Sulfonamides

Description

The present invention relates to sulfonamides of the formula I ##STR2## where A is ##STR3## W is oxygen or sulfur; B is 2-, 3-, 4- or 5-furyl, 2-, 3-, 4- or 5-thienyl, each trisubstituted by R.sup.8 ; 2-, 3-, 4- or 5-pyrrol which is trisubstituted on carbon by R.sup.8 and monosubstituted on nitrogen by R.sup.9 ; 2-, 4- or 5-oxazolyl, 3-, 4- or 5-isoxazolyl 2-, 4- or 5-thiazolyl or 3-, 4- or 5-isothiazolyl, each disubstituted by R.sup.8 ; 2-, 4- or 5-imidazolyl or 3-, 4- or 5-pyrazolyl, each disubstituted on carbon by R.sup.8 and monosubstituted on nitrogen by R.sup.9 ; 1,3,4-thiadiazol-2-yl,-5-y1,1,3,4-oxadiazol-2-yl,-5-yl, 2,4-thiadiazol-3-yl,-5-yl, 1,2,4-oxadiazol-3-yl,-5-yl, 1,2,3-thiadiazol-4-yl,-5-yl, 1,2,3-oxadiazol-4-yl,-5-yl, 1,2,5-thiadiazol-3-yl,-4-yl, 1,2,5-oxadiazol-3-yl,-4-yl, each of which is monosubstituted by R.sup.8 ; 1,2,4-triazol-3-yl, substituted on carbon by R.sup.10 and on N-1 by R.sup.11 ; 1,2,4-triazol-5-yl or 1,2,3-triazol-4-yl or -5-yl, each substituted on carbon by R.sup.8 and on N-1 by R.sup.9 ;
X is oxygen, sulfur or NR.sup.1 ;
R.sup.1 is hydrogen; C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by one to five halogens and or phenyl; C.sub.2 -C.sub.4 -alkenyl; phenyl which is unsubstituted or substituted by one to five halogens and/or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, nitro or cyano;
R.sup.2 is halogen; cyano; thiocyano; C.sub.1 -C.sub.6 -alkyl which can be substituted by one to five halogens and/or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, phenyl, phenoxy or phenylthio, where each of the phenyls can be substituted by one to five halogens and/or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.8 -cycloalkoxy, C.sub.3 -C.sub.6 -cycloalkylthio, C.sub.5 -C.sub.6 -cycloalkenyl, C.sub.5 -C.sub.8 -cycloalkenyloxy or C.sub.5 614 C.sub.6 -cycloalkenylthio, each of which may be substituted by one to five halogens and/or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub. 1 -C.sub.4 -haloalkylthio; phenyl, phenoxy, benzyloxy or benzylthio, each of which may be substituted by one to five halogens and/or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; saturated, singly or doubly unsaturated 5-7-membered heterocycle which contains one or two nitrogen, oxygen and/or sulfur atoms and is unsubstituted or substituted by up to two of the following: halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -haloalkylthio; C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio, C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkenyloxy or C.sub.2 -C.sub.6 -alkenylthio, C.sub.2 -C.sub.6 -alkynyl, C.sub.2 -C.sub.6 -alkynyloxy or C.sub.2 -C.sub.6 -alkynylthio, where the said alkoxy, alkylthio, alkenyl, alkynyl, alkenyloxy(thio) and alkynyloxy(thio) may be substituted by one to five halogens and/or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio; phenyl, phenoxy, phenylthio, benzyloxy or benzylthio;
COR.sup.12 ; COQR.sup.13 ; SO.sub.2 NR.sup.15 R.sup.16 ; SO.sub.2 OR.sup.17 ; OSO.sub.2 R.sup.18 ; S(O).sub.n R.sup.19 ;
R.sup.3 is R.sup.6 ; COQR.sup.13 ; SO.sub.2 NR.sup.15 R.sup.16 ; SO.sub.2 OR.sup.16 ; OSO.sub.2 R.sup.16 ; S(O).sub.n R.sup.19 ;
R.sup.4 is hydrogen; halogen; cyano; C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkyl substituted by one to five halogens; C.sub.1 -C.sub.4 -alkoxy; C.sub.1 -C.sub.4 -haloalkoxy; C.sub.1 -C.sub.4 -alkylthio; C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.5 is hydrogen; nitro or R.sup.2 ;
R.sup.6 is hydrogen; halogen; cyano; C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkyl substituted by one to five halogens and/or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, OH, SH or cyano; C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -haloalkylthio, each of which may be substituted by the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.7 is nitro; or R.sup.2 ;
R.sup.8 is hydrogen; nitro;
or R.sup.2, or two vicinal R.sup.2 together form a C.sub.3 chain or a C.sub.4 -C.sub.6 chain in which one methylene can be replaced by oxygen or C.sub.1 -C.sub.4 -alkylimino;
R.sup.9 is hydrogen;
C.sub.1 -C.sub.6 -alkyl which may be substituted by one to five halogens and/or one of the following: C.sub.1 -C.sub.4 -alkoxy; C.sub.1 -C.sub.4 -haloalkoxy; C.sub.1 -C.sub.4 -alkylthio; C.sub.1 -C.sub.4 -haloalkylthio, phenyl, phenoxy or phenylthio, it being possible for the cyclic groups to be substituted by one to five halogens and/or one to three of the following: cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; C.sub.3 -C.sub.6 -cycloalkyl or C.sub.5 -C.sub.6 -cycloalkenyl, each of which may be substituted by one to five halogens and/or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; phenyl which may be substituted by one to five halogens and/or one to three of the following: cyano, nitro, C.sub.1 -C.sub. 4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkynyl, each of which may be substituted by one to five halogens and/or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio, phenyl, phenoxy, phenylthio, benzyloxy or benzylthio; COR.sup.21 ;
R.sup.10 is phenyl, benzyl, phenoxy, benzyloxy, phenylthio or benzylthio, each of which may be substituted by one to five halogens and/or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub..sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.11 is hydrogen; phenyl or benzyl, each of which may be substituted by one to five halogens and/or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.12 is C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by halogen or methoxy; C.sub.3 -C.sub.5 -cycloalkyl which is unsubstituted or substituted by chlorine or fluorine; C.sub.3 -C.sub.4 -alkenyl;
Q is oxygen or NR.sup.14 ;
R.sup.13 is hydrogen; C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkyl, substituted by one to three of the following: halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 C.sub.4 -alkoxy-C.sub.1 -C.sub.2 -alkoxy, C.sub.3 -C.sub..sub.6 -cycloalkyl and/or phenyl; C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.6 -cycloalkyl which is substituted once to three times by C.sub.1 -C.sub.4 -alkyl; C.sub.3 -C.sub.6 -alkenyl; C.sub.3 -C.sub.6 -alkynyl; phenyl, phenyl substituted by one to five halogens and/or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub..sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.14 is OR.sup.20 ; R.sup.13 or forms together with another R.sup.13 a C.sub.4 -C.sub.6 -alkylene chain in which one methylene can be replaced by oxygen or C.sub.1 -C.sub.4 -alkylimino;
R.sup.15 is C.sub.1 -C.sub.4 -alkyl; C.sub.3 C.sub.4 -alkenyl; C.sub.3 -C.sub.4 -alkynyl; cyclopropylmethyl; C.sub.3 -C.sub.4 -cycloalkyl;
R.sup.16 is hydrogen; C.sub.1 -C.sub.4 -alkyl; C.sub.3 -C.sub.4 -alkenyl; or forms together with R.sup.15 a C.sub.4 -C.sub.6 alkylene chain in which one methylene can be replaced by oxygen;
R.sup.17 is C.sub.1 -C.sub.4 -alkyl; C.sub.1 -C.sub.4 -haloalkyl;
R.sup.18 is C.sub.1 -C.sub.4 -alkyl; N,N-dimethylamino;
R.sup.19 is C.sub.1 -C.sub.4 -alkyl; C.sub.1 -C.sub.4 -haloalkyl; C.sub.2 -C.sub.4 -alkoxyalkyl; C.sub.3 -C.sub.4 -alkenyl; C.sub.3 -C.sub.4 -alkynyl; C.sub.3 -C.sub.4 -haloalkenyl; phenyl; phenyl substituted by fluorine, chlorine, bromine, methyl or methoxy;
n is 1 or 2;
R.sup.20 is hydrogen or C.sub.1 -C.sub.4 -alkyl;
R.sup.21 is R.sup.12 ; phenyl or benzyl, each of which may be substituted by one to five halogens and/or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
and the environmentally compatible salts thereof.
The present invention relates to processes for preparing the novel sulfonamides and to herbicides and bioregulators containing the compounds I and to the use thereof for controlling undesired plant growth.
It has been disclosed that certain sulfonylated 1-carbamoyl-2-pyrazolines have herbicidal and/or growth-regulatory properties (EP-A-269 141). In addition, some sulfonylated bi- or tricyclic carboxamides have herbicidal and growth-regulatory activities (EP-A-244 166).
It is an object of the present invention to find sulfonamides with satisfactory properties as herbicides and/or bioregulators.
We have found that this object is achieved by the sulfonamides I which are defined in the first paragraph and are prepared as described. The present invention also relates to herbicides and agents for controlling plant growth which contain the novel compounds I, and to a process for influencing and controlling plant growth with these compounds.
The compounds of the formula I may contain one or more centers of chirality and then exist as mixtures of diastereomers. The present invention embraces both the pure enantiomers or diastereomers and the mixtures thereof.
The compounds of the formula I are able to form salts in which the hydrogen of the --SO.sub.2 --NH-- group is replaced by an agriculturally suitable cation. These salts are generally of metals, in particular alkali metals or alkaline earth metals, but may be of alkylated ammonium or organic amines. They are preferably prepared in inert solvents such as water, methanol or acetone at 0.degree.-100.degree. C. Examples of bases suitable for preparing the salts according to the invention are alkali metal carbonates such as potassium carbonate, alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal alcoholates, ammonia or ethanolamine.
The term alkyl in the above definitions in each case means straight-chain or branched alkyl.
Likewise, alkenyl and alkynyl mean straight-chain or branched radicals.
The term halogen means fluorine, chlorine, bromine or iodine.
Preferred compounds of the formula I are those where
A is (A1), (A2), (A7), (A8) or (A9),
W is oxygen
X is sulfur
B is 2-, 4- or 5-oxazolyl, 3-, 4- or 5-isoxazolyl, 2-, 4- or 5-thiazolyl or 3-, 4- or 5-isothiazolyl, each of these being disubstituted by R:;
2-, 4- or 5-imidazolyl or 3-, 4- or 5-pyrazolyl, each of these being disubstituted on carbon by R: and monosubstituted on nitrogen by R.sup.9 ;
R.sup.4 is hydrogen, and the environmentally compatible salts thereof.
Particularly preferred compounds of the formula I are those where
A is (A1) and
B is 3-, 4- or 5-pyrazolyl, disubstituted on carbon by R.sup.8 and monosubstituted on nitrogen by R.sup.9, and the environmentally compatible salts thereof.

The compounds of the formula I can be obtained in a wide variety of ways similar to known reaction methods. Seven processes (A to G) are explained hereinafter by way of example.
PROCESS A
Compounds of the formula I with W.dbd.O are obtained in a conventional manner (M. L. Crossley, E. H. Northey, M. E. Hultquist, J. Am. Chem. Soc. 61, (1939), 2950-2955) by reacting an appropriate sulfonamide II in an inert organic solvent in the presence of a base with an acid halide of the formula III as shown below: ##STR4## Hal in formula III is chlorine or bromine.
The solvents expediently used for these reactions are halohydrocarbons, e.g. tetrachloromethane, chloroform, methylene chloride, dichloroethane, chlorobenzene and 1,2-dichlorobenzene; ethers, e.g. diethyl ether, methyl tert-butyl ether, dimethoxyethane, diethylene glycol dimethyl ether, tetrahydrofuran and dioxane; ketones, e.g. acetone, ethyl methyl ketone and cyclohexanone; dipolar aprotic solvents, e.g. acetonitrile and N-methylpyrrolidone; aromatic compounds e.g. benzene, toluene, xylene, pyridine, quinoline or mixtures thereof.
The reaction can be carried out at from 0.degree. C. to the reflux temperature of the particular solvent or mixture thereof.
Suitable bases are aromatic nitrogen bases such as pyridine, 4-dimethylaminopyridine or quinoline; tertiary aliphatic amines such as triethylamine, N-ethyl-N,N-diisopropylamine and N-methylmorpholine; bi- and tricyclic amines such as diazabicycloundecene (DBU) or diazabicyclooctane (DABCO) and hydroxides, hydrides, alkoxides, carbonates and bicarbonates of alkali metals and alkaline earth metals, especially sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride, calcium hydride, lithium hydride, sodium methanolate, sodium ethanolate, potassium tert-butylate, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate. It may also be beneficial to use combinations of the abovementioned bases.
The starting materials II and III are normally employed in the stoichiometric ratio, but an excess of one of the components may be advantageous.
The molar ratio of sulfonamide II to base is generally from 1:1 to 1:3.
The concentration of the precursors in the solvent is generally from 0.1 to 5.0 mol/l, preferably 0.2 to 2.0 mol/l.
It is particularly preferable to use inert aprotic solvents such as methylene chloride, acetone or toluene with sodium hydride, sodium carbonate or potassium carbonate as bases.
PROCESS B
Compounds of the formula I with W.dbd.O are obtained in a conventional manner (J. T. Drummond, G. Johnson, Tetrahedron Lett. 29, (1988), 1653-1656) by reacting a compound of the formula IV, in the presence of activating reagents such 2-chloro-1-methylpyridinium iodide, dicyclohexylcarbodiimide or 1,1-carbonyldiimidazole, and in the presence or absence of a base, with a compound of the formula II. ##STR5## The activated carboxylic acid is expediently reacted without intermediate isolation with component II in the presence or absence of a base.
The reactions are expediently carried out in solvents such as halohydrocarbons, e.g. chloroform, methylene chloride, dichloroethane, chlorobenzene or 1,2-dichlorobenzene; ethers, e.g. diethyl ether, methyl tert-butyl ether, dimethoxyethane, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane; dipolar aprotic solvents, e.g. acetonitrile; aromatic compounds, e.g. benzene, toluene or xylene or mixture thereof.
The reactions can be carried out at from -30.degree. C. to the reflux temperature of the particular solvent or mixture thereof.
Examples of bases which are used are organic nitrogen bases such as pyridine, 4-dimethylaminopyridine, quinoline, triethylamine, N-ethyl-N,N-diisopropylamine, diazabicycloundecene (DBU) etc., and hydroxides, hydrides, alkoxides, carbonates and bicarbonates of alkali metals and alkaline earth metals, especially sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride, sodium methanolate, sodium ethanolate, potassium tert-butylate, sodium carbonate, calcium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate. It may also be advantageous to use combinations of the abovementioned bases.
The starting materials II and IV, and the activating reagent, are normally employed in the stoichiometric ratio, but an excess of one of the components may be advantageous.
PROCESS C
Compounds of the formula I with W.dbd.O can be obtained in a conventional manner (M. Seefelder, Chem. Ber. 96, (1963), 3243-3253) by reacting a compound of the formula V with a compound of the formula VI ##STR6## M in formula VI is hydrogen or lithium.
It is expedient to use inert solvents such as halohydrocarbons, e.g. chloroform, methylene chloride, dichloroethane, chlorobenzene or 1,2-dichlorobenzene; ethers, e.g. tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; aromatic compounds, e.g. benzene, toluene, xylene or nitrobenzene, or mixtures thereof.
The reactions can be carried out at from -78.degree. C. to the reflux temperature of the particular solvent or mixture thereof.
The precursors V and VI are normally employed in the stoichiometric ratio, but an excess of one of the components may be advantageous in a few cases.
PROCESS D
Compounds of the formula I with W.dbd.O can be obtained in a conventional manner (GB-2 092 136) by reacting a compound of the formula VII with a compound of the formula VIII in the presence of a strong base. ##STR7## It is expedient to polar, aprotic solvents, e.g. acetonitrile, nitromethane, nitroethane, nitrobenzene, pyridine, benzonitrile, N,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, dioxane, tetrahydrofuran, dimethoxyethane, diethylene glycol dimethyl ether or mixtures thereof.
