CA2025932C - Pyrazole-3-carboxamides - Google Patents

Pyrazole-3-carboxamides Download PDF

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CA2025932C
CA2025932C CA002025932A CA2025932A CA2025932C CA 2025932 C CA2025932 C CA 2025932C CA 002025932 A CA002025932 A CA 002025932A CA 2025932 A CA2025932 A CA 2025932A CA 2025932 C CA2025932 C CA 2025932C
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alkyl
methyl
pyrazole
hydrogen
group
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CA2025932A1 (en
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Klaus Ditrich
Gerhard Hamprecht
Peter Plath
Bruno Wuerzer
Karl-Otto Westphalen
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Pyrazole-3-carboxamide of the general formula (I):
where the substituents have the following meanings:
R1 and R4 hydrogen;

C1-C4-alkyl or C3-C8-cycloalkyl, hydrogen;
C1-C4-alkyl;
phenyl which may carry from one to three of the following radicals; halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and/or C1-C4-alkylthio;

a COYR6 group;
Y
oxygen;

hydrogen, or an -N=CR7R8 group where R7 is hydrogen or C1-C4-alkyl and R8 is C3-C6-cycloalkyl or a radical R7, or R7 and R8 together form a 4- to 7-membered alkylene chain, or an agriculturally useful salt thereof.

Description

The present invention relates to a pyrazole-3-carboxamide of the general formula (I):

Rs I ~ NRiR2 (I) R3.
where:
R1 and R4 hydrogen;

C1-C4-alkyl or C3-Cg-cycloalkyl, hydrogen;
C1-C4-alkyl;
phenyl which may carry from one to three of the following radicals; halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and/or C1-C4-alkylthio;

a COYR6 group;
Y
oxygen;

hydrogen, or an -N=CR~R8 group where R~ is hydrogen or C1-C4-alkyl and R8 is C3-C6-cycloalkyl or a radical R~, or la R~ and R8 together form a 4- to 7-membered alkylene chain, or an agriculturally useful salt thereof.
The present invention also relates to a pyrazole-3-carboxamide of the general formula I:

