The invention relates to new substituted 
1-benzylsulphonyl-3-heteroaryl-(thio)ureas, a process and new intermediate 
products for their preparation and their use as herbicides. 
It is known that certain 1-benzylsulphonyl-3-heteroaryl-(thio)ureas, such 
as, for example, 
1-(2-methoxycarbonyl-benzylsulphonyl)-3-(4,6-dimethoxy-pyrimidin-2-yl)-ure 
a, have a herbicidal action. However, the action of these compounds is not 
always completely satisfactory (compare U.S. Pat. No. 4,420,325). 
New substituted 1-benzylsulphonyl-3-heteroaryl(thio)ureas of the general 
formula (I) 
##STR2## 
in which Q represents oxygen or sulphur, 
R.sup.1 represents hydrogen, or represents optionally substituted radicals 
from the series comprising alkyl, alkenyl, alkynyl and aralkyl, 
R.sup.2 represents hydrogen, halogen, hydroxyl, alkyl, halogenoalkyl, 
alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, amino, alkylamino or 
dialkylamino, 
R.sup.3 represents hydrogen or alkyl, 
R.sup.4 represents halogenoalkyl, 
X represents nitrogen or a --CH grouping, 
Y represents nitrogen or a --CR.sup.5 grouping, 
wherein 
R.sup.5 represents hydrogen, halogen, cyano, alkyl, formyl, alkyl-carbonyl 
or alkoxy-carbonyl and 
Z represents nitrogen or a --CR.sup.6 grouping, 
wherein 
R.sup.6 represents hydrogen, halogen, hydroxyl, alkyl, halogenoalkyl, 
alkoxy, halogenoalkoxy, alkylthio, alkylamino or dialkylamino, 
and salts of compounds of the formula (I) with metals and basic organic 
nitrogen compounds have now been found. 
The new substituted 1-benzylsulphonyl-3-heteroaryl-(thio)ureas of the 
formula (I) are obtained by a process in which 
2-halogenoalkoxy-benzylsulphonyl iso(thio)cyanates of the formula (II) 
##STR3## 
in which Q, R.sup.3 and R.sup.4 have the abovementioned meanings, are 
reacted with heteroarylamines of the formula (III) 
##STR4## 
in which R.sup.1, R.sup.2, X, Y and Z have the abovementioned meanings, if 
appropriate in the presence of diluents and if appropriate in the presence 
of catalysts, and, if appropriate, the products thus obtained are 
converted into salts by customary methods. 
The new substituted 1-benzylsulphonyl-3-heteroaryl-(thio)ureas of the 
formula (I) are distinguished by a powerful herbicidal activity. 
Surprisingly, the new compounds of the formula (I) exhibit a considerably 
better herbicidal action than the already known 
1-benzylsulphonyl-3-heteroaryl-(thio)ureas of the same type of action. 
Other possible methods for the preparation of the compounds of the formula 
(I) according to the invention are given below, Q, R.sup.1, R.sup.2, 
R.sup.3, R.sup.4, X, Y and Z having the abovementioned meanings: 
(a) reaction of 2-halogenoalkoxy-benzylsulphonamides (IV) with 
N-heteroaryl-urethanes (V) (R.sup.7 : alkyl, benzyl or phenyl): 
##STR5## 
(b) reaction of N-(2-halogenoalkoxy-benzylsulphonyl)-urethanes (VI) 
(R.sup.8 : alkyl, benzyl or phenyl) with heteroacrylamines (III): 
##STR6## 
(c) reaction of 1-benzylsulphonyl-3-heteroaryl-(thio)ureas (VII) with 
"alkylating agents" (VIII) (W: nucleophilic leaving group): 
##STR7## 
The invention preferably relates to compounds of the formula (I) 
in which 
Q represents oxygen or sulphur, 
R.sup.1 represents hydrogen, or represents C.sub.1 -C.sub.6 -alkyl [which 
is optionally substituted by fluorine, cyano, C.sub.1 -C.sub.4 -alkoxy or 
C.sub.1 -C.sub.4 -alkylthio], or represents C.sub.3 -C.sub.6 -alkenyl or 
C.sub.3 -C.sub.6 -alkynyl [which are optionally substituted by fluorine or 
chlorine], or represents phenyl-C.sub.1 -C.sub.2 -alkyl [which is 
optionally substituted in the phenyl part by fluorine, chlorine, nitro, 
cyano, methyl, methoxy or C.sub.1 -C.sub.2 -alkoxycarbonyl], 
R.sup.2 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, 
trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio, ethylthio, 
amino, methylamino, ethylamino, dimethylamino or diethylamino, 
R.sup.3 represents hydrogen or C.sub.1 -C.sub.4 -alkyl, 
R.sup.4 represents halogeno-C.sub.1 -C.sub.4 -alkyl, 
wherein 
halogen represents fluorine and/or chlorine, 
X represents nitrogen or a --CH grouping, 
Y represents nitrogen or a --CR.sup.5 grouping, 
wherein 
R.sup.5 represents hydrogen, fluorine, chlorine, 
bromine, methyl, formyl, acetyl, methoxycarbonyl or ethoxycarbonyl and 
Z represents nitrogen or a --CR.sup.6 grouping, 
wherein 
R.sup.6 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, 
trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, difluoromethoxy, 
methylthio, ethylthio, methylamino, ethylamino, dimethylamino or 
diethylamino. 
