KR900003153A - Novel substituted 2-aryloxy and 2-arylthiotriazine derivatives, methods for their preparation and their use as herbicides and plant growth regulators - Google Patents

Abstract

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Novel substituted 2-aryloxy- and 2-arylthiotriazine derivatives, methods for their preparation and their use as herbicides and plant growth regulators

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Claims (4)

2-aryloxy- and 2-arylthiotriazine derivatives of the general formula (I) and salts of these compounds. Here, A is group A-1 or A-2 of the following general formula, R ¹ is —COOR ⁴ or —CONR ⁵ R ⁶ and R ² , R ³ , R ⁷ and R ⁸ are the same or different from each other and are hydrogen or C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl groups, wherein each one or more of the same or different halogen, hydroxy, halo-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, halo-C ₁ -C ₄ alkoxy, C Optionally substituted by _1- C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl), halogen C ₁ -C ₄ alkoxy, halo-C ₁ -C ₄ alkoxy, Group R ¹¹ -O-CO, carbamoyl group R ⁹ R ¹⁰ -CO-, amino group R ⁹ R ¹⁰ N-, cyano, nitro, group R ¹¹ -S (O) n-, acyl group R ¹¹ -CO- , May be optionally substituted by groups R ″ -O-CO- (CH ₂ ) _7- , phenyl (C ₁ -C ₄ ) alkyl, halogen or nitro group), phenoxy (C ₁ -C ₄ alkyl, halogen or nitro may optionally be substituted by a) only provided that, when A = A-2, R ² is halogen, C ₁ -C ₄ alkoxy or halo -C ₁ -C ₄ al On the assumption that it is not a group and, R ⁴ is disturbed by one or more oxygen or sulfur atom, hydrogen, C ₁ -C ₁₂ alkyl or C ₂ -C ₁₂ alkyl (wherein each of the groups hydroxy, halogen, C ₁ -C ₃ alkoxy, C ₁ -C ₄ alkylthio, C ₃ -C ₆ cycloalkyl, benzyl, furyl, tetrafuryl, phenyl, halophenyl, C ₁ -C ₄ alkylphenyl, C ₁ -C ₄ alkoxyphenyl, nitro phenyl, cyano, carboxy, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylamino or di -C ₁ may be optionally substituted by -C ₄ alkylamino group), C ₃ -C ₈ alkenyl, or C ₃ -C ₈ alkynyl group, each of which may be optionally substituted by C ₁ -C ₄ alkoxy phenyl or halogen C ₃ -C ₆ cycloalkyl di-C ₁ -C ₄ which may be optionally substituted by methyl group An alkylmethyleneamino group or an alkali metal alkaline earth metal, manganese, copper, iron, zinc and a cation from the group consisting of organic ammonium compounds, R ⁵ And R ⁶ is the same or different and is C ₁ -C ₄ alkyl or C ₁ -C ₃ alkylthio which may be optionally substituted by hydrogen or one or more hydroxy, halogen, C ₁ -C ₃ -alkoxy or C ₃ -C ₈ alkenyl or C ₃ -C ₈ alkynyl group, when R ⁵ is hydrogen, R ⁶ also amino, dimethylamino, acetamido amino or anilino, or R ⁵ and R ⁶ together with the carbon atom to which they are attached Form a 3 to 7 membered saturated heterocyclic ring, wherein the carbon atoms may be optionally substituted by oxygen or sulfur atoms, and R ⁹ , R ¹⁰ and R ¹¹ are the same or different and are hydrogen or each C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, which may be optionally substituted by one or more identical or different halogen, hydroxy or C ₁ -C ₄ alkoxy groups or R ⁹ and R ¹⁰ is the same or different C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl, which may be hydrogen or each may be optionally substituted by one or more identical or different halogen, hydroxy or C ₁ -C ₄ alkoxy groups Or R ⁹ and R ¹⁰ together with the carbon atom to which they are attached form a pilolidino, pyreridino or morpholino group or R ¹¹ is also one or more identical or different halogen, hydroxy or C ₁ -C ₄ alkoxy groups Phenyl-C ₁ -C ₄ alkyl which may be optionally substituted by phenyl or phenyl optionally substituted by one or more identical or different halogen, nitro or C ₁ -C ₄ alkyl and X is oxygen or sulfur atom and n Is 0,1 or 2 and m is 0 or 1. The compound of claim 1, wherein R ¹ is —COOR ⁴ and R ² is hydrogen, C ₁ -C ₂ alkyl, alkylthio, halo-C ₁ -C ₂ alkyl, C ₁ -C ₂ alkylamino or di-C ₁ -C ₂ alkylamino group, R ³ is hydrogen, halogen, C ₁ -C ₂ alkyl, C ₁ -C ₂ alkylthio, C ₁ -C ₂ alkoxy, halo-C ₁ -C ₂ alkyl, halo-C _1- C ₂ alkoxy, C ₁ -C ₂ alkylamino or di-C ₁ -C ₂ alkylamino and R ⁴ is hydrogen, C ₁ -C ₆ alkyl, benzyl, C ₃ -C ₈ alkenyl, C ₃ -C ₈ alkoxy Or a single equivalent metal, and R ⁷ and R ⁸ are hydrogen, halogen, C ₁ -C ₂ alkyl group, C ₁ -C ₂ alkoxy, C ₁ -C ₂ alkylthio, halo-C ₁ -C ₂ alkyl or halo- C ₁ -C ₂ alkoxy group, m is 0. A herbicide composition comprising the compound of claim 1 or 2 in admixture with an agriculturally acceptable carrier or diluent. A method for combating weeds by applying the compound according to claim 1 or 2 to weeds or their location. ※ Note: The disclosure is based on the initial application.