Patent EP-0468766-A1 (EP)
Inventor: GOH ATSUSHI
IPC: C07D239/60
Filed: 1991-07-24
Abstract: Halogen-containing compounds represented by the formula
       
 wherein 
   X represents a halogen atom, 
   W represents an oxygen atom, sulfur atom or group -OCH₂-, 
   Z¹ and Z² each represent a nitrogen atom or group CH, but when Z¹ is a nitrogen atom, Z² represents nitrogen atom or group CH and when Z¹ is a group CH, Z² represents a nitrogen atom, 
   R¹ and R² each independently represent either a hydrogen atom, halogen atom or mono- or dilower alkyl-substituted amino, or a lower alkyl, lower alkoxy or lower alkylthio each of which may be substituted with a halogen atom, 
   R³ and R⁴ each independently represent a hydrogen atom, halogen atom, hydroxycarbonyl, lower alkoxycarbonyl, lower alkyl, lower alkenyl, lower alkynyl, aryl or aralkyl, or R³ and R⁴ form together with the carbon atoms to which they bind respectively a 5- to 8-membered carbon ring or heterocycle and these rings may optionally be substituted with one or the same or different two of hydroxy, lower alkyl, lower alkenyl, lower alkynyl, lower alkoxy, lower alkoxycarbonyl, lower alkylcarbonyloxy and a group = 0, and may have unsaturated bond(s) therein, 
   R⁵ represents a hydrogen atom or lower alkyl group, or may form together with part of R³ a double bond, 
   A represents an oxygen atom, sulfur atom or group = N-B wherein B represents hydroxy or lower alkylcarbonyloxy, or lower alkoxy optionally substituted with hydroxycarbonyl or lower alkoxycarbonyl, and 
   Y either represents a hydrogen atom, a hydroxy, a mercapto, or 
   a lower alkoxy, lower alkenoxy, lower alkynoxy, lower alkylthio, aryloxy, aralkyloxy, arylthio, aralkylthio, lower cycloalkoxy, lower cycloalkenyloxy, pyridylthio, furylmethyloxy, furylthio or thienyloxy each optionally substituted with a halogen atom, hydroxy, lower alkyl, lower alkoxy, lower alkylthio, lower alkoxycarbonyl, lower alkylcarbonyl, cyano, nitro or azido, or 
   an azido, a trilower alkyl-substituted silyloxy or an imidooxy, or represents a group
       
 [wherein 
   R⁶ and R⁷ each independently represent a hydrogen atom, lower alkyl, lower alkoxy, aryl or aralkyl, or R⁶ and R⁷ may form together with the carbon atom to which they bind a lower cycloalkane ring, and 
   R⁸ and R⁹ each independently represent a hydrogen atom, a hydroxy, a lower alkyl, a lower alkenyl, a lower alkynyl, a lower alkoxy, a lower alkylcarbonyloxy, a cyano, a lower alkylsulfonyl optionally substituted with a halogen atom, a lower alkyl substituted with lower alkoxycarbonyl, a lower alkyl substituted with hydroxycarbonyl, a lower alkoxy substituted with lower alkoxycarbonyl, a lower alkoxy substituted with hydroxycarbonyl, or 
   an aryl, aralkyl, aryloxy, aralkyloxy, arylcarbonyloxy, pyridyl,
     
       
 (wherein Z³ represents an oxygen atom, group CH or sulfur atom, Z⁴ represents a nitrogen atom or group CH, Z¹ and Z² are as defined above, and m represents an integer of 0 or 1) each optionally substituted with a halogen atom, hydroxy, lower alkyl, lower alkoxy, lower alkyl substituted with halogen atoms, cyano, nitro, amino, mono- or dilower-alkyl-substituted amino or lower alkoxycarbonyl,
       
 (wherein R¹⁰ and R¹¹ each represent a hydrogen atom, a lower alkyl, a lower alkoxycarbonyl, a lower alkyl substituted with lower alkoxycarbonyl, a lower alkyl substituted with hydroxycarbonyl, or an aryl, aralkyl, pyridyl or benzothiazolyl each optionally substituted with a halogen atom, lower alkyl, lower alkyl substituted with a halogen atom, lower alkoxy, cyano, amino or nitro)), and salts thereof, are herbicidally active.