The invention furthermore preferably relates to salts of compounds of the 
formula (I)--as defined above--with sodium, potassium, magnesium and 
calcium, and with monoalkyl-, dialkyl-, trialkyl-, benzyl-alkyl- and 
benzyl-dialkylamines with in each case up to 4 carbon atoms in the alkyl 
radicals, the alkyl radicals optionally in each case containing one 
substituent from the series comprising fluorine, chlorine, hydroxyl, 
methoxy, ethoxy and cyano. 
The invention particularly relates to compounds of the formula (I) 
in which 
Q represents oxygen, 
R.sup.1 represents hydrogen or methyl, 
R.sup.2 represents hydrogen, chlorine, methyl, ethyl, trifluoromethyl, 
methoxy, ethoxy or difluoromethoxy, 
R.sup.3 represents hydrogen, 
R.sup.4 represents halogeno-C.sub.1 -C.sub.2 -alkyl, 
wherein 
halogen represents fluorine and/or chlorine, 
X represents nitrogen or a --CH grouping, 
Y represents nitrogen or a --CR.sup.5 grouping, 
wherein 
R.sup.5 represents hydrogen, fluorine, chlorine or methyl and 
Z represents nitrogen or a --CR.sup.6 grouping, 
wherein 
R.sup.6 represents hydrogen, chlorine, methyl, ethyl, trifluoromethyl, 
methoxy, ethoxy or difluoromethoxy. 
If, for example, 2-trifluoromethoxy-benzylsulphonyl isocyanate and 
2-amino-4,6-dimethyl-pyrimidine are used as starting substances for the 
process according to the invention, the course of the reaction can be 
outlined by the following equation: 
##STR8## 
Formula (II) provides a definition of the 2-halogenoalkoxy-benzylsulphonyl 
iso(thio)cyanates to be used as starting substances in the process 
according to the invention. In this formula, Q, R.sup.3 and R.sup.4 
preferably or particularly represent those radicals which have already 
been mentioned as preferred or as particularly preferred in connection 
with the description of the compounds of the formula (I) according to the 
invention. 
Examples which may be mentioned of the starting substances of the formula 
(II) are: 2-difluoromethoxy-, 2-trifluoromethoxy-, 
2-chlorodifluoromethoxy-, 2-dichlorofluoromethoxy-, 2-(2-chloro-ethoxy-, 
2-(2,2,2-trifluoroethoxy)-, 2-(1,1,2,2-tetrafluoro-ethoxy)- and 
2-(2-chloro-1,1,2-trifluoro-ethoxy)-benzylsulphonyl isocyanate and 
-benzylsulphonyl isothiocyanate, and 2-difluoromethoxy-, 
2-trifluoromethoxy-, 2-chlorodifluoromethoxy-, 2-dichlorofluoromethoxy-, 
2-(2-chloro-ethoxy)-, 2-(1,1,2,2-tetrafluoro-ethoxy)- and 
2-(2-chloro-1,1,2-trifluoro-ethoxy)-.alpha.-methyl-benzylsulphonyl 
isocyanate and -.alpha.-methyl-benzylsulphonyl isothiocyanate. 
The starting compounds of the formula (II) are not yet described in the 
literature. These compounds are obtained by a process in which 
(a) in the case where Q represents oxygen, 
2-halogenoalkoxy-benzylsulphonamides of the formula (IV) 
##STR9## 
in which R.sup.3 and R.sup.4 have the abovementioned meanings, are reacted 
with about the equimolar amount of an alkyl isocyanate, such as, for 
example, butyl isocyanate, if appropriate in the presence of a catalyst, 
such as, for example, diazabicyclo-[2,2,2]-octane (DABCO), and in the 
presence of a diluent, such as, for example, xylene, at temperatures 
between 50.degree. C. and 200.degree. C., preferably between 80.degree. C. 
