WO2012096061A1 - Dérivé de pyrimidine en tant qu'agent de lutte contre les organismes nuisibles à usage agricole et horticole - Google Patents

Dérivé de pyrimidine en tant qu'agent de lutte contre les organismes nuisibles à usage agricole et horticole Download PDF

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WO2012096061A1
WO2012096061A1 PCT/JP2011/077128 JP2011077128W WO2012096061A1 WO 2012096061 A1 WO2012096061 A1 WO 2012096061A1 JP 2011077128 W JP2011077128 W JP 2011077128W WO 2012096061 A1 WO2012096061 A1 WO 2012096061A1
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carbon atoms
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Japanese (ja)
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誠 番場
智子 村木
新一郎 ▲高▼島
陽子 小橋
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株式会社エス・ディー・エス バイオテック
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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
    • 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

Definitions

  • the present invention relates to a novel pyrimidine derivative that is useful as a pest control agent, particularly an agricultural and horticultural pest control agent.
  • the pyrimidine derivative of the present invention is a novel compound and is not known to have agricultural and horticultural pest control activities.
  • 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 pyrimidine 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 pyrimidine 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).
  • a chain-like or branched alkyl group
  • the second invention is a method for producing a pyrimidine derivative represented by the formula [I].
  • the third invention is a pest control agent comprising one or more pyrimidine derivatives represented by the formula [I] as an active ingredient.
  • novel pyrimidine derivative of the present invention represented by the formula [I] has an excellent control effect against pests, particularly agricultural and horticultural pests.
  • the pyrimidine derivative in the present invention includes, in addition to the pyrimidine derivative represented by the formula [I], salts (sodium salt, potassium salt, magnesium salt, calcium salt, aluminum salt, etc.), hydrates, and solvates of the derivative. And polymorphic substances are also included. 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 any ratio are also represented by the compound of the present invention (pyrimidine derivative represented by the formula [I]). Included in the range.
  • 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 ).
  • 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,
  • examples of the substituent 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 -SiR 5 R
  • 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, and 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.
  • haloalkyl group in R 2 a monofluoromethyl group, a difluoromethyl group, and a trifluoromethyl group are preferable, and as the haloalkoxy group, a monofluoromethoxy group, a difluoromethoxy group, and a trifluoromethoxy group are preferable.
  • halogen atom for 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.
  • 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, methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, or isopropylsulfonyl 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 Examples thereof include an ethyl group, a trimethylsiloxypropyl group, a triethylsiloxymethyl group, and a t-butyldimethylsiloxy group.
  • 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.
  • 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 from room temperature to the boiling point of the solvent used, and room temperature is preferred.
  • 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, and R 2 and R 3 are as defined above.
  • Compound [II] used in the present synthesis method can be produced, for example, by the method shown in the following formula according to the method described in WO2004 / 65380.
  • the 3-butynylamine derivative [III] used in this synthesis can be a commercially available product. If necessary, it can be produced, for example, according to the method described below. However, the method described below does not limit the scope of the present invention. (Synthesis method 1)
  • 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.
  • a product [VIII] is synthesized from a substituted butynyl alcohol [X] and a phthalimide [XI] by Mitsunobu reaction, and the product [VIII] is subjected to Sonogashira reaction and deprotection in the same manner as in Synthesis Method 1. Can produce the 3-butynylamine derivative [III].
  • 3-Butynylamine derivative [III] can be produced from 4-pentylamide [XX] by Hofmann rearrangement.
  • 3-Butynylamine derivative [III] can be produced from acyl azide [XXI] by Curtius transfer.
  • the term “pest” here includes all pathogenic fungi for agricultural and horticultural plants, all pests and mites for agricultural and horticultural plants.
  • pathogenic fungi for agricultural and horticultural plants examples include algae fungi (Omycetes), ascomycetes (Ascomycetes), incomplete fungi (Deuteromycetes), basidiomycetes (Basidiomycetes), and bacteria
  • algae fungi Omycetes
  • ascomycetes Ascomycetes
  • Deuteromycetes Deuteromycetes
  • Basidiomycetes basidiomycetes
  • bacteria The pyrimidine derivatives used in the present invention can control plant diseases caused by these pathogenic fungi.
