# Patent

## Title
Sulfonylamino(thio)carbonyl compounds

## Abstract

Sulfonylamino(thio)carbonyl compounds are used to control unwanted plants or to regulate growth in plants. Sulfonylamino(thio)carbonyl compounds are applied to plants, the seed or the area on which the plants are growing to control the growth of such plants.

## Background
It is known that substituted sulfonylamino(thio)carbonyl compounds may possess herbicidal properties. These compounds are, for example, phenyl derivatives with single or multiple substitution (e.g., EP 283876, EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266, EP 569810, WO 93/24482, WO 94/08979, WO 95/27703, WO 96/22982, WO 97/03056, WO 97/16449, WO 97/32876, DE 03934081, DE 04029753, DE 04110795, DE 10117673, DE 19540737, DE 19615900, DE 19621685, DE 19632945, DE 19823131). The effect of these compounds, however, is not satisfactory in every respect.
Specific iodine-substituted phenylsulfonylamino(thio)carbonyl compounds have now surprisingly been found which are suitable with particular advantage as herbicides or plant growth regulators.
The present invention accordingly provides compounds of the formula (I) and/or salts thereof,




in which

    R is a hydrocarbon radical or hydrocarbonoxy radical, preferably a radical from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, cycloalkenyloxy, aryl and aryloxy, which is unsubstituted or substituted and inclusive of substituents has 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, or R is a heterocyclyl radical or heterocyclyloxy radical which is unsubstituted or substituted,
    
        or R is a hydrogen atom, halogen or a radical C(O)R3, OC(O)R3, S(O)nR3, OS(O)nR3, OH, CN, NO2, NH2, SF5, NR4R5 or Si(R6)3, where n is 0, 1 or 2,
    
    
    R1 independently at each occurrence is halogen, OH, SH, a carbon-free, nitrogen-containing radical or a carbon-containing radical having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms,
    I is 0, 1, 2 or 3, preferably 0, 1 or 2, more preferably 0 to 1, very preferably 0,
    R2 is a substituted or unsubstituted heterocyclyl radical having 5 ring members, of which preferably at least one is oxygen, sulfur or nitrogen and one to four further ring members may be nitrogen,
    R3 is a hydrocarbon radical or hydrocarbonoxy radical, preferably a radical from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, cycloalkenyloxy, aryl and aryloxy, which is unsubstituted or substituted and inclusive of substituents has 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms,
    
        or R3 is a heterocyclyl radical or heterocyclyloxy radical which is unsubstituted substituted, or R3 is a hydrogen atom, CN or NR4R5 ist,
    
    
    R4 is a group of the formula R0-Q0-, in which
    
        R0 is a hydrogen atom, an acyl radical, a hydrocarbon radical or a heterocyclyl radical, each of the last-mentioned two radicals being unsubstituted or substituted and inclusive of substituents having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, and
        Q0 is a direct bond or a divalent group of the formula —O— or —N(R#)—, R# being a hydrogen atom, an acyl radical or a hydrocarbon radical and the last-mentioned radical being unsubstituted or substituted and inclusive of substituents having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, or
        or R0 and R# form with one another a nitrogen-containing heterocyclic ring,
    
    
    R5 is a hydrogen atom, an acyl radical, a hydrocarbon radical or a heterocyclyl radical, each of the last-mentioned two radicals being unsubstituted or substituted and inclusive of substituents having 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, or
    R4 and R5 form with one another a nitrogen-containing heterocyclic ring,
    R6 is a hydrocarbon radical which is unsubstituted or substituted and inclusive of substituents has 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, preferably (C1-C4)alkyl or (C6-C10)aryl, and
    W is an oxygen atom or a sulfur atom.


The compounds of the formula (I) may form salts, examples being those in which the hydrogen of the —SO2—NH— group is replaced by an agriculturally suitable cation. These salts are, for example, metal salts, especially alkali metal salts or alkaline earth metal salts, particularly sodium and potassium salts, or else ammonium salts or salts with organic amines. Formation of salts may likewise take place by addition of an acid onto basic groups, such as amino and alkylamino. Suitable acids for this purpose are strong organic and inorganic acids, such as HCl, HBr, H2SO4 or HNO3, for example.
Carbon-containing radicals are organic radicals which contain at least one carbon atom, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and also at least one atom of one or more other elements of the Periodic Table of the Elements, such as H, Si, N, P, O, S, F, Cl, Br or I. Examples of carbon-containing radicals are unsubstituted or substituted hydrocarbon radicals, which may be attached to the parent structure directly or via a heteroatom such as N, S, P or O, unsubstituted or substituted heterocyclyl radicals which may be attached to the parent structure directly or via a heteroatom such as N, S, P or O, carbon-containing acyl radicals or cyano.
In formula (I) and all subsequent formulae the carbon-containing radicals such as alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and also the corresponding unsaturated and/or substituted radicals in the carbon skeleton are in each case linear or branched. Unless specifically indicated, for these radicals the lower carbon frameworks, with 1 to 6 carbon atoms or, in the case of unsaturated groups, with 2 to 6 carbon atoms, for example, are preferred. Alkyl radicals, both alone and in composite definitions such as alkoxy, haloalkyl, etc., are for example methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, tert-butyl or 2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl, and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the definition of the possible unsaturated radicals corresponding to the alkyl radicals; alkenyl is for example allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; alkynyl is for example propargyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl.
Alkenyl in the form (C3-C4)alkenyl, (C3-C5)alkenyl, (C3-C6)alkenyl, (C3-C8)alkenyl or (C3-C12)alkenyl is preferably an alkenyl radical having 3 to 4, 3 to 5, 3 to 6, 3 to 8 or 3 to 12 carbon atoms, respectively, in which the double bond is not at the carbon atom joined to the remainder of the molecule of the compound (I) (“yl” position). Similar comments apply to (C3-C4)alkynyl etc., (C3-C4)alkenyloxy etc., and (C3-C4)alkynyloxy etc.
Cycloalkyl is a carbocyclic, saturated ring system having preferably 3-8 carbon atoms, e.g., cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Carbon-free, nitrogen-containing radicals are radicals which contain preferably 1 to 10 nitrogen atoms, more preferably 1 or 2 nitrogen atoms, and additionally, preferably, one or more atoms of one or more non-carbon elements of the Periodic Table of the Elements, such as H, O or S. Examples of carbon-free, nitrogen-containing radicals are NH2, NO2, NHOH, NO, NH—NH2 or N3.
Halogen is for example fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl or alkynyl, respectively, each of which is fully or partly substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, examples being CF3, CHF2, CH2F, CF3CF2, CH2FCHCl, CCl3, CHCl2, CH2CH2Cl; haloalkoxy is for example OCF3, OCHF2, OCH2F, CF3CF2O, OCH2CF3 and OCH2CH2Cl; similar comments apply to haloalkenyl and other halogen-substituted radicals.
A hydrocarbon radical is a linear, branched or cyclic, saturated or unsaturated, aliphatic or aromatic hydrocarbon radical, e.g., alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl; aryl is a monocyclic, bicyclic or polycyclic aromatic system, examples being phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl;
a hydrocarbon radical is preferably alkyl, alkenyl or alkynyl having up to 12 carbon atoms or cycloalkyl having 3, 4, 5, 6 or 7 ring atoms, or phenyl.
A heterocyclic radical or ring (heterocyclyl) can be saturated, unsaturated or heteroaromatic and unsubstituted or substituted; it contains preferably one or more heteroatoms in the ring, preferably from the group N, O and S; preferably it is an aliphatic heterocyclyl radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms, and contains 1, 2 or 3 heteroatoms. The heterocyclic radical may be, for example, a heteroaromatic radical or ring (heteroaryl), such as a monocyclic, bicyclic or polycyclic aromatic system in which at least one ring contains one or more heteroatoms, examples being pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, or is a partly or fully hydrogenated radical such as oxiranyl, oxetanyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl or tetrahydrofuryl. Suitable substituents for a substituted heterocyclic radical are the substituents specified later on below, and oxo as well. The oxo group may also occur on the ring heteroatoms, which can exist in different oxidation states, in the case of N and S, for example.
Substituted radicals, such as substituted hydrocarbon radicals, e.g., substituted alkyl, alkenyl, alkynyl, aryl, phenyl, and benzyl, or substituted heterocyclyl or heteroaryl, are for example a substituted radical derived from the unsubstituted parent structure, the substituents being, for example, one or more, preferably 1, 2 or 3, radicals from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, and, in the case of cyclic radicals, alkyl and haloalkyl as well, and also unsaturated aliphatic radicals corresponding to the stated saturated, hydrocarbon-containing radicals, such as alkenyl, alkynyl, alkenyloxy, alkynyloxy etc. In the case of radicals containing carbon atoms preference is given to those having 1 to 4 carbon atoms, particularly 1 or 2 carbon atoms. Preference is generally given to substituents from the group consisting of halogen, such as fluorine and chlorine (C1-C4)alkyl, preferably methyl or ethyl, (C1-C4)haloalkyl, preferably trifluoromethyl, (C1-C4)alkoxy, preferably methoxy or ethoxy, (C1-C4)haloalkoxy, nitro, and cyano. Particular preference here is given to the substituents methyl, methoxy, and chlorine. Optionally substituted phenyl is preferably phenyl which is unsubstituted or is substituted one or more times, preferably up to three times, by identical or different radicals from the group consisting of halogen, (C1-C4)alkyl, (C1-C4)alkoxy, (C1-C4)haloalkyl, (C1-C4)haloalkoxy, and nitro, examples being o-, m- and p-tolyl, dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-trifluoro- and -trichlorophenyl, 2,4-, 3,5-, 2,5-, and 2,3-dichlorophenyl, and o-, m- and p-methoxyphenyl.
Monosubstituted or disubstituted amino is a chemically stable radical from the group of substituted amino radicals, which are N-substituted by, for example, one radical or two identical or different radicals from the group consisting of alkyl, alkoxy, acyl and aryl; preferably monoalkylamino, dialkylamino, acylamino, arylamino, N-alkyl-N-arylamino, and N-heterocycles; preference is given here to alkyl radicals having 1 to 4 carbon atoms; aryl here is preferably phenyl or substituted phenyl; acyl is subject to the definition given later on below, preferably formyl, (C1-C4)alkylcarbonyl or (C1-C4)alkylsulfonyl. Similar comments apply to substituted hydroxylamino or hydrazino.
An acyl radical is the radical of an organic acid formed formally by elimination of an OH group from the organic acid, such as the radical of a carboxylic acid and radicals of acids derived therefrom, such as of thiocarboxylic acid, optionally N-substituted iminocarboxylic acids, or the radicals of carbonic monoesters, or optionally N-substituted carbamic acids, sulfonic acids, sulfinic acids, phosphonic acids or phosphinic acids.
An acyl radical is preferably formyl or aliphatic acyl from the group CO—Rx, CS—Rx, CO—ORx, CS—ORx, CS—SRx, SORY or SO2RY, where Rx and RY are each a C1-C10 hydrocarbon radical which is unsubstituted or substituted, or aminocarbonyl or aminosulfonyl, the two last-mentioned radicals being unsubstituted, N-monosubstituted or N,N-disubstituted.
Acyl is for example formyl, haloalkylcarbonyl, alkylcarbonyl such as (C1-C4)alkylcarbonyl, phenylcarbonyl, it being possible for the phenyl ring to be substituted, for example as indicated above for phenyl, or alkyloxycarbonyl, phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl, N-alkyl-1-iminoalkyl, and other radicals of organic acids.
The invention also provides all stereoisomers that are embraced by formula (I), and mixtures thereof. Such compounds of the formula (I) contain one or more asymmetric carbon atoms or else double bonds, which are not indicated separately in the general formula (I). The possible stereoisomers, defined by their specific three-dimensional form, such as enantiomers, diastereomers, Z-isomers, and E isomers, are all embraced by the formula (I) and may be obtained by customary methods from mixtures of the stereoisomers, or else prepared by stereoselective reactions in combination with the use of stereochemically pure starting materials.
The above examples of radicals or radical ranges which are subsumed under the general terms such as “alkyl”, “acyl”, “substituted radicals”, etc., do not constitute a complete enumeration. The general terms also embrace the definitions, given later on below, of radical ranges in groups of preferred compounds, especially radical ranges which embrace specific radicals from the tabular examples.
Preferred compounds of the invention, of the formula (I), and/or salts thereof are those in which

    R is (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C6)cycloalkyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkynyl, (C1-C6)alkyloxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C3-C6)cycloalkyloxy, phenyl, phenyloxy, H, F, Cl, Br, I, OH, CN, NO2, NH2, SF5, C(O)R3, Si((C1-C6)alkyl)3, N((C1-C6)alkyl)2, NH(C1-C6)alkyl, N((C2-C6)alkenyl)2, NH(C2-C6)alkenyl, N((C2-C6)alkynyl)2, NH(C2-C6)alkynyl, NH((C3-C6)cycloalkyl)2, NH(C3-C6)cycloalkyl, N(C1-C6)alkyl(C3-C6)cycloalkyl, N(C1-C6)alkyl C(O)R3, NHC(O)R3, N(C1-C6)alkyl S(O)nR3, NHS(O)nR3, S(O)n(C1-C4)alkyl, S(O)n(C3-C6)cycloalkyl, S(O)n(C1-C6)alkenyl, S(O)n(C1-C6)alkynyl, S(O)nNHR3, S(O)nN(C1-C6)alkyl R3, OSO2(C1-C6)alkyl, OSO2(C3-C6)cycloalkyl, OSO2(C1-C6)alkenyl, OSO2(C1-C6)alkynyl, OS(O)nphenyl, OSO2N((C1-C6)alkyl)2, OSO2NH(C1-C6)alkyl, OSO2N((C3-C6)cycloalkyl)2, OSO2NH(C3-C6)cycloalkyl, OSO2N((C2-C6)alkenyl)2, OSO2NH(C2-C6)alkenyl, OSO2N((C2-C6)alkynyl)2, OSO2NH(C2-C6)alkynyl, OC(O)R3 or heterocyclyl,
    
        the stated radicals alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, alkyloxy, alkenyloxy, alkynyloxy, cycloalkoxy, phenyl, phenyloxy and heterocyclyl being unsubstituted or substituted, e.g., by one or more radicals from the group consisting of halogen, CN, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C3-C6)cycloalkyl, phenyl, phenyloxy, and heterocyclyloxy, with the two last-mentioned radicals possible being substituted one or more times by radicals from the group consisting of halogen, CN, methyl, methoxy, trifluoromethyl, and trifluoromethoxy,
        n is 0, 1 or 2, and R3 is H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C6)cycloalkyl, (C1-C6)alkyloxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C3-C6)-cycloalkyloxy, phenyl, heterocyclyl, CN, NH(C1-C6)alkyl or N((C1-C6)alkyl)2,
        the stated radicals alkyl, alkenyl, alkynyl, cycloalkyl, alkyloxy, alkenyloxy, alkynyloxy, cycloalkyloxy, phenyl, and heterocyclyl being unsubstituted or substituted, e.g., by one or more radicals from the group consisting of halogen, CN, (C1-C6)akyl, (C1-C6)alkenyl, (C1-C6)alkynyl, and (C1-C6)alkyloxy,
    
    
    R1 independently at each occurrence is (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)alkyloxy, (C1-C6)haloalkoxy or halogen,
    I is 0, 1 or 2, preferably 0 or 1, more preferably 0,
    R2 is in each case optionally substituted heterocyclyl, preferably of the following formulae






in which

    Q1, Q2 and Q3 are each oxygen or sulfur, and
    R7 is hydrogen, hydroxy, amino, cyano, is (C2-C10)alkylideneamino, is (C1-C6)alkyl optionally substituted by fluorine, chlorine, bromine, cyano, (C1-C4)alkoxy, (C1-C4)alkyl-carbonyl or (C1-C4)alkoxycarbonyl, is (C2-C6)alkenyl or (C2-C6)alkynyl each of which is optionally substituted by fluorine, chlorine and/or bromine, is (C1-C6)alkoxy, (C1-C6)alkylamino or (C1-C6)alkyl-carbonylamino, each of which is optionally substituted by fluorine, chlorine, bromine, cyano, (C1-C4)alkoxy or (C1-C4)alkoxy-carbonyl, is (C3-C6)alkenyloxy, is di((C1-C4)alkyl(amino), is (C3-C6)cycloalkyl, (C3-C6)cycloalkylamino or (C3-C6)cycloalkyl-(C1-C4)alkyl, each of which is optionally substituted by fluorine, chlorine, bromine, cyano and/or (C1-C4)alkyl, or is phenyl or phenyl-(C1-C4)alkyl each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, (C1-C4)alkyl, trifluoromethyl and/or (C1-C4)alkoxy,
    R8 is hydrogen, hydroxy, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, is (C1-C6)alkyl optionally substituted by fluorine, chlorine, bromine, cyano, (C1-C4)alkoxy, (C1-C4)alkyl-carbonyl or (C1-C4)alkoxy-carbonyl, is (C2-C6)alkenyl or (C2-C6)alkynyl each of which is optionally substituted by fluorine, chlorine and/or bromine, is (C1-C6)alkoxy, (C1-C6)alkylthio, (C1-C6)alkylamino or (C1-C6)alkyl-carbonylamino each of which is optionally substituted by fluorine, chlorine, cyano (C1-C4)alkoxy or (C1-C4)alkoxycarbonyl, is (C3-C6)alkenyloxy, (C3-C6)alkynyloxy, (C3-C6)alkenylthio, (C3-C6)alkynylthio, (C3-C6)alkenylamino or (C3-C6)alkynylamino, is di((C1-C4)alkyl)amino, is aziridino, pyrrolidino, piperidino or morpholino each of which is optionally substituted by methyl and/or ethyl, is (C3-C6)cycloalkyl, (C5-C6)cycloalkenyl, (C3-C6)cycloalkyloxy, (C3-C6)cycloalkylthio, (C3-C6)cycloalkylamino, (C3-C6)cycloalkyl-(C1-C4)alkyl, (C3-C6)cycloalkyl-(C1-C4)alkoxy, (C3-C6)cycloalkyl-(C1-C4)alkylthio or (C3-C6)cycloalkyl-(C1-C4)alkylamino, each of which is optionally substituted by fluorine, chlorine, bromine, cyano and/or (C1-C4)alkyl, or is phenyl, phenyl-(C1-C4)alkyl, phenoxy, phenyl-(C1-C4)alkoxy, phenylthio, phenyl-(C1-C4)alkylthio, phenylamino or phenyl-(C1-C4)alkylamino each of which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, (C1-C4)alkyl, trifluoromethyl, (C1-C4)alkoxy and/or (C1-C4)alkoxycarbonyl, or
    R7 and R8 together are optionally branched alkanediyl having 3 to 11 carbon atoms, and additionally
    R9, R10 and R11 are identical or different and are hydrogen, cyano, fluorine, chlorine, bromine, or are alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylsulfinyl or alkylsulfonyl having in each case up to 6 carbon atoms, or are cycloalkyl having 3 to 6 carbon atoms and being optionally substituted by cyano, fluorine, chlorine, bromine or (C1-C4)alkyl, and
    W is an oxygen atom.


Particularly preferred compounds of the formula (I) and/or salts thereof are those in which

    R is (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C6)cycloalkyl, (C1-C4)alkyloxy, (C2-C4)alkenyloxy, (C2-C4)alkynyloxy, (C3-C6)cycloalkyloxy, phenyl, phenyloxy, H, F, Cl, Br, I, C(O)R3, CN, NO2, NH2, N((C1-C4)alkyl)2, NH(C1-C4)alkyl, NH(C2-C4)alkenyl, NH(C2-C4)alkynyl, NH(C3-C6)cycloalkyl, N(C1-C4)alkyl(C3-C6)cycloalkyl, S(C1-C4)alkyl, S(C2-C4)alkenyl, S(C2-C4)alkynyl, S(C3-C6)cycloalkyl, S(O)(C1-C4)alkyl, S(O)(C1-C4)alkenyl, S(O)(C2-C4)alkynyl, S(O)(C3-C6)cycloalkyl, SO2(C1-C4)alkyl, SO2(C2-C4)alkenyl, SO2(C2-C4)alkynyl, SO2(C3-C6)cycloalkyl, SO2NH(C1-C4)alkyl, SO2N((C1-C4)alkyl)2, SO2NH(C3-C6)cycloalkyl, OSO2(C1-C4)alkyl, OSO2NH(C1-C4)alkyl, OSO2N((C1-C4)alkyl)2 or NHC(O)R3, NHSO2R3, OC(O)R3, R3 being H, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C6)cycloalkyl, (C1-C4)alkyloxy, (C2-C4)alkenyloxy, (C2-C4)alkynyloxy, (C3-C6)cycloalkyloxy, (C1-C4)haloalkyl, NH(C1-C4)alkyl or N((C1-C4)alkyl)2,
    
        the stated radicals alkyl, alkenyl, alkynyl, cycloalkyl, alkyloxy, alkenyloxy, alkynyloxy, cycloalkyloxy, phenyl and phenyloxy being unsubstituted or substituted by, for example, one or more radicals, preferably one, two or three radicals, from the group consisting of halogen (F, Cl, Br, I), (C1-C4)alkyl, (C1-C4)alkyloxy, (C1-C4)haloalkyl(C1-C4)haloalkyloxy and (C3-C6)cycloalkyl,
    
    
    R1 is halogen (F, Cl, Br, I), (C1-C4)alkyl, (C1-C4)alkyloxy, (C1-C4)haloalkyl or (C1-C4)haloalkyloxy,
    I is 0 or 1, preferably 0,
    R2 is in each case optionally substituted heterocyclyl, preferably of the following formulae






in which

    Q1, Q2 and Q3 are each oxygen or sulfur and
    R7 is hydrogen, hydroxy, amino, is (C3-C8)alkylideneamino, is methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl in each case optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, is propenyl, butenyl, propynyl or butynyl in each case optionally substituted by fluorine, chlorine or bromine, is methoxy, ethoxy, n-propoxy or isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, methylamino, ethylamino, n-propylamino or isopropylamino, n-butylamino, isobutylamino, sec-butylamino or tert-butylamino, in each case optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, is propenyloxy or butenyloxy, is dimethylamino or diethylamino, is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl in each case optionally substituted by fluorine, chlorine, methyl and/or ethyl, or is phenyl or benzyl in each case optionally substituted by fluorine, chlorine, methyl, trifluoromethyl and/or methoxy,
    R8 is hydrogen, hydroxy, mercapto, amino, fluorine, chlorine, bromine, is methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl in each case optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, is ethenyl, propenyl, butenyl, propynyl or butynyl in each case optionally substituted by fluorine, chlorine or bromine, is methoxy, ethoxy, n-propoxy or isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, methylthio, ethylthio, n-propylthio or isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, methylamino, ethylamino, n-propylamino or isopropylamino, n-butylamino, isobutylamino, sec-butylamino or tert-butylamino, in each case optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, is propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, propadienylthio, butenylthio, propynylthio, butynylthio, propenylamino, butenylamino, propynylamino or butynylamino, is dimethylamino, diethylamino or dipropylamino, is cyclopropyl cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropyl methyl, cyclobutyl methyl, cyclopentyl methyl, cyclohexyl methyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino in each case optionally substituted by fluorine, chlorine, methyl and/or ethyl, or is phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino in each case optionally substituted by fluorine, chlorine, methyl, trifluoromethyl, methoxy and/or methoxycarbonyl, or
    R7 and R8 together are optionally branched alkanediyl having 3 to 11 carbon atoms, and additionally
    R9, R10 and R11 are identical or different and are hydrogen, cyano, fluorine, chlorine, bromine, or are methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, propenyl, butenyl, propynyl, butynyl, methoxy, ethoxy, n-propoxy or isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, propenyloxy, butenyloxy, propynyloxy, butynyloxy, methylthio, ethylthio, n-propylthio or isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, propenylthio, butenylthio, propynylthio, butynylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, each of which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, or are cyclopropyl, and
    W is a hydrogen atom.


Especially preferred compounds of the invention, of the formula (I), and/or salts thereof, are those in which

    R is CH3, CH2CH3, (CH2)2CH3, CH(CH3)2, C(CH3)3, CH═CH2, C≡CH, CH2CH═CH2, CH2C≡CH, cyclopropyl, phenyl, H, F, Cl, Br, I, CN, NO2, NH2, CH2OCH3, CF3, CHF2, C(O)H, C(O)CH3, C(O)CH2CH3, C(O)OCH3, C(O)OCH2CH3, NHCH3, N(CH3)2, NH-cyclopropyl, N(CH3)-cyclopropyl, NHC(O)H, NHC(O)CH3, NHC(O)OCH3, NHSO2CH3, NHSO2CF3, NHSO2CHF2, OCH3, OCH2CH3, O(CH2)2CH3, OCH(CH3)2, O(CH2)3CH3, OCH2CH(CH3)2, OCH(CH3)CH2CH3, OC(CH3)3, OCH═CH2, OC≡CH, OCH2CH═CH2, OCH2C≡CH, O-cyclopropyl, OCH2-cyclopropyl, O(CH2)2Cl, O(CH2)3Cl, OCH2OCH3, Ophenyl, OCH2phenyl, OCF3, OCHF2, OCH2F, OCH2CF3, OCH2CHF2, OCH(CH3)CF3, OCH2CF2CF3, SCH3, SCH2CH3, S(O)CH3, S(O)CH2CH3, SO2CH3, SO2CH2CH3, SO2NHCH3, SO2N(CH3)2, SO2NHCF3, SO2NHCHF2, OSO2CH3, OSO2CF3, OSO2CHF2, OSO2N(CH3)2, OSO2NHCF3, OSO2NHCHF2, OC(O)H, OC(O)CH3, OC(O)OCH3, OC(O)N(CH3)2,
    I is 0,
    R2 is optionally substituted triazolinyl, preferably of the following formula






in which

    Q1 is oxygen or sulfur, and
    R7 is methyl, ethyl, n-propyl or isopropyl each of which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, is propenyl or propynyl, is methoxy, ethoxy, n-propoxy or isopropoxy, or is cyclopropyl,
    R8 is hydrogen, chlorine, brome, is methyl, ethyl, n-propyl or isopropyl each of which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, is propenyl or propynyl each of which is optionally substituted by fluorine and/or chlorine, is methoxy, ethoxy, n-propoxy or isopropoxy, methylthio, ethylthio, n-propylthio or isopropylthio, each of which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, or is propenyloxy or cyclopropyl, and
    W is oxygen.


Particular preference is also given to compounds of the invention of the formula (I) and salts thereof which contain a combination of radicals from the preferred compounds specified above, and to those which contain individual or multiple radicals from the compounds listed in table 1 of this description.
The present invention also provides processes for preparing the compounds of the invention of the formula (I) and/or salts thereof, comprising

    (a) reacting an aminosulfonyl compound of the formula (II)






with a (thio)carboxylic acid derivative of the formula (III)





in which

    R* is halogen or an unsubstituted or substituted (C1-C20)hydrocarbonoxy radical, such as unsubstituted or substituted alkoxy, aryloxy, aralkoxy or alkylaryloxy, preferred substituents for the four last-mentioned radicals being halogen, (C1-C4)alkyl, (C1-C4)alkyloxy and (C1-C4)haloalkyl, R* preferably being fluorine, chlorine, bromine, (C1-C6)alkoxy, (C6-C10)aryloxy, (C6-C10)aryl (C1-C6)alkoxy or (C1-C6)alkyl(C6-C10)aryloxy,

optionally in the presence of a reaction auxiliary, in particular an acid acceptor, and optionally in the presence of a diluent, or

    (b) reacting a sulfonyliso(thio)cyanate of the formula (IV)






with a heterocyclyl compound of the formula (V)

H—R2  (V)

optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, or

    (c) reacting a halosulfonyl compound of the formula (VI)






with a heterocyclyl compound of the formula (V)

H—R2  (V)

and a metal (thio)cyanate of the formula (VII)

MWCN  (VII)

in which

    M is a cation, such as an ammonium cation or alkali metal cation, preferably a sodium or potassium ion, and
    W is an oxygen atom or a sulfur atom,

optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,

or

    (d) reacting a halosulfonyl compound of the formula (VI)






with a (thio)carboxamide of the formula (VIII).





optionally in the presence of a reaction auxiliary, in particular an acid acceptor, and optionally in the presence of a diluent,

or

    (e) reacting a sulfonylamino(thio)carbonyl compound of the formula (IX)






in which

    R** is halogen or an unsubstituted or substituted (C1-C20)hydrocarbonoxy radical such as unsubstituted or substituted alkoxy, aryloxy, aralkoxy or alkylaryloxy, preferred substituents for the four last-mentioned radicals being halogen, (C1-C4)alkyl, (C1-C4)alkyloxy and (C1-C4)haloalkyl, R* preferably being fluorine, chlorine, bromine, (C1-C6)alkoxy, (C6-C10)aryloxy, (C6-C10)aryl (C1-C6)alkoxy or (C1-C6)alkyl(C6-C10)aryloxy,

with a heterocyclyl compound of the formula (V)

H—R2  (V)

optionally in the presence of reaction auxiliary, in particular an acid acceptor, and optionally in the presence of a diluent,

and optionally converting the compound of the formula (I) obtained by process (a), (b), (c), (d) or (e) into a salt by customary methods,

the radicals, groups, and indices R, R1, R2, W and I in the formulae (II)-(IX) being defined as in formula (I), and also the same ranges of preference applying as indicated for formula (I).



The reaction of the compounds of the formula (II) and (III) in accordance with version a) takes place preferably under base catalysis in an inert organic solvent, such as dichloromethane, acetonitrile, dioxane or THF, at temperatures between 0° C. and the boiling point of the solvent, preferably at room temperature (cf. DE 19621685). The base used comprises, for example, organic amine bases, such as 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), alkali metal tert-butoxides, such as NaO-t-C4H9, or alkali metal hydroxides, such as NaOH, particularly when R*=(substituted) aryloxy (cf. EP 44 807), or trialkylaluminum such as trimethylaluminum or triethylaluminum, the latter in particular when R* is alkyloxy (cf. EP 166 516). The respective base is used, for example, in the range from 1 to 3 mole equivalents, based on the compound of formula (II) (scheme 0).




The sulfonamides of the formula (II), the compounds of the formulae (IV), (VI) and (IX), and the compounds of the formula (XIV) described below are new compounds, which, like their preparation and their use for preparing compounds of the formula (I) and/or salts thereof, are provided by the present invention.
The compounds of the formula (II) can be obtained, for example, as shown in schemes 1 to 8 below.




Starting from commercially available compounds of the formula (X) it is possible, such as by diazotizing the amino group with an alkali metal nitrite, e.g., sodium nitrite, in the presence of hydrochloric acid at temperatures between −10° C. and 10° C., and by subsequent exchange of the resulting diazo group with, for example, sulfur dioxide in the presence of a diluent, such as dichloromethane, 1,2-dichloroethane or acetic acid, and in the presence of a catalyst, such as copper(I) chloride and/or copper(II) chloride, at temperatures between −10° C. and 50° C., to obtain the compounds of the formula (XI) (cf. Meerwein, Chem. Ber. 1957, 90, 841) (scheme 1).
By treating sulfochlorides of the formula (XI) with tert-butylamine it is possible to obtain sulfonamides of the formula (XII). The formation of sulfonamide is carried out in, for example, inert solvents, such as dichloromethane, tetrahydrofuran (THF), dioxane, toluene or dimethylformamide (DMF), at temperatures between −70° C. up to the boiling point of the solvent used, preferably at 25° C. The amount of amine employed here is preferably 1.5-2.5 equivalents based on the sulfochloride used.




The reduction of the nitro compounds (XII) to the amines of the formula (XIII) takes place in the same way as by known methods (in this regard cf. Houben-Weyl, “Methoden der Organischen Chemie”, 4th ed., vol. XI/1 p. 360 ff., Thieme Verlag Stuttgart, 1957) (Scheme 2).




The compounds of the formula (XIII) can be diazotized under customary conditions for diazotization reactions and then converted into compounds of the formula (XIV). By way of example the diazotization takes place in the presence of the acid H+X−, where X− is preferably Cl−, I− or HSO4−, in aqueous solution, optionally with the use of an organic solvent which is inert under the reaction conditions, using a nitrite. Diazotization is carried out with, for example, an alkali metal nitrite such as NaNO2 (sodium nitrite) in amounts of 1.0-1.2 mol of nitrite, preferably 1.01-1.05 mol of nitrite, per mole of the compound of the formula (XIII). Suitable acids include mineral acids or strong organic acids, preference being given to hydrochloric acid or sulfuric acid. The solvent is water or a mixture of water with an organic solvent which is inert under the reaction conditions. The reaction temperature is generally between −5° C. and 50° C., preferably 10° C. to 20° C. (scheme 3).
The reaction of the resultant diazonium salts to give the aryl iodides of the formula (XIV) takes place in general without isolation and is carried out in the same aqueous or aqueous-organic solvent or solvent mixture as the diazotization. In the course of the reaction the diazonium group is replaced by the iodine atom, either by the anion of the diazonium salt (if in the acid X−═I−) or (if X− is not I−) by reaction with added iodide, e.g., alkali metal iodide, preferably sodium iodide or potassium iodide. The amount of iodide here is for example 1.1 to 1.5 mol of iodide per mole of the compound of the formula (XIII) originally employed. The reaction temperature here runs in general to 10° C. to 40° C., preferably 15° C. to 30° C. (in this regard cf., e.g., DE 19625831 and Bioorg. Med. Chem. 2004, 12, 2079) (scheme 3).




