Substituted sulfonylureas of the general formula I ##STR1## where n and m are each 0 or 1, and PA1 R.sup.1 is hydrogen, alkyl, alkenyl or alkynyl; PA1 R.sup.2 is halogen or trifluoromethyl when m is 0, or, when m is 1, alkyl, alkenyl or alkynyl and, when X is 0 or S and m is 1, is trifluoromethyl or chlorodifluoromethyl; PA1 X is 0, S or N--R.sup.4, where R.sup.4 is hydrogen or alkyl; PA1 R.sup.3 is hydrogen, halogen, alkyl, haloalkyl or alkoxy; PA1 A is haloalkyl, halogen or ##STR2## where Z is oxygen or alkylimino N--R.sup.6 ; PA1 R.sup.5 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, alkenyl or alkynyl; PA1 R.sup.6 is hydrogen, alkyl, or together with R.sup.5 is a C.sub.4 -C.sub.6 -alkylene chain, where one methylene may be replaced by an oxygen atom or a C.sub.1 -C.sub.4 -alkylimino group, and PA1 R.sup.7 is hydrogen or halogen, and environmentally tolerated salts thereof, processes and intermediates for the manufacture of compounds I, and their use as herbicides and bioregulators.

The present invention relates to substituted sulfonylureas of the formula I 
##STR3## 
where n and m are each 0 or 1, and 
R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl or 
C.sub.3 -C.sub.6 -alkynyl, 
R.sup.2 is halogen or trifluoromethyl when m is 0, or C.sub.1 -C.sub.4 
-alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl when m is 
1, or trifluoromethyl or chlorodifluoromethyl when X is 0 or S and m is 1, 
X is 0, S or N--R.sup.4 where R.sup.4 is hydrogen or C.sub.1 -C.sub.4 
-alkyl, 
R.sup.3 is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 
-haloalkyl or C.sub.1 -C.sub.4 -alkoxy, 
A is C.sub.1 -C.sub.4 -haloalkyl, halogen or 
##STR4## 
where Z is oxygen or alkylimino NR.sup.6, 
R.sup.5 is hydrogen, C.sub.1 -C.sub.6 -alkyl which can carry up to three of 
the following: halogen, C.sub.1 -C.sub.4 -alkoxyl 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.7 -cycloalkyl and/or phenyl, or C.sub.5 
-C.sub.7 -cycloalkyl which can carry up to three C.sub.1 -C.sub.4 -alkyl 
groups, or C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl, 
R.sup.6 is hydrogen, C.sub.1 -C.sub.6 -alkyl, or together with R.sup.5 is 
C.sub.4 -C.sub.6 -alkylene in which one methylene can be replaced by 
oxygen or C.sub.1 -C.sub.4 -alkylimino, 
R.sup.7 is hydrogen or halogen. 
The present invention also relates to a process for preparing the compounds 
I and to the use thereof as herbicides and intermediates for preparing 
sulfonylureas I. 
U.S. Pat. No. 4,547,215 discloses various sulfonylpyrimidylureas which are 
substituted by chlorine in the pyrimidine moiety as herbicides. 
EP-A-84,020 and 169,815 describe sulfonylureas which are substituted in 
the pyrimidine moiety by difluoromethoxy or bromodifluoromethoxy. However, 
these compounds are unsatisfactory because the selectivity for noxious 
plants is inadequate. 
It is an object of the present invention to provide novel 
sulfonylpyrimidylureas with improved herbicidal properties. We have found 
that this object is achieved by the sulfonylureas defined in the 
introduction. 
We have also found that the compounds of the formula I and their alkali 
metal and alkaline earth metal salts act highly selectively against 
noxious plants in crops such as cereals and corn. 
We have also found chemically original processes for preparing the 
compounds I. Unexpectedly by comparison with the prior art, the 
sulfonylureas I can be prepared regioselectively and in high yield and 
purity starting from substituted 2-amino-4-fluoroalkoxypyrimidines of the 
formula IIIa 
##STR5## 
where m is 1 and n is 0 or 1, and 
R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl or 
C.sub.3 -C.sub.6 -alkynyl, 
R.sup.2 is C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 
-C.sub.6 -alkynyl, 
R.sup.7 is hydrogen or halogen, 
X is 0, S or N--R.sup.4 where 
R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl. 
The present invention also relates to these intermediates and the 
preparation thereof. 
The preparation of compounds which are halogen-substituted in the 
pyrimidine moiety (R.sup.2 =Hal, m=0) starts from appropriately 
substituted 2-amino-4-fluoroalkoxy-6-halopyrimidines of the structure IIIb 
(see scheme 2) to whose preparation the application U.S. Ser. No. 
07/663,975, filed Mar. 4, 1991 relates. Pyrimidine intermediates with m=0 
and R.sup.2 =trifluoromethyl are obtained in a similar manner as shown in 
scheme 3. 
The sulfonylureas of the formula I according to the invention can be 
obtained by routes A, B and C shown in scheme 1:

EMBODIMENT A 
A sulfonyl isocyanate II is reacted in a conventional manner (EP-A-162,723) 
in an inert organic solvent with approximately the stoichiometric amount 
of a 2-aminopyrimidine III at from 0.degree. to 120.degree. C., preferably 
10.degree. to 100.degree. C. The reaction can be carried out under 
atmospheric or superatmospheric (up to 50 bar) pressure, preferably under 
1 to 5 bar, continuously or batchwise. Suitable solvents are listed in the 
abovementioned literature. 
EMBODIMENT B 
An appropriate sulfonylcarbamate of the formula IV is reacted in a 
conventional manner (EP-A-162,723) in an inert organic solvent at from 
0.degree. to 120.degree. C., preferably 10.degree. to 100.degree. C., with 
a 2-aminopyrimidine. It is possible to add bases such as tertiary amines 
to increase the reaction rate and improve the product quality. 
Examples of bases suitable for this purpose are tertiary amines such as 
pyridine, the picolines, 2,4- and 2,6-lutidine, 2,4,6-collidine, 
p-dimethylaminopyridine, 1,4-diaza[2.2.2]bicyclooctane (DABCO) and 
1,8-diazabicyclo[5.4.0]undec-7-ene. 
The solvents which are expediently used are those indicated in the 
literature and/or halohydrocarbons such as dichloromethane and 
chlorobenzene, ethers such as diethyl ether, tetrahydrofuran and dioxane, 
acetonitrile, dimethylformamide and/or ethyl acetate, in an amount of from 
100 to 4000% by weight, preferably from 1000 to 2000% by weight, based on 
the starting materials II, IV and V. 
For the purpose of preparing the compounds according to the invention, the 
2-aminopyrimidine intermediates III can be obtained in the following 
advantageous manner: 
##STR7## 
The 2-amino-6-trifluoromethylpyrimidine derivatives IIIc are obtained in a 
corresponding manner when the appropriate 
2,4-dihalo-6-trichloromethylpyrimidines are reacted, in place of the 
2,4,6-trihalo compounds VII, as shown in Scheme 3 (see Examples I.1, I.6 
and I.12). 
##STR8## 
are obtained from the intermediates XIV in Scheme 2 by replacement of the 
4-halogen atom by the reaction sequence depicted in Scheme 3 (1. CH.sub.3 
OH, 2. Cl.sub.2, 3. SbF.sub.3) and subsequent reaction with R.sup.1 
NH.sub.2. 
As shown in Scheme 2, for example, a 2,4,6-trihalopyrimidine VII, disclosed 
in J.Med.Chem. 6 (1963) 688, or commercially available, can be reacted in 
an aprotic polar solvent 
a) with methanol VIII in the presence or absence of a base or 
b) with a methanolate VIIIa in the presence of methanol VIII at from 
-40.degree. to 120.degree. C. to give the methoxypyrimidine IX. These 
reactions can be carried out under atmospheric or superatmospheric (1 to 
10 bar, preferably 1 to 5 bar) pressure, continuously or batchwise. 
Hal in formula VII is fluorine, chlorine or bromine. 
M.sup.1 in formula VIIIa is a cation of an alkali metal such as lithium, 
sodium or potassium, or the equivalent of an alkaline earth metal cation 
such as magnesium, calcium or barium. 
The following solvents are suitable for reacting the trihalopyrimidine with 
methanol VIII: 
Ethers such as methyl tert.-butyl ether, diethyl ether, ethyl propyl ether, 
n-butyl ethyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, 
diisopropyl ether, cyclohexyl methyl ether, tetrahydrofuran, 
1,2-dimethoxyethane, diethylene glycol dimethyl ether and anisole, 
chlorohydrocarbons such as 1,1,2,2-tetrachloroethane, 
1,1-dichloroethylene, chlorobenzene, 1,2-dichlorobenzene and 
1-chloronaphthalene, and mixtures thereof. 
The solvent is expediently used in an amount of from 100 to 2000% by 
weight, preferably 500 to 1500% by weight, based on the starting material 
VII. 
However, the reaction of the starting materials VII and VIII is expediently 
carried out directly in excess methanol VIII as solvent. It is possible to 
add an alkali metal methanolate VIIIa in an equivalent amount or in an 
amount which is up to 5 mol % above or below this, based on the starting 
material VII, to a suspension of the starting material VII in from 5 to 20 
times the amount by weight of alcohol VIII as solvent, based on the 
starting material VII, over the course of up to one hour at from about 
-20.degree. to 80.degree. C. To complete the reaction, the mixture is then 
stirred at from 0.degree. to 120.degree. C., preferably 0.degree. to 
100.degree. C., for about 1/2 to 8 hours. 
The methoxypyrimidines are isolated by conventional working up methods. 
The methoxypyrimidine IX is chlorinated to give the 
trichloromethoxypyrimidine XI at, for example, from 60.degree. to 
180.degree. C. 
Suitable chlorinating agents are elemental chlorine and substances which 
release chlorine such as sulfuryl chloride or phosphorus pentachloride. It 
is also possible to generate chlorine in situ by oxidizing hydrochloric 
acid, for example with pyrolusite or by anodic chlorination. 
The chlorination can be carried out in the presence of an inert solvent, 
for example a chlorohydrocarbon such as chloroform, tetrachloromethane, 
chlorobenzene, 1,2- or 1,3- or 1,4-dichlorobenzene, a nitrile such as 
acetonitrile or propionitrile, a nitro compound such as nitrobenzene, a 
carboxylic acid such as acetic or propionic acid, an anhydride such as 
acetic anhydride, an acid chloride such as chloroacetyl chloride, 
.alpha.-chloropropionyl chloride or .alpha.,.alpha.-dichloropropionyl 
chloride, an inorganic acid halide such as phosphorus trichloride or 
phosphorus oxychloride or, preferably, without solvent in the melt of the 
starting material IX. 
