugs.
This application claims priority based on Japanese Patent Application No. 2022-127442 filed in Japan on August 9, 2022, the contents of which are incorporated herein.
殺虫・殺ダニ活性を有する化合物が種々提案されている。そのような化合物を農薬として実用するためには、効力が十分に高いだけでなく、薬剤抵抗性が生じ難いこと、植物に対する薬害や土壌汚染を生じさせないこと、家畜や魚類などに対する毒性が低いことなどが要求される。
Various compounds with insecticidal and acaricidal activity have been proposed. In order for such compounds to be used as agricultural chemicals, they must not only have sufficiently high efficacy, but also be unlikely to cause drug resistance, cause no phytotoxicity to plants or soil contamination, and have low toxicity to livestock and fish. etc. are required.
ところで、特許文献1には、式(A)、式(B)などで表される化合物が開示されている。
Incidentally, Patent Document 1 discloses compounds represented by formula (A), formula (B), etc.
本発明の課題は、有害生物防除活性、その中でも特に殺虫活性および/または殺ダニ活性に優れ、安全性に優れ、かつ工業的に有利に合成できるイミダゾリルアゾール化合物を提供することである。本発明の別の課題は、上記イミダゾリルアゾール化合物を有効成分として含有する有害生物防除剤、殺虫若しくは殺ダニ剤、外部寄生虫防除剤、または内部寄生虫防除若しくは駆除剤を提供することである。
An object of the present invention is to provide an imidazolylazole compound that has excellent pest control activity, particularly insecticidal and/or acaricidal activity, is excellent in safety, and can be industrially advantageously synthesized. 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 extermination agent containing the above imidazolylazole compound as an active ingredient.
上記課題を解決すべく鋭意検討した結果、以下の形態を包含する本発明を完成するに至った。
〔1〕 式(I)で表される化合物またはその塩。
〔式(I)中、Aは、式(A1)で表される基、または式(A2)で表される基であり、
式(A1)および(A2)中、
*は、Bとの結合部位を示し、
R1は、置換もしくは無置換のC1~6アルキル基、置換もしくは無置換のC2~6アルケニル基、または置換若しくは無置換のフェニル基であり、
R2は、置換若しくは無置換のC1~6アルキル基であり、
R3は、水素原子、置換若しくは無置換のC1~6アルキル基、アミノ基、シアノ基、またはハロゲノ基であり、
式(I)中、Bは、式(B1)で表される基、または式(B2)で表される基であり、
式(B1)および(B2)中、
*は、Aとの結合部位を示し、
R4は、水素原子、置換若しくは無置換のC1~6アルキル基、置換若しくは無置換のC2~6アルケニル基、置換若しくは無置換のC2~6アルキニル基、置換若しくは無置換のC1~6アルキルカルボニル基、置換若しくは無置換のC1~6アルコキシカルボニル基、置換若しくは無置換のC3~6シクロアルキル基、置換若しくは無置換のフェニル基、置換若しくは無置換のナフチル基、置換若しくは無置換の5~10員ヘテロシクリル基、置換若しくは無置換のアミノ基、置換若しくは無置換のアミノカルボニル基、-C(=N-ORa)Rbで表される基、ニトロ基、シアノ基、またはハロゲノ基であり、
Raは、水素原子、または置換若しくは無置換のC1~6アルキル基であり、
Rbは、水素原子、または置換若しくは無置換のC1~6アルキル基であり、
R5は、置換若しくは無置換のC1~6アルキル基または置換若しくは無置換のC3~6シクロアルキル基であり、
nは、Oの数を表し、0、1または2である。〕 As a result of intensive studies to solve the above problems, we have completed the present invention, which includes the following embodiments.
[1] A compound represented by formula (I) or a salt thereof.
[In formula (I), A is a group represented by formula (A1) or a group represented by formula (A2),
In formulas (A1) and (A2),
* indicates the binding site with B,
R 1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted phenyl group,
R 2 is a substituted or unsubstituted C1-6 alkyl group,
R 3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, an amino group, a cyano group, or a halogeno group,
In formula (I), B is a group represented by formula (B1) or a group represented by formula (B2),
In formulas (B1) and (B2),
* indicates the binding site with A,
R 4 is a hydrogen atom, 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 substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted C1-6 alkoxycarbonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted 5-10 A membered heterocyclyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a group represented by -C(=N-OR a )R b , a nitro group, a cyano group, or a halogeno group,
R a is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group,
R b is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group,
R 5 is a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group,
n represents the number of O's and is 0, 1 or 2. ]
〔1〕 式(I)で表される化合物またはその塩。
*は、Bとの結合部位を示し、
R1は、置換もしくは無置換のC1~6アルキル基、置換もしくは無置換のC2~6アルケニル基、または置換若しくは無置換のフェニル基であり、
R2は、置換若しくは無置換のC1~6アルキル基であり、
R3は、水素原子、置換若しくは無置換のC1~6アルキル基、アミノ基、シアノ基、またはハロゲノ基であり、
式(I)中、Bは、式(B1)で表される基、または式(B2)で表される基であり、
*は、Aとの結合部位を示し、
R4は、水素原子、置換若しくは無置換のC1~6アルキル基、置換若しくは無置換のC2~6アルケニル基、置換若しくは無置換のC2~6アルキニル基、置換若しくは無置換のC1~6アルキルカルボニル基、置換若しくは無置換のC1~6アルコキシカルボニル基、置換若しくは無置換のC3~6シクロアルキル基、置換若しくは無置換のフェニル基、置換若しくは無置換のナフチル基、置換若しくは無置換の5~10員ヘテロシクリル基、置換若しくは無置換のアミノ基、置換若しくは無置換のアミノカルボニル基、-C(=N-ORa)Rbで表される基、ニトロ基、シアノ基、またはハロゲノ基であり、
Raは、水素原子、または置換若しくは無置換のC1~6アルキル基であり、
Rbは、水素原子、または置換若しくは無置換のC1~6アルキル基であり、
R5は、置換若しくは無置換のC1~6アルキル基または置換若しくは無置換のC3~6シクロアルキル基であり、
nは、Oの数を表し、0、1または2である。〕 As a result of intensive studies to solve the above problems, we have completed the present invention, which includes the following embodiments.
[1] A compound represented by formula (I) or a salt thereof.
* indicates the binding site with B,
R 1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted phenyl group,
R 2 is a substituted or unsubstituted C1-6 alkyl group,
R 3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, an amino group, a cyano group, or a halogeno group,
In formula (I), B is a group represented by formula (B1) or a group represented by formula (B2),
* indicates the binding site with A,
R 4 is a hydrogen atom, 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 substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted C1-6 alkoxycarbonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted 5-10 A membered heterocyclyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a group represented by -C(=N-OR a )R b , a nitro group, a cyano group, or a halogeno group,
R a is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group,
R b is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group,
R 5 is a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group,
n represents the number of O's and is 0, 1 or 2. ]
〔2〕 前記〔1〕に記載の化合物およびその塩からなる群から選ばれる少なくとも1つを有効成分として含有する有害生物防除剤。
〔3〕 前記〔1〕に記載の化合物およびその塩からなる群から選ばれる少なくとも1つを有効成分として含有する殺虫若しくは殺ダニ剤。
〔4〕 前記〔1〕に記載の化合物およびその塩からなる群から選ばれる少なくとも1つを有効成分として含有する外部寄生虫防除剤。
〔5〕 前記〔1〕に記載の化合物およびその塩からなる群から選ばれる少なくとも1つを有効成分として含有する内部寄生虫防除若しくは駆除剤。 [2] A pest control agent containing as an active ingredient at least one selected from the group consisting of the compound described in [1] above and its salt.
[3] An insecticide or acaricide containing as an active ingredient at least one selected from the group consisting of the compounds described in [1] above and salts thereof.
[4] An ectoparasite control agent containing as an active ingredient at least one selected from the group consisting of the compounds described in [1] above and salts thereof.
[5] An endoparasite control or extermination agent containing as an active ingredient at least one selected from the group consisting of the compound described in [1] above and its salt.
〔3〕 前記〔1〕に記載の化合物およびその塩からなる群から選ばれる少なくとも1つを有効成分として含有する殺虫若しくは殺ダニ剤。
〔4〕 前記〔1〕に記載の化合物およびその塩からなる群から選ばれる少なくとも1つを有効成分として含有する外部寄生虫防除剤。
〔5〕 前記〔1〕に記載の化合物およびその塩からなる群から選ばれる少なくとも1つを有効成分として含有する内部寄生虫防除若しくは駆除剤。 [2] A pest control agent containing as an active ingredient at least one selected from the group consisting of the compound described in [1] above and its salt.
[3] An insecticide or acaricide containing as an active ingredient at least one selected from the group consisting of the compounds described in [1] above and salts thereof.
[4] An ectoparasite control agent containing as an active ingredient at least one selected from the group consisting of the compounds described in [1] above and salts thereof.
[5] An endoparasite control or extermination agent containing as an active ingredient at least one selected from the group consisting of the compound described in [1] above and its salt.
本発明のイミダゾリルアゾール化合物(式(I)で表される化合物またはその塩)は、農作物や衛生面で問題となる有害生物を防除することができる。本発明のイミダゾリルアゾール化合物は、特に農業害虫およびダニ類をより低濃度で効果的に防除することができる。本発明のイミダゾリルアゾール化合物は、さらに、人畜を害する外部寄生虫および内部寄生虫を効果的に防除することができる。
The imidazolylazole compound (compound represented by formula (I) or a salt thereof) of the present invention can control pests that cause problems in agricultural crops and hygiene. The imidazolylazole compound of the present invention can effectively control agricultural pests and mites, especially at lower concentrations. The imidazolylazole compound of the present invention can further effectively control ectoparasites and endoparasites that harm humans and livestock.
本発明のイミダゾリルアゾール化合物は、式(I)で表される化合物(以下、化合物(I)と表記することがある。)または化合物(I)の塩である。言い換えれば、本発明のイミダゾリルアゾール化合物は、式(I-1)で表される化合物(以下、化合物(I-1)と表記することがある。)、化合物(I-1)の塩、式(I-2)で表される化合物(以下、化合物(I-2)と表記することがある。)、化合物(I-2)の塩、式(I-3)で表される化合物(以下、化合物(I-3)と表記することがある。)、化合物(I-3)の塩、式(I-4)で表される化合物(以下、化合物(I-4)と表記することがある。)または化合物(I-4)の塩である。
本発明のイミダゾリルアゾール化合物は、化合物(I-1)、化合物(I-1)の塩、化合物(I-2)または化合物(I-2)の塩であることが好ましく、化合物(I-1)または化合物(I-1)の塩であることがより好ましい。 The imidazolylazole compound of the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) or a salt of compound (I). In other words, the imidazolylazole compound of the present invention includes a compound represented by formula (I-1) (hereinafter sometimes referred to as compound (I-1)), a salt of compound (I-1), and a compound represented by formula (I-1). The compound represented by (I-2) (hereinafter sometimes referred to as compound (I-2)), the salt of compound (I-2), the compound represented by formula (I-3) (hereinafter referred to as compound (I-2)) , may be written as compound (I-3)), salt of compound (I-3), compound represented by formula (I-4) (hereinafter may be written as compound (I-4)) ) or a salt of compound (I-4).
The imidazolylazole compound of the present invention is preferably Compound (I-1), a salt of Compound (I-1), Compound (I-2) or a salt of Compound (I-2); ) or a salt of compound (I-1) is more preferable.
本発明のイミダゾリルアゾール化合物は、化合物(I-1)、化合物(I-1)の塩、化合物(I-2)または化合物(I-2)の塩であることが好ましく、化合物(I-1)または化合物(I-1)の塩であることがより好ましい。 The imidazolylazole compound of the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) or a salt of compound (I). In other words, the imidazolylazole compound of the present invention includes a compound represented by formula (I-1) (hereinafter sometimes referred to as compound (I-1)), a salt of compound (I-1), and a compound represented by formula (I-1). The compound represented by (I-2) (hereinafter sometimes referred to as compound (I-2)), the salt of compound (I-2), the compound represented by formula (I-3) (hereinafter referred to as compound (I-2)) , may be written as compound (I-3)), salt of compound (I-3), compound represented by formula (I-4) (hereinafter may be written as compound (I-4)) ) or a salt of compound (I-4).
The imidazolylazole compound of the present invention is preferably Compound (I-1), a salt of Compound (I-1), Compound (I-2) or a salt of Compound (I-2); ) or a salt of compound (I-1) is more preferable.
本発明において、「無置換(unsubstituted)」の用語は、母核となる基のみであることを意味する。「置換」との記載がなく母核となる基の名称のみで記載しているときは、別段の断りがない限り「無置換」の意味である。
一方、「置換(substituted)」の用語は、母核となる基のいずれかの水素原子が、母核と同一または異なる構造の基(置換基)で置換されていることを意味する。従って、「置換基」は、母核となる基に結合した他の基である。置換基は1つであってもよいし、2つ以上であってもよい。2つ以上の置換基は同一であってもよいし、異なっていてもよい。
「C1~6」などの用語は、母核となる基の炭素原子数が1~6個などであることを表している。この炭素原子数には、置換基の中に在る炭素原子の数を含まない。例えば、置換基としてエトキシ基を有するブチル基は、C2アルコキシC4アルキル基に分類する。
「置換基」は化学的に許容され、本発明の効果を有する限りにおいて特に制限されない。 In the present invention, the term "unsubstituted" means only the core group. When "substituted" is not mentioned and only the name of the core group is listed, it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that any hydrogen atom of a group serving as a core is substituted with a group (substituent) having the same or different structure from the core. Therefore, a "substituent" is another group bonded to the core group. The number of substituents may be one, or two or more. Two or more substituents may be the same or different.
A term such as "C1-6" indicates that the number of carbon atoms in the group serving as a core is 1 to 6. This number of carbon atoms does not include the number of carbon atoms present in substituents. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.
The "substituent" is not particularly limited as long as it is chemically permissible and has the effects of the present invention.
一方、「置換(substituted)」の用語は、母核となる基のいずれかの水素原子が、母核と同一または異なる構造の基(置換基)で置換されていることを意味する。従って、「置換基」は、母核となる基に結合した他の基である。置換基は1つであってもよいし、2つ以上であってもよい。2つ以上の置換基は同一であってもよいし、異なっていてもよい。
「C1~6」などの用語は、母核となる基の炭素原子数が1~6個などであることを表している。この炭素原子数には、置換基の中に在る炭素原子の数を含まない。例えば、置換基としてエトキシ基を有するブチル基は、C2アルコキシC4アルキル基に分類する。
「置換基」は化学的に許容され、本発明の効果を有する限りにおいて特に制限されない。 In the present invention, the term "unsubstituted" means only the core group. When "substituted" is not mentioned and only the name of the core group is listed, it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that any hydrogen atom of a group serving as a core is substituted with a group (substituent) having the same or different structure from the core. Therefore, a "substituent" is another group bonded to the core group. The number of substituents may be one, or two or more. Two or more substituents may be the same or different.
A term such as "C1-6" indicates that the number of carbon atoms in the group serving as a core is 1 to 6. This number of carbon atoms does not include the number of carbon atoms present in substituents. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.
The "substituent" is not particularly limited as long as it is chemically permissible and has the effects of the present invention.
以下に「置換基」となり得る基を例示する。
メチル基、エチル基、n-プロピル基、i-プロピル基、n-ブチル基、s-ブチル基、i-ブチル基、t-ブチル基、n-ペンチル基、n-ヘキシル基などのC1~6アルキル基;
ビニル基、1-プロペニル基、2-プロペニル基(アリル基)、1-ブテニル基、2-ブテニル基、3-ブテニル基、1-メチル-2-プロペニル基、2-メチル-2-プロペニル基などのC2~6アルケニル基;
エチニル基、1-プロピニル基、2-プロピニル基、1-ブチニル基、2-ブチニル基、3-ブチニル基、1-メチル-2-プロピニル基などのC2~6アルキニル基; Examples of groups that can be "substituents" are shown 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 group;
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;
メチル基、エチル基、n-プロピル基、i-プロピル基、n-ブチル基、s-ブチル基、i-ブチル基、t-ブチル基、n-ペンチル基、n-ヘキシル基などのC1~6アルキル基;
ビニル基、1-プロペニル基、2-プロペニル基(アリル基)、1-ブテニル基、2-ブテニル基、3-ブテニル基、1-メチル-2-プロペニル基、2-メチル-2-プロペニル基などのC2~6アルケニル基;
エチニル基、1-プロピニル基、2-プロピニル基、1-ブチニル基、2-ブチニル基、3-ブチニル基、1-メチル-2-プロピニル基などのC2~6アルキニル基; Examples of groups that can be "substituents" are shown 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 group;
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;
シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などのC3~6シクロアルキル基;
フェニル基、ナフチル基;
ベンジル基、フェネチル基などのフェニルC1~6アルキル基;
3~6員ヘテロシクリル基;
3~6員へテロシクリルC1~6アルキル基; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group;
Phenyl group, naphthyl group;
Phenyl C1-6 alkyl groups such as benzyl group and phenethyl group;
3-6 membered heterocyclyl group;
3-6 membered heterocyclyl C1-6 alkyl group;
フェニル基、ナフチル基;
ベンジル基、フェネチル基などのフェニルC1~6アルキル基;
3~6員ヘテロシクリル基;
3~6員へテロシクリルC1~6アルキル基; C3-6 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group;
Phenyl group, naphthyl group;
Phenyl C1-6 alkyl groups such as benzyl group and phenethyl group;
3-6 membered heterocyclyl group;
3-6 membered heterocyclyl C1-6 alkyl group;
水酸基;
メトキシ基、エトキシ基、n-プロポキシ基、i-プロポキシ基、n-ブトキシ基、s-ブトキシ基、i-ブトキシ基、t-ブトキシ基などのC1~6アルコキシ基;
ビニルオキシ基、アリルオキシ基、プロペニルオキシ基、ブテニルオキシ基などのC2~6アルケニルオキシ基;
エチニルオキシ基、プロパルギルオキシ基などのC2~6アルキニルオキシ基;
フェノキシ基、ナフトキシ基;
ベンジルオキシ基、フェネチルオキシ基などのフェニルC1~6アルコキシ基;
チアゾリルオキシ基、ピリジルオキシ基などの5~6員ヘテロアリールオキシ基;
チアゾリルメチルオキシ基、ピリジルメチルオキシ基などの5~6員ヘテロアリールC1~6アルキルオキシ基; Hydroxyl 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 group and pyridyloxy group;
5- to 6-membered heteroaryl C1-6 alkyloxy group such as thiazolylmethyloxy group and pyridylmethyloxy group;
メトキシ基、エトキシ基、n-プロポキシ基、i-プロポキシ基、n-ブトキシ基、s-ブトキシ基、i-ブトキシ基、t-ブトキシ基などのC1~6アルコキシ基;
ビニルオキシ基、アリルオキシ基、プロペニルオキシ基、ブテニルオキシ基などのC2~6アルケニルオキシ基;
エチニルオキシ基、プロパルギルオキシ基などのC2~6アルキニルオキシ基;
フェノキシ基、ナフトキシ基;
ベンジルオキシ基、フェネチルオキシ基などのフェニルC1~6アルコキシ基;
チアゾリルオキシ基、ピリジルオキシ基などの5~6員ヘテロアリールオキシ基;
チアゾリルメチルオキシ基、ピリジルメチルオキシ基などの5~6員ヘテロアリールC1~6アルキルオキシ基; Hydroxyl 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 group and pyridyloxy group;
5- to 6-membered heteroaryl C1-6 alkyloxy group such as thiazolylmethyloxy group and pyridylmethyloxy group;
ホルミル基;
アセチル基、プロピオニル基などのC1~6アルキルカルボニル基;
ホルミルオキシ基;
アセチルオキシ基、プロピオニルオキシ基などのC1~6アルキルカルボニルオキシ基;
ベンゾイル基;
メトキシカルボニル基、エトキシカルボニル基、n-プロポキシカルボニル基、i-プロポキシカルボニル基、n-ブトキシカルボニル基、t-ブトキシカルボニル基などのC1~6アルコキシカルボニル基;
メトキシカルボニルオキシ基、エトキシカルボニルオキシ基、n-プロポキシカルボニルオキシ基、i-プロポキシカルボニルオキシ基、n-ブトキシカルボニルオキシ基、t-ブトキシカルボニルオキシ基などのC1~6アルコキシカルボニルオキシ基;
カルボキシル基; Formyl group;
C1-6 alkylcarbonyl groups such as acetyl group and propionyl group;
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;
アセチル基、プロピオニル基などのC1~6アルキルカルボニル基;
ホルミルオキシ基;
アセチルオキシ基、プロピオニルオキシ基などのC1~6アルキルカルボニルオキシ基;
ベンゾイル基;
メトキシカルボニル基、エトキシカルボニル基、n-プロポキシカルボニル基、i-プロポキシカルボニル基、n-ブトキシカルボニル基、t-ブトキシカルボニル基などのC1~6アルコキシカルボニル基;
メトキシカルボニルオキシ基、エトキシカルボニルオキシ基、n-プロポキシカルボニルオキシ基、i-プロポキシカルボニルオキシ基、n-ブトキシカルボニルオキシ基、t-ブトキシカルボニルオキシ基などのC1~6アルコキシカルボニルオキシ基;
カルボキシル基; Formyl group;
C1-6 alkylcarbonyl groups such as acetyl group and propionyl group;
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;
フルオロ基、クロロ基、ブロモ基、イオド基などのハロゲノ基;
クロロメチル基、クロロエチル基、トリフルオロメチル基、1,2-ジクロロ-n-プロピル基、1-フルオロ-n-ブチル基、パーフルオロ-n-ペンチル基などのC1~6ハロアルキル基;
2-クロロ-1-プロペニル基、2-フルオロ-1-ブテニル基などのC2~6ハロアルケニル基;
4,4-ジクロロ-1-ブチニル基、4-フルオロ-1-ペンチニル基、5-ブロモ-2-ペンチニル基などのC2~6ハロアルキニル基;
トリフルオロメトキシ基、2-クロロ-n-プロポキシ基、2,3-ジクロロブトキシ基などのC1~6ハロアルコキシ基;
2-クロロプロペニルオキシ基、3-ブロモブテニルオキシ基などのC2~6ハロアルケニルオキシ基;
クロロアセチル基、トリフルオロアセチル基、トリクロロアセチル基などのC1~6ハロアルキルカルボニル基; Halogeno groups such as fluoro group, chloro group, bromo group, iodo 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;
C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 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 and 3-bromobutenyloxy group;
C1-6 haloalkylcarbonyl groups such as chloroacetyl group, trifluoroacetyl group, trichloroacetyl group;
クロロメチル基、クロロエチル基、トリフルオロメチル基、1,2-ジクロロ-n-プロピル基、1-フルオロ-n-ブチル基、パーフルオロ-n-ペンチル基などのC1~6ハロアルキル基;
2-クロロ-1-プロペニル基、2-フルオロ-1-ブテニル基などのC2~6ハロアルケニル基;
4,4-ジクロロ-1-ブチニル基、4-フルオロ-1-ペンチニル基、5-ブロモ-2-ペンチニル基などのC2~6ハロアルキニル基;
トリフルオロメトキシ基、2-クロロ-n-プロポキシ基、2,3-ジクロロブトキシ基などのC1~6ハロアルコキシ基;
2-クロロプロペニルオキシ基、3-ブロモブテニルオキシ基などのC2~6ハロアルケニルオキシ基;
クロロアセチル基、トリフルオロアセチル基、トリクロロアセチル基などのC1~6ハロアルキルカルボニル基; Halogeno groups such as fluoro group, chloro group, bromo group, iodo 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;
C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 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 and 3-bromobutenyloxy group;
C1-6 haloalkylcarbonyl groups such as chloroacetyl group, trifluoroacetyl group, trichloroacetyl group;
アミノ基;
メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基などのC1~6アルキル置換アミノ基;
アニリノ基、ナフチルアミノ基;
ベンジルアミノ基、フェネチルアミノ基などのフェニルC1~6アルキルアミノ基;
ホルミルアミノ基;
アセチルアミノ基、プロパノイルアミノ基、ブチリルアミノ基、i-プロピルカルボニルアミノ基などのC1~6アルキルカルボニルアミノ基;
メトキシカルボニルアミノ基、エトキシカルボニルアミノ基、n-プロポキシカルボニルアミノ基、i-プロポキシカルボニルアミノ基などのC1~6アルコキシカルボニルアミノ基;
アミノカルボニル基、ジメチルアミノカルボニル基、フェニルアミノカルボニル基、N-フェニル-N-メチルアミノカルボニル基などの無置換若しくは置換基を有するアミノカルボニル基;
イミノメチル基、(1-イミノ)エチル基、(1-イミノ)-n-プロピル基などのイミノC1~6アルキル基;
N-ヒドロキシ-イミノメチル基、(1-(N-ヒドロキシ)-イミノ)エチル基、(1-(N-ヒドロキシ)-イミノ)プロピル基、N-メトキシ-イミノメチル基、(1-(N-メトキシ)-イミノ)エチル基などの置換若しくは無置換のN-ヒドロキシイミノC1~6アルキル基;
アミノカルボニルオキシ基;
エチルアミノカルボニルオキシ基、ジメチルアミノカルボニルオキシ基などのC1~6アルキル置換アミノカルボニルオキシ基; Amino group;
C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group, diethylamino group;
Anilino group, naphthylamino group;
Phenyl C1-6 alkylamino groups such as benzylamino group and 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;
unsubstituted or substituted aminocarbonyl groups such as aminocarbonyl group, dimethylaminocarbonyl group, phenylaminocarbonyl group, N-phenyl-N-methylaminocarbonyl group;
Imino C1-6 alkyl groups such as iminomethyl group, (1-imino)ethyl group, (1-imino)-n-propyl group;
N-hydroxy-iminomethyl group, (1-(N-hydroxy)-imino)ethyl group, (1-(N-hydroxy)-imino)propyl group, N-methoxy-iminomethyl group, (1-(N-methoxy) - Substituted or unsubstituted N-hydroxyimino C1-6 alkyl group such as imino)ethyl group;
Aminocarbonyloxy group;
C1-6 alkyl-substituted aminocarbonyloxy groups such as ethylaminocarbonyloxy groups and dimethylaminocarbonyloxy groups;
メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基などのC1~6アルキル置換アミノ基;
アニリノ基、ナフチルアミノ基;
ベンジルアミノ基、フェネチルアミノ基などのフェニルC1~6アルキルアミノ基;
ホルミルアミノ基;
アセチルアミノ基、プロパノイルアミノ基、ブチリルアミノ基、i-プロピルカルボニルアミノ基などのC1~6アルキルカルボニルアミノ基;
メトキシカルボニルアミノ基、エトキシカルボニルアミノ基、n-プロポキシカルボニルアミノ基、i-プロポキシカルボニルアミノ基などのC1~6アルコキシカルボニルアミノ基;
アミノカルボニル基、ジメチルアミノカルボニル基、フェニルアミノカルボニル基、N-フェニル-N-メチルアミノカルボニル基などの無置換若しくは置換基を有するアミノカルボニル基;
イミノメチル基、(1-イミノ)エチル基、(1-イミノ)-n-プロピル基などのイミノC1~6アルキル基;
N-ヒドロキシ-イミノメチル基、(1-(N-ヒドロキシ)-イミノ)エチル基、(1-(N-ヒドロキシ)-イミノ)プロピル基、N-メトキシ-イミノメチル基、(1-(N-メトキシ)-イミノ)エチル基などの置換若しくは無置換のN-ヒドロキシイミノC1~6アルキル基;
アミノカルボニルオキシ基;
エチルアミノカルボニルオキシ基、ジメチルアミノカルボニルオキシ基などのC1~6アルキル置換アミノカルボニルオキシ基; Amino group;
C1-6 alkyl-substituted amino groups such as methylamino group, dimethylamino group, diethylamino group;
Anilino group, naphthylamino group;
Phenyl C1-6 alkylamino groups such as benzylamino group and 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;
unsubstituted or substituted aminocarbonyl groups such as aminocarbonyl group, dimethylaminocarbonyl group, phenylaminocarbonyl group, N-phenyl-N-methylaminocarbonyl group;
Imino C1-6 alkyl groups such as iminomethyl group, (1-imino)ethyl group, (1-imino)-n-propyl group;
N-hydroxy-iminomethyl group, (1-(N-hydroxy)-imino)ethyl group, (1-(N-hydroxy)-imino)propyl group, N-methoxy-iminomethyl group, (1-(N-methoxy) - Substituted or unsubstituted N-hydroxyimino C1-6 alkyl group such as imino)ethyl group;
Aminocarbonyloxy group;
C1-6 alkyl-substituted aminocarbonyloxy groups such as ethylaminocarbonyloxy groups and dimethylaminocarbonyloxy groups;
メルカプト基;
メチルチオ基、エチルチオ基、n-プロピルチオ基、i-プロピルチオ基、n-ブチルチオ基、i-ブチルチオ基、s-ブチルチオ基、t-ブチルチオ基などのC1~6アルキルチオ基;
トリフルオロメチルチオ基、2,2,2-トリフルオロエチルチオ基などのC1~6ハロアルキルチオ基;
フェニルチオ基、ナフチルチオ基;
チアゾリルチオ基、ピリジルチオ基などの5~6員ヘテロアリールチオ基; Mercapto group;
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 and 2,2,2-trifluoroethylthio group;
Phenylthio group, naphthylthio group;
5- to 6-membered heteroarylthio groups such as thiazolylthio group and pyridylthio group;
メチルチオ基、エチルチオ基、n-プロピルチオ基、i-プロピルチオ基、n-ブチルチオ基、i-ブチルチオ基、s-ブチルチオ基、t-ブチルチオ基などのC1~6アルキルチオ基;
トリフルオロメチルチオ基、2,2,2-トリフルオロエチルチオ基などのC1~6ハロアルキルチオ基;
フェニルチオ基、ナフチルチオ基;
チアゾリルチオ基、ピリジルチオ基などの5~6員ヘテロアリールチオ基; Mercapto group;
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 and 2,2,2-trifluoroethylthio group;
Phenylthio group, naphthylthio group;
5- to 6-membered heteroarylthio groups such as thiazolylthio group and pyridylthio group;
メチルスルフィニル基、エチルスルフィニル基、t-ブチルスルフィニル基などのC1~6アルキルスルフィニル基;
トリフルオロメチルスルフィニル基、2,2,2-トリフルオロエチルスルフィニル基などのC1~6ハロアルキルスルフィニル基;
フェニルスルフィニル基;
チアゾリルスルフィニル基、ピリジルスルフィニル基などの5~6員ヘテロアリールスルフィニル基; C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group;
C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group;
Phenylsulfinyl group;
5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl groups and pyridylsulfinyl groups;
トリフルオロメチルスルフィニル基、2,2,2-トリフルオロエチルスルフィニル基などのC1~6ハロアルキルスルフィニル基;
フェニルスルフィニル基;
チアゾリルスルフィニル基、ピリジルスルフィニル基などの5~6員ヘテロアリールスルフィニル基; C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group;
C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group;
Phenylsulfinyl group;
5- to 6-membered heteroarylsulfinyl groups such as thiazolylsulfinyl groups and pyridylsulfinyl groups;
メチルスルホニル基、エチルスルホニル基、t-ブチルスルホニル基などのC1~6アルキルスルホニル基;
トリフルオロメチルスルホニル基、2,2,2-トリフルオロエチルスルホニル基などのC1~6ハロアルキルスルホニル基;
フェニルスルホニル基;
チアゾリルスルホニル基、ピリジルスルホニル基などの5~6員ヘテロアリールスルホニル基;
メチルスルホニルオキシ基、エチルスルホニルオキシ基、t-ブチルスルホニルオキシ基などのC1~6アルキルスルホニルオキシ基;
トリフルオロメチルスルホニルオキシ基、2,2,2-トリフルオロエチルスルホニルオキシ基などのC1~6ハロアルキルスルホニルオキシ基; C1-6 alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group;
C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group;
phenylsulfonyl group;
5- to 6-membered heteroarylsulfonyl groups such as thiazolylsulfonyl group and pyridylsulfonyl group;
C1-6 alkylsulfonyloxy groups such as methylsulfonyloxy group, ethylsulfonyloxy group, t-butylsulfonyloxy group;
C1-6 haloalkylsulfonyloxy groups such as trifluoromethylsulfonyloxy group and 2,2,2-trifluoroethylsulfonyloxy group;
トリフルオロメチルスルホニル基、2,2,2-トリフルオロエチルスルホニル基などのC1~6ハロアルキルスルホニル基;
フェニルスルホニル基;
チアゾリルスルホニル基、ピリジルスルホニル基などの5~6員ヘテロアリールスルホニル基;
メチルスルホニルオキシ基、エチルスルホニルオキシ基、t-ブチルスルホニルオキシ基などのC1~6アルキルスルホニルオキシ基;
トリフルオロメチルスルホニルオキシ基、2,2,2-トリフルオロエチルスルホニルオキシ基などのC1~6ハロアルキルスルホニルオキシ基; C1-6 alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group;
C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl group and 2,2,2-trifluoroethylsulfonyl group;
phenylsulfonyl group;
5- to 6-membered heteroarylsulfonyl groups such as thiazolylsulfonyl group and pyridylsulfonyl group;
C1-6 alkylsulfonyloxy groups such as methylsulfonyloxy group, ethylsulfonyloxy group, t-butylsulfonyloxy group;
C1-6 haloalkylsulfonyloxy groups such as trifluoromethylsulfonyloxy group and 2,2,2-trifluoroethylsulfonyloxy group;
トリメチルシリル基、トリエチルシリル基、t-ブチルジメチルシリル基などのトリC1~6アルキル置換シリル基;
トリフェニルシリル基;
シアノ基;ニトロ基。 TriC1-6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
triphenylsilyl group;
Cyano group; Nitro group.
トリフェニルシリル基;
シアノ基;ニトロ基。 TriC1-6 alkyl-substituted silyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
triphenylsilyl group;
Cyano group; Nitro group.
また、これらの「置換基」は、前記置換基中のいずれかの水素原子が、異なる構造の基で置換されていてもよい。その場合の「置換基」としては、C1~6アルキル基、C1~6ハロアルキル基、C1~6アルコキシ基、C1~6ハロアルコキシ基、ハロゲノ基、シアノ基、ニトロ基などを挙げることができる。
Furthermore, in these "substituents", any hydrogen atom in the substituents may be substituted with a group having a different structure. Examples of the "substituent" in this case include a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, a nitro group, and the like.
また、上記の「3~6員ヘテロシクリル基」は、窒素原子、酸素原子および硫黄原子からなる群から選ばれる1~4個のヘテロ原子を環の構成原子として含む。ヘテロシクリル基は、単環および多環のいずれであってもよい。多環ヘテロシクリル基は、少なくとも一つの環がヘテロ環であれば、残りの環が飽和脂環、不飽和脂環または芳香環のいずれであってもよい。「3~6員ヘテロシクリル基」としては、3~6員飽和ヘテロシクリル基、5~6員ヘテロアリール基、5~6員部分不飽和ヘテロシクリル基などを挙げることができる。
Furthermore, the above-mentioned "3- to 6-membered heterocyclyl group" contains 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms, and sulfur atoms as ring constituent atoms. The heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, as long as at least one ring is a heterocycle, the remaining rings may be any of a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the "3- to 6-membered heterocyclyl group" include 3- to 6-membered saturated heterocyclyl groups, 5- to 6-membered heteroaryl groups, and 5- to 6-membered partially unsaturated heterocyclyl groups.
「3~6員飽和ヘテロシクリル基」としては、アジリジニル基、エポキシ基、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。
Examples of the "3- to 6-membered saturated heterocyclyl group" include aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group, etc.
「5員ヘテロアリール基」としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などを挙げることができる。
「6員ヘテロアリール基」としては、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などを挙げることができる。
「5~6員部分不飽和へテロシクリル基」としては、ピロリニル基、ジヒドロフラニル基、ジヒドロチオフェニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基、チアゾリニル基、イソチアゾリニル基などの5員部分不飽和ヘテロシクリル基;ジヒドロピラニル基などの6員部分不飽和へテロシクリル基を挙げることができる。 Examples of the "5-membered heteroaryl group" 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. can be mentioned.
Examples of the "6-membered heteroaryl group" include a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, and triazinyl group.
Examples of "5- to 6-membered partially unsaturated heterocyclyl group" include pyrrolinyl group, dihydrofuranyl group, dihydrothiophenyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group, thiazolinyl group, isothiazolinyl group, etc. A 5-membered partially unsaturated heterocyclyl group; a 6-membered partially unsaturated heterocyclyl group such as a dihydropyranyl group can be mentioned.
「6員ヘテロアリール基」としては、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などを挙げることができる。
「5~6員部分不飽和へテロシクリル基」としては、ピロリニル基、ジヒドロフラニル基、ジヒドロチオフェニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基、チアゾリニル基、イソチアゾリニル基などの5員部分不飽和ヘテロシクリル基;ジヒドロピラニル基などの6員部分不飽和へテロシクリル基を挙げることができる。 Examples of the "5-membered heteroaryl group" 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. can be mentioned.
Examples of the "6-membered heteroaryl group" include a pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, and triazinyl group.
Examples of "5- to 6-membered partially unsaturated heterocyclyl group" include pyrrolinyl group, dihydrofuranyl group, dihydrothiophenyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, isoxazolinyl group, thiazolinyl group, isothiazolinyl group, etc. A 5-membered partially unsaturated heterocyclyl group; a 6-membered partially unsaturated heterocyclyl group such as a dihydropyranyl group can be mentioned.
式(I-1)、(I-2)、(I-3)および(I-4)中のR1は、置換もしくは無置換のC1~6アルキル基、置換もしくは無置換のC2~6アルケニル基、または置換若しくは無置換のフェニル基である。
R1は、置換もしくは無置換のC2~6アルケニル基、または置換若しくは無置換のフェニル基であることが好ましく、置換若しくは無置換のフェニル基であることがより好ましい。 R 1 in formulas (I-1), (I-2), (I-3) and (I-4) is substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted phenyl group.
R 1 is preferably a substituted or unsubstituted C2-6 alkenyl group or a substituted or unsubstituted phenyl group, more preferably a substituted or unsubstituted phenyl group.
R1は、置換もしくは無置換のC2~6アルケニル基、または置換若しくは無置換のフェニル基であることが好ましく、置換若しくは無置換のフェニル基であることがより好ましい。 R 1 in formulas (I-1), (I-2), (I-3) and (I-4) is substituted or unsubstituted C1-6 alkyl group, substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted phenyl group.
R 1 is preferably a substituted or unsubstituted C2-6 alkenyl group or a substituted or unsubstituted phenyl group, more preferably a substituted or unsubstituted phenyl group.
R1における「C1~6アルキル基」は、直鎖であってもよいし、分岐鎖であってもよい。
「C1~6アルキル基」としては、メチル基、エチル基、n-プロピル基、n-ブチル基、n-ペンチル基、n-ヘキシル基、i-プロピル基、i-ブチル基、s-ブチル基、t-ブチル基、i-ペンチル基、ネオペンチル基、2-メチルブチル基、i-ヘキシル基などを挙げることができる。 The "C1-6 alkyl group" in R 1 may be linear or branched.
Examples of "C1-6 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. , t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group, etc.
「C1~6アルキル基」としては、メチル基、エチル基、n-プロピル基、n-ブチル基、n-ペンチル基、n-ヘキシル基、i-プロピル基、i-ブチル基、s-ブチル基、t-ブチル基、i-ペンチル基、ネオペンチル基、2-メチルブチル基、i-ヘキシル基などを挙げることができる。 The "C1-6 alkyl group" in R 1 may be linear or branched.
Examples of "C1-6 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. , t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, i-hexyl group, etc.
R1における「C2~6アルケニル基」としては、ビニル基、1-プロペニル基、2-プロペニル基、1-ブテニル基、2-ブテニル基、3-ブテニル基、1-メチル-2-プロペニル基、2-メチル-2-プロペニル基、1-ペンテニル基、2-ペンテニル基、3-ペンテニル基、4-ペンテニル基、1-メチル-2-ブテニル基、2-メチル-2-ブテニル基、1-ヘキセニル基、2-ヘキセニル基、3-ヘキセニル基、4-ヘキセニル基、5-ヘキセニル基などを挙げることができる。
Examples of the "C2-6 alkenyl group" in R 1 include 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, etc.
R1における「C1~6アルキル基」または「C2~6アルケニル基」上の置換基としては、
ハロゲノ基、水酸基、C1~6アルコキシ基、C1~6ハロアルコキシ基、C3~6シクロアルキル基、フェニル基、5員ヘテロアリール基、6員ヘテロアリール基、シアノ基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換されたフェニル基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された5員ヘテロアリール基;または
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された6員ヘテロアリール基が好ましい。 As the substituent on the "C1-6 alkyl group" or "C2-6 alkenyl group" in R 1 ,
Halogeno group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group;
A phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;
a 5-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a C1-6 A 6-membered heteroaryl group substituted with one or more substituents of a 6-alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred.
ハロゲノ基、水酸基、C1~6アルコキシ基、C1~6ハロアルコキシ基、C3~6シクロアルキル基、フェニル基、5員ヘテロアリール基、6員ヘテロアリール基、シアノ基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換されたフェニル基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された5員ヘテロアリール基;または
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された6員ヘテロアリール基が好ましい。 As the substituent on the "C1-6 alkyl group" or "C2-6 alkenyl group" in R 1 ,
Halogeno group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group;
A phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;
a 5-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a C1-6 A 6-membered heteroaryl group substituted with one or more substituents of a 6-alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred.
R1における「フェニル基」上の置換基としては、
ハロゲノ基、C1~6アルキル基、C1~6ハロアルキル基、水酸基、C1~6アルコキシ基、C1~6ハロアルコキシ基、C3~6シクロアルキル基、フェニル基、5員ヘテロアリール基、6員ヘテロアリール基、シアノ基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換されたフェニル基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された5員ヘテロアリール基;または
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された6員ヘテロアリール基が好ましい。
R1における「置換フェニル基」は、「フェニル基」上にひとつ以上の置換基を有し、複数の置換基は相互に結合して環を形成してもよく、その環は飽和脂環または不飽和脂環のいずれであってもよい。「置換フェニル基」として、例えば、インデニル基、インダニル基、テトラヒドロナフチル基、ジヒドロナフチル基、トリル基、キシリル基、メシチル基、ジュリル基などを含む。 As substituents on the “phenyl group” in R 1 ,
Halogeno group, C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group;
A phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;
a 5-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a C1-6 A 6-membered heteroaryl group substituted with one or more substituents of a 6-alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred.
The "substituted phenyl group" in R 1 has one or more substituents on the "phenyl group", and the plurality of substituents may be bonded to each other to form a ring, and the ring is a saturated alicyclic group or It may be any unsaturated alicyclic ring. Examples of the "substituted phenyl group" include an indenyl group, an indanyl group, a tetrahydronaphthyl group, a dihydronaphthyl group, a tolyl group, a xylyl group, a mesityl group, and a juryl group.
ハロゲノ基、C1~6アルキル基、C1~6ハロアルキル基、水酸基、C1~6アルコキシ基、C1~6ハロアルコキシ基、C3~6シクロアルキル基、フェニル基、5員ヘテロアリール基、6員ヘテロアリール基、シアノ基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換されたフェニル基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された5員ヘテロアリール基;または
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された6員ヘテロアリール基が好ましい。
R1における「置換フェニル基」は、「フェニル基」上にひとつ以上の置換基を有し、複数の置換基は相互に結合して環を形成してもよく、その環は飽和脂環または不飽和脂環のいずれであってもよい。「置換フェニル基」として、例えば、インデニル基、インダニル基、テトラヒドロナフチル基、ジヒドロナフチル基、トリル基、キシリル基、メシチル基、ジュリル基などを含む。 As substituents on the “phenyl group” in R 1 ,
Halogeno group, C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group;
A phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;
a 5-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a C1-6 A 6-membered heteroaryl group substituted with one or more substituents of a 6-alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred.
The "substituted phenyl group" in R 1 has one or more substituents on the "phenyl group", and the plurality of substituents may be bonded to each other to form a ring, and the ring is a saturated alicyclic group or It may be any unsaturated alicyclic ring. Examples of the "substituted phenyl group" include an indenyl group, an indanyl group, a tetrahydronaphthyl group, a dihydronaphthyl group, a tolyl group, a xylyl group, a mesityl group, and a juryl group.
式(I-1)および(I-2)中のR2は、置換若しくは無置換のC1~6アルキル基である。
R2における「置換若しくは無置換のC1~6アルキル基」としては、前記R1において例示したそれらと同じものを挙げることができる。 R 2 in formulas (I-1) and (I-2) is a substituted or unsubstituted C1-6 alkyl group.
Examples of the "substituted or unsubstituted C1-6 alkyl group" for R 2 include the same ones as exemplified for R 1 above.
R2における「置換若しくは無置換のC1~6アルキル基」としては、前記R1において例示したそれらと同じものを挙げることができる。 R 2 in formulas (I-1) and (I-2) is a substituted or unsubstituted C1-6 alkyl group.
Examples of the "substituted or unsubstituted C1-6 alkyl group" for R 2 include the same ones as exemplified for R 1 above.
式(I-3)および(I-4)中のR3は、水素原子、置換若しくは無置換のC1~6アルキル基、アミノ基(-NH3で表される基)、シアノ基、またはハロゲノ基である。
R 3 in formulas (I-3) and (I-4) is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, an amino group (a group represented by -NH 3 ), a cyano group, or a halogeno group. It is the basis.
R3における「置換若しくは無置換のC1~6アルキル基」としては、前記R1において例示したそれらと同じものを挙げることができる。
Examples of the "substituted or unsubstituted C1-6 alkyl group" for R 3 include the same ones as exemplified for R 1 above.
R3における「ハロゲノ基」としては、フルオロ基、クロロ基、ブロモ基、イオド基などを挙げることができる。
Examples of the "halogeno group" for R 3 include a fluoro group, a chloro group, a bromo group, an iodo group, and the like.
式(I-1)、(I-2)、(I-3)および(I-4)中のR4は、水素原子、置換若しくは無置換のC1~6アルキル基、置換若しくは無置換のC2~6アルケニル基、置換若しくは無置換のC2~6アルキニル基、置換若しくは無置換のC1~6アルキルカルボニル基、置換若しくは無置換のC1~6アルコキシカルボニル基、置換若しくは無置換のC3~6シクロアルキル基、置換若しくは無置換のフェニル基、置換若しくは無置換のナフチル基、置換若しくは無置換の5~10員ヘテロシクリル基、置換若しくは無置換のアミノ基、置換若しくは無置換のアミノカルボニル基、-C(=N-ORa)Rbで表される基、ニトロ基、シアノ基、またはハロゲノ基である。
R4は、水素原子、置換若しくは無置換のC1~6アルキル基、置換若しくは無置換のC1~6アルキルカルボニル基、置換若しくは無置換のC1~6アルコキシカルボニル基、置換若しくは無置換の5~10員ヘテロシクリル基、置換若しくは無置換のアミノ基、置換若しくは無置換のアミノカルボニル基、または-C(=N-ORa)Rbで表される基であることが好ましく、置換若しくは無置換の5~10員ヘテロシクリル基、または置換若しくは無置換のアミノカルボニル基であることがより好ましい。 R 4 in formulas (I-1), (I-2), (I-3) and (I-4) is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2 ~6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted C1-6 alkoxycarbonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted 5- to 10-membered heterocyclyl group, substituted or unsubstituted amino group, substituted or unsubstituted aminocarbonyl group, -C( =N-OR a ) A group represented by R b , a nitro group, a cyano group, or a halogeno group.
R 4 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted 5-10 It is preferably a membered heterocyclyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, or a group represented by -C(=N-OR a )R b , and a substituted or unsubstituted 5 A ~10-membered heterocyclyl group or a substituted or unsubstituted aminocarbonyl group is more preferred.
R4は、水素原子、置換若しくは無置換のC1~6アルキル基、置換若しくは無置換のC1~6アルキルカルボニル基、置換若しくは無置換のC1~6アルコキシカルボニル基、置換若しくは無置換の5~10員ヘテロシクリル基、置換若しくは無置換のアミノ基、置換若しくは無置換のアミノカルボニル基、または-C(=N-ORa)Rbで表される基であることが好ましく、置換若しくは無置換の5~10員ヘテロシクリル基、または置換若しくは無置換のアミノカルボニル基であることがより好ましい。 R 4 in formulas (I-1), (I-2), (I-3) and (I-4) is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2 ~6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted C1-6 alkoxycarbonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted 5- to 10-membered heterocyclyl group, substituted or unsubstituted amino group, substituted or unsubstituted aminocarbonyl group, -C( =N-OR a ) A group represented by R b , a nitro group, a cyano group, or a halogeno group.
R 4 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted 5-10 It is preferably a membered heterocyclyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, or a group represented by -C(=N-OR a )R b , and a substituted or unsubstituted 5 A ~10-membered heterocyclyl group or a substituted or unsubstituted aminocarbonyl group is more preferred.
R4における「置換若しくは無置換のC1~6アルキル基」、「置換若しくは無置換のC2~6アルケニル基」としては、前記R1において例示したそれらと同じものを挙げることができる。
Examples of the "substituted or unsubstituted C1-6 alkyl group" and "substituted or unsubstituted C2-6 alkenyl group" for R 4 include the same ones as exemplified for R 1 above.
R4における「C2~6アルキニル基」としては、エチニル基、1-プロピニル基、2-プロピニル基、1-ブチニル基、2-ブチニル基、3-ブチニル基、1-メチル-2-プロピニル基、2-メチル-3-ブチニル基、1-ペンチニル基、2-ペンチニル基、3-ペンチニル基、4-ペンチニル基、1-メチル-2-ブチニル基、2-メチル-3-ペンチニル基、1-ヘキシニル基、1,1-ジメチル-2-ブチニル基などを挙げることができる。
Examples of the "C2-6 alkynyl group" in R 4 include 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 and 1,1-dimethyl-2-butynyl group.
R4における「C1~6アルキルカルボニル基」としては、アセチル基、プロピオニル、n-プロピルカルボニル基、i-プロピルカルボニル基、n-ブチルカルボニル基、t-ブチルカルボニル基などを挙げることができる。
Examples of the "C1-6 alkylcarbonyl group" for R 4 include acetyl group, propionyl, n-propylcarbonyl group, i-propylcarbonyl group, n-butylcarbonyl group, and t-butylcarbonyl group.
R4における「C1~6アルコキシカルボニル基」としては、メトキシカルボニル基、エトキシカルボニル基、n-プロポキシカルボニル基、i-プロポキシカルボニル基、n-ブトキシカルボニル基、t-ブトキシカルボニル基などを挙げることができる。
Examples of the "C1-6 alkoxycarbonyl group" for R 4 include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group, etc. can.
R4における「C1~6アルキル基」、「C2~6アルケニル基」、「C2~6アルキニル基」、「C1~6アルキルカルボニル基」、または「C1~6アルコキシカルボニル基」上の置換基としては、
ハロゲノ基、水酸基、C1~6アルコキシ基、C1~6ハロアルコキシ基、C3~6シクロアルキル基、フェニル基、5員ヘテロアリール基、6員ヘテロアリール基、シアノ基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換されたフェニル基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された5員ヘテロアリール基;または
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された6員ヘテロアリール基が好ましい。 As a substituent on the "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkylcarbonyl group", or "C1-6 alkoxycarbonyl group" in R 4 teeth,
Halogeno group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group;
A phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;
a 5-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a C1-6 A 6-membered heteroaryl group substituted with one or more substituents of a 6-alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred.
