Ciba-geigy Corporation

Werner Fory

Willy Meyer

Rolf Schurter

Georg Pissiotas

Henry Martin

Karl Gass

Werner Topfl

Beat Bohner

Hermann Rempfler

Josef Ehrenfreund

Hans Tobler

Henry Szczepanski

Hans-Georg Brunner

Verena Laanio

Hans Moser

Kurt Burdeska

Robert Nyfeler

Hanspeter Fischer

Dieter Lohmann

Daniel Bellus

Beat Muller

Otto Rohr

Gerd Greber

Haukur Kristinsson

Rene Eric Muntwyler

Rudolph C Thummel

Peter J Diel

Johannes P Pachlatko

Alfons Lukaszczyk

Guglielmo Kabas, Deceased

Manfred Boger

Dieter Durr

Werner Breitenstein

Manfred Hudetz

Elmar Kerber

Karl Gatzi

Hermann Kny

Peter Baccini

Karl Gotzi

Willy Mayer

Erfinders K Gass

Rainer Kuhlmeyer

Mixtures of a herbicidally effective amount of a pyridylsulfonylurea of formula I, ##STR1## wherein R, R.sub.1, R.sub.2 and A are as defined in claim 1, and of a herbicide-antagonistically effective amount of a sulfamoylphenylurea of formula II, ##STR2## wherein R.sub.7 to R.sub.11 and A.sub.2 are as defined in claim 1, are very suitable for controlling weeds in crops of useful plants, especially maize and sugar cane.

Selective safened herbicidal composition

A compound of the formula II ##STR1## in which R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkoxy or CF.sub.3 and A is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each of which is monosubstituted to trisubstituted by halogen, or is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each of which is substituted by C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.2 -C.sub.4 alkenyl, C.sub.5 -C.sub.6 cycloalkenyl, amino, C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 dialkylamino or C.sub.2 -C.sub.4 alkynyl, it being possible for the C.sub.2 -C.sub.4 alkenyl radical and the C.sub.5 -C.sub.6 cycloalkenyl radical to be additionally monosubstituted to trisubstituted by halogen; or A is a 4- to 6-membered saturated heterocycle which contains a hetero atom selected from the group consisting of O, N and SO.sub.2 ; or A is C.sub.1 -C.sub.4 alkyl which is substituted by a 4- to 6-membered saturated heterocycle which contains a hetero atom selected from the group consisting of O, N and SO.sub.2.

Pyridin-2-yl-sulfonamides useful for the preparation of herbicidally

(Cyclopropyl-triazinyl- and cyclopropyl-pyrimidinyl-)pyridylsulfonylureas of formula I ##STR1## wherein R and R.sub.1 are each independently of the other hydrogen or methyl;

Pyridylsulfonylureas

N-pyridinesulfonyl-N'-pyrimidinyl- and -triazinyl-ureas of formula I ##STR1## wherein R.sub.1 is hydrogen or fluorine;

Sulfonylureas

N-Pyridylsulfonyl-N'-pyrimidinylureas of formula I ##STR1## wherein R.sub.1 is methyl or methoxy and R.sub.2 is hydrogen or methyl; and the salts of those compounds with mines, alkali metal or alkaline earth metal bases or with quaternary ammonium bases, have good pre- and post-emergence selective herbicidal and growth-regulating properties.

N-Pyridinesulfonyl-N'-pyrimidinyl- and -triazinylureas of the formula I ##STR1## in which R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 C.sub.4 haloalkoxy or CF.sub.3 ; R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; A is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each of which is monosubstituted to trisubstituted by halogen, or is C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each of which is substituted by C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.2 -C.sub.4 alkenyl, C.sub.5 -C.sub.6 cycloalkenyl, amino, C.sub.1 -C.sub.4 alkylamino, C.sub.1 -C.sub.4 dialkylamino or C.sub.2 -C.sub.4 alkynyl, it being possible for the C.sub.2 -C.sub.4 alkenyl radical and the C.sub.5 -C.sub.6 cycloalkenyl radical to be additionally monosubstituted to trisubstituted by halogen; or A is a 4- to 6-membered saturated heterocycle which contains a hetero atom selected from the group comprising O, N and SO.sub.2 ; or A is C.sub.1 -C.sub.4 alkyl which is substituted by a 4- to 6-membered saturated heterocycle which contains a hetero atom selected from the group comprising O, N and SO.sub.2 ; X is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkyl which is monosubstituted to trisubstituted by halogen, or is C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkoxy which is monosubstituted to trisubstituted by halogen; Y is halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkyl which is monosubstituted to trisubstituted by halogen, or is C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkoxy which is monosubstituted to trisubstituted by halogen, or is cyclopropyl, methylamino or dimethylamino; and E is nitrogen or the methine group, and the salts of these compounds with amines, alkali metal bases or alkaline earth metal bases or with quaternary ammonium bases have good selective herbicidal properties pre-emergence and post-emergence, and good growth-regulating properties.