R5 NRiR1 I
R 4 I N ~N

where l0 Rl is hydrogen;
C3-Ce-cycloalkyl which may carry from one. to three of the following radicals: halogen, Cl-C,,-alkyl, C1-C4-haloalkyl, C1-C,-alkoxy and/or C1-C4-haloalkoxy;
C1-Cs-alkyl which may carry from one to three of the following radicals: hydroxyl, halogen, C1-C~-alkoxy, C=-C~-haloalkoxy, Cl-C,,-alkylthio, C1-C,-haloalkylthio, hydroxycarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkylamino, di-C1-C~-alkylamino and/or C3-Ca-cycloalkylamino and/or a radical Rm where R is cyano; nitro; halogen; C1-C~-alkyl; C1-C4-halo-alkyl; Cl-C~-alkoxy; Cl-C,-haloalkoxy; C1-C,,-alkylthio;
C1-C,-haloalkylthio and/or Cl-C~-alkoxycarbonyl, and m is 0, 1, 2 or 3, it being possible for the radicals R to be different from one another when m is 2 or 3;
RZ is hydroxyl; amino; C1-C~-alkylamino; di-C1-C4-alkyl amino; aminocarbonyl-Cl-CB-alkyl; Cl-C,-alkoxy which 3o may carry a radical Rm - 2 - O.Z. 0050/41113 C3-Ce-alkenyl, C3-C6-alkynyl, phenyl or naphthyl, it being possible for these groups to carry from one to three of the radicals mentioned in the case of R;
a 5- to 6-membered saturated or unsaturated heterocyclic ring containing one or two heteroatoms selected from the group comprising nitrogen, oxygen and sulfur, it being possible for this ring to carry one or two of the follow-ing radicals : halogen, C1-Ca-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkox~ and/or Cl-C4-alkylthio;
one of the groups mentioned in the case of Rl or R1 and RZ together are a 4- to 7-membered chain which may contain one of the following groups as a ring member in addition to methylene groupsa oxygen, sulfur, N-methyl or carbonyl;
R3 is a 5- to 6-membered saturated or unsaturated hetero-cyclic ring containing one or two heteroatoms selected from the group comprising oxygen, sulfur and nitrogen, it being possible for this ring to carry one or two of the following radicals s halogen, C1-C4-alkyl, C1-C4-haloalkyl, Cl-C4-alkoxy, Cl-~C4-haloalkoxy and/or Cl-C4-alk~rlthio;
C3-Ce-alkenyl, C3-CB-alkynyl, 5, 6, 7', 8-tetrahydronaphthyl or phenyl, it being possible for these groups to carry from one to three ~f the radicals mentioned in the case of R, or is one of the groups mentioned in the case of R1;
R4 is vitro;~cyano; carboxyl; halogen;
C1-C4-alkoxy or C1-C4-a.lkylthio, it being possible for these groups to carry from one to nine halogen atoms, or w - 3 - o.z. 0050/41113 is one of the groups mentioned in the case of R3;
RS is 4,5-dihydrooxazol-2-yl or a COYRe group;
Y is oxygen or sulfur;
R~' is hydrogen;
C3-Ce-cycloalkyl;
C1-CB-alkyl which ray carry from one to five halogen atoms or hydroxyl groups and/or one of the following radicals: cyano, aminocarbonyl, carboxyl, tri-methylsilyl, C1-C4-alkoxy, C1-C4-alkoxy-CZ-C4-alkoxy, Ca-C4-alkylthio, Cl-C4-alkylamino, di-Cl-C4-alkylamino, C1-C4-alkylsulfinyl, Cl-C4-alkylsulfonyl, Cl-C4-alkoxy-carbonyl, C~,-C4-alkylaminocarbonyl, di-C1-C4-alkyl-aminocarbonyl, di-C1-C4-alkylphosphonyl, C1-C4-alkyl-iminoxy, phenyl, thienyl, benzyloxy, benzylthio, furyl, tetrahydz~ofuryl, phthalimido, pyridyl and/or benzoyl, it being possible for the cyclic radicals to th~mselves carry from one to three of the radicals mentioned in the case of R;
C3-CB-alkenyl, C3-Cg-al%ynyl or CS~C~-cyc~oalkenyl, it being possible far these groups to carry ore of the following radicals: hydroxyl, halogen, C~-C4-alkox~r or phenyl, it being possible for the phenyl radical to itself harry from one to three of'the radicals mentioned in the case of R;
a 5- 'to 6-member~d saturated or unsaturated hetero-cyclic ring containing one or two heteratoms selec-ted frazn tha group comprising nitrog~n, oxgyen and sulfur;
phthal3mido; tetrahydrophthalimido; sdccinimido;

~~~~ ~' - '~ - O. Z . 0050/41113 maleiimido; benzotriazolyl;
phenyl which may carry from one to three of the radicals mentioned in the case of R;
an -N=CR'R8 group where R' is hydrogen or C1-C8-alkyl and Ra is C3-C6-cycloalkyl, phenyl, furyl or a radical R', or R' and R8 together form a 4- to 7-membered alkylene chain, and agriculturally useful salts thereof, where Y is not oxygen or Rz is not hydrogen if R3 is hydrogen and R" is vitro, trifluoromethyl, halogen or Cl-C4-alkoxy.
Th~ present in:'ention also relates to herbicides containing one or more pyrazole-3-carboximides I and/or pyrazole-3-carboximides of the general formula Ta p 0 R1 RSV i ) N1 Ia R4 ~H R2 where Y is oxygen or Rl is hydrogen if R~ is hydrogen and R~ is vitro, trifluoromethyl, halogen or Cs-C4-alkoxy, and inert additives.
Pyrazole-3-chrboxim3.des are known from the liter~~ure for the following applications:
Application Li~~xature citation Additive for electrocoating paints EP-~A 159 11?
Fungicid~ EP-~ 206 523 - Indian: J: Chem. 13, (1975] 655 In addition, DE~A-33 32 633yrlescribea pyrazole-3 carboxamides which are substituted in the 5-posi~ian of the heterocyclic ring by vitro, trifluoromethyl, halogen or C1-C~-alkoxy, as pharmaceuticals. ' - 5 - O.z. 0050/41113 However, a herbicidal action of substances of this type was not found.
It is an object of the present invention to provide novel herbicidally active substances.
We have found that this ob jeot is achieved by the pyrazole-3-carboxamides I defined at the outset.
We have also found that the pyrazole-3-carbox-amides I and the pyrazole-3-carboxamides Ia are suitable for controlling undesired plant growth.
The pyrazole-3-carboxamides I according to the invention can be prepared by various processes, for example by the following:
1. A process for the preparation of a compound I in which RS is COZR° and R' is C1-C4-alkyl R~ I
(R° - C1-Ca-alkyl) ~ R

These pyrazole-3-carboxamides L are obtained by reacting a dialkyl pyrazole-3,4-dicaxboxylate of the formula II in a conventional manner in an inert organic solvent with an amine of the formula IIT

R. Rr /
R; I ~N + HN\R 2 ~D I ~ R ~ - Ci-C4 a7Lky1 ) II III
R' in the formulae II amd I is C1-C4-alkyl, such as methyl, ethyl, propyl, 1-mathylethyl, butyl, 1-methyl-propyl, 2-metraylpropyl or l,l-dimethylethyl, preferably methyl, ethyl or 1-methylethyl.
The reaction is generally carried out at from 0 to 100°C, preferably from 50 to ~0°C, in an inert organic solvent.

N
R~ I NON \ 2 Suitable solvents are halogenated hydrocarbons, such as chlorob~nzene and. 1,2-dichlorobenzene, ethers, s r~ r~ ~~
~~ a..A~~~
- 6 - O.Z. 0050/41113 such as. methyl tart-butyl ether, 1,2-dimethoxyethane, diethylene glycol dimethyl ether, tetrahydrofuran and dioxane; alcohols, such as methanol, ethanol, propanol and ethylene glycol, dipolar aprotic solvents, such as acetonitrile, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, P1-methylpyrrolidone, 1,3-dimethyl-tetrahydro-2(1H)-pyrimidinone andl,3-dimethylimidazolin-2-one, or aromatic compounds, such as benzene, toluene and xylene. The process is particularly preferably carried out in the alcohol corresponding to the ester component.
The concentration of the starting materials in the solvent is generally from 0.1 to S.O mo1/1, prefer-ably from 0.2 to 2.0 mol/1.
The molar ratio between II and III is generally from 1:2.5 to 1:1, preferably from 1:1.5 to 1:1, A particularly preferred process involves the use of a diester II and an amine III in the ratio 1:1 in the absence of solvents at from 50 to 80°C.
The pyrazoledicarboxy~.ates II required as start-ing materials fax this process are known from the litera-ture or can be pr~pared by methods known from the litera-ture (cf. J. Heterocyclic Chem. 25, (1988) 1293; J. Am.
Chem. Soc. 73, (1951) 3684; J. Org. Chem. 31, (1966) 2491; J. Heterocyclic Chem. 22, (1985) 565; Chem. Ber.
101, (1968) 536; Chem. Ber. 101 , (1968) 1059; Chem. Ber.
107, (1974) 3036).
The annines V' required are either commercially available or can be prepared by conventional processes.
A particularly preferred process for the prepara-tion of the pyrazole-3-carbox~mides bf the formula I
comprises converting a pyrazole-3,4-dicarboxylate of the formula IIa into a monocarboxylic acid ITb using an aqueous base: The comp~und IIb can be converted into the desired amide via the acyl chloride intermediate using an amine of the formula III:

l' ~,.' ~3 ~ 7 ti l ..~ r,' - ~ - O.Z. 0050/41113 R I I CH3 A. R I I H B. R I I N~
R 4 N/N ---~ R 4 tV~N --~ R 4 NON R Z

IId (R~ * CH3) IIb (R' * CH3) I (R5 = COZR~; R~#CH3) R' is C1-C4-alkyl, such as methyl, ethyl, propyl, iso-propyl, n-butyl or sec-butyl, preferably ethyl or iso-propyl.
The reaction is caxried out by reacting a pyrazoledicarboxylate IIa in an inert solvent with an aqueous base at from -30°C to 120°C, preferably from -10°C to 40°C. The pyrazolemonocarboxylic acid of the formula IIa is then liberated at from -30°C to 100°C, preferably from -10°C to ZO°C, by adding a mineral acid.
Suitable salvents are alcohols, such as methanol, ethanol, propanol or ethylene glycol, preferably the alcohol which corresponds to the ester component in II.
The concentration of the starting material II is generally from 0.1 to 0.5 mol/1, preferably from 0.2 to 2.0 moll.
The aqueous base employed is a 5 to 20$ strength aqueous solution of an alkali metal hydroxide or alkaline earth metal hydroxide, such as LiOH, NaOH, KOH, Ca ( OH ) Z or Ba(OH)2, preferably NaOH or ROH.
The molar ratio between the diester IIa and hydroxide is from 1x0.95 to 1:1 for an alkali metal hydroxide and fxom 1:0.48 to 1:0.55 for an alkaline earth metal hydroxide.
The reaction is generally complete after 14 hours. The monocarboxylic acid IIb is then liberated by adding a strong mineral acid such as hydrochloric acid or sulfuric acid and isolated in a conventional manner, for example by suction filtration or extraction with an organic solvent.
For conversion into the acyl halide; the car-boxylic acid IIb is reacted with a halogenating agent, preferably an inorganic acid halide, if desired in an - O.Z. 0050/41113 inert solvent, with addition of a catalytic amount of N,N-dimethylforrnamide or 4-N,N-dimethylaminopyridine, at from 0°C to the boiling point of the solvent (mixture) or halogenating agent used.
Suitable inert solvents are halogenated hydro-carbons, such as tetrachloroethane, methylene chloride, chloroform, dichloroethane, chlorobenzene and 1,2-di-chlorobenzene, or aromatic compounds, such as benzene, toluene or zylene, preferably benzene or toluene.
Expedient halogenating agents are inorganic acid halides, such as thionyl chloride, phosphorus trichloride or phosphorus pentachloride. The carboxylic acid III and halogenating agent are employed in a ratio of from 1:1 to 1:10, preferably from l:l to 1:5. The concentration of the catalyst (N,N-dimethylformamide or 4-N,N-dimethyl-aminopyridine) is from 1 to 20 mol-~, preferably from 1 to 5 mol-$, based on the carboxylic acid IIb employed.
If the reaction is carried out in a solvent, the concentration of the starting material IIb is from 0.1 to 5.O mo1/1, preferalaly from 0.2 to 2.0 mol/1.
The process is particularly preferably carried out using five equivalents of thionyl chloride in the presence of 2 mol-~ of N,N-dimethylformamide at the reflux temperature of the reaction mixture.
The xeaction is generally complete after 5 hours;
the acyl chloride IV can be isolated in a conventional manner, for example by removing the excess inorganic acid halide and solvent by distillation and subsequently distilling the acyl halide which remains, if necessary under reduced pressure:
The amide I is obtained in a conventioa~al manner by reacting a pyrazole-3-carbonyl chloride of the formula IV with an amine V. An expedient procedure is to react a solution of the acyl halide inn an inert solvent with an amine III, l~,kewise in an inert solvent. The acyl chloride and the amine III are expediently employed in a ratio of from 1:2 to 1a5, but it is also possible to s - 9 - O.Z. 0050/41113 carry out the reaction in the presence of an acid acceptor, in which case the acyl chloride and the amine III are expediently employed in a ratio of from 1:1 to 1:1.5 and the acyl chloride and the acid acceptor in a ratio of from 1:1.5 to 1:5.
The solvent used for these reactions is prefer-ably a halogenated hydrocarbon, such as tetrachloro-ethane, methylene chloride, chloroform, dichloroethane, chlorobenzene or 1,2-dichlorobenzene, or an ether, eg.
diethyl ether, methyl tert-butyl ether, 1,2-dimethoxy-ethane, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane; a Bipolar aprotic solvent, eg. acetonitrile, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, 1,3-dimethyltetrahydro-2(1H)-pyrimi-dinone or 1,3-dimethylimidazolin-2-one; an aromatic compound, eg. benzene, toluene or xylene, or a ketone, such as acetone or methyl ethyl ketone. The concentration of the staxting materials. in the solvent is generally from 0.1 to 5.0 mol/1, preferably from 0.2 to 2.0 moll.
The reaction can be carried out at from -30°C to the reflux temperature of the solvent (mixture) used.
Preferred acid acceptors are aromatic nitrogen bases, such as pyridine, 4-dimethylaminopyridine and quinoline; tertiary aliphatic amines, such as triethyl amine, N-ethyldiisopropylaznine and N-methylmorpholine;
bicyclic and tricyclic amines, such as diazabicyclooctane (DABCO) and diazabicycloundecane (DBU); and carbonated or bicarbonates. of alkali metals or of alkaline earth metals, eg. sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate. It may in some cases also be useful to use combinations of the abovemen-tioned bases.
The process is pabticularly preferably carried out at from 0 to 30°C in a halogenated hydrocarbon, such as tetrachloroethane, methylene chloride, chloroform or dichloroethane, in the presence of three equivalents of the amine III. .

T C 6~3 f~ sJ rJ
- 10 - O.Z. 0050/41113 The reaction is generally complete after 14 hours; the mixture can be worked up in a conventional manner, for example by hydrolysis using water and extrac-tion of the amide VI with an organic solvent. The product of formula VI can be purified as usual by recrystallization or chromatography.
2. A process for the preparation of a compound I in Which RS 7.9 COZH

H N/ I
R 4 i P,lsN eR 2 ( RS = COZH ) This compound I is obtained by hydrolyzing a pyrazole-3-carboxamide I in which RS is COZR° and R' is C1-C4-alkyl, in a conventional manner in the presence of an aqueous base. 0 0 R1 R~ ~
R 4 ( N~ -~.~R 2 I (R~ ~ C02R' R'in the formula I is as defined abov~ in the case of process l, but is preferably methyl.
The reaction is carried out by reacting a pyrazolecarboxylate I (RS _ C02R') in an inert solvent with an ague~us ba~~ at from -30 to 120°C, preferably from 10 to ~0°C. The pyrazolecarbox~7ac acid of the formula I (RS _ COZHj is then liberated at from -30 to 100°C, preferably from dl0 t~ 10~C, by adding a mineral acid.
Suitable solvents are alcohols, such as methanol, ethanol, propanol and ethylene glycol.
The concentration of the starting material I is generally from 0.l to S.Q mol/l, preferably from 0.2 to 2.0 mol/1.
The aqueous base employed is a 5 to 20% strength ~~~~3~
- 11 - O.Z. 0050/47.113 aqueous solution of an alkali metal hydroxide or of an alkaline earth metal hydroxide, such as LiOH, NaOH, ROH, Ca(OH)~ or Ba(OH)2, preferably NaOH or KOH.
The molar ratio between the ester I and the hydroxide is from 1:0.95 to 1:1.1 for an alkali metal hydroxide and from 1:0.48 to 1:0.55 for an alkaline earth metal hydroxide.
3. A process for the preparation of a compound I in which RS is COYRe R6Y I I ~~ I
R G t~N R a ( RS = COYRe ) This compound is obtained, for example, by converting a pyrazole-3-carboxamide I in which RS is COZH in a conven-tional manner into an activated form of the carboxylic acid, and subsequently esterifying the latter'using a compound IV.

H N
R~ ~ ~I ~R2 + HYRg -----~ I (R5 = COYR6) I (RS 9 COZH) IY
This reaction is usually carried out at from -20 to 60°C, preferably from 0 to 40°C.