  • specific names of bacteria are given as examples, but are not necessarily limited thereto.
  • Examples of agricultural and horticultural pathogens include, for example, rice blast (Pyricularia oryzae), rice sesame leaf blight (Cochliobolus miyabeanus), rice coat blight (Rhizoctonia solani), rice idiot (Gibberella fujikuroi), barley powdery mildew (Erysiphe graminis) tritici), wheat powdery mildew (Erysiphe graminis f.sp.
  • Potato gray mold (Botrytis cinerea), azuki bean mildew (Erisiphe pisi), azuki bean brown spot (Cercospora canescens), azuki bean sclerotia (Sclerotinia sclerotiorum), azuki bean anthracnose (Colletotri) chum phaseolorum), common bean brown spot (Cercospora canescens), common bean sclerotia (Sclerotinia sclerotiorum), common bean anthracnose (Colletotrichum lindemuthiamum), common bean gray mold (Botrytis cinerea), soybean anthracnose (Colletotrichum trunc) (Cercospora kikuchii), soybean rust (Phakopsora pachyrhizi), konjac anthracnose (Gloeosporium conjac), konjac brown spot (Septoria perillae), tea anthracnose (Colletotrichum
  • Campestris radish soft rot (Erwinia carotovora), Komatsuna Gonorrhea (Colletotrichum higginsianum), Sclerotinia sclerotiorum, Chinese cabbage black spot (Alternaria brassicae, Alternaria brassicicola), Pumpkin black spot (Alternaria cucumerina), Pumpkin gray mold (Botrytis cinerea), Pumpkin mildew (Pseudoperonospora cubensis), cucumber powdery mildew (Sphaerotheca fuliginea), cucumber plague (Phytophthora melonis), cucumber brown spot (Corynespora cassiicola), cucumber sclerotia (Sclerotinia sclerotiorum), cucumber black cucumber (Alternaria black cucumber) Diseases (Colletotrichum lagenarium), cucumber vines (Fusarium oxysporum f.sp.
  • Examples of pests and ticks on agricultural and horticultural plants include the order of Hemiptera, Thysanoptera, Thysanoptera, Acari, etc.
  • the pyrimidine derivatives used in the present invention are: Plant damage caused by these pests and mites can be controlled. Next, specific pests, ticks and the like are given as examples, but not necessarily limited thereto.
  • Pests, mites, etc. include, for example, Plutella xylostella, Agrotis ipsilon, Abratis segetum, Helicoverpa armigera, Tobacco moth (Helicoverpa assulta), Cotton ball worm (Helicoverpa zea), Tobacco Bad Worm (Heliothis virescens), Mamestra brassicae, Naranga aenescens, Tamanaginawaba (Plusia nigrisigna), Ayayoto (Pseudaletia separata), Spodoptera exigua, Spodoptera exigua, Spodoptera exigua, Spodoptera exigua , Fall army worm (Spodoptera frugiperda), Southern army worm (Spodoptera eridania), Tobacco horn worm (Manduca sexta), Grapeberry moss (Endopiza viteana), Ginmon leaf moth (Lyonetia pr
  • Epilachna varivestis Melanonotus tamsuyensis, tobacco beetle (Lasioderma serricorne), Epuraea domina, Henosepilachna vigintioctopunctata, Tribolium castaneum, Anoplophora malasiaca, Monochamus alternatus, Azuki beetle (Callosobruchus chinensis), Urihamushi (Aulacophora femoralis), Oedma orylae Cotton weevil (Anthonomus grandis), Green weevil (Ethinocnemus squameus), Alfalfa weevil (Hypera postica), Green weevil (Lissorhoptrus oryzophilus), Kirch weevil (Sitophilus zeamais), Shivao weevil (tus vest) Insect insects such as Sitophilus granarius, Southern corn rootworm (Diabrotica undecimpunctata), Western
  • Thrips palaids such as Scirtothrips dorsalis, Thrips palmi, Thrips tabaci, Dacus dorsalis, Dacus cucurbitae, H ), Eggplant leaf fly (Liriomyza bryoniae), bean leaf fly (Liriomyza trifolii), fly fly (Hylemya platura), apple magot (Rhagoletis pomonella), fly fly (Mayetiola destructor), house fly (Musca domestica), sand fly cali (S Melophagus ovinus), Hypoderma lineatum, Bullflies (Hypoderma bovis), sheep flies (Oestrus ovis), tsetse flies (Glossina palpalis, Glossina morsitans), yellow-bellied (Prosimulium yezoensis), bullfly (Tabanusmatous) Leptocono ps nipponensis), Culex pip