and 150.degree. C., and at least the equimolar amount of phosgene is at 
the same time passed in, or 
(b) in the case where Q represents sulphur, by a process in which 
2-halogenoalkoxy-benzylsulphonamides of the above formula (IV) are reacted 
with carbon disulphide in the presence of an acid acceptor, such as, for 
example, potassium hydroxide, and if appropriate in the presence of a 
diluent, such as, for example, dimethylformamide, at temperatures between 
0.degree. C. and 50.degree. C., and the product is then reacted with 
phosgene or thionyl chloride, if appropriate in the presence of a diluent, 
such as, for example, methylene chloride, at temperatures between 
0.degree. C. and 50.degree. C. (compare Arch. Pharm. 299 (1966), 174). 
Formula (IV) provides a definition of the 
2-halogenoalkoxy-benzylsulphonamides to be used as intermediate products. 
In this formula, R.sup.3 and R.sup.4 preferably or particularly represent 
those radicals which have already been mentioned as preferred or as 
particularly preferred in connection with the description of the compounds 
of the formula (I) according to the invention. 
Examples which may be mentioned of the intermediate products of the formula 
(IV) are: 2-difluoromethoxy-, 2-trifluoromethoxy-, 
2-chlorodifluoromethoxy-, 2-dichlorofluoromethoxy-, 2-(2-chloro-ethoxy-, 
2-(2,2,2-trifluoroethoxy)-, 2-(1,1,2,2-tetrafluoroethoxy)- and 
2-(2-chloro-1,1,2-trifluoroethoxy)-benzylsulphonamide and the 
corresponding .alpha.-methyl-benzylsulphonamides. 
The intermediate products of the formula (IV) are not yet described in the 
literature. These compounds are obtained by a process in which 
2-halogenoalkoxy-benzylsulphonyl chlorides of the formula (IX) 
##STR10## 
in which R.sup.3 and R.sup.4 have the abovementioned meanings, are reacted 
with ammonia in at least the equimolar amount, if appropriate in the 
presence of a diluent, such as, for example, water, diethyl ether or 
tetrahydrofuran, at temperatures between -20.degree. C. and +100.degree. 
C., preferably between 0.degree. C. and 80.degree. C., and the product is 
worked up by customary methods. 
Formula (IX) provides a definition of the 2-halogenoalkoxy-benzylsulphonyl 
chlorides to be used as intermediate products. In this formula, R.sup.3 
and R.sup.4 preferably or particularly represent those radicals which have 
already been mentioned as preferred or as particularly preferred in 
connection with the description of the compounds of the formula (I) 
according to the invention. 
Examples which may be mentioned of the intermediate products of the formula 
(IX) are: 2-difluoromethoxy-, 2-trifluoromethoxy-, 
2-chlorodifluoromethoxy-, 2-dichlorofluoromethoxy-, 2-(2-chloro-ethoxy)-, 
2-(2,2,2-trifluoro-ethoxy)-, 2-(1,1,2,2-tetrafluoro-ethoxy)- and 
2-(2-chloro-1,1,2-trifluoro-ethoxy)-benzylsulphonyl chloride and the 
corresponding .alpha.-methyl-benzylsulphonyl chlorides. 
The intermediate products of the formula (IX) are not yet described in the 
literature. These compounds are obtained by a process in which 
2-halogenoalkoxy-benzylsulphonic acids or salts thereof, of the formula 
(X) 
##STR11## 
in which M represents hydrogen or an alkali metal and 
R.sup.3 and R.sup.4 have the abovementioned meanings, 
are reacted with at least the equimolar amount of a chlorinating agent, 
such as, for example, phosphorus pentachloride, phosphorus oxychloride or 
thionyl chloride, if appropriate in the presence of a diluent, such as, 
for example, methylene chloride, chloroform or carbon tetrachloride, at 
temperatures between 0.degree. C. and 150.degree. C., preferably between 
20.degree. C. and 100.degree. C., and the mixture is worked up by 
customary methods. 
Formula (X) provides a definition of the 2-halogenoalkoxy-benzylsulphonic 
acids and salts thereof to be used as intermediate products. In this 
formula, R.sup.3 and R.sup.4 preferably or particularly represent those 
radicals which have already been mentioned as preferred or as particularly 
preferred in connection with the description of the compounds of the 
formula (I) according to the invention, and M preferably and particularly 
represents hydrogen, sodium or potassium. 
