WO2020262648A1 - アクリル酸エステル誘導体、その用途及びその製造中間体 - Google Patents
アクリル酸エステル誘導体、その用途及びその製造中間体 Download PDFInfo
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- WO2020262648A1 WO2020262648A1 PCT/JP2020/025341 JP2020025341W WO2020262648A1 WO 2020262648 A1 WO2020262648 A1 WO 2020262648A1 JP 2020025341 W JP2020025341 W JP 2020025341W WO 2020262648 A1 WO2020262648 A1 WO 2020262648A1
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- WIPO (PCT)
- Prior art keywords
- group
- aromatic heterocyclic
- substituted
- substituents selected
- chain hydrocarbon
- Prior art date
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Definitions
- the present invention relates to acrylic ester derivatives, their uses, and their production intermediates.
- Patent Document 1 describes an acrylic acid ester derivative.
- An object of the present invention is to provide a compound having an excellent control effect against pests.
- Equation (I) [In the formula, L represents an oxygen atom or CH 2 E is a methyl group substituted with one or more substituents selected from group A, a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, R 6 C.
- R 1 represents a C1-C3 chain hydrocarbon group, cyclopropyl group or halogen atom which may be substituted with one or more halogen atoms.
- n represents 0, 1, 2 or 3 When n is 2 or 3, multiple R 2s may be the same or different.
- R 2 represents a C1-C3 chain hydrocarbon group, cyclopropyl group or halogen atom which may be substituted with one or more halogen atoms.
- R 3 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, and C3-C6 which may be substituted with one or more substituents selected from group B.
- R 4 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, and C3-C6 which may be substituted with one or more substituents selected from group B.
- Cycloalkyl group, C6-C10 aryl group, or 5-10-membered aromatic heterocyclic group are one or more substituents selected from Group C. May be replaced with ⁇
- R 5 represents a C1-C3 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C3 alkoxy group or a hydrogen atom which may be substituted with one or more halogen atoms.
- R 6 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, and C3-C6 which may be substituted with one or more substituents selected from group B.
- the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group are one or more substituents selected from Group C. May be substituted ⁇ or represents a hydrogen atom
- R 3 and R 5 are 4-7-membered non-aromatic heterocycles together with the nitrogen atom to which R 3 and R 5 are bonded ⁇ the 4-7-membered non-aromatic heterocycle is selected from group B1 It may have the above substituents ⁇ .
- a group consisting of. R 11 and R 12 are the same or different, and are substituted with one or more substituents selected from group D, C1-C6 chain hydrocarbon groups, and one or more substituents selected from group E.
- the 6-membered aromatic heterocyclic group and the 3-8-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group F ⁇ or represent a hydrogen atom.
- R 13 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group D, and C3-C6 which may be substituted with one or more substituents selected from group E.
- Cycloalkyl group, phenyl group, naphthyl group, 5-6 membered aromatic heterocyclic group or 3-8 membered non-aromatic heterocyclic group ⁇ the phenyl group, the naphthyl group, the 5-6 membered aromatic heterocyclic group and The 3-8 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group F ⁇ .
- R 14 , R 15 and R 16 represent the same or different C1-C6 chain hydrocarbon groups or phenyl groups.
- Group D C3-C6 cycloalkyl group ⁇ the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of halogen atoms, cyano groups and C1-C3 alkoxy groups ⁇ , OR 17 , S (O) m R 19 , OS (O) 2 R 19 , C (O) R 17 , C (O) OR 17 , OC (O) R 17 , OC (O) OR 17 , OC (O) ) NR 17 R 18 , NR 17 C (O) NR 18 R 19 , NR 17 R 18 , C (O) NR 17 R 18 , S (O) 2 NR 17 R 18 , NR 18 C (O) R 17 , NR 18 C (O) OR 19 , NR 18 , NR 18 , S (O) 2 NR 17 R 18 , NR 18 C (O) R 17 , NR 18 C (O) OR 19 , NR 18
- R 17 and R 18 are the same or different, C1-C6 chain hydrocarbon group, C3-C6 cycloalkyl group, phenyl group, naphthyl group, 5-6 member aromatic heterocyclic group, 3-8 member non-fragrance.
- Group heterocyclic group ⁇ the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5-6 member aromatic heterocyclic group and the 3-8 member non-aromatic group.
- the heterocyclic group may be substituted with one or more substituents selected from the group consisting of halogen atoms, cyano groups and C1-C3 alkoxy groups ⁇ or represents hydrogen atoms.
- R 19 is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5-6-membered aromatic heterocyclic group or a 3-8-membered non-aromatic heterocyclic group ⁇ the C1-
- the C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5-6 member aromatic heterocyclic group and the 3-8 member non-aromatic heterocyclic group are halogen atoms. It may be substituted with one or more substituents selected from the group consisting of a cyano group and a C1-C3 alkoxy group ⁇ .
- Group E C1-C6 chain hydrocarbon group, C3-C6 cycloalkyl group ⁇ The C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group are composed of a halogen atom, a cyano group and a C1-C3 alkoxy group.
- Group F C1-C6 chain hydrocarbon group, C3-C6 cycloalkyl group, C1-C6 alkoxy group and C1-C6 alkylthio group ⁇ the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the said.
- the C1-C6 alkoxy group and the C1-C6 alkylthio group may be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups ⁇ , halogen atoms, cyano groups, nitro groups and hydroxy groups.
- the compound N of the present invention (Hereinafter referred to as the compound N of the present invention), or its N oxide or an agriculturally acceptable salt (hereinafter referred to as the compound of the present invention).
- E is R 6 C (O)-, R 4 OC (O)-, R 3 R 5 NC (O)-, R 3 R 5 NC (S)-, R 4 S (O) 2- , Or R 3 R 5 NS (O) 2- , the compound according to [1], or its N oxide or an agriculturally acceptable salt.
- [7] One or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound according to any one of [1] to [5].
- a composition containing its N oxide or an agriculturally acceptable salt Group (a): A group consisting of an insecticidal active ingredient, an acaricidal active ingredient and a nematode active ingredient; Group (b): Bactericidal active ingredient; Group (c): Plant growth regulator; Group (d): Repellent component.
- [9] Grow soybean or soybean using the compound according to any one of [1] to [5], or an effective amount of an N oxide or an agriculturally acceptable salt thereof, or the composition according to [7].
- [11] A seed or seed holding the compound according to any one of [1] to [5], or an effective amount of an N oxide or an agriculturally acceptable salt thereof, or the composition according to [7].
- n 0, 1, 2 or 3 When n is 2 or 3, multiple R 2s may be the same or different.
- R 2 represents a C1-C3 chain hydrocarbon group, cyclopropyl group or halogen atom which may be substituted with one or more halogen atoms.
- R 3 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, and C3-C6 which may be substituted with one or more substituents selected from group B.
- Cycloalkyl group, C6-C10 aryl group, 5-10-membered aromatic heterocyclic group ⁇ The C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group are one or more substituents selected from Group C.
- R 4 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, and C3-C6 which may be substituted with one or more substituents selected from group B.
- Cycloalkyl group, C6-C10 aryl group, or 5-10-membered aromatic heterocyclic group ⁇ The C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group are one or more substituents selected from Group C.
- R 5 represents a C1-C3 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C3 alkoxy group or a hydrogen atom which may be substituted with one or more halogen atoms.
- R 6 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, and C3-C6 which may be substituted with one or more substituents selected from group B.
- Cycloalkyl group, C6-C10 aryl group, 5-10-membered aromatic heterocyclic group ⁇ The C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group are one or more substituents selected from Group C.
- R 3 and R 5 are 4-7-membered non-aromatic heterocycles together with the nitrogen atom to which R 3 and R 5 are bonded ⁇ the 4-7-membered non-aromatic heterocycle is selected from group B1 It may have the above substituents ⁇ .
- a group consisting of. R 11 and R 12 are the same or different, and are substituted with one or more substituents selected from group D, C1-C6 chain hydrocarbon groups, and one or more substituents selected from group E.
- the 6-membered aromatic heterocyclic group and the 3-8-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group F ⁇ or represent a hydrogen atom.
- R 13 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group D, and C3-C6 which may be substituted with one or more substituents selected from group E.
- Cycloalkyl group, phenyl group, naphthyl group, 5-6 membered aromatic heterocyclic group or 3-8 membered non-aromatic heterocyclic group ⁇ the phenyl group, the naphthyl group, the 5-6 membered aromatic heterocyclic group and The 3-8 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group F ⁇ .
- R 14 , R 15 and R 16 represent the same or different C1-C6 chain hydrocarbon groups or phenyl groups.
- Group D C3-C6 cycloalkyl group ⁇ the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of halogen atoms, cyano groups and C1-C3 alkoxy groups ⁇ , OR 17 , S (O) m R 19 , OS (O) 2 R 19 , C (O) R 17 , C (O) OR 17 , OC (O) R 17 , OC (O) OR 17 , OC (O) ) NR 17 R 18 , NR 17 C (O) NR 18 R 19 , NR 17 R 18 , C (O) NR 17 R 18 , S (O) 2 NR 17 R 18 , NR 18 C (O) R 17 , NR 18 C (O) OR 19 , NR 18 , NR 18 , S (O) 2 NR 17 R 18 , NR 18 C (O) R 17 , NR 18 C (O) OR 19 , NR 18
- R 17 and R 18 are the same or different, C1-C6 chain hydrocarbon group, C3-C6 cycloalkyl group, phenyl group, naphthyl group, 5-6 member aromatic heterocyclic group, 3-8 member non-fragrance.
- Group heterocyclic group ⁇ the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5-6 member aromatic heterocyclic group and the 3-8 member non-aromatic group.
- the heterocyclic group may be substituted with one or more substituents selected from the group consisting of halogen atoms, cyano groups and C1-C3 alkoxy groups ⁇ or represents hydrogen atoms.
- R 19 is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5-6-membered aromatic heterocyclic group or a 3-8-membered non-aromatic heterocyclic group ⁇ the C1-
- the C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5-6 member aromatic heterocyclic group and the 3-8 member non-aromatic heterocyclic group are halogen atoms. It may be substituted with one or more substituents selected from the group consisting of a cyano group and a C1-C3 alkoxy group ⁇ .
- Group E C1-C6 chain hydrocarbon group, C3-C6 cycloalkyl group ⁇ The C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group are composed of a halogen atom, a cyano group and a C1-C3 alkoxy group.
- Group F C1-C6 chain hydrocarbon group, C3-C6 cycloalkyl group, C1-C6 alkoxy group and C1-C6 alkylthio group ⁇ the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the said.
- the C1-C6 alkoxy group and the C1-C6 alkylthio group may be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups ⁇ , halogen atoms, cyano groups, nitro groups and hydroxy groups.
- a group consisting of. ] (Hereinafter referred to as Intermediate B).
- [15] A methyl group substituted with one or more substituents selected from group A, or a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from group A.
- E is R 6 C (O)-, R 4 OC (O)-, R 3 R 5 NC (O)-, R 3 R 5 NC (S)-, R 4 S (O) 2- , Or R 3 R 5 NS (O) 2- , the compound according to [14].
- Equation (IV) [In the formula, E is a methyl group substituted with one or more substituents selected from group A, a C2-C10 chain hydrocarbon group optionally substituted with one or more substituents selected from group A, R 6 C.
- R 2 represents a C1-C3 chain hydrocarbon group, cyclopropyl group or halogen atom which may be substituted with one or more halogen atoms.
- R 3 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, and C3-C6 which may be substituted with one or more substituents selected from group B.
- Cycloalkyl group, C6-C10 aryl group, 5-10-membered aromatic heterocyclic group ⁇ The C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group are one or more substituents selected from Group C. May be substituted ⁇ or represents a hydrogen atom
- R 4 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, and C3-C6 which may be substituted with one or more substituents selected from group B.
- Cycloalkyl group, C6-C10 aryl group, or 5-10-membered aromatic heterocyclic group are one or more substituents selected from Group C. May be replaced with ⁇
- R 5 represents a C1-C3 chain hydrocarbon group which may be substituted with one or more halogen atoms, a C1-C3 alkoxy group or a hydrogen atom which may be substituted with one or more halogen atoms.
- R 6 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group A, and C3-C6 which may be substituted with one or more substituents selected from group B.
- the C6-C10 aryl group and the 5-10-membered aromatic heterocyclic group are one or more substituents selected from Group C. May be substituted ⁇ or represents a hydrogen atom
- R 3 and R 5 are 4-7-membered non-aromatic heterocycles together with the nitrogen atom to which R 3 and R 5 are bonded ⁇ the 4-7-membered non-aromatic heterocycle is selected from group B1 It may have the above substituents ⁇ .
- a group consisting of. R 11 and R 12 are the same or different, and are substituted with one or more substituents selected from group D, C1-C6 chain hydrocarbon groups, and one or more substituents selected from group E.
- the 6-membered aromatic heterocyclic group and the 3-8-membered non-aromatic heterocyclic group may be substituted with one or more substituents selected from Group F ⁇ or represent a hydrogen atom.
- R 13 is a C1-C6 chain hydrocarbon group which may be substituted with one or more substituents selected from group D, and C3-C6 which may be substituted with one or more substituents selected from group E.
- Cycloalkyl group, phenyl group, naphthyl group, 5-6 membered aromatic heterocyclic group or 3-8 membered non-aromatic heterocyclic group ⁇ the phenyl group, the naphthyl group, the 5-6 membered aromatic heterocyclic group and The 3-8 member non-aromatic heterocyclic group may be substituted with one or more substituents selected from group F ⁇ .
- R 14 , R 15 and R 16 represent the same or different C1-C6 chain hydrocarbon groups or phenyl groups.
- Group D C3-C6 cycloalkyl group ⁇ the C3-C6 cycloalkyl group may be substituted with one or more substituents selected from the group consisting of halogen atoms, cyano groups and C1-C3 alkoxy groups ⁇ , OR 17 , S (O) m R 19 , OS (O) 2 R 19 , C (O) R 17 , C (O) OR 17 , OC (O) R 17 , OC (O) OR 17 , OC (O) ) NR 17 R 18 , NR 17 C (O) NR 18 R 19 , NR 17 R 18 , C (O) NR 17 R 18 , S (O) 2 NR 17 R 18 , NR 18 C (O) R 17 , NR 18 C (O) OR 19 , NR 18 , NR 18 , S (O) 2 NR 17 R 18 , NR 18 C (O) R 17 , NR 18 C (O) OR 19 , NR 18
- R 17 and R 18 are the same or different, C1-C6 chain hydrocarbon group, C3-C6 cycloalkyl group, phenyl group, naphthyl group, 5-6 member aromatic heterocyclic group, 3-8 member non-fragrance.
- Group heterocyclic group ⁇ the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5-6 member aromatic heterocyclic group and the 3-8 member non-aromatic group.
- the heterocyclic group may be substituted with one or more substituents selected from the group consisting of halogen atoms, cyano groups and C1-C3 alkoxy groups ⁇ or represents hydrogen atoms.
- R 19 is a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a 5-6-membered aromatic heterocyclic group or a 3-8-membered non-aromatic heterocyclic group ⁇ the C1-
- the C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the 5-6 member aromatic heterocyclic group and the 3-8 member non-aromatic heterocyclic group are halogen atoms. It may be substituted with one or more substituents selected from the group consisting of a cyano group and a C1-C3 alkoxy group ⁇ .
- Group E C1-C6 chain hydrocarbon group, C3-C6 cycloalkyl group ⁇ The C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group are composed of a halogen atom, a cyano group and a C1-C3 alkoxy group.
- Group F C1-C6 chain hydrocarbon group, C3-C6 cycloalkyl group, C1-C6 alkoxy group and C1-C6 alkylthio group ⁇ the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the said.
- the C1-C6 alkoxy group and the C1-C6 alkylthio group may be substituted with one or more substituents selected from the group consisting of halogen atoms and cyano groups ⁇ , halogen atoms, cyano groups, nitro groups and hydroxy groups.
- a group consisting of. ] (Hereinafter referred to as Intermediate C).
- n is 0, and E may be substituted with a methyl group substituted with one or more substituents selected from group A, or C2- which may be substituted with one or more substituents selected from group A.
- n is 0, and E is R 6 C (O)-, R 4 OC (O)-, R 3 R 5 NC (O)-, R 3 R 5 NC (S)-, R 4
- [22] The compound according to [19], wherein n is 0 and E is R 3 R 5 NC (O) ⁇ .
- pests can be controlled.
- the substituent in the present invention will be described.
- the halogen atom means a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
- the substituent has two or more halogen atoms, it means that the halogen atoms may be the same or different from each other.
- the notation "CX-CY" in the present specification means that the number of carbon atoms is X to Y.
- the notation "C1-C6" means that the number of carbon atoms is 1 to 6.
- the chain hydrocarbon group represents an alkyl group, an alkenyl group or an alkynyl group.
- alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, butyl group, sec-butyl group, tert-butyl group and pentyl group.
- Examples include a hexyl group and a decyl group.
- Examples of the alkenyl group include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methyl-1-propenyl group, a 1-methyl-2-propenyl group, a 1,2-dimethyl-1-propenyl group and a 3-.
- Examples thereof include a butenyl group, a 4-pentenyl group, a 5-hexenyl group, and a 9-decenyl group.
- Examples of the alkynyl group include ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 2-butynyl group, 4-pentynyl group, 5 -Hexynyl group and 9-decynyl group can be mentioned.
- alkoxy group examples include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group.
- alkylthio group examples include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, and a hexylthio group.
- cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
- Examples of the aryl group include a phenyl group, an indenyl group, an indanyl group, a naphthyl group, and a tetrahydronaphthyl group.
- Examples of the aromatic heterocyclic group include a pyrrolyl group, a furyl group, a thienyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group and a pyridyl group.
- non-aromatic heterocyclic group examples include an aziridinyl group, an oxylanyl group, a thiylanyl group, an azetidinyl group, an oxetanyl group, a thietanyl group, a pyrrolidinyl group, a tetrahydrofuranyl group, a tetrahydrothienyl group, a piperidyl group, a pyranyl group and a tetrahydropyranyl group.
- Tetrahydrothiopyranyl group azepanyl group, oxepanyl group, thiepanyl group, pyrazolinyl group, pyrazolydinyl group, imidazolinyl group, imidazolidinyl group, oxazolinyl group, thiazolinyl group, oxazolidinyl group, thiazolidinyl group, isooxazolinyl group, isooxazolinyl group.
- Examples thereof include a ru group, an isothiazolinyl group, an isothiazolidinyl group, a morpholinyl group, a thiomorpholinyl group, and a piperazine group.
- the soybean rust fungus having an amino acid substitution of F129L in the mitochondrial cytochrome b protein has a mutation in the mitochondrial cytochrome b gene encoding the mitochondrial cytochrome protein, and the amino acid substitution of F129L occurs as a result of the mutation, resulting in QoI. It is a soybean rust fungus (scientific name: Phakopsora pachyrhizi) that is resistant to bactericides.
- intermediate A, intermediate B, intermediate C and intermediate D may have one or more stereoisomers.
- Stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
- the present invention includes each stereoisomer and a mixture of stereoisomers in any ratio.
- the compound N of the present invention or its N oxide can be mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, or benzoic acid to cause hydrochloride, sulfate, nitrate, phosphate, acetate, or benzoate. Etc. may form acid addition salts.
- an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, or benzoic acid to cause hydrochloride, sulfate, nitrate, phosphate, acetate, or benzoate.
- Etc. may form acid addition salts.
- Examples of the compound N of the present invention include the following compounds.
- Aspect 1 A compound in which n is 0 in the compound N of the present invention.
- Aspect 2 In Aspect 1, a compound in which R 1 is a methyl group or a chlorine atom.
- Aspect 3 In Aspect 1, a compound in which R 1 is a methyl group.
- Aspect 4 In Aspect 1, a compound in which L is an oxygen atom.
- Aspect 5 In Aspect 2, a compound in which L is an oxygen atom.
- Aspect 6 In Aspect 3, a compound in which L is an oxygen atom.
- Aspect 7 In Aspect 1, a compound in which R 1 is a chlorine atom.
- Aspect 8 A compound in which L is CH 2 in Aspect 1.
- E is a methyl group substituted with one or more substituents selected from group A, or one or more substitutions selected from group A.
- E is R 6 C (O)-, R 4 OC (O)-, R 3 R 5 NC (O)-, R 3 A compound that is R 5 NC (S)-, R 4 S (O) 2- , or R 3 R 5 NS (O) 2- .
- a compound in which E is R 3 R 5 NC (O)-in any of Aspects 1 to 10 or Compound N of the present invention.
- E is a methyl group substituted with one or more substituents selected from group J, and one or more substituents selected from group J.
- R 5 being a methyl group, a methoxy group, or a hydrogen atom
- R 3 and R 5 being a bond of R 3 and R 5.
- Group J OCH 3 , Si (CH 3 ) 3 , C3-C6 cycloalkyl group, cyano group, halogen atom, phenyl group, and 5-6 membered aromatic heterocyclic group ⁇ the phenyl group and the 5-6 membered aromatic
- the group heterocyclic group may be substituted with one or more substituents selected from the group consisting of a trifluoromethyl group, a halogen atom and a cyano group ⁇ .
- Aspect 17 a methyl group in which E is substituted with one or more substituents selected from group J, or a C2-C6 chain optionally substituted with one or more substituents selected from group J.
- E is R 3 R 5 NC (O) ⁇ , and R 3 may be substituted with one or more halogen atoms, or one or more C1-C5 chain hydrocarbon groups.
- a compound in which a phenyl group which may be substituted with a halogen atom and R 5 is a methyl group, a methoxy group, or a hydrogen atom.
- E is R 3 R 5 NC (O) ⁇ , and R 3 and R 5 are 5-6 members together with the nitrogen atom to which R 3 and R 5 are bonded.
- E is a methyl group substituted with one or more substituents selected from group K, and one or more substituents selected from group K.
- R 3 optionally substituted C2-C6 chain hydrocarbon group, or R 3 R 5 NC (O) - and is, R 3 is 1 or more may be substituted by a halogen atom C1-C3 chain hydrocarbon A group, a C3-C6 cycloalkyl group optionally substituted with one or more halogen atoms, or a phenyl group optionally substituted with one or more halogen atoms, where R 5 is a methyl group, a methoxy group, or a hydrogen.
- a compound which is an atom and in which R 3 and R 5 may form a 5-6 member non-aromatic heterocyclic group together with a nitrogen atom to which R 3 and R 5 are bonded.
- Group K OCH 3 , Si (CH 3 ) 3 , C3-C6 cycloalkyl group, cyano group, halogen atom, 3-6 member non-aromatic heterocyclic group, phenyl group, and 5-6 member aromatic heterocyclic group.
- the C3-C6 cycloalkyl group, the 3-6 member non-aromatic heterocyclic group, the phenyl group and the 5-6 member aromatic heterocyclic group are a group consisting of a trifluoromethyl group, a halogen atom and a cyano group. It may be substituted with one or more substituents selected from ⁇ .
- E is R 3 R 5 NC (O) ⁇ , and R 3 may be substituted with one or more halogen atoms C1-.
- Examples of the intermediate A include the following compounds.
- Aspect A1 A compound in which n is 0 in Intermediate A.
- Aspect A2 In Aspect A1, a compound in which R 1 is a methyl group or a chlorine atom.
- Aspect A3 A compound in which R 1 is a methyl group in A1.
- Aspect A4 A compound in which L is an oxygen atom in A1.
- Aspect A6 A compound in which L is an oxygen atom in A3.
- Aspect A7 A compound in which R 1 is a chlorine atom in A1.
- a compound in which L is an oxygen atom.
- Aspect A9 A compound in which L is CH 2 in A1.
- Aspect A10 A compound in which L is CH 2 in aspect A2.
- Aspect A11 A compound in which L is CH 2 in A3.
- Aspect A12 A compound in which L is CH 2 in A7.
- Examples of the intermediate B include the following compounds.
- Aspect B1 A compound in which n is 0 in Intermediate B.
- Aspect B2 In Aspect B1, a compound in which R 1 is a methyl group or a chlorine atom.
- Aspect B3 In Aspect B1, a compound in which R 1 is a methyl group.
- Aspect B4 In Aspect B1, a compound in which L is an oxygen atom.
- Aspect B5 In Aspect B2, a compound in which L is an oxygen atom.
- Aspect B6 In Aspect B3, a compound in which L is an oxygen atom.
- E is a methyl group substituted with one or more substituents selected from group A, or one or more substituents selected from group A.
- a compound which is a C2-C10 chain hydrocarbon group which may be substituted with [Aspect B8] A compound in which E is a methyl group substituted with one or more substituents selected from Group A in any of aspects B1 to B6 or intermediate B.
- E is R 6 C (O)-, R 4 OC (O)-, R 3 R 5 NC (O)-, R 3 R.
- a compound in which E is R 3 R 5 NC (O)-in any of aspects B1 to B6 or intermediate B.
- a compound in which E is a benzyl group or a (C3-C6 cycloalkyl) methyl group in any of aspects B1 to B6 or intermediate B.
- Examples of the intermediate C include the following compounds.
- E is substituted with a methyl group substituted with one or more substituents selected from Group A, or one or more substituents selected from Group A.
- Aspect C5 In either Aspect C1 or Intermediate C, E is R 6 C (O)-, R 4 OC (O)-, R 3 R 5 NC (O)-, R 3 R 5 NC (Aspect C5). A compound that is S)-, R 4 S (O) 2- , or R 3 R 5 NS (O) 2- .
- Aspect C6 A compound in which E is R 3 R 5 NC (O)-in either Aspect C1 or Intermediate C.
- Aspect C7 A compound in which E is a benzyl group or a (C3-C6 cycloalkyl) methyl group in either Aspect C1 or Intermediate C.
- Examples of the intermediate D include the following compounds.
- a compound in which L is an oxygen atom a compound in which L is an oxygen atom.
- a compound in which L is an oxygen atom a compound in which L is an oxygen atom.
- a compound in which L is an oxygen atom.
- Aspect D9 A compound in which L is CH 2 in aspect D1.
- Aspect D10 A compound in which L is CH 2 in aspect D2.
- Aspect D11 A compound in which L is CH 2 in aspect D3.
- Aspect D12 A compound in which L is CH 2 in aspect D7.
- the compound represented by the formula (IE1) (hereinafter referred to as the compound (IE1)) is the intermediate A represented by the formula (II) and the compound represented by the formula (R1) (hereinafter referred to as the compound (R1)).
- E 1 is a methyl group substituted with one or more substituents selected from group A, or a C2-C10 chain hydrocarbon which may be substituted with one or more substituents selected from group A. Represents a group, and other symbols have the same meanings as described above.
- the reaction is usually carried out in a solvent.
- Examples of the solvent used in the reaction include hydrocarbons such as hexane, toluene and xylene (hereinafter referred to as hydrocarbons); methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), and the like.
- hydrocarbons such as hexane, toluene and xylene (hereinafter referred to as hydrocarbons); methyl tert-butyl ether (hereinafter referred to as MTBE), tetrahydrofuran (hereinafter referred to as THF), and the like.
- Ethers such as dimethoxyethane (hereinafter referred to as ethers); halogenated hydrocarbons such as chloroform and chlorobenzene (hereinafter referred to as halogenated hydrocarbons); dimethylformamide (hereinafter referred to as DMF), N-methylpyrrolidone and the
- amides Amides (hereinafter referred to as amides); esters such as methyl acetate and ethyl acetate (hereinafter referred to as esters); nitriles such as acetonitrile and propionitrile (hereinafter referred to as nitriles) and two or more of them.
- esters such as methyl acetate and ethyl acetate
- nitriles such as acetonitrile and propionitrile
- phosphines include triphenylphosphine and trimethylphosphine.
- the azodiesters include diethyl azodicarboxylate, diisopropyl azodicarboxylate and bis (2-methoxyethyl) azodicarboxylate.
- the compound (R1) is usually in a ratio of 1 to 10 mol, phosphines are usually in a ratio of 1 to 10 mol, and azodiesters are usually in a ratio of 1 to 10 mol with respect to 1 mol of intermediate A. Used.
- the reaction temperature is usually in the range of 0 to 150 ° C.
- the reaction time is usually in the range of 0.1-48 hours.
- the compound (IE1) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
- Compound (R1) is known or can be produced according to a known method.
- Manufacturing method B Compound (IE1) is produced by reacting intermediate A represented by the formula (II) with a compound represented by the formula (R2) (hereinafter referred to as compound (R2)) in the presence of a base. You can also do it.
- X 1 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyl group, and a p-toluenesulfonyl group, and other symbols have the same meanings as described above.
- the reaction is usually carried out in a solvent.
- Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more of these.
- Examples of the base include organic bases such as triethylamine and pyridine (hereinafter referred to as organic bases); alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter referred to as alkali metal carbonates); sodium hydrogen carbonate and hydrogen carbonate.
- Alkali metal bicarbonates such as potassium (hereinafter referred to as alkali metal bicarbonates); sodium hydride and tripotassium phosphate can be mentioned.
- compound (R2) is usually used at a ratio of 1 to 10 mol and a base is usually used at a ratio of 1 to 10 mol with respect to 1 mol of Intermediate A.
- the reaction temperature is usually in the range of ⁇ 20 to 150 ° C.
- the reaction time is usually in the range of 0.1-48 hours.
- the compound (IE1) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
- Compound (R2) is known or can be produced according to a known method.
- the compounds represented by the formula (IE2) are the intermediate A represented by the formula (II) and the compound represented by the formula (R3) (hereinafter referred to as the compound (R3)).
- E 2 is R 6 C (O)-, R 4 OC (O)-, R 3 R 5 NC (O)-, R 3 R 5 NC (S)-, R 4 S (O) 2 -Or R 3 R 5 NS (O) 2- , and other symbols have the same meaning as described above.
- the reaction is usually carried out in a solvent.
- Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more of these.
- Examples of the base include organic bases, alkali metal carbonates, alkali metal bicarbonates, sodium hydride and tripotassium phosphate.
- compound (R3) is usually used at a ratio of 1 to 10 mol and a base is usually used at a ratio of 1 to 10 mol with respect to 1 mol of Intermediate A.
- the reaction temperature is usually in the range of ⁇ 78 to 100 ° C.
- the reaction time is usually in the range of 0.1-48 hours.
- the compound (IE2) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
- Compound (R3) is known or can be produced according to a known method.
- the compound represented by the formula (IE3) (hereinafter referred to as compound (IE3)) is prepared by reacting the intermediate A represented by the formula (II) with triphosgene in the presence of a base and then the formula. It can be produced by reacting with the compound represented by (R4) (hereinafter, referred to as compound (R4)). This reaction can also be carried out in one pot.
- E 3 represents R 4 O- or R 3 R 5 N-, and other symbols have the same meanings as described above.
- the reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more of these.
- Examples of the base include organic bases.
- triphosgene is usually used at a ratio of 0.3 to 3 mol
- a base is usually used at a ratio of 1 to 10 mol
- compound (R4) is usually used at a ratio of 1 to 10 mol with respect to 1 mol of intermediate A. Be done.
- the reaction temperature of Intermediate A and triphosgene is usually in the range of ⁇ 78 to 100 ° C.
- the reaction time is usually in the range of 0.1 to 48 hours.
- the reaction temperature with the subsequent compound (R4) is usually in the range of ⁇ 78 to 100 ° C.
- the reaction time is usually in the range of 0.1 to 48 hours.
- the compound (IE3) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
- Compound (R4) is known or can be produced according to a known method.
- the compound N of the present invention can be produced by reacting the intermediate B represented by the formula (III) with iodomethane in the presence of a base.
- a base In the formula, the symbols have the same meanings as described above.
- the reaction is usually carried out in a solvent.
- the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles and mixtures of two or more of these.
- the base used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, sodium hydride and mixtures thereof.
- iodomethane is usually used in a ratio of 1 to 10 mol and a base is usually used in a ratio of 1 to 20 mol with respect to 1 mol of Intermediate B.
- the reaction temperature is usually in the range of ⁇ 20 to 100 ° C.
- the reaction time is usually in the range of 0.1-48 hours.
- the compound N of the present invention can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
- the compound (IE1) can be produced by reacting the intermediate D represented by the formula (VI) with the compound (R1) in the presence of a palladium catalyst.
- a palladium catalyst In the formula, the symbols have the same meanings as described above.
- the reaction is usually carried out in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water and mixtures of two or more of these.
- Examples of the palladium catalyst used in the reaction include palladium (II) acetate, ⁇ 1,1'-bis (diphenylphosphino) ferrocene ⁇ dichloropalladium (II), XPhos Pd G3, Brett Phos Pd G3, tBuBret Phos Pd G3, and Xant Phos. Examples thereof include Pd G3 and RockPhos Pd G3. Ligands, bases or additives may be added to the reaction as needed.
- Ligands used in the reaction include, for example, 2- (di-t-butylphosphino) -1,1'-binaphthyl, BrettPhos, tBuBrettPhos, RockPhos, AdBretPhos, tBuXPhos, and 5- (di-t-butylphos). Fino) -1', 3', 5'-triphenyl-1'H- [1,4'] bipyrazole can be mentioned. When a ligand is used in the reaction, the ligand is usually used at a ratio of 0.01 to 1 mol with respect to 1 mol of Intermediate D.
- Examples of the base used in the reaction include organic bases; alkali metal carbonates; alkali metal alkoxides such as potassium t-butoxide and sodium t-butoxide; and tripotassium phosphate.
- the base is usually used in a ratio of 1 to 10 mol to 1 mol of Intermediate D.
- Examples of the additive used in the reaction include sodium iodide and potassium iodide.
- the additive is usually used at a ratio of 0.1 to 10 mol to 1 mol of Intermediate D.
- compound (R1) is usually used at a ratio of 1 to 10 mol and palladium catalyst is usually used at a ratio of 0.01 to 1 mol with respect to 1 mol of Intermediate D.
- the reaction temperature is usually in the range of 0 to 150 ° C.
- the reaction time is usually in the range of 0.1 to 120 hours.
- the compound (IE1) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
- Compound (R1) is known or can be produced according to a known method.
- the N oxide of the compound N of the present invention can be produced by reacting the compound N of the present invention with an oxidizing agent.
- the reaction can be carried out, for example, according to the method described in US Patent Application Publication No. 2018/0009778 or International Publication No. 2016/121970.
- the intermediate A represented by the formula (II) is a compound represented by the formula (II-A) (hereinafter referred to as compound (II-A)) and a bis (pinacolato) diboron in the presence of a base and a palladium catalyst. It can be produced by reacting to obtain a compound represented by the formula (II-B) (hereinafter referred to as compound (II-B)) and then oxidizing the compound (II-B).
- X 2 represents a bromine atom, an iodine atom or a trifluoromethanesulfonyl group, and other symbols have the same meanings as described above. ]
- the reaction is usually carried out in a solvent.
- the solvent used in the reaction include sulfoxides such as hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, and dimethyl sulfoxide (hereinafter referred to as DMSO) (hereinafter referred to as sulfoxides). , Nitrids and mixtures of two or more of these.
- the base used in the reaction include organic bases, alkali metal carbonates, alkali metal bicarbonates and tripotassium phosphate.
- the palladium catalyst examples include [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride.
- 1 to 5 mol of bis (pinacolato) diboron usually 1 to 5 mol of base, and 0.01 to 0 mol of palladium catalyst are usually used for 1 mol of compound (II-A). Used in proportions of 5 mol.
- the reaction temperature is usually in the range of 0 to 150 ° C. and the reaction time is usually in the range of 0.1 to 48 hours.
- compound (II-B) can be isolated by adding water to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
- the reaction is usually carried out in a solvent.
- the solvent used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; methanol, ethanol, propanol, butanol and other alcohols (hereinafter referred to as alcohols). ); Water and mixtures thereof are mentioned.
- the oxidizing agent used in the reaction include metachloroperbenzoic acid and hydrogen peroxide solution. When hydrogen peroxide solution is used as the oxidizing agent, a base may be added if necessary. Examples of the base include sodium hydroxide and potassium hydroxide.
- an oxidizing agent is usually used at a ratio of 1 to 5 mol to 1 mol of compound (II-B).
- the base is usually used in a ratio of 0.1 to 5 mol to 1 mol of compound (II-B).
- the reaction temperature is usually in the range of ⁇ 20 to 120 ° C. and the reaction time is usually in the range of 0.1 to 48 hours.
- intermediate A is isolated by adding water and a reducing agent such as sodium thiosulfate to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer. be able to.
- Compound (II-A) can be produced according to a known method or a known method.
- the intermediate B represented by the formula (III) can be produced by reacting the compound represented by the formula (V) (hereinafter referred to as compound (V)) with methyl formate in the presence of a base.
- compound (V) the compound represented by the formula (V)
- the symbols have the same meanings as described above.
- the reaction is usually carried out in a solvent.
- the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, nitriles, and mixtures of two or more of these.
- the base examples include alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkoxides such as sodium methoxydo, sodium ethoxydo and potassium t-butoxide; sodium amide, lithium amide, lithium diisopropylamide and sodium hexamethyl. Alkoxide amides such as disilamide, lithium hexamethyldisilazide; and mixtures thereof.
- methyl formate is usually used at a ratio of 1 to 100 mol and a base is usually used at a ratio of 1 to 10 mol with respect to 1 mol of compound (V).
- the reaction temperature is usually in the range of ⁇ 20 to 80 ° C.
- reaction time is usually in the range of 0.1-48 hours.