  • yezoensis mackerel grasshopper
  • mackerel grasshopper mitocerca g
  • butterfly pests such as regaria, termites (Coptotermes formosanus), termites (Reticulitermes speratus), termites pests such as the Odontotermes formosanus, cat fleas (Ctenocephalidae felis), human fleas (Pulex irritans)
  • Flea insects such as Xenopsylla cheopis, chick larvae (Menacanthus stramineus), larvae insects such as bovic larvae (Bovicola bovis), cattle lice (Haematopinus eurysternus), pork lice (Haematopinus suis), cow leopard (Lino capsicum) Lice etc.).
  • spider mites Panonychus citri
  • apple spider mite Panonychus ulmi
  • Kanzawa spider mite Tetranychus kanzawai
  • spider mite Tetranychus urticae
  • Mite Eriophyes chibaensis
  • Tulip mite Aceria tulipae
  • Mite Polyphaotarsonemus latus
  • Mite Tineotarsonemus pallidus
  • Mite Teyrophagus putrescentiae
  • Spider mites such as honeybee mite (Varroa jacobsoni), ticks (Boophilus microplus), ticks (Haemaphysalis longicornis), cucumber mites (Psoroptes ovis), and mite (Sarcoptes scabiei) Etc.
  • crustaceans such as Armadillidium vulgare, Platylenchus penetrans, Prathylenchus vulnus, potato cyst nematode (Globodera rostochiensis), soybean cyst nematode (Heterodera glycerine) hapla), nematodes such as Meloidogyne incognita, Bursaphelenchus lignicolus, Ponacea canaliculata, slugs (Incilaria bilineata), Acusta despecta siebiana (Acusta despecta sieb Mollusks and the like. [Pesticides]
  • the agricultural and horticultural pest control agent of the present invention has particularly remarkable bactericidal and insecticidal effects, 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.
  • Surfactants and salts thereof higher fatty acid salts, polycarboxylic acid type surfactants and salts thereof, and the like.
  • the salts in the above surfactants include salts of sodium, potassium, magnesium, calcium, ammonium, ethanolamine, diethanolamine, triethanolamine, various amines and the like.
  • Examples of 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 above-mentioned preparation contains 1 to 95% by weight, preferably 1 to 50% by weight, of at least one compound [I] of the present invention.
  • 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 active compound of the present invention can be used alone or as a preparation thereof, but it can be used as a bactericidal / fungicidal agent, bactericidal agent, acaricide, nematicide, insecticide, biological pesticide, herbicide, plant hormone agent , Plant growth regulators, synergists, attractants, repellents, pigments, fertilizers, etc., or mixtures of one or more selected from those active ingredients to control pests It can also be used as an 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.
  • bactericides include SH synthesis inhibitory active compounds, nucleic acid biosynthesis inhibitory active compounds, spindle formation inhibitory active compounds, benzanilide compounds, strobilurin compounds, other electron transport inhibitory compounds, amino acid biosynthesis inhibitory active compounds, Sterol biosynthesis-inhibiting active compound, cell wall synthesis-inhibiting active compound, lipid biosynthesis-inhibiting active compound, glucan biosynthesis-inhibiting active compound, melanin biosynthesis-inhibiting active compound, host resistance-inducing compound, compounds having other or unclear effects, etc. Can be mentioned. Specific examples of each will be described below.