Examples which may be mentioned of the intermediate products of the formula 
(X) are: 2-difluoromethoxy-, 2-trifluoromethoxy-, 
2-chlorodifluoromethoxy-, 2-dichlorofluoromethoxy-, 2-(2-chloro-ethoxy)-, 
2-(2,2,2-trifluoro-ethoxy)-, 2-(1,1,2,2-tetrafluoro-ethoxy)- and 
2-(2-chloro-1,1,2-trifluoro-ethoxy)-benzylsulphonic acid and sodium and 
potassium salts thereof, and furthermore the corresponding 
.alpha.-methyl-benzylsulphonic acids and their sodium and potassium salts. 
The intermediate products of the formula (X) are not yet described in the 
literature. These compounds are obtained by a process in which 
2-halogenoalkoxy-benzyl chlorides of the formula (XI) 
##STR12## 
in which R.sup.3 and R.sup.4 have the abovementioned meanings, are reacted 
with at least the equimolar amount of sodium thiosulphate or potassium 
thiosulphate in water at temperatures between 20.degree. C. and 
110.degree. C. and the product is worked up by customary methods. 
Formula (XI) provides a definition of the 2-halogenoalkoxy-benzyl chlorides 
to be used as intermediate products. In this formula, R.sup.3 and R.sup.4 
preferably or particularly represent those radicals which have already 
been mentioned as preferred or as particularly preferred in connection 
with the description of the compounds of the formula (I) according to the 
invention. 
Examples which may be mentioned of the intermediate products of the formula 
(XI) are: 2-difluoromethoxy-, 2-trifluoromethoxy-, 
2-chlorodifluoromethoxy-, 2-dichlorofluoromethoxy-, 2-(2-chloro-ethoxy)-, 
2-(1,1,2,2-tetrafluoro-ethoxy)- and 
2-(2-chloro-1,1,2-trifluoro-ethoxy)-benzyl chloride and the corresponding 
.alpha.-methyl-benzyl chlorides. 
The intermediate products of the formula (XI) are in some cases not yet 
described in the literature. For example, 2-trifluoromethoxy-benzyl 
chloride is as yet unknown. These compounds are obtained by a process in 
which 2-halogenoalkoxy-toluenes, for example 2-trifluoromethoxy-toluene, 
of the formula (XII) 
##STR13## 
in which R.sup.3 and R.sup.4 have the abovementioned meanings, are reacted 
with not more than the equimolar amount of chlorine at temperatures 
between 50.degree. C. and 180.degree. C. under UV irradiation and the 
product is worked up by customary methods (compare, for example, DE-OS 
(German published specification) No. 2,150,955). 
Formula (XII) provides a definition of the 2-halogenoalkoxy-toluenes to be 
used as intermediate products. In this formula, R.sup.3 and R.sup.4 
preferably or particularly represent those radicals which have already 
been mentioned as preferred or as particularly preferred in connection 
with the description of the compounds of the formula (I) according to the 
invention. 
Examples which may be mentioned of the compounds of the formula (XII) are: 
2-difluoromethoxy-, 2-trifluoromethoxy-, 2-chlorodifluoromethoxy-, 
2-dichlorofluoromethoxy-, 2-(2-chloro-ethoxy)-, 
2-(1,1,2,2-tetrafluoroethoxy)- and 
2-(2-chloro-1,1,2-trifluoro-ethoxy)-toluene and the corresponding 
.alpha.-methyltoluenes. 
The intermediate products of the formula (XII) are known and/or can be 
prepared by processes which are know per se (compare, for example, 
Tetrahedron Lett. 25 (1973), 2253-2256; and DE-OS (German published 
specification) No. 1,150,955). 
Formula (III) provides a definition of the heteroarylamines furthermore to 
be used as starting substances in the preparation process according to the 
invention. In this formula, R.sup.1, R.sup.2, X, Y and Z preferably or 
particularly represent those radicals which have already been mentioned as 
preferred or as particularly preferred in connection with the description 
of the compounds of the formula (I) according to the invention. 
Examples of the starting substances of the formula (III) are given in Table 
1 below. 
