US 5,356,863 A · Uracil derivatives

Abstract

The present invention relates to an uracil derivative represented by the formula (1): ##STR1## in which R.sup.1 represents hydrogen, alkyl or haloalkyl; R.sup.2 represents haloalkyl; R.sup.3 represents hydrogen, alkyl, haloalkyl, hydroxymethyl, halogen or nitro; R.sup.4 represents hydrogen or halogen; R.sup.5 represents hydrogen, halogen, nitro or cyano; X represents oxygen or sulfur: provided that the case where both of Da and Db represent hydrogen is excluded and a herbicide containing the same. The compound can be safely applied to important crops and shows high effect against many weeds in a low amount.

An uracil derivative, which is represented by the formula (1):

##STR38## in which R.sup.1 represents a hydrogen atom, a C.sub.1 to C.sub.3 alkyl group or a C.sub.1 to C.sub.3 haloalkyl group;
R.sup.2 represents a C.sub.1 to C.sub.6 haloalkyl group;
R.sup.3 represents a hydrogen atom, a C.sub.1 to C.sub.6 alkyl group, a C.sub.1 to C.sub.6 haloalkyl group, a hydroxymethyl group, a halogen atom or a nitro group;
R.sup.4 represents a hydrogen atom or a halogen atom;
R.sup.5 represents a hydrogen atom, a halogen atom, a nitro group or a cyano group;
X represents an oxygen atom or a sulfur atom;
D.sub.a and D.sub.b each independently represents a hydrogen atom, a C.sub.1 to C.sub.8 alkyl group, a C.sub.1 to C.sub.6 haloalkyl group, a C.sub.3 to C.sub.8 cycloalkyl group, a C.sub.3 to C.sub.8 cycloalkyl(C.sub.1 to C.sub.4)alkyl group, a C.sub.2 to C.sub.8 alkenyl group, a C.sub.3 to C.sub.8 alkynyl group, a C.sub.2 to C.sub.8 haloalkenyl group, a C.sub.3 to C.sub.8 haloalkynyl group, a C.sub.3 to C.sub.8 halocycloalkyl group, a C.sub.3 to C.sub.8 halocycloalkyl(C.sub.1 to C.sub.4)alkyl group, CH(OH)CCl.sub.3, Ar in which Ar represents a phenyl group or a naphthyl group each of which may be substituted by one or two or more substituents and the substituent may be selected from a C.sub.1 to C.sub.4 alkyl group, a C.sub.3 to C.sub.6 cycloalkyl group, a C.sub.1 to C.sub.4 haloalkyl group, a C.sub.3 to C.sub.6 halocycloalkyl group, a halogen atom, a cyano group, a nitro group, a hydroxy group, a C.sub.1 to C.sub.4 alkoxy group, a C.sub.1 to C.sub.4 haloalkoxy group, a C.sub.1 to C.sub.4 alkylcarbonyl group, a carboxyl group, a C.sub.1 to C.sub.4 alkoxycarbonyl group, an amino group, a C.sub.1 to C.sub.4 alkylamino group, an acetamino group, a N,N-dimethylamino group and a methanesulfonyl group,
--L.sup.1 --Ar in which Ar has the same meaning as above, and L.sup.1 represents a C.sub.1 to C.sub.6 alkyl chain, a C.sub.2 to C.sub.6 alkenyl chain or a C.sub.2 to C.sub.6 alkynyl chain each of which may be branched,