The reactions are usually carried out at from -20.degree. C. to the reflux temperature of the particular solvent or mixture thereof.
The bases normally used are inorganic bases such as oxides, hydroxides, hydrides, carbonates, bicarbonates and alkali metal alkoxides, especially sodium oxide, lithium oxide, potassium oxide, sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride, calcium hydride, sodium methanolate, sodium ethanolate, potassium tert-butylate, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate. It may also be advantageous to use combinations of the abovementioned bases.
As a rule, the starting materials VII and VIII and the base are employed in the stoichiometric ratio, but an excess of one of the components may be advantageous.
PROCESS E
Compounds of the formula I with W.dbd.O are obtained in a conventional manner (M. M. Kremlev, V. G. Dolyuk, J. Org. Chem. (USSR) 10, (1974), 671-672) by reacting a compound of the formula IX and a compound of the formula X with a compound of the formula XI, ##STR8## where T is alkali metal and Hal is chlorine or bromine.
It is expedient to use inert solvents such as halohydrocarbons, e.g. chloroform, methylene chloride, dichloroethane, tetrachloromethane, chlorobenzene or 1,2-dichlorobenzene; aromatic compounds, e.g. benzene, toluene, xylene or nitrobenzene or mixtures thereof. The reactions can be carried out at from 0.degree. C. to the reflux temperature of the particular solvent or mixture thereof.
The precursors are normally employed in the stoichiometric ratio, but an excess of one of the components may be advantageous in a few cases.
PROCESS F
Compounds of the formula I with W.dbd.S are obtained by processes similar to those disclosed in the literature (S. Scheibye, B. S. Pederson, S. O. Lawesson, Bull. Soc. Chim. Belg. 87, (1978), 229-238) by reacting a compound of the formula I obtained by process A to E with the compound of the formula XII ##STR9## in an inert aprotic solvent such as benzene, toluene, xylene, HMPA, dimethoxyethane or diethylene glycol dimethyl ether or mixtures thereof.
The reaction can be carried out at from about 0.degree. C. to the reflux temperature of the particular solvent or mixture thereof.
The starting materials I (W.dbd.O) and XII are normally employed in the stoichiometric ratio, but an excess of one component may be advantageous.
PROCESS G
Compounds of the formula I are obtained by processes known from the literature or similar thereto (T. L. Gilchrist, Heterocyclic Chemistry, Pitman Publisher, London (1985)) by reacting a compound of the formula XIII obtained by process A to E with a nucleophile ##STR10## where the heterocycle B' carries a C-bonded substituent which acts as leaving group. This entails the leaving group, such as phenolate, chloride, bromide, etc., being replaced by the nucleophile unit.
Examples of nucleophiles which can be used are alcoholates, thiolates, hydrides and alkali metal alkyls.
It is expedient to use, appropriate for the particular nucleophile, polar aprotic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), polar solvents such as alcohols, water, etc., inert solvents such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran (THF), dioxane, dimethoxyethane and diethylene glycol dimethyl ether or mixtures thereof.
The reactions are normally carried out at from -78.degree. C. to the reflux temperature of the particular solvent or mixture thereof.
As a rule, the starting materials are employed in the stoichiometric ratio, but an excess of one of the components may be advantageous.
The sulfonamides of the formula II employed in processes A and B are in many cases commercially available. Novel sulfonamides of the formula II can be prepared by conventional methods (S. Pawlenko in Methoden der organischen Chemie, Houben-Weyl, vol. E 11/II, pages 1098 et seq. 4th edition, Thieme Verlag, Stuttgart 1985).
The acid halides of the formula III used in process A can be prepared in a conventional manner (M. F. Ansell, in The Chemistry of acyl halides (ed. S. Patai), pages 35 et seq., 1st edition, Interscience Publishers, London (1972)) from the corresponding carboxylic acids (IV) ##STR11## or the salts thereof, with organic acid halides such as oxalyl chloride, phosgene or benzoyl chloride or with inorganic acid halides such as POHal.sub.3, PHal.sub.3, PHal.sub.5, SOCl.sub.2, P(C.sub.6 H.sub.5).sub.3 Hal.sub.2 etc. or binary systems such as P(C.sub.6 H.sub.5).sub.3 /CCl.sub.4 etc.
It may in some cases be expedient to add a suitable base, especially organic nitrogen bases such as pyridine, 2,6-lutidine or triethylamine, or a suitable catalyst such as dimethylformamide or 4-dimethylaminopyridine.
The carboxylic acids of the formula IV are known from the literature or can be prepared by methods similar to those disclosed in the literature (R. Sustmann, H. G. Korth in Methoden der organischen Chemie, Houben-Weyl, vol. E 5/I, pages 193 et seq., 4th edition, Thieme Verlag, Stuttgart 1985).
The sulfonyl isocyanates of the formula V are prepared by standard processes known to those skilled in the art (Newer Methods of Preparative Organic Chemistry, vol. VI, pages 223 et seq., Academic Press, New York).
The compounds of the formula VI required for process C can likewise be prepared by standard processes.
The sulfonyl chlorides of the formula VII employed for process D are in many cases commercially available. Novel sulfonyl chlorides of the formula VII can be prepared by processes known to those skilled in the art (S. Pawlenko in Methoden der organischen Chemie, Houben-Weyl, vol. E 11/I, pages 1067 et seq., 4th edition, Thieme Verlag, Stuttgart 1985).
Compounds of the formula VIII are known from the literature or can be prepared by known methods (D. Deopp, H. Dopp in Methoden der organischen Chemie, Houben-Weyl, vol. E 5/II, pages 934 et seq., 4th edition, Thieme Verlag, Stuttgart 1985).
The salts of the formula IX are prepared by standard processes (F. Muth in Methoden der organischen Chemie, Houben-Weyl, vol. 9, pages 629 et seq., 4th edition, Thieme Verlag, Stuttgart 1955).
The halosulfonamides of the formula X are likewise known from the literature or can be prepared in a conventional manner (F. Muth in Methoden der organischen Chemie, Houben-Weyl, vol. 9, pages 641 et seq., 4th edition, Thieme Verlag, Stuttgart 1955).
The aldehydes of the formula XI can be synthesized by known processes (O. Bayer in Methoden der organischen Chemie, Houben-Weyl, vol. 7/1, 4th edition, Thieme Verlag, Stuttgart 1954; vol. E3, 4th edition, Thieme Verlag, Stuttgart 1983).
With a view to the intended use, the preferred compounds of the formula I have substituents with the following meanings:
X is oxygen, sulfur or NR.sup.1,
R.sup.1 is hydrogen; C.sub.1 C.sub.6 -alkyl, especially C.sub.1 -C.sub.4 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, which is unsubstituted or substituted by 1 to 5, in particular 1 to 3, halogens such as fluorine, chlorine or bromine and/or by phenyl. C.sub.2 -C.sub.4 -alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-2-propenyl, 1-methyl-2-propenyl, 2-methyl-1-propenyl, phenyl or phenyl substituted by 1 to 5 halogens such as fluorine, chlorine or bromine and/or one to three of the initially mentioned substituents.
R.sup.2 is halogen such as fluorine, chlorine, bromine or iodine, especially fluorine, chlorine and bromine, cyano and thiocyano; C.sub.1 -C.sub.6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-methylpropyl and 1-ethyl-2-methylpropyl which is substituted by 1 to 5 halogens, especially fluorine, chlorine or bromine, and/or by one of the following: C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy and the corresponding alkylthios, which may be substituted by halogen, especially fluorine, chlorine or bromine, or phenyl, phenoxy, phenylthio, optionally substituted by one to five halogens, especially fluorine, chlorine and bromine and/or one to three C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy radicals; C.sub.3 -C.sub.6 -cycloalkyl and C.sub.3 -C.sub.6 -cycloalkylthio, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, especially cyclopropyl, cyclopentyl, cyclohexyl, which can carry one to five halogens, especially fluorine, chlorine and bromine, and/or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub..sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, especially methyl, and the corresponding cycloalkylthio radicals; C.sub.3 -C.sub.8 -cycloalkoxy such as cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexoxy, cycloheptoxy, cyclooctoxy, especially cyclopropoxy, cyclopentoxy and cycloheptoxy, which can be substituted by one to five halogens, especially fluorine, chlorine and bromine, and/or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -haloalkylthio, especially methyl; C.sub.5 -C.sub.6 -cycloalkenyl such as 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl or 3-cyzlohexenyl, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and/or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -haloalkylthio and C.sub.1 -C.sub.4 -alkylthio especially methyl; C.sub.5 -C.sub.8 -cycloalkenyloxy or C.sub.5 -C.sub.6 -cycloalkenylthio, such as 1-cyclopentenyloxy, 2-cyclopentenyloxy, 3-cyclopentenyloxy, 1-cyclohexenyloxy, 2-cyclohexenyloxy, 3-cyclohexenyloxy, 1-cycloheptenyloxy, 2-cycloheptenyloxy, 3-cycloheptenyloxy, 4-cycloheptenyloxy, 1-cyclooctenyloxy, 2-cyclooctenyloxy, 3-cyclooctenyloxy, 4-cyclooctenyloxy, which can carry one to five of the following: fluorine, chlorine, bromine or iodine, especially fluorine, chlorine or bromine, and/or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio, especially methyl; phenyl, phenoxy, benzyloxy or benzylthio, each of which can be substituted by 1 to 5 halogens, especially fluorine, chlorine or bromine, and/or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -haloalkylthio; saturated, singly or doubly unsaturated 5-7-membered heterocycle containing one or two nitrogen, oxygen and/or sulfur atoms, e.g. thiophene, furan, isoxazole, pyrazole, thiazole, oxazole, oxadiazole, thiadiazole, tetrahydrofuran or tetrahydropyran, where the heterocyclic heteroaromatic radicals can be substituted once or twice by the following: halogen such as fluorine, chlorine, bromine or iodine, especially fluorine, chlorine and bromine, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkythio, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl, which can be substituted by one to five halogens, especially fluorine, chlorine and bromine, and the corresponding alkoxy and alkylthio radicals; C.sub.1 -C.sub.4 -alkoxy or alkylthio such as methoxy, ethoxy propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and/or by one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio, and the corresponding alkylthio radicals; C.sub.3 -C.sub.6 -alkenyl, alkenyloxy or alkenylthio such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1 -pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1,-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and/or by one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 614 C.sub.4 -haloalkylthio, and the corresponding alkenyloxy and alkenylthio radicals; C.sub.2 -C.sub.6 -alkynyl, alkynyloxy or alkynylthio, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and/or by one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub..sub.4 -haloalkylthio, and the corresponding alkynyloxy and alkynylthio radicals; COR.sup.12 such as alkylcarbonyl with C.sub.1 -C.sub.4 -alkyl as mentioned for R.sup.12, such as cycloalkylcarbonyl with C.sub.3 -C.sub.5 -cycloalkyl as mentioned for R.sup.12, such as alkenylcarbonyl with C.sub.3 -C.sub.4 -alkenyl as mentioned for R.sup.12, especially methylcarbonyl, ethylcarbonyl and cyclopropylcarbonyl; COQR.sup.13 such as carboxyl, such as alkoxycarbonyl with C.sub.1 -C.sub.6 -alkyl as mentioned for R.sup.13, cycloalkoxycarbonyl with C.sub.3 -C.sub.6 -cycloalkyl as mentioned for R.sup.13, such as alkenyloxycarbonyl with C.sub.3 -C.sub.6 -alkenyl as mentioned for R.sup.13 such as alkynyloxycarbonyl with C.sub.3 -C.sub.6 -alkynyl as mentioned for R.sup.13, such as phenoxycarbonyl with phenyl as mentioned for R.sup.13, such as carboxamide, such as N-alkylaminocarbonyl with C.sub.1 -C.sub.6 -alkyl as mentioned for R.sup.13, such as N-cycloalkylaminocarbonyl with C.sub.3 -C.sub.6 -cycloalkyl as mentioned for R.sup.13, such as N-alkenylaminocarbonyl with C.sub.3 -C.sub.6 -alkenyl as mentioned for R.sup.13, such as N-alkynylaminocarbonyl with C.sub.3 -C.sub.6 -alkynyl as mentioned for R.sup.13, such as N-phenylaminocarbonyl with phenyl as mentioned for R.sup.13, such as N,N-dialkylaminocarbonyl with C.sub.3 -C.sub.6 -alkyl as mentioned for R.sup.13, such as N-alkyl-N-cycloalkylaminocarbonyl with C.sub.3 -C.sub.6 -alkyl as mentioned for R.sup.13 and C.sub.1 -C.sub..sub.6 -cycloalkyl as mentioned for R.sup.13, such as N-alkyl-N-phenylaminocarbonyl with C.sub.1 -C.sub.16 -alkyl as mentioned for R.sup.13 and phenyl as mentioned for R.sup.13, such as N-alkoxyaminocarbonyl with alkoxy as described for R.sup.14, such as 1-azacycloalkylcarbonyl with 1-azacycloalkyl as described for R.sup.14, especially methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, N-methylaminocarbonyl, and N,N-dimethylaminocarbonyl; SO.sub.2 NR.sup.15 R.sup.16 such as N-alkylaminosulfonyl with C.sub.1 -C.sub.4 -alkyl as described for R.sup.15, such as N-alkenylaminosulfonyl with C.sub.3 -C.sub.4 -alkenyl as described for R.sup.15, such as N-alkynylaminosulfonyl with C.sub.3 -C.sub.4 -alkynyl as described for R.sup.15, such as N-cyclopropylmethylaminosulfonyl, such as N-cycloalkylaminosulfonyl with C.sub.3 -C.sub.4 -cycloalkyl as described for R.sup.15, such as N,N-dialkylaminosulfonyl with C.sub.1 -C.sub.4 -alkyl as described for R.sup.15 and with C.sub.1 -C.sub.4 -alkyl as described for R.sup.16, such as N-alkyl-N-alkenylaminosulfonyl with C.sub.1 -C.sub.4 -alkyl as described for R.sup.15 and C.sub.3 -C.sub.4 -alkenyl as described for R.sup.16, such as N-alkyl-N-alkynylaminosulfonyl with C.sub.1 -C.sub.4 -alkyl as described for R.sup.16 and C.sub.3 -C.sub.4 -alkynyl as mentioned for R.sup.15, such as N-alkyl-N-cyclopropylmethylaminosulfonyl with C.sub.1 -C.sub..sub.4 -alkyl as described for R.sup.16, such as N-alkyl-N-cycloalkylaminosulfonyl with C.sub.1 -C.sub.4 -alkyl as mentioned for R.sup.16 and C.sub.3 -C.sub.4 -cycloalkyl as described for R.sup.15, such as 1-azacycloalkylsulfonyl with 1-azacycloalkyl as described for R.sup.16, especially N,N-dimethylaminosulfonyl and N,N-diethylaminosulfonyl; SO.sub.2 OR.sup.17 such as alkoxysulfonyl with C.sub.1 -C.sub.4 -alkyl as described for R.sup.17, such as haloalkoxysulfonyl with C.sub.1 -C.sub.4 -haloalkyl as described for R.sup.17, especially methoxysulfonyl, ethoxysulfonyl and isopropoxysulfonyl; OSO.sub.2 R.sup.18 such as alkylsulfonyloxy with C.sub.1 -C.sub.4 -alkyl as described for R.sup.18, such as N,N-dimethylsulfonyloxy, especially methylsulfonyloxy and ethylsulfonyloxy; S(O).sub.n R.sup.19 such as alkylsulfonyl with C.sub.1 -C.sub.4 -alkyl as described for R.sup.19, such as haloalkylsulfonyl with C.sub.1 -C.sub.4 -haloalkyl as described for R.sup.19, such as alkoxyalkylsulfonyl with C.sub.2 -C.sub.4 -alkoxyalkyl as described for R.sup.19, such as alkenylsulfonyl with C.sub.3 -C.sub.4 -alkenyl as mentioned for R.sup.19, such as alkynylsulfonyl with C.sub.3 -C.sub.4 -alkynyl as described for R.sup.19, such as C.sub.3 -C.sub.4 -haloalkenylsulfonyl with C.sub.3 -C.sub.4 -haloalkenyl as described for R.sup.19, such as phenylsulfonyl with phenyl as described for R.sup.19, such alkylsulfinyl with C.sub.1 -C.sub.4 -alkyl as mentioned for R.sup.19, such as haloalkylsulfinyl with C.sub.1 -C.sub.4 -haloalkyl as described for R.sup.19, such as phenylsulfinyl with phenyl as described for R.sup.19, especially methylsulfonyl, ethylsulfonyl, isopropylsulfonyl, propylsulfonyl, methylsulfinyl, and ethylsulfinyl.