Ths solvent used is expediently a halogenated hydroaarbon, such as tetrachloromethane, methylene chloxide, chloroform, dichloxoethane, chlorobenzene or 1,2-dichlorobenzene, an et3~er, eg. methyl tert-butyl ether, 1,2-dimethoxyethane, diethylene glycal dimethyl ether, tetrahydrofuran or dioxane; a Bipolar aprotic solvent, eg. acetonitrile, d3.methylformamide, dimethyl-acetamide, dimethyl sulfoxide, N-methylpyrrolidone, 1,3-dimethyltetrahydro-2(1H)-pyrimidinone or 1,3-dimethyl-imidazolin-2-one, or an aromatic compound, eg. benzene, - 12 - O.Z. 0050/41113 toluene or xylene. The concentration of the starting materials in the solvent is generally from 0.1 to 5.Omo1/1, preferably from 0.2 to 2.0 mol/1.
In general, from 1 to 1.5 mol equivalents, preferably from 1 to 1.15 mol equivalents, of the compound IV are employed, based on the carboxylic acid I
( RS = COZH ) .
Suitable dehydrating agents are diimides, such as dicyclohexylcarbodiimide, or anhydrides, such as propane phosphonic anhydride. The reaction is also successful in the presence of 1-methyl-2-halopyridinium iodides as the dehydrating agent (cf. Chem. Lett., (1975) 1045; ibid., (1976), 13; ibid., (1976), 49.
The process is particularly preferably carried out at from 20 to 40°C in an inert solvent, such as tetrahydrofuran, dichloromethane or toluene, in the presence of dicyclohexylcarbodiimide as the dehydrating agent, the carboxylic acid I, the compound IV and the dehydrating agent being employed in stoichiometric amounts.
The reaction is generally complete after 14 hours; the pyrazole-3-carboxamide is isolated in a conventional manner ( for example by diluting the reaction mixture with water and extracting the product' with an organic solvent) and purified by conv~ntional standard methods, such as recrystallization or chromatography.
4. A process for the preparation of a compound I in which RS is 4,5-dihydrooxazol-2-yl o R1 (R3 = 4,5-dihydrooxazol-2-yl) . R; ) ! I \R y' This compound is obtained by reacting a pyrazole-3-carboxamide I in which R5 is C02R ~ or COON and R' is Cl-C4-alkyl in a conventional manner with an amino alcohol of formula V.

13 ° O.Z. 0050/41213 R 0 0 N/R1 i 0 N/R1 H ZN-CH Z-CIi 2'011 I I

~3 v R3 (RS = C00R' or COOH) (RS = 4,5-dihydrooxazol-2-yl) The reaction is carried out by reacting .the compound at from 0 to 180°C, preferably at the reflux temperature of the mixture used, with an aminoalcohol V, if desired in the presence of an inert solvent. The ester or carboxylic acid T and the aminoalcohol V are employed in a ratio of from l:l to 1:2.5, preferably from 1:1 to 1:1.5.
The solvent used is expediently a halogenated hydrocarbon, such as ehlorobenzene or 1,2-dichloro benzene, an ether, eg. methyl text-butyl ether, 1,2 dimethoxyethane, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane~ an alcohol, such as methanol, ethanol, propanol or ethylene glycol, a Bipolar aprotic solvent, eg. acetonitrile, d3methylformamide, dimethyl-acetamide, dimethyl sulfoxide, N-methylpyrrolidone, 1,3-dimethyltetrahydro-2(1H)~pyr~midinone or 1,3-dime~hyl-imidazolin-2-on~, ox an aromatic compound, eg: benzene, toluene or xylene. The concentration of the starting materials in the solvent is generally from 0.1 to 5.0 mol/1, preferably from 0':2 to 2:O mol/1.
The reactibn is generally complete after 14 hours; the gyrazolecarbo~amide I is then precipitated, if necessary, by adding water, filtered off with suction or extracted with an organic solvent and purified by conventional standard methods, such as recrystallization or chromatography.
With respect to the intended use of the compounds I, preferred substituen~s are the following radicals:
R1 is hydrogen;

- 14 - O.Z. 0050/41123 C3-C8-cycloalkyl, such as cyclopropyl, cyclobutyl, cyclo-pentyl, cyclohexyl, cycloheptyl or cyclooctyl, in par-ticular cyclopropyl, cyclobutyl, cyclopentyl or cyclo-hexyl, which may carry from one to three of the following radicalse halogen, such as fluorine, chlorine, bromine or iodine, in particular fluorine or chlorine; alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl, in particular methyl and ethyl; haloalkyl such as fluoro-methyl, difluoromethyl, trifluoromethyl, chlorodifluoro-methyl, dichlorofluoromethyl, trichloromethyl, 1-fluoro-ethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoro-ethyl,2-chloro-2,2-difluoroethy1,2,2-dichloro-2-fluoro-ethyl, 2,2,2-trichloroethyl or pentafluoroethyl, in particular trifluoromethyl; alkoxy such as methoxy, ethoxy, n-propoxy, 2-methylethoxy, n-butoxy, 1-methyl-propoxy, 2-methylpropoxy or 1,1-dimethylethoxy, in particular methoxy or ethoxy,; haloalkoxy, such as difluoromethoxy, trifluoromethoxy, chlorodifluormethoxy, 20~ dichlorofluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2,2,2-trifluo-roethoxy, 2-chloro-1,1,2-trifluoroethoxy or pentafluoroethoxy, in particular trifluorometk~oxy;
alkyl as mentioned above, and pentyl, l~methyl butyl, 2-methylbutyl, 3=methylbutyl, 1,1-da.methylpropyl, 1,2-daxaethylpropyl, 2,2-diznethylpropyl, l-ethylpropyl, beryl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, Z,3-d3.methylbutyl, 2,2-dime~hylbutyl, 2,3-dimethylbutyl, 3,3-dime~hylbutyl, I-ethylbutyl, 2-ethylbutyl, 1,1,2-trim~thylpropyl, 1,2,2-tacimethypropyl, l-ethyl-1-methyl-propyl or 1-ethyl-2-methylpropyl, in particular methyl, ethyl, 1-methylethyl or 1,1-dimethylethyl, which may carry from one to three of the following radicalse hydroxyl;. halogen as mentioned above, in particular fluorine or chlorine; alkoxy as mentioned above, in particular methoxy ar etho~ey; haloalkoxy as mentioned f - 15 - O.Z. 0050/41113 above, in particular trifluoromethoxy; alkylthio, such as methylthio, ethylthio, n-propylthio, 1-methylethyl-thio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio or 1,1-dimethylethylthio, in particular methylthio or ethylthio; haloalkylthio such as difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, 1-fluoro-ethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthia, 2,2,2-trichloroethylthio or pentafluoroethylthio, in particular trifluoromethyl-thio or pentafluoroethylthio; hydroxycarbonyl; alkoxyiso-propyloxycarbonyl; alkylamino such as methylamino, ethylamino, propylamino, isopropylamino, in particular methylamino; dialkylamino such as dimethylamino, diethyl-amino, dipropylamino, diisopropylamino, methylethylamino, in particular dimethylamino; cycloalkylamino such as cyclopropylamino, cycylobutylamino, cyclopentylamino or cyclohexylamino, in particular cyclopropylamino; and/or a radical ~m where R is cyano; nitro; halogen such as, in particular, fluorine or chlorine; alkyl such as, in particular, methyl, ethyl or l-methylethyl; haloalkyl such as, in particular, trifiuoroethyl; alkoxy such as, in particular, methoxy, ethoxy or 1-methylethoxy;
haloalkoxy such as, in particular, difluorom~thoxy or trifluoromethoacy; alkylthio such as, in par-ticular, methylthio or ethylthio; haloalkylthio such as, in particular, difluoromethylthio or trifluoro-methylthio andlor alkoarycarbonyl such as methoxycar bonyl, ethoxycarbonyl, propyloxycarbonyl, 1-methyl ethoxycarbonyl, butoxycarbonyl, 1-methylpropoxy carbonyl, 2-msthylpropoxycarbonyl or 1,1-dimethyl ethoxycarbonyl, in particular metho~cycarbonyl or ethoxycarbonyl, ~''~'~l Toi ~~ 'tl (.~ iI
- 16 - o.z. ooso~~am3 m is 0, 1, 2 or 3, it being possible for the radicals R to be different from one another if m is 2 or 3;
RZ is hydroxyl; amino;
alkylamino, such as, in particular, methylamino or ethylamino;
dialkylamino, such as, in particular, dimethylamino or diethylamino; alkyl as mentioned in the case of R1 and carrying an aminocarbonyl group;
alkoxy, such as, in particular, methoxy or ethoxy, which may carry a radical ~Rm 'v alkenyl, such as 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-psntenyl, 3-methyl-2-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1=methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-~dimsthyl~-~2-propenyl, 1, 2-dimethyl--2-propenyl, 1-ethyl-2~propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-h~xenyl, 1-methyl-2-pentenlrl, 2-methyl-2-pentenyl, 3-m~thyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pent~nyl, 2-methyl-3~pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1'-methyl-4-pentenyl, 2-methyl-4-p~ntenyl, 3-methyl-4-pemtenyl:, 4-methyl-~-pentenyl,l,1-dimethyl-2-butenyl,l,l-dimethyl~3-butenyl, 1,2-dimethyl-2-butenyl; 1,2-dimethyl-3-butenyl, 1,3-d3.methyl-2-baatenyl,l,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-- butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl 2-butenyl,,2-ethyl-3-butenyl,l,l,2~trimethyl-2-propenyl, ,3D 1-ethyl-1-methyl-2-propenyl or 1-ethyl-2-methyl-2 ~~l~~r~