The elimination of the tert-butyl protective group in the compounds of the formula (XIV) to form the sulfonamides of the formula (II) is accomplished by, for example, treatment with a strong acid (see WO 89/10921). Examples of suitable strong acids include mineral acids, such as H2SO4 or HCl, or strong organic acids, such as trifluoroacetic acid. The reaction takes place at, for example, temperatures from −20° C. up to the respective reflux temperature of the reaction mixture, preferably at 0° C. to 40° C. The reaction can be carried out in bulk (without solvent) or else in an inert solvent, such as dichloromethane or trichloromethane (scheme 4).
Certain sulfonamides of the formula ((II) are known:

    5-amino-2-iodobenzenesulfonamide [477932-67-5] (WO 2002098424); 2-iodo-4-methoxybenzenesulfonamide [342411-62-5] (Nippon Kagaku Kaishi 1978, (2), 259); (2E)-N-{2-[3-(aminosulfonyl)-4-iodophenyl]ethyl}-3-(2,4-dimethoxyphenyl)acrylamide [308336-46-1] (DE 19923086); 5-(2-aminoethyl)-2-iodobenzenesulfonamide [308336-44-9] (DE 19923086); N-{2-[3-(aminosulfonyl)-4-iodophenyl]ethyl}-2,2,2-trifluoroacetamide [308336-43-8] (DE 19923086, DE 10054482, DE 10054481); 5-bromo-2-iodobenzenesulfonamide [273208-19-8]; 5-chloro-2-iodobenzenesulfonamide [273208-17-6]; 4-bromo-2-iodobenzenesulfonamide [273208-14-3]; 2-iodo-4-(trifluoromethyl)benzenesulfonamide [273208-12-1]; 2-iodo-4,5-dimethylbenzenesulfonamide [273208-09-6]; 4-chloro-2-iodobenzenesulfonamide [271796-28-2] (WO 2002003978, WO 2001660553); N-{2-[3-(aminosulfonyl)-4-iodophenyl]ethyl}-5-chloro-2-methoxybenzamide [254974-16-8](J. Med. Chem. 2001, 44-1085, DE 19832009); 2-iodo-5-methylbenzenesulfonamide [200060-22-6]; 2-amino-6-iodobenzenesulfonamide [153439-32-8](WO 9321171, WO 9321170); ethyl{[2-(aminosulfonyl)-3-iodophenyl]amino}(oxo)acetate [153439-30-6] (WO9321171); methyl 2-(aminosulfonyl)-3-iodobenzoate [144550-90-3] (WO 9213845); methyl 3-(aminosulfonyl)-4-iodobenzoate [144550-86-7] (WO 9213845); isopropyl 3-(aminosulfonyl)-2-iodobenzoate [144550-85-6] (WO 9213845); propyl 3-(aminosulfonyl)-2-iodobenzoate [144550-84-5] (WO 9213845); ethyl 3-(aminosulfonyl)-2-iodobenzoate [144550-81-2] (WO 9213845); methyl 3-(aminosulfonyl)-2-iodobenzoate [144550-75-4] (WO 9213845); N-[4-(aminosulfonyi)-2,3-diiodophenyl]acetamide [118427-12-6] (HU 44481); 4-amino-2,3-diiodobenzenesulfonamide [118427-08-0] (HU 44481); 4-amino-2,5-diiodobenzenesulfonamide [118427-07-9] (HU 44481); 4-amino-2,6-diiodobenzenesulfonamide [100377-04-6] (HU 44481); 2-iodo-3,5-dimethylbenzenesulfonamide [100377-04-6] (J. Chem. Soc., Abstr. 1956, 3668); 4-iodobenzene-1,3-disulfonamide [91425-72-8] (GB 93228); 4-amino-6-iodobenzene-1,3-disulfonamide [89891-29-2] (e.g., J. Pharm. Sci. 1997, 86, 631); 3-(aminosulfonyl)-4-iodobenzoic acid [82608-96-6] (FR 2493702, JP 57081411); 2-iodobenzenesulfonamide [53730-99-7] (e.g., WO 2002003978, EP 96002); 5-{[(1E)-(dimethylamino)methylene]amino}-2,4-diiodobenzenesulfonamide [22184-83-4] (Ces.-Slov. Farm. 1968, 17-272); 5-amino-2,4-diiodobenzenesulfonamide [22184-81-2] (Ces.-Slov. Farm. 1968, 17-272).


Certain sulfonyliso(thio)cyanates of the formula (IV) are known:

    methyl 2-iodo-3-(isocyanatosulfonyl)benzoate [144550-98-1] (WO 9213845); ethyl 2-iodo-3-(isocyanatosulfonyl)benzoate [144550-93-6] (WO 9213845); propyl 2-iodo-3-(isocyanatosulfonyl)benzoate [144550-92-5] (WO 9213845); isopropyl 2-iodo-3-(isocyanatosulfonyl)benzoate [144550-91-4] (WO 9213845); methyl 3-iodo-2-(isocyanatosulfonyl)benzoate [144550-83-4] (WO 9213845).


Certain sulfonyl halides of the formula (VI) are known:

    2,4-diiodobenzenesulfonyl chloride [686350-22-1] (Dok. Akad. Nauk SSR 1954, 99, 995); 3-(chlorosulfonyl)-4-iodobenzoic acid [402934-49-0] (Ind. J. Heterocycl. Chem. 2001, 11, 79; (R)-3-chloro-2-iodo-4-[(3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl)amino]benzenesulfonyl chloride [329901-78-2] (WO 2001017956, WO 2001017955); methyl 3-(chlorosulfonyl)-2-iodobenzoate [144550-99-2] (WO 9213845); ethyl 3-(chlorosulfonyl)-2-iodobenzoate [144550-80-1] (WO 9213845); 5-(chlorosulfonyl)-2,4,6-triiodoisophthaloyl dichloride [135466-77-2](FR 2649698); 5-chloro-2-iodobenzenesulfonyl chloride [124866-38-2] (FR 2626000); 4-(acetylamino)-2,3-diiodobenzenesulfonyl chloride [118427-11-5] (HU 44481); 2-iodo-3,5-dimethylbenzenesulfonyl chloride [98545-86-9] (J. Chem. Soc. Abstr. 1956, 3668); 2-iodobenzenesulfonyl chloride [63059-29-0] (e.g., J. Med. Chem. 2005, 48, 353, EP 516392).


Certain tert-butylaminosulfonyl compounds of the formula (XIV) are known: N-(tert-butyl)-4-chloro-2-iodobenzenesulfonamide [271796-71-5]; N-(tert-butyl)-2-iodobenzenesulfonamide [146720-72-1] (EP 516392); methyl 3-[(tert-butylamino)sulfonyl]-2-iodobenzoate [144550-74-3] (WO 9213845).
Of the compounds of the formula (II), it is preferred to exclude those in which R is H and I is 1 or 2 and R1 independently at each occurrence is one or more of the radicals NH2, halogen, CH3, CF3, CO2H, CO2(C1-C3)alkyl, SO2NH2, OCH3, NHC(O)CH3, N═CHN(CH3)2, (CH2)2NH2 or (CH2)2NHC(O)CF3;

    R is H and I is 0;
    R is NH2 and I is 0;
    R is NHC(O)CO2CH2CH3 and I is 0;
    R is CO2CH3 and I is 0, and also the compounds (2E)-N-{2-[3-(aminosulfonyl)-4-iodophenyl]ethyl}-3-(2,4-dimethoxyphenyl)acrylamide and N-{2-[3-(aminosulfonyl)-4-iodophenyl]ethyl}-5-chloro-2-methoxybenzamide.


Of the compounds of the formula (IV) it is preferred to exclude those in which W is O or S and R is H, I is 1, and R1 is CO2(C1-C3)alkyl;

    W is O or S and R is CO2(C1-C3)alkyl, and I is 0.


Of the compounds of the formula (VI) it is preferred to exclude those in which Hal is Cl and R is H, I is 1 or 2, and R1 independently at each occurrence is one or more halogen, CH3, CO2H, CO2(C1-C3)alkyl or NHC(O)CH3 radicals;

    Hal is Cl and R is H, and I is 0, and also the compounds (R)-3-chloro-2-iodo-4-[(3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl)amino]-benzenesulfonyl chloride and 5-(chlorosulfonyl)-2,4,6-triiodoisophthaloyl dichloride.


Of the compounds of the formula (XIV) it is preferred to exclude those in which R is H and I is 0 or 1 and R1 is halogen or CO2(C1-C3)alkyl.




Substituted tert-butylaminosulfonyl compounds of the formula (XIV) can also be obtained by metalating compounds of the formula (XVI)—that is, replacing the hydrogen atom ortho to the SO2NH-tert-butyl group in the compound of the formula (XVI) by a metal atom—said compounds (XIV) being obtainable by reacting commercially available sulfochlorides of the formula (XV) with tert-butylamine (see scheme 1) (sulfochlorides of the formula (XV) can also be prepared by diazotizing the corresponding amino compounds and subsequently sulfochlorinating the diazo products as indicated in scheme 1), the metallization being carried out using an organometallic compound, such as alkyl- or aryllithium, preferably n- or sec-butyllithium in hexane, optionally in the presence of a (further) inert diluent, such as tetrahydrofuran, and under an inert gas atmosphere, such as under argon or nitrogen, at temperatures between −70° C. and 20° C., and then, following metallization, reacting the product with iodine in the same reaction medium at temperatures between −100° C. and 40° C., preferably between −70° C. and 20° C., so as to replace the metal atom by iodine (scheme 5) (in this context see also: V. Snieckus et al., J. Org. Chem. 2001, 66, 3662 and Synlett 2000, (9), 1294).




Specific sulfonamides of the formula (II-a) with R′=hydrocarbon radical such as alkyl, heterocyclyl radical, CO—R3 or S(O)n—R3 can be prepared by reacting hydroxybenezenesulfonamides of the formula (XVII) with compounds of the formula (XVIII-a or XVIII-b), in which case one or more reaction auxiliaries may be used. In the compounds of the formula (XVIII-a) employed in this reaction the radical R′ is for example a hydrocarbon radical such as alkyl, a heterocyclyl radical, CO—R3 or S(O)nR3, and Hal is halogen, with alkyl, halogen, n and R3 being as defined in formula (I). In the compounds of the formula (XVIII-b) R′ may in particular be CO—R3 or S(O)nR3. Examples of suitable reaction auxiliaries include the customary acidic acceptors such as organic or inorganic bases. These include, preferably, alkali metal compounds or alkaline earth metal compounds, such as the acetates, amides, carbonates, hydrogencarbonates, hydrides, hydroxides, or alkanoates of alkali metals or alkaline earth metals—mention may be made in particular here of potassium carbonate, cesium carbonate, lithium hydroxide, sodium hydroxide, and sodium ethoxide—and also basic organic nitrogen compounds, such as triethylamine, ethyldiisopropylamine, alkyl-substituted pyridines, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).
Suitable solvents include not only water but also, in particular, inert organic solvents. These include, in particular, benzene, toluene, xylene, dichloromethane, chloroform, diethyl ether, dioxane, tetrahydrofuran, acetone, acetonitrile, N,N-dimethylformamide, N-methylpyrrolidone or ethyl acetate. The reaction temperatures range between 0° C. and the reflux temperature of the solvent used, preferably between 10° C. and 120° C. (scheme 6) (in this context cf. also WO 02/072560).




Hydroxybenzenesulfonamides of the formula (XVII) can be obtained, for example, from the ortho-alkoxy-substituted benzenesulfonamides of the formula (II-b) (obtainable, for example, by the reactions of schemes 1-6), it being possible for R′′ to be, in particular, (C1-C4)alkyl. For this purpose it is possible to treat the alkoxy compound of the formula (II-b) with a Lewis acid, preferably boron trihalides, such as BBr3, in an inert solvent such as dichloromethane, dichloroethane or chloroform, preferably dichloromethane or dichloroethane. The reaction temperature is generally between −30° C. and the reflux temperature of the solvent, preferably from 0° C. to 40° C. (scheme 7) (see for example EP044807 and WO 97/03056).




Benzenesulfonamides of the formula (II-d) can be obtained by exchanging the fluorine atom in the ortho-fluorobenzenesulfonamide of the formula (II-c) (obtainable, for example, by the reactions of schemes 1-6) by reaction with nuclophiles of the general formula R′′′. R′′′ can be, in particular, alkyloxy, cycloalkoxy, alkenyloxy, alkynyloxy, aryloxy, heterocyclyloxy, alkylthio, alkenylthio, alkynylthio, arylthio, heterocyclylthio, N(alkyl)2, NHalkyl, N(alkenyl)2, NHalkenyl, N(alkynyl)2, NHalkynyl, NHaryl, NHheterocyclyl or NH2, it being possible for all said radicals (apart from the last one) to be substituted or unsubstituted. In the context of this reaction it is also possible for one or more reaction auxiliaries to be employed, such as the typical acid acceptors, such as organic or inorganic bases. These include, preferably, alkali metal compounds or alkaline earth metal compounds, such as acetates, amides, carbonates, hydrogencarbonates, hydrides, hydroxides, or alkanoates of alkali metals or alkaline earth metals—mention may be made in particular here of potassium carbonate, cesium carbonate, lithium hydroxide, sodium hydroxide, and sodium ethoxide, and especially sodium hydride—and also basic organic nitrogen compounds, such as triethylamine, ethyldiisopropylamine, alkyl-substituted pyridines, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Suitable solvents include not only water but also, in particular, inert organic solvents. These include, in particular, benzene, toluene, xylene, dichloromethane, chloroform, diethyl ether, dioxane, tetrahydrofuran, acetone, acetonitrile, N,N-dimethylformamide, N-methylpyrrolidone or ethyl acetate, among which particular emphasis may be given to diethyl ether, dioxane, and tetrahydrofuran. The reaction temperature is generally between −20° C. and the reflux temperature of the solvent used, in particular between 0° C. and the reflux temperature of the solvent used.
Besides the purely thermal conduct of the reaction, it is also possible to accelerate the reaction using microwave energy. For this purpose it is possible to use a commercially available microwave apparatus designed for chemical use. The reactions in this case are carried out in general at temperatures between 20° C. and 200° C., preferably between 40° C. and 170° C., and with an energy output of between 20 and 200 watts, preferably between 50 and 180 watts, for a reaction time of between 2 min and 60 min, preferably between 5 min and 45 min.
Benzenesulfonamides of the formula (II-d) with R′′′=alkylthio, alkenylthio, alkynylthio, arylthio or heterocyclylthio can be converted into the corresponding sulfoxides or sulfones in analogy to reactions known from the literature, by treatment with oxidizing agent, preferably metachloroperbenzoic acid, hydrogen peroxide, sodium metaperiodate or Oxone (cf., e.g., “Reactions of Organosulfur Compounds”; Academic Press, New York, 1978, p. 16).
The (thio)carboxylic acid derivatives of the formula (III) used as starting materials in process a) of the invention for preparing compounds of the formula (I) are known and/or can be prepared by methods which are known per se (cf. EP 459244, EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266).
The sulfonyliso(thio)cyanates of the formula (IV) of the invention that are used in process b) of the invention for preparing compounds of the formula (I) can be prepared by methods known per se from the sulfonamides of the formula (II) of the invention (cf. DE 3208189, EP 23422, EP 64322, EP 44807, EP 216504). The aryl sulfonyliso(thio)cyanates are obtained with phosgene or thiophosgene, respectively, optionally in the presence of an alkyl isocyanate, such as butyl isocyanate, optionally in the presence of a reaction auxiliary, such as diazabicyclo[2.2.2]octane, and in the presence of a diluent, such as toluene, xylene or chlorobenzene, carrying out reaction at temperatures between 80° C. and 150° C. and following the reaction by distillative removal of the volatile components under reduced pressure.
The heterocyclyl compounds of the formula (V) used in processes b), c) and e) of the invention for preparing the compounds of the formula (I) are known and/or can be prepared by methods which are known per se (cf. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266).
The sulfonyl halides of the formula (VI) used in processes c) and d) of the invention for preparing the compounds of the formula (I) can be prepared by a variety of methods known from the literature, such as i) oxidative chlorination of thioether (Recl. Trav. Chim. Pays-Bas 1982, 101, 91, ii) diazotization of aromatic amines with sodium nitrite in hydrochloric acid, followed by reaction of the resulting diazonium salt with sulfur dioxide and copper chloride (J. Org. Chem. 1960, 1824), iii) heteroatom-controlled lithiation, followed by sulfonylation (EP 73562; Org. React. 1979, 26, I), iv) Newman rearrangement and subsequent oxidative chlorination (U.S. Pat. No. 5,157,119), v) reaction of a sulfonamide of the formula (II) with thienyl chloride (Bull. Kor. Chem. Soc. 1994, 15, 323).
In one embodiment of process c) the reaction mixture obtained by reacting the sulfonyl halide (VI) with a (thio)cyanate is used directly for coupling with a heterocyclyl compound of the formula (V) for the synthesis of the compound of the formula (I) (in this context cf. WO 2003 091228 and U.S. Pat. No. 5,550,238).
The (thio)carbamides of the formula (VIII) for use in process d) of the invention for preparing the compounds of the formula (I) are known and/or can be prepared by methods which are known per se (cf. EP 45924).
The sulfonylamino(thio)carbonyl compounds of the formula (IX) used in process e) of the invention for preparing compounds of the formula (I) are prepared in analogy to reactions which are known per se (cf. EP 120 814). Alternatively the sulfonyliso(thio)cyanates of the formula (IV) can also be converted into the carbamates of the formula (IX) in a straightforward reaction in an inert solvent, preferably diethyl ether or dichloromethane, using phenol, for example.
The processes a), b), c), d) and e) of the invention for preparing the compounds of the formula (I) are preferably carried out using diluents. Suitable diluents in this context include, in particular, inert organic solvents, examples being aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, tetrachloromethane, chlorobenzene und o-dichlorobenzene, ethers such as diethyl ether and dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran, and dioxane, ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone, esters such as methyl acetate and ethyl acetate, nitriles such as acetonitrile and propionitrile, amides, such as dimethylformamide, dimethylacetamide and N-methylpyrrolidone and also dimethyl sulfoxide, tetramethylene sulfone, and hexamethylphosphoramide.
Reaction auxiliaries which can be used for processes a), b), c), d) and e) of the invention include, for example, Lewis acids or acid acceptors which can be employed for reactions of this kind. Preferential suitability is possessed by acid acceptors, examples being alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides, such as calcium hydroxide, alkali metal carbonates and alkali metal alkoxides, such as sodium carbonate and potassium carbonate, sodium tert-butoxide and potassium tert-butoxide and also basic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N,N-dimethylbenzylamine, N,N-dimethylaniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4-ethyl- and 5-ethyl-2-methylpyridine, 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,8-diazabicyclo[5.4.0]-undec-7-en (DBU) and 1,4-diazabicyclo[2.2.2]octane (DABCO).
The reaction temperatures in processes a), b), c), d), and e) of the invention can be varied within a relatively wide range. It is usual to operate at temperatures between −20° C. and +150° C., preferably at temperatures between 0° C. and +100° C.
Processes a), b), c), d), and e) of the invention are generally carried out under atmospheric pressure. It is also possible, though, to operate under increased or reduced pressure.
Processes a), b), c), d), and e) of the invention are carried out using the respectively required starting materials in amounts which in general are approximately equimolar. It is also possible, though, to use one of the respectively employed components in a relatively large excess. The reactions are optionally carried out in a suitable diluent in the presence of a reaction auxiliary, such as an acid acceptor, and the reaction mixture is stirred at the respectively required temperature for a number of hours. Work up is accomplished, for processes a), b), c), d), and e) of the invention, by customary methods in each case (cf. the cited references).
The salts of the compounds of the formula (I) are prepared preferably in inert polar solvents, such as water, methanol or acetone, at temperatures from 0° C. to 100° C. Examples of suitable bases for preparing the salts of the invention are alkali metal carbonates, such as potassium carbonate, alkali metal hydroxides and alkaline earth metal hydroxides, such as NaOH or KOH, or alkali metal alkoxides, such as sodium methoxide or sodium tert-butoxide, or ammonia or ethanolamine.
The “inert solvents” identified in the above process versions refer in each case to solvents which are inert under the respective reaction conditions, but which need not necessarily be inert under any reaction conditions.
Collections of compounds of the formula (I) and/or salts thereof, which can be synthesized by the reactions identified above, can also be prepared parallelwise, in a manual, semiautomated or fully automated procedure. In this context it is possible, for example, to automate the implementation of the reaction, the workup or the purification of the products and/or intermediates. Overall this refers to a procedure as described for example by S. H. DeWitt in “Annual Reports in Combinatorial Chemistry and Molecular Diversity: Automated Synthesis”, volume 1, Escom 1997, pages 69 to 77.
Microwave-assisted syntheses can be carried out using a microwave apparatus, one example being the “Discover” model from CEM GmbH Mikrowellen-Analysentechnik, Carl-Friedrich-Gauβ-Str. 9, 47475 Kamp-Linffort, DE.
For the parallelized reaction procedure and workup it is possible to use a range of commercially available instruments, of the kind offered by, for example, the companies Stem Corporation, Woodrolfe Road, Tollesbury, Essex, GB, H+P Labortechnik GmbH, Bruckmannring 28, 85764 Oberschleiβheim, DE, or Radleys, Shirehill, Saffron Walden, Essex, CB 11 3AZ, GB. For the parallelized purification of compounds of the formula (I) and salts thereof and/or of intermediates obtained in the course of the preparation, the apparatus available includes chromatography apparatus, such as that from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, US.
The apparatus recited result in a modular procedure, in which the individual worksteps are automated and yet manual operations have to be carried out between the worksteps. This can be overcome by using partly or fully integrated automation systems in which the respective automation modules are served, for example, by robots. Automation systems of this kind can be acquired from, for example, Zymark Corporation, Zymark Center, Hopkinton, Mass. 01748, US.
Besides the methods described here, the preparation of compounds of the formula (I) and salts thereof may take place entirely or partly by means of solid-phase-supported methods. For this purpose, individual intermediates or all intermediates in the synthesis, or in a synthesis adapted for the corresponding procedure, are bound to a synthetic resin. Solid-phase-supported synthesis methods are well described in the technical literature, e.g., Barry A. Bunin in “The Combinatorial Index”, Academic Press, 1998.
The use of solid-phase-supported synthesis methods permits a range of protocols which are known from the literature and which in turn can be formed manually or automatively. For example it is possible to carry out partial automation of the “teabag” method (Houghten, U.S. Pat. No. 4,631,211; Houghten et al., Proc. Natl. Acad. Sci, 1985, 82, 5131-35) using products from IRORI, 11149 North Torrey Pines Road, La Jolla, Calif. 92037, US. Solid-phase-supported parallel syntheses are automated, for example, using apparatus from Argonaut Technologies, Inc., 887 Industrial Road, San Carlos, Calif. 94070, US or MultiSynTech GmbH, Wullener Feld 4, 58454 Witten, Del.
Preparation in accordance with the processes described here yields compounds of the formula (I) and salts thereof in the form of substance collections, referred to as libraries. The present invention additionally provides libraries comprising at least two compounds of the formula (I) and salts thereof.
The compounds of the formula (I) of the invention and/or salts thereof, referred to below collectively as “compounds of the invention”, exhibit excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous weed plants. Even perennial weeds which produce shoots from rhizomes, rootstocks or other perennial organs, and which cannot easily be controlled, are effectively controlled by the active substances.
The present invention hence also provides a method of controlling unwanted plants or of regulating growth of plants, preferably in crops of plants, in which one or more compounds of the invention are applied to the plants (e.g., weed plants such as monocot or dicot weeds or unwanted crop plants), the seed (e.g., grains, seeds or vegetative propagation organs such as tubers or shoots with buds) or the area on which the plants are growing (e.g., the area under cultivation). The compounds of the invention can be applied, for example, before sowing, pre-emergence or post-emergence. Specific mention may be made, by way of example, of certain representatives of the monocot and dicot weed flora which can be controlled by the compounds of the invention, although the naming of specific species should not be taken to imply any restriction.
Among the monocot weed species those controlled effectively include, for example, Apera spica venti, Avena spp., Alopecurus spp., Brachiaria spp., Digitaria spp., Lolium spp., Echinochloa spp., Panicum spp., Phalaris spp., Poa spp., Setaria spp. and also Bromus spp. such as Bromus catharticus, Bromus secalinus, Bromus erectus, Bromus tectorum, and Bromus japonicus, and Cyperus species from the annual group, and, among the perennial species, Agropyron, Cynodon, Imperata, and Sorghum, and also perennial Cyperus species.
In the case of dicot weed species, the spectrum of activity extends to species such as, for example, Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp. such as Galium aparine, Ipomoea spp., Kochia spp., Lamium spp., Matricaria spp., Pharbitis spp., Polygonum spp., Sida spp., Sinapis spp., Solanum spp., Stellaria spp., Veronica spp., and Viola spp., Xanthium spp., among the annuals, and also Convolvulus, Cirsium, Rumex and Artemisia among the perennial weeds.
Weed plants which occur in rice under the specific culture conditions, such as Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus, are likewise controlled to outstanding effect by the active substances of the invention.
If the compounds of the invention are applied to the soil surface prior to germination, then either emergence of the weed seedlings is prevented completely, or the weeds grow until they have reached the cotyledon stage, but their growth then comes to a standstill and, after three or four weeks have elapsed, they die off completely.
When the active substances are applied post-emergence to the green parts of plants there is likewise a drastic arrest in growth very soon after the treatment, and the weed plants remain at the growth stage they were in at the time of application, or die off completely after a certain time, so that in this way competition by the weeds, which is detrimental to the crop plants, is eliminated at a very early stage and in a sustained manner.
Although the compounds of the invention exhibit excellent herbicidal activity with respect to monocot or dicot weeds, crop plants of economic importance, examples being dicotyledonous crops such as soybean, cotton, oilseed rape, sugarbeet, or gramineous crops such as wheat, barley, rye, maize or rice, especially maize and wheat, are damaged either not at all or insignificantly. For these reasons, the present compounds possess excellent suitability for selectively controlling unwanted plant growth in plant crops such as agricultural stands of useful plants or stands of ornamentals.
Furthermore, the compounds of the invention exhibit outstanding growth-regulatory properties in respect of crop plants. They exert regulatory intervention in the plants' own metabolism and can therefore be employed to exert a controlled influence on plant constituents and to facilitate harvesting, such as by initiating desiccation and stunting of growth, for example. They are also suitable, moreover, for the general control and inhibition of unwanted vegetative growth, without killing off the plants. Inhibition of vegetative growth plays an important part in numerous monocot and dicot crops, since it allows their susceptibility to lodging to be reduced or prevented completely.
On the basis of their herbicidal and plant growth-regulatory properties, the active substances can also be used for controlling weed plants in crops of genetically modified plants which are known or are yet to be developed. As a rule, the transgenic plants are distinguished by particular advantageous properties, such as by resistances to certain pesticides, especially certain herbicides, resistances to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms, for instance fungi, bacteria or viruses. Other particular properties relate for example to the harvested material, in terms of quantity, quality, storage properties, composition, and specific constituents. For instance, transgenic plants are known which feature increased starch content or modified quality of starch, or whose fatty acid composition in the harvested material is different.
The compounds of the invention are employed preferably in economically important transgenic crops of useful plants and ornamentals, such as of cereals such as wheat, barley, rye, oats, millet, rice, cassaya, and maize, or else crops of sugarbeet, cotton, soybean, oilseed rape, potato, tomato, pea, and other vegetables. The compounds of the invention can be used with preference as herbicides in crops of useful plants which are resistant or have been made genetically resistant to the phytotoxic effects of the herbicides.
Conventional routes to the generation of new plants which have modified properties as compared with existing plants include, for example, the traditional breeding methods and the production of mutants. Alternatively, novel plants with modified properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044 and EP-A-0131624). Descriptions have been given, for example, in a number of cases, of:

    
    
        genetic modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g., WO 92/11376, WO 92/14827 and WO 91/19806);
        transgenic crop plants which are resistant to certain herbicides of the glufosinate type (cf., e.g., EP-A-0242236, EP-A-242246) or glyphosate type (WO 92/00377) or of the sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659);
        transgenic crop plants, cotton for example, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make the plants resistant to certain pests (EP-A-0142924 and EP-A-0193259); and
        transgenic crop plants with modified fatty acid composition (WO 91/13972).
    
    


Numerous techniques of molecular biology which allow new transgenic plants having modified properties to be generated are known in principle (see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene und Klone”, VCH Weinheim, 2nd edition, 1996; or Christou, Trends in Plant Science 1 (1996) 423-31).
For genetic manipulations of this kind it is possible to introduce nucleic acid molecules into plasmids that permit mutagenesis or a sequence alteration by recombination of DNA sequences. With the aid of the abovementioned standard techniques it is possible, for example, to carry out base substitutions, to remove part-sequences or to add natural or synthetic sequences. The fragments can be provided with adapters or linkers to link the DNA fragments to one another.
Plant cells featuring reduced activity of a gene product can be produced, for example, by expressing at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect, or expressing at least one appropriately constructed ribozyme which specifically cleaves transcripts of the above-mentioned gene product.
For this purpose it is possible on the one hand to use DNA molecules which encompass the entire coding sequence of a gene product, including any flanking sequences that may be present, and also DNA molecules which encompass only parts of the coding sequence, in which case these parts must be long enough to produce an antisense effect in the cells. A further possibility is the use of DNA sequences which have a high degree of homology with the coding sequences of a gene product and yet are not entirely identical.
In the context of expressing nucleic acid molecules in plants, the synthesized protein may be localized in any desired compartment of the plant cell. However, in order to achieve localization in one particular compartment, the coding region can be linked, for example, to DNA sequences which ensure localization in one particular compartment. Sequences of this kind are known to the skilled worker (see, for example, Braun et al., EMBO J. 11 (1992), 3219-27; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-50; Sonnewald et al., Plant J. 1 (1991), 95-106).
The transgenic plant cells can be regenerated by known techniques to form whole plants. In principle, the transgenic plants can be plants of any desired plant species, i.e., both monocotyledonous and dicotyledonous plants.
Thus it is possible to obtain transgenic plants which exhibit modified properties through overexpression, suppression or inhibition of homologous (i.e., natural) genes or gene sequences, or expression of heterologous (i.e., foreign) genes or gene sequences.
The compounds of the invention can be used with preference in transgenic crops which are resistant to herbicides from the group of sulfonylaminocarbonyl compounds, sulfonylureas, glufosinate-ammonium or glyphosate-isopropylammonium, and analogous active substances.
When the compounds of the invention are employed in transgenic crops, effects are frequently apparent—in addition to the effects on weed plants that are observed in other crops—that are specific to application in the particular transgenic crop: for example, a modified or specifically widened controllable weed spectrum, modified application rates which can be used for application, preferably effective capacity for combination with the herbicides to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.
The invention hence also provides for the use of the compounds of the invention as herbicides for controlling weed plants in transgenic and nontransgenic plant crops.
The compounds of the invention can be employed in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary preparations. The invention therefore also provides herbicidal and plant growth regulating compositions which comprise the compounds of the invention.
The compounds of the invention can be formulated in a variety of ways as a function of the prevailing biological and/or chemicophysical parameters. Examples of suitable formulation options include the following: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), seed-dressing products, granules for spreading and soil application, granules (GR) in the form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules, and waxes. These individual types of formulation are known in principle and are described in, for example, Winnacker-Küchler, “Chemische Technologie”, volume 7, C. Hanser Verlag Munich, 4th ed. 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.
The formulation auxiliaries required, such as inert materials, surfactants, solvents, and further adjuvants, are likewise known and are described in, for example, the following: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd ed., Darland Books, Caldwell N.J., H.v. Olphen, “Introduction to Clay Colloid Chemistry”; 2nd ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd ed., Interscience, N. Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N. Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte”, Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie”, volume 7, C. Hanser Verlag Munich, 4th ed. 1986.
On the basis of these formulations it is also possible to produce combinations with other pesticidal substances, such as insecticides, acaricides, herbicides, and fungicides, and also with safeners, fertilizers and/or growth regulators, in the form, for example, of a ready-to-use formulation, or as a tank mix.
Wettable powders are products which can be dispersed uniformly in water and which also include, besides the active substance, and in addition to a diluent or inert substance, ionic and/or nonionic surfactants (wetting agents, dispersants), examples being polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium ligninsulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurate. To prepare the wettable powders, the active herbicidal substances, for example, are finely ground in customary apparatus such as hammer mills, blower mills, and air-jet mills, and are simultaneously or subsequently mixed with the formation auxiliaries.
Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons, or mixtures of the organic solvents with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which can be used include the following: calcium alkylarylsulfonate salts such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglyol ethers, fatty alcohol polyglycol ethers, propylene oxide ethylene oxide-condensates, alkyl polyethers, sorbitan esters such as sorbitan fatty acid esters or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters.
Dusts are obtained by grinding the active substance with finely divided solid materials, such as talc, natural clays, such as kaolin, bentonite, and pyrophyllite, or diatomaceous earth.
Suspension concentrates can be water-based or oil-based. One example of their possible preparation is by wet grinding using commercially customary bead mills, where appropriate with addition of surfactants, as have already been recited above in connection with the other types of formulation, for example.
Emulsions, such as oil-in-water emulsions (EW), for example, can be prepared for example by means of stirrers, colloid mills and/or static mixers, using aqueous organic solvents and, where appropriate, surfactants as have already been recited above in relation to the other types of formulation.
Granules can be produced either by spraying the active substance through nozzles onto adsorptive, granulated inert material or by applying active substance concentrates to the surface of carriers such as sand, kaolinites or else granulated inert material with the aid of tackifiers, such as polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active substances can also be granulated in the way which is conventional for the production of fertilizer granules, and if desired as a mixture with fertilizers.
Water-dispersible granules are produced generally by the customary methods such as spray drying, fluidized-bed granulation, disk granulation, mixing with high-speed mixers, and extrusion without solid inert material.
To produce disk granules, fluidized-bed granules, extruder granules, and spray granules, see, for example, methods in “Spray-Drying Handbook”, 3rd ed., 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 ff; “Perry's Chemical Engineer's Handbook”, 5th ed., McGraw-Hill, New York 1973, p. 8-57.
For further details on the formulation of crop protection products see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
The agrochemical preparations contain in general 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds of the invention. In wettable powders the active substance concentration is for example about 10% to 90% by weight, the remainder to 100% by weight being composed of typical formation ingredients. In the case of emulsifiable concentrates the active substance concentration can be about 1% to 90%, preferably 5% to 80% by weight. Dust formulations contain 1% to 30% by weight of active substance, preferably mostly 5% to 20% by weight of active substance; sprayable solutions contain about 0.05% to 80%, preferably 2% to 50% by weight of active substance. In the case of water-dispersible granules the active substance content depends partly on whether the active compound is in solid or in liquid form and on what granulating assistants, fillers, etc. are used. For the water-dispersible granules, the active substance content is for example between 1% and 95% by weight, preferably between 10% and 80% by weight.
In addition, the stated active substance formulations comprise, where appropriate, the stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, frost preventives, solvents, fillers, carriers, colorants, defoamers, antievaporants, pH modifiers, and viscosity modifiers that are customary in each case.
Candidate co-components for the compounds of the invention in mixture formulations or in a tank mix are, for example, known active substances which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, by Weed Research 26 (1986) 441-45 or “The Pesticide Manual”, 13th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003, and references cited therein. Examples of known herbicides which can be combined with the compounds of the invention include the following active substances (note: the compounds are designated either by their “common name” in accordance with the International Organization for Standardization (ISO) or by the chemical name, together where appropriate with a customary code number), which in each case include all use forms, such as acids, salts, esters, and isomers such as stereoisomers and optical isomers. The citation given is of one use form and in some cases of two or more use forms:
2,4-D, acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidosulfuron, aminopyralid, amitrole, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfuresate, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclon, benzofenap, bifenox, bilanafos, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone-ethyl, chlomethoxyfen, chloridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron, chlorsulfuron, cinidon-ethyl, cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam-methyl, cumyluron, cyanazine, cyclosulfamuron, cycloxydim, cyhalofop-butyl, desmedipham, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, dikegulac-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, triaziflam, diquat-dibromide, dithiopyr, diuron, dymron, EPTC, esprocarb, ethalfluralin, ethametsulfuron-methyl, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-butyl, fluazifop-butyl, fluazolate, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flumetsulam, flumiclorac-pentyl, flumioxazin, fluometuron, fluorochloridone, fluoroglycofen-ethyl; flupoxam, flupyrsulfuron-methyl-sodium, fluridone, fluroxypyr, fluroxypyr-butoxypropyl, fluroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, glufosinate, glufosinate-ammonium, glyphosate, halosulfuron-methyl, haloxyfop, haloxyfop-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, indanofan, iodosulfuron-methyl-sodium, ioxynil, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, ketospiradox, lactofen, lenacil, linuron, MCPA, mecoprop, mecoprop-P, mefenacet, mesosulfuron-methyl, mesotrione, metamifop, metamitron, metazachlor, methabenzthiazuron, methyldymron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron-methyl, molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, penoxsulam, pentoxazone, pethoxamid, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron-methyl, profluazol, profoxydim, prometryn, propachlor, propanil, propaquizafop, propisochlor, propoxycarbazone-sodium, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen-ethyl, pyrazolate, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, quinclorac, quinmerac, quinoclamine, quizalofop-ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, sethoxydim, simazine, simetryn, S-metolachlor, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosate, sulfosulfuron, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thifensulfuron-methyl, thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron-methyl, triclopyr, tridiphane, trifloxysulfuron, trifluralin, triflusulfuron-methyl, and tritosulfuron.
The compounds of the invention can also be used in combination with one or more compounds which act as safeners. Examples of safeners include the following compounds:

    a) Compounds of formulae (XIX) to (XXI),






where the symbols and indices have the following definitions:

    n′ is a natural number from 0 to 5, preferably 0 to 3;
    T is a (C1 or C2)alkanediyl chain which is unsubstituted or substituted by one or two (C1-C4)alkyl radicals or by [(C1-C3)alkoxy]carbonyl;
    W+ is an unsubstituted or substituted divalent heterocyclic radical from the group of partly unsaturated or aromatic five-membered-ring heterocycles having 1 to 3 ring heteroatoms of N or O type, including at least one nitrogen atom and not more than one oxygen atom in the ring, preferably a radical from the group (W+1) to (W+4),






    m′ is 0 or 1;
    R12 and R14 are identical or different and are hydrogen, halogen, (C1-C4)alkyl, (C1-C4)alkoxy, nitro or (C1-C4)haloalkyl;
    R13 and R15 are identical or different and are OR19, SR19 or NR19R20 or are a saturated or unsaturated 3- to 7-membered heterocycle having at least one nitrogen atom and up to 3 heteroatoms, preferably from the group of O and S, which is attached via the nitrogen atom to the carbonyl group in (XIX) or (XX) and is unsubstituted or substituted by radicals from the group consisting of (C1-C4)alkyl, (C1-C4)alkoxy or optionally substituted phenyl, and are preferably a radical of the formula OR19, NHR20 or N(CH3)2, particularly of the formula OR19;
    R19 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 carbon atoms;
    R20 is hydrogen, (C1-C6)alkyl, (C1-C6)alkoxy or substituted or unsubstituted phenyl;
    R21 is hydrogen, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C4)alkoxy-(C1-C4)alkyl, (C1-C4)hydroxyalkyl, (C3-C12)cycloalkyl or tri-(C1-C4)alkylsilyl;
    R22, R23 and R24 are identical or different and are hydrogen, (C1-C8)alkyl, (C1-C8)haloalkyl, (C3-C12)cycloalkyl or substituted or unsubstituted phenyl;
    R16 is (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkenyl, (C2-C4)haloalkenyl, (C3-C7)cycloalkyl, preferably dichloromethyl;
    R17 and R18 are each identical or different and are hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C1-C4)haloalkyl, (C2-C4)haloalkenyl, (C1-C4)alkylcarbamoyl-(C1-C4)alkyl, (C2-C4)alkenylcarbamoyl-(C1-C4)alkyl, (C1-C4)alkoxy-(C1-C4)alkyl, dioxolanyl-(C1-C4)alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or R12 and R13 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, dihydropyrimidine or benzoxazine ring; or
    b) one or more compounds from the following group:
    
