Uracil derivatives and herbicides containing the same as active ingredient

An uracil derivative represented by the formula (I):

• ##STR294## wherein R.sup.1 represents hydrogen, C.sub.1-3 alkyl, hydroxymethyl or C.sub.1-3 haloalkyl,
• R.sup.2 represents C.sub.1-6 haloalkyl,
• R.sup.3 represents hydrogen, C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, hydroxymethyl, halogen or nitro,
• R.sup.4 represents hydrogen or halogen,
• (i) when R.sup.5 and R.sup.6 are taken separately,
• R.sup.5 represents halogen, nitro or cyano,
• R.sup.6 represents --S--B.sup.1 [wherein B.sup.1 represents hydrogen, C.sub.1-5 alkyl, C.sub.3-6 cyoloalkyl, C.sub.2-4 alkenyl, C.sub.3-4 alkynyl, cyanomethyl, hydroxymethyl, chloromethyl, benzyl, ##STR295## [in which B.sup.21 represents hydrogen, C.sub.1-3 alkyl, methylthio, phenylthio or methoxymethyl, and B.sup.22 represents hydrogen, sodium, potassium, ammonium, isopropylammonium, C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.3-5 alkynyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkyl-C.sub.1-2 alkyl, C.sub.2-3 haloalkyl, phenethyl, .alpha.-methylbenzyl, 3-dimethylaminopropyl, phenyl which may be substituted with one or more substituent (the substituent is at least one of halogen, C.sub.1-4 alkyl, C.sub.1-3 alkoxyl, C.sub.1-2 alkylamino, dimethylamino, C.sub.1-2 alkoxy-carbonyl, C.sub.2-3 acyl, C.sub.1-2 haloalkyl or C.sub.1-2 haloalkyloxyl), or benzyl which may be substituted with one or more substituent (the substituent is at least one of halogen, C.sub.1-4 alkyl, C.sub.1-3 alkoxyl, C.sub.1-2 alkylamino, dimethylamino, C.sub.2-3 acyl, trifluoroacetylamino, C.sub.1-2 alkoxy-carbonyl, methylsulfonyl, trifluoromethyl-Sulfonyl, C.sub.1-2 haloalkyl or C.sub.1-2 haloalkyloxyl)], CH.sub.2 --CH.sub.2n CO.sub.2 B.sup.22 (wherein B.sup.22 is the same meaning as defined above, and n is an integer of 1 to 4), CH.sub.2 -- Y--B.sup.23 (wherein B.sup.23 is hydrogen, C.sub.1-5 alkyl, cyanomethyl, C.sub.2-5 acyl, chloroacetyl or dimethylcarbamoyl, and Y is oxygen or sulfur) CH.sub.2 --Y--CH(B.sup.21)CO.sub.2 B.sup.22 (wherein B.sup.21, B.sup.22 and Y are the same meanings as defined above), or CH.sub.2 --Y--CH.sub.2 --CH.sub.2n CO.sub.2 B.sup.22 (wherein B.sup.22, n and Y are the same meanings as defined above)];
• ##STR296## [wherein D.sup.21 represents hydrogen, C.sub.1-3 alkyl, C.sub.1-3 alkoxyl or C.sub.1-3 alkoxy-C.sub.1-2 alkyl, and D.sup.22 represents hydrogen, C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, C.sub.2-3 haloalkyl, phenyl or benzyl];
• ##STR297## [wherein D.sup.21 and D.sup.22 are the same meanings as defined above, and D.sup.23 represents hydrogen or C.sub.1-3 alkyl];
• ##STR298## [wherein D.sup.22 is the same meaning as defined above, D.sup.24 represents hydrogen, C.sub.1-3 alkyl or C.sub.1-3 alkoxy-C.sub.1-2 alkyl, and Z represents oxygen, sulfur or NH];
• ##STR299## [wherein D.sup.25 represents hydrogen, sodium, C.sub.1-4 alkyl, C.sub.2-5 alkenyl, C.sub.3-5 alkynyl, C.sub.2-5 acyl, C.sub.1-4 alkylsulfonyl or C.sub.1-3 alkoxy-C.sub.1-2 alkyl, and D.sup.26 represents C.sub.1-4 alkyl or C.sub.1-3 haloalkyl];
• ##STR300## [wherein D.sup.27 represents hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.1-3 haloalkyl, C.sub.1-4 alkoxyl, C.sub.1-4 alkylthio, C.sub.1-4 alkoxy-carbonyl, mercapto, hydroxyl, C.sub.1-3 alkoxy -C.sub.1-2 alkyl, C.sub.1-4 alkylamino, ND.sup.28 (D.sup.29) (wherein D.sup.28 and D.sup.29 represent independently C.sub.1-4 alkyl), dimethylcarbamoyl, CONHSO.sub.2 CH.sub.3, C.sub.1-4 alkylsulfonyl, or N(D.sup.30)SO.sub.2 D.sup.31 (wherein D.sup.30 represents hydrogen, sodium, C.sub.1-4 alkyl, C.sub.1-4 alkylsulfonyl, C.sub.1-3 alkoxy-C.sub.1-2 alkyl, and D.sup.31 represents C.sub.1-4 alkyl or C.sub.1-3 haloalkyl)];
• ##STR301## [wherein D.sup.32 represents C.sub.1-6 alkyl or C.sub.3-6 cycloalkyl];
• ##STR302## [wherein D.sup.33, D.sup.34 and D.sup.35 represent independently hydrogen or C.sub.1-6 alkyl];
• ##STR303## [wherein D.sup.36 and D.sup.37 represent independently hydrogen, C.sub.1-6 alkyl or dimethylamino];