R.sup.3 is R.sub.6, especially methyl, ethyl, trifluoromethyl, chloromethyl, methoxymethyl, methylthiomethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 2-methoxyethoxy, methylthio and ethylthio; chlorodifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloroethoxy, 2-methoxyethoxy, methylthio and ethylthio; COQR.sup.13 such as carboxyl, such as alkoxycarbonyl with C.sub.1 -C.sub.6 -alkyl as mentioned for R.sup.13, cycloalkoxycarbonyl with C.sub.3 -C.sub.6 -cycloalkyl as mentioned for R.sup.13 such as alkenyloxycarbonyl with C.sub.3 -C.sub.6 -alkenyl as mentioned for R.sup.13, such as alkynyloxycarbonyl with C.sub.3 -C.sub..sub.6 -alkynyl as mentioned for R.sup.13, such as phenoxycarbonyl with phenyl as mentioned for R.sup.13, such as carboxamide, such as N-alkylaminocarbonyl with C.sub.1 -C.sub.6 -alkyl as mentioned for R.sup.13, such as N-cycloalkylaminocarbonyl with C.sub.3 -C.sub.6 -cycloalkyl as mentioned for R.sup.13, such as N-alkenylaminocarbonyl with C.sub.3 -C.sub.6 -alkenyl as mentioned for R.sup.13, such as N-alkynylaminocarbonyl with C.sub.3 -C.sub.6 -alkynyl as mentioned for R.sup.13, such as N-phenylaminocarbonyl with phenyl as mentioned for R.sup.13, such as N,N-dialkylaminocarbonyl with C.sub.3 -C.sub.6 -alkyl as mentioned for R.sup.13 , such as N-alkyl-N-cycloalkylaminocarbonyl with C.sub.3 -C.sub.6 -alkyl as mentioned for R.sup.13 and C.sub.3 -C.sub.6 -cycloalkyl as mentioned for R.sup.13, such as N-alkyl-N-phenylaminocarbonyl with C.sub.1 -C.sub.6 -alkyl as mentioned for R.sup.13 and phenyl as mentioned for R.sup.13, such as N-alkoxyaminocarbonyl with alkoxy as described for R.sup.14, such as 1-azacycloalkylcarbonyl with 1-azacycloalkyl as described for R.sup.14, especially methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, N-methylaminocarbonyl, and N,N-dimethylaminocarbonyl; SO.sub.2 NR.sup.15 R.sup.16 such as N-alkylaminosulfonyl with C.sub.1 -C.sub.4 -alkyl as described for R.sup.15, such as N-alkenylaminosulfonyl with C.sub.3 -C.sub.4 -alkenyl as described for R.sup.15, such as N-alkynylaminosulfonyl with C.sub.3 -C.sub.4 -alkynyl as described for R.sup.15, such as N-cyclopropylmethylaminosulfonyl, such as N-cycloalkylaminosulfonyl with C.sub.3 -C.sub.4 -cycloalkyl as described for R.sup.15, such as N,N-dialkylaminosulfonyl with C.sub.1 -C.sub.4 -alkyl as described for R.sup.15 and with C.sub.1 -C.sub.4 -alkyl as described for R.sup.16, such as N-alkyl-N-alkenylaminosulfonyl with C.sub.1 -C.sub.4 -alkyl as described for R.sup.15 and C.sub.3 -C.sub.4 -alkenyl as described for R.sup.16, such as N-alkyl-N-alkynylaminosulfonyl with C.sub.1 -C.sub.4 -alkyl as described for R.sup.16 and C.sub.3 -C.sub.4 -alkynyl as mentioned for R.sup.15, such as N-alkyl-N-cyclopropylmethylaminosulfonyl with C.sub.1 -C.sub.4 -alkyl as described for R.sup.16, such as N-alkyl-N-cycloalkylaminosulfonyl with C.sub.1 -C.sub.4 -alkyl as mentioned for R.sup.16 and C.sub.3 -C.sub.4 -cycloalkyl as described for R.sup.15, such as 1-azacycloalkylsulfonyl with 1-azacycloalkyl as described for R.sup.16, especially N,N-dimethylaminosulfonyl and N,N-diethylaminosulfonyl; SO.sub.2 OR.sup.17 such as alkoxysulfonyl with C.sub.1 -C.sub.4 -alkyl as described for R.sup.17, such as haloalkoxysulfonyl with C.sub.1 -C.sub.4 -haloalkyl as described for R.sup.17, especially methoxysulfonyl, ethoxysulfonyl and isopropoxysulfonyl; OSO.sub.2 R.sup.18 alkylsulfonyloxy with C.sub.1 -C.sub.4 -alkyl as described for R.sup.18, such as N,N-dimethylsulfonyloxy, especially methylsulfonyloxy and ethylsulfonyloxy; S(O).sub.n R.sup.19 such as alkylsulfonyl with C.sub.1 -C.sub.4 -alkyl as described for R.sup.19, such as haloalkylsulfonyl with C.sub.1 -C.sub.4 -haloalkyl as described for R.sup.19, such as alkoxyalkylsulfonyl with C.sub.2 -C.sub.4 -alkoxyalkyl as described for R.sup.19, such as alkenylsulfonyl with C.sub.3 -C.sub.4 -alkenyl as mentioned for R.sup.19, such as alkynylsulfonyl with C.sub.3 -C.sub.4 -alkynyl as described for R.sup.19, such as C.sub.3 -C.sub.4 -haloalkenylsulfonyl with C.sub.3 -C.sub.4 -haloalkenyl as described for R.sup.19, such as phenylsulfonyl with phenyl as described for R.sup.19, such alkylsulfinyl with C.sub.1 -C.sub.4 -alkyl as mentioned for R.sup.19, such as haloalkylsulfinyl with C.sub.1 -C.sub.4 -haloalkyl as described for R.sup.19, such as phenylsulfinyl with phenyl as described for R.sup.19, especially methylsulfonyl, ethylsulfonyl, isopropylsulfonyl, propylsulfonyl, methylsulfinyl, and ethylsulfinyl.
R.sup.4 is hydrogen, halogen, especially fluorine, chlorine or bromine, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and the corresponding alkoxy and alkylthio radicals, especially methyl, ethyl, fluoromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, methoxy, ethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy,chlorodifluoromethoxy,trifluoromethoxy, dichlorofluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 2-chloroethoxy;
R.sup.5 is hydrogen; nitro or R.sup.2, especially fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, 2-chloroethoxy, 2-methoxyethoxy, trifluoromethoxy, methoxycarbonyl, ethoxycarbonyl, N,N-dimethylaminocarbonyl, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, N-isopropylaminosulfonyl and N,N-dimethylaminosulfonyl;
R.sup.6 is hydrogen; halogen such as fluorine, chlorine, bromine or iodine, especially fluorine, chlorine and bromine; cyano; C.sub.1 -C.sub.4 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, which can be substituted by one to five halogens especially fluorine, chlorine or bromine and/or one of the following: hydroxyl, mercapto, cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, such as methoxy, ethoxy, propoxy, butoxy, 1-methylethoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and the corresponding alkylthio radicals, especially methyl, ethyl, trifluoromethyl, chloromethyl, methoxymethyl and methylthiomethyl; C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, such as methoxy, ethoxy, propoxy, butoxy, 1-methylethoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, which can be substituted by one to five halogens, especially fluorine, chlorine or bromine, and/or by the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, such as methoxy, ethoxy, propoxy, butoxy, 1-methylethoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy, which can be substituted by halogens, especially fluorine, chlorine or bromine, and the corresponding alkylthio radicals, especially methoxy, ethoxy, isopropyloxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, difluoromethoxy, 2-chloroethoxy, 2-methoxyethoxy, methylthio and ethylthio;
R.sup.7 is nitro or R.sup.2, especially fluorine, chlorine, bromine, methyl, ethyl, chloromethyl, fluoromethyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, dichlorofluoromethyl, methoxymethyl, methoxycarbonyl, N,N-dimethylaminocarbonyl and ethoxycarbonyl;
R.sup.8 is hydrogen, nitro or R.sup.2, especially fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, trifluoromethyl, trichloromethyl, 2-fluoroethyl, 2-chloroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, methoxymethyl, 2-mathoxyethyl, 1-methoxyethyl, 2-methoxy-1-methylethyl, ethoxymethyl, benzyl, cyclopropyl, cyclopentyl, cyclohexyl, phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 1-methyl-3-pyrazolyl, 1-methyl-4-pyrazolyl, 1-methyl-5-pyrazolyl, 1-ethyl-3-pyrazolyl, 1-ethyl-4-pyrazolyl, 1-ethyl-5-pyrazolyl, methoxy, ethoxy, isopropoxy, 2-chloroethoxy, 2-methoxyethoxy, trifluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, 2,2,2-trifluoroethoxy, phenoxy, benzyloxy, methylthio, ethylthio, phenylthio, benzylthio, 2-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 2-propynyl, 1-methyl-2-propynyl, 2-butynyl, methylcarbonyl, ethylcarbonyl, cyclopropylcarbonyl, chloromethylcarbonyl, bromomethylcarbonyl, fluoromethylcarbonyl, trifluoromethylcarbonyl, methoxymethylcarbonyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-methoxyethoxcarbonyl, benzyloxycarbonyl, aminocarbonyl, N-methylaminocarbonyl, N,N-dimethylaminocarbonyl, N-ethylaminocarbonyl, N,N-diethylaminocarbonyl, N-isopropylaminocarbonyl, N-benzylaminocarbonyl, N-phenylaminocarbonyl, N-methoxyaminocarbonyl, N-ethoxyaminocarbonyl, N,N-dimethylaminosulfonyl, N-methyl-N-ethylaminosulfonyl, N,N-diethylaminosulfonyl, N-methylaminosulfonyl, N-ethylaminosulfonyl, methoxysulfonyl, ethoxysulfonyl, isopropoxysulfonyl, 2-chloroethoxysulfonyl, 2,2,2-trifluoroethoxysulfonyl, methylsulfonyloxy, ethylsulfonyloxy, isopropylsulfonyloxy, N,N-dimethylaminosulfonyloxy, methylsulfinyl, ethylsulfinyl, isopropylsulfinyl, phenylsulfinyl, methylsulfonyl, ethylsulfonyl, isopropylsulfonyl or propylsulfonyl; or 2 vicinal R.sup.2 radicals together form a C.sub.3 chain such as propylene or a C.sub.4 -C.sub.6 chain in which one methylene can be replaced by oxygen or C.sub.1 -C.sub.4 -alkylamino such as methyl-, ethyl-, propyl- or butylimino;
R.sup.9 is hydrogen; unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl, especially C.sub.1 -C.sub.4 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, particularly suitable substituents being the following: fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkoxy, especially methoxy, ethoxy, or phenyl; C.sub.3 -C.sub.6 -cycloalkyl or cycloalkenyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl or 3-cyclohexenyl, each of which can be further substituted, preferably by methyl, ethyl, fluorine, chlorine or trifluromethyl; unsubstituted or substituted phenyl; C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkynyl as mentioned for R.sup.2, especially vinyl, 2-propenyl and 2-propynyl; COR.sup.21, especially methylcarbonyl, ethylcarbonyl and phenylcarbonyl;
R.sup.10 is unsubstituted or substituted phenyl, benzyl, phenoxy, phenylthio, benzyloxy or benzylthio, suitable and preferred substituents being fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy and ethoxy;
R.sup.11 is hydrogen; unsubstituted or substituted phenyl or benzyl, e.g. 2-substituted or 2,4-disubstituted or 2,6-disubstituted or 2,4,6-trisubstituted phenyl or benzyl, suitable substituents being the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 - haloalkoxy, C.sub.1 -C.sub.4 -haloalkylthio, especially phenyl, 2-chlorophenyl, 2-fluorophenyl, 2-methylphenyl, 2-trifluoromethylphenyl, 2-mathoxyphenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 2,6-difluorophenyl, 2,6-dimethylphenyl, 2-chloro-4-trifluoromethylphenyl and 2,6-dichloro-4-trifluoromethylphenyl;
R.sup.12 is C.sub.1 -C.sub.4 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, each of which may be substituted by halogen, especially fluorine or chlorine or by methoxy; C.sub.3 -C.sub.5 -cycloalkyl such as cyclopropyl, cyclobutyl or cyclopentyl, unsubstituted or substituted by chlorine or fluorine; C.sub.3 -C.sub.4 -alkenyl such as 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl or 2-methyl-2-propenyl;
Q is oxygen or NR.sup.14
R.sup.13 is hydrogen; C.sub.1 -C.sub.6 -alkyl, especially C.sub.1 -C.sub.4 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, substituted alkyl e.g. by halogen, especially fluorine, chlorine or bromine, C.sub.1 -C.sub.4 -alkoxy, especially methoxy or ethoxy; unsubstituted or substituted C.sub.3 -C.sub..sub.9 -cycloalkyl as mentioned for R.sup.9, unsubstituted or substituted by methyl or ethyl; C.sub.3 -C.sub.6 -alkenyl such as 2-propenyl, 2-butenyl, 3-butenyl, 1methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1,-dimethyl-3-butenyl, 1,2 -dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl; C.sub.3 -C.sub.6 -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl; unsubstituted or substituted phenyl, e.g. by halogen, especially fluorine, chlorine or bromine, C.sub.1 -C.sub.4 -alkyl, especially methyl or ethyl, C.sub.1 -C.sub.4 -haloalkyl, especially trifluoromethyl, difluoromethyl, chlorodifluoromethyl or trichloromethyl, C.sub.1 -C.sub.4 -alkoxy, especially methoxy or ethoxy, C.sub.1 -C.sub.4 -haloalkoxy, especially trifluoromethoxy, difluoromethoxy or chlorodifluoromethoxy;
R.sup.14 is OR.sup.20, especially methyl or ethyl; R.sup.13 or forms together with R.sup.13 a C.sub.4 -C.sub.6 -alkylene chain such as butylene, pentylene or hexylene in which one methylene can be replaced by oxygen or C.sub.1 -C.sub.4 -alkylamino, e.g. methyl- or ethylimino;
R.sup.15 is C.sub.1 -C.sub.4 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl; C.sub.3 -C.sub.4 -alkenyl or alkynyl, e.g. 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butynyl, 2-propynyl, 3-butynyl, cyclopropylmethyl, cyclopropyl or cyclobutyl;
R.sup.16 is hydrogen; C.sub.1 -C.sub.4 -alkyl as mentioned for R.sup.15, C.sub.3 -C.sub..sub.4 -alkenyl, e.g. 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl; a C.sub.4 -C.sub.6 -alkylene chain in which one methylene can be replaced by oxygen;
R.sup.17 is C.sub.1 -C.sub.4 -alkyl as mentioned for R.sup.15, C.sub.1 -C.sub.4 -haloalkyl, especially C.sub.1 -C.sub.2 -haloalkyl, such as chloromethyl, dichloromethyl, trichloromethyl, chlorofluoromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
R.sup.18 is C.sub.1 -C.sub.4 -alkyl as mentioned for R.sup.15 or N,N-dimethylamino;
R.sup.19 is C.sub.1 -C.sub.4 alkyl or haloalkyl as mentioned for R.sup.17, C.sub.2 -C.sub.4 -alkoxyalkyl such as methoxy or ethoxyethyl; C.sub.3 -C.sub.4 -alkenyl such as 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl, unsubstituted or substituted by halogen, especially fluorine or chlorine; C.sub.3 -C.sub.4 -alkynyl such as 2-propynyl, 2-butynyl or 3-butynyl; phenyl or phenyl substituted by one to three fluorine, chlorine, bromine, methyl or methoxy;
n is 1 or 2
R.sup.20 is hydrogen or C.sub.1 -C.sub.4 -alkyl as mentioned for R.sup.15 ;
R.sup.21 is R.sup.12, especially methyl, ethyl, trifluoromethyl, difluoromethyl or cyclopropyl; phenyl, benzyl, unsubstituted or substituted by, for example, halogen, especially fluorine, chlorine or bromine, cyano, C.sub.1 -C.sub.4 -alkyl, especially methyl or ethyl, C.sub.1 -C.sub.4 -alkoxy which is unsubstituted or substituted by halogen, especially methoxy, ethoxy or 2-chloroethoxy.