ハロゲノ基、水酸基、C1~6アルコキシ基、C1~6ハロアルコキシ基、C3~6シクロアルキル基、フェニル基、5員ヘテロアリール基、6員ヘテロアリール基、シアノ基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換されたフェニル基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された5員ヘテロアリール基;または
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された6員ヘテロアリール基が好ましい。 As a substituent on the "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkylcarbonyl group", or "C1-6 alkoxycarbonyl group" in R 4 teeth,
Halogeno group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group;
A phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;
a 5-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a C1-6 A 6-membered heteroaryl group substituted with one or more substituents of a 6-alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred.
R4における「C3~6シクロアルキル基」としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などを挙げることができる。
Examples of the "C3-6 cycloalkyl group" for R 4 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like.
R4における「5~10員ヘテロシクリル基」とは、窒素原子、酸素原子および硫黄原子からなる群から選ばれる1、2、3または4個のヘテロ原子を環の構成原子として含む基である。ヘテロ原子が2個以上であるとき、それらは同じでもよいし、異なってもよい。単環および多環のいずれでもよい。
「5~10員ヘテロシクリル基」としては、5~10員飽和ヘテロシクリル基、5~10員ヘテロアリール基、5~10員部分不飽和ヘテロシクリル基などを挙げることができる。 The "5- to 10-membered heterocyclyl group" in R 4 is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms as ring constituent atoms. When there are two or more heteroatoms, they may be the same or different. It may be either monocyclic or polycyclic.
Examples of the "5- to 10-membered heterocyclyl group" include 5- to 10-membered saturated heterocyclyl groups, 5- to 10-membered heteroaryl groups, and 5- to 10-membered partially unsaturated heterocyclyl groups.
「5~10員ヘテロシクリル基」としては、5~10員飽和ヘテロシクリル基、5~10員ヘテロアリール基、5~10員部分不飽和ヘテロシクリル基などを挙げることができる。 The "5- to 10-membered heterocyclyl group" in R 4 is a group containing 1, 2, 3 or 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms as ring constituent atoms. When there are two or more heteroatoms, they may be the same or different. It may be either monocyclic or polycyclic.
Examples of the "5- to 10-membered heterocyclyl group" include 5- to 10-membered saturated heterocyclyl groups, 5- to 10-membered heteroaryl groups, and 5- to 10-membered partially unsaturated heterocyclyl groups.
5~10員飽和ヘテロシクリル基としては、ピロリジニル基、テトラヒドロフラニル基、チアゾリジニル基、テトラヒドロ-2H-ピラニル基、ピペリジル基、ピペラジニル基、モルホリニル基、ジオキソラニル基、ジオキサニル基などを挙げることができる。
5員ヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などを挙げることができる。
6員ヘテロアリール基としては、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などを挙げることができる。
7員ヘテロアリール基としては、3-アザビシクロ[3.2.0]ヘプタン-1,4-ジエン-2-イル基、3-アザビシクロ[3.2.0]ヘプタン-1,4,6-トリエン-6-イル基などを挙げることができる。
8員ヘテロアリール基としては、2,4,5,6-テトラヒドロシクロペンタ[c]ピロール2-イル基、2,4-ジヒドロシクロペンタ[c]ピロール-4-イル基などを挙げることができる。
9員ヘテロアリール基としては、インドリル基、イソインドリル基、ベンゾフラニル基、ベンゾチエニル基、インダゾリル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾイソオキサオゾリル基、ベンゾチアゾリル基、ベンゾイソチアゾリル基などを挙げることができる。
10員ヘテロアリール基としては、キノリニル基、イソキノリニル基、シンノリニル基、フタラジニル基、キナゾリニル基、キノキサリニル基などを挙げることができる。 Examples of the 5- to 10-membered saturated heterocyclyl group include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl 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 isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group. Can be done.
Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
As the 7-membered heteroaryl group, 3-azabicyclo[3.2.0]heptane-1,4-dien-2-yl group, 3-azabicyclo[3.2.0]heptane-1,4,6-trien-6-yl Examples include groups.
Examples of the 8-membered heteroaryl group include a 2,4,5,6-tetrahydrocyclopenta[c]pyrrol-2-yl group, a 2,4-dihydrocyclopenta[c]pyrrol-4-yl group, and the like. .
Examples of the 9-membered heteroaryl group include an indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, indazolyl group, benzimidazolyl group, benzoxazolyl group, benzisoxaozolyl group, benzothiazolyl group, benzisothiazolyl group, etc. can be mentioned.
Examples of the 10-membered heteroaryl group include a quinolinyl group, an isoquinolinyl group, a cinnolinyl group, a phthalazinyl group, a quinazolinyl group, and a quinoxalinyl group.
5員ヘテロアリール基としては、ピロリル基、フリル基、チエニル基、イミダゾリル基、ピラゾリル基、オキサゾリル基、イソオキサゾリル基、チアゾリル基、イソチアゾリル基、トリアゾリル基、オキサジアゾリル基、チアジアゾリル基、テトラゾリル基などを挙げることができる。
6員ヘテロアリール基としては、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、トリアジニル基などを挙げることができる。
7員ヘテロアリール基としては、3-アザビシクロ[3.2.0]ヘプタン-1,4-ジエン-2-イル基、3-アザビシクロ[3.2.0]ヘプタン-1,4,6-トリエン-6-イル基などを挙げることができる。
8員ヘテロアリール基としては、2,4,5,6-テトラヒドロシクロペンタ[c]ピロール2-イル基、2,4-ジヒドロシクロペンタ[c]ピロール-4-イル基などを挙げることができる。
9員ヘテロアリール基としては、インドリル基、イソインドリル基、ベンゾフラニル基、ベンゾチエニル基、インダゾリル基、ベンゾイミダゾリル基、ベンゾオキサゾリル基、ベンゾイソオキサオゾリル基、ベンゾチアゾリル基、ベンゾイソチアゾリル基などを挙げることができる。
10員ヘテロアリール基としては、キノリニル基、イソキノリニル基、シンノリニル基、フタラジニル基、キナゾリニル基、キノキサリニル基などを挙げることができる。 Examples of the 5- to 10-membered saturated heterocyclyl group include a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a tetrahydro-2H-pyranyl 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 isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, and a tetrazolyl group. Can be done.
Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.
As the 7-membered heteroaryl group, 3-azabicyclo[3.2.0]heptane-1,4-dien-2-yl group, 3-azabicyclo[3.2.0]heptane-1,4,6-trien-6-yl Examples include groups.
Examples of the 8-membered heteroaryl group include a 2,4,5,6-tetrahydrocyclopenta[c]pyrrol-2-yl group, a 2,4-dihydrocyclopenta[c]pyrrol-4-yl group, and the like. .
Examples of the 9-membered heteroaryl group include an indolyl group, isoindolyl group, benzofuranyl group, benzothienyl group, indazolyl group, benzimidazolyl group, benzoxazolyl group, benzisoxaozolyl group, benzothiazolyl group, benzisothiazolyl group, etc. can be mentioned.
Examples of the 10-membered heteroaryl group include a quinolinyl group, an isoquinolinyl group, a cinnolinyl group, a phthalazinyl group, a quinazolinyl group, and a quinoxalinyl group.
5~10員部分不飽和へテロシクリル基としては、ピロリニル基、ジヒドロフラニル基、イミダゾリニル基、ピラゾリニル基、オキサゾリニル基、イソオキサゾリニル基などの5員部分不飽和ヘテロシクリル基;ジヒドロピラニル基などの6員部分不飽和へテロシクリル基;インドリニル基、イソインドリニル基、2,3-ジヒドロベンゾフラニル基、1,3-ジヒドロベンゾフラニル基などの9員部分不飽和ヘテロシクリル基;1,2,3,4-テトラヒドロキノリニル基などの10員部分不飽和ヘテロシクリル基;を挙げることができる。
Examples of 5- to 10-membered partially unsaturated heterocyclyl groups include 5-membered partially unsaturated heterocyclyl groups such as pyrrolinyl group, dihydrofuranyl group, imidazolinyl group, pyrazolinyl group, oxazolinyl group, and isoxazolinyl group; dihydropyranyl group, etc. 6-membered partially unsaturated heterocyclyl group; 9-membered partially unsaturated heterocyclyl group such as indolinyl group, isoindolinyl group, 2,3-dihydrobenzofuranyl group, 1,3-dihydrobenzofuranyl group; 1,2,3 , 10-membered partially unsaturated heterocyclyl groups such as 4-tetrahydroquinolinyl groups;
R4における「C3~6シクロアルキル基」、「フェニル基」、「ナフチル基」、または「5~10員ヘテロシクリル基」上の置換基としては、
ハロゲノ基、C1~6アルキル基、C1~6ハロアルキル基、水酸基、C1~6アルコキシ基、C1~6ハロアルコキシ基、C3~6シクロアルキル基、フェニル基、5員ヘテロアリール基、6員ヘテロアリール基、シアノ基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換されたフェニル基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された5員ヘテロアリール基;または
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された6員ヘテロアリール基が好ましい。 The substituents on the "C3-6 cycloalkyl group", "phenyl group", "naphthyl group", or "5- to 10-membered heterocyclyl group" in R 4 include:
Halogeno group, C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group;
A phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;
a 5-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a C1-6 A 6-membered heteroaryl group substituted with one or more substituents of a 6-alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred.
ハロゲノ基、C1~6アルキル基、C1~6ハロアルキル基、水酸基、C1~6アルコキシ基、C1~6ハロアルコキシ基、C3~6シクロアルキル基、フェニル基、5員ヘテロアリール基、6員ヘテロアリール基、シアノ基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換されたフェニル基;
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された5員ヘテロアリール基;または
C1~6アルキル基、C1~6アルコキシ基、ハロゲノ基、C1~6ハロアルキル基、若しくはC1~6ハロアルコキシ基のいずれか1つ以上の置換基で置換された6員ヘテロアリール基が好ましい。 The substituents on the "C3-6 cycloalkyl group", "phenyl group", "naphthyl group", or "5- to 10-membered heterocyclyl group" in R 4 include:
Halogeno group, C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, C3-6 cycloalkyl group, phenyl group, 5-membered heteroaryl group, 6-membered heteroaryl group, cyano group;
A phenyl group substituted with one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group;
a 5-membered heteroaryl group substituted with any one or more substituents of a C1-6 alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group; or a C1-6 A 6-membered heteroaryl group substituted with one or more substituents of a 6-alkyl group, a C1-6 alkoxy group, a halogeno group, a C1-6 haloalkyl group, or a C1-6 haloalkoxy group is preferred.
R4における「置換フェニル基」若しくは「置換ナフチル基」は、「フェニル基」若しくは「ナフチル基」上にひとつ以上の置換基を有し、複数の置換基は相互に結合して環を形成してもよく、その環は飽和脂環または不飽和脂環のいずれであってもよい。「置換フェニル基」若しくは「置換ナフチル基」として、例えば、インデニル基、インダニル基、テトラヒドロナフチル基、ジヒドロナフチル基、トリル基、キシリル基、メシチル基、ジュリル基などを含む。
The "substituted phenyl group" or "substituted naphthyl group" in R 4 has one or more substituents on the "phenyl group" or "naphthyl group", and the plurality of substituents are bonded to each other to form a ring. The ring may be either a saturated alicyclic ring or an unsaturated alicyclic ring. The "substituted phenyl group" or "substituted naphthyl group" includes, for example, an indenyl group, an indanyl group, a tetrahydronaphthyl group, a dihydronaphthyl group, a tolyl group, a xylyl group, a mesityl group, a juryl group, and the like.
R4における「置換若しくは無置換のアミノ基」は、「-NRcRd」で表される基である。R4における「置換若しくは無置換のアミノカルボニル基」は、「-CO-NRcRd」で表される基である。式中、RcおよびRdは、それぞれ独立して、水素原子、C1~6アルキル基、ホルミル基、C1~6アルキルカルボニル基、置換若しくは無置換のアミノカルボニル基などを挙げることができる。
R4における「置換若しくは無置換のアミノ基」としては、例えば、アミノ基、メチルアミノ基、エチルアミノ基、ジメチルアミノ基などを挙げることができる。
R4における「置換若しくは無置換のアミノカルボニル基」としては、例えば、メチルアミノカルボニル基、エチルアミノカルボニル基、ジメチルアミノカルボニル基などを挙げることができる。 The "substituted or unsubstituted amino group" in R 4 is a group represented by "-NR c R d ". The "substituted or unsubstituted aminocarbonyl group" in R 4 is a group represented by "-CO-NR c R d ". In the formula, R c and R d each independently include a hydrogen atom, a C1-6 alkyl group, a formyl group, a C1-6 alkylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, and the like.
Examples of the "substituted or unsubstituted amino group" for R 4 include an amino group, a methylamino group, an ethylamino group, a dimethylamino group, and the like.
Examples of the "substituted or unsubstituted aminocarbonyl group" for R 4 include a methylaminocarbonyl group, an ethylaminocarbonyl group, and a dimethylaminocarbonyl group.
R4における「置換若しくは無置換のアミノ基」としては、例えば、アミノ基、メチルアミノ基、エチルアミノ基、ジメチルアミノ基などを挙げることができる。
R4における「置換若しくは無置換のアミノカルボニル基」としては、例えば、メチルアミノカルボニル基、エチルアミノカルボニル基、ジメチルアミノカルボニル基などを挙げることができる。 The "substituted or unsubstituted amino group" in R 4 is a group represented by "-NR c R d ". The "substituted or unsubstituted aminocarbonyl group" in R 4 is a group represented by "-CO-NR c R d ". In the formula, R c and R d each independently include a hydrogen atom, a C1-6 alkyl group, a formyl group, a C1-6 alkylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, and the like.
Examples of the "substituted or unsubstituted amino group" for R 4 include an amino group, a methylamino group, an ethylamino group, a dimethylamino group, and the like.
Examples of the "substituted or unsubstituted aminocarbonyl group" for R 4 include a methylaminocarbonyl group, an ethylaminocarbonyl group, and a dimethylaminocarbonyl group.
RcおよびRdにおける「C1~6アルキル基」としては、R1において例示したそれらと同じものを挙げることができる。
Examples of the "C1-6 alkyl group" for R c and R d include the same groups as exemplified for R 1 .
RcおよびRdにおける「C1~6アルキルカルボニル基」としては、アセチル基、プロピオニル基などを挙げることができる。
Examples of the "C1-6 alkylcarbonyl group" for R c and R d include an acetyl group and a propionyl group.
RcおよびRdにおける「置換若しくは無置換のアミノカルボニル基」は、「-CO-NReRf」で表される基である。式中、ReおよびRfは、それぞれ独立して、水素原子、C1~6アルキル基、ホルミル基、C1~6アルキルカルボニル基、置換若しくは無置換のアミノカルボニル基などを挙げることができる。ReおよびRfにおける「C1~6アルキル基」、「C1~6アルキルカルボニル基」、「置換若しくは無置換のアミノカルボニル基」としては、RcおよびRdにおいて例示したそれらと同じものを挙げることができる。
The "substituted or unsubstituted aminocarbonyl group" in R c and R d is a group represented by "-CO-NR e R f ". In the formula, R e and R f each independently include a hydrogen atom, a C1-6 alkyl group, a formyl group, a C1-6 alkylcarbonyl group, a substituted or unsubstituted aminocarbonyl group, and the like. Examples of the "C1-6 alkyl group", "C1-6 alkylcarbonyl group", and "substituted or unsubstituted aminocarbonyl group" in R e and R f include the same ones as exemplified in R c and R d . be able to.
-C(=N-ORa)Rbで表される基中のRaは、水素原子、または置換若しくは無置換のC1~6アルキル基であり、Rbは、水素原子、または置換若しくは無置換のC1~6アルキル基である。
R a in the group represented by -C(=N-OR a )R b is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, and R b is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. It is a substituted C1-6 alkyl group.
RaおよびRbにおける「置換若しくは無置換のC1~6アルキル基」としては、R1において例示したそれらと同じものを挙げることができる。
Examples of the "substituted or unsubstituted C1-6 alkyl group" for R a and R b include the same ones as exemplified for R 1 .
式(I-1)、(I-2)、(I-3)および(I-4)中のR5は、置換若しくは無置換のC1~6アルキル基または置換若しくは無置換のC3~6シクロアルキル基である。
R5は、置換若しくは無置換のC1~6アルキル基であることが好ましい。
R5における「置換若しくは無置換のC1~6アルキル基」としては、R1において例示したそれらと同じものを挙げることができる。R5における「置換若しくは無置換のC1~6アルキル基」の具体例として、シクロプロピルメチル基などのC3~6シクロアルキルC1~6アルキル基を挙げることができる。
R5における「置換若しくは無置換のC3~6シクロアルキル基」としては、R4において例示したそれらと同じものを挙げることができる。 R 5 in formulas (I-1), (I-2), (I-3) and (I-4) is a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cyclo It is an alkyl group.
R 5 is preferably a substituted or unsubstituted C1-6 alkyl group.
Examples of the "substituted or unsubstituted C1-6 alkyl group" for R 5 include the same ones as exemplified for R 1 . Specific examples of the "substituted or unsubstituted C1-6 alkyl group" for R 5 include C3-6 cycloalkyl C1-6 alkyl groups such as cyclopropylmethyl group.
Examples of the "substituted or unsubstituted C3-6 cycloalkyl group" for R 5 include the same ones as exemplified for R 4 .
R5は、置換若しくは無置換のC1~6アルキル基であることが好ましい。
R5における「置換若しくは無置換のC1~6アルキル基」としては、R1において例示したそれらと同じものを挙げることができる。R5における「置換若しくは無置換のC1~6アルキル基」の具体例として、シクロプロピルメチル基などのC3~6シクロアルキルC1~6アルキル基を挙げることができる。
R5における「置換若しくは無置換のC3~6シクロアルキル基」としては、R4において例示したそれらと同じものを挙げることができる。 R 5 in formulas (I-1), (I-2), (I-3) and (I-4) is a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cyclo It is an alkyl group.
R 5 is preferably a substituted or unsubstituted C1-6 alkyl group.
Examples of the "substituted or unsubstituted C1-6 alkyl group" for R 5 include the same ones as exemplified for R 1 . Specific examples of the "substituted or unsubstituted C1-6 alkyl group" for R 5 include C3-6 cycloalkyl C1-6 alkyl groups such as cyclopropylmethyl group.
Examples of the "substituted or unsubstituted C3-6 cycloalkyl group" for R 5 include the same ones as exemplified for R 4 .
式(I-1)、(I-2)、(I-3)および(I-4)中のnは、Oの数を表し、0、1または2である。すなわち、R5-S(O)n-で表される基は、R5-S-で表される基、R5-SO-で表される基、またはR5-SO2-で表される基を示す。
nは、2であることが好ましい。 n in formulas (I-1), (I-2), (I-3) and (I-4) represents the number of O, and is 0, 1 or 2. That is, the group represented by R 5 --S(O) n -- is a group represented by R 5 --S-, a group represented by R 5 --SO-, or a group represented by R 5 --SO 2 --. indicates a group.
It is preferable that n is 2.
nは、2であることが好ましい。 n in formulas (I-1), (I-2), (I-3) and (I-4) represents the number of O, and is 0, 1 or 2. That is, the group represented by R 5 --S(O) n -- is a group represented by R 5 --S-, a group represented by R 5 --SO-, or a group represented by R 5 --SO 2 --. indicates a group.
It is preferable that n is 2.
化合物(I)の塩は、農園芸学的に許容される塩であれば、特に制限されない。化合物(I)の塩としては、例えば、塩酸、硫酸などの無機酸の塩; 酢酸、乳酸などの有機酸の塩;リチウム、ナトリウム、カリウムなどのアルカリ金属の塩;カルシウム、マグネシウムなどのアルカリ土類金属の塩;鉄、銅などの遷移金属の塩;アンモニア;トリエチルアミン、トリブチルアミン、ピリジン、ヒドラジンなどの有機塩基の塩などを挙げることができる。
The salt of compound (I) is not particularly limited as long as it is an agriculturally and horticulturally acceptable salt. Examples of salts of compound (I) include 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; alkaline earths such as calcium and magnesium. Examples include salts of similar metals; salts of transition metals such as iron and copper; ammonia; salts of organic bases such as triethylamine, tributylamine, pyridine and hydrazine.
化合物(I)または化合物(I)の塩の製造方法は特に限定されない。例えば、化合物(I)または化合物(I)の塩は、実施例等に記載した公知の製造方法によって得ることができる。また、化合物(I)の塩は、化合物(I)から公知の手法によって得ることができる。
The method for producing compound (I) or a salt of compound (I) is not particularly limited. For example, compound (I) or a salt of compound (I) can be obtained by a known production method described in Examples and the like. Moreover, the salt of compound (I) can be obtained from compound (I) by a known method.
本願化合物の内で、式(1)中のB部分がB2であり、nが2である化合物(下記の図中の式中の(P-1))は以下の通り、反応させることで製造することができる。
下記の図中の化合物(IM-1)中のAおよびR5は、式(1)中のそれらと同じ意味を示す。
化合物(P-3)中のAおよびR5は、式(1)中のそれらと同じ意味を示す。
化合物(P-2)中のAおよびR5は、式(1)中のそれらと同じ意味を示す。
化合物(P-1)中のA、R4、およびR5は、式(1)中のそれらと同じ意味を示す。
化合物(IM-2)中のR4は、式(1)中のそれらと同じ意味を示し、X1はハロゲノ基を示す。 Among the compounds of the present application, a compound in which the B moiety in formula (1) is B2 and n is 2 ((P-1) in the formula in the figure below) is produced by the reaction as follows. can do.
A and R 5 in compound (IM-1) in the figure below have the same meanings as those in formula (1).
A and R 5 in compound (P-3) have the same meanings as in formula (1).
A and R 5 in compound (P-2) have the same meanings as in formula (1).
A, R 4 and R 5 in compound (P-1) have the same meanings as in formula (1).
R 4 in compound (IM-2) has the same meaning as those in formula (1), and X 1 represents a halogeno group.
下記の図中の化合物(IM-1)中のAおよびR5は、式(1)中のそれらと同じ意味を示す。
化合物(P-3)中のAおよびR5は、式(1)中のそれらと同じ意味を示す。
化合物(P-2)中のAおよびR5は、式(1)中のそれらと同じ意味を示す。
化合物(P-1)中のA、R4、およびR5は、式(1)中のそれらと同じ意味を示す。
化合物(IM-2)中のR4は、式(1)中のそれらと同じ意味を示し、X1はハロゲノ基を示す。 Among the compounds of the present application, a compound in which the B moiety in formula (1) is B2 and n is 2 ((P-1) in the formula in the figure below) is produced by the reaction as follows. can do.
A and R 5 in compound (IM-1) in the figure below have the same meanings as those in formula (1).
A and R 5 in compound (P-3) have the same meanings as in formula (1).
A and R 5 in compound (P-2) have the same meanings as in formula (1).
A, R 4 and R 5 in compound (P-1) have the same meanings as in formula (1).
R 4 in compound (IM-2) has the same meaning as those in formula (1), and X 1 represents a halogeno group.
化合物(IM-1)は、公知であるか、国際公開第2018/052035号、国際公開第2023/090345号などに記載の方法に準じて製造することができる。
化合物(P-3)は、化合物(IM-1)とN,N-ジメチルホルムアミドジメチルアセタール(略名:DMF-DMA)とを反応させることにより製造することができる。反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばエーテル類、芳香族炭化水素類、ニトリル類、非プロトン性極性溶媒、およびこれらの2つ以上の混合物が挙げられる。反応には、化合物(IM-1)1モルに対して、DMF-DMAが通常1~10モルの割合で用いられる。反応温度は、通常0℃~120℃の範囲である。反応時間は通常0.5~24時間の範囲である。反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮するなどの後処理操作を行うことにより、化合物(P-3)を得ることができる。 Compound (IM-1) is known or can be produced according to the method described in International Publication No. 2018/052035, International Publication No. 2023/090345, etc.
Compound (P-3) can be produced by reacting compound (IM-1) with N,N-dimethylformamide dimethyl acetal (abbreviation: DMF-DMA). The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of these. In the reaction, DMF-DMA is usually used in a ratio of 1 to 10 mol per 1 mol of compound (IM-1). The reaction temperature is usually in the range of 0°C to 120°C. Reaction times usually range from 0.5 to 24 hours. After the reaction is completed, compound (P-3) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
化合物(P-3)は、化合物(IM-1)とN,N-ジメチルホルムアミドジメチルアセタール(略名:DMF-DMA)とを反応させることにより製造することができる。反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばエーテル類、芳香族炭化水素類、ニトリル類、非プロトン性極性溶媒、およびこれらの2つ以上の混合物が挙げられる。反応には、化合物(IM-1)1モルに対して、DMF-DMAが通常1~10モルの割合で用いられる。反応温度は、通常0℃~120℃の範囲である。反応時間は通常0.5~24時間の範囲である。反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮するなどの後処理操作を行うことにより、化合物(P-3)を得ることができる。 Compound (IM-1) is known or can be produced according to the method described in International Publication No. 2018/052035, International Publication No. 2023/090345, etc.
Compound (P-3) can be produced by reacting compound (IM-1) with N,N-dimethylformamide dimethyl acetal (abbreviation: DMF-DMA). The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures of two or more of these. In the reaction, DMF-DMA is usually used in a ratio of 1 to 10 mol per 1 mol of compound (IM-1). The reaction temperature is usually in the range of 0°C to 120°C. Reaction times usually range from 0.5 to 24 hours. After the reaction is completed, compound (P-3) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
化合物(P-2)は、化合物(P-3)とヒドラジンとを反応させることにより製造することができる。反応は、有機酸存在下、通常溶媒中で行われる。反応に用いられる有機酸としては、例えば酢酸が挙げられる。反応に用いられる溶媒としては、例えばエーテル類、芳香族炭化水素類、ニトリル類、非プロトン性極性溶媒、アルコール類、およびこれらの2つ以上の混合物が挙げられる。反応には、化合物(P-3)1モルに対して、ヒドラジンが通常1~5モルの割合で用いられる。反応温度は、通常-20℃~120℃の範囲である。反応時間は通常0.1~24時間の範囲である。反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮するなどの後処理操作を行うことにより、化合物(P-2)を得ることができる。
Compound (P-2) can be produced by reacting compound (P-3) with hydrazine. The reaction is carried out in the presence of an organic acid, usually in a solvent. An example of the organic acid used in the reaction is acetic acid. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, alcohols, and mixtures of two or more of these. In the reaction, hydrazine is usually used in a ratio of 1 to 5 mol per 1 mol of compound (P-3). The reaction temperature is usually in the range of -20°C to 120°C. Reaction times usually range from 0.1 to 24 hours. After the reaction is completed, compound (P-2) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
化合物(P-1)は、化合物(P-2)と化合物(IM-2)とを、塩基の存在下で反応させることにより製造することができる。反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばエーテル類、芳香族炭化水素類、非プロトン性極性溶媒、およびこれらの2つ以上の混合物が挙げられる。反応に用いられる塩基としては、有機塩基類、アルカリ金属水素化物類、およびアルカリ金属炭酸塩類が挙げられる。反応には、化合物(P-2)1モルに対して、化合物(IM-2)が通常1~10モルの割合、塩基が通常0.1~5モルの割合で用いられる。反応温度は、通常-20℃~120℃の範囲である。反応時間は通常0.1~24時間の範囲である。
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮するなどの後処理操作を行うことにより、化合物(P-1)を得ることができる。
化合物(IM-2)は、市販の化合物であるか、または既知の方法を用いて製造することができる。 Compound (P-1) can be produced by reacting compound (P-2) and compound (IM-2) in the presence of a base. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, and mixtures of two or more of these. Bases used in the reaction include organic bases, alkali metal hydrides, and alkali metal carbonates. In the reaction, compound (IM-2) is usually used in a proportion of 1 to 10 moles and a base is used in a proportion of usually 0.1 to 5 moles per mole of compound (P-2). The reaction temperature is usually in the range of -20°C to 120°C. Reaction times usually range from 0.1 to 24 hours.
After completion of the reaction, compound (P-1) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
Compound (IM-2) is a commercially available compound or can be produced using known methods.
反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮するなどの後処理操作を行うことにより、化合物(P-1)を得ることができる。
化合物(IM-2)は、市販の化合物であるか、または既知の方法を用いて製造することができる。 Compound (P-1) can be produced by reacting compound (P-2) and compound (IM-2) in the presence of a base. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, aprotic polar solvents, and mixtures of two or more of these. Bases used in the reaction include organic bases, alkali metal hydrides, and alkali metal carbonates. In the reaction, compound (IM-2) is usually used in a proportion of 1 to 10 moles and a base is used in a proportion of usually 0.1 to 5 moles per mole of compound (P-2). The reaction temperature is usually in the range of -20°C to 120°C. Reaction times usually range from 0.1 to 24 hours.
After completion of the reaction, compound (P-1) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, drying and concentrating the organic layer.
Compound (IM-2) is a commercially available compound or can be produced using known methods.
本願化合物の内で、式(1)中のB部分がB1であり、nが2である化合物(下記の図中の式中の(T-1))の化合物は以下の通り、反応させることで製造することができる。
下記の図中の化合物(IM-3)中のAおよびR5は、式(1)中のそれらと同じ意味を示す。
化合物(T-3)中のAおよびR5は、式(1)中のそれらと同じ意味を示し、X2はハロゲノ基を示す。
化合物(T-2)中のA、R4、およびR5は、式(1)中のそれらと同じ意味を示す。
化合物(IM-4)中のR4は、式(1)中のそれらと同じ意味を示す。
化合物(T-1)中のA、R4、およびR5は、式(1)中のそれらと同じ意味を示す。 Among the compounds of the present application, a compound in which the B moiety in formula (1) is B1 and n is 2 ((T-1) in the formula in the figure below) can be reacted as follows. It can be manufactured in
A and R 5 in compound (IM-3) in the figure below have the same meanings as those in formula (1).
A and R 5 in compound (T-3) have the same meanings as those in formula (1), and X 2 represents a halogeno group.
A, R 4 and R 5 in compound (T-2) have the same meanings as in formula (1).
R 4 in compound (IM-4) has the same meaning as in formula (1).
A, R 4 and R 5 in compound (T-1) have the same meanings as in formula (1).
下記の図中の化合物(IM-3)中のAおよびR5は、式(1)中のそれらと同じ意味を示す。
化合物(T-3)中のAおよびR5は、式(1)中のそれらと同じ意味を示し、X2はハロゲノ基を示す。
化合物(T-2)中のA、R4、およびR5は、式(1)中のそれらと同じ意味を示す。
化合物(IM-4)中のR4は、式(1)中のそれらと同じ意味を示す。
化合物(T-1)中のA、R4、およびR5は、式(1)中のそれらと同じ意味を示す。 Among the compounds of the present application, a compound in which the B moiety in formula (1) is B1 and n is 2 ((T-1) in the formula in the figure below) can be reacted as follows. It can be manufactured in
A and R 5 in compound (IM-3) in the figure below have the same meanings as those in formula (1).
A and R 5 in compound (T-3) have the same meanings as those in formula (1), and X 2 represents a halogeno group.
A, R 4 and R 5 in compound (T-2) have the same meanings as in formula (1).
R 4 in compound (IM-4) has the same meaning as in formula (1).
A, R 4 and R 5 in compound (T-1) have the same meanings as in formula (1).
化合物(IM-3)は、公知であるか、国際公開第2018/052035号、国際公開第2023/090345号などに記載の方法に準じて製造することができる。
化合物(T-3)は、化合物(IM-3)と塩素化剤または臭素化剤とを反応させることにより製造することができる。反応は、通常溶媒の存在下で行われる。溶媒としては、例えばハロゲン化炭化水素類、アルコール類、エーテル類、DMF、NMP、DMI、DMSOなどの非プロトン性極性溶媒、酢酸、水およびこれらの混合物が挙げられる。塩素化剤としては、例えば塩素およびN-クロロスクシンイミドが挙げられ、臭素化剤としては、例えば臭素およびN-ブロモスクシンイミドが挙げられる。反応には、化合物(IM-3)1モルに対して、塩素化剤または臭素化剤が通常0.9~1.2モルの割合で用いられる。 Compound (IM-3) is known or can be produced according to the method described in International Publication No. 2018/052035, International Publication No. 2023/090345, etc.
Compound (T-3) can be produced by reacting compound (IM-3) with a chlorinating agent or a brominating agent. The reaction is usually carried out in the presence of a solvent. Examples of the solvent include halogenated hydrocarbons, alcohols, ethers, aprotic polar solvents such as DMF, NMP, DMI, and DMSO, acetic acid, water, and mixtures thereof. Chlorinating agents include, for example, chlorine and N-chlorosuccinimide, and brominating agents include, for example, bromine and N-bromosuccinimide. In the reaction, a chlorinating agent or a brominating agent is usually used in a ratio of 0.9 to 1.2 mol per 1 mol of compound (IM-3).
化合物(T-3)は、化合物(IM-3)と塩素化剤または臭素化剤とを反応させることにより製造することができる。反応は、通常溶媒の存在下で行われる。溶媒としては、例えばハロゲン化炭化水素類、アルコール類、エーテル類、DMF、NMP、DMI、DMSOなどの非プロトン性極性溶媒、酢酸、水およびこれらの混合物が挙げられる。塩素化剤としては、例えば塩素およびN-クロロスクシンイミドが挙げられ、臭素化剤としては、例えば臭素およびN-ブロモスクシンイミドが挙げられる。反応には、化合物(IM-3)1モルに対して、塩素化剤または臭素化剤が通常0.9~1.2モルの割合で用いられる。 Compound (IM-3) is known or can be produced according to the method described in International Publication No. 2018/052035, International Publication No. 2023/090345, etc.
Compound (T-3) can be produced by reacting compound (IM-3) with a chlorinating agent or a brominating agent. The reaction is usually carried out in the presence of a solvent. Examples of the solvent include halogenated hydrocarbons, alcohols, ethers, aprotic polar solvents such as DMF, NMP, DMI, and DMSO, acetic acid, water, and mixtures thereof. Chlorinating agents include, for example, chlorine and N-chlorosuccinimide, and brominating agents include, for example, bromine and N-bromosuccinimide. In the reaction, a chlorinating agent or a brominating agent is usually used in a ratio of 0.9 to 1.2 mol per 1 mol of compound (IM-3).
化合物(T-2)は、化合物(T-3)と化合物(IM-4)を反応させることにより製造することができる。反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばエーテル類、芳香族炭化水素類、ニトリル類、非プロトン性極性溶媒、アルコール類、およびこれらの2つ以上の混合物が挙げられる。反応には、化合物(T-3)1モルに対して、化合物(IM-4)が通常1~5モルの割合で用いられる。反応温度は、通常は室温~100℃の範囲である。反応時間は通常0.1~24時間の範囲である。反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を乾燥、濃縮するなどの後処理操作を行うことにより、化合物(T-2)を得ることができる。
化合物(IM-4)は、市販の化合物であるか、または既知の方法を用いて製造することができる。 Compound (T-2) can be produced by reacting compound (T-3) and compound (IM-4). The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, alcohols, and mixtures of two or more of these. In the reaction, compound (IM-4) is usually used in a ratio of 1 to 5 mol per 1 mol of compound (T-3). The reaction temperature is usually in the range of room temperature to 100°C. Reaction times usually range from 0.1 to 24 hours. After the reaction is completed, compound (T-2) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
Compound (IM-4) is a commercially available compound or can be produced using known methods.
化合物(IM-4)は、市販の化合物であるか、または既知の方法を用いて製造することができる。 Compound (T-2) can be produced by reacting compound (T-3) and compound (IM-4). The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, alcohols, and mixtures of two or more of these. In the reaction, compound (IM-4) is usually used in a ratio of 1 to 5 mol per 1 mol of compound (T-3). The reaction temperature is usually in the range of room temperature to 100°C. Reaction times usually range from 0.1 to 24 hours. After the reaction is completed, compound (T-2) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
Compound (IM-4) is a commercially available compound or can be produced using known methods.
化合物(T-3)は、化合物(T-2)と酸化剤とを反応させることにより製造することができる。反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えばハロゲン化炭化水素類、ニトリル類、アルコール類、酢酸、水およびこれらの2つ以上の混合物が挙げられる。反応に用いられる酸化剤としては、例えばmCPBAおよび過酸化水素が挙げられる。酸化剤として過酸化水素を用いる場合は、必要に応じて塩基または触媒を用いてもよい。塩基としては、炭酸ナトリウムが挙げられる。反応に塩基を用いる場合、化合物(T-2)1モルに対して、塩基が通常0.01~1モルの割合で用いられる。触媒としては、例えばタングステン酸ナトリウムが挙げられる。反応に触媒を用いる場合、化合物(T-2)1モルに対して、触媒が通常0.01~0.5モルの割合で用いられる。反応には、化合物(T-2)1モルに対して、酸化剤が通常2~5モルの割合で用いられる。反応温度は、通常-20~60℃の範囲である。反応時間は通常0.1~12時間の範囲である。反応終了後は、反応混合物に水を加え、有機溶媒で抽出し、有機層を必要に応じて還元剤(例えば亜硫酸ナトリウム、チオ硫酸ナトリウム)の水溶液、および塩基(例えば炭酸水素ナトリウム)の水溶液で洗浄する。この有機層を乾燥、濃縮することにより、化合物(T-3)を得ることができる。
Compound (T-3) can be produced by reacting compound (T-2) with an oxidizing agent. The reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures of two or more thereof. Examples of the oxidizing agent used in the reaction include mCPBA and hydrogen peroxide. When using hydrogen peroxide as an oxidizing agent, a base or a catalyst may be used as necessary. Examples of the base include sodium carbonate. When a base is used in the reaction, it is usually used in a ratio of 0.01 to 1 mol per 1 mol of compound (T-2). Examples of the catalyst include sodium tungstate. When a catalyst is used in the reaction, it is usually used in a ratio of 0.01 to 0.5 mol per 1 mol of compound (T-2). In the reaction, the oxidizing agent is usually used in a ratio of 2 to 5 mol per 1 mol of compound (T-2). The reaction temperature is usually in the range of -20 to 60°C. Reaction times usually range from 0.1 to 12 hours. After the reaction is complete, water is added to the reaction mixture, extracted with an organic solvent, and the organic layer is optionally treated with an aqueous solution of a reducing agent (e.g., sodium sulfite, sodium thiosulfate) and an aqueous solution of a base (e.g., sodium bicarbonate). Wash. Compound (T-3) can be obtained by drying and concentrating this organic layer.
本発明のイミダゾリルアゾール化合物(以下、「本発明化合物」という。)は、植物の生育に影響する各種の農業害虫およびダニ類などの有害生物の防除効果に優れている。
また、本発明化合物は、作物に対する薬害が少なく、魚類や温血動物への毒性が低いため、安全性の高い物質である。そのため、殺虫剤または殺ダニ剤の有効成分として有用である。
さらに、近年、コナガ、ウンカ、ヨコバイ、アブラムシなど多くの害虫において各種既存薬剤に対する抵抗性が発達し、それら薬剤の効力不足問題を生じており、抵抗性系統の害虫にも有効な薬剤が望まれている。本発明化合物は、感受性系統のみならず、各種抵抗性系統の害虫や、さらに殺ダニ剤抵抗性系統のダニ類にも優れた防除効果を示す。 The imidazolylazole compound of the present invention (hereinafter referred to as "the compound of the present invention") has an excellent control effect on pests such as various agricultural pests and mites that affect the growth of plants.
Furthermore, the compound of the present invention has low phytotoxicity to crops and low toxicity to fish and warm-blooded animals, so it is a highly safe substance. Therefore, it is useful as an active ingredient in insecticides or acaricides.
Furthermore, in recent years, many insect pests such as diamondback moths, planthoppers, leafhoppers, and aphids have developed resistance to various existing pesticides, resulting in the lack of efficacy of these drugs.Therefore, there is a need for drugs that are effective against resistant insect pests. ing. The compounds of the present invention exhibit excellent control effects not only on susceptible strains, but also on various resistant strains of insect pests, and furthermore against acaricide-resistant strains of mites.
また、本発明化合物は、作物に対する薬害が少なく、魚類や温血動物への毒性が低いため、安全性の高い物質である。そのため、殺虫剤または殺ダニ剤の有効成分として有用である。
さらに、近年、コナガ、ウンカ、ヨコバイ、アブラムシなど多くの害虫において各種既存薬剤に対する抵抗性が発達し、それら薬剤の効力不足問題を生じており、抵抗性系統の害虫にも有効な薬剤が望まれている。本発明化合物は、感受性系統のみならず、各種抵抗性系統の害虫や、さらに殺ダニ剤抵抗性系統のダニ類にも優れた防除効果を示す。 The imidazolylazole compound of the present invention (hereinafter referred to as "the compound of the present invention") has an excellent control effect on pests such as various agricultural pests and mites that affect the growth of plants.
Furthermore, the compound of the present invention has low phytotoxicity to crops and low toxicity to fish and warm-blooded animals, so it is a highly safe substance. Therefore, it is useful as an active ingredient in insecticides or acaricides.
Furthermore, in recent years, many insect pests such as diamondback moths, planthoppers, leafhoppers, and aphids have developed resistance to various existing pesticides, resulting in the lack of efficacy of these drugs.Therefore, there is a need for drugs that are effective against resistant insect pests. ing. The compounds of the present invention exhibit excellent control effects not only on susceptible strains, but also on various resistant strains of insect pests, and furthermore against acaricide-resistant strains of mites.
本発明化合物は、人獣に害を及ぼす外部寄生虫および内部寄生虫の防除効果に優れている。また、魚類や温血動物への毒性が低いため、安全性の高い物質である。そのため、外部寄生虫および内部寄生虫の防除剤の有効成分として有用である。
The compound of the present invention has an excellent control effect on ectoparasites and endoparasites that are harmful to humans and animals. It is also a highly safe substance as it has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient in agents for controlling ectoparasites and endoparasites.
また、本発明化合物は、防除の対象となる生物のすべての発育ステージにおいて効力を示し、例えば、ダニ、昆虫などの卵、若虫、幼虫、蛹、成虫に対して優れた防除効果を示す。
Furthermore, the compounds of the present invention exhibit efficacy at all developmental stages of organisms to be controlled, and exhibit excellent control effects against eggs, nymphs, larvae, pupae, and adults of mites and insects, for example.
〔有害生物防除剤〕
本発明の有害生物防除剤は、本発明化合物から選ばれる少なくともひとつを有効成分として含有する。本発明の有害生物防除剤に含まれる本発明化合物の量は有害生物の防除効果を示す限りにおいて特に制限されない。有害生物防除剤は、有害生物を防除する剤であり、殺虫若しくは殺ダニ剤、外部寄生虫防除剤、または内部寄生虫防除若しくは駆除剤などを包含する。 [Pest control agent]
The pest 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 pest control agent of the present invention is not particularly limited as long as it exhibits a pest control effect. Pest control agents are agents for controlling harmful organisms, and include insecticides or acaricides, ectoparasite control agents, endoparasite control or exterminators, and the like.
本発明の有害生物防除剤は、本発明化合物から選ばれる少なくともひとつを有効成分として含有する。本発明の有害生物防除剤に含まれる本発明化合物の量は有害生物の防除効果を示す限りにおいて特に制限されない。有害生物防除剤は、有害生物を防除する剤であり、殺虫若しくは殺ダニ剤、外部寄生虫防除剤、または内部寄生虫防除若しくは駆除剤などを包含する。 [Pest control agent]
The pest 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 pest control agent of the present invention is not particularly limited as long as it exhibits a pest control effect. Pest control agents are agents for controlling harmful organisms, and include insecticides or acaricides, ectoparasite control agents, endoparasite control or exterminators, and the like.
〔殺虫若しくは殺ダニ剤〕
本発明の殺虫若しくは殺ダニ剤は、本発明化合物から選ばれる少なくともひとつを有効成分として含有する。本発明の殺虫若しくは殺ダニ剤に含まれる本発明化合物の量は殺虫若しくは殺ダニ効果を示す限りにおいて特に制限されない。 [Insecticide or acaricide]
The 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 compound of the present invention contained in the insecticidal or acaricidal agent of the present invention is not particularly limited as long as it exhibits an insecticidal or acaricidal effect.
本発明の殺虫若しくは殺ダニ剤は、本発明化合物から選ばれる少なくともひとつを有効成分として含有する。本発明の殺虫若しくは殺ダニ剤に含まれる本発明化合物の量は殺虫若しくは殺ダニ効果を示す限りにおいて特に制限されない。 [Insecticide or acaricide]
The 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 compound of the present invention contained in the insecticidal or acaricidal agent of the present invention is not particularly limited as long as it exhibits an insecticidal or acaricidal effect.
本発明の有害生物防除剤、または殺虫若しくは殺ダニ剤は、穀物類;野菜類;根菜類;イモ類;花卉類;果樹類;観葉植物、茶、コーヒー、カカオなどの樹木類;牧草類;芝類;ワタなどの植物に対して用いることが好ましい。
植物への施用において、本発明の有害生物防除剤、または殺虫若しくは殺ダニ剤は、葉、茎、柄、花、蕾、果実、種子、スプラウト、根、塊茎、塊根、苗条、挿し木などのいずれの部位に用いてもよい。
また、本発明の有害生物防除剤、または殺虫若しくは殺ダニ剤は、施用される植物の種によって特に制限されない。植物の種としては、例えば、原種、変種、改良品種、栽培品種、突然変異体、ハイブリッド体、遺伝子組み換え体(GMO)などを挙げることができる。
本発明の有害生物防除剤は、各種の農業害虫およびダニ類を防除するために、種子処理、茎葉散布、土壌施用、水面施用などに使用することができる。 The pest control agent, insecticide or acaricide of the present invention can be applied to cereals; vegetables; root vegetables; tubers; flowers; fruit trees; ornamental plants, trees such as tea, coffee and cacao; grasses; Turf; preferably used for plants such as cotton.
When applied to plants, the pest control agent, insecticide or acaricide of the present invention can be applied to any plant such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, cuttings, etc. It may be used in the following areas.
Further, 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, cultivated varieties, mutants, hybrids, and genetically modified plants (GMO).
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.
植物への施用において、本発明の有害生物防除剤、または殺虫若しくは殺ダニ剤は、葉、茎、柄、花、蕾、果実、種子、スプラウト、根、塊茎、塊根、苗条、挿し木などのいずれの部位に用いてもよい。
また、本発明の有害生物防除剤、または殺虫若しくは殺ダニ剤は、施用される植物の種によって特に制限されない。植物の種としては、例えば、原種、変種、改良品種、栽培品種、突然変異体、ハイブリッド体、遺伝子組み換え体(GMO)などを挙げることができる。
本発明の有害生物防除剤は、各種の農業害虫およびダニ類を防除するために、種子処理、茎葉散布、土壌施用、水面施用などに使用することができる。 The pest control agent, insecticide or acaricide of the present invention can be applied to cereals; vegetables; root vegetables; tubers; flowers; fruit trees; ornamental plants, trees such as tea, coffee and cacao; grasses; Turf; preferably used for plants such as cotton.
When applied to plants, the pest control agent, insecticide or acaricide of the present invention can be applied to any plant such as leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, cuttings, etc. It may be used in the following areas.
Further, 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, cultivated varieties, mutants, hybrids, and genetically modified plants (GMO).
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.
本発明の有害生物防除剤によって防除可能な各種の農業害虫およびダニ類の具体例を以下に示す。
Specific examples of various agricultural pests and mites that can be controlled by the pest control agent of the present invention are shown below.