- intermediate B can be isolated by adding an acidic aqueous solution such as dilute hydrochloric acid to the reaction mixture, extracting with an organic solvent, and performing post-treatment operations such as drying and concentrating the organic layer.
- the compounds represented by the formula (VE1) are the compound represented by the formula (VA) (hereinafter referred to as compound (VA)) and the compound (R1). ) Can be produced by reacting in the presence of phosphines and azodiesters. [In the formula, the symbols have the same meanings as described above. ] The reaction can be carried out according to the production method A using the compound (VA) instead of the intermediate A. Compound (VA) can be produced according to a known method or a known method.
- Reference manufacturing method D The compound represented by the formula (VE2) (hereinafter referred to as compound (VE2)) is produced by reacting compound (VA) and compound (R3) in the presence of a base. Can be done. [In the formula, the symbols have the same meanings as described above. ] The reaction can be carried out according to the production method C by using the compound (VA) instead of the intermediate A.
- Reference manufacturing method E Intermediate D can be produced by reacting a compound represented by the formula (VI-A) (hereinafter referred to as compound (VI-A)) with iodomethane in the presence of a base. [In the formula, the symbols have the same meanings as described above. ] The reaction can be carried out according to the production method E using the compound (VI-A) instead of the intermediate B.
- Reference manufacturing method F Compound (VI-A) can be produced by reacting a compound represented by the formula (VI-B) (hereinafter referred to as compound (VI-B)) with methyl formate in the presence of a base. [In the formula, the symbols have the same meanings as described above. ] The reaction can be carried out according to the reference production method B by using the compound (VI-B) instead of the compound (V).
- the compound (VI-B) is known or can be produced according to a known method.
- the compound of the present invention may be mixed or used in combination with one or more components (hereinafter referred to as this component) selected from the group consisting of the following groups (a), group (b), group (c) and group (d). it can.
- the mixed use or combined use means that the compound of the present invention and the present component are used at the same time, separately or at intervals of time.
- the compound of the present invention and the present component may be contained in separate preparations or may be contained in one preparation.
- One aspect of the present invention contains one or more components selected from the group consisting of group (a), group (b), group (c) and group (d), and the compound of the present invention (hereinafter, composition). It is written as A).
- Group (a) includes acetylcholine esterase inhibitors (eg, carbamate pesticides, organic phosphorus pesticides), GABAergic chlorine ion channel blockers (eg, phenylpyrazole pesticides), sodium channel modulators (eg, pyrethroid pesticides).
- acetylcholine esterase inhibitors eg, carbamate pesticides, organic phosphorus pesticides
- GABAergic chlorine ion channel blockers eg, phenylpyrazole pesticides
- sodium channel modulators eg, pyrethroid pesticides.
- Nicotinic acetylcholine receptor competitive modulators eg, neonicotinoid pesticides
- nicotinic acetylcholine receptor allosteric modulators glutamate-operated chlorine ion channel allosteric modulators (eg, macrolide pesticides)
- immature hormones Mimics multisite inhibitors, chord organ TRPV channel modulators, tick growth inhibitors, microbial-derived insect midgut intestinal membrane disruptors, mitochondrial ATP synthase inhibitors, oxidative phosphorylation deconjugation agents, nicotinic acetylcholine receptor channels
- Blockers eg, nelystoxin pesticides
- chitin synthesis inhibitors shedding inhibitors, ecdison receptor agonists, octopamine receptor agonists, mitochondrial ion channel complex I, II, III and IV inhibitors, potential dependent A group of sex sodium channel blockers, acetyl CoA carb
- Group (b) includes nucleic acid synthesis inhibitors (eg, phenylamide fungicides, acylaminomic fungicides), cell division and cytoskeletal inhibitors (eg, MBC fungicides), respiratory inhibitors (eg, QoI fungicides).
- nucleic acid synthesis inhibitors eg, phenylamide fungicides, acylaminomic fungicides
- cell division and cytoskeletal inhibitors eg, MBC fungicides
- respiratory inhibitors eg, QoI fungicides.
- QiI fungicides amino acid synthesis and protein synthesis inhibitors (eg, anilinopyridine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (eg, triazoles and other DMIs) It is a group consisting of fungicides), cell wall synthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, multi-action point contact active fungicides, microbial fungicides, and other fungicides. These are described in the classification based on the mechanism of action of FRAC.
- Group (c) is a group of plant growth regulator components (including mycorrhizal fungi and rhizobia).
- Group (d) is a group of repellent components.
- alanical carb + SX means a combination of alanical carb and SX.
- the abbreviation of SX means any one compound of the present invention selected from the compound groups SX1 to SX80 described in Examples.
- all of the following components are known components and can be obtained from commercially available preparations or produced by a known method. If this component is a microorganism, it can also be obtained from a fungus depository.
- the numbers in parentheses represent CAS RN (registered trademark).
- Kurstaki strain EVB113-19 + SX Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp.
- the ratio of the compound of the present invention to the present component is not particularly limited, but the weight ratio (compound of the present invention: the present component) is 1000: 1 to 1: 1000, 500: 1 to 1: 500, 100: 1. ⁇ 1: 100, 50: 1, 20: 1, 10: 1, 9: 1, 8: 1, 7: 1, 6: 1, 5: 1, 4: 1, 3: 1, 2: 1, 1 1, 1, 2, 1: 3, 1: 4, 1: 5, 1: 6, 1: 7, 1: 8, 1: 9, 1:10, 1:20, 1:50 and the like. ..
- the compound of the present invention is effective against pests.
- pests include phytopathogenic microorganisms, harmful arthropods such as harmful insects and mites, harmful nematodes, and harmful mollusks.
- the compound of the present invention can control plant diseases caused by phytopathogenic microorganisms such as fungi, oomycete, Phytomyxea, and bacteria.
- Fungi include, for example, Ascomycota, Basidiomycota, Blassoladiomycota, Cytridiomycota, Mucoromycota and Oldiomycota.
- Ascomycota Basidiomycota
- Blassoladiomycota Blassoladiomycota
- Cytridiomycota Cytridiomycota
- Mucoromycota and Oldiomycota.
- the numbers in parentheses indicate the scientific names of the phytopathogenic microorganisms that cause each disease.
- Rice diseases blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), yellowing dwarf disease (Sclerophthora macrospora), rhizoctonia and Blight (Epicoccum nigrum), Blight (Trichoderma viride, Rhizopus oryzae); Diseases of wheat: Udonko disease (Blumeria graminis), red mold disease (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust disease (Puccinia striiformis), black rust disease (Puccinia graminis), red rust disease (Puccinia graminis) ), Monographella nivalis (Microdochium nivale, Microdochium majus),
- Lachrymans Eggplant wilt (Ralstonia solanacearum), Canker scab (Xanthomonas citri) ), Hakusai soft rot (Erwinia carotovora), potato scab (Streptomyces scabiei), corn Goss's wilt disease (Clavibacter michiganensis), grapes, olives, peaches and other piercing diseases (Xylella fastidiosa), apples, peaches, cherry blossoms Pseudomonas chinensis (Agrobacterium tumefaciens) in Burkholderia.
- harmful arthropods examples include the following.
- Hemiptera Himetobiunka (Laodelphax striatellus), Tobiirounka (Nilaparvata lugens), Sejirounka (Sogatella furcifera), Corn unkah (Peregrinus maidis), Kitonka (Javesella pellucida), Kitownka (Javesella pellucida) Aphidaceae (Delphacidae); Aphid aphid (Nephotettix cincticeps), Thai one aphid aphid (Nephotettix virescens), Aphid aphid aphid (Nephotettix nigropictus), Inazuma yokobai (Recilia dorsalis), Chanomidori (Recilia dorsalis) , Cornleaf hopper (Dalbulus maidis), Shiroo yokobai (Cofana spectra), Amrasca biguttula bigut
- Aphidellidae African spittle bug (Philaenus spumalis), etc.
- Aphid worm family (Aphrophoridae) Aphis aphid (Cercopidae); Aphis aphid, Aphis aphid, Aphis gossypii, European apple aphid (Aphis pomi), Yukiyanagi aphid (Aphis aphid) Myzus persicae), wheat aphid (Brachycaudus helichrysi), daikon aphid (Brevicoryne brassicae), rosy apple aphid (Dysaphis plantaginea), fake aphid (Lipaphis erysimi), tulip aphid (Lipaphis erysimi), tulip aphid Aphididae (Aulacorthum solani), Lettuce aphididae (Nasonovia ribisnigri
- Aphididae (Aphididae) , Phylloxera devastatrix, Phylloxera notabilis, Southern Pecan Reef Philoxerae, etc. Phylloxeridae; Adelges aphididae, Adelges tsugae , Aphrastasia pectinatae and other aphids (Adelgidae); rice aphids (Scotinophara lurida), black paddy bugs (Scotinophara coarctata), blue-spotted aphids (Nezara antennata), spider aphids (Nezara antennata) Aphididae (Eysarcoris lewisi), Aphididae (Eysarcoris ventralis), Aphididae aphididae (Eysarcoris annamita), Aphididae (Halyomorpha aphididae), Aphididae (Halyomorpha aphi
- Whitefly (Aleyrodidae); Whitefly (Abgrallaspis cyanophylli), Aonidiella aurantii, Nashimarukaigaramushi (Diaspidiotus perniciosus), Kuwashirokaigaramushi (Pseudaulacaspis) Whitefly (Unaspis citri) and other whiteflies Family (Diaspididae); Psyllidae (Coccidae) such as Ruby scale insect (Ceroplastes rubens); Psyllidae (Icerya seychellarum) and other Psyllidae (Psyllidae) solani), Psyllidae (Phenacoccus solenopsis), Psyllidae (Planococcus kraunhiae), Psyllidae (Pseudococcus comstocki), Psyllidae (Planococcus citri), Ps
- Lepidoptera Nikameiga (Chilo suppressalis), Dark Hedid Stem Borer (Chilo polychrysus), White Stem Borer (Scirpophaga innotata), Itten Omeiga (Scirpophaga incertulas), Rupela albina, Kobunomeiga (Cnaphalo) Snout moth (Marasmia exigua), Watanomeiga (Notarcha derogata), Awanomeiga (Ostrinia furnacalis), European corn moth (Ostrinia nubilalis), Hymadalanomeiga (Hellula undalis), Monki chronomeiga (Hellula undalis), Monki chronomeiga (Hellula undalis) , Rice case worm (Nymphula depunctalis), sugar cane bowler (Diatraea saccharalis), egg plant fruit bowler (Leucinodes orbonalis), etc.
- Helicoverpa spp. Velvet bean caterpillar (Anticarsia gemmatalis), cotton leaf worm (Alabama argillacea), hop wine borer (Hydraecia immanis), etc. ); Shirocho family (Pieridae) such as Monshirocho (Pieris rapae); Nashihimeshinki (Grapholita molesta), Sumomohimeshinkui (Grapholita dimorpha), Mameshiniga (Leguminivora glycinivorella), Azukisayamushiga (Matsumuraeses) ), Chanokokakumonhamaki (Adoxophyes honmai), Chahamaki (Homona magnanima), Midarekakumonhamaki (Archips fuscocupreanus), Kodling moss (Cydia pomonella), Kansha sinkihamaki (Tetramoera schistaceana), Bean chute bora Fruit bowler (Citripestis sagitt
- Thrips Thysanoptera: Mikankiiro thrips (Frankliniella occidentalis), Minamikiiro thrips (Thrips palmi), Chanokiiro thrips (Scirtothrips dorsalis), Negia thrips (Thrips thrips), Thrips thrips (Thrips) , Thripidae such as Thripidae, Thripidae such as Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thri
- Agromyzidae such as Delia platura, Delia antiqua, Pegomya cunicularia; Agromyzidae (Tetanops myopaeformis), etc.
- Agromyzidae Agromyza oryzae
- Tomato leafminer Liriomyza sativae
- Agromyzidae Liriomyza trifolii
- Agromyzidae Chromatomyia horticola
- Agromyzidae (Agromyzidae); Agromyzidae (Chromamyzidae); Agromyzidae (Chromamyzidae); Bactrocera cucurbitae, Mikankomi fly (Bactrocera dorsalis), Nasumi fly (Bactrocera latifurons), Olive mibae (Bactrocera oleae), Quisland mibae (Bactrocera tryoni), Chichukai mibae (Ceratitis mibae), Chichukai mibae (Ceratitis mibae) ), Etc.
- Agromyzidae (Tephritidae); Agromyzidae (Hydrellia griseola), Agromyzidae (Hydrellia philippina), Fruitfly (Hydrellia sasakii), etc.
- Agromyzidae (Drosophila melanogaster) and other leafminers (Drosophilidae); Agromyzidae (Megaselia spiracularis) and other leafminers (Phoridae); Agromyzidae (Clogmia albipunctata) and other leafminers (Clogmia albipunctata) and other leafminers (Psychodidae) Agromyzidae (Sciaridae); Agromyzidae (Mayetiola dest) Anopheles mosquitoes (Cecidomyiidae) such as ructor) and Anopheles mosquitoes (Orseolia oryzae); Anopheles mosquitoes (Diopsidae) such as Diopsis macrophthalma; Anopheles mosquitoes (Glossinidae) Simul, Anopheles mosquitoes (Glossinid)
- Diabrotica spp For example, Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm.
- Western corn root worm (Diabrotica virgifera virgifera)
- Southern corn root worm (Diabrotica undecimpunctata howardi)
- Northern corn root worm Diabrotica barberi
- Mexican corn root worm Mexican corn root worm.
- Ugane buoy (Anomala cuprea), Himekogane (Anomala rufocuprea), Anomala albopilosa, Japanese beetle (Popillia japonica), Nagachakogane (Heptophylla picea), European genus Holotrichia (Rhizotrogus), European genus Holotrichia (Rhizotrogus) .), Phyllophaga crinita, etc., Phyllophaga spp., Diloboderus abderus, etc., Holotrichia (Scarabaeidae), etc.; Watamihigenagazoumushi (Arae), etc.
- Anthriibidae Japanese beetle (Aponidae) such as Cylas formicarius; Japanese beetle (Bruchidae) such as Brazilian beetle (Zabrotes subfasciatus); Japanese beetle (Bruchidae), Japanese beetle (Tomic) Hampei, etc., Scolytidae; Anomala albopilosa (Euscepes postfasciatus), Alfera postica, Sitophilus zeamais, Sitophilus zeamais, Sitophilus soryzae, Granaria coccineus , Japanese beetle (Lissorhoptrus oryzophilus), Japanese beetle (Rhabdoscelus lineaticollis), Japanese beetle (Anthonomus grandis), Japanese beetle (Sphenophorus venatus), Southern cornville bug (Sphenophorus venatus), Southern cornville bug (Sphenophorus
- Orthoptera Tonosama grasshopper (Locusta migratoria), Sydney locust (Dociostaurus maroccanus), Australian locust (Chortoicetes terminifera), Akato locust (Nomadacris septemfasciata), Brown locust (Locustana) Locust (Calliptamus italicus), differential glass hopper (Melanoplus differentialis), two-striped glass hopper (Melanoplus bivittatus), migretry glass hopper (Melanoplus sanguinipes), red legged glass hopper (Melanoplus femurrubrum), clear winged glass hopper (Melanoplus femurrubrum) Sabaquat locust (Schistocerca gregaria), yellow wing locust (Gastrimargus musicus), spar slaughtered locust (Austracris guttulosa), kobane locust (Oxya yezoensis),
- Hymenoptera Hymenoptera (Athalia rosae), Japanese ant (Athalia japonica) and other Hymenoptera (Tenthredinidae); Fire ant (Solenopsis invicta), Red imported fire ant (Solenopsis geminata) and other genus Tofushiari (Solenopsis geminata) Reef cutting ant (Atta capiguara) and other Hymenoptera (Atta spp.), Fire ant (Acromyrmex spp.), Sashihariari (Paraponera clavata), Luriari (Ochetellus glaber), Fire ant (Monomorium pharaonis), Argentine , Fire ant (Formica japonica), Amime ant (Pristomyrmex punctutus), Fire ant (Pheidole noda), Fire ant (Pheidole megacephala), Fire ant (Camponotus japonicus
- Termites (Blattodea): Termite family (Ectobiidae) such as termites (Blattella germanica); termites (Periplaneta fuliginosa), termites (Periplaneta aamericana), termites (Periplaneta australasiae), termites (periplaneta, termites) Blatta orientalis and other termites (Blattidae); Yamato termites (Reticulitermes speratus), termites (Coptotermes formosanus), American termites (Incisitermes minor), termites (Cryptotermes termites), termites (Cryptotermes termites), termites (Cryptotermes termites) Neotermes koshunensis, Satsuma termites (Glyptotermes satsumensis), Nakajima termites (Glyptotermes nakajimai), Catan termites (Glyptotermes fuscus), termites (Hodotermopsis
- Fleas Pulex spp. Such as human fleas (Pulex irritans), Ctenocephalides felis such as cat fleas, Ctenocephalides spp. Such as dog fleas (Ctenocephalides canis), Keops fleas. Xenopsylla spp. Such as Xenopsylla cheopis, Tunga spp. Such as Tunga penetrans, Echidnophaga gallinacea such as Echidnophaga gallinacea, Echidnophaga spp. ) Etc. (Nosopsyllus spp.).
- Pulex spp. Such as human fleas (Pulex irritans), Ctenocephalides felis such as cat fleas, Ctenocephalides spp. Such as dog fleas (Ctenocephalides canis), Keops fleas. Xenopsylla spp. Such as Xenopsylla
- Psocodea Head lice (Pediculus humanus capitis) and other genus Pediculus (Pediculus spp.); Crab lice (Pthirus pubis) and other genus Phtirus (Phtirus spp.); Crab lice (Haematopinus eurysternus), etc. Haematopinus spp.; Bovicola spp., Bovicola spp., Bovicola spp., Damalinia forficula, etc. Damalinia forficula, etc. Linognathus spp. Such as head louse (Linognathus ovillus); Solenopotes spp.
- Solenopotes spp. Such as Kebukaushijirami (Solenopotes capillatus); Menopon (Menopon) Cummingsia spp.; Trinoton spp.; Trichodectes spp. Such as Inuhajirami (Trichodectes canis); Felicola subrostratus and other Felicola spp.
- Thysanura Lepismatidae such as Ctenolepisma villosa and Lepisma saccharina.
- Tick (Acari): Nami spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), Mitsuyubinami spider mite (Tetranychus evansi), Panonychus citri, Panonychus ulmi, Panonychus ulmi, Panonychus ulmi, Panonychus ulmi, Panonychus ulmi ); Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Panonychus ulnaris, Panonychus ulata, Panonychus ulata Aculus convincedendali, Aceria diospyri, Aceria tosichella, Shevtchenkella sp., Etc.
- Fushidani family Eriophyidae); Chano dust mite (Polyphagotarsonemus latus), etc. Dust mite family (Tarsonemidae), etc. Family (Tenui palpidae); Spider mite (Tuckerellidae); Panonychus ulnaris (Haemaphysalis longicornis), Panonychus ulva (Haemaphysalis flava), Yamato tick (Haemaphysalis japonica), Tsuriganechi tick (Haemaphysalis campanulata) Dermacentor taiwanensis), Rocky Mountain Wood Chick (Dermacentor andersoni), Amimekakumadani (Dermacentor reticulatus), Yamato tick (Ixodes ovatus), Schultz tick (Ixodes persulcatus), Black legd tick (Ixodes scapularis), Western black tick (Ixodes pacificus
- Dermatophagoides farinae, Dermatophagoides pteronyssinus and other dust mites (Pyroglyphidae); Hosotsumedani (Cheyletus eruditus), Kuwagatatsumedani (Cheyletus malaccensis), Mite (Cheyletus malaccensis) Cheyletidae); itch mite (Psoroptes ovis), itch mite (Psoroptes equi), Knemidocoptes mutans, itch mite (Otodectes cynotis), genus Chorioptes itch mite (Chorioptes spp.), Etc.
- Spider order (Araneae): Cheiracanthium japonicum and other spiders (Eutichuridae); Latrodectus hasseltii and other spiders (Theridiidae).
- Polydesmida Polydesmida (Paradoxosomatidae) such as Polydesmida (Oxidus gracilis) and Nedyopus tambanus.
- Isopoda Armadillidium vulgare and other Armadillidium vulgare.
- Chilopoda Centipede (Scutigeridae) such as Thereuonema hilgendorfi; Scolopendridae (Scolopendra subspinipes); Scolopendridae (Bothropolys rugosus) and other centipedes (Bothropolys rugosus).
- Gastropoda Keelback slug (Limax marginatus), Keelback slug (Limax flavus) and other snails (Limacidae); Austropeplea occidentalis (Meghimatium bilineatum) and other snails (Philomycidae); Apple snails (Ampullariidae); Monoaragai (Lymnaeidae) such as Austropeplea ollula.
- Aphelenchoididae such as Aphelenchoides besseyi; Pratylenchus coffeae, Pratylenchus brachyurus, Pratylenchus radinus, Pratylenchus Root-knot nematode, Pratylenchus nematode, Root-knot nematode, Root-knot nematode, Root-knot nematode, Root-knot nematode, Root-knot nematode, Root-knot nematode, Root-knot nematode, Root-knot nematode, etc.
- Lenkus family (Pratylenchidae); Javanese root-knot nematode (Meloidogyne javanica), Root-knot nematode (Meloidogyne incognita), guava root-knot nematodes (Meloidogyne enterolobii), Root-knot nematode (Meloidogyne enterolobii), Root-knot nematode (Meloidogyne) Heteroderidae such as Globodera rostochiensis, Globodera pallida; Hoplara imidae such as Rothelenchulus reniformis; Nothotylenchus acris, Namiku nematode, etc.
- Tylenchulidae such as Tylenchulus semipenetrans
- Longidoridae such as grape root-knot (Xiphinema index)
- Trichodoridae Trichodoridae
- Bursaphelenchus Aferenx family Parasitaphelenchidae
- Harmful arthropods such as harmful insects and mites, harmful mollusks and harmful nematodes have reduced drug sensitivity or drug resistance to pesticides, acaricides, mollusks and nematodes. It may be a developed harmful insect, a harmful arthropod such as a harmful mite, a harmful mollusk and a harmful nematode.
- an effective amount of the compound or composition A of the present invention is applied directly to the pest and / or to the habitat of the pest (plant, soil, house, animal, etc.). It is done by.
- the pest control method of the present invention include foliage treatment, soil treatment, root treatment, shower treatment, smoke treatment, water surface treatment and seed treatment.
- the compound or composition A of the present invention is usually mixed with an inert carrier such as a solid carrier, a liquid carrier, or a gaseous carrier, and if necessary, a surfactant or other formulation auxiliary is added to the emulsion.
- an inert carrier such as a solid carrier, a liquid carrier, or a gaseous carrier
- a surfactant or other formulation auxiliary is added to the emulsion.
- These preparations may be processed and used as mosquito coils, electric mosquito repellent mats, liquid mosquito repellent preparations, smoke agents, fumigants, and sheet preparations. These preparations usually contain 0.01 to 95 by weight of the compound or composition A of the present invention.
- Solid carriers used in the formulation include, for example, clays (kaolin clay, diatomaceous earth, bentonite, acidic white clay, etc.), dry silica, wet silica, talc, ceramics, and other inorganic minerals (serisite, quartz, sulfur).
- liquid carrier examples include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic charcoal.
- alcohols methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.
- ketones acetone, methyl ethyl ketone, cyclohexanone, etc.
- Hydrogens toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylyl ethane, methylnaphthalene, etc.
- aliphatic hydrocarbons hexane, cyclohexane, kerosene, light oil, etc.
- esters ethyl acetate, butyl acetate, isopropyl myristate, etc.
- nitriles acetritale, isobutyronitrile, etc.
- ethers diisopropyl ether, 1,4-dioxane, 1,2-dimethoxy, etc. Ethan, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether
- gaseous carrier examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide gas.
- surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether and polyethylene glycol fatty acid ester, and anionic surfactants such as alkyl sulfonates, alkyl benzene sulfonates and alkyl sulfates. Examples include ionic surfactants.
- Other pharmaceutical aids include fixatives, dispersants, colorants, stabilizers, etc., specifically, for example, casein, gelatin, saccharides (phenols, arabic gum, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, etc.
- Synthetic water-soluble polymers polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.
- acidic isopropyl phosphate 2,6-di-tert-butyl-4-methylphenol, BHA (2-tert-butyl-4-methoxyphenol) And 3-tert-butyl-4-methoxyphenol).
- Nimbus registered trademark
- Assist registered trademark
- Aureo registered trademark
- Iharol registered trademark
- Silwet L-77 registered trademark
- BreakThru registered trademark
- SundanceII registered trademark
- Induce registered trademark
- Penetrator registered trademark
- AgriDex registered trademark
- Lutensol A8 registered trademark
- NP-7 registered trademark
- Triton registered trademark
- Nufilm registered trademark
- Emulgator NP7 registered trademark
- Emulad trademark registered trademark
- TRITONX45 registered trademark
- AGRAL90 registered trademark
- AGROTIN registered trademark
- ARPON registered trademark
- EnSprayN registered trademark
- BANOLE registered trademark
- Examples of the base material of the resin preparation include vinyl chloride-based polymers and polyurethanes, and phthalates (dimethyl phthalate, dioctyl phthalate, etc.) and adipates may be used as necessary for these base materials.
- a plasticizer such as phthalate or phthalate may be added.
- the resin preparation is obtained by kneading the compound in the base material using a normal kneading device and then molding it by injection molding, extrusion molding, press molding or the like, and if necessary, further through steps such as molding and cutting. It can be processed into resin preparations such as plate, film, tape, net, and string.
- These resin formulations are processed, for example, as animal collars, animal ear tags, sheet formulations, drawstrings, and horticultural struts.
- the base material of the poison bait include grain flour, vegetable oil, sugar, crystalline cellulose and the like, and if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguairetinic acid, dehydroacetic acid and the like.
- antioxidants such as dibutylhydroxytoluene and nordihydroguairetinic acid, dehydroacetic acid and the like.
- Preservatives, preventive agents for children and pets such as pepper powder, cheese flavors, onion flavors, pest-attracting flavors such as peanut oil, etc. are added.
- examples of the plant include whole plant, stem and leaf, flower, ear, fruit, trunk, branch, canopy, seed, vegetative reproduction organ and seedling.
- the vegetative reproduction organ means a plant root, stem, leaf, etc. that has the ability to grow when the part is separated from the main body and placed in the soil.
- vegetative reproductive organs include tuberous root, creeping root, bulb, bulb, tuber, rhizome, and stolon. , Rhizophore, stem fragments (cane cuttings), bulbs (propagule) and vines (vine cutting).
- the stolon is sometimes called a runner, and the propagule is also called a pearl bud, and is divided into a granuloma (broad bud) and a scale bud (bulbil).
- Tsuru means seedlings (collective term for leaves and stems, shoot) of sweet potatoes, yams, etc. Bulbs, bulbs, tubers, rhizomes, stem fragments, root-bearing bodies or tubers are also collectively referred to as bulbs. Cultivation of potatoes begins by planting tubers in the soil, but the tubers used are commonly referred to as seed potatoes.
- the compound or composition A of the present invention can be applied to the soil before or after planting a plant.
- a method of applying an effective amount a method of applying an effective amount of the compound or composition A of the present invention to the rhizosphere of a crop to be protected from damage such as feeding by harmful arthropods, and a method of applying an effective amount of the compound or composition A from the root to the inside of the plant Examples thereof include a method in which an effective amount of the compound or composition A of the present invention is permeated and transferred to control harmful arthropods that feed on plants.
- planting hole treatment planting hole spraying, planting hole treatment soil mixing
- stock source treatment stock source spraying, stock source soil mixing, stock source irrigation, seedling raising period latter half stock source treatment
- planting groove Treatment planting ditch, mixing of soil with planting ditch
- streak treatment spraying of streak, mixing of streak soil, spraying of growing season
- streak treatment at seeding spraying of crop at seeding, mixing of cropping soil at seeding
- Full treatment whole soil spraying, full soil mixing
- side strip treatment water surface treatment (water surface application, after flooding water surface application), other soil spray treatment (growth season granule foliar spray, under tree canopy or around the main trunk)
- irrigation treatments irrigation, seedling raising period irrigation, chemical injection treatment, ground irrigation, chemical drip irrigation, chemigation
- Nursery box treatment planting box spraying, nursery box irrigation, nursery box chemical flooding
- Examples of the seed treatment include treatment of the compound or composition A of the present invention on seeds or vegetative reproduction organs. Specifically, for example, a suspension of the compound or composition A of the present invention is atomized to form a seed surface. Alternatively, a spray treatment of spraying the surface of the vegetative reproduction organ, a smear treatment of applying the compound or composition A of the present invention to the seed or the vegetative reproduction organ, or an immersion treatment of immersing the seed in the chemical solution of the compound or composition A of the present invention for a certain period of time , A method of coating seeds or vegetative reproduction organs with a carrier containing the compound of the present invention or composition A (film coating treatment, pellet coating treatment, etc.). Examples of the vegetative reproduction organs include seed potatoes.
- the composition A When the composition A is processed into seeds or vegetative reproduction organs, the composition A can be processed into seeds or vegetative reproduction organs as one preparation, or the composition A can be divided into a plurality of different preparations and seeds. Alternatively, it can be processed into vegetative reproduction organs.
- a method for treating the composition A as a plurality of different preparations in a plurality of times for example, a preparation containing only the compound of the present invention as an active ingredient is treated, the seeds or vegetative reproduction organs are air-dried, and then the present ingredient is treated.
- the seed or vegetative reproduction organ holding the compound or composition A of the present invention in the present invention means a state in which the compound or composition A of the present invention is attached to the surface of the seed or vegetative reproduction organ. ..
- the seed or vegetative reproduction organ holding the above-mentioned compound or composition A of the present invention is other than the compound or composition A of the present invention before and after the compound or composition A of the present invention is attached to the seed or vegetative reproduction organ. Materials may be attached.
- the layer is composed of one layer or a plurality of layers.
- each layer is a layer containing one or more active ingredients, or is composed of a layer containing one or more active ingredients and a layer not containing the active ingredient.
- the seed or vegetative reproduction organ carrying the compound or composition A of the present invention is obtained, for example, by applying a preparation containing the compound or composition A of the present invention to the seed or vegetative reproduction organ by the above-mentioned seed treatment method. be able to.
- the application rate thereof is usually 1 to 10000 g per 10,000 m 2 .
- the amount of the compound of the present invention is usually in the range of 0.001 to 100 g per 1 kg of seeds or vegetative reproduction organs.
- the compound or composition A of the present invention is formulated in an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water so that the concentration of the active ingredient is 0.01 to 10000 ppm, and the granules are applied.
- the agent, powder, etc. are usually applied as they are.
- It can also be treated by wrapping a resin preparation processed into a sheet or string around the crop, stretching it near the crop, or laying it on the soil at the root of the plant.
- the application rate is usually the amount of the compound of the present invention per 1 m 2 of the treated area when treated on a surface.
- the amount is 0.01 to 1000 mg
- the amount of the compound of the present invention per 1 m 3 of the treatment space when treated in a space is usually 0.01 to 500 mg.
- the compound or composition A of the present invention is formulated in an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the concentration of the active ingredient becomes 0.1 to 10000 ppm, and applied as an oil preparation. , Aerosol, smoke, poison bait, etc. are applied as they are.
- the compound or composition A of the present invention can be used as a control agent for harmful arthropods in agricultural lands such as fields, paddy fields, lawns and orchards.
- agricultural lands such as fields, paddy fields, lawns and orchards.
- plants include the following.
- the above plants also include genetically modified crops.
- Me represents a methyl group
- Et represents an ethyl group
- Pr represents a propyl group
- Bu represents a butyl group
- Pen represents a pentyl group
- i-Pr represents an isopropyl group
- i. -Bu represents an isobutyl group
- c-Pr represents a cyclopropyl group
- c-Bu represents a cyclobutyl group
- c-Pen represents a cyclopentyl group
- c-Hex represents a cyclohexyl group
- Ph represents a phenyl group.
- LCMS compound liquid chromatography / mass spectrometry
- MS mass spectrometry
- Reference manufacturing example 1 Methyl (Z) -2- (5-bromo-2-methylphenoxy) -3-methoxyacrylate (manufactured by the method described in International Publication No. 2001/000562) 20.0 g, bis (pinacolato) diboron 20.2 g , [1,1'-Bis (diphenylphosphino) ferrocene]
- a mixture of 2.43 g of palladium (II) dichloride, 19.5 g of potassium acetate and 250 mL of DMSO was stirred at 80 ° C. for 10 hours. Water was added to the obtained mixture, and the mixture was extracted with ethyl acetate.
- Reference manufacturing example 2 At room temperature, 0.43 g of metachloroperbenzoic acid (including 70% pure, 30% water) was added to a mixture of 0.50 g of Intermediate 1, 20 mL of ethanol, 20 mL of acetonitrile and 20 mL of water, and the mixture was stirred for 3 hours. A saturated aqueous sodium thiosulfate solution and a saturated aqueous ammonium chloride solution were sequentially added to the obtained mixture, and the mixture was stirred for 1 hour. The resulting mixture was concentrated under reduced pressure and extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
- Reference manufacturing example 3 A mixture of 0.50 g of methyl 2- (5-hydroxy-2-methylphenoxy) acetate, 0.82 g of triphenylphosphine, 0.39 mL of benzyl alcohol and 10 mL of chloroform in a mixture of bis (2-methoxyethyl) azodicarboxy at 0 ° C. 0.78 g of rat was added and stirred at room temperature for 22 hours. A saturated aqueous sodium hydrogen carbonate solution was added to the obtained mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
- Equation (1b1) Among the compounds shown by, E is the compound shown below.
- Reference manufacturing example 4 At room temperature, add 0.29 g of N-methyl-N-phenylcarbamoyl chloride to a mixture of 0.30 g of methyl 2- (5-hydroxy-2-methylphenoxy) acetate, 0.28 g of potassium carbonate and 10 mL of DMF, and stir for 3 hours. did. A saturated aqueous solution of ammonium chloride was added to the obtained mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.47 g of Intermediate C2 represented by the following formula.
- Equation (1d1) Among the compounds shown by, E is the compound shown below.
- Reference manufacturing example 7 A mixture of 108.43 g of Intermediate 4, 5.52 g of cobalt (II) chloride and 1084 mL of methanol was cooled to ⁇ 54 ° C., 40.35 g of sodium borohydride was added thereto, and the mixture was stirred at ⁇ 24 ° C. for 6 hours. A 10% aqueous ammonium chloride solution was added to the obtained mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 93.91 g of Intermediate 5 represented by the following formula.
- Reference manufacturing example 8 A mixture of 3.80 g of Intermediate 5 and 137 mL of THF was cooled to ⁇ 72 ° C., 27 mL of lithium diisopropylamide (1.08 M hexane-THF solution) was added thereto, and the mixture was stirred at ⁇ 66 ° C. for 30 minutes. 7.10 g of methyl formate was added to the obtained mixture, and the mixture was stirred at ⁇ 63 ° C. for 1 hour. A 10% aqueous sodium hydrogensulfate solution was added to the obtained mixture, and the mixture was extracted with ethyl acetate.
- Reference manufacturing example 8-1 Reference The compounds produced according to Production Example 8 and their physical property values are shown below.
- Equation (1a1) A compound in which E, R 1 and L are any combination shown in [Table 1-1] to [Table 1-6].
- Compound 80 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.30 (1H, s), 7.29-7.25 (2H, m), 7.21-7.15 (3H, m), 7.02 (1H, d), 6.43 (1H) , dd), 6.31 (1H, d), 3.91-3.87 (2H, m), 3.85 (3H, s), 3.69 (3H, s), 2.70-2.63 (2H, m), 2.26 (3H, s), 1.80-1.75 (4H, m).
- Production Example 2-1 The compounds produced according to Production Example 2 and their physical property values are shown below. A compound in which E, R 1 and L are any combination shown in [Table 2-1] in the compound represented by the formula (1a1).
- Production Example 3-1 The compounds produced according to Production Example 3 and their physical property values are shown below.
- the compound represented by the formula (1a1) a compound in which E, R 1 and L are any combination shown in [Table 3-1].
- Production Example 4-1 The compounds produced according to Production Example 4 and their physical property values are shown below. A compound in which E, R 1 and L are any combination shown in [Table 4-1] among the compounds represented by the formula (1a1).
- Production Example 5-1 The compounds produced according to Production Example 5 and their physical property values are shown below.
- the compound represented by the formula (1a1) a compound in which E, R 1 and L are any combination shown in [Table 5-1].
- Production Example 6-1 The compounds produced according to Production Example 6 and their physical property values are shown below.
- the compound represented by the formula (1a1) a compound in which E, R 1 and L are any combination shown in [Table 6-1].
- Compound 69 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.33 (1H, s), 7.14 (1H, d), 6.83 (1H, dd), 6.69 (1H, d), 3.88 (3H, s), 3.71 (3H, s), 2.90 (6H, s), 2.32 (3H, s).
- Compound 70 of the present invention 1 H-NMR (CDCl 3 ) ⁇ : 7.33 (1H, s), 7.13 (1H, d), 6.81 (1H, dd), 6.67 (1H, d), 3.87 (3H, s), 3.71 (3H, s), 3.30 (4H, q), 2.32 (3H, s), 1.16 (6H, t).