TABLE 1 
__________________________________________________________________________ 
##STR14## (III) 
R.sup.1 
##STR15## R.sup.1 
##STR16## 
__________________________________________________________________________ 
CH.sub.3 
##STR17## CH.sub.3 
##STR18## 
CH.sub.3 
##STR19## CH.sub.3 
##STR20## 
CH.sub.3 
##STR21## CH.sub.3 
##STR22## 
CH.sub.3 
##STR23## CH.sub.3 
##STR24## 
CH.sub.3 
##STR25## CH.sub.3 
##STR26## 
CH.sub.3 
##STR27## CH.sub.3 
##STR28## 
CH.sub.3 
##STR29## CH.sub.3 
##STR30## 
CH.sub.3 
##STR31## CH.sub. 3 
##STR32## 
CH.sub.3 
##STR33## CH.sub.3 
##STR34## 
CH.sub.3 
##STR35## CH.sub.3 
##STR36## 
CH.sub.3 
##STR37## CH.sub.3 
##STR38## 
CH.sub.3 
##STR39## CH.sub.3 
##STR40## 
CH.sub.3 
##STR41## CH.sub.3 
##STR42## 
CH.sub. 3 
##STR43## CH.sub.3 
##STR44## 
CH.sub.3 
##STR45## CH.sub.3 
##STR46## 
CH.sub.3 
##STR47## CH.sub.3 
##STR48## 
CH.sub.3 
##STR49## CH.sub.3 
##STR50## 
CH.sub.3 
##STR51## CH.sub.3 
##STR52## 
CH.sub.3 
##STR53## CH.sub.3 
##STR54## 
CH.sub.3 
##STR55## CH.sub.3 
##STR56## 
CH.sub.3 
##STR57## CH.sub.3 
##STR58## 
CH.sub.3 
##STR59## CH.sub.3 
##STR60## 
CH.sub.3 
##STR61## CH.sub.3 
##STR62## 
##STR63## H 
##STR64## 
H 
##STR65## H 
##STR66## 
H 
##STR67## H 
##STR68## 
H 
##STR69## CH.sub.3 
##STR70## 
H 
##STR71## H 
##STR72## 
H 
##STR73## H 
##STR74## 
H 
##STR75## 
##STR76## 
##STR77## 
H 
##STR78## 
C.sub.2 H.sub.5 
##STR79## C.sub.2 H.sub.5 
##STR80## 
C.sub.2 H.sub.5 
##STR81## C.sub.2 H.sub.5 
##STR82## 
C.sub.2 H.sub.5 
##STR83## C.sub.2 H.sub.5 
##STR84## 
C.sub.2 H.sub.5 
##STR85## CH.sub.3 
##STR86## 
CH.sub.3 
##STR87## CH.sub.3 
##STR88## 
C.sub.2 H.sub.5 
##STR89## C.sub.2 H.sub.5 
##STR90## 
C.sub.2 H.sub.5 
##STR91## C.sub.2 H.sub.5 
##STR92## 
C.sub.2 H.sub.5 
##STR93## C.sub.2 H.sub.5 
##STR94## 
C.sub.2 H.sub.5 
##STR95## C.sub.2 H.sub.5 
##STR96## 
C.sub.2 H.sub.5 
##STR97## C.sub.2 H.sub.5 
##STR98## 
C.sub.2 H.sub.5 
##STR99## C.sub.2 H.sub.5 
##STR100## 
C.sub.2 H.sub.5 
##STR101## 
C.sub.2 H.sub.5 
##STR102## 
C.sub.2 H.sub.5 
##STR103## 
C.sub.2 H.sub.5 
##STR104## 
C.sub.2 H.sub.5 
##STR105## 
C.sub.2 H.sub.5 
##STR106## 
C.sub.2 H.sub.5 
##STR107## 
C.sub.2 H.sub.5 
##STR108## 
C.sub.2 H.sub.5 
##STR109## 
C.sub.2 H.sub.5 
##STR110## 
C.sub.2 H.sub.5 
##STR111## 
C.sub.2 H.sub.5 
##STR112## 
C.sub.2 H.sub.5 
##STR113## 
C.sub.2 H.sub.5 
##STR114## 
C.sub.2 H.sub.5 
##STR115## 
C.sub.2 H.sub.5 
##STR116## 
C.sub.2 H.sub.5 
##STR117## 
C.sub.2 H.sub.5 
##STR118## 
C.sub.2 H.sub.5 
##STR119## 
C.sub.2 H.sub.5 
##STR120## 
C.sub.2 H.sub.5 
##STR121## 
C.sub.2 H.sub.5 
##STR122## 
C.sub.2 H.sub. 5 
##STR123## 
C.sub.2 H.sub.5 
##STR124## 
C.sub.2 H.sub.5 
##STR125## 
C.sub.2 H.sub.5 
##STR126## 
CH.sub.3 
##STR127## 
##STR128## 
##STR129## 
CH.sub.3 
##STR130## 
##STR131## 
##STR132## 
CH.sub.3 
##STR133## 
##STR134## 
##STR135## 
C.sub.3 H.sub.7n 
##STR136## 
C.sub.3 H.sub.7n 
##STR137## 
C.sub.3 H.sub. 7n 
##STR138## 
C.sub.3 H.sub.7n 
##STR139## 
C.sub.3 H.sub.7n 
##STR140## 
C.sub.3 H.sub.7n 
##STR141## 
C.sub.3 H.sub.7n 
##STR142## 
C.sub.3 H.sub.7n 
##STR143## 
C.sub.3 H.sub.7n 
##STR144## 
C.sub.3 H.sub.7n 
##STR145## 
C.sub.3 H.sub.7n 
##STR146## 
C.sub.3 H.sub.7n 
##STR147## 
C.sub.3 H.sub.7n 
##STR148## 
C.sub.3 H.sub.7n 
##STR149## 
CH.sub.2CHCH.sub.2 
##STR150## 
CH.sub.2CHCH.sub.2 
##STR151## 
CH.sub.2CHCH.sub.2 
##STR152## 
CH.sub.2CHCH.sub.2 
##STR153## 
CH.sub.2CHCH.sub.2 
##STR154## 
CH.sub.2CHCH.sub.2 
##STR155## 
CH.sub.2CHCH.sub.2 
##STR156## 
CH.sub.2CHCH.sub.2 
##STR157## 
CH.sub.2CHCH.sub.2 
##STR158## 
