TH40593A - The phenoxypropionic acid compound N-alkyl-N-2-fluorophenyl amide is used as a herbicide. - Google Patents

Abstract

DC60 (10/09/42) This invention relates to the new herbicide phenoxypropionic acid N-alkyl-N-2-fluorophenyl amide substituted in the following formulation (1), the method for the preparation of these substances, their use for the control of barnyard grasses produced from rice, and the composition as a suitable herbicide (chemical formula) (I), where R is a methyl or ethyl group; X represents hydrogen, halogen, cyano, C1~C6 alkyl, C1~C6 alkoxy, C1~C3 haloalkyl substituted by 1 to 3 halogen atoms, C1~C3 haloalkoxy substituted by 1 to 3 halogen atoms, C2~C4 alkoxyalkoxy, phenoxy, benzyloxy, C2~C6 alkenyl, C2~C6 alkinyl, C2~C6 alkenyloxy, C2~C6 alkinyloxy, or phenyl group; Y represents hydrogen or fluoro; n is an integer of 1 or 2, and when n is 2, X is capable of combining with other substituents. This invention relates to the herbicide phenoxypropionic acid N-alkyl-N-2-fluorophenylamide. The new type is replaced in the following formula (1), the method for the preparation of these substances, their use to control barnyard grass produced from rice and the components as a suitable herbicide (chemical formula) (I) where, R is a methyl or ethyl group; X is hydrogen, halogen, cyano, C1~C6 alkyl, C1~C6 alkoxy, C1~C3 haloalkyl replaced by 1 to 3 of halogen atoms, C1~C3 haloalkoxy replaced by 1 to 3 of halogen atoms, C2~C4 alkoxyalkoxy, phenoxy, benzyloxy, C2~C6 alkenyl, C2~C6 alkinyl, C2~C6 alkinyloxy, C2~C4 alkinyloxy, or phenyl group; Y is hydrogen or fluoro; n is an integer of 1 or 2, and when n is 2, X is capable of combining with other substituent groups.

Claims (21)