The herbicidal and growth-regulating compounds I according to the invention and the agents containing them can be applied, for example, in the form of directly sprayable solutions, powders, suspensions, including high percentage aqueous, oily or other suspensions or dispersions, emulsions, oily dispersions, pastes, dusting agents, broadcasting agents or granules by spraying, atomizing, dusting, broadcasting or watering. The application forms depend on the purposes for which they are used; in any event, they should ensure maximum dispersion of the active ingredients according to the invention.
The compounds I are suitable in general for preparing directly sprayable solutions, emulsions, pastes or oily dispersions. Suitable inert additives are mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, also coaltar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons e.g. toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, chlorobenzene, isophorone or highly polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone or water.
Aqueous application forms can be prepared from emulsion concentrates, dispersions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oily dispersions, the substances can be homogenized as such or dissolved in an oil or solvent, using wetting agents, adhesion promoters, dispersants or emulsifiers, in water. However, concentrates which are suitable for dilution with water can also be prepared from active substance, wetting agent, adhesion promoter, dispersant or emulsifier and, possibly, solvent or oil.
Suitable surfactants are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, e.g. lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenol and tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulfite waste liquors or methylcellulose.
Powders, dusting and broadcasting agents can be prepared by mixing or milling the active substances together with a solid carrier.
Granules, for example coated, impregnated or homogeneous granules, can be prepared by binding the active ingredients to solid carriers such as mineral earths such as silica gel, silicic acids, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, milled plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas and vegetable products such as cereal meal, bark meal, wood meal and nutshell meal, cellulose powder or other solid carriers.
The formulations contain from 0.1 to 95% by weight, preferably from 0.5 to 90% by weight, of active ingredient. The active ingredients are employed in a purity of from 90 to 100%, preferably 95% to 100% (according to the NMR spectrum).
The compounds I according to the invention can be formulated as follows, for example:
I. 90 parts by weight of compound No 40 are mixed with 10 parts by weight of N-methyl-.alpha.-pyrrolidone to give a solution which is suitable for application in the form of very small droplets.
II. 20 parts by weight of compound No. 40 are dissolved in a mixture composed of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Dispersing the solution in 100,000 parts by weight of water results in an aqueous dispersion which contains 0.02% by weight of the active ingredient.
III. 20 parts by weight of compound No. 40 are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Dispersing the solution in 100,000 parts by weight of water results in an aqueous dispersion containing 0.02% by weight of the active ingredient.
IV. 20 parts by weight of active ingredient No. 40 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210.degree. to 280.degree. C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Dispersing the solution in 100,000 parts by weight of water results in an aqueous dispersion containing 0.02% by weight of the active ingredient.
V. 20 parts by weight of active ingredient No. 40 are thoroughly mixed with 3 parts by weight of sodium diisobutylnaphthylene-.alpha.-sulfonate, 17 parts by weight of the sodium salt of a ligninsulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and milled in a hammer mil. Dispersing the mixture in 20,000 parts by weight of water results in a spray liquor containing 0.1% by weight of the active ingredient.
VI. 3 parts by weight of active ingredient No. 40 are mixed with 97 parts by weight of finely divided kaolin. This results in a dusting agent containing 3% by weight of active ingredient.
VII. 30 parts by weight of active ingredient No. 40 are intimately mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of liquid paraffin which has been sprayed on to the surface of this silica gel. This results in a formulation of the active ingredient with good adhesion.
VIII. 20 parts by weight of active ingredient No. 40 are intimately mixed with 2 parts by weight of calcium dodecylbenzosulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a liquid paraffin.
This results in a stable oily dispersion.
The herbicidal and growth-regulating agents for the active ingredients can be applied in the pre-emergence or post-emergence process. If the active ingredients are less well tolerated by certain crop plants it is possible to employ application techniques in which the herbicides are spray on in such a way that the leaves of the sensitive crop plants are touched as little as possible while the active ingredients reach the leaves of unwanted plants growing thereunder or the uncovered surface of the soil (post-directed, lay-by).
The application rates of active ingredient when used as herbicides depend on the control to be achieved, the season, the target plants and the growth stage and are from 0.001 to 3, preferably 0.01 to 2 kg/ha active substance.
The compounds of the formula I are able to influence virtually all stages of development of a plant in various ways and are therefore employed as plant growth regulators. The variety of effects of the growth regulators depends, in particular,
a) on the species and variety of the plant,
b) on the time of application relative to the stage of development of the plant and to the season,
c) on the site and method of application (e.g. seed dressing, soil treatment, leaf application or trunk injection for trees)
d) on climatic factors, e.g. temperature, amount of precipitation, also on length of daylight and light intensity
e) on the soil characteristics (including fertilization),
f) on the formulation or application form of the active ingredient and, finally,
g) on the active substance concentrations used.
A few of the range of possible uses of the plant growth regulators of the formula I according to the invention in crop cultivation, in agriculture and horticulture are mentioned hereinafter.
A. The compounds according to the invention can be used to inhibit greatly the vegetative growth of the plants, which is evident, in particular, from a reduction in the height of growth. The treated plants accordingly exhibit stunted growth; there is also seen to be a darker color of the leaves.
It is advantageous in practice to reduce the vigor of grass growth on the edges of roads, hedgerows, canal banks and on grassed areas such as parks, sports grounds and orchards, lawns and airports to reduce the labor and cost of grass cutting.
Also of economic interest is the increase in the resistance to lodging of crops prone to this, such as cereals, corn, sunflowers and soybean. The shortening and strengthening of the stalk caused thereby reduces or eliminates the risk of lodging (bending over) of plants under unfavorable weather conditions before harvest.
Another important use of growth regulators is to reduce the height of growth and to alter the timing of ripening of cotton. This makes possible completely mechanized harvesting of this important crop plant.
The costs of pruning fruit and other trees can be saved by using the growth regulators. In addition, the alternation of fruit trees can be stopped by growth regulators.
Growth regulators can also be used to increase or inhibit the production of lateral branches by the plants. This is of interest when, for example, the production of side shoots (suckers) by tobacco plants is to be inhibited in favor of leaf growth.
Growth regulators can be used, for example, to increase considerably the frost resistance of winter rape. On the one hand, this reduces the height of growth and the development of an excessive (and thus particularly frost-susceptible) leaf or plant mass. On the other hand, the young rape plants are, after sowing and before onset of winter frosts, held back in the vegetative stage of development despite favorable growth conditions. This also eliminates the risk of frost on such plants which are prone to premature breakdown of flowering inhibition and to transition into the generative phase. It is also advantageous for other crops, e.g. winter cereals, to be treated with the compounds according to the invention in the fall and thus be well tillered but not too lush for the start of the winter. It is possible in this way to avert an increased sensitivity to frost and, because of the relatively low leaf and plant mass, attack by various diseases (e.g. fungal disease). The inhibition of vegetative growth additionally makes it possible with many crop plants to plant the soil more densely so that a higher yield per soil area can be achieved.
B. The growth regulators can be used to achieve higher yields both of plants parts and of plant constituents. Thus, for example, it is possible to induce the growth of larger amounts of buds, flowers, leaves, fruit, seed kernels, roots and tubers, to increase the content of sugar in sugar beet, sugar cane and citrus fruit, to raise the protein content in cereals or soybean or to stimulate rubber trees to an increased flow of latex.
In this connection, the compounds of the formula I can bring about increased yields by intervening in the plant metabolism or by promoting or inhibiting vegetative and/or generative growth.
C. Finally, plant growth regulators can be used to achieve both an increase or reduction in the length of stages of development and an increase or reduction in the rate of ripening of the harvested parts of the plants before or after the harvest.
Of economic interest is, for example, the facilitation of harvesting which is made possible by the concentration in time of the fall or reduced adhesion to the tree in the case of citrus fruit, olives or other species and varieties of pomes, drupes and caryopses. The same mechanism, i.e. the promotion of the development of separating tissue between the fruit and the leaf and shoot part of the plant is also essential for well-controlled defoliation of crop plants such as cotton.
D. Furthermore, growth-regulators can be used to reduce the water requirement of plants. This is particularly important for agricultural land which needs very costly artificial irrigation, e.g. in arid or semi-arid areas. Use of the substances according to the invention allows the intensity of irrigation to be reduced and thus improves the economics of farming. Growth regulators have the effect of improving utilization of the available water because, inter alia,
the width of opening of the stomata is reduced
a thicker epidermis and cuticula is formed
the spread of roots in the soil is improved and
the microclimate in the crop is beneficially affected by more compact growth.
The growth regulators of the formula I to be used according to the invention can be delivered to the crop plants both as seeds (as seed dressing) and via the soil, i.e. through the roots and, particularly preferably, through the leaf by spraying.
A wide variation in the application rate is possible because they are well tolerated by plants.
In view of the wide variety of application methods, the compounds according to the invention or the agents containing them can be used to eradicate unwanted plants in a large number of crops.
______________________________________Crop list:Botanical name English name______________________________________Allium cepa cooking onionAnanas comusus pineappleArachis hypogaea peanutAsparagus officinalis asparagusBeta vulgaris spp. altissima sugar beetBeta vulgaris spp. rapa fodder beetBrassica napus var. napus rapeBrassica napus var. napobrassica cabbage rapeBrassica rapa var. silvestris turnip rapeCamellia sinensis tea plantCarthamus tinctorius safflowerCarya illinoinensis pecan nutCitrus limon lemonCitrus sinensis orangeCoffea arabica (Coffea canephora, coffeeCoffea liberica)Cucumis sativus cucumberCynodon dactylon Bermuda grassDaucus carota carrotElaeis guineensis oil palmFragaria vesca strawberryGlycine max soybeanGossypium hirsutum (Gossypium cottonaboreum, Gossypium herbaceumGossypium vitifolium)Helianthus annuus sunflowerHevea brasiliensis para rubber treeHordeum vulgare barleyHumulus lupulus hopsIpomoea batatas sweet potatoJuglans regia walnutLens culinaris lentilLinum usitatissimum flaxLycopersicon lycopersicum tomatoMalus spp. appleManihot esculenta cassavaMedicago sativa alfalfaMusa spp. bananasNicotiana tabacum ( N. rustica) tobaccoOlea europaea oliveOryza sativa ricePhaseolus lunatus lima beanPhaseolus vulgaris bush beanPicea abies sprucePinus spp. pinePisum sativum garden peaPrunus avium sweet cherryPrunus persica peachPyrus communis pearRibes sylvestre redcurrantRicinus communis castor beanSaccharum officinarum sugar caneSecale cereale ryeSolanum tuberosum potatoSorghum bicolor (S. vulgare) milletTheobroma cacao cocoaTrifolium pratense red cloverTriticum aestivum wheatTriticum durum durum wheatVicia faba horse beanVitis vinifera grape vineZea mays corn______________________________________
To extend the spectrum of action and to achieve synergistic effects, the compounds I according to the invention can be mixed and applied together with numerous representatives of other groups of herbicides or growth regulators. Examples of suitable mixing partners are diazine, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiolcarbamates, halo carboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1,3-dione derivatives, quinolinecarboxylic acid derivatives, sulfonylurea derivatives, aryloxy- and heteroaryloxyphenoxypropionic acids and the salts, esters and amides thereof, and others.
It may also be beneficial to apply the compounds I, alone or combined with other herbicides, mixed together with other crop protection agents, for example with pesticides, fungicides or bactericides. Also of interest is the possibility of mixing with mineral salt solutions which are employed to eliminate deficiencies in nutrients or trace elements. It is also possible to add non-phytotoxic oils and oil concentrates.
The examples which follow describe examples of the preparation of the compounds according to the invention.
EXAMPLE 1
N-(2-Methoxycarbonylphenylsulfonyl)-1,5-dimethylpyrazole-3-carboxamide
10.8 g of 2-methoxycarbonylphenylsulfonamide, 8.6 g of 1,5-dimethylpyrazole-3-carbonyl chloride and 13.8 g of potassium carbonate in 200 ml of absolute acetone are refluxed for 8 h. The solvent is removed by distillation and then the residue is taken up in water and the pH is adjusted to 2. The precipitate is filtered off with suction and washed with H.sub.2 O until neutral. The residue is stirred with ether, filtered off with suction and dried under reduced pressure. 11.6 g of N-(2-methoxycarbonylphenylsulfonyl)-1,5-dimethylpyrazole-3-carboxamide with a melting point of 176.degree.-177.degree. C. are obtained (active ingredient Example No. 40).
EXAMPLE 2
N-(2-Thienylsulfonyl)-1-methylpyrazole-4-carboxamide
3.8 g of 1-methylpyrazole-4-carboxylic acid and 4.9 g of carbonyldiimidazole in 100 ml of 1,2-dichloroethane are heated at 55.degree. C. for 3.5 h. 4.9 g of 2-thienylsulfonamide and 5.4 ml of triethylamine are added and then the mixture is heated at 55.degree. C. for 13 h. After cooling, 40 ml of 10% strength aqueous NaOH solution are added and then the pH of the aqueous phase is adjusted to 1. The precipitate is removed and dried under reduced pressure. 5.2 g of N-(2-thienylsulfonyl)-1-methylpyrazole-4-carboxamide with a melting point of 174.degree.-180.degree. C. are obtained (active ingredient Example No. 103).
EXAMPLE 3
N-(2-Chlorophenylsulfonyl)-1,4-dimethylimidazole-2-carboxamide
2.0 g of 1,4-dimethylimidazole and 4.3 g of 2-chlorophenylsulfonyl isocyanate in 200 ml of toluene are refluxed for 6 h. The precipitate which forms on cooling is filtered off with suction and washed with acetone. The residue is suspended in acetonitrile/methanol and refluxed for 0.5 h. After cooling, the solid is filtered off with suction and dried under reduced pressure. 2.3 g of N-(2-chlorophenylsulfonyl)-1,4-dimethylimidazole-2-carboxamide with a melting point of 230.degree.-231.degree. C. are obtained. (Active ingredient Example No. 113).
EXAMPLE 4
N-(2,6-Dichlorophenylsulfonyl)-2-methoxythiazole-4-carboxamide
2.3 g of N-(2,6-dichlorophenylsulfonyl)-2-bromothiazole-4-carboxamide and 1.6 g of sodium methanolate in 45 ml of methanol are refluxed for 12 h. After cooling, the precipitate is filtered off with suction, washed with methanol and then dried under reduced pressure. 1.8 g of N-(2,6-dichlorophenylsulfonyl)-2-methoxythiazole-4-carboxamide with a melting point of 162.degree.-165.degree. C. are obtained. (Active ingredient Example No. 34).
The compounds which are listed in Table 1 which follows and in which the substituents A are as follows can be obtained correspondingly by appropriate choice of the starting materials and adjustment of the process conditions.