A radical initiator can be used to increase the reaction rate; suitable for 
this is irradiation with light, preferably UV light, or addition of 
.alpha.,.alpha.'-azoisobutyronitrile, expediently in an amount of from 0.2 
to 7 mol % based on the starting material IX. The reaction rate can also 
be increased by addition of a catalyst; suitable for this is phosphorus 
pentachloride, expediently in an amount of from 0.5 to 7 mol % based on 
the starting material IX. In this case, the starting material IX is mixed 
with the catalyst and then the chlorination is started. In place of 
phosphorus pentachloride, it is also possible to add components which form 
it under the reaction conditions, e.g. phosphorus trichloride or yellow 
phosphorus, and then to start with the chlorination. 
Starting material IX can be reacted with chlorine in approximately 
stoichiometric amount or, preferably, in excess, advantageously with from 
3.1 to 11, in particular 3.3 to 5, moles of Cl.sub.2 per methoxy 
equivalent in the starting material IX. The reaction can be carried out at 
from 60.degree. to 180.degree. C., advantageously from 100.degree. to 
150.degree. C., under atmospheric or superatmospheric pressure 
continuously or batchwise. 
When chlorination is carried out under 1 bar, it is expedient to employ 
from 3.3 to 5 moles of chlorine gas based on one methoxy equivalent in the 
starting material IX, which corresponds to a chlorine conversion of from 
91 to 60%. It is possible, by suitable measures, e.g. by use of moderate 
superatmospheric pressure, expediently from 1 to 10 bar, or by use of a 
bubble column, to increase the chlorine conversion. It is advantageous to 
maximize the time during which the chlorine gas is in contact with the 
organic phase by, for example, vigorously stirring the latter or forcing 
the chlorine gas to pass through a thick layer of the organic phase. 
The reaction time is generally from about 0.5 to 12 hours. 
The procedure in a preferred embodiment of the process is to pass the 
required amount of chlorine gas over the course of from 0.5 to 12 hours, 
preferably 1 to 10 hours, into the vigorously stirred liquid starting 
material IX, starting at from 60.degree. to 80.degree. C. and increasing 
the temperature continuously, possibly by utilizing the exothermic nature 
of the reaction, to from 100.degree. to 150.degree. C. at the end of the 
reaction. In the case of large batches, the exothermic nature of the 
reaction must be taken into account by applying external cooling or by 
suitable metering in of the chlorine; when the reaction subsides the 
cooling bath is removed and the mixture may then be heated. 
The final products are worked up and isolated in a conventional manner. For 
example, residual hydrogen chloride, chlorine or catalyst can be driven 
out of the hot organic phase using an inert gas; this results in a high 
yield of a reasonably pure crude product. It can be further purified by 
distillation or chromatography or else employed immediately for further 
reactions. 
The reaction of the trichloromethoxypyrimidine XI with a fluorinating agent 
is carried out at from 0.degree. to 170.degree. C., for example. 
Suitable fluorinating agents are antimony trifluoride in the presence or 
absence of catalytic amounts of an antimony(V) salt, e.g. antimony(V) 
chloride, and hydrogen fluoride. 
It is expedient to use an excess of from 1 to 200, preferably 5 to 20, mol 
% of antimony trifluoride per trichloromethyl equivalent. The amount of 
antimony(V) salt catalyst is from 1 to 20, preferably 5 to 18, mol % per 
trichloromethyl equivalent. The starting material XI is preferably metered 
at from 90.degree. to 130.degree. C. into the mixture containing the 
fluorinating agent, which is then heated at from 140.degree. to 
170.degree. C. for from 10 to about 120 minutes. Working up is then 
carried out by distillation. 
However, the reaction can also be carried out continuously by adding the 
starting material XI at from 140.degree. to 170.degree. C. over the course 
of from 10 to about 120 minutes and simultaneously distilling out under 
reduced pressure the lower boiling final product XIV. Traces of antimony 
salts which have been carried over can be removed by extraction with 
concentrated hydrochloric acid. 
Halogen replacement can be stopped at the chlorodifluoromethoxy stage by 
using only small amounts, e.g. from 0.2 to 1 mol %, of antimony(V) salt 
catalyst, or none at all, and reducing the amount of antimony trifluoride 
to from 60 to 90 mol % per trichloromethyl equivalent. 
In place of antimony trifluoride it is possible to use hydrogen fluoride at 
from 0.degree. to 170.degree. C., preferably 40.degree. to 120.degree. C. 
This is carried out by mixing the starting material XI with an excess of 
from 300 to 700, preferably 350 to 400, mol % hydrogen fluoride per 
trichloromethyl equivalent in an autoclave and stirring for from 10 
minutes to about 10 hours. After the pressure has been released and 
volatiles have been removed, working up is carried out as described. 
The reaction of the fluoromethoxypyrimidine XIV with an amine XV is carried 
out, for example, at from -80.degree. to 40.degree. C. 
R.sup.1 in formula XV is, for example, hydrogen, C.sub.1 -C.sub.4 -alkyl 
such as methyl, ethyl, n-propyl, i-propyl, n-butyl, sec.-butyl, i-butyl or 
tert.-butyl, C.sub.3 -C.sub.4 -alkenyl such as 2-propenyl, 
2-methylethenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl or 
2-methyl-2-propenyl, or C.sub.3 -C.sub.4 -alkynyl such as propargyl, 
2-butynyl, 3-butynyl or 1-methyl-2-propynyl. 
Among the amines which can be employed, the following may be mentioned: 
ammonia, methylamine, ethylamine, n-propylamine, isopropylamine, 
n-butylamine, isobutylamine, sec.-butylamine, tert.-butylamine, 
2-propenylamine, 2-methylethenylamine, 2-butenylamine, 3-butenylamine, 
1-methyl-2-propenylamine, 2-methyl-2-propenylamine, propargylamine, 
2-butynylamine, 3-butynylamine and 1-methyl-2-propynylamine. 
The 2,6-dihalopyrimidines XIV can be reacted with the amines XV in an 
aprotic polar solvent at from -80.degree. to 40.degree. C., either 
employing the amine XV in excess or using an additional organic base. 
Examples of solvents suitable for the reaction of the 2,6-dihalopyrimidine 
XIV with the amine XV are the following: 
Ethers such as methyl tert.-butyl ether, diethyl ether, ethyl propyl ether, 
n-butyl ethyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, 
diisopropyl ether, cyclohexyl methyl ether, tetrahydrofuran, 1 
2-dimethoxyethane, diethylene glycol dimethyl ether and anisole, esters 
such as ethyl acetate, n-butyl acetate and isobutyl acetate, and 
chlorohydrocarbons such as methylene chloride, 1,1,2,2-tetrachloroethane, 
1,1-dichloroethylene, 1,2-dichloroethane, chlorobenzene, 
1,2-dichlorobenzene and 1-chloronaphthalene, and mixtures of these 
solvents. 
The solvent is expediently used in an amount of from 100 to 2000% by 
weight, preferably 400 to 1200% by weight, based on the starting material 
XIV. 
It is advantageous to add from 1. 8 to 2.5, in particular 1.95 to 2.2, mole 
equivalents of the amine XV based on the starting material XIV over the 
course of 0.5 to 2 hours to the starting material XIV in one of the 
abovementioned solvents at from (-80.degree.) to 40.degree. C., preferably 
-70.degree. to 25.degree. C., to stir until the reaction is complete 
(after about 3 hours) and then to allow to warm to 25.degree. C. for the 
working up. 
If only approximately the stoichiometric amount of the amine XV is 
employed, it is expedient to add from 0.9 to 1.1 equivalents of an 
additional organic base based on starting material XIV. Suitable for this 
are the customary organic bases such as trimethylamine, triethylamine, 
ethyldiisopropylamine, triisopropylamine, N,N-dimethylaniline, 
N,N-dimethylcyclohexylamine, N-methylpyrrolidine, pyridine, quinoline, 
.alpha.-, .beta.- or .gamma.-picoline, 2,4- and 2,6-lutidine and 
triethylenediamine. 
The reaction can be carried out under atmospheric or superatmospheric 
pressure, continuously or batchwise. 
For the working up the reaction mixture is extracted with water to remove 
the salts, and the organic phase is dried and purified, e.g. by 
chromatography. However, it is also possible to concentrate the organic 
phase directly and to stir the residue with a solvent. 
The 2-amino-4-fluoroalkoxypyrimidines of the formula IIIa according to the 
invention are advantageously obtained by reacting 
2-amino-4-fluoroalkoxy-6-halopyrimidines of the formula IIIb 
##STR9## 
where Hal is fluorine, chlorine or bromine, and R.sup.1 and n have the 
abovementioned meaning, with a nucleophile of the formula XVI 
EQU H-X-R.sup.2 XVI 
where X and R.sup.2 have the abovementioned meanings, or the salt thereof. 
The reaction between 2-amino-4-fluoro-6-trifluoromethoxypyrimidine and 
methylamine is depicted in the following scheme: 
##STR10## 
The reaction between 2-amino-4-fluoro-6-chlorodifluoromethoxypyrimidine 
and sodium methylate is depicted in the following scheme: 
##STR11## 
The process provides novel 2-amino-4-fluorolkoxypyrimidines in high yield 
and purity in a straight-forward and economic way. Unexpectedly, there is 
no substitution of fluoroalkoxy groups. The chlorine atom in the ether 
side chain is also retained despite the alkaline reaction conditions. In 
view of the prior art (see, for example, EP-A-70,804), all these 
advantageous properties are surprising. 
Preferred intermediates IIIa and correspondingly preferred starting 
materials IIIb are those in whose formulae R.sup.1 and R.sup.2 are each 
C.sub.1 -C.sub.4 -alkyl such as methyl, ethyl, n-propyl, i-propyl, 
n-butyl, sec.-butyl, i-butyl or tert.-butyl, C.sub.3 -C.sub.4 -alkenyl 
such as 2-propenyl, 2-methylethenyl, 2-butenyl, 3-butenyl, 
1-methyl-2-propenyl or 2-methyl-2-propenyl, or C.sub.3 -C.sub.4 -alkynyl 
such as propargyl, 2-butynyl, 3-butynyl or 1-methyl-2-propynyl, and 
R.sup.1 can also be hydrogen. 
X is 0, S or N--R.sup.4, where 
R.sup.4 is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, 
sec.-butyl, i-butyl or tert.-butyl, 
R.sup.7 is hydrogen and 
n is 0 or 1. 
The reaction of the 2-amino-4-fluoroalkoxypyrimidine IIIb with a 
nucleophile XVI or salt thereof XVIa is carried out, for example, at from 
-80.degree. to 80.degree. C. Suitable nucleophiles XVI are ammonia, 
aliphatic amines, alcohols and thiols. 
Among the amines which can be employed as nucleophiles, the following 
should be mentioned: ammonia, methylamine, ethylamine, n-propylamine, 
isopropylamine, n-butylamine, isobutylamine, sec.-butylamine, 
tert.-butylamine, 2-propenylamine, 2-methylethenylamine, 2-butenylamine, 
3-butenylamine, 1-methyl-2-propenylamine, 2-methyl-2-propenylamine, 
propargylamine, 2-butynylamine, 3-butynylamine and 
1-methyl-2-propynylamine, dimethylamine, diethylamine, di-n-propylamine, 
di-n-butylamine, N-methylethylamine, N-ethyl-n-propylamine, 
N-methylallylamine and N-methylpropargylamine. 