Pyridyl sulfonylurea herbicides

N-Arylsulfonyl-N'-pyrimidinyl-and N'-triazinylureas of formula I ##STR1## wherein Q is ##STR2## R is hydrogen or methyl; R.sub.1 is hydrogen, fluoro, chloro, C.sub.1 -C.sub.4 alkyl or methoxy;

N-Pyridinesulfonyl-N'-pyrimidinyl- and -triazinylureas of the formula I ##STR1## in which R.sub.1 and R.sub.2 independently of one another are hydrogen, C.sub.1 -C.sub.8 alkyl or C.sub.3 -C.sub.8 cycloalkyl; C.sub.2 -C.sub.8 alkyl or C.sub.3 -C.sub.8 cycloalkyl, each of which is monosubstituted or polysubstituted by halogen; C.sub.1 -C.sub.8 alkyl or C.sub.3 -C.sub.8 cycloalkyl, each of which is substituted by --NR.sub.5 R.sub.6, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkyl--S(O).sub.n --; C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl, each of which is substituted by C.sub.2 -C.sub.4 alkenyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.2 -C.sub.6 alkynyl or C.sub.4 -C.sub.8 alkadienyl; it being possible for the C.sub.2 -C.sub.4 alkenyl, C.sub.5 -C.sub.6 cycloalkenyl and C.sub.4 -C.sub.8 alkadienyl radicals to be monosubstituted or polysubstituted by halogen; or R.sub.1 and R.sub.2 together are a 4-5-membered C.sub.4 -C.sub.10 alkylene chain which can be interrupted by oxygen, sulfur or N--R.sub. 7 ; R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio; C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio, each of which is monosubstituted or polysubstituted by halogen; R.sub.4, R.sub.5, R.sub.6 and R.sub.7 independently of one another are hydrogen or C.sub.1 -C.sub.4 alkyl; n is 0, 1 or 2; X is C.sub.1 -C.sub.3 alkyl, or C.sub.1 -C.sub.3 alkyl which is monosubstituted to trisubstituted by halogen; C.sub.1 -C.sub.3 alkoxy, or C.sub.1 -C.sub.3 alkoxy which is monosubstituted to trisubstituted by halogen; Y is halogen, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkyl which is monosubstituted to trisubstituted by halogen; C.sub.1 -C.sub.3 alkoxy, or C.sub.1 -C.sub.3 alkoxy which is monosubstituted to trisubstituted by halogen; cyclopropyl, methylamino or dimethylamino; and E is nitrogen or the methine group, and the salts of these compounds with amines, alkali metal bases or alkaline earth metal bases or with quaternary ammonium bases have good selective herbicidal and growth-regulating properties when used pre- and post-emergence.

Certain-3-amino-2-pyridine-sulfonamide intermediates

N-Pyridinesulfonyl-N'-pyrimidinyl- and -triazinylureas of the formula I ##STR1## in which R.sub.1 and R.sub.2 independently of one another are hydrogen, C.sub.1 -C.sub.8 alkyl or C.sub.3 -C.sub.8 cycloalkyl; C.sub.2 -C.sub.8 alkyl or C.sub.3 -C.sub.8 cycloalkyl substituted by halogen; C.sub.1 -C.sub.8 alkyl or C.sub.3 -C.sub.8 cycloalkyl substituted by --NR.sub.5 R.sub.6, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkyl-S(O).sub.n --; C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.6 cycloalkyl substituted by C.sub.2 -C.sub.4 alkenyl, C.sub.5 -C.sub.6 cycloalkenyl, C.sub.2 -C.sub.6 alkynyl or C.sub.4 -C.sub.8 alkadienyl; or C.sub.2 -C.sub.4 alkenyl, C.sub.5 -C.sub.6 cycloalkenyl and C.sub.4 -C.sub.8 alkadienyl substituted by halogen; or R.sub.1 and R.sub.2 together are a 4-5-membered C.sub.4 -C.sub.10 alkylene chain which can be interrupted by oxygen, sulfur or N--R.sub.7 ; R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 - C.sub.4 alkylthio; C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio substituted by halogen; R.sub.4, R.sub.5, R.sub.6 and R.sub.7 independently of one another are hydrogen or C.sub.1 -C.sub.4 alkyl; n is 0, 1 or 2; X is C.sub.1 -C.sub.3 alkyl, or C.sub.1 -C.sub.3 alkyl which is substituted by 1 to 3 halogens; C.sub.1 -C.sub.3 alkoxy, or C.sub.1 -C.sub.3 alkoxy which is substituted by 1 to 3 halogens; Y is halogen, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkyl which is substituted by 1 to 3 halogens; C.sub.1 -C.sub.3 alkoxy, or C.sub.1 -C.sub.3 alkoxy which is substituted by 1 to 3 halogens; cyclopropyl, methylamino or dimethylamino; and E is nitrogen or the methine group, and the salts of these compounds with amines, alkali metal bases or alkaline earth metal bases or with quaternary ammonium bases have good selective herbicidal and growth-regulating properties when used pre- and post-emergence.