(1)鱗翅目(Lepidoptera)のチョウまたは蛾
(a)ヒトリガ科(Arctiidae)のガ、例えば、アメリカシロヒトリ(Hyphantria cunea)、クワゴマダラヒトリ(Lemyra imparilis);
(b)チビガ科(Bucculatricidae)のガ、例えば、ナシチビガ(Bucculatrix pyrivorella);
(c)シンクイガ科(Carposinidae)のガ、例えば、モモシンクイガ(Carposina sasakii);
(d)ツトガ科(Crambidae)のガ、例えば、ジアファニア属種(Diaphania spp.)の、ワタヘリクロノメイガ(Diaphania indica)、アメリカウリノメイガ(Diaphania nitidalis);例えば、オストリニア属種(Ostrinia spp.)の、アワノメイガ(Ostrinia furnacalis)、ヨーロピアンコーンボーラー(Ostrinia nubilalis)、アズキノメイガ(Ostrinia scapulalis);その他、ニカメイガ(Chilo suppressalis)、コブノメイガ(Cnaphalocrocis medinalis)、モモノゴマダラノメイガ(Conogethes punctiferalis)、サウスウエスタンコンボーラー(Diatraea grandiosella)、クワノメイガ(Glyphodes pyloalis)、ハイマダラノメイガ(Hellula undalis)、シバツトガ(Parapediasia teterrella);
(e)キバガ科(Gelechiidae)のガ、例えば、イモキバガ(Helcystogramma triannulella)、ワタアカミムシ(Pectinophora gossypiella)、ジャガイモキバガ(Phthorimaeaoperculella)、バクガ(Sitotroga cerealella);
(f)シャクガ科(Geometridae)のガ、例えば、ヨモギエダシャク(Ascotis selenaria);
(g)ホソガ科(Gracillariidae)のガ、例えば、チャノホソガ(Caloptilia theivora)、ミカンハモグリガ(Phyllocnistis citrella)、キンモンホソガ(Phyllonorycter ringoniella);
(h)セセリチョウ科(Hesperiidae)のチョウ、例えば、イチモンジセセリ(Parnara guttata);
(i)カレハガ科(Lasiocampidae)のガ、例えば、オビカレハ(Malacosoma neustria);
(j)ドクガ科(Lymantriidae)のガ、例えば、リマントリア属種(Lymantria spp.)の、マイマイガ(Lymantria dispar)、ノンネマイマイ(Lymantria monacha);その他の、チャドクガ(Euproctis pseudoconspersa)、ヒメシロモンドクガ(Orgyia thyellina); (1) Lepidoptera butterflies or moths (a) Arctiidae moths, such as Hyphantria cunea, Lemyra imparilis;
(b) moths of the Bucculatricidae family, such as Bucculatrix pyrivorella;
(c) moths of the Carposinidae family, such as Carposina sasakii;
(d) Moths of the Crambidae family, such as Diaphania spp., Diaphania indica, Diaphania nitidalis; for example, Ostrinia spp. Ostrinia furnacalis, European corn borer (Ostrinia nubilalis), Ostrinia scapulalis; others include Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Southwestern corn borer ( Diatraea grandiosella), Glyphodes pyloalis, Hellula undalis, Parapediasia teterrella;
(e) moths of the Gelechiidae family, such as Helcystogramma triannullella, Pectinophora gossypiella, Phthorimaea operculella, Sitotroga cerealella;
(f) Moths of the family Geometridae, such as Ascotis selenaria;
(g) Moths of the Gracillariidae family, such as Caloptilia theivora, Phyllocnistis citrella, Phyllonorycter ringoniella;
(h) Butterflies of the Hesperiidae family, such as Parnara guttata;
(i) Moths of the Lasiocampidae family, such as Malacosoma neustria;
(j) Lymantriidae moths, such as Lymantria spp., Lymantria dispar, Lymantria monacha; other moths, Euproctis pseudoconspersa, Orgyia thyellina);
(a)ヒトリガ科(Arctiidae)のガ、例えば、アメリカシロヒトリ(Hyphantria cunea)、クワゴマダラヒトリ(Lemyra imparilis);
(b)チビガ科(Bucculatricidae)のガ、例えば、ナシチビガ(Bucculatrix pyrivorella);
(c)シンクイガ科(Carposinidae)のガ、例えば、モモシンクイガ(Carposina sasakii);
(d)ツトガ科(Crambidae)のガ、例えば、ジアファニア属種(Diaphania spp.)の、ワタヘリクロノメイガ(Diaphania indica)、アメリカウリノメイガ(Diaphania nitidalis);例えば、オストリニア属種(Ostrinia spp.)の、アワノメイガ(Ostrinia furnacalis)、ヨーロピアンコーンボーラー(Ostrinia nubilalis)、アズキノメイガ(Ostrinia scapulalis);その他、ニカメイガ(Chilo suppressalis)、コブノメイガ(Cnaphalocrocis medinalis)、モモノゴマダラノメイガ(Conogethes punctiferalis)、サウスウエスタンコンボーラー(Diatraea grandiosella)、クワノメイガ(Glyphodes pyloalis)、ハイマダラノメイガ(Hellula undalis)、シバツトガ(Parapediasia teterrella);
(e)キバガ科(Gelechiidae)のガ、例えば、イモキバガ(Helcystogramma triannulella)、ワタアカミムシ(Pectinophora gossypiella)、ジャガイモキバガ(Phthorimaeaoperculella)、バクガ(Sitotroga cerealella);
(f)シャクガ科(Geometridae)のガ、例えば、ヨモギエダシャク(Ascotis selenaria);
(g)ホソガ科(Gracillariidae)のガ、例えば、チャノホソガ(Caloptilia theivora)、ミカンハモグリガ(Phyllocnistis citrella)、キンモンホソガ(Phyllonorycter ringoniella);
(h)セセリチョウ科(Hesperiidae)のチョウ、例えば、イチモンジセセリ(Parnara guttata);
(i)カレハガ科(Lasiocampidae)のガ、例えば、オビカレハ(Malacosoma neustria);
(j)ドクガ科(Lymantriidae)のガ、例えば、リマントリア属種(Lymantria spp.)の、マイマイガ(Lymantria dispar)、ノンネマイマイ(Lymantria monacha);その他の、チャドクガ(Euproctis pseudoconspersa)、ヒメシロモンドクガ(Orgyia thyellina); (1) Lepidoptera butterflies or moths (a) Arctiidae moths, such as Hyphantria cunea, Lemyra imparilis;
(b) moths of the Bucculatricidae family, such as Bucculatrix pyrivorella;
(c) moths of the Carposinidae family, such as Carposina sasakii;
(d) Moths of the Crambidae family, such as Diaphania spp., Diaphania indica, Diaphania nitidalis; for example, Ostrinia spp. Ostrinia furnacalis, European corn borer (Ostrinia nubilalis), Ostrinia scapulalis; others include Chilo suppressalis, Cnaphalocrocis medinalis, Conogethes punctiferalis, Southwestern corn borer ( Diatraea grandiosella), Glyphodes pyloalis, Hellula undalis, Parapediasia teterrella;
(e) moths of the Gelechiidae family, such as Helcystogramma triannullella, Pectinophora gossypiella, Phthorimaea operculella, Sitotroga cerealella;
(f) Moths of the family Geometridae, such as Ascotis selenaria;
(g) Moths of the Gracillariidae family, such as Caloptilia theivora, Phyllocnistis citrella, Phyllonorycter ringoniella;
(h) Butterflies of the Hesperiidae family, such as Parnara guttata;
(i) Moths of the Lasiocampidae family, such as Malacosoma neustria;
(j) Lymantriidae moths, such as Lymantria spp., Lymantria dispar, Lymantria monacha; other moths, Euproctis pseudoconspersa, Orgyia thyellina);
(k)モグリガ科(Lyonetiidae )のガ、例えば、リオネチア属種(Lyonetia spp.)の、モモハモグリガ(Lyonetia clerkella)、ギンモンハモグリガ(Lyonetia prunifoliella malinella);
(l)ヤガ科(Noctuidae)のガ、例えば、スポドプテラ属種(Spodoptera spp.)の、スジキリヨトウ(Spodoptera depravata)、サザンアーミーワーム(Spodoptera eridania)、シロイチモジヨトウ(Spodoptera exigua)、ツマジロクサヨトウ(Spodoptera frugiperda)、アフリカヨトウ(Spodoptera littoralis)、ハスモンヨトウ(Spodoptera litura);例えば、オートグラファ属種(Autographa spp.)の、ガマキンウワバ(Autographa gamma)、タマナギンウワバ(Autographa nigrisigna);例えば、アグロチス属種(Agrotis spp.)の、タマナヤガ(Agrotis ipsilon)、カブラヤガ(Agrotis segetum);
例えば、ヘリコベルパ属種(Helicoverpa spp.)の、オオタバコガ(Helicoverpa armigera)、タバコガ(Helicoverpa assulta)、コットンボールワーム(Helicoverpa zea);例えば、ヘリオチス属種(Heliothis spp.)の、ワタキバガ (Heliothis armigera)、ニセアメリカタバコガ(Heliothis virescens);その他の、ナカジロシタバ(Aedia leucomelas)、ミツモンキンウワバ(Ctenoplusia agnata)、アケビコノハ(Eudocima tyrannus)、ヨトウガ(Mamestra brassicae)、アワヨトウ(Mythimna separata)、フタオビコヤガ(Naranga aenescens)、マツキリガ(Panolis japonica)、ニセタマナヤガ(Peridroma saucia)、ソイビーンルーパー(Pseudoplusia includens)、イラクサギンウワバ(Trichoplusia ni);
(m)コブガ科(Nolidae) のガ、例えば、ミスジアオリンガ (Earias insulana);
(n)シロチョウ科(Pieridae)のチョウ、例えば、モンシロチョウ属種(Pieris spp.)のオオモンシロチョウ(Pieris brassicae)、モンシロチョウ(Pieris rapae crucivora);
(o)コナガ科(Plutellidae)のガ、例えば、アクロレピオプシス属種(Acrolepiopsis spp.)の、ネギコガ(Acrolepiopsis sapporensis)、ヤマノイモコガ(Acrolepiopsis suzukiella);その他、コナガ(Plutella xylostella);
(p)メイガ科(Pyralidae)のガ、例えば、スジマダラメイガ(Cadra cautella)、モロコシマダラメイガ(Elasmopalpus lignosellus)、シロイチモジマダラメイガ(Etiella zinckenella)、ハチノスツヅリガ (Galleria mellonella);
(q)スズメガ科(Sphingidae)のガ、例えば、マンジュカ属種(Manduca spp.)の、トマトホーンワーム(Manduca quinquemaculata)、タバコホーンワーム(Manduca sexta); (k) moths of the family Lyonetiidae, such as Lyonetia clerkella and Lyonetia prunifoliella malinella of the genus Lyonetia spp.;
(l) Moths of the family Noctuidae, such as Spodoptera spp., Spodoptera depravata, Southern armyworm (Spodoptera eridania), Spodoptera exigua, Spodoptera frugiperda ), Spodoptera littoralis, Spodoptera litura; for example, Autographa spp., Autographa gamma, Autographa nigrisigna; for example, Agrotis spp. Agrotis ipsilon, Agrotis segetum;
For example, Helicoverpa armigera, Helicoverpa assulta, cotton ball worm (Helicoverpa zea) of the Helicoverpa spp.; Heliothis armigera, of the Heliothis spp. Heliothis virescens; others, Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, Mythimna separata, Naranga aenescens, Panolis japonica, Peridroma saucia, Pseudoplusia includens, Trichoplusia ni;
(m) moths of the Nolidae family, such as Earias insulana;
(n) Butterflies of the Pieridae family, such as Pieris brassicae and Pieris rapae crucivora of Pieris spp.;
(o) Moths of the family Plutellidae, such as Acrolepiopsis spp., Acrolepiopsis sapporensis, Acrolepiopsis suzukiella; others, Plutella xylostella;
(p) Moths of the Pyralidae family, such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Galleria mellonella;
(q) moths of the family Sphingidae, such as Manduca spp., tomato hornworm (Manduca quinquemaculata), tobacco hornworm (Manduca sexta);
(l)ヤガ科(Noctuidae)のガ、例えば、スポドプテラ属種(Spodoptera spp.)の、スジキリヨトウ(Spodoptera depravata)、サザンアーミーワーム(Spodoptera eridania)、シロイチモジヨトウ(Spodoptera exigua)、ツマジロクサヨトウ(Spodoptera frugiperda)、アフリカヨトウ(Spodoptera littoralis)、ハスモンヨトウ(Spodoptera litura);例えば、オートグラファ属種(Autographa spp.)の、ガマキンウワバ(Autographa gamma)、タマナギンウワバ(Autographa nigrisigna);例えば、アグロチス属種(Agrotis spp.)の、タマナヤガ(Agrotis ipsilon)、カブラヤガ(Agrotis segetum);
例えば、ヘリコベルパ属種(Helicoverpa spp.)の、オオタバコガ(Helicoverpa armigera)、タバコガ(Helicoverpa assulta)、コットンボールワーム(Helicoverpa zea);例えば、ヘリオチス属種(Heliothis spp.)の、ワタキバガ (Heliothis armigera)、ニセアメリカタバコガ(Heliothis virescens);その他の、ナカジロシタバ(Aedia leucomelas)、ミツモンキンウワバ(Ctenoplusia agnata)、アケビコノハ(Eudocima tyrannus)、ヨトウガ(Mamestra brassicae)、アワヨトウ(Mythimna separata)、フタオビコヤガ(Naranga aenescens)、マツキリガ(Panolis japonica)、ニセタマナヤガ(Peridroma saucia)、ソイビーンルーパー(Pseudoplusia includens)、イラクサギンウワバ(Trichoplusia ni);
(m)コブガ科(Nolidae) のガ、例えば、ミスジアオリンガ (Earias insulana);
(n)シロチョウ科(Pieridae)のチョウ、例えば、モンシロチョウ属種(Pieris spp.)のオオモンシロチョウ(Pieris brassicae)、モンシロチョウ(Pieris rapae crucivora);
(o)コナガ科(Plutellidae)のガ、例えば、アクロレピオプシス属種(Acrolepiopsis spp.)の、ネギコガ(Acrolepiopsis sapporensis)、ヤマノイモコガ(Acrolepiopsis suzukiella);その他、コナガ(Plutella xylostella);
(p)メイガ科(Pyralidae)のガ、例えば、スジマダラメイガ(Cadra cautella)、モロコシマダラメイガ(Elasmopalpus lignosellus)、シロイチモジマダラメイガ(Etiella zinckenella)、ハチノスツヅリガ (Galleria mellonella);
(q)スズメガ科(Sphingidae)のガ、例えば、マンジュカ属種(Manduca spp.)の、トマトホーンワーム(Manduca quinquemaculata)、タバコホーンワーム(Manduca sexta); (k) moths of the family Lyonetiidae, such as Lyonetia clerkella and Lyonetia prunifoliella malinella of the genus Lyonetia spp.;
(l) Moths of the family Noctuidae, such as Spodoptera spp., Spodoptera depravata, Southern armyworm (Spodoptera eridania), Spodoptera exigua, Spodoptera frugiperda ), Spodoptera littoralis, Spodoptera litura; for example, Autographa spp., Autographa gamma, Autographa nigrisigna; for example, Agrotis spp. Agrotis ipsilon, Agrotis segetum;
For example, Helicoverpa armigera, Helicoverpa assulta, cotton ball worm (Helicoverpa zea) of the Helicoverpa spp.; Heliothis armigera, of the Heliothis spp. Heliothis virescens; others, Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, Mythimna separata, Naranga aenescens, Panolis japonica, Peridroma saucia, Pseudoplusia includens, Trichoplusia ni;
(m) moths of the Nolidae family, such as Earias insulana;
(n) Butterflies of the Pieridae family, such as Pieris brassicae and Pieris rapae crucivora of Pieris spp.;
(o) Moths of the family Plutellidae, such as Acrolepiopsis spp., Acrolepiopsis sapporensis, Acrolepiopsis suzukiella; others, Plutella xylostella;
(p) Moths of the Pyralidae family, such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Galleria mellonella;
(q) moths of the family Sphingidae, such as Manduca spp., tomato hornworm (Manduca quinquemaculata), tobacco hornworm (Manduca sexta);
(r)ニセマイコガ科(Stathmopodidae)のガ、例えば、カキノヘタムシガ(Stathmopoda masinissa);
(s)ヒロズコガ科(Tineidae)のガ、例えば、イガ(Tinea translucens);
(t)ハマキガ科(Tortricidae)のガ、例えば、アドキソフィエス属種(Adoxophyes spp.)の、チャノコカクモンハマキ(Adoxophyes honmai)、リンゴコカクモンハマキ(Adoxophyes orana);例えば、アルチプス属種(Archips spp.)の、リンゴモンハマキ(Archips breviplicanus)、ミダレカクモンハマキ(Archips fuscocupreanus);その他の、トウヒノシントメハマキ (Choristoneura fumiferana)、コドリンガ(Cydia pomonella)、ブドウホソハマキ(Eupoecilia ambiguella)、ナシヒメシンクイ(Grapholitha molesta)、チャハマキ(Homona magnanima)、マメシンクイガ(Leguminivora glycinivorella)、ホソバヒメハマキ(Lobesia botrana)、マメヒメサヤムシガ(Matsumuraeses phaseoli)、トビハマキ(Pandemis heparana)、テングハマキ(Sparganothis pilleriana);
(u)スガ科(Yponomeutidae)のガ、例えば、リンゴヒメシンクイ(Argyresthia conjugella)。 (r) moths of the family Stathmopodidae, such as Stathmopoda masinissa;
(s) moths of the Tineidae family, such as Tinea translucens;
(t) Moths of the Tortricidae family, such as Adoxophyes honmai, Adoxophyes orana of the Adoxophyes spp.; for example, Archipus spp. ), Archips breviplicanus, Archips fuscocupreanus; others, Choristoneura fumiferana, Cydia pomonella, Eupoecilia ambiguella, Grapholitha molesta. ), Homona magnanima, Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana, Sparganothis pilleriana;
(u) A moth of the family Yponomeutidae, such as Argyrethia conjugella.
(s)ヒロズコガ科(Tineidae)のガ、例えば、イガ(Tinea translucens);
(t)ハマキガ科(Tortricidae)のガ、例えば、アドキソフィエス属種(Adoxophyes spp.)の、チャノコカクモンハマキ(Adoxophyes honmai)、リンゴコカクモンハマキ(Adoxophyes orana);例えば、アルチプス属種(Archips spp.)の、リンゴモンハマキ(Archips breviplicanus)、ミダレカクモンハマキ(Archips fuscocupreanus);その他の、トウヒノシントメハマキ (Choristoneura fumiferana)、コドリンガ(Cydia pomonella)、ブドウホソハマキ(Eupoecilia ambiguella)、ナシヒメシンクイ(Grapholitha molesta)、チャハマキ(Homona magnanima)、マメシンクイガ(Leguminivora glycinivorella)、ホソバヒメハマキ(Lobesia botrana)、マメヒメサヤムシガ(Matsumuraeses phaseoli)、トビハマキ(Pandemis heparana)、テングハマキ(Sparganothis pilleriana);
(u)スガ科(Yponomeutidae)のガ、例えば、リンゴヒメシンクイ(Argyresthia conjugella)。 (r) moths of the family Stathmopodidae, such as Stathmopoda masinissa;
(s) moths of the Tineidae family, such as Tinea translucens;
(t) Moths of the Tortricidae family, such as Adoxophyes honmai, Adoxophyes orana of the Adoxophyes spp.; for example, Archipus spp. ), Archips breviplicanus, Archips fuscocupreanus; others, Choristoneura fumiferana, Cydia pomonella, Eupoecilia ambiguella, Grapholitha molesta. ), Homona magnanima, Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana, Sparganothis pilleriana;
(u) A moth of the family Yponomeutidae, such as Argyrethia conjugella.
(2)アザミウマ目(Thysanoptera)害虫
(a)クダアザミウマ科(Phlaeothripidae)の、例えば、カキクダアザミウマ(Ponticulothrips diospyrosi);
(b)アザミウマ科(Thripidae)の、例えば、フランクリニェラ属種(Frankliniella spp.)の、ヒラズハナアザミウマ(Frankliniella intonsa)、ミカンキイロアザミウマ(Frankliniella occidentalis);例えば、トリプス属種(Thrips spp.)の、ミナミキイロアザミウマ(Thrips palmi)、ネギアザミウマ(Thrips tabaci);その他の、クロトンアザミウマ(Heliothrips haemorrhoidalis)、チャノキイロアザミウマ(Scirtothrips dorsalis)。 (2) Thysanoptera pests (a) Phlaeothripidae, for example, Ponticulothrips diospyrosi;
(b) Thripidae, for example, Frankliniella spp., Frankliniella intonsa, Frankliniella occidentalis; for example, Thrips spp., Southern yellow thrips; Thrips palmi, Thrips tabaci; others, Heliothrips haemorrhoidalis, Scirtothrips dorsalis.
(a)クダアザミウマ科(Phlaeothripidae)の、例えば、カキクダアザミウマ(Ponticulothrips diospyrosi);
(b)アザミウマ科(Thripidae)の、例えば、フランクリニェラ属種(Frankliniella spp.)の、ヒラズハナアザミウマ(Frankliniella intonsa)、ミカンキイロアザミウマ(Frankliniella occidentalis);例えば、トリプス属種(Thrips spp.)の、ミナミキイロアザミウマ(Thrips palmi)、ネギアザミウマ(Thrips tabaci);その他の、クロトンアザミウマ(Heliothrips haemorrhoidalis)、チャノキイロアザミウマ(Scirtothrips dorsalis)。 (2) Thysanoptera pests (a) Phlaeothripidae, for example, Ponticulothrips diospyrosi;
(b) Thripidae, for example, Frankliniella spp., Frankliniella intonsa, Frankliniella occidentalis; for example, Thrips spp., Southern yellow thrips; Thrips palmi, Thrips tabaci; others, Heliothrips haemorrhoidalis, Scirtothrips dorsalis.
(3)カメムシ目(Hemiptera)の害虫
(A)頸吻亜目(Archaeorrhyncha)
(a)ウンカ科(Delphacidae)の、例えば、ヒメトビウンカ(Laodelphax striatella)、トビイロウンカ(Nilaparvata lugens)、クロフツノウンカ(Perkinsiella saccharicida)、セジロウンカ(Sogatella furcifera)。 (3) Pests of the order Hemiptera (A) Archaeorrhyncha
(a) Members of the family Delphacidae, such as Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, and Sogatella furcifera.
(A)頸吻亜目(Archaeorrhyncha)
(a)ウンカ科(Delphacidae)の、例えば、ヒメトビウンカ(Laodelphax striatella)、トビイロウンカ(Nilaparvata lugens)、クロフツノウンカ(Perkinsiella saccharicida)、セジロウンカ(Sogatella furcifera)。 (3) Pests of the order Hemiptera (A) Archaeorrhyncha
(a) Members of the family Delphacidae, such as Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, and Sogatella furcifera.
(B)頸吻亜目(Clypeorrhyncha)
(a)ヨコバイ科(Cicadellidae)の、例えば、エンポアスカ属種(Empoasca spp.)の、ジャガイモヒメヨコバイ(Empoasca fabae)、カキノヒメヨコバイ(Empoasca nipponica)、チャノミドリヒメヨコバイ(Empoasca onukii)、マメノミドリヒメヨコバイ(Empoasca sakaii)、;その他の、フタテンヒメヨコバイ(Arboridia apicalis)、ミドリナガヨコバイ(Balclutha saltuella)、フタテンオオヨコバイ(Epiacanthus stramineus)、ヒメフタテンヨコバイ(Macrosteles striifrons)、ツマグロヨコバイ(Nephotettix cinctinceps)。 (B) Clypeorrhyncha
(a) Empoasca fabae, Empoasca nipponica, Empoasca onukii, Empoasca onukii, Empoasca spp. of the family Cicadellidae, for example Empoasca spp. Empoasca sakaii; Other leafhoppers: Arboridia apicalis, Balclutha saltuella, Epicanthus stramineus, Macrosteles striifrons, Nephotettix cinctinceps ).
(a)ヨコバイ科(Cicadellidae)の、例えば、エンポアスカ属種(Empoasca spp.)の、ジャガイモヒメヨコバイ(Empoasca fabae)、カキノヒメヨコバイ(Empoasca nipponica)、チャノミドリヒメヨコバイ(Empoasca onukii)、マメノミドリヒメヨコバイ(Empoasca sakaii)、;その他の、フタテンヒメヨコバイ(Arboridia apicalis)、ミドリナガヨコバイ(Balclutha saltuella)、フタテンオオヨコバイ(Epiacanthus stramineus)、ヒメフタテンヨコバイ(Macrosteles striifrons)、ツマグロヨコバイ(Nephotettix cinctinceps)。 (B) Clypeorrhyncha
(a) Empoasca fabae, Empoasca nipponica, Empoasca onukii, Empoasca onukii, Empoasca spp. of the family Cicadellidae, for example Empoasca spp. Empoasca sakaii; Other leafhoppers: Arboridia apicalis, Balclutha saltuella, Epicanthus stramineus, Macrosteles striifrons, Nephotettix cinctinceps ).
(C)カメムシ亜目(Heteroptera)
(a)ホソヘリカメムシ科(Alydidae)の、例えば、ホソヘリカメムシ(Riptortus clavatus);
(b)ヘリカメムシ科(Coreidae)の、例えば、ホソハリカメムシ(Cletus punctiger)、クモヘリカメムシ(Leptocorisa chinensis);
(c)ナガカメムシ科(Lygaeidae)の、例えば、アメリカコバネナガカメムシ (Blissus leucopterus)、カンシャコバネナガカメムシ(Cavelerius saccharivorus)、コバネヒョウタンナガカメムシ(Togo hemipterus);
(d)カスミカメムシ科(Miridae)の、例えば、クロトビカスミカメ(Halticus insularis)、サビイロカスミカメ (Lygus lineolaris)、コットンフリーホッパー(Psuedatomoscelis seriatus)、ナガムギカスミカメ(Stenodema sibiricum)、アカスジカスミカメ(Stenotus rubrovittatus)、イネホソミドリカスミカメ(Trigonotylus caelestialium); (C) Heteroptera
(a) Alydidae, for example, Riptortus clavatus;
(b) Coreidae, for example Cletus punctiger, Leptocorisa chinensis;
(c) Lygaeidae, such as Blissus leucopterus, Cavelerius saccharivorus, Togo hemipterus;
(d) Members of the Miridae family, such as Halticus insularis, Lygus lineolaris, Cotton Free Hopper (Psuedatomoscelis seriatus), Stenodema sibiricum, and Stenotus rubrovitttatus. ), Trigonotylus caelestialium;
(a)ホソヘリカメムシ科(Alydidae)の、例えば、ホソヘリカメムシ(Riptortus clavatus);
(b)ヘリカメムシ科(Coreidae)の、例えば、ホソハリカメムシ(Cletus punctiger)、クモヘリカメムシ(Leptocorisa chinensis);
(c)ナガカメムシ科(Lygaeidae)の、例えば、アメリカコバネナガカメムシ (Blissus leucopterus)、カンシャコバネナガカメムシ(Cavelerius saccharivorus)、コバネヒョウタンナガカメムシ(Togo hemipterus);
(d)カスミカメムシ科(Miridae)の、例えば、クロトビカスミカメ(Halticus insularis)、サビイロカスミカメ (Lygus lineolaris)、コットンフリーホッパー(Psuedatomoscelis seriatus)、ナガムギカスミカメ(Stenodema sibiricum)、アカスジカスミカメ(Stenotus rubrovittatus)、イネホソミドリカスミカメ(Trigonotylus caelestialium); (C) Heteroptera
(a) Alydidae, for example, Riptortus clavatus;
(b) Coreidae, for example Cletus punctiger, Leptocorisa chinensis;
(c) Lygaeidae, such as Blissus leucopterus, Cavelerius saccharivorus, Togo hemipterus;
(d) Members of the Miridae family, such as Halticus insularis, Lygus lineolaris, Cotton Free Hopper (Psuedatomoscelis seriatus), Stenodema sibiricum, and Stenotus rubrovitttatus. ), Trigonotylus caelestialium;
(e)カメムシ科(Pentatomidae)の、例えば、ネザラ属種(Nezara spp.)の、アオクサカメムシ(Nezara antennata)、ミナミアオカメムシ(Nezara viridula);例えば、シラホシカメムシ属種(Eysarcoris spp.)の、トゲシラホシカメムシ(Eysarcoris aeneus)、オオトゲシラホシカメムシ(Eysarcoris lewisi)、シラホシカメムシ(Eysarcoris ventralis)、その他の、ブチヒゲカメムシ(Dolycoris baccarum)、ナガメ(Eurydema rugosum)、ツヤアオカメムシ(Glaucias subpunctatus)、サギカメムシ(Halyomorpha halys)、クイチモンジカメムシ(Piezodorus hybneri)、チャバネアオカメムシ(Plautia crossota)、イネクロカメムシ(Scotinophora lurida);
(f)ホシカメムシ科(Pyrrhocoridae)の、例えば、アカホシカメムシ(Dysdercus cingulatus);
(g)ヒメヘリカメムシ科(Rhopalidae)の、例えば、アカヒメヘリカメムシ(Rhopalusmsculatus);
(h)キンカメムシ科(Scutelleridae)の、例えば、ムギチャイロカメムシ(Eurygaster integriceps);
(i)グンバイムシ科(Tingidae)の、例えば、ナシグンバイ(Stephanitis nashi)。 (e) Pentatomidae, such as Nezara spp., Nezara antennata, Nezara viridula; for example, Eysarcoris spp. , Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, others, Dolycoris baccarum, Eurydema rugosum, Glaucias subpunctatus, and Eysarcoris ventralis. Halyomorpha halys), Piezodorus hybneri, Plautia crossota, Scotinophora lurida;
(f) Pyrrhocoridae, for example, Dysdercus cingulatus;
(g) Rhopalus musculatus of the family Rhopalidae, for example;
(h) Scutelleridae, for example, Eurygaster integriceps;
(i) Tingidae, for example Stephanitis nashi.
(f)ホシカメムシ科(Pyrrhocoridae)の、例えば、アカホシカメムシ(Dysdercus cingulatus);
(g)ヒメヘリカメムシ科(Rhopalidae)の、例えば、アカヒメヘリカメムシ(Rhopalusmsculatus);
(h)キンカメムシ科(Scutelleridae)の、例えば、ムギチャイロカメムシ(Eurygaster integriceps);
(i)グンバイムシ科(Tingidae)の、例えば、ナシグンバイ(Stephanitis nashi)。 (e) Pentatomidae, such as Nezara spp., Nezara antennata, Nezara viridula; for example, Eysarcoris spp. , Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, others, Dolycoris baccarum, Eurydema rugosum, Glaucias subpunctatus, and Eysarcoris ventralis. Halyomorpha halys), Piezodorus hybneri, Plautia crossota, Scotinophora lurida;
(f) Pyrrhocoridae, for example, Dysdercus cingulatus;
(g) Rhopalus musculatus of the family Rhopalidae, for example;
(h) Scutelleridae, for example, Eurygaster integriceps;
(i) Tingidae, for example Stephanitis nashi.
(D)腹吻亜目(Sternorrhyncha)
(a)カサアブラムシ科(Adelgidae)の、例えば、カラマツカサアブラムシ(Adelges laricis);
(b)コナジラミ科(Aleyrodidae)の、例えば、ベミシア属種(Bemisia spp.)の、シルバーリーフコナジラミ(Bemisia argentifolii)、タバココナジラミ(Bemisia tabaci);その他の、ミカントゲコナジラミ(Aleurocanthus spiniferus)、ミカンコナジラミ(Dialeurodes citri)、オンシツコナジラミ(Trialeurodes vaporariorum);
(c)アブラムシ科(Aphididae)の、例えば、アフィス属種(Aphis spp.)の、マメアブラムシ(Aphis craccivora)、マメクロアブラムシ(Aphis fabae)、イチゴネアブラムシ(Aphis forbesi)、ワタアブラムシ(Aphis gossypii)、ヨーロッパリンゴアブラムシ(Aphis pomi)、ニワトコアブラムシ(Aphis sambuci)、ユキヤナギアブラムシ(Aphis spiraecola);例えば、ロパロシフム属種(Rhopalosiphum spp.)の、トウモロコシアブラムシ(Rhopalosiphum maidis)、ムギクビレアブラムシ(Rhopalosiphum padi);例えば、ジサフィス属種(Dysaphis spp.)の、オオバコアブラムシ(Dysaphis plantaginea)、ギシギシネアブラムシ(Dysaphis radicola);例えば、マクロシフム属種(Macrosiphum spp.)の、ムギヒゲナガアブラムシ(Macrosiphum avenae)、チューリップヒゲナガアブラムシ(Macrosiphum euphorbiae);例えば、ミズス属種(Myzus spp.)の、ニワウメクロコブアブラムシ (Myzus cerasi)、モモアカアブラムシ(Myzus persicae)、カワリコブアブラムシ(Myzus varians);その他の、エンドウヒゲナガアブラムシ(Acyrthosiphon pisum)、ジャガイモヒゲナガアブラムシ(Aulacorthum solani)、ムギワラギクオマルアブラムシ(Brachycaudus helichrysi)、ダイコンアブラムシ(Brevicoryne brassicae)、イチゴケナガアブラムシ(Chaetosiphon fragaefolii)、モモコフキアブラムシ(Hyalopterus pruni)、チシャミドリアブラムシ(Hyperomyzus lactucae)、ニセダイコンアブラムシ(Lipaphis erysimi)、ソラマメヒゲナガアブラムシ(Megoura viciae)、ムギウスイロアブラムシ(Metopolophium dirhodum)、レタスアブラムシ(Nasonovia ribis-nigri)、ホップイボアブラムシ(Phorodon humuli)、ムギミドリアブラムシ(Schizaphis graminum)、ムギヒゲナガアブラムシ(Sitobion avenae)、コミカンアブラムシ(Toxoptera aurantii); (D) Sternorrhyncha
(a) Adelgidae, for example, the larch aphid (Adelges laricis);
(b) Bemisia argentifolii, Bemisia tabaci of the family Aleyrodidae, such as Bemisia spp.; other, Aleurocanthus spiniferus, citrus whitefly; (Dialeurodes citri), whitefly (Trialeurodes vaporariorum);
(c) Aphis craccivora, Aphis fabae, Aphis forbesi, and Aphis gossypii of the Aphidae family, such as Aphis spp. ), European apple aphid (Aphis pomi), elderberry aphid (Aphis sambuci), snow willow aphid (Aphis spiraecola); for example, Rhopalosiphum spp., corn aphid (Rhopalosiphum maidis), wheat aphid (Rhopalosiphum padi) For example, Dysaphis spp., Dysaphis plantaginea, Dysaphis radicola; For example, Macrosiphum avenae, Macrosiphum avenae, Tulip beard moth. Aphids (Macrosiphum euphorbiae); for example, Myzus spp., Myzus cerasi, Myzus persicae, Myzus varians; other aphids (Macrosiphum euphorbiae); Acyrthosiphon pisum), Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, Chaetosiphon fragaefolii, Hyalopterus pruni, Hyperomyzus lactuc ae ), Japanese radish aphid (Lipaphis erysimi), broad bean aphid (Megoura viciae), wheat aphid (Metopolophium dirhodum), lettuce aphid (Nasonovia ribis-nigri), hop aphid (Phorodon humuli), wheat aphid (Schizaphis graminum) ), wheat aphid (Sitobion avenae), comic cane aphid (Toxoptera aurantii);
(a)カサアブラムシ科(Adelgidae)の、例えば、カラマツカサアブラムシ(Adelges laricis);
(b)コナジラミ科(Aleyrodidae)の、例えば、ベミシア属種(Bemisia spp.)の、シルバーリーフコナジラミ(Bemisia argentifolii)、タバココナジラミ(Bemisia tabaci);その他の、ミカントゲコナジラミ(Aleurocanthus spiniferus)、ミカンコナジラミ(Dialeurodes citri)、オンシツコナジラミ(Trialeurodes vaporariorum);
(c)アブラムシ科(Aphididae)の、例えば、アフィス属種(Aphis spp.)の、マメアブラムシ(Aphis craccivora)、マメクロアブラムシ(Aphis fabae)、イチゴネアブラムシ(Aphis forbesi)、ワタアブラムシ(Aphis gossypii)、ヨーロッパリンゴアブラムシ(Aphis pomi)、ニワトコアブラムシ(Aphis sambuci)、ユキヤナギアブラムシ(Aphis spiraecola);例えば、ロパロシフム属種(Rhopalosiphum spp.)の、トウモロコシアブラムシ(Rhopalosiphum maidis)、ムギクビレアブラムシ(Rhopalosiphum padi);例えば、ジサフィス属種(Dysaphis spp.)の、オオバコアブラムシ(Dysaphis plantaginea)、ギシギシネアブラムシ(Dysaphis radicola);例えば、マクロシフム属種(Macrosiphum spp.)の、ムギヒゲナガアブラムシ(Macrosiphum avenae)、チューリップヒゲナガアブラムシ(Macrosiphum euphorbiae);例えば、ミズス属種(Myzus spp.)の、ニワウメクロコブアブラムシ (Myzus cerasi)、モモアカアブラムシ(Myzus persicae)、カワリコブアブラムシ(Myzus varians);その他の、エンドウヒゲナガアブラムシ(Acyrthosiphon pisum)、ジャガイモヒゲナガアブラムシ(Aulacorthum solani)、ムギワラギクオマルアブラムシ(Brachycaudus helichrysi)、ダイコンアブラムシ(Brevicoryne brassicae)、イチゴケナガアブラムシ(Chaetosiphon fragaefolii)、モモコフキアブラムシ(Hyalopterus pruni)、チシャミドリアブラムシ(Hyperomyzus lactucae)、ニセダイコンアブラムシ(Lipaphis erysimi)、ソラマメヒゲナガアブラムシ(Megoura viciae)、ムギウスイロアブラムシ(Metopolophium dirhodum)、レタスアブラムシ(Nasonovia ribis-nigri)、ホップイボアブラムシ(Phorodon humuli)、ムギミドリアブラムシ(Schizaphis graminum)、ムギヒゲナガアブラムシ(Sitobion avenae)、コミカンアブラムシ(Toxoptera aurantii); (D) Sternorrhyncha
(a) Adelgidae, for example, the larch aphid (Adelges laricis);
(b) Bemisia argentifolii, Bemisia tabaci of the family Aleyrodidae, such as Bemisia spp.; other, Aleurocanthus spiniferus, citrus whitefly; (Dialeurodes citri), whitefly (Trialeurodes vaporariorum);
(c) Aphis craccivora, Aphis fabae, Aphis forbesi, and Aphis gossypii of the Aphidae family, such as Aphis spp. ), European apple aphid (Aphis pomi), elderberry aphid (Aphis sambuci), snow willow aphid (Aphis spiraecola); for example, Rhopalosiphum spp., corn aphid (Rhopalosiphum maidis), wheat aphid (Rhopalosiphum padi) For example, Dysaphis spp., Dysaphis plantaginea, Dysaphis radicola; For example, Macrosiphum avenae, Macrosiphum avenae, Tulip beard moth. Aphids (Macrosiphum euphorbiae); for example, Myzus spp., Myzus cerasi, Myzus persicae, Myzus varians; other aphids (Macrosiphum euphorbiae); Acyrthosiphon pisum), Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, Chaetosiphon fragaefolii, Hyalopterus pruni, Hyperomyzus lactuc ae ), Japanese radish aphid (Lipaphis erysimi), broad bean aphid (Megoura viciae), wheat aphid (Metopolophium dirhodum), lettuce aphid (Nasonovia ribis-nigri), hop aphid (Phorodon humuli), wheat aphid (Schizaphis graminum) ), wheat aphid (Sitobion avenae), comic cane aphid (Toxoptera aurantii);
(d)カタカイガラムシ科(Coccidae)の、例えば、セロプラスター属種(Ceroplastesspp.)の、ツノロウムシ(Ceroplastes ceriferus)、ルビーロウムシ(Ceroplastes rubens);
(e)マルカイガラムシ科(Diaspididae)の、シューダウラカスピス属種(Pseudaulacaspis spp.)の、クワシロカイガラムシ(Pseudaulacaspis pentagona)、ウメシロカイガラムシ(Pseudaulacaspis prunicola);例えば、ウナスピス属種(Unaspis spp.)の、マサキナガカイガラムシ(Unaspis euonymi)、ヤノネカイガラムシ(Unaspis yanonensis);その他の、アカマルカイガラムシ(Aonidiella aurantii)、ナシマルカイガラムシ(Comstockaspis perniciosa)、チャコノハカイガラムシ(Fiorinia theae)、チャノマルカイガラムシ(Pseudaonidia paeoniae);
(f)ワタフキカイガラムシ科(Margarodidae)の、例えば、オオワラジカイガラムシ(Drosicha corpulenta)、イセリアカイガラムシ(Icerya purchasi);
(g)ネアブラムシ科(Phylloxeridae)の、例えば、ブドウネアブラムシ(Viteus vitifolii);
(h)コナカイガラムシ科(Pseudococcidae )の、例えば、プラノコッカス属種(Planococcus spp.)の、ミカンコナカイガラムシ(Planococcus citri)、フジコナカイガラムシ(Planococcus kuraunhiae);その他の、ナスコナカイガラムシ(Phenacoccus solani)、クワコナカイガラムシ(Pseudococcus comstocki);
(i)キジラミ科(Psyllidae)の、例えば、プスルラ属種(Psylla spp.)の、リンゴキジラミ(Psylla mali)、ナシキジラミ(Psylla pyrisuga);その他の、ミカンキジラミ(Diaphorina citri)。 (d) Cerophlastes ceriferus, Ceroplastes rubens of the family Coccidae, for example, Ceroplastesspp.;
(e) Pseudaulacaspis pentagona, Pseudaulacaspis prunicola of Pseudaulacaspis spp. of Diaspididae; For example, Unaspis spp. Unaspis euonymi, Unaspis yanonensis; others, Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, Pseudaonidia paeoniae );
(f) family Margarodidae, such as Drosicha corpulenta, Icerya purchasi;
(g) of the family Phylloxeridae, for example Viteus vitifolii;
(h) Planococcus citri, Planococcus kuraunhiae of the Pseudococcidae family, such as Planococcus spp.; other Phenacoccus solani , Pseudococcus comstocki;
(i) Psylla mali, Psylla pyrisuga of the family Psyllidae, such as Psylla spp.; and other, Diaphorina citri.
(e)マルカイガラムシ科(Diaspididae)の、シューダウラカスピス属種(Pseudaulacaspis spp.)の、クワシロカイガラムシ(Pseudaulacaspis pentagona)、ウメシロカイガラムシ(Pseudaulacaspis prunicola);例えば、ウナスピス属種(Unaspis spp.)の、マサキナガカイガラムシ(Unaspis euonymi)、ヤノネカイガラムシ(Unaspis yanonensis);その他の、アカマルカイガラムシ(Aonidiella aurantii)、ナシマルカイガラムシ(Comstockaspis perniciosa)、チャコノハカイガラムシ(Fiorinia theae)、チャノマルカイガラムシ(Pseudaonidia paeoniae);
(f)ワタフキカイガラムシ科(Margarodidae)の、例えば、オオワラジカイガラムシ(Drosicha corpulenta)、イセリアカイガラムシ(Icerya purchasi);
(g)ネアブラムシ科(Phylloxeridae)の、例えば、ブドウネアブラムシ(Viteus vitifolii);
(h)コナカイガラムシ科(Pseudococcidae )の、例えば、プラノコッカス属種(Planococcus spp.)の、ミカンコナカイガラムシ(Planococcus citri)、フジコナカイガラムシ(Planococcus kuraunhiae);その他の、ナスコナカイガラムシ(Phenacoccus solani)、クワコナカイガラムシ(Pseudococcus comstocki);
(i)キジラミ科(Psyllidae)の、例えば、プスルラ属種(Psylla spp.)の、リンゴキジラミ(Psylla mali)、ナシキジラミ(Psylla pyrisuga);その他の、ミカンキジラミ(Diaphorina citri)。 (d) Cerophlastes ceriferus, Ceroplastes rubens of the family Coccidae, for example, Ceroplastesspp.;
(e) Pseudaulacaspis pentagona, Pseudaulacaspis prunicola of Pseudaulacaspis spp. of Diaspididae; For example, Unaspis spp. Unaspis euonymi, Unaspis yanonensis; others, Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, Pseudaonidia paeoniae );
(f) family Margarodidae, such as Drosicha corpulenta, Icerya purchasi;
(g) of the family Phylloxeridae, for example Viteus vitifolii;
(h) Planococcus citri, Planococcus kuraunhiae of the Pseudococcidae family, such as Planococcus spp.; other Phenacoccus solani , Pseudococcus comstocki;
(i) Psylla mali, Psylla pyrisuga of the family Psyllidae, such as Psylla spp.; and other, Diaphorina citri.
(4)カブトムシ亜目(Polyphaga)の害虫
(a)シバンムシ科(Anobiidae)の、例えば、タバコシバンムシ(Lasioderma serricorne);
(b)オトシブミ科(Attelabidae)の、例えば、ドロハマキチョッキリ(Byctiscus betulae)、モモチョッキリゾウムシ(Rhynchites heros);
(c)ナガシンクイムシ科(Bostrichidae)の、例えば、ヒラタキクイムシ(Lyctus brunneus);
(d)ミツギリゾウムシ科(Brentidae)の、例えば、アリモドキゾウムシ(Cylas formicarius);
(e)タマムシ科(Buprestidae )の、例えば、アカバナガタマムシ (Agrilus sinuatus);
(f)カミキリムシ科(Cerambycidae)の、例えば、ゴマダラカミキリ(Anoplophora malasiaca)、マツノマダラカミキリ(Monochamus alternatus)、キボシカミキリ(Psacothea hilaris)、ブドウトラカミキリ(Xylotrechus pyrrhoderus);
(g)ハムシ科(Chrysomelidae)の、例えば、ブルクス属種(Bruchus spp.)の、エンドウマメゾウムシ (Bruchus pisorum)、ソラマメゾウムシ(Bruchus rufimanus);例えば、ジアブロチカ属種(Diabrotica spp.)の、ノーザンコーンルートワーム(Diabrotica barberi)、サザンコーンルートワーム(Diabrotica undecimpunctata)、ウエスタンコーンルートワーム(Diabrotica virgifera);例えば、フィロトレタ属種(Phyllotreta spp.)の、ノミトビヨロイムシ(Phyllotreta nemorum)、キスジノミハムシ(Phyllotreta striolata);その他の、ウリハムシ(Aulacophora femoralis)、アズキゾウムシ(Callosobruchus chinensis)、カメノコハムシ(Cassida nebulosa)、テンサイトビハムシ(Chaetocnema concinna)、コロラドハムシ(Leptinotarsa decemlineata)、イネクビホソハムシ(Oulema oryzae)、ナスナガスネトビハムシ(Psylliodes angusticollis); (4) Pests of the suborder Polyphaga (a) of the family Anobiidae, for example, the tobacco beetle (Lasioderma serricorne);
(b) family Attelabidae, such as Byctiscus betulae, Rhynchites heros;
(c) Bostrichidae, for example, Lyctus brunneus;
(d) of the family Brentidae, for example, Cylas formicarius;
(e) Buprestidae, for example, Agrilus sinuatus;
(f) Cerambycidae, such as Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, and Xylotrechus pyrrhoderus;
(g) Chrysomelidae, e.g. Bruchus spp., pea weevil (Bruchus pisorum), broad bean weevil (Bruchus rufimanus); e.g. Diabrotica spp., northern corn; rootworm (Diabrotica barberi), southern corn rootworm (Diabrotica undecimpunctata), western corn rootworm (Diabrotica virgifera); e.g., Phyllotreta spp. ); Others, Aulacophora femoralis, Callosobruchus chinensis, Cassida nebulosa, Chaetocnema concinna, Colorado potato beetle (Leptinotarsa decemlineata), Oulema oryzae, eggplant Psylliodes angusticollis;
(a)シバンムシ科(Anobiidae)の、例えば、タバコシバンムシ(Lasioderma serricorne);
(b)オトシブミ科(Attelabidae)の、例えば、ドロハマキチョッキリ(Byctiscus betulae)、モモチョッキリゾウムシ(Rhynchites heros);
(c)ナガシンクイムシ科(Bostrichidae)の、例えば、ヒラタキクイムシ(Lyctus brunneus);
(d)ミツギリゾウムシ科(Brentidae)の、例えば、アリモドキゾウムシ(Cylas formicarius);
(e)タマムシ科(Buprestidae )の、例えば、アカバナガタマムシ (Agrilus sinuatus);
(f)カミキリムシ科(Cerambycidae)の、例えば、ゴマダラカミキリ(Anoplophora malasiaca)、マツノマダラカミキリ(Monochamus alternatus)、キボシカミキリ(Psacothea hilaris)、ブドウトラカミキリ(Xylotrechus pyrrhoderus);
(g)ハムシ科(Chrysomelidae)の、例えば、ブルクス属種(Bruchus spp.)の、エンドウマメゾウムシ (Bruchus pisorum)、ソラマメゾウムシ(Bruchus rufimanus);例えば、ジアブロチカ属種(Diabrotica spp.)の、ノーザンコーンルートワーム(Diabrotica barberi)、サザンコーンルートワーム(Diabrotica undecimpunctata)、ウエスタンコーンルートワーム(Diabrotica virgifera);例えば、フィロトレタ属種(Phyllotreta spp.)の、ノミトビヨロイムシ(Phyllotreta nemorum)、キスジノミハムシ(Phyllotreta striolata);その他の、ウリハムシ(Aulacophora femoralis)、アズキゾウムシ(Callosobruchus chinensis)、カメノコハムシ(Cassida nebulosa)、テンサイトビハムシ(Chaetocnema concinna)、コロラドハムシ(Leptinotarsa decemlineata)、イネクビホソハムシ(Oulema oryzae)、ナスナガスネトビハムシ(Psylliodes angusticollis); (4) Pests of the suborder Polyphaga (a) of the family Anobiidae, for example, the tobacco beetle (Lasioderma serricorne);
(b) family Attelabidae, such as Byctiscus betulae, Rhynchites heros;
(c) Bostrichidae, for example, Lyctus brunneus;
(d) of the family Brentidae, for example, Cylas formicarius;
(e) Buprestidae, for example, Agrilus sinuatus;
(f) Cerambycidae, such as Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, and Xylotrechus pyrrhoderus;
(g) Chrysomelidae, e.g. Bruchus spp., pea weevil (Bruchus pisorum), broad bean weevil (Bruchus rufimanus); e.g. Diabrotica spp., northern corn; rootworm (Diabrotica barberi), southern corn rootworm (Diabrotica undecimpunctata), western corn rootworm (Diabrotica virgifera); e.g., Phyllotreta spp. ); Others, Aulacophora femoralis, Callosobruchus chinensis, Cassida nebulosa, Chaetocnema concinna, Colorado potato beetle (Leptinotarsa decemlineata), Oulema oryzae, eggplant Psylliodes angusticollis;
(h)テントウムシ科(Coccinellidae)の、例えば、エピラクナ属種(Epilachna spp.)の、インゲンテントウ(Epilachna varivestis)、ニジュウヤホシテントウ(Epilachna vigintioctopunctata);
(i)ゾウムシ科(Curculionidae)の、例えば、アントノムス属種(Anthonomus spp.)の、ワタミゾウムシ(Anthonomus grandis)、ナシハナゾウムシ(Anthonomus pomorum);例えば、シトフィルスコクゾウムシ属種(Sitophilus spp.)の、グラナリーウィービル(Sitophilus granarius)、コクゾウムシ(Sitophilus zeamais);その他の、イネゾウムシ(Echinocnemus squameus)、イモゾウムシ(Euscepes postfasciatus)、マツアナアキゾウムシ(Hylobius abietis)、アルファルファタコゾウムシ(Hypera postica)、イネミズゾウムシ(Lissohoptrus oryzophilus)、キンケクチブトゾウムシ(Otiorhynchus sulcatus)、アカアシチビコフキゾウムシ (Sitona lineatus)、シバオサゾウムシ(Sphenophorus venatus);
(j)コメツキムシ科(Elateridae)の、例えば、メラノツス属種(Melanotus spp.)の、マルクビクシコメツキ(Melanotus fortnumi)、カンシャクシコメツキ(Melanotus tamsuyensis);
(k)ケシキスイ科(Nitidulidae)の、例えば、ヒメヒラタケシキスイ(Epuraea domina);
(l)コガネムシ科(Scarabaeidae)の、例えば、アノマラ属種(Anomala spp.)の、ドウガネブイブイ(Anomala cuprea)、ヒメコガネ(Anomala rufocuprea);その他の、キンイロハナムグリ(Cetonia aurata)、コアオハナムグリ(Gametis jucunda)、ナガチャコガネ(Heptophylla picea)、ヨーロッパコフキコガネ (Melolontha melolontha)、マメコガネ(Popillia japonica);
(m)キクイムシ科(Scolytidae)の、例えば、ヤツバキクイ (Ips typographus);
(n)ハネカクシ科(Staphylinidae)の、例えば、アオバアリガタハネカクシ(Paederus fuscipes);
(o)ゴミムシダマシ科(Tenebrionidae)の、例えば、チャイロコメノゴミムシダマシ(Tenebrio molitor)、コクヌストモドキ(Tribolium castaneum);
(p)コクヌスト科(Trogossitidae)の、例えば、コクヌスト(Tenebroides mauritanicus)。 (h) Coccinellidae, for example, Epilachna spp., Epilachna varivestis, Epilachna vigintioctopunctata;
(i) of the family Curculionidae, e.g. Anthonomus spp., boll weevil (Anthonomus grandis), pear weevil (Anthonomus pomorum); e.g. of Sitophilus spp. , granary weevil (Sitophilus granarius), grain weevil (Sitophilus zeamais); other rice weevil (Echinocnemus squameus), corn weevil (Euscepes postfasciatus), pine burrow weevil (Hylobius abietis), alfalfa weevil (Hypera postica), rice water weevil ( Lissohoptrus oryzophilus), Otiorhynchus sulcatus, Sitona lineatus, Sphenophorus venatus;
(j) Melanotus fortnumi, Melanotus tamsuyensis of the family Elateridae, such as Melanotus spp.;
(k) of the family Nitidulidae, for example, Epuraea domina;
(l) Scarabaeidae, such as Anomala spp., Anomala cuprea, Anomala rufocuprea; other species, Cetonia aurata, Gametis jucunda; ), Heptophylla picea, Melolontha melolontha, Popillia japonica;
(m) Scolytidae, for example, Ips typographus;
(n) Staphylinidae, for example, Paederus fuscipes;
(o) Tenebrio molitor, for example, Tenebrio molitor, Tribolium castaneum;
(p) Trogossitidae, for example Tenebroides mauritanicus.