CH.sub.2CHCH.sub.2 
##STR159## 
CH.sub.2CHCH.sub.2 
##STR160## 
CH.sub.2CHCH.sub.2 
##STR161## 
CH.sub.2CHCH.sub.2 
##STR162## 
H 
##STR163## 
H 
##STR164## 
H 
##STR165## 
H 
##STR166## 
H 
##STR167## 
H 
##STR168## 
H 
##STR169## 
H 
##STR170## 
H 
##STR171## 
H 
##STR172## 
H 
##STR173## 
H 
##STR174## 
__________________________________________________________________________ 
The compounds of the formula (III) are known and can be prepared by 
processes which are known per se (compare, for example, Chem. Pharm. Bull. 
11 (1963), 1382 and U.S. Pat. No. 4,299,960, European Pat. No. A-121,082, 
European Pat. No. A-125,205, European Pat. No. A-126,711 and European Pat. 
No. A-152,378). 
The process according to the invention for the preparation of the new 
compounds of the formula (I) is preferably carried out using diluents. 
Possible diluents here are virtually all the inert organic solvents. These 
include, preferably, aliphatic and aromatic, optionally halogenated 
hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum 
ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, 
ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and 
o-dichlorobenzene, ethers, such as diethyl ether, dibutyl ether, glycol 
dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, 
ketones, such as acetone, methyl ethyl ketone, methyl isopropyl ketone and 
methyl isobutyl ketone, esters, such as methyl acetate and ethyl acetate, 
nitriles, such as, for example, acetonitrile and propionitrile, amides, 
such as, for example, dimethylformamide, dimethylacetamide and 
N-methyl-pyrrolidone, and dimethylsulphoxide, tetramethylene sulphone and 
hexamethylphosphoric acid triamide. 
If appropriate, the process according to the invention is carried out in 
the presence of a catalyst. Catalysts include, in particular, aliphatic, 
aromatic or heterocyclic amines, such as triethylamine, 
N,N-dimethylaniline, pyridine, 2-methyl-5-ethyl-pyridine, 
4-dimethylamino-pyridine, diazabicyclooctane (DABCO), diazabicyclononene 
(DBN) and diazabicycloundecene (DBU). 
The reaction temperatures can be varied within a substantial range in the 
process according to the invention. The reaction is in general carried out 
at temperatures between 0.degree. C. and 150.degree. C., preferably at 
temperatures between 20.degree. C. and 100.degree. C. 
The process according to the invention is in general carried out under 
normal pressure. However, it is also possible for the process to be 
carried out under increased or reduced pressure. 
For carrying out the process according to the invention, in general 1.0 to 
3.0 mols, preferably 1.0 to 2.0 mols, of 2-halogenoalkoxy-benzenesulphonyl 
iso(thio)cyanate of the formula (II) are employed per mol of 
hetereoarylamine of the formula (III). 
The starting substances of the formulae (II) and (III) and if appropriate 
the catalyst and the diluent are in general brought together at room 
temperature or with gentle external cooling and the reaction mixture is 
stirred, if appropriate at elevated temperature, until the reaction has 
ended. 
The new compounds of the formula (I) are worked up and isolated by 
customary methods: if the compounds of the formula (I) are obtained as 
crystals, they are isolated by filtration with suction. Otherwise--if 
appropriate after concentration--water and an organic solvent which is 
virtually water-immiscible are added and, after thorough shaking, the 
organic phase is separated off, dried, filtered and concentrated, the 
products of the formula (I) remaining in the residue. 
