WO2011007839A1 - 農園芸用の有害生物防除剤としての4-(3-ブチニル)アミノピリミジン誘導体 - Google Patents
農園芸用の有害生物防除剤としての4-(3-ブチニル)アミノピリミジン誘導体 Download PDFInfo
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- WO2011007839A1 WO2011007839A1 PCT/JP2010/061993 JP2010061993W WO2011007839A1 WO 2011007839 A1 WO2011007839 A1 WO 2011007839A1 JP 2010061993 W JP2010061993 W JP 2010061993W WO 2011007839 A1 WO2011007839 A1 WO 2011007839A1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
-
- 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
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Definitions
- the present invention relates to a novel 4- (3-butynyl) aminopyrimidine derivative that is useful as a pest control agent, particularly an agricultural and horticultural pest control agent.
- the 4- (3-butynyl) aminopyrimidine derivative of the present invention is a novel compound and is not known to have pest control activity in agriculture and horticulture.
- JP-A-5-230036 JP-A-6-25187 JP-A-8-113564 JP-A-11-302261 JP-A-11-158161 JP 2006-8542 A WO2007 / 135029 WO2007 / 46809 WO2006 / 47397
- An object of the present invention is to provide a novel 4- (3-butynyl) aminopyrimidine derivative, a production method thereof, and an agricultural and horticultural pest control agent comprising the same as an active ingredient.
- the present invention is as follows.
- the first invention relates to a 4- (3-butynyl) aminopyrimidine derivative represented by the following formula [I].
- R 1 is a) phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolinyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl 0 to 3 heterozygous selected from the group consisting of benzoisothiazolyl, pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl Monocyclic or bicyclic rings optionally containing atoms, b) Linear or branched alkyl
- R 1 is —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O ) R, —C (O) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, — NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is Linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched having 2 to 8 carbon atoms number alkynyl or carbon
- a branched alkynyl or a cycloalkyl having 3 to 8 carbon atoms or (6) a haloalkyl (identical or different, a straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms).
- R 4 is a hydrogen atom, a halogen atom, an alkyl having 1 to 6 carbon atoms, nitro, amino, phenyl, benzyl, or a thiophene ring, a pyridine ring, a pyrrole ring formed together with a carbon atom on the pyrimidine ring by combining with R 3 Imidazole ring, benzene ring, naphthalene ring, pyrimidine ring, furan ring, pyrazine ring, pyrazole ring and oxazole ring. ]
- the second invention is a method for producing a 4- (3-butynyl) aminopyrimidine derivative represented by the formula [I].
- the third invention is a pest control agent comprising one or more 4- (3-butynyl) aminopyrimidine derivatives represented by the formula [I] as active ingredients.
- novel 4- (3-butynyl) aminopyrimidine derivative of the present invention represented by the formula [I] has an excellent control effect against pests, particularly agricultural and horticultural pests.
- the 4- (3-butynyl) aminopyrimidine derivative in the present invention includes, in addition to the 4- (3-butynyl) aminopyrimidine derivative represented by the formula [I], salts of the derivative (sodium salt, potassium salt, magnesium salt) Salts, calcium salts, aluminum salts, etc.), hydrates, solvates, polymorphic substances. Furthermore, all possible stereoisomers or optical isomers present in the compound of the present invention, and a mixture containing two or more kinds of isomers in an arbitrary ratio are also represented by the compound of the present invention (4- ( 3-butynyl) aminopyrimidine derivatives).
- R 1 is a substituent selected from any of the following a) to d).
- R 1 is —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O ) NHR, —C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, — NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is a carbon atom number of 1 to 8) Linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or 3 to 3 carbon atoms 8 cycloalkyl
- alkyl group alkylthioalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by a linear or branched alkylthio group having 1 to 8 carbon atoms), dialkoxyacetal ( A dialkoxymethyl group in which a linear or branched alkoxy group having 1 to 8 carbon atoms is substituted with two methyl groups), alkoxyalkoxy (a linear or branched alcohol having 1 to 8 carbon atoms) C1-C3 linear or branched alkyl group substituted by a xy group), cyanoalkyl (C1-C3 linear or branched alkyl group substituted by a cyano group) Halogen, cyano, nitro, amino, hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidin
- R 2 is a hydrogen atom, —R, —OR, —C (O) OR, —C (O) NHR, —CONR 2 (where R is linear or branched having 1 to 8 carbon atoms) Alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms) , Hydroxyalkyl (linear or branched alkyl group having 1 to 3 carbon atoms substituted by a hydroxyl group), alkoxyalkyl (substituted by linear or branched alkoxy group having 1 to 8 carbon atoms) Straight chain or branched alkyl group having 1 to 3 carbon atoms), haloalkoxyalkyl (the same or different, straight chain having 1 to 4 carbon atoms substituted with halogen atoms 1 to 9) Or substituted by a branched haloalkoxy group
- R 3 is an acyloxy represented by (1) a hydrogen atom, (2) a halogen atom, (3) (a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— Alkyl having 1 to 6 carbon atoms substituted with a halogen atom or a hydroxyl group, (4) unsubstituted alkyl having 1 to 6 carbon atoms, (5) —OR, —SR, —SO 2 R (here R represents a straight or branched alkyl having 1 to 8 carbon atoms, a straight or branched alkenyl having 2 to 8 carbon atoms, or a straight chain having 2 to 8 carbon atoms.
- a branched alkynyl or a cycloalkyl having 3 to 8 carbon atoms or (6) a haloalkyl (identical or different, a straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms).
- a chain-like or branched alkyl group ).
- R 4 is a hydrogen atom, a halogen atom, an alkyl having 1 to 6 carbon atoms, nitro, amino, phenyl, benzyl, or a thiophene ring, a pyridine ring, a pyrrole ring formed together with a carbon atom on the pyrimidine ring by combining with R 3 Imidazole ring, benzene ring, naphthalene ring, pyrimidine ring, furan ring, pyrazine ring, pyrazole ring and oxazole ring.
- Monocyclic or bicyclic rings optionally containing 0 to 3 heteroatoms in R 1 include phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl , Isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolinyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzoisothiazolyl, pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, Benzimidazolyl, pyrazolyl, and pyridonyl groups can be mentioned, but phenyl, oxazolyl, thiazolyl,
- substituents include —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, — C (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is a straight chain having 1 to 8 carbon atoms) Straight or branched alkyl, straight or branched alkenyl having 2 to 8 carbon atoms, straight or branched alkynyl having 2 to 8 carbon atoms, or cyclo having 3 to 8 carbon atoms -S
- R 1 straight or branched alkyl having 1 to 6 carbon atoms, straight or branched alkenyl having 2 to 8 carbon atoms, linear or branched having 2 to 8 carbon atoms
- Alkynyl having 3 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms or cycloalkenyl having 3 to 8 carbon atoms includes n-butyl, s-butyl, t-butyl, n-hexyl,
- a propenyl group, a 2-propenyl group and an isopropenyl group can be exemplified, and an n-butyl group, a s-butyl group, a t-butyl group, a 1-propenyl group and an isopropenyl group are preferable.
- the substituents include —C (O) OR, —C (O) R, —R, —OR, —SR, —SO 2 R, —OC (O) R, —C (O) NHR, —C. (O) NR 2 , —NHSO 2 R, —NRSO 2 R, —NHR, —NR 2 , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR , —N (OR) C (O) OR, —NHSO 2 R, —NRSO 2 R, —SO 2 NHR, —SO 2 NR 2 (where R is a straight chain having 1 to 8 carbon atoms) Or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms -SiR 5 R
- R 5 R 6 R 7 is C 1 -C 6 linear or branched alkyl, phenyl, also two or all in the same substituent
- substituents may be trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, t-butyldimethylsilyl group, t-butyldiphenylsilyl group. preferable.
- R 2 is preferably a hydrogen atom or a cyano group
- the linear or branched alkyl having 1 to 8 carbon atoms is preferably a methyl group or an ethyl group, and is a straight chain having 2 to 8 carbon atoms or
- the branched alkenyl, an ethynyl group and a propenyl group are preferable.
- R 2 includes —C (O) OR, —C (O) NHR, —CONR 2 (wherein R is linear or branched alkyl having 1 to 6 carbon atoms, carbon atoms of 2 -8 linear or branched alkenyl, linear or branched alkynyl having 2 to 8 carbon atoms or cycloalkyl having 3 to 8 carbon atoms), phenyl group, heteroaryl group A phenyl group is preferable.
- halogen atom for R 2 examples include a chlorine atom, an iodine atom, a bromine atom, and a fluorine atom, with a chlorine atom and a fluorine atom being preferred.
- Examples of the alkoxy group for R 2 include a methoxy group, an ethoxy group, an n-propoxy group, and an isopropoxy group, and a methoxy group and an ethoxy group are preferable.
- the haloalkyl group in R 2 is preferably a monofluoromethyl group, a difluoromethyl group, or a trifluoromethyl group, and the haloalkoxy group is preferably a monofluoromethoxy group, a difluoromethoxy group, or a trifluoromethoxy group.
- halogen atom in R 3 examples include a chlorine atom, an iodine atom, a bromine atom, and a fluorine atom, and a chlorine atom, a bromine atom, and an iodine atom are preferable.
- R 3 a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms
- alkyl group chloromethyl group, 1-chloroethyl group, 1-bromoethyl group, 1-fluoroethyl group, acetyloxymethyl group, 1-acetyloxyethyl group, 1-propionyloxyethyl group, 1-hydroxyethyl group 1-chloroethyl group, 1-fluoroethyl group, 1-acetyloxyethyl group or 1-hydroxyethyl group is preferable.
- the unsubstituted alkyl group having 1 to 6 carbon atoms in R 3 is preferably a methyl group or an ethyl group.
- R 3 includes —OR, —SR, —SO 2 R (wherein R is linear or branched alkyl having 1 to 8 carbon atoms, linear having 2 to 8 carbon atoms) Or a branched alkenyl, a linear or branched alkynyl group having 2 to 8 carbon atoms, or a cycloalkyl group having 3 to 8 carbon atoms. Group and ethylthio group are preferred.
- haloalkyl group in R 3 examples include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a heptafluoroisopropyl group.
- Group, trifluoromethyl group is preferred.
- halogen atom in R 4 examples include a chlorine atom, an iodine atom, a bromine atom, and a fluorine atom, and a chlorine atom, a bromine atom, and an iodine atom are preferable.
- the linear or branched alkyl group having 1 to 6 carbon atoms for R 4 is preferably a methyl group or an ethyl group.
- the thiophene ring formed by combining with R 3 in R 4 together with the carbon atom on the pyrimidine ring includes the following formula (IV-1) (In the formula, R 8 represents a hydrogen atom, a methyl group, a fluorine atom or a chlorine atom.)
- R 8 represents a hydrogen atom, a methyl group, a fluorine atom or a chlorine atom.
- a thieno [2,3-d] pyrimidine ring in which R 8 is a hydrogen atom or a chlorine atom is preferable.
- the benzene ring formed by combining with R 3 in R 4 together with the carbon atom on the pyrimidine ring includes the following formula (IV-2) (In the formula, R 8 represents a hydrogen atom, a methyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, a trifluoromethyl group, a cyano group, a nitro group, a methylthio group, a propargyl group, a propargyloxy group, and benzyl.
- R 8 represents a hydrogen atom, a methyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, a trifluoromethyl group, a cyano group, a nitro group, a methylthio group, a propargyl group, a propargyloxy group, and benzy
- a quinazoline ring in which R 8 is a hydrogen atom, a fluorine atom or a chlorine atom is preferable.
- alkyl refers to a linear or branched alkyl group having 1 to 8 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group. And isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-heptyl, and n-octyl groups.
- alkenyl refers to a linear or branched alkenyl group having 2 to 8 carbon atoms, such as an ethenyl group, a 1-propenyl group, a 2-propenyl group, an isopropenyl group, 1 -Butenyl group, 2-butenyl group, 3-butenyl group and the like can be mentioned.
- alkynyl refers to a linear or branched alkynyl group having 2 to 8 carbon atoms, for example, ethynyl group, 2-propynyl group, 2-butynyl group, or 3-butynyl group. Groups and the like.
- cycloalkyl refers to a cycloalkyl group having 3 to 8 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
- cycloalkenyl refers to a cycloalkenyl group having 3 to 8 carbon atoms, such as a 1-cyclopentyl group, 2-cyclopentyl group, 3-cyclopentyl group, 1-cyclohexyl group, 2- A cyclohexyl group or a 3-cyclohexyl group can be mentioned.
- heteroatom includes a nitrogen atom, an oxygen atom and a sulfur atom.
- halogen includes fluorine, chlorine, bromine and iodine.
- halo in “halo...” (For example, “haloalkyl”) includes fluorine, chlorine, bromine and iodine.
- haloalkyl is the same or different and represents a linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms. Examples thereof include a methyl group, a monochloromethyl group, a monobromomethyl group, a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, an n-heptafluoropropyl group, and an isoheptafluoropropyl group.
- haloalkenyl is the same or different and represents a linear or branched alkenyl group having 2 to 6 carbon atoms, which is substituted with 1 to 4 halogen atoms.
- a 2-difluoroethenyl group, a 2,2-difluoroethenyl group, a 3,3-difluoro-2-propenyl group, and the like can be given.
- alkoxy refers to an (alkyl) -O— group in which the alkyl moiety has the above meaning, for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group. , S-butoxy group, t-butoxy group and the like.