(i)ゾウムシ科(Curculionidae)の、例えば、アントノムス属種(Anthonomus spp.)の、ワタミゾウムシ(Anthonomus grandis)、ナシハナゾウムシ(Anthonomus pomorum);例えば、シトフィルスコクゾウムシ属種(Sitophilus spp.)の、グラナリーウィービル(Sitophilus granarius)、コクゾウムシ(Sitophilus zeamais);その他の、イネゾウムシ(Echinocnemus squameus)、イモゾウムシ(Euscepes postfasciatus)、マツアナアキゾウムシ(Hylobius abietis)、アルファルファタコゾウムシ(Hypera postica)、イネミズゾウムシ(Lissohoptrus oryzophilus)、キンケクチブトゾウムシ(Otiorhynchus sulcatus)、アカアシチビコフキゾウムシ (Sitona lineatus)、シバオサゾウムシ(Sphenophorus venatus);
(j)コメツキムシ科(Elateridae)の、例えば、メラノツス属種(Melanotus spp.)の、マルクビクシコメツキ(Melanotus fortnumi)、カンシャクシコメツキ(Melanotus tamsuyensis);
(k)ケシキスイ科(Nitidulidae)の、例えば、ヒメヒラタケシキスイ(Epuraea domina);
(l)コガネムシ科(Scarabaeidae)の、例えば、アノマラ属種(Anomala spp.)の、ドウガネブイブイ(Anomala cuprea)、ヒメコガネ(Anomala rufocuprea);その他の、キンイロハナムグリ(Cetonia aurata)、コアオハナムグリ(Gametis jucunda)、ナガチャコガネ(Heptophylla picea)、ヨーロッパコフキコガネ (Melolontha melolontha)、マメコガネ(Popillia japonica);
(m)キクイムシ科(Scolytidae)の、例えば、ヤツバキクイ (Ips typographus);
(n)ハネカクシ科(Staphylinidae)の、例えば、アオバアリガタハネカクシ(Paederus fuscipes);
(o)ゴミムシダマシ科(Tenebrionidae)の、例えば、チャイロコメノゴミムシダマシ(Tenebrio molitor)、コクヌストモドキ(Tribolium castaneum);
(p)コクヌスト科(Trogossitidae)の、例えば、コクヌスト(Tenebroides mauritanicus)。 (h) Coccinellidae, for example, Epilachna spp., Epilachna varivestis, Epilachna vigintioctopunctata;
(i) of the family Curculionidae, e.g. Anthonomus spp., boll weevil (Anthonomus grandis), pear weevil (Anthonomus pomorum); e.g. of Sitophilus spp. , granary weevil (Sitophilus granarius), grain weevil (Sitophilus zeamais); other rice weevil (Echinocnemus squameus), corn weevil (Euscepes postfasciatus), pine burrow weevil (Hylobius abietis), alfalfa weevil (Hypera postica), rice water weevil ( Lissohoptrus oryzophilus), Otiorhynchus sulcatus, Sitona lineatus, Sphenophorus venatus;
(j) Melanotus fortnumi, Melanotus tamsuyensis of the family Elateridae, such as Melanotus spp.;
(k) of the family Nitidulidae, for example, Epuraea domina;
(l) Scarabaeidae, such as Anomala spp., Anomala cuprea, Anomala rufocuprea; other species, Cetonia aurata, Gametis jucunda; ), Heptophylla picea, Melolontha melolontha, Popillia japonica;
(m) Scolytidae, for example, Ips typographus;
(n) Staphylinidae, for example, Paederus fuscipes;
(o) Tenebrio molitor, for example, Tenebrio molitor, Tribolium castaneum;
(p) Trogossitidae, for example Tenebroides mauritanicus.
(5)ハエ目(Diptera)の害虫
(A)ハエ亜目(Brachycera)
(a)ハモグリバエ科(Agromyzidae)の、例えば、リリオマイザ属種(Liriomyza spp.)の、ナスハモグリバエ(Liriomyza bryoniae)、ネギハモグリバエ(Liriomyza chinensis)、トマトハモグリバエ(Liriomyza sativae)、マメハモグリバエ(Liriomyza trifolii);その他の、ナモグリバエ(Chromatomyia horticola)、イネハモグリバエ(Agromyza oryzae);
(b)ハナバエ科(Anthomyiidae)の、例えば、デリア属種(Delia spp.)の、タネバエ(Delia platura)、キャベツハナバエ (Delia radicum);その他の、テンサイモグリハナバエ(Pegomya cunicularia);
(c)ショウジョウバエ科(Drosophilidae)の、例えば、ショウジョウバエ属種(Drosophila spp.)の、キイロショウジョウバエ(Drosophila melanogaster)、オウトウショウジョウバエ(Drosophila suzukii);
(d)ミギワバエ科(Ephydridae)の、例えば、イネヒメハモグリバエ(Hydrellia griseola);
(e)ハネオレバエ科(Psilidae)の、例えば、ニンジンサビバエ (Psila rosae);
(f)ミバエ科(Tephritidae)の、例えば、バクトロセラ属種(Bactrocera spp.)の、ウリミバエ(Bactrocera cucurbitae)、ミカンコミバエ(Bactrocera dorsalis);例えば、ラゴレチス属種(Rhagoletis spp.)の、ヨーロッパオウトウミバエ (Rhagoletis cerasi)、リンゴミバエ (Rhagoletis pomonella);その他の、チチュウカイミバエ(Ceratitis capitata)、オリーブミバエ(Dacus oleae)。 (5) Pests of Diptera (A) Brachycera
(a) family Agromyzidae, for example, Liriomyza spp., Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, Liriomyza trifolii; Others, Chromatomyia horticola, Agromyza oryzae;
(b) Anthomyiidae, such as Delia spp., Delia platura, and Delia radicum; other Pegomya cunicularia;
(c) Drosophila melanogaster, Drosophila suzukii of the family Drosophilidae, for example, Drosophila spp.;
(d) Ephydridae, for example, Hydrellia griseola;
(e) Psilidae, for example, Psila rosae;
(f) Bactrocera cucurbitae, Bactrocera dorsalis of the family Tephritidae, e.g. Bactrocera spp., Bactrocera dorsalis; European fruit fly (Rhagoletis spp.); Rhagoletis cerasi), Rhagoletis pomonella; others, Ceratitis capitata, Dacus oleae.
(A)ハエ亜目(Brachycera)
(a)ハモグリバエ科(Agromyzidae)の、例えば、リリオマイザ属種(Liriomyza spp.)の、ナスハモグリバエ(Liriomyza bryoniae)、ネギハモグリバエ(Liriomyza chinensis)、トマトハモグリバエ(Liriomyza sativae)、マメハモグリバエ(Liriomyza trifolii);その他の、ナモグリバエ(Chromatomyia horticola)、イネハモグリバエ(Agromyza oryzae);
(b)ハナバエ科(Anthomyiidae)の、例えば、デリア属種(Delia spp.)の、タネバエ(Delia platura)、キャベツハナバエ (Delia radicum);その他の、テンサイモグリハナバエ(Pegomya cunicularia);
(c)ショウジョウバエ科(Drosophilidae)の、例えば、ショウジョウバエ属種(Drosophila spp.)の、キイロショウジョウバエ(Drosophila melanogaster)、オウトウショウジョウバエ(Drosophila suzukii);
(d)ミギワバエ科(Ephydridae)の、例えば、イネヒメハモグリバエ(Hydrellia griseola);
(e)ハネオレバエ科(Psilidae)の、例えば、ニンジンサビバエ (Psila rosae);
(f)ミバエ科(Tephritidae)の、例えば、バクトロセラ属種(Bactrocera spp.)の、ウリミバエ(Bactrocera cucurbitae)、ミカンコミバエ(Bactrocera dorsalis);例えば、ラゴレチス属種(Rhagoletis spp.)の、ヨーロッパオウトウミバエ (Rhagoletis cerasi)、リンゴミバエ (Rhagoletis pomonella);その他の、チチュウカイミバエ(Ceratitis capitata)、オリーブミバエ(Dacus oleae)。 (5) Pests of Diptera (A) Brachycera
(a) family Agromyzidae, for example, Liriomyza spp., Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, Liriomyza trifolii; Others, Chromatomyia horticola, Agromyza oryzae;
(b) Anthomyiidae, such as Delia spp., Delia platura, and Delia radicum; other Pegomya cunicularia;
(c) Drosophila melanogaster, Drosophila suzukii of the family Drosophilidae, for example, Drosophila spp.;
(d) Ephydridae, for example, Hydrellia griseola;
(e) Psilidae, for example, Psila rosae;
(f) Bactrocera cucurbitae, Bactrocera dorsalis of the family Tephritidae, e.g. Bactrocera spp., Bactrocera dorsalis; European fruit fly (Rhagoletis spp.); Rhagoletis cerasi), Rhagoletis pomonella; others, Ceratitis capitata, Dacus oleae.
(B)カ亜目(Nematocera)
(a)タマバエ科(Cecidomyiidae)の、例えば、ダイズサヤタマバエ(Asphondylia yushimai)、ソルガムタマバエ(Contarinia sorghicola)、ヘシアンバエ(Mayetiola destructor)、ムギアカタマバエ(Sitodiplosis mosellana)。 (B) Nematocera
(a) Family Cecidomyiidae, such as Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor, and Sitodiplosis mosellana.
(a)タマバエ科(Cecidomyiidae)の、例えば、ダイズサヤタマバエ(Asphondylia yushimai)、ソルガムタマバエ(Contarinia sorghicola)、ヘシアンバエ(Mayetiola destructor)、ムギアカタマバエ(Sitodiplosis mosellana)。 (B) Nematocera
(a) Family Cecidomyiidae, such as Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor, and Sitodiplosis mosellana.
(6)バッタ目(Orthoptera)の害虫
(a)バッタ科(Acrididae)の、例えば、スキストセルカ属種(Schistocerca spp.)の、アメリカイナゴ (Schistocerca americana)、サバクトビバッタ(Schistocerca gregaria);その他の、オーストラリアトビバッタ(Chortoicetes terminifera)、モロッコイナゴ (Dociostaurus maroccanus)、トノサマバッタ(Locusta migratoria)、ブラウンイナゴ(Locustana pardalina)、アカトビバッタ (Nomadacris septemfasciata)、コバネイナゴ(Oxya yezoensis);
(b)コオロギ科(Gryllidae)の、例えば、ヨーロッパイエコオロギ (Acheta domestica)、エンマコオロギ(Teleogryllus emma);
(c)ケラ科(Gryllotalpidae)の、例えば、ケラ(Gryllotalpa orientalis);
(d)キリギリス科(Tettigoniidae)の、例えば、クラズミウマ (Tachycines asynamorus)。 (6) Pests of the order Orthoptera (a) Acrididae, such as Schistocerca spp., Schistocerca americana, Schistocerca gregaria; other, Australian locust (Chortoicetes terminifera), Moroccan locust (Dociostaurus maroccanus), brown locust (Locusta migratoria), brown locust (Locustana pardalina), red kite locust (Nomadacris septemfasciata), brown locust (Oxya yezoensis);
(b) Gryllidae, for example, European house cricket (Acheta domestica), Enma cricket (Teleogryllus emma);
(c) Molecular family (Gryllotalpidae), for example, Molecular mole (Gryllotalpa orientalis);
(d) Members of the family Tettigoniidae, such as Tachycines asynamorus.
(a)バッタ科(Acrididae)の、例えば、スキストセルカ属種(Schistocerca spp.)の、アメリカイナゴ (Schistocerca americana)、サバクトビバッタ(Schistocerca gregaria);その他の、オーストラリアトビバッタ(Chortoicetes terminifera)、モロッコイナゴ (Dociostaurus maroccanus)、トノサマバッタ(Locusta migratoria)、ブラウンイナゴ(Locustana pardalina)、アカトビバッタ (Nomadacris septemfasciata)、コバネイナゴ(Oxya yezoensis);
(b)コオロギ科(Gryllidae)の、例えば、ヨーロッパイエコオロギ (Acheta domestica)、エンマコオロギ(Teleogryllus emma);
(c)ケラ科(Gryllotalpidae)の、例えば、ケラ(Gryllotalpa orientalis);
(d)キリギリス科(Tettigoniidae)の、例えば、クラズミウマ (Tachycines asynamorus)。 (6) Pests of the order Orthoptera (a) Acrididae, such as Schistocerca spp., Schistocerca americana, Schistocerca gregaria; other, Australian locust (Chortoicetes terminifera), Moroccan locust (Dociostaurus maroccanus), brown locust (Locusta migratoria), brown locust (Locustana pardalina), red kite locust (Nomadacris septemfasciata), brown locust (Oxya yezoensis);
(b) Gryllidae, for example, European house cricket (Acheta domestica), Enma cricket (Teleogryllus emma);
(c) Molecular family (Gryllotalpidae), for example, Molecular mole (Gryllotalpa orientalis);
(d) Members of the family Tettigoniidae, such as Tachycines asynamorus.
(7)ダニ類(Acari)
(A)無気門目(Astigmata)のコナダニ類(Acaridida)
(a)コナダニ科(Acaridae)のダニ、例えば、リゾギルホス属種(Rhizoglyphus spp.)の、ネダニ(Rhizoglyphus echinopus)、ロビンネダニ(Rhizoglyphus robini);例えば、ケナガコナダニ属種(Tyrophagus spp.)の、オンシツケナガコナダニ(Tyrophagus neiswanderi)、オオケナガコナダニ(Tyrophagus perniciosus)、ケナガコナダニ(Tyrophagus putrescentiae)、ホウレンソウケナガコナダニ(Tyrophagus similis);その他、アシブトコナダニ(Acarus siro)、ムギコナダニ(Aleuroglyphus ovatus)、ニセケナガコナダニ(Mycetoglyphus fungivorus); (7) Acari
(A) Acaridida of the order Astigmata.
(a) Mites of the family Acaridae, such as Rhizoglyphus echinopus, Rhizoglyphus robini of the genus Rhizoglyphus spp.; for example, mites of the genus Tyrophagus spp. (Tyrophagus neiswanderi), Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; Others include Acarus siro, Aleuroglyphus ovatus, Mycetog lyphus fungivorus);
(A)無気門目(Astigmata)のコナダニ類(Acaridida)
(a)コナダニ科(Acaridae)のダニ、例えば、リゾギルホス属種(Rhizoglyphus spp.)の、ネダニ(Rhizoglyphus echinopus)、ロビンネダニ(Rhizoglyphus robini);例えば、ケナガコナダニ属種(Tyrophagus spp.)の、オンシツケナガコナダニ(Tyrophagus neiswanderi)、オオケナガコナダニ(Tyrophagus perniciosus)、ケナガコナダニ(Tyrophagus putrescentiae)、ホウレンソウケナガコナダニ(Tyrophagus similis);その他、アシブトコナダニ(Acarus siro)、ムギコナダニ(Aleuroglyphus ovatus)、ニセケナガコナダニ(Mycetoglyphus fungivorus); (7) Acari
(A) Acaridida of the order Astigmata.
(a) Mites of the family Acaridae, such as Rhizoglyphus echinopus, Rhizoglyphus robini of the genus Rhizoglyphus spp.; for example, mites of the genus Tyrophagus spp. (Tyrophagus neiswanderi), Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; Others include Acarus siro, Aleuroglyphus ovatus, Mycetog lyphus fungivorus);
(B)前気門目(Prostigmata)のケダニ類(Actinedida)
(a)ハダニ科(Tetranychidae)のダニ、例えば、ブリオビア属種(Bryobia spp.)の、クローバーハダニ(Bryobia praetiosa)、ニセクローバーハダニ(Bryobia rubrioculus);例えば、エオテトラニクス属種(Eotetranychus spp.)の、コウノシロハダニ(Eotetranychus asiaticus)、アンズハダニ(Eotetranychus boreus)、エノキハダニ(Eotetranychus celtis)、ミチノクハダニ(Eotetranychus geniculatus)、ミヤケハダニ(Eotetranychus kankitus)、クリハダニ(Eotetranychus pruni)、シイノキハダニ(Eotetranychus shii)、スミスハダニ(Eotetranychus smithi)、スギナミハダニ(Eotetranychus suginamensis)、クルミハダニ(Eotetranychus uncatus);例えば、オリゴニクス属種(Oligonychus spp.)の、スギノハダニ(Oligonychus hondoensis)、チビコブハダニ(Oligonychus ilicis)、カラマツハダニ(Oligonychus karamatus)、マンゴーハダニ(Oligonychus mangiferus)、サトウキビハダニ(Oligonychus orthius)、アボガドハダニ(Oligonychus perseae)、エゾスギハダニ(Oligonychus pustulosus)、イネハダニ(Oligonychus shinkajii)、トドマツハダニ(Oligonychus ununguis);例えば、パノニクス属種(Panonychus spp.)の、ミカンハダニ(Panonychus citri)、クワオオハダニ(Panonychus mori)、リンゴハダニ(Panonychus ulmi);例えば、テトラニクス属種(Tetranychus spp.)の、ニセナミハダニ(Tetranychus cinnabarinus)、カンザワハダニ(Tetranychus kanzawai)、アシノワハダニ(Tetranychus ludeni)、ミズナラハダニ(Tetranychus quercivorus)、サガミハダニ(Tetranychus phaselus)、ナミハダニ(Tetranychus urticae)、オウトウハダニ(Tetranychus viennensis)ミツユビナミハダニ (Tetranychus evansi);例えば、アポニクス属(Aponychus spp.)の、イトマキハダニ(Aponychus corpuzae)、タイリクハダニ(Aponychus firmianae);例えば、ミドリハダニ属(Sasanychus spp.)の、ミドリハダニ(Sasanychus akitanus)、ヒメミドリハダニ(Sasanychus pusillus);例えば、シゾテトラニクス属(Shizotetranychus spp.)の、タケスゴモリハダニ(Shizotetranychus celarius)、ケナガスゴモリハダニ(Shizotetranychus longus)、ススキスゴモリハダニ(Shizotetranychus miscanthi)、ヒメササハダニ(Shizotetranychus recki)、ヤナギハダニ(Shizotetranychus schizopus);その他、カタバミハダニ(Tetranychina harti)、ナミケナガハダニ(Tuckerella pavoniformis)、ケウスハダニ(Yezonychus sapporensis); (B) Actinedida of the order Prostigmata.
(a) Mites of the family Tetranychidae, such as Bryobia spp., Bryobia praetiosa, Bryobia rubrioculus; e.g. Eotetranychus spp. There of the stork (eOTETETRANYCHUS ASIATICUS), Ans spider mites (Eotetranychus Boreus), Eotetranychus Celtis, Michinok Hadani (EOTETETRANYCHUS GENICULATUS), Miyakehaha Eotetranychus kankitus, chrysannie (EOTETRANYCHUS PRUNI), EOTETETRANYCHUS SHII, Smith flashy (Eotetranychus smithi), Eotetranychus suginamensis, walnut spider mite (Eotetranychus uncatus); for example, Oligonychus hondoensis, small-knot spider mite (Oligonychus ilicis), larch spider mite (Oligonychus karamatus), of Oligonychus spp. Oligonychus Mangiferus, Oligonychus Orthius, Avocado Perseae, Oligonychus Pustulosus (OLIGONYCHUS PUSTUSUS) Hus shinkajii, oligonychus UNUNGUIS (for example, panychus spp.) For example, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus ludeni of Tetranychus spp. ), Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Tetranychus viennensis, Tetranychus evansi; for example, Aponychus corpuzae, Aponychus spp. ), Aponychus firmianae; for example, Sasanychus akitanus, Sasanychus pusillus, of the genus Sasanychus spp.; for example, Aponychus firmianae, of the genus Shizotetranychus spp. Shizotetranychus celarius), Shizotetranychus longus, Shizotetranychus miscanthi, Shizotetranychus recki, Willow spider mite (Shizotetranychus schizopus); Others, Tetranychina harti, Tuckerella pavoniformis ), Caeus spider mite (Yezonychus sapporensis);
(a)ハダニ科(Tetranychidae)のダニ、例えば、ブリオビア属種(Bryobia spp.)の、クローバーハダニ(Bryobia praetiosa)、ニセクローバーハダニ(Bryobia rubrioculus);例えば、エオテトラニクス属種(Eotetranychus spp.)の、コウノシロハダニ(Eotetranychus asiaticus)、アンズハダニ(Eotetranychus boreus)、エノキハダニ(Eotetranychus celtis)、ミチノクハダニ(Eotetranychus geniculatus)、ミヤケハダニ(Eotetranychus kankitus)、クリハダニ(Eotetranychus pruni)、シイノキハダニ(Eotetranychus shii)、スミスハダニ(Eotetranychus smithi)、スギナミハダニ(Eotetranychus suginamensis)、クルミハダニ(Eotetranychus uncatus);例えば、オリゴニクス属種(Oligonychus spp.)の、スギノハダニ(Oligonychus hondoensis)、チビコブハダニ(Oligonychus ilicis)、カラマツハダニ(Oligonychus karamatus)、マンゴーハダニ(Oligonychus mangiferus)、サトウキビハダニ(Oligonychus orthius)、アボガドハダニ(Oligonychus perseae)、エゾスギハダニ(Oligonychus pustulosus)、イネハダニ(Oligonychus shinkajii)、トドマツハダニ(Oligonychus ununguis);例えば、パノニクス属種(Panonychus spp.)の、ミカンハダニ(Panonychus citri)、クワオオハダニ(Panonychus mori)、リンゴハダニ(Panonychus ulmi);例えば、テトラニクス属種(Tetranychus spp.)の、ニセナミハダニ(Tetranychus cinnabarinus)、カンザワハダニ(Tetranychus kanzawai)、アシノワハダニ(Tetranychus ludeni)、ミズナラハダニ(Tetranychus quercivorus)、サガミハダニ(Tetranychus phaselus)、ナミハダニ(Tetranychus urticae)、オウトウハダニ(Tetranychus viennensis)ミツユビナミハダニ (Tetranychus evansi);例えば、アポニクス属(Aponychus spp.)の、イトマキハダニ(Aponychus corpuzae)、タイリクハダニ(Aponychus firmianae);例えば、ミドリハダニ属(Sasanychus spp.)の、ミドリハダニ(Sasanychus akitanus)、ヒメミドリハダニ(Sasanychus pusillus);例えば、シゾテトラニクス属(Shizotetranychus spp.)の、タケスゴモリハダニ(Shizotetranychus celarius)、ケナガスゴモリハダニ(Shizotetranychus longus)、ススキスゴモリハダニ(Shizotetranychus miscanthi)、ヒメササハダニ(Shizotetranychus recki)、ヤナギハダニ(Shizotetranychus schizopus);その他、カタバミハダニ(Tetranychina harti)、ナミケナガハダニ(Tuckerella pavoniformis)、ケウスハダニ(Yezonychus sapporensis); (B) Actinedida of the order Prostigmata.
(a) Mites of the family Tetranychidae, such as Bryobia spp., Bryobia praetiosa, Bryobia rubrioculus; e.g. Eotetranychus spp. There of the stork (eOTETETRANYCHUS ASIATICUS), Ans spider mites (Eotetranychus Boreus), Eotetranychus Celtis, Michinok Hadani (EOTETETRANYCHUS GENICULATUS), Miyakehaha Eotetranychus kankitus, chrysannie (EOTETRANYCHUS PRUNI), EOTETETRANYCHUS SHII, Smith flashy (Eotetranychus smithi), Eotetranychus suginamensis, walnut spider mite (Eotetranychus uncatus); for example, Oligonychus hondoensis, small-knot spider mite (Oligonychus ilicis), larch spider mite (Oligonychus karamatus), of Oligonychus spp. Oligonychus Mangiferus, Oligonychus Orthius, Avocado Perseae, Oligonychus Pustulosus (OLIGONYCHUS PUSTUSUS) Hus shinkajii, oligonychus UNUNGUIS (for example, panychus spp.) For example, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus ludeni of Tetranychus spp. ), Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Tetranychus viennensis, Tetranychus evansi; for example, Aponychus corpuzae, Aponychus spp. ), Aponychus firmianae; for example, Sasanychus akitanus, Sasanychus pusillus, of the genus Sasanychus spp.; for example, Aponychus firmianae, of the genus Shizotetranychus spp. Shizotetranychus celarius), Shizotetranychus longus, Shizotetranychus miscanthi, Shizotetranychus recki, Willow spider mite (Shizotetranychus schizopus); Others, Tetranychina harti, Tuckerella pavoniformis ), Caeus spider mite (Yezonychus sapporensis);
(b)ヒメハダニ科(Tenuipalpidae)のダニ、例えば、ブレビパルプス属種(Brevipalpus spp.)の、ブドウヒメハダニ(Brevipalpus lewisi)、チャノヒメハダニ(Brevipalpus obovatus)、ミナミヒメハダニ(Brevipalpus phoenicis)、サボテンヒメハダニ(Brevipalpus russulus)、オンシツヒメハダニ(brevipalpus californicus);例えば、テニパルプス属種(Tenuipalpus spp.)の、ランヒメハダニ(Tenuipalpus pacificus)、カキヒメハダニ(Tenuipalpus zhizhilashviliae);その他、パイナップルヒメハダニ(Dolichotetranychus floridanus);
(c)フシダニ科(Eriophyidae)のダニ、例えば、アセリア属種(Aceria spp.)の、カキサビダニ(Aceria diospyri)、イチジクモンサビダニ(Aceria ficus)、クリフシダニ(Aceria japonica)、クコフシダニ(Aceria kuko)、カーネーションサビダニ(Aceria paradianthi)、クコハモグリダニ(Aceria tiyingi)、チューリップサビダニ(Aceria tulipae)、シバハマキフシダニ(Aceria zoysiea);例えば、エリオフィエス属種(Eriophyes spp.)の、ニセナシサビダニ(Eriophyes chibaensis)、ウメフシダニ(Eriophyes emarginatae);例えばアクロプス属種(Aculops spp.)の、トマトサビダニ(Aculops lycopersici)、ミカンサビダニ(Aculops pelekassi);例えば、アクルス属種(Aculus spp.)の、モモサビダニ(Aculus fockeui)、リンゴサビダニ(Aculus schlechtendali);その他、チャノナガサビダニ(Acaphylla theavagrans)、チャノサビダニ(Calacarus carinatus)、ブドウハモグリダニ(Colomerus vitis)、ブドウサビダニ(Calepitrimerus vitis)、ナシサビダニ(Epitrimerus pyri)、キンモクサビダニ(Paraphytoptus kikus)、マキサビダニ(Paracalacarus podocarpi)、リュウキュウミカンサビダニ(Phyllocotruta citri);
(d)ホコリダニ科(Transonemidae)のダニ、例えば、タルソネムス属種(Tarsonemusspp.)の、スジブトホコリダニ(Tarsonemus bilobatus)、アシボソホコリダニ(Tarsonemus waitei);その他、シクラメンホコリダニ(Phytonemus pallidus)、チャノホコリダニ(Polyphagotarsonemus latus);
(e)ハシリダニ科(Penthaleidae)のダニ、例えば、ペンタレウス属種(Penthaleus spp.)の、ハクサイダニ(Penthaleus erythrocephalus)、ムギダニ(Penthaleus major)。 (b) Mites of the Tenuipalpidae family, such as Brevipalpus spp., Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Brevipalpus spp. russulus), Brevipalpus californicus; For example, Tenuipalpus spp. Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; Others, Dolichotetranychus floridanus;
(c) Mites of the family Eriophyidae, such as Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, and carnations of the Aceria spp. Aceria paradianthi, Aceria tiyingi, tulip rust mite, Aceria zoysiea; for example, Eriophyes spp., Eriophyes chibaensis, Eriophyes emarginatae); e.g., Aculops spp., tomato rust mite (Aculops lycopersici), orange rust mite (Aculops pelekassi); e.g., Aculus spp., peach rust mite (Aculus fockeui), apple rust mite (Aculus) schlechtendali; others: Acaphylla theavagrans, Calacarus carinatus, Colomerus vitis, Calepitrimerus vitis, Epitrimerus pyri, Paraphytoptus kikus, Paracalacarus podocarpi), Ryukyu citrus rust mite (Phyllocotruta citri);
(d) Mites of the family Transonemidae, such as Tarsonemus sp., Tarsonemus bilobatus, Tarsonemus waitei; others, Phytonemus pallidus, Polyphagotarsonemus latus ;
(e) Mites of the family Penthaleidae, such as Penthaleus erythrocephalus, Penthaleus major, of the genus Penthaleus spp.
(c)フシダニ科(Eriophyidae)のダニ、例えば、アセリア属種(Aceria spp.)の、カキサビダニ(Aceria diospyri)、イチジクモンサビダニ(Aceria ficus)、クリフシダニ(Aceria japonica)、クコフシダニ(Aceria kuko)、カーネーションサビダニ(Aceria paradianthi)、クコハモグリダニ(Aceria tiyingi)、チューリップサビダニ(Aceria tulipae)、シバハマキフシダニ(Aceria zoysiea);例えば、エリオフィエス属種(Eriophyes spp.)の、ニセナシサビダニ(Eriophyes chibaensis)、ウメフシダニ(Eriophyes emarginatae);例えばアクロプス属種(Aculops spp.)の、トマトサビダニ(Aculops lycopersici)、ミカンサビダニ(Aculops pelekassi);例えば、アクルス属種(Aculus spp.)の、モモサビダニ(Aculus fockeui)、リンゴサビダニ(Aculus schlechtendali);その他、チャノナガサビダニ(Acaphylla theavagrans)、チャノサビダニ(Calacarus carinatus)、ブドウハモグリダニ(Colomerus vitis)、ブドウサビダニ(Calepitrimerus vitis)、ナシサビダニ(Epitrimerus pyri)、キンモクサビダニ(Paraphytoptus kikus)、マキサビダニ(Paracalacarus podocarpi)、リュウキュウミカンサビダニ(Phyllocotruta citri);
(d)ホコリダニ科(Transonemidae)のダニ、例えば、タルソネムス属種(Tarsonemusspp.)の、スジブトホコリダニ(Tarsonemus bilobatus)、アシボソホコリダニ(Tarsonemus waitei);その他、シクラメンホコリダニ(Phytonemus pallidus)、チャノホコリダニ(Polyphagotarsonemus latus);
(e)ハシリダニ科(Penthaleidae)のダニ、例えば、ペンタレウス属種(Penthaleus spp.)の、ハクサイダニ(Penthaleus erythrocephalus)、ムギダニ(Penthaleus major)。 (b) Mites of the Tenuipalpidae family, such as Brevipalpus spp., Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Brevipalpus spp. russulus), Brevipalpus californicus; For example, Tenuipalpus spp. Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; Others, Dolichotetranychus floridanus;
(c) Mites of the family Eriophyidae, such as Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, and carnations of the Aceria spp. Aceria paradianthi, Aceria tiyingi, tulip rust mite, Aceria zoysiea; for example, Eriophyes spp., Eriophyes chibaensis, Eriophyes emarginatae); e.g., Aculops spp., tomato rust mite (Aculops lycopersici), orange rust mite (Aculops pelekassi); e.g., Aculus spp., peach rust mite (Aculus fockeui), apple rust mite (Aculus) schlechtendali; others: Acaphylla theavagrans, Calacarus carinatus, Colomerus vitis, Calepitrimerus vitis, Epitrimerus pyri, Paraphytoptus kikus, Paracalacarus podocarpi), Ryukyu citrus rust mite (Phyllocotruta citri);
(d) Mites of the family Transonemidae, such as Tarsonemus sp., Tarsonemus bilobatus, Tarsonemus waitei; others, Phytonemus pallidus, Polyphagotarsonemus latus ;
(e) Mites of the family Penthaleidae, such as Penthaleus erythrocephalus, Penthaleus major, of the genus Penthaleus spp.
本発明の有害生物防除剤は、殺菌剤、殺虫・殺ダニ剤、殺線虫剤、殺土壌害虫剤などの他の有効成分; 植物調節剤、共力剤、肥料、土壌改良剤、動物用飼料などと混用または併用してもよい。
本発明化合物と他の有効成分との組合せは、殺虫・殺ダニ・殺線虫活性に関して相乗効果が期待できる。相乗効果は、定法に従ってコルビーの式(Colby.S.R. ; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations ; Weeds 15, 20-22頁, 1967)により確認することができる。 The pest control agent of the present invention may contain other active ingredients such as fungicides, insecticides/acaricides, nematicides, and soil insecticides; plant regulators, synergists, fertilizers, soil conditioners, and animals. It may be mixed or used in combination with feed etc.
The combination of the compound of the present invention and other active ingredients can be expected to have a synergistic effect with respect to insecticidal, acaricidal, and nematocidal activities. 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 standard method.
本発明化合物と他の有効成分との組合せは、殺虫・殺ダニ・殺線虫活性に関して相乗効果が期待できる。相乗効果は、定法に従ってコルビーの式(Colby.S.R. ; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations ; Weeds 15, 20-22頁, 1967)により確認することができる。 The pest control agent of the present invention may contain other active ingredients such as fungicides, insecticides/acaricides, nematicides, and soil insecticides; plant regulators, synergists, fertilizers, soil conditioners, and animals. It may be mixed or used in combination with feed etc.
The combination of the compound of the present invention and other active ingredients can be expected to have a synergistic effect with respect to insecticidal, acaricidal, and nematocidal activities. 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 standard method.
本発明の有害生物防除剤と混用または併用することができる、殺虫・殺ダニ剤の具体例を以下に示す。
(1B)アセチルコリンエステラーゼ(AChE)阻害剤(有機リン系)
アセフェート(Acephate)、アザメチホス(Azamethiphos)、アジンホスエチル(Azinphos-ethyl)、アジンホスメチル(Azinphosmethyl)、カズサホス(Cadusafos)、クロレトキシホス(Chlorethoxyfos)、クロルフェンビンホス(Chlorfenvinphos)、クロルメホス(Chlormephos)、クロルピリホス(Chlorpyrifos)、クロルピリホスメチル(Chlorpyrifos-methyl)、クマホス(Coumaphos)、シアノホス(Cyanophos)、ジメトン-S-メチル(Demeton-S-methyl)、ダイアジノン(Diazinon)、ジクロルボス(Dichlorvos/ DDVP)、ジクロトホス(Dicrotophos)、ジメトエート(Dimethoate)、ジメチルビンホス(Dimethylvinphos)、ジスルホトン(Disulfoton)、EPN、エチオン(Ethion)、エトプロホス(Ethoprophos)、ファンフル(Famphur)、フェナミホス(Fenamiphos)、フェニトロチオン(Fenitrothion)、フェンチオン(Fenthion)、ホスチアゼート(Fosthiazate)、ヘプテノホス(Heptenophos)、イミシアホス(Imicyafos)、イソフェンホス(Isofenphos)、イソプロピル=O-(メトキシアミノチオホスホリル)サリチラート(Isopropyl O-(methoxyaminothio-phosphoryl) salicylate)、イソキサチオン(Isoxathion)、マラチオン(Malathion)、メカルバム(Mecarbam)、メタミドホス(Methamidophos)、メチダチオン(Methidathion)、メビンホス(Mevinphos)、モノクロトホス(Monocrotophos)、ナレッド(Naled)、オメトエート(Omethoate)、オキシジメトンメチル(Oxydemeton-methyl)、パラチオン(Parathion)、パラチオンメチル(Parathion-methyl)、フェントエート(Phenthoate)、ホレート(Phorate)、ホサロン(Phosalone)、ホスメット(Phosmet)、ホスファミドン(Phosphamidon)、ホキシム(Phoxim)、ピリミホスメチル(Pirimiphos- methyl)、プロフェノホス(Profenofos)、プロペタムホス(Propetamphos)、プロチオホス(Prothiofos)、ピラクロホス(Pyraclofos)、ピリダフェンチオン(Pyridaphenthion)、キナルホス(Quinalphos)、スルホテップ(Sulfotep)、テブピリムホス(Tebupirimfos)、テメホス(Temephos)、テルブホス(Terbufos)、テトラクロルビンホス(Tetrachlorvinphos)、チオメトン(Thiometon)、トリアゾホス(Triazophos)、トリクロルホン(Trichlorfon)、バミドチオン(Vamidothion)。
ブロモホス-エチル(Bromophos-e)、シアノフェンホス(Cyanofenphos)、デメトン-S-メチルスルホン(Demeton-S-methylsulfone )、ジアリホス(Dialifos)、ジクロフェンチオン(Dichlofenthion)、ジオキサベンゾホス(Dioxabenzofos)、エトリムホス(Etrimfos)、フェンスルホチオン(Fensulfothion)、ホノホス(Fonofos)、ホルモチオン(Formothion)、ヨードフェンホス(iodofenphos)、イサゾホス(Isazofos)、イソカルボホス(Isocarbofos)、メタクリホス(Methacrifos)、ホスホカルブ(Phosphocarb)、ピリミホス-エチル(Pirimiphos-e)、プロパホス(Propaphos)、プロトエート(Prothoate)、スルプロホス(Sulprofos)。 Specific examples of insecticides and acaricides that can be mixed or used in combination with the pest control agent of the present invention are shown below.
(1B) Acetylcholinesterase (AChE) inhibitor (organophosphorus)
Acephate, Azamethiphos, Azinphos-ethyl, Azinphosmethyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoate ( Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate Fosthiazate), Heptenophos, Imicyafos, Isofenphos, Isopropyl O-(methoxyaminothio-phosphoryl) salicylate, Isoxathion, Malathion , Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion , Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos- methyl, Profenofos , Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos (Tetrachlorvinphos), Thiometon, Triazophos, Trichlorfon, Vamidothion.
Bromophos-e, Cyanofenphos, Demeton-S-methylsulfone, Dialifos, Dichlofenthion, Dioxabenzofos, Etrimphos ( Etrimfos, Fensulfothion, Fonofos, Formothion, iodofenphos, Isazofos, Isocarbofos, Methacrifos, Phosphocarb, Pirimiphos -e), Propaphos, Prothoate, Sulprofos.
(1B)アセチルコリンエステラーゼ(AChE)阻害剤(有機リン系)
アセフェート(Acephate)、アザメチホス(Azamethiphos)、アジンホスエチル(Azinphos-ethyl)、アジンホスメチル(Azinphosmethyl)、カズサホス(Cadusafos)、クロレトキシホス(Chlorethoxyfos)、クロルフェンビンホス(Chlorfenvinphos)、クロルメホス(Chlormephos)、クロルピリホス(Chlorpyrifos)、クロルピリホスメチル(Chlorpyrifos-methyl)、クマホス(Coumaphos)、シアノホス(Cyanophos)、ジメトン-S-メチル(Demeton-S-methyl)、ダイアジノン(Diazinon)、ジクロルボス(Dichlorvos/ DDVP)、ジクロトホス(Dicrotophos)、ジメトエート(Dimethoate)、ジメチルビンホス(Dimethylvinphos)、ジスルホトン(Disulfoton)、EPN、エチオン(Ethion)、エトプロホス(Ethoprophos)、ファンフル(Famphur)、フェナミホス(Fenamiphos)、フェニトロチオン(Fenitrothion)、フェンチオン(Fenthion)、ホスチアゼート(Fosthiazate)、ヘプテノホス(Heptenophos)、イミシアホス(Imicyafos)、イソフェンホス(Isofenphos)、イソプロピル=O-(メトキシアミノチオホスホリル)サリチラート(Isopropyl O-(methoxyaminothio-phosphoryl) salicylate)、イソキサチオン(Isoxathion)、マラチオン(Malathion)、メカルバム(Mecarbam)、メタミドホス(Methamidophos)、メチダチオン(Methidathion)、メビンホス(Mevinphos)、モノクロトホス(Monocrotophos)、ナレッド(Naled)、オメトエート(Omethoate)、オキシジメトンメチル(Oxydemeton-methyl)、パラチオン(Parathion)、パラチオンメチル(Parathion-methyl)、フェントエート(Phenthoate)、ホレート(Phorate)、ホサロン(Phosalone)、ホスメット(Phosmet)、ホスファミドン(Phosphamidon)、ホキシム(Phoxim)、ピリミホスメチル(Pirimiphos- methyl)、プロフェノホス(Profenofos)、プロペタムホス(Propetamphos)、プロチオホス(Prothiofos)、ピラクロホス(Pyraclofos)、ピリダフェンチオン(Pyridaphenthion)、キナルホス(Quinalphos)、スルホテップ(Sulfotep)、テブピリムホス(Tebupirimfos)、テメホス(Temephos)、テルブホス(Terbufos)、テトラクロルビンホス(Tetrachlorvinphos)、チオメトン(Thiometon)、トリアゾホス(Triazophos)、トリクロルホン(Trichlorfon)、バミドチオン(Vamidothion)。
ブロモホス-エチル(Bromophos-e)、シアノフェンホス(Cyanofenphos)、デメトン-S-メチルスルホン(Demeton-S-methylsulfone )、ジアリホス(Dialifos)、ジクロフェンチオン(Dichlofenthion)、ジオキサベンゾホス(Dioxabenzofos)、エトリムホス(Etrimfos)、フェンスルホチオン(Fensulfothion)、ホノホス(Fonofos)、ホルモチオン(Formothion)、ヨードフェンホス(iodofenphos)、イサゾホス(Isazofos)、イソカルボホス(Isocarbofos)、メタクリホス(Methacrifos)、ホスホカルブ(Phosphocarb)、ピリミホス-エチル(Pirimiphos-e)、プロパホス(Propaphos)、プロトエート(Prothoate)、スルプロホス(Sulprofos)。 Specific examples of insecticides and acaricides that can be mixed or used in combination with the pest control agent of the present invention are shown below.
(1B) Acetylcholinesterase (AChE) inhibitor (organophosphorus)
Acephate, Azamethiphos, Azinphos-ethyl, Azinphosmethyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoate ( Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate Fosthiazate), Heptenophos, Imicyafos, Isofenphos, Isopropyl O-(methoxyaminothio-phosphoryl) salicylate, Isoxathion, Malathion , Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion , Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos- methyl, Profenofos , Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos (Tetrachlorvinphos), Thiometon, Triazophos, Trichlorfon, Vamidothion.
Bromophos-e, Cyanofenphos, Demeton-S-methylsulfone, Dialifos, Dichlofenthion, Dioxabenzofos, Etrimphos ( Etrimfos, Fensulfothion, Fonofos, Formothion, iodofenphos, Isazofos, Isocarbofos, Methacrifos, Phosphocarb, Pirimiphos -e), Propaphos, Prothoate, Sulprofos.
(2)GABA作動性塩化物イオン(塩素イオン)チャネルブロッカー
クロルデン(Chlordane)、エンドスルファン(Endosulfan);エチプロール(Ethiprole)、フィプロニル(Fipronil)。
アセトプロール(Acetoprole)、カンフェクロル(Camphechlor)、ジエノクロル(Dienochlor)、ヘプタクロル(Heptachlor)、ピラフルプロール(Pyrafluprole)、ピリプロール(Pyriprole);フルフィプロル(Flufiprole)。
(3A)ナトリウムチャネルモジュレーター(ピレスロイド系)
アクリナトリン(Acrinathrin)、アレスリン(Allethrin)、d-シス-トランス-アレスリン(d-cis-trans Allethrin)、d-トランス-アレスリン(d-transAllethrin)、ビフェントリン(Bifenthrin)、ビオアレスリン(Bioallethrin)、ビオアレスリン-S-シクロペンテニル-異性体(Bioallethrin S-cyclopentenyl-isomer)、ビオレスメトリン(Bioresmethrin)、シクロプロトリン(Cycloprothrin)、シフルトリン(Cyfluthrin)、β-シフルトリン(beta-Cyfluthrin)、シハロトリン(Cyhalothrin)、λ-シハロトリン(lambda-Cyhalothrin)、γ-シハロトリン(gamma-Cyhalothrin)、シペルメトリン(Cypermethrin)、α-シペルメトリン(alpha-Cypermethrin)、β-シペルメトリン(beta-Cypermethrin)、θ-シペルメトリン(theta-Cypermethrin)、ζ-シペルメトリン(zeta-Cypermethrin)、シフェノトリン[(1R)-トランス異性体](Cyphenothrin [(1R)-trans-isomers] )、デルタメトリン(Deltamethrin)、エンペントリン[(EZ)-(1R)-異性体](Empenthrin[(EZ)-(1R)-isomers] )、エスフェンバレレート(Esfenvalerate)、エトフェンプロックス(Etofenprox)、フェンプロパトリン(Fenpropathrin)、フェンバレレート(Fenvalerate)、フルシトリネート(Flucythrinate)、フルメトリン(Flumethrin)、τ-フルバリネート(tau-Fluvalinate)、ハルフェンプロックス(Halfenprox)、イミプロトリン(Imiprothrin)、カデスリン(Kadethrin)、ペルメトリン(Permethrin)、フェノトリン[(1R)-トランス異性体](Phenothrin [(1R)-trans-isomer] )、プラレトリン(Prallethrin)、ピレトリン(Pyrethrins)、レスメトリン(Resmethrin)、シラフルオフェン(Silafluofen)、テフルトリン(Tefluthrin)、テトラメスリン(Tetramethrin)、テトラメスリン[(1R)-異性体](Tetramethrin[(1R)-isomers] )、トラロメトリン(Tralomethrin)、トランスフルトリン(Transfluthrin)。
κ-ビフェントリン(kappa-Bifenthrin)、ビオペルメトリン(Biopermethrin)、クロロプラレスリン(Chloroprallethrin)、ジメフルトリン(Dimefluthrin)、フェンフルトリン(Fenfluthrin)、フェンピリトリン(Fenpirithrin)、フルフェンプロックス(Flufenprox)、ヘプタフルスリン(Heptafluthrin)、メペルフルスリン(Meperfluthrin)、ε-メトフルトリン(epsilon-Metofluthrin)、モンフルオロトリン(Momfluorothrin)、ε-モンフルオロトリン(epsilon-Momfluorothrin)、トランス-ペルメトリン(trans-Permethrin)、プロフルトリン(Profluthrin)、プロトリフェンブト(Protrifenbute)、κ-テフルトリン(kappa-Tefluthrin)、テラレトリン(Terallethrin)、テトラメチルフルスリン(Tetramethylfluthrin);ビオエタノメトリン(Bioethanomethrin)。
(3B)ナトリウムチャネルモジュレーター(DDT類)
DDT、メトキシクロル(Methoxychlor)。 (2) GABAergic chloride ion (chloride ion) channel blockers Chlordane, Endosulfan; Ethiprole, Fipronil.
Acetoprole, Camphechlor, Dienochlor, Heptachlor, Pyrafluprole, Pyriprole; Flufiprole.
(3A) Sodium channel modulator (pyrethroid)
Acrinathrin, Allethrin, d-cis-trans Allethrin, d-transAllethrin, Bifenthrin, Bioallethrin, Bioallethrin -S-cyclopentenyl-isomer (Bioallethrin), Bioresmethrin, Cycloprothrin, Cyfluthrin, Beta-Cyfluthrin, Cyhalothrin, λ- Lambda-Cyhalothrin, gamma-Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin ), zeta-Cypermethrin, Cyphenothrin [(1R)-trans-isomers], Deltamethrin, Empenthrin [(EZ)-(1R) -isomers] (Empenthrin[(EZ)-(1R)-isomers]), Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucitrinate ( Flucythrinate), Flumethrin, tau-Fluvalinate, Halfenprox, Imiprothrin, Kadethrin, Permethrin, Phenothrin [(1R)-trans isomer] (Phenothrin [(1R)-trans-isomer]), Prallethrin, Pyrethrins, Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)-trans-isomer] Tetramethrin [(1R)-isomers], Tralomethrin, Transfluthrin.
Kappa-Bifenthrin, Biopermethrin, Chloroprallethrin, Dimefluthrin, Fenfluthrin, Fenpirithrin, Flufenprox, Heptaflu Heptafluthrin, Meperfluthrin, epsilon-Metofluthrin, Momfluorothrin, epsilon-Momfluorothrin, trans-Permethrin, Profluthrin , Protrifenbute, kappa-Tefluthrin, Terallethrin, Tetramethylfluthrin; Bioethanomethrin.
(3B) Sodium channel modulators (DDTs)
DDT, Methoxychlor.
クロルデン(Chlordane)、エンドスルファン(Endosulfan);エチプロール(Ethiprole)、フィプロニル(Fipronil)。
アセトプロール(Acetoprole)、カンフェクロル(Camphechlor)、ジエノクロル(Dienochlor)、ヘプタクロル(Heptachlor)、ピラフルプロール(Pyrafluprole)、ピリプロール(Pyriprole);フルフィプロル(Flufiprole)。
(3A)ナトリウムチャネルモジュレーター(ピレスロイド系)
アクリナトリン(Acrinathrin)、アレスリン(Allethrin)、d-シス-トランス-アレスリン(d-cis-trans Allethrin)、d-トランス-アレスリン(d-transAllethrin)、ビフェントリン(Bifenthrin)、ビオアレスリン(Bioallethrin)、ビオアレスリン-S-シクロペンテニル-異性体(Bioallethrin S-cyclopentenyl-isomer)、ビオレスメトリン(Bioresmethrin)、シクロプロトリン(Cycloprothrin)、シフルトリン(Cyfluthrin)、β-シフルトリン(beta-Cyfluthrin)、シハロトリン(Cyhalothrin)、λ-シハロトリン(lambda-Cyhalothrin)、γ-シハロトリン(gamma-Cyhalothrin)、シペルメトリン(Cypermethrin)、α-シペルメトリン(alpha-Cypermethrin)、β-シペルメトリン(beta-Cypermethrin)、θ-シペルメトリン(theta-Cypermethrin)、ζ-シペルメトリン(zeta-Cypermethrin)、シフェノトリン[(1R)-トランス異性体](Cyphenothrin [(1R)-trans-isomers] )、デルタメトリン(Deltamethrin)、エンペントリン[(EZ)-(1R)-異性体](Empenthrin[(EZ)-(1R)-isomers] )、エスフェンバレレート(Esfenvalerate)、エトフェンプロックス(Etofenprox)、フェンプロパトリン(Fenpropathrin)、フェンバレレート(Fenvalerate)、フルシトリネート(Flucythrinate)、フルメトリン(Flumethrin)、τ-フルバリネート(tau-Fluvalinate)、ハルフェンプロックス(Halfenprox)、イミプロトリン(Imiprothrin)、カデスリン(Kadethrin)、ペルメトリン(Permethrin)、フェノトリン[(1R)-トランス異性体](Phenothrin [(1R)-trans-isomer] )、プラレトリン(Prallethrin)、ピレトリン(Pyrethrins)、レスメトリン(Resmethrin)、シラフルオフェン(Silafluofen)、テフルトリン(Tefluthrin)、テトラメスリン(Tetramethrin)、テトラメスリン[(1R)-異性体](Tetramethrin[(1R)-isomers] )、トラロメトリン(Tralomethrin)、トランスフルトリン(Transfluthrin)。
κ-ビフェントリン(kappa-Bifenthrin)、ビオペルメトリン(Biopermethrin)、クロロプラレスリン(Chloroprallethrin)、ジメフルトリン(Dimefluthrin)、フェンフルトリン(Fenfluthrin)、フェンピリトリン(Fenpirithrin)、フルフェンプロックス(Flufenprox)、ヘプタフルスリン(Heptafluthrin)、メペルフルスリン(Meperfluthrin)、ε-メトフルトリン(epsilon-Metofluthrin)、モンフルオロトリン(Momfluorothrin)、ε-モンフルオロトリン(epsilon-Momfluorothrin)、トランス-ペルメトリン(trans-Permethrin)、プロフルトリン(Profluthrin)、プロトリフェンブト(Protrifenbute)、κ-テフルトリン(kappa-Tefluthrin)、テラレトリン(Terallethrin)、テトラメチルフルスリン(Tetramethylfluthrin);ビオエタノメトリン(Bioethanomethrin)。
(3B)ナトリウムチャネルモジュレーター(DDT類)
DDT、メトキシクロル(Methoxychlor)。 (2) GABAergic chloride ion (chloride ion) channel blockers Chlordane, Endosulfan; Ethiprole, Fipronil.
Acetoprole, Camphechlor, Dienochlor, Heptachlor, Pyrafluprole, Pyriprole; Flufiprole.
