Herbicidal 5-amino-1-phenylpyrazoles

• US 4,614,533 A
• Filed: 01/10/1985
• Issued: 09/30/1986
• Est. Priority Date: 01/24/1984
• Status: Expired due to Term

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Schallner, Otto, Santel, Hans-Joachim, Schmidt, Robert R., Gehring, Reinhold, Wroblowsky, Heinz-Jurgen, Stetter, Jorg, Klauke, Erich
• Primary Examiner(s): Schwartz, Richard A.
• Assistant Examiner(s): Briscoe, Kurt G.
• Application Number:
  US06/690,347
• Time in Patent Office: 628 Days
• Field of Search: 71/92, 71/86, 71/87
• US Class Current: 504/282
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 47/02 the carbon atom having no bond to a nitrogen atom
• CPC Class Codes: A01N 47/18 containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
• CPC Class Codes: A01N 47/22 O-Aryl or S-Aryl esters thereof
• CPC Class Codes: A01N 47/36 containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
• CPC Class Codes: A01N 53/00 Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
• CPC Class Codes: A01N 57/22 containing aromatic radicals
• CPC Class Codes: C07D 231/38 Nitrogen atoms nitro radicals C07D231/16
• CPC Class Codes: C07D 231/40 Acylated on said nitrogen atom
• CPC Class Codes: C07F 9/4015 Esters of acyclic unsaturated acids
• CPC Class Codes: C07F 9/650905 having the nitrogen atoms in the positions 1 and 2

Abstract

Herbicidally active 5-amino-1-phenyl-pyrazoles, most of which are new, of the formula ##STR1##

Claims

1. A method of combating unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation a herbicidally effective amount of a 5-amino-1-phenyl-pyrazole of the formula ##STR113## in which R¹ represent hydrogen, nitroso, nitro, halogen, C_1-6 alkyl, C_1-6 halogenoalkyl with up to 9 halogen atoms, or represents unsubstituted phenyl or phenyl substituted by halogen, nitro, alkyl, alkoxy, and/or halogenoalkyl, each having up to 4 carbon atoms, or represents one of the radicals --S(O)_n --R⁹ ;

##STR114## R² represents hydrogen or a radical ##STR115## R³ independently or R² represents the same radicals as R² and additionally represents alkyl having up to 4 carbon atoms,

R⁴ and R⁶ independently of one another represent cyano, nitro, halogen, alkyl, alkoxy, alkoxy carbonyl, each of which has up to 4 carbon atoms and furthermore represents halogenoalkyl or halogenoalkoxy, each of which has up to 4 carbon atoms and up to 9 halogen atoms or represents a radical --S(O)_n --R¹³, and

R⁵, R⁷ and R⁸ independently of one another and of R⁴ and R⁶ represent the same radicals as R⁴ and R⁶ and additionally represent hydrogen, and

R⁹ represents hydrogen, hydroxyl, amino, fluorine, chlorine, bromine, alkylamino, dialkylamino, alkyl, halogenoalkyl, each of which has up to 4 carbon atoms in the individual alkyl parts, and said halogenoalkyl having up to 9 halogen atoms and R⁹ also represents unsubstituted phenyl or phenyl substituted by halogen, alkyl, alkoxy and/or halogenoalkyl, each of which has up to 4 carbon atoms, and said halogenoalkyl having up to 9 halogen atoms,

R¹⁰ represents hydrogen, alkyl having up to 4 carbon atoms, or unsubstituted phenyl or phenyl substituted by halogen, alkyl, alkoxy and or halogenoalkyl, each of which has up to 4 carbon atoms, said halogenoalkyl having up to 9 halogen atoms,

R¹¹ represents hydrogen, alkyl alkenyl or alkinyl, each of which has up to 8 carbon atoms, halogenoalkyl having up to 4 carbon atoms and up to 6 halogen atoms and phenylalkyl having up to 4 carbon atoms in the alkyl part,

R¹² represents hydrogen, alkyl which has 1 to 12 carbon atoms, alkenyl, alkinyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio, alkylamino, dialkylamino or halogenoalkyl, each of which has up to 4 carbon atoms in the individual alkyl parts, said halogenoalkyl having up to 9 halogen atoms and furthermore represents unsubstituted cycloalkyl which has 3 to 7 carbon atoms or cycloalkyl substituted by halogen, lower alkyl and/or lower halogenoalkyl, or represents phenyl, phenoxy, phenylthio or phenylamino, each of which is unsubstituted or substituted by halogen, alkyl, alkoxy and/or halogenoalkyl, each of which has up to 4 carbon atoms, and the halogenoalkyl having up to 9 halogen atoms,

R¹³ represents amino, alkyl, halogenoalkyl, alkylamino or dialkylamino, each of which has up to 4 carbon atoms in the individual alkyl parts and, the halogenoalkyl having up to 9 halogen atoms,

X represents oxygen or sulphur, and

n represents the numbers 0, 1 or 2.