  • Nucleic acid biosynthesis inhibiting active compounds metalaxyl, metalaxyl-M, oxadixyl, bupirimate, hymexazol, oxolinic acid, etc.
  • Benzanilide compounds furametpyr, penthiopyrad, thifluzamide, boscalid, oxycarboxin, carboxyxin, fluopyram, flutolanil, mepronil ),etc.
  • Stravylline compounds azoxystrobin, picoxystrobin, kresoximmethyl, trifloxystrobin, orysastrobin, metinominostrobin, pyraclostrobin ), Famoxadone, fenamidone, pyribencarb, dimoxystrobin, pyrametostrobin, pyraoxystrobin, etc.
  • Amino acid biosynthesis inhibitory active compounds cyprodinil, mepanipyrim, pyrimethanil, blastcidin-S, streptomycin, kasugamycin, etc.
  • Sterol biosynthesis inhibiting active compounds azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, epoxiconazole, fenbuconazole, Fluconazole, hexaconazole, imibenconazole, metoconazole, microbutanil, penconazole, propiconazole, simeconazole, teconazole , Triadimefon, triadimenol, triticonazole, imazalil, triflumizole, pefurazoate ), Prochloraz, fenarimol, fenhexamid, fenpropimorph, piperalin, spiroxamine, and the like.
  • Cell wall synthesis inhibitory active compounds iprodione, myclozolin, procymidone, vinclozolin, quinoxyfen, fludioxonil, etc.
  • Lipid biosynthesis inhibiting active compounds iprobenfos, isoprothiolane, quintozene, propamocarb, prothicarb, dimethomorph, iprovalicarb, benchavalicarb, benthiavali carb Mandipropamid, etc.
  • Glucan biosynthesis inhibitory active compounds validamycin, polyoxin B, etc.
  • Melanin biosynthesis inhibiting active compounds pyroquion, tricyclazole, carpropamid, diclocymet, fenoxanil, etc.
  • Host resistance-inducing compounds acibenzolar-S-methyl, probenazole, isothianil, laminarin, etc.
  • insecticides / acaricides / nematicides include acetylcholinesterase inhibitor compounds, GABA-dependent chloride ion channel inhibitor compounds, sodium ion channel inhibitor compounds, nicotinic acetylcholine receptor inhibitor compounds, chloride channel inhibitor compounds Compound, pseudo-juvenile hormone compound, non-selective inhibitor compound, selective feeding inhibitor compound, tick growth inhibitor compound, Bt agent, ATP synthesis inhibitor compound, oxidative phosphorylation uncoupling compound, nicotinic acetylcholine receptor channel inhibitor compound , Chitin biosynthesis inhibiting compounds, molting / transformation disrupting compounds, octopamine antagonist compounds, electron transport system inhibiting compounds, voltage-gated sodium channel inhibiting compounds, lipid synthesis inhibiting compounds, ryanodine receptor inhibiting compounds, other compounds with unclear effects , Etc. It can be. Specific examples of each will be described below.
  • Acetylcholinesterase inhibitors aldicarb, benfuracarb, carbaryl, carbofuran, carbosulfan, fenobucarb, methiocarb, methiocarb ), Thiodicarb, etc.
  • GABA-dependent chloride ion channel inhibitory compounds endosulfan, ethiprole, fipronil, acetoprole, etc.
  • Sodium ion channel inhibiting compounds bifenthrin, cypermethrin, esfenvalerate, etofenprox, lambda-cyhalothrin, tefluthrin, DDT (DDT), Methoxychlor, etc.
  • Nicotinic acetylcholine receptor inhibitory compounds acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, thiamethoxam, etc.
  • Chloride channel inhibitory compounds abamectin, emamectin benzoate, milbemectin, lepimectin, etc.
  • Pseudo-juvenile hormone compounds kinoprene, methoprene, phenoxycarb, pyriproxyfen, etc.
  • Non-selective inhibiting compounds methyl bromide, chloropicrin, etc.