(3A) Sodium channel modulator (pyrethroid)
Acrinathrin, Allethrin, d-cis-trans Allethrin, d-transAllethrin, Bifenthrin, Bioallethrin, Bioallethrin -S-cyclopentenyl-isomer (Bioallethrin), Bioresmethrin, Cycloprothrin, Cyfluthrin, Beta-Cyfluthrin, Cyhalothrin, λ- Lambda-Cyhalothrin, gamma-Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin ), zeta-Cypermethrin, Cyphenothrin [(1R)-trans-isomers], Deltamethrin, Empenthrin [(EZ)-(1R) -isomers] (Empenthrin[(EZ)-(1R)-isomers]), Esfenvalerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucitrinate ( Flucythrinate), Flumethrin, tau-Fluvalinate, Halfenprox, Imiprothrin, Kadethrin, Permethrin, Phenothrin [(1R)-trans isomer] (Phenothrin [(1R)-trans-isomer]), Prallethrin, Pyrethrins, Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)-trans-isomer] Tetramethrin [(1R)-isomers], Tralomethrin, Transfluthrin.
Kappa-Bifenthrin, Biopermethrin, Chloroprallethrin, Dimefluthrin, Fenfluthrin, Fenpirithrin, Flufenprox, Heptaflu Heptafluthrin, Meperfluthrin, epsilon-Metofluthrin, Momfluorothrin, epsilon-Momfluorothrin, trans-Permethrin, Profluthrin , Protrifenbute, kappa-Tefluthrin, Terallethrin, Tetramethylfluthrin; Bioethanomethrin.
(3B) Sodium channel modulators (DDTs)
DDT, Methoxychlor.
(4)ニコチン性アセチルコリン受容体(nAChR)競合的モジュレーター
アセタミプリド(Acetamiprid)、クロチアニジン(Clothianidin)、ジノテフラン(Dinotefuran)、イミダクロプリド(Imidacloprid)、ニテンピラム(Nitenpyram)、チアクロプリド(Thiacloprid)、チアメトキサム(Thiamethoxam);ニコチン(Nicotine);スルホキサフロル(Sulfoxaflor);フルピラジフロン(Flupyradifurone);トリフルメゾピリム(Triflumezopyrim)。
ニチアジン(Nithiazine);ジクロロメゾチアズ(Dicloromezotiaz)、フルピリミン(Flupyrimin)。
(5)ニコチン性アセチルコリン受容体(nAChR)アロステリックモジュレーター
スピネトラム(Spinetoram)、スピノサド(Spinosad)。
(6)グルタミン酸作動性塩化物イオン(塩素イオン)チャネル(GluCl) アロステリックモジュレーター
アバメクチン(Abamectin)、エマメクチン(Emamectin)、エマメクチン安息香酸塩(Emamectin-benzoate)、レピメクチン(Lepimectin)、ミルベメクチン(Milbemectin)。
ドラメクチン(Doramectin)、エプリノメクチン(Eprinomectin)、イベルメクチン(Ivermectin)、モキシデクチン(Moxidectin)、セラメクチン(Selamectin)。 (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam; Nicotine (Nicotine); Sulfoxaflor; Flupyradifurone; Triflumezopyrim.
Nithiazine; Dicloromezotiaz, Flupyrimin.
(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators Spinetoram, Spinosad.
(6) Glutamatergic chloride ion (chloride ion) channel (GluCl) allosteric modulator Abamectin, Emamectin, Emamectin-benzoate, Lepimectin, Milbemectin.
Doramectin, Eprinomectin, Ivermectin, Moxidectin, Selamectin.
アセタミプリド(Acetamiprid)、クロチアニジン(Clothianidin)、ジノテフラン(Dinotefuran)、イミダクロプリド(Imidacloprid)、ニテンピラム(Nitenpyram)、チアクロプリド(Thiacloprid)、チアメトキサム(Thiamethoxam);ニコチン(Nicotine);スルホキサフロル(Sulfoxaflor);フルピラジフロン(Flupyradifurone);トリフルメゾピリム(Triflumezopyrim)。
ニチアジン(Nithiazine);ジクロロメゾチアズ(Dicloromezotiaz)、フルピリミン(Flupyrimin)。
(5)ニコチン性アセチルコリン受容体(nAChR)アロステリックモジュレーター
スピネトラム(Spinetoram)、スピノサド(Spinosad)。
(6)グルタミン酸作動性塩化物イオン(塩素イオン)チャネル(GluCl) アロステリックモジュレーター
アバメクチン(Abamectin)、エマメクチン(Emamectin)、エマメクチン安息香酸塩(Emamectin-benzoate)、レピメクチン(Lepimectin)、ミルベメクチン(Milbemectin)。
ドラメクチン(Doramectin)、エプリノメクチン(Eprinomectin)、イベルメクチン(Ivermectin)、モキシデクチン(Moxidectin)、セラメクチン(Selamectin)。 (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, Thiamethoxam; Nicotine (Nicotine); Sulfoxaflor; Flupyradifurone; Triflumezopyrim.
Nithiazine; Dicloromezotiaz, Flupyrimin.
(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators Spinetoram, Spinosad.
(6) Glutamatergic chloride ion (chloride ion) channel (GluCl) allosteric modulator Abamectin, Emamectin, Emamectin-benzoate, Lepimectin, Milbemectin.
Doramectin, Eprinomectin, Ivermectin, Moxidectin, Selamectin.
(7)幼若ホルモン類似剤
ヒドロプレン(Hydroprene)、キノプレン(Kinoprene)、メトプレン(Methoprene);フェノキシカルブ(Fenoxycarb);ピリプロキシフェン(Pyriproxifen)。
ジオフェノラン(Diofenolan)、エポフェノナン(Epofenonane)、トリプレン(Triprene)。
(8)その他の非特異的(マルチサイト)阻害剤
臭化メチル(Methyl bromide)、ハロゲン化アルキル類(alkyl halides);クロルピクリン(Chloropicrin);弗化アルミニウムナトリウム(Sodium aluminum fluoride)、フッ化スルフリル(Sulfuryl fluoride);ホウ砂(Borax)、ホウ酸(Boric acid)、オクタホウ酸ニナトリウム塩(Disodium octaborate)、ホウ酸ナトリウム塩(Sodium borate)、メタホウ酸ナトリウム塩(Sodium metaborate);吐酒石(Tartar emetic);ダゾメット(Dazomet)、メタム(Metam)、メタムカリウム塩(Metam Sodium)、メタムナトリウム塩(Metam Potassium)。
(9)弦音器官TRPVチャネルモジュレーター
ピメトロジン(Pymetrozine)、ピリフルキナゾン(Pyrifluquinazon);アフィドピロペン(Afidopyropen)。
(10)ダニ類成長阻害剤
クロフェンテジン(Clofentezine)、ジフロビダジン(Diflovidazin)、ヘキシチアゾクス(Hexythiazox);エトキサゾール(Etoxazole)。 (7) Juvenile hormone analogs Hydroprene, Kinoprene, Methoprene; Fenoxycarb; Pyriproxifen.
Diofenolan, Epofenonane, Triprene.
(8) Other non-specific (multisite) inhibitors Methyl bromide, alkyl halides; Chloropicrin; Sodium aluminum fluoride, sulfuryl fluoride ( Sulfuryl fluoride; Borax, Boric acid, Disodium octaborate, Sodium borate, Sodium metaborate; Tartar Dazomet, Metam, Metam Sodium, Metam Potassium.
(9) chordotonal organ TRPV channel modulators Pymetrozine, Pyrifluquinazon; Afidopyropene;
(10) Mite growth inhibitors Clofentezine, Diflovidazin, Hexythiazox; Etoxazole.
ヒドロプレン(Hydroprene)、キノプレン(Kinoprene)、メトプレン(Methoprene);フェノキシカルブ(Fenoxycarb);ピリプロキシフェン(Pyriproxifen)。
ジオフェノラン(Diofenolan)、エポフェノナン(Epofenonane)、トリプレン(Triprene)。
(8)その他の非特異的(マルチサイト)阻害剤
臭化メチル(Methyl bromide)、ハロゲン化アルキル類(alkyl halides);クロルピクリン(Chloropicrin);弗化アルミニウムナトリウム(Sodium aluminum fluoride)、フッ化スルフリル(Sulfuryl fluoride);ホウ砂(Borax)、ホウ酸(Boric acid)、オクタホウ酸ニナトリウム塩(Disodium octaborate)、ホウ酸ナトリウム塩(Sodium borate)、メタホウ酸ナトリウム塩(Sodium metaborate);吐酒石(Tartar emetic);ダゾメット(Dazomet)、メタム(Metam)、メタムカリウム塩(Metam Sodium)、メタムナトリウム塩(Metam Potassium)。
(9)弦音器官TRPVチャネルモジュレーター
ピメトロジン(Pymetrozine)、ピリフルキナゾン(Pyrifluquinazon);アフィドピロペン(Afidopyropen)。
(10)ダニ類成長阻害剤
クロフェンテジン(Clofentezine)、ジフロビダジン(Diflovidazin)、ヘキシチアゾクス(Hexythiazox);エトキサゾール(Etoxazole)。 (7) Juvenile hormone analogs Hydroprene, Kinoprene, Methoprene; Fenoxycarb; Pyriproxifen.
Diofenolan, Epofenonane, Triprene.
(8) Other non-specific (multisite) inhibitors Methyl bromide, alkyl halides; Chloropicrin; Sodium aluminum fluoride, sulfuryl fluoride ( Sulfuryl fluoride; Borax, Boric acid, Disodium octaborate, Sodium borate, Sodium metaborate; Tartar Dazomet, Metam, Metam Sodium, Metam Potassium.
(9) chordotonal organ TRPV channel modulators Pymetrozine, Pyrifluquinazon; Afidopyropene;
(10) Mite growth inhibitors Clofentezine, Diflovidazin, Hexythiazox; Etoxazole.
(11)微生物由来昆虫中腸内膜破壊剤
B.t. subsp. israelensis、B.t. subsp. aizawai、B.t. subsp. kurstaki、B.t. subsp.tenebrionis;B.t.作物に含まれるタンパク質(B.t. crop proteins):Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、 Vip3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/Cry35Ab1;Bacillus sphaericus。
(12)ミトコンドリアATP合成酵素阻害剤
ジアフェンチウロン(Diafenthiuron);アゾシクロチン(Azocyclotin)、シヘキサチン(Cyhexatin)、酸化フェンブタスズ(Fenbutatin-oxide);プロパルギット(Propargite);テトラジホン(Tetradifon)。
(13)プロトン勾配を撹乱する酸化的リン酸化脱共役剤
クロルフェナピル(Chlorfenapyr)、DNOC(4,6-dinitro-o-cresol)、スルフルラミド(Sulfluramid)。
ビナパクリル(Binapacryl)、ジノブトン(Dinobuton)、ジノカップ(Dinocap)。
(14)ニコチン性アセチルコリン受容体(nAChR)チャネルブロッカー
ベンスルタップ(Bensultap)、カルタップ塩酸塩(Cartap hydrochloride)、チオシクラム(Thiocyclam)、チオスルタップ-ナトリウム塩(Thiosultap-sodium)。 (11) Microbial-derived insect midgut lining disrupting agent
Bt subsp. israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, Bt subsp. tenebrionis; Proteins contained in Bt crops (Bt crop proteins): Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1; Bacillus sphaericus.
(12) Mitochondrial ATP synthase inhibitor Diafenthiuron; Azocyclotin, Cyhexatin, Fenbutatin-oxide; Propargite; Tetradifon.
(13) Oxidative phosphorylation uncoupler agents that disrupt proton gradients: Chlorfenapyr, DNOC (4,6-dinitro-o-cresol), Sulfluramid.
Binapacryl, Dinobuton, Dinocap.
(14) Nicotinic acetylcholine receptor (nAChR) channel blockers Bensultap, Cartap hydrochloride, Thiocyclam, Thiosultap-sodium.
B.t. subsp. israelensis、B.t. subsp. aizawai、B.t. subsp. kurstaki、B.t. subsp.tenebrionis;B.t.作物に含まれるタンパク質(B.t. crop proteins):Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、 Vip3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/Cry35Ab1;Bacillus sphaericus。
(12)ミトコンドリアATP合成酵素阻害剤
ジアフェンチウロン(Diafenthiuron);アゾシクロチン(Azocyclotin)、シヘキサチン(Cyhexatin)、酸化フェンブタスズ(Fenbutatin-oxide);プロパルギット(Propargite);テトラジホン(Tetradifon)。
(13)プロトン勾配を撹乱する酸化的リン酸化脱共役剤
クロルフェナピル(Chlorfenapyr)、DNOC(4,6-dinitro-o-cresol)、スルフルラミド(Sulfluramid)。
ビナパクリル(Binapacryl)、ジノブトン(Dinobuton)、ジノカップ(Dinocap)。
(14)ニコチン性アセチルコリン受容体(nAChR)チャネルブロッカー
ベンスルタップ(Bensultap)、カルタップ塩酸塩(Cartap hydrochloride)、チオシクラム(Thiocyclam)、チオスルタップ-ナトリウム塩(Thiosultap-sodium)。 (11) Microbial-derived insect midgut lining disrupting agent
Bt subsp. israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, Bt subsp. tenebrionis; Proteins contained in Bt crops (Bt crop proteins): Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1; Bacillus sphaericus.
(12) Mitochondrial ATP synthase inhibitor Diafenthiuron; Azocyclotin, Cyhexatin, Fenbutatin-oxide; Propargite; Tetradifon.
(13) Oxidative phosphorylation uncoupler agents that disrupt proton gradients: Chlorfenapyr, DNOC (4,6-dinitro-o-cresol), Sulfluramid.
Binapacryl, Dinobuton, Dinocap.
(14) Nicotinic acetylcholine receptor (nAChR) channel blockers Bensultap, Cartap hydrochloride, Thiocyclam, Thiosultap-sodium.
(15)キチン生合成阻害剤、タイプ0
ビストリフルロン(Bistrifluron)、クロルフルアズロン(Chlorfluazuron)、ジフルベンズロン(Diflubenzuron)、フルシクロクスロン(Flucycloxuron)、フルフェノクスロン(Flufenoxuron)、ヘキサフルムロン(Hexaflumuron)、ルフェヌロン(Lufenuron)、ノバルロン(Novaluron)、ノビフルムロン(Noviflumuron)、テフルベンズロン(Teflubenzuron)、トリフルムロン(Triflumuron)。
フルアズロン(Fluazuron)。
(16)キチン生合成阻害剤、タイプ1
ブプロフェジン(Buprofezin)。
(17)脱皮阻害剤
シロマジン(Cyromazine)。
(18)脱皮ホルモン(エクダイソン)受容体アゴニスト
クロマフェノジド(Chromafenozide)、ハロフェノジド(Halofenozid)、メトキシフェノジド(Methoxyfenozide)、テブフェノジド(Tebufenozide)。 (15) Chitin biosynthesis inhibitor, type 0
Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron ), Noviflumuron, Teflubenzuron, Triflumuron.
Fluazuron.
(16) Chitin biosynthesis inhibitor, type 1
Buprofezin.
(17) Cyromazine, an ecdysis inhibitor.
(18) Ecdysone receptor agonists Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide.
ビストリフルロン(Bistrifluron)、クロルフルアズロン(Chlorfluazuron)、ジフルベンズロン(Diflubenzuron)、フルシクロクスロン(Flucycloxuron)、フルフェノクスロン(Flufenoxuron)、ヘキサフルムロン(Hexaflumuron)、ルフェヌロン(Lufenuron)、ノバルロン(Novaluron)、ノビフルムロン(Noviflumuron)、テフルベンズロン(Teflubenzuron)、トリフルムロン(Triflumuron)。
フルアズロン(Fluazuron)。
(16)キチン生合成阻害剤、タイプ1
ブプロフェジン(Buprofezin)。
(17)脱皮阻害剤
シロマジン(Cyromazine)。
(18)脱皮ホルモン(エクダイソン)受容体アゴニスト
クロマフェノジド(Chromafenozide)、ハロフェノジド(Halofenozid)、メトキシフェノジド(Methoxyfenozide)、テブフェノジド(Tebufenozide)。 (15) Chitin biosynthesis inhibitor, type 0
Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron ), Noviflumuron, Teflubenzuron, Triflumuron.
Fluazuron.
(16) Chitin biosynthesis inhibitor, type 1
Buprofezin.
(17) Cyromazine, an ecdysis inhibitor.
(18) Ecdysone receptor agonists Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide.
(19)オクトパミン受容体アゴニスト
アミトラズ(Amitraz)。
クロルジメホルム(Chlordimeform)。
(20)ミトコンドリア電子伝達系複合体III阻害剤
ヒドラメチルノン(Hydramethylnon);アセキノシル(Acequinocyl);フルアクリピリム(Fluacrypyrim);ビフェナゼート(Bifenazate)。
(21)ミトコンドリア電子伝達系複合体I阻害剤(METI)
フェナザキン(Fenazaquin)、フェンピロキシメート(Fenpyroximate)、ピリダベン(Pyridaben)、ピリミジフェン(Pyrimidifen)、テブフェンピラド(Tebufenpyrad)、トルフェンピラド(Tolfenpyrad);ロテノン(Rotenone)。
(22)電位依存性ナトリウムチャネルブロッカー
インドキサカルブ(Indoxacarb);メタフルミゾン(Metaflumizone)。
(23)アセチルCoAカルボキシラーゼ阻害剤
スピロジクロフェン(Spirodiclofen)、スピロメシフェン(Spiromesifen)、スピロテトラマト(Spirotetramat)。
スピロピジオン(Spiropidion)。
(24)ミトコンドリア電子伝達系複合体IV阻害剤
リン化アルミニウム (Al-phosphide)、リン化カルシウム(Ca-phosphide)、リン化亜鉛(Zn-phosphide)、ホスフィン(Phosphine);シアン化カルシウム(Ca-cyanide)シアン化ナトリウム(Na-cyanide)、シアン化カリウム(K-cyanide)。
(25)ミトコンドリア電子伝達系複合体II阻害剤
シエノピラフェン(Cyenopyrafen)、シフルメトフェン(Cyflumetofen);ピフルブミド(Pyflubumide)。 (19) Octopamine receptor agonist Amitraz.
Chlordimeform.
(20) Mitochondrial electron transport chain complex III inhibitors Hydramethylnon; Acequinocyl; Fluacrypyrim; Bifenazate.
(21) Mitochondrial electron transport chain complex I inhibitor (METI)
Fenazaquin, Fenpyroximate, Pyridaben, Pyrimidifen, Tebufenpyrad, Tolfenpyrad; Rotenone.
(22) Voltage-gated sodium channel blocker Indoxacarb; Metaflumizone.
(23) Acetyl-CoA carboxylase inhibitors Spirodiclofen, Spiromesifen, Spirotetramat.
Spiropidion.
(24) Mitochondrial electron transport chain complex IV inhibitors Al-phosphide, Ca-phosphide, Zn-phosphide, Phosphine; Calcium cyanide (Ca- cyanide) Sodium cyanide (Na-cyanide), Potassium cyanide (K-cyanide).
(25) Mitochondrial electron transport chain complex II inhibitors Cyenopyrafen, Cyflumetofen; Pyflubumide.
アミトラズ(Amitraz)。
クロルジメホルム(Chlordimeform)。
(20)ミトコンドリア電子伝達系複合体III阻害剤
ヒドラメチルノン(Hydramethylnon);アセキノシル(Acequinocyl);フルアクリピリム(Fluacrypyrim);ビフェナゼート(Bifenazate)。
(21)ミトコンドリア電子伝達系複合体I阻害剤(METI)
フェナザキン(Fenazaquin)、フェンピロキシメート(Fenpyroximate)、ピリダベン(Pyridaben)、ピリミジフェン(Pyrimidifen)、テブフェンピラド(Tebufenpyrad)、トルフェンピラド(Tolfenpyrad);ロテノン(Rotenone)。
(22)電位依存性ナトリウムチャネルブロッカー
インドキサカルブ(Indoxacarb);メタフルミゾン(Metaflumizone)。
(23)アセチルCoAカルボキシラーゼ阻害剤
スピロジクロフェン(Spirodiclofen)、スピロメシフェン(Spiromesifen)、スピロテトラマト(Spirotetramat)。
スピロピジオン(Spiropidion)。
(24)ミトコンドリア電子伝達系複合体IV阻害剤
リン化アルミニウム (Al-phosphide)、リン化カルシウム(Ca-phosphide)、リン化亜鉛(Zn-phosphide)、ホスフィン(Phosphine);シアン化カルシウム(Ca-cyanide)シアン化ナトリウム(Na-cyanide)、シアン化カリウム(K-cyanide)。
(25)ミトコンドリア電子伝達系複合体II阻害剤
シエノピラフェン(Cyenopyrafen)、シフルメトフェン(Cyflumetofen);ピフルブミド(Pyflubumide)。 (19) Octopamine receptor agonist Amitraz.
Chlordimeform.
(20) Mitochondrial electron transport chain complex III inhibitors Hydramethylnon; Acequinocyl; Fluacrypyrim; Bifenazate.
(21) Mitochondrial electron transport chain complex I inhibitor (METI)
Fenazaquin, Fenpyroximate, Pyridaben, Pyrimidifen, Tebufenpyrad, Tolfenpyrad; Rotenone.
(22) Voltage-gated sodium channel blocker Indoxacarb; Metaflumizone.
(23) Acetyl-CoA carboxylase inhibitors Spirodiclofen, Spiromesifen, Spirotetramat.
Spiropidion.
(24) Mitochondrial electron transport chain complex IV inhibitors Al-phosphide, Ca-phosphide, Zn-phosphide, Phosphine; Calcium cyanide (Ca- cyanide) Sodium cyanide (Na-cyanide), Potassium cyanide (K-cyanide).
(25) Mitochondrial electron transport chain complex II inhibitors Cyenopyrafen, Cyflumetofen; Pyflubumide.
(28)リアノジン受容体モジュレーター
クロラントラニリプロール(Chlorantraniliprole)、シアントラニリプロール(Cyantraniliprole)、シクラニリプロール(Cyclaniliprole)、フルベンジアミド(Flubendiamide)。
シハロジアミド(Cyhalodiamide)、テトラクロラントラニリプロール(Tetrachlorantraniliprole)、テトラニリプロール(Tetraniliprole)。
(29)弦音器官モジュレーター 標的部位未特定
フロニカミド(Flonicamid)。
(30)GABA作動性塩化物イオン(塩素イオン)チャネルアロステリックモジュレーター
ブロフラニリド(Broflanilide)、フルキサメタミド(Fluxametamide)。
イソシクロセラム(Isocycloseram);アフォキソラネル(Afoxolaner)、フルララネル(Fluralaner)、ロチラネル(Lotilaner)、サロラネル(Sarolaner)。 (28) Ryanodine receptor modulators Chlorantraniliprole, Cyantraniliprole, Cyclaniliprole, Flubendiamide.
Cyhalodiamide, Tetrachlorantraniliprole, Tetraniliprole.
(29) Choronic organ modulator: Flonicamid, target site unspecified.
(30) GABAergic chloride channel allosteric modulators Broflanilide, Fluxametamide.
Isocycloseram; Afoxolaner, Fluralaner, Lotilaner, Sarolaner.
クロラントラニリプロール(Chlorantraniliprole)、シアントラニリプロール(Cyantraniliprole)、シクラニリプロール(Cyclaniliprole)、フルベンジアミド(Flubendiamide)。
シハロジアミド(Cyhalodiamide)、テトラクロラントラニリプロール(Tetrachlorantraniliprole)、テトラニリプロール(Tetraniliprole)。
(29)弦音器官モジュレーター 標的部位未特定
フロニカミド(Flonicamid)。
(30)GABA作動性塩化物イオン(塩素イオン)チャネルアロステリックモジュレーター
ブロフラニリド(Broflanilide)、フルキサメタミド(Fluxametamide)。
イソシクロセラム(Isocycloseram);アフォキソラネル(Afoxolaner)、フルララネル(Fluralaner)、ロチラネル(Lotilaner)、サロラネル(Sarolaner)。 (28) Ryanodine receptor modulators Chlorantraniliprole, Cyantraniliprole, Cyclaniliprole, Flubendiamide.
Cyhalodiamide, Tetrachlorantraniliprole, Tetraniliprole.
(29) Choronic organ modulator: Flonicamid, target site unspecified.
(30) GABAergic chloride channel allosteric modulators Broflanilide, Fluxametamide.
Isocycloseram; Afoxolaner, Fluralaner, Lotilaner, Sarolaner.
(31)その他の殺虫剤、殺ダニ剤
アザジラクチン(Azadirachtin)、ベンゾキシメート(Benzoximate)、ブロモプロピレート(Bromopropylate)、キノメチオナート(Chinomethionat)、ジコホル(Dicofol)、石灰硫黄合剤(Lime sulfur)、マンコゼブ(Mancozeb)、ピリダリル(Pyridalyl)、硫黄(Sulfur)。
アシノナピル(Acynonapyr)、アミドフルメット(Amidoflumet)、ベンゾメート(Benzomate)、ベンズピリモキサン(Benzpyrimoxan)、クロルベンジレート(Chlorobenzilate)、ジシクラニル(Dicyclanil)、フェノキサクリム(Fenoxacrim)、フェントリファニル(Fentrifanil)、フロメトキン(Flometoquin)、フルベンジミン(Flubenzimine)、フルフェンジン(Flufenzine)、フルヘキサホン(Fluhexafon)、フルオピラム(Fluopyram)、メタフルミゾン(Metaflumizone)、メトキサジアゾン(Metoxadiazone)、オキサゾスルフィル(Oxazosulfyl)、テトラスル(Tetrasul)、トリアラセン(Triarathene)、チクロピラゾフロル(Tyclopyrazoflor)。 (31) Other insecticides, acaricides Azadirachtin, Benzoximate, Bromopropylate, Chinomethionat, Dicofol, Lime sulfur, Mancozeb (Mancozeb), Pyridalyl, Sulfur.
Acynonapyr, Amidoflumet, Benzomate, Benzpyrimoxan, Chlorobenzilate, Dicyclanil, Fenoxacrim, Fentrifanil, Flometoquin, Flubenzimine, Flufenzine, Fluhexafon, Fluopyram, Metaflumizone, Metoxadiazone, Oxazosulfyl, Tetrasul, Triaracene ( Triarathene), Tyclopyrazoflor.
アザジラクチン(Azadirachtin)、ベンゾキシメート(Benzoximate)、ブロモプロピレート(Bromopropylate)、キノメチオナート(Chinomethionat)、ジコホル(Dicofol)、石灰硫黄合剤(Lime sulfur)、マンコゼブ(Mancozeb)、ピリダリル(Pyridalyl)、硫黄(Sulfur)。
アシノナピル(Acynonapyr)、アミドフルメット(Amidoflumet)、ベンゾメート(Benzomate)、ベンズピリモキサン(Benzpyrimoxan)、クロルベンジレート(Chlorobenzilate)、ジシクラニル(Dicyclanil)、フェノキサクリム(Fenoxacrim)、フェントリファニル(Fentrifanil)、フロメトキン(Flometoquin)、フルベンジミン(Flubenzimine)、フルフェンジン(Flufenzine)、フルヘキサホン(Fluhexafon)、フルオピラム(Fluopyram)、メタフルミゾン(Metaflumizone)、メトキサジアゾン(Metoxadiazone)、オキサゾスルフィル(Oxazosulfyl)、テトラスル(Tetrasul)、トリアラセン(Triarathene)、チクロピラゾフロル(Tyclopyrazoflor)。 (31) Other insecticides, acaricides Azadirachtin, Benzoximate, Bromopropylate, Chinomethionat, Dicofol, Lime sulfur, Mancozeb (Mancozeb), Pyridalyl, Sulfur.
Acynonapyr, Amidoflumet, Benzomate, Benzpyrimoxan, Chlorobenzilate, Dicyclanil, Fenoxacrim, Fentrifanil, Flometoquin, Flubenzimine, Flufenzine, Fluhexafon, Fluopyram, Metaflumizone, Metoxadiazone, Oxazosulfyl, Tetrasul, Triaracene ( Triarathene), Tyclopyrazoflor.
本発明の有害生物防除剤と混用または併用することができる、駆虫剤の具体例を以下に示す。
(a)ベンズイミダゾール系: フェンベンダゾール、アルベンダゾール、トリクラベンダゾール、オキシベンダゾール、メベンダゾール、オクスフェンダゾール、パーベンダゾール、フルベンダゾール;フェバンテル、ネトビミン、チオファネート;チアベンダゾール、カンベンダゾール;
(b)サリチルアニリド系: クロサンテル、オキシクロザニド、ラフォキサニド、ニクロサミド;
(c)置換フェノール系: ニトロキシニル、ニトロスカネイト;
(d)ピリミジン系: ピランテル、モランテル;
(e)イミダゾチアゾール系: レバミソール、テトラミソール;
(f)テトラヒドロピリミジン系: プラジカンテル、エプシプランテル;
(g)その他の駆虫薬: シクロジエン、リアニア、クロルスロン、メトロニダゾール、デミジトラズ;ピペラジン、ジエチルカルバマジン、ジクロロフェン、モネパンテル、トリベンジミジン、アミダンテル;チアセタルサミド、メラルサミン、アルセナマイド。 Specific examples of anthelmintic agents that can be used in combination or in combination with the pest control agent of the present invention are shown below.
(a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, perbendazole, flubendazole; febantel, netovimine, thiophanate; thiabendazole, cambendazole;
(b) Salicylanilide series: closantel, oxyclozanide, lafoxanide, niclosamide;
(c) Substituted phenolics: nitroxynil, nitroscanate;
(d) Pyrimidine series: pyrantel, morantel;
(e) Imidazothiazole series: levamisole, tetramisole;
(f) Tetrahydropyrimidine series: praziquantel, epciprantel;
(g) Other anthelmintics: cyclodiene, liania, clorsulon, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophene, monepantel, tribendimidine, amidantel; thiacetalsamide, melarsamine, arsenamide.
(a)ベンズイミダゾール系: フェンベンダゾール、アルベンダゾール、トリクラベンダゾール、オキシベンダゾール、メベンダゾール、オクスフェンダゾール、パーベンダゾール、フルベンダゾール;フェバンテル、ネトビミン、チオファネート;チアベンダゾール、カンベンダゾール;
(b)サリチルアニリド系: クロサンテル、オキシクロザニド、ラフォキサニド、ニクロサミド;
(c)置換フェノール系: ニトロキシニル、ニトロスカネイト;
(d)ピリミジン系: ピランテル、モランテル;
(e)イミダゾチアゾール系: レバミソール、テトラミソール;
(f)テトラヒドロピリミジン系: プラジカンテル、エプシプランテル;
(g)その他の駆虫薬: シクロジエン、リアニア、クロルスロン、メトロニダゾール、デミジトラズ;ピペラジン、ジエチルカルバマジン、ジクロロフェン、モネパンテル、トリベンジミジン、アミダンテル;チアセタルサミド、メラルサミン、アルセナマイド。 Specific examples of anthelmintic agents that can be used in combination or in combination with the pest control agent of the present invention are shown below.
(a) Benzimidazoles: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, oxfendazole, perbendazole, flubendazole; febantel, netovimine, thiophanate; thiabendazole, cambendazole;
(b) Salicylanilide series: closantel, oxyclozanide, lafoxanide, niclosamide;
(c) Substituted phenolics: nitroxynil, nitroscanate;
(d) Pyrimidine series: pyrantel, morantel;
(e) Imidazothiazole series: levamisole, tetramisole;
(f) Tetrahydropyrimidine series: praziquantel, epciprantel;
(g) Other anthelmintics: cyclodiene, liania, clorsulon, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophene, monepantel, tribendimidine, amidantel; thiacetalsamide, melarsamine, arsenamide.
本発明の有害生物防除剤と混用または併用することができる、殺菌剤の具体例を以下に示す。
(A)核酸合成代謝の阻害剤
A1)RNAポリメラーゼI阻害剤
ベナラキシル(benalaxyl)、ベナラキシルM(benalaxyl-M)、フララキシル(furalaxyl)、メタラキシル(metalaxyl)、メタラキシルM(metalaxyl-M);オキサジキシル(oxadixyl);オフラセ(ofurace)。
A2)アデノシンデアミナーゼ阻害剤
ブピリメート(bupirimate)、ジメチリモール(dimethirimol)、エチリモール(ethirimol)。
A3)DNA/RNA生合成阻害剤
ヒメキサゾール(hymexazole)、オクチリノン(octhilinone)。
A4)DNAトポイソメラーゼ タイプII阻害剤
オキソリニック酸(oxolinic acid)。 Specific examples of fungicides that can be mixed or used in combination with the pest control agent of the present invention are shown below.
(A) Inhibitor of nucleic acid synthesis metabolism A1) RNA polymerase I inhibitor benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M; oxadixyl ); ofurace.
A2) Adenosine deaminase inhibitors bupirimate, dimethirimol, ethirimol.
A3) DNA/RNA biosynthesis inhibitors hymexazole and octhilinone.
A4) DNA topoisomerase type II inhibitor oxolinic acid.
(A)核酸合成代謝の阻害剤
A1)RNAポリメラーゼI阻害剤
ベナラキシル(benalaxyl)、ベナラキシルM(benalaxyl-M)、フララキシル(furalaxyl)、メタラキシル(metalaxyl)、メタラキシルM(metalaxyl-M);オキサジキシル(oxadixyl);オフラセ(ofurace)。
A2)アデノシンデアミナーゼ阻害剤
ブピリメート(bupirimate)、ジメチリモール(dimethirimol)、エチリモール(ethirimol)。
A3)DNA/RNA生合成阻害剤
ヒメキサゾール(hymexazole)、オクチリノン(octhilinone)。
A4)DNAトポイソメラーゼ タイプII阻害剤
オキソリニック酸(oxolinic acid)。 Specific examples of fungicides that can be mixed or used in combination with the pest control agent of the present invention are shown below.
(A) Inhibitor of nucleic acid synthesis metabolism A1) RNA polymerase I inhibitor benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M; oxadixyl ); ofurace.
A2) Adenosine deaminase inhibitors bupirimate, dimethirimol, ethirimol.
A3) DNA/RNA biosynthesis inhibitors hymexazole and octhilinone.
A4) DNA topoisomerase type II inhibitor oxolinic acid.
(B)細胞骨格とモーター蛋白質に作用する剤
B1)~B3)β-チューブリン重合阻害
ベノミル(benomyl)、カルベンダジム(carbendazim)、フベリダゾール(fuberidazole)、チアベンダゾール(thiabendazole)、チオファネート(thiophanate)、チオファネートメチル(thiophanate-methyl)、ジエトフェンカルブ(diethofencarb)、ゾキサミド(zoxamide)、
エタボキサム(ethaboxam)。
クロルフェナゾール(chlorfenazole)、デバカルブ(debacarb)、トリクラミド(trichlamide)、ザリラミド(zarilamid)。
B4)細胞分裂(作用点不明)
ペンシクロン(pencycuron)。
B5)スペクトリン様蛋白質の非局在化
フルオピコリド(fluopicolide)、フルオピモミド(fluopimomide)。
B6)アクチン/ミオシン/フィンブリン機能
フェナマクリル(phenamacril)、メトラフェノン(metrafenone)、ピリオフェノン(pyriofenone)。 (B) Agents that act on the cytoskeleton and motor proteins B1) to B3) β-tubulin polymerization inhibition benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate methyl (thiophanate-methyl), diethofencarb, zoxamide,
Ethaboxam.
Chlorfenazole, debacarb, trichlamide, zarilamid.
B4) Cell division (point of action unknown)
pencycuron.
B5) Delocalization of spectrin-like proteins fluopicolide, fluopimomide.
B6) Actin/myosin/fimbrin function phenamacryl, metrafenone, pyriofenone.
B1)~B3)β-チューブリン重合阻害
ベノミル(benomyl)、カルベンダジム(carbendazim)、フベリダゾール(fuberidazole)、チアベンダゾール(thiabendazole)、チオファネート(thiophanate)、チオファネートメチル(thiophanate-methyl)、ジエトフェンカルブ(diethofencarb)、ゾキサミド(zoxamide)、
エタボキサム(ethaboxam)。
クロルフェナゾール(chlorfenazole)、デバカルブ(debacarb)、トリクラミド(trichlamide)、ザリラミド(zarilamid)。
B4)細胞分裂(作用点不明)
ペンシクロン(pencycuron)。
B5)スペクトリン様蛋白質の非局在化
フルオピコリド(fluopicolide)、フルオピモミド(fluopimomide)。
B6)アクチン/ミオシン/フィンブリン機能
フェナマクリル(phenamacril)、メトラフェノン(metrafenone)、ピリオフェノン(pyriofenone)。 (B) Agents that act on the cytoskeleton and motor proteins B1) to B3) β-tubulin polymerization inhibition benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate methyl (thiophanate-methyl), diethofencarb, zoxamide,
Ethaboxam.
Chlorfenazole, debacarb, trichlamide, zarilamid.
B4) Cell division (point of action unknown)
pencycuron.
B5) Delocalization of spectrin-like proteins fluopicolide, fluopimomide.
B6) Actin/myosin/fimbrin function phenamacryl, metrafenone, pyriofenone.
(C)呼吸阻害剤
C1)複合体I: NADH酸化還元酵素
ジフルメトリム(diflumetorim)、トルフェンピラド(tolfenpyrad)、フェナザキン(fenazaquin)。
C2)複合体II:コハク酸脱水素酵素
ベノダニル(benodanil)、フルトラニル(flutolanil)、メプロニル(mepronil);イソフェタミド(isofetamid);フルオピラム(fluopyram);シクロブトリフルラム(cyclobutrifluram);フェンフラム(fenfuram);カルボキシン(carboxin)、オキシカルボキシン(oxycarboxin);チフルザミド(thifluzamide);ベンゾビンジフルピル(benzovindiflupyr)、ビキサフェン(bixafen)、フルインダピル(fluindapyr)、フルキサピロキサド(fluxapyroxad)、フラメトピル(furametpyr)、インピルフルキサム(inpyrfluxam)、イソピラザム(isopyrazam)、ペンフルフェン(penflufen)、ペンチオピラド(penthiopyrad)、セダキサン(sedaxane);イソフルシプラム(isoflucypram);ピジフルメトフェン(pydiflumetofen);ボスカリド(boscalid);ピラジフルミド(pyraziflumid)。
フルメシクロックス(furmecyclox)。
C3)複合体III:チトクローム bc1(ユビキノール酸化酵素)Qo部位(cyt b遺伝子)
アゾキシストロビン(azoxystrobin)、クモキシストロビン(coumoxystrobin)、エノキサストロビン(enoxastrobin)、フルフェノキシストロビン(flufenoxystrobin)、ピコキシストロビン(picoxystrobin)、ピラオキシストロビン(pyraoxystrobin);マンデストロビン (mandestrobin);ピラクロストロビン(pyraclostrobin)、ピラメトストロビン(pyrametostrobin)、トリクロピリカルブ(triclopyricarb);クレソキシムメチル(kresoxim-methyl)、トリフロキシストロビン(trifloxystrobin);ジモキシストロビン(dimoxystrobin)、フェナミンストロビン(fenaminstrobin)、メトミノストロビン(metominostrobin)、オリサストロビン(orysastrobin);ファモキサドン(famoxadone);フルオキサストロビン(fluoxastrobin);フェンアミドン(fenamidone);ピリベンカルブ(pyribencarb);メチルテトラプロール(metyltetraprole)。
C4)複合体III:ユビキノン還元酵素 Qi部位
シアゾファミド(cyazofamid);アミスルブロム(amisulbrom);フェンピコキサミド(fenpicoxamid)、フロリルピコキサミド(florylpicoxamid)。
C5)酸化的リン酸化の脱共役
ビナパクリル(binapacryl)、ジノカップ(dinocap)、メプチルジノカップ(meptyldinocap);フルアジナム(fluazinam)。
C6)酸化的リン酸化、ATP合成酵素の阻害
酢酸トリフェニルスズ(fentin acetate)、塩化トリフェニルスズ(fentin chloride)、水酸化トリフェニルスズ(fentin hydroxide)。
C7)ATP輸送
シルチオファム(silthiofam)。
C8)複合体III:ユビキノン還元酵素(Qo部位、スチグマテリン結合サブサイト)
アメトクトラジン(ametoctradin)。 (C) Respiratory inhibitor C1) Complex I: NADH oxidoreductase diflumetorim, tolfenpyrad, fenazaquin.
C2) Complex II: Succinate dehydrogenase benodanil, flutolanil, mepronil; isofetamid; fluopyram; cyclobutrifluram; fenfuram; carboxy carboxin, oxycarboxin; thifluzamide; benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, impyr inpyrfluxam, isopyrazam, penflufen, penthiopyrad, sedaxane; isoflucypram; pydiflumetofen; boscalid; pyraziflumid .
Furmecyclox.
C3) Complex III: Cytochrome bc1 (ubiquinol oxidase) Qo site (cyt b gene)
azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin; mandestrobin (mandestrobin); pyraclostrobin, pyrametostrobin, triclopyricarb; kresoxim-methyl, trifloxystrobin; dimoxystrobin, phenaminest fenaminstrobin, metominostrobin, orysastrobin; famoxadone; fluoxastrobin; fenamidone; pyribencarb; methyltetraprole.
C4) Complex III: Ubiquinone reductase Qi site cyazofamid; amisulbrom; fenpicoxamide, florylpicoxamid.
C5) Uncoupling of oxidative phosphorylation binapacryl, dinocap, meptyldinocap; fluazinam.
C6) Oxidative phosphorylation, inhibition of ATP synthase fentin acetate, fentin chloride, fentin hydroxide.
C7) ATP transport silthiofam.
C8) Complex III: Ubiquinone reductase (Qo site, stigmatellin binding subsite)
Ametoctradin.
C1)複合体I: NADH酸化還元酵素
ジフルメトリム(diflumetorim)、トルフェンピラド(tolfenpyrad)、フェナザキン(fenazaquin)。
C2)複合体II:コハク酸脱水素酵素
ベノダニル(benodanil)、フルトラニル(flutolanil)、メプロニル(mepronil);イソフェタミド(isofetamid);フルオピラム(fluopyram);シクロブトリフルラム(cyclobutrifluram);フェンフラム(fenfuram);カルボキシン(carboxin)、オキシカルボキシン(oxycarboxin);チフルザミド(thifluzamide);ベンゾビンジフルピル(benzovindiflupyr)、ビキサフェン(bixafen)、フルインダピル(fluindapyr)、フルキサピロキサド(fluxapyroxad)、フラメトピル(furametpyr)、インピルフルキサム(inpyrfluxam)、イソピラザム(isopyrazam)、ペンフルフェン(penflufen)、ペンチオピラド(penthiopyrad)、セダキサン(sedaxane);イソフルシプラム(isoflucypram);ピジフルメトフェン(pydiflumetofen);ボスカリド(boscalid);ピラジフルミド(pyraziflumid)。
フルメシクロックス(furmecyclox)。
C3)複合体III:チトクローム bc1(ユビキノール酸化酵素)Qo部位(cyt b遺伝子)
アゾキシストロビン(azoxystrobin)、クモキシストロビン(coumoxystrobin)、エノキサストロビン(enoxastrobin)、フルフェノキシストロビン(flufenoxystrobin)、ピコキシストロビン(picoxystrobin)、ピラオキシストロビン(pyraoxystrobin);マンデストロビン (mandestrobin);ピラクロストロビン(pyraclostrobin)、ピラメトストロビン(pyrametostrobin)、トリクロピリカルブ(triclopyricarb);クレソキシムメチル(kresoxim-methyl)、トリフロキシストロビン(trifloxystrobin);ジモキシストロビン(dimoxystrobin)、フェナミンストロビン(fenaminstrobin)、メトミノストロビン(metominostrobin)、オリサストロビン(orysastrobin);ファモキサドン(famoxadone);フルオキサストロビン(fluoxastrobin);フェンアミドン(fenamidone);ピリベンカルブ(pyribencarb);メチルテトラプロール(metyltetraprole)。
C4)複合体III:ユビキノン還元酵素 Qi部位
シアゾファミド(cyazofamid);アミスルブロム(amisulbrom);フェンピコキサミド(fenpicoxamid)、フロリルピコキサミド(florylpicoxamid)。
C5)酸化的リン酸化の脱共役
ビナパクリル(binapacryl)、ジノカップ(dinocap)、メプチルジノカップ(meptyldinocap);フルアジナム(fluazinam)。
C6)酸化的リン酸化、ATP合成酵素の阻害
酢酸トリフェニルスズ(fentin acetate)、塩化トリフェニルスズ(fentin chloride)、水酸化トリフェニルスズ(fentin hydroxide)。
C7)ATP輸送
シルチオファム(silthiofam)。
C8)複合体III:ユビキノン還元酵素(Qo部位、スチグマテリン結合サブサイト)
アメトクトラジン(ametoctradin)。 (C) Respiratory inhibitor C1) Complex I: NADH oxidoreductase diflumetorim, tolfenpyrad, fenazaquin.
C2) Complex II: Succinate dehydrogenase benodanil, flutolanil, mepronil; isofetamid; fluopyram; cyclobutrifluram; fenfuram; carboxy carboxin, oxycarboxin; thifluzamide; benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, furametpyr, impyr inpyrfluxam, isopyrazam, penflufen, penthiopyrad, sedaxane; isoflucypram; pydiflumetofen; boscalid; pyraziflumid .
Furmecyclox.
C3) Complex III: Cytochrome bc1 (ubiquinol oxidase) Qo site (cyt b gene)
azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin; mandestrobin (mandestrobin); pyraclostrobin, pyrametostrobin, triclopyricarb; kresoxim-methyl, trifloxystrobin; dimoxystrobin, phenaminest fenaminstrobin, metominostrobin, orysastrobin; famoxadone; fluoxastrobin; fenamidone; pyribencarb; methyltetraprole.
C4) Complex III: Ubiquinone reductase Qi site cyazofamid; amisulbrom; fenpicoxamide, florylpicoxamid.
C5) Uncoupling of oxidative phosphorylation binapacryl, dinocap, meptyldinocap; fluazinam.
C6) Oxidative phosphorylation, inhibition of ATP synthase fentin acetate, fentin chloride, fentin hydroxide.
C7) ATP transport silthiofam.
C8) Complex III: Ubiquinone reductase (Qo site, stigmatellin binding subsite)
Ametoctradin.
(D)アミノ酸および蛋白質合成の阻害剤
D1)メチオニン生合成(cgs遺伝子)
シプロジニル(cyprodinil)、メパニピリム(mepanipyrim)、ピリメタニル(pyrimethanil)。
D2)蛋白質合成(リボソーム 翻訳終了段階)
ブラストサイジンS(blasticidin-S)。
D3)、D4)蛋白質合成(リボソーム 翻訳開始段階)
カスガマイシン(kasugamycin)、カスガマイシン塩酸塩(kasugamycin hydrochloride)、ストレプトマイシン(streptomycin)。
D5)蛋白質合成(リボソーム ポリペプチド伸長段階)
オキシテトラサイクリン(oxytetracycline)。 (D) Inhibitor of amino acid and protein synthesis D1) Methionine biosynthesis (cgs gene)
Cyprodinil, mepanipyrim, pyrimethanil.
D2) Protein synthesis (ribosome translation termination stage)
Blasticidin-S.
D3), D4) Protein synthesis (ribosome translation initiation stage)
Kasugamycin, kasugamycin hydrochloride, streptomycin.
D5) Protein synthesis (ribosome polypeptide elongation stage)
Oxytetracycline.
D1)メチオニン生合成(cgs遺伝子)
シプロジニル(cyprodinil)、メパニピリム(mepanipyrim)、ピリメタニル(pyrimethanil)。
D2)蛋白質合成(リボソーム 翻訳終了段階)
ブラストサイジンS(blasticidin-S)。
D3)、D4)蛋白質合成(リボソーム 翻訳開始段階)
カスガマイシン(kasugamycin)、カスガマイシン塩酸塩(kasugamycin hydrochloride)、ストレプトマイシン(streptomycin)。
D5)蛋白質合成(リボソーム ポリペプチド伸長段階)
オキシテトラサイクリン(oxytetracycline)。 (D) Inhibitor of amino acid and protein synthesis D1) Methionine biosynthesis (cgs gene)
Cyprodinil, mepanipyrim, pyrimethanil.
D2) Protein synthesis (ribosome translation termination stage)
Blasticidin-S.
D3), D4) Protein synthesis (ribosome translation initiation stage)
Kasugamycin, kasugamycin hydrochloride, streptomycin.
D5) Protein synthesis (ribosome polypeptide elongation stage)
Oxytetracycline.
(E)シグナル伝達阻害剤
E1)シグナル伝達(作用機構不明)
キノキシフェン(quinoxyfen)、プロキナジド(proquinazid)。
E2)浸透圧シグナル伝達におけるMAP/ヒスチジンキナーゼ(os-2、HOG1)
フェンピクロニル(fenpiclonil)、フルジオキソニル(fludioxonil)。
E3)浸透圧シグナル伝達におけるMAP/ヒスチジンキナーゼ(os-1、Daf1)
クロゾリネート(chlozolinate)、ジメタクロン(dimethachlone)、イプロジオン(iprodione)、プロシミドン(procymidone)、ビンクロゾリン(vinclozolin)。 (E) Signal transduction inhibitor E1) Signal transduction (mechanism of action unknown)
Quinoxyfen, proquinazid.
E2) MAP/histidine kinase (os-2, HOG1) in osmotic signal transduction
Fenpiclonil, fludioxonil.
E3) MAP/histidine kinases (os-1, Daf1) in osmotic signal transduction
chlozolinate, dimethachlone, iprodione, procymidone, vinclozolin.
E1)シグナル伝達(作用機構不明)
キノキシフェン(quinoxyfen)、プロキナジド(proquinazid)。
E2)浸透圧シグナル伝達におけるMAP/ヒスチジンキナーゼ(os-2、HOG1)
フェンピクロニル(fenpiclonil)、フルジオキソニル(fludioxonil)。
E3)浸透圧シグナル伝達におけるMAP/ヒスチジンキナーゼ(os-1、Daf1)
クロゾリネート(chlozolinate)、ジメタクロン(dimethachlone)、イプロジオン(iprodione)、プロシミドン(procymidone)、ビンクロゾリン(vinclozolin)。 (E) Signal transduction inhibitor E1) Signal transduction (mechanism of action unknown)
Quinoxyfen, proquinazid.
E2) MAP/histidine kinase (os-2, HOG1) in osmotic signal transduction
Fenpiclonil, fludioxonil.
E3) MAP/histidine kinases (os-1, Daf1) in osmotic signal transduction
chlozolinate, dimethachlone, iprodione, procymidone, vinclozolin.
(F)脂質生合成または輸送/細胞膜の構造または機能を阻害する剤
F2)リン脂質生合成、メチルトランスフェラーゼ
エジフェンホス(edifenphos)、イプロベンホス(iprobenfos)、ピラゾホス(pyrazophos);イソプロチオラン(isoprothiolane)。
F3)細胞の過酸化
ビフェニル(biphenyl)、クロロネブ(chloroneb)、ジクロラン(dicloran)、キントゼン(quintozene)、テクナゼン(tecnazene)、トルクロホスメチル(tolclofos-methyl);エトリジアゾール(etridiazole)。
F4)細胞膜透過性、脂肪酸
ヨードカルブ(iodocarb)、プロパモカルブ(propamocarb)、プロパモカルブ塩酸塩(propamocarb hydrochloride)、プロチオカルブ(prothiocarb)。
F8)エルゴステロール結合
ナタマイシン(natamycin)。
F9)脂質恒常性および輸送/貯蔵
オキサチアピプロリン(oxathiapiprolin)、フルオキサピプロリン(fluoxapiprolin)。 (F) Agents that inhibit lipid biosynthesis or transport/cell membrane structure or function F2) Phospholipid biosynthesis, methyltransferases edifenphos, iprobenfos, pyrazophos; isoprothiolane.