- Group X Et, Pr, i-Pr, (CH 2 ) 3 CH 3 , CH 2 CH (CH 3 ) 2 , CH (CH 3 ) CH 2 CH 3 , C (CH 3 ) 3 , CH 2 c-Pr , (CH 2 ) 4 CH 3 , (CH 2 ) 2 CH (CH 3 ) 2 , CH (CH 3 ) (CH 2 ) 2 CH 3 , CH (CH 2 CH 3 ) CH 2 CH 3 , CH 2 CH (CH 2 CH 3 ) CH 3 ) CH 2 CH 3 , C (CH 3 ) 2 CH 2 CH 3 , CH 2 C (CH 3 ) 3 , CH 2 c-Bu, CH 2 c-Pen, CH 2 c-Hex, (CH 2 ) 2 c-Pr, (1-methylcyclopropyl) methyl, (2-methylcyclopropyl) methyl, 1-cyclopropylethyl, (CH 2 ) 3 c-Pr, (CH 2 ) 5 CH 3 ,
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 1 is any substituent selected from the group X (hereinafter, referred to as the compound group SX2). ..
- R 1 is a methyl group
- L is CH 2
- R X 1 is any substituent selected from the group X (hereinafter, referred to as compound group SX3). ..
- R 1 is a chlorine atom
- L is CH 2
- R X 1 is any substituent selected from the group X (hereinafter, referred to as compound group SX4). ..
- Combination A comprises substituents ZA1 to ZA311.
- the substituent number ZA2, R X2 is a methyl group
- R X3, R X4, R X5 and R X6 means a combination of a hydrogen atom.
- R 1 is a chlorine atom
- L is an oxygen atom
- m is 1
- R X2 , R X3 , R X4 , R X5 and R X 6 are described in Combination A.
- a compound that is a combination of any of the above hereinafter referred to as compound group SX6).
- R 1 is a methyl group
- L is CH 2
- m is 1
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- a compound that is a combination of any of the above hereinafter referred to as compound group SX7).
- R 1 is a chlorine atom
- L is CH 2
- m is 1
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- a compound that is a combination of any of the above hereinafter referred to as compound group SX8).
- R 1 is a methyl group
- L is an oxygen atom
- m is 2
- R X2 , RX3 , RX4 , RX5 and RX6 are described in Combination A.
- a compound that is a combination of any of the above hereinafter referred to as compound group SX9).
- R 1 is a chlorine atom
- L is an oxygen atom
- m is 2
- R X2 , R X3 , R X4 , R X5 and R X 6 are described in Combination A.
- a compound that is a combination of any of the above hereinafter referred to as compound group SX10).
- R 1 is a methyl group
- L is CH 2
- m is 2
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- a compound that is a combination of any of the above hereinafter referred to as compound group SX11).
- R 1 is a chlorine atom
- L is CH 2
- m is 2
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- a compound that is a combination of any of the above hereinafter referred to as compound group SX12).
- R 1 is a methyl group
- L is an oxygen atom
- m is 3
- R X2 , RX3 , RX4 , RX5 and RX6 are described in Combination A.
- a compound that is a combination of any of the above hereinafter referred to as compound group SX13).
- R 1 is a chlorine atom
- L is an oxygen atom
- m is 3
- R X2 , R X3 , R X4 , R X5 and R X 6 are described in Combination A.
- a compound that is a combination of any of the above hereinafter referred to as compound group SX14).
- R 1 is a methyl group
- L is CH 2
- m is 3
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- a compound that is a combination of any of the above hereinafter referred to as compound group SX15).
- R 1 is a chlorine atom
- L is CH 2
- m is 3
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- a compound that is a combination of any of the above hereinafter referred to as compound group SX16).
- Combination B comprises substituents ZB1 to ZB1145.
- Substituent numbers ZB1 to ZB1145 are substituents R corresponding to the structure of G and the structure of G in the compound represented by the formula (1C), the compound represented by the formula (2C), and the compound represented by the formula (3C). It represents a combination of X7 , R X8 , R X9 and R X10 , and is hereinafter referred to as [substituent number; G, R X7 , R X8 , R X9 , R X10 ].
- the substituent number ZB2 is G1, R X7 is a methyl group, R X8, R X9 and R X10 is meant the combination of a hydrogen atom.
- R 1 is a chlorine atom
- L is an oxygen atom
- m is 1
- X9 and R X10 is any combination according to the combination B compound (hereinafter referred to as compound group SX18).
- R 1 is a methyl group
- L is CH 2
- m is 1
- X9 and R X10 is any combination according to the combination B compound (hereinafter referred to as compound group SX19).
- R 1 is a chlorine atom
- L is CH 2
- m is 1
- R X7 , RX8 , R corresponding to the structure of G and the structure of G.
- SX20 A compound in which X9 and RX10 are any combination described in Combination B (hereinafter referred to as compound group SX20).
- R 1 is a methyl group
- L is an oxygen atom
- m is 2
- X9 and R X10 is any combination according to the combination B compound (hereinafter referred to as compound group SX21).
- R 1 is a chlorine atom
- L is an oxygen atom
- m is 2
- X9 and R X10 is any combination according to the combination B compound (hereinafter referred to as compound group SX22).
- R 1 is a methyl group
- L is CH 2
- m is 2
- X9 and R X10 is any combination according to the combination B compound (hereinafter referred to as compound group SX23).
- R 1 is a chlorine atom
- L is CH 2
- m is 2
- X9 and R X10 is any combination according to the combination B compound (hereinafter referred to as compound group SX24).
- R 1 is a methyl group
- L is an oxygen atom
- m is 3
- X9 and R X10 is any combination according to the combination B compound (hereinafter referred to as compound group SX25).
- R 1 is a chlorine atom
- L is an oxygen atom
- m is 3
- X9 and R X10 is any combination according to the combination B compound (hereinafter referred to as compound group SX26).
- R 1 is a methyl group
- L is CH 2
- m is 3
- X9 and R X10 is any combination according to the combination B compound (hereinafter referred to as compound group SX27).
- R 1 is a chlorine atom
- L is CH 2
- m is 3
- X9 and R X10 is any combination according to the combination B compound (hereinafter referred to as compound group SX28).
- Group Y Me, Ph, CH 2 Ph, (CH 2 ) 2 Ph, (CH 2 ) 3 Ph, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl.
- Group Z A group consisting of 1-pyrrolidinyl, 1-piperidinyl, and 4-morpholinyl.
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 11 is a substituent selected from Group X, Group Y and Group Z (hereinafter,).
- Compound group SX30 is a substituent selected from Group X, Group Y and Group Z (hereinafter,).
- R 1 is a methyl group
- L is CH 2
- R X 11 is a substituent selected from groups X, Y, and Z (hereinafter referred to as a compound).
- Compound group SX31 is a substituent selected from groups X, Y, and Z (hereinafter referred to as a compound).
- R 1 is a chlorine atom
- L is CH 2
- R X 11 is a substituent selected from Group X, Group Y and Group Z (hereinafter,).
- Compound group SX32 is a substituent selected from Group X, Group Y and Group Z (hereinafter,).
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 12 is a substituent selected from groups X and Y (hereinafter, compound group SX34). ).
- R 1 is a methyl group
- L is CH 2
- R X 12 is a substituent selected from groups X and Y (hereinafter, compound group SX35). ).
- R 1 is a chlorine atom
- L is CH 2
- R X 12 is a substituent selected from groups X and Y (hereinafter, compound group SX36). ).
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 13 is a hydrogen atom
- R X 14 is any substituent selected from the group X and the group Y.
- a compound (hereinafter referred to as compound group SX38).
- R 1 is a methyl group
- L is CH 2
- R X 13 is a hydrogen atom
- R X 14 is any substituent selected from the group X and the group Y.
- a compound (hereinafter referred to as compound group SX39).
- R 1 is a chlorine atom
- L is CH 2
- R X 13 is a hydrogen atom
- R X 14 is any substituent selected from group X and group Y.
- a compound (hereinafter referred to as compound group SX40).
- R 1 is a methyl group
- L is an oxygen atom
- R X13 is a methyl group
- R X14 is selected from the group X and the group Y
- SX41 A compound (hereinafter referred to as compound group SX41).
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 13 is a methyl group
- R X 14 is any substituent selected from the group X and the group Y.
- a compound (hereinafter referred to as compound group SX42).
- R 1 is a methyl group
- L is CH 2
- R X13 is a methyl group
- R X14 is selected from the group X and the group Y
- SX43 A compound (hereinafter referred to as compound group SX43).
- R 1 is a chlorine atom
- L is CH 2
- R X 13 is a methyl group
- R X 14 is any substituent selected from group X and group Y.
- a compound (hereinafter referred to as compound group SX44).
- R 1 is a methyl group
- L is an oxygen atom
- R X 13 is an ethyl group
- R X 14 is any substituent selected from the group X and the group Y.
- a compound (hereinafter referred to as compound group SX45).
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 13 is an ethyl group
- R X 14 is any substituent selected from the group X and the group Y.
- a compound (hereinafter referred to as compound group SX46).
- R 1 is a methyl group
- L is CH 2
- R X 13 is an ethyl group
- R X 14 is any substituent selected from group X and group Y.
- a compound (hereinafter referred to as compound group SX47).
- R 1 is a chlorine atom
- L is CH 2
- R X 13 is an ethyl group
- R X 14 is any substituent selected from group X and group Y.
- a compound (hereinafter referred to as compound group SX48).
- a compound that is a combination of the above hereinafter referred to as compound group SX49).
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 13 is a hydrogen atom
- R X 2 , R X 3 , R X 4 , R X 5 and R X 6 are combined A.
- Compounds that are any combination described in hereinafter referred to as compound group SX50).
- R 1 is a methyl group
- L is CH 2
- R X 13 is a hydrogen atom
- R X 2 , R X 3 , R X 4 , R X 5 and R X 6 are combined A.
- Compounds that are any combination described in hereinafter referred to as compound group SX51).
- R 1 is a chlorine atom
- L is CH 2
- R X 13 is a hydrogen atom
- R X 2 , R X 3 , R X 4 , R X 5 and R X 6 are combined A.
- Compounds that are any combination described in hereinafter referred to as compound group SX52).
- R 1 is a methyl group
- L is an oxygen atom
- R X13 is a methyl group
- R X2, R X3, R X4, R X5 and R X6 combinations A Compounds that are any combination described in (hereinafter referred to as compound group SX53).
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 13 is a methyl group
- R X 2 , R X 3 , R X 4 , R X 5 and R X 6 are combined A.
- Compounds that are any combination described in hereinafter referred to as compound group SX54).
- R 1 is a methyl group
- L is CH 2
- R X13 is a methyl group
- R X2, R X3, R X4, R X5 and R X6 combinations A Compounds that are any combination described in (hereinafter referred to as compound group SX55).
- R 1 is a chlorine atom
- L is CH 2
- R X 13 is a methyl group
- R X 2 , R X 3 , R X 4 , R X 5 and R X 6 are combined A.
- Compounds that are any combination described in hereinafter referred to as compound group SX56).
- R 1 is a methyl group
- L is an oxygen atom
- R X13 is an ethyl group
- R X2, R X3, R X4, R X5 and R X6 combinations A Compounds that are any combination described in (hereinafter referred to as compound group SX57).
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 13 is an ethyl group
- R X 2 , R X 3 , R X 4 , R X 5 and R X 6 are combined A.
- Compounds that are any combination described in hereinafter referred to as compound group SX58).
- R 1 is a methyl group
- L is CH 2
- R X 13 is an ethyl group
- R X 2 , R X 3 , R X 4 , R X 5 and R X 6 are combined A.
- Compounds that are any combination described in hereinafter referred to as compound group SX59).
- R 1 is a chlorine atom
- L is CH 2
- R X 13 is an ethyl group
- R X 2 , R X 3 , R X 4 , R X 5 and R X 6 are combined A.
- Compounds that are any combination described in hereinafter referred to as compound group SX60).
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 15 is a hydrogen atom
- R X 16 is any substituent selected from the group X and the group Y.
- a compound (hereinafter referred to as compound group SX62).
- R 1 is a methyl group
- L is CH 2
- R X 15 is a hydrogen atom
- R X 16 is any substituent selected from groups X and Y.
- a compound (hereinafter referred to as compound group SX63).
- R 1 is a chlorine atom
- L is CH 2
- R X 15 is a hydrogen atom
- R X 16 is any substituent selected from the group X and the group Y.
- a compound (hereinafter referred to as compound group SX64).
- R 1 is a methyl group
- L is an oxygen atom
- R X 15 is a methyl group
- R X 16 is any substituent selected from the group X and the group Y.
- a compound (hereinafter referred to as compound group SX65).
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 15 is a methyl group
- R X 16 is any substituent selected from the group X and the group Y.
- a compound (hereinafter referred to as compound group SX66).
- R 1 is a methyl group
- L is CH 2
- R X 15 is a methyl group
- R X 16 is any substituent selected from group X and group Y.
- a compound (hereinafter referred to as compound group SX67).
- R 1 is a chlorine atom
- L is CH 2
- R X 15 is a methyl group
- R X 16 is any substituent selected from group X and group Y.
- Compound (hereinafter referred to as compound group SX68).
- R 1 is a chlorine atom
- L is an oxygen atom
- the compounds are any of the substituents R X17 is selected from the group X and the group Y (hereinafter, compounds SX70 ).
- R 1 is a methyl group
- L is CH 2
- R X 17 is any substituent selected from group X and group Y (hereinafter, compound group SX71). ).
- R 1 is a chlorine atom
- L is CH 2
- R X 17 is a substituent selected from Group X and Group Y (hereinafter, Compound Group SX72). ).
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 18 is a hydrogen atom
- R X 19 is any substituent selected from the group X and the group Y.
- a compound (hereinafter referred to as compound group SX74).
- R 1 is a methyl group
- L is CH 2
- R X 18 is a hydrogen atom
- R X 19 is any substituent selected from the group X and the group Y.
- a compound (hereinafter referred to as compound group SX75).
- R 1 is a chlorine atom
- L is CH 2
- R X 18 is a hydrogen atom
- R X 19 is any substituent selected from group X and group Y.
- a compound (hereinafter referred to as compound group SX76).
- R 1 is a methyl group
- L is an oxygen atom
- R X 18 is a methyl group
- R X 19 is any substituent selected from group X and group Y.
- Compound hereinafter referred to as compound group SX77).
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 18 is a methyl group
- R X 19 is any substituent selected from the group X and the group Y.
- a compound (hereinafter referred to as compound group SX78).
- R 1 is a methyl group
- L is CH 2
- R X 18 is a methyl group
- R X 19 is any substituent selected from group X and group Y.
- a compound (hereinafter referred to as compound group SX79).
- R 1 is a chlorine atom
- L is CH 2
- R X 18 is a methyl group
- R X 19 is any substituent selected from group X and group Y.
- a compound (hereinafter referred to as compound group SX80).
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 1 is any substituent selected from the group X.
- R 1 is a methyl group
- L is CH 2
- R X 1 is any substituent selected from the group X.
- R 1 is a chlorine atom
- L is CH 2
- R X 1 is any substituent selected from the group X.
- R 1 is a chlorine atom
- L is an oxygen atom
- m is 1
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- R 1 is a methyl group
- L is CH 2
- m is 1
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- R 1 is a chlorine atom
- L is CH 2
- m is 1
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- R 1 is a methyl group
- L is an oxygen atom
- m is 2
- R X2 , RX3 , RX4 , RX5 and RX6 are described in Combination A.
- R 1 is a chlorine atom
- L is an oxygen atom
- m is 2
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- R 1 is a methyl group
- L is CH 2
- m is 2
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- R 1 is a chlorine atom
- L is CH 2
- m is 2
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- R 1 is a methyl group
- L is an oxygen atom
- m is 3
- R X2 , RX3 , RX4 , RX5 and RX6 are described in Combination A.
- R 1 is a chlorine atom
- L is an oxygen atom
- m is 3
- R X2 , R X3 , R X4 , R X5 and R X 6 are described in Combination A.
- R 1 is a methyl group
- L is CH 2
- m is 3
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- R 1 is a chlorine atom
- L is CH 2
- m is 3
- R X2 , R X3 , R X4 , R X5 and R X6 are described in Combination A.
- R 1 is a chlorine atom
- L is an oxygen atom
- m is 1, and the substituents RX7 , RX8 , R corresponding to the structure of G and the structure of G.
- X9 and RX10 are any combination described in Combination B.
- R 1 is a methyl group
- L is CH 2
- m is 1
- X9 and RX10 are any combination described in Combination B.
- R 1 is a chlorine atom
- L is CH 2
- m is 1
- X9 and RX10 are any combination described in Combination B.
- R 1 is a methyl group
- L is an oxygen atom
- m is 2
- X9 and RX10 are any combination described in Combination B.
- R 1 is a chlorine atom
- L is an oxygen atom
- m is 2
- X9 and RX10 are any combination described in Combination B.
- R 1 is a methyl group
- L is CH 2
- m is 2
- X9 and RX10 are any combination described in Combination B.
- R 1 is a chlorine atom
- L is CH 2
- m is 2
- X9 and RX10 are any combination described in Combination B.
- R 1 is a methyl group
- L is an oxygen atom
- m is 3
- X9 and RX10 are any combination described in Combination B.
- R 1 is a chlorine atom
- L is an oxygen atom
- m is 3
- X9 and RX10 are any combination described in Combination B.
- R 1 is a methyl group
- L is CH 2
- m is 3
- X9 and RX10 are any combination described in Combination B.
- R 1 is a chlorine atom
- L is CH 2
- m is 3
- X9 and RX10 are any combination described in Combination B.
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 11 is a substituent selected from Group X, Group Y and Group Z.
- R 1 is a methyl group
- L is CH 2
- R X 11 is any substituent selected from group X, group Y and group Z.
- R 1 is a chlorine atom
- L is CH 2
- R X 11 is a substituent selected from Group X, Group Y and Group Z.
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 13 is a hydrogen atom
- R X 14 is any substituent selected from the group X and the group Y.
- R 1 is a methyl group
- L is CH 2
- R X 13 is a hydrogen atom
- R X 14 is any substituent selected from group X and group Y.
- R 1 is a chlorine atom
- L is CH 2
- R X 13 is a hydrogen atom
- R X 14 is any substituent selected from the group X and the group Y.
- R 1 is a methyl group
- L is an oxygen atom
- R X13 is a methyl group
- R X14 is selected from the group X and the group Y A compound.
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 13 is a methyl group
- R X 14 is any substituent selected from the group X and the group Y.
- R 1 is a methyl group
- L is CH 2
- R X13 is a methyl group
- R X14 is selected from the group X and the group Y A compound.
- R 1 is a chlorine atom
- L is CH 2
- R X 13 is a methyl group
- R X 14 is any substituent selected from group X and group Y.
- R 1 is a methyl group
- L is an oxygen atom
- R X 13 is an ethyl group
- R X 14 is any substituent selected from the group X and the group Y.
- R 1 is a chlorine atom
- L is an oxygen atom
- R X 13 is an ethyl group
- R X 14 is any substituent selected from the group X and the group Y.
- R 1 is a methyl group
- L is CH 2
- R X 13 is an ethyl group
- R X 14 is any substituent selected from group X and group Y.
- R 1 is a chlorine atom
- L is CH 2
- R X 13 is an ethyl group
- R X 14 is any substituent selected from group X and group Y.
- m is 3, and RX2 , RX3 , RX4 , RX5 and RX6 are any combination described in Combination A.
- m is 2, in any combination of substituents corresponds to the structure of the structure and G G R X7, R X8, R X9 and R X10 is described in combination B A compound.
- R X13 is a methyl group and R X14 is a substituent selected from groups X and Y.
- R X13 is an ethyl group and R X14 is a substituent selected from groups X and Y.
- Group W A group consisting of Me, Et, Pr, c-Pr, CF 3 , F, Cl, Br, I.
- L is CH 2 and R 1 is any substituent selected from the group W.
- R X1 is any substituent selected from the group X.
- Equation (5B) In the compound represented by, m is 1, and R X2 , RX3 , RX4 , RX5 and RX6 are any combination described in Combination A.
- RX2 , RX3 , RX4 , RX5 and RX6 are any combination described in Combination A.
- RX2 , RX3 , RX4 , RX5 and RX6 are any combination described in Combination A.
- Equation (5C) In in the compound represented, m is 1, substituents correspond to the structure of the structure and G G R X7, R X8, R X9 and R X10 is, any combination, compound according to the combination B.
- m is 2, in any combination of substituents corresponds to the structure of the structure and G G R X7, R X8, R X9 and R X10 is described in combination B A compound.
- Equation (5F) In the compound represented by, R X13 is a hydrogen atom and R X14 is a substituent selected from the group X and the group Y.
- R X13 is a methyl group and R X14 is a substituent selected from groups X and Y.
- R X13 is an ethyl group and R X14 is a substituent selected from Group X and Group Y.
- the part represents a weight part.
- the compound S of the present invention represents the compounds described in the compound groups SX1 to SX80.
- Formulation Example 1 A preparation is obtained by thoroughly pulverizing and mixing 50 parts of any one of the compounds S of the present invention, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic silicon hydroxide.
- Preparation example 2 20 parts of any one of the compounds S of the present invention and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, finely pulverized by a wet pulverization method, and then contained therein. 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and mixed by stirring to obtain a preparation.
- Preparation example 3 A preparation is obtained by thoroughly pulverizing and mixing 2 parts of any one of the compounds S of the present invention, 88 parts of kaolin clay and 10 parts of talc.
- Preparation example 4 A preparation is obtained by thoroughly mixing 5 parts of any one of the compounds S of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.
- Formulation Example 5 After thoroughly pulverizing and mixing 2 parts of any one of the compounds S of the present invention, 1 part of synthetic silicon hydroxide-containing, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, water is added and kneaded well to prepare. The preparation is obtained by drying the grains.
- Formulation Example 6 20 parts of any one of the compounds S of the present invention; 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water are mixed to make a total of 100 parts, and a crusher is used. The preparation is obtained by processing.
- Test Examples 1 to 9 The untreated group in Test Examples 1 to 9 is a test group performed under the same conditions as described in each Test Example except that DMSO is dispensed in place of the DMSO diluent containing the compound of the present invention. Represents. Further, "no treatment" in Test Examples 10 to 22 means that the aqueous diluted solution of the preparation containing the compound of the present invention was not sprayed.
- Test Example 1 Control test against Zymoseptoria tritici Compounds 1-16, 18-23, 25, 26, 28-30, 33-35, 37, 38-40, 42-52, 54-87 of the present invention , 89 or 90 is diluted with DMSO so as to contain 150 ppm, 1 ⁇ L is dispensed into a titer plate (96 wells), and then 150 ⁇ L of potato decoction liquid medium (PDB medium) previously inoculated with spores of Zymoseptoria trifolia is used. Noted. This plate was cultured at 18 ° C.
- the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of wheat leaf blight.
- the growth rate in the treated group of each compound was 50% or less of the growth rate in the untreated group.
- Test Example 2 Control test against soybean anthrax (Colletotrichum truncatum) Compounds 2-16, 18-20, 25, 26, 29, 38, 40, 42-44, 46-49, 51, 52, 55, 57- Dilute 64, 71 or 76 with DMSO so as to contain 150 ppm, dispense 1 ⁇ L into a titer plate (96 wells), and then add 150 ⁇ L of potato decoction liquid medium (PDB medium) inoculated with spores of soybean anthrax in advance. Noted. This plate was cultured at 18 ° C.
- PDB medium potato decoction liquid medium
- the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth degree of soybean anthrax.
- the growth rate in the treated group of each compound was 50% or less of the growth rate in the untreated group.
- Test Example 3 Control test against Phytophthora capsici Compounds 1-20, 23, 25, 26, 29, 34, 37, 38, 40-49, 51, 52, 54-64, 68, A potato decoction liquid inoculated with spores of Phytophthora phytophthora in advance after diluting 71, 73-76, 80, 89 or 90 with DMSO so as to contain 150 ppm, dispensing 1 ⁇ L into a titer plate (96 wells). 150 ⁇ L of the medium (PDB medium) was dispensed. This plate was cultured at 27 ° C.
- the growth rate in the treated group of each compound was 50% or less of the growth rate in the untreated group.
- Test Example 4 Control test against seedling blight fungus (Pythium ultimum) Compounds 1 to 20, 23, 25, 26, 29, 34, 37, 38, 40 to 49, 51, 52, 54 to 64, 66, 68 of the present invention , 71-76, 79-81, 84-86, 89 or 90 was diluted with DMSO so as to contain 150 ppm, 1 ⁇ L was dispensed into a titer plate (96 wells), and then spores of seedling blight were inoculated in advance. 150 ⁇ L of potato decoction liquid medium (PDB medium) was dispensed. After culturing this plate at 23 ° C.
- PDB medium potato decoction liquid medium
- the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of the seedling blight.
- the growth rate in the treated group of each compound was 50% or less of the growth rate in the untreated group.
- Test Example 5 Control test against corn smut fungus (Ustilago maydis) Compounds 1 to 20, 23, 25, 26, 29, 30, 34, 37 to 49, 51, 52, 54 to 64, 68, 71 to 76, Dilute with DMSO so as to contain 78 to 87, 89 or 90 in 150 ppm, dispense 1 ⁇ L into a titer plate (96 wells), and then prepare a potato decoction liquid medium (PDB medium) inoculated with spores of corn smut in advance. 150 ⁇ L was dispensed. After culturing this plate at 18 ° C.
- PDB medium potato decoction liquid medium
- the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of corn smut.
- the growth rate in the treated group of each compound was 50% or less of the growth rate in the untreated group.
- Test Example 6 Control test against barley cloud fungus (Rhynchosporium secalis) Compounds 1 to 20, 23, 25, 26, 29 to 49, 51, 52, 54 to 64, 66 to 68, 71 to 87, 89 or 90 of the present invention. It was diluted with DMSO so as to contain 150 ppm, and 1 ⁇ L was dispensed into a titer plate (96 wells), and then 150 ⁇ L of potato decoction liquid medium (PDB medium) previously inoculated with spores of barley cloud fungus was dispensed. This plate was cultured at 18 ° C.
- PDB medium potato decoction liquid medium
- the absorbance at 550 nm of each well of the titer plate was measured, and the value was used as the growth rate of barley cloud disease bacteria.
- the growth rate in the treated group of each compound was 50% or less of the growth rate in the untreated group.
- Test Example 7 Control test against Botrytis cinerea of cucumber Compounds 1 to 20, 23, 25, 26, 29 to 34, 36 to 49, 51, 52, 54 to 64, 66, 68, 71 to 85 of the present invention. , 87, 89 or 90 was diluted with DMSO so as to contain 150 ppm, and 1 ⁇ L was dispensed into a titer plate (96 wells), and then 150 ⁇ L of YB liquid medium previously inoculated with spores of Botrytis cinerea was dispensed. This plate was cultured at 18 ° C.
- the growth rate in the treated group of each compound was 50% or less of the growth rate in the untreated group.
- Test Example 8 Control test against Cladosporium carpophilum Compounds 1 to 20, 23, 25, 26, 29 to 49, 51, 52, 54 to 64, 66 to 68, 71 to 87, 89 or 90 of the present invention. It was diluted with DMSO so as to contain 150 ppm, and 1 ⁇ L was dispensed into a titer plate (96 wells), and then 150 ⁇ L of YB liquid medium previously inoculated with spores of Cladosporium peach was dispensed. This plate was cultured at 18 ° C.
- the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of peach scab.
- the growth rate in the treated group of each compound was 50% or less of the growth rate in the untreated group.
- Test Example 9 Control test against rice sesame leaf blight (Cochliobolus miyabeanus) Compounds 28, 30-33, 35, 37, 39, 50, 66, 67, 69, 70, 72-75, 77-89 or 90 of the present invention. It was diluted with DMSO so as to contain 150 ppm, and 1 ⁇ L was dispensed into a titer plate (96 wells), and then 150 ⁇ L of YB liquid medium previously inoculated with spores of Cochliobolus communis was dispensed. This plate was cultured at 23 ° C.
- the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth rate of rice sesame leaf blight.
- the growth rate in the treated group of each compound was 50% or less of the growth rate in the untreated group.
- Test Example 10 Control test for soybean rust (Phakopsora pachyrhizi) The true leaves of soybean (variety: Kurosengoku) were cut out to a diameter of 1 cm to prepare leaf discs. After 1 mL of agar medium (agar concentration 1.2%) was dispensed into each well of the 24-well microplate, one leaf disk was placed on the agar medium of each well. To a mixture of 0.5 ⁇ L of Solpol® 1200 KX, 4.5 ⁇ L of DMSO and 5 ⁇ L of xylene, 20 ⁇ L of DMSO solution containing 10000 ppm of the test compound was added and mixed.
- the obtained mixture was diluted with ion-exchanged water to prepare a mixture containing a predetermined concentration of the test compound.
- the resulting mixture was sprayed at 10 ⁇ L per leaf disc.
- the soybean rust fungi with an amino acid substitution F129L the mitochondrial cytochrome b protein (Phakopsora pachyrhizi) aqueous suspension (1.0 ⁇ 10 5 / mL) of spores was inoculated by spraying on leaf disks. After inoculation, it was placed in an artificial meteorological device (lighted for 6 hours, turned off for 18 hours, temperature 23 ° C., humidity 60%).
- the leaf disc was air-dried until there were no water droplets on the surface, and the leaf disc was placed in the artificial meteorological instrument again for 12 days. After that, the lesion area of soybean rust was investigated.
- the predetermined concentration was set to 50 ppm, and as test compounds, the compounds of the present invention 1 to 10, 15 to 20, 23, 28 to 31, 33 to 35, 37, 39, 40, 50, 55, 56, 66 to 68,
- the lesion area of the leaf disc treated with any one of 70, 71 to 87, 89 or 90 was 30% or less of the lesion area of the untreated leaf disc.
- Test Example 11 Control test for rice blast (Pyricularia oryzae) A plastic pot was filled with soil, and rice (variety; Hinohikari) was sown in the soil and cultivated in a greenhouse for 20 days. Then, the compound 19, 44 or 80 of the present invention formulated according to the method described in Preparation Example 6 was mixed with water so as to have a concentration of 200 ppm, and the obtained mixture was sufficiently applied to the leaf surface of the rice. The foliage was sprayed so as to adhere.
- the rice After spraying, the rice is air-dried and left at 24 ° C during the day and 20 ° C at night under high humidity for 6 to 7 days while contacting the sprayed rice with the rice seedlings (variety; Hinohikari) infected with the rice blast fungus. After that, the lesion area was investigated. As a result, the lesion area in the rice treated with each compound of the present invention was 30% or less of the lesion area in the untreated rice.
- Test Example 12 Control test for barley net spot disease (Pyrenophora teres) A plastic pot was filled with soil, and barley (variety; Nishinohoshi) was sown in the plastic pot and cultivated in a greenhouse for 7 days. Compounds 2, 4 to 6, 13, 14, 16, 18 to 20, 26, 34, 39, 46 to 49, 51, 52, 54, 55 of the present invention formulated according to the method described in Preparation Example 6. , 57, 58, 64, 67, 68, 75-77, 80-83, 85-88 or 89 were mixed with water to a concentration of 200 ppm. The obtained mixture was sprayed on the foliage so as to sufficiently adhere to the leaf surface of the barley.
- the barley After spraying, the barley was air-dried, and one day later, a water suspension of barley net spot disease spores was spray-inoculated. After inoculation, the barley was placed in a greenhouse at 23 ° C. in the daytime and 20 ° C. in the nighttime under high humidity for 3 days, and then cultivated in the greenhouse for 7 days, and then the lesion area was investigated. As a result, the lesion area in the barley treated with each compound of the present invention was 30% or less of the lesion area in the untreated barley.
- Test Example 13 Control test for downy mildew (Pseudoperonospora cubensis) A plastic pot was filled with soil, and cucumber (variety; Sagami Hanshiro) was sown in the plastic pot and grown in a greenhouse for 12 days.
- Compound 2, 47 or 61 of the present invention formulated according to the method described in Formulation Example 6 is mixed with water so as to have a concentration of 200 ppm, and the obtained mixture is sufficiently adhered to the cucumber leaf surface.
- the foliage was sprayed as in. After spraying, the cucumber was air-dried, and one day later, a suspension of cucumber and diseased spores was spray-inoculated. After inoculation, the cucumber was placed in a greenhouse at 23 ° C.
- the lesion area of the cucumbers treated with each of the compounds of the present invention was 30% or less of the lesion area of the untreated cucumbers.
- Test Example 14 Control test for wheat leaf rust (Puccinia recondita) A plastic pot was filled with soil, and wheat (variety; white gane) was sown in the plastic pot and cultivated in a greenhouse for 9 days. Compounds 2-6, 10-16, 18, 19, 20, 25, 26, 29, 31, 32, 34, 35, 39-42, 46 formulated according to the method described in Formulation Example 6. , 47, 49, 52-64, 66-68, 73, 75-78, 80, 81, 83-89 or 90 were mixed with water to a concentration of 200 ppm, and the obtained mixture was obtained from the above wheat. The foliage was sprayed so that it adhered sufficiently to the leaf surface.
- the wheat was air-dried, cultivated at 20 ° C. under lighting for 5 to 7 days, and then sprinkled with spores of wheat rust. After inoculation, wheat was placed at 23 ° C. in dark and humid for 1 day, and then cultivated at 20 ° C. under lighting for 8 days, and the lesion area was investigated. As a result, the lesion area of the wheat treated with each of the compounds of the present invention was 30% or less of the lesion area of the untreated wheat.
- Test Example 15 Control test for wheat leaf blight (Septoria tritici) A plastic pot was filled with soil, and wheat (variety; apogee) was sown in the plastic pot and cultivated in a greenhouse for 10 days. Compounds 1, 3 to 6, 10, 11, 13 to 16, 18 to 21, 25, 26, 29 to 37, 39, 40, 46 to 49 of the present invention formulated according to the method described in Preparation Example 6. , 51, 53-55, 57, 58, 64, 72, 73, 75, 77-80, 82, 83, 85-88 or 89 were mixed with water to a concentration of 200 ppm, and the obtained mixture was obtained. , The foliage was sprayed so as to sufficiently adhere to the leaf surface of the wheat.
- the wheat After spraying, the wheat was air-dried, and 4 days later, a water suspension containing spores of Zymoseptoria trifolia was spray-inoculated. After inoculation, the wheat was placed under high humidity at 18 ° C. for 3 days, then cultivated under illumination for 14 to 18 days, and then the lesion area was investigated. As a result, the lesion area of the wheat treated with each of the compounds of the present invention was 30% or less of the lesion area of the untreated wheat.
- Test Example 16 Control test for wheat leaf blight (Septoria tritici) Fill a plastic pot with soil, sow wheat (variety; apogee) in it, cultivate it in a greenhouse for 10 days, and suspend wheat leaf blight spores in water. The liquid was sprayed. After inoculation, the wheat was placed in a humid environment at 18 ° C. for 3 days, and then the compounds of the present invention, which were formulated according to the method described in Preparation Example 6, 3 to 5, 7 to 11, 15, 16, 21, 25, 26, 29, 31, 34, 37, 39, 44, 46, 47, 49, 57, 58, 71-75, 77-82, 84, 88, 89 or 90 were mixed with water to a concentration of 200 ppm.
- the obtained mixture was sprayed on the foliage so as to sufficiently adhere to the leaf surface of the wheat. After spraying, the wheat was air-dried and left under illumination for 14 to 18 days, and then the lesion area was investigated. As a result, the lesion area of the wheat treated with each of the compounds of the present invention was 30% or less of the lesion area of the untreated wheat.
- Test Example 17 Control test against tomato epidemic (Phytophthora infestans) Soil was filled in a plastic pot, tomatoes (varieties; patio) were sown in the plastic pots, and cultivated in a greenhouse for 20 days. Compounds 2, 11-14, 16, 18-21, 29, 35, 39, 49, 51, 52, 55, 56, 60-64, 66 of the present invention formulated according to the method described in Formulation Example 6. , 76, 80, 85 or 86 was mixed with water to a concentration of 200 ppm, and the obtained mixture was sprayed on the foliage so as to sufficiently adhere to the leaf surface of the tomato.
- the tomatoes After spraying, the tomatoes were air-dried, and one day later, a water suspension containing spores of Phytophthora tomatoes was spray-inoculated. After inoculation, the tomatoes were placed in a greenhouse at 23 ° C. in the daytime and 20 ° C. in the nighttime under high humidity for 1 day, then cultivated in the greenhouse for 4 days, and then the lesion area was investigated. As a result, the lesion area in the tomatoes treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated tomatoes.
- Test Example 18 Control test for soybean rust (Phakopsora pachyrhizi) Soil was filled in a plastic pot, soybean (variety; Kurosengoku) was sown in it, and it was grown in a greenhouse for 10 to 14 days. Compounds 1-16, 18-23, 25, 26, 29-32, 34, 35, 37-40, 44-46, 48, 49, 51 of the present invention formulated according to the method described in Formulation Example 6. To 59, 61 to 64, 68, 71 to 73, 75 to 77, 79 to 83, 85 to 89 or 90 were mixed with water so as to have a concentration of 200 ppm, and the obtained mixture was used as the leaf surface of the soybean. The foliage was sprayed so that it adhered sufficiently to the plants.