______________________________________A1-1: R.sup.2 = CO.sub.2 CH.sub.3 R.sup.3, R.sup.4 = HA1-2: R.sup.2 = CO.sub.2 CH.sub.2 CH.sub.3 R.sup.3, R.sup.4 = HA1-3: R.sup.2 = CO.sub.2 CH(CH.sub.3).sub.2 R.sup.3, R.sup.4 = HA1-4: R.sup.2 = CO.sub.2 CH.sub.3 R.sup.3 = 6-Cl, R.sup.4 = HA1-5: R.sup.2 = CO.sub.2 CH.sub.3 R.sup.3 = 6-OCH.sub.3, R.sup.4 = HA1-6: R.sup.2 = CO.sub.2 CH.sub.3 R.sup.3 = 6-CH.sub.3, R.sup.4 = HA1-7: R.sup.2 = CO.sub.2 CH.sub.3 R.sup.3 = 6-F, R.sup.4 = HA1-8: R.sup.2 = CO.sub.2 CH.sub.3 R.sup.3 = 3-Cl, R.sup.4 = HA1-9: R.sup.2 = CO.sub.2 CH.sub.3 R.sup.3 = 3-F, R.sup.4 = HA1-10: R.sup.2 = CO.sub.2 CH.sub.3 R.sup.3 = 4-Cl, R.sup.4 = HA1-11: R.sup.2 = CO.sub.2 CH.sub.3 R.sup.3 = 5-Cl, R.sup.4 = HA1-12: R.sup.2 = CO.sub.2 CH.sub.3 R.sup.3 = 5-F, R.sup.4 = HA1-13: R.sup.2 = CO.sub.2 CH.sub.3 R.sup.3 = 5-OCH.sub.3, R.sup.4 = HA1-14: R.sup.2 = CO.sub.2 CH.sub.3 R.sup.3 = 5-OCHF.sub.2, R.sup.4 = HA1-15: R.sup.2 = CO N(CH.sub.3).sub.2 R.sup.3, R.sup.4 = HA1-16: R.sup.2 = CO N(CH.sub.3).sub.2 R.sup.3 = 3-Cl R.sup.4 = HA1-17: R.sup.2 = CO N(CH.sub.3).sub.2 R.sup.3 = 3-F R.sup.4 = HA1-18: R.sup.2 = CH.sub.3 R.sup.3 = H, R.sup.4 = HA1-19: R.sup.2 = CH.sub.2 Cl R.sup.3, R.sup.4 = HA1-20: R.sup.2 = CH.sub.2 OCH.sub.3 R.sup.3, R.sup.4 = HA1-21: R.sup.2 = CH.sub.2 SCH.sub.3 R.sup.3, R.sup.4 = HA1-22: R.sup.2 = CF.sub.3 R.sup.3, R.sup.4 = HA1-23: R.sup.2 = CH.sub.3 R.sup.3 = 5-Cl, R.sup.4 = HA1-24: R.sup.2 = CH.sub.3 R.sup.3 = 5-CH.sub.3, R.sup.4 = HA1-25: R.sup.2 = CH.sub.3 R.sup.3 = 5-OCH.sub.3, R.sup.4 = HA1-26: R.sup.2 = F R.sup.3, R.sup.4 = HA1-27: R.sup.2 = F R.sup.3 = 6-F, R.sup.4 = HA1-28: R.sup.2 = Cl R.sup.3, R.sup.4 = HA1-29: R.sup.2 = Cl R.sup. 3 = 6-Cl, R.sup.4 = HA1-30: R.sup.2 = Cl R.sup.3 = 6-CH.sub.3, R.sup.4 = HA1-31: R.sup.2 = Cl R.sup.3 = 6-OCH.sub.3, R.sup.4 = HA1-32: R.sup.2 = Cl R.sup.3 = 5-CO.sub.2 CH.sub.3, R.sup.4 = HA1-33: R.sup.2 = Cl R.sup.3 = 5-Cl, R.sup.4 = HA1-34: R.sup.2 = Cl R.sup.3 = 3-Cl, R.sup.4 = HA1-35: R.sup.2 = Cl R.sup.3 = 6-Cl, R.sup.4 = 5-ClA1-36: R.sup.2 = Cl R.sup.3 = 6-Cl, R.sup.4 = 4-ClA1-37: R.sup.2 = Br R.sup.3, R.sup.4 = HA1-38: R.sup.2 = Br R.sup.3 = 6-Br, R.sup.4 = HA1-39: R.sup.2 = CN R.sup.3, R.sup.4 = HA1-40: R.sup.2 = OCH.sub.3 R.sup.3, R.sup.4 = HA1-41: R.sup.2 = OCH.sub.2 CH.sub.3 R.sup.3, R.sup.4 = HA1-42: R.sup.2 = OCH(CH.sub.3).sub.2 R.sup.3, R.sup.4 = HA1-43: R.sup.2 = OCH.sub.2 CH.sub.2 Cl R.sup.3, R.sup.4 = HA1-44: R.sup.2 = CH.sub.2 CH.sub.2 OCH.sub.3 R.sup.3, R.sup.4 = HA1-45: R.sup.2 = OCH.sub.2 CF.sub.3 R.sup.3, R.sup.4 = HA1-46: R.sup.2 = OCF.sub.3 R.sup.3, R.sup.4 = HA1-47: R.sup.2 = OCF.sub.2 H R.sup.3, R.sup.4 = HA1-48: R.sup.2 = OCH.sub.3 R.sup.3 = 5-Br, R.sup.4 = HA1-49: R.sup.2 = OCH.sub.3 R.sup.3 = 5-OCH.sub.3, R.sup.4 = HA1-50: R.sup.2 = OCH.sub.2 CF.sub.3 R.sup.3 = 5-OCH.sub.2 CF.sub.3, R.sup.4 = HA1-51: R.sup.2 = SCH.sub.3 R.sup.3, R.sup.4 = HA1-52: R.sup.2 = SCH.sub.2 CH.sub.3 R.sup.3, R.sup.4 = HA1-53: R.sup.2 = SO.sub.2 CH.sub.3 R.sup.3, R.sup.4 = HA1-54: R.sup.2 = SO.sub.2 CH.sub.2 CH.sub.3 R.sup.3, R.sup.4 = HA1-55: R.sup.2 = SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3 R.sup.3, R.sup.4 = HA1-56: R.sup.2 = SO.sub.2 CH(CH.sub.3).sub.2 R.sup.3, R.sup.4 = HA1-57: R.sup.2 = SO.sub.2 N(CH.sub.3).sub.2 R.sup.3, R.sup.4 = HA1-58: R.sup.2 = OSO.sub.2 CH.sub.3 R.sup.3, R.sup.4 = HA1-59: R.sup.2 = OSO.sub.2 CH.sub.2 CH.sub.3 R.sup. 3, R.sup.4 = HA1-60: R.sup.2 = COCH.sub.3 R.sup.3, R.sup.4 = HA1-61: ##STR12## R.sup.3, R.sup.4 = HA2-1: R.sup.5 = H R.sup.6 = HA2-2: R.sup.5 = CO.sub.2 CH.sub.3 R.sup.6 = HA2-3: R.sup.5 = CO.sub.2 CH.sub.2 CH.sub.3 R.sup.6 = HA2-4: R.sup.5 = CON(CH.sub.3).sub.2 R.sup.6 = HA2-5: R.sup.5 = Cl R.sup.6 = HA2-6: R.sup.5 = CF.sub.3 R.sup.6 = HA2-7: R.sup.5 = OCH.sub.2 CH.sub.3 R.sup.6 = HA2-8: R.sup.5 = SO.sub.2 CH.sub.3 R.sup.6 = HA2-9: R.sup.5 = SO.sub.2 CH.sub.2 CH.sub.3 R.sup.6 = HA3-1: R.sup.5 = H R.sup.6 = HA3-2: R.sup.5 = CON(CH.sub.3).sub.2 R.sup.6 = HA6-1: R.sup.5 = H R.sup.4 = H X = SA6-2: R.sup.5 = Cl R.sup.4 = H X = SA6-3: R.sup.5 = H R.sup.4 = 4-Cl X = SA6-4: R.sup.5 = H R.sup.4 = 5-Cl X = SA6-5: R.sup.5 = CO.sub.2 CH.sub.3 R.sup.4 = H X = SA7-1: R.sup.6 = H R.sup.7 = CO.sub.2 CH.sub.3 X = SA7-2: R.sup.6 = H R.sup.7 = CON(CH.sub.3).sub.2 X = SA8-1: R.sup.6 = H R.sup.7 = CO.sub.2 CH.sub.3 X = SA9-1: R.sup.5 = H R.sup.4 = HA9-2: R.sup.5 = 2-CO.sub.2 CH.sub.3 R.sup.4 = HA9-3: R.sup.5 = 2-Cl R.sup.4 = HA9-4: R.sup.5 = 8-CO.sub.2 CH.sub.3 R.sup.4 = HA9-5: R.sup.5 = 8-Cl R.sup.4 = HA9-6: R.sup.5 = 8-OCH.sub.3 R.sup.4 = HA9-7: R.sup.5 = 8-OCH.sub.2 CH.sub.2 OCH.sub.3 R.sup.4 = HA9-8: R.sup.5 = 8-OCH.sub.2 CH.sub.2 Cl R.sup.4 = HA10-1: R.sup.5 = H R.sup.4 = HA10-2: R.sup.5 = 1-CO.sub.2 CH.sub.3 R.sup.4 = HA10-3: R.sup.5 = 1-Cl R.sup.4 = HA10-4: R.sup.5 = 1-OCH.sub.2 CH.sub.2 OCH.sub.3 R.sup.4 = HA10-5: R.sup.5 = 1-OCH.sub.2 CH.sub.2 Cl R.sup.4 = H______________________________________
TABLE 1______________________________________ ##STR13##No. A B M.p. (.degree.C.)______________________________________ 1 A1-1 2-furyl 2 A1-26 2-furyl 158-160 3 A1-29 2-furyl 4 A1-1 2,5-dimethyl-3-furyl 148-150 5 A1-11 2,5-dimethyl-3-furyl 6 A1-1 5-nitro-2-furyl 7 A6-1 5-nitro-2-furyl 8 A1-40 5-chloro-2-thienyl 175-177 9 A1-1 5-chloro-2-thienyl10 A1-1 5-methyl-2-thienyl 180-18111 A1-18 5-methyl-2-thienyl12 A1-1 2-pyrrolyl 22013 A1-29 2-pyrrolyl 21014 A1-1 1-methyl-2-pyrrolyl 162-16415 A1-28 1-methyl-2-pyrrolyl16 A1-1 3-isoxazolyl17 A1-26 3-isoxazolyl 170-17118 A1-29 5-methyl-3-isoxazolyl 13819 A1-1 5-methyl-3-isoxazolyl20 A1-1 5-chloromethyl-3-isoxazolyl21 A1-40 5-chloromethyl-3-isoxazolyl22 A1-30 5-phenyl-3-isoxazolyl 200-20223 A1-1 3-methyl-4-isoxazolyl 142-14324 A1-1 3,5-dimethyl-4-isoxazolyl25 A1-28 3,5-dimethyl-4-isoxazolyl26 A1-1 5-isoxazolyl27 A1-27 5-isoxazolyl28 A1-1 3-methyl-5-isoxazolyl 123-12729 A1-30 3-methyl-5-isoxazolyl 137-13930 A1-1 2-bromo-4-thiazolyl31 A1-29 2-bromo-4-thiazolyl >23032 Al-30 2-bromo-4-thiazolyl 15133 A1-1 2-methoxy-4-thiazolyl34 A1-29 2-methoxy-4-thiazolyl 162-16535 A1-30 2-methoxy-4-thiazolyl 13836 A1-1 2-methyl-4-thiazolyl37 A1-29 2-methyl-4-thiazolyl38 A1-1 4-methyl-2-thiazolyl39 A1-30 4-methyl-2-thiazolyl40 A1-1 1,5-dimethyl-3-pyrazolyl 176-17741 A1-29 1,5-dimethyl-3-pyrazolyl 135-13842 A1-30 1,5-dimethyl-3-pyrazolyl 12343 A1-28 1,5-dimethyl-3-pyrazolyl 89-9144 A1-40 1,4-dimethyl-3-pyrazolyl 12345 A1-18 1,5-dimethyl-3-pyrazolyl 144-14546 A1-27 1,5-dimethyl-3-pyrazolyl 145-14747 A1-33 1,5-dimethyl-3-pyrazolyl 172-17848 A1-11 1,5-dimethyl-3-pyrazolyl 172-17449 A1-10 1,5-dimethyl-3-pyrazolyl 166-16950 A1-9 1,5-dimethyl-3-pyrazolyl 168-16951 A1-2 1,5-dimethyl-3-pyrazolyl 124-12552 A1-3 1,5-dimethyl-3-pyrazolyl53 A1-15 1,5-dimethyl-3-pyrazolyl 201-20354 A2-9 1,5-dimethyl-3-pyrazolyl 185-18855 A7-1 1,5-dimethyl-3-pyrazolyl 140-14256 A9-1 1,5-dimethyl-3-pyrazolyl 125-12857 A1-1 4-bromo-1,5-dimethyl-3-pyrazolyl 204-20558 A1-28 4-bromo-1,5-dimethyl-3-pyrazolyl 200-20159 A1-26 4-bromo-1,5-dimethyl-3-pyrazolyl 194-19560 A1-30 4-bromo-1,5-dimethyl-3-pyrazolyl 205-20661 A1-29 4-bromo-1,5-dimethyl-3-pyrazolyl 21062 A1-27 4-bromo-1,5-dimethyl-3-pyrazolyl 192-19363 A1-9 4-bromo-1,5-dimethyl-3-pyrazolyl 192-19364 A1-2 4-bromo-1,5-dimethyl-3-pyrazolyl 180-18265 A1-3 4-bromo-1,5-dimethyl-3-pyrazolyl66 A2-9 4-bromo-1,5-dimethyl-3-pyrazolyl67 A1-1 4-chloro-1,5-dimethyl-3-pyrazolyl 192-19468 A1-11 4-chloro-1,5-dimethyl-3-pyrazolyl 196-19769 A1-29 4-chloro-1,5-dimethyl-3-pyrazolyl 21070 A1-30 4-chloro-1,5-dimethyl-3-pyrazolyl 194-19571 A1-40 4-chloro-1,5-dimethyl-3-pyrazolyl 201-20472 A1-1 1,4-dimethyl-3-pyrazolyl73 A1-2 1,4-dimethyl-3-pyrazolyl74 A1-28 1,4-dimethyl-3-pyrazolyl75 A1-27 1,4-dimethyl-3-pyrazolyl76 A1-30 1,4-dimethyl-3-pyrazolyl77 A1-1 1,4,5-trimethyl-3-pyrazolyl 184-18678 A1-29 1,4,5-trimethyl-3-pyrazolyl 145-14679 A1-40 1,4,5-trimethyl-3-pyrazolyl80 A1-1 4-ethoxycarbonyl-1-methyl-3-pyrazoyl 162-16481 A1-30 4-ethoxycarbonyl-1-methyl-3-pyrazoyl 197-20082 A1-1 1-ethyl-5-methyl-3-pyrazolyl 35-3783 A1-11 1-ethyl-5-methyl-3-pyrazolyl 62-6384 A1-27 1-ethyl-5-methyl-3-pyrazolyl85 A1-43 1-ethyl-5-methyl-3-pyrazolyl86 A1-29 1-ethyl-5-methyl-3-pyrazolyl 171-17387 A1-1 1-isopropyl-5-methyl-3-pyrazolyl 156-15888 A1-29 1-isopropyl-5-methyl-3-pyrazolyl 206-20889 A1-40 1-isopropyl-5-methyl-3-pyrazolyl90 A1-1 1-methyl-1,4,5,6-tetrahydrocyclo- 187-188 pentapyrazol-3-yl91 A1-28 1-methyl-1,4,5,6-tetrahydrocyclo- pentapyrazol-3-yl92 A1-30 1-methyl-1,4,5,6-tetrahydrocyclo- pentapyrazol-3-yl93 A1-40 1-methyl-1,4,5,6-tetrahydrocyclo- pentapyrazol-3-yl94 A1-1 1-methyl-4,5,6,7-tetrahydrobenzo 157-158 pyrazol-3-yl95 A1-26 1-methyl-4,5,6,7-tetrahydro 134-135 benzopyrazol-3-yl96 A1-43 1-methyl-4,5,6,7-tetrahydro benzopyrazol-3-yl97 A1-2 1-methyl-4,5,6,7-tetrahydro benzopyrazol-3-yl98 A1-1 1,3-dimethyl-5-pyrazolyl 158-16299 A1-30 1,3-dimethyl-5-pyrazolyl 203100 A1-29 1,3-dimethyl-5-pyrazolyl >230101 A1-1 1-methyl-4-pyrazolyl 174-178102 A1-30 1-methyl-4-pyrazolyl 208103 A6-1 1-methyl-4-pyrazolyl 174-180104 A9-1 1-methyl-4-pyrazolyl 220-227105 A1-1 5-cyclopropyl-1-methyl-3-pyrazolyl 150-152106 A1-27 5-cyclopropyl-1-methyl-3-pyrazolyl107 A1-30 5-cyclopropyl-1-methyl-3-pyrazolyl 148-150108 A1-40 5-cyclopropyl-1-methyl-3-pyrazolyl109 A1-1 5-ethyl-1-methyl-3-pyrazolyl110 A1-15 5-ethyl-1-methyl-3-pyrazolyl111 A1-30 5-ethyl-1-methyl-3-pyrazolyl112 A1-43 5-ethyl-1-methyl-3-pyrazolyl113 A1-28 1,4-dimethyl-2-imidazolyl 230-231114 A1-1 1,4-dimethyl-2-imidazolyl115 A1-28 1-methyl-2-imidazolyl 162-165116 A1-1 1-methyl-2-imidazolyl117 A1-29 1-methyl-2-imidazolyl118 A1-1 1-methyl-5-imidazolyl 220119 A1-26 1-methyl-5-imidazolyl, Na salt >300120 A1-30 1-methyl-5-imidazolyl 255121 A1-30 1-methyl-5-imidazolyl Na salt >300122 A1-40 1-methyl-5-imidazolyl 260-265123 A1-29 1-methyl-5-imidazolyl 295-300124 A1-1 2-methyl-4-oxazolyl125 A1-26 2-methyl-4-oxazolyl126 A1-30 2-methyl-4-oxazolyl127 A1-44 2-methyl-4-oxazolyl128 A1-1 2-cyclopropyl-4-oxazolyl 110-112129 A1-2 2-cyclopropyl-4-oxazolyl130 A1-27 2-cyclopropyl-4-oxazolyl 164-166131 A9-1 2-cyclopropyl-4-oxazolyl132 A1-1 1,2,3-thiadiazolyl-4-yl 110133 A1-28 1,2,3-thiadiazolyl-4-yl 173-176134 A1-29 1,2,3-thiadiazolyl-4-yl >230135 A1-33 1,2,3-thiadiazolyl-4-yl 139136 A1-1 4-methyl-1,2,3-thiadiazolyl-5-yl137 A1-28 4-methyl-1,2,3-thiadiazol-5-yl138 A1-27 4-chloro-1,5-dimethyl-3-pyrazolyl 198-200139 A1-1 5-phenyl-3-isoxazolyl 205-206140 A1-11 4-bromo-1,5-dimethyl-3-pyrazolyl >210141 A1-26 1,5-dimethyl-3-pyrazolyl 146-147142 A1-22 1,5-dimethyl-3-pyrazolyl 152-153143 A1-28 5-methyl-3-isoxazolyl 190-191144 A2-4 1,5-dimethyl-3-pyrazolyl 191-192145 A1-49 1,5-dimethyl-3-pyrazolyl 153-155146 