- haloalkoxy refers to a (haloalkyl) -O— group in which the haloalkyl moiety has the above meaning, for example, a monofluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, 2,2-difluoro An ethoxy group, a 2,2,2-trifluoroethoxy group, etc. can be mentioned.
- acyl or the term “acyl” in acylalkoxy, the term “acyl” in acyloxyalkyl, and the term “acyl” in acyloxy are all (with 1 to 8 carbon atoms).
- the aliphatic hydrocarbon group means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkynyl.
- acylalkoxy refers to a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by the acyl group shown above, and includes, for example, an acetylmethoxy group, an acetylethoxy group And acetylpropoxy group.
- acyloxy refers to a (linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— group, for example, an acetoxy group, propionyloxy group , An isopropionyloxy group, or a pivaloyloxy group.
- acyloxyalkyl refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by the acyl group shown above, for example, an acetoxymethyl group, an acetoxyethyl group Or an acetoxypropyl group.
- alkylsulfonyl refers to an (alkyl) -SO 2 — group in which the alkyl moiety has the above meaning, for example, a methylsulfonyl group, an ethylsulfonyl group, an n-propylsulfonyl group, or an isopropylsulfonyl group. Groups and the like.
- alkylsulfonylalkyl refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by the alkylsulfonyl group shown above, such as a methylsulfonylmethyl group, A methylsulfonylethyl group, a methylsulfonylpropyl group, etc. can be mentioned.
- the term “siloxy” means —OSiR 5 R 6 R 7 (R 5 , R 6 , R 7 are linear or branched alkyl having 1 to 6 carbon atoms, phenyl, 2
- R 5 , R 6 , R 7 are linear or branched alkyl having 1 to 6 carbon atoms, phenyl, 2
- trimethylsiloxy group, triethylsiloxy group, triisopropylsiloxy group, t-butyldimethylsiloxy group, t-butyldiphenylsiloxy group, etc. be able to.
- siloxyalkyl refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by the above-mentioned siloxy group, such as trimethylsiloxymethyl group, trimethylsiloxy ethyl group, and trimethylsiloxy-propyl group, triethylsiloxy methyl group, or t- butyl dimethyl siloxy group or the like.
- hydroxyalkyl refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by a hydroxyl group, such as a hydroxymethyl group, a hydroxyethyl group, or a hydroxypropyl group. Groups and the like.
- alkoxyalkyl refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by the alkoxy group shown above, and includes, for example, a methoxymethyl group, an ethoxymethyl group , Propoxymethyl group, isopropoxymethyl group, and the like.
- alkylthio refers to an (alkyl) -S— group in which the alkyl moiety has the above meaning, and examples include a methylthio group, an ethylthio group, or a propylthio group.
- alkylthioalkyl refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by the alkylthio group shown above, for example, methylthiomethyl group, ethylthiomethyl group, Group, methylthioethyl group, or ethylthioethyl group.
- dialkoxyacetal refers to a dialkoxymethyl group in which the above-mentioned alkoxy group is substituted by two methyl groups, such as a dimethoxymethyl group, a diethoxymethyl group, or a dipropoxymethyl group. Can be mentioned.
- alkoxyalkoxy refers to a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by the alkoxy group shown above, for example, a methoxymethoxy group, a methoxyethoxy group, or the like. Or a methoxypropoxy group.
- haloalkoxyalkyl means a linear or branched alkyl group having 1 to 3 carbon atoms substituted by the haloalkoxy group shown above, for example, a monofluoromethoxymethyl group , Difluoromethoxymethyl group, trifluoromethoxymethyl group and the like.
- cyanoalkyl represents a linear or branched alkyl group having 1 to 3 carbon atoms substituted by a cyano group, such as a cyanomethyl group, a cyanoethyl group, or a cyanopropyl group. Can be mentioned.
- phenyl”, “thienyl”, “pyridyl”, “oxazolyl”, “furanyl”, “thiazolyl”, “naphthyl”, “pyrimidinyl”, “benzothiazolyl”, “benzoxazolyl”, “benzodi” “Oxolyl” may have one or more substituents which may be the same or different, and may not have a substituent.
- phenoxy includes a phenoxy group having one or more substituents which may be the same or different, and an unsubstituted phenoxy group.
- benzyl includes a benzyl group having one or more substituents which are the same or different and an unsubstituted benzyl group.
- benzyloxy includes a benzyloxy group having one or more substituents which are the same or different and an unsubstituted benzyloxy group.
- propargyl includes propargyl groups having a substituent at the alkyne end and unsubstituted propargyl groups.
- propargyloxy includes a propargyloxy group having a substituent at the alkyne end and an unsubstituted propargyloxy group.
- heteroaryl includes oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolinyl, quinolyl, isoquinolyl, indolyl, isoindolyl, imidazolyl, pyrazolyl, pyridyl, furyl, thienyl, pyrrolyl. . These groups may have one or more substituents which may be the same or different, and may not have a substituent.
- cyclic ether includes epoxy, oxetane, tetrahydrofuran, tetrahydropyran, dioxolane, and dioxane.
- cyclic amine includes pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholinyl.
- the term “imide” includes a chain imide and a cyclic imide.
- acids that form acid addition salts include inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, and phosphoric acid, formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, and aconitic acid.
- R 2 is —R, —OR, —C (O) OR, —C (O) NHR, —CONR 2 (where R is the number of carbon atoms) 1-8 linear or branched alkyl, 2-8 carbon straight or branched alkenyl, 2-8 carbon linear or branched alkynyl or carbon 3 to 8 cycloalkyl), hydroxyalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by a hydroxyl group), alkoxyalkyl (having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a linear or branched alkoxy group), phenyl, heteroaryl, halogen, cyano, haloalkyl (identical or different, halogen atoms 1 to Carbon substituted with 9 Linear or branched alkyl group having 1 to 4 atoms), halo
- acyloxy wherein R 3 of the compound of the present invention represented by the formula [I] is represented by (a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O—, Any of the individual optical isomers, racemates or mixtures thereof derived from asymmetric carbon atoms generated in the case of alkyl having 1 to 6 carbon atoms substituted with a halogen atom or a hydroxyl group are included in the present invention.
- the compound [I] of the present invention represented by the following formula includes, for example, a chloropyrimidine derivative represented by the general formula [II] and a 3-butynylamine derivative represented by the general formula [III] as shown in the following reaction process formula. It can be produced by reacting in the presence of a base and a solvent.
- R 1 , R 2 , R 3 and R 4 are as defined above.
- the type of the solvent is not particularly limited as long as it does not directly participate in this reaction.
- the amount of the solvent used can be such that the compound [II] is 5 to 80% by weight, but preferably 10 to 70% by weight.
- the type of base is not particularly limited, and organic and inorganic bases such as tertiary amines (such as triethylamine), organic bases such as DBU, alkali metal and alkaline earth metal hydrides, hydroxides, carbonates, Although inorganic bases, such as hydrogencarbonate, can be mentioned, organic bases, such as tertiary amine (triethylamine etc.) and DBU, are preferable.
- organic bases such as tertiary amine (triethylamine etc.) and DBU, are preferable.
- the amount of the base to be used is 1.0 to 5.0 mol, preferably 1.2 to 2.0 mol, relative to 1.0 mol of compound [II].
- the amount of the raw material compound used is 1.0 to 5.0 mol of compound [III] with respect to 1.0 mol of compound [II], preferably 1.0 to 1.2 mol.
- the reaction temperature is not particularly limited, but is within a temperature range below the boiling point of the solvent used at room temperature, preferably 60 ⁇ 110 ° C..
- the reaction time varies depending on the concentration and temperature, but is usually 0.5 to 8 hours.
- the compound [I] produced as described above is subjected to usual post-treatments such as extraction, concentration and filtration after completion of the reaction, and is appropriately purified by known means such as recrystallization and various chromatography as necessary. can do.
- R 1 is phenyl, heteroaryl, alkenyl, R 2 , R 3 and R 4 are as defined above.
- Compound [II] used in this synthesis method can be produced, for example, according to the method described in Non-Patent Document 1 by the method shown in the following formula.
- the 3-butynylamine derivative [III] used in this synthesis can be a commercially available product, but can be produced, for example, according to the method described below if necessary. However, the method described below does not limit the scope of the present invention.
- N- (3-butynyl) phthalimide derivative [VIII] is subjected to Sonogashira reaction with iodide or phenyl bromide, iodide, bromide or heteroaryl chloride, iodide or alkenyl bromide [V], and then product
- the 3-butynylamine derivative [III] can be produced by deprotecting [IX] with hydrazine or a base.
- X is iodine, bromine or chlorine
- R 1 is phenyl, heteroaryl, alkenyl
- R 2 is as defined above.
- Azide compound [XIV] is produced by reacting sodium azide with compound [XVIII] in which substituted butynyl alcohol [XIV] is protected with a tosyl group. Thereafter, 3-butynylamine derivative [III] can be produced by reducing this azide compound [XIV] with lithium aluminum hydride.
- the 3-butynylamine derivative [III] can be produced from the acyl azide [XXI] by the Curtius transfer.
- the term “pest” includes all pests on agricultural and horticultural plants and all pathogenic fungi on agricultural and horticultural plants.
- Agricultural and horticultural pests include, for example, Plutella xylostella, Agrotis ipsilon, Agrotis segetum, Helicoverpa armigera, Tobacco moth (Helicoverpa assulta), Cotton ball worm (Helicoverpa zea), Tobacco ba Heliothis virescens), Mamestra brassicae, Naranga aenescens, Tamanaginawaba (Plusia nigrisigna), Ayayoto (Pseudaletia separata), Sirochimoyoto (Spodoptera exigua) Worm (Spodoptera frugiperda), Southern army worm (Spodoptera eridania), Tobacco horn worm (Manduca sexta), Grapeberry moss (Endopiza viteana), Ginmon leafworm (Lyonetia prunifoliella malinella), Kinmonhosoga (hringone moter) Riga (Phylloc
- Cucumber mites such as Scaroptes scabiei, crustaceans such as Armadillidium vulgare, Prathylenchus penetrans, Prathylenchus vulnus obodera rostochiensis), soybean cyst nematode (Heterodera inesglycines), fox root nematode (Meloidogyne hapla), honey beetle nematode (Meloidogyne incognita), pine moth ali , Mollusks such as Acusta despecta sieboldiana and Mishamai mai (Euhadra peliomphala).
- rice blast Panararia oryzae
- rice sesame leaf blight Cochliobolus miyabeanus
- rice blight Rhizoctonia solani
- rice idiot Gibberella fujikuroi
- barley powdery mildew Erysiphe graminis f.sp. tritici
- wheat powdery mildew Edrysiphe graminis f.sp.
- Leaf blight (Septoria tritici)
- wheat cloud phytonchosporium secalis f.sp.
- Botrytis cinerea azuki bean powder disease (Erisiphe pisi), azuki bean brown disease (Cercosporaescanescens), azuki bean sclerotia (Sclerotinia sclerot) iorum), azuki bean anthracnose (Colletotrichum phaseolorum), common bean brown spot (Cercospora canescens), kidney bean sclerotia (Sclerotinia sclerotiorum), common bean anthracnose (Colletotrichum lindemuthiamum), kidney bean gray vine rot (Botrytis Colletotrichum Diseases (Cercospora beticola), spinach anthracnose (Colletotrichum spinaciae), spinach downy mildew (Peronospora effusa), cabbage black spot (Alternaria brassicae), cabbage black soot (Alternaria brassicicola), cabbage fungus Cabbage gray
- Watermelon powdery mildew (Sphaerotheca fuliginea), watermelon plague (Phytophthora cryptogea), watermelon sclerotia (Sclerotinia sclerotiorum), Watermelon anthracnose (Colletotrichum orbiculare), watermelon downy mildew (Pseudoperonospora cubensis), melon brown spot (Corynespora cassiicola), melon sclerotia (Sclerotinia sclerotiorum), melon vine split disease (Fusarium oxysporum f.sp.
- apple soot spot Zygophiala jamaicensis
- apple apple anthracnose Glomerella cingulata
- apple gray mold Botrytis cinerea
- apple spotted leaf disease Alternaria alternata
- grape powdery mildew Uncinula necator
- grape blight Mycorrhizal disease Sclerotinia sclerotiorum
- Grape late rot Glomerellamercingulata
- Grape brown spot Pseudocercospora vitis
- Grape brown leaf blight (Briosia ampelophaga), Grape black rot (Elsinoe ampelina), Grape black rot (Phyllosticta ampelicida), grape vine split disease (Phomopsis viticola), grape downy mildew (Plasmopara viticola), chestnut anthracnose (Glomerella cingulata), chestnut soot (Capnodium salicinum
- the agricultural and horticultural pest control agent of the present invention is particularly effective in sterilizing effect and insecticidal effect, and contains one or more compounds represented by the formula [I] as active ingredients.
- the compound of the present invention represented by the formula [I] is applied to the plant by spraying, spraying, applying, or the like with the active ingredient, or sowing the seed of the plant or the soil or seed around the plant. It can be performed by treating soil, paddy field, hydroponics water with active ingredients.
- the application can be done before or after the plant is infected with the pathogen.
- application can be performed before or after the occurrence of pests.
