Herbicidal phenoxypropionic acid N-alkyl-N-2-fluorophenyl amide compounds

A method of controlling barnyard grass produced while growing rice without inflicting any substantial harm to said rice which comprises applying an effective amount of at least one compound of the formula (1):

• wherein,
• R is a methyl group or ethyl group;
• X is a hydrogen, halogen, cyano, C1˜C6 alkyl, C1˜C6 alkoxy, C1˜C3 haloalkyl substituted with 1 to 3 of halogen atom(s), C1˜C3 haloalkoxy substituted with 1 to 3 of halogen atom(s), C2˜C4 alkoxyalkoxy, phenoxy, benzyloxy, C2˜C6 alkenyl, C2˜C6 alkinyl, C2˜C6 alkenyloxy, C2˜C6 alkinyloxy, or phenyl group;
• Y is a hydrogen or fluoro group;
• and
• n is an integer of 1 or 2, provided that when n is 2, X can be the same or different.

A herbicidal composition comprising at least one compound of the formula (1) together with at least one member selected from the group consisting of:

• an agriculturally acceptable carrier, a supplement agent, a surfactant and at least one other herbicidal compound.
• wherein,
• R a methyl or ethyl group;
• X is a hydrogen, halogen, cyano, C1˜C6 alkyl, C1˜C6 alkoxy, C1˜C3 haloalkyl substituted with 1 to 3 of halogen atom(s), C1˜C3 haloalkoxy substituted with 1 to 3 of halogen atom(s), C2˜C4 alkoxyalkoxy, phenoxy, benzyloxy, C2˜C6 alkenyl, C2˜C6 alkinyl, C2˜C6 alkenyloxy, C2˜C6 alkinyloxy, or phenyl group;
• Y is a hydrogen or fluoro group;
• and
• n is an integer of 1 or 2, provided that when n is 2, X can be the same or different.

A method for preparing a compound of formula (1) comprising reacting a compound of the formula (6) with a compound of the formula (7):

• wherein,
• R is a methyl or ethyl group;
• X is a hydrogen, halogen, cyano, C1˜C6 alkyl, C1˜C6 alkoxy, C1˜C3 haloalkyl substituted with 1 to 3 of halogen atom(s), C1˜C3 haloalkoxy substituted with 1 to 3 of halogen atom(s), C2˜C4 alkoxyalkoxy, phenoxy, benzyloxy, C2˜C6 alkenyl, C2˜C6 alkinyl, C2˜C6 alkenyloxy, C2˜C6 alkinyloxy, or phenyl group;
• Y is a hydrogen or fluoro group;.
• n is an integer of 1 or 2, provided that when n is 2, X can be the same or different;
• and
• X′ is an OH, Cl, Br or phenoxy group.

A herbicidal compound of the formula (1):

• wherein,
• R is CH3;
• X is hydrogen, fluorine, chlorine, methyl or methoxy Y is hydrogen or fluoro;
• and
• n is 1.

A herbicidal composition comprising at least one compound of the formula (1) together with at least one member selected from the group consisting of:

• an agriculturally acceptable carrier, a supplement agent, a surfactant and at least one other herbicidal compound:
• wherein,
• R is a methyl group;
• X is a hydrogen, fluoro, chloro, bromo, cyano, methyl, or methoxy group;
• Y is hydrogen or fluoro;
• and
• n is 1.

A method for preparing a compound of formula (1) comprising reacting a compound of the formula (6) with a compound of the formula (7):

• wherein,
• R is a methyl group;
• X is a hydrogen, fluoro, chloro, bromo, cyano, methyl, or methoxy group;
• Y is hydrogen or fluoro;
• n is 1;
• and
• X′ is OH, Cl, Br or phenoxy group.

A method of controlling barnyard grass produced while growing rice without inflicting any substantial harm to said rice which comprises applying an effective amount of at least one compound of the formula (1):

• wherein,
• R is a methyl group;
• X is a hydrogen, fluoro, chloro, bromo, cyano, methyl or methoxy group;
• Y is a hydrogen or fluoro group;
• and
• n is 1.