Among the alcohols which can be employed as nucleophiles, the following 
should be mentioned: methanol, ethanol, n-propanol, i-propanol, n-butanol, 
i-butanol, sec.-butanol, tert.-butanol, 2-propenol, 2-methylethenol, 
2-butenol, 3-butenol, 1-methyl-2-propenol, 2-methyl-2-propenol, propynol, 
2-butynol, 3-butynol and 1-methyl-2-propynol. 
Among the thiols which can be employed as nucleophiles, the following 
should be mentioned: methanethiol, ethanethiol, n-propanethiol, 
i-propanethiol, n-butanethiol, i-butanethiol, sec.-butanethiol, 
tert.-butanethiol, 2-butenethiol, 2-methylethenethiol, 2-butenethiol, 
3-butenethiol, 1-methyl-2-propenethiol, 2-methyl-2-propenethiol, 
propynthiol, 2-butynthiol, 3-butynthiol and 1-methyl-2-propynthiol. 
The 4-halopyrimidines IIIb can be reacted with the amines XVI in an aprotic 
polar solvent at from -80.degree. to +80.degree. C., preferably 
-30.degree. to +20.degree. C., either employing the amine XVI in excess or 
using an additional organic base. 
The following solvents are suitable for the reaction of the 
4-halopyrimidine IIIb with the amine XVI: 
Ethers such as methyl tert.-butyl ether, diethyl ether, ethyl propyl ether, 
n-butyl ethyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, 
diisopropyl ether, cyclohexyl methyl ether, tetrahydrofuran, 
1,2-dimethoxyethane, diethylene glycol dimethyl ether and anisole, esters 
such as ethyl acetate, n-butyl acetate and isobutyl acetate, and 
chlorohydrocarbons such as methylene chloride, 1,1,2,2-tetrachloroethane, 
1,1-dichloroethylene, 1,2-dichloroethane, chlorobenzene, 
1,2-dichlorobenzene and 1-chloronaphthalene, and mixtures of these 
solvents. 
The solvent is expediently used in an amount of from 100 to 2000% by 
weight, preferably 400 to 1200% by weight, based on the starting material 
IIIb. 
It is advantageous to add from 1.8 to 2.5, in particular 1.95 to 2.2, mole 
equivalents of the amine XVI based on the starting material IIIb over the 
course of 0.5 to 2 hours to the starting material IIIb in one of the 
abovementioned solvents at from (-80.degree.) to 80.degree. C., preferably 
-30.degree. to 25.degree. C., to stir until the reaction is complete 
(after about 3 hours) and then to allow to warm to 25.degree. C. for the 
working up. 
If only approximately stoichiometric amounts of the amine XVI is employed, 
it is expedient to add from 0.9 to 1.1 equivalents of an additional 
organic base based on starting material IIIb. Suitable for this are 
organic bases such as trimethylamine, triethylamine, 
ethyldiisopropylamine, triisopropylamine, N,N-dimethylaniline, 
N,N-dimethylcyclohexylamine, N-methylpyrrolidine, pyridine, quinoline, 
.alpha.-, .beta.- or .gamma.-picoline, 2,4- or 2,6-lutidine and 
triethylenediamine. 
The reaction with alcohols or thiols can be carried out in a similar manner 
to that described for amines. The nucleophile is advantageously added in 
an amount of from 0.9 to 1.3 mole equivalents based on starting material 
IIIb over the course of from 0.5 to 2 hours together with one of the 
abovementioned bases to a mixture of starting material IIIb with one of 
the above-mentioned solvents at -30.degree. to 20.degree. C., and the 
mixture is then stirred until the reaction is complete (about 3 hours) and 
then allowed to warm to 25.degree. C. for the working up. 
Besides the solvents mentioned, also suitable are ketones, e.g. acetone or 
methyl ethyl ketone, dipolar aprotic solvents, e.g. acetonitrile, 
dimethylformamide, dimethylacetamide, dimethyl sulfoxide, 
N-methylpyrrolidone and 1,3-dimethylimidazolin-2-one, aromatic compounds, 
e.g. benzene, toluene or xylene, or mixtures thereof. It is possible and 
advantageous when alcohols are employed as nucleophiles to use the latter 
directly as solvents. Salts of alcohols or thiols are particularly 
preferred and make the use of an additional organic base unnecessary. They 
are prepared in a conventional manner by use of alkali metals or alkaline 
earth metals or metal hydrides, e.g. NaH, KH, CaH.sub.2 or LiH. 
The reaction can be carried out under atmospheric or superatmospheric 
pressure, continuously or batchwise. 
To work up the reaction mixture it is extracted with water to remove salts 
and is dried, and the organic phase is purified, e.g. by chromatography. 
However, in most cases the reaction products are sufficiently pure so that 
it is merely necessary to filter off the precipitated salt and to 
concentrate the organic phase. 
Examples of preferred intermediates of the formula IIIa are: 
2-amino-4-methoxy-6-trifluoromethoxypyrimidine, 
2-amino-4-chlorodifluoromethoxy-6-methoxypyrimidine, 
2-amino-4-ethoxy-6-trifluoromethoxypyrimidine, 
2-amino-4-chlorodifluoromethoxy-6-ethoxypyrimidine, 
2-amino-4-allyloxy-6-trifluoromethoxypyrimidine, 
2-amino-4-allyloxy-6-chlorodifluoromethoxypyrimidine, 
2-amino-4-methylthio-6-trifluoromethoxypyrimidine, 
2-amino-4-chlorodifluoromethoxy-6-methylthiopyrimidine, 
2-amino-4-ethylthio-6-trifluoromethoxypyrimidine, 
2-amino-4-chlorodifluoromethoxy-6-ethylthiopyrimidine, 
2-amino-4-methylamino-6-trifluoromethoxypyrimidine, 
2-amino-4-chlorodifluoromethoxy-6-methylaminopyrimidine, 
2-amino-4-ethylamino-6-trifluoromethoxypyrimidine, 
2-amino-4-chlorodifluoromethoxy-6-ethylaminopyrimidine, 
2-amino-4-dimethylamino-6-trifluoromethoxypyrimidine, 
2-amino-4-chlorodifluoromethoxy-6-dimethylaminopyrimidine, 
4-methoxy-2-methylamino-6-trifluoromethoxypyrimidine, 
4-chlorodifluoromethoxy-6-methoxy-2-methylaminopyrimidine, 
4-ethoxy-2-methylamino-6-trifluoromethoxypyrimidine, 
4-chlorodifluoromethoxy-6-ethoxy-2-methylaminopyrimidine, 
2,4-bis(methylamino)-6-trifluoromethoxypyrimidine, 
4-chlorodifluoromethoxy-2,6-bis(methylamino)pyrimidine, 
4-ethylamino-2-methylamino-6-trifluoromethoxypyrimidine, 
4-chlorodifluoromethoxy-6-ethylamino-2-methylaminopyrimidine, 
4-dimethylamino-2-methylamino-6-trifluoromethoxypyrimidine, 
4-chlorodifluoromethoxy-6-dimethylamino-2-methylaminopyrimidine. 
EMBODIMENT C 
A sulfonamide of the formula V is reacted in a conventional manner 
(EP-A-141,777) in an inert organic solvent with approximately the 
stoichiometric amount of a phenyl carbamate VI at from 0.degree. to 
120.degree. C., preferably 20.degree. to 100.degree. C. The reaction can 
be carried out under atmospheric or superatmospheric (up to 50 bar) 
pressure, preferably under from 1 to 5 bar, continuously or batchwise. 
Suitable solvents are, besides those listed in the literature cited above, 
e.g. nitrohydrocarbons such as nitroethane and nitrobenzene, nitriles such 
as acetonitrile and benzonitrile, esters such as ethyl acetate, amides 
such as dimethylformamide and/or ketones such as acetone. The reaction is 
preferably carried out in ethyl acetate as solvent and with pyridine or 
one of the abovementioned tertiary amines as base. 
The sulfonamides required as starting materials of the formula V can be 
prepared from substituted anilines, e.g. anthranilic esters or imides, 
2-haloanilines or 2-haloalkylanilines by the Meerwein reaction and 
subsequent reaction with ammonia. 
Compounds of the formula I where R.sup.5 is hydrogen are obtained by 
hydrolysis of esters of the formula I where R.sup.5 is C.sub.1 -C.sub.6 
-alkyl. The hydrolysis is carried out with at least twice the amount of a 
base such as sodium or potassium hydroxide, expediently in a solvent 
mixture containing 2 to 8 times the amount of methanol and 10 to 40 times 
the amount of water based on the weight of the relevant ester of the 
formula I, at from 30.degree. to 80.degree. C. for from 1 to 20 hours. The 
sulfonamide carboxylic acids of the formula I are precipitated by 
acidification. 
With a view to the biological activity, preferred compounds of the formula 
I have the following meanings for the substituents: 
R.sup.1 is hydrogen or methyl, 
R.sup.2 is fluorine, chlorine, bromine or trifluoromethyl (m=0), and 
methyl, ethyl, n-propyl or isopropyl (m=1), 
R.sup.3 is hydrogen, fluorine, chlorine, bromine, methyl, methoxy or 
trifluoromethyl, 
X is oxygen, sulfur or -NR.sup.4 where 
R.sup.4 is hydrogen, methyl or ethyl, 
A is chlorine, trifluoromethyl, carboxyl or carbamoyl, 
R.sup.5 is C.sub.3 -C.sub.6 -alkyl such as methyl, ethyl, n-propyl or 
isopropyl, alkenyl such as allyl, crotyl or but-1-en-3-yl, alkynyl such as 
propargyl, but-1-yn-3-yl and but-2-ynyl, haloalkyl such as 2-chloroethyl, 
2-chloro-n-propyl, 3-chloro-n-propyl, 1-chloro-2-butyl, 2-chloroisobutyl, 
4-chloro-n-butyl, chloro-tert.-butyl, 3-chloro-2-propyl and 
2,2,2-trifluoroethyl, alkoxyalkyl such as 2-methoxyethyl, 2-ethoxyethyl, 
3-methoxy-n-propyl, 2-methoxy-n-propyl, 3-methoxy-n-butyl, 
1-methoxy-2-butyl, methoxy-tert.-butyl, 2-methoxy-n-butyl and 
4-methoxy-n-butyl, alkoxyalkoxyalkyl such as 2-methoxyethoxymethyl, 
2-(ethoxy)ethoxymethyl, 2-(propoxy)ethoxymethyl, 2-methoxyethoxyethyl, 
2-(ethoxy)ethoxyethyl and 2-(methoxymethoxy)ethyl, haloalkoxyalkyl such as 
2-(.beta.-chloroethoxy)ethyl, 3-(.beta.-chloroethoxy)-n-propyl and 
3-(.gamma.-chloro-n-propoxy)-n-propyl, cycloalkyl such as cyclopentyl and 
cyclohexyl, 
R.sup.6 is hydrogen, alkyl such as methyl, ethyl, n-propyl, isopropyl and 
n-butyl, or together with R.sup.5 is tetramethylene, pentamethylene, 
hexamethylene, ethyleneoxyethylene and ethylene-N-methyliminoethylene, 
R.sup.7 is hydrogen and 
n is 0 or 1. 