1. Herbicide compounds of formula (I) (chemical formula) (i) where R is a methyl or aryl group: X is hydrogen, halogen, cyano, C1~C6 alkyl, C1~C6 alkoxy, C1~C3 haloalkyl replaced by 1 to 3 of a halogen atom, C1~C3 haloalkoxy replaced by 1 to 3 of a halogen atom, C2~C4 alkoxyalkoxy, phenoxy, benzyloxy, C2~C6 alkenyl, C2~C6 alkinyl, C2~C6 alkenyloxy, C2~C6 alkinyloxy, or phenyl group; Y is hydrogen or fluoro: n is an integer of 1 or 2, when n is 2, X can combine with other substituents. 2. Herbicide compounds as defined in Claim 1, where R is CH3; X is H,F,CI,Br,CN,CH3 or OCH3; Y is H, or F; n is 1. 3. Herbicide compounds as defined in Claim 1, where R is CH3; X is H; Y is H, 4. Herbicide compounds as defined in Claim 1, where R is CH3; X is 5-CH3; Y is H. 5. Herbicide compounds as defined in Claim 1, where R is CH3; X is 4,5-F2; Y is H. 6. Method of controlling barnyard weeds produced from unharmed rice growing using a compound formula (I) with an effective quantity (chemical formula) (1) where R is a methyl or aryl group; X is hydrogen, halogen, cyano, C1~C6 alkyl, C1~C6 alkoxy, C1~C3 haloalkyl replaced by 1 to 3 halogen atoms (S), C1~C3 haloalkoxy replaced by 1 to 3 halogen atoms, C2~C4 alkoxyalkoxy, phenoxy, benzyloxy, C2~C6 alkenyl, C2~C6 to alkynyl, C2~C6 alkynyloxy, C2~C6 alkynyloxy, or phenyl group; Y is hydrogen or fluoro; n is an integer of 1 or 2, where n is 2, X is capable of combining with Other representative groups 7. Methods of controlling barnyard grass as defined in claim 6, where the compound of formula (1) is R as CH3; X as H,F,CI,Br,CN,CH3 or OCH3; Y as H, or F; n as 1. 8. Methods of controlling barnyard grass as defined in claim 6, where the compound of formula (1) is such that R is CH3; X is H; Y is H. 9. Methods of controlling barnyard grass as defined in claim 6, where the compound of formula (1) is such that R is CH3; X is 5-CH3; Y is H. 10. Method of controlling barnyard grass as defined in claim 6, where the compound of formula (1) is such that R is CH3; X is 4,5-F2; Y is H. 11. The herbicide compound consists of a compound of formula (1) and an agriculturally acceptable carrier, adjuvant, surfactant, or other herbicide compound (chemical formula) (1), where R is a methyl or aryl group; X is hydrogen, halogen, cyano, C1~C6 alkyl, C1~C6 alkoxy, C1~C3 haloalkyl replaced by 1 to 3 halogen atoms (S), C1~C3 haloalkoxy replaced by 1 to 3 halogen atoms, C2~C4 alkoxyalkoxy, phenoxy, benzyloxy, C2~C6 alkenyl, C2~C6 to alkynyl, C2~C6 alkynyloxy, C2~C6 alkynyloxy, or phenyl group; Y is hydrogen or fluoro; n is an integer of 1 or 2; when n is 2, X is capable of combining with other substituents. 12. The herbicide compound as defined in claim 11, where the compound of formula (1) is such that R is CH3; X is H,F,CI,Br,CN,CH3 or OCH3; Y is H, or F; n is 1. 13. The herbicide compound as defined in claim 11, where the compound of formula (1) is such that R is CH3; X is H; Y is H. 14. The herbicide compound as defined in claim 11, where the compound of formula (1) is such that R is CH3; X is 5-CH3; Y is H. 15. The herbicide compound as defined in claim 11, where the compound of formula (1) is such that R is CH3; X is 4,5-F2; Y is H. 16. Method for preparing compounds (1) by reacting compounds of formula (6) and compounds of formula (7) (chemical formula) (6) (chemical formula) (7) (chemical formula) (1) where, R is a methyl group or an aryl group: X is hydrogen, halogen, cyano, C1~C6 alkyl, C1~C6 alkoxy, C1~C3 haloalkyl replaced by 1 to 3 of halogen atoms, C1~C3 haloalkoxy replaced by 1 to 3 of halogen atoms, C2~C4 alkoxyalkoxy, phenoxy, benzyloxy, C2~C6 alkenyl, C2~C6 alkynyl, C2~C6 alkynyloxy, C2~C6 alkynyloxy, or phenyl group; Y is hydrogen or fluorocarbon: n is an integer of 1 or 2; when n is 2, X is capable of combining with other substituents; and 17. Method for preparing compound (1) by reacting compound of formula (8) and compound of formula (9) (Chemical formula) (8) R—X” (9) (Chemical formula) (1) where, R is a methyl or ethyl group: X is hydrogen, halogen, cyano, C1~C6 alkyl, C1~C6 alkoxy, C1~C3 haloalkyl replaced by 1 to 3 of halogen atoms, C1~C3 haloalkoxy replaced by 1 to 3 of halogen atoms, C2~C4 alkoxyalkoxy, phenoxy, benzyloxy, C2~C6 alkenyl, C2~C6 alkynyl, C2~C6 alkynyloxy, C2~C6 alkynyloxy, or phenyl group; Y is hydrogen or fluorocarbon; n is an integer of 1 or 2; when n is 2, X is capable of combining with other substituent groups; and X” is a group of Cl, Br, I, benzene sulfonyloxy, toluene sulfonyloxy, methane sulfonyloxy, or small alkyl sulfate. 18. Method for preparing compound (1) by reacting compound of formula (10) and compound of formula (11) (chemical formula) (10) (chemical formula) (11) (chemical formula) (1) where, R is a methyl or ethyl group; X is hydrogen, halogen, cyano, C1~C6 alkyl, C1~C6 alkoxy, C1~C3 haloalkyl replaced by 1 to 3 of halogen atoms, C1~C3 haloalkoxy replaced by 1 to 3 of halogen atoms, C2~C4 alkoxyalkoxy, phenoxy, benzyloxy, C2~C6 alkenyl, C2~C6 alkynyl, C2~C6 alkynyloxy, C2~C6 alkynyloxy, or phenyl group; Y is hydrogen or fluorocarbon; n is an integer of 1 or 2, where n is 2, X is capable of combining with other substituents; and Y' is a halogen, alkylsulfonyloxy, haloalkylsulfonyloxy, benzenesulfonyloxy, or toluenesulfonyloxy group. 19. Method for preparing compounds (1) by reaction. Compounds of formula (12) and compounds of formula (13) (chemical formula) (12) (chemical formula) (13) (chemical formula) (1) where, R is a methyl or ethyl group; X is hydrogen, halogen, cyano, C1~C6 alkyl, C1~C6 alkoxy, C1~C3 haloalkyl replaced by 1 to 3 of halogen atoms, C1~C3 haloalkoxy replaced by 1 to 3 of halogen atoms, C2~C4 alkoxyalkoxy, phenoxy, benzyloxy, C2~C6 alkenyl, C2~C6 alkynyl, C2~C6 alkynyloxy, C2~C6 alkynyloxy, or phenyl group; Y is hydrogen or fluorocarbon; n is an integer of 1 or 2; when n is 2, X is capable of combining with other substituents; and Y' is a halogen, alkylsulfonyloxy, haloalkylsulfonyloxy, benzenesulfonyloxy, or toluenesulfonyloxy group. 20. Intermediate compounds of formula (11) (chemical formula) (11) where, R is a methyl or ethyl group; X is hydrogen, halogen, cyano, C1~C6 alkyl, C1~C6 alkoxy, C1~C3 haloalkyl replaced by 1 to 3 of a halogen atom, C1~C3 haloalkoxy replaced by 1 to 3 of a halogen atom, C2~C4 alkoxyalkoxy, phenoxy, benzyloxy, C2~C6 alkenyl, C2~C6 alkynyl, C2~C6 alkynyloxy, C2~C6 alkynyloxy, or phenyl group; Y is hydrogen or fluoro: n is an integer of 1 or 2, where n is 2, X is capable of combining with Other substituent groups Y' are halogenated, alkylsulfonyloxy, haloalkylsulfonyloxy, benzenesulfonyloxy, or toluenesulfonyloxy. 21. Intermediate compounds of formula (11) (chemical formula) (13) where, R is a methyl or ethyl group; X is hydrogen, halogen, cyano, C1~C6 alkyl, C1~C6 alkoxy, C1~C3 haloalkyl replaced by 1 to 3 of a halogen atom, C1~C3 haloalkoxy replaced by 1 to 3 of a halogen atom, C2~C4 alkoxyalkoxy, phenoxy, benzyloxy, C2~C6 alkenyl, C2~C6 alkynyl, C2~C6 alkynyloxy, C2~C6 alkynyloxy, or phenyl group; Y is hydrogen or fluoro; n is an integer of 1 or 2, where n is 2, X is capable of combining with other substituents.