KR880005096A - Aralkylaminopyrimidine derivatives, preparation methods thereof, and insecticides, acaricides and fungicides containing the derivatives as active ingredients - Google Patents

Abstract

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Description

Aralkylaminopyrimidine derivatives, preparation methods thereof, and insecticides, acaricides and fungicides containing the derivatives as active ingredients

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Claims (7)

Compound represented by the following structural formula (I) or its acid addition salt. Wherein R ₁ is a hydrogen atom or a lower alkyl group (substituted by an unsubstituted or halogen atom), and R ₂ and R ₃ are each independently a halogen atom or a lower alkyl group (substituted by an unsubstituted or halogen atom), lower An alkoxy group or lower alkyl thi group, R ₄ is a hydrogen atom, a halogen atom or a lower alkyl group, n is an integer of 1 or 2, Q is a phenyl group or a heterocyclic group, and these groups are each unsubstituted or halogen Substituted with at least one substituent selected from the group consisting of atoms, nitro groups, lower alkoxy groups, lower alkylthio groups, lower alkyl groups (substituted with unsubstituted or halogen atoms or substituted with unsubstituted or halogen atom substituted lower alkyl groups); , The heterocyclic group is oxo group, C _5-10 alkyl group, allyl group, geranyl group, farnesyl group, lower alkyl group substituted with 1-4 halogen atoms, C _3-6 cycloal A methyl group, an ethyl group substituted with a lower alkoxy group, a lower alkoxyalkyl group, a lower alkylthio group, a lower alkylsulfonyl group, or a phenoxy group (which may be substituted with one or two lower alkyl groups), glycidyl group, acetonyl group, phenoxy Dioxolanyl group, 2,2-diethoxyethyl group, 1-ethoxycarbonylethyl group, trimethylsilylmethyl group, 1-pyridylethyl group, benzylimino group (lower alkoxyimino group substituted with a methyl group (which may be substituted with a chlorine atom)) Or a lower alkyl group substituted with an optionally substituted lower alkyl group, and A is a lower alkylene group (unsubstituted or C _3-5 cycloalkyl group, lower alkynyl group, lower substituted with halogen atom) May be substituted with one or two substituents selected from the group consisting of an alkyl group, a lower alkoxy group or a lower alkylthio group), and B is a direct bond, oxygen atom, sulfur atom, straight chain or branched A chain lower alkylene group or a lower alkyleneoxy group. The compound according to claim 1, wherein the compound is a compound represented by the following structural formula (I ') or an acid addition salt thereof. Wherein A 'is a methylene group substituted with a methyl group, an ethyl group, an isopropyl group or a cyclopropyl group, and Q is a phenyl group substituted with a fluorine atom, a chlorine atom or a methyl group at the 4-position, 2-pyridyl group and 5-chloropyridine -3-yl group, 5-chloro-6-ethylpyrimidin-4-yl group, 5-chloro-6-methylpyrimidin-4-yl group or 6-chloro-5-methylpyrimidin-4-yl group, O- The Q 'group is substituted at the 3- or 4- position relative to A'. The compound according to claim 1, which is a compound represented by the following structural formula (I ″) or an acid addition salt thereof. Wherein R ₂ , R ₃ , R ₄ and n have the same meaning as described above, R ₅ is a lower alkyl group or a cycloalkyl group having 3 to 5 carbon atoms, and Q ″ is an alkyl group having 5 to 10 atoms , Allyl group, geranyl group, farnesyl group, lower alkyl group substituted with 1 to 4 halogen atoms, cycloalkylmethyl group having 3 to 6 carbon atoms, lower alkoxy group, lower alkoxyalkyl group, lower alkylthio group, lower alkylsulfo An ethyl group substituted with a phenoxy group which may be substituted with one or two lower alkyl groups, a glycidyl group, an acetonyl group, a dioxoranyl group substituted with a phenoxymethyl group which may be substituted with a chlorine atom, and a 2,2-diethoxyethyl group And a lower alkyl group substituted with a benzylimino group which may be substituted with a 1-ethoxycarbonylethyl group, trimethylsilylmethyl group, 1-pyridylethyl group, lower alkoxyimino group or lower alkyl group. Structural formula Wherein X is a group that can be removed. Structural formula (I) characterized by reacting with a compound of [Wherein R ₁ is a hydrogen atom or