The active compounds according to the invention can be used as defoliants, 
desiccants, agents for destroying broad-leaved plants and, especially, as 
weedkillers. By weeds, in the broadest sense, there are to be understood 
all plants which grow in locations where they are undesired. Whether the 
substances according to the invention act as total or selective herbicides 
depends essentially on the amount used. 
The active compounds according to the invention can be used, for example, 
in connection with the following plants: 
Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, 
Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, 
Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, 
Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, 
Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver and Centaurea. 
Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, 
Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, 
Arachis, Brassica, Lactuca, Cucumis and Cucurbita. 
Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, 
Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, 
Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, 
Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, 
Dactyloctenium, Agrostis, Alopecurus and Apera. 
Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, 
Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium. 
However, the use of the active compounds according to the invention is in 
no way restricted to these genera, but also extends in the same manner to 
other plants. 
The compounds are suitable, depending on the concentration, for the total 
combating of weeds, for example on industrial terrain and rail tracks, and 
on paths and squares with or without tree plantings. Equally, the 
compounds can be employed for combating weeds in perennial cultures, for 
example afforestations, decorative tree plantings, orchards, vineyards, 
citrus groves, nut orchards, banana plantations, coffee plantations, tea 
plantations, rubber plantations, oil palm plantations, cocoa plantations, 
soft fruit plantings and hopfields, and for the selective combating of 
weeds in annual cultures. 
The new active compounds of the formula (I) are suitable for selectively 
combating dicotyledon weeds in monocotyledon crops by the pre-emergence 
and post-emergence method. 
The active compounds can be converted to the customary formulations, such 
as solutions, emulsions, wettable powders, suspensions, powders, dusting 
agents, pastes, soluble powders, granules, suspension-emulsion 
concentrates, natural and synthetic materials impregnated with active 
compound, and very fine capsules in polymeric substances. 
These formulations are produced in known manner, for example by mixing the 
active compounds with extenders, that is liquid solvents and/or solid 
carriers, optionally with the use of surface-active agents, that is 
emulsifying agents and/or dispersing agents and/or foam-forming agents. 
In the case of the use of water as an extender, organic solvents can, for 
example, also be used as auxiliary solvents. As liquid solvents, there are 
suitable in the main: aromatics, such as xylene, toluene or alkyl 
naphthalenes, chlorinated aromatics and chlorinated aliphatic 
hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene 
chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for 
example petroleum fractions, mineral and vegetable oils, alcohols, such as 
butanol or glycol as well as their ethers and esters, ketones, such as 
acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, 
strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, 
as well as water. 
As solid carriers there are suitable: for example ammonium salts and ground 
natural minerals, such as kaolins, clays, talc, chalk, quartz, 
attapulgite, montmorillonite or diatomaceous earth, and ground synthetic 
minerals, such as highly disperse silicic acid, alumina and silicates, as 
solid carriers for granules there are suitable: for example crushed and 
fractionated natural rocks such as calcite, marble, pumice, sepiolite and 
dolomite, as well as synthetic granules of inorganic and organic meals, 
and granules of organic material such as sawdust, coconut shells, corn 
cobs and tobacco stalks; as emulsifying and/or foam-forming agents there 
are suitable: for example non-ionic and anionic emulsifiers, such has 
polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, 
for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, 
arylsulphonates as well as albumin hydrolysis products; as dispersing 
agents there are suitable: for example lignin-sulphite waste liquors and 
methylcellulose. 
Adhesives such as carboxymethylcellulose and natural and synthetic polymers 
in the form of powders, granules or latices, such as gum arabic, polyvinyl 
alcohol and polyvinyl acetate, as well as natural phospholipids, such as 
cephalins and lecithins, and synthetic phospholipids, can be used in the 
formulations. Further additives can be mineral and vegetable oils. 
It is possible to use colorants such as inorganic pigments, for example 
iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such 
as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, 
and trace nutrients such as salts of iron, manganese, boron, copper, 
cobalt, molybdenum and zinc. 
The formulations in general contain between 0.1 and 95 percent by weight of 
active compound, preferably between 0.5 and 90%. 
The active compounds according to the invention, as such or in the form of 
their formulations, can also be used, for combating weeds, as mixtures 
with known herbicides, finished formulations or tank mixes being possible. 
