Patent EA-001145-B1 (EA)
Title: 1,3-oxazin-4-one derivatives as herbicides
Inventor: CRAMP MPCHAEL COLIN
IPC: A01N43/86
Filed: 1996-06-18
Abstract: 1. A 1,3-oxazin-4-one derivative of the formula (I):    wherein: R<1> represents phenyl optionally substituted by from one to five groups which may be the same or different selected from halogen, methoxy and and optionally halogenated methyl; R<2> represents:a straight- or branched- chain alkyl having from one to four carbon atoms which is substituted by one or more groups R<8> which may be the same or different; or a group selected from cyano, -CHO, -COR<7> -CO2H, -CO2R<7>, -COSR<7>, -CONR<9>R<10>, -CH=NOH, -CH=NOR<7>, -CH=NOCOR<7>, -CH=NNR<9>R<10>, -CH2CN, -CH2NO2 and oxiranyl; R<3> represents phenyl optionally substituted by from one to five groups which may be the same or different selected from halogen, hydroxy, lower alkyl, haloalkyl, R<4> and R<5> independently represent lower alkyl; W represents -NH-; R<7> represents lower alkyl or haloalkyl; n represents zero, one or two; q represents one or two; R<8> represents a member of the group consisting of halogen, -OH, -OR<7>, -OCOR<7>, -S(O)nR<7> and -NR<9>R<10>;  R<9> and R<10> independently represent hydrogen, lower alkyl or haloalkyl;  or an agriculturally acceptable salt thereof. 2. A compound according to claim 1 in which R1 represents phenyl optionally substituted by one or more halogen groups. 3. A compound according to claim 2 in which R1 represents phenyl. 4. A compound according to any one of claims 1 to 3 in which R<8> represents -S(O)nR<7>, (wherein R<7> is alkyl) or halogen. 5. A compound according to claim 4 in which R<7> is methyl. 6. A compound according to any one of claims 1 to 3 in which R<2> represents methyl substituted by fluorine, methoxy, ethoxy or -S(O)nCH3. 7. A compound according to claim 1 in which R<3> represents phenyl optionally substituted by one or two groups which be the same or different selected from halogen and haloalkyl. 8. A compound according to claim 1 in which R<4> and R<5> each represent methyl. 9. A compound according to claim 1 which is:  N-(2,5-difluorophenyl)-2-(2,3-dihydro-6-methylsulphonylmethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(2,5-difluorophenyl)-2-(2,3-dihydro-6-methylthiomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-trifluoromethylphenyl)-2-(2,3-dihydro-6-methylthiomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-trifluoromethylphenyl)-2-(6-difluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(6-bromomethy1-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(2,5-difluorophenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(2,3-dihydro-6-methoxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(2,5-difluorophenyl)-2-(2,3-dihydro-6-methoxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-trifluoromethylphenyl)-2-(2,3-dihydro-6-methoxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(6-fluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(2,5-difluorophenyl)-2-(6-fluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(2,5-difluorophenyl)-2-(6-chloromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(6-chloromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-trifluorophenyl)-2-(6-chloromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(5-chloro-2-methylphenyl)-2-(2,3-dihydro-6-methoxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-chlorophenyl)-2-(2,3-dihydro-6-methoxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(2-fluoro-5-trifluoromethylphenyl)-2-(2,3-dihydro-6-methoxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(2,5-difluorophenyl)-2-(6-ethoxymethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-trifluoromethylphenyl)-2-(6-ethoxymethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(6-ethoxymethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(2-fluoro-5-trifluoromethylphenyl)-2-(6-fluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,4,5-trifluorophenyl)-2-(6-fluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-difluorophenyl)-2-(6-fluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(2-chloro-3,5-difluorophenyl)-2-(6-fluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-trifluoromethylphenyl)-2-(6-fluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-chlorophenyl)-2-(6-fluoromethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-[6-(3-chloropropyl)-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl]-2-methylpropanamide,  N-(3-chlorophenyl-2-[6-(3-chloropropyl)-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl]-2-methylpropanamide,  N-(3-trifluoromethylphenyl)-2-[6-(3-chloropropyl)-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl]-2-methylpropanamide,  N-(2,5-difluorophenyl)-2-[6-(3-chloropropyl)-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl]-2-methylpropanamide,  N-(2,5-difluorophenyl)-2-(2,3-dihydro-6-methylsulphinylmethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-trifluoromethylphenyl)-2-(2,3-dihydro-6-methylsulphinylmethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-chlorophenyl)-2-(2,3-dihydro-6-iodomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-chlorophenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-trifluoromethylphenyl)-2-(6-bromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-chlorophenyl)-2-(6-dibromomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl-2-(2,3-dihydro-6-methylthiomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(6-ethylthiomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-trifluoromethylphenyl)-2-(6-ethylthiomethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-trifluoromethylphenyl)-2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide, N-(3,5-dichlorophenyl)-2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(2,5-difluorophenyl)-2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-trifluoromethylphenyl)-2-(6-acetoxymethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(6-acetoxymethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-trifluoromethylphenyl)-2-(2,3-dihydro-6-methylaminomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3-trifluoromethylphenyl)-2-(2,3-dihydro-6-dimethylaminomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(2,3-dihydro-6-dimethylaminomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(2,3-dihydro-6-methylaminomethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(2,3-dihydro-6-formyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(6-acetyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(2,5-difluorophenyl)-2-(6-acetoxymethyl-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(2,3-dihydro-6-hydroxyiminomethylene-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(6-ethoxyiminomethylene-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(2,3-dihydro-6-methoxyiminomethylene-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(2,5-difluorophenyl)-2-(2,3-dihydro-6-methoxyiminomethylene-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(6-acetoxyiminomethylene-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(6-aminoiminomethylene-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(2,3-dihydro-6-methylaminoiminomethylene-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2-(6-cyano-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide,  N-(3,5-dichlorophenyl)-2[2,3-dihydro-6-(1-hydroxyethyl)-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl]-2-methylpropanamide or  N-(2,5-difluorophenyl)-2-(2,3-dihydro-6-formyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide. 10. A herbicidal composition comprising an effective amount of a 1,3-oxazin-4-one derivative in association with an agriculturally acceptable diluent or carrier and/or surface acting agent, wherein contains a 3-oxazin-4-one derivative according to any one of claims 1 to 9 or an agriculturally acceptable salt thereof. 11. A method according to claim 16 wherein the locus is an area to be used, or to be used for the growing of crops and the 1,3-oxazin-4-one derivative is applied at an application rate of from 0.001 to 1.0 kg/ha. 12. A compound of formula   where R<1>, R<2> R<4> and R<5> are as defined in claim 1, and A group is selected from COOH and COCl groups.