a lower alkyl group (unsubstituted or substituted by a halogen atom), and R ₂ and R ₃ are each independently a halogen atom or a lower alkyl group (unsubstituted or a halogen atom substituted) ), A lower alkoxy group or a lower alkyl thi group, R ₄ is a hydrogen atom, a halogen atom or a lower alkyl group, n is an integer of 1 or 2, Q is a phenyl group or a heterocyclic group, each of which is unsubstituted Or halogen atom, nitro group, lower alkoxy group, lower alkylthio group, lower alkyl group (substituted by unsubstituted or halogen atom or lower alkoxy group), phenyl group (substituted by unsubstituted or lower alkoxy group) and phenoxy group (beach Substituted with at least one substituent selected from the group consisting of a ring or a halogen atom, or an unsubstituted or halogen atom substituted lower alkyl group), and Interrogating cyclic group oxo group, a C _5-10 alkyl group, an allyl group, a galley group, Parr four groups, 1-4 halogen atoms substituted lower alkyl group, a C _3-6 cycloalkyl group, an ethyl group, a lower alkoxy group substituted by a lower Substituted by an alkoxyalkyl group, lower alkylthio group, lower alkylsulfonyl group, or phenoxy group (which may be substituted with one or two lower alkyl groups), glycidyl group, acetonyl group, phenoxymethyl group (which may be substituted with chlorine atoms) Substituted dioxoranyl group, 3,2-diethoxyethyl group, 1-ethoxycarbonylethyl group, trimethylsilylmethyl group, 1-pyridylethyl group, benzylimino group (which may be substituted with lower alkoxyimino group or lower alkyl group) Lower alkyl group, and A is selected from the group consisting of lower alkylene group (unsubstituted or C _3-5 cycloalkyl group, lower alkynyl group, lower alkyl group substituted by halogen atom, lower alkoxy group or lower alkylthio group) And B is a direct bond, an oxygen atom, a sulfur atom, a straight chain or branched chain lower alkylene group or a lower alkyleneoxy group) or a method for producing an acid addition salt thereof. . A pesticide comprising the following structural formula or its acid addition salt as an active ingredient. Wherein R ₁ is a hydrogen atom or a lower alkyl group (substituted by an unsubstituted or halogen atom), R ₂ and R ₃ are each independently a halogen atom or a lower alkyl group (substituted by an unsubstituted or halogen atom), A lower alkoxy group or a lower alkylthio group, R ₄ is a hydrogen atom, a halogen atom or a lower alkyl group, n is an integer of 1 or 2, Q is a phenyl group or a heterocyclic group, each of which is unsubstituted or Halogen atom, nitro group, lower alkoxy group, lower alkylthio group, lower alkyl group (unsubstituted or substituted by halogen atom or lower alkoxy group), phenyl group (substituted by unsubstituted or lower alkoxy group) and phenoxy group (unsubstituted or Substituted with a halogen atom, or substituted with at least one substituent selected from the group consisting of an unsubstituted or substituted halogen atom lower alkyl group, and Interrogating cyclic group oxo group, a C _5-10 alkyl group, an allyl group, a galley group, Parr four groups, 1-4 halogen atoms substituted lower alkyl group, a C _3-6 cycloalkyl group, an ethyl group, a lower alkoxy group substituted by a lower Substituted by an alkoxyalkyl group, lower alkylthio group, lower alkylsulfonyl group, or phenoxy group (which may be substituted with one or two lower alkyl groups), glycidyl group, acetonyl group, phenoxymethyl group (which may be substituted with chlorine atoms) Substituted dioxolanyl group, 2,2-diethoxyethyl group, 1-ethoxycarbonylethyl group, trimethylsilylmethyl group, 1-pyridylethyl group, benzylimino group (can be substituted with lower alkoxyimino group or lower alkyl group) may be) of which may be substituted with a substituted lower alkyl group, a is a lower alkylene group (which is unsubstituted or C _3-5 cycloalkyl group, a lower alkynyl group, a halogen atom substituted lower alkyl group, a lower alkoxy group or lower alkylthio group May be substituted with one or two substituents selected from the group), and, B is an alkylene group directly bonded to an oxygen atom, a sulfur atom, a straight chain or branched chain lower alkylene group or lower alkyl. An antimicrobial agent characterized by containing the compound of the following structural formula or its acid addition salt as an active ingredient. Wherein R ₁ is a hydrogen atom or a lower alkyl group (substituted by an unsubstituted or halogen atom), R ₂ and R ₃ are each independently a halogen atom or a lower alkyl group (substituted by an unsubstituted or halogen atom), A lower alkoxy group or a lower alkylthio group, R ₄ is a hydrogen atom, a halogen atom or a lower alkyl group, n is an integer of 1 or 2, Q is a phenyl group or a heterocyclic group, each of which is unsubstituted or Halogen atom, nitro group, lower alkoxy group, lower alkylthio group, lower alkyl group (unsubstituted or substituted by halogen atom or lower alkoxy group), phenyl group (substituted by unsubstituted or lower alkoxy group) and phenoxy group (unsubstituted or Substituted with a halogen atom, or substituted with at least one substituent selected from the group consisting of an unsubstituted or substituted halogen atom lower alkyl group, and Interrogating cyclic group oxo group, a C _5-10 alkyl group, an allyl group, a galley group, Parr four groups, 1-4 halogen atoms substituted lower alkyl group, a C _3-6 cycloalkyl group, an ethyl group, a lower alkoxy group substituted by a lower Substituted by an alkoxyalkyl group, lower alkylthio group, lower alkylsulfonyl group, or phenoxy group (which may be substituted with one or two lower alkyl groups), glycidyl group, acetonyl group, phenoxymethyl group (which may be substituted with chlorine atoms) Substituted dioxolanyl group, 2,2-diethoxyethyl group, 1-ethoxycarbonylethyl group, trimethylsilylmethyl group, 1-pyridylethyl group, benzylimino group (can be substituted with lower alkoxyimino group or lower alkyl group) may be) of which may be substituted with a substituted lower alkyl group, a is a lower alkylene group (which is unsubstituted or C _3-5 cycloalkyl group, a lower alkynyl group, a halogen atom substituted lower alkyl group, a lower alkoxy group or lower alkylthio group May be substituted with one or two substituents selected from the group), and, B is an alkylene group directly bonded to an oxygen atom, a sulfur atom, a straight chain or branched chain lower alkylene group or lower alkyl. A fungicide comprising a compound of the following structural formula or an acid addition salt thereof as an active ingredient. Wherein R ₁ is a hydrogen atom or a lower alkyl group (substituted by an unsubstituted or halogen atom), R ₂ and R ₃ are each independently a halogen atom or a lower alkyl group (substituted by an unsubstituted or halogen atom), A lower alkoxy group or a lower alkylthio group, R ₄ is a hydrogen atom, a halogen atom or a lower alkyl group, n is an integer of 1 or 2, Q is a phenyl group or a heterocyclic group, each of which is unsubstituted or Halogen atom, nitro group, lower alkoxy group, lower alkylthio group, lower alkyl group (unsubstituted or substituted by halogen atom or lower alkoxy group), phenyl group (substituted by unsubstituted or lower alkoxy group) and phenoxy group (unsubstituted or Substituted with a halogen atom, or substituted with at least one substituent selected from the group consisting of an unsubstituted or substituted halogen atom lower alkyl group, and Interrogating cyclic group oxo group, a C _5-10 alkyl group, an allyl group, a galley group, Parr four groups, 1-4 halogen atoms substituted lower alkyl group, a C _3-6 cycloalkyl group, an ethyl group, a lower alkoxy group substituted by a lower Substituted by an alkoxyalkyl group, lower alkylthio group, lower alkylsulfonyl group, or phenoxy group (which may be substituted with one or two lower alkyl groups), glycidyl group, acetonyl group, phenoxymethyl group (which may be substituted with chlorine atoms) Substituted dioxolanyl group, 2,2-diethoxyethyl group, 1-ethoxycarbonylethyl group, trimethylsilylmethyl group, 1-pyridylethyl group, benzylimino group (can be substituted with lower alkoxyimino group or lower alkyl group) may be) of which may be substituted with a substituted lower alkyl group, a is a lower alkylene group (which is unsubstituted or C _3-5 cycloalkyl group, a lower alkynyl group, a halogen atom substituted lower alkyl group, a lower alkoxy group or lower alkylthio group May be substituted with one or two substituents selected from the group), and, B is an alkylene group directly bonded to an oxygen atom, a sulfur atom, a straight chain or branched chain lower alkylene group or lower alkyl. ※ Note: The disclosure is based on the initial application.