A1-1 1,5-dimethyl-3-pyrazolyl, Na salt >220147 A1-1 1,5-dimethyl-3-pyrazolyl, Ca salt >220148 A1-11 1-methyl-1,4,5,6-tetrahydrocyclo- 184-187 pentapyrazol-3-yl149 A1-27 5-methyl-3-isoxazolyl 160-161150 A1-22 5-methyl-3-isoxazolyl 160-162151 A1-10 2-cyclopropyl-4-oxazolyl 150-152152 A1-30 2-cyclopropyl-4-oxazolyl 131-132153 A1-22 2-cyclopropyl-4-oxazolyl 129-131154 A1-44 1,5-dimethyl-3-pyrazolyl 83-85155 A6-1 1,5-dimethyl-3-pyrazolyl 130-132156 A1-9 5-cyclopropyl-1-methyl-3-pyrazolyl 100-101157 A1-10 4-chloro-1,5-dimethyl-3-pyrazolyl 210-212158 A1-9 4-chloro-1,5-dimethyl-3-pyrazolyl 194-195159 A2-4 4-bromo-1,5-dimethyl-3-pyrazolyl 199160 A1-22 4-bromo-1,5-dimethyl-3-pyrazolyl 175-177161 A1-18 4-bromo-1,5-dimethyl-3-pyrazolyl 155-157162 A1-1 1,4,5-trimethyl-3-pyrazolyl, Na salt >220163 A1-30 1,4,5-trimethyl-3-pyrazolyl 148-150164 A1-1 4,5-diethyl-1-methyl-3-pyrazolyl 154-156165 A1-1 4,5-diethyl-1-methyl-3-pyrazolyl, 90-92 Na salt166 A1-2 4,5-diethyl-1-methyl-3-pyrazolyl 137-139167 A1-2 4,5-diethyl-1-methyl-3-pyrazolyl, 157-159 Na salt168 A1-9 4,5-diethyl-1-methyl-3-pyrazolyl 167-169169 A1-9 4,5-diethyl-1-methyl-3-pyrazolyl, 130-132 Na salt170 A1-10 4,5-diethyl-1-methyl-3-pyrazolyl 116-118171 A2-4 4,5-diethyl-1-methyl-3-pyrazolyl 121-123172 A1-29 4,5-diethyl-1-methyl-3-pyrazolyl 128-130173 A1-29 4,5-diethyl-1-methyl-3-pyrazolyl 141-143 Na salt174 A1-27 4,5-diethyl-1-methyl-3-pyrazolyl, >220 Na salt175 A1-30 4,5-diethyl-1-methyl-3-pyrazolyl 96-98176 A1-30 4,5-diethyl-1-methyl-3-pyrazolyl, >220 Na salt177 A1-22 4,5-diethyl-1-methyl-3-pyrazolyl 93-95178 A1-22 4,5-diethyl-1-methyl-3-pyrazolyl, 82-84 Na salt179 A1-28 4,5-diethyl-1-methyl-3-pyrazolyl 150-152180 A1-28 4,5-diethyl-1-methyl-3-pyrazolyl, 120-122 Na salt181 A1-9 1-methyl-4,5,6,7-tetrahydro- 177-178 benzopyrazol-3-yl182 A1-10 1-methyl-4,5,6,7-tetrahydro- 180-181 benzopyrazol-3-yl183 A1-29 1-methyl-4,5,6,7-tetrahydro- 210 benzopyrazol-3-yl184 A1-30 1-methyl-4,5,6,7-tetrahydro- 167-168 benzopyrazol-3-yl185 A1-27 1-methyl-4,5,6,7-tetrahydro- 161-162 benzopyrazol-3-yl186 A1-28 1-methyl-4,5,6,7-tetrahydro- 125-126 benzopyrazol-3-yl187 A1-1 1-ethyl-5-methyl-3-pyrazolyl, Na salt 168-170188 A1-2 1-ethyl-5-methyl-3-pyrazolyl 90-92189 A1-30 1-ethyl-5-methyl-3-pyrazolyl 120-121190 A1-28 1-ethyl-5-methyl-3-pyrazolyl 133-135191 A1-1 1-methyl-3-phenyl-4-pyrazolyl 32-34192 A1-30 1-methyl-5-phenyl-4-pyrazolyl 199-201______________________________________
It is also possible in a similar way to prepare further compounds of the structure ##STR14## where A can be a radical from the group E1 to E97
B can be a radical from the group G1 to G12
X can be O, S or NR.sup.9
W can be O or S
R.sup.8 can be a radical from the group L1 to L140
R.sup.9 can be a radical from the group V1 to V35 for example, and any combination of E, G, L, V, W and X is possible,
or where
A can be a radical from the group E1 to E97
B can be a radical from the group G13 to G14
X can be O or S
W can be O or S
R.sup.8 can be a radical from the group L1 to L140 for example, and any combination of E, G, L, W and X is possible,
or where
A can be a radical from the group E1 to E97
B can be the radical G15
X can be N
W can be O or S
R.sup.10 can be a radical from the group Y1 to Y16
R.sup.11 can be a radical from the group Z1 to Z13 for example, and any combination of E, G, W, Y and Z is possible
Examples of possible meanings of A, B, R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are the following:
______________________________________Comp. No.______________________________________ AE1 2-CO.sub.2 CH.sub.3C.sub.6 H.sub.4E2 2-CO.sub.2 CH.sub.2 CH.sub.3C.sub.6 H.sub.4E3 2-CO.sub.2 CH(CH.sub.3).sub.2C.sub.6 H.sub.4E4 2-CO.sub.2 CH.sub.3 -6-ClC.sub.6 H.sub.3E5 2-CO.sub.2 CH.sub.3 -6-OCH.sub.3C.sub.6 H.sub.3E6 2-CO.sub.2 CH.sub.3 -6-CH.sub.3C.sub.6 H.sub.3E7 2-CO.sub.2 CH.sub.3 -3-ClC.sub.6 H.sub.3E8 2-CO.sub.2 CH.sub.3 -3-FC.sub.6 H.sub.3E9 2-CO.sub.2 CH.sub.3 -6-FC.sub.6 H.sub.3E10 2-CO.sub.2 CH.sub.3 -4-ClC.sub.6 H.sub.3E11 2-CO.sub.2 CH.sub.3 -5-ClC.sub.6 H.sub.3E12 2-CO.sub.2 CH.sub.3 -5-FC.sub.6 H.sub.3E13 2-CO.sub.2 CH.sub.3 -5-OCH.sub.3C.sub.6 H.sub.3E14 2-CO.sub.2 CH.sub.3 -5-OCHF.sub.2C.sub.6 H.sub.3E15 2-CON(CH.sub.3).sub.2C.sub.6 H.sub.4E16 2-CON(CH.sub.3).sub.2 -3-ClC.sub.6 H.sub.3E17 2-CON(CH.sub.3).sub.2 -3-FC.sub.6 H.sub.3E18 2-CH.sub.3C.sub.6 H.sub.4E19 2-CH.sub.2 ClC.sub.6 H.sub.4E20 2-CH.sub.2 OCH.sub.3C.sub.6 H.sub.4E21 2-CH.sub.2 SCH.sub.3C.sub.6 H.sub.4E22 2-CF.sub.3C.sub.6 H.sub.4E23 2-CH.sub.3 -5-ClC.sub.6 H.sub.3E24 2,5-(CH.sub.3).sub.2C.sub.6 H.sub.3E25 2-CH.sub.3 -5-OCH.sub.3C.sub.6 H.sub.3E26 2-FC.sub.6 H.sub.4E27 2,6-F.sub.2C.sub.6 H.sub.3E28 2-ClC.sub.6 H.sub.4E29 2,6-Cl.sub.2C.sub.6 H.sub.3E30 2-Cl-6-CH.sub.3C.sub.6 H.sub.3E31 2-Cl-6-OCH.sub.3C.sub.6 H.sub.3E32 2-Cl-5-CO.sub.2 CH.sub.3C.sub.6 H.sub.3E33 2,5-Cl.sub.2C.sub.6 H.sub.3E34 2,3-Cl.sub.2C.sub.6 H.sub.3E35 2,5,6-Cl.sub.3C.sub.6 H.sub.2E36 2,4,6-Cl.sub.3C.sub.6 H.sub.2E37 2-BrC.sub.6 H.sub.4E38 2,6-Br.sub.2C.sub.6 H.sub.3E39 2-CNC.sub.6 H.sub.4E40 2-OCH.sub.3C.sub.6 H.sub.4E41 2-OCH.sub.2 CH.sub.3C.sub.6 H.sub.4E42 2-OCH(CH.sub.3).sub.2C.sub.6 H.sub.4E43 2-OCH.sub.2 CH.sub.2 ClC.sub.6 H.sub.4E44 2-OCH.sub.2 CH.sub.2 OCH.sub.3C.sub.6 H.sub.4E45 2-OCH.sub.2 CF.sub.3E46 2-OCF.sub. 3E47 2-OCF.sub.2 HC.sub.6 H.sub.4E48 2-OCH.sub.3 -5-BrC.sub.6 H.sub.3E49 2,5-(OCH.sub.3).sub.2C.sub.6 H.sub.3E50 2,5-(OCH.sub.2 CF.sub.3).sub.2C.sub.6 H.sub.3E51 2-SCH.sub.3C.sub.6 H.sub.4E52 2-SCH.sub.2 CH.sub.3C.sub.6 H.sub.4E53 2-SO.sub.2 CH.sub.3C.sub.6 H.sub.4E54 2-SO.sub.2 CH.sub.2 CH.sub.3C.sub.6 H.sub.4E55 2-SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3C.sub.6 H.sub.4E56 2-SO.sub.2 CH(CH.sub.3).sub.2C.sub.6 H.sub.4E57 2-SO.sub.2 N(CH.sub.3).sub.2C.sub.6 H.sub.4E58 2-OSO.sub.2 CH.sub.3C.sub.6 H.sub.4E59 2-OSO.sub.2 CH.sub.2 CH.sub.3C.sub.6 H.sub.4E60 2-COCH.sub.3C.sub.6 H.sub.4E61 2-C.sub.6 H.sub.5C.sub.6 H.sub.4E62 Pyrid-2-ylE63 3-CO.sub.2 CH.sub.3 -pyrid-2-ylE64 3-CO.sub.2 CH.sub.2 CH.sub.3 -pyrid-2-ylE65 3-CON(CH.sub.3).sub.2 -pyrid-2-ylE66 3-Cl-pyrid-2-ylE67 3-CF.sub.3 -pyrid-2-ylE68 3-OCH.sub.2 CH.sub.3 -pyrid-2-ylE69 3-SO.sub.2 CH.sub.3 -pyrid-2-ylE70 3-SO.sub.2 CH.sub.2 CH.sub.3 -pyrid-2-ylE71 3-SOCH.sub.3 -pyrid-2-ylE72 3-SOC.sub.2 H.sub. 5 -pyrid-2-ylE73 3-SO.sub.2 N(CH.sub.3).sub.2 -pyrid-2-ylE74 3-SO.sub.2 NHCH(CH.sub.3).sub.2 -pyrid-2-ylE75 Pyrid-3-ylE76 2-CON(CH.sub.3).sub.2 -pyrid-3-ylE77 Thien-2-ylE78 3-Cl-thien-2-ylE79 4-Cl-thien-2-ylE80 5-Cl-thien-2-ylE81 3-CO.sub.2 CH.sub.3 -thien-2-ylE82 2-CO.sub.2 CH.sub.3 -thien-3-ylE83 2-CON(CH.sub.3).sub.2 -thien-3-ylE84 4-CO.sub.2 CH.sub.3 -thien-3-ylE85 Naphth-1-ylE86 2-CO.sub.2 CH.sub.3 -naphth-1-ylE87 2-Cl-naphth-1-ylE88 8-CO.sub.2 CH.sub.3 -naphth-1-ylE89 8-Cl-naphth-1-ylE90 8-OCH.sub.3 -naphth-1-ylE91 8-OCH.sub.2 CH.sub.2 OCH.sub.3 -naphth-1-ylE92 8-OCH.sub.2 CH.sub.2 Cl-naphth-1-ylE93 Naphth-2-ylE94 1-CO.sub.2 CH.sub.3 -naphth-2-ylE95 1-Cl-naphth-2-ylE96 1-OCH.sub.2 CH.sub.2 OCH.sub.3 -naphth-2-ylE97 1-OCH.sub.2 CH.sub.2 Cl-naphth-2-yl BG1 ##STR15##G2 ##STR16##G3 ##STR17##G4 ##STR18##G5 ##STR19##G6 ##STR20##G7 ##STR21##G8 ##STR22##G9 ##STR23##G10 ##STR24##G11 ##STR25##G12 ##STR26##G13 ##STR27##G14 ##STR28##G15 ##STR29## R.sup.8L1 HL2 FL3 ClL4 BrL5 JL6 CNL7 NO.sub.2L8 CH.sub.3L9 C.sub.2 H.sub.5L10 n-C.sub.3 H.sub.7L11 i-C.sub.3 H.sub.7L12 n-C.sub.4 H.sub.9L13 i-C.sub.4 H.sub.9L14 s-C.sub.4 H.sub.9L15 tert.-C.sub.4 H.sub.9L16 CH.sub.2 FL17 CH.sub.2 ClL18 CH.sub.2 BrL19 CHF.sub.2L20 CF.sub.3L21 CCl.sub.3L22 CH.sub.2CH.sub.2 FL23 CH.sub.2CH.sub.2 ClL24 CH.sub.2CHF.sub.2L25 CH.sub.2CF.sub.3L26 CH.sub.2CCl.sub.3L27 CF.sub.2CF.sub.3L28 CH.sub.2OCH.sub.3L29 CH.sub.2CH.sub.2OCH.sub.3L30 CH(CH.sub.3)OCH.sub.3L31 CH(CH.sub.3)CH.sub.2 OCH.sub.3L32 CH.sub.2 OC.sub.2 H.sub.5L33 CH.sub.2 C.sub.6 H.sub.5L34 cyclo-C.sub.3 H.sub.5L35 cyclo-C.sub.4 H.sub.7L36 cyclo-C.sub.5 H.sub.9L37 cyclo-C.sub.6 H.sub.11L38 Tetrahydropyran-2-ylL39 Tetrahydropyran-3-ylL40 Tetrahydrofuran-2-ylL41 Tetrahydrofuran-3-ylL42 Thien-2-ylL43 Thien-3-ylL44 Furan-2-ylL45 Furan-3-ylL46 1-Methylpyrazol-3-ylL47 1-Methylpyrazol-4-ylL48 1-Methylpyrazol-5-ylL49 1-Ethylpyrazol-3-ylL50 1-Ethylpyrazol-4-ylL51 1-Ethylpyrazol-5-ylL52 OCH.sub.3L53 OC.sub.2 H.sub.5L54 OCH(CH.sub.3).sub.2L55 OCH.sub.2 CH.sub.2 ClL56 OCH.sub.2 CH.sub.2 OCH.sub.3L57 OCF.sub.3L58 OCHF.sub.2L59 OCH.sub.2 CF.sub.3L60 OC.sub.6 H.sub.5L61 OCH.sub.2 C.sub.6 H.sub.5L62 SCH.sub.3L63 SCH.sub.2 CH.sub.3L64 SC.sub.6 H.sub.5L65 SCH.sub.2 C.sub.6 H.sub.5L66 CH.sub.2CHCH.sub.2L67 CH(CH.sub.3)CHCH.sub.2L68 CH.sub.2C(CH.sub.3) CH.sub.2L69 CH.sub.2CHCHCH.sub.3L70 CH.sub.2CCHL71 CH(CH.sub.3)CCHL72 CH.sub.2CCCH.sub.3L73 C.sub.6 H.sub.5L74 2-CH.sub.3C.sub.6 H.sub.4L75 3-CH.sub.3C.sub.6 H.sub.4L76 4-CH.sub.3C.sub.6 H.sub.4L77 2-CF.sub.3C.sub.6 H.sub.4L78 3-CF.sub.3C.sub.6 H.sub.4L79 4-CF.sub.3C.sub.6 H.sub.4L80 2-FC.sub.6 H.sub.4L81 3-FC.sub.6 H.sub.4L82 4-FC.sub.6 H.sub.4L83 2-ClC.sub.6 H.sub.4L84 3-ClC.sub.6 H.sub.4L85 4-ClC.sub.6 H.sub.4L86 2-NO.sub.2C.sub.6 H.sub.4L87 3-NO.sub.2C.sub.6 H.sub.4L88 4-NO.sub.2C.sub.6 H.sub.4L89 2-CH.sub.3C.sub.6 H.sub.4L90 3-CH.sub.3 OC.sub.6 H.sub.4L91 4-CH.sub.3 OC.sub.6 H.sub.4L92 COCH.sub.3L93 COCH.sub.2 CH.sub.3L94 CO(cycloC.sub.3 H.sub.5)L95 COCH.sub.2 ClL96 COCH.sub.2 BrL97 COCH.sub.2 FL98 COCF.sub.3L99 COCH.sub.2 OCH.sub.3L100 CO.sub.2 HL101 CO.sub.2 CH.sub.3L102 CO.sub.2 CH.sub.2 CH.sub.3L103 CO.sub.2 CH(CH.sub.3).sub.2L104 CO.sub.2 CH.sub.2 CF.sub.3L105 CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3L106 CO.sub.2 CH.sub.2 C.sub.6 H.sub.5L107 CONH.sub.2L108 CONHCH.sub.3L109 CON(CH.sub.3).sub.2L110 CONHC.sub.2 H.sub.5L111 CON(C.sub.2 H.sub.5).sub.2L112 CONHCH(CH.sub.3).sub.2L113 CONHCH.sub.2 C.sub.6 H.sub.5L114 CONHC.sub.6 H.sub.5L115 CONHOCH.sub.3L116 CONHOC.sub.2 H.sub.5L117 SO.sub.2 N(CH.sub.3).sub.2L118 SO.sub.2 NCH.sub.3 (C.sub.2 H.sub.5)L119 SO.sub.2 N(C.sub.2 H.sub.5).sub.2L120 SO.sub.2 NHCH.sub.3L121 SO.sub.2 NHC.sub.2 H.sub.5L122 SO.sub.2 OCH.sub.3L123 SO.sub.2 OC.sub.2 H.sub.5L124 SO.sub.2 OCH(CH.sub.3).sub.2L125 SO.sub.2 OCH.sub.2 CH.sub.2 ClL126 SO.sub.2 OCH.sub.2 CF.sub.3L127 OSO.sub.2 CH.sub.3L128 OSO.sub.2 C.sub.2 H.sub.5L129 OSO.sub.2 CH(CH.sub.3).sub.2L130 OSO.sub.2 N(CH.sub.3).sub.2L131 SOCH.sub.3L132 SOC.sub.2 H.sub.5L133 SOCH(CH.sub.3).sub.2L134 SOC.sub.6 H.sub.5L135 SO.sub.2 CH.sub.3L136 SO.sub.2 CH.sub.2 CH.sub.3L137 SO.sub.2 CH(CH.sub.3).sub.2L138 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3L139 two vicinal R.sup.8 radicals together form a trimethylene chainL140 two vicinal R.sup.8 radicals together form a tetramethylene chain R.sup.9V1 HV2 CH.sub.3V3 CH.sub.2 CH.sub.3V4 CH.sub.2 