        1,8-naphthalic anhydride,
        methyl diphenylmethoxyacetate,
        cyanomethoxyimino(phenyl)acetonitrile (cyometrinil),
        1,3-dioxolane-2-ylmethoxyimino(phenyl)acetonitrile (oxabetrinil),
        4′-chloro-2,2,2-trifluoroacetophenone O-1,3-dioxolan-2-ylmethyloxime (fluxofenim),
        4,6-dichloro-2-phenylpyrimidine (fenclorim),
        benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole),
        2-dichloromethyl-2-methyl-1,3-dioxolan (MG-191),
        N-(4-methylphenyl)-N′-(1-methyl-1-phenylethyl)urea (dymron),
        1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea,
        1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea,
        1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea,
        1-[4-(N-naphthoylsulfamoyl)phenyl]-3,3-dimethylurea,
        (2,4-dichlorophenoxy)acetic acid (2,4-D),
        (4-chlorophenoxy)acetic acid,
        (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),
        4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),
        (4-chloro-o-tolyloxy)acetic acid (MCPA),
        4-(4-Chloro-o-tolyloxy)butyric acid,
        4-(4-chlorophenoxy)butyric acid,
        3,6-dichloro-2-methoxybenzoic acid (dicamba),
        1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor),
        and also salts and esters thereor, preferably (C1-C8) esters;
    
    
    c) N-acylsulfonamides of the formula (XXII) and salts thereof,






in which

    R25 is hydrogen, a hydrocarbon radical, a hydrocarbonoxy radical, a hydrocarbonthio radical or a heterocyclyl radical, each of the last-mentioned four radicals being unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, cyano, nitro, amino, hydroxy, carboxyl, formyl, carbonamide, sulfonamide, and radicals of the formula —Za—Ra,
    
        each hydrocarbon moiety having preferably 1 to 20 carbon atoms, and a carbon-containing radical R25, inclusive of substituents, having preferably 1 to 30 carbon atoms;
    
    
    R26 is hydrogen or (C1-C4)alkyl, preferably hydrogen, or
    R25 and R26 together with the group of the formula —CO—N— are the radical of a 3- to 8-membered saturated or unsaturated ring;
    R27 is identical or different at each occurrence and is halogen, cyano, nitro, amino, hydroxy, carboxyl, formyl, CONH2, SO2NH2 or a radical of the formula —Zb—Rb;
    R28 is hydrogen or (C1-C4)alkyl, preferably H;
    R29 is identical or different at each occurrence and is halogen, cyano, nitro, amino, hydroxy, carboxyl, CHO, CONH2, SO2NH2 or a radical of the formula —Zc—Rc;
    Ra is a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, cyano, nitro, amino, hydroxy, and mono- and di-[(C1-C4)alkyl]amino, or is an alkyl radical in which 2 or more, preferably 2 or 3, nonadjacent CH2 groups are each replaced by an oxygen atom;
    Rb and Rc are identical or different and are each a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals from the group consisting of halogen, cyano, nitro, amino, hydroxy, phosphoryl, halo-(C1-C4)alkoxy, and mono- and di-[(C1-C4)alkyl]amino, or are each an alkyl radical in which 2 or more, preferably 2 or 3, nonadjacent CH2 groups are each replaced by an oxygen atom;
    Za is a divalent group of the formula —O—, —S—, —CO—, —CS—, —CO—O—, —CO—S—, —O—CO—, —S—CO—, —SO—, —SO2—, —NR+—, —CO—NR+—, —NR+—CO—, —SO2—NR+— or —NR+—SO2—, the bond indicated on the right in the respective divalent group, being the bond to the radical Ra, and the R+ in the last-mentioned 5 radicals each being, independently of one another, H, (C1-C4)alkyl or halo-(C1-C4)-alkyl;
    Zb and Zc independently of one another are each a direct bond or a divalent group of the formula —O—, —S—, —CO—, —CS—, —CO—O—, —CO—S—, —O—CO—, —S—CO—, —SO—, —SO2—NR+—, —SO2—NR+—, —NR+—SO2—, —CO—NR+—
    
        or —NR+—CO—, the bond indicated on the right in the respective divalent group being the bond to the radical Rb or Rc, respectively, and the R+ in the last-mentioned 5 radicals each being, independently of one another, H, (C1-C4)alkyl or halo-(C1-C4)alkyl;
    
    
    n is an integer from 0 to 4, preferably 0, 1 or 2, particularly 0 or 1, and
    m is an integer from 0 to 5, preferably 0, 1, 2 or 3, particularly 0, 1 or 2;
    d) acylsulfamoylbenzamides of the formula (XXIII), where appropriate also in salt form,






in which

    X3 is CH or N;
    R30 is hydrogen, heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals being optionally substituted by one or more, identical or different radicals from the group consisting of halogen, cyano, nitro, amino, hydroxy, carboxyl, CHO, CONH2, SO2NH2 and Za—Ra;
    R31 is hydrogen, hydroxy, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C2-C6)alkenyloxy, the five last-mentioned radicals being optionally substituted by one or more, identical or different radicals from the group consisting of halogen, hydroxy, (C1-C4)alkyl, (C1-C4)alkoxy, and (C1-C4)alkylthio, or
    R30 and R31 together with the nitrogen atom which carries them are a 3- to 8-membered saturated or unsaturated ring;
    R32 is halogen, cyano, nitro, amino, hydroxy, carboxyl, CHO, CONH2, SO2NH2 or Zb—Rb;
    R33 is hydrogen, (C1-C4)alkyl, (C2-C4)alkenyl or (C2-C4)alkynyl;
    R34 is halogen, cyano, nitro, amino, hydroxy, carboxyl, phosphoryl, CHO, CONH2, SO2NH2 or Zc—Rc;
    Ra is a (C2-C20)alkyl radical whose carbon chain is interrupted one or more times by oxygen atoms, or is heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals being optionally substituted by one or more, identical or different radicals from the group consisting of halogen, cyano, nitro, amino, hydroxy, and mono- and di-[(C1-C4)alkyl]amino;
    Rb and Rc are identical or different and are each a (C2-C20)alkyl radical whose carbon chain is interrupted one or more times by oxygen atoms, or are heterocyclyl or a hydrocarbon radical, the two last-mentioned radicals being optionally substituted by one or more, identical or different radicals from the group consisting of halogen, cyano, nitro, amino, hydroxy, phosphoryl, (C1-C4)-haloalkoxy, and mono- and di-[(C1-C4)alkyl]amino;
    Za is a divalent unit from the group O, S, CO, CS, C(O)O, C(O)S, SO, SO2, NRd, C(O)NRd or SO2NRd;
    Zb and Zc are identical or different and are each a direct bond or a divalent unit from the group O, S, CO, CS, C(O)O, C(O)S, SO, SO2, NRd, SO2, NRd or C(O)NRd;
    Rd is hydrogen, (C1-C4)alkyl or (C1-C4)haloalkyl;
    n is an integer from 0 to 4, and
    m, if X is CH, is an integer from 0 to 5 and, if X is N, is an integer from 0 to 4;
    e) Compounds of formula (XXIV),






in which the symbols and indices have the following definitions:

    R35 is H, (C1-C4)alkyl, (C1-C4)alkyl substituted by (C1-C4)alkyl-X4 or (C1-C4)haloalkyl-X4, (C1-C4)haloalkyl, NO2, CN, —COO—R38, NR239, SO2NR240 or CONR241;
    R36 is H, halogen, (C1-C4)alkyl, CF3, (C1-C4)alkoxy or (C1-C4)haloalkoxy;
    R37 is H, halogen or (C1-C4)alkyl;
    Q1 and Q2, E and G are identical or different and are —O—, —S—, —CR242—, —CO—, NR43—or a group of formula (XXV),






     with the provisos that
    a) at least one of groups Q1, Q2, E, and G is a carbonyl group, that exactly one of these groups is a radical of the formula (XXV), and that the group of formula (XXV) is adjacent to a carbonyl group, and
    b) two adjacent groups Q1, Q2, E, and G cannot simultaneously be oxygen;
    Ra is identical or different at each occurrence and is H or (C1-C8)alkyl, or the two radicals Ra together are (C2-C6)alkylene;
    A is Rb—Y3— or —NR244;
    X4 is —O— or —S(O)p—;
    Y3 is —O— or —S—;
    Rb is H, (C1-C8)alkyl, (C1-C8)haloalkyl, (C1-C4)alkoxy-(C1-C8)alkyl, (C3-C6)alkenyloxy-(C1-C8)alkyl, or phenyl-(C1-C8)alkyl, the phenyl ring being optionally substituted by halogen, (C1-C4)alkyl, CF3, methoxy or methyl-S(O)p; (C3-C6)alkenyl, (C3-C6)haloalkenyl, phenyl-(C3-C6)alkenyl, (C3-C6)alkynyl, phenyl-(C3-C6)alkynyl, oxetanyl, furfuryl, tetrahydrofuryl;
    R38 is H or (C1-C4)alkyl;
    R39 is identical or different at each occurrence and is H, (C1-C4)alkyl, (C1-C4)alkylcarbonyl, or the two radicals R39 together are (C4-C5)alkylene;
    R40 and R41 are independently of one another each identical or different and are H, (C1-C4)alkyl, or the two radicals R40 and/or R41 together are (C4-C5)alkylene, it being possible for one CH2 group to be replaced by O or S or for one or two CH2 groups to be replaced by —NRc—;
    Rc is H or (C1-C8)alkyl;
    R42 is identical or different at each occurrence and is H, (C1-C8)alkyl, or the two radicals R42 together are (C2-C6)alkylene;
    R43 is H, (C1-C8)alkyl, substituted or unsubstituted phenyl, or benzyl which is unsubstituted or is substituted on the phenyl ring;
    R44 is identical or different at each occurrence and is H, (C1-C8)alkyl, phenyl, phenyl-(C1-C8)alkyl, it being possible for a phenyl ring to be substituted by F, Cl, Br, NO2, CN, OCH3, (C1-C4)alkyl or CH3SO2—; (C1-C4)alkoxy-(C1-C8)alkyl, (C3-C6)alkenyl, (C3-C6)alkynyl, (C3-C6)cycloalkyl or two radicals R44 together are (C4-C5)alkylene, it being possible for one CH2 group to be replaced by O or S or for one or two CH2 groups to be replaced by —NRd—;
    Rd is H or (C1-C4)alkyl;
    m′′ is 0 or 1, and
    p is 0, 1 or 2;

including the stereoisomers and the agriculturally useful salts.



For the purpose of application, the formations in their commercially customary form are where appropriate subjected to customary dilution, by means of water in the case for example of wettable powders, emulsifiable concentrates, dispersions, and water-dispersible granules. Preparations in dust form, soil granules and broadcasting granules, and also sprayable solutions, are typically not diluted with further inert substances prior to their application.
The application rate of the compounds of the invention that is required varies with the external conditions such as temperature, humidity, and identity of the herbicide used. The rate may fluctuate within wide limits—for example, between 0.001 and 10.0 kg or more of active substance per hectare—and is preferably between 0.005 and 5 kg/ha.


EXAMPLES
A. Synthesis Examples
Example A1
N-(tert-Butyl)-2-methoxybenzenesulfonamide
A solution of 30.00 g (145.17 mmol) of 2-methoxybenzenesulfonyl chloride in 150 ml of dichloromethane is admixed dropwise at 5-10° C. with 22.30 g (304.87 mmol) of tert-butylamine. The mixture is then stirred at room temperature for 2 h. Following extraction with water, the organic phase is dried over sodium sulfate and evaporated to dryness. This gives 31.10 g (88% of theory) of N-(tert-butyl)-2-methoxybenzenesulfonamide.
1H NMR (CDCl3): 7.91 (dd, J=1.7, 7.8, 1H); 7.50 (m, 1H); 7.03 (m, 2H); 4.93 (br s, 1H); 3.98 (s, 3H); 1.17 (s, 9H).
Example A2
N-(tert-Butyl)-2-iodo-6-methoxybenzenesulfonamide (Example 2.092b)
A solution of 30.00 g (123.29 mmol) of N-(tert-butyl)-2-methoxybenzenesulfonamide in 400 ml of tetrahydrofuran is cooled to −70° C. and slowly admixed with a solution of 110.96 ml (277.41 mmol) of a 2.5 molar n-butyllithium solution in THF. The solution is subsequently warmed briefly to −30° C. and then cooled again to −60° C. At this temperature a solution of 31.29 g (123.29 mmol) of iodine in 200 ml of tetrahydrofuran is added dropwise. Subsequently the reaction solution is stirred at room temperature overnight. Following extraction with water, the organic phase is dried over sodium sulfate and evaporated to dryness. This gives 42.40 g (93% of theory) of N-(tert-butyl)-2-iodo-6-methoxybenzenesulfonamide.
Example A3
2-Iodo-6-methoxybenzenesulfonamide (Example 2.092a)
42.40 g (114.84 mmol) N-(tert-butyl)-2-iodo-6-methoxybenzenesulfonamide are stirred in 265 ml of trifluoroacetic acid at room temperature for 3 h. Thereafter the reaction mixture is poured into ice-water and the precipitate is isolated by filtration and washed to neutrality with water. This gives 32.40 g (90% of theory) of 2-iodo-6-methoxybenzenesulfonamide.
Example A4
4-Cyclopropyl-3-ethoxy-N-[(2-iodo-6-methoxyphenyl)sulfonyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxamide (Example 1.191)
A solution of 250 mg (0.80 mmol) of 2-iodo-6-methoxybenzenesulfonamide in 3 ml of acetonitrile is admixed at room temperature first with 254.08 mg (0.88 mmol) of 4-cyclopropyl-3-ethoxy-5-oxo-1-phenyloxycarbonyl-4,5-dihydro-1H-1,2,4-triazole and then slowly with 0.24 ml (1.60 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. After 60 min of stirring at room temperature the solution is adjusted slowly to a pH of 1 using 2 N salt solution. The precipitated solid is filtered off with suction, washed with diisopropyl ether and acetonitrile, and dried. This gives 267 mg (62% of theory) of 4-cyclopropyl-3-ethoxy-N-[(2-iodo-6-methoxyphenyl)sulfonyl]-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxamide.
Example A5
2-Hydroxy-6-iodobenzenesulfonamide (Example 2.300a)
0.50 g (1.60 mmol) of 2-iodo-6-methoxybenzenesulfonamide are introduced in 10 ml of dichloromethane at room temperature and this initial charge is cautiously admixed with 0.6 g (2.40 mmol) of boron tribromide. The reaction solution is stirred at room temperature for a further 45 min and then added to 2 N hydrochloric acid. Following extraction with dichloromethane, the organic phase is dried and evaporated. This gives 0.43 g (90% of theory) of 2-hydroxy-6-iodobenzenesulfonamide.
Example A6
2-Iodo-6-propoxybenzenesulfonamide (Example 2.095a)
5.00 g (16.72 mmol) of 2-hydroxy-6-iodobenzenesulfonamide are introduced in 50 ml of dimethylformamide and this initial charge is admixed with 2.54 g (18.39 mmol) of potassium carbonate. This mixture is stirred at room temperature for 1 h. Thereafter 3.13 g (18.39 mmol) of propyl iodide are added dropwise and the reaction mixture is stirred at room temperature for 3 h. It is then poured into water, and the product precipitates out. The solid is washed with water and dried. This gives 4.00 g (70% of theory) of 2-iodo-6-propoxybenzenesulfonamide.
Example A7
N-(tert-Butyl)-2-fluoro-6-iodobenzenesulfonamide (Example 2.001 b)
30 g (0.13 mol) of (N-tert-butyl)-2-fluorobenzenesulfonamide, obtained from the reaction of 2-fluorobenzenesulfonyl chloride with N-tert-butylamine in analogy to example A1, are introduced in 300 ml of dry tetrahydrofuran. The solution is cooled to −70° C. and a solution of 18.28 g (0.285 mol) of n-butyllithium (2.5 molar in tetrahydrofuran) is added dropwise. Thereafter the reaction solution is warmed to −30° C. over 30 min, after which it is cooled again to −70° C. Then 36.21 g (0.143 mol) of iodine in 200 ml of dry tetrahydrofuran are added dropwise. Following the addition the reaction solution is warmed slowly to room temperature and stirred for 12 h. Thereafter it is washed with 50% strength aqueous sodium thiosulfate solution and water. The organic phase is dried and evaporated. This gives 40.8 g (88% of theory) of N-(tert-butyl)-2-fluoro-6-iodobenzenesulfonamide.
Example A8
2-(2,2-Difluoroethoxy)-6-iodobenzenesulfonamide (Example 2.187a)
0.64 g (26.57 mmol) of sodium hydride is introduced in 10 ml of dry tetrahydrofuran and this initial charge is slowly admixed at room temperature with 2.18 g (26.57 mmol) of 2,2-difluoroethanol. The reaction mixture is stirred at room temperature until the evolution of gas ceases. Thereafter 4.00 g (13.29 mmol) of 2-fluoro-6-iodo-benzenesulfonamide, obtained from the reaction of N-(tert-butyl)-2-fluoro-6-iodobenzenesulfonamide with trifluoroacetic acid in analogy to example A3, in solution in 20 ml of dry tetrahydrofuran, are added dropwise. This reaction mixture is exposed to a microwave energy of 100 watts at 150° C. for 30 min. Thereafter the pH is adjusted to 4-5 using 2 N hydrochloric acid and the mixture is partitioned in water/ethyl acetate, the organic phase being dried and evaporated. This gives 3.00 g (62% of theory) of 2-(2,2-difluoroethoxy)-6-iodobenzenesulfonamide.
Example A9
2-Iodo-6-(methylthio)benzenesulfonamide (Example 2.208a)
30.00 g (99.64 mmol) of 2-fluoro-6-iodobenzenesulfonamide, obtained from the reaction of N-(tert-butyl)-2-fluoro-6-iodobenzenesulfonamide with trifluoroacetic acid in analogy to example A3, are introduced together with 15.15 g (109.61 mmol) of potassium carbonate in 250 ml of dimethylformamide. At room temperature 7.68 g (109.61 mmol) of sodium thiomethoxide are added in portions, after which the mixture is stirred at room temperature for 12 h. It is poured into 150 ml of ice-water, adjusted to a pH of 4-5 using 2 N hydrochloric acid, and extracted with ethyl acetate. The organic phase is dried and evaporated. Preparative HPLC (reversed phase, 0.05% trifluoroacetic acid in water/acetonitrile, gradient: in 30 min, 25% to 100% acetonitrile) gives 7.40 g (23% of theory) of 2-iodo-6-(methylthio)benzenesulfonamide.
The compounds described in tables 1 and 2 below are obtained in the same way as examples A1-A9 above.
Abbreviations in tables 1 and 2 below:

    *=1H NMR data are listed after tables 1 and 2, respectively
    Me=methyl
    Ph=phenyl
    Het=heterocycle, with Het standing for one of the radicals H1 to H20 below
















TABLE 1







Compounds of the formula (I-a)









(I-a)








 