Het in which Her represents a 5-membered heterocyclic residue, a 6-membered heterocyclic residue or a fused heterocyclic residue each of which contains, as a ring constituent atom, at least one atom selected from a sulfur atom, an oxygen atom and a nitrogen atom and may be substituted by one or two or more substituents, and the substituent may be selected from a C.sub.1 to C.sub.4 alkyl group, a C.sub.3 to C.sub.6 cycloalkyl group, a C.sub.1 to C.sub.4 haloalkyl group, a C.sub.3 to C.sub.6 halocycloalkyl group, a halogen atom, a cyano group, a nitro group, a hydroxy group, a C.sub.1 to C.sub.4 alkoxy group, a C.sub.1 to C.sub.4 haloalkoxy group, a C.sub.1 to C.sub.4 alkylcarbonyl group, a carboxyl group, a C.sub.1 to C.sub.4 alkoxycarbonyl group, an amino group, a C.sub.1 to C.sub.4 alkylamino group, an acetamino group, a N,N-dimethylamino group and a methanesulfonyl group,
--L.sup.1 --Het in which Het and L.sup.1 have the same meanings as above,
--L.sup.2 --D.sup.52 in which D.sup.52 represents a hydrogen atom, a C.sub.1 to C.sub.20 alkyl group, a C.sub.1 to C.sub.20 haloalkyl group, a C.sub.3 to C.sub.8 cycloalkyl group, a C.sub.3 to C.sub.8 cycloalkyl(C.sub.1 to C.sub.4)alkyl group, a C.sub.2 to C.sub.8 alkenyl group, a C.sub.3 to C.sub.8 alkynyl group, a C.sub.2 to C.sub.8 haloalkenyl group, a C.sub.3 to C.sub.8 haloalkynyl group, a C.sub.3 to C.sub.8 halocycloalkyl group, a C.sub.3 to C.sub.8 halocycloalkyl (C.sub.1 to C.sub.4)alkyl group, a C.sub.1 to C.sub.4 alkoxy(C.sub.1 to C.sub.4)alkyl group,
Ar (Ar has the same meaning as above), --L.sup.1 --Ar group (Ar and L.sup.1 have the same meanings as above), Het (Het has the same meaning as above)or --L.sup.1 --Het (Het and L.sup.1 have the same meanings as above), and L.sup.2 represents --(O)--, --C(S)--, --SO.sub.2 --, --S(O)--, --S--, --O--, --C(O)O--, --C(O)S--, --C(S)O--, --C(S)S-- or --C(O)C(O)O--,
--L.sup.3 --O--D.sup.52 in which D.sup.52 has the same meaning as above, and L.sup.3 represents a C.sub.1 to C.sub.6 alkyl chain, a C.sub.2 to C.sub.6 alkenyl chain or a C.sub.2 to C.sub.6 alkynyl chain each of which may be substituted by one or two or more substituents and may be branched and the substituent may be selected from a C.sub.1 to C.sub.4 alkyloxycarbonyl group, a C.sub.1 to C.sub.4 haloalkyl group, a C.sub.1 to C.sub.4 alkoxy(C.sub.1 to C.sub.4)alkyl group, a C.sub.1 to C.sub.4 alkylthio group,
Ar (Ar has the same meaning as above), --L.sup.1 --Ar group (Ar and L.sup.1 have the same meanings as above), Het (Het has the same meaning as above)and --L.sup.1 --Het (Het and L.sup.1 have the same meanings as above),
--L.sup.3 --S--D.sup.52 in which D.sup.52 and L.sup.3 have the same meanings as above,
--L.sup.3 --(O)--D.sup.52 in which D.sup.52 and L.sup.3 have the same meanings as above,
--L.sup.3 --C(S)--D.sup.52 in which D.sup.52 and L.sup.3 have the same meanings as above,
--L.sup.3 --C(O)O--D.sup.52 in which D.sup.52 and L.sup.3 have the same meanings as above,
--O--L.sup.3 --C(O)O--D.sup.52 in which D.sup.52 and L.sup.3 have the same meanings as above,
--L.sup.3 --C(O)S--D.sup.52 in which D.sup.52 and L.sup.3 have the same meaning as above,
--O--L.sup.3 --C(O)S--D.sup.52 in which D.sup.52 and L.sup.3 have the same meanings as above,