- soybeans After spraying, the soybeans were air-dried, and 2 to 5 days later, a water suspension of soybean rust spores was spray-inoculated. After inoculation, soybeans were placed in a greenhouse at 23 ° C. in the daytime and 20 ° C. in the nighttime under high humidity for 1 to 2 days, and then cultivated in the greenhouse for 12 days, and then the lesion area was investigated. As a result, the lesion area in the soybeans treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated soybeans.
- Test Example 19 Control test for soybean rust (Phakopsora pachyrhizi) Fill a plastic pot with soil, sow soybean (variety; Kurosengoku) in it, grow it in a greenhouse for 10 days, and water it with spores of soybean rust. The turbid liquid was sprayed. After inoculation, soybeans were placed in a greenhouse at 23 ° C. during the day and 20 ° C. at night under high humidity for 1 day, then cultivated in the greenhouse for 2 days, and then the compound 1 of the present invention formulated according to the method described in Preparation Example 6.
- Test Example 20 Control test for soybean spot disease (Cercospora sojina) Soil was filled in a plastic pot, soybean (variety; Tachinagaha) was sown in the plastic pot, and the plant was grown in a greenhouse for 13 days. Compounds 1-16, 18-21, 25, 26, 29-35, 37, 39, 40, 44, 46-49, 54-58, 64 of the present invention formulated according to the method described in Formulation Example 6. , 71-89 or 90 was mixed with water so as to have a concentration of 200 ppm, and the obtained mixture was sprayed on the foliage so as to sufficiently adhere to the leaf surface of the soybean.
- soybeans After spraying, the soybeans were air-dried, and one day later, a water suspension of soybean spot disease spores was spray-inoculated. After inoculation, soybeans were placed in a greenhouse at 23 ° C. in the daytime and 20 ° C. in the nighttime under high humidity for 3 days, then cultivated in the greenhouse for 16 days, and then the lesion area was investigated. As a result, the lesion area in the soybeans treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated soybeans.
- Test Example 21 Control test for tomato ring pattern disease (Alternaria solani) A plastic pot was filled with soil, and tomatoes (varieties; patio) were sown in the plastic pots and grown in a greenhouse for 20 days. Compounds 3-6, 9, 11-16, 18-20, 29, 32, 35, 36, 44, 51, 57-59, 68, 71 formulated according to the method described in Formulation Example 6. , 75, 76, 80, 86 or 87 were mixed with water to a concentration of 200 ppm, and the obtained mixture was sprayed on the foliage so as to sufficiently adhere to the leaf surface of the tomato. After spraying, the tomatoes were air-dried, and one day later, a water suspension of tomato ring-spotted spores was spray-inoculated.
- the tomatoes were placed at 18 ° C. and under high humidity for 6 days, and then the lesion area was investigated. As a result, the lesion area in the tomatoes treated with each of the compounds of the present invention was 30% or less of the lesion area in the untreated tomatoes.
- Test Example 22 Control test against sclerotinia sclerotiorum (Sclerotinia sclerotiorum) Soil was filled in plastic pots, green beans (varieties; long bean beans) were sown, and they were grown in a greenhouse for 8 days.
- the common bean After spraying, the common bean was air-dried, and a PDA medium containing hyphae of Sclerotinia sclerotitus was placed on the leaf surface of the common bean. After inoculation, all green beans were kept under high humidity only at night, and the lesion area was investigated 4 days after inoculation. As a result, the lesion area of the kidney beans treated with each compound of the present invention was 30% or less of the lesion area of the untreated kidney beans.
- Test method 23 The compound of the present invention is prepared according to the method described in Preparation Example 6, and water containing 0.03% by volume of the spreading agent is added thereto to prepare a diluted solution containing the compound of the present invention at a predetermined concentration.
- Test Example 23 As a result of conducting a test according to the test method 23 using the compound 28 of the present invention at a predetermined concentration of 500 ppm, the compound 28 of the present invention showed a mortality rate of 100%.
- the compound of the present invention has a control effect on pests and can be used for pest control.
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Abstract
Description
すなわち、本発明は以下のとおりである。
〔1〕 式(I):
Lは、酸素原子又はCH2を表し、
Eは、群Aより選ばれる1以上の置換基で置換されているメチル基、群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-を表し、
R1は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表し、
nは、0、1、2又は3を表し、
nが2又は3である場合、複数のR2は同一又は異なっていてもよく、
R2は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表し、
R3は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R4は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、又は5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}を表し、
R5は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、1以上のハロゲン原子で置換されていてもよいC1-C3アルコキシ基又は水素原子を表し、
R6は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R3及びR5は、R3とR5とが結合する窒素原子と一緒になって4-7員非芳香族複素環{該4-7員非芳香族複素環は群Bより選ばれる1以上の置換基を有していてもよい}を形成していてもよい。
群A:OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基及びニトロ基からなる群。
R11及びR12は、同一又は相異なり、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R13は、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基又は3-8員非芳香族複素環基{該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表し、
R14、R15及びR16は、同一又は相異なり、C1-C6鎖式炭化水素基又はフェニル基を表し、
mは、0、1又は2を表す。
群B:群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、オキソ基、チオキソ基、ハロゲン原子、シアノ基及びニトロ基からなる群。
群C:群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基及びニトロ基からなる群。
群D:C3-C6シクロアルキル基{該C3-C6シクロアルキル基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、OR17、S(O)mR19、OS(O)2R19、C(O)R17、C(O)OR17、OC(O)R17、OC(O)OR17、OC(O)NR17R18、NR17C(O)NR18R19、NR17R18、C(O)NR17R18、S(O)2NR17R18、NR18C(O)R17、NR18C(O)OR19、NR18S(O)2R19、C(R18)=N-OR17、O-N=CR17R19、SiR14R15R16、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、フェノキシ基、フェニル基、ナフチル基、5-6員芳香族複素環基及び3-8員非芳香族複素環基{該フェノキシ基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}からなる群。
R17及びR18は、同一又は相異なり、C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R19は、C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基又は3-8員非芳香族複素環基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}を表す。
群E:C1-C6鎖式炭化水素基、C3-C6シクロアルキル基{該C1-C6鎖式炭化水素基及び該C3-C6シクロアルキル基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、OR17、S(O)mR19、OS(O)2R19、C(O)R17、C(O)OR17、OC(O)R17、OC(O)OR17、OC(O)NR17R18、NR17C(O)NR18R19、NR17R18、C(O)NR17R18、S(O)2NR17R18、NR18C(O)R17、NR18C(O)OR19、NR18S(O)2R19、C(R18)=N-OR17、O-N=CR17R19、SiR14R15R16、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、フェノキシ基、フェニル基、ナフチル基、5-6員芳香族複素環基及び3-8員非芳香族複素環基{該フェノキシ基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}からなる群。
群F:C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、C1-C6アルコキシ基及びC1-C6アルキルチオ基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該C1-C6アルコキシ基及び該C1-C6アルキルチオ基は、ハロゲン原子及びシアノ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基、ニトロ基及びヒドロキシ基からなる群。〕
で示される化合物(以下、本発明化合物Nと記す)、又はそのNオキシド若しくは農業上許容可能な塩(以下、本発明化合物と記す)。
〔2〕 Eが、群Aより選ばれる1以上の置換基で置換されているメチル基、又は群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基である、〔1〕に記載の化合物、又はそのNオキシド若しくは農業上許容可能な塩。
〔3〕 Eが、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-である、〔1〕に記載の化合物、又はそのNオキシド若しくは農業上許容可能な塩。
〔4〕 Eが、R3R5NC(O)-である、〔1〕に記載の化合物、又はそのNオキシド若しくは農業上許容可能な塩。
〔5〕 R1が、メチル基又は塩素原子であり、nが0であり、Lが酸素原子である、〔1〕~〔4〕のいずれか1つに記載の化合物、又はそのNオキシド若しくは農業上許容可能な塩。
〔6〕 〔1〕~〔5〕のいずれか1つに記載の化合物、又はそのNオキシド若しくは農業上許容可能な塩と不活性担体とを含有する有害生物防除組成物(以下、本発明組成物と記す)。
〔7〕 群(a)、群(b)、群(c)及び群(d)からなる群より選ばれる1以上の成分、並びに〔1〕~〔5〕のいずれか1つに記載の化合物、又はそのNオキシド若しくは農業上許容可能な塩を含有する組成物:
群(a):殺虫活性成分、殺ダニ活性成分及び殺線虫活性成分からなる群;
群(b):殺菌活性成分;
群(c):植物成長調整成分;
群(d):忌避成分。
〔8〕 〔1〕~〔5〕のいずれか1つに記載の化合物、若しくはそのNオキシド若しくは農業上許容可能な塩の有効量又は〔7〕に記載の組成物を植物又は土壌に処理することによる有害生物の防除方法。
〔9〕 〔1〕~〔5〕のいずれか1つに記載の化合物、若しくはそのNオキシド若しくは農業上許容可能な塩の有効量又は〔7〕に記載の組成物をダイズ又はダイズを生育する土壌に施用することによる、ミトコンドリアチトクロームbタンパク質にF129Lのアミノ酸置換を有するダイズさび病菌の防除方法。
〔10〕 有害生物を防除するための、〔1〕~〔5〕のいずれか1つに記載の化合物、若しくはそのNオキシド若しくは農業上許容可能な塩又は〔7〕に記載の組成物の使用。
〔11〕 〔1〕~〔5〕のいずれか1つに記載の化合物、若しくはそのNオキシド若しくは農業上許容可能な塩の有効量又は〔7〕に記載の組成物を保持している種子又は栄養生殖器官。
〔12〕 式(II):
Lは、酸素原子又はCH2を表し、
R1は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表し、
nは、0、1、2又は3を表し、
nが2又は3である場合、複数のR2は同一又は異なっていてもよく、
R2は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表す。〕
で示される化合物(以下、中間体Aと記す)。
〔13〕 R1が、メチル基又は塩素原子であり、nが0である、〔12〕に記載の化合物。
〔14〕 式(III):
Lは、酸素原子又はCH2を表し、
Eは、群Aより選ばれる1以上の置換基で置換されているメチル基、群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-を表し、
R1は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表し、
nは、0、1、2又は3を表し、
nが2又は3である場合、複数のR2は同一又は異なっていてもよく、
R2は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表し、
R3は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R4は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、又は5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}を表し、
R5は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、1以上のハロゲン原子で置換されていてもよいC1-C3アルコキシ基又は水素原子を表し、
R6は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R3及びR5は、R3とR5とが結合する窒素原子と一緒になって4-7員非芳香族複素環{該4-7員非芳香族複素環は群Bより選ばれる1以上の置換基を有していてもよい}を形成していてもよい。
群A:OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基及びニトロ基からなる群。
R11及びR12は、同一又は相異なり、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R13は、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基又は3-8員非芳香族複素環基{該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表し、
R14、R15及びR16は、同一又は相異なり、C1-C6鎖式炭化水素基又はフェニル基を表し、
mは、0、1又は2を表す。
群B:群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、オキソ基、チオキソ基、ハロゲン原子、シアノ基及びニトロ基からなる群。
群C:群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基及びニトロ基からなる群。
群D:C3-C6シクロアルキル基{該C3-C6シクロアルキル基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、OR17、S(O)mR19、OS(O)2R19、C(O)R17、C(O)OR17、OC(O)R17、OC(O)OR17、OC(O)NR17R18、NR17C(O)NR18R19、NR17R18、C(O)NR17R18、S(O)2NR17R18、NR18C(O)R17、NR18C(O)OR19、NR18S(O)2R19、C(R18)=N-OR17、O-N=CR17R19、SiR14R15R16、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、フェノキシ基、フェニル基、ナフチル基、5-6員芳香族複素環基及び3-8員非芳香族複素環基{該フェノキシ基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}からなる群。
R17及びR18は、同一又は相異なり、C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R19は、C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基又は3-8員非芳香族複素環基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}を表す。
群E:C1-C6鎖式炭化水素基、C3-C6シクロアルキル基{該C1-C6鎖式炭化水素基及び該C3-C6シクロアルキル基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、OR17、S(O)mR19、OS(O)2R19、C(O)R17、C(O)OR17、OC(O)R17、OC(O)OR17、OC(O)NR17R18、NR17C(O)NR18R19、NR17R18、C(O)NR17R18、S(O)2NR17R18、NR18C(O)R17、NR18C(O)OR19、NR18S(O)2R19、C(R18)=N-OR17、O-N=CR17R19、SiR14R15R16、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、フェノキシ基、フェニル基、ナフチル基、5-6員芳香族複素環基及び3-8員非芳香族複素環基{該フェノキシ基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}からなる群。
群F:C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、C1-C6アルコキシ基及びC1-C6アルキルチオ基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該C1-C6アルコキシ基及び該C1-C6アルキルチオ基は、ハロゲン原子及びシアノ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基、ニトロ基及びヒドロキシ基からなる群。〕
で示される化合物(以下、中間体Bと記す)。
〔15〕 Eが、群Aより選ばれる1以上の置換基で置換されているメチル基、又は群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基である、〔14〕に記載の化合物。
〔16〕 Eが、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-である、〔14〕に記載の化合物。
〔17〕 Eが、R3R5NC(O)-である、〔14〕に記載の化合物。
〔18〕 R1が、メチル基又は塩素原子であり、nが0であり、Lが酸素原子である、〔14〕~〔17〕のいずれか1つに記載の化合物。
〔19〕 式(IV):
Eは、群Aより選ばれる1以上の置換基で置換されているメチル基、群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-を表し、
nは、0、1、2又は3を表し、
nが2又は3である場合、複数のR2は同一又は異なっていてもよく、
R2は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表し、
R3は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R4は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、又は5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}を表し、
R5は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、1以上のハロゲン原子で置換されていてもよいC1-C3アルコキシ基又は水素原子を表し、
R6は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R3及びR5は、R3とR5とが結合する窒素原子と一緒になって4-7員非芳香族複素環{該4-7員非芳香族複素環は群Bより選ばれる1以上の置換基を有していてもよい}を形成していてもよい。
群A:OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基及びニトロ基からなる群。
R11及びR12は、同一又は相異なり、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R13は、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基又は3-8員非芳香族複素環基{該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表し、
R14、R15及びR16は、同一又は相異なり、C1-C6鎖式炭化水素基又はフェニル基を表し、
mは、0、1又は2を表す。
群B:群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、オキソ基、チオキソ基、ハロゲン原子、シアノ基及びニトロ基からなる群。
群C:群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基及びニトロ基からなる群。
群D:C3-C6シクロアルキル基{該C3-C6シクロアルキル基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、OR17、S(O)mR19、OS(O)2R19、C(O)R17、C(O)OR17、OC(O)R17、OC(O)OR17、OC(O)NR17R18、NR17C(O)NR18R19、NR17R18、C(O)NR17R18、S(O)2NR17R18、NR18C(O)R17、NR18C(O)OR19、NR18S(O)2R19、C(R18)=N-OR17、O-N=CR17R19、SiR14R15R16、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、フェノキシ基、フェニル基、ナフチル基、5-6員芳香族複素環基及び3-8員非芳香族複素環基{該フェノキシ基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}からなる群。
R17及びR18は、同一又は相異なり、C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R19は、C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基又は3-8員非芳香族複素環基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}を表す。
群E:C1-C6鎖式炭化水素基、C3-C6シクロアルキル基{該C1-C6鎖式炭化水素基及び該C3-C6シクロアルキル基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、OR17、S(O)mR19、OS(O)2R19、C(O)R17、C(O)OR17、OC(O)R17、OC(O)OR17、OC(O)NR17R18、NR17C(O)NR18R19、NR17R18、C(O)NR17R18、S(O)2NR17R18、NR18C(O)R17、NR18C(O)OR19、NR18S(O)2R19、C(R18)=N-OR17、O-N=CR17R19、SiR14R15R16、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、フェノキシ基、フェニル基、ナフチル基、5-6員芳香族複素環基及び3-8員非芳香族複素環基{該フェノキシ基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}からなる群。
群F:C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、C1-C6アルコキシ基及びC1-C6アルキルチオ基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該C1-C6アルコキシ基及び該C1-C6アルキルチオ基は、ハロゲン原子及びシアノ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基、ニトロ基及びヒドロキシ基からなる群。〕
で示される化合物(以下、中間体Cと記す)。
〔20〕 nが0であり、Eが、群Aより選ばれる1以上の置換基で置換されているメチル基、又は群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基である、〔19〕に記載の化合物。
〔21〕 nが0であり、Eが、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-である、〔19〕に記載の化合物。
〔22〕 nが0であり、Eが、R3R5NC(O)-である、〔19〕に記載の化合物。
〔23〕 式(VI):
Lは、酸素原子又はCH2を表し、
R1は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表し、
R2は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表し、
nは、0、1、2又は3を表し、
nが2又は3である場合、複数のR2は同一又は異なっていてもよい。〕
で示される化合物(以下、中間体Dと記す)。
〔24〕 R1が、メチル基又は塩素原子であり、nが0である、〔23〕に記載の化合物。
ハロゲン原子とは、フッ素原子、塩素原子、臭素原子、又はヨウ素原子を意味する。
置換基が2以上のハロゲン原子を有している場合、それらのハロゲン原子は各々同一でも異なっていてもよいことを表す。
本明細書における「CX-CY」との表記は、炭素原子数がX乃至Yであることを意味する。例えば「C1-C6」との表記は、炭素原子数が1乃至6であることを意味する。
鎖式炭化水素基とは、アルキル基、アルケニル基又はアルキニル基を表す。
アルキル基としては、例えばメチル基、エチル基、プロピル基、イソプロピル基、1,1-ジメチルプロピル基、1,2-ジメチルプロピル基、ブチル基、sec-ブチル基、tert-ブチル基、ペンチル基、ヘキシル基、及びデシル基が挙げられる。
アルケニル基としては、例えばビニル基、1-プロペニル基、2-プロペニル基、1-メチル-1-プロペニル基、1-メチル-2-プロペニル基、1,2-ジメチル-1-プロペニル基、3-ブテニル基、4-ペンテニル基、5-ヘキセニル基、及び9-デセニル基が挙げられる。
アルキニル基としては、例えばエチニル基、1-プロピニル基、2-プロピニル基、1-メチル-2-プロピニル基、1,1-ジメチル-2-プロピニル基、2-ブチニル基、4-ペンチニル基、5-ヘキシニル基、及び9-デシニル基が挙げられる。
アルキルチオ基としては、例えばメチルチオ基、エチルチオ基、プロピルチオ基、イソプロピルチオ基、ブチルチオ基、tert-ブチルチオ基、ペンチルチオ基、及びヘキシルチオ基が挙げられる。
芳香族複素環基としては、例えばピロリル基、フリル基、チエニル基、ピラゾリル基、イミダゾリル基、トリアゾリル基、テトラゾリル基、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、オキサジアゾリル基、チアジアゾリル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、テトラジニル基、インドリル基、インダゾリル基、ベンゾイミダゾリル基、イミダゾピリジル、ベンゾチオフェニル基、ベンゾフラニル基、キノリル基、イソキノリル基、キナゾリニル基、及びキノキサリニル基が挙げられる。
非芳香族複素環基としては、例えば、アジリジニル基、オキシラニル基、チイラニル基、アゼチジニル基、オキセタニル基、チエタニル基、ピロリジニル基、テトラヒドロフラニル基、テトラヒドロチエニル基、ピペリジル基、ピラニル基、テトラヒドロピラニル基、テトラヒドロチオピラニル基、アゼパニル基、オキセパニル基、チエパニル基、ピラゾリニル基、ピラゾリジニル基、イミダゾリニル基、イミダゾリジニル基、オキサゾリニル基、チアゾリニル基、オキサゾリジニル基、チアゾリジニル基、イソオキサゾリニル基、イソオキサゾリジニル基、イソチアゾリニル基、イソチアゾリジニル基、モルホリニル基、チオモルホリニル基、及びピペラジニル基が挙げられる。
ミトコンドリアチトクロームbタンパク質にF129Lのアミノ酸置換を有するダイズさび病菌とは、ミトコンドリアチトクロームタンパク質をコードするミトコンドリアチトクロームb遺伝子中に変異を有し、該変異の結果としてF129Lのアミノ酸置換が起こったことにより、QoI殺菌剤に抵抗性を示すダイズさび病菌(学名:Phakopsora pachyrhizi)である。
〔態様2〕態様1において、R1がメチル基又は塩素原子である化合物。
〔態様3〕態様1において、R1がメチル基である化合物。
〔態様4〕態様1において、Lが酸素原子である化合物。
〔態様5〕態様2において、Lが酸素原子である化合物。
〔態様6〕態様3において、Lが酸素原子である化合物。
〔態様7〕態様1において、R1が塩素原子である化合物。
〔態様8〕態様1において、LがCH2である化合物。
〔態様9〕態様2において、LがCH2である化合物。
〔態様10〕態様3において、LがCH2である化合物。
〔態様11〕態様1~態様10又は本発明化合物Nのいずれかにおいて、Eが、群Aより選ばれる1以上の置換基で置換されているメチル基、又は群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基である化合物。
〔態様12〕態様1~態様10又は本発明化合物Nのいずれかにおいて、Eが群Aより選ばれる1以上の置換基で置換されているメチル基である化合物。
〔態様13〕態様1~態様10又は本発明化合物Nのいずれかにおいて、Eが群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基である化合物。
〔態様14〕態様1~態様10又は本発明化合物Nのいずれかにおいて、Eが、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-である化合物。
〔態様15〕態様1~態様10又は本発明化合物Nのいずれかにおいて、EがR3R5NC(O)-である化合物。
〔態様16〕態様1~態様10又は本発明化合物Nのいずれかにおいて、Eが群Jより選ばれる1以上の置換基で置換されているメチル基、群Jより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基、又はR3R5NC(O)-であり、R3が1以上のハロゲン原子で置換されていてもよいC1-C5鎖式炭化水素基、又は1以上のハロゲン原子で置換されていてもよいフェニル基であり、R5がメチル基、メトキシ基、又は水素原子であり、R3及びR5が、R3とR5とが結合する窒素原子と一緒になって5-6員非芳香族複素環基を形成していてもよい化合物。
群J:OCH3、Si(CH3)3、C3-C6シクロアルキル基、シアノ基、ハロゲン原子、フェニル基、及び5-6員芳香族複素環基{該フェニル基及び該5-6員芳香族複素環基は、トリフルオロメチル基、ハロゲン原子及びシアノ基からなる群より選ばれる1以上の置換基で置換されていてもよい}からなる群。
〔態様17〕態様16において、Eが群Jより選ばれる1以上の置換基で置換されているメチル基、又は群Jより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基である化合物。
〔態様18〕態様16において、EがR3R5NC(O)-であり、R3が1以上のハロゲン原子で置換されていてもよいC1-C5鎖式炭化水素基、又は1以上のハロゲン原子で置換されていてもよいフェニル基であり、R5がメチル基、メトキシ基、又は水素原子である化合物。
〔態様19〕態様16において、EがR3R5NC(O)-であり、R3及びR5が、R3とR5とが結合する窒素原子と一緒になって5-6員非芳香族複素環基を形成していてもよい化合物。
〔態様20〕態様1~態様10又は本発明化合物Nのいずれかにおいて、Eが群Kより選ばれる1以上の置換基で置換されているメチル基、群Kより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基、又はR3R5NC(O)-であり、R3が1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、1以上のハロゲン原子で置換されていてもよいC3-C6シクロアルキル基、又は1以上のハロゲン原子で置換されていてもよいフェニル基であり、R5がメチル基、メトキシ基、又は水素原子であり、R3及びR5が、R3とR5とが結合する窒素原子と一緒になって5-6員非芳香族複素環基を形成していてもよい化合物。
群K:OCH3、Si(CH3)3、C3-C6シクロアルキル基、シアノ基、ハロゲン原子、3-6員非芳香族複素環基、フェニル基、及び5-6員芳香族複素環基{該C3-C6シクロアルキル基、該3-6員非芳香族複素環基、該フェニル基及び該5-6員芳香族複素環基は、トリフルオロメチル基、ハロゲン原子及びシアノ基からなる群より選ばれる1以上の置換基で置換されていてもよい}からなる群。
〔態様21〕態様1~態様10又は本発明化合物Nのいずれかにおいて、Eが群Kより選ばれる1以上の置換基で置換されているメチル基、又は群Kより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基である化合物。
〔態様22〕態様1~態様10又は本発明化合物Nのいずれかにおいて、Eが群Kより選ばれる1以上の置換基で置換されているメチル基である化合物。
〔態様23〕態様1~態様10又は本発明化合物Nのいずれかにおいて、Eが群Kより選ばれる1以上の置換基で置換されていてもよいC2-C6鎖式炭化水素基である化合物。
〔態様24〕態様1~態様10又は本発明化合物Nのいずれかにおいて、Eが1以上のハロゲン原子で置換されていてもよいC2-C6鎖式炭化水素基である化合物。
〔態様25〕態様1~態様10又は本発明化合物Nのいずれかにおいて、EがR3R5NC(O)-であり、R3が1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、1以上のハロゲン原子で置換されていてもよいC3-C6シクロアルキル基、又は1以上のハロゲン原子で置換されていてもよいフェニル基であり、R5がメチル基、メトキシ基、又は水素原子であり、R3及びR5が、R3とR5とが結合する窒素原子と一緒になって5-6員非芳香族複素環基を形成していてもよい化合物。
〔態様26〕態様1~態様10又は本発明化合物Nのいずれかにおいて、EがR3R5NC(O)-であり、R3及びR5が、R3とR5とが結合する窒素原子と一緒になって5-6員非芳香族複素環基を形成していてもよい化合物。
〔態様A2〕態様A1において、R1がメチル基又は塩素原子である化合物。
〔態様A3〕態様A1において、R1がメチル基である化合物。
〔態様A4〕態様A1において、Lが酸素原子である化合物。
〔態様A5〕態様A2において、Lが酸素原子である化合物。
〔態様A6〕態様A3において、Lが酸素原子である化合物。
〔態様A7〕態様A1において、R1が塩素原子である化合物。
〔態様A8〕態様A7において、Lが酸素原子である化合物。
〔態様A9〕態様A1において、LがCH2である化合物。
〔態様A10〕態様A2において、LがCH2である化合物。
〔態様A11〕態様A3において、LがCH2である化合物。
〔態様A12〕態様A7において、LがCH2である化合物。
〔態様B2〕態様B1において、R1がメチル基又は塩素原子である化合物。
〔態様B3〕態様B1において、R1がメチル基である化合物。
〔態様B4〕態様B1において、Lが酸素原子である化合物。
〔態様B5〕態様B2において、Lが酸素原子である化合物。
〔態様B6〕態様B3において、Lが酸素原子である化合物。
〔態様B7〕態様B1~態様B6又は中間体Bのいずれかにおいて、Eが、群Aより選ばれる1以上の置換基で置換されているメチル基、又は群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基である化合物。
〔態様B8〕態様B1~態様B6又は中間体Bのいずれかにおいて、Eが群Aより選ばれる1以上の置換基で置換されているメチル基である化合物。
〔態様B9〕態様B1~態様B6又は中間体Bのいずれかにおいて、Eが群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基である化合物。
〔態様B10〕態様B1~態様B6又は中間体Bのいずれかにおいて、Eが、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-である化合物。
〔態様B11〕態様B1~態様B6又は中間体Bのいずれかにおいて、EがR3R5NC(O)-である化合物。
〔態様B12〕態様B1~態様B6又は中間体Bのいずれかにおいて、Eがベンジル基又は(C3-C6シクロアルキル)メチル基である化合物。
〔態様C2〕態様C1又は中間体Cのいずれかにおいて、Eが、群Aより選ばれる1以上の置換基で置換されているメチル基、又は群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基である化合物。
〔態様C3〕態様C1又は中間体Cのいずれかにおいて、Eが群Aより選ばれる1以上の置換基で置換されているメチル基である化合物。
〔態様C4〕態様C1又は中間体Cのいずれかにおいて、Eが群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基である化合物。
〔態様C5〕態様C1又は中間体Cのいずれかにおいて、Eが、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-である化合物。
〔態様C6〕態様C1又は中間体Cのいずれかにおいて、EがR3R5NC(O)-である化合物。
〔態様C7〕態様C1又は中間体Cのいずれかにおいて、Eがベンジル基又は(C3-C6シクロアルキル)メチル基である化合物。
〔態様D2〕態様D1において、R1がメチル基又は塩素原子である化合物。
〔態様D3〕態様D1において、R1がメチル基である化合物。
〔態様D4〕態様D1において、Lが酸素原子である化合物。
〔態様D5〕態様D2において、Lが酸素原子である化合物。
〔態様D6〕態様D3において、Lが酸素原子である化合物。
〔態様D7〕態様D1において、R1が塩素原子である化合物。
〔態様D8〕態様D7において、Lが酸素原子である化合物。
〔態様D9〕態様D1において、LがCH2である化合物。
〔態様D10〕態様D2において、LがCH2である化合物。
〔態様D11〕態様D3において、LがCH2である化合物。
〔態様D12〕態様D7において、LがCH2である化合物。
式(I-E1)で示される化合物(以下、化合物(I-E1)と記す)は、式(II)で示される中間体Aと式(R1)で示される化合物(以下、化合物(R1)と記す)とを、ホスフィン類及びアゾジエステル類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、ヘキサン、トルエン、キシレン等の炭化水素(以下、炭化水素類と記す);メチルtert-ブチルエーテル(以下、MTBEと記す)、テトラヒドロフラン(以下、THFと記す)、ジメトキシエタン等のエーテル(以下、エーテル類と記す);クロロホルム、クロロベンゼン等のハロゲン化炭化水素(以下、ハロゲン化炭化水素類と記す);ジメチルホルムアミド(以下、DMFと記す)、N-メチルピロリドン等のアミド(以下、アミド類と記す);酢酸メチル、酢酸エチル等のエステル(以下、エステル類と記す);アセトニトリル、プロピオニトリル等のニトリル(以下、ニトリル類と記す)及びこれらの2つ以上の混合物が挙げられる。
ホスフィン類としては、例えば、トリフェニルホスフィン及びトリメチルホスフィンが挙げられる。
アゾジエステル類としては、例えば、ジエチル アゾジカルボキシラート、ジイソプロピル アゾジカルボキシラート及びビス(2-メトキシエチル) アゾジカルボキシラートが挙げられる。
反応には、1モルの中間体Aに対して、化合物(R1)が通常1~10モルの割合、ホスフィン類が通常1~10モルの割合、アゾジエステル類が通常1~10モルの割合で用いられる。
反応温度は通常0~150℃の範囲内である。反応時間は通常0.1~48時間の範囲内である。
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、濃縮する等の後処理操作を行うことにより、化合物(I-E1)を単離することができる。
化合物(R1)は、公知であるか、公知の方法に準じて製造することができる。
化合物(I-E1)は、式(II)で示される中間体Aと式(R2)で示される化合物(以下、化合物(R2)と記す)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もできる。
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、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類及びこれらの2つ以上の混合物が挙げられる。
塩基としては例えば、トリエチルアミン、ピリジン等の有機塩基(以下、有機塩基類と記す);炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩(以下、アルカリ金属炭酸塩類と記す);炭酸水素ナトリウム、炭酸水素カリウム等のアルカリ金属炭酸水素塩(以下、アルカリ金属炭酸水素塩類と記す);水素化ナトリウム及びリン酸三カリウムが挙げられる。
反応には、1モルの中間体Aに対して、化合物(R2)が通常1~10モルの割合、塩基が通常1~10モルの割合で用いられる。
反応温度は通常-20~150℃の範囲内である。反応時間は通常0.1~48時間の範囲内である。
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、濃縮する等の後処理操作を行うことにより、化合物(I-E1)を単離することができる。
化合物(R2)は、公知であるか、公知の方法に準じて製造することができる。
式(I-E2)で示される化合物(以下、化合物(I-E2)と記す)は、式(II)で示される中間体Aと式(R3)で示される化合物(以下、化合物(R3)と記す)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、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類及びこれらの2つ以上の混合物が挙げられる。
塩基としては例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、水素化ナトリウム及びリン酸三カリウムが挙げられる。
反応には、1モルの中間体Aに対して、化合物(R3)が通常1~10モルの割合、塩基が通常1~10モルの割合で用いられる。
反応温度は通常-78~100℃の範囲内である。反応時間は通常0.1~48時間の範囲内である。
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、濃縮する等の後処理操作を行うことにより、化合物(I-E2)を単離することができる。
化合物(R3)は、公知であるか、公知の方法に準じて製造することができる。
式(I-E3)で示される化合物(以下、化合物(I-E3)と記す)は、式(II)で示される中間体Aとトリホスゲンとを、塩基の存在下で反応させた後に、式(R4)で示される化合物(以下、化合物(R4)と記す)と反応させることにより製造することができる。またこの反応はワンポットで実施することができる。
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、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類及びこれらの2つ以上の混合物が挙げられる。
塩基としては例えば、有機塩基類が挙げられる。
反応には、1モルの中間体Aに対して、トリホスゲンが通常0.3~3モルの割合、塩基が通常1~10モルの割合、化合物(R4)が通常1~10モルの割合で用いられる。
中間体Aとトリホスゲンとの反応温度は通常-78~100℃の範囲内であり、反応時間は通常0.1~48時間の範囲内である。続く化合物(R4)との反応温度は通常-78~100℃の範囲内であり、反応時間は通常0.1~48時間の範囲内である。
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、濃縮する等の後処理操作を行うことにより、化合物(I-E3)を単離することができる。
化合物(R4)は、公知であるか、公知の方法に準じて製造することができる。
本発明化合物Nは、式(III)で示される中間体Bとヨードメタンとを、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、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類及びこれらの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例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類、水素化ナトリウム及びこれらの混合物が挙げられる。
反応には、1モルの中間体Bに対して、ヨードメタンが通常1~10モルの割合、塩基が通常1~20モルの割合で用いられる。
反応温度は通常-20~100℃の範囲内である。反応時間は通常0.1~48時間の範囲内である。
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、濃縮する等の後処理操作を行うことにより、本発明化合物Nを単離することができる。
化合物(I-E1)は、式(VI)で示される中間体Dと化合物(R1)とをパラジウム触媒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、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ニトリル類、水及びこれらの2つ以上の混合物が挙げられる。
反応に用いられるパラジウム触媒としては、例えば、酢酸パラジウム(II)、{1,1’-ビス(ジフェニルホスフィノ)フェロセン}ジクロロパラジウム(II)、XPhos Pd G3、BrettPhos Pd G3、tBuBrettPhos Pd G3、XantPhos Pd G3、及びRockPhos Pd G3が挙げられる。
反応には必要に応じて、配位子、塩基又は添加物を加えてもよい。
反応に用いられる配位子としては例えば、2-(ジ-t-ブチルホスフィノ)-1,1’-ビナフチル、BrettPhos、tBuBrettPhos、RockPhos、AdBrettPhos、tBuXPhos、及び5-(ジ-t-ブチルホスフィノ)-1’,3’,5’-トリフェニル-1’H-[1,4’]ビピラゾールが挙げられる。
反応に配位子が用いられる場合、1モルの中間体Dに対して、配位子が通常0.01~1モルの割合で用いられる。
反応に用いられる塩基としては例えば、有機塩基類;アルカリ金属炭酸塩類;カリウムt-ブトキシド、ナトリウムt-ブトキシド等のアルカリ金属アルコキシド;及びリン酸三カリウムが挙げられる。
反応に塩基が用いられる場合、1モルの中間体Dに対して、塩基が通常1~10モルの割合で用いられる。
反応に用いられる添加物としては例えば、ヨウ化ナトリウム及びヨウ化カリウムが挙げられる。
反応に添加物が用いられる場合、1モルの中間体Dに対して、添加物が通常0.1~10モルの割合で用いられる。
反応には、1モルの中間体Dに対して、化合物(R1)が通常1~10モルの割合、パラジウム触媒が通常0.01~1モルの割合で用いられる。
反応温度は通常0~150℃の範囲内である。反応時間は通常0.1~120時間の範囲内である。
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、濃縮する等の後処理操作を行うことにより、化合物(I-E1)を単離することができる。
化合物(R1)は、公知であるか、公知の方法に準じて製造することができる。
本発明化合物NのNオキシドは、本発明化合物N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、例えば、米国特許出願公開第2018/0009778号明細書又は国際公開第2016/121970号に記載の方法に準じて実施することができる。
