Ciba-geigy Corporation

Deutsche Gold- Und Silber-scheideanstalt Vormals Roessler

Ciba-geigy Corportion

Willy Meyer

Werner Fory

Beat Bohner

Werner Topfl

Karl Gass

Rolf Schurter

Dag Dawes

Laurenz Gsell

Konrad Oertle

Jozef Drabek

Saleem Farooq

Friedrich Karrer

Dieter Reinehr

Georg Pissiotas

Odd Kristiansen

Haukur Kristinsson

Rudolph C Thummel

Hans-Dieter Schneider

Werner F/o/ Ry

Josef Ehrenfreund

Dieter Durr

Ludwig Maier

Adrian Waldner

Jean-Marc Schlaeppi

Kurt Rufenacht

Achim Roloff

Klaus Ramsteiner

Jean Perchais

Beat Boehner

Werner Fury

Henry Szczepanski

Wolfgang Eckhardt

Pierre Martin

Daniel Bellus

Alfred Sallmann

Werner Schwarze

Herbert Klenk

Hanspeter Fischer

Hans Tobler

Karl Hoegerle

Urs Siegrist

Hans Greuter

Wolfgang Stutz

Hermann Kny

Erfinders K Gass

Wolfgang Leuchtenberg

Werner T/o/ Pfl

Franz Weibel

Bernard Wirz

N-Phenylsulfonyl-N'-pyrimidinylureas and -thioureas of formula I ##STR1## in which X is oxygen, sulfur, SO or SO.sub.2 ; W is oxygen or sulfur; R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, bromine, iodine, (X).sub.n R.sub.3, NO.sub.2, NR.sub.4 R.sub.5, ##STR2## or cyano; n is the number 0 or 1; R.sub.3 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl which is substituted by 1-4 halogen atoms, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio; or C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkenyl which is substituted by 1-4 halogen atoms; R.sub.4 is hydrogen, CH.sub.3 O, CH.sub.3 CH.sub.2 O or C.sub.1 -C.sub.3 alkyl; R.sub.5 is hydrogen or C.sub.1 -C.sub.3 alkyl; R.sub.6 is hydrogen, methyl or ethyl; R.sub.7 is hydrogen or methyl; Z is ##STR3## E is methine; R.sub.8 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; R.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, C.sub.2 -C.sub.5 alkylthioalkyl or cyclopropyl; and the salts of these compounds with amines, alkali metal or alkaline earth metal bases or quaternary ammonium bases have good pre- and postemergence selective herbicidal and growth-regulating properties.

Sulfonylureas

The present invention relates to monoclonal antibodies that are distinguished by a high degree of selectivity and affinity towards triasulfurone and that are therefore outstandingly suitable for use in an immunoassay for the rapid and effective detection of triasulfurone. The present invention relates also to hybridoma cell lines that produce the said monoclonal antibodies and to immunological methods for the detection of triasulfurone in soil, water or air samples using the said monoclonal antibodies and to test kits that may be used in those detection methods.

Immunological detection methods

N-Phenylsulfonyl-N'-pyrimidinyl-,-N'-triazinyl-and-N'-triazolylureas and-thioureas of formula I ##STR1## in which X is oxygen, sulfur, SO or SO.sub.2 ; W is oxygen or sulfur; R.sub.1 is hydrogen or methyl;

Sulfonylcarbamates and sulfonylthiocarbamates which are useful as intermediates for the preparation of N-phenylsulfonyl-N'-pyrimidinyl (or triazinyl or triazolyl)-ureas (or thioureas), said intermediates being of the formula: ##STR1## whererin X is oxygen, sulfur, SO or SO.sub.2 ; W is oxygen or sulfur, R.sub.2 is hydron, fluorine, chlorine bromine, iodine, (X).sub.n R.sub.3, NO.sub.2, NR.sub.4 R.sub.5, --C.tbd.CR.sub.6, ##STR2## or cyano; n is the number 0 or 1; R.sub.3 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl which is substituted by 1-4 halogen atoms, C.sub.1 -C.sub.3 alkosy or C.sub.1 -C.sub.3 -alkylthio; or C.sub.2 -C.sub.4 alkenyl or C.sub.2 C.sub.4 alkenyl which is substituted by 1-4 halogen atoms; R.sub.4 is hydrogen, CH.sub.3 O, CH.sub.3 CH.sub.2 O or C.sub.1 -C.sub.3 alkyl; R.sub.5 is hydrogen of C.sub.1 -C.sub.3 alkyl; R.sub.6 is hydrogen, methyl or ethyl; R.sub.7 is hydrogen or methyl; and R.sub.15 is phenyl or phenyl which is substituted by C.sub.1 -C.sub.4 alkly or halogen. The final product ureas and thioureas and their salts have good preemergence and postemergence selectie herbicidal and growth-regulating properties.