- This compound is in the form of normal preparations such as granules, powders, aqueous solvents, oils, emulsions, microemulsions, suspoemulsions, solutions, wettable powders, emulsions, suspensions, tablets, granules It can be used as an agent suitable for agricultural and horticultural pest control agents such as wettable powders, microcapsules, aerosols, pastes, jumbo agents, powders, smoke agents, fumigants and the like.
- Such embodiments include at least one compound of the invention and a suitable solid or liquid carrier, and, if desired, suitable adjuvants (eg, surfactants) to improve the dispersibility of the active ingredient and other properties.
- suitable adjuvants eg, surfactants
- solid carriers or diluents include plant materials (eg, crystalline cellulose, starch, wood flour, cork, coffee husk, etc.), fibrous materials, artificial plastic powders, clays (eg, kaolin, bentonite) , White clay, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, acid clay, etc., talc and minerals (eg, vermulite, montmorillonite, pumice, sulfur powder, apatite, mica, sericite, quartz powder, activated carbon, calcium carbonate Etc.), polymer compounds (polyvinyl chloride, petroleum resins, etc.), chemical fertilizers (eg, ammonium sulfate, phosphorous acid, ammonium nitrate, ammonium chloride, calcium chloride, urea, etc.).
- plant materials eg, crystalline cellulose, starch, wood flour, cork, coffee husk, etc.
- fibrous materials eg, artificial plastic powders, clays (
- Liquid carriers and diluents include water, alcohols (eg, methanol, ethanol, isopropanol, cyclohexanol, etc.), ketones (eg, acetone, methyl ethyl ketone, cyclohexanone, etc.), ethers (eg, ethyl cellosolve, butyl cellosolve) , Dioxane, etc.), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (eg, kerosene, paraffin, etc.), and swells (eg, isopropyl acetate, benzyl acetate, etc.) Nitriles, amides (eg, N, N-dimethylformamide, dimethyl sulfoxide, etc.), halogenated hydrocarbons (eg, chlor
- gaseous carriers examples include carbon dioxide gas, butane gas, and fluorocarbon.
- surfactants include various anionic surfactants and nonionic surfactants conventionally used in the field of agrochemical formulations.
- anionic surfactant include sulfonic acid-based surfactants such as alkyl sulfonic acid, alpha olefin sulfonic acid, lignin sulfonic acid, alkylbenzene sulfonic acid, alkyl naphthalene sulfonic acid, naphthalene sulfonic acid formalin condensate, and dialkyl sulfosuccinate.
- the salts in the above surfactants include salts of sodium, potassium, magnesium, calcium, ammonium, ethanolamine, diethanolamine, triethanolamine, various amines and the like.
- the nonionic surfactant include polyoxyethylene alkyl allyl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene alkyl ether, polyoxyethylene phenyl alkyl allyl ether, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycol.
- Polyoxyethylene alkyl ester polyoxyethylene polyoxypropylene block copolymer, polyoxyalkylene glycol, alkyne diol (acetylene glycol), alkynylene polyoxyethylene diol, sorbitan fatty acid ester, alkyl aryl ether formalin condensate, etc. it can.
- Stabilizers include isopropyl phosphate mixture, tricresyl phosphate, true oil, epoxy oil, surfactants, fatty acids and esters thereof.
- the compounds of the present invention can be formulated in admixture with other fungicides, insecticides, herbicides, or fertilizers.
- the formulation at least one of the compounds of the present invention [I], 1 ⁇ 95 wt%, preferably 1-50 wt%.
- these preparations can be used alone or diluted, and the compound [I] of the present invention is used in an amount of about 1 to 5 kg / ha, preferably about 2 to 100 g / ha, usually about 1 to 50000 ppm, preferably about Used at a concentration of 50-1000 ppm.
- the compound of the present invention represented by the formula [I] can be used alone or as a preparation thereof, but a bactericidal / fungicidal agent, bactericidal agent, acaricide, nematicide, insecticide, biological pesticide, A mixture of herbicides, plant hormones, plant growth regulators, synergists, attractants, repellents, pigments, fertilizers, etc., or a mixture of one or more selected from those active ingredients
- the preparation can also be used as a pest control agent. There, it can be expected that the action, pests to be controlled, expansion of the appropriate period of use, or reduction of dosage, synergistic effect, or prevention of development of resistance, etc. Shinogi, cooperative medicinal effects with joint ingredients are achieved.
- Examples of co-components in the mixture include the following compounds.
- the fungicides are azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, epoxiconazole, fenbuconazole, fluconazole furconazole), hexaconazole, imibenconazole, metoconazole, microbutanil, penconazole, propiconazole, simeconazole, tebuconazole, tebuconazole, tebuconazole (triadimefon), triadimenol, triticonazole, imazalil, triflumizole, pefurazoate, prochloraz, fenarimol, fenhexamid ), Fenpropimorph, piperalin, spiroxamine, iprodione, microzoline, procymidone, vinclozolin, quinoxyfen, fludioxonil, fludioxonil, fludi
- Insecticides, acaricides, and nematicides include aldicarb, benfuracarb, carbaryl, carbofuran, carbofuran, carbosulfan, fenobcarb, methiocarb , Metomyl, oxamyl, thiodicarb, azephate, chlorpyrifos, diazinon, dimethoate, malathion, methamidophos, monocrotophos ), Parathion-methyl, profenofos, terbufos, endosulfan, ethiprole, fipronil, bifenthrin, cypermethrin, esfenvalen Esfenvalerate, etofenprox, Lambda-cyhalothrin, tefluthrin, DDT (DDT), methoxychlor, acetamiprid, clothianidin, dinotefuran, imida
- herbicides include bensulfuron-methyl, azimsulfuron, cinosulfuron, cyclosulfamuron, pyrazosulfuron-ethyl, imazosulfuron, indanophane indanofan), cyhalofop-butyl, thenylchlor, esprocarb, etobenzanid, caffenstrole, clomeprop, dimethametryn, fenmuron, fenmuron ), Pyributicarb, pyriminobac-methyl, pretilachlor, bromobutide, benzofenap, benthiocarb, bentoxazone, benfuresate, mefe Nasset (mefenacet), fenoxaprop-P-ethyl, phenmedipham, diclofop-methyl, desmedipham, etofumesate, isoproturon ( isoproturon), amidosulfuron
- Biopesticides include nuclear polyhedrosis virus (Nuclear polyhedrosis virus, NPV), granule disease virus (Granulosis virus, GV), cytoplasmic polyhedrosis virus (Cytoplasmic polyhedrosis virus ⁇ , CPV), Steinernema carpocapsae (Steinernema Steinernema glaseri, Monocrosporium ⁇ ⁇ phymatophagum, Steinernema kushidai, Pasteuria penetrans, Agrobacterium radiobacter A. ⁇ Bacillus subtilis, Erwinia carotovora, Pseudomonas fluorescens, Talaromyces flavus, Trichoderma atroviride, Trichoderma atroviride Bacillus thuringiensis, Beauveria brongniartii, Beauveria bassiana, Paecilomyces fumosoroseus, Verticillium) lecanii, Verticill
- Pheromone agents include: cordrelure ((E, E) -8,10-Dodecadien-1-ol), doot armoria B ((Z) -9-Tetradecen-1-ol), tetradodecenyl acetate ((Z ) -11-Tetradecenyl acetate), Pyrimalua (14-Methyl-1-octadecene), Peach Fluor ((Z) -13-Eicosen-10-one) and the like.
- Natural fungicides and natural insecticides include machine oil (Machine oils), methylphenylacetate ( ⁇ ), pinned ( ⁇ -Pinene), carbohydrate degradation product (Protein hydrolysate), (Z) -1-Tetradecen- 1-ol, turpentine, etc. can be mentioned.
- R 1 TMS (trimethylsilyl)
- R 2 H
- R 3 -R 4 thiophene
- Step B 4-Trimethylsilanyl-3-butynyl p-toluenesulfonate 130 ml of dry tetrahydrofuran and 6.45 g of the O-tosyl compound obtained in the above step were added to a flask purged with nitrogen, and the solution was cooled to -78 ° C.
- Step C 2- (4-Trimethylsilanyl-3-butynyl) isoindole-1,3-dione N, N-dimethylformamide 64 ml, the trimethylsilyl compound obtained in the above step 8.37 g, potassium phthalimide 7.85 g, 0.46 g of potassium iodide was added, and the mixture was stirred at 140 ° C. for 2 hours. After cooling to room temperature, 100 ml of water was added to the reaction solution, and extracted twice with 100 ml of ethyl acetate. The organic layer was washed twice with 100 ml of water and once with 100 ml of saturated brine, and then dried over magnesium sulfate.
- Step D 4-Trimethylsilanyl-3-butynylamine To 3.28 g of the phthalimide compound obtained in the above step, 121 ml of methanol and 2.25 g of hydrazine monohydrate (80%) were added and stirred overnight. The reaction solution was concentrated, the residue was suspended in 50 ml of chloroform, insoluble matters were filtered off, the filtrate was concentrated and dried under reduced pressure to obtain 1.72 g of amine.
- Step E 4- (4-Trimethylsilanyl-3-butynylamino) thieno [2,3-d] pyrimidine 1.72 g of the amine obtained in the previous step, 4-chlorothieno [2, to 32 ml of N, N-dimethylformamide 3-72] pyrimidine (1.72 g) and triethylamine (1.7 ml) were added, and the mixture was stirred at 80 ° C. for 4 hours. The reaction mixture was cooled, 50 ml of water was added, and the mixture was extracted twice with 50 ml of ethyl acetate.
- Step B 2- (6-Methyl-3-heptynyl) isoindole-1,3-dione 168 ml of dry tetrahydrofuran in a nitrogen purged flask, 3.78 g of alcohol obtained in the above step, 4.06 g of phthalimide, triphenylphosphine 7.21 g was added, and 13.9 ml of diethyl azodicarboxylate (40% toluene solution) was slowly added dropwise to this solution at room temperature, followed by stirring at room temperature for 1 day. The reaction mixture was concentrated, 200 ml of water was added to the residue, and the mixture was extracted twice with 150 ml of ethyl acetate.
- Step C 6-Methyl-3-heptynylamine To 5.08 g of the phthalimide compound obtained in the above step, 200 ml of methanol and 3.73 g of hydrazine monohydrate (80%) were added and stirred overnight. The reaction solution was concentrated, and the residue was washed with 50 ml of chloroform and suspended in the washed chloroform.
- Step D 4- (6-Methyl-3-heptynylamino) thieno [2,3-d] pyrimidine 1.65 g of the amine obtained in the above step and 2.13 g of 4-chlorothieno [2,3-d] pyrimidine in 42 ml of DMF , 1.9 ml of triethylamine was added, and the mixture was stirred at 85 ° C. for 4 hours. The reaction mixture was cooled, 100 ml of water was added, and the mixture was extracted twice with 100 ml of ethyl acetate.
- Step B 4-Phenyl-3-butynylamine To 3.70 g of the phthalimide compound obtained in the above step, 135 ml of methanol and 2.52 g of hydrazine monohydrate (80%) were added and stirred overnight.
- Step C 4- (4-Phenyl-3-butynylamino) thieno [2,3-d] pyrimidine 1.94 g of the amine obtained in the previous step, 4-chlorothieno [2,3- d] 1.90 g of pyrimidine and 1.9 ml of triethylamine were added, and the mixture was stirred at 85 ° C. for 4 hours. After cooling to the reaction solution, 50 ml of water was added, followed by extraction twice with 50 ml of ethyl acetate.
- the reaction mixture was concentrated, 300 ml of water was added to the residue, and the mixture was extracted twice with 250 ml of ethyl acetate.
- the organic layer was washed with 200 ml of water and 200 ml of saturated brine and then dried over magnesium sulfate. After filtering magnesium sulfate, the organic layer was concentrated, and the residue was purified by column chromatography (Wakogel C-200, toluene) to obtain 2.20 g of a phthalimide compound.
- Step B 2- (1-methyl-4-phenyl-3-butynyl) isoindole-1,3-dione 367 mg dichlorobis (triphenylphosphine) palladium, 100 mg copper iodide, phthalimide compound obtained in the above step Under a nitrogen atmosphere, 20 ml of tetrahydrofuran, 2.11 g of iodobenzene, and 6.2 ml of triethylamine were added to 20 g, and the mixture was stirred for 8 hours under reflux. After stirring, the reaction solution was cooled to room temperature, and the solid was filtered.
- dichlorobis triphenylphosphine
- Step C 1-methyl-4-phenyl-3-butynylamine
- 63 ml of methanol and 1.18 g of hydrazine monohydrate (80%) were added and stirred overnight.
- the reaction solution was concentrated, the residue was suspended in 30 ml of chloroform, the insoluble material was filtered, the filtrate was concentrated, and dried under reduced pressure to obtain the amine quantitatively.
- Step D 4- (1-Methyl-4-phenyl-3-butynylamino) thieno [2,3-d] pyrimidine
- 4-chlorothieno [2,3 -D] 1.02 g of pyrimidine and 0.9 ml of triethylamine were added, and the mixture was stirred at 80 ° C. for 4 hours.
- 30 ml of water was added and extracted twice with 50 ml of ethyl acetate.
- the organic layer was washed twice with 30 ml of water and once with 30 ml of saturated brine, and then dried over magnesium sulfate.