R
R1
M
Het
1H NMR
















1.001
H
—
H
H1
*


1.002
H
—
Na
H1


1.003
H
5-CH3
H
H1


1.004
H
—
H
H2
*


1.005
H
—
H
H3
*


1.006
H
—
H
H4


1.007
H
—
H
H5


1.008
H
—
H
H6
*


1.009
H
—
Na
H6


1.010
H
5-CH3
H
H6


1.011
H
—
H
H7
*


1.012
H
—
Na
H1


1.013
H
5-CH3
H
H7


1.014
H
—
H
H8
*


1.015
H
—
H
H11


1.016
H
—
H
H13


1.017
H
—
H
H14


1.018
H
—
H
H15


1.019
H
—
H
H16


1.020
H
—
H
H17


1.021
F
—
H
H1
*


1.022
F
—
H
H2
*


1.023
F
—
H
H3
*


1.024
F
—
H
H4
*


1.025
F
—
H
H5


1.026
F
—
H
H6


1.027
F
—
H
H7
*


1.028
F
—
H
H8
*


1.029
F
—
H
H11


1.030
F
—
H
H15


1.031
F
—
H
H16


1.032
Cl
—
H
H1


1.033
Cl
—
H
H6


1.034
Cl
—
H
H1


1.035
Br
—
H
H1


1.036
I
—
H
H1


1.037
CH3
—
H
H1
*


1.038
CH3
—
H
H2
*


1.039
CH3
—
H
H3
*


1.040
CH3
—
H
H4
*


1.041
CH3
—
H
H5


1.042
CH3
—
H
H6
*


1.043
CH3
—
H
H1
*


1.044
CH3
—
H
H8
*


1.045
CH3
—
H
H11


1.046
CH3
—
H
H13


1.047
CH3
—
H
H14


1.048
CH3
—
H
H15


1.049
CH3
—
H
H16


1.050
CH3
—
H
H17


1.051
CH2CH3
—
H
H1


1.052
CH2CH3
—
H
H2


1.053
CH2CH3
—
H
H6


1.054
CH2CH3
—
H
H7


1.055
(CH2)2CH3
—
H
H1


1.056
CH(CH3)2
—
H
H1


1.057
(CH2)3CH3
—
H
H1


1.058
CH(CH3)CH2CH3
—
H
H1


1.059
CH2CH(CH3)2
—
H
H1


1.060
C(CH3)3
—
H
H1


1.061
C(CH3)3
—
H
H2


1.062
C(CH3)3
—
H
H6


1.063
C(CH3)3
—
H
H7


1.064
CH═CH2
—
H
H1


1.065
CH═CH2
—
H
H2


1.066
CH═CH2
—
H
H6


1.067
CH═CH2
—
H
H7


1.068
C(CH3)═CH2
—
H
H1


1.069
C≡CH
—
H
H1


1.070
C≡CH
—
H
H2


1.071
C≡CH
—
H
H6


1.072
C≡CH
—
H
H1


1.073
C≡CCH3
—
H
H1


1.074
C≡CCH2CH3
—
H
H1


1.075
CH2CH═CH2
—
H
H1


1.076
CH2C(CH3)═CH2
—
H
H1


1.077
CH2C≡CH
—
H
H1


1.078
CH2C≡CCH3
—
H
H1


1.079
CH2C≡CCH2CH3
—
H
H1


1.080
cyclopropyl
—
H
H1


1.081
cyclopropyl
—
H
H2


1.082
cyclopropyl
—
H
H3


1.083
cyclopropyl
—
H
H4


1.084
cyclopropyl
—
H
H5


1.085
cyclopropyl
—
H
H6


1.086
cyclopropyl
—
H
H7


1.087
cyclopropyl
—
H
H8


1.088
cyclopropyl
—
H
H11


1.089
cyclopropyl
—
H
H13


1.090
cyclopropyl
—
H
H14


1.091
cyclopropyl
—
H
H15


1.092
cyclopropyl
—
H
H16


1.093
cyclopropyl
—
H
H17


1.094
2,2-di-F-cyclopropyl
—
H
H1


1.095
2,2-di-Cl-cyclopropyl
—
H
H1


1.096
2,2-di-CH3-cyclopropyl
—
H
H1


1.097
cyclobutyl
—
H
H1


1.098
cyclopentyl
—
H
H1


1.099
cyclohexyl
—
H
H1


1.100
CH2cyclopropyl
—
H
H1


1.101
CH2cyclobutyl
—
H
H1


1.102
CH2cyclopentyl
—
H
H1


1.103
CH2cyclohexyl
—
H
H1


1.104
CH2OCH3
—
H
H1


1.105
CH2OCH2CH3
—
H
H1


1.106
CH(CH3)OCH3
—
H
H1


1.107
Ph
—
H
H1


1.108
2-F-Ph
—
H
H1


1.109
3-F-Ph
—
H
H1


1.110
4-F-Ph
—
H
H1


1.111
2,6-di-F-Ph
—
H
H1


1.112
2,4-di-F-Ph
—
H
H1


1.113
2-Cl-Ph
—
H
H1


1.114
3-Cl-Ph
—
H
H1


1.115
4-Cl-Ph
—
H
H1


1.116
2,6-di-Cl-Ph
—
H
H1


1.117
2,4-di-Cl-Ph
—
H
H1


1.118
2-MeO-Ph
—
H
H1


1.119
3-MeO-Ph
—
H
H1


1.120
4-MeO-Ph
—
H
H1


1.121
2,4-di-MeO-Ph
—
H
H1


1.122
2-Me-Ph
—
H
H1


1.123
3-Me-Ph
—
H
H1


1.124
4-Me-Ph
—
H
H1


1.125
2-CF3-Ph
—
H
H1


1.126
3-CF3-Ph
—
H
H1


1.127
4-CF3-Ph
—
H
H1


1.128
CH2Ph
—
H
H1


1.129
CH2-2-F-Ph
—
H
H1


1.130
CH2-2,4-di-F-Ph
—
H
H1


1.131
CH2-2-MeO-Ph
—
H
H1


1.132
CH2-3-MeO-Ph
—
H
H1


1.133
CF3
—
H
H1
*


1.134
CF3
—
Na
H1


1.135
CF3
5-CH3
H
H1


1.136
CF3
—
H
H2
*


1.137
CF3
—
H
H3
*


1.138
CF3
—
H
H4
*


1.139
CF3
—
H
H5


1.140
CF3
—
H
H6
*


1.141
CF3
—
Na
H6


1.142
CF3
5-CH3
H
H6


1.143
CF3
—
H
H7
*


1.144
CF3
—
Na
H7


1.145
CF3
5-CH3
H
H7


1.146
CF3
—
H
H8


1.147
CF3
—
H
H11


1.148
CF3
—
H
H13


1.149
CF3
—
H
H14


1.150
CF3
—
H
H15


1.151
CF3
—
H
H16


1.152
CF3
—
H
H17


1.153
CHF2
—
H
H1


1.154
CHF2
—
H
H2


1.155
CHF2
—
H
H6


1.156
CHF2
—
H
H7


1.157
CH2F
—
H
H1


1.158
CH2CF3
—
H
H1


1.159
CH2CHF2
—
H
H1


1.160
CH2CH2F
—
H
H1


1.161
CF═CH2
—
H
H1


1.162
CH═CF2
—
H
H1


1.163
CF2CH═CH2
—
H
H1


1.164
CH═CH-CF3
—
H
H1


1.165
CHFCH═CH2
—
H
H1


1.166
CN
—
H
H1


1.167
NO2
—
H
H1


1.168
NH2
—
H
H1


1.169
NHCH3
—
H
H1


1.170
N(CH3)2
—
H
H1


1.171
N(CH3)CH2CH═CH2
—
H
H1


1.172
N(CH3)CH2C≡CH
—
H
H1


1.173
NH-cyclopropyl
—
H
H1


1.174
NH-cyclopropyl
—
H
H2


1.175
NH-cyclopropyl
—
H
H3


1.176
NH-cyclopropyl
—
H
H4


1.177
NH-cyclopropyl
—
H
H5


1.178
NH-cyclopropyl
—
H
H6


1.179
NH-cyclopropyl
—
H
H7


1.180
NH-cyclopropyl
—
H
H8


1.181
N(CH3)-cyclopropyl
—
H
H1


1.182
N(CH2CH3)-cyclopropyl
—
H
H1


1.183
NHO(O)H
—
H
H1


1.184
NHC(O)CH3
H
H1


1.185
NHC(O)OCH3
—
H
H1


1.186
NHSO2CH3
—
H
H1


1.187
NHSO2CF3
—
H
H1


1.188
NHSO2CHF2
—
H
H1


1.189
NHSO2CH2F
—
H
H1


1.190
OH
—
H
H1


1.191
OCH3
—
H
H1
*


1.192
OCH3
—
Na
H1


1.193
OCH3
5-CH3
H
H1


1.194
OCH3
—
H
H2
*


1.195
OCH3
—
H
H3
*


1.196
OCH3
—
H
H4
*


1.197
OCH3
—
H
H5
*


1.198
OCH3
—
H
H6
*


1.199
OCH3
—
Na
H6


1.200
OCH3
5-CH3
H
H6


1.201
OCH3
—
H
H7
*


1.202
OCH3
—
Na
H7


1.203
OCH3
5-CH3
H
H7


1.204
OCH3
—
H
H8
*


1.205
OCH3
—
H
H11


1.206
OCH3
—
H
H13


1.207
OCH3
—
H
H14


1.208
OCH3
—
H
H15


1.209
OCH3
—
H
H16


1.210
OCH3
—
H
H17


1.211
OCH2CH3
—
H
H1
*


1.212
OCH2CH3
—
Na
H1


1.213
OCH2CH3
5-CH3
H
H1


1.214
OCH2CH3
—
H
H2
*


1.215
OCH2CH3
—
H
H3
*


1.216
OCH2CH3
—
H
H4


1.217
OCH2CH3
—
H
H5


1.218
OCH2CH3
—
H
H6
*


1.219
OCH2CH3
—
Na
H6


1.220
OCH2CH3
5-CH3
H
H6


1.221
OCH2CH3
—
H
H7
*


1.222
OCH2CH3
—
Na
H7


1.223
OCH2CH3
5-CH3
H
H7


1.224
OCH2CH3
—
H
H8


1.225
OCH2CH3
—
H
H11


1.226
OCH2CH3
—
H
H13


1.227
OCH2CH3
—
H
H14


1.228
OCH2CH3
—
H
H15


1.229
OCH2CH3
—
H
H16


1.230
OCH2CH3
—
H
H17


1.231
O(CH2)2CH3
—
H
H1
*


1.232
O(CH2)2CH3
—
Na
H1


1.233
O(CH2)2CH3
5-CH3
H
H1


1.234
O(CH2)2CH3
—
H
H2


1.235
O(CH2)2CH3
—
H
H3
*


1.236
O(CH2)2CH3
—
H
H4
*


1.237
O(CH2)2CH3
—
H
H5
*


1.238
O(CH2)2CH3
—
H
H6
*


1.239
O(CH2)2CH3
—
Na
H6


1.240
O(CH2)2CH3
5-CH3
H
H6


1.241
O(CH2)2CH3
—
H
H7
*


1.242
O(CH2)2CH3
—
Na
H7


1.243
O(CH2)2CH3
5-CH3
H
H7


1.244
O(CH2)2CH3
—
H
H8
*


1.245
O(CH2)2CH3
—
H
H11


1.246
O(CH2)2CH3
—
H
H13


1.247
O(CH2)2CH3
—
H
H14


1.248
O(CH2)2CH3
—
H
H15


1.249
O(CH2)2CH3
—
H
H16


1.250
O(CH2)2CH3
—
H
H17


1.251
OCH(CH3)2
—
H
H1
*


1.252
OCH(CH3)2
—
Na
H1


1.253
OCH(CH3)2
5-CH3
H
H1


1.254
OCH(CH3)2
—
H
H2
*


1.255
OCH(CH3)2
—
H
H3
*


1.256
OCH(CH3)2
—
H
H4
*


1.257
OCH(CH3)2
—
H
H5


1.258
OCH(CH3)2
—
H
H6
*


1.259
OCH(CH3)2
—
Na
H6


1.260
OCH(CH3)2
5-CH3
H
H6


1.261
OCH(CH3)2
—
H
H7
*


1.262
OCH(CH3)2
—
Na
H7


1.263
OCH(CH3)2
5-CH3
H
H7


1.264
OCH(CH3)2
—
H
H8
*


1.265
OCH(CH3)2
—
H
H11


1.266
OCH(CH3)2
—
H
H13


1.267
OCH(CH3)2
—
H
H14


1.268
OCH(CH3)2
—
H
H15


1.269
OCH(CH3)2
—
H
H16


1.270
OCH(CH3)2
—
H
H17


1.271
OCH(CH3)2
—
Na
H1


1.272
OCH(CH3)2
5-CH3
H
H1


1.273
O(CH2)3CH3
—
H
H1
*


1.274
O(CH2)3CH3
—
H
H2
*


1.275
O(CH2)3CH3
—
H
H3
*


1.276
O(CH2)3CH3
—
H
H4
*


1.277
O(CH2)3CH3
—
H
H5


1.278
O(CH2)3CH3
—
H
H6
*


1.279
O(CH2)3CH3
—
H
H7
*


1.280
O(CH2)3CH3
—
H
H8
*


1.281
OCH(CH3)CH2CH3
—
H
H1
*


1.282
OCH(CH3)CH2CH3
—
H
H2


1.283
OCH(CH3)CH2CH3
—
H
H3


1.284
OCH(CH3)CH2CH3
—
H
H4


1.285
OCH(CH3)CH2CH3
—
H
H5


1.286
OCH(CH3)CH2CH3
—
H
H6
*


1.287
OCH(CH3)CH2CH3
—
H
H7


1.288
OCH(CH3)CH2CH3
—
H
H8


1.289
OCH2CH(CH3)2
—
H
H1
*


1.290
OCH2CH(CH3)2
—
H
H2
*


1.291
OCH2CH(CH3)2
—
H
H3


1.292
OCH2CH(CH3)2
—
H
H4


1.293
OCH2CH(CH3)2
—
H
H5


1.294
OCH2CH(CH3)2
—
H
H6
*


1.295
OCH2CH(CH3)2
—
H
H7
*


1.296
OCH2CH(CH3)2
—
H
H8


1.297
OC(CH3)3
—
H
H1


1.298
OC(CH3)3
—
H
H2


1.299
OC(CH3)3
—
H
H3


1.300
OC(CH3)3
—
H
H4


1.301
OC(CH3)3
—
H
H5


1.302
OC(CH3)3
—
H
H6


1.303
OC(CH3)3
—
H
H1


1.304
OC(CH3)3
—
H
H8


1.305
OCH═CH2
—
H
H1


1.306
OCH═CH2
—
H
H2


1.307
OCH═CH2
—
H
H6


1.308
OCH═CH2
—
H
H1


1.309
OC(CH3)═CH2
—
H
H1


1.310
OCH═CH(CH3)
—
H
H1


1.311
OCH═C(CH3)2
—
H
H1


1.312
OC(CH3)═CHCH3
—
H
H1


1.313
OC(CH3)═C(CH3)2
—
H
H1


1.314
OC≡CH
—
H
H1


1.315
OC≡CH
—
H
H2


1.316
OC≡CH
—
H
H6


1.317
OC≡CH
—
H
H1


1.318
OC≡CCH3
—
H
H1


1.319
OC≡CCH2CH3
—
H
H1


1.320
OCH2OH═CH2
—
H
H1


1.321
OCH2CH═CH2
—
H
H2


1.322
OCH2CH═CH2
—
H
H6


1.323
OCH2CH═CH2
—
H
H7


1.324
OCH2C(CH3)═CH2
—
H
H1


1.325
OCH2CH═CHCH3
—
H
H1


1.326
OCH2CH═C(CH3)2
—
H
H1


1.327
OCH2C(CH3)═CHCH3
—
H
H1


1.328
OCH2C(CH3)═C(CH3)2
—
H
H1


1.329
OCH(CH3)CH═CH2
—
H
H1


1.330
OCH2C≡CH
—
H
H1


1.331
OCH2C≡CH
—
H
H2


1.332
OCH2C≡CH
—
H
H6


1.333
OCH2C≡CH
—
H
H7


1.334
OCH2C≡CCH3
—
H
H1


1.335
OCH2C≡CCH2CH3
—
H
H1


1.336
OCH(CH3)C≡CH
—
H
H1


1.337
O-cyclopropyl
—
H
H1


1.338
O-cyclopropyl
—
H
H2


1.339
O-cyclopropyl
—
H
H6


1.340
O-cyclopropyl
—
H
H7


1.341
O-2,2-di-Cl-cyclopropyl
—
H
H1


1.342
O-2,2-di-F-cyclopropyl
—
H
H1


1.343
O-cyclobutyl
—
H
H1


1.344
O-cyclopentyl
—
H
H1


1.345
O-cyctohexyl
—
H
H1


1.346
OCH2-cyclopropyl
—
H
H1
*


1.347
OCH2-cyclopropyl
—
Na
H1


1.348
OCH2-cyclopropyl
5-CH3
H
H1


1.349
OCH2-cyclopropyl
—
H
H2
*


1.350
OCH2-cyclopropyl
—
H
H3
*


1.351
OCH2-cyclopropyl
—
H
H4


1.352
OCH2-cyclopropyl
—
H
H5


1.353
OCH2-cyclopropyl
—
H
H6
*


1.354
OCH2-cyclopropyl
—
Na
H6


1.355
OCH2-cyclopropyl
5-CH3
H
H6


1.356
OCH2-cyclopropyl
—
H
H7
*


1.357
OCH2-cyclopropyl
—
Na
H7


1.358
OCH2-cyclopropyl
5-CH3
H
H7


1.359
OCH2-cyclopropyl
—
H
H8
*


1.360
OCH2-cyclopropyl
—
H
H11


1.361
OCH2-cyclopropyl
—
H
H13


1.362
OCH2-cyclopropyl
—
H
H14


1.363
OCH2-cyclopropyl
—
H
H15


1.364
OCH2-cyclopropyl
—
H
H16


1.365
OCH2-cyclopropyl
—
H
H17


1.366
OCH(CH3)-cyclopropyl
—
H
H1


1.367
OCH(CH3)-cyclopropyl
—
H
H2


1.368
OCH(CH3)-cyclopropyl
—
H
H6


1.369
OCH(CH3)-cyclopropyl
—
H
H7


1.370
OCH2-2-Me-cyclopropyl
—
H
H1


1.371
OCH2-2,2-di-Me-
—
H
H1



cyclopropyl


1.372
OCH2-2,2-di-Cl-
—
H
H1



cyclopropyl


1.373
OCH2-2,2-di-F-
—
H
H1



cyclopropyl


1.374
OCH2-cyclobutyl
—
H
H1


1.375
OCH2-cyclopentyl
—
H
H1


1.376
OCH2-cyclopentyl
—
H
H2


1.377
OCH2-cyclopentyl
—
H
H6


1.378
OCH2-cyclopentyl
—
H
H1


1.379
OCH(CH3)-cyclopentyl
—
H
H1


1.380
OCH2-cyclohexyl
—
H
H1


1.381
OCH(CH3)-cyclohexyl
—
H
H1


1.382
OCH2OCH3
—
H
H1


1.383
O(CH2)2OCH3
—
H
H1


1.384
OCH2OCH2CH3
—
H
H1


1.385
C(CH2)2OCH2CH3
—
H
H1


1.386
OCH(CH3)OCH3
—
H
H1


1.387
O(CH2)2Cl
—
H
H1


1.388
O(CH2)2Cl
—
H
H2


1.389
O(CH2)2Cl
—
H
H3


1.390
O(CH2)2Cl
—
H
H4


1.391
O(CH2)2Cl
—
H
H5


1.392
O(CH2)2Cl
—
H
H6


1.393
O(CH2)2Cl
—
H
H7


1.394
O(CH2)2Cl
—
H
H8


1.395
O(CH2)3Cl
—
H
H1


1.396
O(CH2)3Cl
—
H
H2


1.397
O(CH2)3Cl
—
H
H3


1.398
O(CH2)3Cl
—
H
H4


1.399
O(CH2)3Cl
—
H
H5


1.400
O(CH2)3Cl
—
H
H6


1.401
O(CH2)3Cl
—
H
H7


1.402
O(CH2)3Cl
—
H
H8


1.403
OPh
—
H
H1


1.404
O-2-F-Ph
—
H
H1


1.405
O-3-F-Ph
—
H
H1


1.406
O-4-F-Ph
—
H
H1


1.407
O-2,6-di-F-Ph
—
H
H1


1.408
O-2,4-di-F-Ph
—
H
H1


1.409
O-2-Cl-Ph
—
H
H1


1.410
O-3-Cl-Ph
—
H
H1


1.411
O-4-Cl-Ph
—
H
H1


1.412
O-2,6-di-Cl-Ph
—
H
H1


1.413
O-2,4-di-Cl-Ph
—
H
H1


1.414
O-2-CF3-Ph
—
H
H1


1.415
O-3-CF3-Ph
—
H
H1


1.416
O-4-CF3-Ph
—
H
H1


1.417
O-2-MeO-Ph
—
H
H1


1.418
O-3-MeO-Ph
—
H
H1


1.419
O-4-MeO-Ph
—
H
H1


1.420
O-2,4-di-MeO-Ph
—
H
H1


1.421
O-2-Me-Ph
—
H
H1


1.422
O-3-Me-Ph
—
H
H1


1.423
O-4-Me-Ph
—
H
H1


1.424
OCH2Ph
—
H
H1


1.425
OCH(CH3)Ph
—
H
H1


1.426
OCH2-2-F-Ph
—
H
H1


1.427
OCH2-3-F-Ph
—
H
H1


1.428
OCH2-4-F-Ph
—
H
H1


1.429
OCH2-2,4-di-F-Ph
—
H
H1


1.430
OCH2-2-Cl-Ph
—
H
H1


1.431
OCH2-3-Cl-Ph
—
H
H1


1.432
OCH2-4-Cl-Ph
—
H
H1


1.433
OCH2-2,4-di-Cl-Ph
—
H
H1


1.434
OCH2-2-MeO-Ph
—
H
H1


1.435
OCH2-3-MeO-Ph
—
H
H1


1.436
OCH2-4-MeO-Ph
—
H
H1


1.437
OCH2-2-CF3-Ph
—
H
H1


1.438
OCH2-3-CF3-Ph
—
H
H1


1.439
OCH2-4-CF3-Ph
—
H
H1


1.440
OCF3
—
H
H1
*


1.441
OCF3
—
Na
H1


1.442
OCF3
5-CH3
H
H1


1.443
OCF3
—
H
H2
*


1.444
OCF3
—
H
H3
*


1.445
OCF3
—
H
H4


1.446
OCF3
—
H
H5


1.447
OCF3
—
H
H6
*


1.448
OCF3
—
Na
H6


1.449
OCF3
5-CH3
H
H6


1.450
OCF3
—
H
H7
*


1.451
OCF3
—
Na
H7


1.452
OCF3
5-CH3
H
H7


1.453
OCF3
—
H
H8
*


1.454
OCF3
—
H
H11


1.455
OCF3
—
H
H13


1.456
OCF3
—
H
H14


1.457
OCF3
—
H
H15


1.458
OCF3
—
H
H16


1.459
OCF3
—
H
H17


1.460
OCHF2
—
H
H1
*


1.461
OCHF2
—
Na
H1


1.462
OCHF2
5-CH3
H
H1


1.463
OCHF2
—
H
H2
*


1.464
OCHF2
—
H
H3
*


1.465
OCHF2
—
H
H4
*


1.466
OCHF2
—
H
H5


1.467
OCHF2
—
H
H6
*


1.468
OCHF2
—
Na
H6


1.469
OCHF2
5-CH3
H
H6


1.470
OCHF2
—
H
H7
*


1.471
OCHF2
—
Na
H7


1.472
OCHF2
5-CH3
H
H7


1.473
OCHF2
—
H
H8
*


1.474
OCHF2
—
H
H11


1.475
OCHF2
—
H
H13


1.476
OCHF2
—
H
H14


1.477
OCHF2
—
H
H15


1.478
OCHF2
—
H
H16


1.479
OCHF2
—
H
H17


1.480
OCH2F
—
H
H1


1.481
OCH2CF3
—
H
H1
*


1.482
OCH2CF3
—
Na
H1


1.483
OCH2CF3
5-CH3
H
H1


1.484
OCH2CF3
—
H
H2


1.485
OCH2CF3
—
H
H3


1.486
OCH2CF3
—
H
H4


1.487
OCH2CF3
—
H
H5


1.488
OCH2CF3
—
H
H6
*


1.489
OCH2CF3
—
Na
H6


1.490
OCH2CF3
5-CH3
H
H6


1.491
OCH2CF3
—
H
H7


1.492
OCH2CF3
—
Na
H7


1.493
OCH2CF3
5-CH3
H
H7


1.494
OCH2CF3
—
H
H8


1.495
OCH2CF3
—
H
H11


1.496
OCH2CF3
—
H
H13


1.497
OCH2CF3
—
H
H14


1.498
OCH2CF3
—
H
H15


1.499
OCH2CF3
—
H
H16


1.500
OCH2CF3
—
H
H17


1.501
OCH2CHF2
—
H
H1
*


1.502
OCH2CHF2
—
Na
H1


1.503
OCH2CHF2
5-CH3
H
H1


1.504
OCH2CHF2
—
H
H2
*


1.505
OCH2CHF2
—
H
H3
*


1.506
OCH2CHF2
—
H
H4
*


1.507
OCH2CHF2
—
H
H5


1.508
OCH2CHF2
—
H
H6
*


1.509
OCH2CHF2
—
Na
H6


1.510
OCH2CHF2
5-CH3
H
H6


1.511
OCH2CHF2
—
H
H7
*


1.512
OCH2CHF2
—
Na
H7


1.513
OCH2CHF2
5-CH3
H
H7


1.514
OCH2CHF2
—
H
H8
*


1.515
OCH2CHF2
—
H
H11


1.516
OCH2CHF2
—
H
H13


1.517
OCH2CHF2
—
H
H14


1.518
OCH2CHF2
—
H
H15


1.519
OCH2CHF2
—
H
H16


1.520
OCH2CHF2
—
H
H17


1.521
OCH2CH2F
—
H
H1


1.522
OCH(CH3)CF3
—
H
H1


1.523
OCH(CH3)CF3
—
Na
H1


1.524
OCH(CH3)CF3
5-CH3
H
H1


1.525
OCH(CH3)CF3
—
H
H2
*


1.526
OCH(CH3)CF3
—
H
H3
*


1.527
OCH(CH3)CF3
—
H
H4
*


1.528
OCH(CH3)CF3
—
H
H5


1.529
OCH(CH3)CF3
—
H
H6
*


1.530
OCH(CH3)CF3
—
Na
H6


1.531
OCH(CH3)CF3
5-CH3
H
H6


1.532
OCH(CH3)CF3
—
H
H7
*


1.533
OCH(CH3)CF3
—
Na
H7


1.534
OCH(CH3)CF3
5-CH3
H
H7


1.535
OCH(CH3)CF3
—
H
H8
*


1.536
OCH(CH3)CF3
—
H
H11


1.537
OCH(CH3)CF3
—
H
H13


1.538
OCH(CH3)CF3
—
H
H14


1.539
OCH(CH3)CF3
—
H
H15


1.540
OCH(CH3)CF3
—
H
H16


1.541
OCH(CH3)CF3
—
H
H17


1.542
OCH(CH3)CHF2
—
H
H1


1.543
OCH(CH3)CH2F
—
H
H1


1.544
OCH2CF2CF3
—
H
H1
*


1.545
OCH2CF2CF3
—
Na
H1


1.546
OCH2CF2CF3
5-CH3
H
H1


1.547
OCH2CF2CF3
—
H
H1


1.548
OCH2CF2CF3
—
H
H2


1.549
OCH2CF2CF3
—
H
H3
*


1.550
OCH2CF2CF3
—
H
H4
*


1.551
OCH2CF2CF3
—
H
H5


1.552
OCH2CF2CF3
—
H
H6
*


1.553
OCH2CF2CF3
—
Na
H6


1.554
OCH2CF2CF3
5-CH3
H
H6


1.555
OCH2CF2CF3
—
H
H7
*


1.556
OCH2CF2CF3
—
Na
H7


1.557
OCH2CF2CF3
5-CH3
H
H7


1.558
OCH2CF2CF3
—
H
H8
*


1.559
OCH2CF2CF3
—
H
H11


1.560
OCH2CF2CF3
—
H
H13


1.561
OCH2CF2CF3
—
H
H14


1.562
OCH2CF2CF3
—
H
H15


1.563
OCH2CF2CF3
—
H
H16


1.564
OCH2CF2CHF2
—
H
H17


1.565
OCH2CF2CH2F
—
H
H1


1.566
OCH(CH3)CF2CF3
—
H
H1


1.567
OCH(CH3)CF2CHF2
—
H
H1


1.568
OCH(CH3)CF2CH2F
—
H
H1


1.569
OCH2CHFCF3
—
H
H1


1.570
O(CH2)2CF3
—
H
H1


1.571
O(CH2)2CHF2
—
H
H1


1.572
O(CH2)3CF3
—
H
H1


1.573
O(CH2)3CHF2
—
H
H1


1.574
OCF═CH2
—
H
H1


1.575
OCH═CF2
—
H
H1


1.576
OCF2CH═CH2
—
H
H1


1.577
OCHFCH═CH2
—
H
H1


1.578
OCH═CHCF3
—
H
H1
*


1.579
SCH3
—
H
H1


1.580
SCH3
—
H
H2


1.581
SCH3
—
H
H3
*


1.582
SCH3
—
H
H4
*


1.583
SCH3
—
H
HS


1.584
SCH3
—
H
H6
*


1.585
SCH3
—
H
H7
*


1.586
SCH3
—
H
H8
*


1.587
SCH3
—
H
H11


1.588
SCH3
—
H
H13


1.589
SCH3
—
H
H14


1.590
SCH3
—
H
H15


1.591
SCH3
—
H
H16


1.592
SCH3
—
H
H17


1.593
SCH2CH3
—
H
H1


1.594
SCH2CH3
—
H
H2


1.595
SCH2CH3
—
H
H3


1.596
SCH2CH3
—
H
H4


1.597
SCH2CH3
—
H
H5


1.598
SCH2CH3
—
H
H6


1.599
SCH2CH3
—
H
H7


1.600
SCH2CH3
—
H
H8


1.601
S(CH2)2CH3
—
H
H1


1.602
SCH(CH3)2
—
H
H1


1.603
SC(CH3)3
—
H
H1


1.604
SCH2Ph
—
H
H1


1.605
SPh
—
H
H1


1.606
SCF3
—
H
H1


1.607
SCF3
—
H
H2


1.608
SCF3
—
H
H6


1.609
SCF3
—
H
H7


1.610
SCHF2
—
H
H1


1.611
SCHF2
—
H
H2


1.612
SCHF2
—
H
H6


1.613
SCHF2
—
H
H7


1.614
SCH2F
—
H
H1


1.615
SCH═CH2
—
H
H1


1.616
SCH2CH═CH2
—
H
H1


1.617
SCH2CH═CH2
—
H
H2


1.618
SCH2CH═CH2
—
H
H6


1.619
SCH2CH═CH2
—
H
H7


1.620
SC≡CH
—
H
H1


1.621
SCH2C≡CH
—
H
H1


1.622
SCH2C≡CH
—
H
H2


1.623
SCH2C≡CH
—
H
H6


1.624
SCH2C≡CH
—
H
H7


1.625
S-cyclopropyl
—
H
H1


1.626
SCH2-cyclopropyl —
H
H1


1.627
SCH2-cyclopropyl —
H
H2


1.628
SCH2-cyclopropyl —
H
H6


1.629
SCH2-cyclopropyl —
H
H7


1.630
SF5
—
H
H1


1.631
S(O)CH3
—
H
H1


1.632
S(O)CH3
—
H
H2


1.633
S(O)CH3
—
H
H3


1.634
S(O)CH3
—
H
H4


1.635
S(O)CH3
—
H
H5


1.636
S(O)CH3
—
H
H6


1.637
S(O)CH3
—
H
H7


1.638
S(O)CH3
—
H
H8


1.639
S(O)CH2CH3
—
H
H1


1.640
S(O)CH2CH3
—
H
H2


1.641
S(O)CH2CH3
—
H
H3


1.642
S(O)CH2CH3
—
H
H4


1.643
S(O)CH2CH3
—
H
H5


1.644
S(O)CH2CH3
—
H
H6


1.645
S(O)CH2CH3
—
H
H7


1.646
S(O)CH2CH3
—
H
H8


1.647
S(O)(CH2)2CH3
—
H
H1


1.648
S(O)CH(CH3)2
—
H
H1


1.649
S(O)C(CH3)3
—
H
H1


1.650
S(O)CH2Ph
—
H
H1


1.651
S(O)Ph
—
H
H1


1.652
S(O)CF3
—
H
H1


1.653
S(O)CHF2
—
H
H1


1.654
S(O)CH2F
—
H
H1


1.655
S(O)CH═CH2
—
H
H1


1.656
S(O)CH2CH═CH2
—
H
H1


1.657
S(O)C≡CH
—
H
H1


1.658
S(O)CH2C≡CH
—
H
H1


1.659
S(O)-cyclopropyl
—
H
H1


1.660
S(O)CH2-cyclopropyl
—
H
H1


1.661
SO2CH3
—
H
H1


1.662
SO2CH3
—
H
H2


1.663
SO2CH3
—
H
H3


1.664
SO2CH3
—
H
H4


1.665
SO2CH3
—
H
H5


1.666
SO2CH3
—
H
H6


1.667
SO2CH3
—
H
H7


1.668
SO2CH3
—
H
H8


1.669
SO2CH3
—
H
H11


1.670
SO2CH3
—
H
H13


1.671
SO2CH3
—
H
H14


1.672
SO2CH3
—
H
H15


1.673
SO2CH3
—
H
H16


1.674
SO2CH3
—
H
H17


1.675
SO2CH2CH3
—
H
H1


1.676
SO2CH2CH3
—
H
H2


1.677
SO2CH2CH3
—
H
H3


1.678
SO2CH2CH3
—
H
H4


1.679
SO2CH2CH3
—
H
H5


1.680
SO2CH2CH3
—
H
H6


1.681
SO2CH2CH3
—
H
H7


1.682
SO2CH2CH3
—
H
H8


1.683
SO2(CH2)2CH3
—
H
H1


1.684
SO2CH(CH3)2
—
H
H1


1.685
SO2C(CH3)3
—
H
H1


1.686
SO2CH2Ph
—
H
H1


1.687
SO2Ph
—
H
H1


1.688
SO2CF3
—
H
H1


1.689
SO2CF3
—
H
H2


1.690
SO2CF3
—
H
H6


1.691
SO2CF3
—
H
H7


1.692
SO2CHF2
—
H
H1


1.693
SO2CH2F
—
H
H1


1.694
SO2CH═CH2
—
H
H1


1.695
SO2CH2CH═CH2
—
H
H1


1.696
SO2CH2CH═CH2
—
H
H2


1.697
SO2CH2CH═CH2
—
H
H6


1.698
SO2CH2CH═CH2
—
H
H7


1.699
SO2C≡CH
—
H
H1


1.700
SO2CH2C≡CH
—
H
H1


1.701
SO2CH2C≡CH
—
H
H2


1.702
SO2CH2C≡CH
—
H
H6


1.703
SO2CH2C≡CH
—
H
H7


1.704
SO2-cyclopropyl
—
H
H1


1.705
SO2-cyclopropyl
—
H
H2


1.706
SO2-cyclopropyl
—
H
H6


1.707
SO2-cyclopropyl
—
H
H7


1.708
SO2CH2-cyclopropyl
—
H
H1


1.709
SO2NHCH3
—
H
H1


1.710
SO2N(CH3)2
—
H
H1


1.711
OSO2CH3
—
H
H1
*


1.712
OSO2CH3
—
H
H2
*


1.713
OSO2CH3
—
H
H3
*


1.714
OSO2CH3
—
H
H4


1.715
OSO2CH3
—
H
H5
*


1.716
OSO2CH3
—
H
H6


1.717
OSO2CH3
—
H
H7
*


1.718
OSO2CH3
—
H
H8
*


1.719
OSO2CH3
—
H
H11


1.720
OSO2CH3
—
H
H15


1.721
OSO2CH3
—
H
H16


1.722
OSO2CH2CH3
—
H
H1


1.723
OSO2CH(CH3)2
—
H
H1


1.724
OSO2C(CH3)3
—
H
H1


1.725
OSO2CH2Ph
—
H
H1


1.726
OSO2CF3
—
H
H1


1.727
OSO2CF3
—
H
H2


1.728
OSO2CF3
—
H
H6


1.729
OSO2CF3
—
H
H7


1.730
OSO2CHF2
—
H
H1


1.731
OSO2CHF2
—
H
H2


1.732
OSO2CHF2
—
H
H6


1.733
OSO2CHF2
—
H
H7


1.734
OSO2CH2F
—
H
H1


1.735
OSO2CH2CF3
—
H
H1


1.736
OSO2CH2CHF2
—
H
H1


1.737
OSO2(CH2)2F
—
H
H1


1.738
OSO2CH═CH2
—
H
H1


1.739
OSO2CH2CH═CH2
—
H
H1


1.740
OSO2C≡CH
—
H
H1


1.741
OSO2CH2C≡CH
—
H
H1


1.742
OSO2-cyclopropyl
—
H
H1


1.743
OSO2CH2-cyclopropyl
—
H
H1


1.744
OSO2CH2CN
—
H
H1


1.745
OSO2CH2CN
—
H
H2


1.746
OSO2CH2CN
—
H
H6


1.747
OSO2CH2CN
—
H
H7


1.748
OSO2NHCH3
—
H
H1


1.749
OSO2N(CH3)2
—
H
H1
*


1.750
OSO2N(CH3)2
—
H
H2
*


1.751
OSO2N(CH3)2
—
H
H3
*


1.752
OSO2N(CH3)2
—
H
H4


1.753
OSO2N(CH3)2
—
H
H5


1.754
OSO2N(CH3)2
—
H
H6
*


1.755
OSO2N(CH3)2
—
H
H7
*


1.756
OSO2N(CH3)2
—
H
H8
*


1.757
OSO2N(CH3)2
—
H
H11


1.758
OSO2N(CH3)2
—
H
H15


1.759
OSO2N(CH3)2
—
H
H16


1.760
OSO2NHCH2CH═CH2
—
H
H1


1.761
OSO2NHCH2C≡CH
—
H
H1


1.762
OSO2NHCF3
—
H
H1


1.763
OSO2NHCF3
—
H
H2


1.764
OSO2NHCF3
—
H
H6


1.765
OSO2NHCF3
—
H
H7


1.766
OSO2NHCHF2
—
H
H1


1.767
OSO2NHCHF2
—
H
H2


1.768
OSO2NHCHF2
—
H
H6


1.769
OSO2NHCHF2
—
H
H7


1.770
OSO2NHCH2F
—
H
H1


1.771
OC(O)H
—
H
H1


1.772
OC(O)CH3
—
H
H1


1.773
OC(O)CH2CH3
—
H
H1


1.774
OC(O)OCH3
—
H
H1


1.775
OC(O)OCH2CH3
—
H
H1


1.776
OC(O)NH2
—
H
H1


1.777
OC(O)NHCH3
—
H
H1


1.778
OC(O)N(CH3)2
—
H
H1


1.779
OC(O)N(CH2CH3)2
—
H
H1


1.780
Si(CH3)3
—
H
H1


1.781
2-thienyl
—
H
H1


1.782
3-thienyl
—
H
H1


1.783
2-pyridyl
—
H
H1


1.784
3-pyridyl
H
H1


1.785
4-pyridyl
H
H1


1.786
OH
H
H1


1.787
C(O)H
—
H
H1


1.788
C(O)H
—
H
H2


1.789
C(O)H
—
H
H6


1.790
C(O)H
—
H
H7


1.791
C(O)CH3
—
H
H1


1.792
C(O)CH3
—
H
H2


1.793
C(O)CH3
—
H
H6


1.794
C(O)CH3
—
H
H7


1.795
C(O)OCH3
—
H
H1


1.796
C(O)OCH3
—
H
H2


1.797
C(O)OCH3
—
H
H6


1.798
C(O)OCH3
—
H
H7


1.799
C(O)OCH2CH3
—
H
H1


1.800
C(O)OCH2CH2CH3
—
H
H1


1.801
C(O)OCH(CH3)2
—
H
H1


1.802
C(O)OC(CH3)3
—
H
H1


1.803
C(O)NH2
—
H
H1


1.804
C(O)N(CH3)2
—
H
H1


1.805
C(O)N(CH3)2
—
H
H2


1.806
C(O)N(CH3)2
—
H
H6


1.807
C(O)N(CH3)2
—
H
H1


1.808
C(O)N(CH2CH3)2
—
H
H1


1.809
C(O)NHCH3
—
H
H1


1.810
C(O)NHCH2CH3
—
H
H1


1.811
C(O)NH-cyclopropyl
—
H
H1


1.812
C(O)NH-cyclopropyl
—
H
H2


1.813
C(O)N H-cyclopropyl
—
H
H6


1.814
C(O)NH-cyclopropyl
—
H
H1


1.815
CH3
H
H
H10
*


1.816
OCH3
3-Cl
H
H1
*


1.817
OCH3
3-Cl
H
H2
*


1.818
OCH3
3-Cl
H
H3
*


1.819
OCH3
3-Cl
H
H4
*


1.820
OCH3
3-Cl
H
H6
*


1.821
OCH3
3-Cl
H
H1
*


1.822
OCH3
3-Cl
H
H8
*


1.823
H
4-F
H
H1
*


1.824
H
4-F
H
H3
*


1.825
H
4-F
H
H6
*


1.826
H
4-F
H
H1
*


1.827
H
4-F
H
H8
*


1.828
H
3-Cl
H
H1
*


1.829
H
3-Cl
H
H2
*


1.830
H
3-Cl
H
H3
*


1.831
H
3-Cl
H
H4
*


1.832
H
3-Cl
H
H6
*


1.833
H
3-Cl
H
H7
*


1.834
H
3-Cl
H
H8
*


1.835
H
5-CF3
H
H1
*


1.836
H
5-CF3
H
H2
*


1.837
H
5-CF3
H
H3
*


1.838
H
5-CF3
H
H4
*


1.839
H
5-CF3
H
H6
*


1.840
H
5-CF3
H
H7
*


1.841
H
5-CF3
H
H8
*


1.842
Cl
4-CF3
H
H1
*


1.843
Cl
4-CF3
H
H2
*


1.844
Cl
4-CF3
H
H3
*


1.845
Cl
4-CF3
H
H4
*


1.846
Cl
4-CF3
H
H6
*


1.847
Cl
4-CF3
H
H7
*


1.848
Cl
4-CF3
H
H8
*


1.849
Cl
3-Cl
H
H1
*


1.850
Cl
3-Cl
H
H2
*


1.851
Cl
3-Cl
H
H3
*


1.852
Cl
3-Cl
H
H4
*


1.853
Cl
3-Cl
H
H6
*


1.854
Cl
3-Cl
H
H7
*


1.855
H
3-F, 4-CH3
H
H1
*


1.856
H
3-F, 4-CH3
H
H2
*


1.857
H
3-F, 4-CH3
H
H3
*


1.858
H
3-F, 4-CH3
H
H4
*


1.859
H
3-F, 4-CH3
H
H6
*


1.860
H
3-F, 4-CH3
H
H7
*


1.861
H
3-F, 4-CH3
H
H8
*


1.862
H
4-CH3, 5-CH3
H
H1
*


1.863
H
4-CH3, 5-CH3
H
H2
*


1.864
H
4-CH3, 5-CH3
H
H3
*


1.865
H
4-CH3, 5-CH3
H
H4
*


1.866
H
4-CH3, 5-CH3
H
H6
*


1.867
H
4-CH3, 5-CH3
H
H7
*


1.868
H
4-CH3, 5-CH3
H
H8
*


1.869
H
4-Cl
H
H1
*


1.870
H
4-Cl
H
H2
*


1.871
H
4-Cl
H
H3
*


1.872
H
4-Cl
H
H4
*


1.873
H
4-Cl
H
H6
*


1.874
H
4-Cl
H
H7
*


1.875
H
4-Cl
H
H8
*


1.876
H
4-(CH2)2CH3
H
H1
*


1.877
H
4-(CH2)2CH3
H
H2
*


1.878
H
4-(CH2)2CH3
H
H3
*


1.879
H
4-(CH2)2CH3
H
H4
*


1.880
H
4-(CH2)2CH3
H
H6
*


1.881
H
4-(CH2)2CH3
H
H7
*


1.882
H
4-(CH2)2CH3
H
H8
*


1.883
H
4-(CH2)3CH3
H
H2
*


1.884
H
4-(CH2)3CH3
H
H3
*


1.885
H
4-(CH2)3CH3
H
H1
*


1.886
H
4-(CH2)3CH3
H
H6
*


1.887
H
4-(CH2)3CH3
H
H7
*


1.888
H
4-(CH2)3CH3
H
H8
*


1.889
H
4-(CH2)3CH3
H
H4
*


1.890
H
4-CF3
H
H2
*


1.891
H
4-CF3
H
H7
*


1.892
H
4-CF3
H
H10
*


1.893
H
4-CF3
H
H1
*


1.894
H
4-CF3
H
H3
*


1.895
H
4-CF3
H
H4
*


1.896
H
4-CF3
H
H6
*


1.897
H
4-CF3
H
H8
*





1H NMR data for compounds of table 1:






Example 1.001 (d6-DMSO): 8.20 (dd, J=1.5, 8.0, 1H); 8.17 (dd, J=1.1, 7.9, 1H); 7.67 (td, J=1.2, 7.5, 1H); 7.41 (td, J=1.6, 7.6, 1H); 3.98 (s, 3H); 3.06 (s, 3H).
Example 1.004 (d6-DMSO): 8.19 (m, 2H); 7.67 (td, J=1.2, 7.5, 1H); 7.41 (td, J=1.6, 7.6, 1H); 4.36 (q, J=7.1, 2H); 3.05 (s, 3H); 1.35 (t, 3H).
Example 1.005 (d6-DMSO): 8.18 (m, 2H); 7.67 (td, J=1.2, 7.5, 1H); 7.41 (td, J=1.6, 7.6, 1H); 4.27 (t, J=6.5, 2H); 3.06 (s, 3H); 1.74 (m, 2H); 0.94 (t, J=7.4, 3H).
Example 1.008 (d6-DMSO): 8.17 (m, 2H); 7.66 (td, J=1.2, 7.5, 1H); 7.4 (td, J=1.6, 7.6, 1H); 3.96 (s, 3H); 2.75 (m, 1H); 0.90 (m, 4H).
Example 1.011 (d6-DMSO): 8.19 (m, 2H); 7.67 (td, J=1.3, 7.5, 1H); 7.42 (td, J=1.6, 7.5, 1H); 4.34 (q, J=7.1, 2H); 2.75 (m, 1H); 1.35 (t, J=7.1, 3H); 0.91 (m, 4H).
Example 1.014 (d6-DMSO): 8.21 (dd, J=1.5, 5.5, 1H); 8.18 (dd, J=1.6, 5.4, 1H); 7.68 (dd, J=1.2, 7.5, 1H); 7.42 (dd, J=1.6, 7.6, 1H); 4.25 (t=6.4, 2H); 2.76 (m, 1H); 1.74 (m, 2H); 0.93 (m, 7H).
Example 1.021 (CDCl3): 7.88 (m, 1H); 7.15 (m, 2H); 4.00 (s, 3H); 3.13 (s, 3H).
Example 1.022 (CDCl3): 11.00 (br s, 1H); 7.94 (m, 1H); 7.20 (m, 2H); 4.45 (q, J=7.1, 2H); 3.20 (s, 3H); 1.43 (t, J=7.1, 3H).
Example 1.023 (CDCl3): 7.94 (m, 1H); 7.20 (m, 2H); 4.34 (t, J=6.7, 2H); 3.20 (s, 3H); 1.82 (m, 2H); 0.99 (t, J=7.4, 3H).
Example 1.024 (CDCl3): 11.01 (br s, 1H); 7.94 (m, 1H); 7.20 (m, 2H); 5.16 (m, 1H); 3.17 (s, 3H); 1.40 (d, J=6.2, 6H).
Example 1.027 (CDCl3): 11.03 (br s, 1H); 7.94 (m, 1H); 7.20 (m, 2H); 4.43 (q, J=7.1, 2H); 2.73 (m, 1H); 1.43 (t, J=7.1, 3H); 1.03 (m, 4H).
Example 1.028 (CDCl3): 11.02 (br s, 1H); 7.93 (m, 1H); 7.19 (m, 2H); 4.32 (t, J=6.5, 2H); 2.74 (m, 1H); 1.81 (m, 2H); 1.02 (m, 4H); 1.00 (t, J=7.4, 3H).
Example 1.037 (CDCl3): 11.00 (br s, 1H); 8.00 (dd, J=0.7, 7.5, 1H); 7.31 (br d, J=7.5, 1H); 7.04 (t, J=7.8, 1H); 4.07 (s, 3H); 3.21 (s, 3H); 2.89 (s, 3H).
Example 1.038 (CDCl3): 11.03 (br s, 1H); 8.00 (d, J=7.8, 1H); 7.30 (d, J=7.5, 1H); 7.04 (t, J=7.5, 1H); 4.45 (q, J=7.2, 1H); 3.20 (s, 3H); 2.89 (s, 3H); 1.43 (t, J=7.2, 3H).
Example 1.039 (CDCl3): 11.02 (br s, 1H); 8.00 (br d, J=7.8, 1H); 7.30 (br d, J=7.5, 1H); 7.03 (t, J=7.8, 1H); 4.34 (t, J=6.5, 1H); 3.20 (s, 3H); 2.89 (s, 3H); 1.81 (m, 2H); 0.99 (t, J=7.5, 3H).
Example 1.040 (CDCl3): 11.06 (br s, 1H); 8.00 (dd, J=0.7, 7.8, 1H); 7.30 (br d, J=7.8, 1H); 7.04 (t, J=7.8, 1H); 5.16 (m, 1H); 3.17 (s, 3H); 2.89 (s, 3H); 1.40 (d, J=6.2, 6H).
Example 1.042 (CDCl3): 11.03 (br s, 1H); 8.00 (dd, J=0.7, 7.8, 1H); 7.30 (br d, J=7.5, 1H); 7.03 (t, J=7.8, 1H); 4.06 (s, 3H); 2.88 (s, 3H); 2.74 (m, 1H); 1.03 (m, 4H).
Example 1.043 (CDCl3): 11.07 (br s, 1H); 8.00 (dd, J=1.0, 7.8, 1H); 7.30 (br d, J=7.5, 1H); 7.03 (t, J=7.5, 1H); 4.43 (q, J=6.8, 2H); 2.88 (s, 3H); 2.74 (m, 1H); 1.43 (t, J=7.2, 3H); 1.03 (m, 4H).
Example 1.044 (CDCl3): 11.05 (br s, 1H); 7.99 (dd, J=0.7, 7.8, 1H); 7.30 (dd, J=0.7, 7.8, 1H); 7.03 (t, J=7.8, 1H); 4.32 (t, J=6.5, 2H); 2.88 (s, 3H); 2.74 (m, 1H); 1.81 (m, 2H); 1.03 (m, 4H); 1.00 (t, J=7.5, 3H).
Example 1.133 (CDCl3): 11.17 (br s, 1H); 8.37 (dd, J=1.2, 8.0, 1H); 7.97 (br d, J=8.0, 1H); 7.29 (t, J=8.0, 1H); 4.06 (s, 3H); 3.21 (s, 3H).
Example 1.136 (CDCl3): 11.19 (br s, 1H); 8.37 (dd, J=1.1, 7.9, 1H); 7.96 (br d, J=7.9, 1H); 7.29 (br t, J=7.7, 1H); 4.44 (m, 2H); 3.21 (s, 3H); 1.42 (t, J=7.1, 3H).
Example 1.137 (CDCl3): 11.17 (br s, 1H); 8.36 (dd, J=1.2, 8.0, 1H); 7.95 (br d, J=8.0, 1H); 7.28 (br t, J=8.0, 1H); 4.33 (t, J=6.7, 2H); 3.21 (s, 3H); 1.81 (m, 2H); 0.98 (t, J=7.4, 3H).
Example 1.138 (CDCl3): 11.24 (br s, 1H); 8.37 (dd, J=1.2, 8.0, 1H); 7.96 (dd, J=0.7, 8.0, 1H); 7.29 (td, 0.7, 8.0, 1H); 5.15 (m, 1H); 3.18 (s, 3H); 1.39 (d, J=6.2, 6H).
Example 1.140 (CDCl3): 11.19 (br s, 1H); 8.36 (dd, J=1.2, 8.0, 1H); 7.96 (br dd, J=0.6, 8.0, 1H); 7.28 (td, J=0.7, 8.1, 1H); 4.05 (s, 3H); 2.75 (m, 1H); 1.04 (m, 4H).
Example 1.143 (CDCl3): 11.23 (br s, 1H); 8.36 (dd, J=1.2, 8.0, 1H); 7.96 (dd, J=0.6, 8.0, 1H); 7.28 (t, J=8.0, 1H); 4.42 (q, J=7.1, 2H); 2.74 (m, 1H); 1.42 (t, J=7.1, 3H); 1.04 (m, 4H).
Example 1.191 (CDCl3): 10.76 (br s, 1H); 7.81 (dd, J=1.1, 7.8, 1H); 7.11 (t, J=84.4, 1H); 7.00 (dd, J=1.2, 8.3, 1H); 4.07 (s, 3H); 3.93 (s, 3H); 3.19 (s, 3H).
Example 1.194 (d6-DMSO): 7.82 (m, 1H); 7.31 (m, 2H); 4.37 (q, J=7.2, 2H); 3.86 (s, 3H); 3.05 (s, 3H); 1.38 (t, J=7.2, 3H).
Example 1.195 (CDCl3): 10.78 (br s, 1H); 7.81 (dd, J=0.8, 8.0, 1H); 7.11 (t, J=8.0, 1H); 6.99 (dd, J=0.8, 8.0, 1H); 4.33 (t, J=7.2, 2H); 3.94 (s, 3H); 3.19 (s, 3H); 1.81 (m, 2H); 0.99 (t, J=7.2, 3H).
Example 1.196 (CDCl3): 10.77 (br s, 1H); 7.79 (dd, J=0.8, 7.9, 1H); 7.09 (t, J=8.1, 1H); 6.99 (dd, J=0.9, 8.4, 1H); 5.14 (m, 1H); 3.93 (s, 3H); 3.16 (s, 3H); 1.38 (d, J=6.2, 6H).
Example 1.197 (CDCl3): 10.86 (s, 1H); 7.81 (dd, J=1.2, 7.9, 1H); 7.11 (t, J=8.4, 1H); 7.00 (dd, J=1.2, 8.5, 1H); 3.94 (s, 3H); 3.21 (m, 5H); 1.41 (t, J=7.4, 3H).
Example 1.198 (CDCl3): 10.77 (br s, 1H); 7.79 (dd, J=1.1, 7.9, 1H); 7.09 (t, J=8.3, 1H); 7.00 (dd, J=1.0, 8.4, 1H); 4.04 (s, 3H); 3.93 (s, 3H); 2.72 (m, 1H); 1.02 (m, 4H).
Example 1.201 (d6-DMSO): 7.80 (m, 1H); 7.30 (m, 2H); 4.35 (q, J=7.1, 2H); 3.87 (s, 3H); 2.76 (m, 1H); 1.35 (t, J=7.0, 3H); 0.91 (m, 4H).
Example 1.204 (d6-DMSO): 7.80 (m, 1H); 7.29 (m, 2H); 4.25 (t, J=6.4, 2H); 3.87 (s, 3H); 2.77 (m, 1H); 1.75 (m, 2H); 0.94 (m, 7H).
Example 1.211 (d6-DMSO): 7.80 (m, 1H); 7.28 (m, 2H); 4.17 (q, J=7.0, 2H); 3.98 (s, 3H); 3.06 (s, 3H); 1.34 (t, J=6.9, 3H).
Example 1.214 (d6-DMSO): 10.88 (br s, 1H); 7.80 (dd, J=2.2, 6.7, 1H); 7.28 (m, 2H); 4.36 (q, J=7.1, 2H); 4.17 (q, J=7.0, 2H); 3.06 (s, 3H); 1.35 (m, 6H).
Example 1.215 (CDCl3): 10.70 (br s, 1H); 7.79 (dd, J=1.0, 7.6, 1H); 7.07 (t, J=8.3, 1H); 6.97 (dd, J=1.1, 8.4, 1H); 4.33 (t, J=6.6, 2H); 4.16 (q, J=7.0, 2H); 3.19 (s, 3H); 1.81 (m, 2H); 1.51 (t, J=7.0, 3H); 0.98 (t, J=7.4, 3H).
Example 1.218 (CDCl3): 10.69 (br s, 1H); 7.77 (dd, J=1.1, 7.9, 1H); 7.05 (t, J=8.3, 1H); 6.95 (dd, J=1.1, 8.4, 1H); 4.15 (q, J=7.0, 2H); 4.03 (s, 3H); 2.72 (m, 1H); 1.50 (t, J=7.0, 3H); 1.01 (m, 4H).
Example 1.221 (d6-DMSO): 10.92 (br s, 1H), 7.79 (dd, J=2.1, 6.8, 1H); 7.28 (m, 2H); 4.34 (q, J=7.0, 2H); 4.17 (q, J=7.0, 2H); 2.76 (m, 1H); 1.35 (m, 6H), 0.92 (m, 4H).
Example 1.231 (CDCl3): 10.63 (br s, 1H); 7.77 (dd, J=1.1, 8.4, 1H); 7.05 (t, J=8.4, 1H); 6.96 (dd, J=1.1, 8.4, 1H); 4.05 (s, 3H); 4.03 (t, J=6.7, 2H); 3.18 (s, 3H); 1.91 (m, 2H); 1.07 (t, J=7.4, 3H).
Example 1.235 (CDCl3): 10.67 (br s, 1H); 7.79 (dd, J=1.1, 7.8, 1H); 7.07 (t, J=8.3, 1H); 6.98 (dd, J=1.0, 8.4, 1H); 4.33 (t, J=6.7, 2H); 4.04 (t, J=6.6, 2H); 3.19 (s, 3H); 1.91 (m, 2H); 1.80 (m, 2H); 1.07 (t, J=7.4, 3H); 0.98 (t, t, J=7.4, 3H).
Example 1.236 (CDCl3): 10.70 (br s, 1H); 7.79 (br d, J=7.8, 1H); 7.07 (br t, J=7.9, 1H); 6.98 (br d, J=8.4, 1H); 5.15 (m, 1H); 4.04 (t, J=6.6, 2H); 3.16 (s, 3H); 1.91 (m, 2H); 1.38 (d, J=6.2, 6H); 1.07 (t, J=7.5, 3H).
Example 1.237 (CDCl3): 10.76 (br s, 1H); 7.79 (dd, 1.1, 7.9, 1H); 7.06 (m, 2H); 4.04 (t, J=6.6, 2H); 3.20 (s, 3H); 3.07 (q, J=7.4, 2H); 1.92 (m, 2H); 1.40 (t, J=7.4, 3H); 1.10 (t, J=7.4, 3H).
Example 1.238 (CDCl3): 10.66 (br s, 1H); 7.77 (dd, J=1.1, 7.9, 1H); 7.06 (t, J=8.4, 1H); 6.96 (dd, J=1.1, 8.4, 1H); 4.04 (s, 3H); 4.03 (t, J=6.6, 2H); 2.72 (m, 1H); 1.90 (m, 2H); 1.07 (t, J=7.4, 3H); 1.01 (m, 4H).
Example 1.241 (CDCl3): 10.71 (br s, 1H); 7.78 (dd, J=1.1, 7.8, 1H); 7.06 (t, J=8.4, 1H); 6.97 (dd, J=1.1, 8.4, 1H); 4.42 (q, J=7.1, 2H); 4.03 (t, J=6.6, 2H); 2.72 (m, 1H); 1.91 (m, 2H); 1.42 (t, J=7.1, 3H); 1.07 (t, J=7.4, 3H); 1.03 (m, 4H).
Example 1.244 (CDCl3): 10.67 (br s, 1H); 7.76 (dd, J=1.2, 7.8, 1H); 7.04 (t, J=8.4, 1H); 6.95 (dd, J=1.1, 8.4, 1H); 4.30 (t, J=6.5, 2H); 4.02 (t, J=6.6, 2H); 2.72 (m, 1H); 1.91 (m, 2H); 1.80 (m, 2H); 1.07 (t, J=7.4, 3H); 1.04 (m, 4H); 0.99 (t, J=7.4, 3H).
Example 1.251 (CDCl3): 10.62 (br s, 1H); 7.76 (dd, J=1.1, 7.8, 1H); 7.05 (m, 1H); 6.97 (m, 1H); 4.70 (m, 1H); 4.06 (s, 3H); 3.19 (s, 3H); 1.40 (d, J=6.1, 6H).
Example 1.254 (CDCl3): 10.65 (br s, 1H); 7.77 (dd, J=1.1, 7.8, 1H); 7.05 (t, J=7.9, 1H); 6.97 (br d, J=8.4, 1H); 4.70 (m, 1H); 4.43 (q, J=7.1, 2H); 3.18 (s, 3H); 1.42 (t, J=7.1, 3H); 1.40 (d, J=6.1, 6H).
Example 1.255 (CDCl3): 10.65 (br s, 1H); 7.76 (dd, J=1.1, 7.8, 1H); 7.06 (dd, J=7.8, 8.4, 1H); 6.97 (br d, J=8.4, 1H); 4.71 (m, 1H); 4.33 (t, J=6.7, 2H); 3.19 (s, 3H); 1.80 (m, 2H); 1.40 (d, J=6.1, 6H); 0.98 (t, J=7.4, 3H).
Example 1.256 (CDCl3): 10.68 (br s, 1H); 7.77 (br d, J=7.8, 1H); 7.06 (br t, J=8.4, 1H); 6.97 (br d, J=8.4, 1H); 5.15 (m, 1H); 4.71 (m, 1H); 3.16 (br s, 3H); 1.40 (m, 12H).
Example 1.258 (CDCl3): 10.67 (br s, 1H); 7.76 (m, 1H); 7.05 (m, 1H); 6.97 (m, 1H); 4.70 (m, 1H); 4.04 (s, 3H); 2.72 (m, 1H); 1.40 (d, J=6.1, 6H); 0.98 (m, 4H).
Example 1.261 (CDCl3): 10.70 (br s, 1H); 7.76 (dd, J=1.1, 7.8, 1H); 7.06 (t, J=8.4, 1H); 6.97 (br d, J=7.9, 1H); 4.71 (m, 1H); 4.42 (q, J=7.1, 2H); 2.73 (m, 1H); 1.42 (d, J=7.1, 3H); 1.40 (d, J=6.1, 6H); 1.01 (m, 4H).
Example 1.264 (CDCl3): 10.69 (br s, 1H); 7.76 (dd, J=1.0, 7.8, 1H); 7.05 (t, J=8.2, 1H); 6.97 (br d, J=7.9, 1H); 4.71 (m, 1H); 4.31 (t, J=6.6, 2H); 2.73 (m, 1H); 1.80 (m, 2H); 1.40 (d, J=6.1, 6H); 1.02 (m, 4H); 1.00 (t, J=7.4, 3H).
Example 1.273 (CDCl3): 10.65 (br s, 1H); 7.79 (dd, J=1.1, 7.8, 1H); 7.07 (t, J=8.4, 1H); 6.98 (dd, J=1.1, 8.4, 1H); 4.07 (t, J=6.6, 2H); 4.06 (s, 3H); 3.19 (s, 3H); 1.85 (m, 2H); 1.52 (m, 2H); 0.98 (t, J=7.4, 3H).
Example 1.274 (CDCl3): 10.67 (br s, 1H); 7.81 (dd, 1.1, 7.8, 1H); 7.07 (t, J=8.3, 1H); 6.98 (dd, J=1.1, 8.4, 1H); 4.44 (q, J=7.1, 2H); 4.07 (t, J=6.6, 2H); 3.18 (s, 3H); 1.86 (m, 2H); 1.52 (m, 2H); 1.42 (t, J=7.1, 3H); 0.98 (t, J=7.4, 3H).
Example 1.275 (CDCl3): 10.67 (br s, 1H); 7.79 (dd, J=1.1, 7.8, 1H); 7.07 (t, J=8.4, 1H); 6.98 (dd, J=1.1, 8.4, 1H); 4.33 (t, J=6.7, 2H); 4.07 (t, J=6.6, 2H); 3.19 (s, 3H); 1.83 (m, 4H); 1.52 (m, 4H); 0.98 (t, J=7.4, 3H); 0.98 (t, J=7.4, 3H).
Example 1.276 (CDCl3): 10.71 (br s, 1H); 7.79 (dd, J=1.1, 7.8, 1H); 7.07 (t, J=8.4, 1H); 6.98 (dd, J=1.1, 8.4, 1H); 5.15 (m, 1H); 4.08 (t, J=6.6, 2H); 3.16 (s, 3H); 1.86 (m, 2H); 1.52 (m, 2H); 1.39 (d, J=6.2, 6H); 0.98 (t, J=7.4, 3H).
Example 1.278 (CDCl3): 10.70 (br s, 1H); 7.79 (dd, J=1.1, 7.8, 1H); 7.07 (t, J=8.4, 1H); 6.98 (dd, J=1.1, 8.4, 1H); 4.07 (t, J=6.6, 2H); 4.05 (s, 3H); 2.72 (m, 1H); 1.86 (m, 2H); 1.52 (m, 2H); 1.02 (m, 4H); 0.99 (t, J=7.4, 3H).
Example 1.279 (CDCl3): 10.72 (br s, 1H); 7.79 (dd, J=1.1, 7.8, 1H); 7.06 (t, J=8.4, 1H); 6.98 (dd, J=1.1, 8.4, 1H); 4.42 (q, J=7.1, 2H); 4.07 (t, J=6.6, 2H); 2.72 (m, 1H); 1.86 (m, 2H); 1.52 (m, 2H); 1.42 (t, J=7.1, 3H); 1.02 (m, 4H); 0.99 (t, J=7.3, 3H).
Example 1.280 (CDCl3): 10.71 (br s, 1H); 7.79 (dd, J=1.1, 7.8, 1H); 7.06 (t, J=8.4, 1H); 6.98 (dd, J=1.1, 8.4, 1H); 4.31 (t, J=6.6, 2H); 4.07 (t, J=6.6, 1H); 2.73 (m, 1H); 1.83 (m, 4H); 1.52 (m, 2H); 1.01 (m, 10H).
Example 1.281 (CDCl3): 10.60 (br s, 1H); 7.77 (dd, J=1.1, 7.8, 1H); 7.05 (t, J=8.4, 1H); 6.96 (br d, J=8.0, 1H); 4.48 (m, 1H); 4.06 (s, 3H); 3.19 (s, 3H); 1.88 (m, 1H); 1.70 (m, 1H); 1.31 (d, J=6.1, 3H, 0.97 (t, J=7.5, 3H).
Example 1.286 (CDCl3): 10.65 (br s, 1H); 7.76 (dd, J=1.1, 7.8, 1H); 7.05 (t, J=8.3, 1H); 6.96 (br d, J=8.1, 1H); 4.48 (m, 1H); 4.04 (s, 3H); 2.72 (m, 1H); 1.88 (m, 1H); 1.70 (m, 1H); 1.32 (d, J=6.1, 3H); 1.00 (m, 4H); 0.98 (t, J=7.5, 3H).
Example 1.289 (CDCl3): 10.63 (br s, 1H); 7.79 (dd, J=1.1, 7.8, 1H); 7.07 (t, J=8.4, 1H); 6.98 (dd, J=1.1, 8.4, 1H); 4.06 (s, 3H); 3.83 (d, J=6.7, 2H); 3.18 (s, 3H); 2.21 (m, 1H); 1.06 (d, J=6.7, 6H).
Example 1.290 (CDCl3): 10.65 (br s, 1H); 7.79 (dd, J=1.1, 7.8, 1H); 7.07 (t, J=8.4, 1H); 6.97 (dd, J=1.1, 8.4, 1H); 4.43 (q, J=7.1, 2H); 2.83 (d, J=6.7, 2H); 3.18 (s, 3H); 2.22 (m, 1H); 1.42 (t, J=7.1, 3H); 1.07 (d, J=6.7, 6H).
Example 1.294 (CDCl3): 10.67 (br s, 1H); 7.79 (dd, J=1.1, 7.8, 1H); 7.06 (t, J=8.4, 1H); 6.97 (dd, J=1.1, 8.4, 1H); 4.04 (s, 3H); 3.83 (d, J=6.7, 2H); 2.72 (m, 1H); 2.22 (m, 1H); 1.06 (d, J=6.7, 6H); 1.01 (m, 4H).
Example 1.295 (CDCl3): 10.69 (br s, 1H); 7.79 (dd, J=1.1, 7.8, 1H); 7.06 (t, J=8.4, 1H); 6.97 (dd, J=1.1, 8.4, 1H); 4.42 (q, J=7.1, 2H); 3.83 (d, J=6.7, 2H); 2.72 (m, 1H); 2.22 (m, 1H); 1.42 (t, J=7.1, 3H); 1.06 (d, J=6.7, 6H); 1.02 (m, 4H).
Example 1.346 (CDCl3): 10.63 (br s, 1H); 7.73 (dd, J=1.1, 7.9, 1H); 7.02 (t, J=8.0, 1H); 6.92 (dd, J=1.0, 8.4, 1H); 4.00 (s, 3H); 3.87 (d, J=7.1, 2H); 3.12 (s, 3H); 1.28 (m, 1H); 0.60 (m, 2H); 0.30 (m, 2H).
Example 1.349 (CDCl3): 10.71 (br s, 1H); 7.81 (dd, J=1.1, 7.9, 1H); 7.07 (t, J=8.3, 1H); 6.96 (dd, J=1.0, 8.4, 1H); 4.45 (q, J=7.1, 2H); 3.94 (d, J=7.1, 2H); 3.19 (s, 3H); 1.43 (t, J=7.1, 3H); 1.37 (m, 1H); 0.67 (m, 2H); 0.37 (m, 2H).
Example 1.350 (CDCl3): 10.70 (br s, 1H); 7.80 (dd, J=1.2, 7.8, 1H); 7.06 (dd, J=7.9, 8.3, 1H); 6.96 (dd, J=1.1, 8.4, 1H); 4.33 (t, J=6.7, 2H); 3.93 (d, J=7.1, 2H); 3.18 (s, 3H); 1.80 (m, 2H); 1.36 (m, 1H); 0.98 (t, J=7.4, 3H); 0.67 (m, 2H); 0.36 (m, 2H).
Example 1.353 (CDCl3): 10.71 (br s, 1H); 7.79 (dd, J=1.1, 7.9, 1H); 7.06 (t, J=8.3, 1H); 6.96 (dd, J=1.0, 8.4, 1H); 4.05 (s, 3H); 3.93 (d, J=7.9, 2H); 2.72 (m, 1H); 1.36 (m, 1H); 1.01 (m, 4H); 0.67 (m, 2H); 0.36 (m, 2H).
Example 1.356 (CDCl3): 10.73 (br s, 1H); 7.79 (dd, J=0.6, 7.8, 1H); 7.06 (t, J=8.3, 1H); 6.95 (br d, J=8.3, 1H); 4.42 (q, J=7.0, 2H); 3.93 (d, J=7.1, 2H); 2.72 (m, 1H); 1.42 (t, J=7.1, 3H); 1.36 (m, 1H); 1.01 (m, 4H); 0.67 (m, 2H); 0.36 (m, 2H).
Example 1.359 (CDCl3): 10.73 (br s, 1H); 7.80 (dd, J=1.1, 7.8, 1H); 7.06 (t, J=8.1, 1H); 6.96 (dd, J=1.0, 8.4, 1H); 4.32 (t, J=6.6, 2H); 3.94 (d, J=7.1, 2H); 2.73 (m, 1H); 1.81 (m, 2H); 1.37 (m, 1H); 1.01 (m, 4H); 1.00 (t, J=7.4, 3H); 0.68 (m, 2H); 0.37 (m, 2H).
Example 1.440 (d6-DMSO): 8.25 (dd, J=0.8, 8.0, 1H); 7.62 (dt, J=0.8, 8.0, 1H); 7.44 (t, J=8.0, 1H); 3.98 (s, 3H); 3.04 (s, 3H).
Example 1.443 (d6-DMSO): 8.26 (dd, J=0.8, 8.0, 1H); 7.63 (dt, J=0.8, 8.0, 1H); 7.47 (t, J=8.0, 1H); 4.37 (q, J=7.2, 2H); 3.04 (s, 3H); 1.36 (t, J=7.2, 3H).
Example 1.444 (d6-DMSO): 8.27 (dd, J=0.8, 8.0, 1H); 7.64 (dt, J=0.8, 8.0, 1H); 7.46 (t, J=8.0, 1H); 4.28 (t, J=7.2, 2H); 3.06 (s, 3H); 1.76 (m, 2H); 0.96 (t, J=7.2, 3H).
Example 1.447 (d6-DMSO): 8.25 (dd, J=1.2, 7.9, 1H); 7.62 (dt, J=1.3, 8.3, 1H); 7.46 (t, J=8.1, 1H); 3.96 (s, 3H); 2.75 (m, 1H); 0.90 (m, 4H).
Example 1.450 (CDCl3): 11.00 (br s, 1H); 8.13 (dd, J=1.2, 8.0, 1H); 7.40 (m, 1H); 7.22 (t, J=8.1, 1H); 4.42 (q, J=7.1, 2H); 2.74 (m, 1H); 1.42 (t, J=7.1, 3H); 1.03 (m, 4H).
Example 1.453 (CDCl3): 11.00 (br s, 1H); 8.12 (dd, J=1.2, 8.0, 1H); 7.40 (dt, J=1.4, 8.3, 1H); 7.22 (t, J=8.1, 1H); 4.32 (t, J=6.6, 2H); 2.74 (m, 1H); 1.81 (m, 2H); 1.03 (m, 4H); 1.00 (t, J=7.4, 3H).
Example 1.460 (CDCl3): 11.02 (br s, 1H); 8.08 (dd, J=1.2, 7.8, 1H); 7.36 (br dd, J=1.0, 8.2, 1H); 7.21 (t, J=8.1, 1H); 6.78 (t, J=74.2, 1H); 4.08 (s, 3H); 3.21 (s, 3H).
Example 1.463 (CDCl3): 11.05 (br s, 1H); 8.08 (dd, J=1.2, 8.0, 1H); 7.36 (dd, J=1.1, 8.2, 1H); 7.21 (t, J=8.1, 1H); 6.78 (t, J=74.2, 1H); 4.45 (q, J=7.1, 2H); 3.21 (s, 3H); 1.43 (t, J=7.1, 3H).
Example 1.464 (CDCl3): 11.04 (br s, 1H); 8.07 (br d, J=7.9, 1H); 7.39 (br d, J=8.2, 1H); 7.20 (t, J=8.0, 1H); 6.78 (t, J=74.2, 1H); 4.34 (t, J=6.7, 2H); 3.21 (s, 3H); 1.81 (m, 2H); 0.91 (t, J=7.4, 3H).
Example 1.465 (CDCl3): 11.09 (br s, 1H); 8.07 (dd, J=1.2, 8.0, 1H); 7.36 (dd, J=1.1, 8.2, 1H); 7.21 (t, J=8.0, 1H); 6.77 (t, J=74.3, 1H); 5.16 (m, 1H); 3.18 (s, 3H); 1.40 (d, J=6.2, 6H).
Example 1.467 (CDCl3): 11.05 (br s, 1H); 8.07 (dd, J=1.2, 8.0, 1H); 7.36 (br dd, J=1.1, 8.2, 1H); 7.21 (t, J=8.1, 1H); 6.78 (t, J=74.2, 1H); 4.07 (s, 3H); 2.75 (m, 1H); 1.04 (m, 4H).
Example 1.470 (CDCl3): 11.09 (br s, 1H); 8.07 (dd, J=1.2, 8.0, 1H); 7.36 (dd, J=1.1, 8.2, 1H); 7.21 (t, J=8.1, 1H); 6.79 (t, J=74.3, 1H); 4.44 (q, J=7.1, 2H); 2.75 (m, 1H); 1.43 (t, J=7.1, 3H); 1.04 (m, 4H).
Example 1.473 (CDCl3): 11.09 (br s, 1H); 8.07 (dd, J=1.2, 8.0, 1H); 7.36 (br dd, J=1.1, 8.2, 1H); 7.20 (t, J=8.1, 1H); 6.79 (t, J=74.3, 1H); 4.33 (t, J=6.6, 2H); 2.75 (m, 1H); 1.82 (m, 2H); 1.04 (m, 4H); 1.00 (t, J=7.4, 3H).
Example 1.481 (CDCl3): 10.76 (br s, 1H); 7.96 (dd, J=1.2, 7.8, 1H); 7.17 (t, J=8.3, 1H); 7.10 (dd, J=1.1, 8.3, 1H); 4.52 (q, J=8.2, 2H); 4.07 (s, 3H); 3.19 (s, 3H).
Example 1.488 (CDCl3): 10.81 (br s, 1H); 7.95 (dd, J=1.4, 7.7, 1H); 7.16 (t, J=8.3; 1H); 7.09 (dd, J=1.3, 8.3, 1H); 4.52 (q, J=8.2, 2H); 4.05 (s, 3H); 2.73 (m, 1H); 1.02 (m, 4H).
Example 1.501 (CDCl3): 10.76 (br s, 1H); 7.90 (dd, J=1.0, 7.9, 1H); 7.14 (t, J=8.2, 1H); 7.03 (dd, J=1.0, 8.4, 1H); 6.24 (tt, J=4.2, 54.9, 1H); 4.31 (td, J=4.2, 12.7, 2H); 4.06 (s, 3H); 3.19 (s, 3H).
Example 1.504 (CDCl3): 10.78 (br s, 1H); 7.90 (d, J=7.9, 1H); 7.14 (t, J=8.0, 1H); 7.03 (d, J=8.3, 1H); 6.23 (tt, J=4.1, 54.9, 1H); 4.44 (q, J=7.1, 2H); 4.31 (td, J=4.0, 12.7, 2H); 3.19 (s, 3H); 1.42 (t, J=7.1, 3H).
Example 1.505 (CDCl3): 10.78 (br s, 1H); 7.90 (dd, J=1.1, 7.9, 1H); 7.14 (t, J=8.2, 1H); 7.03 (dd, J=1.1, 8.4, 1H); 6.23 (tt, J=4.2, 55.0, 1H); 4.31 (m, 4H); 3.19 (s, 3H); 1.80 (m, 2H); 0.98 (t, J=7.4, 3H).
Example 1.506 (CDCl3): 10.81 (br s, 1H); 7.90 (dd, J=1.1, 7.9, 1H); 7.14 (t, J=8.3, 1H); 7.03 (dd, J=1.1, 8.4, 1H); 6.24 (tt, J=4.2, 55.0, 1H); 5.15 (m, 1H); 4.31 (td, J=4.2, 12.7, 2H); 3.16 (s, 3H); 1.39 (d, J=6.2, 6H).
Example 1.508 (CDCl3): 10.80 (br s, 1H); 7.90 (dd, J=1.1, 7.9, 1H); 7.13 (t, J=8.2, 1H); 7.02 (dd, J=1.0, 8.4, 1H); 6.24 (tt, J=4.2, 54.9, 1H); 4.31 (td, J=4.1, 12.7, 2H); 4.05 (s, 3H); 2.72 (m, 1H); 1.02 (m, 4H).
Example 1.511 (CDCl3): 10.82 (br s, 1H); 7.89 (dd, J=1.0, 7.9, 1H); 7.13 (t, J=8.2, 1H); 7.02 (dd, J=0.8, 8.3, 1H); 6.24 (tt, J=4.2, 54.9, 1H); 4.42 (q, J=7.1, 2H); 4.31 (td, J=4.2, 12.7, 2H); 2.73 (m, 1H); 1.42 (t, J=7.1, 3H); 1.02 (m, 4H).
Example 1.514 (CDCl3): 10.84 (br s, 1H); 7.90 (dd, J=1.1, 7.9, 1H); 7.13 (t, J=8.9, 1H); 7.02 (dd, J=1.1, 8.3, 1H); 6.24 (tt, J=4.2, 55.0, 1H); 4.31 (m, 4H); 2.73 (m, 1H); 1.81 (m, 2H); 1.02 (m, 4H).
Example 1.522 (CDCl3): 10.70 (br s, 1H); 7.91 (dd, J=1.1, 7.8, 1H); 7.13 (t, J=8.4, 1H); 7.04 (br d, J=8.1, 1H); 4.83 (m, 1H); 4.06 (s, 3H); 3.19 (s, 3H); 1.59 (d, J=6.5, 3H).
Example 1.525 (CDCl3): 10.73 (br s, 1H); 7.91 (dd, J=1.1, 7.8, 1H); 7.12 (t, J=8.3, 1H); 7.04 (br d, J=8.3, 1H); 4.83 (m, 1H); 4.44 (q, J=7.1, 2H); 3.18 (s, 3H); 1.59 (d, J=6.5, 3H); 1.42 (t, J=7.1, 3H).
Example 1.526 (CDCl3): 10.72 (br s, 1H); 7.91 (dd, J=1.1, 7.8, 1H); 7.12 (t, J=8.4, 1H); 7.04 (d, J=8.1, 1H); 4.83 (m, 1H); 4.33 (m, 2H); 3.19 (s, 3H); 1.81 (m, 2H); 1.59 (d, J=6.5, 3H); 0.99 (t, J=7.4, 3H).
Example 1.527 (CDCl3): 10.75 (br s, 1H); 7.91 (dd, J=1.1, 7.8, 1H); 7.12 (t, J=8.4, 1H); 7.04 (br d, J=8.0, 1H); 5.15 (m, 1H); 4.83 (m, 1H); 3.16 (s, 3H).
Example 1.529 (CDCl3): 10.74 (br s, 1H); 7.91 (dd, J=1.1, 7.8, 1H); 7.12 (t, J=8.4, 1H); 7.04 (br d, J=8.1, 1H); 4.82 (m, 1H); 4.05 (s, 3H); 2.72 (m, 1H); 1.59 (d, J=6.5, 3H); 1.00 (m, 4H).
Example 1.532 (CDCl3): 10.78 (br s, 1H); 7.91 (dd, J=1.1, 7.8, 1H); 7.12 (t, J=8.2, 1H); 7.04 (d, J=8.2, 1H); 4.82 (m, 1H); 4.42 (m, 2H); 2.72 (m, 1H); 1.59 (d, J=6.5, 3H); 1.42 (t, J=7.1, 3H); 1.01 (m, 4H).
Example 1.535 (CDCl3): 10.77 (br s, 1H); 7.91 (dd, J=1.1, 7.8, 1H); 7.12 (t, J=8.4, 1H); 7.04 (br d, J=8.0, 1H); 4.82 (m, 1H); 4.31 (td, J=1.6, 6.6, 2H); 2.73 (m, 1H); 1.81 (m, 2H); 1.60 (d, J=6.5, 3H); 1.01 (m, 4H); 1.00 (t, J=7.4, 3H).