CH.sub.2 FV5 CH.sub.2 CF.sub.3V6 CH.sub.2 CH.sub.2 ClV7 CH.sub.2 CH.sub.2 OCH.sub.3V8 CH.sub.2 C.sub.6 H.sub.5V9 CH(CH.sub.3).sub.2V10 cyclo-C.sub.3 H.sub.5V11 cyclo-C.sub.4 H.sub.7V12 cyclo-C.sub.5 H.sub.9V13 C.sub.6 H.sub.5V14 2-CH.sub.3C.sub.6 H.sub.4V15 2-C.sub.2 H.sub.5C.sub.6 H.sub.4V16 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3V17 2,6-(C.sub.2 H.sub.5).sub.2C.sub.6 H.sub.3V18 2-CH.sub.3 -6-C.sub.2 H.sub.5C.sub.6 H.sub.3V19 2-ClC.sub.6 H.sub.4V20 2,4-Cl.sub.2C.sub.6 H.sub.3V21 2,6-Cl.sub.2C.sub.6 H.sub.3V22 2,4,6-Cl.sub.3C.sub.6 H.sub.2V23 2,6-Cl.sub. 2 -4-CF.sub.3C.sub.6 H.sub.2V24 2-Cl-4-CF.sub.3C.sub.6 H.sub.3V25 CH.sub.2CHCH.sub.2V26 CHCH.sub.2V27 CH.sub.2CCHV28 CH.sub.2 C.sub.6 H.sub.5V29 COCH.sub.3V30 COC.sub.2 H.sub.5V31 COC.sub.6 H.sub.5V32 CH.sub.2 FV33 CHF.sub.2V34 CF.sub.3V35 CF.sub.2 Cl R.sup.10Y1 C.sub.6 H.sub.5Y2 2-ClC.sub.6 H.sub.4Y3 2-FC.sub.6 H.sub.4Y4 2-CH.sub.3C.sub.6 H.sub.3Y5 2-CF.sub.3C.sub.6 H.sub.3Y6 2-OCH.sub.3C.sub.6 H.sub.3Y7 2,3-Cl.sub.2C.sub.6 H.sub.3Y8 2,4-Cl.sub.2C.sub.6 H.sub.3Y9 2,5-Cl.sub.2C.sub.6 H.sub.3Y10 2,6-Cl.sub.2C.sub.6 H.sub.3Y11 2,4,6-Cl.sub.3C.sub.6 H.sub.2Y12 CH.sub.2 C.sub.6 H.sub.5Y13 OC.sub.6 H.sub.5Y14 OCH.sub.2 C.sub.6 H.sub.5Y15 SC.sub.6 H.sub.5Y16 SCH.sub.2 C.sub.6 H.sub.5 R.sup.11Z1 HZ2 C.sub.6 H.sub.5Z3 2-ClC.sub.6 H.sub.4Z4 2-FC.sub. 6 H.sub.4Z5 2-CH.sub.3C.sub.6 H.sub.4Z6 2-CF.sub.3C.sub.6 H.sub.4Z7 2-OCH.sub.3C.sub.6 H.sub.4Z8 2,4-Cl.sub.2C.sub.6 H.sub.3Z9 2,6-Cl.sub.2C.sub.6 H.sub.3Z10 2,6-F.sub.2C.sub.6 H.sub.3Z11 2,6-(CH.sub.3).sub.2C.sub.6 H.sub.3Z12 2-Cl-4-CF.sub.3C.sub.6 H.sub.3Z13 2,6-Cl.sub.2 -4-CF.sub.3C.sub.6 H.sub.2______________________________________
EXAMPLES OF USE
A Herbicidal action
The herbicidal action of the sulfonamides of the formula I was demonstrated in glasshouse tests:
The plants were grown in plastic flower pots containing loamy sand with about 3% humus as substrate. The seeds of the test plants were sown separately for each species.
In the case of pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing using finely dispersing nozzles. The pots were lightly watered in order to promote germination and growth and were then covered with transparent plastic covers until the plants had started to grow. This covering results in uniform germination of the test plants unless this has been impaired by the active ingredients. The application rates were 0.125 kg/ha active substance.
For post-emergence treatment, the test plants were treated with the active ingredients suspended or emulsified in water after they had grown to a height of from 3 to 15 cm depending on species. The application rate for the post-emergence treatment was 0.25 kg/ha active substance.
The plants were kept at 10.degree.-25.degree. C. or 20.degree.-35.degree. C. depending on the species. The test period lasted 2 to 4 weeks during which time the plants were tended and their reaction to the individual treatments was evaluated.
A scale from 0 to 100 was used for evaluation. 100 means no emergence of the parts or complete destruction of, at least, the above-ground parts and zero means no damage or normal growth.
The plants used in the glasshouse tests comprised the following species:
______________________________________Latin name English Name______________________________________Abutilon theophr. Chinese hempChenopodium album white goosefootTriticum aestivum summer wheat______________________________________
When 0.25 kg/ha active substance was employed in the post-emergence procedure there is very good control with Example 40 of broad-leaved weeds while the exemplary crop wheat tolerates the treatment.
B Growth-regulating action
The growth-regulating properties of the test substances were determined by growing test plants on substrate with an adequate nutrient supply in plastic containers of diameter about 12.5 cm.
The test substances in aqueous formulations were sprayed in the post-emergence method onto the plants. The growth-regulating action was established from the measured height of growth at the end of the test. The measurements were related to the height of growth of untreated plants. 2-Chloroethyltrimethylammonium chloride was used as comparative substance A.
The reduction in longitudinal growth was accompanied by a simultaneous increase in leaf color intensity. The increased chlorophyll content suggests that the photosynthesis rate, and thus the yield, is increased.
The individual data are to be found in Tables B-1 and B-2 below.
TABLE B-1______________________________________Summer wheat "Ralle"; post-emergence leaf treatment Concentration Rel. growthChem. example No. mg AS/container height______________________________________Untreated -- 100A 1.5 82.2 1.5 73.1______________________________________
TABLE B-2______________________________________Summer barley "Aramir"; post-emergence leaf treatment Concentration Rel. growthChem. example No. mg AS/container height______________________________________Untreated -- 100A 1.5 90.7 1.5 69.4______________________________________

Claims

1. A sulfonamide of the formula I ##STR30## where A is ##STR31## W is oxygen or sulfur; B is 3-, 4- or 5-pyrazol disubstituted on carbon by R.sup.8 and monosubstituted on nitrogen by R.sup.9 ;
R.sup.2 is halogen; cyano; thiocyano;
C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, phenyl, phenoxy or phenylthio, where each of the phenyls is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.8 -cycloalkoxy, C.sub.3 -C.sub.6 -cycloalkylthio, C.sub.5 -C.sub.6 -cycloalkenyl, C.sub.5 -C.sub.8 -cycloalkenyloxy or C.sub.5 -C.sub.8 -cycloalkenylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
phenyl, phenoxy, benzyloxy or benzylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
saturated, or unsaturated 5-7-membered heterocycle, said unsaturated 5-7 membered heterocycle having one or two double bonds, said saturated or unsaturated 5-7 membered heterocycle having one or two heteroatoms selected from nitrogen, oxygen and sulfur and which is unsubstituted or substituted by one or two of the following: halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -haloalkylthio;
C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio, C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkenyloxy or C.sub.2 -C.sub.6 -alkenylthio, C.sub.2 -C.sub.6 -alkynyl, C.sub.2 -C.sub.6 -alkynyloxy or C.sub.2 -C.sub.6 -alkynylthio, where the said alkoxy, alkylthio, alkenyl, alkynyl, alkenyloxy(thio) and alkynyloxy(thio) is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio; phenyl, phenoxy, phenylthio, benzyloxy or benzylthio; COR.sup.12 ; COQR.sup.13 ; SO.sub.2 NR.sup.15 R.sup.16 ; SO.sub.2 OR.sup.17 ; OSO.sub.2 R.sup.18 ; S(O).sub.n R.sup.19 ;
R.sup.3 is R.sup.6 ; COQR.sup.13 ; SO.sub.2 NR.sup.15 R.sup.16 ; SO.sub.2 OR.sup.17 ; OSO.sub.2 R.sup.18 ; S(O).sub.n R.sup.19 ;
R.sup.4 is hydrogen; halogen; cyano;
C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkyl substituted by one to five halogens; C.sub.1 -C.sub.4 -alkoxy; C.sub.1 -C.sub.4 -haloalkoxy; C.sub.1 -C.sub.4 -alkylthio; C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.5 is hydrogen; nitro or R.sup.2 ;
R.sup.6 is hydrogen; halogen; cyano;
C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkyl substituted by at least one of the following: one to five halogens, or one of the following:
C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, OH, SH or cyano;
C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -haloalkylthio, each of which is unsubstituted or substituted by the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.8 is hydrogen; nitro; or R.sup.2, or two vicinal R.sup.2 together form a C.sub.3 chain or a C.sub.4 -C.sub.6 chain unsubstituted or in which one methylene is replaced by oxygen or C.sub.1 -C.sub.4 -alkylimino;
R.sup.9 is C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy; C.sub.1 -C.sub.4 -haloalkoxy; C.sub.1 -C.sub.4 -alkylthio;
C.sub.1 -C.sub.4 -haloalkylthio, phenyl, phenoxy or phenylthio, wherein cyclic groups are unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
C.sub.3 -C.sub.6 -cycloalkyl or C.sub.5 -C.sub.6 -cycloalkenyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, or C.sub.1 -C.sub.4 -haloalkylthio;
phenyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkynyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio, phenyl, phenoxy, phenylthio, benzyloxy or benzylthio;
COR.sup.21 ;
R.sup.10 is phenyl, benzyl, phenoxy, benzyloxy, phenylthio or benzylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.11 is hydrogen; phenyl or benzyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following:
cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.12 is C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by halogen or methoxy; C.sub.3 -C.sub.5 -cycloalkyl which is unsubstituted or substituted by chlorine or fluorine; C.sub.3 -C.sub.4 -alkenyl;
Q is oxygen or NR.sup.14 ;
R.sup.13 is hydrogen;
C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkyl substituted by one to three of the following: halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.2 -alkoxy, C.sub.3 -C.sub.6 -cycloalkyl, or phenyl;
C.sub.3 -C.sub.6 -cycloalkyl, which is substituted one to three times by C.sub.1 -C.sub.4 -alkyl; C.sub.3 -C.sub.6 -alkenyl; C.sub.3 -C.sub.6 -alkynyl;
phenyl, phenyl substituted by at least one of the following:
one to five halogens, or one to three of the following:
cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.14 is OR.sup.20 ; R.sup.13 or forms together with another R.sup.13 a C.sub.4 -C.sub.6 -alkylene chain or a C.sub.4 -C.sub.6 -alkylene chain in which one methylene is replaced by oxygen or C.sub.1 -C.sub.4 -alkylimino;
R.sup.15 is C.sub.1 -C.sub.4 -alkyl; C.sub.3 -C.sub.4 -alkenyl; C.sub.3 -C.sub.4 -alkynyl; cyclopropylmethyl; C.sub.3 -C.sub.4 -cycloalkyl;
R.sup.16 is hydrogen; C.sub.1 -C.sub.4 -alkyl; C.sub.3 -C.sub.4 -alkenyl; or forms together with R.sup.15 a C.sub.4 -C.sub.6 -alkylene chain in which one methylene can be replaced by oxygen;
R.sup.17 is C.sub.1 -C.sub.4 -alkyl; C.sub.1 -C.sub.4 -haloalkyl;
R.sup.18 is C.sub.1 -C.sub.4 -alkyl; N,N-dimethylamino;
R.sup.19 is C.sub.1 -C.sub.4 -alkyl; C.sub.1 -C.sub.4 -haloalkyl; C.sub.2 -C.sub.4 -alkoxyalkyl; C.sub.3 -C.sub.4 -alkenyl; C.sub.3 -C.sub.4 -alkynyl; C.sub.3 -C.sub.4 -haloalkenyl; phenyl; phenyl substituted by fluorine, chlorine, bromine, methyl or methoxy;
n is 1 or 2;
R.sup.20 is hydrogen or C.sub.1 -C.sub.4 -alkyl;
R.sup.21 is R.sup.12 ; phenyl or benzyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
and the environmentally compatible salts thereof.