- R 1 4-methoxycarbonylphenyl
- R 2 H
- R 3 -R 4 thiophene
- Step B 2- [4- (2-Phenylthiazol-4-yl) -3-butynyl] isoindole-1,3-dione dichlorobis (triphenylphosphine) palladium 221 mg, copper iodide 60 mg, N- (3- Butynyl) phthalimide (1.24 g) was added with 15 ml of tetrahydrofuran, 1.50 g of 2-phenyl-4-bromothiazole obtained in the above step and 3.8 ml of triethylamine under a nitrogen atmosphere, and stirred for 4 hours under reflux. After stirring, the reaction solution was cooled to room temperature, and the solid was filtered.
- dichlorobis triphenylphosphine
- Step C 4- (2-Phenylthiazol-4-yl) -3-butynylamine
- 35 ml of methanol and 0.65 g of hydrazine monohydrate (80%) were added. Stir overnight. After stirring, the reaction solution was concentrated, the residue was suspended in 20 ml of chloroform, insoluble matter was filtered off, the filtrate was concentrated, and dried under reduced pressure to obtain 0.96 g of amine.
- Step D 4- [4- (2-Phenylthiazol-4-yl) -3-butynylamino] thieno [2,3-d] pyrimidine 0.96 g of the amine obtained in the above step in 13 ml of N, N-dimethylformamide 4-chlorothieno [2,3-d] pyrimidine (0.68 g) and triethylamine (0.6 ml) were added, and the mixture was stirred at 85 ° C. for 4 hours. After cooling to the reaction solution, 25 ml of water was added and extracted twice with 30 ml of ethyl acetate.
- Step B 2- [4- (2-Benzylthiazol-4-yl) -3-butynyl] isoindole-1,3-dione dichlorobis (triphenylphosphine) palladium 143 mg, copper iodide 38 mg, N- (3- To 0.80 g of butynyl) phthalimide were added 9 ml of tetrahydrofuran, 1.02 g of 2-benzyl-4-bromothiazole obtained in the above step and 2.3 ml of triethylamine under a nitrogen atmosphere, and the mixture was stirred for 4 hours under reflux. After stirring, the reaction solution was cooled to room temperature, and the solid was filtered.
- dichlorobis triphenylphosphine
- Step C 4- (2-Benzylthiazol-4-yl) -3-butynylamine
- To 1.00 g of the phthalimide compound obtained in the above step was added 26 ml of methanol and 0.50 g of hydrazine monohydrate (80%). Stir overnight. After stirring, the reaction solution was concentrated, the residue was suspended in 25 ml of chloroform, the insoluble material was filtered off, the filtrate was concentrated and dried under reduced pressure to obtain 0.12 g of amine.
- Step D 4- [4- (2-Benzylthiazol-4-yl) -3-butynylamino] thieno [2,3-d] pyrimidine
- the amine 0 obtained in the above step was added to 1.5 ml of N, N-dimethylformamide. .12 g, 4-chlorothieno [2,3-d] pyrimidine 0.08 g and triethylamine 0.1 ml were added, and the mixture was stirred at 85 ° C. for 4 hours. After cooling to the reaction solution, 15 ml of water was added and extracted twice with 20 ml of ethyl acetate.
- Step B 2- [4- (2-phenoxythiazol-4-yl) -3-butynyl] isoindole-1,3-dione dichlorobis (triphenylphosphine) palladium 399 mg, copper iodide 109 mg, N- (3- Butynyl) phthalimide (2.24 g) was added with 26 ml of tetrahydrofuran, 2.86 g of the ether compound obtained in the above step and 6.9 ml of triethylamine under a nitrogen atmosphere, and stirred under reflux for 4 hours. After stirring, the reaction solution was cooled to room temperature, and the solid was filtered.
- dichlorobis triphenylphosphine
- Step C 4- (2-phenoxythiazol-4-yl) -3-butynylamine
- methanol 1.76 g of hydrazine monohydrate (80%) were added. Stir overnight.
- the reaction solution was concentrated, the residue was suspended in chloroform (40 ml), insoluble matters were filtered off, the filtrate was concentrated and dried under reduced pressure to obtain 2.24 g of amine.
- Step D 4- [4- (2-Phenoxythiazol-4-yl) -3-butynylamino] thieno [2,3-d] pyrimidine 2.24 g of the amine obtained in the above step in 27 ml of N, N-dimethylformamide 4-chlorothieno [2,3-d] pyrimidine (1.45 g) and triethylamine (1.3 ml) were added, and the mixture was stirred at 85 ° C. for 4 hours. After cooling to the reaction solution, 50 ml of water was added, followed by extraction twice with 50 ml of ethyl acetate.
- Step B 4-thiazolyl-3-butynylamine To 6.35 g of the phthalimide compound obtained in the above step, 115 ml of ethanol, 115 ml of water and 115 ml of ion exchange resin (Diaion WA21J Resin) were added and stirred at 90 ° C. for 2 hours.
- Step C 4-[(4-thiazolyl-3-butynyl) amino] thieno [2,3-d] pyrimidine 2.48 g of the amine obtained in the previous step in 50 ml of N, N-dimethylformamide, 4-chlorothieno [2 , 3-d] pyrimidine (2.60 g) and triethylamine (2.3 ml) were added, and the mixture was stirred at 85 ° C. for 2.5 hours.
- the aqueous layer was further extracted five times with 30 ml of methyl t-butyl ether. After the combined organic layers were concentrated, the residue was dried under vacuum. Water was added to the residue, and the mixture was extracted twice with 30 ml of methyl t-butyl ether. The organic layer was washed twice with 30 ml of water and 30 ml of saturated brine, and then dried over magnesium sulfate. After filtration of magnesium sulfate, the filtrate was concentrated and dried under vacuum to obtain 3.38 g of amine.
- Step B 4-[(1-Phenyl-3-butynyl) amino] quinazoline 11 ml of N, N-dimethylformamide was added with 0.49 g of the amine obtained in the above step, 0.50 g of 4-chloroquinazoline and 0.7 ml of triethylamine. In addition, the mixture was stirred at 85 ° C. for 3 hours. After cooling to the reaction solution, 50 ml of water was added and extracted twice with 20 ml of ethyl acetate. The organic layer was washed twice with 20 ml of water and once with 20 ml of saturated brine, and then dried over magnesium sulfate.
- R 1 phenyl
- R 2 phenyl
- R 3 -R 4 benzene
- Step B 2- (3-Phenyl) propargylglycine ethyl To a flask purged with nitrogen, 20 ml of diethyl ether and 1.80 g of the alcohol obtained in the above step and 20 ml of 1N hydrochloric acid were added and stirred at room temperature for 1 day.
- Step C 4- [2-Ethoxycarbonyl-4-phenyl-3-butynylamino] quinazoline To 15 ml of N, N-dimethylformamide was added 985 mg of the amine obtained in the above step, 720 mg of 4-chloroquinazoline, and 1 ml of triethylamine at 80 ° C. For 4 hours. After cooling the reaction solution, 40 ml of water was added and extracted twice with 70 ml of ethyl acetate. The organic layer was washed twice with 40 ml of saturated brine and then dried over sodium sulfate.
- reaction solution was neutralized by adding aqueous sodium hydrogen carbonate, extracted twice with 40 ml of ethyl acetate, and dried over sodium sulfate. After filtering the sodium sulfate, the organic layer was concentrated and purified using flash chromatography (Biotage AB / Isolera TM ) to obtain 37 mg of 4- [2-hydroxymethyl-4-phenyl-3-butynylamino] quinazoline. It was.
- R 1 phenyl
- R 2 methylaminocarbonyl
- R 3 -R 4 benzene
- the reaction mixture was concentrated and purified using flash chromatography (Biotage AB / Isolera TM ) to obtain 113 mg of 4- [2-methylaminocarbonyl-4-phenyl-3-butynylamino] quinazoline.
- Step B 2- (2-vinyl-4-phenyl-3-butynyl) isoindole-1,3-dione 55 ml of toluene, 1.80 g of 2-vinyl-4-phenyl-3-butynol, phthalimide in a nitrogen purged flask 1.93 g and 3.45 g of triphenylphosphine were added, and 5.30 g of diethyl azodicarboxylate (40% toluene solution) was slowly added dropwise to the solution under ice cooling, and the mixture was warmed to room temperature and stirred for 1 day. After concentrating the reaction solution, 200 ml of diethyl ether was added to the residue, and the resulting solid was filtered off.
- Step C 2-vinyl-4-phenyl-3-butynylamine 2- (2-vinyl-4-phenyl-3-butynyl) isoindole-1,3-dione in 1.00 g and 20 ml of methanol, methylamine solution (40% (Methanol solution) 10 m was added and stirred at 60 ° C. for 1 hour.
- Step D 4- [2-Vinyl-4-phenyl-3-butynylamino] quinazoline 550 mg of 2-vinyl-4-phenyl-3-butynylamine, 500 mg of 4-chloroquinazoline, and 636 ⁇ l of triethylamine are added to 15 ml of DMF, and the mixture is stirred at 80 ° C. for 5 hours. Stir.
- 4,6-dichloro-5-phenylpyrimidine is WO2006 / 138734
- 4,5-dichloro-6- (1-fluoroethyl) pyrimidine is JP-A-2000-7662
- 4-chloro-5-iodo-6- (1-Fluoroethyl) pyrimidine was produced according to the method described in JP-A-2002-275164.
- Table 1 The compounds [I] synthesized as described above and their physical properties are shown in Table 1 (Table 1-1 to Table 1-71). Further, NMR data of the compound [I] are shown in Table 2 (Tables 2-1 to 2-25).
- Table 1 is a generic name (generic name) of Table 1-1 to Table 1-71
- Table 2 is a generic name of Table 2-1 to Table 2-25. (Inclusive name).
- Example 2 [Formulation example] Formulation Example 1: Emulsion 10 parts of the compound of the present invention were dissolved in 45 parts of 1,2-dimethyl-4-ethylbenzene and 35 parts of 1-methyl-2-pyrrolidinone, and this was dissolved in Solpol 3005X (an interface manufactured by Toho Chemical Co., Ltd.). 10 parts of an activator (trade name) was added and stirred to obtain a 10% emulsion.
- Formulation example 2 wettable powder 10 parts of the compound of the present invention was added to a mixture of 2 parts of sodium lauryl sulfate, 4 parts of sodium lignin sulfonate, 20 parts of white carbon and 64 parts of clay. % Wettable powder was obtained.
- Formulation Example 3 Granules To 5 parts of the present compound, 2 parts of sodium dodecylbenzenesulfonate, 2 parts of carboxymethylcellulose, 2 parts of sodium lauryl sulfate, 10 parts of bentonite and 79 parts of clay were added and mixed thoroughly. An appropriate amount of water was added and the mixture was further stirred, granulated with a granulator, and dried by ventilation to obtain a 5% granule.
- Formulation Example 4 Powder 1 part of the original compound is dissolved in 2 parts of soybean oil, 5 parts of white carbon, 0.3 part of isopropyl acid phosphate (PAP) and 91.7 parts of clay are added, and the mixture is stirred and mixed with a juice mixer. A 1% powder was obtained.
- PAP isopropyl acid phosphate
- Formulation Example 5 Flowable agent 20 parts of water containing 20 parts of the present compound, 2 parts, 1 part and 0.2 part of polyoxyethylene alkyl ether, sodium dialkylsulfosuccinate and 1,2-benzisothiazolin-3-one, respectively Were mixed with 60 parts of water containing 8 parts and 0.32 parts of propylene glycol and xanthan gum, respectively, to obtain a 20% suspension in water.
- Formulation Example 6 Granule wettable powder 2 parts of sodium lauryl sulfate, 3 parts of sodium alkylnaphthalene sulfonate, 5 parts of dextrin, 20 parts of white carbon and 50 parts of clay were added to 20 parts of the compound of the present invention and mixed thoroughly. An appropriate amount of water was added, and the mixture was further stirred, granulated with a granulator, and dried by ventilation to obtain a 20% granular wettable powder.
- Example 3 [Efficacy test] (1) Control effect test against tomato plague A potted tomato (variety; sugar lamp, 4.5 leaf stage) is a chemical solution (hereinafter referred to as a reagent solution) in which 10% wettable powder of each test compound is adjusted to 125 ppm. Sprayed with 15 ml per pot using a spray gun, sprayed with a zoospore suspension (Phytophthora infestans) zoospore suspension (zoospore concentration 1.0 ⁇ 10 4 / ml) one day later, and wet at 21 ° C. After standing for 1 day under room conditions and further in a greenhouse for 3 days to cause sufficient disease, the degree of disease on each leaf was examined, and the control value was calculated using the following formula.
- a reagent solution in which 10% wettable powder of each test compound is adjusted to 125 ppm. Sprayed with 15 ml per pot using a spray gun, sprayed with a zoospore suspension (Phytophthora in
- Control value calculation; control value ⁇ (untreated disease area rate ⁇ treated drug disease rate) / untreated disease area rate ⁇ ⁇ 100
- the calculated control value was determined according to the following criteria. The results are shown in Table 3. Control effect High: 100% ⁇ control value ⁇ 60% Control effect Low: 60%> Control value ⁇ 0%
- a potted cucumber (variety: Sagamihanjiro, 2-leaf stage) is a chemical solution in which 10% wettable powder of each test compound is adjusted to 125 ppm (hereinafter referred to as a reagent solution). ) was sprayed at 15 ml per pot using a spray gun, and one day later, a conidial suspension (conidia concentration: 1.0 ⁇ 10 5 cells / ml) of cucumber powdery mildew (Sphaerotheca fuliginea) was spray-inoculated. After sufficient disease was established in a greenhouse for 14 days, the degree of disease on each leaf was compared with the untreated group, and the control effect was determined in the same manner as in Test Example 1. The results are shown in Table 5.