  • Selective feeding inhibitory compounds pymetrozine, flonicamid, etc.
  • Tick growth inhibitory compounds clofentezine, hexythiazox, etoxazole, etc.
  • Bt agent Bacillus thuringiensis, etc.
  • ATP synthesis inhibiting compounds diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon, etc.
  • Oxidative phosphorylation uncoupling compound chlorfenapyr, etc.
  • Nicotinic acetylcholine receptor channel inhibitory compounds bensultap, cartap, thiocyclam, etc.
  • Chitin biosynthesis inhibiting compounds Chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflubenzuron (triflubenzuron) triflumuron), buprofezin, bistrifluron, etc.
  • Molting / transformation disrupting compounds cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, noviflumuron, etc.
  • Octopamine antagonist compounds amitraz, hydramethylnon, acequinocyl, etc.
  • Electron transport system inhibitor compounds fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone, etc.
  • Aluminum phosphate (Aluminium phosphide), etc.
  • Voltage-gated sodium channel inhibitor compounds indoxacarb, metaflumizone, spirodiclofen, etc.
  • Lipid synthesis inhibiting compounds spiromesifen, spirotetramat, etc.
  • Ryanodine receptor inhibitor compounds chlorantranilprole, flubendiamide, cyantranilprol, etc.
  • herbicides include the following compounds.
  • benzobicyclon bensulfuron-methyl, azimsulfuron, cinosulfuron, cyclosulfamuron sulf, pyrazosulfuron-ethyl, imazosulfuron (imazosulfuron) ), Indanofan, cyhalofop-butyl, thenylchlor, esprocarb, etobenzanid, cafenstrole, clomeprop, methatron, dimetametryn Bifenox, pyributicarb, pyriminobac-methyl, pretilachlor, bromobutideide, benzofenap, topramezone, bench ocar (benthiocarb), pentoxazone, benfuresate, mefenacet, fenoxaprop-P-ethyl, phenmedipham, diclofop-methyl , Desmedipham, ethofumesate, isoprotur
  • biological pesticides include the following compounds.
  • NDV Nuclear polyhedrosis virus
  • GV granular disease virus
  • CPV cytoplasmic polyhedrosis virus
  • Steinernema carpocapsae Steinernema glaseri, Monocrosporium phymatophagum, Steinernema kushidai, Steinernema kushidai ,etc.
  • Agrobacterium radiobacter Bacillus subtilis, Erwinia carotovora, Pseudomonas fluorescens, Talaromyces flavus, Talaromyces flavus, Talaromyces flavus (Trichoderma atroviride), etc.
  • Onsatsume wasp (Encarsia formosa), Sakutaku bee (Eretmocerus eremicus), Scarlet wasp (Eretmocerus eremicus), Collared wasp (Aphidius colemani), Aphidoletes aphidimyaly ), Dacnusa sibirica, Phytoseiulus persimilis, Amblyseius cucumeris, Amblyseius californicus, Orius strigicollis, and so on.
  • Examples of pheromone agents include Codrelua ((E, E) -8,10-Dodecadien-1-ol), Dout Armilla B ((Z) -9-Tetradecen-1-ol), Tetradodecenyl acetate ((Z) -11-Tetradecenyl acetate), pyrimalua (14-Methyl-1-octadecene), peach flua ((Z) -13-Eicosen-10-one), and the like.
  • Examples of natural fungicides and natural insecticides are: Machine oils, Methylphenyl acetate, ⁇ -Pinene, Protein hydrolysate, (Z) -1-Tetradecen-1-ol, Turpentine , Etc.
  • Example 1 [Production Example]
  • Step C 4- (4- ⁇ 2-trifluoromethylphenyl ⁇ -3-butynylamino) -6-chloro-pyrimidine-5-carbonitrile
  • the pesticidal composition of the present invention When used, it is formulated into powders, granules, fine granules, tablets, liquids, emulsions, wettable powders, flowables, aerosols and the like that are widely used in agricultural chemical formulations. These can be used in a normal application method such as seed treatment, foliage spraying, soil application or water surface application.