F3) Cellular biphenyl peroxide, chloroneb, dicloran, quintozene, tecnazene, tolclofos-methyl; etridiazole.
F4) Cell membrane permeability, fatty acids iodocarb, propamocarb, propamocarb hydrochloride, prothiocarb.
F8) Ergosterol-conjugated natamycin.
F9) Lipid homeostasis and transport/storage oxathiapiprolin, fluoxapiprolin.
F2)リン脂質生合成、メチルトランスフェラーゼ
エジフェンホス(edifenphos)、イプロベンホス(iprobenfos)、ピラゾホス(pyrazophos);イソプロチオラン(isoprothiolane)。
F3)細胞の過酸化
ビフェニル(biphenyl)、クロロネブ(chloroneb)、ジクロラン(dicloran)、キントゼン(quintozene)、テクナゼン(tecnazene)、トルクロホスメチル(tolclofos-methyl);エトリジアゾール(etridiazole)。
F4)細胞膜透過性、脂肪酸
ヨードカルブ(iodocarb)、プロパモカルブ(propamocarb)、プロパモカルブ塩酸塩(propamocarb hydrochloride)、プロチオカルブ(prothiocarb)。
F8)エルゴステロール結合
ナタマイシン(natamycin)。
F9)脂質恒常性および輸送/貯蔵
オキサチアピプロリン(oxathiapiprolin)、フルオキサピプロリン(fluoxapiprolin)。 (F) Agents that inhibit lipid biosynthesis or transport/cell membrane structure or function F2) Phospholipid biosynthesis, methyltransferases edifenphos, iprobenfos, pyrazophos; isoprothiolane.
F3) Cellular biphenyl peroxide, chloroneb, dicloran, quintozene, tecnazene, tolclofos-methyl; etridiazole.
F4) Cell membrane permeability, fatty acids iodocarb, propamocarb, propamocarb hydrochloride, prothiocarb.
F8) Ergosterol-conjugated natamycin.
F9) Lipid homeostasis and transport/storage oxathiapiprolin, fluoxapiprolin.
(G)細胞膜のステロール生合成の阻害剤
G1)ステロール生合成のC14位のデメチラーゼ(erg11/cyp51)
トリホリン(triforine);ピリフェノックス(pyrifenox)、ピリソキサゾール(pyrisoxazole);フェナリモル(fenarimol)、ヌアリモール(nuarimol);イマザリル(imazalil)、オキスポコナゾール(oxpoconazole)、ペフラゾエート(pefurazoate)、プロクロラズ(prochloraz)、トリフルミゾール(triflumizole);アザコナゾール(azaconazole)、ビテルタノール(bitertanol)、ブロムコナゾール(bromuconazole)、シプロコナゾール(cyproconazole)、ジフェノコナゾール(difenoconazole)、ジニコナゾール(diniconazole)、エポキシコナゾール(epoxiconazole)、エタコナゾール(etaconazole)、フェンブコナゾール(fenbuconazole)、フルキンコナゾール(fluquinconazole)、フルシラゾール(flusilazole)、フルトリアホール(flutriafol)、ヘキサコナゾール(hexaconazole)、イミベンコナゾール(imibenconazole)、イプコナゾール(ipconazole)、メフェントリフルコナゾール(mefentrifluconazole)、メトコナゾール(metconazole)、ミクロブタニル(myclobutanil)、ペンコナゾール(penconazole)、プロピコナゾール(propiconazole)、シメコナゾール(simeconazole)、テブコナゾール(tebuconazole)、テトラコナゾール(tetraconazole)、トリアジメホン(triadimefon)、トリアジメノール(triadimenol)、トリチコナゾール(triticonazole)、プロチオコナゾール(prothioconazole)。
フルコナゾール(furconazole)、フルコナゾール-シス(furconazole-cis)、ジニコナゾールM(diniconazole-M)。
G2)ステロール生合成におけるΔ14還元酵素およびΔ8→Δ7-イソメラーゼ(erg24、erg2)
アルジモルフ(aldimorph)、ドデモルフ(dodemorph)、ドデモルフ酢酸塩(dodemorphacetate)、フェンプロピモルフ(fenpropimorph)、トリデモルフ(tridemorph);フェンプロピジン(fenpropidin)、ピペラリン(piperalin);スピロキサミン(spiroxamine)。
ブチオベート(buthiobate)。
G3)ステロール生合成系のC4位脱メチル化における3-ケト還元酵素(erg27)
フェンヘキサミド(fenhexamid);フェンピラザミン(fenpyrazamine)。
G4)ステロール生合成系のスクワレンエポキシダーゼ(erg1)
ピリブチカルブ(pyributicarb);ナフチフィン(naftifine)、テルビナフィン(terbinafine)。 (G) Inhibitor of sterol biosynthesis in cell membrane G1) Demethylase at position C14 of sterol biosynthesis (erg11/cyp51)
triforine; pyrifenox, pyrisoxazole; fenarimol, nuarimol; imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole; azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, etaconazole ( etaconazole), fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, mefen trifluconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole.
fluconazole, furconazole-cis, diniconazole-M.
G2) Δ14 reductase and Δ8→Δ7-isomerase (erg24, erg2) in sterol biosynthesis
aldimorph, dodemorph, dodemorphacetate, fenpropimorph, tridemorph; fenpropidin, piperalin; spiroxamine.
buthiobate.
G3) 3-keto reductase (erg27) in C4 demethylation of sterol biosynthesis system
Fenhexamid; fenpyrazamine.
G4) Squalene epoxidase (erg1) of sterol biosynthesis system
Pyributicarb; naftifine, terbinafine.
G1)ステロール生合成のC14位のデメチラーゼ(erg11/cyp51)
トリホリン(triforine);ピリフェノックス(pyrifenox)、ピリソキサゾール(pyrisoxazole);フェナリモル(fenarimol)、ヌアリモール(nuarimol);イマザリル(imazalil)、オキスポコナゾール(oxpoconazole)、ペフラゾエート(pefurazoate)、プロクロラズ(prochloraz)、トリフルミゾール(triflumizole);アザコナゾール(azaconazole)、ビテルタノール(bitertanol)、ブロムコナゾール(bromuconazole)、シプロコナゾール(cyproconazole)、ジフェノコナゾール(difenoconazole)、ジニコナゾール(diniconazole)、エポキシコナゾール(epoxiconazole)、エタコナゾール(etaconazole)、フェンブコナゾール(fenbuconazole)、フルキンコナゾール(fluquinconazole)、フルシラゾール(flusilazole)、フルトリアホール(flutriafol)、ヘキサコナゾール(hexaconazole)、イミベンコナゾール(imibenconazole)、イプコナゾール(ipconazole)、メフェントリフルコナゾール(mefentrifluconazole)、メトコナゾール(metconazole)、ミクロブタニル(myclobutanil)、ペンコナゾール(penconazole)、プロピコナゾール(propiconazole)、シメコナゾール(simeconazole)、テブコナゾール(tebuconazole)、テトラコナゾール(tetraconazole)、トリアジメホン(triadimefon)、トリアジメノール(triadimenol)、トリチコナゾール(triticonazole)、プロチオコナゾール(prothioconazole)。
フルコナゾール(furconazole)、フルコナゾール-シス(furconazole-cis)、ジニコナゾールM(diniconazole-M)。
G2)ステロール生合成におけるΔ14還元酵素およびΔ8→Δ7-イソメラーゼ(erg24、erg2)
アルジモルフ(aldimorph)、ドデモルフ(dodemorph)、ドデモルフ酢酸塩(dodemorphacetate)、フェンプロピモルフ(fenpropimorph)、トリデモルフ(tridemorph);フェンプロピジン(fenpropidin)、ピペラリン(piperalin);スピロキサミン(spiroxamine)。
ブチオベート(buthiobate)。
G3)ステロール生合成系のC4位脱メチル化における3-ケト還元酵素(erg27)
フェンヘキサミド(fenhexamid);フェンピラザミン(fenpyrazamine)。
G4)ステロール生合成系のスクワレンエポキシダーゼ(erg1)
ピリブチカルブ(pyributicarb);ナフチフィン(naftifine)、テルビナフィン(terbinafine)。 (G) Inhibitor of sterol biosynthesis in cell membrane G1) Demethylase at position C14 of sterol biosynthesis (erg11/cyp51)
triforine; pyrifenox, pyrisoxazole; fenarimol, nuarimol; imazalil, oxpoconazole, pefurazoate, prochloraz, triflumizole; azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, etaconazole ( etaconazole), fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, mefen trifluconazole, metconazole, myclobutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole.
fluconazole, furconazole-cis, diniconazole-M.
G2) Δ14 reductase and Δ8→Δ7-isomerase (erg24, erg2) in sterol biosynthesis
aldimorph, dodemorph, dodemorphacetate, fenpropimorph, tridemorph; fenpropidin, piperalin; spiroxamine.
buthiobate.
G3) 3-keto reductase (erg27) in C4 demethylation of sterol biosynthesis system
Fenhexamid; fenpyrazamine.
G4) Squalene epoxidase (erg1) of sterol biosynthesis system
Pyributicarb; naftifine, terbinafine.
(H)細胞壁生合成の阻害剤
H4)キチン合成酵素
ポリオキシン(polyoxin)。
ポリオクソリム(polyoxorim)。
H5)セルロース合成酵素
ジメトモルフ(dimethomorph)、フルモルフ(flumorph)、ピリモルフ(pyrimorph);
ベンチアバリカルブ(benthiavalicarb)、イプロバリカルブ(iprovalicarb)、バリフェナレート(valifenalate);マンジプロパミド(mandipropamid)。 (H) Inhibitor of cell wall biosynthesis H4) Chitin synthase polyoxin.
Polyoxorim.
H5) Cellulose synthase dimethomorph, flumorph, pyrimorph;
Benthiavalicarb, iprovalicarb, valifenalate; mandipropamid.
H4)キチン合成酵素
ポリオキシン(polyoxin)。
ポリオクソリム(polyoxorim)。
H5)セルロース合成酵素
ジメトモルフ(dimethomorph)、フルモルフ(flumorph)、ピリモルフ(pyrimorph);
ベンチアバリカルブ(benthiavalicarb)、イプロバリカルブ(iprovalicarb)、バリフェナレート(valifenalate);マンジプロパミド(mandipropamid)。 (H) Inhibitor of cell wall biosynthesis H4) Chitin synthase polyoxin.
Polyoxorim.
H5) Cellulose synthase dimethomorph, flumorph, pyrimorph;
Benthiavalicarb, iprovalicarb, valifenalate; mandipropamid.
(I)細胞壁のメラニン合成の阻害剤
I1)メラニン生合成の還元酵素
フサライド(fthalide);ピロキロン(pyroquilon);トリシクラゾール(tricyclazole)。
I2)メラニン生合成の脱水酵素
カルプロパミド(carpropamid);ジクロシメット(diclocymet);フェノキサニル(fenoxanil)。
I3)メラニン生合成のポリケタイド合成酵素
トルプロカルブ(tolprocarb)。 (I) Inhibitor of cell wall melanin synthesis I1) Melanin biosynthesis reductase fthalide; pyroquilon; tricyclazole.
I2) Melanin biosynthesis dehydratase carpropamid; diclocymet; fenoxanil.
I3) Tolprocarb, a polyketide synthase for melanin biosynthesis.
I1)メラニン生合成の還元酵素
フサライド(fthalide);ピロキロン(pyroquilon);トリシクラゾール(tricyclazole)。
I2)メラニン生合成の脱水酵素
カルプロパミド(carpropamid);ジクロシメット(diclocymet);フェノキサニル(fenoxanil)。
I3)メラニン生合成のポリケタイド合成酵素
トルプロカルブ(tolprocarb)。 (I) Inhibitor of cell wall melanin synthesis I1) Melanin biosynthesis reductase fthalide; pyroquilon; tricyclazole.
I2) Melanin biosynthesis dehydratase carpropamid; diclocymet; fenoxanil.
I3) Tolprocarb, a polyketide synthase for melanin biosynthesis.
(P)宿主植物の抵抗性を誘導する剤
P1~P3)サリチル酸シグナル伝達
アシベンゾラルSメチル(acibenzolar-S-methyl);プロベナゾール(probenazole);チアジニル(tiadinil)、イソチアニル(isotianil)。
P4)多糖類エリシター
ラミナリン(laminarin)。
P5)アントラキノンエリシター
オオイタドリ抽出液(extract from Reynoutria sachalinensis)。
P6)微生物エリシター
バチルス・マイコイデス分離株J(Bacillus mycoides isolate J);サッカロミセス・セレビシア LAS117 株の細胞壁(cell walls of Saccharomyces cerevisiae strain LAS117)。
P7)ホスホナート
ホセチル(fosetyl-Al);亜リン酸および塩(phosphorous acid and salts);ホセチルカルシウム(fosetyl-K)、ホセチルナトリウム(fosetyl-Na)。
P8)サリチル酸関連
ジクロベンチアゾクス(dichlobentiazox)。 (P) Agents that induce host plant resistance P1 to P3) Salicylic acid signal transduction acibenzolar-S-methyl; probenazole; tiadinil, isotianil.
P4) Polysaccharide elicitor laminarin.
P5) Anthraquinone elicitor extract from Reynoutria sachalinensis.
P6) Microorganism elicitor Bacillus mycoides isolate J; cell walls of Saccharomyces cerevisiae strain LAS117.
P7) Phosphonate fosetyl-Al; phosphorous acid and salts; fosetyl-K, fosetyl-Na.
P8) Salicylic acid-related dichlobentiazox.
P1~P3)サリチル酸シグナル伝達
アシベンゾラルSメチル(acibenzolar-S-methyl);プロベナゾール(probenazole);チアジニル(tiadinil)、イソチアニル(isotianil)。
P4)多糖類エリシター
ラミナリン(laminarin)。
P5)アントラキノンエリシター
オオイタドリ抽出液(extract from Reynoutria sachalinensis)。
P6)微生物エリシター
バチルス・マイコイデス分離株J(Bacillus mycoides isolate J);サッカロミセス・セレビシア LAS117 株の細胞壁(cell walls of Saccharomyces cerevisiae strain LAS117)。
P7)ホスホナート
ホセチル(fosetyl-Al);亜リン酸および塩(phosphorous acid and salts);ホセチルカルシウム(fosetyl-K)、ホセチルナトリウム(fosetyl-Na)。
P8)サリチル酸関連
ジクロベンチアゾクス(dichlobentiazox)。 (P) Agents that induce host plant resistance P1 to P3) Salicylic acid signal transduction acibenzolar-S-methyl; probenazole; tiadinil, isotianil.
P4) Polysaccharide elicitor laminarin.
P5) Anthraquinone elicitor extract from Reynoutria sachalinensis.
P6) Microorganism elicitor Bacillus mycoides isolate J; cell walls of Saccharomyces cerevisiae strain LAS117.
P7) Phosphonate fosetyl-Al; phosphorous acid and salts; fosetyl-K, fosetyl-Na.
P8) Salicylic acid-related dichlobentiazox.
(U)作用機構不明の剤
シモキサニル(cymoxanil);テクロフタラム(tecloftalam);トリアゾキシド(triazoxide);フルスルファミド(flusulfamide);ジクロメジン(diclomezine);シフルフェナミド(cyflufenamid);ドジン(dodine)、ドジン遊離塩基(dodine free base);フルチアニル(flutianil);フェリムゾン(ferimzone);テブフロキン(tebufloquin);ピカルブトラゾクス(picarbutrazox);バリダマイシン(validamycin)。
ベトキサジン(bethoxazin)、シプロフラム(cyprofuram)、フルメトベル(flumetover)、
ニトロタールイソプロピル(nitrothal-isopropyl)、プロパミジン(propamidine)。
イプフルフェノキン(ipflufenoquin)、ピリダクロメチル(pyridachlometyl)、ピラプロポイン(pyrapropoyne)、アミノピリフェン(aminopyrifen)、イプフェントリフルコナゾール(ipfentrifluconazole)、キノフメリン(quinofumelin)、ジピメチトロン(dipymetitrone)。 (U) Agents with unknown mechanism of action cymoxanil; tecloftalam; triazoxide; flusulfamide; diclomezine; cyflufenamide; dodine, dodine free base ); flutianil; ferimzone; tebufloquin; picarbutrazox; validamycin.
bethoxazin, cyprofuram, flumetover,
Nitrothal-isopropyl, propamidine.
Ipflufenoquin, pyridachlometyl, pyrapropoyne, aminopyrifen, ipfentrifluconazole, quinofumelin, dipymetitrone.
シモキサニル(cymoxanil);テクロフタラム(tecloftalam);トリアゾキシド(triazoxide);フルスルファミド(flusulfamide);ジクロメジン(diclomezine);シフルフェナミド(cyflufenamid);ドジン(dodine)、ドジン遊離塩基(dodine free base);フルチアニル(flutianil);フェリムゾン(ferimzone);テブフロキン(tebufloquin);ピカルブトラゾクス(picarbutrazox);バリダマイシン(validamycin)。
ベトキサジン(bethoxazin)、シプロフラム(cyprofuram)、フルメトベル(flumetover)、
ニトロタールイソプロピル(nitrothal-isopropyl)、プロパミジン(propamidine)。
イプフルフェノキン(ipflufenoquin)、ピリダクロメチル(pyridachlometyl)、ピラプロポイン(pyrapropoyne)、アミノピリフェン(aminopyrifen)、イプフェントリフルコナゾール(ipfentrifluconazole)、キノフメリン(quinofumelin)、ジピメチトロン(dipymetitrone)。 (U) Agents with unknown mechanism of action cymoxanil; tecloftalam; triazoxide; flusulfamide; diclomezine; cyflufenamide; dodine, dodine free base ); flutianil; ferimzone; tebufloquin; picarbutrazox; validamycin.
bethoxazin, cyprofuram, flumetover,
Nitrothal-isopropyl, propamidine.
Ipflufenoquin, pyridachlometyl, pyrapropoyne, aminopyrifen, ipfentrifluconazole, quinofumelin, dipymetitrone.
(M)多作用点接触活性を示す剤
銅(種々の塩)(copper(different salts))、塩基性硫酸銅(basic copper sulfate)、ボルドー液(Bordeaux mixture)、水酸化銅(copper hydroxide)、銅ナフタレート(copper naphthenate)、オキシ塩化銅(copper oxychloride)、硫酸銅(copper sulfate)、酸化銅(cuprous oxide)、オキシン銅(oxine-copper);硫黄(sulphur)、石灰硫黄合剤(Lime sulfur);アンバム(amobam)、ファーバム(ferbam)、マンゼブ(mancozeb)、マンネブ(maneb)、メチラム(metiram)、プロピネブ(propineb)、チウラム(thiram)、チアゾール亜鉛(zinc thiazole)、ジネブ(zineb)、ジラム(ziram);キャプタン(captan)、カプタホール(captafol)、ホルペット(folpet);クロロタロニル(chlorothalonil);ジクロフルアニド(dichlofluanid)、トリルフルアニド(tolylfluanid);グアザチン(guazatine)、グアザチン酢酸塩(guazatine acetates)、イミノクタジン(iminoctadine)、イミノクタジン酢酸塩(iminoctadine triacetate)、イミノクタジンアルベシル酸塩(iminoctadine trialbesilate;アニラジン(anilazine);ジチアノン(dithianon);キノメチオナート(chinomethionat);フルオルイミド(fluoroimide);メタスルホカルブ(methasulfocarb)。
ダゾメット(dazomet)、クフラネブ(cufraneb)、マンカッパー(mancopper)、ポリカーバメート(polycarbamate)。 (M) Agents that exhibit multi-site contact activity Copper (different salts), basic copper sulfate, Bordeaux mixture, copper hydroxide, copper Copper naphthenate, copper oxychloride, copper sulfate, cuprous oxide, oxine-copper; sulphur, lime sulfur; amobam, ferbam, mancozeb, maneb, metiram, propineb, thiram, zinc thiazole, zineb, ziram ); captan, captafol, folpet; chlorothalonil; dichlofluanid, tolylfluanid; guazatine, guazatine acetates, iminoctadine (iminoctadine), iminoctadine triacetate, iminoctadine trialbesilate; anilazine; dithianon; chinomethionat; fluorimide; methasulfocarb.
dazomet, cufraneb, mancopper, polycarbamate.
銅(種々の塩)(copper(different salts))、塩基性硫酸銅(basic copper sulfate)、ボルドー液(Bordeaux mixture)、水酸化銅(copper hydroxide)、銅ナフタレート(copper naphthenate)、オキシ塩化銅(copper oxychloride)、硫酸銅(copper sulfate)、酸化銅(cuprous oxide)、オキシン銅(oxine-copper);硫黄(sulphur)、石灰硫黄合剤(Lime sulfur);アンバム(amobam)、ファーバム(ferbam)、マンゼブ(mancozeb)、マンネブ(maneb)、メチラム(metiram)、プロピネブ(propineb)、チウラム(thiram)、チアゾール亜鉛(zinc thiazole)、ジネブ(zineb)、ジラム(ziram);キャプタン(captan)、カプタホール(captafol)、ホルペット(folpet);クロロタロニル(chlorothalonil);ジクロフルアニド(dichlofluanid)、トリルフルアニド(tolylfluanid);グアザチン(guazatine)、グアザチン酢酸塩(guazatine acetates)、イミノクタジン(iminoctadine)、イミノクタジン酢酸塩(iminoctadine triacetate)、イミノクタジンアルベシル酸塩(iminoctadine trialbesilate;アニラジン(anilazine);ジチアノン(dithianon);キノメチオナート(chinomethionat);フルオルイミド(fluoroimide);メタスルホカルブ(methasulfocarb)。
ダゾメット(dazomet)、クフラネブ(cufraneb)、マンカッパー(mancopper)、ポリカーバメート(polycarbamate)。 (M) Agents that exhibit multi-site contact activity Copper (different salts), basic copper sulfate, Bordeaux mixture, copper hydroxide, copper Copper naphthenate, copper oxychloride, copper sulfate, cuprous oxide, oxine-copper; sulphur, lime sulfur; amobam, ferbam, mancozeb, maneb, metiram, propineb, thiram, zinc thiazole, zineb, ziram ); captan, captafol, folpet; chlorothalonil; dichlofluanid, tolylfluanid; guazatine, guazatine acetates, iminoctadine (iminoctadine), iminoctadine triacetate, iminoctadine trialbesilate; anilazine; dithianon; chinomethionat; fluorimide; methasulfocarb.
dazomet, cufraneb, mancopper, polycarbamate.
(BM01)複数の作用機構を有する生物農薬/生物由来の農薬
ハウチワマメ苗木の子葉からの抽出物(extract from the cotyledons of lupine plantlets);Swinglea glutinosa からの抽出物 (extract from Swinglea glutinosa);ゴセイカユプテ(ティーツリー)の抽出物(extract from Melaleuca alternifolia (tea treeoil));植物油類(混合物)(plant oils (mixtures)):オイゲノール(eugenol)、ゲラニオール(geraniol)、チモール(thymol)。 (BM01) Biopesticides with multiple mechanisms of action/Biologically derived pesticides Extract from the cotyledons of lupine plantlets; Extract from Swinglea glutinosa; Gosei Kayupte ( extract from Melaleuca alternifolia (tea treeoil); plant oils (mixtures): eugenol, geraniol, thymol.
ハウチワマメ苗木の子葉からの抽出物(extract from the cotyledons of lupine plantlets);Swinglea glutinosa からの抽出物 (extract from Swinglea glutinosa);ゴセイカユプテ(ティーツリー)の抽出物(extract from Melaleuca alternifolia (tea treeoil));植物油類(混合物)(plant oils (mixtures)):オイゲノール(eugenol)、ゲラニオール(geraniol)、チモール(thymol)。 (BM01) Biopesticides with multiple mechanisms of action/Biologically derived pesticides Extract from the cotyledons of lupine plantlets; Extract from Swinglea glutinosa; Gosei Kayupte ( extract from Melaleuca alternifolia (tea treeoil); plant oils (mixtures): eugenol, geraniol, thymol.
(BM02)複数の作用機構を有する生物農薬/生物由来の農薬
トリコデルマ・アトロビリデ I-1237株(Trichoderma atroviride strain I-1237)、トリコデルマ・アトロビリデ LU132株(Trichoderma atroviride strain LU132)、トリコデルマ・アトロビリデ SC1株(Trichoderma atroviride strain SC1)、トリコデルマ・アトロビリデ SKT-1株(Trichoderma atroviride strain SKT-1)、トリコデルマ・アトロビリデ 77B株(Trichoderma atroviride strain 77B);
トリコデルマ・アスペレルム T34 株(Trichoderma asperellum strain T34)、トリコデルマ・アスペレルムkd株(Trichoderma asperellum strain kd);
トリコデルマ・ハルチアナム T-22 株(Trichoderma harzianum strain T-22);
トリコデルマ・ ビレンスG-41株(Trichoderma virens strain G-41);
グリオクラディウム・カテナラタム J1446 株 (Gliocladium catenulatum strain J1446);
クロノスタキス・ロゼアCR-7株(Clonostachys rosea strain CR-7);
コニオチリウム・ミニタンスCON/M/91-08株(Coniothyrium minitans strain CON/M/91-08);
タラロマイセス・ フラバス SAY-Y-94-01 株 (Talaromyces flavus strain SAY-Y-94-01);
サッカロマイセス・セレビシエLAS02株 (Saccharomyces cerevisae strain LAS02);
バチルス・アミロリクエファシエンスQST713 株(Bacillus amyloliquefaciens strain QST713)、バチルス・アミロリクエファシエンスFZB24 株(Bacillus amyloliquefaciens strain FZB24)、バチルス・アミロリクエファシエンスMBI600 株(Bacillus amylolique faciens strain MBI600)、バチルス・アミロリクエファシエンスD747 株(Bacillus amyloliquefaciens strain D747)、バチルス・アミロリクエファシエンスF727 株(Bacillus amyloliquefaciens strain F727)、バチルス・アミロリクエファシエンスAT-332 株(Bacillus amyloliquefaciens strain AT-332);
バチルス・ズブチリスAFS032321 株(Bacillus subtilis strain AFS032321) 、バチルス・ズブチリスY1336 株 (Bacillus subtilis strain Y1336)、バチルス・ズブチリスHAI-0404 株(Bacillus subtilis strain HAI-0404);
シュードモナス・クロロファフィスAFS 009 株(Pseudomonas chlororaphis strain AFS009);
ストレプトミセス・グリセオビリデス K61 株(Streptomyces griseovirides strain K61);
ストレプトミセス・リディクス WYEC 108株(Streptomyces lydicus strain WYEC108)。
(NC)未分類の成分
鉱物油(mineral oils)、有機油(organic oils)、無機塩類(inorganic salts)、天然物起源(material of biological origin)。 (BM02) Biological pesticides with multiple mechanisms of action/Biologically derived pesticides Trichoderma atroviride strain I-1237, Trichoderma atroviride strain LU132, Trichoderma atroviride strain SC1 ( Trichoderma atroviride strain SC1), Trichoderma atroviride strain SKT-1, Trichoderma atroviride strain 77B;
Trichoderma asperellum strain T34, Trichoderma asperellum strain kd;
Trichoderma harzianum strain T-22;
Trichoderma virens strain G-41;
Gliocladium catenulatum strain J1446;
Clonostachys rosea strain CR-7;
Coniothyrium minitans strain CON/M/91-08;
Talaromyces flavus strain SAY-Y-94-01;
Saccharomyces cerevisae strain LAS02;
Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens strain FZB24, Bacillus amyloliquefaciens strain MBI600, Bacillus amyloliquefaciens strain MBI600 Bacillus amyloliquefaciens strain D747, Bacillus amyloliquefaciens strain F727, Bacillus amyloliquefaciens strain AT-332;
Bacillus subtilis strain AFS032321, Bacillus subtilis strain Y1336, Bacillus subtilis strain HAI-0404;
Pseudomonas chlororaphis strain AFS009;
Streptomyces griseovirides strain K61;
Streptomyces lydicus strain WYEC108.
(NC) Unclassified components mineral oils, organic oils, inorganic salts, material of biological origin.
トリコデルマ・アトロビリデ I-1237株(Trichoderma atroviride strain I-1237)、トリコデルマ・アトロビリデ LU132株(Trichoderma atroviride strain LU132)、トリコデルマ・アトロビリデ SC1株(Trichoderma atroviride strain SC1)、トリコデルマ・アトロビリデ SKT-1株(Trichoderma atroviride strain SKT-1)、トリコデルマ・アトロビリデ 77B株(Trichoderma atroviride strain 77B);
トリコデルマ・アスペレルム T34 株(Trichoderma asperellum strain T34)、トリコデルマ・アスペレルムkd株(Trichoderma asperellum strain kd);
トリコデルマ・ハルチアナム T-22 株(Trichoderma harzianum strain T-22);
トリコデルマ・ ビレンスG-41株(Trichoderma virens strain G-41);
グリオクラディウム・カテナラタム J1446 株 (Gliocladium catenulatum strain J1446);
クロノスタキス・ロゼアCR-7株(Clonostachys rosea strain CR-7);
コニオチリウム・ミニタンスCON/M/91-08株(Coniothyrium minitans strain CON/M/91-08);
タラロマイセス・ フラバス SAY-Y-94-01 株 (Talaromyces flavus strain SAY-Y-94-01);
サッカロマイセス・セレビシエLAS02株 (Saccharomyces cerevisae strain LAS02);
バチルス・アミロリクエファシエンスQST713 株(Bacillus amyloliquefaciens strain QST713)、バチルス・アミロリクエファシエンスFZB24 株(Bacillus amyloliquefaciens strain FZB24)、バチルス・アミロリクエファシエンスMBI600 株(Bacillus amylolique faciens strain MBI600)、バチルス・アミロリクエファシエンスD747 株(Bacillus amyloliquefaciens strain D747)、バチルス・アミロリクエファシエンスF727 株(Bacillus amyloliquefaciens strain F727)、バチルス・アミロリクエファシエンスAT-332 株(Bacillus amyloliquefaciens strain AT-332);
バチルス・ズブチリスAFS032321 株(Bacillus subtilis strain AFS032321) 、バチルス・ズブチリスY1336 株 (Bacillus subtilis strain Y1336)、バチルス・ズブチリスHAI-0404 株(Bacillus subtilis strain HAI-0404);
シュードモナス・クロロファフィスAFS 009 株(Pseudomonas chlororaphis strain AFS009);
ストレプトミセス・グリセオビリデス K61 株(Streptomyces griseovirides strain K61);
ストレプトミセス・リディクス WYEC 108株(Streptomyces lydicus strain WYEC108)。
(NC)未分類の成分
鉱物油(mineral oils)、有機油(organic oils)、無機塩類(inorganic salts)、天然物起源(material of biological origin)。 (BM02) Biological pesticides with multiple mechanisms of action/Biologically derived pesticides Trichoderma atroviride strain I-1237, Trichoderma atroviride strain LU132, Trichoderma atroviride strain SC1 ( Trichoderma atroviride strain SC1), Trichoderma atroviride strain SKT-1, Trichoderma atroviride strain 77B;
Trichoderma asperellum strain T34, Trichoderma asperellum strain kd;
Trichoderma harzianum strain T-22;
Trichoderma virens strain G-41;
Gliocladium catenulatum strain J1446;
Clonostachys rosea strain CR-7;
Coniothyrium minitans strain CON/M/91-08;
Talaromyces flavus strain SAY-Y-94-01;
Saccharomyces cerevisae strain LAS02;
Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens strain FZB24, Bacillus amyloliquefaciens strain MBI600, Bacillus amyloliquefaciens strain MBI600 Bacillus amyloliquefaciens strain D747, Bacillus amyloliquefaciens strain F727, Bacillus amyloliquefaciens strain AT-332;
Bacillus subtilis strain AFS032321, Bacillus subtilis strain Y1336, Bacillus subtilis strain HAI-0404;
Pseudomonas chlororaphis strain AFS009;
Streptomyces griseovirides strain K61;
Streptomyces lydicus strain WYEC108.
(NC) Unclassified components mineral oils, organic oils, inorganic salts, material of biological origin.
本発明の有害生物防除剤と混用または併用することができる、植物調節剤の具体例を以下に示す。
アブシジン酸、カイネチン、ベンジルアミノプリン、1,3-ジフェニルウレア、ホルクロルフェヌロン、チジアズロン、クロルフェヌロン、ジヒドロゼアチン、ジベレリンA、ジベレリンA4、ジベレリンA7、ジベレリンA3、1-メチルシクロプロパン、N-アセチルアミノエトキシビニルグリシン(別名:アビグリシン)、アミノオキシ酢酸、硝酸銀、塩化コバルト、IAA、4-CPA、クロプロップ、2,4-D、MCPB、インドール-3-酪酸、ジクロルプロップ、フェノチオール、1-ナフチルアセトアミド、エチクロゼート、クロキシホナック、マレイン酸ヒドラジド、2,3,5-トリヨード安息香酸、サリチル酸、サリチル酸メチル、(-)-ジャスモン酸、ジャスモン酸メチル、(+)-ストリゴール、(+)-デオキシストリゴール、(+)-オロバンコール、(+)-ソルゴラクトン、4-オキソ-4-(2-フェニルエチル)アミノ酪酸;エテホン、クロルメコート、メピコートクロリド、ベンジルアデニン、5-アミノレブリン酸。 Specific examples of plant regulators that can be mixed or used 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 aviglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothiol, 1 -Naphthylacetamide, ethiclozate, cloxyphonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+) -deoxystrigol, (+)-olobanchol, (+)-solgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid; ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid.
アブシジン酸、カイネチン、ベンジルアミノプリン、1,3-ジフェニルウレア、ホルクロルフェヌロン、チジアズロン、クロルフェヌロン、ジヒドロゼアチン、ジベレリンA、ジベレリンA4、ジベレリンA7、ジベレリンA3、1-メチルシクロプロパン、N-アセチルアミノエトキシビニルグリシン(別名:アビグリシン)、アミノオキシ酢酸、硝酸銀、塩化コバルト、IAA、4-CPA、クロプロップ、2,4-D、MCPB、インドール-3-酪酸、ジクロルプロップ、フェノチオール、1-ナフチルアセトアミド、エチクロゼート、クロキシホナック、マレイン酸ヒドラジド、2,3,5-トリヨード安息香酸、サリチル酸、サリチル酸メチル、(-)-ジャスモン酸、ジャスモン酸メチル、(+)-ストリゴール、(+)-デオキシストリゴール、(+)-オロバンコール、(+)-ソルゴラクトン、4-オキソ-4-(2-フェニルエチル)アミノ酪酸;エテホン、クロルメコート、メピコートクロリド、ベンジルアデニン、5-アミノレブリン酸。 Specific examples of plant regulators that can be mixed or used 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 aviglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothiol, 1 -Naphthylacetamide, ethiclozate, cloxyphonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+) -deoxystrigol, (+)-olobanchol, (+)-solgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid; ethephon, chlormequat, mepiquat chloride, benzyladenine, 5-aminolevulinic acid.
〔外部寄生虫防除剤〕
本発明の外部寄生虫防除剤は、本発明化合物から選ばれる少なくともひとつを有効成分として含有する。本発明の外部寄生虫防除剤に含まれる本発明化合物の量は外部寄生虫の防除効果を示す限りにおいて特に制限されない。 [External parasite control agent]
The ectoparasite control agent of the present invention contains at least one compound 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 an ectoparasite control effect.
本発明の外部寄生虫防除剤は、本発明化合物から選ばれる少なくともひとつを有効成分として含有する。本発明の外部寄生虫防除剤に含まれる本発明化合物の量は外部寄生虫の防除効果を示す限りにおいて特に制限されない。 [External parasite control agent]
The ectoparasite control agent of the present invention contains at least one compound 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 an ectoparasite control effect.
本発明の外部寄生虫防除剤の処理の対象となる宿主動物としては、ヒト、家畜哺乳動物(例えば、ウシ、ウマ、ブタ、ヒツジ、ヤギなど)、実験動物(例えば、マウス、ラット、スナネズミなど)、愛玩動物(例えば、ハムスター、モルモット、イヌ、ネコ、ウマ、リス、ウサギ、フェレットなど)、野生および動物園の哺乳動物(サル、キツネ、シカ、バッファローなど)、家禽(シチメンチョウ、アヒル、ニワトリ、ウズラ、ガチョウなど)、愛玩鳥(ハト、オウム、九官鳥、文鳥、インコ、ジュウシマツ、カナリアなど)などの温血動物; または、サケ、マス、ニシキゴイなどの魚類を挙げることができる。その他にも、ミツバチ、クワガタムシ、カブトムシを挙げることができる。
Host animals to be treated with the ectoparasite control agent of the present invention include humans, livestock mammals (e.g., cows, horses, pigs, sheep, goats, etc.), experimental animals (e.g., mice, rats, gerbils, etc.). ), companion animals (e.g. hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, buffalo, etc.), poultry (turkeys, ducks, chickens, etc.) Examples include warm-blooded animals such as quail, geese, etc.), pet birds (pigeons, parrots, mynahs, sparrows, parakeets, Japanese pine, canaries, etc.); and fish such as salmon, trout, and carp. Other examples include bees, stag beetles, and rhinoceros beetles.
本発明の外部寄生虫防除剤は、公知の獣医学的な手法(局所、経口、非経口または皮下投与)で施用することができる。その方法として、錠剤、カプセル、飼料混入などにより動物に経口的に投与する方法; 浸漬液、坐薬、注射(筋肉内、皮下、静脈内、腹腔内など)などにより動物に投与する方法; 油性または水性液剤を噴霧、ポアオン、スポットオンなどにより局所的に投与する方法; 樹脂に外部寄生虫防除剤を練り込み、前記混練物を首輪、耳札などの適当な形状に成形し、それを動物に装着し局所的に投与する方法;
などを挙げることができる。 The ectoparasite control agent of the present invention can be applied by known veterinary techniques (topically, orally, parenterally, or subcutaneously). Methods of administration include oral administration to animals using tablets, capsules, and feed mixtures; administration to animals via immersion solutions, suppositories, and injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); oil-based or A method of locally administering an aqueous solution by spraying, pour-on, spot-on, etc.; kneading an ectoparasiticide into a resin, molding the kneaded product into a suitable shape such as a collar or ear tag, and applying it to an animal. Method of wearing and local administration;
etc. can be mentioned.
などを挙げることができる。 The ectoparasite control agent of the present invention can be applied by known veterinary techniques (topically, orally, parenterally, or subcutaneously). Methods of administration include oral administration to animals using tablets, capsules, and feed mixtures; administration to animals via immersion solutions, suppositories, and injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); oil-based or A method of locally administering an aqueous solution by spraying, pour-on, spot-on, etc.; kneading an ectoparasiticide into a resin, molding the kneaded product into a suitable shape such as a collar or ear tag, and applying it to an animal. Method of wearing and local administration;
etc. can be mentioned.
外部寄生虫は、宿主動物、特には温血動物の中および上に寄生する。詳しくは、宿主動物の背、脇下、下腹部、内股部などに寄生して動物から血液やフケなどの栄養源を得て生息する。外部寄生虫としては、ダニ類、シラミ類、ノミ類、カ、サシバエ、ニクバエなどを挙げることができる。本発明の外部寄生虫防除剤によって防除可能な外部寄生虫の具体例を以下に示す。
Ectoparasites live in and on host animals, especially warm-blooded animals. Specifically, they live by parasitizing the back, armpits, lower abdomen, inner thighs, etc. of host animals, and obtain nutrients such as blood and dander from the animals. Examples of external parasites include mites, lice, fleas, mosquitoes, stable flies, and black flies. Specific examples of ectoparasites that can be controlled by the ectoparasiticide of the present invention are shown below.
(1)ダニ類(Acari)
ワクモ科(Dermanyssidae)のダニ、オオサシダニ科(Macronyssidae)のダニ、トゲダニ科(Laelapidae)のダニ、ヘギダニ科(Varroidae)のダニ、ヒメダニ科(Argasidae)のダニ、マダニ科(Ixodidae)のダニ、キュウセンヒゼンダニ科(Psoroptidae)のダニ、ヒゼンダニ科(Sarcoptidae)のダニ、トリヒゼンダニ科(Knemidokoptidae)のダニ、ニキビダニ科(Demodixidae)のダニ、ツツガムシ科(Trombiculidae)のダニ、クワガタナカセ類等の昆虫寄生性のダニ。
(2)シラミ目(Phthiraptera)
ケモノジラミ科(Haematopinidae)のシラミ、ケモノホソジラミ科(Linognathidae)のシラミ、タンカクハジラミ科(Menoponidae)のハジラミ、チョウカクハジラミ科(Philopteridae)のハジラミ、ケモノハジラミ科(Trichodectidae)のハジラミ。
(3)ノミ目(Siphonaptera)
ヒトノミ科(Pulicidae)のノミ、例えば、イヌノミ属種(Ctenocephalides spp.)の、イヌノミ(Ctenocephalides canis)、ネコノミ(Ctenocephalides felis);
スナノミ科(Tungidae)のノミ、ナガノミ科(Ceratophyllidae)のノミ、ホソノミ科(Leptopsyllidae)のノミ。
(4)カメムシ目(Hemiptera)。
(5)ハエ目(Diptera)の害虫カ科(Culicidae)のカ、ブユ科(Simuliidae)のブユ、ヌカカ科(Ceratopogonidae)のヌカカ、アブ科(Tabanidae)のアブ、イエバエ科(Muscidae)のハエ、ツエツエバエ科(Glossinidae)のシェシェバエ、ニクバエ科のニクバエ、シラミバエ科(Hippoboscidae)のハエ、クロバエ科(Calliphoridae)のハエ、ヒツジバエ科(Oestridae)のハエ。 (1) Acari
Mites of the family Dermanyssidae, mites of the family Macronyssidae, mites of the family Laelapidae, mites of the family Varroidae, mites of the family Argasidae, mites of the family Ixodidae, and mites of the family Ixodidae Insect parasitic mites such as Psoroptidae, Sarcoptidae, Knemidokoptidae, Demodixidae, Trombiculidae, and other insect parasitic mites. .
(2) Phthiraptera
Lice of the family Haematopinidae, lice of the family Linognathidae, lice of the family Menoponidae, lice of the family Philopteridae, lice of the family Trichodectidae.
(3) Siphonaptera
fleas of the family Pulicidae, such as Ctenocephalides spp., dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis);
Fleas of the family Tungidae, fleas of the family Ceratophyllidae, and fleas of the family Leptopsyllidae.
(4) Hemiptera.
(5) Pests of the order Diptera; mosquitoes of the family Culicidae; blackflies of the family Simuliidae; midges of the family Ceratopogonidae; horseflies of the family Tabanidae; flies of the family Muscidae; Sheshe flies of the family Glossinidae, flies of the family Hippoboscidae, flies of the family Hippoboscidae, flies of the family Calliphoridae, and flies of the family Oestridae.
ワクモ科(Dermanyssidae)のダニ、オオサシダニ科(Macronyssidae)のダニ、トゲダニ科(Laelapidae)のダニ、ヘギダニ科(Varroidae)のダニ、ヒメダニ科(Argasidae)のダニ、マダニ科(Ixodidae)のダニ、キュウセンヒゼンダニ科(Psoroptidae)のダニ、ヒゼンダニ科(Sarcoptidae)のダニ、トリヒゼンダニ科(Knemidokoptidae)のダニ、ニキビダニ科(Demodixidae)のダニ、ツツガムシ科(Trombiculidae)のダニ、クワガタナカセ類等の昆虫寄生性のダニ。
(2)シラミ目(Phthiraptera)
ケモノジラミ科(Haematopinidae)のシラミ、ケモノホソジラミ科(Linognathidae)のシラミ、タンカクハジラミ科(Menoponidae)のハジラミ、チョウカクハジラミ科(Philopteridae)のハジラミ、ケモノハジラミ科(Trichodectidae)のハジラミ。
(3)ノミ目(Siphonaptera)
ヒトノミ科(Pulicidae)のノミ、例えば、イヌノミ属種(Ctenocephalides spp.)の、イヌノミ(Ctenocephalides canis)、ネコノミ(Ctenocephalides felis);
スナノミ科(Tungidae)のノミ、ナガノミ科(Ceratophyllidae)のノミ、ホソノミ科(Leptopsyllidae)のノミ。
(4)カメムシ目(Hemiptera)。
(5)ハエ目(Diptera)の害虫カ科(Culicidae)のカ、ブユ科(Simuliidae)のブユ、ヌカカ科(Ceratopogonidae)のヌカカ、アブ科(Tabanidae)のアブ、イエバエ科(Muscidae)のハエ、ツエツエバエ科(Glossinidae)のシェシェバエ、ニクバエ科のニクバエ、シラミバエ科(Hippoboscidae)のハエ、クロバエ科(Calliphoridae)のハエ、ヒツジバエ科(Oestridae)のハエ。 (1) Acari
Mites of the family Dermanyssidae, mites of the family Macronyssidae, mites of the family Laelapidae, mites of the family Varroidae, mites of the family Argasidae, mites of the family Ixodidae, and mites of the family Ixodidae Insect parasitic mites such as Psoroptidae, Sarcoptidae, Knemidokoptidae, Demodixidae, Trombiculidae, and other insect parasitic mites. .
(2) Phthiraptera
Lice of the family Haematopinidae, lice of the family Linognathidae, lice of the family Menoponidae, lice of the family Philopteridae, lice of the family Trichodectidae.
(3) Siphonaptera
fleas of the family Pulicidae, such as Ctenocephalides spp., dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis);
Fleas of the family Tungidae, fleas of the family Ceratophyllidae, and fleas of the family Leptopsyllidae.
(4) Hemiptera.
(5) Pests of the order Diptera; mosquitoes of the family Culicidae; blackflies of the family Simuliidae; midges of the family Ceratopogonidae; horseflies of the family Tabanidae; flies of the family Muscidae; Sheshe flies of the family Glossinidae, flies of the family Hippoboscidae, flies of the family Hippoboscidae, flies of the family Calliphoridae, and flies of the family Oestridae.
〔内部寄生虫防除若しくは駆除剤〕
本発明の内部寄生虫防除若しくは駆除剤は、本発明化合物から選ばれる少なくともひとつを有効成分として含有する。本発明の内部寄生虫防除若しくは駆除剤に含まれる本発明化合物の量は内部寄生虫の防除効果を示す限りにおいて特に制限されない。 [Internal parasite control or extermination agent]
The endoparasite controlling or exterminating agent of the present invention contains at least one compound 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 exhibits an endoparasite control effect.
本発明の内部寄生虫防除若しくは駆除剤は、本発明化合物から選ばれる少なくともひとつを有効成分として含有する。本発明の内部寄生虫防除若しくは駆除剤に含まれる本発明化合物の量は内部寄生虫の防除効果を示す限りにおいて特に制限されない。 [Internal parasite control or extermination agent]
The endoparasite controlling or exterminating agent of the present invention contains at least one compound 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 exhibits an endoparasite control effect.
本発明の内部寄生虫防除若しくは駆除剤の対象となる寄生虫は、宿主動物、特には温血動物や魚類の中に寄生する(内部寄生虫)。本発明の内部寄生虫防除若しくは駆除剤が有効な宿主動物としては、ヒト、家畜哺乳動物(例えば、ウシ、ウマ、ブタ、ヒツジ、ヤギなど)、実験動物(例えば、マウス、ラット、スナネズミなど)、愛玩動物(例えば、ハムスター、モルモット、イヌ、ネコ、ウマ、リス、ウサギ、フェレットなど)、野生および動物園の哺乳動物(サル、キツネ、シカ、バッファローなど)、家禽(シチメンチョウ、アヒル、ニワトリ、ウズラ、ガチョウなど)、愛玩鳥(ハト、オウム、九官鳥、文鳥、インコ、ジュウシマツ、カナリアなど)などの温血動物;または、サケ、マス、ニシキゴイなどの魚類を挙げることができる。寄生虫を防除および駆除することで、寄生虫が媒介する寄生虫疾患を予防または治療することができる。
The parasites targeted by the endoparasite control or extermination agent of the present invention parasitize host animals, particularly warm-blooded animals and fish (endoparasites). Host animals for which the endoparasite control or extermination agent of the present invention is effective include humans, livestock mammals (e.g., cows, horses, pigs, sheep, goats, etc.), and laboratory animals (e.g., mice, rats, gerbils, etc.). , companion animals (e.g. hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, buffaloes, etc.), poultry (turkeys, ducks, chickens, quails, etc.) warm-blooded animals such as pet birds (pigeons, parrots, mynahs, sparrows, parakeets, Japanese pine, canaries, etc.); and fish such as salmon, trout, and carp. By controlling and exterminating parasites, parasitic diseases transmitted by the parasites can be prevented or treated.
防除または駆除対象の寄生虫としては、以下のものを挙げることができる。
(1)腎虫目(Dioctophymatida)の線虫類
(a)腎虫科(Dioctophymatidae)の腎虫、例えば、ディオクトフィーマ属種(Dioctophyma spp.)の、腎虫(Dioctophyma renale);
(b)ソブリフィメ科(Soboliphymatidae)の腎虫、例えば、ソブリフィメ属種(Soboliphyme spp.)の、ソブリフィメ・アベイ(Soboliphyme abei)、ソブリフィメ・ブツリニ(Soboliphyme baturini)。 Parasites to be controlled or exterminated include the following:
(1) Nematodes of the order Dioctophymatida (a) Kidney worms of the family Dioctophymatidae, for example, Dioctophyma renale of the genus Dioctophyma spp.;
(b) Kidney insects of the family Soboliphymatidae, such as Soboliphyme abei, Soboliphyme baturini of the Soboliphyme spp.
(1)腎虫目(Dioctophymatida)の線虫類
(a)腎虫科(Dioctophymatidae)の腎虫、例えば、ディオクトフィーマ属種(Dioctophyma spp.)の、腎虫(Dioctophyma renale);
(b)ソブリフィメ科(Soboliphymatidae)の腎虫、例えば、ソブリフィメ属種(Soboliphyme spp.)の、ソブリフィメ・アベイ(Soboliphyme abei)、ソブリフィメ・ブツリニ(Soboliphyme baturini)。 Parasites to be controlled or exterminated include the following:
(1) Nematodes of the order Dioctophymatida (a) Kidney worms of the family Dioctophymatidae, for example, Dioctophyma renale of the genus Dioctophyma spp.;
(b) Kidney insects of the family Soboliphymatidae, such as Soboliphyme abei, Soboliphyme baturini of the Soboliphyme spp.
(2)毛頭虫目(Trichocephalida)の線虫類
(a)旋毛虫科(Trichinellidae)の旋毛虫、例えば、旋毛虫属種(Trichinella spp.)の、旋毛虫(Trichinella spiralis);
(b)鞭虫科(Trichuridae)の鞭虫、例えば、キャピラリア属種(Capillaria spp.)の、有環毛細線虫(Capillaria annulata)、捻転毛細線虫(Capillaria contorta)、肝毛細線虫(Capillaria hepatica)、穿通毛細線虫(Capillaria perforans)、キャピラリア・プリカ(Capillaria plica)、豚毛細線虫(Capillaria suis);トリキュリス属種(Trichuris spp.)の、犬鞭虫(Trichuris vulpis)、牛鞭虫(Trichuris discolor)、羊鞭虫(Trichuris ovis)、トリキュリス・スクリジャビニー(Trichuris skrjabini)、豚鞭虫(Trichuris suis)。 (2) Nematodes of the order Trichocephalida (a) Trichinella of the family Trichinellidae, for example, Trichinella spiralis of the Trichinella spp.;
(b) Whipworms of the family Trichuridae, such as Capillaria spp., Capillaria annulata, Capillaria contorta, hepatic capillary nematodes ( Capillaria hepatica), Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris spp., Trichuris vulpis, cattle Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris suis.