- nymph mite eggs A 3 cm diameter kidney bean leaf was placed on a moist sponge in a plastic cup and 10 female nymph mite (Tetranychus urticae) females were released and allowed to lay overnight at room temperature. Thereafter, the released female adults were removed. 0.4 ml of a chemical solution prepared by diluting a 10% wettable powder of the compounds described in Table 1 to 250 ppm was sprayed, and the number of unhatched eggs after 6 days was investigated to calculate the ovicidal rate. An egg killing rate of 95% or more was judged as A, 80% or more and less than 95% as B, and 60% or more and less than 80% as C. The results are shown in Table 8.
- Efficacy test against sweet potato nematode Take 1 ml of a diluted solution prepared by adding 10% wettable powder of the compound shown in Table 1 to 5000 ppm in a test tube and add 9 ml of distilled water containing about 200 heads of Meloidogyne incognita. And left at room temperature for 48 hours. Thereafter, nematodes treated with the chemical solution were washed out, life and death were determined under a microscope, and the nematicidal rate was calculated. A mortality rate of 95% or more was judged as A, and 80% or more and less than 95% as B. The results are shown in Table 10.
- novel compound of the present invention represented by the formula [I] exhibits an excellent control activity against pests such as pathogens, insects, mites, nematodes and the like that particularly affect agricultural and horticultural plants, it is extremely useful as a new agricultural chemical. It is.
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Abstract
Description
a)フェニル、ベンジル、オキサゾリル、イソオキサゾリル、フリル、ベンゾフリル、イソベンゾフリル、ジヒドロベンゾフリル、チアゾリル、イソチアゾリル、ナフチル、ピリミジニル、ピラジニル、キノキサリル、キナゾリニル、ピリジル、キノリル、イソキノリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ピロリル、インドリル、イソインドリル、ベンゾオキサゾリル、ベンゾイソオキサゾリル、チエニル、ベンゾチエニル、イミダゾリル、ベンズイミダゾリル、ピラゾリル、ピリドニルから成る群より選択される、0~3個のヘテロ原子を場合によっては含有する単環式もしくは二環式の環、
b)炭素原子数1~6個の直鎖状又は分岐状のアルキル、炭素原子数2~8個の直鎖状又は分岐状のアルケニル、炭素原子数2~8個の直鎖状又は分岐状のアルキニル、炭素原子数3~8個のシクロアルキルまたは炭素原子数3~8個のシクロアルケニル、
c)-SiR5R6R7(R5,R6,R7は炭素原子数1~6個の直鎖状又は分岐状のアルキル、フェニルであり、2つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい)、
d)水素原子
から選択され、a)b)の場合、R1は-C(O)OR、-C(O)R、-R、-OR、-SR、-SO2R、-OC(O)R、-C(O)NHR、-C(O)NR2、-NHSO2R、-NRSO2R、-NHR、-NR2、-NHC(O)R、-NRC(O)R、-NHC(O)OR、-NRC(O)OR、-N(OR)C(O)OR、-NHSO2R、-NRSO2R、-SO2NHR、-SO2NR2(ここでのRは、炭素原子数1~8個の直鎖状又は分岐状のアルキル、炭素原子数2~8個の直鎖状又は分岐状のアルケニル、炭素原子数2~8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3~8個のシクロアルキルである)、-SiR5R6R7、-OSiR5R6R7(R5,R6,R7は炭素原子数1~6個の直鎖状又は分岐状のアルキル、フェニルであり、2つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい)、ハロアルキル(同一又は異なって、ハロゲン原子1~9で置換されている炭素原子数が1~4の直鎖状又は分岐状のアルキル基)、ハロアルケニル(同一又は異なって、ハロゲン原子1~4で置換されている炭素原子数が2~6の直鎖状又は分岐状のアルケニル基)、ハロアルコキシ(同一又は異なって、ハロゲン原子1~9で置換されている炭素原子数が1~4の直鎖状又は分岐状のアルコキシ基)、アシルアルコキシ((炭素原子数が1~8の直鎖状又は分岐状の脂肪族炭化水素基)-CO-で表されるアシル基により置換された炭素原子数1~3の直鎖状又は分岐状のアルコキシ基)、アシルオキシアルキル((炭素原子数が1~8の直鎖状又は分岐状の脂肪族炭化水素基)-CO-O-で表されるアシルオキシ基により置換された炭素原子数1~3の直鎖状又は分岐状のアルキル基)、アルキルスルホニルアルキル(炭素原子数が1~8の直鎖状又は分岐状のアルキルスルホニル基により置換された炭素原子数1~3の直鎖状又は分岐状のアルキル基)、シロキシアルキル(-OSiR5R6R7(R5,R6,R7は炭素原子数1~6個の直鎖状又は分岐状のアルキル、フェニルであり、2つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい)により置換された炭素原子数1~3の直鎖状又は分岐状のアルキル基)、ヒドロキシアルキル(ヒドロキシル基により置換された炭素原子数1~3の直鎖状又は分岐状のアルキル基)、アルコキシアルキル(炭素原子数が1~8の直鎖状又は分岐状のアルコキシ基により置換された炭素原子数1~3の直鎖状又は分岐状のアルキル基)、ハロアルコキシアルキル(同一又は異なって、ハロゲン原子1~9で置換されている炭素原子数が1~4の直鎖状又は分岐状のハロアルコキシ基により置換された炭素原子数1~3の直鎖状又は分岐状のアルキル基)、アルキルチオアルキル(炭素原子数が1~8の直鎖状又は分岐状のアルキルチオ基により置換された炭素原子数1~3の直鎖状又は分岐状のアルキル基)、ジアルコキシアセタール(炭素原子数が1~8の直鎖状又は分岐状のアルコキシ基がメチル基に2個置換したジアルコキシメチル基)、アルコキシアルコキシ(炭素原子数が1~8の直鎖状又は分岐状のアルコキシ基により置換された炭素原子数1~3の直鎖状又は分岐状のアルキル基)、シアノアルキル(シアノ基により置換された炭素原子数1~3の直鎖状又は分岐状のアルキル基)、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾジオキソリル、イミド、ホルミル(-CHO)、カルボキシル(-COOH)、ホルムアミド(-NHCHO)、環状エーテル、および環状アミンで置換されていてもよく、
R2は水素原子、-R、-OR、-C(O)OR、-C(O)NHR、-CONR2(ここでのRは、炭素原子数1~8個の直鎖状又は分岐状のアルキル、炭素原子数2~8個の直鎖状又は分岐状のアルケニル、炭素原子数2~8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3~8個のシクロアルキルである)、ヒドロキシアルキル(ヒドロキシル基により置換された炭素原子数1~3の直鎖状又は分岐状のアルキル基)、アルコキシアルキル(炭素原子数が1~8の直鎖状又は分岐状のアルコキシ基により置換された炭素原子数1~3の直鎖状又は分岐状のアルキル基)、ハロアルコキシアルキル(同一又は異なって、ハロゲン原子1~9で置換されている炭素原子数が1~4の直鎖状又は分岐状のハロアルコキシ基により置換された炭素原子数1~3の直鎖状又は分岐状のアルキル基)、フェニル、ヘテロアリール、ハロゲン、シアノ、ハロアルキル(同一又は異なって、ハロゲン原子1~9で置換されている炭素原子数が1~4の直鎖状又は分岐状のアルキル基)、ハロアルコキシ(同一又は異なって、ハロゲン原子1~9で置換されている炭素原子数が1~4の直鎖状又は分岐状のアルコキシ基)を表し、
R3は(1)水素原子、(2)ハロゲン原子、(3)(炭素原子数1~8個の直鎖状又は分岐状の脂肪族炭化水素基)-CO-O-で表されるアシルオキシ、ハロゲン原子若しくは水酸基で置換された炭素原子数1~6個のアルキル、(4)無置換の炭素原子数1~6個のアルキル、(5)-OR、-SR、-SO2R(ここでのRは、炭素原子数1~8個の直鎖状又は分岐状のアルキル、炭素原子数2~8個の直鎖状又は分岐状のアルケニル、炭素原子数2~8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3~8個のシクロアルキルである)、または(6)ハロアルキル(同一又は異なって、ハロゲン原子1~9で置換されている炭素原子数が1~4の直鎖状又は分岐状のアルキル基)を表し、
R4は水素原子、ハロゲン原子、炭素原子数1~6個のアルキル、ニトロ、アミノ、フェニル、ベンジル又はR3と結合してピリミジン環上の炭素原子と共に形成するチオフェン環、ピリジン環、ピロール環、イミダゾール環、ベンゼン環、ナフタレン環、ピリミジン環、フラン環、ピラジン環、ピラゾール環、オキサゾール環を表す。]
a)フェニル、ベンジル、オキサゾリル、イソオキサゾリル、フリル、ベンゾフリル、イソベンゾフリル、ジヒドロベンゾフリル、チアゾリル、イソチアゾリル、ナフチル、ピリミジニル、ピラジニル、キノキサリル、キナゾリニル、ピリジル、キノリル、イソキノリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ピロリル、インドリル、イソインドリル、ベンゾオキサゾリル、ベンゾイソオキサゾリル、チエニル、ベンゾチエニル、イミダゾリル、ベンズイミダゾリル、ピラゾリル、ピリドニルから成る群より選択される、0~3個のヘテロ原子を場合によっては含有する単環式もしくは二環式の環を構成する任意の環原子(炭素原子またはヘテロ原子)を結合手とする基。
b)炭素原子数1~6個の直鎖状又は分岐状のアルキル、炭素原子数2~8個の直鎖状又は分岐状のアルケニル、炭素原子数2~8個の直鎖状又は分岐状のアルキニル、炭素原子数3~8個のシクロアルキルまたは炭素原子数3~8個のシクロアルケニル。
c)-SiR5R6R7(R5,R6,R7は炭素原子数1~6個の直鎖状又は分岐状のアルキル、フェニルであり、2つ若しくは全てが同じ置換基でも全てが違う置換基でもよい)。
d)水素原子。
を挙げることができるが、R8が水素原子若しくは塩素原子であるチエノ[2,3-d]ピリミジン環が好ましい。
を挙げることができるが、R8が水素原子、フッ素原子若しくは塩素原子であるキナゾリン環が好ましい。
N-(3-ブチニル)フタルイミド誘導体[VIII]とヨウ化若しくは臭化フェニル、ヨウ化、臭化若しくは塩化へテロアリール、ヨウ化若しくは臭化アルケニル[V]で薗頭反応を行った後、生成物[IX]をヒドラジン(hydrazine)若しくは塩基により脱保護することにより3-ブチニルアミン誘導体[III]を製造できる。
置換ブチニルアルコール[X]とフタルイミド[XI]から光延反応(Mitsunobu reaction)により生成物[XII]を合成し、生成物[XII]を合成法1と同様、薗頭反応、脱保護を行うことにより3-ブチニルアミン誘導体[III]を製造できる。
末端アルキン[XII]をグリニヤール試薬と反応後、さらにエチレンオキシド[XIII]と反応させて3-ブチニルアルコール誘導体[XIV]を合成する。その後、このアルコールを光延反応、脱保護を行うことにより3-ブチニルアミン誘導体[III]を製造できる。
置換ブチニルアルコール(X)をトシル基で保護した後、アルキルリチウムにより末端アルキン炭素にアニオンを発生させ、求核置換反応により末端アルキン炭素に置換基を導入し生成物[XVI]を製造する。その後、ヨウ化カリウム存在下、カリウムフタルイミド[XVII]と反応させ、生成物[IX]を得る。その後、脱保護を行うことにより3-ブチニルアミン誘導体[III]を製造できる。
置換ブチニルアルコール[XIV]をトシル基で保護した化合物[XVIII]にアジ化ナトリウムを反応させて、アジド化合物[XIV]を製造する。その後、このアジド化合物[XIV]を水素化アルミニウムリチウムで還元する事により、3-ブチニルアミン誘導体[III]を製造できる。
4-ペンチルアミド[XX]からHofmann転移により、3-ブチニルアミン誘導体[III]を製造できる。
アジ化アシル[XXI]からCurtius転移により、3-ブチニルアミン誘導体[III]を製造できる。
本願発明において、「有害生物」という用語は、農園芸用植物に対するあらゆる病害虫及び農園芸用植物に対するあらゆる病原菌を包含する。
本発明の農園芸用の有害生物防除剤は、特に、殺菌効果および殺虫効果が顕著であり、式[I]で示される化合物の1種若しくは2種以上を有効成分として含有するものである。
(1)一般式(I)においてR1=TMS(トリメチルシリル),R2=H,R3-R4=チオフェン(表1、化合物No.2の合成)
段階A:3-ブチニル p-トルエンスルホネート