N-Phenylsulfonyl-N'-pyrimidinyl-,-N'-triazinyl- and-N'-triazolylureas and -thioureas of formula I ##STR1## in which X is oxygen, sulfur, SO or SO.sub.2 ; W is oxygen or sulfur, R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, bromine, iodine, (X).sub.n R.sub.3, NO.sub.2, NR.sub.4 R.sub.5, --C.tbd.CR.sub.6, ##STR2## or cyano; n is the number 0 or 1; R.sub.3 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl which is substituted by 1-4 halogen atoms, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio; or C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkenyl which is substituted by 1-4 halogen atoms; R.sub.4 is hydrogen, CH.sub.3 O, CH.sub.3 CH.sub.2 O or C.sub.1 -C.sub.3 alkyl; R.sub.5 is hydrogen or C.sub.1 -C.sub.3 alkyl; R.sub.6 is hydrogen, methyl or ethyl; R.sub.7 is hydrogen or methyl; Z is ##STR3## E is methine or nitrogen; R.sub.8 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; R.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, C.sub.2 -C.sub.5 alkylthioalkyl or cyclopropyl; R.sub.10 is hydrogen, fluorine, chlorine, methyl, trifluoromethyl, CH.sub.3 O, CH.sub.3 CH.sub.2 O, CH.sub.3 S, CH.sub.3 SO, CH.sub.3 SO.sub.2 or cyano; R.sub.11 is methyl, ethyl, CH.sub.3 O, CH.sub.3 CH.sub.2 O, fluorine or chlorine; R.sub.12 is methyl, ethyl, CH.sub.3 O, CH.sub.3 CH.sub.2 O, fluorine or chlorine; R.sub.13 is C.sub.1 -C.sub.3 alkyl; and R.sub.14 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, chlorine or OCHF.sub. 2 ; and the salts of these compounds; with the provisos that E is methine if R.sub.8 is halogen; and E is methine if R.sub.8 or R.sub.9 is OCHF.sub.2 or SCHF.sub.2, and the salts of these compounds with amines, alkali metal or alkaline earth metal bases or quaternary ammonium bases have good pre- and postemergence selective herbicidal and growth-regulating properties.

N-Phenylsulfonyl-N'-pyrimidinyl-, -N'-triazinyl- and -N'-triazolylureas and -thioureas of formula I ##STR1## in which X is oxygen, sulfur, SO or SO.sub.2 ; W is oxygen or sulfur; R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, bromine, iodine, (X).sub.n R.sub.3, NO.sub.2, NR.sub.4 R.sub.5, --C.tbd.CR.sub.6, ##STR2## or cyano; n is the number 0 or 1; R.sub.3 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl which is substituted by 1-4 halogen atoms, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio; or C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkenyl which is substituted by 1-4 halogen atoms; R.sub.4 is hydrogen, CH.sub.3 O, CH.sub.3 CH.sub.2 O or C.sub.1 -C.sub.3 alkyl; R.sub.5 is hydrogen or C.sub.1 -C.sub.3 alkyl; R.sub.6 is hydrogen, methyl or ethyl; R.sub.7 is hydrogen or methyl; Z is ##STR3## E is methine or nitrogen; R.sub.8 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, haloge n, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alky l)amino; R.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, C.sub.2 -C.sub.5 alkylthioalkyl or cyclopropyl; R.sub.10 is hydrogen, fluorine, chlorine, methyl, trifluoromethyl, CH.sub.3 O, CH.sub.3 CH.sub.2 O, CH.sub.3 S, CH.sub.3 SO, CH.sub.3 SO.sub.2 or cyano; R.sub.11 is methyl, ethyl, CH.sub.3 O, CH.sub.3 CH.sub.2 O, fluorine or chlorine; R.sub.12 is methyl, ethyl, CH.sub.3 O, CH.sub.3 CH.sub.2 O, fluorine or chlorine; R.sub.13 is C.sub.1 -C.sub.3 alkyl; and R.sub.14 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, chlorine or OCHF.sub.2 ; and the salts of these compounds; with the provisos that E is methine if R.sub.8 is halogen; and E is methine if R.sub.8 or R.sub.9 is OCHF.sub.2 or SCHF.sub.2, and the salts of these compounds with amines, alkali metal or alkaline earth metal bases or quaternary ammonium bases have good pre- and postemergence selective herbicidal and growth-regulating properties.