(a)旋毛虫科(Trichinellidae)の旋毛虫、例えば、旋毛虫属種(Trichinella spp.)の、旋毛虫(Trichinella spiralis);
(b)鞭虫科(Trichuridae)の鞭虫、例えば、キャピラリア属種(Capillaria spp.)の、有環毛細線虫(Capillaria annulata)、捻転毛細線虫(Capillaria contorta)、肝毛細線虫(Capillaria hepatica)、穿通毛細線虫(Capillaria perforans)、キャピラリア・プリカ(Capillaria plica)、豚毛細線虫(Capillaria suis);トリキュリス属種(Trichuris spp.)の、犬鞭虫(Trichuris vulpis)、牛鞭虫(Trichuris discolor)、羊鞭虫(Trichuris ovis)、トリキュリス・スクリジャビニー(Trichuris skrjabini)、豚鞭虫(Trichuris suis)。 (2) Nematodes of the order Trichocephalida (a) Trichinella of the family Trichinellidae, for example, Trichinella spiralis of the Trichinella spp.;
(b) Whipworms of the family Trichuridae, such as Capillaria spp., Capillaria annulata, Capillaria contorta, hepatic capillary nematodes ( Capillaria hepatica), Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris spp., Trichuris vulpis, cattle Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris suis.
(3)桿線虫目(Rhabditida)の線虫類
糞線虫科(Strongyloididae)の糞線虫、例えば、糞線虫属種(Strongyloides spp.)の、乳頭糞線虫(Strongyloides papillosus)、猫糞線虫(Strongyloides planiceps)、豚糞線虫(Strongyloides ransomi)、豚糞線虫(Strongyloides suis)、糞線虫(Strongyloides stercoralis)、アメリカ猫糞線虫(Strongyloides tumefaciens)、ネズミ糞線虫(Strongyloides ratti)。 (3) Nematodes of the order Rhabditida Strongyloididae of the family Strongyloididae, such as Strongyloides papillosus of the genus Strongyloides spp., cat feces Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, Strongyloides ratti .
糞線虫科(Strongyloididae)の糞線虫、例えば、糞線虫属種(Strongyloides spp.)の、乳頭糞線虫(Strongyloides papillosus)、猫糞線虫(Strongyloides planiceps)、豚糞線虫(Strongyloides ransomi)、豚糞線虫(Strongyloides suis)、糞線虫(Strongyloides stercoralis)、アメリカ猫糞線虫(Strongyloides tumefaciens)、ネズミ糞線虫(Strongyloides ratti)。 (3) Nematodes of the order Rhabditida Strongyloididae of the family Strongyloididae, such as Strongyloides papillosus of the genus Strongyloides spp., cat feces Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, Strongyloides ratti .
(4)円虫目(Strongylida)の線虫類
鈎虫科(Ancylostomatidae)の鉤虫、例えば、鉤虫属種(Ancylostoma spp.)の、ブラジル鉤虫(Ancylostoma braziliense)、犬鉤虫(Ancylostoma caninum)、ズビニ鉤虫(Ancylostoma duodenale)、ネコ鈎虫(Ancylostoma tubaeforme);ウンシナリア属種(Uncinaria stenocephala)の、狭頭鉤虫(Uncinaria stenocephala);ブノストマム属種(Bunostomum spp.)の、牛鉤虫(Bunostomum phlebotomum)、羊鉤虫(Bunostomum trigonocephalum)。 (4) Nematodes of the order Strongylida Hookworms of the family Ancylostomatidae, such as Ancylostoma braziliense, Ancylostoma caninum, and Zubini hookworm of the Ancylostoma spp. Ancylostoma duodenale, Ancylostoma tubaeforme; Uncinaria stenocephala, Uncinaria stenocephala; Bunostomum spp., Bunostomum phlebotomum, sheep hookworm ( Bunostomum trigonocephalum).
鈎虫科(Ancylostomatidae)の鉤虫、例えば、鉤虫属種(Ancylostoma spp.)の、ブラジル鉤虫(Ancylostoma braziliense)、犬鉤虫(Ancylostoma caninum)、ズビニ鉤虫(Ancylostoma duodenale)、ネコ鈎虫(Ancylostoma tubaeforme);ウンシナリア属種(Uncinaria stenocephala)の、狭頭鉤虫(Uncinaria stenocephala);ブノストマム属種(Bunostomum spp.)の、牛鉤虫(Bunostomum phlebotomum)、羊鉤虫(Bunostomum trigonocephalum)。 (4) Nematodes of the order Strongylida Hookworms of the family Ancylostomatidae, such as Ancylostoma braziliense, Ancylostoma caninum, and Zubini hookworm of the Ancylostoma spp. Ancylostoma duodenale, Ancylostoma tubaeforme; Uncinaria stenocephala, Uncinaria stenocephala; Bunostomum spp., Bunostomum phlebotomum, sheep hookworm ( Bunostomum trigonocephalum).
(5)円虫目(Strongylida)の線虫類
(a)住血線虫科(Angiostrongylidae)の線虫、例えば、ネコ肺虫属種(Aelurostrongylus spp.)の、猫肺虫(Aelurostrongylus abstrusus);住血線虫属種(Angiostrongylus spp.)の、住血線虫(Angiostrongylus vasorum)、広東住血線虫(Angiostrongylus cantonesis);
(b)クレノゾーマ科(Crenosomatidae)の線虫、例えば、クレノゾーマ属種(Crenosoma spp.)の、肺毛細線虫(Crenosoma aerophila)、キツネ肺虫(Crenosoma vulpis);
(c)フィラロイデス科(Filaroididae)の線虫、例えば、フィラロイデス属種(Filaroides spp.)の、犬肺虫(Filaroides hirthi)、フィラロイデス・オスレリ(Filaroidesosleri);
(d)肺虫科(Metastrongylidae)の肺虫、例えば、豚肺虫属種(Metastrongylus spp.)の、豚肺虫(Metastrongylus apri)、メタストロンギルス・アシムメトリクス(Metastrongylus asymmetricus)、メタストロンギルス・プデンドテクタス(Metastrongylus pudendotectus)、メタストロンギルス・サルミィ(Metastrongylus salmi);
(e)開嘴虫科(Syngamidae)の開嘴虫、例えば、シアトストーマ属種(Cyathostoma spp.)の、水鳥肺虫(Cyathostoma bronchialis);シンガムス属種(Syngamus spp.)の、スクリジャビン開嘴虫(Syngamus skrjabinomorpha)、鶏開嘴虫(Syngamus trachea)。 (5) Nematodes of the order Strongylida (a) Nematodes of the family Angiostrongylidae, for example Aelurostrongylus abstrusus of the genus Aelurostrongylus spp.; Angiostrongylus vasorum, Angiostrongylus cantonesis of the genus Angiostrongylus spp.;
(b) Nematodes of the family Crenosomatidae, such as Crenosoma spp., Crenosoma aerophila, Crenosoma vulpis;
(c) nematodes of the family Filaroididae, such as Filaroides spp., canine lungworm (Filaroides hirthi), Filaroidesosleri;
(d) Lungworms of the family Metastrongylidae, such as Metastrongylus spp., Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus pudendotectus ( Metastrongylus pudendotectus), Metastrongylus salmi;
(e) Cyathostoma bronchialis of the family Syngamidae, such as Cyathostoma bronchialis of the genus Cyathostoma spp.; Cyathostoma bronchialis of the genus Syngamus spp. Syngamus skrjabinomorpha), chicken beak insect (Syngamus trachea).
(a)住血線虫科(Angiostrongylidae)の線虫、例えば、ネコ肺虫属種(Aelurostrongylus spp.)の、猫肺虫(Aelurostrongylus abstrusus);住血線虫属種(Angiostrongylus spp.)の、住血線虫(Angiostrongylus vasorum)、広東住血線虫(Angiostrongylus cantonesis);
(b)クレノゾーマ科(Crenosomatidae)の線虫、例えば、クレノゾーマ属種(Crenosoma spp.)の、肺毛細線虫(Crenosoma aerophila)、キツネ肺虫(Crenosoma vulpis);
(c)フィラロイデス科(Filaroididae)の線虫、例えば、フィラロイデス属種(Filaroides spp.)の、犬肺虫(Filaroides hirthi)、フィラロイデス・オスレリ(Filaroidesosleri);
(d)肺虫科(Metastrongylidae)の肺虫、例えば、豚肺虫属種(Metastrongylus spp.)の、豚肺虫(Metastrongylus apri)、メタストロンギルス・アシムメトリクス(Metastrongylus asymmetricus)、メタストロンギルス・プデンドテクタス(Metastrongylus pudendotectus)、メタストロンギルス・サルミィ(Metastrongylus salmi);
(e)開嘴虫科(Syngamidae)の開嘴虫、例えば、シアトストーマ属種(Cyathostoma spp.)の、水鳥肺虫(Cyathostoma bronchialis);シンガムス属種(Syngamus spp.)の、スクリジャビン開嘴虫(Syngamus skrjabinomorpha)、鶏開嘴虫(Syngamus trachea)。 (5) Nematodes of the order Strongylida (a) Nematodes of the family Angiostrongylidae, for example Aelurostrongylus abstrusus of the genus Aelurostrongylus spp.; Angiostrongylus vasorum, Angiostrongylus cantonesis of the genus Angiostrongylus spp.;
(b) Nematodes of the family Crenosomatidae, such as Crenosoma spp., Crenosoma aerophila, Crenosoma vulpis;
(c) nematodes of the family Filaroididae, such as Filaroides spp., canine lungworm (Filaroides hirthi), Filaroidesosleri;
(d) Lungworms of the family Metastrongylidae, such as Metastrongylus spp., Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus pudendotectus ( Metastrongylus pudendotectus), Metastrongylus salmi;
(e) Cyathostoma bronchialis of the family Syngamidae, such as Cyathostoma bronchialis of the genus Cyathostoma spp.; Cyathostoma bronchialis of the genus Syngamus spp. Syngamus skrjabinomorpha), chicken beak insect (Syngamus trachea).
(6)円虫目(Strongylida)の線虫類
(a)モリネウス科(Molineidae)の線虫、例えば、ネマトジルス属種(Nematodirus spp.)の、細頸毛円虫(Nematodirus filicollis)、ネマトジルス・スパティガー(Nematodirus spathiger);
(b)ディクチオカウルス科(Dictyocaulidae)の線虫、例えば、ディクチオカウルス属種(Dictyocaulus spp.)の、糸状肺虫(Dictyocaulus filaria)、牛肺虫(Dictyocaulus viviparus );
(c)捻転胃虫科(Haemonchidae )の線虫、例えば、ヘモンクス属種(Haemonchus spp.)の、捻転胃虫(Haemonchus contortus);メキストシリウス属種(Mecistocirrus spp.)の、牛捻転胃虫(Mecistocirrus digitatus);
(d)捻転胃虫科(Haemonchidae)の線虫、例えば、胃虫属種(Ostertagia spp.)の、オステルターグ胃虫(Ostertagia ostertagi );
(e)ヘリグモネラ科(Heligmonellidae )の線虫、例えば、ニッポストロンジルス属種(Nippostrongylus spp.)の、ネズミ円虫(Nippostrongylus braziliensis);
(f)毛様線虫科(Trichostrongylidae)の線虫、例えば、毛様線虫属種(Trichostrongylus spp.)の、皺胃毛様線虫(Trichostrongylus axei )、蛇状毛様線虫(Trichostrongylus colubriformis )、毛様線虫科(Trichostrongylus tenuis);ヒオストロンギルス属種(Hyostrongylus spp.)の、紅色毛様線虫(Hyostrongylus rubidus);オベリスコイデス属種(Obeliscoides spp.)の、オベリスコイデス・クニクリ(Obeliscoides cuniculi)。 (6) Nematodes of the order Strongylida (a) Nematodes of the family Molineidae, such as Nematodirus filicollis, Nematodirus spp. Tigger (Nematodirus spathiger);
(b) Nematodes of the family Dictyocauridae, such as Dictyocaulus spp., filamentous lungworm (Dictyocaulus filaria), bovine lungworm (Dictyocaulus viviparus);
(c) Nematodes of the family Haemonchidae, such as Haemonchus contortus of the genus Haemonchus spp.; bovine contortus of the genus Mecistocirrus spp. (Mecistocirrus digitatus);
(d) nematodes of the family Haemonchidae, such as Ostertagia ostertagi of the genus Ostertagia spp.;
(e) Nematodes of the family Heligmonellaceae, such as Nippostrongylus braziliensis of the genus Nippostrongylus spp.;
(f) Nematodes of the family Trichostrongylidae, such as Trichostrongylus spp., Trichostrongylus axei, Trichostrongylus colubriformis; ), Trichostrongylus tenuis; Hyostrongylus rubidus of the genus Hyostrongylus spp.; Obeliscoides cuniculi of the genus Obeliscoides spp. ).
(a)モリネウス科(Molineidae)の線虫、例えば、ネマトジルス属種(Nematodirus spp.)の、細頸毛円虫(Nematodirus filicollis)、ネマトジルス・スパティガー(Nematodirus spathiger);
(b)ディクチオカウルス科(Dictyocaulidae)の線虫、例えば、ディクチオカウルス属種(Dictyocaulus spp.)の、糸状肺虫(Dictyocaulus filaria)、牛肺虫(Dictyocaulus viviparus );
(c)捻転胃虫科(Haemonchidae )の線虫、例えば、ヘモンクス属種(Haemonchus spp.)の、捻転胃虫(Haemonchus contortus);メキストシリウス属種(Mecistocirrus spp.)の、牛捻転胃虫(Mecistocirrus digitatus);
(d)捻転胃虫科(Haemonchidae)の線虫、例えば、胃虫属種(Ostertagia spp.)の、オステルターグ胃虫(Ostertagia ostertagi );
(e)ヘリグモネラ科(Heligmonellidae )の線虫、例えば、ニッポストロンジルス属種(Nippostrongylus spp.)の、ネズミ円虫(Nippostrongylus braziliensis);
(f)毛様線虫科(Trichostrongylidae)の線虫、例えば、毛様線虫属種(Trichostrongylus spp.)の、皺胃毛様線虫(Trichostrongylus axei )、蛇状毛様線虫(Trichostrongylus colubriformis )、毛様線虫科(Trichostrongylus tenuis);ヒオストロンギルス属種(Hyostrongylus spp.)の、紅色毛様線虫(Hyostrongylus rubidus);オベリスコイデス属種(Obeliscoides spp.)の、オベリスコイデス・クニクリ(Obeliscoides cuniculi)。 (6) Nematodes of the order Strongylida (a) Nematodes of the family Molineidae, such as Nematodirus filicollis, Nematodirus spp. Tigger (Nematodirus spathiger);
(b) Nematodes of the family Dictyocauridae, such as Dictyocaulus spp., filamentous lungworm (Dictyocaulus filaria), bovine lungworm (Dictyocaulus viviparus);
(c) Nematodes of the family Haemonchidae, such as Haemonchus contortus of the genus Haemonchus spp.; bovine contortus of the genus Mecistocirrus spp. (Mecistocirrus digitatus);
(d) nematodes of the family Haemonchidae, such as Ostertagia ostertagi of the genus Ostertagia spp.;
(e) Nematodes of the family Heligmonellaceae, such as Nippostrongylus braziliensis of the genus Nippostrongylus spp.;
(f) Nematodes of the family Trichostrongylidae, such as Trichostrongylus spp., Trichostrongylus axei, Trichostrongylus colubriformis; ), Trichostrongylus tenuis; Hyostrongylus rubidus of the genus Hyostrongylus spp.; Obeliscoides cuniculi of the genus Obeliscoides spp. ).
(7)円虫目(Strongylida)の線虫類
(a)シャベルティア科(Chabertiidae)の線虫、例えば、シャベルティア属種(Chabertia spp.)の、羊縮小線虫(Chabertia ovina);腸結節虫属種(Oesophagostomum spp.)の、腸結節虫(豚)(Oesophagostomum brevicaudatum)、コロンビア腸結節虫(Oesophagostomum columbianum)、豚腸結節虫(Oesophagostomum dentatum)、腸結節虫(豚)(Oesophagostomum georgianum)、腸結節虫(Oesophagostomum maplestonei)、腸結節虫(豚)(Oesophagostomum quadrispinulatum)、牛腸結節虫(Oesophagostomum radiatum)、山羊腸結節虫(Oesophagostomum venulosum)、腸結節虫(イノシシ)(Oesophagostomum watanabei);
(b)豚腎虫科(Stephanuridae)の線虫、例えば、ステファヌラス属種(Stephanurus spp.)の、豚腎虫(Stephanurus dentatus );
(c)円虫科(Strongylidae)の線虫、例えば、円虫属種(Strongylus spp.)の、ロバ円虫(Strongylus asini )、無歯円虫(Strongylus edentatus)、馬円虫(Strongylusequinus)、普通円虫(Strongylus vulgaris)。 (7) Nematodes of the order Strongylida (a) Nematodes of the family Chabertiidae, such as Chabertia ovina of Chabertia spp.; intestinal nodules Oesophagostomum brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum, Oesophagostomum georgianum, of the genus Oesophagostomum spp. Intestinal noduleworm (Oesophagostomum maplestonei), Intestinal noduleworm (pig) (Oesophagostomum quadrispinulatum), Bovine intestinal noduleworm (Oesophagostomum radiatum), Goat intestinal noduleworm (Oesophagostomum venulosum), Intestinal noduleworm (boar) (Oesophagostomum watanabei);
(b) nematodes of the Stephanuridae family, such as Stephanurus dentatus of the Stephanurus spp.;
(c) Nematodes of the strongyle family (Strongylidae), such as Strongylus spp., Strongylus asini, Strongylus edentatus, Strongylusequinus, Strongylus vulgaris.
(a)シャベルティア科(Chabertiidae)の線虫、例えば、シャベルティア属種(Chabertia spp.)の、羊縮小線虫(Chabertia ovina);腸結節虫属種(Oesophagostomum spp.)の、腸結節虫(豚)(Oesophagostomum brevicaudatum)、コロンビア腸結節虫(Oesophagostomum columbianum)、豚腸結節虫(Oesophagostomum dentatum)、腸結節虫(豚)(Oesophagostomum georgianum)、腸結節虫(Oesophagostomum maplestonei)、腸結節虫(豚)(Oesophagostomum quadrispinulatum)、牛腸結節虫(Oesophagostomum radiatum)、山羊腸結節虫(Oesophagostomum venulosum)、腸結節虫(イノシシ)(Oesophagostomum watanabei);
(b)豚腎虫科(Stephanuridae)の線虫、例えば、ステファヌラス属種(Stephanurus spp.)の、豚腎虫(Stephanurus dentatus );
(c)円虫科(Strongylidae)の線虫、例えば、円虫属種(Strongylus spp.)の、ロバ円虫(Strongylus asini )、無歯円虫(Strongylus edentatus)、馬円虫(Strongylusequinus)、普通円虫(Strongylus vulgaris)。 (7) Nematodes of the order Strongylida (a) Nematodes of the family Chabertiidae, such as Chabertia ovina of Chabertia spp.; intestinal nodules Oesophagostomum brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum, Oesophagostomum georgianum, of the genus Oesophagostomum spp. Intestinal noduleworm (Oesophagostomum maplestonei), Intestinal noduleworm (pig) (Oesophagostomum quadrispinulatum), Bovine intestinal noduleworm (Oesophagostomum radiatum), Goat intestinal noduleworm (Oesophagostomum venulosum), Intestinal noduleworm (boar) (Oesophagostomum watanabei);
(b) nematodes of the Stephanuridae family, such as Stephanurus dentatus of the Stephanurus spp.;
(c) Nematodes of the strongyle family (Strongylidae), such as Strongylus spp., Strongylus asini, Strongylus edentatus, Strongylusequinus, Strongylus vulgaris.
(8)蟯虫目(Oxyurida)の線虫類
蟯虫科(Oxyuridae)の線虫、例えば、エンテロビウス属種(Enterobius spp.)の、チンパンジー蟯虫(Enterobius anthropopitheci)、蟯虫(Enterobius vermicularis);
オキシルス属(Oxyuris spp.)の、馬蟯虫(Oxyuris equi);パサルルス属種(Passalurus spp.)の、ウサギ蟯虫(Passalurus ambiguus)。 (8) Nematodes of the order Oxyurida Nematodes of the family Oxyuridae, such as Enterobius spp., chimpanzee pinworms (Enterobius anthropopitheci), pinworms (Enterobius vermicularis);
Oxyuris equi, of the genus Oxyuris; Passalurus ambiguus, of the genus Passalurus spp.
蟯虫科(Oxyuridae)の線虫、例えば、エンテロビウス属種(Enterobius spp.)の、チンパンジー蟯虫(Enterobius anthropopitheci)、蟯虫(Enterobius vermicularis);
オキシルス属(Oxyuris spp.)の、馬蟯虫(Oxyuris equi);パサルルス属種(Passalurus spp.)の、ウサギ蟯虫(Passalurus ambiguus)。 (8) Nematodes of the order Oxyurida Nematodes of the family Oxyuridae, such as Enterobius spp., chimpanzee pinworms (Enterobius anthropopitheci), pinworms (Enterobius vermicularis);
Oxyuris equi, of the genus Oxyuris; Passalurus ambiguus, of the genus Passalurus spp.
(9)回虫目(Ascaridida)の線虫類
(a)ニワトリ回虫科(Ascaridiidae)の線虫、例えば、ニワトリ回虫属種(Ascaridia spp.)の、ニワトリ回虫(Ascaridia galli);
(b)盲腸虫科(Heterakidae)の線虫、例えば、ヘテラキス属種(Heterakis spp.)の、ヘテラキス・ベラムポリア(Heterakis beramporia)、ヘテラキス・ブレビスピクルム(Heterakis brevispiculum)、鶏盲腸虫(Heterakis gallinarum)、ヘテラキス・プシーラ(Heterakis pusilla)、ヘテラキス・プトオーストラリス(Heterakis putaustralis);
(c)アニサキス科(Anisakidae)の線虫、例えば、アニサキス属種(Anisakis spp.)の、アニサキス線虫(Anisakis simplex);
(d)回虫科(Ascarididae)の線虫、例えば、回虫属種(Ascaris spp.)の、ヒト回虫(Ascaris lumbricoides)、豚回虫(Ascaris suum);パラスカリア属種(Parascaris spp.)の、馬回虫(Parascaris equorum);
(e)トキソカーラ科(Toxocaridae)の線虫、例えば、トキソカーラ属種(Toxocara spp.)の、犬回虫(Toxocara canis)、犬小回虫(Toxocara leonina)、豚回虫(Toxocarasuum)、牛回虫(Toxocara vitulorum)、猫回虫(Toxocara cati)。 (9) Nematodes of the order Ascaridida (a) Nematodes of the family Ascaridiidae, such as Ascaridia galli of the Ascaridia spp.;
(b) Nematodes of the family Heterakidae, such as Heterakis spp., Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum; , Heterakis pusilla, Heterakis putaustralis;
(c) nematodes of the family Anisakidae, such as Anisakis simplex of the genus Anisakis spp.;
(d) Nematodes of the Ascarididae family, such as Ascaris lumbricoides of the Ascaris spp., Ascaris suum; horse roundworms of the Parascaris spp. (Parascaris equorum);
(e) Nematodes of the family Toxocaridae, such as Toxocara spp., Toxocara canis, Toxocara leonina, Toxocarasuum, Toxocara vitulorum; ), Toxocara cati.
(a)ニワトリ回虫科(Ascaridiidae)の線虫、例えば、ニワトリ回虫属種(Ascaridia spp.)の、ニワトリ回虫(Ascaridia galli);
(b)盲腸虫科(Heterakidae)の線虫、例えば、ヘテラキス属種(Heterakis spp.)の、ヘテラキス・ベラムポリア(Heterakis beramporia)、ヘテラキス・ブレビスピクルム(Heterakis brevispiculum)、鶏盲腸虫(Heterakis gallinarum)、ヘテラキス・プシーラ(Heterakis pusilla)、ヘテラキス・プトオーストラリス(Heterakis putaustralis);
(c)アニサキス科(Anisakidae)の線虫、例えば、アニサキス属種(Anisakis spp.)の、アニサキス線虫(Anisakis simplex);
(d)回虫科(Ascarididae)の線虫、例えば、回虫属種(Ascaris spp.)の、ヒト回虫(Ascaris lumbricoides)、豚回虫(Ascaris suum);パラスカリア属種(Parascaris spp.)の、馬回虫(Parascaris equorum);
(e)トキソカーラ科(Toxocaridae)の線虫、例えば、トキソカーラ属種(Toxocara spp.)の、犬回虫(Toxocara canis)、犬小回虫(Toxocara leonina)、豚回虫(Toxocarasuum)、牛回虫(Toxocara vitulorum)、猫回虫(Toxocara cati)。 (9) Nematodes of the order Ascaridida (a) Nematodes of the family Ascaridiidae, such as Ascaridia galli of the Ascaridia spp.;
(b) Nematodes of the family Heterakidae, such as Heterakis spp., Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum; , Heterakis pusilla, Heterakis putaustralis;
(c) nematodes of the family Anisakidae, such as Anisakis simplex of the genus Anisakis spp.;
(d) Nematodes of the Ascarididae family, such as Ascaris lumbricoides of the Ascaris spp., Ascaris suum; horse roundworms of the Parascaris spp. (Parascaris equorum);
(e) Nematodes of the family Toxocaridae, such as Toxocara spp., Toxocara canis, Toxocara leonina, Toxocarasuum, Toxocara vitulorum; ), Toxocara cati.
(10)旋尾線虫目(Spirurida)の線虫類
(a)オンコセルカ科(Onchocercidae)の線虫、例えば、ブルギア属種(Brugia spp.)の、マレー糸状虫(Brugia malayi)、ブルギア・パハンギィ(Brugia pahangi)、ブルギア・パティ(Brugia patei);ディペタロネーマ属種(Dipetalonema spp.)の、ディペタロネーマ・リコンディトゥム(Dipetalonema reconditum);イヌ糸状虫属種(Dirofilaria spp.)の、イヌ糸状虫(Dirofilaria immitis);フィラリア属種(Filaria spp.)の、フィラリア・オクリィ(Filaria oculi);オンコセルカ属種(Onchocerca spp.)の、頸部糸状虫(Onchocerca cervicalis)、ギブソン糸状虫(Onchocerca gibsoni)、咽頭糸状虫(Onchocerca gutturosa);
(b)セタリア科(Setariidae)の線虫、例えば、セタリア属種(Setaria spp.)の、指状糸状虫(Setaria digitata)、馬糸条虫(Setaria equina)、唇乳頭糸状虫(Setarialabiatopapillosa)、マーシャル糸状虫(Setaria marshalli);ブケレリア属種(Wuchereria spp.)の、バンクロフト糸状虫(Wuchereria bancrofti);
(c)糸状虫科(Filariidae)の線虫、例えば、パラフィラリア属種(Parafilaria spp.)の、多乳頭糸状虫(Parafilaria multipapillosa);ステファノフィラリア属種(Stephanofilaria spp.)の、ステファノフィラリア・アッサムエンシス(Stephanofilaria assamensis)、ステファノフィラリア・デドエシー(Stephanofilaria dedoesi)、ステファノフィラリア・カエリー(Stephanofilaria kaeli)、沖縄糸状虫(Stephanofilaria okinawaensis)、ステファノフィラリア・スティレシー(Stephanofilaria stilesi)。 (10) Nematodes of the order Spirurida (a) Nematodes of the family Onchocercidae, such as Brugia spp., Brugia malayi, Brugia pahangii (Brugia pahangi), Brugia patei; Dipetalonema spp., Dipetalonema reconditum; Dirofilaria spp., Dirofilaria Filaria oculi; Onchocerca spp.; Cervical threadworm (Onchocerca cervicalis); Onchocerca gibsoni; Pharyngeal threadworm Insect (Onchocerca gutturosa);
(b) Nematodes of the Setariidae family, such as Setaria digitata, Setaria equina, Setaria labiatopapillosa, of the Setaria spp. Setaria marshalli; Wuchereria bancrofti, of the genus Wuchereria spp.;
(c) Nematodes of the family Filariidae, such as Parafilaria multipapillosa of the genus Parafilaria spp.; Stephanofilaria assumum of the genus Stephanofilaria spp. Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.
(a)オンコセルカ科(Onchocercidae)の線虫、例えば、ブルギア属種(Brugia spp.)の、マレー糸状虫(Brugia malayi)、ブルギア・パハンギィ(Brugia pahangi)、ブルギア・パティ(Brugia patei);ディペタロネーマ属種(Dipetalonema spp.)の、ディペタロネーマ・リコンディトゥム(Dipetalonema reconditum);イヌ糸状虫属種(Dirofilaria spp.)の、イヌ糸状虫(Dirofilaria immitis);フィラリア属種(Filaria spp.)の、フィラリア・オクリィ(Filaria oculi);オンコセルカ属種(Onchocerca spp.)の、頸部糸状虫(Onchocerca cervicalis)、ギブソン糸状虫(Onchocerca gibsoni)、咽頭糸状虫(Onchocerca gutturosa);
(b)セタリア科(Setariidae)の線虫、例えば、セタリア属種(Setaria spp.)の、指状糸状虫(Setaria digitata)、馬糸条虫(Setaria equina)、唇乳頭糸状虫(Setarialabiatopapillosa)、マーシャル糸状虫(Setaria marshalli);ブケレリア属種(Wuchereria spp.)の、バンクロフト糸状虫(Wuchereria bancrofti);
(c)糸状虫科(Filariidae)の線虫、例えば、パラフィラリア属種(Parafilaria spp.)の、多乳頭糸状虫(Parafilaria multipapillosa);ステファノフィラリア属種(Stephanofilaria spp.)の、ステファノフィラリア・アッサムエンシス(Stephanofilaria assamensis)、ステファノフィラリア・デドエシー(Stephanofilaria dedoesi)、ステファノフィラリア・カエリー(Stephanofilaria kaeli)、沖縄糸状虫(Stephanofilaria okinawaensis)、ステファノフィラリア・スティレシー(Stephanofilaria stilesi)。 (10) Nematodes of the order Spirurida (a) Nematodes of the family Onchocercidae, such as Brugia spp., Brugia malayi, Brugia pahangii (Brugia pahangi), Brugia patei; Dipetalonema spp., Dipetalonema reconditum; Dirofilaria spp., Dirofilaria Filaria oculi; Onchocerca spp.; Cervical threadworm (Onchocerca cervicalis); Onchocerca gibsoni; Pharyngeal threadworm Insect (Onchocerca gutturosa);
(b) Nematodes of the Setariidae family, such as Setaria digitata, Setaria equina, Setaria labiatopapillosa, of the Setaria spp. Setaria marshalli; Wuchereria bancrofti, of the genus Wuchereria spp.;
(c) Nematodes of the family Filariidae, such as Parafilaria multipapillosa of the genus Parafilaria spp.; Stephanofilaria assumum of the genus Stephanofilaria spp. Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.
(11)旋尾線虫目(Spirurida)の線虫類
(a)顎口虫科(Gnathostomatidae)の線虫、例えば、顎口虫属種(Gnathostoma spp.)の、顎口虫(Gnathostoma doloresi)、有棘顎口虫(Gnathostoma spinigerum);
(b)ハブロネーマ科(Habronematidae)の線虫、例えば、ハブロネーマ属種(Habronema spp.)の、小口胃虫(Habronema majus)、小口胃虫(Habronema microstoma)、蠅馬胃虫(Habronema muscae);ドラスキア属種(Draschia spp.)の、大口馬胃虫(Draschia megastoma);
(c)フィザロプテラ科(Physalopteridae)の線虫、例えば、フィサロプテラ属種(Physaloptera spp.)の、犬胃虫(Physaloptera canis)、キツネ胃虫(Physaloptera cesticillata)、フィサロプテラ・エルドシオーナ(Physaloptera erdocyona)、フィサロプテラ・フェリディス(Physaloptera felidis)、エジプト猫胃虫(Physaloptera gemina)、フィサロプテラ・パピロラディラータ(Physaloptera papilloradiata)、猫胃虫(Physaloptera praeputialis)、フィサロプテラ・シュードプラエルティアリス(Physaloptera pseudopraerutialis)、ラーラ胃虫(Physaloptera rara)、フィサロプテラ・シビリカ(Physaloptera sibirica)、フィサロプテラ・ブルピニウス(Physaloptera vulpineus);
(d)ゴンギロネマ科(Gongylonematidae)の線虫、例えば、ゴンギロネマ属種(Gongylonema spp.)の、美麗食道虫(Gongylonema pulchrum);
(e)スピロセルカ科(Spirocercidae)の線虫、例えば、アスカロプス属種(Ascarops spp.)の、類円豚胃虫(Ascarops strongylina);
(f)テラジア科(Thelaziidae)の線虫、例えば、テラジア属種(Thelazia spp.)の、東洋眼虫(Thelazia callipaeda)、テラジア・グローサ(Thelazia gulosa)、涙眼虫(Thelazia lacrymalis)、ロデシア眼虫(Thelazia rhodesi)、スクリャービン眼虫(Thelazia skrjabini)。 (11) Nematodes of the order Spirurida (a) Nematodes of the family Gnathostomatidae, such as Gnathostoma doloresi of the genus Gnathostoma spp. , Gnathostoma spinigerum;
(b) Nematodes of the family Habronematidae, such as Habronema majus, Habronema microstoma, Habronema muscae of the genus Habronema spp.; Draschia Draschia megastoma of the genus and species (Draschia spp.);
(c) Nematodes of the family Physalopteridae, such as Physaloptera spp., Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera spp. Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaloptera rara), Physaloptera sibirica, Physaloptera vulpineus;
(d) nematodes of the family Gongylonematidae, such as Gongylonema pulchrum of the genus Gongylonema spp.;
(e) nematodes of the Spirocercidae family, such as Ascarops spp., Ascarops strongylina;
(f) Nematodes of the family Thelaziidae, such as Thelazia spp., Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Rhodesian eye; worm (Thelazia rhodesi), Scriabin's eye worm (Thelazia skrjabini).
(a)顎口虫科(Gnathostomatidae)の線虫、例えば、顎口虫属種(Gnathostoma spp.)の、顎口虫(Gnathostoma doloresi)、有棘顎口虫(Gnathostoma spinigerum);
(b)ハブロネーマ科(Habronematidae)の線虫、例えば、ハブロネーマ属種(Habronema spp.)の、小口胃虫(Habronema majus)、小口胃虫(Habronema microstoma)、蠅馬胃虫(Habronema muscae);ドラスキア属種(Draschia spp.)の、大口馬胃虫(Draschia megastoma);
(c)フィザロプテラ科(Physalopteridae)の線虫、例えば、フィサロプテラ属種(Physaloptera spp.)の、犬胃虫(Physaloptera canis)、キツネ胃虫(Physaloptera cesticillata)、フィサロプテラ・エルドシオーナ(Physaloptera erdocyona)、フィサロプテラ・フェリディス(Physaloptera felidis)、エジプト猫胃虫(Physaloptera gemina)、フィサロプテラ・パピロラディラータ(Physaloptera papilloradiata)、猫胃虫(Physaloptera praeputialis)、フィサロプテラ・シュードプラエルティアリス(Physaloptera pseudopraerutialis)、ラーラ胃虫(Physaloptera rara)、フィサロプテラ・シビリカ(Physaloptera sibirica)、フィサロプテラ・ブルピニウス(Physaloptera vulpineus);
(d)ゴンギロネマ科(Gongylonematidae)の線虫、例えば、ゴンギロネマ属種(Gongylonema spp.)の、美麗食道虫(Gongylonema pulchrum);
(e)スピロセルカ科(Spirocercidae)の線虫、例えば、アスカロプス属種(Ascarops spp.)の、類円豚胃虫(Ascarops strongylina);
(f)テラジア科(Thelaziidae)の線虫、例えば、テラジア属種(Thelazia spp.)の、東洋眼虫(Thelazia callipaeda)、テラジア・グローサ(Thelazia gulosa)、涙眼虫(Thelazia lacrymalis)、ロデシア眼虫(Thelazia rhodesi)、スクリャービン眼虫(Thelazia skrjabini)。 (11) Nematodes of the order Spirurida (a) Nematodes of the family Gnathostomatidae, such as Gnathostoma doloresi of the genus Gnathostoma spp. , Gnathostoma spinigerum;
(b) Nematodes of the family Habronematidae, such as Habronema majus, Habronema microstoma, Habronema muscae of the genus Habronema spp.; Draschia Draschia megastoma of the genus and species (Draschia spp.);
(c) Nematodes of the family Physalopteridae, such as Physaloptera spp., Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera spp. Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaloptera rara), Physaloptera sibirica, Physaloptera vulpineus;
(d) nematodes of the family Gongylonematidae, such as Gongylonema pulchrum of the genus Gongylonema spp.;
(e) nematodes of the Spirocercidae family, such as Ascarops spp., Ascarops strongylina;
(f) Nematodes of the family Thelaziidae, such as Thelazia spp., Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Rhodesian eye; worm (Thelazia rhodesi), Scriabin's eye worm (Thelazia skrjabini).
〔その他の有害生物についての防除剤〕
本発明化合物は、その他にも、毒針や毒液を持ち、人獣に被害を加える害虫、各種の病原体・病原菌を媒介する害虫、人に不快感を与える害虫(有毒害虫・衛生害虫・不快害虫など)の防除効果に優れている。 [Control agents for other pests]
The compounds of the present invention can also be applied to pests that have poisonous stingers and venom and cause damage to humans and animals, pests that transmit various pathogens and germs, and pests that cause discomfort to humans (toxic pests, sanitary pests, unpleasant pests). etc.) has excellent control effects.
本発明化合物は、その他にも、毒針や毒液を持ち、人獣に被害を加える害虫、各種の病原体・病原菌を媒介する害虫、人に不快感を与える害虫(有毒害虫・衛生害虫・不快害虫など)の防除効果に優れている。 [Control agents for other pests]
The compounds of the present invention can also be applied to pests that have poisonous stingers and venom and cause damage to humans and animals, pests that transmit various pathogens and germs, and pests that cause discomfort to humans (toxic pests, sanitary pests, unpleasant pests). etc.) has excellent control effects.
以下に、その具体例を示す。
(1)ハチ目(Hymenoptera)の害虫
ミフシババチ科(Argidae)のハチ、タマバチ科(Cynipidae)のハチ、マツハバチ科(Diprionidae)のハチ、アリ科(Formicidae)のアリ、アリバチ科(Mutillidae )のハチ、スズメバチ科(Vespidae)のハチ。 A specific example is shown below.
(1) Pests of the order Hymenoptera Wasps of the family Argidae, wasps of the family Cynipidae, wasps of the family Diprionidae, ants of the family Formicidae, wasps of the family Mutillidae, A wasp of the family Vespidae.
(1)ハチ目(Hymenoptera)の害虫
ミフシババチ科(Argidae)のハチ、タマバチ科(Cynipidae)のハチ、マツハバチ科(Diprionidae)のハチ、アリ科(Formicidae)のアリ、アリバチ科(Mutillidae )のハチ、スズメバチ科(Vespidae)のハチ。 A specific example is shown below.
(1) Pests of the order Hymenoptera Wasps of the family Argidae, wasps of the family Cynipidae, wasps of the family Diprionidae, ants of the family Formicidae, wasps of the family Mutillidae, A wasp of the family Vespidae.
(2)その他の害虫
ゴキブリ類(Blattodea)、シロアリ類(termite)、クモ類(Araneae)、ムカデ類(cetipede)、ヤスデ類(millipede)、甲殻類(crustacea)、南京虫(Cimex lectularius)。 (2) Other pests such as cockroaches (Blattodea), termites (termites), arachnids (Araneae), centipedes (cetipede), millipedes (millipedes), crustaceans (crustacea), and bedbugs (Cimex lectularius).
ゴキブリ類(Blattodea)、シロアリ類(termite)、クモ類(Araneae)、ムカデ類(cetipede)、ヤスデ類(millipede)、甲殻類(crustacea)、南京虫(Cimex lectularius)。 (2) Other pests such as cockroaches (Blattodea), termites (termites), arachnids (Araneae), centipedes (cetipede), millipedes (millipedes), crustaceans (crustacea), and bedbugs (Cimex lectularius).
〔製剤処方〕
本発明の有害生物防除剤、殺虫若しくは殺ダニ剤、外部寄生虫防除剤、または内部寄生虫防除若しくは駆除剤の製剤処方を若干示すが、添加物および添加割合は、これら実施例に限定されるべきではなく、広範囲に変化させることが可能である。製剤処方中の部は重量部を示す。
以下に農園芸用および水稲用の製剤処方を示す。 [Prescription]
Some formulations of the pest control agent, insecticide or acaricide, ectoparasite control agent, or endoparasite control or extermination agent of the present invention are shown below, but the additives and addition ratios are limited to these examples. This should not be the case and can vary widely. Parts in the pharmaceutical formulation indicate parts by weight.
The formulations for agriculture, horticulture, and paddy rice are shown below.
本発明の有害生物防除剤、殺虫若しくは殺ダニ剤、外部寄生虫防除剤、または内部寄生虫防除若しくは駆除剤の製剤処方を若干示すが、添加物および添加割合は、これら実施例に限定されるべきではなく、広範囲に変化させることが可能である。製剤処方中の部は重量部を示す。
以下に農園芸用および水稲用の製剤処方を示す。 [Prescription]
Some formulations of the pest control agent, insecticide or acaricide, ectoparasite control agent, or endoparasite control or extermination agent of the present invention are shown below, but the additives and addition ratios are limited to these examples. This should not be the case and can vary widely. Parts in the pharmaceutical formulation indicate parts by weight.
The formulations for agriculture, horticulture, and paddy rice are shown below.
(製剤1:水和剤)
本発明化合物40部、珪藻土53部、高級アルコール硫酸エステル4部、およびアルキルナフタレンスルホン酸塩3部を均一に混合して微細に粉砕して、有効成分40%の水和剤を得る。
(製剤2:乳剤)
本発明化合物30部、キシレン33部、ジメチルホルムアミド30部、およびポリオキシエチレンアルキルアリルエーテル7部を混合溶解して、有効成分30%の乳剤を得る。
(製剤3:粒剤)
本発明化合物5部、タルク40部、クレー38部、ベントナイト10部、およびアルキル硫酸ソーダ7部を均一に混合して微細に粉砕後、直径0.5~1.0mmの粒状に造粒して有効成分5%の粒剤を得る。
(製剤4:粒剤)
本発明化合物5部、クレー73部、ベントナイト20部、ジオクチルスルホサクシネートナトリウム塩1部、およびリン酸カリウム1部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥して有効成分5%の粒剤を得る。
(製剤5:懸濁剤)
本発明化合物10部、ポリオキシエチレンアルキルアリルエーテル4部、ポリカルボン酸ナトリウム塩2部、グリセリン10部、キサンタンガム0.2部、および水73.8部を混合し、粒度が3ミクロン以下になるまで湿式粉砕し、有効成分10%の懸濁剤を得る。 (Formulation 1: Hydrating agent)
40 parts of the compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely ground to obtain a wettable powder containing 40% of the active ingredient.
(Formulation 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.
(Formulation 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 mixed uniformly, pulverized finely, and then granulated into particles with a diameter of 0.5 to 1.0 mm. Granules with 5% active ingredient are obtained.
(Formulation 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 the mixture was thoroughly kneaded, and then granulated and dried. Granules with 5% active ingredient are obtained.
(Formulation 5: Suspension agent)
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 parts of xanthan gum, and 73.8 parts of water are mixed to obtain a particle size of 3 microns or less. Wet milling to obtain a suspension containing 10% of the active ingredient.
本発明化合物40部、珪藻土53部、高級アルコール硫酸エステル4部、およびアルキルナフタレンスルホン酸塩3部を均一に混合して微細に粉砕して、有効成分40%の水和剤を得る。
(製剤2:乳剤)
本発明化合物30部、キシレン33部、ジメチルホルムアミド30部、およびポリオキシエチレンアルキルアリルエーテル7部を混合溶解して、有効成分30%の乳剤を得る。
(製剤3:粒剤)
本発明化合物5部、タルク40部、クレー38部、ベントナイト10部、およびアルキル硫酸ソーダ7部を均一に混合して微細に粉砕後、直径0.5~1.0mmの粒状に造粒して有効成分5%の粒剤を得る。
(製剤4:粒剤)
本発明化合物5部、クレー73部、ベントナイト20部、ジオクチルスルホサクシネートナトリウム塩1部、およびリン酸カリウム1部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥して有効成分5%の粒剤を得る。
(製剤5:懸濁剤)
本発明化合物10部、ポリオキシエチレンアルキルアリルエーテル4部、ポリカルボン酸ナトリウム塩2部、グリセリン10部、キサンタンガム0.2部、および水73.8部を混合し、粒度が3ミクロン以下になるまで湿式粉砕し、有効成分10%の懸濁剤を得る。 (Formulation 1: Hydrating agent)
40 parts of the compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely ground to obtain a wettable powder containing 40% of the active ingredient.
(Formulation 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.
(Formulation 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 mixed uniformly, pulverized finely, and then granulated into particles with a diameter of 0.5 to 1.0 mm. Granules with 5% active ingredient are obtained.
(Formulation 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 the mixture was thoroughly kneaded, and then granulated and dried. Granules with 5% active ingredient are obtained.
(Formulation 5: Suspension agent)
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 parts of xanthan gum, and 73.8 parts of water are mixed to obtain a particle size of 3 microns or less. Wet milling to obtain a suspension containing 10% of the active ingredient.
以下に外部寄生虫防除剤、または内部寄生虫防除もしくは駆除剤の製剤処方を示す。
(製剤6:顆粒剤)
本発明化合物5部を有機溶媒中で溶解させて溶液を得、前記溶液をカオリン94部およびホワイトカーボン1部の上に噴霧し、次いで溶媒を減圧下蒸発させる。この種の顆粒は動物の餌と混合できる。
(製剤7:注入剤)
本発明化合物0.1~1部とラッカセイ油99~99.9部を均一に混合し、次いで滅菌フィルターによりろ過滅菌する。
(製剤8:ポアオン剤)
本発明化合物5部、ミリスチン酸エステル10部、およびイソプロパノール85部を均一に混合してポアオン剤を得る。
(製剤9:スポットオン剤)
本発明化合物10~15部、パルミチン酸エステル10部、およびイソプロパノール75~80部を均一に混合してスポットオン剤を得る。
(製剤10:スプレー剤)
本発明化合物1部、プロピレングリコール10部、およびイソプロパノール89部を均一に混合してスプレー剤を得る。 The formulation of the ectoparasite control agent or the internal parasite control or extermination agent is shown below.
(Formulation 6: Granules)
5 parts of the compound of the invention are dissolved in an organic solvent to obtain a solution, said solution is sprayed onto 94 parts of kaolin and 1 part of white carbon, and the solvent is then evaporated under reduced pressure. Granules of this type can be mixed with animal feed.
(Formulation 7: Injection)
0.1 to 1 part of the compound of the present invention and 99 to 99.9 parts of peanut oil are uniformly mixed, and then sterilized by filtration using a sterilizing filter.
(Formulation 8: pour-on agent)
A pour-on 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.
(Formulation 9: Spot-on agent)
A spot-on agent is obtained by uniformly mixing 10 to 15 parts of the compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol.
(Formulation 10: Spray)
A spray is obtained by uniformly mixing 1 part of the compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol.
(製剤6:顆粒剤)
本発明化合物5部を有機溶媒中で溶解させて溶液を得、前記溶液をカオリン94部およびホワイトカーボン1部の上に噴霧し、次いで溶媒を減圧下蒸発させる。この種の顆粒は動物の餌と混合できる。
(製剤7:注入剤)
本発明化合物0.1~1部とラッカセイ油99~99.9部を均一に混合し、次いで滅菌フィルターによりろ過滅菌する。
(製剤8:ポアオン剤)
本発明化合物5部、ミリスチン酸エステル10部、およびイソプロパノール85部を均一に混合してポアオン剤を得る。
(製剤9:スポットオン剤)
本発明化合物10~15部、パルミチン酸エステル10部、およびイソプロパノール75~80部を均一に混合してスポットオン剤を得る。
(製剤10:スプレー剤)
本発明化合物1部、プロピレングリコール10部、およびイソプロパノール89部を均一に混合してスプレー剤を得る。 The formulation of the ectoparasite control agent or the internal parasite control or extermination agent is shown below.
(Formulation 6: Granules)
5 parts of the compound of the invention are dissolved in an organic solvent to obtain a solution, said solution is sprayed onto 94 parts of kaolin and 1 part of white carbon, and the solvent is then evaporated under reduced pressure. Granules of this type can be mixed with animal feed.
(Formulation 7: Injection)
0.1 to 1 part of the compound of the present invention and 99 to 99.9 parts of peanut oil are uniformly mixed, and then sterilized by filtration using a sterilizing filter.
(Formulation 8: pour-on agent)
A pour-on 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.
(Formulation 9: Spot-on agent)
A spot-on agent is obtained by uniformly mixing 10 to 15 parts of the compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol.
(Formulation 10: Spray)
A spray is obtained by uniformly mixing 1 part of the compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol.
次に、実施例を示し、本発明をより具体的に説明する。ただし、本発明は以下の実施例によって何ら制限されない。
Next, the present invention will be described in more detail with reference to Examples. However, the present invention is not limited in any way by the following examples.
〔実施例1〕
以下の工程を経て、(Z)-2-(3-(5-(2-クロロ-3,3,3-トリフルオロプロプ-1-エン-1-イル)-1-メチル-1H-イミダゾール-2-イル)-4-(エチルスルホニル)-1H-ピラゾール-1-イル)ピリミジン〔英名:(Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine〕(化合物番号A-17)を合成した。 [Example 1]
Through the following steps, (Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazole- 2-yl)-4-(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine [English name: (Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1) -en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine] (Compound No. A-17) was synthesized.
以下の工程を経て、(Z)-2-(3-(5-(2-クロロ-3,3,3-トリフルオロプロプ-1-エン-1-イル)-1-メチル-1H-イミダゾール-2-イル)-4-(エチルスルホニル)-1H-ピラゾール-1-イル)ピリミジン〔英名:(Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine〕(化合物番号A-17)を合成した。 [Example 1]
Through the following steps, (Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazole- 2-yl)-4-(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine [English name: (Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1) -en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine] (Compound No. A-17) was synthesized.
(工程1)
1-(5-((Z)-2-クロロ-3,3,3-トリフルオロプロプ-1-エン-1-イル)-1-メチル-1H-イミダゾール-2-イル)-3-(ジメチルアミノ)-2-(エチルスルホニル)プロプ-2-エン-1-オン〔1-(5-((Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-3-(dimethylamino)-2-(ethylsulfonyl)prop-2-en-1-one〕の合成 (Step 1)
1-(5-((Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-3-(dimethyl Amino)-2-(ethylsulfonyl)prop-2-en-1-one [1-(5-((Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)- Synthesis of 1-methyl-1H-imidazol-2-yl)-3-(dimethylamino)-2-(ethylsulfonyl)prop-2-en-1-one]
1-(5-((Z)-2-クロロ-3,3,3-トリフルオロプロプ-1-エン-1-イル)-1-メチル-1H-イミダゾール-2-イル)-3-(ジメチルアミノ)-2-(エチルスルホニル)プロプ-2-エン-1-オン〔1-(5-((Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-3-(dimethylamino)-2-(ethylsulfonyl)prop-2-en-1-one〕の合成 (Step 1)
1-(5-((Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-3-(dimethyl Amino)-2-(ethylsulfonyl)prop-2-en-1-one [1-(5-((Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)- Synthesis of 1-methyl-1H-imidazol-2-yl)-3-(dimethylamino)-2-(ethylsulfonyl)prop-2-en-1-one]
得られた目的物の1H-NMRを以下に示す。
1H-NMR(400 MHz, CDCl3): δ 7.91 (s, 1H), 7.83 (s, 1H), 7.13 (s, 1H), 3.85 (s, 3H), 3.49 (q, 2H), 3.33 (s, 3H), 2.80 (s, 3H), 1.32 (t, 3H).