- 17 - O.Z. 0050/41113 propenyl;
alkynyl, such as 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-alkynyl, S-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;
in particular 2-propenyl or 2-propynyl, or phenyl or naphthyl, it being possible for these groups to carry from one to three of the radicals mentioned in general and specific terms in the case of R;
a 5- to 6-membered heterocyclic ring containing one or two heteroatoms selected from the group comprising nitrogen, oxygen and sulfur, such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydro-thienyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetxahydropyranyl, 2-furanyl, 3-furanyl, 2-thienyl, 3-thienyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazol.yl, 3-isothiazolyl, 4-isothiazolyl, 5-iso~thiazolyl, 2-oxazolyl, 4-oxazolyl, 5=oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-.imidazolyl, 5--imidazolyl, 2-pyrrol:yl, 4-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl or 2-(4,6-dimethylpyrimidinyl), it being possible for this ring to contain one or two of he following radicals: halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, and/or alkylthio as mentioned in general and specific terms in the case of R1;

- lg - O.Z. 0050/41113 one of the groups mentioned in general or specific terms in the case of R1, or R1 and RZ together are a 4-. to 7-membered chain which may contain one of the following groups as a ring member in addition to methylene groups: oxygen, sulfur, N(CH3)- or -CO-, such as CH
-( 2)3-i °(CH2)4-I -(CHZ)5-i (CH2)8-~
-CHZ-0-CHz-, -CHZ-CHZ-O-CHZ-CH2-, -CH -S-CH
2 2- ~
-CHz-CH2-S-CHZ-CHZ-, -CH2-CHZ-N ( CHI ) -CHZ-CHZ or - ( CH2 ) 3-CO-, in particular - ( CHZ ) S- or -CH2-CHZ-0-CHZ-CHZ;
R3 is a 5- to 6-membered heterocyclic ring containing one or two heteroatoms taken from the group comprising oxygen, sulfur and nitrogen, as mentioned in the case of R~, it being possible for this ring to carry one or two of the following radicals: halogen, such as, in particular, fluorine or chlorine, alkyl, such as, in particular, methyl, haloalkyl, such as, in particular, trifluoro-methyl or chlorodifluoromethyl, alkoxy, such as, in particular, methoxy or ethoxy, haloalkoxy, such as, in particular, trifluoromethoxy, trichloromethoxy or penta-fluoroethoxy, alkylthio, such as, in particular, methyl-thio, and/or haloalkylthio, such as, in particular, trifluoromethylthio;
alkenyl as mentioned in the case of RZ~ in particular 2-propenyl, alkynyl as mentioned in the case of RZ, in particular 2~propy°nyl, or phenyl, ~.t being possible for these groups to card from one to three of the radicals mentioned in g~neral and,sp~cific terms in the case of R, one of the groups mentioned in general ax specific terms in the case of R1;
R" is vitro; cyano; carboxyl;
halogen, such as, in particular, fluorine, chlorine or - 19 - O.z. 0050/41113 bromine;
alkoxy or alkylthio, such as, in particular, methoxy, ethoxy, methylthio or ethylthio, it being possible for these groups to carry from one to nine halogen atoms, such as, in particular, fluorine or chlorine;
or one of the groups mentioned in general or specific terms in the case of R3, it being possible for phenyl and alkynyl in this position also to have the foilowing meanings:
ethenyl, 1-propenyl, 1-methylethenyl, 1-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-pentenyl, 1-methyl-Z-butenyl, 2-methyl-1-butenyl, 1,1-dimethyl-1-propenyl, 1-ethyl-1-propenyl, 1-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pent~nyl, 4-methyl-1-pentenyl, 1,2-dimethyl-1-butenyl, 1,3-dimethyl-1-buteny1,2,3-dimethyl-1-butenyl,3,3-dimethyl-1-butenyl, 1-ethyl-1-butenyl, 2-ethyl-1-butenyl, 1-ethyl-2-methyl-1-propenyl, ethynyl, 1-propynyl, 1-butynyl, 1-pentynyl, 3-methyl-1-butynyl, 1-hexynyl, 3-methyl-1-pentynyl, 4-methyl-1-pentynyl or 3,3-dimethyl-1-butynyl;
RS is 4,5-dihydrooxazol-2-yl or COYRe;
Y is oxygen or sulfur;
RB is hydrogen;
cycloalkyi as mentioned in the case of R1, in particular cyclopentyl or cyclohexyl;
alkyl as mentioned in the case of R1, in particular methyl, ethyl, propyl, 1-methylethyl or hexyl, which may carry from one to five halogen atoms, such as, in par-ticular, fluorine or chlorine, or hydroxyl groups and/or one of the following radicalsa cyano,,aminocarbonyl, ~~r~:
- 20 - O.Z. 0050/1113 carboxyl, trimethylsilyl, alkoxy, such as, in particular, methoxy or ethoxy, alkoxyalkoxy, such as methoxyethoxy, ethoxyethoxy or propyloxyethoxy, in particular methoxy-ethoxy, alkylthio, such as, in particular, methylthio ox ethylthio; alkylamino, such as, in particular, methylamino or ethylamino, dialkylamino, such as, in particular, dimethylthio or methylethylamino, alkyl-sulfinyl, such as methylsulfinyl, ethylsulfinyl, propyl-sulfinyl, isopropylsulfinyl, in particular methylsulfinyl or ethylsulfinyl; aklylsulfonyl such as methylsulfonyl;
ethylsulfonyl, propylsulfonyl or isopropylsulfonyl, in particular methylsulfonyl or ethylsulfonyl; alkoxy-carbonyl, such as, in particular, methoxycarbonyl; alkyl-aminocarbonyl such as methylaminocarbonyl, ethylaminocar-bonyl, propylaminocarbonyl or isopropylaminocarbonyl, in particular methylaminocarbonyl or ethylaminocarbonyl;
dialkylaminocarbonyl, such as di.methylaminocarbonyl, diethylaminocarbonyl,dipropylaminocarbonyl,diisopropyl-aminocarbonyl, dicyclopropylaminocarbonyl or methylethyl-aminocarbonyl, in particular dimethylaminocarbonyl or diethylaminocarbonyl; dialkoxyphosphonyl, such as di-methoxyphosphonyl, diethoxyphosphonyl, dipropoxy-phosphonyl or diisopropoxyphosphonyl, in particular dimethoxyphosphonyl or diethoxyphosphonyl; alkaniminooxy, such as, in particular, 2-propaniminoxy; phenyl, thienyl, benzyloxy, benzylthio, furyl, tetrahydrofuryl, phthalimi do and/or benzoyl, it being possible for the cyclic radicals to themselves carry from one to three of the radicals m~ntioned in general or specific terms in the case of R;
alkenyl, such as, in particular, 2-propenyl or 2-butenyl, alkynyl, such as, in particular, 2-prnpynyl, or cyclo-alkenyl, such as, in particular, 2-cyclopentenyl or 2-cyclolaexenyl, it being possible for these groups to carry one of the following radicalss: hydroxyl, halogen, such as, in particular, fluorine or chlorine, alkoxy, ~ '~"'~~,~s tx %:f -:;~ r.~ s.'~, - 21 - O.Z. 0050/41113 such as, in particular, metho~cy or ethoxy, or phenyl, which may itself carry from ons to three of the radicals mentioned in general or specific terms in the case of R;
a 5- to 6-membered heterocyclic ring containing one or two heteraatoms selected from the group comprising nitrogen, oxygen and sulfur, as mentioned in the case of RZ, in particular tetrahydrofuranyl or tetrahydropyranyl;
phthalimido; tetrahydrophthalimido; succinimido;
maleiimido; benzotriazolyl;
phenyl which may carry from one to three of the radicals mentioned in general or specific terms in the case of R;
N=CR'R~ where R' is hydrogen or alkyl as mentioned in the case of Rl, in particular methyl, ethyl or 1-methylethyl, and R8 is cycloalkyl, such as, in particular, cyclopropyl, phenyl, furyl or one of the groups mentioned in the case of R', or R' and R~ together form an alkylene chain, such as butylene, pentylene, hexylene or heptylene, in particular butylene or pentylene, and agriculturally useful salts'thereof.
Particularly preferred compounds l or Ia are those in which R~ and R4 are hydrogen, and compounds z and Ia where Rx is hydrogen;
R2 is alkyl, such as, in particular, m~thyl, ethyl, propyl, 1-methyl~thyl or 1,1-dimethylethyl, or cycio-alkyl, such as, in particular, cyclopropyl, cyclopentyl or cyclohexyl;

- 22 - O.Z. 0050/43.113 R3 is hydrogen;