  • the application rate of the pest control composition according to the present invention varies depending on the target disease, the occurrence tendency of pests, the degree of damage, environmental conditions, the formulation type to be used, etc., but the general application rate is 0.1 g per 10 ares. ⁇ 1kg.
  • diluting liquids, emulsions, wettable powders, flowables, etc. with water use them at a dilution concentration in the range of 1 to 10,000 ppm.
  • the pest control composition according to the present invention is sterilized with fungicides, fungicides, bactericides, acaricides, nematicides, insecticides, biopesticides, herbicides, plant hormones, plant growth regulators, synergists.
  • Pesticides, repellents, pigments, fertilizers, etc., or a combination of one or more selected from those active ingredients in combination with a pest control compound Fluctuates depending on the type of disease, target disease, incidence, degree of damage, environmental conditions, formulation type used
  • the weight of one or more pyrimidine derivatives which are the compound group described in [Table 1] and the weight of one or more existing agricultural and horticultural fungicidal and / or insecticidal compounds listed above The mixing ratio is a ratio of 1: 0.1 to 1: 100,000, and a typical application rate is 0.1 g to 1 kg per 10 ares.
  • liquids, emulsions, wettable powders, flowables and the like are diluted with water, they are used at a dilution concentration ranging from 1 to 10,000 ppm.
  • the active ingredient can be used in an appropriate dosage form depending on the purpose.
  • the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, a surfactant or the like is added thereto, and it can be used in the form of a powder, wettable powder, emulsion, granule or the like.
  • suitable carriers include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea, and liquid carriers such as isopropyl alcohol, xylene, cyclohexanone, and methylnaphthalene. It is done.
  • solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea
  • liquid carriers such as isopropyl alcohol, xylene, cyclohexanone, and methylnaphthalene. It is done.
  • surfactant and dispersant examples include dinaphthyl methane sulfonate, alcohol sulfate ester salt, alkylaryl sulfonate, lignin sulfonate, Examples include polyoxyethylene glycol ether, polyoxyethylene alkyl aryl ether, polyoxyethylene sorbitan monoalkylate and the like.
  • auxiliary agent examples include carboxymethyl cellulose.
  • agricultural and horticultural pest control composition of the present invention may be used in combination with insecticides, other fungicides, herbicides, plant growth regulators, fertilizers and the like as necessary.
  • 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 Industry Co., Ltd.). 10 parts of an activator (trade name) was added and mixed by stirring to obtain a 10% emulsion.
  • Formulation example 2 wettable powder 10 parts of the compound of the present invention was added to 2 parts of sodium lauryl sulfate, 4 parts of sodium lignin sulfonate, 20 parts of white carbon and 64 parts of clay, and mixed by stirring with a juice mixer. % Wettable powder was obtained.
  • Formulation Example 3 Granules To 5 parts of the compound of the present invention, 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 present compound is dissolved in 2 parts of soybean oil, 5 parts of white carbon, 0.3 part of isopropyl 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 phosphate
  • Formulation Example 5 Flowable agent 20 parts of water containing 20 parts of the present compound and 2 parts, 1 part and 0.2 parts 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 To 20 parts of the present compound, 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 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]
  • Test Example 1 Control effect against tomato plague
  • Potted tomato seedlings (variety: sugar lamp, 4.5 leaf stage), a chemical solution prepared by adjusting 10% wettable powder of the compound group (pyrimidine derivative) shown in [Table 1] to 50 ppm (hereinafter referred to as a reagent solution) Sprayed with 15 ml per pot using a spray gun, sprayed with a zoospore suspension (Phytophthora infestans) zoospore suspension (sporemide concentration of 1.0 ⁇ 10 4 cells / 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 diseased area ratio of each leaf was examined, and the control value was calculated using the following formula.
