3-(4-cyanophenyl) uracils

• US 6,656,884 B2
• Filed: 12/20/2002
• Issued: 12/02/2003
• Est. Priority Date: 02/09/1995
• Status: Expired due to Fees

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: von dem Bussche-Hünnefeld, Christoph-Sweder, Götz, Norbert, Walter, Helmut, Hamprecht, Gerhard, Schäfer, Peter, Westphalen, Karl-Otto, Misslitz, Ulf, Harreus, Albrecht, Heistracher, Elisabeth, Klintz, Ralf
• Primary Examiner(s): Ford, John M.
• Application Number:
  US10/323,931
• Publication Number:
  US 20030181335A1
• Time in Patent Office: 347 Days
• Field of Search: 504/243, 514/312
• US Class Current: 504/243
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: C07C 255/60 at least one of the singly-bound nitrogen atoms being acylated
• CPC Class Codes: C07C 275/42 being further substituted by carboxyl groups
• CPC Class Codes: C07D 239/54 as doubly bound oxygen atoms or as unsubstituted hydroxy radicals

Abstract

3-(4-Cyanophenyl)uracils of the formula I

wherein

A is hydrogen, methyl or amino;

Y is oxygen or sulfur;

R¹ is hydrogen or halogen;

R² is hydrogen, halogen, alkyl, haloalkyl, alkylthio, alkylsulfenyl or alkylsulfonyl;

R³ is hydrogen, halogen or alkyl;

R⁴ is hydrogen, haloalkyl; or unsubstituted or substituted alkyl, cycloalkyl, alkenyl, alkynyl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl or alkylsulfonyl,

methods and intermediates for their manufacture, and their use as herbicides or for the desiccation or defoliation of plants.

Claims

1. A compound of formula I

wherein

A is methyl;

Y is oxygen or sulfur;

R¹ is hydrogen or fluorine;

R² is trifluoromethyl;

R³ is hydrogen; and

R⁴ is hydrogen, methyl, isopropyl, propargyl, CH₂—

COOCH₃, CH₂—

COOC₂H₅, CH(CH₃)—

COOCH₃ or CH(CH₃)—

COOC₂H₅.

2. The compound of formula I defined in claim 1, wherein R⁴ denotes methyl, isopropyl, propargyl, CH₂—

COOCH₃, CH₂—

COOC₂H₅, CH(CH₃)—

COOCH₃ or CH(CH₃)—

COOC₂H₅.

3. The compound of formula I defined in claim 1 wherein Y is oxygen.

4. A herbicidal composition comprising an effective amount of at least one compound of formula I

wherein

A is methyl;

Y is oxygen or sulfur;

R¹ is hydrogen or fluorine;

R² is trifluoromethyl;

R³ is hydrogen; and

R⁴ is hydrogen, methyl, isopropyl, propargyl, CH₂—

COOCH₃, CH₂—

COOC₂H₅, CH(CH₃)—

COOCH₃ or CH(CH₃)—

COOC₂H₅,

or of an agriculturally useful salt thereof, and at least one inert liquid or solid carrier and optionally at least one surfactant.

6. The composition defined in claim 4, wherein R⁴ denotes methyl, isopropyl, propargyl, CH₂—

COOCH₃, CH₂—

COOC₂H₅, CH(CH₃)—

COOCH₃ or CH(CH₃)—

COOC₂H₅.

5. A composition for the desiccation or defoliation of plants, comprising an effective amount of at least one compound of formula I

wherein

A is methyl;

Y is oxygen or sulfur;

R¹ is hydrogen or fluorine;

R² is trifluoromethyl;

R³ is hydrogen; and

R⁴ is hydrogen, methyl, isopropyl, propargyl, CH₂—

COOCH₃, CH₂—

COOC₂H₅, CH(CH₃)—

COOCH₃ or CH(CH₃)—

COOC₂H₅,

or of an agriculturally useful salt thereof, and at least one inert liquid or solid carrier and optionally at least one surfactant.

7. The composition defined in claim 5, wherein R⁴ denotes methyl, isopropyl, propargyl, CH₂—

COOCH₃, CH₂—

COOC₂H₅, CH(CH₃)—

COOCH₃ or CH(CH₃)—

COOC₂H₅.

8. A method of controlling undesired vegetation, which comprises allowing an effective amount of at least one compound of formula I

wherein

A is methyl;

Y is oxygen or sulfur;

R¹ is hydrogen or fluorine;

R² is trifluoromethyl;

R³ is hydrogen; and

R⁴ is hydrogen, methyl, isopropyl, propargyl, CH₂—

COOCH₃, CH₂—

COOC₂H₅, CH(CH₃)—

COOCH₃ or CH(CH₃)—

COOC₂H₅,

or of an agriculturally useful salt thereof, to act on plants, their habitat or on seed.

10. The method of claim 8, wherein R⁴ denotes methyl, isopropyl, propargyl, CH₂—

COOCH₃, CH₂—

COOC₂H₅, CH(CH₃)—

COOCH₃ or CH(CH₃)—

COOC₂H₅.

9. A method for desiccating or defoliating plants, which comprises applying to the plants an effective amount of at least one compound of formula I

wherein

A is methyl;

Y is oxygen or sulfur;

R¹ is hydrogen or fluorine;

R² is trifluoromethyl;

R³ is hydrogen; and

R⁴ is hydrogen, methyl, isopropyl, propargyl, CH₂—

COOCH₃, CH₂—

COOC₂H₅, CH(CH₃)—

COOCH₃ or CH(CH₃)—

COOC₂H₅,

or an agriculturally useful salt thereof.

11. The method of claim 9, wherein R⁴ denotes methyl, isopropyl, propargyl, CH₂—

COOCH₃, CH₂—

COOC₂H₅, CH(CH₃)—

COOCH₃ or CH(CH₃)—

COOC₂H₅.