Example 1.544 (CDCl3): 7.97 (dd, J=1.3, 7.7, 1H); 7.18 (t, J=8.3, 1H); 7.12 (dd, J=1.3, 8.3, 1H); 4.59 (td, J=0.9, 13.0, 2H); 4.07 (s, 3H); 3.19 (s, 3H).
Example 1.549 (CDCl3): 7.97 (dd, J=1.4, 7.7, 1H); 7.17 (t, J=8.3, 1H); 7.12 (dd, J=1.3, 8.3, 1H); 4.59 (td, J=0.7, 12.9, 2H); 4.33 (t, J=6.7, 2H); 3.19 (s, 3H); 1.81 (m, 2H); 0.99 (t, J=7.4, 3H).
Example 1.550 (CDCl3): 10.77 (br s, 1H); 7.97 (dd, J=1.5, 7.5, 1H); 7.18 (t, J=8.3, 1H); 7.12 (dd, J=1.5, 8.3, 1H); 5.16 (m, 1H); 4.59 (td, J=0.9, 13.0, 2H); 3.16 (s, 3H); 1.39 (d, J=6.2, 6H).
Example 1.552 (CDCl3): 10.78 (br s, 1H); 7.97 (dd, J=1.3, 7.7, 1H); 7.17 (t, J=8.3, 1H); 7.11 (dd, J=1.2, 8.3, 1H); 4.59 (td, J=0.8, 12.9, 2H); 4.05 (s, 3H); 2.73 (m, 1H); 1.02 (m, 4H).
Example 1.555 (CDCl3): 10.81 (br s, 1H); 7.97 (dd, J=1.1, 7.7, 1H); 7.17 (t, J=8.2, 1H); 7.11 (dd, J=1.2, 8.2, 1H); 4.59 (t, J=13.0, 2H); 4.42 (q, J=7.1, 2H); 2.73 (m, 1H); 1.43 (t, J=7.1, 3H); 1.02 (m, 4H).
Example 1.558 (CDCl3): 7.97 (dd, J=1.3, 7.7, 1H); 7.17 (t, J=8.3, 1H); 7.11 (dd, J=1.3, 8.4, 1H); 4.59 (td, J=0.7, 13.0, 2H); 4.32 (t, J=6.6, 2H); 2.73 (m, 1H); 1.81 (m, 2H); 1.02 (m, 4H); 1.00 (t, J=7.4, 3H).
Example 1.579 (CDCl3): 11.00 (br s, 1H); 7.93 (dd, J=1.1, 7.8, 1H); 7.32 (d, J=7.9, 1H); 7.04 (t, J=7.9, 1H); 4.06 (s, 3H); 3.20 (s, 3H); 2.45 (s, H).
Example 1.581 (CDCl3): 11.02 (br s, 1H); 7.93 (dd, J=1.1, 7.8, 1H); 7.32 (d, J=8.1, 1H); 7.03 (t, J=7.9, 1H); 4.32 (t, J=6.7, 2H); 3.20 (s, 3H); 2.45 (s, 3H); 1.80 (m, 2H); 0.98 (t, J=7.4, 3H).
Example 1.582 (CDCl3): 11.05 (br s, 1H); 7.93 (dd, J=1.1, 7.7, 1H); 7.32 (dd, J=0.7, 8.1, 1H); 7.03 (t, J=7.7, 1H); 5.14 (m, 1H); 3.17 (s, 3H); 2.45 (s, 3H); 1.39 (d, J=6.2, 6H).
Example 1.584 (CDCl3): 11.04 (br s, 1H); 7.93 (dd, J=1.1, 7.7, 1H); 7.31 (dd, J=0.5, 8.2, 1H); 7.03 (t, J=8.0, 1H); 4.04 (s, 3H); 2.73 (m, 1H); 2.45 (s, 3H); 1.02 (m, 4H).
Example 1.585 (CDCl3): 11.00 (br s, 1H); 7.93 (dd, J=1.1, 7.7, 1H); 7.31 (d, J=7.7, 1H); 7.03 (t, J=7.9, 1H); 4.41 (q, J=7.1, 2H); 2.73 (m, 1H); 2.45 (s, 3H); 1.42 (t, J=7.1, 3H); 1.02 (m, 4H).
Example 1.586 (CDCl3): 11.06 (br s, 1H); 7.93 (dd, J=1.1, 7.8, 1H); 7.31 (d, J=8.2, 1H); 7.03 (t, J=7.9, 1H); 4.31 (t, J=6.6, 2H); 2.73 (m, 1H); 2.45 (s, 3H); 1.80 (m, 2H); 1.02 (m, 4H); 0.99 (t, J=7.4, 3H).
Example 1.711 (CDCl3): 11.11 (br s, 1H); 8.10 (dd, J=1.2, 8.0, 1H); 7.63 (dd, J=1.2, 8.3, 1H); 7.23 (t, J=8.1, 1H); 4.07 (s, 3H); 3.44 (s, 3H); 3.21 (s, 3H).
Example 1.712 (CDCl3): 11.17 (br s, 1H); 8.09 (dd, J=1.2, 8.0, 1H); 7.62 (dd, J=1.2, 8.3, 1H); 7.22 (t, J=8.11, 1H); 4.45 (q, J=7.1, 2H); 3.44 (s, 3H); 3.20 (s, 3H); 1.42 (t, J=7.1, 3H).
Example 1.713 (CDCl3): 11.16 (br s, 1H); 8.10 (dd, J=1.2, 8.0, 1H); 7.62 (dd, J=1.1, 8.3, 1H); 7.23 (t, J=8.1, 1H); 4.34 (t, J=6.6, 2H); 3.44 (s, 3H); 3.21 (s, 3H); 1.59 (m, 2H); 0.99 (t, J=7.4, 3H).
Example 1.716 (CDCl3): 11.14 (br s, 1H); 8.10 (dd, J=1.1, 8.0, 1H); 7.63 (dd, J=1.1, 8.3, 1H); 7.23 (t, J=8.2, 1H); 4.06 (s, 3H); 3.44 (s, 3H); 2.75 (m, 1H); 1.04 (m, 4H).
Example 1.717 (CDCl3): 11.17 (br s, 1H); 8.09 (dd, J=1.2, 8.0, 1H); 7.62 (dd, J=1.2, 8.3, 1H); 7.22 (t, J=8.2, 1H); 4.43 (q, J=7.1, 2H); 3.44 (s, 3H); 2.74 (m, 1H); 1.43 (t, J=7.1, 3H); 1.03 (m, 4H).
Example 1.718 (CDCl3): 11.18 (br s, 1H); 8.10 (dd, J=1.2, 8.0, 1H); 7.62 (dd, J=1.2, 8.3, 1H); 7.22 (t, J=8.1, 1H); 4.33 (t, J=6.6, 2H); 3.44 (s, 3H); 2.75 (m, 1H); 1.81 (m, 2H); 1.03 (m, 4H); 1.00 (t, J=7.4, 3H).
Example 1.749 (CDCl3): 10.97 (br s, 1H); 8.04 (dd, J=1.2, 8.0, 1H); 7.75 (dd, J=1.2, 8.4, 1H); 7.19 (dd, J=8.0, 8.4, 1H); 4.07 (s, 3H); 3.20 (s, 3H); 3.13 (s, 6H).
Example 1.751 (CDCl3): 10.99 (br s, 1H); 8.03 (dd, J=1.1, 8.0, 1H); 7.74 (dd, J=1.1, 8.4, 1H); 7.19 (t, J=8.0, 1H); 4.34 (t, J=6.7, 2H); 3.19 (s, 3H); 3.13 (s, 6H); 1.80 (m, 2H); 0.98 (t, J=7.4, 3H).
Example 1.752 (CDCl3): 11.03 (br s, 1H); 8.04 (dd, J=1.1, 7.9, 1H); 7.75 (dd, J=1.1, 8.4, 1H); 7.19 (t, J=8.2, 1H); 5.16 (m, 2H); 3.17 (s, 3H); 3.13 (s, 6H); 1.39 (d, J=6.2, 6H).
Example 1.754 (CDCl3): 10.99 (br s, 1H); 8.03 (dd, J=1.1, 7.9, 1H); 7.75 (dd, J=1.1, 8.4, 1H); 7.18 (t, J=8.2, 1H); 4.05 (s, 3H); 3.13 (s, 6H); 2.73 (m, 1H); 1.02 (m, 4H).
Example 1.755 (CDCl3): 11.02 (br s, 1H); 8.03 (dd, J=1.2, 7.9, 1H); 7.74 (dd, J=1.1, 8.4, 1H); 7.18 (dd, J=8.0, 8.4, 1H); 4.43 (q, J=7.1, 2H); 3.13 (s, 6H); 2.73 (m, 1H); 1.42 (t, J=7.1, 3H); 1.02 (m, 4H).
Example 1.756 (CDCl3): 11.02 (br s, 1H); 8.03 (dd, J=1.1, 7.9, 1H); 7.74 (dd, J=1.1, 8.4, 1H); 7.18 (t, J=8.0, 1H); 4.32 (t, J=6.6, 2H); 3.13 (s, 6H); 2.74 (m, 1H); 1.31 (m, 2H); 1.01 (m, 4H); 1.00 (t, J=7.4, 3H).
Example 1.815 (CDCl3): 11.24 (br s, 1H); 7.99 (dd, J=0.8, 7.8, 1H); 7.29 (dd, J=0.6, 7.7, 1H); 7.03 (t, J=7.8, 1H); 2.87 (m, 1H); 2.87 (s, 3H); 1.91 (m, 1H); 1.12 (m, 8H).
Example 1.816 (d6-DMSO): 7.89 (d, J=9.1, 1H); 7.37 (d, J=9.2, 1H); 3.99 (s, 3H); 3.87 (s, 3H); 3.07 (s, 3H).
Example 1.817 (d6-DMSO): 7.89 (d, J=9.0, 1H); 7.37 (d, J=9.2, 1H); 4.37 (q, J=7.1, 2H); 3.87 (s, 3H); 3.06 (s, 3H); 1.36 (t, J=7.1, 3H).
Example 1.818 (d6-DMSO): 7.89 (d, J=9.1, 1H); 7.37 (d, J=9.2, 1H); 4.28 (t, J=6.5, 2H); 3.87 (s, 3H); 3.07 (s, 2H); 1.75 (m, 2H); 0.95 (t, J=7.3, 3H).
Example 1.819 (d6-DMSO): 7.89 (d, J=9.1, 1H); 7.37 (d, J=9.2, 1H); 5.02 (m, 1H); 3.88 (s, 3H); 3.04 (s, 3H); 1.36 (d, J=6.2, 6H).
Example 1.820 (CDCl3): 10.87 (br s, 1H); 7.65 (d, J=9.0, 1H); 7.00 (d, J=9.0, 1H); 4.05 (s, 3H); 3.95 (s, 3H); 2.73 (m, 1H), 1.03 (m, 4H).
Example 1.821 (d6-DMSO): 7.89 (d, J=9.1, 1H); 7.37 (d, J=9.1, 1H); 4.35 (q, J=7.1, 2H); 3.88 (s, 3H); 2.76 (m, 1H); 1.35 (t, J=7.1, 3H); 0.93 (m, 4H).
Example 1.822 (d6-DMSO): 7.89 (d, J=9.0, 1H); 7.37 (d, J=9.2, 1H); 4.26 (t, J=6.4, 2H); 3.88 (s, 3H); 2.76 (m, 1H); 1.75 (m, 2H); 0.96 (t, J=7.3, 3H); 0.92 (m, 4H).
Example 1.823 (CDCl3): 10.99 (br s, 1H); 8.42 (dd, J=5.6, 8.9, 1H); 7.76 (dd, J=2.5, 7.8, 1H); 7.24 (ddd, J=2.5, 7.5, 8.9, 1H); 4.07 (s, 3H); 3.21 (s, 3H).
Example 1.824 (CDCl3): 11.02 (br s, 1H); 8.41 (dd, J=5.6, 8.9, 1H); 7.76 (dd, J=2.5, 7.8, 1H); 7.23 (ddd, J=2.5, 7.5, 8.9, 1H); 4.34 (t, J=6.7, 2H); 3.21 (s, 3H); 1.81 (m, 2H); 0.99 (t, J=7.4, 3H).
Example 1.825 (CDCl3): 11.02 (br s, 1H); 8.41 (dd, J=5.6, 8.9, 1H); 7.76 (dd, J=2.5, 7.8, 1H); 7.23 (ddd, J=2.6, 7.6, 8.9, 1H); 4.06 (s, 3H); 2.74 (m, 1H); 1.04 (m, 4H).
Example 1.826 (CDCl3): 11.05 (br s, 1H); 8.40 (dd, J=5.6, 8.9, 1H); 7.76 (dd, J=2.5, 7.8, 1H); 7.23 (ddd, J=2.6, 7.6, 8.9, 1H); 4.43 (q, J=7.1, 2H); 2.74 (m, 1H); 1.43 (t, J=7.1, 3H); 1.03 (m, 4H).
Example 1.827 (CDCl3): 11.04 (br s, 1H); 8.40 (dd, J=5.6, 8.9, 1H); 7.76 (dd, J=2.5, 7.8, 1H); 7.22 (ddd, J=2.6, 7.6, 8.9, 1H); 4.33 (t, J=6.6, 2H); 2.75 (m, 1H); 1.81 (m, 2H); 1.03 (m, 4H); 1.00 (t, J=7.4, 3H).
Example 1.828 (CDCl3): 11.10 (br s, 1H); 8.32 (dd, J=1.5, 7.9, 1H); 7.69 (dd, J=1.5, 8.0, 1H); 7.48 (t, J=8.0, 1H); 4.07 (s, 3H); 3.21 (s, 3H).
Example 1.829 (CDCl3): 11.13 (br s, 1H); 8.31 (dd, J=1.5, 7.9, 1H); 7.69 (dd, J=1.5, 8.0, 1H); 7.48 (t, J=8.0, 1H); 4.44 (q, J=7.1, 2H); 3.20 (s, 3H); 1.42 (t, J=7.1, 3H).
Example 1.830 (CDCl3): 11.13 (br s, 1H); 8.31 (dd, J=1.5, 8.0, 1H); 7.69 (dd, J=1.5, 8.0, 1H); 7.48 (t, J=8.0, 1H); 4.33 (t, J=6.6, 2H); 3.20 (s, 3H); 1.81 (m, 2H); 0.98 (t, J=7.4, 3H).
Example 1.831 (CDCl3): 11.15 (br s, 1H); 8.31 (dd, J=1.6, 8.0, 1H); 7.69 (dd, J=1.6, 8.0, 1H); 7.48 (t, J=8.0, 1H); 5.15 (m, 1H); 3.17 (s, 3H); 1.39 (d, J=6.2, 6H).
Example 1.832 (CDCl3): 11.14 (br s, 1H); 8.31 (dd, J=1.5, 7.9, 1H); 7.69 (dd, J=1.5, 8.0, 1H); 7.47 (t, J=8.0, 1H); 4.06 (s, 3H); 2.74 (m, 1H); 1.03 (m, 4H).
Example 1.833 (CDCl3): 11.17 (br s, 1H); 8.30 (dd, J=1.5, 8.0, 1H); 7.68 (dd, J=1.6, 8.0, 1H); 7.47 (t, J=8.0, 1H); 4.42 (q, J=7.1, 2H); 2.73 (m, 1H); 1.42 (t, J=7.1, 3H); 1.03 (m, 4H).
Example 1.834 (CDCl3): 11.16 (br s, 1H); 8.28 (dd, J=1.5, 8.0, 1H); 7.67 (dd, J=1.5, 8.0, 1H); 7.46 (t, J=8.0, 1H); 4.31 (t, J=6.5, 2H); 2.74 (m, 1H); 1.80 (m, 2H); 1.02 (m, 2H); 0.99 (t, J=7.4, 3H).
Example 1.835 (CDCl3): 11.09 (br s, 1H); 8.63 (br s, 1H); 8.19 (d, J=8.2, 1H); 7.48 (ddd, J=0.6, 2.2, 8.2, 1H); 4.07 (s, 3H); 3.21 (s, 3H).
Example 1.836 (CDCl3): 11.11 (br s, 1H); 8.63 (d, J=2.1, 1H); 8.19 (dd, J=0.5, 8.2, 1H); 7.48 (ddd, J=0.6, 2.2, 8.2, 1H); 4.45 (q, J=7.1, 2H); 3.21 (s, 3H); 1.42 (t, J=7.1, 3H).
Example 1.837 (CDCl3): 11.11 (br s, 1H); 8.63 (d, J=2.0, 1H); 8.19 (d, J=8.3, 1H); 7.48 (dd, J=1.8, 7.8, 1H); 4.34 (t, J=6.7, 2H); 3.21 (s, 3H); 1.81 (m, 2H); 0.99 (t, J=7.4, 3H).
Example 1.838 (CDCl3): 11.14 (br s, 1H); 8.63 (d, J=2.1, 1H); 8.20 (br d, J=8.0, H); 7.48 (ddd, J=0.6, 2.2, 8.2, 1H); 5.16 (m, 1H); 3.18 (s, 3H); 1.39 (d, J=6.2, 6H).
Example 1.839 (CDCl3): 11.11 (br s, 1H); 8.62 (br d, J=1.8, 1H); 8.19 (dd, J=0.5, 8.2, 1H); 7.48 (ddd, J=0.6, 2.2, 8.1, 1H); 4.06 (s, 3H); 2.75 (m, 1H); 1.04 (m, 4H).
Example 1.840 (CDCl3): 11.14 (br s, 1H); 8.62 (d, J=2.1, 1H); 8.19 (br d, J=8.2, 1H); 7.47 (ddd, J=0.5, 2.1, 8.2, 1H); 4.43 (q, J=7.1, 2H); 2.74 (m, 1H); 1.43 (t, J=7.1, 3H); 1.04 (m, 4H).
Example 1.841 (CDCl3): 11.14 (br s, 1H); 8.62 (d, J=1.3, 1H); 8.19 (br d, J=8.2, 1H); 7.47 (ddd, J=0.6, 2.2, 8.2, 1H); 4.32 (t, J=6.6, 2H); 2.75 (m, 1H); 1.81 (m, 2H); 1.03 (m, 4H); 1.00 (t, J=7.4, 3H).
Example 1.842 (CDCl3): 11.11 (br s, 1H); 8.36 (br s, 1H); 7.77 (br s, 1H); 4.08 (s, 3H); 3.21 (s, 3H).
Example 1.843 (CDCl3): 11.15 (br s, 1H); 8.36 (br s, 1H); 7.77 (br s, 1H); 4.45 (q, J=7.1, 2H); 3.21 (s, 3H); 1.43 (t, J=7.1, 3H).
Example 1.844 (CDCl3): 11.15 (br s, 1H); 8.36 (br s, 1H); 7.77 (br s, 1H); 4.34 (t, J=6.7, 2H); 3.21 (s, 3H); 1.81 (m, 2H); 0.99 (t, J=7.4, 3H).
Example 1.845 (CDCl3): 8.36 (br s, 1H); 7.76 (br s, 1H); 5.16 (m, 1H); 3.18 (s, 3H); 1.39 (d, J=6.2, 6H).
Example 1.846 (CDCl3): 11.13 (br s, 1H); 8.35 (br s, 1H); 7.76 (br s, 1H); 4.06 (s, 3H); 2.74 (m, 1H); 1.03 (m, 4H).
Example 1.847 (CDCl3): 11.17 (br s, 1H); 8.35 (br s, 1H); 7.76 (br s, 1H); 4.43 (q, J=7.1, 2H); 2.74 (m, 1H); 1.42 (t, J=7.1, 3H); 1.04 (m, 4H).
Example 1.848 (CDCl3): 11.19 (br s, 1H); 8.35 (br s, 1H); 7.76 (br s, 1H); 4.32 (t, J=6.6, 2H); 2.75 (m, 1H); 1.81 (m, 2H); 1.03 (m, 4H); 1.00 (t, J=7.4, 3H).
Example 1.849 (CDCl3): 7.60 (d, J=8.6, 1H); 7.49 (d, J=8.6, 1H); 4.07 (s, 3H); 3.21 (s, 3H).
Example 1.850 (CDCl3): 11.16 (br s, 1H); 7.60 (d, J=8.6, 1H); 7.49 (d, J=8.6, 1H); 4.45 (q, J=J=7.1, 2H); 3.20 (s, 3H); 1.42 (t, J=7.1, 3H).
Example 1.851 (CDCl3): 11.16 (br s, 1H); 7.60 (d, J=8.6, 1H); 7.49 (d, J=8.7, 1H); 4.34 (t, J=6.7, 2H); 3.21 (s, 3H); 1.81 (m, 2H); 0.98 (t, J=7.4, 3H).
Example 1.852 (CDCl3): 11.19 (br s, 1H); 7.60 (d, J=8.7, 1H); 7.49 (d, J=8.6, 1H); 5.15 (m, 1H); 3.18 (s, 3H); 1.39 (d, J=6.2, 1H).
Example 1.853 (CDCl3): 11.16 (br s, 1H); 7.59 (d, J=8.6, 1H); 7.49 (d, J=8.6, 1H); 4.05 (s, 3H); 2.74 (m, 1H); 1.03 (m, 4H).
Example 1.854 (CDCl3): 11.20 (br s, 1H); 7.59 (d, J=8.6, 1H); 7.49 (d, J=8.6, 1H); 4.43 (q, J=7.1, 2H); 2.74 (m, 1H); 1.42 (t, J=7.1, 3H); 1.03 (m, 4H).
Example 1.855 (CDCl3): 10.99 (br s, 1H); 8.11 (dd, J=1.1, 8.1, 1H); 7.34 (m, 1H); 4.06 (s, 3H); 3.20 (s, 3H); 2.37 (d, J=1.9, 3H).
Example 1.856 (CDCl3): 11.01 (br s, 1H); 8.10 (dd, J=1.1, 8.1, 1H); 7.33 (m, 1H); 4.43 (q, J=7.1, 2H); 3.19 (s, 3H); 2.37 (d, J=1.8, 3H); 1.42 (t, J=7.1, 3H).
Example 1.857 (CDCl3): 11.02 (br s, 1H); 8.10 (dd, J=1.1, 8.1, 1H); 7.33 (ddd, J=0.7, 7.2, 7.9, 1H); 4.33 (t, J=6.7, 2H); 3.20 (s, 3H); 2.37 (d, J=2.3, 3H); 1.80 (sxt, J=7.4, 2H); 0.98 (t, J=7.4, 3H).
Example 1.858 (CDCl3): 11.04 (br s, 1H); 8.10 (dd, J=1.0, 8.0, 1H); 7.33 (m, 1H); 5.14 (m, 1H); 3.17 (s, 3H); 2.37 (br d, J=2.4, 3H); 1.39 (d, J=6.2, 6H).
Example 1.859 (CDCl3): 11.03 (br s, 1H); 8.10 (dd, J=1.0, 8.1, 1H); 7.33 (m, 1H); 4.05 (s, 3H); 2.73 (m, 1H); 2.37 (d, J=2.4, 3H); 1.03 (m, 4H).
Example 1.860 (CDCl3): 11.05 (br s, 1H); 8.10 (dd, J=1.1, 8.1, 1H); 7.32 (ddd, J=0.8, 7.2, 8.0, 1H); 4.42 (q, J=7.1, 2H); 2.73 (m, 1H); 2.37 (d, J=2.3, 3H); 1.42 (t, J=7.1, 3H); 1.02 (m, 4H).
Example 1.861 (CDCl3): 11.05 (br s, 1H); 8.10 (dd, J=1.1, 8.1, 1H); 7.33 (ddd, J=0.8, 7.2, 8.0, 1H); 4.31 (t, J=6.6, 2H); 2.74 (m, 1H); 2.37 (d, J=2.3, 3H); 1.81 (sxt, J=7.5, 2H); 1.03 (m, 4H).
Example 1.862 (CDCl3): 10.89 (br s, 1H); 8.14 (s, 1H); 7.79 (s, 1H); 4.06 (s, 3H); 3.20 (s, 3H); 2.28 (s, 3H); 2.25 (s, 3H).
Example 1.863 (CDCl3): 10.91 (br s, 1H); 8.13 (s, 1H); 7.78 (s, 1H); 4.43 (q, J=7.1, 2H); 3.18 (s, 3H); 2.27 (s, 3H); 2.24 (s, 3H); 1.41 (t, J=7.1, 3H).
Example 1.864 (CDCl3): 10.90 (br s, 1H); 8.12 (s, 1H); 7.78 (s, 1H); 4.31 (t, J=6.6, 2H); 3.19 (s, 3H); 2.26 (s, 3H); 2.24 (s, 3H); 1.79 (sxt, J=7.4, 2H); 0.97 (t, J=7.4, 3H).
Example 1.865 (CDCl3): 10.94 (br s, 1H); 8.14 (s, 1H); 7.79 (s, 1H); 5.14 (spt, J=6.2, 1H); 3.16 (s, 3H); 2.27 (s, 3H); 2.25 (s, 3H); 1.39 (d, J=6.2, 6H).
Example 1.866 (CDCl3): 10.91 (br s, 1H); 8.13 (s, 1H); 7.78 (s, 1H); 4.04 (s, 3H); 2.72 (m, 1H); 2.26 (s, 3H); 2.24 (s, 3H); 1.01 (m, 4H).
Example 1.867 (CDCl3): 10.94 (br s, 1H); 8.12 (s, 1H); 7.78 (s, 1H); 4.41 (q, J=7.1, 2H); 2.72 (m, 1H); 2.26 (s, 3H); 2.24 (s, 3H); 1.41 (t, J=7.1, 3H); 1.01 (m, 4H).
Example 1.868 (CDCl3): 10.93 (br s, 1H); 8.12 (s, 1H); 7.78 (s, 1H); 4.30 (t, J=6.6, 2H); 2.73 (m, 1H); 2.26 (s, 3H); 2.24 (s, 3H); 1.80 (sxt, J=7.3, 2H); 1.01 (m, 4H); 0.99 (t, J=7.4, 3H).
Example 1.869 (CDCl3): 10.99 (br s, 1H); 8.32 (d, J=8.6, 1H); 8.04 (d, J=2.1, 1H); 7.51 (dd, J=2.1, 8.6, 1H); 4.07 (s, 3H); 3.21 (s, 3H).
Example 1.870 (CDCl3): 11.02 (br s, 1H); 8.31 (d, J=8.6, 1H); 8.04 (d, J=2.1, 1H); 7.51 (dd, J=2.0, 8.6, 1H); 4.45 (q, J=7.1, 2H); 3.20 (s, 3H); 1.43 (t, J=7.1, 3H).
Example 1.871 (CDCl3): 11.03 (br s, 1H); 8.31 (d, J=8.6, 1H); 8.04 (d, J=2.0, 1H); 7.51 (dd, J=2.1, 8.6, 1H); 4.34 (t, J=6.7, 2H); 3.21 (s, 3H); 1.81 (sxt, J=7.5, 2H); 0.99 (t, J=7.4, 3H).
Example 1.872 (CDCl3): 11.08 (br s, 1H); 8.31 (d, J=8.6, 1H); 8.04 (d, J=2.0, 1H); 7.51 (dd, J=2.1, 8.6, 1H); 5.16 (spt, J=6.2, 1H); 3.18 (s, 3H); 1.39 (d, J=6.2, 6H).
Example 1.873 (CDCl3): 11.02 (br s, 1H); 8.29 (d, J=8.6, 1H); 8.02 (d, J=1.9, 1H); 7.50 (dd, J=2.0, 8.6, 1H); 4.05 (s, 3H); 2.73 (m, 1H); 1.02 (m, 4H).
Example 1.874 (CDCl3): 11.06 (br s, 1H); 8.30 (d, J=8.6, 1H); 8.03 (d, J=2.1, 1H); 7.50 (dd, J=2.1, 8.6, 1H); 4.43 (q, J=7.1, 2H); 2.74 (m, 1H); 1.43 (t, J=7.1, 3H); 1.03 (m, 4H).
Example 1.875 (CDCl3): 11.05 (br s, 1H); 8.30 (d, J=8.6, 1H); 8.03 (d, J=2.1, 1H); 7.50 (dd, J=2.1, 8.6, 1H); 4.32 (t, J=6.5, 2H); 2.74 (m, 1H); 1.81 (sxt, J=7.4, 2H); 1.03 (m, 4H); 1.00 (t, J=7.4, 3H).
Example 1.876 (CDCl3): 10.93 (br s, 1H); 8.28 (d, J=8.2, 1H); 7.85 (d, J=1.2, 1H); 7.32 (br d, J=8.2, 1H); 4.06 (s, 3H); 3.20 (s, 3H); 2.58 (t, J=7.4, 2H); 1.49 (sxt, J=7.4, 2H); 0.95 (t, J=7.4, 3H).
Example 1.877 (CDCl3): 10.94 (br s, 1H); 8.28 (d, J=8.2, 1H); 7.85 (d, J=1.7, 1H); 7.32 (dd, J=1.7, 8.1, 1H); 4.44 (q, J=7.1, 2H); 3.19 (s, 3H); 2.57 (t, J=7.4, 2H); 1.64 (sxt, J=7.3, 2H); 1.42 (t, J=7.1, 3H); 0.95 (t, J=7.3, 3H).
Example 1.878 (CDCl3): 10.96 (br s, 1H); 8.27 (d, J=8.2, 1H); 7.85 (br s, 1H); 7.32 (br d, J=8.2, 1H); 4.33 (t, J=6.7, 2H); 3.19 (s, 3H); 2.57 (t, J=7.3, 2H); 1.80 (sxt, J=7.3, 2H); 1.63 (sxt, J=7.4, 2H); 0.98 (t, J=7.4, 3H); 0.94 (t, J=7.3, 3H).
Example 1.879 (CDCl3): 10.98 (br s, 1H); 8.27 (d, J=8.2, 1H); 7.85 (d, J=1.7, 1H); 7.31 (1.7, 8.2, 1H); 5.14 (spt, J=6.2, 1H); 3.16 (s, 3H); 2.57 (t, J=7.5, 2H); 1.63 (sxt, J=7.4, 2H); 1.38 (d, J=6.2, 6H); 0.94 (t, J=7.3, 3H).
Example 1.880 (CDCl3): 10.96 (br s, 1H); 8.28 (d, J=8.2, 1H); 7.85 (br s, 1H); 7.32 (br d, J=8.2, 1H); 4.05 (s, 3H); 2.73 (m, 1H); 2.57 (t, J=7.4, 2H); 1.64 (sxt, J=7.4, 2H); 1.02 (m, 4H); 0.95 (t, J=7.3, 3H).
Example 1.881 (CDCl3): 10.99 (br s, 1H); 8.27 (d, J=8.2, 1H); 7.85 (d, J=1.7, 1H); 7.31 (dd, J=1.7, 8.2, 1H); 4.42 (q, J=7.1, 2H); 2.73 (m, 1H); 2.57 (t, J=7.4, 2H); 1.63 (sxt, J=7.4, 2H); 1.42 (t, J=7.1, 3H); 1.02 (m, 4H); 0.94 (t, J=7.3, 3H).
Example 1.882 (CDCl3): 10.98 (br s, 1H); 8.27 (d, J=8.2, 1H); 7.85 (d, J=1.7, 1H); 7.31 (dd, J=1.7, 8.2, 1H); 4.31 (t, J=6.6, 2H); 2.74 (m, 1H); 2.57 (t, J=7.4, 2H); 1.80 (sxt, J=7.4, 2H); 1.63 (sxt, J=7.4, 2H); 1.02 (m, 4H); 0.99 (t, J=7.4, 3H); 0.94 (t, J=7.3, 3H).
Example 1.883 (CDCl3): 10.96 (br s, 1H); 8.28 (d, J=8.2, 1H); 7.85 (d, J=1.6, 1H); 7.32 (dd, J=1.7, 8.2, 1H); 4.44 (q, J=7.1, 2H); 3.19 (s, 3H); 2.60 (t, J=7.6, 2H); 1.58 (m, 2H); 1.42 (t, J=7.1, 3H); 1.35 (sxt, J=7.5, 2H); 0.93 (t, J=7.3, 3H).
Example 1.884 (CDCl3): 10.95 (br s, 1H); 8.27 (d, J=8.2, 1H); 7.85 (d, J=1.6, 1H); 7.32 (dd, J=1.7, 8.2, 1H); 4.33 (t, J=6.6, 2H); 3.20 (s, 3H); 2.59 (t, J=7.7, 2H); 1.80 (sxt, J=7.4, 2H); 1.58 (sxt, J=7.5, 2H); 1.35 (sxt, J=7.4, 2H); 0.98 (t, J=7.4, 3H); 0.93 (t, J=7.3, 3H).
Example 1.885 (CDCl3): 10.92 (br s, 1H); 8.26 (d, J=8.2, 1H); 7.85 (d, J=1.6, 1H); 7.31 (dd, J=1.7, 8.2, 1H); 4.05 (s, 3H); 3.19 (s, 3H); 2.59 (t, J=7.7, 2H); 1.58 (m, 2H); 1.34 (sxt, J=7.4, 2H); 0.92 (t, J=7.3, 3H).
Example 1.886 (CDCl3): 10.95 (br s, 1H); 8.26 (d, J=8.2, 1H); 7.84 (d, J=1.7, 1H); 7.31 (dd, J=1.7, 8.2, 1H); 4.04 (s, 3H); 2.73 (m, 1H); 2.59 (t, J=7.7, 2H); 1.57 (m, 2H); 1.34 (sxt, J=7.4, 2H); 1.01 (m, 4H); 0.92 (t, J=7.3, 3H).
Example 1.887 (CDCl3): 10.98 (br s, 1H); 8.26 (d, J=8.2, 1H); 7.85 (d, J=1.6, 1H); 7.31 (dd, J=1.7, 8.2, 1H); 4.42 (q, J=7.1, 2H); 2.73 (m, 2H); 2.59 (t, J=7.7, 2H); 1.58 (m, 2H); 1.41 (t, J=7.1, 3H); 1.34 (sxt, J=7.4, 2H); 1.02 (m, 4H); 0.92 (t, J=7.3, 3H).
Example 1.888 (CDCl3): 10.99 (br s, 1H); 8.27 (d, J=8.2, 1H); 7.85 (d, J=1H); 7.31 (dd, J=1.7, 8.2, 1H); 4.31 (t, J=6.6, 2H); 2.74 (m, 2H); 2.59 (t, J=7.7, 2H); 1.81 (sxt, J=7.5, 2H); 1.58 (m, 2H); 1.35 (sxt, J=7.4, 2H); 1.03 (m, 4H); 1.00 (t, J=7.4, 3H); 0.93 (t, J=7.3, 3H).
Example 1.889 (CDCl3): 10.97 (br s, 1H); 8.26 (d, J=8.2, 1H); 7.85 (d, J=1.6, 1H); 7.31 (dd, J=1.6, 8.2, 1H); 5.13 (spt, J=6.1, 1H); 3.16 (s, 3H); 2.59 (t, J=7.6, 2H); 1.57 (m, 2H); 1.38 (d, J=6.2, 6H); 1.34 (m, 2H); 0.92 (t, J=7.3, 3H).
Example 1.890 (CDCl3): 11.11 (br s, 1H); 8.51 (dd, J=0.5, 8.3, 1H); 8.26 (d, J=0.8, 1H); 7.80 (ddd, J=0.6, 1.7, 8.3, 1H); 4.45 (q, J=7.1, 2H); 3.21 (s, 3H); 1.42 (t, J=7.1, 3H).
Example 1.891 (CDCl3): 11.14 (br s, 1H); 8.51 (d, J=8.3, 1H); 8.26 (d, J=1.0, 1H); 7.79 (dd, J=1.2, 8.3, 1H); 4.43 (q, J=7.1, 2H); 2.75 (m, 1H); 1.43 (t, J=7.1, 3H); 1.04 (m, 4H).
Example 1.892 (CDCl3): 11.34 (br s, 1H); 8.50 (dd, J=0.6, 8.3, 1H); 8.25 (d, J=1.2, 1H); 7.79 (ddd, J=0.6, 1.8, 8.4, 1H); 2.88 (m, 1H); 1.91 (m, 1H); 1.13 (m, 8H).
Example 1.893 (CDCl3): 11.10 (br s, 1H); 8.51 (d, J=8.3, 1H); 8.26 (br s, 1H); 7.80 (br d, J=8.3, 1H); 4.07 (s, 3H); 3.21 (s, 3H).
Example 1.894 (CDCl3): 11.14 (br s, 1H); 8.50 (d, J=8.3, 1H); 8.26 (br s, 1H); 7.79 (br d, J=8.3, 1H); 4.33 (t, J=6.7, 2H); 3.21 (s, 3H); 1.80 (sxt, J=6.9, 2H); 0.98 (t, J=7.4, 3H).
Example 1.895 (CDCl3): 11.15 (br s, 1H); 8.50 (d, J=8.3, 1H); 8.26 (d, J=1.0, 1H); 7.79 (dd, J=1.2, 8.3, 1H); 5.15 (spt, J=6.2, H); 3.18 (s, 3H); 1.39 (d, J=6.2, 6H).
Example 1.896 (CDCl3): 11.12 (br s, 1H); 8.49 (d, J=8.3, 1H); 8.25 (br s, 1H); 7.79 (br d, J=8.3, 1H); 4.05 (s, 3H); 2.74 (m, 1H); 1.03 (m, 4H).
Example 1.897 (CDCl3): 11.15 (br s, 1H); 8.49 (d, J=8.3, 1H); 8.25 (br s, 1H); 7.78 (br d, J=8.4, 1H); 4.31 (t, J=6.5, 2H); 2.75 (m, 1H); 1.81 (sxt, J=6.6, 2H); 1.01 (m, 4H); 0.99 (t, J=7.4, 3H).