ジクロロメタン500mlに3-ブチン-1-オール10.00g、トリエチルアミン40mlを加えて溶液を0℃に冷却した。その溶液にパラトルエンスルホニルクロリド30.00gをゆっくり加え、その後室温で一晩撹拌後、反応液に水を加え、ジクロロメタン200mlで2回抽出した。有機層を2回水200mlで洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、ヘキサン:酢酸エチル=6:1)で精製することによってO-トシル化合物13.52gを得た。
段階B:4-トリメチルシラニル-3-ブチニル p-トルエンスルホネート
窒素置換したフラスコに乾燥テトラヒドロフラン130ml、上記段階で得られたO-トシル化合物6.45gを加え、溶液を-78℃に冷却した。冷却後この溶液に1.6Mのn-ブチルリチウムヘキサン溶液18.9mlをゆっくりと滴下した。滴下後-78℃で溶液を2時間撹拌し、トリメチルシリルクロリド5.5mlをゆっくりと滴下した。滴下後-78℃で溶液を15分間撹拌し、さらに室温で1時間撹拌した。撹拌後反応液に水150mlを加え、ジクロロメタン150mlで2回抽出後、硫酸マグネシウムで乾燥した。有機層を濃縮し、残渣を真空下乾燥させる事でトリメチルシリル化合物8.37gを得た。
段階C:2-(4-トリメチルシラニル-3-ブチニル)イソインドール-1,3-ジオン
N,N-ジメチルホルムアミド64mlに上記段階で得られたトリメチルシリル化合物8.37g、フタルイミドカリウム7.85g、ヨウ化カリウム0.46gを加え、140℃で2時間撹拌した。室温まで冷却後、反応液に水100mlを加え、酢酸エチル100mlで2回抽出した。有機層を水100mlで2回、飽和食塩水100mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=4:1)で精製することによってフタルイミド化合物3.28gを得た。
段階D:4-トリメチルシラニル-3-ブチニルアミン
上記段階で得られたフタルイミド化合物3.28gにメタノール121ml、ヒドラジン一水和物(80%)2.25gを加え、一晩撹拌した。反応液を濃縮し、残渣をクロロホルム50mlに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミン1.72gを得た。
段階E:4-(4-トリメチルシラニル-3-ブチニルアミノ)チエノ[2,3-d]ピリミジン
N,N-ジメチルホルムアミド32mlに上記段階で得られたアミン1.72g、4-クロロチエノ[2,3-d]ピリミジン1.72g、トリエチルアミン1.7mlを加え、80℃で4時間撹拌した。反応液を冷却後、水50mlを加え、酢酸エチル50mlで2回抽出した。有機層を水50mlで2回、さらに飽和食塩水50mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=4:1)で精製することによって目的生成物1.83gを得た。
同様の製造法により、表1、化合物No.3~5、87を合成した。
窒素置換したフラスコにテトラヒドロフラン16ml、(1)で得られた4-(4-トリメチルシラニル-3-ブチニルアミノ)チエノ[2,3-d]ピリミジン0.37g、1Mのテトラブチルアンモニウムフルオライドテトラヒドロフラン溶液2.1mlを加え、室温で5時間撹拌した。撹拌後、反応液に飽和塩化アンモニウム水溶液50mlを加え、ジクロロメタン30mlで2回抽出した。有機層を飽和食塩水30mlで洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=4:1)で精製することによって4-(3-ブチニルアミノ)チエノ[2,3-d]ピリミジン0.20gを得た。
同様の製造法により、表1、化合物No.86を合成した。
段階A:6-メチル-3-ヘプチン-1-オール
窒素置換したフラスコに乾燥テトラヒドロフラン22ml、1Mのエチルマグネシウムブロミドテトラヒドロフラン溶液25mlを加え、この溶液に4-メチルペンチン2.9mlをゆっくりと滴下した。この溶液を1時間室温で撹拌し、室温下で1.1Mのエチレンオキシドテトラヒドロフラン溶液25mlをゆっくり滴下し、さらに室温で一晩撹拌した。この反応液に飽和塩化アンモニウム水溶液100mlを加え、ジエチルエーテル100mlで2回抽出し、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、生成したアルコールはそのまま次の反応に使用した(収量3.78g)。
段階B:2-(6-メチル-3-ヘプチニル)イソインドール-1,3-ジオン
窒素置換したフラスコに乾燥テトラヒドロフラン168ml、上記段階で得られたアルコール3.78g、フタルイミド4.06g、トリフェニルホスフィン7.21gを加え、この溶液に室温下でジエチルアゾジカルボキシレート(40%トルエン溶液)13.9mlをゆっくり滴下し、そのまま室温で1日撹拌した。反応液を濃縮後、残渣に水200mlを加え酢酸エチル150mlで2回抽出した。有機層を水200ml及び飽和食塩水200mlで洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン)で精製することによってフタルイミド化合物5.08gを得た。
段階C:6-メチル-3-ヘプチニルアミン
上記段階で得られたフタルイミド化合物5.08gにメタノール200ml、ヒドラジン一水和物(80%)3.73gを加え、一晩撹拌した。反応液を濃縮し、残渣をクロロホルム50mlで洗浄し、洗浄したクロロホルムに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミン1.65gを得た。
段階D:4-(6-メチル-3-ヘプチニルアミノ)チエノ[2,3-d]ピリミジン
DMF42mlに上記段階で得られたアミン1.65g、4-クロロチエノ[2,3-d]ピリミジン2.13g、トリエチルアミン1.9mlを加え、85℃で4時間撹拌した。反応液を冷却後、水100mlを加え、酢酸エチル100mlで2回抽出した。有機層を水100mlで2回、さらに飽和食塩水100mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=4:1)で精製することによって目的生成物2.14gを得た。
同様の製造法により、表1、化合物No.6,8,9,88~91,94を合成した。
段階A:2-(4-フェニル-3-ブチニル)イソインドール-1,3-ジオン
ジクロロビス(トリフェニルホスフィン)パラジウム535mg、ヨウ化銅145mg、N-(3-ブチニル)フタルイミド3.00gに窒素雰囲気下、テトラヒドロフラン35ml、ヨードベンゼン3.06g、トリエチルアミン9.0mlを加え、還流下4時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=4:1)で精製することによって、フタルイミド化合物3.70gを得た。
段階B:4-フェニル-3-ブチニルアミン
上記段階で得られたフタルイミド化合物3.70gにメタノール135ml、ヒドラジン一水和物(80%)2.52gを加え、一晩撹拌した。撹拌後、反応液を濃縮し、残渣をクロロホルム50mlに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミン1.94gを得た。
段階C:4-(4-フェニル-3-ブチニルアミノ)チエノ[2,3-d]ピリミジン
N,N-ジメチルホルムアミド31mlに上記段階で得られたアミン1.94g、4-クロロチエノ[2,3-d]ピリミジン1.90g、トリエチルアミン1.9mlを加え、85℃で4時間撹拌した。反応液に冷却後水50mlを加え、酢酸エチル50mlで2回抽出した。有機層を水30mlで2回、さらに飽和食塩水30mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=4:1)で精製することによって目的生成物1.68gを得た。
同様の製造法により、表1、化合物No.11~28,32~54,64~67,84,85,96~100,102~126,128,130~209,211~214,306~342,355~380を合成した。
段階A:2-(1-メチル-3-ブチニル)イソインドール-1,3-ジオン
窒素置換したフラスコに乾燥テトラヒドロフラン400ml、4-ペンチン-2-オール5.00g、フタルイミド9.65g、トリフェニルホスフィン17.13gを加え、この溶液に室温下でジエチルアゾジカルボキシレート(40%トルエン溶液)30mlをゆっくり滴下し、そのまま室温で1日撹拌した。反応液を濃縮後、残渣に水300mlを加え酢酸エチル250mlで2回抽出した。有機層は水200ml及び飽和食塩水200mlで洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン)で精製することによってフタルイミド化合物2.20gを得た。
段階B:2-(1-メチル-4-フェニル-3-ブチニル)イソインドール-1,3-ジオン
ジクロロビス(トリフェニルホスフィン)パラジウム367mg、ヨウ化銅100mg、上記段階で得られたフタルイミド化合物2.20gに窒素雰囲気下、テトラヒドロフラン24ml、ヨードベンゼン2.11g、トリエチルアミン6.2mlを加え、還流下8時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=9:1)で精製することによって、フタルイミド化合物1.82gを得た。
段階C:1-メチル-4-フェニル-3-ブチニルアミン
上記段階で得られたフタルイミド体1.82gにメタノール63ml、ヒドラジン一水和物(80%)1.18gを加え、一晩撹拌した。撹拌後、反応液を濃縮し、残渣をクロロホルム30mlに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミンを定量的に得た。
段階D:4-(1-メチル-4-フェニル-3-ブチニルアミノ)チエノ[2,3-d]ピリミジン
N,N-ジメチルホルムアミド20mlに上記段階で得られたアミン、4-クロロチエノ[2,3-d]ピリミジン1.02g、トリエチルアミン0.9mlを加え、80℃で4時間撹拌した。反応液に冷却後水30mlを加え、酢酸エチル50mlで2回抽出した。有機層を水30mlで2回、さらに飽和食塩水30mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=9:1)で精製することによって目的生成物0.46gを得た。
同様の製造法により、表1、化合物No.230~295,298,343~354,381~389を合成した。
ジクロロビス(トリフェニルホスフィン)パラジウム170mg、ヨウ化銅46mg、(2)で得られた4-[(3-ブチニル)アミノ]チエノ[2,3-d]ピリミジン0.97gに窒素雰囲気下、テトラヒドロフラン11m4-ヨード安息香酸メチル1.25g、トリエチルアミン2.9mlを加え、還流下4時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=1:1)で精製することによって、4-[4-(チエノ[2,3-d]ピリミジン-4-イルアミノ)-1-ブチニル]ベンゾエート1.09gを得た。
同様の製造法により、表1、化合物No.30,31,92,93,95,127,129を合成した。
段階A:4-ブロモ-2-フェニルチアゾール
テトラキス(トリフェニルホスフィン)パラジウム238mg、フェニルボロン酸0.55g、2,4-ジブロモチアゾール1.00gを入れたフラスコを窒素置換し、このフラスコにトルエン30ml、エタノール6.1ml、2Mの炭酸ナトリウム水溶液9.1mlを加え、還流下6時間撹拌した。室温まで冷却後、反応液に水50mlを加え酢酸エチル50mlで2回抽出した。有機層を飽和食塩水30mlで洗浄し、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、ヘキサン:酢酸エチル=14:1)で精製することによって2-フェニル-4-ブロモチアゾール0.71gを得た。
段階B:2-[4-(2-フェニルチアゾール-4-イル)-3-ブチニル]イソインドール-1,3-ジオン
ジクロロビス(トリフェニルホスフィン)パラジウム221mg、ヨウ化銅60mg、N-(3-ブチニル)フタルイミド1.24gに窒素雰囲気下、テトラヒドロフラン15ml、上記段階で得られた2-フェニル-4-ブロモチアゾール1.50g、トリエチルアミン3.8mlを加え、還流下4時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=9:1)で精製することによって、フタルイミド化合物1.24gを得た。
段階C:4-(2-フェニルチアゾール-4-イル)-3-ブチニルアミン
上記段階で得られたフタルイミド化合物1.24gにメタノール35ml、ヒドラジン一水和物(80%)0.65gを加え、一晩撹拌した。撹拌後、反応液を濃縮し、残渣をクロロホルム20mlに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミン0.96gを得た。
段階D:4-[4-(2-フェニルチアゾール-4-イル)-3-ブチニルアミノ]チエノ[2,3-d]ピリミジン
N,N-ジメチルホルムアミド13mlに上記段階で得られたアミン0.96g、4-クロロチエノ[2,3-d]ピリミジン0.68g、トリエチルアミン0.6mlを加え、85℃で4時間撹拌した。反応液に冷却後水25mlを加え、酢酸エチル30mlで2回抽出した。有機層を水30mlで2回、さらに飽和食塩水30mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=2:1)で精製することによって目的生成物0.70gを得た。
同様の製造法により、表1、化合物No.77~82を合成した。
段階A:2-ベンジル-4-ブロモチアゾール
テトラキス(トリフェニルホスフィン)パラジウム267mg、2,4-ジブロモチアゾール1.00gを入れたフラスコを窒素置換し、このフラスコに乾燥テトラヒドロフラン9ml、0.5Mの臭化ベンジル亜鉛テトラヒドロフラン溶液9.9mlを加え、70℃で6時間撹拌した。室温まで冷却後、反応液に水30mlを加え酢酸エチル30mlで2回抽出した。有機層を水30mlで2回、さらに飽和食塩水30mlで1回洗浄し、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、ヘキサン:酢酸エチル=14:1)で精製することによって2-ベンジル-4-ブロモチアゾール0.36gを得た。
段階B:2-[4-(2-ベンジルチアゾール-4-イル)-3-ブチニル]イソインドール-1,3-ジオン
ジクロロビス(トリフェニルホスフィン)パラジウム143mg、ヨウ化銅38mg、N-(3-ブチニル)フタルイミド0.80gに窒素雰囲気下、テトラヒドロフラン9ml、上記段階で得られた2-ベンジル-4-ブロモチアゾール1.02g、トリエチルアミン2.3mlを加え、還流下4時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=9:1)で精製することによって、フタルイミド化合物1.00gを得た。