1 H-NMR of the obtained target product is shown below.
1 H-NMR (400 MHz, CDCl 3 ): δ 7.91 (s, 1H), 7.83 (s, 1H), 7.13 (s, 1H), 3.85 (s, 3H), 3.49 (q, 2H), 3.33 ( s, 3H), 2.80 (s, 3H), 1.32 (t, 3H).
(工程2)
(Z)-3-(5-(2-クロロ-3,3,3-トリフルオロプロプ-1-エン-1-イル)-1-メチル-1H-イミダゾール-2-イル)-4-(エチルスルホニル)-1H-ピラゾール〔(Z)-3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazole〕の合成 (Step 2)
(Z)-3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethyl sulfonyl)-1H-pyrazole [(Z)-3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl) Synthesis of -4-(ethylsulfonyl)-1H-pyrazole
(Z)-3-(5-(2-クロロ-3,3,3-トリフルオロプロプ-1-エン-1-イル)-1-メチル-1H-イミダゾール-2-イル)-4-(エチルスルホニル)-1H-ピラゾール〔(Z)-3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazole〕の合成 (Step 2)
(Z)-3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethyl sulfonyl)-1H-pyrazole [(Z)-3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl) Synthesis of -4-(ethylsulfonyl)-1H-pyrazole
1-(5-((Z)-2-クロロ-3,3,3-トリフルオロプロプ-1-エン-1-イル)-1-メチル-1H-イミダゾール-2-イル)-3-(ジメチルアミノ)-2-(エチルスルホニル)プロプ-2-エン-1-オン(1.2g)を酢酸(5ml)に溶解させて、室温下で撹拌した。これにヒドラジン一水和物(0.17g)を加え、室温で2時間撹拌した。得られた液を減圧濃縮し、得られた濃縮物を飽和炭酸水素ナトリウム水溶液に注加し、ジクロロメタンで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた濃縮物をシリカゲルカラムクロマトグラフィーで精製することによって目的物0.040g(収率3%)を得た。
得られた目的物の1H-NMRを以下に示す。
1H-NMR(400 MHz, CDCl3): δ 8.22 (s, 1H), 8.08 (s, 1H), 7.15 (s, 1H), 3.84 (s, 3H), 3.80 (1q 2H), 1.33 (t, 3H). 1-(5-((Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-3-(dimethyl Amino)-2-(ethylsulfonyl)prop-2-en-1-one (1.2 g) was dissolved in acetic acid (5 ml) and stirred at room temperature. Hydrazine monohydrate (0.17 g) was added to this, and the mixture was stirred at room temperature for 2 hours. The obtained liquid was concentrated under reduced pressure, and the obtained concentrate was poured into a saturated aqueous sodium hydrogen carbonate solution, and extracted with dichloromethane. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to obtain 0.040 g (yield: 3%) of the target product.
1 H-NMR of the obtained target product is shown below.
1 H-NMR (400 MHz, CDCl 3 ): δ 8.22 (s, 1H), 8.08 (s, 1H), 7.15 (s, 1H), 3.84 (s, 3H), 3.80 (1q 2H), 1.33 (t , 3H).
得られた目的物の1H-NMRを以下に示す。
1H-NMR(400 MHz, CDCl3): δ 8.22 (s, 1H), 8.08 (s, 1H), 7.15 (s, 1H), 3.84 (s, 3H), 3.80 (1q 2H), 1.33 (t, 3H). 1-(5-((Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-3-(dimethyl Amino)-2-(ethylsulfonyl)prop-2-en-1-one (1.2 g) was dissolved in acetic acid (5 ml) and stirred at room temperature. Hydrazine monohydrate (0.17 g) was added to this, and the mixture was stirred at room temperature for 2 hours. The obtained liquid was concentrated under reduced pressure, and the obtained concentrate was poured into a saturated aqueous sodium hydrogen carbonate solution, and extracted with dichloromethane. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to obtain 0.040 g (yield: 3%) of the target product.
1 H-NMR of the obtained target product is shown below.
1 H-NMR (400 MHz, CDCl 3 ): δ 8.22 (s, 1H), 8.08 (s, 1H), 7.15 (s, 1H), 3.84 (s, 3H), 3.80 (1q 2H), 1.33 (t , 3H).
(工程3)
(Z)-2-(3-(5-(2-クロロ-3,3,3-トリフルオロプロプ-1-エン-1-イル)-1-メチル-1H-イミダゾール-2-イル)-4-(エチルスルホニル)-1H-ピラゾール-1-イル)ピリミジン〔(Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine〕の合成 (Step 3)
(Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4 -(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine [(Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)- Synthesis of 1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine]
(Z)-2-(3-(5-(2-クロロ-3,3,3-トリフルオロプロプ-1-エン-1-イル)-1-メチル-1H-イミダゾール-2-イル)-4-(エチルスルホニル)-1H-ピラゾール-1-イル)ピリミジン〔(Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine〕の合成 (Step 3)
(Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4 -(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine [(Z)-2-(3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)- Synthesis of 1-methyl-1H-imidazol-2-yl)-4-(ethylsulfonyl)-1H-pyrazol-1-yl)pyrimidine]
(Z)-3-(5-(2-クロロ-3,3,3-トリフルオロプロプ-1-エン-1-イル)-1-メチル-1H-イミダゾール-2-イル)-4-(エチルスルホニル)-1H-ピラゾール(0.040g)をN,N-ジメチルホルムアミド(2ml)に溶解させて、室温で撹拌した。これに2-クロロピリミジン(0.023g)と炭酸カリウム(0.040g)を加え、50℃で1時間撹拌した。得られた液を飽和塩化アンモニウム水溶液に注加し、酢酸エチルで抽出した。得られた有機層を水及び飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた濃縮物をシリカゲルカラムクロマトグラフィーで精製することによって目的物0.013g(収率26%)を得た。
得られた目的物の1H-NMRを以下に示す。
1H-NMR(400 MHz, CDCl3): δ 9.26 (s, 1H), 8.86 (d, 2H), 8.10 (s, 1H), 7.41 (t, 1H), 7.16 (s, 1H), 3.87 (s, 3H), 3.83 (q, 2H), 1.40 (t, 3H). (Z)-3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethyl Sulfonyl)-1H-pyrazole (0.040 g) was dissolved in N,N-dimethylformamide (2 ml) and stirred at room temperature. 2-chloropyrimidine (0.023g) and potassium carbonate (0.040g) were added to this, and the mixture was stirred at 50°C for 1 hour. The obtained liquid was poured into a saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to obtain 0.013 g (yield: 26%) of the target product.
1 H-NMR of the obtained target product is shown below.
1 H-NMR (400 MHz, CDCl 3 ): δ 9.26 (s, 1H), 8.86 (d, 2H), 8.10 (s, 1H), 7.41 (t, 1H), 7.16 (s, 1H), 3.87 ( s, 3H), 3.83 (q, 2H), 1.40 (t, 3H).
得られた目的物の1H-NMRを以下に示す。
1H-NMR(400 MHz, CDCl3): δ 9.26 (s, 1H), 8.86 (d, 2H), 8.10 (s, 1H), 7.41 (t, 1H), 7.16 (s, 1H), 3.87 (s, 3H), 3.83 (q, 2H), 1.40 (t, 3H). (Z)-3-(5-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-1-methyl-1H-imidazol-2-yl)-4-(ethyl Sulfonyl)-1H-pyrazole (0.040 g) was dissolved in N,N-dimethylformamide (2 ml) and stirred at room temperature. 2-chloropyrimidine (0.023g) and potassium carbonate (0.040g) were added to this, and the mixture was stirred at 50°C for 1 hour. The obtained liquid was poured into a saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting concentrate was purified by silica gel column chromatography to obtain 0.013 g (yield: 26%) of the target product.
1 H-NMR of the obtained target product is shown below.
1 H-NMR (400 MHz, CDCl 3 ): δ 9.26 (s, 1H), 8.86 (d, 2H), 8.10 (s, 1H), 7.41 (t, 1H), 7.16 (s, 1H), 3.87 ( s, 3H), 3.83 (q, 2H), 1.40 (t, 3H).
〔実施例2〕
5-(エチルスルホニル)-4-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)-2-(ピリミジン-2-イル)チアゾール〔5-(ethylsulfonyl)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole〕(化合物番号A-4)の合成 [Example 2]
5-(ethylsulfonyl)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole [5-( Synthesis of (compound number A-4)
5-(エチルスルホニル)-4-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)-2-(ピリミジン-2-イル)チアゾール〔5-(ethylsulfonyl)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole〕(化合物番号A-4)の合成 [Example 2]
5-(ethylsulfonyl)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole [5-( Synthesis of (compound number A-4)
(工程1)
2-クロロ-1-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)エタン-1-オン〔2-chloro-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one〕の合成 (Step 1)
2-chloro-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethane-1-one [2-chloro-1-(1-methyl-5 -(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one]
2-クロロ-1-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)エタン-1-オン〔2-chloro-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one〕の合成 (Step 1)
2-chloro-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethane-1-one [2-chloro-1-(1-methyl-5 -(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one]
窒素雰囲気下、1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール(0.50g)をテトラヒドロフラン(10.3ml)へ溶解させ、-70℃で攪拌した。これに2.6Mn-ブチルリチウムヘキサン溶媒(0.95ml)を滴下し30分間攪拌した後、2-クロロ-N-メトキシーN-メチルアセトアミド(0.341g)を加え、さらに2.5時間攪拌した。得られた液を飽和塩化アンモニウム水溶液へ注加し、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することで目的物0.178g(収率28%)を得た。
得られた目的物の1H-NMRを以下に示す。
1H‐NMR (400 MHz, CDCl3):δ 7.46 - 7.39 (m, 2H), 7.34 (d, 2H), 7.23 (s, 1H), 4.96 (s, 2H), 3.95 (s, 3H). Under a nitrogen atmosphere, 1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazole (0.50 g) was dissolved in tetrahydrofuran (10.3 ml) and stirred at -70°C. 2.6M n-butyllithium hexane solvent (0.95 ml) was added dropwise to this and stirred for 30 minutes, then 2-chloro-N-methoxy N-methylacetamide (0.341 g) was added, and the mixture was further stirred for 2.5 hours. . The obtained liquid was poured into a saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 0.178 g (yield: 28%) of the target product.
1 H-NMR of the obtained target product is shown below.
1H -NMR (400 MHz, CDCl3 ): δ 7.46 - 7.39 (m, 2H), 7.34 (d, 2H), 7.23 (s, 1H), 4.96 (s, 2H), 3.95 (s, 3H).
得られた目的物の1H-NMRを以下に示す。
1H‐NMR (400 MHz, CDCl3):δ 7.46 - 7.39 (m, 2H), 7.34 (d, 2H), 7.23 (s, 1H), 4.96 (s, 2H), 3.95 (s, 3H). Under a nitrogen atmosphere, 1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazole (0.50 g) was dissolved in tetrahydrofuran (10.3 ml) and stirred at -70°C. 2.6M n-butyllithium hexane solvent (0.95 ml) was added dropwise to this and stirred for 30 minutes, then 2-chloro-N-methoxy N-methylacetamide (0.341 g) was added, and the mixture was further stirred for 2.5 hours. . The obtained liquid was poured into a saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 0.178 g (yield: 28%) of the target product.
1 H-NMR of the obtained target product is shown below.
1H -NMR (400 MHz, CDCl3 ): δ 7.46 - 7.39 (m, 2H), 7.34 (d, 2H), 7.23 (s, 1H), 4.96 (s, 2H), 3.95 (s, 3H).
(工程2)
2-(エチルチオ)-1-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)エタン-1-オン〔2-(ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one〕の合成 (Step 2)
2-(ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethane-1-one [2-(ethylthio)-1-(1 -methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one]
2-(エチルチオ)-1-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)エタン-1-オン〔2-(ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one〕の合成 (Step 2)
2-(ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethane-1-one [2-(ethylthio)-1-(1 -methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one]
2-クロロ-1-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)エタン-1-オン(0.187g)をテトラヒドロフラン(5.90ml)へ溶解させ、室温で攪拌した。これにナトリウムエタンチオラート(0.068g)を加え、18時間攪拌した。得られた液を飽和塩化アンモニウム水溶液へ注加し、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することで目的物0.138g(収率68%)を得た。
得られた目的物の1H-NMRを以下に示す。
1H‐NMR (400 MHz, CDCl3) δ 7.46 - 7.38 (m, 2H), 7.33 (d, 2H), 7.21 (s, 1H), 3.98 (s, 2H), 3.93 (s, 3H), 2.67 (q, 2H), 1.29 (t, 3H). 2-chloro-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one (0.187 g) was added to tetrahydrofuran (5.90 ml). Dissolved and stirred at room temperature. Sodium ethanethiolate (0.068 g) was added to this and stirred for 18 hours. The obtained liquid was poured into a saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 0.138 g (yield: 68%) of the target product.
1 H-NMR of the obtained target product is shown below.
1 H-NMR (400 MHz, CDCl 3 ) δ 7.46 - 7.38 (m, 2H), 7.33 (d, 2H), 7.21 (s, 1H), 3.98 (s, 2H), 3.93 (s, 3H), 2.67 (q, 2H), 1.29 (t, 3H).
得られた目的物の1H-NMRを以下に示す。
1H‐NMR (400 MHz, CDCl3) δ 7.46 - 7.38 (m, 2H), 7.33 (d, 2H), 7.21 (s, 1H), 3.98 (s, 2H), 3.93 (s, 3H), 2.67 (q, 2H), 1.29 (t, 3H). 2-chloro-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one (0.187 g) was added to tetrahydrofuran (5.90 ml). Dissolved and stirred at room temperature. Sodium ethanethiolate (0.068 g) was added to this and stirred for 18 hours. The obtained liquid was poured into a saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 0.138 g (yield: 68%) of the target product.
1 H-NMR of the obtained target product is shown below.
1 H-NMR (400 MHz, CDCl 3 ) δ 7.46 - 7.38 (m, 2H), 7.33 (d, 2H), 7.21 (s, 1H), 3.98 (s, 2H), 3.93 (s, 3H), 2.67 (q, 2H), 1.29 (t, 3H).
(工程3)
2-クロロ-2-(エチルチオ)-1-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)エタン-1-オン〔2-chloro-2-(ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one〕の合成 (Step 3)
2-chloro-2-(ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one [2-chloro-2- Synthesis of (ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one]
2-クロロ-2-(エチルチオ)-1-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)エタン-1-オン〔2-chloro-2-(ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one〕の合成 (Step 3)
2-chloro-2-(ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one [2-chloro-2- Synthesis of (ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one]
2-(エチルチオ)-1-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)エタン-1-オン(1.20g)を四塩化炭素(17.4ml)へ溶解させ、0℃で攪拌した。これにN-クロロスクシンイミド(0.512g)を加え、室温で16時間攪拌した。得られた液をセライトろ過し、ろ液を減圧濃縮することで粗生成物1.52gを得た。この化合物はさらに、精製することなく、次の工程に直接使用された。
2-(Ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethane-1-one (1.20 g) was dissolved in carbon tetrachloride (17 .4 ml) and stirred at 0°C. N-chlorosuccinimide (0.512 g) was added to this, and the mixture was stirred at room temperature for 16 hours. The obtained liquid was filtered through Celite, and the filtrate was concentrated under reduced pressure to obtain 1.52 g of a crude product. This compound was used directly in the next step without further purification.
(工程4)
5-(エチルチオ)-4-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)-2-(ピリミジン-2-イル)チアゾール〔5-(ethylthio)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole〕の合成 (Step 4)
5-(ethylthio)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole )-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole]
5-(エチルチオ)-4-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)-2-(ピリミジン-2-イル)チアゾール〔5-(ethylthio)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole〕の合成 (Step 4)
5-(ethylthio)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole )-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole]
2-クロロ-2-(エチルチオ)-1-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)エタン-1-オン(1.30g)をエタノール(17.0ml)へ溶解させ、室温で攪拌した。これにピリミジン-2-カルボチオアミド(0.716g)を加え、加熱還流下で8時間攪拌した。得られた液を飽和炭酸水素ナトリウム水溶液へ注加し、クロロホルムで抽出した。得られた有機層を無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することで目的物0.238g(収率15%)を得た。
得られた目的物の1H-NMRを以下に示す。
1H‐NMR (400 MHz, CDCl3) δ 8.88 (d, 2H), 7.51 - 7.43 (m, 2H), 7.32 (d, 2H), 7.18 (t, 1H), 7.17 (s, 1H), 4.17 (s, 3H), 3.13 (q, 2H), 1.49 (t, 3H). 2-chloro-2-(ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one (1.30 g) was dissolved in ethanol. (17.0 ml) and stirred at room temperature. Pyrimidine-2-carbothioamide (0.716 g) was added to this, and the mixture was stirred under heating under reflux for 8 hours. The obtained liquid was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 0.238 g (yield: 15%) of the target product.
1 H-NMR of the obtained target product is shown below.
1 H-NMR (400 MHz, CDCl 3 ) δ 8.88 (d, 2H), 7.51 - 7.43 (m, 2H), 7.32 (d, 2H), 7.18 (t, 1H), 7.17 (s, 1H), 4.17 (s, 3H), 3.13 (q, 2H), 1.49 (t, 3H).
得られた目的物の1H-NMRを以下に示す。
1H‐NMR (400 MHz, CDCl3) δ 8.88 (d, 2H), 7.51 - 7.43 (m, 2H), 7.32 (d, 2H), 7.18 (t, 1H), 7.17 (s, 1H), 4.17 (s, 3H), 3.13 (q, 2H), 1.49 (t, 3H). 2-chloro-2-(ethylthio)-1-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)ethan-1-one (1.30 g) was dissolved in ethanol. (17.0 ml) and stirred at room temperature. Pyrimidine-2-carbothioamide (0.716 g) was added to this, and the mixture was stirred under heating under reflux for 8 hours. The obtained liquid was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 0.238 g (yield: 15%) of the target product.
1 H-NMR of the obtained target product is shown below.
1 H-NMR (400 MHz, CDCl 3 ) δ 8.88 (d, 2H), 7.51 - 7.43 (m, 2H), 7.32 (d, 2H), 7.18 (t, 1H), 7.17 (s, 1H), 4.17 (s, 3H), 3.13 (q, 2H), 1.49 (t, 3H).
(工程5)
5-(エチルスルホニル)-4-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)-2-(ピリミジン-2-イル)チアゾール〔5-(ethylsulfonyl)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole〕の合成 (Step 5)
5-(ethylsulfonyl)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole [5-( Synthesis of ethylsulfonyl)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole]
5-(エチルスルホニル)-4-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)-2-(ピリミジン-2-イル)チアゾール〔5-(ethylsulfonyl)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole〕の合成 (Step 5)
5-(ethylsulfonyl)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole [5-( Synthesis of ethylsulfonyl)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole]
5-(エチルチオ)-4-(1-メチル-5-(4-(トリフルオロメトキシ)フェニル)-1H-イミダゾール-2-イル)-2-(ピリミジン-2-イル)チアゾール(0.176g)をジクロロメタン(4.0ml)へ溶解させ、0℃で攪拌した。これにメタクロロ過安息香酸(0.150g)を加え、室温で16時間攪拌した。得られた液を飽和チオ硫酸ナトリウム水溶液へ注加し、酢酸エチルで抽出した。得られた有機層を飽和炭酸水素ナトリウム水溶液で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することで目的物0.108g(収率57%)を得た。
得られた目的物の1H-NMRを以下に示す。
1H‐NMR (400 MHz, CDCl3) δ 8.91 (d, 2H), 7.50 - 7.42 (m, 2H), 7.38 (t, 1H), 7.34 (d, 2H), 7.23 (s, 1H), 4.13 (s, 3H), 3.96 (q, 2H), 1.47 (t, 3H). 5-(Ethylthio)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole (0.176g) was dissolved in dichloromethane (4.0 ml) and stirred at 0°C. Metachloroperbenzoic acid (0.150 g) was added to this, and the mixture was stirred at room temperature for 16 hours. The obtained liquid was poured into a saturated aqueous sodium thiosulfate solution and extracted with ethyl acetate. The obtained organic layer was washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 0.108 g (yield: 57%) of the target product.
1 H-NMR of the obtained target product is shown below.
1 H-NMR (400 MHz, CDCl 3 ) δ 8.91 (d, 2H), 7.50 - 7.42 (m, 2H), 7.38 (t, 1H), 7.34 (d, 2H), 7.23 (s, 1H), 4.13 (s, 3H), 3.96 (q, 2H), 1.47 (t, 3H).
得られた目的物の1H-NMRを以下に示す。
1H‐NMR (400 MHz, CDCl3) δ 8.91 (d, 2H), 7.50 - 7.42 (m, 2H), 7.38 (t, 1H), 7.34 (d, 2H), 7.23 (s, 1H), 4.13 (s, 3H), 3.96 (q, 2H), 1.47 (t, 3H). 5-(Ethylthio)-4-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-2-(pyrimidin-2-yl)thiazole (0.176g) was dissolved in dichloromethane (4.0 ml) and stirred at 0°C. Metachloroperbenzoic acid (0.150 g) was added to this, and the mixture was stirred at room temperature for 16 hours. The obtained liquid was poured into a saturated aqueous sodium thiosulfate solution and extracted with ethyl acetate. The obtained organic layer was washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to obtain 0.108 g (yield: 57%) of the target product.
1 H-NMR of the obtained target product is shown below.
1 H-NMR (400 MHz, CDCl 3 ) δ 8.91 (d, 2H), 7.50 - 7.42 (m, 2H), 7.38 (t, 1H), 7.34 (d, 2H), 7.23 (s, 1H), 4.13 (s, 3H), 3.96 (q, 2H), 1.47 (t, 3H).
実施例1と同様の方法で本発明化合物を合成した。それらのうちの一部を表1に示す。物性欄には融点(mp)を記載した。物性がAmorphousである化合物についてはNMRのデータを記した。
The compound of the present invention was synthesized in the same manner as in Example 1. Some of them are shown in Table 1. The melting point (mp) is listed in the physical properties column. NMR data is recorded for compounds with amorphous physical properties.
物性がAMORPHOUSの化合物は1H-NMRによって分析した。
化合物番号A-7: 1H NMR (400MHz, CDCl3) δ 7.46 - 7.39 (m, 2H), 7.28 (d, 2H), 7.23 (s, 1H), 3.73 (s, 3H), 3.03 (q, 2H), 1.56 (s, 18H), 1.35 (t, 3H).
化合物番号A-18: 1H-NMR (CDCl3) δ: 8.92(2H, d), 8.11(1H, s), 7.45(1H,dd), 7.12(1H,s), 4.03(2H, q), 3.87(3H, s), 1.46(3H, t). Compounds with physical properties of AMORPHOUS were analyzed by 1 H-NMR.
Compound number A-7: 1 H NMR (400MHz, CDCl 3 ) δ 7.46 - 7.39 (m, 2H), 7.28 (d, 2H), 7.23 (s, 1H), 3.73 (s, 3H), 3.03 (q, 2H), 1.56 (s, 18H), 1.35 (t, 3H).
Compound number A-18: 1 H-NMR (CDCl 3 ) δ: 8.92(2H, d), 8.11(1H, s), 7.45(1H,dd), 7.12(1H,s), 4.03(2H, q) , 3.87(3H, s), 1.46(3H, t).
化合物番号A-7: 1H NMR (400MHz, CDCl3) δ 7.46 - 7.39 (m, 2H), 7.28 (d, 2H), 7.23 (s, 1H), 3.73 (s, 3H), 3.03 (q, 2H), 1.56 (s, 18H), 1.35 (t, 3H).
化合物番号A-18: 1H-NMR (CDCl3) δ: 8.92(2H, d), 8.11(1H, s), 7.45(1H,dd), 7.12(1H,s), 4.03(2H, q), 3.87(3H, s), 1.46(3H, t). Compounds with physical properties of AMORPHOUS were analyzed by 1 H-NMR.
Compound number A-7: 1 H NMR (400MHz, CDCl 3 ) δ 7.46 - 7.39 (m, 2H), 7.28 (d, 2H), 7.23 (s, 1H), 3.73 (s, 3H), 3.03 (q, 2H), 1.56 (s, 18H), 1.35 (t, 3H).
Compound number A-18: 1 H-NMR (CDCl 3 ) δ: 8.92(2H, d), 8.11(1H, s), 7.45(1H,dd), 7.12(1H,s), 4.03(2H, q) , 3.87(3H, s), 1.46(3H, t).
〔生物試験〕
本発明化合物が、有害生物防除剤および外部寄生虫防除剤の有効成分として有用であることを以下の試験例で示す。「部」は重量基準である。 [Biological test]
The following test examples demonstrate that the compounds of the present invention are useful as active ingredients for pest control agents and ectoparasite control agents. "Parts" are based on weight.
本発明化合物が、有害生物防除剤および外部寄生虫防除剤の有効成分として有用であることを以下の試験例で示す。「部」は重量基準である。 [Biological test]
The following test examples demonstrate that the compounds of the present invention are useful as active ingredients for pest control agents and ectoparasite control agents. "Parts" are based on weight.
(試験用乳剤の調製)
本発明化合物5部、ジメチルホルムアミド93.6部、およびポリオキシエチレンアルキルアリールエーテル1.4部を混合して有効成分5%の乳剤(I)を得た。対照のために、ジメチルホルムアミド98.5部、およびポリオキシエチレンアルキルアリールエーテル1.5部を混合して乳剤(II)を得た。 (Preparation of test emulsion)
5 parts of the compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkylaryl ether were mixed to obtain an emulsion (I) containing 5% active ingredient. For control, emulsion (II) was obtained by mixing 98.5 parts of dimethylformamide and 1.5 parts of polyoxyethylene alkylaryl ether.
本発明化合物5部、ジメチルホルムアミド93.6部、およびポリオキシエチレンアルキルアリールエーテル1.4部を混合して有効成分5%の乳剤(I)を得た。対照のために、ジメチルホルムアミド98.5部、およびポリオキシエチレンアルキルアリールエーテル1.5部を混合して乳剤(II)を得た。 (Preparation of test emulsion)
5 parts of the compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkylaryl ether were mixed to obtain an emulsion (I) containing 5% active ingredient. For control, emulsion (II) was obtained by mixing 98.5 parts of dimethylformamide and 1.5 parts of polyoxyethylene alkylaryl ether.
殺虫率は、下記の式により計算した。
殺虫率(%)=(死亡虫数/供試虫数)×100
防除率は、下記の式により計算した。
防除率(%)={1-(化合物処理区幼虫数/対照区幼虫数)}×100 The insecticidal rate was calculated using the following formula.
Insect killing rate (%) = (number of dead insects / number of tested insects) x 100
The control rate was calculated using the following formula.
Control rate (%) = {1 - (number of larvae in compound treatment area/number of larvae in control area)} x 100
殺虫率(%)=(死亡虫数/供試虫数)×100
防除率は、下記の式により計算した。
防除率(%)={1-(化合物処理区幼虫数/対照区幼虫数)}×100 The insecticidal rate was calculated using the following formula.
Insect killing rate (%) = (number of dead insects / number of tested insects) x 100
The control rate was calculated using the following formula.
Control rate (%) = {1 - (number of larvae in compound treatment area/number of larvae in control area)} x 100
(試験例1)コナガに対する効力試験
乳剤(I)を、本発明化合物の濃度が125ppmになるように水で希釈した。キャベツ葉を前記希釈液中に30秒間浸漬した。このキャベツ葉をシャーレに入れた。これにコナガ2齢幼虫5頭を放した。シャーレを温度25℃、湿度60%の恒温室内に置いた。放虫から3日間経過したときに生死判定を行い、殺虫率を算出した。これを2反復行った。 (Test Example 1) Efficacy test against diamondback moth Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Cabbage leaves were immersed in the diluted solution for 30 seconds. This cabbage leaf was placed in a petri dish. Five second-instar diamondback moth larvae were released into this. The petri dish was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%. Three days after the insects were released, the insects were determined to be alive or dead, and the killing rate was calculated. This was repeated twice.
乳剤(I)を、本発明化合物の濃度が125ppmになるように水で希釈した。キャベツ葉を前記希釈液中に30秒間浸漬した。このキャベツ葉をシャーレに入れた。これにコナガ2齢幼虫5頭を放した。シャーレを温度25℃、湿度60%の恒温室内に置いた。放虫から3日間経過したときに生死判定を行い、殺虫率を算出した。これを2反復行った。 (Test Example 1) Efficacy test against diamondback moth Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Cabbage leaves were immersed in the diluted solution for 30 seconds. This cabbage leaf was placed in a petri dish. Five second-instar diamondback moth larvae were released into this. The petri dish was placed in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%. Three days after the insects were released, the insects were determined to be alive or dead, and the killing rate was calculated. This was repeated twice.
化合物番号A-1、A-2、A-6、A-8、A-10、A-14、A-16およびA-18の化合物について、コナガに対する効力試験を行った。いずれの化合物もコナガに対して80%以上の殺虫率を示した。
Efficacy tests were conducted on the diamondback moth for compounds with compound numbers A-1, A-2, A-6, A-8, A-10, A-14, A-16, and A-18. All compounds showed an insecticidal rate of 80% or more against diamondback moths.
(試験例2)ナシヒメシンクイに対する効力試験
リンゴ果実をケースに入れた。ケースを温度25℃、湿度60%の恒温室内に置いた。これにナシヒメシンクイ成虫10頭を放し、2日後に成虫10頭を除去した。果実に卵が産み付けられていた。卵の数を計数した。乳剤(I)を、本発明化合物の濃度が125ppmになるように水で希釈した。リンゴ果実に前記希釈液を散布した。散布から12日間経過したときに卵と幼虫の生死判定を行った。産卵数に対する死亡卵および死亡幼虫の数から殺虫率を算出した。これを2反復行った。 (Test Example 2) Efficacy test against Pygmy chinensis Apple fruits were placed in a case. The case was placed in a constant temperature room at a temperature of 25° C. and a humidity of 60%. 10 adult Nashihimeshinkoi were released into this, and 10 adults were removed 2 days later. Eggs were laid on the fruit. The number of eggs was counted. Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. The diluted solution was sprayed on apple fruits. The eggs and larvae were determined to be alive or dead 12 days after spraying. The insecticidal rate was calculated from the number of dead eggs and dead larvae relative to the number of eggs laid. This was repeated twice.
リンゴ果実をケースに入れた。ケースを温度25℃、湿度60%の恒温室内に置いた。これにナシヒメシンクイ成虫10頭を放し、2日後に成虫10頭を除去した。果実に卵が産み付けられていた。卵の数を計数した。乳剤(I)を、本発明化合物の濃度が125ppmになるように水で希釈した。リンゴ果実に前記希釈液を散布した。散布から12日間経過したときに卵と幼虫の生死判定を行った。産卵数に対する死亡卵および死亡幼虫の数から殺虫率を算出した。これを2反復行った。 (Test Example 2) Efficacy test against Pygmy chinensis Apple fruits were placed in a case. The case was placed in a constant temperature room at a temperature of 25° C. and a humidity of 60%. 10 adult Nashihimeshinkoi were released into this, and 10 adults were removed 2 days later. Eggs were laid on the fruit. The number of eggs was counted. Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. The diluted solution was sprayed on apple fruits. The eggs and larvae were determined to be alive or dead 12 days after spraying. The insecticidal rate was calculated from the number of dead eggs and dead larvae relative to the number of eggs laid. This was repeated twice.
化合物番号A-1の化合物について、ナシヒメシンクイに対する効力試験を行った。この化合物はナシヒメシンクイに対して80%以上の殺虫率を示した。
Efficacy tests were conducted on the compound No. A-1 against Nasihimeshinkui. This compound showed an insecticidal rate of more than 80% against the Japanese snail.
(試験例3)キスジノミハムシに対する効力試験
乳剤(I)を、本発明化合物が125ppmになるように水で希釈し、試験用薬液を調製した。3寸鉢に植えたチンゲンサイ苗(第7本葉展開期)に試験用薬液を散布した。チンゲンサイ苗を風乾させ、次いでプラスチックカップに入れた。これに、キスジノミハムシ成虫10頭を放した。温度25℃、湿度65%の恒温室内で保管し、放虫から7日間経過したときに成虫の生死判定を行い、殺虫率を算出した。これを2反復行った。 (Test Example 3) Efficacy test against leaf beetles Emulsion (I) was diluted with water so that the compound of the present invention was 125 ppm to prepare a test drug solution. The test chemical solution was sprayed on bok choy seedlings (7th true leaf development stage) planted in 3-inch pots. Bok choy seedlings were air-dried and then placed in plastic cups. To this, 10 adult beetles were released. The insects were stored in a thermostatic chamber at a temperature of 25° C. and a humidity of 65%, and the adult insects were determined to be alive or dead after 7 days from release, and the killing rate was calculated. This was repeated twice.
乳剤(I)を、本発明化合物が125ppmになるように水で希釈し、試験用薬液を調製した。3寸鉢に植えたチンゲンサイ苗(第7本葉展開期)に試験用薬液を散布した。チンゲンサイ苗を風乾させ、次いでプラスチックカップに入れた。これに、キスジノミハムシ成虫10頭を放した。温度25℃、湿度65%の恒温室内で保管し、放虫から7日間経過したときに成虫の生死判定を行い、殺虫率を算出した。これを2反復行った。 (Test Example 3) Efficacy test against leaf beetles Emulsion (I) was diluted with water so that the compound of the present invention was 125 ppm to prepare a test drug solution. The test chemical solution was sprayed on bok choy seedlings (7th true leaf development stage) planted in 3-inch pots. Bok choy seedlings were air-dried and then placed in plastic cups. To this, 10 adult beetles were released. The insects were stored in a thermostatic chamber at a temperature of 25° C. and a humidity of 65%, and the adult insects were determined to be alive or dead after 7 days from release, and the killing rate was calculated. This was repeated twice.
化合物番号A-16およびA-18の化合物について、キスジノミハムシ成虫に対する効力試験を行った。この化合物はキスジノミハムシ成虫に対して80%以上の殺虫率を示した。
Efficacy tests were conducted on compounds numbered A-16 and A-18 against adult leaf beetles. This compound showed an insecticidal rate of 80% or more against adult leaf beetles.
(試験例4)ワタアブラムシに対する効力試験
3寸鉢にキュウリを播種した。発芽から10日間経過したキュウリに、ワタアブラムシ雌成虫を放した。翌日に、産下された1齢幼虫を残し、雌成虫を除去した。
乳剤(I)を本発明化合物が125ppmになるように水で希釈した。この希釈液を前記のキュウリに散布した。その後、キュウリを、温度25℃、湿度60%の恒温室内で保管し、5日間経過したときに生死判定を行い、殺虫率を算出した。これを2反復行った。 (Test Example 4) Efficacy test against cotton aphids Cucumbers were sown in 3-inch pots. Adult female cotton aphids were released on cucumbers 10 days after germination. The next day, the female adults were removed, leaving the first instar larvae that had been laid down.
Emulsion (I) was diluted with water so that the compound of the present invention was 125 ppm. This diluted solution was sprinkled on the cucumbers. Thereafter, the cucumbers were stored in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%, and after 5 days had elapsed, the survival and death determination was performed to calculate the insecticidal rate. This was repeated twice.
3寸鉢にキュウリを播種した。発芽から10日間経過したキュウリに、ワタアブラムシ雌成虫を放した。翌日に、産下された1齢幼虫を残し、雌成虫を除去した。
乳剤(I)を本発明化合物が125ppmになるように水で希釈した。この希釈液を前記のキュウリに散布した。その後、キュウリを、温度25℃、湿度60%の恒温室内で保管し、5日間経過したときに生死判定を行い、殺虫率を算出した。これを2反復行った。 (Test Example 4) Efficacy test against cotton aphids Cucumbers were sown in 3-inch pots. Adult female cotton aphids were released on cucumbers 10 days after germination. The next day, the female adults were removed, leaving the first instar larvae that had been laid down.
Emulsion (I) was diluted with water so that the compound of the present invention was 125 ppm. This diluted solution was sprinkled on the cucumbers. Thereafter, the cucumbers were stored in a thermostatic chamber at a temperature of 25° C. and a humidity of 60%, and after 5 days had elapsed, the survival and death determination was performed to calculate the insecticidal rate. This was repeated twice.
化合物番号A-16およびA-18の化合物について、ワタアブラムシ成虫に対する効力試験を行った。この化合物はワタアブラムシ成虫に対して80%以上の殺虫率を示した。
Efficacy tests against adult cotton aphids were conducted for compounds numbered A-16 and A-18. This compound showed an insecticidal rate of over 80% against adult cotton aphids.
(試験例5)トビイロウンカに対する効力試験
乳剤(I)を、本発明化合物の濃度が125ppmになるように水で希釈した。前記希釈液にイネ幼苗を30秒間浸漬し、風乾させた。それをプラスチックケースに入れ、トビイロウンカ2齢幼虫5頭を放した。温度25℃、湿度65%の恒温室内で保管し、放虫から7日間経過したときに生死判定を行い、殺虫率を算出した。これを2反復行った。 (Test Example 5) Efficacy test against brown planthopper Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Rice seedlings were immersed in the diluted solution for 30 seconds and air-dried. They placed it in a plastic case and released five second-instar brown planthopper larvae. The insects were stored in a constant temperature room at a temperature of 25° C. and a humidity of 65%, and 7 days after release, the insects were determined to be alive or dead, and the killing rate was calculated. This was repeated twice.
乳剤(I)を、本発明化合物の濃度が125ppmになるように水で希釈した。前記希釈液にイネ幼苗を30秒間浸漬し、風乾させた。それをプラスチックケースに入れ、トビイロウンカ2齢幼虫5頭を放した。温度25℃、湿度65%の恒温室内で保管し、放虫から7日間経過したときに生死判定を行い、殺虫率を算出した。これを2反復行った。 (Test Example 5) Efficacy test against brown planthopper Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Rice seedlings were immersed in the diluted solution for 30 seconds and air-dried. They placed it in a plastic case and released five second-instar brown planthopper larvae. The insects were stored in a constant temperature room at a temperature of 25° C. and a humidity of 65%, and 7 days after release, the insects were determined to be alive or dead, and the killing rate was calculated. This was repeated twice.
化合物番号A-1およびA-16の化合物について、トビイロウンカに対する効力試験を行った。いずれの化合物も80%以上の殺虫率を示した。
Efficacy tests were conducted on the brown planthopper for compounds numbered A-1 and A-16. All compounds showed an insecticidal rate of 80% or more.
(試験例6)ミナミキイロアザミウマに対する効力試験(125ppm)
キュウリ苗にミナミキイロアザミウマ成虫10頭を放した。乳剤(I)を、本発明化合物の濃度が125ppmになるように水で希釈して、試験用薬液を得た。乳剤(II)を乳剤(I)と同じ倍率に水で希釈して、対照用薬液を得た。前記試験用薬液または対照用薬液をキュウリ苗に散布し、風乾した。散布から2日間経過したときに成虫を除去した。キュウリ苗に卵が産み付けられていた。散布から7日間経過したときに卵から孵化した寄生幼虫を計数した。防除率を算出した。これを2反復行った。 (Test Example 6) Efficacy test against southern yellow thrips (125 ppm)
Ten adult southern yellow thrips were released onto cucumber seedlings. Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm to obtain a test drug solution. Emulsion (II) was diluted with water to the same ratio as emulsion (I) to obtain a control drug solution. The test chemical solution or control chemical solution was sprayed on cucumber seedlings and air-dried. Adults were removed 2 days after spraying. Eggs were laid on cucumber seedlings. Parasitic larvae that hatched from eggs were counted 7 days after spraying. The control rate was calculated. This was repeated twice.
キュウリ苗にミナミキイロアザミウマ成虫10頭を放した。乳剤(I)を、本発明化合物の濃度が125ppmになるように水で希釈して、試験用薬液を得た。乳剤(II)を乳剤(I)と同じ倍率に水で希釈して、対照用薬液を得た。前記試験用薬液または対照用薬液をキュウリ苗に散布し、風乾した。散布から2日間経過したときに成虫を除去した。キュウリ苗に卵が産み付けられていた。散布から7日間経過したときに卵から孵化した寄生幼虫を計数した。防除率を算出した。これを2反復行った。 (Test Example 6) Efficacy test against southern yellow thrips (125 ppm)
Ten adult southern yellow thrips were released onto cucumber seedlings. Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm to obtain a test drug solution. Emulsion (II) was diluted with water to the same ratio as emulsion (I) to obtain a control drug solution. The test chemical solution or control chemical solution was sprayed on cucumber seedlings and air-dried. Adults were removed 2 days after spraying. Eggs were laid on cucumber seedlings. Parasitic larvae that hatched from eggs were counted 7 days after spraying. The control rate was calculated. This was repeated twice.
化合物番号A-16の化合物について、ミナミキイロアザミウマに対する効力試験を行った。この化合物は防除率が80%以上であった。
An efficacy test was conducted on the compound number A-16 against southern thrips. This compound had a control rate of 80% or more.
(試験例7)ネコノミに対する効力試験
本発明化合物をイソプロパノールに溶解させ、濃度20ppmの薬液を調製した。この薬液100μLをガラス製バイアル瓶(φ330mm)の底の内面に塗布し、風乾して、本発明化合物の薄膜を形成させた。
バイアル瓶内にネコノミ(Cat flea、Ctenocephalides felis)の成虫(雌雄混合)4頭を放した。蓋をして25℃の恒温室に置いた。放虫から4日間経過したときにネコノミの生死判定を行い、殺虫率を算出した。これを2反復行った。 (Test Example 7) Efficacy test against cat fleas The compound of the present invention was dissolved in isopropanol to prepare a drug solution with a concentration of 20 ppm. 100 μL of this chemical solution was applied to the inner surface of the bottom of a glass vial (φ330 mm) and air-dried to form a thin film of the compound of the present invention.
Four adult cat fleas (Ctenocephalides felis) (mixed sexes) were released into a vial. It was covered and placed in a constant temperature room at 25°C. Four days after the release of the insects, the cat fleas were determined to be alive or dead, and the insecticidal rate was calculated. This was repeated twice.
本発明化合物をイソプロパノールに溶解させ、濃度20ppmの薬液を調製した。この薬液100μLをガラス製バイアル瓶(φ330mm)の底の内面に塗布し、風乾して、本発明化合物の薄膜を形成させた。
バイアル瓶内にネコノミ(Cat flea、Ctenocephalides felis)の成虫(雌雄混合)4頭を放した。蓋をして25℃の恒温室に置いた。放虫から4日間経過したときにネコノミの生死判定を行い、殺虫率を算出した。これを2反復行った。 (Test Example 7) Efficacy test against cat fleas The compound of the present invention was dissolved in isopropanol to prepare a drug solution with a concentration of 20 ppm. 100 μL of this chemical solution was applied to the inner surface of the bottom of a glass vial (φ330 mm) and air-dried to form a thin film of the compound of the present invention.
Four adult cat fleas (Ctenocephalides felis) (mixed sexes) were released into a vial. It was covered and placed in a constant temperature room at 25°C. Four days after the release of the insects, the cat fleas were determined to be alive or dead, and the insecticidal rate was calculated. This was repeated twice.
化合物番号A-1、A-16、A-17およびA-18の化合物について、ネコノミに対する効力試験を行った。いずれの化合物もネコノミに対して80%以上の殺虫率を示した。
Efficacy tests against cat fleas were conducted on compounds with compound numbers A-1, A-16, A-17, and A-18. All compounds showed an insecticidal rate of 80% or more against cat fleas.
(試験例7)フタトゲチマダニに対する効力試験
本発明化合物をイソプロパノールに溶解させ、濃度20ppmの薬液を調製した。この薬液20μLをガラス製試験管(φ12mm)の底の内面に塗布し、風乾して、本発明化合物の薄膜を形成させた。
試験管内にフタトゲチマダニ(Haemophysalis longicornis)の若虫4頭を放した。蓋をして25℃の恒温室に置いた。放虫から4日間経過したときにフタトゲチマダニの生死判定を行い、殺虫率を算出した。これを2反復行った。 (Test Example 7) Efficacy test against Ixodes ticks The compound of the present invention was dissolved in isopropanol to prepare a drug solution with a concentration of 20 ppm. 20 μL of this chemical solution was applied to the inner surface of the bottom of a glass test tube (φ12 mm) and air-dried to form a thin film of the compound of the present invention.
Four nymphs of Haemophysalis longicornis were released into a test tube. It was covered and placed in a constant temperature room at 25°C. After 4 days had elapsed from the release of the insects, the survival of the ticks was determined, and the killing rate was calculated. This was repeated twice.
本発明化合物をイソプロパノールに溶解させ、濃度20ppmの薬液を調製した。この薬液20μLをガラス製試験管(φ12mm)の底の内面に塗布し、風乾して、本発明化合物の薄膜を形成させた。
試験管内にフタトゲチマダニ(Haemophysalis longicornis)の若虫4頭を放した。蓋をして25℃の恒温室に置いた。放虫から4日間経過したときにフタトゲチマダニの生死判定を行い、殺虫率を算出した。これを2反復行った。 (Test Example 7) Efficacy test against Ixodes ticks The compound of the present invention was dissolved in isopropanol to prepare a drug solution with a concentration of 20 ppm. 20 μL of this chemical solution was applied to the inner surface of the bottom of a glass test tube (φ12 mm) and air-dried to form a thin film of the compound of the present invention.
Four nymphs of Haemophysalis longicornis were released into a test tube. It was covered and placed in a constant temperature room at 25°C. After 4 days had elapsed from the release of the insects, the survival of the ticks was determined, and the killing rate was calculated. This was repeated twice.
化合物番号A-17の化合物について、フタトゲチマダニに対する効力試験を行った。いずれの化合物もフタトゲチマダニに対して80%以上の殺虫率を示した。
Efficacy tests were conducted on compound number A-17 against the red-spotted tick. All of the compounds showed an insecticidal rate of 80% or more against the Phyllis tick.
本発明のイミダゾリルアゾール化合物の中から無作為に選択したものが、いずれも上記のような効果を奏することから、本発明のイミダゾリルアゾール化合物は、例示しきれなかった化合物を含め、有害生物防除、特に殺ダニ、殺虫などの効果を有する化合物であることが理解できる。また、外部寄生虫などの人畜に害のある寄生虫にも効果を有する化合物であることが理解できる。
Since all of the imidazolylazole compounds randomly selected from the imidazolylazole compounds of the present invention exhibit the above-mentioned effects, the imidazolylazole compounds of the present invention, including compounds not fully exemplified, can be used for pest control, It can be understood that it is a compound that has particularly acaricidal and insecticidal effects. It can also be understood that the compound is effective against parasites that are harmful to humans and animals, such as ectoparasites.
優れた殺虫活性および/または殺ダニ活性を有し、安全性に優れ、且つ工業的に有利に合成できるイミダゾリルアゾール化合物、ならびにこれを有効成分として含有する有害生物防除剤を提供することができる。
It is possible to provide an imidazolylazole compound that has excellent insecticidal and/or acaricidal activity, is highly safe, and can be industrially advantageously synthesized, and a pest control agent containing this as an active ingredient.
Claims (5)
- 式(I)で表される化合物またはその塩。
*は、Bとの結合部位を示し、
R1は、置換もしくは無置換のC1~6アルキル基、置換もしくは無置換のC2~6アルケニル基、または置換若しくは無置換のフェニル基であり、
R2は、置換若しくは無置換のC1~6アルキル基であり、
R3は、水素原子、置換若しくは無置換のC1~6アルキル基、アミノ基、シアノ基、またはハロゲノ基であり、
式(I)中、Bは、式(B1)で表される基、または式(B2)で表される基であり、
*は、Aとの結合部位を示し、
R4は、水素原子、置換若しくは無置換のC1~6アルキル基、置換若しくは無置換のC2~6アルケニル基、置換若しくは無置換のC2~6アルキニル基、置換若しくは無置換のC1~6アルキルカルボニル基、置換若しくは無置換のC1~6アルコキシカルボニル基、置換若しくは無置換のC3~6シクロアルキル基、置換若しくは無置換のフェニル基、置換若しくは無置換のナフチル基、置換若しくは無置換の5~10員ヘテロシクリル基、置換若しくは無置換のアミノ基、置換若しくは無置換のアミノカルボニル基、-C(=N-ORa)Rbで表される基、ニトロ基、シアノ基、またはハロゲノ基であり、
Raは、水素原子、または置換若しくは無置換のC1~6アルキル基であり、
Rbは、水素原子、または置換若しくは無置換のC1~6アルキル基であり、
R5は、置換若しくは無置換のC1~6アルキル基または置換若しくは無置換のC3~6シクロアルキル基であり、
nは、Oの数を表し、0、1または2である。〕 A compound represented by formula (I) or a salt thereof.
* indicates the binding site with B,
R 1 is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, or a substituted or unsubstituted phenyl group,
R 2 is a substituted or unsubstituted C1-6 alkyl group,
R 3 is a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, an amino group, a cyano group, or a halogeno group,
In formula (I), B is a group represented by formula (B1) or a group represented by formula (B2),
* indicates the binding site with A,
R 4 is a hydrogen atom, 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 substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted C1-6 alkoxycarbonyl group, substituted or unsubstituted C3-6 cycloalkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted 5-10 A membered heterocyclyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a group represented by -C(=N-OR a )R b , a nitro group, a cyano group, or a halogeno group,
R a is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group,
R b is a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group,
R 5 is a substituted or unsubstituted C1-6 alkyl group or a substituted or unsubstituted C3-6 cycloalkyl group,
n represents the number of O's and is 0, 1 or 2. ] - 請求項1に記載の化合物およびその塩からなる群から選ばれる少なくとも1つを有効成分として含有する有害生物防除剤。 A pest control agent containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and its salt.
- 請求項1に記載の化合物およびその塩からなる群から選ばれる少なくとも1つを有効成分として含有する殺虫または殺ダニ剤。 An insecticide or acaricide containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and its salt.
- 請求項1に記載の化合物およびその塩からなる群から選ばれる少なくとも1つを有効成分として含有する外部寄生虫防除剤。 An ectoparasite control agent containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and its salt.
- 請求項1に記載の化合物およびその塩からなる群から選ばれる少なくとも1つを有効成分として含有する内部寄生虫防除若しくは駆除剤。 An endoparasite control or extermination agent containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and its salt.
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WO2013180193A1 (en) * | 2012-05-31 | 2013-12-05 | 住友化学株式会社 | Fused heterocyclic compound |
JP2016528189A (en) * | 2013-07-02 | 2016-09-15 | シンジェンタ パーティシペーションズ アーゲー | Bicyclic or tricyclic heterocycles with sulfur-containing substituents active in pest control |
WO2021209265A1 (en) * | 2020-04-14 | 2021-10-21 | Basf Se | Tricyclic pesticidal compounds |
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