TABLE 2







Compounds of the general formula (II*)









(II*)








 









Z*
















R
R1
a
b
c
d
e
f



















2.001 a-f
F
—
*
*






2.002 a-f
Br
—


2.003 a-f
I
—


2.004 a-f
CH3
—
*
*


2.005 a-f
CH3
5-CH3


2.006 a-f
CH2CH3
—


2.007 a-f
(CH2)2CH3
—


2.008 a-f
CH(CH3)2
—


2.009 a-f
(CH2)3CH3
—


2.010 a-f
CH(CH3)CH2CH3
—


2.011 a-f
CH2CH(CH3)2
—


2.012 a-f
C(CH3)3
—


2.013 a-f
CH═CH2
—


2.014 a-f
C(CH3)CH2
—


2.015 a-f
C≡CH
—


2.016 a-f
C≡CCH3
—


2.017 a-f
C≡CCH2CH3
—


2.018 a-f
CH2CHCH2
—


2.019 a-f
CH2C(CH3)CH2
—


2.020 a-f
CH2C≡CH
—


2.021 a-f
CH2C≡CCH3
—


2.022 a-f
CH2C≡CCH2CH3
—


2.023 a-f
Cyclopropyl
—


2.024 a-f
2,2-di-F-cyclopropyl
—


2.025 a-f
2,2-di-Cl-cyclopropyl
—


2.026 a-f
2,2-di-CH3-cyclopropyl
—


2.027 a-f
Cyclobutyl
—


2.028 a-f
Cyclopentyl
—


2.029 a-f
Cyclohexyl
—


2.030 a-f
CH2cyclopropyl
—


2.031 a-f
CH2cyclobutyl
—


2.032 a-f
CH2cyclopentyl
—


2.033 a-f
CH2cyclohexyl
—


2.034 a-f
CH2CCH3
—


2.035 a-f
CH2CCH2CH3
—


2.036 a-f
CH(CH3)OCH3
—


2.037 a-f
Ph
—


2.038 a-f
2-F-Ph
—


2.039 a-f
3-F-Ph
—


2.040 a-f
4-F-Ph
—


2.041 a-f
2,6-di-F-Ph
—


2.042 a-f
2,4-di-F-Ph
—


2.043 a-f
2-Cl-Ph
—


2.044 a-f
3-Cl-Ph
—


2.045 a-f
4-Cl-Ph
—


2.046 a-f
2,6-di-Cl-Ph
—


2.047 a-f
2,4-di-Cl-Ph
—


2.048 a-f
2-MeO-Ph
—


2.049 a-f
3-MeO-Ph
—


2.050 a-f
4-MeO-Ph
—


2.051 a-f
2,4-di-MeO-Ph
—


2.052 a-f
2-Me-Ph
—


2.053 a-f
3-Me-Ph
—


2.054 a-f
4-Me-Ph
—


2.055 a-f
2-CF3-Ph
—


2.056 a-f
3-CF3-Ph
—


2.057 a-f
4-CF3-Ph
—


2.058 a-f
CH2Ph
—


2.059 a-f
CH2-2-F-Ph
—


2.060 a-f
CH2-2,4-di-F-Ph
—


2.061 a-f
CH2-2-MeO-Ph
—


2.062 a-f
CH2-3-MeO-Ph
—


2.063 a-f
CF3
—
*
*


2.064 a-f
CF3
5-CH3


2.065 a-f
CHF2
—


2.066 a-f
CH2F
—


2.067 a-f
CH2CF3
—


2.068 a-f
CH2CHF2
—


2.069 a-f
CH2CH2F
—


2.070 a-f
CF═CH2
—


2.071 a-f
CH═CF2
—


2.072 a-f
CF2CH═CH2
—


2.073 a-f
CH═CH—CF3
—


2.074 a-f
CHFCH═CH2
—


2.075 a-f
CN
—


2.076 a-f
NO2
—


2.077 a-f
NH2
—


2.078 a-f
NHCH3
—


2.079 a-f
N(CH3)2
—


2.080 a-f
N(CH3)CH2CH═CH2
—


2.081 a-f
N(CH3)CH2C≡CH
—


2.082 a-f
NH-cyclopropyl
—


2.083 a-f
N(CH3)-cyclopropyl
—


2.084 a-f
N(CH2CH3)-cyclopropyl
—


2.085 a-f
NHC(O)H
—


2.086 a-f
NHC(O)CH3
—


2.087 a-f
NHC(O)OCH3
—


2.088 a-f
NHSO2CH3
—


2.089 a-f
NHSO2CF3
—


2.090 a-f
NHSO2CHF2
—


2.091 a-f
NHSO2CH2F
—


2.092 a-f
OCH3
—
*
*


2.093 a-f
OCH3
5-CH3


2.094 a-f
OCH2CH3
—
*


2.095 a-f
O(CH2)2CH3
—
*


2.096 a-f
OCH(CH3)2
—
*


2.097 a-f
OCH(CH3)2
5-CH3


2.098 a-f
O(CH2)3CH3
—


2.099 a-f
OCH(CH3)CH2CH3
—


2.100 a-f
OCH2CH(CH3)2
—


2.101 a-f
OC(CH3)3
—


2.102 a-f
OCH═CH2
—


2.103 a-f
OC(CH3)═CH2
—


2.104 a-f
OCH═CH(CH3)
—


2.105 a-f
OCH═C(CH3)2
—


2.106 a-f
OC(CH3)═CHCH3
—


2.107 a-f
OC(CH3)═C(CH3)2
—


2.108 a-f
OC≡CH
—


2.109 a-f
OC≡CCH3
—


2.110 a-f
OC≡CCH2CH3
—


2.111 a-f
OCH2CH═CH2
—


2.112 a-f
OCH2C(CH3)═CH2
—


2.113 a-f
OCH2CH═CHCH3
—


2.114 a-f
OCH2CH═C(CH3)2
—


2.115 a-f
OCH2C(CH3)═CHCH3
—


2.116 a-f
OCH2C(CH3)═C(CH3)2
—


2.117 a-f
OCH(CH3)CH═CH2
—


2.118 a-f
OCH2C≡CH
—


2.119 a-f
OCH2C≡CCH3
—


2.120 a-f
OCH2C≡CCH2CH3
—


2.121 a-f
OCH(CH3)C≡CH
—


2.122 a-f
O-cyclopropyl
—


2.123 a-f
O-2,2-di-Cl-cyclopropyl
—


2.124 a-f
O-2,2-di-F-cyclopropyl
—


2.125 a-f
O-cyclobutyl
—


2.126 a-f
O-cyclopentyl
—


2.127 a-f
O-cyclohexyl
—


2.128 a-f
OCH2-cyclopropyl
—
*


2.129 a-f
OCH2-cyclopropyl
5-CH3


2.130 a-f
OCH(CH3)-cyclopropyl
—


2.131 a-f
OCH2-2-Me-cyclopropyl
—


2.132 a-f
OCH2-2,2-di-Me-cyclopropyl
—


2.133 a-f
OCH2-2,2-di-Cl-cyclopropyl
—


2.134 a-f
OCH2-2,2-di-F-cyclopropyl
—


2.135 a-f
OCH2-cyclobutyl
—


2.136 a-f
OCH2-cyclopentyl
—


2.137 a-f
OCH(CH3)-cyclopentyl
—


2.138 a-f
OCH2-cyclohexyl
—


2.139 a-f
OCH(CH3)-cyclohexyl
—


2.140 a-f
OCH2CCH3
—


2.141 a-f
O(CH2)2OCH3
—


2.142 a-f
OCH2CCH2CH3
—


2.143 a-f
O(CH2)2OCH2CH3
—


2.144 a-f
OCH(CH3)OCH3
—


2.145 a-f
OPh
—


2.146 a-f
O-2-F-Ph
—


2.147 a-f
O-3-F-Ph
—


2.148 a-f
O-4-F-Ph
—


2.149 a-f
O-2,6-di-F-Ph
—


2.150 a-f
O-2,4-di-F-Ph
—


2.151 a-f
O-2-Cl-Ph
—


2.152 a-f
O-3-Cl-Ph
—


2.153 a-f
O-4-Cl-Ph
—


2.154 a-f
O-2,6-di-Cl-Ph
—


2.155 a-f
O-2,4-di-Cl-Ph
—


2.156 a-f
O-2-CF3-Ph
—


2.157 a-f
O-3-CF3-Ph
—


2.158 a-f
O-4-CF3-Ph
—


2.159 a-f
O-2-MeO-Ph
—


2.160 a-f
O-3-MeO-Ph
—


2.161 a-f
O-4-MeO-Ph
—


2.162 a-f
O-2,4-di-MeO-Ph
—


2.163 a-f
O-2-Me-Ph
—


2.164 a-f
O-3-Me-Ph
—


2.165 a-f
O-4-Me-Ph
—


2.166 a-f
OCH2Ph
—


2.167 a-f
OCH(CH3)Ph
—


2.168 a-f
OCH2-2-F-Ph
—


2.169 a-f
OCH2-3-F-Ph
—


2.170 a-f
OCH2-4-F-Ph
—


2.171 a-f
OCH2-2,4-di-F-Ph
—


2.172 a-f
OCH2-2-Cl-Ph
—


2.173 a-f
OCH2-3-Cl-Ph
—


2.174 a-f
OCH2-4-Cl-Ph
—


2.175 a-f
OCH2-2,4-di-Cl-Ph
—


2.176 a-f
OCH2-2-MeO-Ph
—


2.177 a-f
OCH2-3-MeO-Ph
—


2.178 a-f
OCH2-4-MeO-Ph
—


2.179 a-f
OCH2-2-CF3-Ph
—


2.180 a-f
OCH2-3-CF3-Ph
—


2.181 a-f
OCH2-4-CF3-Ph
—


2.182 a-f
OCF3
—
*
*


2.183 a-f
OCF3
5-CH3


2.184 a-f
OCHF2
—
*


2.185 a-f
OCHF2
5-CH3


2.186 a-f
OCH2CF3
—
*


2.187 a-f
OCH2CHF2
—
*


2.188 a-f
OCH2CH2F
—


2.189 a-f
OCH(CH3)CF3
—
*


2.190 a-f
OCH(CH3)CHF2
—


2.191 a-f
OCH(CH3)CH2F
—


2.192 a-f
OCH2CF2CF3
—
*


2.193 a-f
OCH2CF2CHF2
—


2.194 a-f
OCH2CF2CH2F
—


2.195 a-f
OCH(CH3)CF2CF3
—


2.196 a-f
OCH(CH3)CF2CHF2
—


2.197 a-f
OCH(CH3)CF2CH2F
—


2.198 a-f
OCH2CHFCF3
—


2.199 a-f
O(CH2)2CF3
—


2.200 a-f
O(CH2)2CHF2
—


2.201 a-f
O(CH2)3CF3
—


2.202 a-f
O(CH2)3CHF2
—


2.203 a-f
OCF═CH2
—


2.204 a-f
OCH═CF2
—


2.205 a-f
OCF2CH═CH2
—


2.206 a-f
OCHFCH═CH2
—


2.207 a-f
OCH═CHCF3
—


2.208 a-f
SCH3
—
*
*


2.209 a-f
SCH2CH3
—


2.210 a-f
S(CH2)2CH3
—


2.211 a-f
SCH(CH3)2
—


2.212 a-f
SC(CH3)3
—


2.213 a-f
SCH2Ph
—


2.214 a-f
SPh
—


2.215 a-f
SCF3
—


2.216 a-f
SCHF2
—


2.217 a-f
SCH2F
—


2.218 a-f
SCH═CH2
—


2.219 a-f
SCH2CH═CH2
—


2.220 a-f
SC≡CH
—


2.221 a-f
SCH2C≡CH
—


2.222 a-f
S-cyclopropyl
—


2.223 a-f
SCH2-cyclopropyl
—


2.224 a-f
SF5
—


2.225 a-f
S(O)CH3
—


2.226 a-f
S(O)CH2CH3
—


2.227 a-f
S(O)(CH2)2CH3
—


2.228 a-f
S(O)CH(CH3)2
—


2.229 a-f
S(O)C(CH3)3
—


2.230 a-f
S(O)CH2Ph
—


2.231 a-f
S(O)Ph
—


2.232 a-f
S(O)CF3
—


2.233 a-f
S(O)CHF2
—


2.234 a-f
S(O)CH2F
—


2.235 a-f
S(O)CH═CH2
—


2.236 a-f
S(O)CH2CH═CH2
—


2.237 a-f
S(O)C≡CH
—


2.238 a-f
S(O)CH2C≡CH
—


2.239 a-f
S(O)-cyclopropyl
—


2.240 a-f
S(O)CH2-cyclopropyl
—


2.241 a-f
SO2CH3
—


2.242 a-f
SO2CH2CH3
—


2.243 a-f
SO2(CH2)2CH3
—


2.244 a-f
SO2CH(CH3)2
—


2.245 a-f
SO2C(CH3)3
—


2.246 a-f
SO2CH2Ph
—


2.247 a-f
SO2Ph
—


2.248 a-f
SO2CF3
—


2.249 a-f
SO2CHF2
—


2.250 a-f
SO2CH2F
—


2.251 a-f
SO2CH═CH2
—


2.252 a-f
SO2OH2CH═CH2
—


2.253 a-f
SO2C≡CH
—


2.254 a-f
SO2CH2C≡CH
—


2.255 a-f
SO2-cyclopropyl
—


2.256 a-f
SO2CH2-cyclopropyl
—


2.257 a-f
SO2NHCH3
—


2.258 a-f
SO2N(CH3)2
—


2.259 a-f
OSO2CH3
—
*


2.260 a-f
OSO2CH3
5-CH3


2.261 a-f
OSO2CH2CH3
—


2.262 a-f
OSO2CH(CH3)2
—


2.263 a-f
OSO2C(CH3)3
—


2.264 a-f
OSO2CH2Ph
—


2.265 a-f
OSO2CF3
—


2.266 a-f
OSO2CHF2
—


2.267 a-f
OSO2CH2F
—


2.268 a-f
OSO2CH2CF3
—


2.269 a-f
OSO2CH2CHF2
—


2.270 a-f
OSO2(CH2)2F
—


2.271 a-f
OSO2CH═CH2
—


2.272 a-f
OSO2CH2CH═CH2
—


2.273 a-f
OSO2C≡CH
—


2.274 a-f
OSO2CH2C≡CH
—


2.275 a-f
OSO2-cyclopropyl
—


2.276 a-f
OSO2CH2-cyclopropyl
—


2.277 a-f
OSO2CH2CN
—


2.278 a-f
OSO2NHCH3
—


2.279 a-f
OSO2N(CH3)2
—
*


2.280 a-f
OSO2NHCH2CH═CH2
—


2.281 a-f
OSO2NHCH2C≡CH
—


2.282 a-f
OSO2NHCF3
—


2.283 a-f
OSO2NHCHF2
—


2.284 a-f
OSO2NHCH2F
—


2.285 a-f
OC(O)H
—


2.286 a-f
OC(O)CH3
—


2.287 a-f
OC(O)CH2CH3
—


2.288 a-f
OC(O)OCH3
—


2.289 a-f
OC(O)OCH2CH3
—


2.290 a-f
OC(O)NH2
—


2.291 a-f
OC(O)NHCH3
—


2.292 a-f
OC(O)N(CH3)2
—


2.293 a-f
OC(O)N(CH2CH3)2
—


2.294 a-f
Si(CH3)3
—


2.295 a-f
2-thienyl
—


2.296 a-f
3-thienyl
—


2.297 a-f
2-pyridyl
—


2.298 a-f
3-pyridyl
—


2.299 a-f
4-pyridyl
—


2.300 a-f
OH
—
*


2.301 a-f
H
3-Cl
*
*


2.302 a-f
H
3-Cl, 6-Cl
*
*


2.303 a-f
H
4-Cl, 6-Cl
*
*


2.304 a-f
H
5-CF3
*
*


2.305 a-f
H
4-CF3, 6-Cl
*
*


2.306 a-f
H
3-F, 4-CH3
*
*


2.307 a-f
H
4-(CH2)2CH3
*
*


2.308 a-f
H
4-CH(CH3)2
*
*


2.309 a-f
H
4-(CH2)3CH3
*
*


2.310 a-f
H
4-C(CH3)3
*
*


2.311 a-f
H
4-CH2CH3
*
*





Compounds a: Z* = NH2


Compounds b: Z* = NH-tert-butyl


Compounds c: z ̃ = NH-C(O)Ophenyl


Compounds d: Z* = NH-C(S)Ophenyl


Compounds e: Z* = NCO


Compounds f: Z* = NCS






1H NMR data for compounds of table 2:
Example: 2.001a (d6-DMSO): 7.96 (dt, J=0.9, 7.8, 1H); 7.78 (br s, 2H); 7.43 (ddd, J=1.1, 8.3, 11.2, 1H); 7.28 (dt, J=5.4, 8.0, 1H).
Example: 2.004a (d6-DMSO): 7.89 (br d, J=7.8, 1H); 7.55 (td, J=0.9, 7.6, 1H); 7.49 (br s, 2H); 7.40 (td, J=1.2, 7.9, 1H), 3.34 (s, 3H).
Example: 2.063a (d6-DMSO): 8.48 (dd, J=1.0, 7.9, 1H); 7.95 (dd, J=1.0, 8.0, 1H); 7.74 (br s, 2H); 7.39 (br t, J=8.3, 1H).
Example: 2.092a (d6-DMSO): 7.70 (dd, J=1.1, 7.7, 1H); 7.25 (dd, J=0.9, 8.4, 1H); 7.20 (br s, 2H); 7.17 (t, J=7.9, 1H); 3.90 (s, 3H).
Example: 2.094a (d6-DMSO): 7.70 (dd, J=1.0, 7.8, 1H); 7.26 (br d, J=8.4, 1H); 7.15 (t, J=8.0, 1H); 7.03 (br s, 2H); 4.23 (q, J=7.0, 2H); 1.37 (t, J=6.9, 3H).
Example: 2.095a (d6-DMSO): 7.70 (dd, J=1.0, 7.8, 1H); 7.26 (dd, J=0.9, 8.4, 1H); 7.15 (t, J=7.9, 1H); 6.98 (br s, 2H); 4.12 (t, J=6.6, 2H); 1.80 (m, 2H); 0.96 (t, J=7.4, 3H).
Example: 2.096a (d6-DMSO): 7.69 (dd, J=1.0, 1H); 7.29 (br d, J=8.1, 1H); 7.14 (t, J=8.0, 1H); 6.91 (br s, 2H); 4.82 (m, 1H); 1.34 (d, J=6.0, 6H).
Example: 2.128a (d6-DMSO): 7.71 (dd, J=1.1, 7.8, 1H); 7.27 (dd, J=1.1, 8.4, 1H); 7.15 (t, J=7.8, 1H); 7.01 (br s, 2H); 4.04 (d, J=7.2, 2H); 1.33 (m, 1H); 0.56 (m, 2H); 0.36 (m, 2H).
Example: 2.182a (d6-DMSO): 8.19 (dd, J=1.1, 7.9, 1H); 7.67 (br s, 2H); 7.55 (dt, J=1.3, 8.3, 1H); 7.34 (t, J=8.1, 1H).
Example: 2.184a (CDCl3): 7.96 (dd, J=1.2, 8.0, 1H); 7.25 (m, 1H); 7.07 (t, J=8.1, 1H); 6.51 (t, J=73.8, 1H); 6.37 (br s, 2H).
Example: 2.186a (d6-DMSO): 7.84 (dd, J=0.9, 7.9, 1H); 7.40 (br d, J=8.2, 1H); 7.23 (t, J=8.0, 1H); 7.07 (br s, 2H); 4.99 (q, J=8.8, 2H).
Example: 2.187a (d6-DMSO): 7.79 (dd, J=1.0, 7.8, 1H); 7.35 (dd, J=0.8, 8.4, 1H); 7.20 (t, J=7.9, 1H); 7.10 (br s, 2H); 6.53 (tt, J=3.7, 54.7, 1H); 4.51 (td, J=3.7, 14.3, 2H).
Example: 2.189a (d6-DMSO): 7.83 (dd, J=0.8, 7.9, 1H); 7.46 (br d, J=8.3, 1H); 7.22 (t, J=8.1, 1H); 6.91 (br s, 2H); 5.50 (m, 1H); 1.48 (d, J=6.4, 3H).
Example: 2.192a (d6-DMSO): 7.85 (dd, J=1.0, 7.9, 1H); 7.42 (br d, J=8.3, 1H); 7.24 (t, J=8.0, 1H); 7.00 (br s, 2H); 5.07 (t, J=13.9, 2H).
Example: 2.208a (d6-DMSO): 7.95 (dd, J=0.9, 7.7, 1H); 7.46 (m, 3H); 7.12 (t, J=7.9, 1H); 2.41 (s, 3H).
Example: 2.259a (d6-DMSO): 8.13 (dd, J=1.2, 7.9, 1H); 7.60 (br s, 2H); 7.53 (dd, J=1.2, 8.2, 1H); 7.31 (t, J=8.0, 1H); 3.53 (s, 3H).
Example: 2.279a (d6-DMSO): 8.07 (dd, J=1.2, 7.9, 1H); 7.52 (dd, J=1.2, 8.2, 1H); 7.19 (t, J=8.1, 1H); 5.48 (br s, 2H); 3.10 (s, 6H).
Example 2.301a (CDCl3): 7.97 (m, 1H); 7.52 (m, 1H); 7.35 (m, 1H); 6.91 (br s, 2H).
Example 2.302a (CDCl3): 7.58 (d, J=8.6, 1H); 7.50 (d, J=8.6, 1H); 5.49 (br s, 2H).
Example 2.303a (CDCl3): 8.15 (d, J=2.1, 1H); 7.57 (d, J=2.1, 1H); 5.36 (br s, 2H).
Example 2.304a (CDCl3): 8.43 (br d, J=1.9, 1H); 8.22 (dd, J=0.5, 8.2, 1H); 7.47 (ddd, J=0.6, 2.2, 8.2, 1H); 5.21 (br s, 2H).
Example 2.305a (CDCl3): 8.35 (dd, J=0.8, 1.8, 1H); 7.81 (dd, J=0.5, 1.8, 1H); 5.43 (br s, 2H).
Example 2.306a (CDCl3): 7.89 (dd, J=1.0, 8.1, 1H); 7.30 (m, 1H); 5.15 (br s, 2H); 2.39 (dd, J=0.5, 2.3, 3H).
Example 2.307a (CDCl3): 8.06 (d, J=8.1, 1H); 7.88 (br s, 1H); 7.28 (d, J=9.0, 1H); 5.17 (br s, 2H); 2.59 (t, J=7.4, 2H).
Example 2.308a (CDCl3): 8.08 (d, J=8.2, 1H); 7.91 (d, J=1.7, 1H); 7.34 (dd, J=1.8, 8.2, 1H); 5.21 (br s, 2H); 2.92 (spt, J=7.1, 1H); 1.26 (d, J=6.9, 6H).
Example 2.309a (CDCl3): 8.05 (d, J=8.0, 1H); 7.87 (br s, 1H); 7.27 (br d, J=7.3, 1H); 5.17 (br s, 2H); 2.60 (t, J=7.5, 2H); 1.59 (m, 2H); 1.34 (sxt, J=7.5, 2H); 0.92 (t, J=7.2, 3H).
Example 2.310a (d6-DMSO): 8.02 (d, J=1.9, 1H); 7.92 (d, J=8.3, 1H); 7.59 (dd, J=2.0, 8.4, 1H); 7.41 (br s, 2H); 1.28 (s, 9H).
Example 2.311a (d6-DMSO): 7.94 (m, 2H); 7.40 (m, 3H); 2.63 (q, J=7.6, 2H); 1.17 (t, J=7.5, 3H).
Example: 2.300a (CDCl3): 9.91 (s, 1H); 7.60 (m, 1H); 7.05 (m, 2H); 5.49 (br s, 2H).
Example 2.001 b (d6-DMSO): 7.99 (dt, J=0.7, 7.7, 1H); 7.79 (br s, 1H); 7.42 (ddd, J=1.1, 8.1, 11.0, 1H); 7.28 (td, J=5.1, 7.7, 1H); 1.13 (s, 9H).
Example 2.004b (d6-DMSO): 7.92 (dd, J=1.1, 7.7, 1H); 7.55 (m, 2H); 7.39 (m, 1H); 3.31 (s, 3H); 1.14 (s, 9H).
Example 2.063b (d6-DMSO): 8.49 (dd, J=1.1, 7.7, 1H); 7.97 (dd, J=1.1, 8.1, 1H); 7.78 (br s, 1H); 7.40 (td, J=0.7, 8.1, 1H); 1.07 (s, 9H).
Example 2.092b (CDCl3): 7.80 (m, 1H); 7.06 (m, 2H); 5.28 (br s, 1H); 3.99 (s, 3H); 1.22 (s, 9H).
Example 2.182b (CDCl3): 8.12 (dd, J=0.8, 8.0, 1H); 7.41 (dt, J=0.8, 8.0, 1H); 7.18 (t, J=8.0, 1H); 5.12 (br s, 1H); 1.27 (s, 9H).
Example 2.208b (CDCl3): 7.96 (dd, J=1.0, 7.5, 1H); 7.35 (dd, J=0.7, 8.5, 1H); 7.00 (t, J=7.8, 1H); 5.74 (br s, 1H); 2.47 (s, 3H); 1.25 (s, 9H).
Example 2.301b (CDCl3): 8.13 (dd, J=1.6, 7.9, 1H); 7.62 (dd, J=1.5, 8.0, 1H); 7.42 (t, J=7.9, 1H); 5.35 (br s, 1H); 1.23 (s, 9H).
Example 2.302b (CDCl3): 7.55 (d, J=9.0, 1H); 7.49 (d, J=9.0, 1H); 5.55 (br s, 1H); 1.28 (s, 9H).
Example 2.303b (CDCl3): 8.15 (d, J=2.2, 1H); 7.55 (d, J=2.2, 1H); 5.30 (br s, 2H); 1.27 (s, 9H).
Example 2.304b (CDCl3): 8.45 (br d, J=2.2, 1H); 8.19 (br d, J=8.1, 1H); 7.42 (m, 1H); 5.21 (br s, 1H); 1.24 (s, 9H).
Example 2.305b (CDCl3): 8.35 (dd, J=0.7, 1.8, 1H); 7.78 (dd, J=0.6, 1.9, 1H); 5.37 (s, 2H); 1.28 (s, 9H).
Example 2.306b (CDCl3): 7.91 (dd, J=1.0, 8.0, 1H); 7.28 (ddd, J=0.7, 7.2, 8.0, 1H); 5.18 (br s, 1H); 2.38 (dd, J=0.6, 2.3, 3H); 1.22 (s, 9H).
Example 2.307b (CDCl3): 8.09 (d, J=8.1, 1H); 7.85 (d, J=1.3, 1H); 7.27 (dd, J=1.2, 8.1, 1H); 5.14 (br s, 2H); 2.58 (t, J=7.4, 2H); 1.65 (sxt, J=7.5, 2H); 1.21 (s, 9H); 0.94 (t, J=7.3, 3H).
Example 2.308b (CDCl3): 8.10 (d, J=8.2, 1H); 7.87 (d, J=1.6, 1H); 7.31 (dd, J=1.7, 8.2, 1H); 5.15 (br s, 1H); 2.90 (spt, J=6.9, 1H); 1.25 (d, J=6.9, 6H); 1.22 (s, 9H).
Example 2.309b (CDCl3): 8.08 (d, J=8.1, 1H); 7.85 (d, J=1.7, 1H); 7.26 (dd, J=1.7, 8.1, 1H); 5.15 (br s, 1H); 2.60 (t, J=7.6, 2H); 1.60 (m, 2H); 1.34 (sxt, J=7.4, 2H); 1.21 (s, 9H); 0.93 (t, J=7.3, 3H).
Example 2.310b (CDCl3): 8.10 (d, J=8.3, 1H); 8.00 (d, J=1.8, 1H); 7.46 (dd, J=1.9, 8.4, 1H); 5.15 (br s, 1H); 1.32 (s, 9H); 1.22 (s, 9H).
Example 2.311b (CDCl3): 8.09 (d, J=8.1, 1H); 7.87 (br d, J=1.7, 1H); 7.29 (br dd, J=1.7, 8.1, 1H); 5.15 (br s, 1H); 2.65 (q, J=7.6, 2H); 1.25 (t, J=7.6, 3H); 1.22 (s, 9H).
B. Formulation Examples


    a) A dust is obtained by mixing 10 parts by weight of a compound of the formula (I) and/or salts thereof and 90 parts by weight of talc as inert substance and comminuting the mixture in a hammer mill.
    b) A wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of a compound of the formula (I) and/or salts thereof, 64 parts by weight of kaolin-containing quartz as inert substance, 10 parts by weight of potassium ligninsulfonate and 1 part by weight of sodium oleoylmethyltaurate as wetter and dispersant, and grinding the mixture in a pinned-disk mill.
    c) A readily water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of the formula (I) and/or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range for example about 255 to above 277° C.) and grinding the mixture in a ball mill to a fineness of below 5 microns.
    d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and/or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxethylated nonylphenol as emulsifier.
    e) Water-dispersible granules are obtained by mixing
    
        75 parts by weight of a compound of the formula (I) and/or salts thereof,
        10 parts by weight of calcium ligninsulfonate,
        5 parts by weight of sodium lauryl sulfate,
        3 parts by weight of polyvinyl alcohol and
        7 parts by weight of kaolin,
        grinding the mixture in a pinned-disk mill, and granulating the powder in a fluidized bed by spraying on Water as granulating liquid.
    
    
    f) Water-dispersible granules are also obtained by homogenizing and precomminuting
    
        25 parts by weight of a compound of the formula (I) and/or salts thereof,
        5 parts by weight of sodium 2,2′-dinaphthylmethane-6,6′-disulfonate,
        2 parts by weight of sodium oleoylmethyltaurate,
        1 part by weight of polyvinyl alcohol,
        17 parts by weight of calcium carbonate and
        50 parts by weight of water
        in a colloid mill, then grinding the mixture in a bead mill, and atomizing and drying the resulting suspension in a spraying tower, using a single-fluid nozzle.
    