alkyl, such as, in particular, methyl, ethyl, propyl or 1-methylethyl, or phenyl which may carry from one to three of the following radicals: halogen, such as, in particular, fluorine or chlorine, alkyl, such as, in particular, methyl, ethyl or 1-methylethyl, haloalkyl, such as, in particular, tri-fluaromethyl, haloalkoxy, such as, in particular, tri-fluoromethoxy, alkylthio, such as, in particular, methyl-thio, and/or haloalkylthio, such as, in particular, trifluoromethylthio;
R~ is hydrogen;
RS is COYRs;
Y is oxygen;
Rg is hydrogen or -N=R'R8, and R' is hydrogen or alkyl, as mentioned in general or specific terms in the case of R3;
R8 is cycloalkyl, as mentioned in specific terms in the cas~ of RZ, or one of the groups mentioned in the case of R', or R' and R8 together are an alkylene chain, such as, in particular, butylene or pentylene.
Examples of particularly preferred pyrazole-3 carboxamides of general formula Ia are listed in the table belo~r>

~>~.~
r ~e :~ ~a : ~
M

t0 \ ~ x x x x x xx x x x x x x x x x x x O

O

O r O O O O O OO O O O O O O O O O O
O

N

O

N

O

r. ,-.~ '-'r-r. n-.n--~r.,_.r-.~ .rr r-r.
~-.

T r~3~~ T >fT ~ T ~ aT T ~,T T.~ T

+~ +~+~+~+~d~-0~~H+>~i-~.d.~+~+~+~+'~ +~
-1~

7 7 7 7 7 77.7.7 3 7 7 3.7 7 7 7 a a a a .o.ca a asa .c~a a a a a a I I I 1 1 I1 I I I .c 1 I I 1 1 I
I
I

L L L L L LL L L L L L L L L L L
L

N N N y G)N NN N N N N N N N N N N
d fp d ~' i~1~+~i~+~i~i~i~.~1-~~ i-~+~-N+~+~+~
1~

(h r-~

a; x x S Z x Sx x x Z Z x x x x Z Z
x -z M r z-x ~ = x x x x xx r x x x x x x x x r x r ~ ~ r"

~ a a ~

oc +~.~s a~

E d u~

1-.1 o 0 ~ ,...L L

s y,O O

N r -4~C

r.y~,...y~ N O .-..C
.-r-. ~ T -F~T .H I .a4-V
?~

,~y~.1,~C aCa. T L ..-. r-.
~ i~ ~

r.G ~~ 7 N GDNV ~C~0L L
.

7~O ~ ~7 a fl..CL O V isi~
O

y-. fl.L ~,7a I I i I s r~I I ~' I

W 7, ~ O G.+~aI O.O O -1~X N N ~-~0 O

.- .!_.7~L 1 -11 i~r . n..(yO ~ L
N r.

a +1 .G!3.O.a OV 'LV V V E .CN N
V

.
~D M G7 .faI tnI NW N 9s~ ~ 1 i~ ~~N
T

~ ~ E y C .,..C .,..y~.y,iV V V N d N N rt9E
V

M

rr .-a ac x s xx x x x x x xx x x x x xx x x x x xx x x x u, o r O O OO O O O O O OO O O O O OO O O O O OO O O O

N

d N

r-.~,r-~~ r-~r.er-1rrn-.e-.e-y-.r-.r-~H r~rrr..rr r r-r r r-rr a T aa ~,7,',T T aa a a ~ T Ta a a T ~,~,~,a >,a > > >> > > > > > a~ ~ ~ ~ ~ >> ~ ~ 3 ~ a~

.a .~to.o.G~ .o.e.b.o.a~ .G~ .a.aa s~.a.a.Q.o~ .a~
I I 1I 1 I 1 i I 1I I I I .I:I 1 1 1 I 11 1 1 I
I

+s +~+s+~+~+~~ +~+~+~.+~.v-s+~.a.~+~+~+s+~.cue+>+~+~+~.a;~ +~

L. L LL L L L L L LL L L L L L.L L L L L LL L L L

N N N NN N O N d W NN N N d N NN N O N GlNN ~ d d LY is d-~i~+~~Ni~~i-~~1-~i~i~i~i~i~-I-~i~i~i~-S~d~d-~i~i~i~i~d-~i~

N

~ .
~ x x xx x x x x S xx x x x x xx x x x x Zx x x x ~ x x xx x x x x g aa x a z x xx a x ~ x xx x x s c c ~, L ~ T r, ~ d. ~ T

' ~' c '' ~ - v a a~~ ~ w . r., o .~a~V V u. T a s '.. L a.s ~n .-. ~ c a r,..r-.e--~ILM r.'-..~yv-.$iN r..
y, 4 ~ ~

r r V ?~T U liT a CT at.CT
~ 1 y N .-...-..rT T :...... CC . V C C WC ~ d Q.

.C.-....t T T TC s=V 1..~ NN rr N d .eG?...~ O

.-.G:T W -' C C CN C1. V V t.GV 4..G.CG.. S.a L
.C

a 1~ e,~, d ~ ~s .sr.-~ ...o.a ~---a.ss1a .h.a~o.

~ ~ ~T L ~ "",~~ aG.Cta.~.V 4.I II I 1 1 1 ~~I 1 7 I

T N Ii.~r0N T d.C.dI 1 '-~v ~ MM ~DtON N rM ~Q,pO

+s C ~~ fl..GC I 1 1~ r I I 4.'t_ O O Vx 1 vl p ~ ~..~tl4 i1C~lila.u.V U d'~'~ VV ~ J'Z Z VV ~ -t-~

en L ..~.1I L I .Ci I II I 11 1 I 11 1 1 U U MN A M Ct.~M N~ N N N N ~c'~N N ~ N 3'd'N ~ N
~

. .

M

~ z x xx x x x xx x x x x x xx s x x xx x x x x o r O O OO O O O OO O O O O O OO O O O OO O O O
O

N

O

N

O

r.

,..r,r.,-.-..-,-. r.,-.r.~ ~-.-.-..-..r.rr....-...~ ..a ~

,.,~.,>,~,',~,9, y,>,~,a ~,a a 7,a aa a,a a a ao.
a +~ +?..1.~+~+~i.~+~ +>+~i.~+~+~~ +~+~i~+~+.~+~+~i-Ii.~+~O
+~

O 7 7 O 77 7 7 7 7O ~ ~ 7 7 7 77 7 7 7 7 7L

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66 O.Z. 0050/41113 Suitable salts of compounds of the formula Ia are agriculturally useful salts, for example alkali metal salts, such as potassium and sodium salts, alkaline earth metal salts, such as calcium, magnesium and barium salts, manganese, copper, zinc or iron salts, e.g., ammonium salts, tetraalkyl-ammonium salts, benzyltrialkylammonium salts, trialkylsulfonium salts and trialkylsulfoxonium salts.
The herbicidal compounds I, or agents containing them, may be applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), disper-lions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used, but they must ensure as fine a distribution of the active ingredients according to the invention as possible.
For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, and oils of vege-'table or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphtha-lenes and their derivatives, methanol, ethanol, propanol, butanol, cyclo-hexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc. are suitable.
Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concen-trates which are suitable for dilution with water may be prepared from active ingredient, wetting agent; adherent, emulsifying or dispersing agent and possibly solvent or oil.
Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid, phenoisulfonic acid, naphthalenesulfonic acid and dibutylnaphthalene-sulfonic acid, and of fatty acids, alkyl and alkylaryl sulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, s r~ m a~.'.~~
67 O.Z. 0050/41113 polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxyl-ated octylphenol and ethoxylated nonyiphenol, alkytphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated potyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite waste liquors and methyl cellulose.
Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.
Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain meals, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.
The formulations contain from 0.1 to 95, and preferably 0.5 to 90, ~o by weight of active ingredient. The active ingredients are used in a purity of 90 to 100, and preferably 95 to 100, fo (according to the NMR spectrum).
Compounds I according to the invention may be formulated as follows:
I. 90 parts by weight of compound no. 1.014 is mixed with 10 parts by weight of N-methyl-alpha-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.
II. 20 parts by weight of compound no. 1.022 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and l mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzene-sulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dis-persion is obtained containing 0.02% by weight of the active ingredient.
III. 20 parts by weight of compaund no. 1.008 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the ~~~~~'~~y~
r t" Pl fl 68 O.Z. 0050/41113 solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained containing 0.02 by weight of the active ingredient.
IV. 20 parts by weight of compound no. 1.040 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction having a boiling point between 210 and 280°C, and parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of 10 water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.029'° by weight of the active ingredient.
V. 20 parts by weight of compound no. 1.014 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 17 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained containing O.l~o by weight of the active ingredient.
VI. 3 parts by weight of compound no. 1.016 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3~0 by weight of the active ingredient.
VII. 30 parts by weight of compound no. 1.022 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.
VIII. 20 parts by weight of compound no. 1.004 is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8,parts of a fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenol-sulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.
The active ingredients or the herbicidal agents containing them may be applied pre- or postemergence. If certain crop plants tolerate tha active ingredients less well, application techniques may be used in which the herbicidal agents are sprayed from suitable equipment in such a manner that the leaves of sensitive crop plants are if possible not touched, and the agents reach the soil or the unwanted plants growing beneath the crop plants (post-directed, lay-by treatment).

