Halogen-containing compounds, herbicidal composition containing the same as an active ingredient, and intermediary compounds therefor

Halogen-containing compounds represented by the formula ##STR44## wherein Z.sup.1 is a nitrogen atom and Z.sup.2 is group CH,

• X represents a fluorine atom,
• W represents an oxygen atom, sulfur atom or --OCH.sub.2 --,
• n represents an integer of 0, 1, 2 or 3,
• R.sup.1 and R.sup.2 each independently represent either a hydrogen atom, halogen atom or mono- or dilower alkylsubstituted amino, or a lower alkyl, lower alkoxy or lower alkylthio each of which may be substituted with a halogen atom,
• R.sup.5 represents a hydrogen atom or lower alkyl group,
• A represents an oxygen atom, sulfur atom or group .dbd.N--B wherein B represents hydroxy, lower alkenyloxy, lower alkynyloxy, benzyloxy or lower alkylcarbonyloxy, or lower alkoxy optionally substituted with hydroxycarbonyl, phenylcarbonyl or lower alkoxycarbonyl, and
• Y either represents a hydrogen atom, a hydroxy, a mercapto, or
• a lower alkoxy, lower alkenoxy, lower alkynoxy, lower alkylthio, phenoxy, benzyloxy, phenylthio, benzylthio, lower cycloalkoxy, lower cycloalkenyloxy, pyridylthio, furylmethyloxy, furylthio or thienyloxy each optionally substituted with a halogen atom, hydroxy, lower alkyl, lower alkoxy, leroy alkylthio, lower alkoxycarbonyl, lower alkylcarbonyl, cyano, nitro or azido, or
• an azido, a trilower alkyl-substituted silyloxy or an imidooxy, or represents a group ##STR45## {wherein R.sup.6 and R.sup.7 each independently represent a hydrogen atom, lower alkyl, lower alkoxy, phenyl or benzyl or R.sup.6 and R.sup.7 may form together with the carbon atom to which they bind a lower cycloalkane ring, and
• R.sup.8 and R.sup.9 each independently represent a hydrogen atom, a hydroxy, a lower alkyl, a lower alkenyl, a lower alkynyl, a lower alkoxy, a lower alkenyloxy, lower alkynyloxy, 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
• a phenyl, benzyl, phenyloxy, benzyloxy, and phenylcarbonyloxy, pyridyl, ##STR46## (wherein Z.sup.3 represents an oxygen atom, CH or sulfur atom, Z.sup.4 represents a nitrogen atom or CH, Z.sup.1 and Z.sup.2 are as defined above, and m represents an integer of 0or 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-alkylsubstituted amino or lower alkoxycarbonyl, ##STR47## (wherein R.sup.10 and R.sup.11 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 a phenyl, benzyl, 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.