--(O)--ND.sup.52 D.sup.53 in which D.sup.52 has the same meaning as above, and D.sup.53 represents a hydrogen atom, a C.sub.1 to C.sub.8 alkyl group, a C.sub.1 to C.sub.8 haloalkyl group, a C.sub.1 to C.sub.6 alkoxy group, a C.sub.1 to C.sub.6 alkylcarbonyl group, a C.sub.1 to C.sub.6 haloalkylcarbonyl group, a C.sub.1 to C.sub.6 alkoxycarbonyl group, a C.sub.1 to C.sub.6 alkylsulfonyl group, a C.sub.1 to C.sub.6 haloalkylsulfonyl group, Ar (Ar has the same meaning as above), --L.sup.1 --Ar group (Ar and L.sup.1 have the same meanings as above), --(O)--Ar (Ar has the same meaning as above), --C(O)--Ar (Ar has the same meaning as above)or --SO.sub.2 --Ar (Ar has the same meaning as above), and alternatively D.sup.52 and D.sup.53 together with a nitrogen atom to which they are attached may form a 5- to 7-membered ring, and ring constituent atoms are selected from a carbon atom, a nitrogen atom, an oxygen atom and a sulfur atom,
--C(S)--ND.sup.52 D.sup.53 in which D.sup.52 and D.sup.53 have the same meanings as above,
--L.sup.3 --C(O)--ND.sup.52 D.sup.53 in which D.sup.52 D.sup.53 and L.sup.3 have the same meanings as above,
--L.sup.3 --C(S)--ND.sup.52 D.sup.53 in which D.sup.52 D.sup.53 and L.sup.3 have the same meanings as above,
--SO.sub.2 --ND.sup.52 D.sup.53 in which D.sup.52 and D.sup.53 have the same meanings as above,
--SO.sub.2 O--D.sup.53 in which D.sup.53 has the same meaning as above,
--SO.sub.2 O--Si(CH.sub.3).sub.3,
--SO.sub.2 --L.sup.1 --Si(CH.sub.3).sub.3 in which L.sup.1 has the same meaning as above,
--SO.sub.2 CH.sub.2 SO.sub.2 CH.sub.3,
--P(O)(OD.sup.52)(OD.sup.53) in which D.sup.52 and D.sup.53 have the same meanings as above,
--P(O)(OD.sup.52)(SD.sup.53) in which D.sup.52 and D.sup.53 have the same meanings as above,
--P(O)(OD.sup.52)D.sup.53 in which D.sup.52 and D.sup.53 have the same meanings as above,
--P(O)(SD.sup.52)D.sup.53 in which D.sup.52 and D.sup.53 have the same meanings as above,
--P(S)(OD.sup.52)(OD.sup.53) in which D.sup.52 and D.sup.53 have the same meanings as above,
--P(S)(OD.sup.52)(SD.sup.53) in which D.sup.52 and D.sup.53 have the same meanings as above,
--P(S)(OD.sup.52)D.sup.53 in which D.sup.52 and D.sup.53 have the same meanings as above,
--P(S)(SD.sup.52)D.sup.53 in which D.sup.52 and D.sup.53 have the same meanings as above,
--L.sup.3 --P(O)(OD.sup.52)(OD.sup.53) in which D.sup.52 D.sup.53 and L.sup.3 have the same meanings as above,
--L.sup.3 --P(O)(OD.sup.52)(SD.sup.53) in which D.sup.52 D.sup.53 and L.sup.3 have the same meanings as above,
--L.sup.3 --P(O)(OD.sup.52)D.sup.53 in which D.sup.52 D.sup.53 and L.sup.3 have the same meanings as above,
--L.sup.3 --P(O)(SD.sup.52)D.sup.53 in which D.sup.52 D.sup.53 and L.sup.3 have the same meanings as above,
--L.sup.3 --P(S)(OD.sup.52)(OD.sup.53)in which D.sup.52 D.sup.53 and L.sup.3 have the same meanings as above,
--L.sup.3 P--P(S)(OD.sup.52)(SD.sup.53)in which D.sup.52 D.sup.53 and L.sup.3 have the same meanings as above,