~~~J~~~

BASF Aktiengesellschaft 69 O.Z. 0050/41113 When the active ingredients are used as herbicides, the application rates depend on the objective to be achieved, the time of the year, the plants to be combated and their growth stage, and are from 0.001 to 5, preferably 0.01 to 2, kg of active ingredient per hectare.
To increase the spectrum of action and to achieve synergistic effects, the compounds I may be mixed with each other, or mixed and applied together with numerous representatives of other herbicidal or growth-regulating active ingredient groups. Examples of suitable components are diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiolcarbamates, halocarboxylic acids, triazines, amides, ureas, Biphenyl ethers, triazinones, uracils, benzofuran deriva-tives, cyclohexane-1,3-dione derivatives, quinolinecarboxylic acids, (het-ero)-aryloxyphenoxypropionic acids and salts, esters, amides thereof, etc.
It may also be useful to apply the herbicidal compounds Ia, either alone or in combination with other herbicides, in admixture with other crop protection agents, e.g., agents for combating pests or phytopathogenic fungi or bacteria. The compounds may also be mixed with solutions of mineral salts used to remedy nutritional or trace element deficiencies.
Non-phytotoxic oils and oil concentrates may also be added.
Synthesis examples The directions given in the synthesis examples below were used, after appropriate modification of the starting materials, to obtain further compounds Ia. The compounds thus obtained are given below with their physical data.
Manufacturing examples 1. 1(H)-4-ethoxycarbonyl-1-methylpyrazole-3-carboxylic acid A solution of 10.5 g (50 mmol) of diethyl 1(H)-1-methylpyrazote-3,4-dicarboxylate (J. Org. Chem. 31, 2491 (1966)) in 200 ml of ethanol/water (1:1) was cooled to 0°C, and a solution of 1.96 g (0.049 mol) of sodium hydroxide solution in 50 ml of water was dripped in over a 30-minute period. The mixture was allowed to stand for l4 hours at room temperature, the solvent mixture was removed under reduced pressure, the solid residue was taken up in 100 ml of water and acidified with 10~ strength hydro-chloric acid, and the precipitated solid was removed by suction filtra-tion. There was obtained 7.40 g (74~) of the hemiester of m.p. 182°C
(from water) as a white powder.