式(II)で示される中間体Aは、式(II-A)で示される化合物(以下、化合物(II-A)と記す)とビス(ピナコラト)ジボロンとを塩基及びパラジウム触媒の存在下で反応させて式(II-B)で示される化合物(以下、化合物(II-B)と記す)を得た後、化合物(II-B)を酸化す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、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、エステル類、ジメチルスルホキシド(以下、DMSOと記す)等のスルホキシド(以下、スルホキシド類と記す。)、ニトリル類及びこれらの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例えば、有機塩基類、アルカリ金属炭酸塩類、アルカリ金属炭酸水素塩類及びリン酸三カリウムが挙げられる。
パラジウム触媒としては、例えば、[1,1’-ビス(ジフェニルホスフィノ)フェロセン]パラジウム(II)ジクロリドが挙げられる。
反応には、化合物(II-A)1モルに対して、ビス(ピナコラト)ジボロンが通常1~5モルの割合、塩基が通常1~5モルの割合、パラジウム触媒が通常0.01~0.5モルの割合で用いられる。
反応温度は通常0~150℃の範囲内であり、反応時間は通常0.1~48時間の範囲内である。
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、濃縮する等の後処理操作を行うことにより、化合物(II-B)を単離することができる。
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、炭化水素類;エーテル類;ハロゲン化炭化水素類;アミド類;エステル類;ニトリル類;メタノール、エタノール、プロパノール、ブタノール等のアルコール(以下、アルコール類と記す。);水及びこれら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、メタクロロ過安息香酸及び過酸化水素水が挙げられる。
酸化剤として過酸化水素水を用いる場合は、必要に応じて塩基を加えてもよい。
塩基としては、水酸化ナトリウム及び水酸化カリウムが挙げられる。
反応には、化合物(II-B)1モルに対して、酸化剤が通常1~5モルの割合で用いられる。
反応に塩基が用いられる場合、化合物(II-B)1モルに対して、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℃の範囲内であり、反応時間は通常0.1~48時間の範囲内である。
反応終了後は、反応混合物に水及びチオ硫酸ナトリウム等の還元剤を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、中間体Aを単離することができる。
化合物(II-A)は、公知であるか、公知の方法に準じて製造することができる。
式(III)で示される中間体Bは、式(V)で示される化合物(以下、化合物(V)と記す)とギ酸メチル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、炭化水素類、エーテル類、ハロゲン化炭化水素類、アミド類、ニトリル類及びこれらの2つ以上の混合物が挙げられる。
塩基としては例えば、水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物;ナトリウムメトキシド、ナトリウムエトキシド、カリウムt-ブトキシド等のアルカリ金属アルコキシド;ナトリウムアミド、リチウムアミド、リチウムジイソプロピルアミド、ナトリウムヘキサメチルジシラジド、リチウムヘキサメチルジシラジド等のアルカリ金属アミド;及びこれらの混合物が挙げられる。
反応には、化合物(V)1モルに対して、ギ酸メチルが通常1~100モルの割合、塩基が通常1~10モルの割合で用いられる。
反応温度は通常-20~80℃の範囲内である。反応時間は通常0.1~48時間の範囲内である。
反応終了後は、反応混合物に希塩酸などの酸性水溶液を加え、有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、中間体Bを単離することができる。
式(V-E1)で示される化合物(以下、化合物(V-E1)と記す)は、式(V-A)で示される化合物(以下、化合物(V-A)と記す)と化合物(R1)とを、ホスフィン類及びアゾジエステル類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、中間体Aに代えて化合物(V-A)を用い、製造法Aに準じて実施することができる。
化合物(V-A)は、公知であるか、公知の方法に準じて製造することができる。
式(V-E2)で示される化合物(以下、化合物(V-E2)と記す)は、化合物(V-A)と化合物(R3)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、中間体Aに代えて化合物(V-A)を用い、製造法Cに準じて実施することができる。
中間体Dは、式(VI-A)で示される化合物(以下、化合物(VI-A)と記す)とヨードメタンとを、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、中間体Bに代えて化合物(VI-A)を用い、製造法Eに準じて実施することができる。
化合物(VI-A)は、式(VI-B)で示される化合物(以下、化合物(VI-B)と記す)とギ酸メチル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、化合物(V)に代えて化合物(VI-B)を用い、参考製造法Bに準じて実施することができる。
化合物(VI-B)は、公知であるか、公知の方法に準じて製造することができる。
前記混用又は併用とは、本発明化合物と本成分とを、同時に、別々に又は時間間隔をおいて使用することを意味する。
本発明化合物と本成分とを同時に使用する場合、本発明化合物及び本成分が、それぞれ別個の製剤に含まれていてもよく、1つの製剤に含まれていてもよい。
本発明の1つの側面は、群(a)、群(b)、群(c)及び群(d)からなる群より選ばれる1以上の成分、並びに本発明化合物を含有する(以下、組成物Aと記す)である。
なお、SXの略号は、実施例に記載の化合物群SX1~SX80から選ばれるいずれか1つの本発明化合物を意味する。また、以下に記載する本成分はいずれも公知の成分であり、市販の製剤から得るか、公知の方法により製造することができる。本成分が微生物の場合は、菌寄託機関から入手することもできる。なお、括弧内の数字はCAS RN(登録商標)を表す。
アバメクチン(abamectin) + SX, アセフェート(acephate) + SX, アセキノシル(acequinocyl) + SX, アセタミプリド(acetamiprid) + SX, アセトプロール(acetoprole) + SX, アクリナトリン(acrinathrin) + SX, アシノナピル(acynonapyr) + SX, アフィドピロペン(afidopyropen) + SX, アフォキソラネル(afoxolaner) + SX, アラニカルブ(alanycarb) + SX, アルジカルブ(aldicarb) + SX, アレスリン(allethrin) + SX, アルファシペルメトリン(alpha-cypermethrin) + SX, アルファエンドスルファン(alpha-endosulfan) + SX, リン化アルミニウム(aluminium phosphide) + SX, アミトラズ(amitraz) + SX, アザジラクチン(azadirachtin) + SX, アザメチホス(azamethiphos) + SX, アジンホスエチル(azinphos-ethyl) + SX, アジンホスメチル(azinphos-methyl) + SX, アゾシクロチン(azocyclotin) + SX, Celastrus angulatus樹皮(bark of Celastrus angulatus) + SX, ベンダイオカルブ(bendiocarb) + SX, ベンフルトリン(benfluthrin) + SX, ベンフラカルブ(benfuracarb) + SX, ベンスルタップ(bensultap) + SX, ベンゾキシメート(benzoximate) + SX, ベンズピリモキサン(benzpyrimoxan) + SX, ベータシフルトリン(beta-cyfluthrin) + SX, べータシペルメトリン(beta-cypermethrin) + SX, ビフェナゼート(bifenazate) + SX, ビフェントリン(bifenthrin) + SX, ビオアレスリン(bioallethrin) + SX, ビオレスメトリン(bioresmethrin) + SX, ビストリフルロン(bistrifluron) + SX, ホウ砂(borax) + SX, ホウ酸(boric acid) + SX, ブロフラニリド(broflanilide) + SX, ブロモプロピレート(bromopropylate) + SX, ブプロフェジン(buprofezin) + SX, ブトカルボキシム(butocarboxim) + SX, ブトキシカルボキシム(butoxycarboxim) + SX, カズサホス(cadusafos) + SX, リン化カルシウム(calcium phosphide) + SX, カルバリル(carbaryl) + SX, カルボフラン(carbofuran) + SX, カルボスルファン(carbosulfan) + SX, カルタップ塩酸塩(cartap hydrochloride) + SX, カルタップ(cartap) + SX, キノメチオナート(chinomethionat) + SX, クロラントラニリプロール(chlorantraniliprole) + SX, クロルデン(chlordane) + SX, クロレトキシホス(chlorethoxyfos) + SX, クロルフェナピル(chlorfenapyr) + SX, クロルフェンビンホス(chlorfenvinphos) + SX, クロルフルアズロン(chlorfluazuron) + SX, クロルメホス(chlormephos) + SX, クロルピクリン(chloropicrin) + SX, クロルピリホス(chlorpyrifos) + SX, クロルピリホスメチル(chlorpyrifos-methyl) + SX, クロマフェノジド(chromafenozide) + SX, クロフェンテジン(clofentezine) + SX, クロチアニジン(clothianidin) + SX, コンカナマイシンA(concanamycin A) + SX, クマホス(coumaphos) + SX, クリオライト(cryolite) + SX, シアノホス(cyanophos) + SX, シアントラニリプロール(cyantraniliprole) + SX, シクラニリプロール(cycloniliprole) + SX, シクロプロトリン(cycloprothrin) + SX, シクロキサプリド(cycloxaprid) + SX, シエノピラフェン(cyenopyrafen) + SX, シフルメトフェン(cyflumetofen) + SX, シフルトリン(cyfluthrin) + SX, シハロジアミド(cyhalodiamide) + SX, シハロトリン(cyhalothrin) + SX, シヘキサチン(cyhexatin) + SX, シペルメトリン(cypermethrin) + SX, シフェノトリン(cyphenothrin) + SX, シロマジン(cyromazine) + SX, ダゾメット(dazomet) + SX, デルタメトリン(deltamethrin) + SX, デメトン-S-メチル(demeton-S-methyl) + SX, ジアフェンチウロン(diafenthiuron) + SX, ダイアジノン(diazinon) + SX, ジクロルボス(dichlorvos) + SX, ジクロロメゾチアズ(dicloromezotiaz) + SX, ジコホル(dicofol) + SX, ジクロトホス(dicrotophos) + SX, ジフロビダジン(diflovidazin) + SX, ジフルベンズロン(diflubenzuron) + SX, ジメフルトリン(dimefluthrin) + SX, ジメトエート(dimethoate) + SX, ジメチルビンホス(dimethylvinphos) + SX, dimpropyridaz + SX, ジノテフラン(dinotefuran) + SX, 八ホウ酸二ナトリウム(disodium octaborate) + SX, ジスルホトン(disulfoton) + SX, DNOC(2-methyl-4,6-dinitrophenol) + SX, ドラメクチン(doramectin) + SX, セイヨウオシダ乾燥葉(dried leaves of Dryopteris filix-mas) + SX, エマメクチン安息香酸塩(emamectin-benzoate) + SX, エンペントリン(empenthrin) + SX, エンドスルファン(endosulfan) + SX, EPN(O-ethyl O-(4-nitrophenyl) phenylphosphonothioate) + SX, イプシロンメトフルトリン(epsilon-metofluthrin) + SX, イプシロンモンフルオロトリン(epsilon-momfluorothrin) + SX, エスフェンバレレート(esfenvalerate) + SX, エチオフェンカルブ(ethiofencarb) + SX, エチオン(ethion) + SX, エチプロール(ethiprole) + SX, エトプロホス(ethoprophos) + SX, エトフェンプロックス(etofenprox) + SX, エトキサゾール(etoxazole) + SX, ニガヨモギ抽出物(extract of Artemisia absinthium) + SX, Cassia nigricans抽出物(extract of Cassia nigricans) + SX, クリトリア・テルナテアの抽出物(extract of clitoria ternatea) + SX, ヒレハリソウ抽出物(extract of Symphytum officinale) + SX, アリタソウ抽出物(extracts or simulated blend of Chenopodium ambrosioides) + SX, タンジー抽出物(extract of Tanacetum vulgare) + SX, セイヨウイラクサ抽出物(extract of Urtica dioica) + SX, ヤドリギ抽出物(extract of Viscum album) + SX, ファンフル(famphur) + SX, フェナミホス(fenamiphos) + SX, フェナザキン(fenazaquin) + SX, 酸化フェンブタスズ(fenbutatin oxide) + SX, フェニトロチオン(fenitrothion) + SX, フェノブカルブ(fenobucarb) + SX, フェノキシカルブ(fenoxycarb) + SX, フェンプロパトリン(fenpropathrin) + SX, フェンピロキシメート(fenpyroximate) + SX, フェンチオン(fenthion) + SX, フェンバレレート(fenvalerate) + SX, フィプロニル(fipronil) + SX, フロメトキン(flometoquin) + SX, フロニカミド(flonicamid) + SX, フルアクリピリム(fluacrypyrim) + SX, フルアザインドリジン(fluazaindolizine) + SX, フルアズロン(fluazuron) + SX, フルベンジアミド(flubendiamide) + SX, フルシクロクスロン(flucycloxuron) + SX, フルシトリネート(flucythrinate) + SX, フルエンスルホン(fluensulfone) + SX, フルフェンプロックス(flufenoprox) + SX, フルフェノクスロン(flufenoxuron) + SX, フルフィプロール(flufiprole) + SX, フルメトリン(flumethrin) + SX, フルピラジフロン(flupyradifurone) + SX, フルピリミン(flupyrimin) + SX, フルララネル(fluralaner) + SX, フルバリネート(fluvalinate) + SX, フルキサメタミド(fluxametamide) + SX, ホルメタネート(formetanate) + SX, ホスチアゼート(fosthiazate) + SX, フラメトリン(furamethrin) + SX, フラチオカルブ(furathiocarb) + SX, ガンマシハロトリン(gamma-cyhalothrin) + SX, GS-オメガ/カッパHXTX-Hv1aペプチド(GS-omega/kappa HXTX-Hv1a peptide) + SX, ハルフェンプロックス(halfenprox) + SX, ハロフェノジド(halofenozide) + SX, ヘプタフルトリン(heptafluthrin) + SX, ヘプテノホス(heptenophos) + SX, ヘキサフルムロン(hexaflumuron) + SX, ヘキシチアゾクス(hexythiazox) + SX, ホップベータ酸のカリウム塩(potassium salt of hop beta acid) + SX, ヒドラメチルノン(hydramethylnon) + SX, ヒドロプレン(hydroprene) + SX, イミシアホス(imicyafos) + SX, イミダクロプリド(imidacloprid) + SX, イミダクロチズ(imidaclothiz) + SX, イミプロトリン(imiprothrin) + SX, インドキサカルブ(indoxacarb) + SX, イソシクロセラム(isocycloseram) + SX, イソフェンホス(isofenphos) + SX, イソプロカルブ(isoprocarb) + SX, 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-(methoxyaminothiophosphoryl) salicylate) + SX, イソキサチオン(isoxathion) + SX, イベルメクチン(ivermectin) + SX, カデスリン(kadethrin) + SX, カッパテフルトリン(kappa-tefluthrin) + SX, カッパビフェントリン(kappa-bifenthrin) + SX, キノプレン(kinoprene) + SX, ラムダシハロトリン(lambda-cyhalothrin) + SX, レノレマイシン(lenoremycin) + SX, レピメクチン(lepimectin) + SX, 石灰硫黄合剤(lime sulfur) + SX, ロチラネル(lotilaner) + SX, ルフェヌロン(lufenuron) + SX, マシン油(machine oil) + SX, マラチオン(malathion) + SX, メカルバム(mecarbam) + SX, メペルフルトリン(meperfluthrin) + SX, メタフルミゾン(metaflumizone) + SX, メタム(metam) + SX, メタミドホス(methamidophos) + SX, メチダチオン(methidathion) + SX, メチオカルブ(methiocarb) + SX, メソミル(methomyl) + SX, メトプレン(methoprene) + SX, メトキシクロル(methoxychlor) + SX, メトキシフェノジド(methoxyfenozide) + SX, 臭化メチル(methyl bromide) + SX, メトフルトリン(metofluthrin) + SX, メトルカルブ(metolcarb) + SX, メトキサジアゾン(metoxadiazone) + SX, メビンホス(mevinphos) + SX, ミルベメクチン(milbemectin) + SX, ミルベマイシンオキシム(milbemycin oxime) + SX, モンフルオロトリン(momfluorothrin) + SX, モノクロトホス(monocrotophos) + SX, モキシデクチン(moxidectin) + SX, ナレッド(naled) + SX, ニーム油(neem oil) + SX, ニコチン(nicotine) + SX, 硫酸ニコチン(nicotine-sulfate) + SX, ニテンピラム(nitenpyram) + SX, ノバルロン(novaluron) + SX, ノビフルムロン(noviflumuron) + SX, アメリカアリタソウ種子油(oil of the seeds of Chenopodium anthelminticum) + SX, オメトエート(omethoate) + SX, オキサミル(oxamyl) + SX, オキサゾスルフィル(oxazosulfyl) + SX, オキシジメトンメチル(oxydemeton-methyl) + SX, パラチオン(parathion) + SX, パラチオンメチル(parathion-methyl) + SX, ペルメトリン(permethrin) + SX, フェノトリン(phenothrin) + SX, フェントエート(phenthoate) + SX, ホレート(phorate) + SX, ホサロン(phosalone) + SX, ホスメット(phosmet) + SX, ホスファミドン(phosphamidon) + SX, ホスフィン(phosphine) + SX, ホキシム(phoxim) + SX, ピリミカーブ(pirimicarb) + SX, ピリミホスメチル(pirimiphos-methyl) + SX, プラレトリン(prallethrin) + SX, プロフェノホス(profenofos) + SX, プロフルトリン(profluthrin) + SX, プロパルギット(propargite) + SX, プロペタムホス(propetamphos) + SX, プロポキスル(propoxur) + SX, アルギニン酸プロピレングリコール(propylene glycol alginate) + SX, プロチオホス(prothiofos) + SX, ピフルブミド(pyflubumide) + SX, ピメトロジン(pymetrozine) + SX, ピラクロホス(pyraclofos) + SX, ピレトリン(pyrethrins) + SX, ピリダベン(pyridaben) + SX, ピリダリル(pyridalyl) + SX, ピリダフェンチオン(pyridaphenthion) + SX, ピリフルキナゾン(pyrifluquinazone) + SX, ピリミジフェン(pyrimidifen) + SX, ピリミノストロビン(pyriminostrobin) + SX, ピリプロール(pyriprole) + SX, ピリプロキシフェン(pyriproxyfen) + SX, キナルホス(quinalphos) + SX, レスメトリン(resmethrin) + SX, ロテノン(rotenone) + SX, リアノジン(ryanodine) + SX, サロラネル(sarolaner) + SX, セラメクチン(selamectin) + SX, シグマシペルメトリン(sigma-cypermethrin) + SX, シラフルオフェン(silafluofen) + SX, ホウ酸ナトリウム(sodium borate) + SX, メタホウ酸ナトリウム(sodium metaborate) + SX, スピネトラム(spinetoram) + SX, スピノサド(spinosad) + SX, スピロジクロフェン(spirodiclofen) + SX, スピロメシフェン(spiromesifen) + SX, スピロピジオン(spiropidion) + SX, スピロテトラマト(spirotetramat) + SX, スルフルラミド(sulfluramid) + SX, スルホテップ(sulfotep) + SX, スルホキサフロル(sulfoxaflor) + SX, 硫黄(sulfur) + SX, フッ化スルフリル(sulfuryl fluoride) + SX, 吐酒石(tartar emetic) + SX, タウフルバリネート(tau-fluvalinate) + SX, テブフェノジド(tebufenozide) + SX, テブフェンピラド(tebufenpyrad) + SX, テブピリムホス(tebupirimfos) +
SX, テフルベンズロン(teflubenzuron) + SX, テフルトリン(tefluthrin) + SX, テメホス(temephos) + SX, テルブホス(terbufos) + SX, アリタソウから抽出したテルペン成分(terpene constituents of the extract of chenopodium ambrosioides near ambrosioides) + SX, テトラクロラントラニリプロール(tetrachlorantraniliprole) + SX, テトラクロルビンホス(tetrachlorvinphos) + SX, テトラジホン(tetradifon) + SX, テトラメトリン(tetramethrin) + SX, テトラメチルフルトリン(tetramethylfluthrin) + SX, テトラニリプロール(tetraniliprole) + SX, シータシペルメトリン(theta-cypermethrin) + SX, チアクロプリド(thiacloprid) + SX, チアメトキサム(thiamethoxam) + SX, チオシクラム(thiocyclam) + SX, チオジカルブ(thiodicarb) + SX, チオファノックス(thiofanox) + SX, チオメトン(thiometon) + SX, チオスルタップ二ナトリウム塩(thiosultap-disodium) + SX, チオスルタップ一ナトリウム塩(thiosultap-monosodium) + SX, チオキサザフェン(tioxazafen) + SX, トルフェンピラド(tolfenpyrad) + SX, トラロメトリン(tralomethrin) + SX, トランスフルトリン(transfluthrin) + SX, トリアザメート(triazamate) + SX, トリアゾホス(triazophos) + SX, トリクロルホン(trichlorfon) + SX, トリフルメゾピリム(triflumezopyrim) + SX, トリフルムロン(triflumuron) + SX, トリメタカルブ(trimethacarb) + SX, チクロピラゾフロル(tyclopyrazoflor) + SX, バミドチオン(vamidothion) + SX, スリナムニガキ木材抽出成分(wood extract of Quassia amara) + SX, XMC (3,5-dimethylphenyl N-methylcarbamate) + SX, キシリルカルブ(xylylcarb) + SX, ゼータシペルメトリン(zeta-cypermethrin) + SX, リン化亜鉛(zinc phosphide) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoropropanesulfinyl)propanamide (1477923-37-7) + SX, 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide (1241050-20-3) + SX, 3-methoxy-N-(5-{5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}indan-1-yl)propanamide (1118626-57-5) + SX, N-[2-bromo-6-chloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-{ethyl[(pyridin-4-yl)carbonyl]amino}-2-methoxybenzamide (1429513-53-0) + SX, N-[2-bromo-6-chloro-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-[ethyl(4-cyanobenzoyl)amino]-2-methoxybenzamide (1609007-65-9) + SX, N-[2-bromo-6-(difluoromethoxy)-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-3-{methyl[(pyridin-4-yl)carbonyl]amino}-2-methoxybenzamide (1630969-78-6) + SX, 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfanyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (885026-50-6) + SX, (1Z)-2-(4-tert-butylphenyl)-2-cyano-1-(1-ethyl-3-methyl-1H-pyrazol-5-yl)ethenyl 2,2-dimethylpropanoate (1253429-01-4) + SX, N-[(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide + SX, BT作物のタンパク質Cry1Ab (BT crop protein Cry1Ab) + SX, BT作物のタンパク質Cry1Ac (BT crop protein Cry1Ac) + SX, BT作物のタンパク質Cry1Fa (BT crop protein Cry1Fa) + SX, BT作物のタンパク質Cry1A.105 (BT crop protein Cry1A.105) + SX, BT作物のタンパク質Cry2Ab (BT crop protein Cry2Ab) + SX, BT作物のタンパク質Vip3A (BT crop protein Vip3A) + SX, BT作物のタンパク質Cry3A (BT crop protein Cry3A) + SX, BT作物のタンパク質Cry3Ab (BT crop protein Cry3Ab) + SX, BT作物のタンパク質Cry3Bb (BT crop protein Cry3Bb) + SX, BT作物のタンパク質Cry34Ab1/Cry35Ab1 (BT crop protein Cry34Ab1/Cry35Ab1) + SX, アドクソフィエス・オラナ顆粒病ウイルスBV-0001株(Adoxophyes orana granulosis virus strain BV-0001) + SX, アンチカルシア・ゲマタリス核多角体病ウイルス(Anticarsia gemmatalis mNPV) + SX, オートグラファ・カリフォルニア核多角体病ウイルス(Autographa californica mNPV) + SX, シジア・ポモネラ顆粒病ウイルスV15株(Cydia pomonella GV strain V15) + SX, シジア・ポモネラ顆粒病ウイルスV22株(Cydia pomonella GV strain V22) + SX, クリプトフレビア・ロイコトレタ顆粒病ウイルス(Cryptophlebia leucotreta GV) + SX, デンドロリムス・プンクタタス細胞質多面体ウイルス(Dendrolimus punctatus cypovirus) + SX, ヘリコベルパ・アルミゲラ核多角体病ウイルスBV-0003株(Helicoverpa armigera NPV strain BV-0003) + SX, ヘリコベルパ・ゼア核多角体病ウイルス(Helicoverpa zea NPV) + SX, リュマントリア・ディスパル核多角体病ウイルス(Lymantria dispar NPV) + SX, マメストラ・ブラシカエ核多角体病ウイルス(Mamestra brassicae NPV) + SX, マメストラ・コンフィグラタ核多角体病ウイルス(Mamestra configurata NPV) + SX, ネオディプリオン・アビエンティス核多角体病ウイルス(Neodiprion abietis NPV) + SX, ネオディプリオン・レコンテイ核多角体病ウイルス(Neodiprion lecontei NPV) + SX, ネオディプリオン・セルティファー核多角体病ウイルス(Neodiprion sertifer NPV) + SX, ノゼマ・ロクスタエ(Nosema locustae) + SX, オルギイア・プソイドツガタ核多角体病ウイルス(Orgyia pseudotsugata NPV) + SX, ピエリス・ラパエ顆粒病ウイルス(Pieris rapae GV) + SX, プロジア・インテルプンクテラ顆粒病ウイルス(Plodia interpunctella GV) + SX, スポドプテラ・エクシグア核多角体病ウイルス(Spodoptera exigua mNPV) + SX, スポドプテラ・リットラリス核多角体病ウイルス(Spodoptera littoralis mNPV) + SX, スポドプテラ・リツラ核多角体病ウイルス(Spodoptera litura NPV) + SX, Arthrobotrys dactyloides + SX, Bacillus firmus strain GB-126 + SX, Bacillus firmus strain I-1582 + SX, Bacillus megaterium + SX, Bacillus sp. strain AQ175 + SX, Bacillus sp. strain AQ177 + SX, Bacillus sp. strain AQ178 + SX, Bacillus sphaericus strain 2362 + SX, Bacillus sphaericus strain ABTS1743 + SX, Bacillus sphaericus Serotype strain H5a5b + SX, Bacillus thuringiensis strain AQ52 + SX, Bacillus thuringiensis strain BD#32 + SX, Bacillus thuringiensis strain CR-371 + SX, Bacillus thuringiensis subsp. Aizawai strain ABTS-1857 + SX, Bacillus thuringiensis subsp. Aizawai strain AM65-52 + SX, Bacillus thuringiensis subsp. Aizawai strain GC-91 + SX, Bacillus thuringiensis subsp. Aizawai Serotype strain H-7 + SX, Bacillus thuringiensis subsp. Kurstaki strain ABTS351 + SX, Bacillus thuringiensis subsp. Kurstaki strain BMP123 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG234 + SX, Bacillus thuringiensis subsp. Kurstaki strain EG7841 + SX, Bacillus thuringiensis subsp. Kurstaki strain EVB113-19 + SX, Bacillus thuringiensis subsp. Kurstaki strain F810 + SX, Bacillus thuringiensis subsp. Kurstaki strain HD-1 + SX, Bacillus thuringiensis subsp. Kurstaki strain PB54 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-11 + SX, Bacillus thuringiensis subsp. Kurstaki strain SA-12 + SX, Bacillus thuringiensis subsp. Tenebriosis strain NB176 + SX, Bacillus thuringiensis subsp. Thuringiensis strain MPPL002 + SX, Bacillus thuringiensis subsp.morrisoni + SX, Bacillus thuringiensis var. colmeri + SX, Bacillus thuringiensis var. darmstadiensis strain 24-91 + SX, Bacillus thuringiensis var. dendrolimus + SX, Bacillus thuringiensis var. galleriae + SX, Bacillus thuringiensis var. israelensis strain BMP144 + SX, Bacillus thuringiensis var. israelensis serotype strain H-14 + SX, Bacillus thuringiensis var. japonensis strain buibui + SX, Bacillus thuringiensis var. san diego strain M-7 + SX, Bacillus thuringiensis var.7216 + SX, Bacillus thuringiensis var.aegypti + SX, Bacillus thuringiensis var. T36 + SX, Beauveria bassiana strain ANT-03 + SX, Beauveria bassiana strain ATCC74040 + SX, Beauveria bassiana strain GHA + SX, Beauveria brongniartii + SX, Burkholderia rinojensis strain A396 + SX, Chromobacterium subtsugae strain PRAA4-1T + SX, Dactyllela ellipsospora + SX, Dectylaria thaumasia + SX, Hirsutella minnesotensis + SX, Hirsutella rhossiliensis + SX, Hirsutella thompsonii + SX, Lagenidium giganteum + SX, Lecanicillium lecanii strain KV01 + SX, Lecanicillium lecanii conidia of strain DAOM198499 + SX, Lecanicillium lecanii conidia of strain DAOM216596 + SX, Lecanicillium muscarium strain Ve6 + SX, Metarhizium anisopliae strain F52 + SX, Metarhizium anisopliae var. acridum + SX, Metarhizium anisopliae var. anisopliae BIPESCO 5/F52 + SX, Metarhizium flavoviride + SX, Monacrosporium phymatopagum + SX, Paecilomyces fumosoroseus Apopka strain 97 + SX, Paecilomyces lilacinus strain 251 + SX, Paecilomyces tenuipes strain T1 + SX, Paenibacillus popilliae + SX, Pasteuria nishizawae strain Pn1 + SX, Pasteuria penetrans + SX, Pasteuria usgae + SX, Pasteuria thoynei + SX, Serratia entomophila + SX, Verticillium chlamydosporium + SX, Verticillium lecani strain NCIM1312 + SX, 2-chloro-4-fluoro-5-{[5-(trifluoromethylthio)pentyl]oxy}phenyl 2,2,2-trifluoroethyl sulfoxide (1472050-04-6) + SX, 4-chloro-5-[2,2-difluoro-2-(3,4,5-trifluorophenyl)ethoxy]-2-methylphenyl 2,2,2-trifluoroethyl sulfoxide (1632218-00-8) + SX, 4-fluoro-5-[2,2-difluoro-2-(3,4,5-trifluorophenyl)ethoxy]-2-methylphenyl 2,2,2-trifluoroethyl sulfoxide (1632217-98-1) + SX, 2-({2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}imino)-3-(2,2,2-trifluoroethyl)-1,3-thiazolidin-4-one (1445683-71-5) + SX, (3R)-3-(2-chlorothiazol-5-yl)-8-methyl-7-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-4-ium-5-olate (2249718-27-0) + SX, N-{4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl}-1-methyl-4-(methanesulfonyl)-3-(1,1,2,2,2-pentafluoroethyl)-1H-pyrazole-3-carboxamide (1400768-21-9) + SX, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]tetradec-11-en-10-one (907187-07-9) + SX, 3-(4'-fluoro-2,4-dimethyl[1,1'-biphenyl]-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one (1031385-91-7) + SX, N-[3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl]-2-(methanesulfonyl)propanamide (2396747-83-2) + SX, 2-isopropyl-5-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]-1,3,4-thiadiazole (2058052-95-0) + SX, ニコフルプロール(nicofluprole) + SX, 1,4-dimethyl-2-[2-(3-pyridinyl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione (2171099-09-3) + SX。
アシベンゾラルSメチル(acibenzolar-S-methyl) + SX, アルジモルフ(aldimorph) + SX, アメトクトラジン(ametoctradin) + SX, アミノピリフェン(aminopyrifen) + SX, アミスルブロム(amisulbrom) + SX, アニラジン(anilazine) + SX, アザコナゾール(azaconazole) + SX, アゾキシストロビン(azoxystrobin) + SX, 塩基性硫酸銅(basic copper sulfate) + SX, ベナラキシル(benalaxyl) + SX, ベナラキシルM(benalaxyl-M) + SX, ベノダニル(benodanil) + SX, ベノミル(benomyl) + SX, ベンチアバリカルブ(benthiavalicarb) + SX, ベンチアバリカルブイソプロピル(benthivalicarb-isopropyl) + SX, ベンゾビンジフルピル(benzovindiflupyr) + SX, ビナパクリル(binapacryl) + SX, ビフェニル(biphenyl) + SX, ビテルタノール(bitertanol) + SX, ビキサフェン(bixafen) + SX, ブラストサイジンS(blasticidin-S) + SX, ボルドー液(Bordeaux mixture) + SX, ボスカリド(boscalid) + SX, ブロモタロニル(bromothalonil) + SX, ブロムコナゾール(bromuconazole) + SX, ブピリメート(bupirimate) + SX, キャプタホール(captafol) + SX, キャプタン(captan) + SX, カルベンダジム(carbendazim) + SX, カルボキシン(carboxin) + SX, カルプロパミド(carpropamid) + SX, キノメチオナート(chinomethionat) + SX, キチン(chitin) + SX, クロロネブ(chloroneb) + SX, クロロタロニル(chlorothalonil) + SX, クロゾリネート(chlozolinate) + SX, コレトクロリンB(colletochlorin B) + SX, 酢酸銅(II) (copper(II) acetate) + SX, 水酸化銅(II) (copper(II) hydroxide) + SX, 塩基性塩化銅(copper oxychloride) + SX, 硫酸銅(II) (copper(II) sulfate) + SX, クモキシストロビン(coumoxystrobin) + SX, シアゾファミド(cyazofamid) + SX, シフルフェナミド(cyflufenamid) + SX, シモキサニル(cymoxanil) + SX, シプロコナゾール(cyproconazole) + SX, シプロジニル(cyprodinil) + SX, ジクロベンチアゾクス(dichlobentiazox) + SX, ジクロフルアニド(dichlofluanid) + SX, ジクロシメット(diclocymet) + SX, ジクロメジン(diclomezine) + SX, ジクロラン(dicloran) + SX, ジエトフェンカルブ(diethofencarb) + SX, ジフェノコナゾール(difenoconazole) + SX, ジフルメトリム(diflumetorim) + SX, ジメタクロン(dimethachlone) + SX, ジメチリモール(dimethirimol) + SX, ジメトモルフ(dimethomorph) + SX, ジモキシストロビン(dimoxystrobin) + SX, ジニコナゾール(diniconazole) + SX, ジニコナゾールM(diniconazole-M) + SX, ジノカップ(dinocap) + SX, 亜リン酸水素二カリウム(dipotassium hydrogenphosphite) + SX, ジピメティトロン(dipymetitrone) + SX, ジチアノン(dithianon) + SX, ドデシルベンゼンスルホン酸ビスエチレンジアミン銅(II)錯塩(dodecylbenzenesulphonic acid bisethylenediamine copper(II) salt) + SX, ドデモルフ(dodemorph) + SX, ドジン(dodine) + SX, エジフェンホス(edifenphos) + SX, エノキサストロビン(enoxastrobin) + SX, エポキシコナゾール(epoxiconazole) + SX, エタコナゾール(etaconazole) + SX, エタボキサム(ethaboxam) + SX, エチリモール(ethirimol) + SX, エトリジアゾール(etridiazole) + SX, ティーツリー抽出物(extract from Melaleuca alternifolia) + SX, オオイタドリ抽出物(extract from Reynoutria sachalinensis) + SX, ハウチワマメ苗木の子葉からの抽出物(extract from the cotyledons of lupine plantlets("BLAD")) + SX, ニンニク抽出成分(extract of Allium sativum) + SX, スギナ抽出成分(extract of Equisetum arvense) + SX, キンレンカ抽出成分(extract of Tropaeolum majus) + SX, ファモキサドン(famoxadone) + SX, フェンアミドン(fenamidone) + SX, フェナミンストロビン(fenaminstrobin) + SX, フェナリモル(fenarimol) + SX, フェンブコナゾール(fenbuconazole) + SX, フェンフラム(fenfuram) + SX, フェンヘキサミド(fenhexamid) + SX, フェノキサニル(fenoxanil) + SX, フェンピクロニル(fenpiclonil) + SX, フェンピコキサミド(fenpicoxamid) + SX, フェンプロピジン(fenpropidin) + SX, フェンプロピモルフ(fenpropimorph) + SX, フェンピラザミン(fenpyrazamine) + SX, 酢酸トリフェニル錫(fentin acetate) + SX, 塩化トリフェニル錫(fentin chloride) + SX, 水酸化トリフェニル錫(fentin hydroxide) + SX, フェルバム(ferbam) + SX, フェリムゾン(ferimzone) + SX, フロリルピコキサミド(florylpicoxamid) + SX, フルアジナム(fluazinam) + SX, フルジオキソニル(fludioxonil) + SX, フルフェノキシストロビン(flufenoxystrobin) + SX, フルインダピル(fluindapyr) + SX, フルモルフ(flumorph) + SX, フルオピコリド(fluopicolide) + SX, フルオピラム(fluopyram) + SX, フルオピモミド(fluopimomide) + SX, フルオルイミド(fluoroimide) + SX, フルオキサピプロリン(fluoxapiprolin) +SX, フルオキサストロビン(fluoxastrobin) + SX, フルキンコナゾール(fluquinconazole) + SX, フルシラゾール(flusilazole) + SX, フルスルファミド(flusulfamide) + SX, フルチアニル(flutianil) + SX, フルトラニル(flutolanil) + SX, フルトリアホール(flutriafol) + SX, フルキサピロキサド(fluxapyroxad) + SX, ホルペット(folpet) + SX, ホセチル(fosetyl) + SX, ホセチルアルミニウム(fosetyl-aluminium) + SX, フベリダゾール(fuberidazole) + SX, フララキシル(furalaxyl) + SX, フラメトピル(furametpyr) + SX, グアザチン(guazatine) + SX, ヘキサコナゾール(hexaconazole) + SX, ヒメキサゾール(hymexazole) + SX, イマザリル(imazalil) + SX, イミベンコナゾール(imibenconazole) + SX, イミノクタジン(iminoctadine) + SX, イミノクタジン酢酸塩(iminoctadine triacetate) + SX, インピルフルキサム(inpyrfluxam) + SX, ヨードカルブ(iodocarb) + SX, イプコナゾール(ipconazole) + SX, イプフェントリフルコナゾール(ipfentrifluconazole) + SX, イプフルフェノキン(ipflufenoquin) + SX, イプロベンホス(iprobenfos) + SX, イプロジオン(iprodione) + SX, イプロバリカルブ(iprovalicarb) + SX, イソフェタミド(isofetamid) + SX, イソフルシプラム(isoflucypram) + SX, イソプロチオラン(isoprothiolane) + SX, イソピラザム(isopyrazam) + SX, イソチアニル(isotianil) + SX, カスガマイシン(kasugamycin) + SX, クレソキシムメチル(kresoxim-methyl) + SX, ラミナリン(laminarin) + SX, オークの葉及び樹皮(leaves and bark of Quercus) + SX, マンコゼブ(mancozeb) + SX, マンデストロビン(mandestrobin) + SX, マンジプロパミド(mandipropamid) + SX, マンネブ(maneb) + SX, メフェントリフルコナゾール(mefentrifluconazole) + SX, メパニピリム(mepanipyrim) + SX, メプロニル(mepronil) + SX, メプチルジノカップ(meptyldinocap) + SX, メタラキシル(metalaxyl) + SX, メタラキシルM(metalaxyl-M) + SX, メトコナゾール(metconazole) + SX, メタスルホカルブ(methasulfocarb) + SX, メチラム(metiram) + SX, メトミノストロビン(metominostrobin) + SX, メトラフェノン(metrafenone) + SX, メチルテトラプロール(metyltetraprole) + SX, マシン油(mineral oils) + SX, ミクロブタニル(myclobutanil) + SX, ナフチフィン(naftifine) + SX, ヌアリモール(nuarimol) + SX, オクチリノン(octhilinone) + SX, オフラセ(ofurace) + SX, オリサストロビン(orysastrobin) + SX, オキサジキシル(oxadixyl) + SX, オキサチアピプロリン(oxathiapiprolin) + SX, oxine-copper + SX, オキソリニック酸(oxolinic acid) + SX, オキスポコナゾール(oxpoconazole) + SX, オキスポコナゾールフマル酸塩(oxpoconazole fumarate) + SX, オキシカルボキシン(oxycarboxin) + SX, オキシテトラサイクリン(oxytetracycline) + SX, ペフラゾエート(pefurazoate) + SX, ペンコナゾール(penconazole) + SX, ペンシクロン(pencycuron) + SX, ペンフルフェン(penflufen) + SX, ペンチオピラド(penthiopyrad) + SX, フェナマクリル(phenamacril) + SX, 亜リン酸(phosphorous acid) + SX, フサライド(phthalide) + SX, ピカルブトラゾクス(picarbutrazox) + SX, ピコキシストロビン(picoxystrobin) + SX, ピペラリン(piperalin) + SX, ポリオキシン(polyoxins) + SX, 炭酸水素カリウム(potassium hydrogencarbonate) + SX, 亜リン酸二水素カリウム(potassium dihydrogenphosphite) + SX, プロベナゾール(probenazole) + SX, プロクロラズ(prochloraz) + SX, プロシミドン(procymidone) + SX, プロパミジン(propamidine) + SX, プロパモカルブ(propamocarb) + SX, プロピコナゾール(propiconazole) + SX, プロピネブ(propineb) + SX, プロキナジド(proquinazid) + SX, プロチオカルブ(prothiocarb) + SX, プロチオコナゾール(prothioconazole) + SX, ピジフルメトフェン(pydiflumetofen) + SX, ピラクロストロビン(pyraclostrobin) + SX, ピラメトストロビン(pyrametostrobin) + SX, ピラオキシストロビン(pyraoxystrobin) + SX, ピラプロポイン(pyrapropoyne) + SX, ピラジフルミド(pyraziflumid) + SX, ピラゾホス(pyrazophos) + SX, ピリベンカルブ(pyribencarb) + SX, ピリブチカルブ(pyributicarb) + SX, ピリダクロメチル(pyridachlometyl) + SX, ピリフェノックス(pyrifenox) + SX, ピリメタニル(pyrimethanil) + SX, ピリモルフ(pyrimorph) + SX, ピリオフェノン(pyriofenone) + SX, ピリソキサゾール(pyrisoxazole) + SX, ピロキロン(pyroquilon) + SX, キラヤ科植物抽出成分(Quillaja extract) + SX, キンコナゾール(quinconazole) + SX, キノフメリン(quinofumelin) + SX, キノキシフェン(quinoxyfen) + SX, キントゼン(quintozene) + SX, キヌアのサポニン(Saponins of Chenopodium quinoa) + SX, セダキサン(sedaxane) + SX, シルチオファム(silthiofam) + SX, シメコナゾール(simeconazole) + SX, 炭酸水素ナトリウム(sodium hydrogencarbonate) + SX, スピロキサミン(spiroxamine) + SX, ストレプトマイシン(streptomycin) + SX, 硫黄(sulfur) + SX, テブコナゾール(tebuconazole) + SX, テブフロキン(tebufloquin) + SX, テクロフタラム(teclofthalam) + SX, テクナゼン(tecnazene) + SX, テルビナフィン(terbinafine) + SX, テトラコナゾール(tetraconazole) + SX, チアベンダゾール(thiabendazole) + SX, チフルザミド(thifluzamide) + SX, チオファネート(thiophanate) + SX, チオファネートメチル(thiophanate-methyl) + SX, チウラム(thiram) + SX, チモール(thymol) + SX, チアジニル(tiadinil) + SX, トルクロホスメチル(tolclofos-methyl) + SX, トルフェンピラド(tolfenpyrad) + SX, トルプロカルブ(tolprocarb) + SX, トリルフルアニド(tolylfluanid) + SX, トリアジメホン(triadimefon) + SX, トリアジメノール(triadimenol) + SX, トリアゾキシド(triazoxide) + SX, トリクロピリカルブ(triclopyricarb) + SX, トリシクラゾール(tricyclazole) + SX, トリデモルフ(tridemorph) + SX, トリフロキシストロビン(trifloxystrobin) + SX, トリフルミゾール(triflumizole) + SX, トリホリン(triforine) + SX, トリチコナゾール(triticonazole) + SX, バリダマイシン(validamycin) + SX, バリフェナレート(valifenalate) + SX, ビンクロゾリン(vinclozolin) + SX, マスタードパウダー(yellow mustard powder) + SX, zinc thiazole + SX, ジネブ(zineb) + SX, ジラム(ziram) + SX, ゾキサミド(zoxamide) + SX, N'-[4-({3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide (1202781-91-6) + SX, N'-{4-[(4,5-dichlorothiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylmethanimidamide (929908-57-6) + SX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, N'-[5-choro-4-(2-fluorophenoxy)-2-methylphenyl)-N-ethyl-N-methylmethanimidamide (2055589-28-9) + SX, N'-[2-choro-4-(2-fluorophenoxy)-5-methylphenyl)-N-ethyl-N-methylmethanimidamide (2055756-21-1) + SX, N'-[4-(1-hydroxy-1-phenyl-2,2,2-trifluoroethyl)-2-m