  • 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. A: 100% ⁇ control value ⁇ 98% B: 98%> control value ⁇ 60% C: 60%> control value ⁇ 20% D: 20%> control value ⁇ 0%
  • a potted cucumber seedling (variety: Sagamihanjiro, 2.5 leaf stage) is a chemical solution (hereinafter referred to as a reagent solution) prepared by adjusting 10% wettable powder of the compound group (pyrimidine derivative) shown in [Table 1] to 50 ppm. ) was sprayed at 15 ml per pot using a spray gun, and one day later, a conidia suspension of cucumber downy mildew (Pseudoperonospora cubensis) (conidia concentration of 1.0 ⁇ 10 4 cells / ml) was spray-inoculated. After inoculation, the sample was placed in a humid chamber condition at 21 ° C. for 1 day and further placed in a greenhouse for 3 days to cause sufficient disease, and then the diseased area of each leaf was compared with the untreated group. In the same manner as above, the control effect was determined. The results are shown in Table 4.
  • a potted cucumber seedling (variety: Sagamihanjiro, 2-leaf stage) with a chemical solution (hereinafter referred to as a reagent solution) prepared by adjusting 10% wettable powder of the compound group (pyrimidine derivative) shown in [Table 1] to 50 ppm.
  • a spray gun was used to spray 15 ml per pot, and one day later, a conidial suspension of cucumber powdery mildew (Sphaerotheca fuliginea) (conidial concentration 1.0 ⁇ 10 5 cells / ml) 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.
  • the compound was diluted with a 10% wettable powder of the compound group (pyrimidine derivative) shown in [Table 1] to 50 ppm. Cucumber leaf pieces having a diameter of 3 cm were placed in a plastic cup filled with 0.5% soft agar, and 5 female Aphis gossypi females were released. After standing overnight, the number of larvae larvae was counted, and 0.4 ml of the adjusted medicinal solution was sprayed, and the number of dead insects after 2 days was counted to calculate the mortality. The calculated death rate was applied to the following criteria to determine the insecticidal effect. The results are shown in Table 6. A: 100% ⁇ mortality ⁇ 98% B: 98%>mortality> 60% C: 60%> mortality ⁇ 20% D: 20%> death rate ⁇ 0%
  • Test Example 5 The effect of killing insects against adult female spider mite
  • the compound was diluted with a 10% wettable powder of the compound group (pyrimidine derivative) shown in [Table 1] so that the compound became 100 ppm.
  • a 3 cm diameter kidney bean leaf was placed on a plastic cup filled with 0.5% soft agar, and 10 female adults of Tetanychus urticae were released.
  • the adjusted chemical solution was sprayed at 0.4 ml each, and the number of dead insects after 2 days was counted to calculate the mortality rate. Determination was made according to the same criteria as in Test Example 4 from the calculated mortality rate. The results are shown in Table 7.
  • the compound was diluted with a 10% wettable powder of the compound group (pyrimidine derivative) shown in [Table 1] so that the compound became 100 ppm.
  • a 3 cm diameter kidney bean leaf was placed on a plastic cup filled with 0.5% soft agar, and 10 female adults of Tetanychus urticae were released. After removing the female larvae that were allowed to stand overnight at room temperature for egg laying and releasing, 0.4 ml each of the prepared medicinal solution was sprayed, and the number of dead insects after 6 days was counted to calculate the mortality. Determination was made according to the same criteria as in Test Example 4 from the calculated mortality rate. The results are shown in Table 8.
  • the compound was diluted with a 10% wettable powder of the compound group (pyrimidine derivative) shown in [Table 1] so that the compound became 100 ppm. 3 cm diameter Chinese cabbage leaf pieces were immersed in each chemical solution, then air-dried and housed in a plastic petri dish, and 10 third-instar larvae of Spodoptera litra were released. The mortality was calculated by counting the number of dead insects 2 days after treatment. Determination was made according to the same criteria as in Test Example 4 from the calculated mortality rate. The results are shown in Table 9.
  • the expected effect of the combination of individual active compounds was determined by the Colby calculation formula.
  • the experimental value is larger than the calculated value E, the effect of the combination shows a synergistic effect.
  • Colby's formula (Colby, SR, “Calculating synergistic and antagonistic responses of herbicide combinations”, Weeds 15, 20-22 (1967)) Is shown below.
