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US 2004/0106520 A1Published application
Herbicidal heterocycles
AssigneeE. I. Du Pont de Nemours and Company
InventorsClifford Daniel Cotterman, Chi-Ping Tseng
Life of this patent
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Abstract
Compounds of Formula (1), their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation, wherein A, R1, R2a, R2b, W, Y, and Z are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula (1) and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula (1).
Claims20
A compound selected from Formula 1, an N-oxide or an agriculturally suitable salt thereof,
- 31
- wherein:
- A is an optionally substituted aryl or heteroaromatic ring, wherein the optional substituents are selected from halogen, cyano, C1-C6 alkyl, C1-C4 haloallcyl, C2-C6 alkenyl, C2-C6 alkenyl, OR8, —S(O)kR9, —C(O)R10, —C(O)OR11 and —C(O)NR12R13;
- two substituents of the group A may combine to form a fused 5- or 6-membered saturated or partially saturated carbocyclic or heterocyclic ring, and said fused ring system is optionally substituted with one or more R7;
- Y is O or S;
- Z is O, S(O)n or CR3R4;
- W is (CR3R4)q;
- R1 is H, C1-C12 alkyl, C1-C12 haloallyl, C3-C12 cycloalkyl, C3-C12 halocycloalkyl, C4-C12 alkylcycloalkyl, C4-C12 alkylhalocycloalkyl, C1-C12 alkoxy, C1-C12 alkylthio, di-(C1-C2 alkyl)amino, Cl, Br, I, —C(O)R5, —C(O)OR5, —C(O)NR5R6 or tri(C1-C4 alkyl)silyl;
- R2a is H, C1-C4 alkyl or C1-C4 haloalkyl;
- and R2a only exists when the carbon atom to which it is connected is a quaternary carbon center in which case the dotted line in Formula 1, together with the parallel solid line, represents a single bond;
- R2b is H, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, F or Cl;
- or
- R1 and R2b are taken together as —C(R3R4)CH2CH2—, —C(R3R4)CH2CH2CH2— or —(CH2)mO(CH2)t—;
- each R3 and R4 are independently H, C1-6 alkyl or C1-C6 haloalkyl;
- R5 is C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl or C1-C6 haloallyl;
- R6 is H or C1-C6 alkyl;
- each R7 is independently C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, halogen, CN, NO2 or hydroxy;
- each R8 is independently C1-C4 alkyl or C1-C4 haloalkyl;
- each R9 is independently C1-C4 alkyl or C1-C4 haloalkyl;
- each R10 is independently C1-C4 alkyl or C1-C4 haloalkyl;
- each R11 is independently C1-C4 alkyl, C1-C3 haloalkyl, C2-C4 alkenyl, C2-C3 haloalkenyl, C2-C4 alkynyl, C3-C6 cycloalkyl, C3-C5 halocycloalkyl, C3-C6 cycloalkenyl or C4-C6 cycloalkylalkyl;
- each R12 is independently H or C1-C2 alkyl;
- each R13 is independently C1-C4 alkyl;
- or
- R12 and R13 are taken together as —(CH2)4—, —(CH2)5— or —(CH2)2O(CH2)2—;
- each k is independently 0, 1 or 2;
- n is 0, 1 or 2;
- q is 1 or 2;
- m is 0, 1 or 2;
- t is 0, 1 or 2;
- and
- m+t is 2 or 3;
- provided that:
- (a) each position on the aryl or heteroaromatic ring A vicinal (ortho) to the point of attachment of the aryl or heteroaromatic ring to the Formula 1 backbone is independently substituted with fluorine or not substituted;
- (b) when A is a phenyl ring with a fluorine substituent meta to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone, then attached at the other meta position of the phenyl ring is a substituent other than fluorine;
- (c) when A is a phenyl ring with at least one —C(O)NR12R13 substituent, then the at least one —C(O)NR12R13 substituent is at a position other than meta to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone;
- (d) when A is a phenyl ring, the position para to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone is unsubstituted or substituted by a substituent other than alkoxy,
- (e) when A is a phenyl ring with a —C(O)OR11 substituent at the position para to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone, then a substituent is attached to a position on the phenyl ring meta to the point of attachment of the phenyl ring to the remainder of the Formula 1 backbone;
- (f) when A is a pyridine ring connected at the 2-position to the remainder of the Formula 1 backbone and methyl is at the 6-position of the pyridine ring, then the pyridine ring is substituted at the 4-position;
- (g) when A is a pyrimidine ring connected at the 2-position to the remainder of the Formula 1 backbone, and when the 4-position of the pyrimidine ring is unsubstituted or is substituted with methyl, then the substituent at the 6-position of the pyrimidine ring is other than methyl, and when a methoxy substituent is at the 4-position of the pyrimidine ring, then the substituent at the 6-position of the pyrimidine ring is other than methoxy,
- (h) when A is an isothiazole ring connected at the 5-position to the remainder of the Formula 1 backbone, then the isothiazole ring is substituted with a substituent other than alkyl;
- (i) when R1 is a C3-C12 alkoxy group, then the alkyl moiety of the alkoxy group is branched at the carbon atom attached to the oxygen atom;
- (j) when R1 and R2b are taken together as —C(R3R4)CH2CH2—, —C(R3R4)CH2CH2CH2— or —(CH2)mO(CH2)t— then Z is O or CR3R4;
- and
- (k) when R2b is connected to a quaternary carbon center, then R2b is H, C1-C4 alkyl or C1-C4 haloalkyl.
42 more elements
Dependencies are inferred from the claim text.