Suitable salts of the compounds of the formula I are salts which can be 
used in agriculture, for example alkali metal salts such as the potassium 
or sodium salt, alkaline earth metal salts such as the calcium, magnesium 
or barium salt, manganese, copper, zinc or iron salts, and ammonium, 
phosphonium, sulfonium or sulfoxonium salts, for example ammonium salts, 
tetraalkylammonium salts, benzyltrialkylammonium salts, trialkylsulfonium 
salts or trialkylsulfoxonium salts. 
The herbicidal and growth-regulating compounds I, or agents containing 
them, may be applied for instance in the form of directly sprayable 
solutions, powders, suspensions (including high-percentage aqueous, oily 
or other suspensions), dispersions, emulsions, oil dispersions, pastes, 
dusts, broadcasting agents, or granules by spraying, atomizing, dusting, 
broadcasting or watering. The forms of application depend entirely on the 
purpose for which the agents are being used, but they must ensure as fine 
a distribution of the active ingredients according to the invention as 
possible. 
For the preparation of solutions, emulsions, pastes and oil dispersions to 
be sprayed direct, mineral oil fractions of medium to high boiling point, 
such as kerosene or diesel oil, further coal-tar oils, and oils of 
vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons 
such as toluene, xylene, paraffin, tetrahydronaphthalene, alkylated 
naphthalenes and their derivatives, methanol, ethanol, propanol, butanol, 
cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly 
polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, 
N-methylpyrrolidone, water, etc. are suitable. 
Aqueous formulations may be prepared from emulsion concentrates, pastes, 
oil dispersions, wettable powders or water-dispersible granules by adding 
water. To prepare emulsions, pastes and oil dispersions the ingredients as 
such or dissolved in an oil or solvent may be homogenized in water by 
means of wetting or dispersing agents, adherents or emulsifiers. 
Concentrates which are suitable for dilution with water may be prepared 
from active ingredient, wetting agent, adherent, emulsifying or dispersing 
agent and possibly solvent or oil. 
Examples of surfactants are: alkali metal, alkaline earth metal and 
ammonium salts of aromatic sulfonic acids, e.g., ligninsulfonic acid, 
phenolsulfonic acid, naphthalenesulfonic acid and 
dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylaryl 
sulfonates, and alkyl, lauryl ether and fatty alcohol sulfates, and salts 
of sulfated hexadecanols, heptadecanols, and octadecanols, salts of fatty 
alcohol glycol ethers, condensation products of sulfonated naphthalene and 
naphthalene derivatives with formaldehyde, condensation products of 
naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, 
polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, 
ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol 
polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether 
alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, 
ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated 
polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, 
lignin-sulfite waste liquors and methyl cellulose. 
Powders, dusts and broadcasting agents may be prepared by mixing or 
grinding the active ingredients with a solid carrier. 
Granules, e.g., coated, impregnated or homogeneous granules, may be 
prepared by bonding the active ingredients to solid carriers. Examples of 
solid carriers are mineral earths such as silicic acids, silica gels, 
silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, 
loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium 
sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium 
sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable 
products such as grain meals, bark meal, wood meal, and nutshell meal, 
cellulosic powders, etc. 
The formulations contain from 0.1 to 95, and preferably 0.5 to 90%, by 
weight of active ingredient. The active ingredients are employed in a 
purity of from 90 to 100, and preferably from 95 to 100%, (according to 
the NMR spectrum). 
The compounds I according to the invention may be formulated for instance 
as follows: 
I. 90 parts by weight of compound no. 1.001 is mixed with 10 parts by 
weight of N-methyl-alpha-pyrrolidone. A mixture is obtained which is 
suitable for application in the form of very fine drops. 
II. 20 parts by weight of compound no. 1.003 is dissolved in a mixture 
consisting 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 the calcium salt of 
dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 
moles of ethylene oxide and 1 mole of castor oil. By pouring the solution 
into 100,000 parts by weight of water and uniformly distributing it 
therein, an aqueous dispersion is obtained containing 0.02% by weight of 
the active ingredient. 
III. 20 parts by weight of compound no. 2.001 is dissolved in a mixture 
consisting 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. By pouring the solution 
into 100,000 parts by weight of water and finely distributing it therein, 
an aqueous dispersion is obtained containing 0.02% by weight of the active 
ingredient. 
IV. 20 parts by weight of compound no. 3.001 is dissolved in a mixture 
consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a 
mineral oil fraction having a boiling point between 210.degree. and 
280.degree. C., and 10 parts by weight of the adduct of 40 moles of 
ethylene oxide and 1 mole of castor oil. By pouring the solution into 
100,000 parts by weight of water and uniformly distributing it therein, an 
aqueous dispersion is obtained containing 0.02% by weight of the active 
ingredient. 
V. 20 parts by weight of compound no. 5.001 is well mixed with 3 parts by 
weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 17 
parts by weight of the sodium salt of a lignin-sulfonic acid obtained from 
a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and 
triturated in a hammer mill. By uniformly distributing the mixture in 
20,000 parts by weight of water, a spray liquor is obtained containing 
0.1% by weight of the active ingredient. 
VI. 3 parts by weight of compound no. 6.001 is intimately mixed with 97 
parts by weight of particulate kaolin. A dust is obtained containing 3% by 
weight of the active ingredient. 
VII. 30 parts by weight of compound no. 7.001 is intimately mixed with a 
mixture consisting of 92 parts by weight of powdered silica gel and 8 
parts by weight of paraffin oil which has been sprayed onto the surface of 
this silica gel. A formulation of the active ingredient is obtained having 
good adherence. 
VIII. 20 parts by weight of compound no. 1.001 is intimately mixed with 2 
parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a 
fatty alcohol polyglycol ether, 2 parts of the sodium salt of a 
phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a 
paraffinic mineral oil. A stable oily dispersion is obtained. 
The active ingredients or the herbicidal and growth-regulating agents 
containing them may be applied pre- or postemergence. If certain crop 
plants tolerate the active ingredients less well, application techniques 
may be used in which the herbicidal agents are sprayed from suitable 
equipment in such a manner that the leaves of sensitive crop plants are if 
possible not touched, and the agents reach the soil or the unwanted plants 
growing beneath the crop plants (post-directed, lay-by treatment). 
When the active ingredients are used as herbicides, the application rates 
depend on the objective to be achieved, the time of the year, the plants 
to be combated and their growth stage, and are from 0.001 to 2, preferably 
0.01 to 1, kg of active ingredient per hectare. 
The compounds of the formula I may exercise a variety of influences on 
practically all plant development stages, and are therefore used as growth 
regulators. The diversity of action of growth regulators depends 
especially on 
a) the type and variety of plant; 
b) the time applied, with reference to the development stage of the plants 
and the time of the year; 
c) the place and method of application (seed treatment, soil treatment, 
application to foliage, or trunk injection in the case of trees); 
d) climatic factors, e.g., average temperature, amount of precipitate, 
sunshine and duration; 
e) soil conditions (including fertilization); 
f) the formulation of the active ingredient; and 
g) the concentration at which the active ingredient is applied. 
A description of some of the various possibilities of using the growth 
regulators according to the invention in agriculture and horticulture is 
given below. 
A. vegetative plant growth can be inhibited to a considerable extent, a 
fact which is manifested particularly in a reduction in plant height. The 
treated plants thus have a compact habit; furthermore, the leaf color is 
darker. 
Of advantage in practice is for example the reduction in grass growth on 
roadsides, hedges, canal embankments and on areas such as parks, 
sportsgrounds, fruit orchards, lawns and airfields, thus reducing 
expensive and time-consuming mowing. 
A further feature of economic interest is the increase in the rigor of 
crops which tend to lodge, such as cereals, Indian corn, sunflowers and 
soybeans. The shortening and strengthening of the stem thus caused reduces 
or eliminates the danger of lodging under unfavorable weather conditions. 
The use of growth regulators is also important for inhibiting plant height 
and changing the time of ripening in cotton. It is thus possible for this 
important crop to be harvested completely mechanically. 
In fruit and other trees, pruning costs can be reduced with growth 
regulators. With growth regulators, it is also possible to break up the 
alternate breeding rhythm of fruit trees. 
Growth regulators may also increase or inhibit lateral branching. This is 
of interest when, for instance in tobacco plants, it is desired to inhibit 
the formation of lateral shoots (suckers) in favor of leaf development. 
With growth regulators, it is possible for instance in winter rape to 
considerably increase the resistance to freeze injury. On the one hand, 
upward growth and the development of a too luxuriant (and thus 
particularly frost-susceptible) leaf or plant mass are inhibited; on the 
other, the young rape plants are kept, in spite of favorable growth 
conditions, in the vegetative development stage before winter frosts 
begin. The danger of freeze injury is thus eliminated in plants which tend 
to lose prematurely their inhibition to bloom and pass into the generative 
phase. In other crops, too, e.g., winter cereals, it is advantageous if 
the plants are well tillered in the fall as a result of treatment with the 
compounds according to the invention, but enter winter with not too lush a 
growth. This is a preventive measure against increased susceptibility to 
freeze injury and--because of the relatively low leaf or plant 
mass--attack by various (especially fungus) diseases. The inhibition of 
vegetative growth also makes closer planting possible in numerous crops, 
which means an increase in yield, based on the area cropped. 
B. Better yields both of plant parts and plant materials may be obtained 
with the novel agents. It is thus for instance possible to induce 
increased formation of buds, blossom, leaves, fruit, seed grains, roots 
and tubers, to increase the sugar content of sugarbeets, sugarcane and 
citrus fruit, to raise the protein content of cereals and soybeans, and to 
stimulate the increased formation of latex in rubber trees. 
The compounds of the formula I may raise the yield by influencing plant 
metabolism or by promoting or inhibiting vegetative and/or generative 
plant growth. 
C. It is also possible with growth regulators to shorten or lengthen growth 
stages and to accelerate or retard the ripening process in plant parts 
either before or after harvesting. 
A factor of economic interest is for example the facilitation of harvesting 
made possible by a chemical, temporally concentrated loosening 
(abscission) of the adherence of stalks to the branches of citrus fruit, 
olive trees, and other kinds of pomes, drupes and indehiscent fruit. The 
same mechanism, i.e., promotion of the formation of separation layers 
between fruit or leaf and stem of the plant, is also essential for a 
readily controllable defoliation of crop plants, e.g., cotton. 