2. A compound of the formula I as claimed in claim 1 or the environmentally compatible salts thereof, where
A is (A1) or (A9),
W is oxygen and
R.sup.4 is hydrogen.
3. A compound of the formula I as claimed in claim 1 or the environmentally compatible salts thereof, where
A is (A1) or (A9),
W is oxygen and
R.sup.4 is hydrogen.
4. A herbicide containing an effective amount of a sulfonamide of the formula I as claimed in claim 1 or the salt thereof in addition to conventional herbicidal carriers.
5. A herbicide containing an effective amount of a sulfonamide of the formula I as claimed in claim 1, where
A is a radical of the formula (A1),
W is oxygen, and
R.sup.4 is hydrogen,
or a salt thereof, and conventional herbicidal carriers.
6. An agent for influencing plant growth, containing an effective amount of a sulfonamide of the formula I as claimed in claim 1 or the salt thereof in addition to conventional inert additives.
7. A process for controlling undesired plant growth, which comprises allowing a sulfonamide of the formula I: ##STR32## where A is ##STR33## W is oxygen or sulfur; B is 3-, 4- or 5-pyrazolyl, disubstituted on carbon by R.sup.8 and monosubstituted on nitrogen by R.sup.9 ;
R.sup.2 is halogen; cyano; thiocyano;
C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, phenyl, phenoxy or phenylthio, where each of the phenyls is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.8 -cycloalkoxy, C.sub.3 -C.sub.6 -cycloalkylthio, C.sub.5 -C.sub.6 -cycloalkenyl, C.sub.5 -C.sub.8 -cycloalkenyloxy or C.sub.5 -C.sub.8 -cycloalkenylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
phenyl, phenoxy, benzyloxy or benzylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
saturated, or unsaturated 5-7-membered heterocycle, said unsaturated 5-7 membered heterocycle having one or two double bonds, said saturated or unsaturated 5-7 membered heterocycle having one or two heteroatoms selected from nitrogen, oxygen and sulfur and which is unsubstituted or substituted by one or two of the following: halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -haloalkylthio;
C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio, C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkenyloxy or C.sub.2 -C.sub.6 -alkenylthio, C.sub.2 -C.sub.6 -alkynyl, C.sub.2 -C.sub.6 -alkynyloxy or C.sub.2 -C.sub.6 -alkynylthio, where the said alkoxy, alkylthio, alkenyl, alkynyl, alkenyloxy(thio) and alkynyloxy(thio) is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio; phenyl, phenoxy, phenylthio, benzyloxy or benzylthio; COR.sup.12 ; COQR.sup.13 ; SO.sub.2 NR.sup.15 R.sup.16 ; SO.sub.2 OR.sup.17 ; OSO.sub.2 R.sup.18 ; S(O).sub.n R.sup.19 ;
R.sup.3 is R.sup.6 ; COQR.sup.13 ; SO.sub.2 NR.sup.15 R.sup.16 ; SO.sub.2 OR.sup.17 ; OSO.sub.2 R.sup.18 ; S(O).sub.n R.sup.19 ;
R.sup.4 is hydrogen; halogen; cyano;
C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkyl substituted by one to five halogens; C.sub.1 -C.sub.4 -alkoxy; C.sub.1 -C.sub.4 -haloalkoxy; C.sub.1 -C.sub.4 -alkylthio; C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.5 is hydrogen; nitro or R.sup.2 ;
R.sup.6 is hydrogen; halogen; cyano;
C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkyl substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, OH, SH or cyano;
C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -haloalkylthio, each of which is unsubstituted or substituted by the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.8 is hydrogen; nitro; or R.sup.2, or two vicinal R.sup.2 together form a C.sub.3 chain or a C.sub.4 -C.sub.6 chain unsubstituted or in which one methylene is replaced by oxygen or C.sub.1 -C.sub.4 -alkylimino;
R.sup.9 is hydrogen;
C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy; C.sub.1 -C.sub.4 -haloalkoxy; C.sub.1 -C.sub.4 -alkylthio; C.sub.1 -C.sub.4 -haloalkylthio, phenyl, phenoxy or phenylthio, wherein cyclic groups are unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; C.sub.3 -C.sub.6 -cycloalkyl or C.sub.5 -C.sub.6 -cycloalkenyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, or C.sub.1 -C.sub.4 -haloalkylthio;
phenyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkynyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio, phenyl, phenoxy, phenylthio, benzyloxy or benzylthio; COR.sup.21 ;
R.sup.10 is phenyl, benzyl, phenoxy, benzyloxy, phenylthio or benzylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.11 is hydrogen; phenyl or benzyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.12 is C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by halogen or methoxy; C.sub.3 -C.sub.5 -cycloalkyl which is unsubstituted or substituted by chlorine or fluorine; C.sub.3 -C.sub.4 -alkenyl;
Q is oxygen or NR.sup.14 ;
R.sup.13 is hydrogen;
C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkyl substituted by one to three of the following: halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.2 -alkoxy, C.sub.3 -C.sub.6 -cycloalkyl, or phenyl;
C.sub.3 -C.sub.6 -cycloalkyl, which is substituted one to three times by C.sub.1 -C.sub.4 -alkyl; C.sub.3 -C.sub.6 -alkenyl; C.sub.3 -C.sub.6 -alkynyl; phenyl, phenyl substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.14 is OR.sup.20 ; R.sup.13 or forms together with another R.sup.13 a C.sub.4 -C.sub.6 -alkylene chain or a C.sub.4 -C.sub.6 -alkylene chain in which one methylene is replaced by oxygen or C.sub.1 -C.sub.4 -alkylimino;
R.sup.15 is C.sub.1 -C.sub.4 -alkyl; C.sub.3 -C.sub.4 -alkenyl; C.sub.3 -C.sub.4 -alkynyl; cyclopropylmethyl; C.sub.3 -C.sub.4 -cycloalkyl;
R.sup.16 is hydrogen; C.sub.1 -C.sub.4 -alkyl; C.sub.3 -C.sub.4 -alkenyl; or forms together with R.sup.15 a C.sub.4 -C.sub.6 -alkylene chain in which one methylene can be replaced by oxygen;
R.sup.17 is C.sub.1 -C.sub.4 -alkyl; C.sub.1 -C.sub.4 -haloalkyl;
R.sup.18 is C.sub.1 -C.sub.4 -alkyl; N,N-dimethylamino;
R.sup.19 is C.sub.1 -C.sub.4 -alkyl; C.sub.1 -C.sub.4 -haloalkyl; C.sub.2 -C.sub.4 -alkoxyalkyl; C.sub.3 -C.sub.4 -alkenyl; C.sub.3 -C.sub.4 -alkynyl; C.sub.3 -C.sub.4 -haloalkenyl; phenyl; phenyl substituted by fluorine, chlorine, bromine, methyl or methoxy;
n is 1 or 2;
R.sup.20 is hydrogen or C.sub.1 -C.sub.4 -alkyl;
R.sup.21 is R.sup.12 ; phenyl or benzyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; or the salt thereof to act on plants or their habitat.
8. A process for influencing plant growth, which comprises allowing a sulfonamide of the formula I: ##STR34## where A is ##STR35## W is oxygen or sulfur; B is 3-, 4- or 5-pyrazolyl, disubstituted on carbon by R.sup.8 and monosubstituted on nitrogen by R.sup.9 ;
R.sup.2 is halogen; cyano; thiocyano;
C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, phenyl, phenoxy or phenylthio, where each of the phenyls is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.8 -cycloalkoxy, C.sub.3 -C.sub.6 -cycloalkylthio, C.sub.5 -C.sub.6 -cycloalkenyl, C.sub.5 -C.sub.8 -cycloalkenyloxy or C.sub.5 -C.sub.8 -cycloalkenylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; phenyl, phenoxy, benzyloxy or benzylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; saturated, or unsaturated 5-7-membered heterocycle, said unsaturated 5-7 membered heterocycle having one or two double bonds, said saturated or unsaturated 5-7 membered heterocycle having one or two heteroatoms selected from nitrogen, oxygen and sulfur and which is unsubstituted or substituted by one or two of the following: halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -haloalkylthio; C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio, C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkenyloxy or C.sub.2 -C.sub.6 -alkenylthio, C.sub.2 -C.sub.6 -alkynyl, C.sub.2 -C.sub.6 -alkynyloxy or C.sub.2 -C.sub.6 -alkynylthio, where the said alkoxy, alkylthio, alkenyl, alkynyl, alkenyloxy(thio) and alkynyloxy(thio) is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio; phenyl, phenoxy, phenylthio, benzyloxy or benzylthio; COR.sup.12 ; COQR.sup.13 ; SO.sub.2 NR.sup.15 R.sup.16 ; SO.sub.2 OR.sup.17 ; OSO.sub.2 R.sup.18 ; S(O).sub.n R.sup.19 ;
R.sup.3 is R.sup.6 ; COQR.sup.13 ; SO.sub.2 NR.sup.15 R.sup.16 ; SO.sub.2 OR.sup.17 ; OSO.sub.2 R.sup.18 ; S(O).sub.n R.sup.19 ;
R.sup.4 is hydrogen; halogen; cyano; C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkyl substituted by one to five halogens; C.sub.1 -C.sub.4 -alkoxy; C.sub.1 -C.sub.4 -haloalkoxy; C.sub.1 -C.sub.4 -alkylthio; C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.5 is hydrogen; nitro or R.sup.2 ;
R.sup.6 is hydrogen; halogen; cyano;
C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkyl substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkylthio, OH, SH or cyano; C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -haloalkylthio, each of which is unsubstituted or substituted by the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.8 is hydrogen; nitro; or R.sup.2, or two vicinal R.sup.2 together form a C.sub.3 chain or a C.sub.4 -C.sub.6 chain unsubstituted or in which one methylene is replaced by oxygen or C.sub.1 -C.sub.4 -alkylimino;
R.sup.9 is hydrogen; C.sub.1 -C.sub.6 -alkyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy; C.sub.1 -C.sub.4 -haloalkoxy; C.sub.1 -C.sub.4 -alkylthio; C.sub.1 -C.sub.4 -haloalkylthio, phenyl, phenoxy or phenylthio, wherein cyclic groups are unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; C.sub.3 -C.sub.6 -cycloalkyl or C.sub.5 -C.sub.6 -cycloalkenyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, or C.sub.1 -C.sub.4 -haloalkylthio;
phenyl which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkynyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one of the following: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio, phenyl, phenoxy, phenylthio, benzyloxy or benzylthio; COR.sup.21 ;
R.sup.10 is phenyl, benzyl, phenoxy, benzyloxy, phenylthio or benzylthio, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.11 is hydrogen; phenyl or benzyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.12 is C.sub.1 -C.sub.4 -alkyl which is unsubstituted or substituted by halogen or methoxy; C.sub.3 -C.sub.5 -cycloalkyl which is unsubstituted or substituted by chlorine or fluorine; C.sub.3 -C.sub.4 -alkenyl;
Q is oxygen or NR.sup.14 ;
R.sup.13 is hydrogen; C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkyl substituted by one to three of the following: halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.2 -alkoxy, C.sub.3 -C.sub.6 -cycloalkyl, or phenyl;
C.sub.3 -C.sub.6 -cycloalkyl, which is substituted one to three times by C.sub.1 -C.sub.4 -alkyl; C.sub.3 -C.sub.6 -alkenyl; C.sub.3 -C.sub.6 -alkynyl; phenyl, phenyl substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio;
R.sup.14 is OR.sup.20 ; R.sup.13 or forms together with another R.sup.13 a C.sub.4 -C.sub.6 -alkylene chain or a C.sub.4 -C.sub.6 -alkylene chain in which one methylene is replaced by oxygen or C.sub.1 -C.sub.4 -alkylimino;
R.sup.15 is C.sub.1 -C.sub.4 -alkyl; C.sub.3 -C.sub.4 -alkenyl; C.sub.3 -C.sub.4 -alkynyl; cyclopropylmethyl; C.sub.3 -C.sub.4 -cycloalkyl;
R.sup.16 is hydrogen; C.sub.1 -C.sub.4 -alkyl; C.sub.3 -C.sub.4 -alkenyl; or forms together with R.sup.15 a C.sub.4 -C.sub.6 -alkylene chain in which one methylene can be replaced by oxygen;
R.sup.17 is C.sub.1 -C.sub.4 -alkyl; C.sub.1 -C.sub.4 -haloalkyl;
R.sup.18 is C.sub.1 -C.sub.4 -alkyl; N,N-dimethylamino;
R.sup.19 is C.sub.1 -C.sub.4 -alkyl; C.sub.1 -C.sub.4 -haloalkyl; C.sub.2 -C.sub.4 -alkoxyalkyl; C.sub.3 -C.sub.4 -alkenyl; C.sub.3 -C.sub.4 -alkynyl; C.sub.3 -C.sub.4 -haloalkenyl; phenyl; phenyl substituted by fluorine, chlorine, bromine, methyl or methoxy;
n is 1 or 2;
R.sup.20 is hydrogen or C.sub.1 -C.sub.4 -alkyl;
R.sup.21 is R.sup.12 ; phenyl or benzyl, each of which is unsubstituted or substituted by at least one of the following: one to five halogens, or one to three of the following: cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or C.sub.1 -C.sub.4 -haloalkylthio; or the salt thereof to act on plants or their habitat.

Priority Claims (1)

Number	Date	Country	Kind
4029753	Sep 1990	DEX

Foreign Referenced Citations (2)

Number	Date	Country
0244166	Nov 1987	EPX
0269141	Jun 1988	EPX

Non-Patent Literature Citations (3)

Entry
Egg, Chem. Abstracts, vol. 71, No. 21; 101768c (1969).
Arzneimittel-Forschung (Drug Research), vol. 24, Mar. 1974, pp. 363-374, V. H. Plumpe, et al., "Isoxazolcarboxamidoalkyl-Benzolsulfonyl-Harnstoffe,-Semicarbazide und -Aminopyrimidine Sowie Damit Verwandte Verbindungen und Ihre Blutzuckersenkende Wirkung".
Chemische Berichte, vol. 106, Jan. 1973, pp. 1290-1302, G. Siewert, et al., "Hydroxylierung Von 5-Alkyl-2-(Benzolsulfonylamino) Pyrimidines und Strukturverwandten Antidiabetika".

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