ethyl-5-methoxyphenyl)-N-isopropyl-N-methylmethanimidamide (2101814-55-3) + SX, N'-[5-bromo-6-(1-methyl-2-propoxyethoxy)-2-methylpyridin-3-yl)-N-ethyl-N-methylmethanimidamide (1817828-69-5) + SX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline (1257056-97-5) + SX, 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one (1616664-98-2) + SX, ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate (39491-78-6) + SX, N-[(2-chlorothiazol-5-yl)methyl]-N-ethyl-6-methoxy-3-nitropyridin-2-amine (1446247-98-8) + SX, 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-11-4) + SX, (1R, 2S, 5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-06-2) + SX, (1S, 2R, 5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-07-3) + SX, 2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1394057-13-6) + SX, (1R, 2S, 5S)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-08-4) + SX, (1S, 2R, 5R)-2-(chloromethyl)-5-(4-fluorobenzyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-ol (1801930-09-5) + SX, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)cyclopentan-1-carboxylate (1791398-02-1) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-bromo-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-86-0) + SX, 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)-1-[1-(4-chloro-2,6-difluorophenoxy)cyclopropyl]ethanol (2019215-84-8) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018316-13-5) + SX, 1-[2-(1-chlorocyclopropyl)-3-(2,3-difluorophenyl)-2-hydroxypropyl]-1H-imidazole-5-carbonitrile (2018317-25-2) + SX, 4-({6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl]pyridin-3-yl}oxy)benzonitrile (2046300-61-0) + SX, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082661-43-4) + SX, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)pyridin-3-yl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (2082660-27-1) + SX, methyl ({2-methyl-5-[1-(4-methoxy-2-methylphenyl)-1H-pyrazol-3-yl]phenyl}methyl)carbamate (1605879-98-8) + SX, 2-(difluoromethyl)-N-[1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1616239-21-4) + SX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-02-9) + SX, 2-(difluoromethyl)-N-[3-propyl-1,1-dimethyl-2,3-dihydro-1H-inden-4-yl]pyridine-3-carboxamide (1847460-05-2) + SX, (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-27-0) + SX, (2E,3Z)-5-{[1-(2,4-dichlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide (1445331-54-3) + SX, 5-chloro-4-({2-[6-(4-chlorophenoxy)pyridin-3-yl]ethyl}amino)-6-methylpyrimidine (1605340-92-8) + SX, N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (2132414-04-9), N-(1-benzyl-3,3,3-trifluoro-1-methylpropyl)-8-fluoroquinoline-3-carboxamide (2132414-00-5) + SX, 4,4-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-25-1) + SX, 5,5-dimethyl-2-({4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}methyl)isoxazolidin-3-one (2098918-26-2) + SX, Agrobacterium radiobactor strain K1026 + SX, Agrobacterium radiobactor strain K84 + SX, Bacillus amyloliquefaciens (Aveo(商標) EZ Nematicide) + SX, Bacillus amyloliquefaciens strain AT332 + SX, Bacillus amyloliquefaciens strain B3 + SX, Bacillus amyloliquefaciens strain D747 + SX, Bacillus amyloliquefaciens strain DB101 + SX, Bacillus amyloliquefaciens strain DB102 + SX, Bacillus amyloliquefaciens strain GB03 + SX, Bacillus amyloliquefaciens strain FZB24 + SX, Bacillus amyloliquefaciens strain FZB42 + SX, Bacillus amyloliquefaciens strain IN937a + SX, Bacillus amyloliquefaciens strain MBI600 + SX, Bacillus amyloliquefaciens strain QST713 + SX, Bacillus amyloliquefaciens isolate strain B246 + SX, Bacillus amyloliquefaciens strain F727 + SX, Bacillus amyloliquefaciens subsp. plantarum strain D747 + SX, Bacillus licheniformis strain HB-2 + SX, Bacillus licheniformis strain SB3086 + SX, Bacillus pumilus strain AQ717 + SX, Bacillus pumilus strain BUF-33 + SX, Bacillus pumilus strain GB34 + SX, Bacillus pumilus strain QST2808 + SX, Bacillus simplex strain CGF2856 + SX, Bacillus subtilis strain AQ153 + SX, Bacillus subtilis strain AQ743 + SX, Bacillus subtilis strain BU1814 + SX, Bacillus subtilis strain D747 + SX, Bacillus subtilis strain DB101 + SX, Bacillus subtilis strain FZB24 + SX, Bacillus subtilis strain GB03 + SX, Bacillus subtilis strain HAI0404 + SX, Bacillus subtilis strain IAB/BS03 + SX, Bacillus subtilis strain MBI600 + SX, Bacillus subtilis strain QST30002/AQ30002 + SX, Bacillus subtilis strain QST30004/AQ30004 + SX, Bacillus subtilis strain QST713 + SX, Bacillus subtilis strain QST714 + SX, Bacillus subtilis var. Amyloliquefaciens strain FZB24 + SX, Bacillus subtilis strain Y1336 + SX, Burkholderia cepacia + SX, Burkholderia cepacia type Wisconsin strain J82 + SX, Burkholderia cepacia type Wisconsin strain M54 + SX, Candida oleophila strain O + SX, Candida saitoana + SX, Chaetomium cupreum + SX, Clonostachys rosea + SX, Coniothyrium minitans strain CGMCC8325 + SX, Coniothyrium minitans strain CON/M/91-8 + SX, cryptococcus albidus + SX, Erwinia carotovora subsp.carotovora strain CGE234M403 + SX, Fusarium oxysporum strain Fo47 + SX, Gliocladium catenulatum strain J1446 + SX, Paenibacillus polymyxa strain AC-1 + SX, Paenibacillus polymyxa strain BS-0105 + SX, Pantoea agglomerans strain E325 + SX, Phlebiopsis gigantea strain VRA1992 + SX, Pseudomonas aureofaciens strain TX-1 + SX, Pseudomonas chlororaphis strain 63-28 + SX, Pseudomonas chlororaphis strain AFS009 + SX, Pseudomonas chlororaphis strain MA342 + SX, Pseudomonas fluorescens strain 1629RS + SX, Pseudomonas fluorescens strain A506 + SX, Pseudomonas fluorescens strain CL145A + SX, Pseudomonas fluorescens strain G7090 + SX, Pseudomonas sp. strain CAB-02 + SX, Pseudomonas syringae strain 742RS + SX, Pseudomonas syringae strain MA-4 + SX, Pseudozyma flocculosa strain PF-A22UL + SX, Pseudomonas rhodesiae strain HAI-0804 + SX, Pythium oligandrum strain DV74 + SX, Pythium oligandrum strain M1 + SX, Streptomyces griseoviridis strain K61 + SX, Streptomyces lydicus strain WYCD108US + SX, Streptomyces lydicus strain WYEC108 + SX, Talaromyces flavus strain SAY-Y-94-01 + SX, Talaromyces flavus strain V117b + SX, Trichoderma asperellum strain ICC012 + SX, Trichoderma asperellum SKT-1 + SX, Trichoderma asperellum strain T25 + SX, Trichoderma asperellum strain T34 + SX, Trichoderma asperellum strain TV1 + SX, Trichoderma atroviride strain CNCM 1-1237 + SX, Trichoderma atroviride strain LC52 + SX, Trichoderma atroviride strain IMI 206040 + SX, Trichoderma atroviride strain SC1 + SX, Trichoderma atroviride strain SKT-1 + SX, Trichoderma atroviride strain T11 + SX, Trichoderma gamsii strain ICC080 + SX, Trichoderma harzianum strain 21 + SX, Trichoderma harzianum strain DB104 + SX, Trichoderma harzianum strain DSM 14944 + SX, Trichoderma harzianum strain ESALQ-1303 + SX, Trichoderma harzianum strain ESALQ-1306 + SX, Trichoderma harzianum strain IIHR-Th-2 + SX, Trichoderma harzianum strain ITEM908 + SX, Trichoderma harzianum strain kd + SX, Trichoderma harzianum strain MO1 + SX, Trichoderma harzianum strain SF + SX, Trichoderma harzianum strain T22 + SX, Trichoderma harzianum strain T39 + SX, Trichoderma harzianum strain T78 + SX, Trichoderma harzianum strain TH35 + SX, Trichoderma polysporum strain IMI206039 + SX, trichoderma stromaticum + SX, Trichoderma virens strain G-41 + SX, Trichoderma virens strain GL-21 + SX, Trichoderma viride + SX, Variovorax paradoxus strain CGF4526 + SX, Harpin protein + SX, フルベネテラム(flubeneteram) + SX, N-acetyl-2-(ethanesulfonyl)-N-[2-(methoxycarbonyl)-4-(trifluoromethoxy)phenyl]-4-(trifluoromethyl)benzamide (2043675-28-9) + SX, (2S,3S)-3-(2-methylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate (2376210-00-1) + SX, (2S,3S)-3-(4-fluoro-2-methylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(4-methoxy-2-methylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate + SX, (2S,3S)-3-(2,4-dimethylphenyl)butan-2-yl N-[(3-acetoxy-4-methoxypyridin-2-yl)carbonyl]-L-alaninate (2376209-13-9) + SX, (2S,3S)-3-(2-methylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate (2376210-02-3) + SX, (2S,3S)-3-(4-fluoro-2-methylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate + SX, (2S,3S)-3-(4-methoxy-2-methylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate (2376209-40-2) + SX, (2S,3S)-3-(2,4-dimethylphenyl)butan-2-yl N-({3-[(2-methylpropanoyl)oxy]-4-methoxypyridin-2-yl}carbonyl)-L-alaninate (2376209-15-1) + SX。
1-メチルシクロプロペン(1-methylcyclopropene) + SX, 1,3-ジフェニルウレア(1,3-diphenylurea) + SX, 2,3,5-トリヨード安息香酸(2,3,5-triiodobenzoic acid) + SX, IAA ((1H-indol-3-yl)acetic acid) + SX, IBA (4-(1H-indol-3-yl)butyric acid) + SX, MCPA (2-(4-chloro-2-methylphenoxy)acetic acid) + SX, MCPB (4-(4-chloro-2-methylphenoxy)butyric acid) + SX, 4-CPA (4-chlorophenoxyacetic acid) + SX, 5-アミノレブリン酸塩酸塩(5-aminolevulinic acid hydrochloride) + SX, 6-ベンジルアミノプリン(6-benzylaminopurine) + SX, アブシシン酸(abscisic acid) + SX, AVG (aminoethoxyvinylglycine) + SX, アンシミドール(ancymidol) + SX, ブトルアリン(butralin) + SX, 炭酸カルシウム(calcium carbonate) + SX, 塩化カルシウム(calcium chloride) + SX, ギ酸カルシウム(calcium formate) + SX, 過酸化カルシウム(calcium peroxide) + SX, 石灰硫黄(calcium polysulfide) + SX, 硫酸カルシウム(calcium sulfate) + SX, クロルメコートクロリド(chlormequat-chloride) + SX, クロロプロファム(chlorpropham) + SX, 塩化コリン(choline chloride) + SX, クロプロップ(cloprop) + SX, シアナミド(cyanamide) + SX, シクラニリド(cyclanilide) + SX, ダミノジッド(daminozide) + SX, デカン-1-オール(decan-1-ol) + SX, ジクロルプロップ(dichlorprop) + SX, ジケグラック(dikegulac) + SX, ジメチピン(dimethipin) + SX, ジクワット(diquat) + SX, エテホン(ethephon) + SX, エチクロゼート(ethychlozate) + SX, フルメトラリン(flumetralin) + SX, フルルプリミドール(flurprimidol) + SX, ホルクロルフェヌロン(forchlorfenuron) + SX, ホルモノネチン(formononetin) + SX, ジベレリンA(Gibberellin A) + SX, ジベレリンA3(Gibberellin A3) + SX, イナベンフィド(inabenfide) + SX, カイネチン(Kinetin) + SX, lipochitooligosaccharide SP104 + SX, マレイン酸ヒドラジド(maleic hydrazide) + SX, メフルイジド(mefluidide) + SX, メピコートクロリド(mepiquat-chloride) + SX, 酸化型グルタチオン(oxidized glutathione) + SX, パクロブトラゾール(pacrobutrazol) + SX, ペンディメタリン(pendimethalin) + SX, プロヘキサジオンカルシウム(prohexandione-calcium) + SX, プロヒドロジャスモン(prohydrojasmon) + SX, ピラフルフェンエチル(pyraflufen-ethyl) + SX, シントフェン(sintofen) + SX, 1-ナフタレン酢酸ナトリウム(sodium 1-naphthaleneacetate) + SX, シアン酸ナトリウム(sodium cyanate) + SX, ストレプトマイシン(streptmycin) + SX, チジアズロン(thidiazuron) + SX, トリアペンテノール(triapenthenol) + SX, トリブホス(Tribufos) + SX, トリネキサパックエチル(trinexapac-ethyl) + SX, ウニコナゾールP (uniconazole-P) + SX, 2-(ナフタレン-1-イル)アセトアミド(2-(naphthalen-1-yl)acetamide) + SX, [4-オキソ-4-(2-フェニルエチル)アミノ]酪酸+ SX, 5-(トリフルオロメチル)ベンゾ[b]チオフェン-2-カルボン酸メチル+ SX, 3-[(6-クロロ-4-フェニルキナゾリン-2-イル)アミノ]-1-プロパノール+ SX, Claroideoglomus etunicatum + SX, Claroideoglomus claroideum + SX, Funneliformis mosseae + SX, Gigaspora margarita + SX, Gigaspora rosea + SX, Glomus aggregatum + SX, Glomus deserticola + SX, Glomus monosporum + SX, Paraglomus brasillianum + SX, Rhizophagus clarus + SX, Rhizophagus intraradices RTI-801 + SX, Rhizophagus irregularis DAOM 197198 + SX, Azorhizobium caulinodans + SX, Azospirillum amazonense + SX, Azospirillum brasilense XOH + SX, Azospirillum brasilense Ab-V5 + SX, Azospirillum brasilense Ab-V6 + SX, Azospirillum caulinodans + SX, Azospirillum halopraeferens + SX, Azospirillum irakense + SX, Azospirillum lipoferum + SX, Bradyrhizobium elkanii SEMIA 587 + SX, Bradyrhizobium elkanii SEMIA 5019 + SX, Bradyrhizobium japonicum TA-11 + SX, Bradyrhizobium japonicum USDA 110 + SX, Bradyrhizobium liaoningense + SX, Bradyrhizobium lupini + SX, Delftia acidovorans RAY209 + SX, Mesorhizobium ciceri + SX, Mesorhizobium huakii + SX, Mesorhizobium loti + SX, Rhizobium etli + SX, Rhizobium galegae + SX, Rhizobium leguminosarum bv. Phaseoli + SX, Rhizobium leguminosarum bv. Trifolii + SX, Rhizobium leguminosarum bv. Viciae + SX, Rhizobium trifolii + SX, Rhizobium tropici + SX, Sinorhizobium fredii + SX, Sinorhizobium meliloti + SX, Zucchini Yellow Mosaik Virus weak strain + SX。
アントラキノン(anthraquinone) + SX, ディート(deet) + SX, イカリジン(icaridin) + SX。
コムギの病害:うどんこ病(Blumeria graminis)、赤かび病(Fusarium graminearum、Fusarium avenaceum、Fusarium culmorum、Microdochium nivale)、黄さび病(Puccinia striiformis)、黒さび病(Puccinia graminis)、赤さび病(Puccinia recondita)、紅色雪腐病(Microdochium nivale、 Microdochium majus)、雪腐小粒菌核病(Typhula incarnata、Typhula ishikariensis)、裸黒穂病(Ustilago tritici)、なまぐさ黒穂病(Tilletia caries、 Tilletia controversa)、眼紋病(Pseudocercosporella herpotrichoides)、葉枯病(Septoria tritici)、ふ枯病(Stagonospora nodorum)、黄斑病(Pyrenophora tritici-repentis)、リゾクトニア属菌による苗立枯れ病(Rhizoctonia solani)、立枯病(Gaeumannomyces graminis)、いもち病(Pyricularia graminis-tritici);
オオムギの病害:うどんこ病(Blumeria graminis)、赤かび病(Fusarium graminearum、Fusarium avenaceum、Fusarium culmorum、Microdochium nivale)、黄さび病(Puccinia striiformis)、黒さび病(Puccinia graminis)、小さび病(Puccinia hordei)、裸黒穂病(Ustilago nuda)、雲形病(Rhynchosporium secalis)、網斑病(Pyrenophora teres)、斑点病(Cochliobolus sativus)、斑葉病(Pyrenophora graminea)、ラムラリアリーフスポット病(Ramularia collo-cygni)、リゾクトニア属菌による苗立枯れ病(Rhizoctonia solani);
トウモロコシの病害:さび病(Puccinia sorghi)、南方さび病(Puccinia polysora)、すす紋病(Setosphaeria turcica)、熱帯性さび病(Physopella zeae)、ごま葉枯病(Cochliobolus heterostrophus)、炭疽病(Colletotrichum graminicola)、グレーリーフスポット病(Cercospora zeae-maydis)、褐斑病(Kabatiella zeae)、ファエオスファエリアリーフスポット病(Phaeosphaeria maydis)、Diplodia病(Stenocarpella maydis、Stenocarpella macrospora)、ストークロット病(Fusarium graminearum、Fusarium verticilioides、Colletotrichum graminicola)、黒穂病(Ustilago maydis)、フイソデルマ病(Physoderma maydis);
ワタの病害:炭疽病(Colletotrichum gossypii)、白かび病(Ramularia areola)、黒斑病(Alternaria macrospora、Alternaria gossypii)、Black root rot病 (Thielaviopsis basicola);
コーヒーの病害:さび病(Hemileia vastatrix)、リーフスポット病(Cercospora coffeicola);
ナタネの病害:菌核病(Sclerotinia sclerotiorum)、黒斑病(Alternaria brassicae)、根朽病(Phoma lingam)、light leaf spot病(Pyrenopeziza brassicae);
サトウキビの病害:さび病 (Puccinia melanocephela、Puccinia kuehnii)、黒穂病 (Ustilago scitaminea);
ヒマワリの病害:さび病 (Puccinia helianthi)、べと病(Plasmopara halstedii);
カンキツ類の病害:黒点病(Diaporthe citri)、そうか病(Elsinoe fawcetti)、緑かび病(Penicillium digitatum)、青かび病(Penicillium italicum)、疫病 (Phytophthora parasitica、Phytophthora citrophthora)、こうじかび病(Aspergillus niger);
リンゴの病害:モニリア病(Monilinia mali)、腐らん病(Valsa ceratosperma)、うどんこ病(Podosphaera leucotricha)、斑点落葉病(Alternaria alternata apple pathotype)、黒星病(Venturia inaequalis)、炭疽病(Glomerella cingulata、Colletotrichum acutatum)、褐斑病(Diplocarpon mali)、輪紋病(Botryosphaeria berengeriana)、疫病 (Phytophtora cactorum)、赤星病(Gymnosporangium juniperi-virginianae、Gymnosporangium yamadae);
ナシの病害:黒星病(Venturia nashicola、Venturia pirina)、黒斑病(Alternaria alternata Japanese pear pathotype)、赤星病(Gymnosporangium haraeanum);
モモの病害:灰星病(Monilinia fructicola)、黒星病(Cladosporium carpophilum)、ホモプシス腐敗病(Phomopsis sp.)、縮葉病(Taphrina deformans);
ブドウの病害:黒とう病(Elsinoe ampelina)、晩腐病(Glomerella cingulata、Colletotrichum acutatum)、うどんこ病(Uncinula necator)、さび病(Phakopsora ampelopsidis)、ブラックロット病(Guignardia bidwellii)、べと病(Plasmopara viticola);
カキの病害:炭疽病(Gloeosporium kaki、Colletotrichum acutatum)、落葉病(Cercospora kaki、Mycosphaerella nawae);
イチジクの病害:さび病(Phakopsora nishidana);
ウリ類の病害:炭疽病(Colletotrichum lagenarium)、うどんこ病(Sphaerotheca fuliginea)、つる枯病(Didymella bryoniae)、褐斑病(Corynespora cassiicola)、つる割病(Fusarium oxysporum)、べと病(Pseudoperonospora cubensis)、疫病(Phytophthora capsici)、苗立枯病(Pythium sp.);
トマトの病害:輪紋病(Alternaria solani)、葉かび病(Cladosporium fulvum)、すすかび病(Pseudocercospora fuligena)、疫病(Phytophthora infestans)、うどんこ病(Leveillula taurica);
ナスの病害:褐紋病(Phomopsis vexans)、うどんこ病(Erysiphe cichoracearum);
アブラナ科野菜の病害:黒斑病(Alternaria japonica)、白斑病(Cercosporella brassicae)、根こぶ病(Plasmodiophora brassicae)、べと病(Peronospora parasitica)、白さび病(Albugo candida);
ネギの病害:さび病(Puccinia allii);
ダイズの病害:紫斑病(Cercospora kikuchii)、黒とう病(Elsinoe glycines)、黒点病(Diaporthe phaseolorum var. sojae)、さび病(Phakopsora pachyrhizi)、褐色輪紋病(Corynespora cassiicola)、炭疽病(Colletotrichum glycines、Colletotrichum truncatum)、葉腐病(Rhizoctonia solani)、褐紋病(Septoria glycines)、斑点病(Cercospora sojina)、菌核病(Sclerotinia sclerotiorum)、うどんこ病(Microsphaera diffusa)、茎疫病 (Phytophthora sojae)、べと病(Peronospora manshurica)、突然死病(Fusarium virguliforme)、黒根腐病(Calonectria ilicicola)、Diaporthe/Phomopsis complex(Diaporthe longicolla);
インゲンの病害:菌核病(Sclerotinia sclerotiorum)、さび病(Uromyces appendiculatus)、角斑病(Phaeoisariopsis griseola)、炭疽病(Colletotrichum lindemuthianum)、根腐病(Fusarium solani);
ラッカセイの病害:黒渋病(Cercospora personata)、褐斑病(Cercospora arachidicola)、白絹病(Sclerotium rolfsii)、黒根腐病(Calonectria ilicicola);
エンドウの病害:うどんこ病(Erysiphe pisi)、根腐病(Fusarium solani);
ジャガイモの病害:夏疫病(Alternaria solani)、疫病(Phytophthora infestans)、緋色腐敗病 (Phytophthora erythroseptica)、粉状そうか病 (Spongospora subterranea f. sp. subterranea)、半身萎凋病(Verticillium albo-atrum、Verticillium dahliae、Verticillium nigrescens)、乾腐病(Fusarium solani)、がん腫病(Synchytrium endobioticum);
イチゴの病害:うどんこ病(Sphaerotheca humuli);
チャの病害:網もち病(Exobasidium reticulatum)、白星病(Elsinoe leucospila)、輪斑病(Pestalotiopsis sp.)、炭疽病(Colletotrichum theae-sinensis);
タバコの病害:赤星病(Alternaria longipes)、炭疽病(Colletotrichum tabacum)、べと病(Peronospora tabacina)、疫病(Phytophthora nicotianae);
テンサイの病害:褐斑病(Cercospora beticola)、葉腐病(Thanatephorus cucumeris)、根腐病(Thanatephorus cucumeris)、黒根病(Aphanomyces cochlioides)、さび病(Uromyces betae);
バラの病害:黒星病(Diplocarpon rosae)、うどんこ病(Sphaerotheca pannosa);
キクの病害:褐斑病(Septoria chrysanthemi-indici)、白さび病(Puccinia horiana);
タマネギの病害:白斑葉枯病(Botrytis cinerea、Botrytis byssoidea、Botrytis squamosa)、灰色腐敗病(Botrytis allii)、小菌核性腐敗病(Botrytis squamosa);
種々の作物の病害:灰色かび病(Botrytis cinerea)、菌核病(Sclerotinia sclerotiorum)、苗立枯病(Pythium aphanidermatum、Pythium irregulare、Pythium ultimum);
ダイコンの病害:黒斑病(Alternaria brassicicola);
シバの病害:ダラースポット病(Sclerotinia homoeocarpa)、ブラウンパッチ病、ラージパッチ病(Rhizoctonia solani)、赤焼病(Pythium aphanidermatum);
バナナの病害:シガトカ病(Mycosphaerella fijiensis、Mycosphaerella musicola);
レンズマメの病害:Ascochyta病(Ascochyta lentis);
ヒヨコマメの病害:Ascochyta病(Ascochyta rabiei);
ピーマンの病害:炭疽病(Colletotrichum scovillei);
マンゴーの病害:炭疽病(Colletotrichum acutatum);
果樹の病害:白紋羽病(Rosellinia necatrix)、紫紋羽病(Helicobasidium mompa);
収穫後のリンゴ、ナシ等の果実の病害:ムコールロット病(Mucor piriformis);
Aspergillus属、Penicillium属、Fusarium属、Gibberella属、Tricoderma属、Thielaviopsis属、Rhizopus属、Mucor属、Corticium属、Phoma属、Rhizoctonia属、Diplodia属等によって引き起こされる種子病害又は生育初期の病害;
ウイルス病:Olpidium brassicaeによって媒介されるレタスのビッグベイン病、Polymyxa属(例えば、Polymyxa betae及びPolymyxa graminis)によって媒介される各種作物のウイルス病;
細菌(bacteria)が引き起こす病害:イネの苗立枯細菌病(Burkholderia plantarii)、キュウリの斑点細菌病(Pseudomonas syringae pv. Lachrymans)、ナスの青枯病(Ralstonia solanacearum)、カンキツのかいよう病(Xanthomonas citri)、ハクサイの軟腐病(Erwinia carotovora)、ジャガイモのそうか病(Streptomyces scabiei)、トウモロコシのGoss's wilt病(Clavibacter michiganensis)、ブドウ、オリーブ、モモ等のピアス病(Xylella fastidiosa)、リンゴ、モモ、サクランボ等のバラ科植物の根頭がんしゅ病(Agrobacterium tumefaciens)。
オビヤスデ目(Polydesmida):ヤケヤスデ(Oxidus gracilis)、アカヤスデ(Nedyopus tambanus)等のヤケヤスデ科(Paradoxosomatidae)。
等脚目(Isopoda):オカダンゴムシ(Armadillidium vulgare)等のオカダンゴムシ科(Armadillidiidae)。
唇脚綱(Chilopoda):ゲジ(Thereuonema hilgendorfi)等のゲジ科(Scutigeridae);トビズムカデ(Scolopendra subspinipes)等のオオムカデ科(Scolopendridae);イッスンムカデ(Bothropolys rugosus)等のイッスンムカデ科(Ethopolyidae)。
腹足綱(Gastropoda):チャコウラナメクジ(Limax marginatus)、キイロコウラナメクジ(Limax flavus)等のコウラナメクジ科(Limacidae);ナメクジ(Meghimatium bilineatum)等のナメクジ科(Philomycidae);スクミリンゴガイ(Pomacea canaliculata)等のリンゴガイ科(Ampullariidae);ヒメモノアラガイ(Austropeplea ollula)等のモノアラガイ科(Lymnaeidae)。
毒餌剤の基材としては、例えば、穀物粉、植物油、糖、結晶セルロース等が挙げられ、更に必要に応じて、ジブチルヒドロキシトルエン、ノルジヒドログアイアレチン酸等の酸化防止剤、デヒドロ酢酸等の保存料、トウガラシ末等の子供やペットによる誤食防止剤、チーズ香料、タマネギ香料、ピーナッツオイル等の害虫誘引性香料等が添加される。
組成物Aを種子又は栄養生殖器官に処理する場合、組成物Aを1つの製剤として種子又は栄養生殖器官に処理することもできるし、組成物Aを異なる複数の製剤として複数回に分けて種子又は栄養生殖器官に処理することもできる。組成物Aを異なる複数の製剤として複数回に分けて処理する方法としては、例えば、有効成分として本発明化合物のみを含む製剤を処理し、種子又は栄養生殖器官を風乾させた後、本成分を含む製剤を処理する方法;及び、有効成分として本発明化合物及び本成分を含む製剤を処理し、種子又は栄養生殖器官を風乾させた後、処理済みの本成分以外の本成分を含む製剤を処理する方法、が挙げられる。
本発明における本発明化合物又は組成物Aを保持している種子又は栄養生殖器官とは、種子又は栄養生殖器官の表面に、本発明化合物又は組成物Aが付着している状態のものを意味する。上記の本発明化合物又は組成物Aを保持している種子又は栄養生殖器官は、種子又は栄養生殖器官へ本発明化合物又は組成物Aが付着される前後に、本発明化合物又は組成物A以外の資材が付着されていてもよい。
また、組成物Aが種子又は栄養生殖器官の表面に層となって付着している場合、該層は、1つの層又は複数の層からなる。また、複数の層からなる場合、各々の層は、1以上の有効成分を含んでいる層であるか、又は、1以上の有効成分を含んでいる層と有効成分を含んでいない層とからなる。
本発明化合物又は組成物Aを保持している種子又は栄養生殖器官は、例えば、本発明化合物又は組成物A含む製剤を前記の種子処理の方法により、種子又は栄養生殖器官に施用することによって得ることができる。
カラム:L-column2 ODS、内径4.6 mm、長さ30 mm、粒子径3 μm(一般財団法人化学物質評価研究機構)
UV測定波長:254nm
移動相:A液:0.1%ギ酸水溶液、B液:0.1%ギ酸アセトニトリル
流速:2.0mL/分
ポンプ:LC-20AD(島津製作所製)2台(高圧グラジエント)
グラジエント条件:[表LC1]に記載の濃度勾配で送液する。
検出器:LCMS-2020(島津製作所製)
イオン化法:DUIS
メチル (Z)-2-(5-ブロモ-2-メチルフェノキシ)-3-メトキシアクリレート(国際公開第2001/000562号に記載の方法で製造した)20.0g、ビス(ピナコラト)ジボロン20.2g、[1,1’-ビス(ジフェニルホスフィノ)フェロセン]パラジウム(II)ジクロリド2.43g、酢酸カリウム19.5g及びDMSO250mLの混合物を、80℃で10時間撹拌した。得られた混合物に水を加え、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順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:4)に付し、次式で示される中間体1を11.8g得た。
メチル (Z)-2-(5-ブロモ-2-メチルフェノキシ)-3-メトキシアクリレートに代えて、国際公開第2001/000562号に記載の方法で製造したメチル (Z)-2-(5-ブロモ-2-メチルベンジル)-3-メトキシアクリレート)を用い、参考製造例1に準じて、次式で示される中間体2を製造した。
メチル (Z)-2-(5-ブロモ-2-メチルフェノキシ)-3-メトキシアクリレートに代えて、国際公開第98/03464号に記載の方法で製造した(Z)-2-(5-ブロモ-2-クロロフェノキシ)-3-メトキシアクリレートを用い、参考製造例1に準じて、次式で示される中間体3を製造した。
室温で、0.50gの中間体1、エタノール20mL、アセトニトリル20mL及び水20mLの混合物に、メタクロロ過安息香酸(純度70%、30%水を含む)0.43gを加え、3時間撹拌した。得られた混合物に、飽和チオ硫酸ナトリウム水溶液及び飽和塩化アンモニウム水溶液を順次加え、1時間撹拌した。得られた混合物を減圧下で濃縮し、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順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体A1を0.29g得た。
参考製造例2に準じて製造した化合物及びその物性値を以下に示す。
メチル 2-(5-ヒドロキシ-2-メチルフェノキシ)アセタート0.50g、トリフェニルホスフィン0.82g、ベンジルアルコール0.39mL及びクロロホルム10mLの混合物に、0℃でビス(2-メトキシエチル) アゾジカルボキシラート0.78gを加え、室温で22時間撹拌した。得られた混合物に、飽和炭酸水素ナトリウム水溶液を加え、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順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体C1を0.55g得た。
1H-NMR (CDCl3) δ: 7.03 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 4.62 (2H, s), 3.87 (2H, t), 3.80 (3H, s), 2.21 (3H, s), 1.84-1.73 (2H, m), 1.02 (3H, t).