D. Further, transpiration in crop plants may be reduced with growth 
regulators. This is particularly important for plants growing in 
agricultural areas which are expensive to irrigate, e.g., in arid or 
semi-arid areas. Irrigation frequency can be reduced by using the 
compounds according to the invention, making for lower costs. As a result 
of the use of growth regulators, the water available can be better 
utilized, because, inter alia, 
the size of the stomata opening is reduced; 
a thicker epidermis and cuticle are formed; 
penetration of the soil by the roots is improved; 
the micro-climate in the stand is favorably influenced by the more compact 
growth. 
The growth regulators to be used according to the invention may be applied 
not only to the seed (as a disinfectant), but also to the soil, i.e., via 
the roots, and--the method particularly preferred--to the foliage by 
spraying. 
As a result of the good tolerance by crop plants, the application rate may 
vary within wide limits. 
In view of the numerous application methods possible, the compounds 
according to the invention, or agents containing them, may be used in a 
large number of crops. Those which follow are given by way of example: 
______________________________________ 
Botanical name Common name 
______________________________________ 
Allium cepa onions 
Ananas comosus pineapples 
Arachis hypogaea peanuts (groundnuts) 
Asparagus officinalis asparagus 
Avena sative oats 
Beta vulgaris spp. altissima 
sugarbeets 
Beta vulgaris spp. rapa 
fodder beets 
Brassica napus var. napus 
rapeseed 
Brassica npaus var. napobrassica 
swedes 
Brassica rapa var. silvestris 
Camellia sinesis tea plants 
Carthamus tinctorius safflower 
Carya illinoinensis pecan trees 
Citrus limon lemons 
Citrus sinensis orange trees 
Coffea arabica (Coffea canephore, 
coffee plants 
Coffea liberica) 
Cucumis sativus cucumbers 
Cynodon dactylon Bermudagrass 
Daucus carota carrots 
Elais guineensis oil palms 
Fragaria vesca strawberries 
Glycine max soybeans 
Gossypium hirsutum (Gossypium 
cotton 
arboreum, Gossypium herbaceum, 
Gossypium vitifolium) 
Hevea brasiliensis rubber plants 
Hordeum vulgare barley 
Humulus lupulus hops 
Ipomoea batatas sweet potatoes 
Juglans regia walnut trees 
Lens culinaris lentils 
Linum usitatissimum flax 
Lycopersicon lycopersicum 
tomatoes 
Malus spp. apple trees 
Manihot esculaenta cassava 
Medicago sativa alfalfa (lucerne) 
Musa spp. banana plants 
Nicotiana tabacum (N. rustica) 
tobacco 
Olea europaea olive trees 
Oryza sative rice 
Phaseolus lunatis limabeans 
Phaseolus vulgaris snapbeans, green 
beans, dry beans 
Picea abies Norway spruce 
Pinus spp. pine trees 
Pisum sativum English peas 
Prunus avium cherry trees 
Prunus persica peach trees 
Pyrus communis pear trees 
Ribes sylvestre redcurrants 
Rincinus communis castor-oil plants 
Saccharum officinarum sugar cane 
Secale cereale rye 
Solanum tuberosum Irish potatoes 
Sorghum bicolor (s. vulgare) 
sorghum 
Theobroma cacoa cacoa plants 
Trifolium pratense red clover 
Triticum aestivum wheat 
Triticum durum durum wheat 
Vicia faba tick beans 
Vitis vinifera grapes 
Zea mays Indian corn, sweet 
corn, maize 
______________________________________ 
To increase the spectrum of action and to achieve synergistic effects, the 
compounds I according to the invention may be mixed with each other, or 
mixed and applied together with numerous representatives of other 
herbicidal or growth-regulating active ingredient groups. Examples of 
suitable components are diazines, 4H-3,1-benzoxazine derivatives, 
benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, 
thiolcarbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl 
ethers, triazinones, uracils, benzofuran derivatives, 
cyclohexane-1,3-dione derivatives, quinolinecarboxylic acid derivatives, 
aryloxy- and heteroaryloxyphenoxypropionic acids and their salts, esters 
and amides, etc. 
It may also be useful to apply the novel compounds of the formula I, either 
alone or in combination with other herbicides, in admixture with other 
crop protection agents, e.g., agents for combating pests or 
phytopathogenic fungi or bacteria. The compounds may also be mixed with 
solutions of mineral salts used to remedy nutritional or trace element 
deficiencies. Non-phytotoxic oils and oil concentrates may also be added. 
SYNTHESIS EXAMPLES 
The directions given in the synthesis examples below were used, after 
appropriate modifications of the starting materials, to produce further 
compounds of the formula I. The compounds obtained are given in the 
following tables with their physical data. Compounds without these data 
may be produced analogously from the appropriate materials. In view of 
their close structural relationship with the compounds which have been 
produced and investigated, they can be expected to have a similar action. 
I MANUFACTURE OF THE PRECURSORS 
Example I.1 
2-Chloro-4-trichloromethoxy-6-trichloromethylpyrimidine 
a) 2-Chloro-4-methoxy-6-trichloromethylpyrimidine 
While stirring and within a period of 1 1/2 hours at 0.degree. to 5.degree. 
C., 293.1 g (1.692 mol) of a 30% strength sodium methylate solution was 
added to a solution of 434 g (1.692 mol) of 
2,6-dichloro-4-trichloromethylpyrimidine in 1 liter of 1,2-dichloroethane. 
The mixture was stirred for 1 hour at 0.degree. to 5.degree. C. and for 12 
hours at 25.degree. C. The reaction mixture was then extracted with water 
and saturated sodium chloride solution. After drying over magnesium 
sulfate and evaporating down, there was obtained 423 g (95% of theory) of 
the title compound as an almost colorless oil of n.sub.D.sup.23 =1.5552. 
.sup.1 H-NMR (CDCl.sub.3) (ppm) OCH.sub.3 (s/3H) 4.1; CH (s/1H) 7.25. 
b) 2-Chloro-4-trichloromethoxy-6-trichloromethylpyrimidine 
At initially 110.degree. C., chlorine was introduced, with infrared 
irradiation and gas-chromatographic monitoring of the course of the 
reaction, into a mixture of 210 g (0.802 mol) of a) and 260 mg (0.0016 
mol) of .alpha.,.alpha.'-azoisobutyronitrile; the reaction temperature 
reached 140.degree. C., even after removal of the heating bath. After the 
reaction had subsided, a total of 341 g (4.8 mol) of chlorine was 
introduced over a period of 5 1/2 hours at 120.degree. C. To aid 
precipitation, 70 ml of n-pentane was stirred into the cooling reaction 
mixture from 40.degree. C. The precipitate was suction filtered, washed 
with ligroin and dried. There was obtained 163 g (55% of theory) of the 
title compound; m.p. 67.degree.-69.degree. C. 
The filtrate (113.8 g) consisted, according to the gas chromatograph, of 
83% of the title compound, 4% of 
2-chloro-4-dichoromethoxy-6-trichloromethylpyrimidine and 9% of 
2,4-dichloro-6-trichloromethylpyrimidine. The total yield of the title 
compound was 87.6% of theory. 
Example I.2 
2,4-Difluoro-6-trichloromethoxypyrimidine 
a) 2,4-Difluoro-6-methoxypyrimidine 
(According to the process of prior German Patent Application P 39 00 471 
(O.Z. 0050/40474)) 
At -20.degree. C. and over a period of 45 minutes, 335.8 g (1.865 mol) of 
30% strength sodium methylate (in methanol) was added to a mixture of 250 
g (1.865 mol) of 2,4,6-trifluoropyrimidine, and the mixture was stirred 
for a further 30 minutes at this temperature. The temperature was then 
allowed to rise to 25.degree. C., and the reaction mixture was evaporated 
down to about one fifth of its volume. 
The mixture obtained was partitioned between diethyl ether and water, after 
which the organic phase was dried over magnesium sulfate and evaporated 
down. Distillation (1.1 meter column, 3 mm V-shaped packings) gave 141.6 g 
(52% of theory) of the title compound of boiling point 
144.degree.-145.degree. C. 
Distillation of the residue through a fractionating column (from Normag) 
gave 114.4 g (42% of theory) of 4,6-difluoro-2-methoxypyrimidine of 
boiling point 157.degree.-161.degree. C. 
b) 2,4-Difluoro-6-trichloromethoxypyrimidine 
With UV irradiation and gas-chromatographic monitoring of the course of the 
reaction, 210 g (2.96 mol) of chlorine was introduced over a period of 2 
1/2 hours and with stirring at 130.degree. C. into 123 g (0.843 mol) of 
2,4-difluoro-6-methoxypyrimidine. The reaction mixture was distilled 
through a 10 cm vigreux column under reduced pressure, 190.2 g (90.5% of 
theory) of the title compound of boiling point 40.degree.-43.degree. 
C./0.2 mbar being obtained. 
Example I.3 
2,4-Dichloro-6-trichloromethoxypyrimidine 
With stirring, UV irradiation and gas-chromatographic monitoring of the 
course of the reaction, 303 g (4.27 mol) of chlorine was passed over a 
period of 30 minutes at 80.degree. C., 1 hour at 100.degree. C., 3 hours 
at 120.degree. C. and 3 hours at 150.degree. C. into a mixture of 209 g 
(1.168 mol) of 2,6-dichloro-4-methoxypyrimidine and 2 g (0.012 mol) of 
.alpha.,.alpha.'-azoisobutyronitrile. The reaction mixture was then 
distilled under reduced pressure through a 50 cm column containing V2-A 
Raschig rings. There was obtained 241.3 g (73% of theory) of the title 
compound of boiling point 87.degree.-88.degree. C./0.4 mbar; melting point 
55.degree.-56.degree. C. 
Example I.4 
2,4-Difluoro-6-trifluoromethoxypyrimidine 
At 100.degree. C. and over a period of 15 minutes, 49.9 g (0.2 mol) of 
2,4-difluoro-6-trichloromethoxypyrimidine was added, with stirring, to a 
mixture of 39.3 g (0.22 mol) of antimony trifluoride and 9.38 g (0.031 
mol) of antimony pentachoride. 
The bath temperature was raised over a period of 25 minutes from 
100.degree. to 150.degree. C. and the mixture was stirred for 30 minutes 
at this temperature, reflux being set up between 120.degree. and 
125.degree. C. Subsequent distillation gave 37.1 g (92.7% of theory) of 
the title compound of boiling point 125.degree.-127.degree. C. and 
n.sub.D.sup.23 =1.3787. 
Example I.5 
6-Chlorodifluoromethoxy-2,4-difluoropyrimidine 
At 100.degree. C. and over a period of 10 minutes, 93 g (0.373 mol) of 
2,4-difluoro-6-trichloromethoxypyrimidine was added with stirring to a 
mixture of 44.5 g (0.249 mol) of antimony trifluoride and 0.94 g (0.0031 
mol) of antimony pentachloride. The bath temperature was raised over a 
period of 25 minutes from 100.degree. to 175.degree. C., reflux being set 
up at 145.degree. C. After the mixture had been stirred for 1 1/2 hours, 
the reaction product was distilled off at 146.degree.-150.degree. C. The 
distillate was dissolved in 200 ml of methylene chloride, extracted twice 
with 6N hydrochloric acid and dried over magnesium sulfate. Evaporation 
under reduced pressure gave as residue the title compound of 
n.sub.D.sup.23 =1.4142 in a yield of 63.7 g (78.8% of theory). 