2. The method according to claim 1, in which

R¹ represents hydrogen, nitroso, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- and i-propyl, n-, i, s- and t-butyl, trifluoromethyl, or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents from amongst fluorine, chlorine, bromine, nitro, methyl, ethyl, methoxy and trifluoromethyl, or represents one of the radicals --S(O)_n --R⁹ ;

##STR116## R³ independently of R² represents the same radicals as R² and additionally represents methyl, ethyl, n- and i-propyl, n-, i-, s- and t-butyl,

R⁴ and R⁶ independently of one another represent cyano, nitro, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- and i-propyl, n-, i-, s- and t-butyl, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, trifluoromethyl, trichloromethyl, dichlorofluoromethyl, difluorochloromethyl, chloromethyl, dichloromethyl, difluoromethyl, pentafluoroethyl, tetrafluoroethyl, trifluorochloroethyl, trifluoroethyl, difluorodichloroethyl, trifluorodichloroethyl, pentachloroethyl, trifluoromethoxy, trichloromethoxy, dichlorofluoromethoxy, difluorochloromethoxy, chloromethoxy, dichloromethoxy, difluoromethoxy, pentafluoroethoxy, tetrafluoroethoxy, trifluorochloroethoxy, trifluoroethoxy, difluorodichloroethoxy, trifluorodichloroethoxy, pentachloroethoxy or a radical --S(O)_n --R¹²,

R⁹ represents hydrogen, hydroxyl, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, ethylamino, diethylamino, diisopropylamino, di-n-butylamino, methyl, ethyl, dichlorofluoromethyl or trifluoromethyl, and represents phenyl which is optionally mono-substituted to trisubstituted by identical or different substituents from amongst methyl, methoxy, trifluoromethyl and chlorine,

R¹⁰ respresents hydrogen, methyl, ethyl, n- and i-propyl, and represents phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents from amongst methyl, methoxy, trifluoromethyl and chlorine,

R¹¹ represents hydrogen, methyl, ethyl, n- and i-propyl, n-, i-, s- and t-butyl, allyl, butenyl, propargyl, benzyl, chloroethyl or bromoethyl,

R¹² represents hydrogen, methyl, ethyl, n- and i-propyl, undecyl, vinyl, allyl, propargyl, butenyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, diethylamino, trifluoromethyl, trichloroethyl, dichlorofluoroethyl, difluorochloroethyl, chloromethyl, iodomethyl, bromomethyl, dichloromethyl, 1-chloroethyl, 2-chloroethyl, 2-bromoethyl, chloropropyl or heptafluoro-n-propyl, or represents cyclopentyl, cyclohexyl or cyclopropyl which is optionally monosubstituted to tetrasubstituted by identical or different substituents from amongst fluorine, chlorine, bromine, methyl and trifluoromethyl, and represents phenyl, phenoxy, phenylthio or phenylamino, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from amongst methyl, methoxy, chlorine and trifluoromethyl, and

R¹³ represents amino, methylamino, ethylamino, dimethylamino, diethylamino, fluorodichloromethyl, difluoromethyl, tetrafluoroethyl, trifluorochloroethyl, trifluoromethyl, methyl or ethyl.

3. The method according to claim 1, wherein the compound is 1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-nitro-5-propionylamido-pyrazole of the formula ##STR117##

4. The method according to claim 1, wherein the compound is 1-(2-chloro-4-trifluoromethyl-phenyl)-4-nitro-5-propionylamido-pyrazole of the formula ##STR118##

5. The method according to claim 1, wherein the compound is 1-(2-chloro-4-trifluoromethoxy-phenyl)-4-nitro-5-propionylamido-pyrazole of the formula ##STR119##

6. The method according to claim 1, wherein the compound is 5-chloroacetylamido-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole of the formula ##STR120##

7. The method according to claim 1, wherein the compound is 5-amino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole of the formula ##STR121##