5-Amino-1-phenyl-pyrazole-4-carboxylic acid derivatives and their use for controlling undesirable plant growth

• US 4,472,192 A
• Filed: 07/20/1982
• Issued: 09/18/1984
• Est. Priority Date: 07/25/1981
• Status: Expired due to Fees

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Plath, Peter, Eicken, Karl, Wuerzer, Bruno
• Primary Examiner(s): Jiles, Henry R.
• Assistant Examiner(s): Briscoe, Kurt G.
• Application Number:
  US06/400,049
• Time in Patent Office: 791 Days
• Field of Search: 71/92, 548/362
• US Class Current: 504/282
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: C07C 255/00 Carboxylic acid nitriles cyanogen or compounds thereof C01C3/00
• CPC Class Codes: C07D 231/38 Nitrogen atoms nitro radicals C07D231/16

Abstract

5-Amino-1-phenyl-pyrazole-4-carboxylic acid derivatives of the formula ##STR1## where R¹, R², R³ and A have the meanings given in the description, are used for controlling undesirable plant growth.

Claims

1. A 5-Amino-1-phenyl-pyrazole-4-carboxylic acid derivative of the formula ##STR10## where R¹ is methyl, trifluoromethyl, chlorine or bromine, R² is chlorine, bromine, iodine or methylsulfonyl, R³ is a methoxy radical in the 5-position or is hydrogen, chlorine or bromine, and A is --OR⁴, where R⁴ is alkenyl of 3 to 12 carbon atoms which is unsubstituted or substituted by phenyl, or is alkynyl of 3 to 10 carbon atoms, phenalkyl, where alkyl is of 1 to 8 carbon atoms, phenoxyalkyl, where alkyl is of 2 to 8 carbon atoms and the phenyl ring is unsubstituted or substituted by halogen, alkyl of 1 to 4 carbon atoms or methoxy, cycloalkylmethyl of 4 to 7 carbon atoms in total, or alkyl of 2 to 4 carbon atoms which is substituted by alkoxy of 1 to 12 carbon atoms, alkylthio of 1 to 12 carbon atoms, allyloxy, propargyloxy, chlorine or bromine, and salts thereof.

2. A 5-Amino-1-phenyl-pyrazole-4-carboxylic acid derivative of the formula I as claimed in claim 1, wherein A is --OR⁴, R⁴ denoting alkenyl of 3 to 12 carbon atoms or alkyl of 2 to 4 carbon atoms which is substituted by alkoxy of 1 to 12 carbon atoms.

3. A compound of formula I as set forth in claim 1, wherein R¹ and R² are chlorine, R³ is 6-chlorine and A is OCH₂ CH═

CH₂.

6. A method of combating the growth of unwanted plants which comprises applying to the plants or their location a herbicidally effective amount of a 5-amino-1-phenyl-pyrazole-4-carboxylic acid derivative of the formula I as set forth in claim 1, or a salt thereof.

4. A herbicidal composition comprising a carrier and a herbicidally effective amount of a 5-amino-1-phenyl-pyrazole-4-carboxylic acid derivative of the formula ##STR11## where R¹ is methyl, trifluoromethyl, chlorine or bromine, R² is chlorine, bromine, iodine or methylsulfonyl, R³ is a methoxy radical in the 5-position or is hydrogen, chlorine or bromine, and A is --OR⁴, where R⁴ is alkenyl of 3 to 12 carbon atoms which is unsubstituted or substituted by phenyl, or is alkynyl of 3 to 10 carbon atoms, phenalkyl, where alkyl is of 1 to 8 carbon atoms, phenoxyalkyl, where alkyl is of 2 to 8 carbon atoms and the phenyl ring is unsubstituted or substituted by halogen, alkyl of 1 to 4 carbon atoms or methoxy, cycloalkylmethyl of 4 to 7 carbon atoms in total, or alkyl of 2 to 4 carbon atoms which is substituted by alkoxy of 1 to 12 carbon atoms, alkylthio of 1 to 12 carbon atoms, allyloxy, propargyloxy, chlorine or bromine, or a salt thereof.

5. A herbicidal composition as set forth in claim 4, and containing a 5-amino-1-phenyl-pyrazole-4-carboxylic acid derivative of the formula I wherein A is --OR⁴, R⁴ denoting alkenyl of 3 to 12 carbon atoms or alkyl of 2 to 4 carbon atoms which is substituted by alkoxy of 1 to 12 carbon atoms.