    


C. Biological Examples
1. Pre-Emergence Effect on Weeds
Seeds or sections of rhizome from monocot and dicot broadleaf weed plants were laid out in sandy loam soil in cardboard pots, and covered with soil. The compounds of the invention, formulated as wettable powders or emulsifiable concentrates, were then applied, in the form of aqueous suspensions or emulsions, at various dosages, onto the surface of the covering earth, at an application rate of 600 to 800 l of water per hectare (converted).
Following the treatment, the pots were placed in a greenhouse and maintained under good growth conditions for the weeds. Visual scoring of the plant damage or emergence damage was made when the test plants had emerged, after a test time of 3 to 4 weeks, in comparison to untreated controls. As the results show, compounds of the invention feature good pre-emergence herbicidal activity against a broad spectrum of gramineous and broadleaf weeds. For example, compounds 1.001, 1.004, 1.005, 1.008, 1.011, 1.014, 1.021, 1.022, 1.023, 1.024, 1.027, 1.028, 1.037, 1.038, 1.039, 1.040, 1.042, 1.043, 1.044, 1.133, 1.136, 1.137, 1.138, 1.140, 1.143, 1.191, 1.194, 1.195, 1.196, 1.197, 1.198, 1.201, 1.204, 1.211, 1.214, 1.215, 1.218, 1.221, 1.231, 1.235, 1.236, 1.237, 1.238, 1.241, 1.244, 1.251, 1.254, 1.255, 1.256, 1.258, 1.261, 1.264, 1.273, 1.274, 1.275, 1.276, 1.278, 1.279, 1.280, 1.281, 1.286, 1.289, 1.290, 1.294, 1.295, 1.346, 1.349, 1.350, 1.353, 1.356, 1.359, 1.440, 1.443, 1.444, 1.447, 1.450, 1.453, 1.460, 1.463, 1.464, 1.465, 1.467, 1.470, 1.473, 1.481, 1.488, 1.501, 1.504, 1.505, 1.506, 1.508, 1.511, 1.514, 1.522, 1.525, 1.526, 1.527, 1.529, 1.532, 1.535, 1.544, 1.549, 1.550, 1.552, 1.555, 1.558, 1.579, 1.581, 1.582, 1.584, 1.585, 1.586, 1.711, 1.712, 1.713, 1.716, 1.717, 1.718, 1.749, 1.751, 1.752, 1.754, 1.755, 1.756, 1.815, 1.816, 1.817, 1.818, 1.819, 1.820, 1.821, 1.822, 1.823, 1.824, 1.825, 1.826, 1.827, 1.828, 1.829, 1.830, 1.831, 1.832, 1.833, 1.834, 1.835, 1.836, 1.837, 1.838, 1.839, 1.840, 1.841, 1.842, 1.843, 1.844, 1.845, 1.846, 1.847, 1.848, 1.849, 1.850, 1.851, 1.852, 1.853, 1.854, 1.855, 1.856, 1.857, 1.858, 1.859, 1.860, 1.861, 1.862, 1.863, 1.864, 1.865, 1.866, 1.867, 1.868, 1.869, 1.870, 1.871, 1.872, 1.873, 1.874, 1.875, 1.876, 1.877, 1.878, 1.879, 1.880, 1.881, 1.882, 1.883, 1.884, 1.885, 1.886, 1.887, 1.888, 1.889, 1.890, 1.891, 1.892, 1.893, 1.894, 1.895, 1.896, 1.997 and other compounds from table 1 have a very good herbidical action against weed plants such as Sinapis alba, Chrysanthemum segetum, Avena sativa, Stellaria media, Echinochloa crus-galli, Lolium multiflorum, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus and Panicum miliaceum when applied pre-emergence at a rate of 0.3 kg or less of active substance per hectare.
2. Post-Emergence Effect on Weeds
Seeds or sections of rhizome from monocot and dicot broadleaf weeds were made out in sandy loam soil in plastic pots, covered with soil, and cultivated in a greenhouse under good growth conditions. Three weeks after sowing, the test plants were treated at the three-leaf stage. The compounds of the invention, formulated as sprayable powders or as emulsion concentrates, were sprayed in different dosages onto the green parts of the plants, at an application rate of 600 to 800 l of water per hectare (converted). After the test plants had stood in the greenhouse under optimum growth conditions for a period of about 3 to 4 weeks, the effect of the products was scored visually in comparison to untreated controls. Post-emergence as well, the compositions of the invention exhibit good herbicidal activity against a broad spectrum of economically important gramineous and broadleaf weeds. For example, compounds 1.001, 1.004, 1.005, 1.008, 1.011, 1.014, 1.021, 1.022, 1.023, 1.024, 1.027, 1.028, 1.037, 1.038, 1.039, 1.040, 1.042, 1.043, 1.044, 1.133, 1.136, 1.137, 1.138, 1.140, 1.143, 1.191, 1.194, 1.195, 1.196, 1.197, 1.198, 1.201, 1.204, 1.211, 1.214, 1.215, 1.218, 1.221, 1.231, 1.235, 1.236, 1.237, 1.238, 1.241, 1.244, 1.251, 1.254, 1.255, 1.256, 1.258, 1.261, 1.264, 1.273, 1.274, 1.275, 1.276, 1.278, 1.279, 1.280, 1.281, 1.286, 1.289, 1.290, 1.294, 1.295, 1.346, 1.349, 1.350, 1.353, 1.356, 1.359, 1.440, 1.443, 1.444, 1.447, 1.450, 1.453, 1.460, 1.463, 1.464, 1.465, 1.467, 1.470, 1.473, 1.481, 1.488, 1.501, 1.504, 1.505, 1.506, 1.508, 1.511, 1.514, 1.522, 1.525, 1.526, 1.527, 1.529, 1.532, 1.535, 1.544, 1.549, 1.550, 1.552, 1.555, 1.558, 1.579, 1.581, 1.582, 1.584, 1.585, 1.586, 1.711, 1.712, 1.713, 1.716, 1.717, 1.718, 1.749, 1.751, 1.752, 1.754, 1.755, 1.756, 1.815, 1.816, 1.817, 1.818, 1.819, 1.820, 1.821, 1.822, 1.823, 1.824, 1.825, 1.826, 1.827, 1.828, 1.829, 1.830, 1.831, 1.832, 1.833, 1.834, 1.835, 1.836, 1.837, 1.838, 1.839, 1.840, 1.841, 1.842, 1.843, 1.844, 1.845, 1.846, 1.847, 1.848, 1.849, 1.850, 1.851, 1.852, 1.853, 1.854, 1.855, 1.856, 1.857, 1.858, 1.859, 1.860, 1.861, 1.862, 1.863, 1.864, 1.865, 1.866, 1.867, 1.868, 1.869, 1.870, 1.871, 1.872, 1.873, 1.874, 1.875, 1.876, 1.877, 1.878, 1.879, 1.880, 1.881, 1.882, 1.883, 1.884, 1.885, 1.886, 1.887, 1.888, 1.889, 1.890, 1.891, 1.892, 1.893, 1.894, 1.895, 1.896, 1.997 and other compounds from table 1 exhibit very good herbicidal action against weed plants such as Sinapis alba, Echinochloa crus-galli, Lolium multiflorum, Chrysanthemum segetum, Setaria viridis, Abutilon theophrasti, Amaranthus retroflexus, Panicum miliaceum and Avena sativa when applied post-emergence at a rate of 0.3 kg or less of active substance per hectare.
3. Crop Plant Tolerance
In further greenhouse experiments, seeds of a very large number of crop plants and weeds were laid out in sandy loam soil and covered with soil. One lot of pots was treated immediately as described in section 1, while the remaining pots were placed in a greenhouse until the plants had developed two to three true leaves, and were then sprayed as described in section 2 with the compounds of the invention at different dosages. Four to five weeks after application and a period of standing in the greenhouse, visual scoring found that compounds of the invention left dicotyledonous crops such as soybean, cotton, oilseed rape, sugarbeet or potato undamaged both pre-emergence and post-emergence and even at high active substance dosages. Some of the substances, moreover, also protected gramineous crops such as barley, wheat, rye, millet, maize or rice. The compounds of the invention in some cases exhibit high selectivity and are therefore suitable for controlling unwanted plant growth in agricultural crops.

## Claims

1. A compound of the formula (I) or salt thereof



in which
R is a hydrocarbon radical or hydrocarbonoxy radical which is unsubstituted or substituted and inclusive of substituents has 1 to 30 carbon atoms, or R is a heterocyclyl radical or heterocyclyloxy radical which is unsubstituted or substituted, wherein when R is substituted, it is substituted by halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, acylamino, monoalkylamino, dialkylamino, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyclic alkyl, cyclic haloalkyl, alkenyl, alkynyl, alkenyloxy, or alkynyloxy,
or R is a hydrogen atom, halogen or a radical C(O)R3, OC(O)R3, S(O)nR3, OS(O)nR3, OH, CN, NO2, NH2, SF5, NR4R5 or Si(R6)3, where n is 0, 1 or 2,
R1 independently at each occurrence is halogen, OH, SH, a carbon-free, nitrogen-containing radical or a carbon-containing radical having 1 to 30 carbon atoms,
p is 0, 1, 2 or 3,
R2 is an unsubstituted or substituted heterocyclyl radical having 5 ring members, wherein when R2 is substituted, it is substituted by halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, acylamino, monoalkylamino, dialkylamino, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyclic alkyl, cyclic haloalkyl, alkenyl, alkynyl, alkenyloxy, or alkynyloxy,
R3 is a hydrocarbon radical or hydrocarbonoxy radical which is unsubstituted or substituted and inclusive of substituents has 1 to 30 carbon atoms, or R3 is a heterocyclyl radical or heterocyclyloxy radical which is unsubstituted or substituted, or R3 is a hydrogen atom, CN or NR4R5, wherein when R3 is substituted, it is substituted by halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, acylamino, monoalkylamino, dialkylamino, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyclic alkyl, cyclic haloalkyl, alkenyl, alkynyl, alkenyloxy, or alkynyloxy,
R4 is a group of the formula R0-Q0-, in which
R0 is a hydrogen atom, an acyl radical, a hydrocarbon radical or a heterocyclyl radical, each of the last-mentioned two radicals being unsubstituted or substituted and inclusive of substituents having 1 to 30 carbon atoms, wherein when R0 is substituted, it is substituted by halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, acylamino, monoalkylamino, dialkylamino, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyclic alkyl, cyclic haloalkyl, alkenyl, alkynyl, alkenyloxy, or alkynyloxy, and
Q0 is a direct bond or a divalent group of the formula —O— or —N(R#)—, R# being a hydrogen atom, an acyl radical or a hydrocarbon radical and the last-mentioned radical being unsubstituted or substituted and inclusive of substituents having 1 to 30 carbon atoms, or R0 and R# form with one another a nitrogen-containing heterocyclic ring, wherein when R# is substituted, it is substituted by halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, acylamino, monoalkylamino, dialkylamino, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyclic alkyl, cyclic haloalkyl, alkenyl, alkynyl, alkenyloxy, or alkynyloxy,
R5 is a hydrogen atom, an acyl radical, a hydrocarbon radical or a heterocyclyl radical, each of the last-mentioned two radicals being unsubstituted or substituted and inclusive of substituents having 1 to 30 carbon atoms, wherein when R5 is substituted, it is substituted by halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, acylamino, monoalkylamino, dialkylamino, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyclic alkyl, cyclic haloalkyl, alkenyl, alkynyl, alkenyloxy, or alkynyloxy, or
R4 and R5 form with one another a nitrogen-containing heterocyclic ring,
R6 is a hydrocarbon radical which is unsubstituted or substituted and inclusive of substituents has 1 to 30 carbon atoms, wherein when R6 is substituted, it is substituted by halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, acylamino, monoalkylamino, dialkylamino, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyclic alkyl, cyclic haloalkyl, alkenyl, alkynyl, alkenyloxy, or alkynyloxy, and
W is an oxygen atom or a sulfur atom,
wherein the salt thereof is a sodium-, potassium-, ammonium- or ethanolamine-salt.

2. A compound of the formula (I) or salt thereof as claimed in claim 1, in which
R is (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C6)cycloalkyl, (C3-C6)-cycloalkenyl, (C3-C6)cycloalkynyl, (C1-C6)alkyloxy, (C2-C6)alkenyloxy, (C2-C6)-alkynyloxy, (C3-C6)cycloalkyloxy, phenyl, phenyloxy, H, F, Cl, Br, I, OH, CN, NO2, NH2, SF5, C(O)R3, Si((C1-C6)alkyl)3, N((C1-C6)alkyl)2, NH(C1-C6)alkyl, N((C2-C6)alkenyl)2, NH(C2-C6)alkenyl, N((C2-C6)alkynyl)2, NH(C2-C6)alkynyl, NH((C3-C6)cycloalkyl)2, NH(C3-C6)cycloalkyl, N(C1-C6)alkyl (C3-C6)cycloalkyl, S(O)n(C1-C4)alkyl, S(O)n(C3-C6)cycloalkyl, S(O) n(C1-C6)alkenyl, S(O)n(C1-C6)alkynyl, OSO2(C1-C6)alkyl, OSO2(C3-C6)cycloalkyl, OSO2(C1-C6)alkenyl, OSO2(C1-C6)alkynyl, OS(O)nphenyl, OSO2N((C1-C6)alkyl)2, OSO2NH(C1-C6)alkyl, OSO2N((C3-C6)cycloalkyl)2, OSO2NH(C3-C6)cycloalkyl, OSO2N((C2-C6)alkenyl)2, OSO2NH(C2-C6)alkenyl, OSO2N((C2-C6)alkynyl)2, OSO2NH(C2-C6)alkynyl, OC(O)R3 or heterocyclyl,
wherein said alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkynyl, alkyloxy, alkenyloxy, alkynyloxy, cycloalkoxy, phenyl, phenyloxy and heterocyclyl radicals are unsubstituted or substituted by halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, acylamino, monoalkylamino, dialkylamino, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyclic alkyl, cyclic haloalkyl, alkenyl, alkynyl, alkenyloxy, or alkynyloxy,
n is 0, 1 or 2, and R3 is H, (C1-C6)alkyl, (C2-C6)alkenyl, (C2-C6)alkynyl, (C3-C6)-cycloalkyl, (C1-C6)alkyloxy, (C2-C6)alkenyloxy, (C2-C6)alkynyloxy, (C3-C6)-cycloalkyloxy, phenyl, heterocyclyl, CN, NH(C1-C6)alkyl or N((C1-C6)alkyl)2,
wherein said alkyl, alkenyl, alkynyl, cycloalkyl, alkyloxy, alkenyloxy, alkynyloxy, cycloalkyloxy, phenyl and heterocyclyl radicals are unsubstituted or substituted by halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, acylamino, monoalkylamino, dialkylamino, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyclic alkyl, cyclic haloalkyl, alkenyl, alkynyl, alkenyloxy, or alkynyloxy,
R1 is (C1-C6)alkyl, (C1-C6)haloalkyl , (C1-C6)alkyloxy, (C1-C6)haloalkoxy or halogen,
p is 0, 1 or 2,
R2 is in each case selected from the group consisting of




in which
Q1, Q2 and Q3 are each oxygen or sulfur, and
R7 is hydrogen, hydroxy, amino, cyano, is (C2-C10)alkylideneamino, is (C1-C6)alkyl which is unsubstituted or substituted by fluorine, chlorine, bromine, cyano, (C1-C4)alkoxy, (C1-C4)alkylcarbonyl or (C1-C4)alkoxycarbonyl, is (C2-C6)alkynyl or (C2-C6)alkenyl each of which is unsubstituted or substituted by fluorine, chlorine or bromine, is (C1-C6)alkoxy, (C1-C6)alkylamino or (C1-C6)alkyl-carbonylamino each of which is unsubstituted or substituted by fluorine, chlorine, bromine, cyano, (C1-C4)alkoxy or (C1-C4)alkoxy-carbonyl, is (C3-C6)alkenyloxy, is di((C1-C4)alkyl(amino), is (C3-C6)cycloalkyl, (C3-C6)cycloalkylamino or (C3-C6)cyclo-alkyl-(C1-C4)alkyl each of which is unsubstituted or substituted by fluorine, chlorine, bromine, cyano or (C1-C4)alkyl, or is phenyl or phenyl-(C1-C4)alkyl each of which is unsubstituted or substituted by fluorine, chlorine, bromine, cyano, nitro, (C1-C4)alkyl, tri-fluoromethyl or (C1-C4)alkoxy,
R8 is hydrogen, hydroxy, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, is (C1-C6)alkyl unsubstituted or substituted by fluorine, chlorine, bromine, cyano, (C1-C4)alkoxy, (C1-C4)alkyl-carbonyl or (C1-C4)alkoxy-carbonyl, is (C2-C6)alkenyl or (C2-C6)alkynyl each of which is unsubstituted or substituted by fluorine, chlorine or bromine, is (C1-C6)alkoxy, (C1-C6)alkylthio, (C1-C6)alkylamino or (C1-C6)alkyl-carbonylamino each of which is unsubstituted or substituted by fluorine, chlorine, cyano (C1-C4)alkoxy or (C1-C4)alkoxy-carbonyl, is (C3-C6)alkenyloxy, (C3-C6)alkynyloxy, (C3-C6)alkenylthio, (C3-C6)alkynylthio, (C3-C6)alkenylamino or (C3-C6)alkynylamino, is di((C1-C4)alkyl)amino, is aziridino, pyrrolidino, piperidino or morpholino each of which is unsubstituted or substituted by methyl or ethyl, is (C-3-C6)cycloalkyl, (C5-C6)cycloalkenyl, (C3-C6)cycloalkyloxy, (C3-C6)cycloalkylthio, (C3-C6)cycloalkylamino, (C3-C6)cycloalkyl-(C1-C4)alkyl, (C3-C6)cyclo-alkyl- (C1-C4)alkoxy, (C3-C6)cycloalkyl-(C1-C4)alkylthio or (C3-C6)cyclo-alkyl-(C1-C4)alkylamino each of which is unsubstituted or substituted by fluorine, chlorine, bromine, cyano or (C1-C4)alkyl, or is phenyl, phenyl-(C1-C4)alkyl, phenoxy, phenyl- (C1-C4)alkoxy, phenylthio, phenyl-(C1-C4)alkylthio, phenylamino or phenyl-(C1-C4)alkylamino each of which is unsubstituted or substituted by fluorine, chlorine, bromine, cyano, nitro, (C1-C4)alkyl, trifluoromethyl, (C1-C4)alkoxy or (C1-C4)alkoxy-carbonyl, or
R7 and R8 together are unbranched or branched alkanediyl having 3 to 11 carbon atoms, and additionally
R9, R10 and R11 are identical or different and are hydrogen, cyano, fluorine, chlorine, bromine, or are alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio, alkynylthio, alkylsulfynyl or alkylsulfonyl having in each case up to 6 carbon atoms and being in each case unsubstituted or substituted by fluorine, chlorine, bromine or (C1-C4)alkoxy, or are cycloalkyl having 3 to 6 carbon atoms and being unsubstituted or substituted by cyano, fluorine, chlorine, bromine or (C1-C4)alkyl, and
W is an oxygen atom.

3. A compound of formula (I) or salt thereof as claimed in claim 1, in which
R is (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C6)cycloalkyl, (C1-C4)-alkyloxy, (C2-C4)alkenyloxy, (C2-C4)alkynyloxy, (C3-C6)cycloalkyloxy, phenyl, phenyloxy, H, F, Cl, Br, I, C(O)R3, CN, NO2, NH2, N((C1-C4)alkyl)2, NH(C1-C4)alkyl, NH(C2-C4)alkenyl, NH(C2-C4)alkynyl, NH(C3-C6)cycloalkyl, N(C1-C4)alkyl (C3-C6)cycloalkyl, S(C1-C4)alkyl, S(C2-C4)alkenyl, S(C2-C4)alkynyl, S(C3-C6)cycloalkyl, S(O)(C1-C4)alkyl, S(O)(C1-C4)alkenyl, S(O)(C2-C4)alkynyl, S(O)(C3-C6)-cycloalkyl, SO2(C1-C4)alkyl, SO2(C2-C4)alkenyl, SO2(C2-C4)alkynyl, SO2(C3-C6)cycloalkyl, SO2NH(C1-C4)alkyl, SO2N((C1-C4)alkyl)2, SO2NH—(C3-C6)cycloalkyl, OSO2(C1-C4)alkyl, OSO2NH(C1-C4)alkyl, OSO2N((C1-C4)alkyl)2 or OC(O)R3, R3 being H, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C3-C6)cycloalkyl, (C1-C4)alkyloxy, (C2-C4)alkenyloxy, (C2-C4)alkynyloxy, (C3-C6)cycloalkyloxy, (C1-C4)haloalkyl, NH(C1-C4)alkyl or N((C1-C4)alkyl)2,
wherein said alkyl, alkenyl, alkynyl, cycloalkyl, alkyloxy, alkenyloxy, alkynyloxy, cycloalkyloxy, phenyl and phenyloxy radicals are unsubstituted or substituted by one or more radicals, preferably one, two or three radicals, from the group consisting of F, Cl, Br, I, (C1-C4)alkyl, (C1-C4)alkyloxy, (C1-C4)haloalkyl and (C1-C4)haloalkyloxy,
R1 is F, Cl, Br, I, (C1-C4)alkyl, (C1-C4)alkyloxy, (C1-C4)haloalkyl or (C1-C4)haloalkyloxy,
p is 0 or 1,
R2 is in each case selected from the group consisting of




in which
Q1, Q2 and Q3 are each oxygen or sulfur and
R7 is hydrogen, hydroxy, amino, is (C3-C8)alkylideneamino, is methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl in each case unsubstituted or substituted by fluorine, chlorine, cyano, methoxy or ethoxy, is propenyl, butenyl, propynyl or butynyl in each case unsubstituted or substituted by fluorine, chlorine or bromine, is methoxy, ethoxy, n-propoxy or isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, methylamino, ethylamino, n-propylamino or isopropylamino, n-butylamino, isobutylamino, sec-butylamino or tert-butylamino, in each case unsubstituted or substituted by fluorine, chlorine, cyano, methoxy or ethoxy, is propenyloxy or butenyloxy, is dimethylamino or diethylamino, is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl in each case unsubstituted or substituted by fluorine, chlorine, methyl or ethyl, or is phenyl or benzyl in each case unsubstituted or substituted by fluorine, chlorine, methyl, trifluoromethyl or methoxy,
R8 is hydrogen, hydroxy, mercapto, amino, fluorine, chlorine, bromine, is methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl in each case unsubstituted or substituted by fluorine, chlorine, cyano, methoxy or ethoxy, is ethenyl, propenyl, butenyl, propynyl or butynyl in each case unsubstituted or substituted by fluorine, chlorine or bromine, is methoxy, ethoxy, n-propoxy or isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, methylthio, ethylthio, n-propylthio or isopropythio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, methylamino, ethylamino, n-propylamino or isopropylamino, n-butylamino, isobutylamino, sec-butylamino or tert-butylamino, in each case unsubstituted or substituted by chlorine, fluorine, cyano, methoxy or ethoxy, is propenyloxy, butenyloxy, propynyloxy, butynyloxy, propenylthio, propadienylthio, butenylthio, propynylthio, butynylthio, propenylamino, butenylamino, propynylamino or butynylamino, is dimethylamino, diethylamino or dipropylamino, is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino , cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino in each case unsubstituted or substituted by fluorine, chlorine, methyl or ethyl, or is phenyl, benzyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylamino or benzylamino in each case unsubstituted or substituted by fluorine, chlorine, methyl, trifluoromethyl, methoxy or methoxycarbonyl, or
R7 and R8 together are unbranched or branched alkanediyl having 3 to 11 carbon atoms, and additionally
R9, R10 and R11 are identical or different and are hydrogen, cyano, fluorine, chlorine, bromine, or are methyl, ethyl, n-propyl or isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, propenyl, butenyl, propynyl, butynyl, methoxy, ethoxy, n-propoxy or isopropyl, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, propenyloxy, butenyloxy, propynyloxy, butynyloxy, methylthio, ethylthio, n-propylthio or isopropylthio, n-butylthio, isobutylthio, sec-butylthio or tert-butylthio, propenylthio, butenylthio, propynylthio, butynylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, in each case unsubstituted or substituted by fluorine, chlorine, methoxy or ethoxy, or are cyclopropyl, and
W is a hydrogen atom.

4. A compound of the formula (I) or salt thereof as claimed in claim 1, in which
R is CH3, CH2CH3, (CH2)2CH3, CH(CH3)2, C(CH3)3, CH═CH2, C≡CH, CH2CH═CH2, CH2C≡CH, cyclopropyl, phenyl, H, F, Cl, Br, I, CN, NO2, NH2, CH2OCH3, CF3, CHF2, C(O)H, C(O)CH3, C(O)CH2CH3, C(O)OCH3, C(O)OCH2CH3, NHCH3, N(CH3)2, NH-cyclopropyl, N(CH3)-cyclopropyl, NHC(O)H, NHC(O)CH3, NHC(O)OCH3, OCH3, OCH2CH3, O(CH2)2CH3, OCH(CH3)2, O(CH2)3CH3, OCH2CH(CH3)2, OCH(CH3)CH2CH3, OC(CH3)3, OCH═CH2, OC≡CH, OCH2CH═CH2, OCH2C≡CH, O-cyclopropyl, OCH2-cyclopropyl, O(CH2)2Cl, O(CH2)3Cl, OCH2OCH3, Ophenyl, OCH2phenyl, OCF3, OCHF2, OCH2F, OCH2CF3, OCH2CHF2, OCH(CH3)CF3, OCH2CF2CF3, SCH3, SCH2CH3, S(O)CH3, S(O)CH2CH3, SO2CH3, SO2CH2CH3, SO2NHCH3, SO2N(CH3)2, SO2NHCF3, SO2NHCHF2, OSO2CH3, OSO2CF3, OSO2CHF2, OSO2N(CH3)2, OSO2NHCF3, OSO2NHCHF2, OC(O)H, OC(O)CH3, OC(O)OCH3, OC(O)N(CH3)2,
p is 0,
R2 is of the following formula




in which
Q1 is oxygen or sulfur, and
R7 is methyl, ethyl, n-propyl or isopropyl each of which is unsubstituted or substituted by fluorine, chlorine, cyano, methoxy or ethoxy, is propenyl or propynyl, is methoxy, ethoxy, n-propoxy or isopropoxy, or is cyclopropyl,
R8 is hydrogen, chlorine, bromine, is methyl, ethyl, n-propyl or isopropyl each of which is unsubstituted or substituted fluorine, chlorine, cyano, methoxy or ethoxy, is unsubstituted propenyl or propynyl, is propenyl or propynyl each of which is unsubstituted or substituted by fluorine or chlorine, is methoxy, ethoxy, n-propoxy or isopropoxy, methylthio, ethylthio, n-propylthio or isopropylthio, each of which is unsubstituted or substituted by fluorine, chlorine, cyano, methoxy or ethoxy, or is propenyloxy or cyclopropyl, and
W is oxygen.

5. A process for preparing a compound of the formula (I) or salt thereof, as defined in claim 1, comprising
(a) reacting an aminosulfonyl compound of the formula (II)




with a (thio)carboxylic acid derivative of the formula (III)




in which
R* is halogen or an unsubstituted or substituted (C1-C20)hydrocarbonoxy radical,
optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,
or
(b) reacting a sulfonyliso(thio)cyanate of the formula (IV)




with a heterocyclyl compound of the formula (V)


H—R2  (V)


optionally in the presence of a reaction auxiliary and optionally in with or without the presence of a diluent,
or
(c) reacting a halosulfonyl compound of the formula (VI)




with a heterocyclyl compound of the formula (V)


H—R2  (V)


and a metal (thio)cyanate of the formula (VII)


MWCN  (VII)


in which
M is a cation and
W is an oxygen atom or a sulfur atom,
optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,
or
(d) reacting a halosulfonyl compound of the formula (VI)




with a (thio)carboxamide of the formula (VIII)




optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,
or
(e) reacting a sulfonylamino(thio)carbonyl compound of the formula (IX)




in which
R** is halogen or an unsubstituted or substituted (C1-C20)hydrocarbon radical with a heterocyclyl compound of the formula (V)


H—R2  (V)


optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent,
and optionally converting the compound of the formula (I) obtained by process (a), (b), (c), (d) or (e) into a salt by customary methods,
the radicals, groups, and indices R, R1, R2, W and 1 in the formulae (II)-(IX) being defined as in formula (I).

6. An agrochemical composition comprising a) at least one compound of the formula (I) or salt thereof, as defined in claim 1, and b) at least one crop protection auxiliary or additive selected from the group of stickers, wetters, dispersants, emulsifiers, penetrants, preservatives, frost preventives, solvents, fillers, carriers, colorants, defoamers, antievaporants, pH modifiers and viscosity modifiers.

7. A compound of formula (II*)



in which
Z* is NH2, NH-tert-butyl, NH—C(O)R**, NH—C(S)R**, NCO, NCS or halogen,
wherein
R1 independently at each occurrence is halogen, OH, SH, a carbon-free, nitrogen-containing radical or a carbon-containing radical having 1 to 30 carbon atoms,
p is 0, 1, 2 or 3,
R** is halogen or an unsubstituted or substituted (C1-C20)hydrocarbon radical
R is a radical C(O)R3; and
R3 is a hydrocarbon radical or hydrocarbonoxy radical which is unsubstituted or substituted and inclusive of substituents has 1 to 30 carbon atoms, or R3 is a heterocyclyl radical or heterocyclyloxy radical which is unsubstituted or substituted, or R3 is a hydrogen atom, CN or NR4R5, wherein when R3 is substituted, it is substituted by halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, acylamino, monoalkylamino, dialkylamino, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyclic alkyl, cyclic haloalkyl, alkenyl, alkynyl, alkenyloxy, or alkynyloxy.

8. The compound of formula I:



wherein R is selected from the group consisting of N(C1-C6)alkyl C(O)R3, NHC(O)R3, N(C1-C6)alkyl S(O)nR3, NHS(O)nR3, S(O)nNHR3, and S(O)nN(C1-C6)alkyl R3,
R1 independently at each occurrence is halogen, OH, SH, a carbon-free, nitrogen-containing radical or a carbon-containing radical having 1 to 30 carbon atoms,
p is 0, 1, 2 or 3,
R2 is an unsubstituted or substituted heterocyclyl radical having 5 ring members, wherein when R2 is substituted, it is substituted by halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, acylamino, monoalkylamino, dialkylamino, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyclic alkyl, cyclic haloalkyl, alkenyl, alkynyl, alkenyloxy, or alkynyloxy,
R3 is a hydrocarbon radical or hydrocarbonoxy radical which is unsubstituted or substituted and inclusive of substituents has 1 to 30 carbon atoms, or R3 is a heterocyclyl radical or heterocyclyloxy radical which is unsubstituted or substituted, or R3 is a hydrogen atom, CN or NR4R5, wherein when R3 is substituted, it is substituted by halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, acylamino, monoalkylamino, dialkylamino, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyclic alkyl, cyclic haloalkyl, alkenyl, alkynyl, alkenyloxy, or alkynyloxy, and
W is an oxygen atom or a sulfur atom.

9. The compound of claim 8, wherein R is selected from the group consisting of NHSO2R3, NHSO2CH3, NHSO2CF3, and NHSO2CHF2.

10. A method of controlling weeds selected from the group consisting of Apera spica venti, Avena species, Alopecurus species, Brachiaria species, Digitaria species, Lolium species, Echinochloa species, Panicum species, Phalaris species, Poa species, Setaria species, Bromus species, annual Cyperus species, perennial Cyperus species, Abutilon species, Amaranthus species, Chenopodium species, Chrysanthemum species, Galium species, Ipomoea species, Kochia species, Lamium species, Matricaria species, Pharbitis species, Polygonum species, Sida species, Sinapis species, Solanum species, Stellaria species, Veronica species, Viola species, Xanthium species, Convolvulus, Cirsium, Rumex, Artemisia, Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus, comprising applying an effective amount of at least one compound of formula (I) or salt thereof, as defined in claim 1, to the weed, to the seed of the weed, or to an area on which the weed is growing.