Example I.6 
2-Fluoro-4-trifluoromethoxy-6-trifluoromethylpyrimidine 
At 100.degree. C. and over a period of 5 minutes, 80 g (0.219 mol) of 
2-chloro-4-trichloromethyl-6-trichloromethoxypyrimidine was added with 
stirring to a mixture of 93.9 g (0.525 mol) of antimony trifluoride and 
18.7 g (0.0627 mol) of antimony pentachloride. The bath temperature was 
raised over a period of 10 minutes to 140.degree. C., and then stirred for 
1 hour, strong reflux being set up. The reaction product distilled over at 
135.degree.-140.degree. C., and toward the end at 95.degree. C./50 mbar. 
The distillate was taken up in methylene chloride, extracted with 6N 
hydrochloric acid and dried over magnesium sulfate. Evaporation under 
reduced pressure gave the title compound in a yield of 35.9 g (65.5% of 
theory). 
Example I.7 
2,4-Dichloro-6-trifluoromethoxypyrimidine 
At 100.degree. C. and over a period of 5 minutes, 115 g (0.407 mol) of 
2,4-dichloro-6-trichloromethoxypyrimidine was added while stirring to a 
mixture of 80 g (0.477 mol) of antimony trifluoride and 18.77 g (0.0627 
mol) of antimony pentachloride, the temperature of the reaction mixture 
increasing to 140.degree. C. The mixture was stirred for a further 45 
minutes at 150.degree. C. For distillation, a pressure of 210 mbar was set 
up, the title compound passing over at 128.degree. C.; the last volatile 
constituents passed over at 110.degree. C./22 mbar. The distillate was 
dissolved in methylene chloride, extracted three times with 6N 
hydrochloric acid and dried over magnesium sulfate. Evaporation under 
reduced pressure gave the title compound in a yield of 80 g (84.4% of 
theory) as a colorless oil of n.sub.D.sup.25 =1.4604. 
Example I.8 
2-Amino-4-chlorodifluoromethoxy-6-fluoropyrimidine 
At -75.degree. to -70.degree. C. and over a period of 1 hour, 9.8 g (0.578 
mol) of gaseous ammonia was gassed while stirring into a mixture of 62.5 g 
(0.289 mol) of 2,4-difluoro-6-chlorodifluoromethoxypyrimidine in 300 ml of 
tetrahydrofuran. The mixture was stirred for 1 hour at -70.degree. C. and 
then heated to room temperature. The precipitate was suction filtered, 
partitioned between ethyl acetate and water, and the organic phase was 
dried over magnesium sulfate. The reaction filtrate was evaporated down, 
dissolved in the abovementioned ethyl acetate phase, chromatographed over 
silica gel (5:1 ligroin/ether mixture) and evaporated down. There was 
obtained 46.5 g (75.3% of theory) of the title compound as colorless 
crystals of melting point 77.degree.-80.degree. C. 
Example 1.9 
2-Amino-4-fluoro-6-trifluoromethoxypyrimidine 
At -75.degree. to -70.degree. C. and over a period of 1 hour, 8.7 g (0.51 
mol) of gaseous ammonia was gassed, while stirring, into a mixture of 51 g 
(0.255 mol) of 2,4-difluoro-6-trifluoromethoxypyrimidine in 200 ml of 
diethyl ether. The mixture was stirred for 1 1/2 hours at -70.degree. C. 
and for 1 hour at room temperature. The reaction mixture was evaporated 
down under reduced pressure, taken up in methylene chloride and extracted 
with water. The organic phase was dried, evaporated down and 
chromatographed over silica gel (8:1 ligroin/ether mixture) to give 38.1 g 
(75.6% of theory) of the title compound as colorless crystals of melting 
point 86.degree.-89.degree. C. 
Example I.10 
2-Amino-4-chloro-6-trifluoromethoxypyrimidine 
At -50.degree. to -45.degree. C. and over a period of 45 minutes, 4.3 g 
(0.25 mol) of gaseous ammonia was passed, while stirring, into a mixture 
of 23.3 g (0.1 mol) of 2,4-dichloro-6-trifluoromethoxypyrimidine in 150 ml 
of methyl tert-butyl ether. The mixture was stirred for 30 minutes at 
-50.degree. C., 1 hour at -30.degree. C. and for 1 hour at 25.degree. C. 
The precipitate was suction filtered, washed with water and dried, giving 
5.4 g (33.1% of theory) of 4-amino-2,4-dichloropyrimidine of melting point 
270.degree.-272.degree. C. as byproduct. The filtrate was washed with 
water, dried, evaporated down partially under reduced pressure, and 
fractionally chromatographed with a 5:1 ligroin/ether mixture, the first 
fractions giving 3 g (12.81% of theory) of the starting material as a 
colorless oil and the last runnings 9 g (42% of theory) of the title 
compound as colorless crystals of melting point 55.degree.-56.degree. C. 
The conversion was 48.3%. 
Example I.11 
4-Chlorodifluoromethoxy-6-fluoro-2-methylaminopyrimidine 
At -70.degree. to -60.degree. C. and over a period of 30 minutes, 5.8 g 
(0.188 mol) of gaseous methylamine was added, with stirring, to 20.3 g 
(0.0938 mol) of 4-chlorodifluoromethoxy-2,6-difluoropyrimidine in 150 ml 
of tetrahydrofuran. The mixture was stirred for 1 hour at -70.degree. C., 
1 hour at 0.degree. C. and 1 hour at 25.degree. C., and then evaporated 
down under reduced pressure. The residue was stirred with water and 
extracted twice with ethyl acetate, and the extract was dried over 
magnesium sulfate. It was evaporated down, partially under reduced 
pressure, and then fractionally chromatographed over silica gel (1:5 
ether/ligroin mixture). The first fractions contained the title compound 
(melting point 57.degree.-61.degree. C.) in a yield of 12.5 g (58.5%). 
Example 1.12 
2-Amino-4-trifluoromethoxy-6-trifluoromethylpyrimidine 
At -75.degree. to -70.degree. C. and over a period of 1 hour, 4.7 g (0.278 
mol) of gaseous ammonia was gassed, while stirring, into a mixture of 38.0 
g (0.147 mol) of 
2-fluoro(chloro)-4-trifluoromethoxy-6-trifluoromethylpyrimidine in 150 ml 
of diethyl ether. The mixture was stirred for 2 hours at -75.degree. C. 
and for 2 hours at 25.degree. C. The precipitate was suction filtered, and 
the organic phase was extracted with water, dried and partially evaporated 
down. Chromatography with methyl tert-butyl ether over silica gel gave 
20.4 g (56.1% of theory) of the title compound of melting point 
47.degree.-49.degree. C. 
II. Manufacture of the intermediates IIIa 
Example II.1 
2-Amino-4-methoxy-6-trifluoromethoxypyrimidine 
At -5.degree. to 0.degree. C. and over a period of 15 minutes, 2.7 g (0.015 
mol) of 30% strength sodium methylate was added, while stirring, to 2.95 g 
(0.015 mol) of 2-amino-4-fluoro-6-trifluoromethoxypyrimidine in 50 ml of 
methanol. The reaction mixture was stirred for 1 hour at 0.degree. C., 
heated to 25.degree. C., evaporated down under reduced pressure, stirred 
with water and extracted twice with methylene chloride. Drying and 
evaporation under reduced pressure gave 3.1 g (98% of theory) of the title 
compound; n.sub.D.sup.25 =1.4770. 
Example II.2 
2-Amino-4-chlorodifluoromethoxy-6-methoxypyrimidine 
At -10.degree. to 0.degree. C. and over a period of 15 minutes, 26.1 g 
(0.145 mol) of 30% strength sodium methylate was added, while stirring, to 
31.0 g (0.145 mol) of 2-amino-4-chlorodifluoromethoxy-6-fluoropyrimidine 
in 300 ml of methanol. The mixture was stirred for 30 minutes at 0.degree. 
C. and for 1 hour at 25.degree. C. The reaction mixture was evaporated 
down under reduced pressure and worked up as above. There was obtained 
31.6 g (96.6% of theory) of the title compound as a colorless oil; 
n.sub.D.sup.22 =1.5039. 
Example II.3 
4-Chlorodifluoromethoxy-2-methylamino-6-methoxypyrimidine 
At 0.degree. C. and over a period of 10 minutes, 4.7 g (0.026 mol) of 30% 
strength sodium methylate was added, while stirring, to 6.0 g (0.0263 mol) 
of 4-chlorodifluoromethoxy-6-fluoro-2-methylaminopyrimidine in 100 ml of 
methanol. The mixture was stirred for 1 hour at 0.degree. C. and for 1 
hour at 25.degree. C. Conventional working up gave 6.3 g (100% of theory) 
of the title compound of melting point 49.degree.-53.degree. C. 
Example II.4 
4-Chlorodifluoromethoxy-6-dimethylamino-2-methylaminopyrimidine 
At 0.degree. C. and over a period of 10 minutes, 1.9 g (0.0417 mol) of 
gaseous dimethylamine was added, while stirring, to a mixture of 8.9 g 
(0.0417 mol) of 2-amino-4-chlorodifluoromethoxy-6-fluoropyrimidine in 100 
ml of tetrahydrofuran. The mixture was stirred for 1 hour at 0.degree. C. 
and for 2 hours at 25.degree. C. Conventional working up gave 9.7 g (97.5% 
of theory) of the title compound of melting point 127.degree.-130.degree. 
C. 
III. MANUFACTURE OF THE SULFONYLUREA COMPOUNDS I 
Example III.1 
Methyl 
2-(((4-fluoro-6-trifluoromethoxy-1,3-pyrimidin-2-yl)-aminocarbonyl)-aminos 
ulfonyl)-benzoate 
At 25.degree. C. and over a period of 15 minutes, 3.6 g (0.015 mol) of 
methyl 2-isocyanatosulfonyl benzoate in 15 ml of 1,2-dichloroethane was 
introduced, while stirring, into a mixture of 2.95 g (0.015 mol) of 
2-amino-4-fluoro-6-trifluoromethoxypyrimidine in 100 ml of 
1,2-dichloroethane, and the whole was stirred for 12 hours at 25.degree. 
C. The reaction solution was evaporated down under reduced pressure and 
the residue was stirred with ether/ligroin (1:1). Suction filtration and 
drying gave 4.8 g (73.3% of theory) of the title compound of melting point 
157.degree.-161.degree. C. 
(Active ingredient example no. 1.001) 
Example III.2 
Ethyl 
2-(((4-chloro-6-trifluoromethoxy-1,3-pyrimidin-2-yl)-aminocarbonyl)aminosu 
lfonyl)-benzoate 
At 25.degree. C. and over a period of 10 minutes, 2,55 g (0.01 mol) of 
ethyl 2-isocyanatosulfonylbenzoate in 10 ml of methylene chloride was 
added, while stirring, to a mixture of 2.1 g (0.01 mol) of 
2-amino-4-chloro-6-trifluoromethoxypyrimidine in 100 ml of methylene 
chloride. The mixture was stirred for 12 hours at 25.degree. C. and 
separated from a small amount of insoluble matter by suction filtration. 