--L.sup.3 --P(S)(OD.sup.52)D.sup.53 in which D.sup.52 D.sup.53 and L.sup.3 have the same meanings as above,
--L.sup.3 --P(S)(SD.sup.52)D.sup.53 in which D.sup.52 D.sup.53 and L.sup.3 have the same meanings as above,
--C(D.sup.53)(P(O)(OD.sup.52).sub.2).sub.2 in which D.sup.52 and D.sup.53 have the same meanings as above,
.dbd.CD.sup.52 D.sup.54 in which D.sup.52 has the same meaning as above, and D.sup.54 represents a hydrogen atom, a halogen atom, a C.sub.1 to C.sub.6 alkyl group, a C.sub.1 to C.sub.6 alkoxy group, a C.sub.1 to C.sub.6 alkylthio group or Ar (Ar has the same meaning as above),
--L.sup.3 --CN in which L.sup.3 has the same meaning as above,
--ND.sup.52 D.sup.53 in which D.sup.52 and D.sup.53 have the same meanings as above,
--CH.dbd.N--O--D.sup.52 in which D.sup.52 has the same meaning as above,
.dbd.CD.sup.54 --ND.sup.52 D.sup.53 in which D.sup.52, D.sup.53 and D.sup.54 have the same meanings as above,
--L.sup.2 --D.sup.55 in which L.sup.2 has the same meaning as above, and D.sup.55 represents a C.sub.1 to C.sub.6 alkyl group, a C.sub.2 to C.sub.6 alkenyl group or a C.sub.2 to C.sub.6 alkynyl group each of which may be substituted by one or two or more of a C.sub.1 to C.sub.6 haloalkyl group or one or two or more of a C.sub.1 to C.sub.4 alkyloxycarbonyl group and may be branched, or
--L.sup.1 --SO.sub.2 --D.sup.56 in which L.sup.1 has the same meaning as above, and D.sup.56 represents a C.sub.1 to C.sub.6 alkyl group;
and alternatively D.sub.a and D.sub.b may form a 3- to 8-membered ring and the ring constituent atoms are selected from a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom and a phosphorus atom, and the ring may be substituted by one or two or more of a substituent, and the substituent may be selected from a C.sub.1 to C.sub.4 alkyl group, a C.sub.3 to C.sub.6 cycloalkyl group, a C.sub.1 to C.sub.4 haloalkyl group, a C.sub.3 to C.sub.6 halocycloalkyl group, a halogen atom, a cyano group, a nitro group, a hydroxy group, a C.sub.1 to C.sub.4 alkoxy group, a C.sub.1 to C.sub.4 haloalkoxy group, a C.sub.1 to C.sub.4 alkylcarbonyl group, a carboxyl group, a C.sub.1 to C.sub.4 alkoxycarbonyl group, an amino group, a C.sub.1 to C.sub.4 alkylamino group, an acetamino group, a N,N-dimethylamino group and a methanesulfonyl group:
provided that except for the case where D.sub.a and D.sub.b both represent hydrogen atoms, the case where D.sub.a represents --L.sup.2 --D.sup.52 (L.sup.2 represents --SO.sub.2 --, and D.sup.52 represents the C.sub.1 to C.sub.4 alkyl group or the C.sub.1 to C.sub.3 haloalkyl group) and D.sub.b represents the hydrogen atom, the C.sub.1 to C.sub.4 alkyl group, the C.sub.2 to C.sub.5 alkenyl group, the C.sub.3 to C.sub.5 alkynyl group, the C.sub.2 to C.sub.5 acyl group, the C.sub.1 to C.sub.4 alkylsulfonyl group or the (C.sub.1 to C.sub.3 alkoxy) C.sub.1 to C.sub.2 alkyl group are excluded.

53 more elements

Uracil derivatives

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Uracil derivatives

Life of this patent

Abstract

Claims6