• ##STR304## [wherein D.sup.38 represents hydrogen, halogen, mercapto, hydroxyl, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.1-3 haloalkyl, C.sub.1-4 alkoxyl, C.sub.1-4 alkylthio, C.sub.1-4 alkoxy-carbonyl, dimethylcarbamoyl, C.sub.1-3 alkoxy-C.sub.1-2 alkyl, C.sub.1-4 alkylamino, ND.sup.28 (D.sup.29) (wherein D.sup.28 and D.sup.29 are the same meanings as defined above), CONHSO.sub.2 CH.sub.3, C.sub.1-4 alkylsulfonyl, phenyl, benzyl or N(D.sup.39)SO.sub.2 D.sup.31 (wherein D.sup.31 is the same meaning as defined above, and D.sup.39 represents hydrogen, C.sub.1-4 alkyl, sodium, potassium, C.sub.1-4 alkylsulfonyl or C.sub.1-3 alkoxy-C.sub.1-2 alkyl)];
• ##STR305## [wherein D.sup.40 represents hydrogen, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, phenyl, benzyl or 2-pyridyl, D.sup.41 represents hydrogen, halogen, mercapto, hydroxyl, amino, C.sub.1-6 alkyl, C.sub.1-4 alkylamino, ND.sup.28 (D.sup.29) (wherein D.sup.28 and D.sup.29 are the same meanings as defined above), C.sub.1-4 alkylthio, CO.sub.2 D.sup.28 (wherein D.sup.28 is the same meaning as defined above), C.sub.1-4 alkylsulfonyl, C.sub.1-4 alkoxyl or N(D.sup.39)SO.sub.2 D.sup.31 (wherein D.sup.31 and D.sup.39 are the same meanings as defined above), and D.sup.42 represents hydrogen, halogen, nitro, amino, cyano, C.sub.1-4 alkylamino, N(D.sup.28)D.sup.29 (wherein D.sup.28 and D.sup.29 are the same meanings as defined above), C.sub.1-4 alkylcarbonyl or C.sub.1-4 alkoxy-carbonyl];
• ##STR306## [wherein D.sup.43 represents hydrogen, hydroxyl, methoxy, amino, benzoyl or C.sub.1-4 alkyl, and D.sup.44 represents hydrogen, cyano, acetyl, C.sub.1-4 alkyl, carboxyl or C.sub.1-4 alkoxy-carbonyl];
• ##STR307## [wherein D.sup.45 and D.sup.46 represent independently hydrogen, phenyl, hydroxyl, methoxy or C.sub.1-4 alkyl];
• or ##STR308## [wherein D.sup.47 and D.sup.48 represent independently hydrogen or C.sub.1-4 alkyl], and
• X represents oxygen or sulfur,
• (ii) when R.sup.5 and R.sup.6 form a ring,
• the said urasil derivatives are represented by either of the following formula (II), (IV-1), (IV-2), (IV-3) or (IV-4):
• ##STR309## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and X are the same meanings as defined above,
• A.sup.1 represents hydrogen and C.sub.1-4 alkyl,
• A.sup.2 represents hydrogen C.sub.1-5 alkyl, C.sub.2-5 alkenyl, C.sub.3-5 alkynyl, C.sub.3-6 cycloalkyl-C.sub.1-2 alkyl, C.sub.1-6 haloalkyl, C.sub.1-6 haloalkenyl, C.sub.1-6 haloalkynyl, cyanomethyl, hydroxymethyl, chloromethyl, C.sub.1-3 alkoxy-C.sub.1-2 alkyl, --CH.sub.2 CO.sub.2 A.sup.21 [wherein A.sup.21 represents hydrogen, C.sub.1-5 alkyl, sodium, phenyl which may be substituted with halogen, or benzyl which may be substituted with halogen], --CH.sub.2 CON(A.sup.22)A.sup.23 [wherein A.sup.22 and A.sup.23 represent independently hydrogen or C.sub.1-3 alkyl], phenyl which may be substituted (the substituent is C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or halogen), benzyl which may be substituted (the substituent is C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkoxy -carbonyl, C.sub.1-3 alkoxy-C.sub.1-2 alkyl or halogen), or --CH.sub.2 A.sup.24 [wherein A.sup.24 represents 2-pyridyl which may be substituted (the substituent is C.sub.1-4 alkyl or halogen), 2-pyridazyl which may be substituted (the substituent is C.sub.1-4 alkyl or halogen), 3-isothiazole or 3-isoxazole], and
• J represents hydrogen, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-4 alkynyl, hydroxymethyl, chloromethyl, carbamoylmethyl, cyanomethyl, C.sub.1-4 alkoxy-carbonylmethyl, ##STR310## C.sub.3-6 cycloalkyl-C.sub.1-2 alkyl, C.sub.1-2 alkoxy-C.sub.1-2 alkyl, phenyl which may be substituted (the substituent is C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkoxy-carbonyl, C.sub.1-4 alkoxy- C.sub.1-2 alkyl or halogen), or benzyl which may be substituted (the substituent is C.sub.1-4 alkyl, C.sub.1-4 alkoxyl, C.sub.1-4 alkoxy-carbonyl, C.sub.1-4 alkoxy-C.sub.1-2 alkyl or halogen).