Phenylsulfonylchloride intermediates useful for the preparation of

Triasulfurone compounds

N-phenylsulfonyl-N'-pyrimidinyl- and -triazinyl-ureas of formula I ##STR1## wherein R is hydrogen or C.sub.1 -C.sub.4 alkyl,

N-Phenylsulfonyl-N'-pyrimidinylureas and -thioureas of formula I ##STR1## in which X is oxygen, sulfur, SO or SO.sub.2 ; W is oxygen or sulfur; R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, bromine, iodine, (X).sub.n R.sub.3, NO.sub.2, NR.sub.4 R.sub.5,--C.tbd.CR.sub.6, ##STR2## or cyano; n is the number 0 or 1; R.sub.3 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl which is substituted by 1-4 halogen atoms, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio; or C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkenyl which is substituted by 1-4 halogen atoms; R.sub.4 is hydrogen, CH.sub.3 O, CH.sub.3 CH.sub.2 O or C.sub.1 -C.sub.3 alkyl; R.sub.5 is hydrogen or C.sub.1 -C.sub.3 alkyl; R.sub.6 is hydrogen, methyl or ethyl; R.sub.7 is hydrogen or methyl; Z is ##STR3## R.sub.10 is hydrogen, fluorine, chlorine, methyl, trifluoromethyl, CH.sub.3 O, CH.sub.3 CH.sub.2 O, CH.sub.3 S, CH.sub.3 SO, CH.sub.3 SO.sub.2 or cyano; R.sub.11 is methyl, ethyl, CH.sub.3 O, CH.sub.3 CH.sub.2 O, fluorine or chlorine; R.sub.12 is methyl, ethyl, CH.sub.3 O, CH.sub.3 CH.sub.2 O, fluorine or chlorine; and the salts of these compounds with amines, alkali metal or alkaline earth metal bases or quaternary ammonium bases, have good pre- and postemergence selective herbicidal and growth-regulating properties.

There is disclosed a multi-step process for the preparation of benzenesulfonamides of general formula ##STR1## wherein R is 3,3-difluorobutyl or 3,3-difluorobuten-1-yl. The benzenesulfonamides obtainable by the process of the invention are intermediates for the synthesis of herbicidally active sulfonyl ureas.

Process for the preparation of benezenesulfonamides

N-Phenylsulfonyl N'-triazinylureas and -thioureas of formula I ##STR1## in which X is oxygen, sulfur, SO or SO.sub.2 ; W is oxygen or sulfur; R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, bromine, iodine, (X).sub.n R.sub.3, NO.sub.2, NR.sub.4 R.sub.5, --C.tbd.CR.sub.6, ##STR2## or cyano; n is the number 0 or 1; R.sub.3 is C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkyl which is substituted by 1-4 halogen atoms, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio; or C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkenyl which is substituted by 1-4 halogen atoms; R.sub.4 is hydrogen, CH.sub.3 O, CH.sub.3 CH.sub.2 O or C.sub.1 -C.sub.3 alkyl; R.sub.5 is hydrogen or C.sub.1 -C.sub.3 alkyl; R.sub.6 is hydrogen, methyl or ethyl; R.sub.7 is hydrogen or methyl; Z is ##STR3## E is nitrogen; R.sub.8 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino and R.sub.9 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, C.sub.2 -C.sub.5 alkylthioalkyl or cyclopropyl, and the salts of these compounds with amines, alkali metal or alkaline earth metal bases or quaternary ammonium bases have good pre- and postemergence selective herbicidal and growth-regulating properties.

A 2-(2-halogenoethylthio)-phenylsulfonamide of the formula I ##STR1## in which Z.sub.1 and Z.sub.2 independently of one another are hydrogen, fluorine or chlorine, is prepared by a process wherein:

Process for the preparation of 2-(2-halogenoethylthio)-phenylsulfonamides

N-phenyl-sulfonyl-N'-pyrimidinyl- and -triazinyl-ureas of formula I ##STR1## wherein R is hydrogen or C.sub.1 -C.sub.4 alkyl;

The invention relates to N-phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N-triazinylures of the general formula ##STR1## wherein R.sub.1 is hydrogen, halogen, nitro, amino, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.4 haloalkyl or a --Q--R.sub.7, --CO--OR.sub.8 or --(CO).sub.n --NR.sub.9 R.sub.10 radical,

N-phenylsulfonyl-N'-pyrimidinylureas

Novel trisubstituted indole compounds of formula ##STR1## wherein R is straight-chain C.sub.2 -C.sub.4 alk-1-en-1-yl, and their salts can be used as pharmaceutical active ingredients and can be manufactured in a manner known per se.

Substituted indoles

Growing community of inventors

Riehen, Switzerland

Willy Meyer