段階C:4-(2-ベンジルチアゾール-4-イル)-3-ブチニルアミン
上記段階で得られたフタルイミド化合物1.00gにメタノール26ml、ヒドラジン一水和物(80%)0.50gを加え、一晩撹拌した。撹拌後、反応液を濃縮し、残渣をクロロホルム25mlに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミン0.12gを得た。
段階D:4-[4-(2-ベンジルチアゾール-4-イル)-3-ブチニルアミノ]チエノ[2,3-d]ピリミジン
N,N-ジメチルホルムアミド1.5mlに上記段階で得られたアミン0.12g、4-クロロチエノ[2,3-d]ピリミジン0.08g、トリエチルアミン0.1mlを加え、85℃で4時間撹拌した。反応液に冷却後水15mlを加え、酢酸エチル20mlで2回抽出した。有機層を水20mlで2回、さらに飽和食塩水20mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=1:1)で精製することによって目的生成物0.07gを得た。
段階A:4-ブロモ-2-フェノキシチアゾール
N,N-ジメチルホルムアミド75mlに2,4-ジブロモチアゾール3.00g、フェノール1.74g、炭酸カリウム3.44gを加え、140℃で6時間撹拌した。室温まで冷却後、反応液に水100mlを加え、酢酸エチル100mlで2回抽出した。有機層を水100mlで2回、飽和食塩水50mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、ヘキサン:酢酸エチル=9:1)で精製することによってエーテル化合物2.86gを得た。
段階B:2-[4-(2-フェノキシチアゾール-4-イル)-3-ブチニル]イソインドール-1,3-ジオン
ジクロロビス(トリフェニルホスフィン)パラジウム399mg、ヨウ化銅109mg、N-(3-ブチニル)フタルイミド2.24gに窒素雰囲気下、テトラヒドロフラン26ml、上記段階で得られたエーテル化合物2.86g、トリエチルアミン6.9mlを加え、還流下4時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=9:1)で精製することによって、フタルイミド化合物3.50gを得た。
段階C:4-(2-フェノキシチアゾール-4-イル)-3-ブチニルアミン
上記段階で得られたフタルイミド化合物3.50gにメタノール90ml、ヒドラジン一水和物(80%)1.76gを加え、一晩撹拌した。撹拌後、反応液を濃縮し、残渣をクロロホルム40mlに懸濁し、不溶物をろ過後、ろ液を濃縮し、減圧下乾燥してアミン2.24gを得た。
段階D:4-[4-(2-フェノキシチアゾール-4-イル)-3-ブチニルアミノ]チエノ[2,3-d]ピリミジン
N,N-ジメチルホルムアミド27mlに上記段階で得られたアミン2.24g、4-クロロチエノ[2,3-d]ピリミジン1.45g、トリエチルアミン1.3mlを加え、85℃で4時間撹拌した。反応液に冷却後水50mlを加え、酢酸エチル50mlで2回抽出した。有機層を水50mlで2回、さらに飽和食塩水30mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=1:1)で精製することによって目的生成物2.79gを得た。
同様の製造法により、表1、化合物No.215~228を合成した。
段階A:2-(4-チアゾリル-3-ブチニル)イソインドール-1,3-ジオン
ジクロロビス(トリフェニルホスフィン)パラジウム1184mg、ヨウ化銅322mg、N-(3-ブチニル)フタルイミド6.64gに窒素雰囲気下、テトラヒドロフラン78ml、4-ブロモチアゾール5.49g、トリエチルアミン20.3mlを加え、還流下5時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=4:1)で精製することによって、フタルイミド化合物6.35gを得た。
段階B:4-チアゾリル-3-ブチニルアミン
上記段階で得られたフタルイミド化合物6.35gにエタノール115ml、水115ml、イオン交換樹脂(Diaion WA21J Resin)115mlを加え、90℃で2時間撹拌した。室温まで冷却後、イオン交換樹脂をろ過し、反応液を減圧下濃縮することによって、アミン2.48g得た。
段階C:4-[(4-チアゾリル-3-ブチニル)アミノ]チエノ[2,3-d]ピリミジン
N,N-ジメチルホルムアミド50mlに上記段階で得られたアミン2.48g、4-クロロチエノ[2,3-d]ピリミジン2.60g、トリエチルアミン2.3mlを加え、85℃で2.5時間撹拌した。反応液を冷却後、水を1L加え、析出した固体をろ過し、ろ物を水100mlで2回洗浄後、真空下乾燥する事で目的生成物3.00gを得た。
同様の製造法により、表1、化合物No.55~60,62,63,68~74,101,210を合成した。
段階A:1-フェニル-3-ブチニルアミン
テトラヒドロフラン4mlにベンズアルデヒド2.97gを加えた溶液に窒素雰囲気下、1Mのリチウムビストリメチルシリルアミドテトラヒドロフラン溶液を0℃で滴下した。この溶液を0℃で15分間、さらに室温で1時間撹拌した。この溶液を溶液Aとする。
亜鉛粉末6.03gに窒素雰囲気下、テトラヒドロフラン4ml、1,2-ジブロモエタン0.63gを加え、還流下1時間撹拌した。撹拌後、室温まで冷却後、クロロトリメチルシランのテトラヒドロフラン溶液(クロロトリメチルシラン0.37g+テトラヒドロフラン8ml)を室温で加えた。この溶液を-10℃に冷却し、プロパルギルブロミドのテトラヒドロフラン溶液(プロパルギルブロミド10.00g+テトラヒドロフラン8ml)を滴下し、さらに-10℃で1.5時間撹拌した。撹拌後、この溶液に溶液Aを-10℃で滴下し、適下後、徐々に室温まで上げ、室温で一晩撹拌した。反応液を0℃に冷却後、飽和炭酸カリウム溶液20mlを加え、さらに水65ml、メチルt-ブチルエーテル30mlを加えた。有機層を分液後、水層をさらにメチルt-ブチルエーテル30mlで5回抽出した。合わせた有機層を濃縮後、残渣を真空下乾燥した。この残渣に水を加え、メチルt-ブチルエーテル30mlで2回抽出し、有機層を水30mlで2回、飽和食塩水30mlで洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、ろ液を濃縮し、真空下乾燥することでアミン3.38gを得た。
段階B:4-[(1-フェニル-3-ブチニル)アミノ]キナゾリン
N,N-ジメチルホルムアミド11mlに上記段階で得られたアミン0.49g、4-クロロキナゾリン0.50g、トリエチルアミン0.7mlを加え、85℃で3時間撹拌した。反応液に冷却後水50mlを加え、酢酸エチル20mlで2回抽出した。有機層を水20mlで2回、さらに飽和食塩水20mlで1回洗浄後、硫酸マグネシウムで乾燥した。硫酸マグネシウムをろ過後、有機層を濃縮し、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=1:1)で精製することによって目的生成物0.69gを得た。
ジクロロビス(トリフェニルホスフィン)パラジウム278mg、ヨウ化銅71mg、(11)で得られた4-[(1-フェニル-3-ブチニル)アミノ]キナゾリン2.00gに窒素雰囲気下、テトラヒドロフラン17m、ヨードベンゼン1.49g、トリエチルアミン4.5mlを加え、還流下3時間撹拌した。撹拌後、反応液を室温まで冷却し、固体をろ過した。ろ液を濃縮後、残渣をカラムクロマトグラフィー(ワコーゲルC-200、トルエン:酢酸エチル=4:1)で精製することによって、4-[(1,4-ジフェニル-3-ブチニル)アミノ]キナゾリン1.03gを得た。
同様の製造法により、表1、化合物No.302を合成した。
段階A:N-(ジフェニルメチレン)-2-(3-フェニル)プロパルギルグリシンエチル
窒素置換したフラスコにアセトニトリル50ml、N-(ジフェニルメチレン)グリシンエチル3.00g、3-フェニルプロパルギルブロマイド2.60g、炭酸カリウム2.32g、テトラブチルアンモニウム硫酸水素塩381mgを加え、24時間70度で撹拌した。室温に冷却後、この反応液に酢酸エチル100mlを加え、セライトろ過後、ろ液を濃縮し、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、N-(ジフェニルメチレン)-2-(3-フェニル)プロパルギルグリシンエチル2.00gを得た。
段階B:2-(3-フェニル)プロパルギルグリシンエチル
窒素置換したフラスコにジエチルエーテル20ml、上記段階で得られたアルコール1.80g、1N塩酸20mlを加え、そのまま室温で1日撹拌した。この反応液に重曹水30mlを加えたのち酢酸エチル50mlで2回抽出し、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、2-(3-フェニル)プロパルギルグリシンエチル985mgを得た。
段階C:4-[2-エトキシカルボニル-4-フェニル-3-ブチニルアミノ]キナゾリン
N,N-ジメチルホルムアミド15mlに上記段階で得られたアミン985mg、4-クロロキナゾリン720mg、トリエチルアミン1mlを加え、80℃で4時間撹拌した。反応液を冷却後、水40mlを加え、酢酸エチル70mlで2回抽出した。有機層を飽和食塩水40mlで2回洗浄後、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、目的生成物1.10gを得た。
同様の製造法により、表1、化合物No.304を合成した。
テトラヒドロフラン10mlに4-[2-エトキシカルボニル-4-フェニル-3-ブチニルアミノ]キナゾリン200mg、リチウムジメチルアミノボロハイドライドの1Mテトラヒドロフラン溶液1mlを加え、室温で1時間撹拌した。反応液に1N塩酸20mlを加え、10分撹拌した。この反応液に重曹水を加え中和した後、酢酸エチル40mlで2回抽出し、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、4-[2-ヒドロキシメチル-4-フェニル-3-ブチニルアミノ]キナゾリン37mgを得た。
テトラヒドロフラン5mlに4-[2-エトキシカルボニル-4-フェニル-3-ブチニルアミノ]キナゾリン130mg、40%メチルアミンメタノール溶液3mlを加え、60℃で1時間、室温で1昼夜撹拌した。反応液を濃縮後、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、4-[2-メチルアミノカルボニル-4-フェニル-3-ブチニルアミノ]キナゾリン113mgを得た。
段階A: 2-ビニル-4-フェニル-3-ブチンオール
窒素置換したフラスコに乾燥テトラヒドロフラン40ml、1.6Mのn-ブチルリチウム溶液20mlを-78℃で加え、30分撹拌した。この溶液にトリフルオロボランテトラヒドロフラン錯体3.5mlをゆっくりと滴下した。さらにこの溶液を15分、-78℃で撹拌し、1,3-ブタジエンモノエポキシド2.00gをゆっくり滴下し、さらに-78℃で3時間撹拌した。この反応液に飽和塩化アンモニウム水溶液50mlを加え、酢酸エチル100mlで1回抽出し、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、2-ビニル-4-フェニル-3-ブチンオール1.80gを得た。
段階B: 2-(2-ビニル-4-フェニル-3-ブチニル)イソインドール-1,3-ジオン
窒素置換したフラスコにトルエン55ml、2-ビニル-4-フェニル-3-ブチンオール1.80g、フタルイミド1.93g、トリフェニルホスフィン3.45gを加え、この溶液に氷冷下でジエチルアゾジカルボキシレート(40%トルエン溶液)5.30gをゆっくり滴下し、室温に昇温し1日撹拌した。反応液を濃縮後、残渣にジエチルエーテル200mlを加え、出てきた固体をろ別した。残渣を濃縮し、フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し、2-(2-ビニル-4-フェニル-3-ブチニル)イソインドール-1,3-ジオン1.00gを得た。
段階C:2-ビニル-4-フェニル-3-ブチニルアミン
2-(2-ビニル-4-フェニル-3-ブチニル)イソインドール-1,3-ジオン1.00gにメタノール20ml、メチルアミン溶液(40%メタノール溶液)10mを加え、1時間60℃で撹拌した。反応液を濃縮し、酢酸エチル50ml、ジエチルエーテル50mlで順次洗浄後、ろ液を濃縮して粗生成物のアミン550mgを得た。
段階D:4-[2-ビニル-4-フェニル-3-ブチニルアミノ]キナゾリン
DMF15mlに2-ビニル-4-フェニル-3-ブチニルアミン550mg、4-クロロキナゾリン500mg、トリエチルアミン636μlを加え、80℃で5時間撹拌した。反応液を冷却後、水20mlを加え、酢酸エチル50mlで2回抽出した。有機層を飽和食塩水50mlで2回洗浄後、硫酸ナトリウムで乾燥した。硫酸ナトリウムをろ過後、有機層を濃縮し、フラッシュ自動生成装置フラッシュクロマトグラフィー(biotage AB社製/IsoleraTM)を用いて精製し目的生成物750mgを得た。
同様の製造法により、表1、化合物No.297を合成した。
製剤例1:乳剤
本発明化合物10部を、1,2-ジメチル-4-エチルベンゼン45部および1-メチル-2-ピロリジノン35部に溶解し、これにソルポール3005X(東邦化学工業株式会社製の界面活性剤の商品名)10部を加え、攪拌混合して10%乳剤を得た。
製剤例2:水和剤
本発明化合物10部を、ラウリル硫酸ナトリウム2部、リグニンスルホン酸ナトリウム4部、ホワイトカーボン20部およびクレー64部を混合した中に加え、ジュースミキサーで攪拌混合して10%水和剤を得た。
製剤例3:粒剤
本発明化合物5部に、ドデシルベンゼンスルホン酸ナトリウム2部、カルボキシメチルセルロース2部、ラウリル硫酸ナトリウム2部、ベントナイト10部およびクレー79部を加え十分攪拌混合した。適当量の水を加えさらに攪拌し、造粒機で造粒し通風乾燥して5%粒剤を得た。
製剤例4:粉剤
本発化合物1部を大豆油2部に溶解し、ホワイトカーボン5部、酸性リン酸イソプロピル(PAP)0.3部およびクレー91.7部を加え、ジュースミキサーで攪拌混合し、1%粉剤を得た。
製剤例5:フロアブル剤
本発明化合物20部とポリオキシエチレンアルキルエーテル、ジアルキルスルホサクシネートナトリウムおよび1,2-ベンズイソチアゾリン-3-オンをそれぞれ2部、1部および0.2部含む水20部を混合しダイノミルを用いて湿式粉砕後、プロピレングリコールおよびキサンタンガムをそれぞれ8部および0.32部含む水60部と混合し20%水中懸濁液を得た。
製剤例6:顆粒水和剤