Possible components for the mixtures are known herbicides, such as, for 
example, N-(2-benzothiazolyl)-N,N'-dimethylurea, 
3-(3-chloro-4-methylphenyl)-1,1-dimethylurea, 
3-(4-isopropylphenyl)-1,1-dimethylurea, 
1-(4-methyl-phenyl)-3-(1-methyl-1-phenyl-ethyl)-urea, 
2-chloro-N-{[4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]carbonyl}-benzen 
esulphonamide, ethyl 
2-{[(4-chloro-6-methoxy-2-pyrimidyl)aminocarbonyl]aminosulphonyl}-benzoate 
, 2-ethylamino-6 (1,1-dimethylethyl-amino)-4-methylthio-1,3,5-triazine, 
2-chloro-4-ethylamino-6-(1-methyl-ethyl)-1,3,5-triazine, 
4-amino-6-(1,1-dimethylethyl)-3-methylthio-1,2,4-triazin-5(4H)-one, 
4-amino-6-(1,1-dimethylethyl)-3-ethylthio-1,2,4-triazin-5(4H)-one, 
1-amino-6-ethylthio-3-(2,2-dimethylpropyl)-1,3,5-triazine-2,4-(1H,3H)-dion 
e, 
5-(2-chloro-4-trifluoromethylphenoxy)-N-methylsulphonyl-2-nitrobenzamide, 
2-ethoxy-1-methyl-2-oxo-ethyl 
5-(2-chloro-4-trifluoromethyl-phenoxy)-2-nitrobenzoate, methyl 
2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionate, 
2-{4-(3-chloro-5-trifluoromethyl-2-pyridinyl)oxy]-phenoxy}-propionic acid, 
the R-enantiomer of (trimethylsilyl)-methyl 2-{4-[(3,5-dichloro- 
2-pyridinyl)-oxy]-phenoxy}-propionate, 2,4-dichlorophenoxyacetic acid, 
2-(2,4-dichlorophenoxy)-propionic acid, 4-chloro-2-methyl-phenoxy-acetic 
acid, 2-(4-chloro-2-methylphenoxy)-propionic acid, 
3,5-diiodo-4-hydroxy-benzonitrile, 3,5-dibromo-4-hydroxy-benzonitrile, 
2-[5-methyl-5-(1-methylethyl)-4-oxo-2-imidazolin-2-yl]-3-pyridinecarboxyli 
c acid, 
2-(1-ethoxyamino-butylidene)-5-(2-ethylthiopropyl)-1,3-cyclohexanedione, 
[(4-amino-3,5-dichloro-6-fluoro-2-pyridyl)oxy]-acetic acid, 
3-isopropyl-2,1,3-benzothiadiazin-4-one 2,2-dioxide, 
2-(2-benzothiazolyloxy)-N-methyl-N-phenyl-acetamide, S-ethyl 
N,N-dipropylthiocarbamate, 1-ethylthiocarbonyl-hexahydro-1H-azepine, 
propionic acid 3,4-dichloroanilide, chloroacetic acid 
N-(2,6-diethyl-phenyl)-N-methoxymethyl-amide, chloroacetic acid 
N-(2-ethyl-6-methyl-phenyl)-N-(2-methoxy-1-methylethyl)-amide, 
chloroacetic acid 
N-(2,6-dimethyl-phenyl)-N-(1H-pyrazol-1-yl-methyl)-amide, chloroacetic 
acid N-(2,6-diethylphenyl)-N-(2-propoxyethyl)-amide, 
3,7-dichloro-8-quinolinecarboxylic acid, 
4-(2,4-dichloro-phenoxy)-2-methoxy-aniline, ethyl 
2-(-((6-chloro-benzoxazol-2-yl)-oxy)-phenoxy)-propionate, 
(2,4-dichlorophenyl)(1,3-dimethyl-5-((4-methyl-phenyl)-sulphonyl-oxy)-1H-p 
yrazol-4-yl)-methanone and 0-(6-chloro-3-phenyl-4-pyridazinyl) S-octyl 
thiocarbonate. Surprisingly, some mixtures also show a synergistic action. 
Mixtures with other known active compounds, such as fungicides, 
insecticides, acaricides, nematicides, bird repellents, plant nutrients 
and agents which improve soil structure, are also possible. 
The active compounds can be used as such, in the form of their formulations 
or in the use forms prepared therefrom by further dilution, such as 
ready-to-use solutions, suspensions, emulsions, powders, pastes and 
granules. They are used in the customary manner, for example by watering, 
spraying, atomizing or scattering. 
The active compounds according to the invention can be applied either 
before or after emergence of the plants. They can also be incorporated 
into the soil before sowing. 
The amount of active compound used can vary within a substantial range. It 
depends essentially on the nature of the desired effect. In general, the 
amounts used are between 0.001 and 5 kg of active compound per hectare of 
soil surface, preferably between 0.01 and 1 kg per ha. 
The preparation and use of the active compounds according to the invention 
can be seen from the following examples.