中間体C4(E:Bu):
1H-NMR (CDCl3) δ: 7.03 (1H, d), 6.43 (1H, dd), 6.30 (1H, d), 4.62 (2H, s), 3.91 (2H, t), 3.80 (3H, s), 2.21 (3H, s), 1.78-1.70 (2H, m), 1.53-1.42 (2H, m), 0.97 (3H, t).
中間体C5(E:i-Bu):
1H-NMR (CDCl3) δ: 7.02 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 4.63 (2H, s), 3.80 (3H, s), 3.66 (2H, d), 2.21 (3H, s), 2.11-1.99 (1H, m), 1.01 (6H, d).
中間体C6(E:Pen):
1H-NMR (CDCl3) δ: 7.03 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 4.62 (2H, s), 3.90 (2H, t), 3.80 (3H, s), 2.21 (3H, s), 1.82-1.70 (2H, m), 1.46-1.31 (4H, m), 0.93 (3H, t).
中間体C7(E:CH2c-Pr):
1H-NMR (CDCl3) δ: 7.02 (1H, d), 6.41 (1H, dd), 6.34 (1H, d), 4.62 (2H, s), 3.80 (3H, s), 3.74 (2H, d), 2.21 (3H, s), 1.31-1.18 (1H, m), 0.68-0.60 (2H, m), 0.37-0.29 (2H, m).
中間体C8(E:CH2c-Pen):
1H-NMR (CDCl3) δ: 7.02 (1H, d), 6.44 (1H, dd), 6.31 (1H, d), 4.63 (2H, s), 3.80 (3H, s), 3.77 (2H, d), 2.39-2.27 (1H, m), 2.21 (3H, s), 1.88-1.76 (2H, m), 1.67-1.53 (4H, m), 1.40-1.28 (2H, m).
中間体C9(E:CH2c-Hex):
1H-NMR (CDCl3) δ: 7.02 (1H, d), 6.43 (1H, dd), 6.30 (1H, d), 4.62 (2H, s), 3.80 (3H, s), 3.70 (2H, d), 2.20 (3H, s), 1.90-1.80 (2H, m), 1.80-1.66 (4H, m), 1.35-1.14 (3H, m), 1.10-0.97 (2H, m).
中間体C10(E:CH2CH2Ph):
1H-NMR (CDCl3) δ: 7.36-7.21 (5H, m), 7.03 (1H, d), 6.44 (1H, dd), 6.30 (1H, d), 4.62 (2H, s), 4.13 (2H, t), 3.80 (3H, s), 3.08 (2H, t), 2.21 (3H, s).
中間体C11(E:CH2C≡CH):
1H-NMR (CDCl3) δ: 7.06 (1H, d), 6.52 (1H, dd), 6.38 (1H, d), 4.64 (2H, d), 4.62 (2H, s), 3.80 (3H, s), 2.52 (1H, t), 2.22 (3H, s).
室温で、メチル 2-(5-ヒドロキシ-2-メチルフェノキシ)アセタート0.30g、炭酸カリウム0.28g及びDMF10mLの混合物に、N-メチル-N-フェニルカルバモイルクロリド0.29gを加え、3時間撹拌した。得られた混合物に、飽和塩化アンモニウム水溶液を加え、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順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体C2を0.47g得た。
参考製造例4に準じて製造した化合物及びその物性値を以下に示す。
0.24gの中間体C1、ギ酸メチル0.15g及びジメトキシエタン5mLの混合物に、氷冷下でカリウムtert-ブトキシド0.21gを加え、室温で1時間撹拌した。得られた混合物に1N塩酸を加え、酢酸エチルで抽出した。得られた有機層を硫酸マグネシウムで乾燥し、減圧下で濃縮して、次式で示される中間体B1を0.19g得た。
中間体B3(E:CH2c-Pr):LCMS: 279 [M+H]+, RT = 1.82 分
中間体B4(E:CH2c-Pen):LCMS: 307 [M+H]+, RT = 2.07 分
中間体B5(E:CH2c-Hex):LCMS: 321 [M+H]+, RT = 2.16 分
5-ブロモ-2-メチルベンズアルデヒド4.58gとTHF185mLの混合物に、氷冷下、水素化ナトリウム(60%、油状)1.00gを加え、氷冷下で20分間撹拌した。得られた混合物に、ジメチルホスホノ酢酸メチル5.00gを加え、室温で4時間撹拌した。得られた混合物に、飽和炭酸水素ナトリウム水溶液を加え、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順次洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、次式で示される中間体4を5.80g得た。
108.43gの中間体4、塩化コバルト(II)5.52g及びメタノール1084mLの混合物を-54℃に冷却し、そこに水素化ホウ素ナトリウム40.35gを加え、-24℃で6時間撹拌した。得られた混合物に10%塩化アンモニウム水溶液を加え、酢酸エチルで抽出した。得られた有機層を水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮することにより、次式で示される中間体5を93.91g得た。
3.80gの中間体5及びTHF137mLの混合物を-72℃に冷却し、そこにリチウムジイソプロピルアミド(1.08M ヘキサン-THF溶液)27mLを加え、-66℃で30分間撹拌した。得られた混合物にギ酸メチル7.10gを加え、-63℃で1時間撹拌した。得られた混合物に10%硫酸水素ナトリウム水溶液を加え、酢酸エチルで抽出した。得られた有機層を水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮することにより、粗メチル 2-(5-ブロモ-2-メチルベンジル)-3-ヒドロキシアクリレートを得た。得られた粗メチル 2-(5-ブロモ-2-メチルベンジル)-3-ヒドロキシアクリレートにDMF137mLを加え、そこに炭酸カリウム6.13g及び硫酸ジメチル4.66gを順次加え、室温で4時間撹拌した。得られた混合物に水を加え、MTBEで抽出した。得られた有機層を水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮することにより、次式で示される中間体E1を3.61g得た。
参考製造例8に準じて製造した化合物及びその物性値を以下に示す。
式(II-A):
5-クロロ-2-メチルフェノール2.00g、炭酸カリウム2.33g及びDMF20mLの混合物に、2-ブロモ酢酸メチル2.58gを加え、室温で3時間撹拌した。得られた混合物に、水を加え、MTBEで抽出した。得られた有機層を水及び飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:4)に付し、次式で示される中間体6を2.94g得た。
3.00gの中間体6、ギ酸メチル2.3mL及び1,2-ジメトキシエタン20mLの混合物に、氷冷下、カリウムt-ブトキシド3.15gを加え、室温で2時間撹拌した。得られた混合物に1N塩酸を加え、酢酸エチルで抽出した。得られた有機層を水で洗浄し、無水硫酸ナトリウムで乾燥し、減圧下で濃縮することにより、次式で示される中間体7を2.44g得た。
1.09gの中間体7、炭酸カリウム0.70g及びDMF10mLの混合物に、氷冷下、ヨードメタン0.62mLを加え、室温で2時間撹拌した。得られた混合物に水を加え、MTBEで抽出した。得られた有機層を水及び飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:4)に付し、次式で示される中間体D2を1.00g得た。
参考製造例11に準じて製造した化合物及びその物性値を以下に示す。
式(VI):
中間体D2:1H-NMR (CDCl3) δ: 7.33 (1H, s), 7.07 (1H, dd), 6.88 (1H, dd), 6.70 (1H, d), 3.89 (3H, s), 3.72 (3H, s), 2.30 (3H, s).
0.25gの中間体A1、トリフェニルホスフィン0.33g、エタノール0.06mL及びクロロホルム5mLの混合物に、0℃でビス(2-メトキシエチル) アゾジカルボキシラート0.32gを加え、室温で16時間撹拌した。得られた混合物に、飽和炭酸水素ナトリウム水溶液を加え、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し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:4)に付し、次式で示される本発明化合物1を0.23g得た。
本発明化合物3:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.03 (1H, d), 6.45 (1H, dd), 6.33 (1H, d), 3.86 (3H, s), 3.84 (2H, t), 3.70 (3H, s), 2.27 (3H, s), 1.82-1.71 (2H, m), 1.01 (3H, t).
本発明化合物4:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.87 (3H, s), 3.71 (3H, s), 3.63 (2H, d), 2.27 (3H, s), 2.09-1.97 (1H, m), 1.00 (6H, d).
本発明化合物5:1H-NMR (CDCl3) δ: 7.33 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.31 (1H, d), 3.88 (3H, s), 3.71 (3H, s), 3.50 (2H, s), 2.26 (3H, s), 1.00 (9H, s).
本発明化合物6:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.88 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.76-1.67 (2H, m), 1.52-1.40 (2H, m), 0.96 (3H, t).
本発明化合物7:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.31 (1H, d), 4.30-4.22 (1H, m), 3.86 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 1.74-1.62 (1H, m), 1.53-1.33 (3H, m), 1.24 (3H, d), 0.92 (3H, t).
本発明化合物8:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.86 (3H, s), 3.76-3.62 (2H, m), 3.70 (3H, s), 2.26 (3H, s), 1.86-1.76 (1H, m), 1.59-1.48 (1H, m), 1.29-1.17 (1H, m), 0.98 (3H, d), 0.93 (3H, t).
本発明化合物9:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.03 (1H, d), 6.45 (1H, dd), 6.32 (1H, d), 3.90 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.84-1.75 (1H, m), 1.63 (2H, q), 0.94 (6H, d).
本発明化合物10:1H-NMR (CDCl3) δ: 7.32 (1H, s), 7.03 (1H, d), 6.46 (1H, dd), 6.32 (1H, d), 3.87 (3H, s), 3.77 (2H, d), 3.71 (3H, s), 2.27 (3H, s), 1.66-1.58 (1H, m), 1.52-1.36 (4H, m), 0.91 (6H, t).
本発明化合物11:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.87 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 1.78-1.69 (2H, m), 1.46-1.31 (4H, m), 0.92 (3H, t).
本発明化合物12:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.43 (1H, dd), 6.37 (1H, d), 3.86 (3H, s), 3.72 (2H, d), 3.70 (3H, s), 2.27 (3H, s), 1.29-1.19 (1H, m), 0.63 (2H, q), 0.32 (2H, q).
本発明化合物13:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.86 (3H, s), 3.74 (2H, d), 3.70 (3H, s), 2.36-2.26 (1H, m), 2.26 (3H, s), 1.87-1.75 (2H, m), 1.66-1.53 (4H, m), 1.38-1.27 (2H, m).
本発明化合物14:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.02 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 3.66 (2H, d), 2.26 (3H, s), 1.89-1.64 (6H, m), 1.34-1.15 (3H, m), 1.07-0.94 (2H, m).
本発明化合物15:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.03 (1H, d), 6.46 (1H, dd), 6.33 (1H, d), 3.95 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.63 (2H, q), 0.87-0.76 (1H, m), 0.50-0.43 (2H, m), 0.12-0.06 (2H, m).
本発明化合物16:1H-NMR (CDCl3) δ: 7.32 (1H, s), 7.04 (1H, d), 6.46 (1H, dd), 6.33 (1H, d), 4.69 (1H, t), 4.57 (1H, t), 4.02 (2H, t), 3.87 (3H, s), 3.71 (3H, s), 2.28 (3H, s), 2.20-2.06 (2H, m).
本発明化合物17:1H-NMR (CDCl3) δ: 7.32 (1H, s), 7.05 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 4.12 (2H, t), 3.87 (3H, s), 3.71 (3H, s), 2.63-2.51 (2H, m), 2.27 (3H, s).
本発明化合物18:1H-NMR (CDCl3) δ: 7.32 (1H, s), 7.04 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 3.93 (2H, t), 3.87 (3H, s), 3.71 (3H, s), 2.33-2.22 (2H, m), 2.27 (3H, s), 2.04-1.96 (2H, m).
本発明化合物19:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.05 (1H, d), 6.45 (1H, dd), 6.36 (1H, d), 4.16 (2H, t), 3.87 (3H, s), 3.77 (2H, t), 3.71 (3H, s), 2.28 (3H, s).
本発明化合物20:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.04 (1H, d), 6.46 (1H, dd), 6.32 (1H, d), 4.03 (2H, t), 3.87 (3H, s), 3.72 (2H, t), 3.71 (3H, s), 2.27 (3H, s), 2.23-2.15 (2H, m).
本発明化合物21:1H-NMR (CDCl3) δ: 7.29 (1H, s), 7.03 (1H, d), 6.46 (1H, dd), 6.40 (1H, d), 4.04 (2H, t), 3.86 (3H, s), 3.71 (2H, t), 3.69 (3H, s), 3.44 (3H, s), 2.27 (3H, s).
本発明化合物22:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.04 (1H, d), 6.45 (1H, dd), 6.38 (1H, d), 4.14 (1H, dd), 3.91-3.85 (1H, m), 3.87 (3H, s), 3.71 (3H, s), 3.34-3.29 (1H, m), 2.91-2.87 (1H, m), 2.74 (1H, dd), 2.27 (3H, s).
本発明化合物23:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.02 (1H, d), 6.45 (1H, dd), 6.38 (1H, d), 4.27-4.19 (1H, m), 3.96-3.78 (4H, m), 3.86 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 2.10-1.88 (3H, m), 1.77-1.67 (1H, m).
本発明化合物24:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.45 (1H, dd), 6.35 (1H, d), 4.02 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.72 (2H, t), 2.53-2.43 (4H, m), 2.26 (3H, s), 1.64-1.56 (4H, m), 1.48-1.40 (2H, m).
本発明化合物25:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 3.99 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.09 (2H, t), 0.06 (9H, s).
本発明化合物26:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.03 (1H, d), 6.44 (1H, dd), 6.33 (1H, d), 3.86 (3H, s), 3.83 (2H, t), 3.70 (3H, s), 2.27 (3H, s), 1.79-1.69 (2H, m), 0.60-0.54 (2H, m), 0.01 (9H, s).
本発明化合物27:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.05 (1H, d), 6.44-6.38 (2H, m), 4.56 (2H, s), 3.87 (3H, s), 3.80 (3H, s), 3.71 (3H, s), 2.28 (3H, s).
本発明化合物28:1H-NMR (CDCl3) δ: 7.46 (1H, s), 7.44-7.28 (5H, m), 7.02 (1H, d), 6.75 (1H, d), 6.69 (1H, dd), 4.99 (2H, s), 3.81 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.28 (3H, s).
本発明化合物29:1H-NMR (CDCl3) δ: 7.35-7.21 (6H, m), 7.03 (1H, d), 6.45 (1H, dd), 6.32 (1H, d), 4.09 (2H, t), 3.85 (3H, s), 3.70 (3H, s), 3.06 (2H, t), 2.27 (3H, s).
本発明化合物30:1H-NMR (CDCl3) δ: 7.40-7.34 (2H, m), 7.29 (1H, s), 7.09-7.01 (3H, m), 6.51 (1H, dd), 6.38 (1H, d), 4.93 (2H, s), 3.84 (3H, s), 3.69 (3H, s), 2.27 (3H, s).
本発明化合物31:1H-NMR (CDCl3) δ: 7.39-7.30 (4H, m), 7.29 (1H, s), 7.14-6.98 (6H, m), 6.54 (1H, dd), 6.41 (1H, d), 4.94 (2H, s), 3.85 (3H, s), 3.69 (3H, s), 2.28 (3H, s).
本発明化合物32:1H-NMR (CDCl3) δ: 7.66 (1H, t), 7.45 (1H, d), 7.31 (1H, s), 7.25 (1H, d), 7.04 (1H, d), 6.50 (1H, dd), 6.40 (1H, d), 5.09 (2H, s), 3.86 (3H, s), 3.70 (3H, s), 2.27 (3H, s).
本発明化合物33:1H-NMR (CDCl3) δ: 8.76 (1H, s), 7.94 (1H, d), 7.70 (1H, d), 7.31 (1H, s), 7.07 (1H, d), 6.51 (1H, dd), 6.38 (1H, d), 5.08 (2H, s), 3.86 (3H, s), 3.70 (3H, s), 2.28 (3H, s).
本発明化合物34:1H-NMR (CDCl3) δ: 7.33-7.29 (2H, m), 7.10-6.98 (3H, m), 6.54 (1H, dd), 6.41 (1H, d), 5.13 (2H, s), 3.85 (3H, s), 3.69 (3H, s), 2.28 (3H, s).
本発明化合物35:1H-NMR (CDCl3) δ: 7.78 (1H, d), 7.35 (1H, d), 7.31 (1H, s), 7.06 (1H, d), 6.55 (1H, dd), 6.44 (1H, d), 5.30 (2H, s), 3.86 (3H, s), 3.70 (3H, s), 2.28 (3H, s).
本発明化合物36:1H-NMR (CDCl3) δ: 7.32 (1H, s), 7.07 (1H, d), 6.72 (1H, s), 6.49 (1H, dd), 6.38 (1H, d), 5.12 (2H, s), 4.44 (2H, q), 3.87 (3H, s), 3.71 (3H, s), 2.28 (3H, s), 1.41 (3H, t).
本発明化合物37:1H-NMR (CDCl3) δ: 7.32 (1H, s), 7.05 (1H, d), 6.46 (1H, dd), 6.37 (1H, d), 5.54-5.52 (1H, m), 5.42-5.40 (1H, m), 4.50 (2H, t), 3.87 (3H, s), 3.71 (3H, s), 2.27 (3H, s).
本発明化合物38:1H-NMR (CDCl3) δ: 7.32 (1H, s), 7.05 (1H, d), 6.43 (1H, dd), 6.32 (1H, d), 6.11 (1H, t), 4.59 (2H, d), 3.87 (3H, s), 3.71 (3H, s), 2.28 (3H, s).
本発明化合物39:1H-NMR (CDCl3) δ: 7.38-7.28 (6H, m), 7.01 (1H, d), 6.46 (1H, dd), 6.36 (1H, d), 5.12 (2H, s), 4.45 (2H, s), 3.85 (3H, s), 3.70 (3H, s), 2.27 (3H, s), 1.97 (3H, s).
本発明化合物71:1H-NMR (CDCl3) δ: 7.47 (1H, s), 7.00 (1H, d), 6.67 (1H, d), 6.61 (1H, dd), 3.85 (2H, t), 3.83 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.27 (3H, s), 1.82-1.71 (2H, m), 1.01 (3H, t).
本発明化合物72:1H-NMR (CDCl3) δ: 7.33 (1H, s), 7.24 (1H, d), 6.48 (1H, dd), 6.39 (1H, d), 3.90-3.85 (5H, m), 3.72 (3H, s), 1.77-1.68 (2H, m), 1.52-1.41 (2H, m), 0.96 (3H, t).
本発明化合物73:1H-NMR (CDCl3) δ: 7.48 (1H, s), 7.00 (1H, d), 6.67 (1H, d), 6.61 (1H, dd), 3.83 (3H, s), 3.67 (3H, s), 3.65 (2H, d), 3.51 (2H, s), 2.27 (3H, s), 2.09-1.98 (1H, m), 0.99 (6H, d).
本発明化合物74:1H-NMR (CDCl3) δ: 7.47 (1H, s), 7.00 (1H, d), 6.69-6.58 (2H, m), 3.88 (2H, t), 3.83 (3H, s), 3.67 (3H, s), 3.51 (2H, s), 2.27 (3H, s), 1.78-1.71 (2H, m), 1.47-1.30 (4H, m), 0.92 (3H, t).
本発明化合物75:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.02 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 3.87 (2H, t), 3.86 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 1.77-1.69 (2H, m), 1.46-1.24 (12H, m), 0.88 (3H, t).
本発明化合物76:1H-NMR (CDCl3) δ: 7.47 (1H, s), 7.00 (1H, d), 6.68 (1H, d), 6.60 (1H, dd), 3.83 (3H, s), 3.72 (2H, d), 3.66 (3H, s), 3.50 (2H, s), 2.26 (3H, s), 1.28-1.19 (1H, m), 0.64-0.58 (2H, m), 0.34-0.29 (2H, m).
本発明化合物77:1H-NMR (CDCl3) δ: 7.42-7.24 (7H, m), 6.57 (1H, dd), 6.48 (1H, d), 4.98 (2H, s), 3.84 (3H, s), 3.70 (3H, s).
本発明化合物78:1H-NMR (CDCl3) δ: 7.47 (1H, s), 7.34-7.19 (5H, m), 7.00 (1H, d), 6.69 (1H, d), 6.62 (1H, dd), 4.11 (2H, t), 3.81 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 3.06 (2H, t), 2.27 (3H, s).
本発明化合物79:1H-NMR (CDCl3) δ: 7.36-7.21 (7H, m), 6.48 (1H, dd), 6.39 (1H, d), 4.09 (2H, t), 3.86 (3H, s), 3.71 (3H, s), 3.06 (2H, t).
本発明化合物80:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.29-7.25 (2H, m), 7.21-7.15 (3H, m), 7.02 (1H, d), 6.43 (1H, dd), 6.31 (1H, d), 3.91-3.87 (2H, m), 3.85 (3H, s), 3.69 (3H, s), 2.70-2.63 (2H, m), 2.26 (3H, s), 1.80-1.75 (4H, m).
本発明化合物81:1H-NMR (CDCl3) δ: 7.48 (1H, s), 7.01 (1H, d), 6.70 (1H, d), 6.63 (1H, dd), 6.10-5.98 (1H, m), 5.42-5.34 (1H, m), 5.28-5.23 (1H, m), 4.49-4.45 (2H, m), 3.83 (3H, s), 3.67 (3H, s), 3.51 (2H, s), 2.28 (3H, s).
本発明化合物82:1H-NMR (CDCl3) δ: 7.48 (1H, s), 7.03 (1H, d), 6.75 (1H, d), 6.69 (1H, dd), 4.62 (2H, d), 3.83 (3H, s), 3.67 (3H, s), 3.51 (2H, s), 2.49 (1H, t), 2.29 (3H, s).
本発明化合物83:1H-NMR (CDCl3) δ: 7.46 (1H, s), 7.34 (2H, d), 7.02 (1H, d), 6.90 (2H, d), 6.74 (1H, d), 6.69 (1H, dd), 4.91 (2H, s), 3.82 (3H, s), 3.81 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.28 (3H, s).
本発明化合物84:1H-NMR (CDCl3) δ: 7.46 (1H, s), 7.36-7.28 (1H, m), 7.20-7.12 (2H, m), 7.04-6.95 (2H, m), 6.73 (1H, d), 6.67 (1H, dd), 4.99 (2H, s), 3.82 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.28 (3H, s).
本発明化合物85:1H-NMR (CDCl3) δ: 7.47 (1H, s), 7.31-7.27 (1H, m), 7.10-6.96 (3H, m), 6.75 (1H, d), 6.70 (1H, dd), 5.14 (2H, s), 3.81 (3H, s), 3.66 (3H, s), 3.51 (2H, s), 2.28 (3H, s).
本発明化合物86:1H-NMR (CDCl3) δ: 7.49-7.46 (1H, m), 7.42-7.40 (1H, m), 7.29 (1H, s), 7.05 (1H, d), 6.52 (1H, dd), 6.47-6.45 (1H, m), 6.39 (1H, d), 4.85 (2H, s), 3.85 (3H, s), 3.69 (3H, s), 2.28 (3H, s).
本発明化合物87:1H-NMR (CDCl3) δ: 8.58-8.55 (2H, m), 7.32 (1H, s), 7.07 (1H, d), 6.52 (1H, dd), 6.42 (1H, d), 5.14 (2H, s), 3.87 (3H, s), 3.71 (3H, s), 2.28 (3H, s).
本発明化合物88:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.02 (1H, d), 6.52-6.46 (1H, m), 6.36-6.27 (1H, m), 4.17-3.98 (2H, m), 3.87 (3H, s), 3.85-3.65 (1H, m), 3.71 (3H, s), 3.43-3.27 (2H, m), 2.26 (3H, s), 2.06-1.77 (4H, m), 1.47 (9H, s).
室温で、0.29gの中間体A1、炭酸カリウム0.25g及びDMF10mLの混合物に、ベンジルブロミド0.16mLを加え、3時間撹拌した。得られた混合物に、水を加え、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し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:4)に付し、次式で示される本発明化合物40を0.31g得た。
製造例2に準じて製造した化合物及びその物性値を以下に示す。
式(1a1)で示される化合物において、E、R1及びLが[表2-1]に記載のいずれかの組合せである化合物。
本発明化合物42:1H-NMR (CDCl3) δ: 7.74 (1H, s), 7.66-7.58 (2H, m), 7.48 (1H, t), 7.32 (1H, s), 7.06 (1H, d), 6.49 (1H, dd), 6.39 (1H, d), 5.00 (2H, s), 3.87 (3H, s), 3.70 (3H, s), 2.28 (3H, s).
本発明化合物43:1H-NMR (CDCl3) δ: 7.67 (2H, d), 7.52 (2H, d), 7.30 (1H, s), 7.06 (1H, d), 6.48 (1H, dd), 6.38 (1H, d), 5.04 (2H, s), 3.86 (3H, s), 3.70 (3H, s), 2.28 (3H, s).
本発明化合物44:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.06 (1H, d), 6.52 (1H, dd), 6.41 (1H, d), 4.61 (2H, d), 3.86 (3H, s), 3.70 (3H, s), 2.50 (1H, t), 2.28 (3H, s).
本発明化合物45:1H-NMR (CDCl3) δ: 7.33 (1H, s), 7.05 (1H, d), 6.44 (1H, dd), 6.32 (1H, d), 4.00 (2H, t), 3.88 (3H, s), 3.72 (3H, s), 2.57 (2H, t), 2.28 (3H, s), 2.14-2.05 (2H, m).
室温で、0.20gの中間体A1、炭酸カリウム0.15g及びDMF5mLの混合物に、ジメチルカルバモイルクロリド0.09mLを加え、19時間撹拌した。得られた混合物に、飽和塩化アンモニウム水溶液を加え、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順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:3)に付し、次式で示される本発明化合物46を0.08g得た。
製造例3に準じて製造した化合物及びその物性値を以下に示す。
式(1a1)で示される化合物において、E、R1及びLが[表3-1]に記載のいずれかの組合せである化合物。
本発明化合物48:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.68 (1H, dd), 6.51 (1H, d), 3.86 (3H, s), 3.71 (3H, s), 3.44-3.32 (4H, m), 2.31 (3H, s), 1.25-1.14 (6H, m).
本発明化合物49:1H-NMR (CDCl3) δ: 7.42-7.30 (4H, m), 7.29 (1H, s), 7.27-7.22 (1H, m), 7.09 (1H, d), 6.75-6.61 (1H, br m), 6.51 (1H, br s), 3.85 (3H, s), 3.69 (3H, s), 3.40 (3H, s), 2.30 (3H, s).
本発明化合物50:1H-NMR (CDCl3) δ: 7.45 (1H, s), 7.41-7.32 (4H, m), 7.25-7.21 (1H, m), 7.06 (1H, d), 6.86-6.77 (2H, m), 3.83 (3H, s), 3.65 (3H, s), 3.51 (2H, s), 3.41 (3H, s), 2.30 (3H, s).
本発明化合物51:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.71 (1H, dd), 6.54 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 3.52 (2H, t), 3.45 (2H, t), 2.31 (3H, s), 1.98-1.85 (4H, m).
本発明化合物52:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.67 (1H, dd), 6.50 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 3.62-3.43 (4H, br m), 2.30 (3H, s), 1.69-1.52 (6H, m).
本発明化合物89:1H-NMR (CDCl3) δ: 7.46 (1H, s), 7.07 (1H, d), 6.85-6.80 (2H, m), 3.83 (3H, s), 3.66 (3H, s), 3.52 (2H, s), 3.07 (3H, s), 2.99 (3H, s), 2.31 (3H, s).
本発明化合物90:1H-NMR (CDCl3) δ: 7.46 (1H, s), 7.07 (1H, d), 6.87-6.80 (2H, m), 3.83 (3H, s), 3.67 (3H, s), 3.53 (2H, s), 3.46-3.32 (4H, m), 2.31 (3H, s), 1.27-1.15 (6H, m).
室温で、0.25gの中間体A1、トリホスゲン0.10g及びクロロホルム5mLの混合物に、N,N-ジイソプロピルエチルアミン0.18mLを加え、2時間撹拌した。得られた混合物に、プロピルアミン0.11mL及びN,N-ジイソプロピルエチルアミン0.27mLを順次加え、16時間撹拌した。得られた混合物に、水を加え、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順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:4)に付し、次式で示される本発明化合物53を0.18g得た。
製造例4に準じて製造した化合物及びその物性値を以下に示す。
式(1a1)で示される化合物において、E、R1及びLが[表4-1]に記載のいずれかの組合せである化合物。
本発明化合物55:1H-NMR (CDCl3) δ: 7.29 (1H, s), 7.10 (1H, d), 6.69 (1H, dd), 6.52 (1H, d), 4.93-4.85 (1H, br m), 3.85 (3H, s), 3.70 (3H, s), 3.23 (2H, q), 2.30 (3H, s), 1.59-1.50 (2H, m), 1.38-1.28 (4H, m), 0.91 (3H, t).
本発明化合物56:1H-NMR (CDCl3) δ: 7.29 (1H, s), 7.09 (1H, d), 6.69 (1H, dd), 6.52 (1H, d), 4.83-4.76 (1H, br m), 3.85 (3H, s), 3.70 (3H, s), 3.58-3.47 (1H, m), 2.30 (3H, s), 2.02-1.94 (2H, m), 1.77-1.66 (2H, m), 1.65-1.57 (1H, m), 1.42-1.29 (2H, m), 1.26-1.12 (3H, m).
本発明化合物57:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.71-6.63 (1H, m), 6.52-6.47 (1H, m), 3.86 (3H, s), 3.70 (3H, s), 3.38-3.25 (2H, m), 3.03 (1.4H, s), 2.97 (1.6H, s), 2.31 (3H, s), 1.68-1.58 (2H, m), 0.98-0.90 (3H, m).
本発明化合物58:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.10 (1H, d), 6.71-6.64 (1H, m), 6.51-6.49 (1H, m), 3.86 (3H, s), 3.70 (3H, s), 3.41-3.28 (2H, m), 3.03 (1.4H, s), 2.96 (1.6H, s), 2.30 (3H, s), 1.64-1.52 (2H, m), 1.41-1.30 (2H, m), 0.98-0.92 (3H, m).
本発明化合物59:1H-NMR (CDCl3) δ: 7.30 (1H, s), 7.13 (1H, d), 6.71 (1H, dd), 6.55 (1H, d), 3.86 (3H, s), 3.78 (3H, s), 3.70 (3H, s), 3.26 (3H, s), 2.32 (3H, s).
室温で、0.20gの中間体A1、プロピオニルクロリド0.09mL及びクロロホルム5mLの混合物に、トリエチルアミン0.17mLを加え、16時間撹拌した。得られた混合物に、水を加え、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順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:4)に付し、次式で示される本発明化合物60を0.18g得た。
製造例5に準じて製造した化合物及びその物性値を以下に示す。
式(1a1)で示される化合物において、E、R1及びLが[表5-1]に記載のいずれかの組合せである化合物。
本発明化合物62:1H-NMR (CDCl3) δ: 8.17 (2H, d), 7.62 (1H, t), 7.49 (2H, t), 7.31 (1H, s), 7.18 (1H, d), 6.79 (1H, dd), 6.60 (1H, d), 3.87 (3H, s), 3.71 (3H, s), 2.35 (3H, s).
本発明化合物63:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.14 (1H, d), 6.76 (1H, dd), 6.57 (1H, d), 4.29 (2H, q), 3.87 (3H, s), 3.71 (3H, s), 2.32 (3H, s), 1.37 (3H, t).
本発明化合物64:1H-NMR (CDCl3) δ: 7.31 (1H, s), 7.12 (1H, d), 6.77 (1H, dd), 6.55 (1H, d), 3.86 (3H, s), 3.70 (3H, s), 2.31 (3H, s), 1.54 (9H, s).
本発明化合物65:1H-NMR (CDCl3) δ: 7.33 (1H, s), 7.17 (1H, d), 6.83 (1H, dd), 6.68 (1H, d), 3.88 (3H, s), 3.72 (3H, s), 3.07 (3H, s), 2.34 (3H, s).
本発明化合物66:1H-NMR (CDCl3) δ: 7.33 (1H, s), 7.16 (1H, d), 6.81 (1H, dd), 6.66 (1H, d), 3.88 (3H, s), 3.72 (3H, s), 3.18-3.12 (2H, m), 2.33 (3H, s), 2.03-1.91 (2H, m), 1.09 (3H, t).
本発明化合物67:1H-NMR (CDCl3) δ: 7.80 (2H, t), 7.64 (1H, t), 7.50 (2H, t), 7.25 (1H, s), 7.01 (1H, d), 6.46 (1H, dd), 6.42 (1H, d), 3.85 (3H, s), 3.70 (3H, s), 2.28 (3H, s).
室温で、0.18gの中間体A1、ジメチルチオカルバモイルクロリド0.11g及びDMF5mLの混合物に、水素化ナトリウム(60%、油状)0.05gを加え、4時間撹拌した。得られた混合物に、飽和塩化アンモニウム水溶液を加え、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順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:3)に付し、次式で示される本発明化合物68を0.12g得た。
製造例6に準じて製造した化合物及びその物性値を以下に示す。
式(1a1)で示される化合物において、E、R1及びLが[表6-1]に記載のいずれかの組合せである化合物。
本発明化合物70:1H-NMR (CDCl3) δ: 7.33 (1H, s), 7.13 (1H, d), 6.81 (1H, dd), 6.67 (1H, d), 3.87 (3H, s), 3.71 (3H, s), 3.30 (4H, q), 2.32 (3H, s), 1.16 (6H, t).