The filtrate was evaporated down under reduced pressure, and the residue 
was stirred with ether/ligroin (1:1), suction filtered and dried. There 
was obtained 4.0 g (85.4% of theory) of the title compound of melting 
point 148.degree.-151.degree. C. 
(Active ingredient example no. 3.003) 
Example III.3 
Methyl 
2-(((4-methoxy-6-trifluoromethoxy-1,3-pyrimidin-2-yl)-aminocarbonyl)-amino 
suifonyl)-benzoate 
At 25.degree. C. and over a period of 15 minutes, 4.8 g (0.02 mol) of 
methyl 2-isocyanatosulfonylbenzoate in 10 ml of acetonitrile was added, 
while stirring, to a mixture of 4.1 g (0.02 mol) of 
2-amino-4-methoxy-6-trifluoromethoxypyrimidine in 100 ml of acetonitrile, 
and the whole was stirred for 12 hours. The precipitate was separated off 
(2.4 g of melting point 141.degree.-143.degree. C.) and the filtrate was 
evaporated down under reduced pressure, stirred with ether/ligroin, 
suction filtered and dried. A further 4.3 g of the title compound of 
melting point 141.degree.-143.degree. C. was obtained. The total yield was 
6.7 g (74.4% of theory). 
(Active ingredient example no. 5.001) 
Example III.4 
Methyl 
2-(((4-methoxy-6-trifluoromethoxy-1,3-pyrimidin-2-yl)-aminocarbonyl)-amino 
sulfonyl)-benzoate, sodium salt 
2.4 g (0.053 mol) of methyl 
2-(((4-methoxy-6-trifluoromethoxy-1,3-pyrimidin-2-yl)-aminocarbonyl)-amino 
sulfonyl)-benzoate (active ingredient example 5.001) was dissolved in 50 ml 
of methanol. At 25.degree. C., 1.0 g (0.053 mol) of 30% strength sodium 
methylate solution in methanol was added and the mixture stirred for 10 
minutes. After the solvent had been distilled off under reduced pressure, 
there was obtained 2.5 g (100% of theory) of the title compound of melting 
point 175.degree. C. (decomposition). 
(Active ingredient example no. 5.019) 
The sulfonylurea derivatives given in the tables which follow were prepared 
analogously. 
TABLE 1 
______________________________________ 
##STR12## 
No. R.sup.1 
R.sup.5 n mp (.degree.C.) 
______________________________________ 
1.001 
H CH.sub.3 0 157-161 
1.002 
CH.sub.3 
CH.sub.3 0 
1.003 
H CH.sub.2 CH.sub.3 
0 148-150 
1.004 
CH.sub.3 
CH.sub.2 CH.sub.3 
0 
1.005 
H (CH.sub.2).sub.2 CH.sub.3 
0 
1.006 
CH.sub.3 
(CH.sub.2).sub.2 CH.sub.3 
0 
1.007 
H CH(CH.sub.3).sub.2 
0 164-168 
1.008 
H CH.sub.2 CHCH.sub.2 
0 
1.009 
H CH.sub.2 CHCHCH.sub.3 
0 
1.010 
H CH.sub.2 CCCH.sub.3 
0 
1.011 
H (CH.sub.2).sub.2 Cl 
0 
1.012 
CH.sub.3 
(CH.sub.2).sub.2 Cl 
0 
1.013 
H (CH.sub.2).sub.2 OCH.sub.3 
0 
1.014 
H (CH.sub.2).sub.2 O(CH.sub.2).sub.2 OCH.sub.3 
0 
1.015 
H Cyclopentyl 0 
1.016 
H Cyclohexyl 0 
1.017 
H CH.sub.2 CF.sub.3 
0 
1.018 
H (CH.sub.2).sub.2 SCH.sub.3 
0 
1.019 
H CH.sub.3 0 113 decomp. 
Na salt 
1.020 
CH.sub.3 
CH.sub.3 0 Na salt 
1.021 
H CH.sub.2 CH.sub.3 
0 130 decomp. 
Na salt 
1.022 
CH.sub.3 
CH.sub.2 CH.sub.3 
0 Na salt 
1.023 
H (CH.sub.2).sub.2 CH.sub.3 
0 Na salt 
1.024 
H (CH.sub.2).sub.2 Cl 
0 Na salt 
1.025 
H CH(CH.sub.3).sub.2 
0 140-145 Na salt 
decomp. 
1.026 
H C.sub.2 H.sub.5 0 135 decomp. 
Ca salt 
______________________________________ 
TABLE 2 
______________________________________ 
##STR13## 
No. R.sup.1 
R.sup.5 n mp (.degree.C.) 
______________________________________ 
2.001 
H CH.sub.3 1 167-170 
2.002 
CH.sub.3 
CH.sub.3 1 
2.003 
H CH.sub.2 CH.sub.3 
1 
2.004 
CH.sub.3 
CH.sub.2 CH.sub.3 
1 
2.005 
H (CH.sub.2).sub.2 CH.sub.3 
1 
2.006 
CH.sub.3 
(CH.sub.2).sub.2 CH.sub.3 
1 
2.007 
H CH(CH.sub.3).sub.2 
1 
2.008 
H CH.sub.2 CHCH.sub.2 
1 
2.009 
H CH.sub.2 CHCHCH.sub.3 
1 
2.010 
H CH.sub.2 CCCH.sub.3 
1 
2.011 
H (CH.sub.2).sub.2 Cl 
1 
2.012 
CH.sub.3 
(CH.sub.2).sub.2 Cl 
1 
2.013 
H (CH.sub.2).sub.2 OCH.sub.3 
1 
2.014 
H (CH.sub. 2).sub.2 O(CH.sub.2).sub.2 OCH.sub.3 
1 
2.015 
H Cyclopentyl 1 
2.016 
H Cyclohexyl 1 
2.017 
H CH.sub.2 CF.sub.3 
1 
2.018 
H (CH.sub.2).sub.2 SCH.sub.3 
1 
2.019 
H CH.sub.3 1 195 decomp. 
Na salt 
2.020 
CH.sub.3 
CH.sub.3 1 Na salt 
2.021 
H CH.sub.2 CH.sub.3 
1 Na salt 
2.022 
CH.sub.3 
CH.sub.2 CH.sub.3 
1 Na salt 
2.023 
H (CH.sub.2).sub.2 CH.sub.3 
1 Na salt 
2.024 
H (CH.sub.2).sub.2 Cl 
1 Na salt 
______________________________________ 
TABLE 3 
______________________________________ 
##STR14## 
No. R.sup.1 
R.sup.5 n mp (.degree.C.) 
______________________________________ 
3.001 
H CH.sub.3 0 186-187 
3.002 
CH.sub.3 
CH.sub.3 0 
3.003 
H CH.sub.2 CH.sub.3 
0 148-151 
3.004 
CH.sub.3 
CH.sub.2 CH.sub.3 
0 
3.005 
H (CH.sub.2).sub.2 CH.sub.3 
0 
3.006 
CH.sub.3 
(CH.sub.2).sub.2 CH.sub.3 
0 
3.007 
H CH(CH.sub.3).sub.2 
0 
3.008 
H CH.sub.2 CHCH.sub.2 
0 
3.009 
H CH.sub.2 CHCHCH.sub.3 
0 
3.010 
H CH.sub.2 CCCH.sub.3 
0 
3.011 
H (CH.sub.2).sub.2 Cl 
0 
3.012 
CH.sub.3 
(CH.sub.2).sub.2 Cl 
0 
3.013 
H (CH.sub.2).sub.2 OCH.sub.3 
0 
3.014 
H (CH.sub.2).sub.2 O(CH.sub.2).sub.2 OCH.sub.3 
0 
3.015 
H Cyclopentyl 0 
3.016 
H Cyclohexyl 0 
3.017 
H CH.sub.2 CF.sub.3 
0 
3.018 
H (CH.sub.2).sub.2 SCH.sub.3 
0 
3.019 
H CH.sub.3 0 188 decomp. 
Na salt 
3.020 
CH.sub.3 
CH.sub.3 0 Na salt 
3.021 
H CH.sub.2 CH.sub.3 
0 Na salt 
3.022 
CH.sub.3 
CH.sub.2 CH.sub.3 
0 Na salt 
3.023 
H (CH.sub.2).sub.2 CH.sub.3 
0 Na salt 
3.024 
H (CH.sub.2).sub.2 Cl 
0 Na salt 
______________________________________ 
TABLE 4 
______________________________________ 
##STR15## 
No. R.sup.1 
R.sup.5 n mp (.degree.C.) 
______________________________________ 
4.001 
H CH.sub.3 1 
4.002 
CH.sub.3 
CH.sub.3 1 
4.003 
H CH.sub.2 CH.sub.3 
1 
4.004 
CH.sub.3 
CH.sub.2 CH.sub.3 
1 
4.005 
H (CH.sub.2).sub.2 CH.sub.3 
1 
4.006 
CH.sub.3 
(CH.sub.2).sub.2 CH.sub.3 
1 
4.007 
H CH(CH.sub.3).sub.2 
1 
4.008 
H CH.sub.2 CHCH.sub.2 
1 
4.009 
H CH.sub.2 CHCHCH.sub.3 
1 
4.010 
H CH.sub.2 CCCH.sub.3 
1 
4.011 
H (CH.sub.2).sub.2 Cl 
1 
4.012 
CH.sub.3 
(CH.sub.2).sub.2 Cl 
1 
4.013 
H (CH.sub.2).sub.2 OCH.sub.3 
1 
4.014 
H (CH.sub.2 ).sub.2 O(CH.sub.2).sub.2 OCH.sub.3 
1 
4.015 
H Cyclopentyl 1 
4.016 
H Cyclohexyl 1 
4.017 
H CH.sub.2 CF.sub.3 
1 
4.018 
H (CH.sub.2).sub.2 SCH.sub.3 
1 
4.019 
H CH.sub.3 1 Na salt 
4.020 
CH.sub.3 
CH.sub.3 1 Na salt 
4.021 
H CH.sub.2 CH.sub.3 
1 Na salt 
4.022 
CH.sub.3 
CH.sub.2 CH.sub.3 
1 Na salt 
4.023 
H (CH.sub.2).sub.2 CH.sub.3 
1 Na salt 
4.024 
H (CH.sub.2).sub.2 Cl 
1 Na salt 
______________________________________ 
TABLE 5 
__________________________________________________________________________ 
##STR16## 
No. 
R.sup.1 R.sup.5 n mp (.degree.C.) 