  • Colby's formula: E A + B-(A x B / 100)
  • E Expected effect (control value) over an untreated control using a mixture of active compound X at concentration x and active compound Y at concentration y
  • B Effect of the active compound Y having a concentration y on the untreated control (control value)
  • a bactericidal active compound (hereinafter, the compound name is indicated by a corresponding alphabet) was diluted with water so as to be an active ingredient having a predetermined concentration, and sprayed with 15 ml per pot using a spray gun. After air-drying, a conidial suspension of cucumber downy mildew (Pseudoperonospora cubensis) was spray-inoculated and immediately maintained at 21 ° C. and 100% humidity for 1 day.
  • the compound group (pyrimidine derivative) shown in [Table 1] and the existing insecticidal active compounds shown in [Table 14] are mixed with water so as to become active ingredients at a predetermined concentration. Diluted with Cucumber leaf pieces having a diameter of 3 cm were placed on a plastic cup filled with 0.5% soft agar, and 5 female Aphis Gossypi adults were released. After standing overnight, the number of larvae larvae was counted, and 0.4 ml of the adjusted chemical solution was sprayed to count the number of dead worms two days later. The death rate was calculated according to Moreover, the effect expected by the combination of the individual active compounds was determined by the Colby formula. Table 14 shows the effects of the individual active compounds, and Table 15 shows the effects of the mixture of the compound of the present invention and the existing insecticidal active compounds.
  • the agricultural and horticultural pest control composition containing one or more of the pyrimidine derivatives of the present invention as an active ingredient is particularly low in pests such as pathogenic bacteria, insects and mites that affect agricultural and horticultural plants. It exhibits excellent control effects and is extremely useful as a new agricultural chemical because of its extremely high safety against useful crops.
  • the experimental value of the mixture of the pyrimidine derivative of the present invention and the existing bactericidal active compound, and the mixture of the pyrimidine derivative of the present invention and the existing insecticidal active compound are both greater than the calculated value E based on Colby's calculation formula. Since the effect of the combination has a synergistic effect, it is extremely useful as a mixture.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
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  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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Abstract

Le nouveau dérivé de pyrimidine de l'invention, se révèle utile en tant qu'agent de lutte contre les organismes nuisibles. (Dans la formule (1): R1 représente un cycle mono- ou bi-cyclique qui comprend selon les cas 0 à 3 hétéroatomes, choisis dans un groupe constitué, par exemple, de phényle, de benzyle, d'oxazolyle, ou similaire; R2 représente, par exemple, un atome d'hydrogène, un hydroxyalkyle, un alcoxyalkyle, un halogénoalcoxyalkyle, un phényle, un hétéroaryle, un halogène, un cyano, un halogénoalkyle, ou un halogénoalcoxy; R3 représente, par exemple, (1) un atome d'hydrogène, (2) un atome d'halogène, (3) un alkyle en C1-6 substitué par un groupe hydroxy, un atome d'halogène, ou un acyloxy représentés par (groupe hydrocarboné aliphatique en C1-8 à chaîne droite ou ramifiée)-CO-O-, (4) un alkyle en C1-6 non-substitué; ou (5) un halogénoalkyle.
PCT/JP2011/077128 2011-01-14 2011-11-25 Dérivé de pyrimidine en tant qu'agent de lutte contre les organismes nuisibles à usage agricole et horticole WO2012096061A1 (fr)

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EP2664238A4 (fr) * 2011-01-14 2014-09-17 Sds Biotech Corp Composition de lutte contre les organismes nuisibles contenant un dérivé de 4-(3-butynyl)aminopyrimidine pour utilisation agricole ou horticole

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CN108178748A (zh) * 2018-01-19 2018-06-19 和记黄埔医药（上海）有限公司 4,6-二氯嘧啶-5-甲腈的合成方法
CN108178748B (zh) * 2018-01-19 2021-04-06 和记黄埔医药（上海）有限公司 4,6-二氯嘧啶-5-甲腈的合成方法

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