BASF Aktiengeseltschaft 70 O.Z. 0050/41113 2. 1(H)-4-ethoxycarbonyl-1-methylpyrazole-3-carboxylic acid chloride 7.20 g (36 mmol) of 1(H)-4-ethoxycarbonyl-1-methylpyrazole-3-carboxylic acid from Example 1 was introduced in portions into 20 ml of thionyl chloride, and the whole was refluxed for 2 hours. Excess thionyl chloride was then removed under reduced pressure, the residue was taken up in 50 ml of diethyl ether and the whole was stirred for 30 minutes with 2.00 g of activated carbon. After filtration the filtrate was concentrated under reduced pressure. The residue was 7.30 g (94%) of the acid chloride as a white solid having a melting point of 65°C.
3. 1(H)-4-ethoxycarbonyl-1-methylpyrazole-3-carboxylic isopropylamide 4.00 g (68 mmol) of isopropylamine was dissolved at 0°C in 100 ml of dichloromethane, the solution obtained was cooled to -10°C, and over a period of 30 minutes at this temperature a solution of 7.20 g (33 mmol) of 1(H)-4-ethoxycarbdnyl-1-methylpyrazole-3-carboxylic acid chloride from Example 2 in 20 ml of dichloromethane was dripped in. After all had been added, the mixture was allowed to warm up to room temperature, after which it was stirred for 2 hours and then hydrolyzed by adding 100 m1 of 100 strength hydrochloric acid. The organic phase was separated off, dried wfith sodium sulfate and evaporated down. The residue was 7.20 g (910) of the amide as a white solid having a melting point of 134°C (from a 1:1 mixture of cyclohexane/ethyl acetate).
4. 1(H)-1-methyl-3-(isopropylaminocarbonyl)-pyrazole-4-carboxylic acid A mixture of 7:00 g (29 mmol) of 1(H)-4-ethoxycarbonyi-1-methylpyrazole-3-carboxylic isopropylamide from Example 3 and 1:85 g (33 mmol) of potassium hydroxide in 60 m1 of a 1:1 mixture of water and methanol was heated at 60°C for 3 hours. The solvent mixture was then reduced under reduced pressure and the solid residue was taken up in 20 ml of water. The mixture was acidified with concentrated hydrochloric acid and the precipitated product was suction filtered, g9ving 6:00 g (98°l0) of the carboxylic acid as a white solid having a melting point of 180'C (from methanol) (active ingredient no. 1001).
5. 1(H)-3-(2-chlorobenzylaminocarbonyl)-1-methylpyrazole-4-carboxylic acid A mixture of 2.55 g (18 mmol) of 2-chlorobenzylamine and 2.00 g (20 mmot) of triethylamine in 50 ml of dichloromethane was cooled to 0'C and a solution of 4.00 g (18 mmol) of 1(H)-4-ethoxycarbonyl-i-methylpyrazole-3-carboxylic acid chloride from Example 2 in 20 ml of dichloromethane. The mixture was allowed to heat up to room temperature, after which it was sASF Aktiengesellschaft 71 O.Z. 0050/41113 stirred for 2 hours and then hydrolyzed by adding 50 ml of 109'o strength hydrochloric acid, and the organic phase was separated. The mixture was concentrated in a rotary evaporator, the residue was taken up with 50 ml of a 1:1 mixture of water and methanol, and a solution of 1.12 g (20 mmol) of potassium hydroxide in 20 ml of water was added. The resulting mixture was heated for 2 hours at 65'C and freed from solvent under reduced pres-sure, and the residue was taken up with 50 ml of water. This mixture was acidified with concentrated hydrochloric acid, and the precipitated prod-uct was suction filtered. There was obtained 5.00 g (95fo) of the amide of melting point 154'C (active ingredient no. 1.018).
6. 1(H)-1-methyl-4-(2-propaniminoxycarbonyl)-pyrazole-3-carboxylic acid tert-butylamide Over a period of 30 minutes, a mixture of 4.50 g (20 mmoi) of 1(H)-3-tert-butylaminocarbonyl-1-methylpyrazole-4-carboxylic acid, 1.50 g {20 mmol) of acetonoxime and 4.80 g (48 mmol) of triethylamine in 20 ml of dichloro-methane was dripped into a suspension of 6.12 g (24 mmoi) of 1-methyl-2-chloropyridinium iodide in 20 ml of dichloromethane. After all had been added, the mixture was refluxed for 3 hours, the solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel using as eluant a 5:1 dichloromethane/ethyl acetate mixture. There was thus obtained 4.40 g (80%) o-f the oxime ester as a white solid having a melting point of 111'C (active ingredient no. 1.014).
The compounds given in the table below were prepared analogously to the examples above.

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I-- W .- r,.~ .~.-...r..~ .-r 76 O.Z. 0050/41113 Use examples The herbicidal action of the pyrazole-3-carboxamides of the formula Ia is demonstrated in greenhouse experiments:
The vessels employed were plastic flowerpots having a volume of 300 cm3 and filled with a sandy loam containing about 3.O~o humus. The seeds of the test plants were sown separately, according to species.
For the preemergence treatment, the formulated active ingredients were applied to the surface of the soil immediately after the seeds had been sown. The compounds were emulsified or suspended in water as vehicle, and sprayed through finely distributing nozzles. After the agents had been applied, the vessels were lightly sprinkler-irrigated to induce germin-ation and growth. Transparent plastic covers were then placed on the vessels until the plants had taken root. The cover ensured uniform germin-ation of the plants, insofar as this was not impaired by the active ingredients.
For the postemergence treatment, the plants were grown, depending on growth form, to a height of 3 to 15 cm before being treated with the com-polands, suspended or emulsified in water. The application rate for post-emergence treatment was 1.0 kg/ha.
The pots were set up in the greenhouse, heat-loving species at 20 to 35°C, and species from moderate climates at 10 to 25°C. The experiments were run for from 2 to 4 weeks. During this period the plants were tended and their reactions to the various treatments assessed. The assessment scats was 0 to 100, 100 denoting nonemergence or complete destruction of at least the visible plant parts, and 0 denoting no damage or normal growth.
The plants used in the experiments were Chenopodium album, Sinapis albs and Solanum nigrum.
Active ingredients nos. 1.014 and 1.022, applied postemergence at a rate of 1.0 kg/ha, provided excellent control of unwanted broadleaved plants.

Claims (5)

1. A pyrazole-3-carboxamide of the general formula (I):
where the substituents have the following meanings:
R1 and R4 hydrogen;

C1-C4-alkyl or C3-C8-cycloalkyl, hydrogen;
C1-C4-alkyl;
phenyl which may carry from one to three of the following radicals; halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and/or C1-C4-alkylthio;

a COYR6 group;
Y
oxygen;

hydrogen, or an -N=CR7R8 group where R7 is hydrogen or C1-C4-alkyl and R8 is C3-C6-cycloalkyl or a radical R7, or R7 and R8 together form a 4- to 7-membered alkylene chain, or an agriculturally useful salt thereof.
2. A process for the manufacture of compound I as set forth in claim 1, R5 denoting a group CO2H, wherein a pyrazole-3-carboxamide I, where R5 is a group CO2R' and R' is C1-C4-alkyl ~~(R5 = CO2R') is hydrolyzed in the presence of an aqueous base.
3. A process for the manufacture of compound I as set forth in claim 1, R5 denoting a group COYR6, wherein a pyrazole-3-carboxamide I, R5 denoting a group CO2H

(R5 = CO2H) is converted to the halide or another activated form of the carboxylic acid, and this derivative is then esterified with a compound IV

where Y and R6 are as defined in claim 1.
4. A herbicide containing at least one pyrazole-3-carboxamide of the general formula I as c3aimed in claim 1 and conventional inert additives.
5. A method of controlling undesired plant growth, wherein the undesired plant and/or its habitat are treated with a herbicidally effective amount of a pyrazole-3-carboxamide as claimed in claim 1.
CA002025932A 1989-09-23 1990-09-21 Pyrazole-3-carboxamides Expired - Fee Related CA2025932C (en)

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