本発明化合物20部に、ラウリル硫酸ナトリウム2部、アルキルナフタレンスルホン酸ナトリウム3部、デキストリン5部、ホワイトカーボン20部、クレー50部を加え十分攪拌混合した。適当量の水を加えさらに攪拌し、造粒機で造粒し通風乾燥して20%顆粒水和剤を得た。
(1)トマト疫病に対する防除効果試験
ポット植えトマト(品種;シュガーランプ、4.5葉期)に各供試化合物の10%水和剤を125ppmに調整した薬液(以下供試薬液と称する。)をスプレーガンを用いポット当たり15ml散布し、1日後にトマト疫病菌(Phytophthora infestans)の遊走子懸濁液(遊走子濃度1.0×104個/ml)を噴霧接種し、21℃の湿室条件下に1日置き、さらに温室に3日間置いて十分に発病させた後、各葉の発病程度を調査し、以下の式を用いて防除価を算出した。
防除価の算出;防除価={(無処理の発病面積率-処理した薬剤の発病面積率)/無処理の発病面積率}×100
算出された防除価を下記の基準に従って判定を行った。結果を表3に示す。
防除効果 高 : 100%≧防除価≧60%
防除効果 低 : 60%>防除価≧0%
ポット植えキュウリ(品種;相模半白、2.5葉期)に各供試化合物の10%水和剤を125ppmに調整した薬液(以下供試薬液と称する。)をスプレーガンを用いポット当たり15ml散布し、1日後にキュウリべと病菌(Pseudoperonospora cubensis)の分生子懸濁液(分生子濃度1.0×104個/ml)を噴霧接種した。接種後21℃の湿室条件下に1日置き、更に温室で3日間置いて充分発病させた後、各葉の発病程度を無処理区と対比し、試験例1と同様にして防除効果の判定を行った。結果を表4に示す。
ポット植えキュウリ(品種;相模半白、2葉期)に各供試化合物の10%水和剤を125ppmに調整した薬液(以下供試薬液と称する。)をスプレーガンを用いポット当たり15ml散布し、1日後にキュウリうどんこ病菌(Sphaerotheca fuliginea)の分生子懸濁液(分生子濃度1.0×105個/ml)を噴霧接種した。温室で14日間置いて充分発病させた後、各葉の発病程度を無処理区と対比し、試験例1と同様にして防除効果の判定を行った。結果を表5に示す。
直径3cmのキュウリ葉片をプラスチックカップ内の湿らせたスポンジ上に置き、ワタアブラムシ(Aphis gossypii)雌成虫5頭を放飼し、一晩静置の後、産仔幼虫数を計数した。表1記載化合物の10%水和剤を250ppmに希釈調製した薬液0.4mlずつを散布し、二日後に死亡虫数を調査して死亡率を算出した。死亡率が95%以上をA、同80%以上95%未満をB、同60%以上80%未満をCと判定した。結果を表6に示す。
直径3cmのインゲン葉片をプラスチックカップ内の湿らせたスポンジ上に置き、ナミハダニ(Tetranychus urticae)雌成虫10頭を放飼した。表1記載化合物の10%水和剤を250ppmに希釈調製した薬液0.4mlずつを散布し、二日後の死亡虫数を調査して死亡率を算出した。死亡率が95%以上をA、同80%以上95%未満をB、同60%以上80%未満をCと判定した。結果を表7に示す。
直径3cmのインゲン葉片をプラスチックカップ内の湿らせたスポンジ上に置き、ナミハダニ(Tetranychus urticae)雌成虫10頭を放飼し、一晩室温条件下にて産卵させた後、放飼した雌成虫を除去した。表1記載化合物の10%水和剤を250ppmに希釈調製した薬液0.4mlずつを散布し、6日後の未孵化卵数を調査して殺卵率を算出した。殺卵率が95%以上をA、同80%以上95%未満をB、同60%以上80%未満をCと判定した。結果を表8に示す。
直径3cmのハクサイ葉片を、表1記載化合物の10%水和剤を500ppmに希釈調製した薬液に浸漬処理した後風乾させ、プラスチックシャーレに収容して、ハスモンヨトウ(Spodptera litura)3令幼虫10頭を放飼した。処理二日後の死亡虫数を調査して死亡率を算出した。死亡率が95%以上をA、同80%以上95%未満をB、同60%以上80%未満をCと判定した。結果を表9に示す。
表1記載化合物の10%水和剤を5000ppmに調製した希釈液を試験管に1mlとり、約200頭のサツマイモネコブセンチュウ(Meloidogyne incognita)を含む蒸留水9mlを添加して、48時間、室温に静置した。その後、薬液処理した線虫を洗い出し、顕微鏡下で生死を判別、殺線虫率を算出した。死亡率が95%以上をA、同80%以上95%未満をBと判定した。結果を表10に示す。
Claims (8)
- 次式[I]:
a)フェニル、ベンジル、オキサゾリル、イソオキサゾリル、フリル、ベンゾフリル、イソベンゾフリル、ジヒドロベンゾフリル、チアゾリル、イソチアゾリル、ナフチル、ピリミジニル、ピラジニル、キノキサリル、キナゾリニル、ピリジル、キノリル、イソキノリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ピロリル、インドリル、イソインドリル、ベンゾオキサゾリル、ベンゾイソオキサゾリル、チエニル、ベンゾチエニル、イミダゾリル、ベンズイミダゾリル、ピラゾリル、ピリドニルから成る群より選択される、0~3個のヘテロ原子を場合によっては含有する単環式もしくは二環式の環、
b)炭素原子数1~6個の直鎖状又は分岐状のアルキル、炭素原子数2~8個の直鎖状又は分岐状のアルケニル、炭素原子数2~8個の直鎖状又は分岐状のアルキニル、炭素原子数3~8個のシクロアルキルまたは炭素原子数3~8個のシクロアルケニル、
c)-SiR5R6R7(R5,R6,R7は炭素原子数1~6個の直鎖状又は分岐状のアルキル、フェニルであり全てが同じ置換基でも全てが異なる置換基でもよい)、
d)水素原子
から選択され、a)またはb)の場合、R1は-C(O)OR、-C(O)R、-R、-OR、-SR、-SO2R、-OC(O)R、-C(O)NHR、-C(O)NR2、-NHSO2R、-NRSO2R、-NHR、-NR2、-NHC(O)R、-NRC(O)R、-NHC(O)OR、-NRC(O)OR、-N(OR)C(O)OR、-NHSO2R、-NRSO2R、-SO2NHR、-SO2NR2(ここでのRは、炭素原子数1~8個の直鎖状又は分岐状のアルキル、炭素原子数2~8個の直鎖状又は分岐状のアルケニル、炭素原子数2~8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3~8個のシクロアルキルである)、-SiR5R6R7、-OSiR5R6R7(R5,R6,R7は炭素原子数1~6個の直鎖状又は分岐状のアルキル、フェニルであり2つ若しくは全てが同じ置換基でも全てが異なる置換基でもよい)、ハロアルキル、ハロアルケニル、ハロアルコキシ、アシルアルコキシ、アシルオキシアルキル、アルキルスルホニルアルキル、シロキシアルキル、ヒドロキシアルキル、アルコキシアルキル、ハロアルコキシアルキル、アルキルチオアルキル、ジアルコキシアセタール、アルコキシアルコキシ、シアノアルキル、ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシ、ペンタハロスルファニル、ベンジル、ベンジルオキシ、フェニル、フェノキシ、ピリジル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、チエニル、ベンゾチアゾリル、ベンゾオキサゾリル、ベンゾジオキソリル、イミド、ホルミル(-CHO)、カルボキシル(-COOH)、ホルムアミド(-NHCHO)、環状エーテル、および環状アミンで置換されていてもよく、
R2は水素原子、-R、-OR、-C(O)OR、-C(O)NHR、-CONR2(ここでのRは、炭素原子数1~8個の直鎖状又は分岐状のアルキル、炭素原子数2~8個の直鎖状又は分岐状のアルケニル、炭素原子数2~8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3~8個のシクロアルキルである)、ヒドロキシアルキル、アルコキシアルキル、ハロアルコキシアルキル、フェニル、ヘテロアリール、ハロゲン、シアノ、ハロアルキル、ハロアルコキシを表し、
R3は(1)水素原子、(2)ハロゲン原子、(3)(炭素原子数1~8個の直鎖状又は分岐状の脂肪族炭化水素基)-CO-O-で表されるアシルオキシ、、ハロゲン原子若しくは水酸基で置換された炭素原子数1~6個のアルキル、(4)無置換の炭素原子数1~6個のアルキル、(5)-OR、-SR、-SO2R(ここでのRは、炭素原子数1~8個の直鎖状又は分岐状のアルキル、炭素原子数2~8個の直鎖状又は分岐状のアルケニル、炭素原子数2~8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3~8個のシクロアルキルである)、または(6)ハロアルキルを表し、
R4は水素原子、ハロゲン原子、炭素原子数1~6個のアルキル、ニトロ、アミノ、フェニル、ベンジル又はR3と結合してピリミジン環上の炭素原子と共に形成するチオフェン環、ピリジン環、ピロール環、イミダゾール環、ベンゼン環、ナフタレン環、ピリミジン環、フラン環、ピラジン環、ピラゾール環、オキサゾール環を表す。]
で示される4-(3-ブチニル)アミノピリミジン誘導体。 - R4がR3と結合してピリミジン環上の炭素原子と共に形成するチオフェン環である、請求項1に記載の化合物。
- R4がR3と結合してピリミジン環上の炭素原子と共に形成するベンゼン環である、請求項1に記載の化合物。
- R3が1ないしは複数個のハロゲン原子で置換された炭素原子数1~6個のアルキル、R4がハロゲン原子である、請求項1に記載の化合物。
- R2が水素原子、ハロゲン原子、シアノ基、フェニル、ヘテロアリール、-R、-C(O)OR、-C(O)NHR(ここでのRは、炭素原子数1~8個の直鎖状又は分岐状のアルキル、炭素原子数2~8個の直鎖状又は分岐状のアルケニル、炭素原子数2~8個の直鎖状又は分岐状のアルキニルまたは炭素原子数3~8個のシクロアルキルである)、ヒドロキシアルキル、アルコキシアルキルである、請求項1に記載の化合物。
- R1がフェニル、オキサゾリル、フリル、チアゾリル、ナフチル、ピリミジニル、ピリジル、ベンゾチアゾリル、ピロリル、ベンゾオキサゾリル、ピラジニル、チエニル、イミダゾリルから成る群より選択される、0~3個のヘテロ原子を場合によっては含有する単環式もしくは二環式の環から選択される、請求項1に記載の化合物。
- 請求項1に記載の式[I]で示される4-(3-ブチニル)アミノピリミジン誘導体を有効成分として1種若しくは2種以上含む有害生物防除剤。
Priority Applications (9)
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US13/378,866 US8586505B2 (en) | 2009-07-16 | 2010-07-15 | 4-(3-butynyl)aminopyrimidine derivatives as pest control agents for agricultural and horticultural use |
NZ597198A NZ597198A (en) | 2009-07-16 | 2010-07-15 | 4-(3-butynyl)aminopyrimidine derivatives as pest control agents for agricultural and horticultural use |
CA2765661A CA2765661C (en) | 2009-07-16 | 2010-07-15 | 4-(3-butynyl)aminopyrimidine derivatives as pest control agents for agricultural and horticultural use |
PL10799897T PL2455371T3 (pl) | 2009-07-16 | 2010-07-15 | Pochodne 4-(3-butynylo)aminopirymidyny jako środki do zwalczania szkodników do stosowania w rolnictwie i ogrodnictwie |
JP2011522855A JP5325297B2 (ja) | 2009-07-16 | 2010-07-15 | 農園芸用の有害生物防除剤としての4−(3−ブチニル)アミノピリミジン誘導体 |
EP10799897.3A EP2455371B1 (en) | 2009-07-16 | 2010-07-15 | 4-(3-butynyl)aminopyrimidine derivatives as pest control agents for agricultural and horticultural use |
AU2010271805A AU2010271805B2 (en) | 2009-07-16 | 2010-07-15 | 4-(3-butynyl)aminopyrimidine derivatives as pest control agents for agricultural and horticultural use |
ES10799897.3T ES2443154T3 (es) | 2009-07-16 | 2010-07-15 | Derivados de 4-(3-butinil) aminopirimidina como agentes pesticidas para uso agrícola y hortícola |
IL217078A IL217078A (en) | 2009-07-16 | 2011-12-19 | Pesticides for use in agriculture and horticulture containing derivatives of 4- (3-butinyl) aminopyrimidine |
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AU2010271805B2 (en) | 2014-11-13 |
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EP2455371A1 (en) | 2012-05-23 |
TW201114748A (en) | 2011-05-01 |
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TWI485138B (zh) | 2015-05-21 |
CA2765661A1 (en) | 2011-01-20 |
US8586505B2 (en) | 2013-11-19 |
PT2455371E (pt) | 2014-01-20 |
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US20120136150A1 (en) | 2012-05-31 |
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