A microbicidal composition contains as active ingredient 2-chloro-4-trifluoromethylthiazol-5-carboxylic acid derivatives of the formula I ##STR1## R is an organic radical with up to 40 carbon atoms, which optionally contains nitrogen, oxygen or sulfur atoms and which can be transformed by hydrolosis or oxydation into the directly to the thiazol ring bound carboxyl rest.

Microbicidal composition

1,5-diphenylpyrazole-3-carboxylic acid derivatives of the formula ##STR1## in which each of R.sub.a and R.sub.b, independently of the other, represents halogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -haloalkyl, C.sub.2 -C.sub.5 -alkenyl, C.sub.2 -C.sub.5 -alkynyl or cyano, n represents zero or an integer from 1 to 3, and OR.sub.1 represents hydroxy, a plant-physiologically tolerable salt radical or any desired ester radical, are capable of antagonizing specifically the phytotoxic action of phenoxypropionic acid ester herbicides of the formula II ##STR2## in which G represents ##STR3## in which Hal.sub.1 represents fluorine, chlorine, bromine, iodine or trifluoromethyl, Hal.sub.2 represents hydrogen, fluorine, chlorine, bromine or trifluoromethyl, Z represents nitrogen or methine (--CH.dbd.), X represents an oxygen or sulphur atom, R.sub.1 ' represents halogen, trifluoromethyl, nitro, cyano, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy and n represents, 0, 1, 2 or 3 and T represents an ester, amide, cyanamide or oxime radical. Compositions, containing those components, as selective herbicides and the use of those two active ingredients for controlling weeds in crops of useful plants are described, as are also novel 1,5-diphenyl-pyrazole-3-carboxylic acid derivatives corresponding to the formula I and the preparation thereof.

1,5-Diphenylpyrazole-3-carboxylic acid derivatives for the protection of

1,5-diphenylpyrazole-3-carboxylic acid derivatives of the formula ##STR1## are capable of antagonising specifically the phytotoxic action of phenoxypropionic acid ester herbicides of the formula II ##STR2## in which G represents ##STR3## Compositions, containing those compositions, as selective herbicides and the use of those two active ingredients for controlling weeds in crops of useful plants are described, as are also novel 1,5-diphenylpyrazole-3-carboxylic acid derivatives corresponding to the formula I and the preparation thereof.

1,5-diphenylpyrazole-3-carboxylic acid derivatives for the protection of

A microbicidal compostion contains as active ingredient 2-chloro-4-trifluoromethylthiazol-5-carbonic acid derivatives of the formula I ##STR1## R is organic radical with up to 40 carbon atoms, which optionally contains nitrogen, oxygen or sulfur atoms and which can be transformed by hydrolosis or oxydation into the directly to the thiazol ring bound carboxyl rest. These compounds have good microbicidal activity and are used for the control and prevention of infestation of plants by phytophathogenic microorganisms.

N-phenylsulfonyl-N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence. In the formula

N-phenylsulfonyl-N'-triazinylureas

1,5-diphenylpyrazole-3-carboxylic acid derivatives of the formula ##STR1## in which each of R.sub.a and R.sub.b, independently of the other represents halogen, C.sub.1 -C.sub.5 -alkyl, C.sub.1 -C.sub.5 -haloalkyl, C.sub.2 -C.sub.5 -alkenyl, C.sub.2 -C.sub.5 -alkynyl or cyano, n represents zero or an integer from 1 to 3, and OR.sub.1 represents hydroxy, a plant-physiologically tolerable salt radical or any desired ester radical, are capable of antagonizing specifically the phytotoxic action of phenoxypropionic acid ester herbicides of the formula II ##STR2## in which G represents ##STR3## in which Hal.sub.1 represents fluorine, chlorine, bromine, iodine or trifluoromethyl, Hal.sub.2 represents hydrogen, fluorine, chlorine, bromine or trifluoromethyl, Z represents nitrogen or methine (--CH.dbd.), X represents an oxygen or sulphur atom, R.sub.1 ' represents halogen, trifluoromethyl, nitro, cyano, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy and n represents 0, 1, 2 or 3 and T represents an ester, amide, cyanamide or oxime radical. Compositions, containing those components, as selective herbicides and the use of those two active ingredients for controlling weeds in crops of useful plants are described, as are also novel 1,5-diphenylpyrazole-3-carboxylic acid derivatives corresponding to the formula I and the preparation thereof.

Growing community of inventors

Basel, Switzerland

Werner Fory