KR830005137A - Method for preparing N-substituted-Δ ^ 1-tetrahydrophthalamide derivative - Google Patents

Abstract

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Description

Method for preparing N-substituted-Δ1-tetrahydrophthalamide derivative

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Claims (2)

A herbicide composition composed of 0.1 to 95% by weight of a novel N-substituted-Δ ¹ -tetrahydrophthalimide derivative represented by the following general formula (I) and 5 to 99.9% by weight of an adjuvant. In the above general formula R ₁ is hydrogen, halogen, lower alkyl, lower alkoxy or nitro, R ₂ is hydrogen, lower alkyl, halogen, R ₃ is hydrogen or lower alkyl, and Z contains hydroxy, alkoxy, alicyclicalkoxy, alkenyloxy or alkynyloxy, which may contain halogen, lower alkoxy, lower alkoxy, alkoxy or cyano groups as substituents, halogen, lower alkyl or lower alkoxy as substituents Phenoxy which may be used, alalkyloxy, alkylthio or amino which may contain halogen, lower alkyl or lower alkoxy as substituent, primary or secondary alkylamino which may contain halogen and hydroxy as substituent, as substituent Alkenyl amino, which may contain halogen, or morpholino or hydroxy metal salt, which may contain lower alkyl as a substituent, provided that Z is not hydroxy when R ₁ R ₂ and R ₃ are hydrogen. (a) Z is one of the groups defined in the following general formula (I) excluding hydroxy metal salts. (1) Δ ¹ -tetrahydro phthalic anhydride (wherein R ₃ is hydrogen or lower alkyl) represented by the following general formula (II) in the presence of a suitable solvent or in the absence of a solvent to the following general formula (III) React with the compound represented, wherein R ₁ is hydrogen, halogen, lower alkyl, lower alkoxy or nitro, R ₂ is hydrogen, halogen or lower alkyl and Z is as defined in the following general formula (I) , (2) under heating, a compound represented by the following general formula (VI), wherein R ₁ , R ₂ , R ₃ and Z are the same as defined in the general formulas (II) and (III) above; , (3) Under heating, a compound represented by the following general formula (X) wherein R ₁ , R ₂ , R ₃ and Z are the same as defined in general formula (VI), and R ₄ is methyl, ethyl, propyl or Lower alkyl, such as butyl), (4) The compound represented by the following general formula (IV) (wherein R ₁ , R ₂ and R ₃ are the same as defined in the general formula (I)) is represented by the following general formula (III ′) Z is the same as the definition of the following general formula (I) and consists of esterifying in the presence of an acid catalyst or (b) reacting a compound of formula (I) with an alkali metal, alkaline earth metal or manganese salt when Z is a hydroxy metal salt, or (c) Z contains chain alkoxy, allylcyclalkoxy, alkenyloxy or alkynyloxy, which may contain halogen, lower alkoxy, lower alkoxy alkoxy or cyano as a substituent, halogen, lower alkyl or lower alkoxy as substituent Phenoxy, which may contain halogen lower alkyl or lower alkoxy as substituent, alkylalkyl or amino, may be halogen or primary or secondary alkylamino which may contain hydroxy groups as substituent, halogen as substituent In the case of alkenyl amino or morpholino, which may contain lower alkyl as a substituent, the compound of the following general formula (IV) is reacted with a halogenating agent such as thionyl chloride or phosphooxyhalide, ) of a compound (wherein R _1, R ₂ and R ₃ are the following general formula (ⅰ) as defined in, and also Hal is represented by Uro or bromo) and then reacting the obtained compound with a compound represented by the following general formula (III) ', wherein Z is as defined in (c) above: A method for producing an N-substituted Δ ¹ -tetrahydrophthalimide derivative represented by (I). In the above general formula R ₁ is hydrogen, halogen, lower alkyl, lower alkoxy or nitro, R ₂ is hydrogen, lower alkyl, halogen, R ₃ is hydrogen or lower alkyl, and Z contains hydroxy, chain alkoxy, alicyclicalkoxy, alkenyloxy or alkynyloxy which may contain halogen, lower alkoxy, lower alkoxyalkoxy or cyano groups as substituents, halogen, lower alkyl or lower alkoxy as substituents Phenoxy which may be, Alalkyloxy alkylthio or amino which may contain halogen, lower alkyl or lower alkoxy as substituent, Primary or secondary alkyl amino which may contain halogen and hydroxy as substituent, Halogen as substituent Alkenyl amino, which may contain a morpholino or hydroxy metal salt, which may contain lower alkyl as a substituent, provided that when R ₁ , R ₂ and R ₃ are hydrogen, Z is not hydroxy. ※ Note: The disclosure is based on the initial application.