0.19gの中間体B1、炭酸カリウム0.10g及びDMF5mLの混合物に、0℃でヨードメタン0.10mLを加え、1時間撹拌した。得られた混合物に、水を加え、MTBEで抽出した。得られた有機層を水及び飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー(酢酸エチル:ヘキサン=1:4)に付し、次式で示される本発明化合物40を0.09g得た。
0.03gの中間体D2、ベンジルアルコール0.02g、酢酸パラジウム(II)0.001g、2-(ジ-t-ブチルホスフィノ)-1,1’-ビナフチル0.002g、炭酸セシウム0.08g及びトルエン2mLの混合物を、40℃で15時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を無水硫酸ナトリウムで乾燥し、減圧下で濃縮し、本発明化合物40を含む粗生成物0.03gを得た。
本発明化合物40:LCMS: 329 [M+H]+, RT = 2.08 分
0.05gの中間体D1、ベンジルアルコール0.04g、0.01gのtBuBrettPhos Pd G3、ナトリウムtert-ブトキシド0.03g及びジオキサン2mLの混合物を、80℃で4時間撹拌した。得られた混合物に水を加え、酢酸エチルで抽出した。得られた有機層を無水硫酸ナトリウムで乾燥し、減圧下で濃縮し、本発明化合物28を含む粗生成物0.05gを得た。
本発明化合物28:LCMS: 327 [M+H]+, RT = 2.22 分
2N(CH2CH3)2,(CH2)3F,(CH2)3Cl,(CH2)3Br,(CH2)3I,(CH2)3CF3,(CH2)3CN,(CH2)3NO2,(CH2)3Si(CH3)3,(CH2)3OCH3,(CH2)3OCH2CH3,(CH2)3SCH3,(CH2)3SCH2CH3,(CH2)3NHCH3,(CH2)3N(CH3)2,(CH2)4F,(CH2)4Cl,(CH2)4CF3,(CH2)4CN,(CH2)4NO2,(CH2)4Ph,(CH2)4OCH3,(CH2)4SCH3,(CH2)4NHCH3,(CH2)4N(CH3)2,(CH2)5F,(CH2)5Cl,(CH2)5CF3,(CH2)5CN,(CH2)5NO2,(CH2)5Ph,(CH2)5OCH3,(CH2)5SCH3,(CH2)5NHCH3,(CH2)5N(CH3)2,(CH2)6F,(CH2)6Cl,(CH2)6CF3,(CH2)6CN,(CH2)6NO2,(CH2)6Ph,(CH2)6OCH3,(CH2)6SCH3,(CH2)6NHCH3,(CH2)6N(CH3)2,CH2CF2CF3,(CH2)2CF2CF3,CH2(CF2)2CF3,(CH2)2CF(CF3)2,(CH2)2(CF2)5CF3,CF3,CF2CHF(CF3),CF2CHF(OCF3),CH2CF2CF2Hからなる群。
[ZA1;H,H,H,H,H],[ZA2;Me,H,H,H,H],[ZA3;F,H,H,H,H],[ZA4;Cl,H,H,H,H],[ZA5;OMe,H,H,H,H],[ZA6;CF3,H,H,H,H],[ZA7;H,Me,H,H,H],[ZA8;H,Et,H,H,H],[ZA9;H,Pr,H,H,H],[ZA10;H,i-Pr,H,H,H],[ZA11;H,t-Bu,H,H,H],[ZA12;H,OMe,H,H,H],[ZA13;H,OEt,H,H,H],[ZA14;H,OPr,H,H,H],[ZA15;H,Oi-Pr,H,H,H],[ZA16;H,CF3,H,H,H],[ZA17;H,CF2H,H,H,H],[ZA18;H,CFH2,H,H,H],[ZA19;H,F,H,H,H],[ZA20;H,Cl,H,H,H],[ZA21;H,Br,H,H,H],[ZA22;H,CN,H,H,H],[ZA23;H,Ph,H,H,H],[ZA24;H,OPh,H,H,H],[ZA25;H,c-Pr,H,H,H],[ZA26;H,c-Pen,H,H,H],[ZA27;H,c-Hex,H,H,H],[ZA28;H,H,Me,H,H],[ZA29;H,H,Et,H,H],[ZA30;H,H,Pr,H,H],[ZA31;H,H,i-Pr,H,H],[ZA32;H,H,t-Bu,H,H],[ZA33;H,H,OMe,H,H],[ZA34;H,H,OEt,H,H],[ZA35;H,H,OPr,H,H],[ZA36;H,H,Oi-Pr,H,H],[ZA37;H,H,CF3,H,H],[ZA38;H,H,CF2H,H,H],[ZA39;H,H,CFH2,H,H],[ZA40;H,H,F,H,H],[ZA41;H,H,Cl,H,H],[ZA42;H,H,Br,H,H],[ZA43;H,H,CN,H,H],[ZA44;H,H,Ph,H,H],[ZA45;H,H,OPh,H,H],[ZA46;H,H,c-Pr,H,H],[ZA47;H,H,c-Pen,H,H],[ZA48;H,H,c-Hex,H,H],[ZA49;H,H,H,H,F],[ZA50;Me,H,H,H,F],[ZA51;F,H,H,H,F],[ZA52;Cl,H,H,H,F],[ZA53;H,Me,H,H,F],[ZA54;H,Et,H,H,F],[ZA55;H,Pr,H,H,F],[ZA56;H,i-Pr,H,H,F],[ZA57;H,t-Bu,H,H,F],[ZA58;H,OMe,H,H,F],[ZA59;H,OEt,H,H,F],[ZA60;H,OPr,H,H,F],[ZA61;H,Oi-Pr,H,H,F],[ZA62;H,CF3,H,H,F],[ZA63;H,CF2H,H,H,F],[ZA64;H,CFH2,H,H,F],[ZA65;H,F,H,H,F],[ZA66;H,Cl,H,H,F],[ZA67;H,Br,H,H,F],[ZA68;H,CN,H,H,F],[ZA69;H,Ph,H,H,F],[ZA70;H,OPh,H,H,F],[ZA71;H,c-Pr,H,H,F],[ZA72;H,c-Pen,H,H,F],[ZA73;H,c-Hex,H,H,F],[ZA74;H,H,Me,H,F],[ZA75;H,H,Et,H,F],[ZA76;H,H,Pr,H,F],[ZA77;H,H,i-Pr,H,F],[ZA78;H,H,t-Bu,H,F],[ZA79;H,H,OMe,H,F],[ZA80;H,H,OEt,H,F],[ZA81;H,H,OPr,H,F],[ZA82;H,H,Oi-Pr,H,F],[ZA83;H,H,CF3,H,F],[ZA84;H,H,CF2H,H,F],[ZA85;H,H,CFH2,H,F],[ZA86;H,H,F,H,F],[ZA87;H,H,Cl,H,F],[ZA88;H,H,Br,H,F],[ZA89;H,H,CN,H,F],[ZA90;H,H,Ph,H,F],[ZA91;H,H,OPh,H,F],[ZA92;H,H,c-Pr,H,F],[ZA93;H,H,c-Pen,H,F],[ZA94;H,H,c-Hex,H,F],[ZA95;H,H,H,H,Cl],[ZA96;Me,H,H,H,Cl],[ZA97;F,H,H,H,Cl],[ZA98;Cl,H,H,H,Cl],[ZA99;H,Me,H,H,Cl],[ZA100;H,Et,H,H,Cl]
で示される化合物において、R1がメチル基であり、Lが酸素原子であり、mが1であり、Gの構造及びGの構造に対応する置換基RX7、RX8、RX9及びRX10が、組合せBに記載のいずれかの組合せである化合物(以下、化合物群SX17と記す)。
[ZB1;G1,H,H,H,H],[ZB2;G1,Me,H,H,H],[ZB3;G1,Et,H,H,H],[ZB4;G1,Pr,H,H,H],[ZB5;G1,i-Pr,H,H,H],[ZB6;G1,c-Pr,H,H,H],[ZB7;G1,Ph,H,H,H],[ZB8;G1,OMe,H,H,H],[ZB9;G1,OEt,H,H,H],[ZB10;G1,OPh,H,H,H],[ZB11;G1,CF3,H,H,H],[ZB12;G1,F,H,H,H],[ZB13;G1,Cl,H,H,H],[ZB14;G1,Br,H,H,H],[ZB15;G1,CN,H,H,H],[ZB16;G1,H,Me,H,H],[ZB17;G1,H,Et,H,H],[ZB18;G1,H,Pr,H,H],[ZB19;G1,H,i-Pr,H,H],[ZB20;G1,H,c-Pr,H,H],[ZB21;G1,H,Ph,H,H],[ZB22;G1,H,OMe,H,H],[ZB23;G1,H,OEt,H,H],[ZB24;G1,H,OPh,H,H],[ZB25;G1,H,CF3,H,H],[ZB26;G1,H,F,H,H],[ZB27;G1,H,Cl,H,H],[ZB28;G1,H,Br,H,H],[ZB29;G1,H,CN,H,H],[ZB30;G1,H,H,Me,H],[ZB31;G1,H,H,Et,H],[ZB32;G1,H,H,Pr,H],[ZB33;G1,H,H,i-Pr,H],[ZB34;G1,H,H,c-Pr,H],[ZB35;G1,H,H,Ph,H],[ZB36;G1,H,H,OMe,H],[ZB37;G1,H,H,OEt,H],[ZB38;G1,H,H,OPh,H],[ZB39;G1,H,H,CF3,H],[ZB40;G1,H,H,F,H],[ZB41;G1,H,H,Cl,H],[ZB42;G1,H,H,Br,H],[ZB43;G1,H,H,CN,H],[ZB44;G1,H,H,H,Me],[ZB45;G1,H,H,H,Et],[ZB46;G1,H,H,H,Pr],[ZB47;G1,H,H,H,i-Pr],[ZB48;G1,H,H,H,c-Pr],[ZB49;G1,H,H,H,Ph],[ZB50;G1,H,H,H,OMe],[ZB51;G1,H,H,H,OEt],[ZB52;G1,H,H,H,OPh],[ZB53;G1,H,H,H,CF3],[ZB54;G1,H,H,H,F],[ZB55;G1,H,H,H,Cl],[ZB56;G1,H,H,H,Br],[ZB57;G1,H,H,H,CN],[ZB58;G2,H,H,H,H],[ZB59;G2,Me,H,H,H],[ZB60;G2,Et,H,H,H],[ZB61;G2,Pr,H,H,H],[ZB62;G2,i-Pr,H,H,H],[ZB63;G2,c-Pr,H,H,H],[ZB64;G2,Ph,H,H,H],[ZB65;G2,OMe,H,H,H],[ZB66;G2,OEt,H,H,H],[ZB67;G2,OPh,H,H,H],[ZB68;G2,CF3,H,H,H],[ZB69;G2,F,H,H,H],[ZB70;G2,Cl,H,H,H],[ZB71;G2,Br,H,H,H],[ZB72;G2,CN,H,H,H],[ZB73;G2,H,Me,H,H],[ZB74;G2,H,Et,H,H],[ZB75;G2,H,Pr,H,H],[ZB76;G2,H,i-Pr,H,H],[ZB77;G2,H,c-Pr,H,H],[ZB78;G2,H,Ph,H,H],[ZB79;G2,H,OMe,H,H],[ZB80;G2,H,OEt,H,H],[ZB81;G2,H,OPh,H,H],[ZB82;G2,H,CF3,H,H],[ZB83;G2,H,F,H,H],[ZB84;G2,H,Cl,H,H],[ZB85;G2,H,Br,H,H],[ZB86;G2,H,CN,H,H],[ZB87;G2,H,H,Me,H],[ZB88;G2,H,H,Et,H],[ZB89;G2,H,H,Pr,H],[ZB90;G2,H,H,i-Pr,H],[ZB91;G2,H,H,c-Pr,H],[ZB92;G2,H,H,Ph,H],[ZB93;G2,H,H,OMe,H],[ZB94;G2,H,H,OEt,H],[ZB95;G2,H,H,OPh,H],[ZB96;G2,H,H,CF3,H],[ZB97;G2,H,H,F,H],[ZB98;G2,H,H,Cl,H],[ZB99;G2,H,H,Br,H],[ZB100;G2,H,H,CN,H]
群Z:1-pyrrolidinyl, 1-piperidinyl, 4-morpholinylからなる群。
本発明化合物Sのいずれか1種50部、リグニンスルホン酸カルシウム3部、ラウリル硫酸マグネシウム2部及び合成含水酸化珪素45部をよく粉砕混合することにより、製剤を得る。
本発明化合物Sのいずれか1種20部とソルビタントリオレエート1.5部とを、ポリビニルアルコール2部を含む水溶液28.5部と混合し、湿式粉砕法で微粉砕した後、この中に、キサンタンガム0.05部及びアルミニウムマグネシウムシリケート0.1部を含む水溶液40部を加え、さらにプロピレングリコール10部を加えて攪拌混合し、製剤を得る。
本発明化合物Sのいずれか1種2部、カオリンクレー88部及びタルク10部をよく粉砕混合することにより、製剤を得る。
本発明化合物Sのいずれか1種5部、ポリオキシエチレンスチリルフェニルエーテル14部、ドデシルベンゼンスルホン酸カルシウム6部及びキシレン75部をよく混合することにより、製剤を得る。
本発明化合物Sのいずれか1種2部、合成含水酸化珪素1部、リグニンスルホン酸カルシウム2部、ベントナイト30部及びカオリンクレー65部をよく粉砕混合した後、水を加えてよく練り合せ、造粒乾燥することにより、製剤を得る。
本発明化合物Sのいずれか1種20部;ホワイトカーボンとポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩との混合物(重量割合1:1)35部及び水を混合し全量を100部とし、粉砕機を用いて処理することにより、製剤を得る。
試験例1~試験例9における無処理区とは、本発明化合物を含有するDMSO希釈液の代わりにDMSOを分注する以外は各々の試験例に記載されたのと同じ条件で行った試験区を表す。また、試験例10~試験例22における無処理とは、本発明化合物を含む製剤の水希釈液の散布を行わなかったことを意味する。
本発明化合物1~16、18~23、25、26、28~30、33~35、37、38~40、42~52、54~87、89又は90を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめコムギ葉枯病菌の胞子を接種したジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを5日間、18℃で培養しコムギ葉枯病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をコムギ葉枯病菌の生育度とした。その結果、各々の化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物2~16、18~20、25、26、29、38、40、42~44、46~49、51、52、55、57~64、71又は76を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめダイズ炭疽病菌の胞子を接種したジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを4日間、18℃で培養しダイズ炭疽菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をダイズ炭疽病菌の生育度とした。その結果、各々の化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物1~20、23、25、26、29、34、37、38、40~49、51、52、54~64、68、71、73~76、80、89又は90を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめウリ類灰色疫病菌の胞子を接種したジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを3日間、27℃で培養しウリ類灰色疫病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をウリ類灰色疫病菌の生育度とした。その結果、各々の化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物1~20、23、25、26、29、34、37、38、40~49、51、52、54~64、66、68、71~76、79~81、84~86、89又は90を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめ苗立枯病菌の胞子を接種したジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを5日間、23℃で培養し苗立枯病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値を苗立枯病菌の生育度とした。その結果、各々の化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物1~20、23、25、26、29、30、34、37~49、51、52、54~64、68、71~76、78~87、89又は90を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめトウモロコシ黒穂病菌の胞子を接種したジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを4日間、18℃で培養しトウモロコシ黒穂病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をトウモロコシ黒穂病菌の生育度とした。その結果、各々の化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物1~20、23、25、26、29~49、51、52、54~64、66~68、71~87、89又は90を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめオオムギ雲形病菌の胞子を接種したジャガイモ煎汁液体培地(PDB培地)を150μL分注した。このプレートを7日間、18℃で培養しオオムギ雲形病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をオオムギ雲形病菌の生育度とした。その結果、各々の化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物1~20、23、25、26、29~34、36~49、51、52、54~64、66、68、71~85、87、89又は90を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめキュウリ灰色かび病菌の胞子を接種したYB液体培地を150μL分注した。このプレートを4日間、18℃で培養しキュウリ灰色かび病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をキュウリ灰色かび病菌の生育度とした。その結果、各々の化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物1~20、23、25、26、29~49、51、52、54~64、66~68、71~87、89又は90を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめモモ黒星病菌の胞子を接種したYB液体培地を150μL分注した。このプレートを5日間、18℃で培養しモモ黒星病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をモモ黒星病菌の生育度とした。その結果、各々の化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
本発明化合物28、30~33、35、37、39、50、66、67、69、70、72~75、77~89又は90を150ppm含有するようにDMSOで希釈し、タイタープレート(96ウェル)に1μL分注した後、あらかじめイネごま葉枯病菌の胞子を接種したYB液体培地を150μL分注した。このプレートを3日間、23℃で培養しイネごま葉枯病菌を増殖させたのち、タイタープレートの各ウェルの550nmの吸光度を測定し、その値をイネごま葉枯病菌の生育度とした。その結果、各々の化合物を処理した区における生育度はいずれも、無処理区における生育度の50%以下であった。
ダイズ(品種:黒千石)の本葉を直径1cmに切り抜きリーフディスクを作製した。24ウェルマイクロプレートの各ウェルに寒天培地(寒天濃度1.2%)を1mLずつ分注した後、各ウェルの寒天培地の上に、当該リーフディスクを1枚ずつ置いた。0.5μLのソルポール(登録商標)1200KX、DMSO4.5μL及びキシレン5μLの混合物に、供試化合物を10000ppm含有するDMSO溶液20 μLを加えて混合した。得られた混合物をイオン交換水で希釈して供試化合物を所定濃度含有する混合物を調製した。得られた混合物を、リーフディスク1枚につき10μL散布した。1日後に、ミトコンドリアチトクロームbタンパク質にF129Lのアミノ酸置換を有するダイズさび病菌(Phakopsora pachyrhizi)の胞子の水懸濁液 (1.0×105/mL)を、リーフディスク上に噴霧接種した。接種後、人工気象器内(6時間点灯、18時間消灯、温度23℃、湿度60%)に置いた。1日後、リーフディスクの表面の水滴が無くなるまで風乾させ、再び人工気象器内に12日間置いた。その後、ダイズさび病の病斑面積を調査した。その結果、所定濃度を50ppmとし、供試化合物として本発明化合物1~10、15~20、23、28~31、33~35、37、39、40、50、55、56、66~68、70、71~87、89又は90のいずれか1つを処理したリーフディスクの病斑面積は、いずれも無処理のリーフディスクの病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにイネ(品種;ヒノヒカリ)を播種し、温室内で20日間栽培した。その後、製剤例6に記載の方法に準じて製剤化された本発明化合物19、44又は80を濃度が200ppmとなるように水と混合し、得られた混合物を、上記イネの葉面に充分付着するように茎葉散布した。散布後、イネを風乾し、昼間24℃、夜間20℃多湿下で、前記散布処理をしたイネと、イネいもち病菌に罹病したイネ苗(品種;ヒノヒカリ)とを接触させながら6~7日間置いた後、病斑面積を調査した。その結果、各々の本発明化合物を処理したイネにおける病斑面積はいずれも、無処理のイネにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにオオムギ(品種;ニシノホシ)を播種し、温室で7日間栽培した。製剤例6に記載の方法に準じて製剤化された本発明化合物2、4~6、13、14、16、18~20、26、34、39、46~49、51、52、54、55、57、58、64、67、68、75~77、80~83、85~88又は89を、濃度が200ppmとなるように水と混合した。得られた混合物を、上記オオムギの葉面に充分付着するように茎葉散布した。散布後オオムギを風乾し、1日後にオオムギ網斑病菌胞子の水懸濁液を噴霧接種した。接種後オオムギを昼間23℃、夜間20℃の温室内で多湿下に3日間置き、次に温室内で7日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したオオムギにおける病斑面積はいずれも、無処理のオオムギにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにキュウリ(品種;相模半白)を播種し、温室内で12日間生育させた。製剤例6に記載の方法に準じて製剤化された本発明化合物2、47又は61を、濃度が200ppmとなるように水と混合し、得られた混合物を、上記キュウリ葉面に充分付着するように茎葉散布した。散布後キュウリを風乾し、1日後にキュウリべと病菌胞子の懸濁液を噴霧接種した。接種後キュウリを昼間23℃、夜間20℃の温室内で多湿下に1日間置き、次に温室内で10日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したキュウリにおける病斑面積はいずれも、無処理のキュウリにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにコムギ(品種;シロガネ)を播種し、温室内で9日間栽培した。製剤例6に記載の方法に準じて製剤化された本発明化合物2~6、10~16、18、19、20、25、26、29、31、32、34、35、39~42、46、47、49、52~64、66~68、73、75~78、80、81、83~89又は90を濃度が200ppmとなるように水と混合し、得られた混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、20℃、照明下で5~7日間栽培した後、コムギさび病菌の胞子をふりかけ接種した。接種後コムギを23℃、暗黒多湿下に1日間置いた後、20℃、照明下で8日間栽培し、病斑面積を調査した。その結果、各々の本発明化合物を処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにコムギ(品種;アポジー)を播種し、温室内で10日間栽培した。製剤例6に記載の方法に準じて製剤化された本発明化合物1、3~6、10、11、13~16、18~21、25、26、29~37、39、40、46~49、51、53~55、57、58、64、72、73、75、77~80、82、83、85~88又は89を濃度が200ppmとなるように水と混合し、得られた混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、4日後にコムギ葉枯病菌の胞子を含む水懸濁液を噴霧接種した。接種後コムギを18℃多湿下に3日間置き、次に照明下で14日から18日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにコムギ(品種;アポジー)を播種し、温室内で10日間栽培し、コムギ葉枯病菌胞子の水懸濁液を噴霧接種した。接種後コムギを18℃多湿下に3日間置いた後、製剤例6に記載の方法に準じて製剤化された本発明化合物3~5、7~11、15、16、21、25、26、29、31、34、37、39、44、46、47、49、57、58、71~75、77~82、84、88、89又は90を濃度が200ppmとなるように水と混合し、得られた混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、照明下に14日から18日間置いた後、病斑面積を調査した。その結果、各々の本発明化合物を処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにトマト(品種;パティオ)を播種し、温室内で20日間栽培した。製剤例6に記載の方法に準じて製剤化された本発明化合物2、11~14、16、18~21、29、35、39、49、51、52、55、56、60~64、66、76、80、85又は86を濃度が200ppmとなるように水と混合し、得られた混合物を、上記トマトの葉面に充分付着するように茎葉散布した。散布後トマトを風乾し、1日後にトマト疫病菌の胞子を含む水懸濁液を噴霧接種した。接種後トマトを昼間23℃、夜間20℃の温室内で多湿下に1日間置き、次に温室内で4日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したトマトにおける病斑面積はいずれも、無処理のトマトにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにダイズ(品種;黒千石)を播種し、温室内で10~14日間生育させた。製剤例6に記載の方法に準じて製剤化された本発明化合物1~16、18~23、25、26、29~32、34、35、37~40、44~46、48、49、51~59、61~64、68、71~73、75~77、79~83、85~89又は90を濃度が200ppmとなるように水と混合し、得られた混合物を、上記ダイズの葉面に充分付着するように茎葉散布した。散布後ダイズを風乾し、2~5日後にダイズさび病菌胞子の水懸濁液を噴霧接種した。接種後ダイズを昼間23℃、夜間20℃の温室内で多湿下に1~2日間置き、次に温室内で12日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したダイズにおける病斑面積はいずれも、無処理のダイズにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにダイズ(品種;黒千石)を播種し、温室内で10日間生育させ、ダイズさび病菌の胞子を含む水懸濁液を噴霧接種した。接種後ダイズを昼間23℃、夜間20℃の温室内で多湿下に1日間置き、次に温室で2日間栽培した後、製剤例6に記載の方法に準じて製剤化された本発明化合物1~16、18、19、21~23、25、26、37、40、44、46、47~49、57、58、68、71~77、80~82、89又は90を濃度が200ppmとなるように水と混合し、得られた混合物を、上記ダイズの葉面に充分付着するように茎葉散布した。散布後ダイズを風乾し、温室内で8日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したダイズにおける病斑面積はいずれも、無処理のダイズにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにダイズ(品種;タチナガハ)を播種し、温室内で13日間生育させた。製剤例6に記載の方法に準じて製剤化された本発明化合物1~16、18~21、25、26、29~35、37、39、40、44、46~49、54~58、64、71~89又は90を濃度が200ppmとなるように水と混合し、得られた混合物を、上記ダイズの葉面に充分付着するように茎葉散布した。散布後ダイズを風乾し、1日後にダイズ斑点病菌胞子の水懸濁液を噴霧接種した。接種後ダイズを昼間23℃、夜間20℃の温室内で多湿下に3日間置き、次に温室内で16日間栽培した後、病斑面積を調査した。その結果、各々の本発明化合物を処理したダイズにおける病斑面積はいずれも、無処理のダイズにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、そこにトマト(品種;パティオ)を播種し、温室内で20日間生育させた。製剤例6に記載の方法に準じて製剤化された本発明化合物3~6、9、11~16、18~20、29、32、35、36、44、51、57~59、68、71、75、76、80、86又は87を濃度が200ppmとなるように水と混合し、得られた混合物を、上記トマトの葉面に充分付着するように茎葉散布した。散布後トマトを風乾し、1日後にトマト輪紋病菌胞子の水懸濁液を噴霧接種した。接種後トマトを18℃、多湿下に6日間置いた後、病斑面積を調査した。その結果、各々の本発明化合物を処理したトマトにおける病斑面積はいずれも、無処理のトマトにおける病斑面積の30%以下であった。
プラスチックポットに土壌を詰め、インゲン(品種;長鶉菜豆)を播種し、温室内で8日間生育させた。製剤例6に記載の方法に準じて製剤化された本発明化合物2~16、18~20、25、26、29、48、53、55、57、58、64、71、76、77又は89を、濃度が200ppmとなるように水と混合し、得られた混合物を、上記インゲン葉面に充分付着するように茎葉散布した。散布後インゲンを風乾し、インゲン菌核病菌の菌糸含有PDA培地をインゲン葉面上に置いた。接種後全てのインゲンは夜間のみ多湿下におき、接種4日後に病斑面積を調査した。その結果、各々の本発明化合物を処理したインゲンにおける病斑面積はいずれも、無処理のインゲンにおける病斑面積の30%以下であった。
本発明化合物を製剤例6に記載の方法に準じて製剤とし、これに展着剤0.03容量%含有する水を加え、本発明化合物を所定濃度含有する希釈液を調製する。容器に植えたキャベツ(Brassicae oleracea)苗(第2~3本葉展開期)に該希釈液を20mL/苗の割合で散布する。その後、この苗の茎葉部を切り取り、ろ紙を敷いた容器内に入れる。これにコナガ2齢幼虫5頭を放す。5日後、生存虫数を数え、次式より死虫率を求める。
死虫率%=(1-生存虫数/5)×100
所定濃度を500ppmとし、本発明化合物28を用いて試験法23に従って試験を行った結果、本発明化合物28は死虫率100%を示した。
Claims (24)
- 式(I):
Lは、酸素原子又はCH2を表し、
Eは、群Aより選ばれる1以上の置換基で置換されているメチル基、群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-を表し、
R1は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表し、
nは、0、1、2又は3を表し、
nが2又は3である場合、複数のR2は同一又は異なっていてもよく、
R2は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表し、
R3は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R4は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、又は5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}を表し、
R5は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、1以上のハロゲン原子で置換されていてもよいC1-C3アルコキシ基又は水素原子を表し、
R6は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R3及びR5は、R3とR5とが結合する窒素原子と一緒になって4-7員非芳香族複素環
{該4-7員非芳香族複素環は群Bより選ばれる1以上の置換基を有していてもよい}を形成していてもよい。
群A:OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基及びニトロ基からなる群。
R11及びR12は、同一又は相異なり、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R13は、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基又は3-8員非芳香族複素環基{該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表し、
R14、R15及びR16は、同一又は相異なり、C1-C6鎖式炭化水素基又はフェニル基を表し、
mは、0、1又は2を表す。
群B:群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、オキソ基、チオキソ基、ハロゲン原子、シアノ基及びニトロ基からなる群。
群C:群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基及びニトロ基からなる群。
群D:C3-C6シクロアルキル基{該C3-C6シクロアルキル基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、OR17、S(O)mR19、OS(O)2R19、C(O)R17、C(O)OR17、OC(O)R17、OC(O)OR17、OC(O)NR17R18、NR17C(O)NR18R19、NR17R18、C(O)NR17R18、S(O)2NR17R18、NR18C(O)R17、NR18C(O)OR19、NR18S(O)2R19、C(R18)=N-OR17、O-N=CR17R19、SiR14R15R16、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、フェノキシ基、フェニル基、ナフチル基、5-6員芳香族複素環基及び3-8員非芳香族複素環基{該フェノキシ基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}からなる群。
R17及びR18は、同一又は相異なり、C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R19は、C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基又は3-8員非芳香族複素環基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}を表す。
群E:C1-C6鎖式炭化水素基、C3-C6シクロアルキル基{該C1-C6鎖式炭化水素基及び該C3-C6シクロアルキル基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、OR17、S(O)mR19、OS(O)2R19、C(O)R17、C(O)OR17、OC(O)R17、OC(O)OR17、OC(O)NR17R18、NR17C(O)NR18R19、NR17R18、C(O)NR17R18、S(O)2NR17R18、NR18C(O)R17、NR18C(O)OR19、NR18S(O)2R19、C(R18)=N-OR17、O-N=CR17R19、SiR14R15R16、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、フェノキシ基、フェニル基、ナフチル基、5-6員芳香族複素環基及び3-8員非芳香族複素環基{該フェノキシ基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}からなる群。
群F:C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、C1-C6アルコキシ基及びC1-C6アルキルチオ基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該C1-C6アルコキシ基及び該C1-C6アルキルチオ基は、ハロゲン原子及びシアノ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基、ニトロ基及びヒドロキシ基からなる群。〕
で示される化合物、又はそのNオキシド若しくは農業上許容可能な塩。 - Eが、群Aより選ばれる1以上の置換基で置換されているメチル基、又は群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基である、請求項1に記載の化合物、又はそのNオキシド若しくは農業上許容可能な塩。
- Eが、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-である、請求項1に記載の化合物、又はそのNオキシド若しくは農業上許容可能な塩。
- Eが、R3R5NC(O)-である、請求項1に記載の化合物、又はそのNオキシド若しくは農業上許容可能な塩。
- R1が、メチル基又は塩素原子であり、nが0であり、Lが酸素原子である、請求項1~4のいずれか1つに記載の化合物、又はそのNオキシド若しくは農業上許容可能な塩。
- 請求項1~5のいずれか1つに記載の化合物、又はそのNオキシド若しくは農業上許容可能な塩と不活性担体とを含有する有害生物防除組成物。
- 群(a)、群(b)、群(c)及び群(d)からなる群より選ばれる1以上の成分、並びに請求項1~5いずれか1つに記載の化合物、又はそのNオキシド若しくは農業上許容可能な塩を含有する組成物:
群(a):殺虫活性成分、殺ダニ活性成分及び殺線虫活性成分からなる群;
群(b):殺菌活性成分;
群(c):植物成長調整成分;
群(d):忌避成分。 - 請求項1~5のいずれか1つに記載の化合物、若しくはそのNオキシド若しくは農業上許容可能な塩の有効量又は請求項7に記載の組成物を植物又は土壌に処理することによる有害生物の防除方法。
- 請求項1~5のいずれか1つに記載の化合物、若しくはそのNオキシド若しくは農業上許容可能な塩の有効量又は請求項7に記載の組成物をダイズ又はダイズを生育する土壌に施用することによる、ミトコンドリアチトクロームbタンパク質にF129Lのアミノ酸置換を有するダイズさび病菌の防除方法。
- 有害生物を防除するための、請求項1~5のいずれか1つに記載の化合物、若しくはそのNオキシド若しくは農業上許容可能な塩又は請求項7に記載の組成物の使用。
- 請求項1~5のいずれか1つに記載の化合物、若しくはそのNオキシド若しくは農業上許容可能な塩の有効量又は請求項7に記載の組成物を保持している種子又は栄養生殖器官。
- R1が、メチル基又は塩素原子であり、nが0である、請求項12に記載の化合物。
- 式(III):
Lは、酸素原子又はCH2を表し、
Eは、群Aより選ばれる1以上の置換基で置換されているメチル基、群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-を表し、
R1は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表し、
nは、0、1、2又は3を表し、
nが2又は3である場合、複数のR2は同一又は異なっていてもよく、
R2は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表し、
R3は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R4は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、又は5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}を表し、
R5は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、1以上のハロゲン原子で置換されていてもよいC1-C3アルコキシ基又は水素原子を表し、
R6は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R3及びR5は、R3とR5とが結合する窒素原子と一緒になって4-7員非芳香族複素環{該4-7員非芳香族複素環は群Bより選ばれる1以上の置換基を有していてもよい}を形成していてもよい。
群A:OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基及びニトロ基からなる群。
R11及びR12は、同一又は相異なり、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R13は、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基又は3-8員非芳香族複素環基{該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表し、
R14、R15及びR16は、同一又は相異なり、C1-C6鎖式炭化水素基又はフェニル基を表し、
mは、0、1又は2を表す。
群B:群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、オキソ基、チオキソ基、ハロゲン原子、シアノ基及びニトロ基からなる群。
群C:群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基及びニトロ基からなる群。
群D:C3-C6シクロアルキル基{該C3-C6シクロアルキル基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、OR17、S(O)mR19、OS(O)2R19、C(O)R17、C(O)OR17、OC(O)R17、OC(O)OR17、OC(O)NR17R18、NR17C(O)NR18R19、NR17R18、C(O)NR17R18、S(O)2NR17R18、NR18C(O)R17、NR18C(O)OR19、NR18S(O)2R19、C(R18)=N-OR17、O-N=CR17R19、SiR14R15R16、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、フェノキシ基、フェニル基、ナフチル基、5-6員芳香族複素環基及び3-8員非芳香族複素環基{該フェノキシ基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}からなる群。
R17及びR18は、同一又は相異なり、C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R19は、C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基又は3-8員非芳香族複素環基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}を表す。
群E:C1-C6鎖式炭化水素基、C3-C6シクロアルキル基{該C1-C6鎖式炭化水素基及び該C3-C6シクロアルキル基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、OR17、S(O)mR19、OS(O)2R19、C(O)R17、C(O)OR17、OC(O)R17、OC(O)OR17、OC(O)NR17R18、NR17C(O)NR18R19、NR17R18、C(O)NR17R18、S(O)2NR17R18、NR18C(O)R17、NR18C(O)OR19、NR18S(O)2R19、C(R18)=N-OR17、O-N=CR17R19、SiR14R15R16、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、フェノキシ基、フェニル基、ナフチル基、5-6員芳香族複素環基及び3-8員非芳香族複素環基{該フェノキシ基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}からなる群。
群F:C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、C1-C6アルコキシ基及びC1-C6アルキルチオ基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該C1-C6アルコキシ基及び該C1-C6アルキルチオ基は、ハロゲン原子及びシアノ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基、ニトロ基及びヒドロキシ基からなる群。〕
で示される化合物。 - Eが、群Aより選ばれる1以上の置換基で置換されているメチル基、又は群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基である、請求項14に記載の化合物。
- Eが、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-である、請求項14に記載の化合物。
- Eが、R3R5NC(O)-である、請求項14に記載の化合物。
- R1が、メチル基又は塩素原子であり、nが0であり、Lが酸素原子である、請求項14~17のいずれかに記載の化合物。
- 式(IV):
Eは、群Aより選ばれる1以上の置換基で置換されているメチル基、群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-を表し、
nは、0、1、2又は3を表し、
nが2又は3である場合、複数のR2は同一又は異なっていてもよく、
R2は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、シクロプロピル基又はハロゲン原子を表し、
R3は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R4は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、又は5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}を表し、
R5は、1以上のハロゲン原子で置換されていてもよいC1-C3鎖式炭化水素基、1以上のハロゲン原子で置換されていてもよいC1-C3アルコキシ基又は水素原子を表し、
R6は、群Aより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Bより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、C6-C10アリール基、5-10員芳香族複素環基{該C6-C10アリール基及び該5-10員芳香族複素環基は、群Cより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R3及びR5は、R3とR5とが結合する窒素原子と一緒になって4-7員非芳香族複素環{該4-7員非芳香族複素環は群Bより選ばれる1以上の置換基を有していてもよい}を形成していてもよい。
群A:OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基及びニトロ基からなる群。
R11及びR12は、同一又は相異なり、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R13は、群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、群Eより選ばれる1以上の置換基で置換されていてもよいC3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基又は3-8員非芳香族複素環基{該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}を表し、
R14、R15及びR16は、同一又は相異なり、C1-C6鎖式炭化水素基又はフェニル基を表し、
mは、0、1又は2を表す。
群B:群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、オキソ基、チオキソ基、ハロゲン原子、シアノ基及びニトロ基からなる群。
群C:群Dより選ばれる1以上の置換基で置換されていてもよいC1-C6鎖式炭化水素基、OR11、S(O)mR13、OS(O)2R13、C(O)R11、C(O)OR11、OC(O)R11、OC(O)OR11、OC(O)NR11R12、NR11C(O)NR12R13、NR11R12、C(O)NR11R12、S(O)2NR11R12、NR12C(O)R11、NR12C(O)OR13、NR12S(O)2R13、C(R12)=N-OR11、O-N=CR11R13、SiR14R15R16、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Eより選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基及びニトロ基からなる群。
群D:C3-C6シクロアルキル基{該C3-C6シクロアルキル基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、OR17、S(O)mR19、OS(O)2R19、C(O)R17、C(O)OR17、OC(O)R17、OC(O)OR17、OC(O)NR17R18、NR17C(O)NR18R19、NR17R18、C(O)NR17R18、S(O)2NR17R18、NR18C(O)R17、NR18C(O)OR19、NR18S(O)2R19、C(R18)=N-OR17、O-N=CR17R19、SiR14R15R16、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、フェノキシ基、フェニル基、ナフチル基、5-6員芳香族複素環基及び3-8員非芳香族複素環基{該フェノキシ基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}からなる群。
R17及びR18は、同一又は相異なり、C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基、3-8員非芳香族複素環基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}又は水素原子を表し、
R19は、C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、フェニル基、ナフチル基、5-6員芳香族複素環基又は3-8員非芳香族複素環基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}を表す。
群E:C1-C6鎖式炭化水素基、C3-C6シクロアルキル基{該C1-C6鎖式炭化水素基及び該C3-C6シクロアルキル基は、ハロゲン原子、シアノ基及びC1-C3アルコキシ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、OR17、S(O)mR19、OS(O)2R19、C(O)R17、C(O)OR17、OC(O)R17、OC(O)OR17、OC(O)NR17R18、NR17C(O)NR18R19、NR17R18、C(O)NR17R18、S(O)2NR17R18、NR18C(O)R17、NR18C(O)OR19、NR18S(O)2R19、C(R18)=N-OR17、O-N=CR17R19、SiR14R15R16、ハロゲン原子、シアノ基、ニトロ基、ヒドロキシ基、フェノキシ基、フェニル基、ナフチル基、5-6員芳香族複素環基及び3-8員非芳香族複素環基{該フェノキシ基、該フェニル基、該ナフチル基、該5-6員芳香族複素環基及び該3-8員非芳香族複素環基は、群Fより選ばれる1以上の置換基で置換されていてもよい}からなる群。
群F:C1-C6鎖式炭化水素基、C3-C6シクロアルキル基、C1-C6アルコキシ基及びC1-C6アルキルチオ基{該C1-C6鎖式炭化水素基、該C3-C6シクロアルキル基、該C1-C6アルコキシ基及び該C1-C6アルキルチオ基は、ハロゲン原子及びシアノ基からなる群より選ばれる1以上の置換基で置換されていてもよい}、ハロゲン原子、シアノ基、ニトロ基及びヒドロキシ基からなる群。〕
で示される化合物。 - nが0であり、Eが、群Aより選ばれる1以上の置換基で置換されているメチル基、又は群Aより選ばれる1以上の置換基で置換されていてもよいC2-C10鎖式炭化水素基である、請求項19に記載の化合物。
- nが0であり、Eが、R6C(O)-、R4OC(O)-、R3R5NC(O)-、R3R5NC(S)-、R4S(O)2-、又はR3R5NS(O)2-である、請求項19に記載の化合物。
- nが0であり、EがR3R5NC(O)-である、請求項19に記載の化合物。
- R1が、メチル基又は塩素原子であり、nが0である、請求項23に記載の化合物。
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