__________________________________________________________________________ 
5.001 
H CH.sub.3 0 141-143 
5.002 
CH.sub.3 CH.sub.3 0 95-98 
5.003 
H CH.sub.2 CH.sub.3 
0 139-140 
5.004 
CH.sub.3 CH.sub.2 CH.sub.3 
0 
5.005 
H (CH.sub.2).sub.2 CH.sub.3 
0 
5.006 
CH.sub.3 (CH.sub.2).sub.2 CH.sub.3 
0 
5.007 
H CH(CH.sub.3).sub.2 
0 
5.008 
H CH.sub.2 CHCH.sub.2 
0 
5.009 
H CH.sub.2 CHCHCH.sub.3 
0 
5.010 
H CH.sub.2 CCCH.sub.3 
0 
5.011 
H (CH.sub.2).sub.2 Cl 
0 
5.012 
CH.sub.3 (CH.sub.2).sub.2 Cl 
0 
5.013 
H (CH.sub.2).sub.2 OCH.sub.3 
0 
5.014 
H (CH.sub.2).sub.2 O(CH.sub.2).sub.2 OCH.sub.3 
0 
5.015 
H Cyclopentyl 0 
5.016 
H Cyclohexyl 0 
5.017 
H CH.sub.2 CF.sub.3 
0 
5.018 
H (CH.sub.2).sub.2 SCH.sub.3 
0 
5.019 
H CH.sub.3 0 175 decomp. 
Na salt 
5.020 
CH.sub.3 CH.sub.3 0 130 decomp. 
Na salt 
5.021 
H CH.sub.2 CH.sub.3 
0 168 decomp. 
Na salt 
5.022 
CH.sub.3 CH.sub.2 CH.sub.3 
0 Na salt 
5.023 
H (CH.sub.2).sub.2 CH.sub.3 
0 Na salt 
5.024 
H (CH.sub.2).sub.2 Cl 
0 Na salt 
5.025 
CH.sub.2 CHCH.sub.2 0 97-99 
__________________________________________________________________________ 
TABLE 6 
______________________________________ 
##STR17## 
No. R.sup.1 
R.sup.5 n mp (.degree.C.) 
______________________________________ 
6.001 
H CH.sub.3 1 124-127 
6.002 
CH.sub.3 
CH.sub.3 1 79-83 
6.003 
H CH.sub.2 CH.sub.3 
1 133-136 
6.004 
CH.sub.3 
CH.sub.2 CH.sub.3 
1 
6.005 
H (CH.sub.2).sub.2 CH.sub.3 
1 
6.006 
CH.sub.3 
(CH.sub.2).sub.2 CH.sub.3 
1 
6.007 
H CH(CH.sub.3).sub.2 
1 
6.008 
H CH.sub.2 CHCH.sub.2 
1 
6.009 
H CH.sub.2 CHCHCH.sub.3 
1 
6.010 
H CH.sub.2 CCCH.sub.3 
1 
6.011 
H (CH.sub.2).sub.2 Cl 
1 
6.012 
CH.sub.3 
(CH.sub.2).sub.2 Cl 
1 
6.013 
H (CH.sub.2).sub.2 OCH.sub.3 
1 
6.014 
H (CH.sub.2).sub.2 O(CH.sub.2).sub.2 OCH.sub.3 
1 
6.015 
H Cyclopentyl 1 
6.016 
H Cyclohexyl 1 
6.017 
H CH.sub.2 CF.sub.3 
1 
6.018 
H (CH.sub.2).sub.2 SCH.sub.3 
1 
6.019 
H CH.sub.3 1 148 decomp. 
Na salt 
6.020 
CH.sub.3 
CH.sub.3 1 Na salt 
6.021 
H CH.sub.2 CH.sub.3 
1 Na salt 
6.022 
CH.sub.3 
CH.sub.2 CH.sub.3 
1 Na salt 
6.023 
H (CH.sub.2).sub.2 CH.sub.3 
1 Na salt 
6.024 
H (CH.sub.2).sub.2 Cl 
1 Na salt 
______________________________________ 
TABLE 7 
__________________________________________________________________________ 
##STR18## 
No. 
R.sup.1 R.sup.5 n mp (.degree.C.) 
__________________________________________________________________________ 
7.001 
H CH.sub.3 0 188 decomp. 
7.002 
CH.sub.3 CH.sub.3 0 
7.003 
H CH.sub.2 CH.sub.3 
0 158 decomp. 
7.004 
CH.sub.3 CH.sub.2 CH.sub.3 
0 
7.005 
H (CH.sub.2).sub.2 CH.sub.3 
0 
7.006 
CH.sub.3 (CH.sub.2).sub.2 CH.sub.3 
0 
7.007 
H CH(CH.sub.3).sub.2 
0 
7.008 
H CH.sub.2 CHCH.sub.2 
0 
7.009 
H CH.sub.2 CHCHCH.sub.3 
0 
7.010 
H CH.sub.2 CCCH.sub.3 
0 
7.011 
H (CH.sub.2).sub.2 Cl 
0 
7.012 
CH.sub.3 (CH.sub.2).sub.2 Cl 
0 
7.013 
H (CH.sub.2).sub.2 OCH.sub.3 
0 
7.014 
H (CH.sub.2).sub.2 O(CH.sub.2).sub.2 OCH.sub.3 
0 
7.015 
H Cyclopentyl 0 
7.016 
H Cyclohexyl 0 
7.017 
H CH.sub.2 CF.sub.3 
0 
7.018 
H (CH.sub.2).sub.2 SCH.sub.3 
0 
7.019 
H CH.sub.3 0 157 decomp. 
Na salt 
7.020 
CH.sub.3 CH.sub.3 0 Na salt 
7.021 
H CH.sub.2 CH.sub.3 
0 Na salt 
7.022 
CH.sub.3 CH.sub.2 CH.sub.3 
0 Na salt 
7.023 
H (CH.sub.2).sub.2 CH.sub.3 
0 Na salt 
7.024 
H (CH.sub.2).sub.2 Cl 
0 Na salt 
7.025 
CH.sub.2 CHCH.sub.2 
CH.sub.3 0 152-154 
__________________________________________________________________________ 
TABLE 8 
______________________________________ 
##STR19## 
No. R.sup.1 
R.sup.5 n mp (.degree.C.) 
______________________________________ 
8.001 
H CH.sub.3 1 186 decomp. 
8.002 
CH.sub.3 
CH.sub.3 1 
8.003 
H CH.sub.2 CH.sub.3 
1 
8.004 
CH.sub.3 
CH.sub.2 CH.sub.3 
1 
8.005 
H (CH.sub.2).sub.2 CH.sub.3 
1 
8.006 
CH.sub.3 
(CH.sub.2).sub.2 CH.sub.3 
1 
8.007 
H CH(CH.sub.3).sub.2 
1 
8.008 
H CH.sub.2 CHCH.sub.2 
1 
8.009 
H CH.sub.2 CHCHCH.sub.3 
1 
8.010 
H CH.sub.2 CCCH.sub.3 
1 
8.011 
H (CH.sub.2).sub.2 Cl 
1 
8.012 
CH.sub.3 
(CH.sub.2).sub.2 Cl 
1 
8.013 
H (CH.sub.2).sub.2 OCH.sub.3 
1 
8.014 
H (CH.sub.2).sub.2 O(CH.sub.2).sub.2 OCH.sub.3 
1 
8.015 
H Cyclopentyl 1 
8.016 
H Cyclohexyl 1 
8.017 
H CH.sub.2 CF.sub.3 
1 
8.018 
H (CH.sub.2).sub.2 SCH.sub.3 
1 
8.019 
H CH.sub.3 1 163 decomp. 
Na salt 
8.020 
CH.sub.3 
CH.sub.3 1 Na salt 
8.021 
H CH.sub.2 CH.sub.3 
1 Na salt 
8.022 
CH.sub.3 
CH.sub.2 CH.sub.3 
1 Na salt 
8.023 
H (CH.sub.2).sub.2 CH.sub.3 
1 Na salt 
8.024 
H (CH.sub.2).sub.2 Cl 
1 Na salt 
______________________________________ 
TABLE 9 
______________________________________ 
##STR20## 
No. R.sup.1 
X R.sup.2 
n mp (.degree.C.) 
______________________________________ 
9.001 H -- F 0 139-141 
9.002 H -- Cl 0 181-183 
9.003 CH.sub.3 
-- F 0 
9.004 CH.sub.3 
-- Cl 0 
9.005 H -- F 1 
9.006 H -- Cl 1 
9.007 CH.sub.3 
-- F 1 
9.008 CH.sub.3 
-- Cl 1 
9.009 H -- F 0 Na salt; 
9.010 H -- Cl 0 Na salt; 
9.011 H O CH.sub.3 
0 150-152 
9.012 H O CH.sub.3 
1 142-143 
9.013 CH.sub.3 
O CH.sub.3 
0 
9.014 CH.sub.3 
O CH.sub.3 
1 
9.015 CH.sub.3 
O CH.sub.3 
0 Na salt 
9.016 CH.sub.3 
O CH.sub.3 
1 Na salt 
9.017 H NH CH.sub.3 
0 177-178 
9.018 H NH CH.sub.3 
1 183-185 
9.019 H NCH.sub.3 
CH.sub.3 
0 185-188 
9.020 H NCH.sub.3 
CH.sub.3 
1 
9.021 CH.sub.3 
NH CH.sub.3 
0 
9.022 H O CH.sub.3 
0 180 decomp. 
Na salt 
9.023 H O CH.sub.3 
1 184 Na salt 
______________________________________ 
TABLE 10 
______________________________________ 
##STR21## 
No. R.sup.1 
X R.sup.2 
n mp (.degree.C.) 
______________________________________ 
10.001 
H -- F 0 
10.002 
H -- Cl 0 
10.003 
H -- F 1 
10.004 
H -- Cl 1 
10.005 
H O CH.sub.3 
0 
10.006 
H O CH.sub.3 
1 
10.007 
H NH CH.sub.3 
0 
10.008 
H NH CH.sub.3 
1 
10.009 
CH.sub.3 
NH CH.sub.3 
0 
10.010 
CH.sub.3 
NH CH.sub.3 
1 
10.011 
H O CH.sub.3 
0 Na salt 
10.012 
H O CH.sub.3 
1 159 Na salt 
10.013 
H O CH.sub.3 
1 150-153 
10.014 
H O CH.sub.3 
0 168-175 
10.015 
H O CH.sub.3 
0 146 Na salt 
10.016 
H NH CH.sub.3 
1 192 
______________________________________ 
TABLE 11 
______________________________________ 
##STR22## 
No. R.sup.1 
X R.sup.2 
R.sup.3 
n mp (.degree.C.) 
______________________________________ 
11.001 H -- F -- 0 
11.002 H -- Cl -- 0 
11.003 H -- F -- 1 
11.004 H -- Cl -- 1 
11.005 H O CH.sub.3 
-- 0 
11.006 H O CH.sub.3 
3-F 1 
11.007 H NH CH.sub.3 
-- 0 
11.008 H NH CH.sub.3 
-- 1 
11.009 H O CH.sub.3 
5-Cl 0 
11.010 H O CH.sub.3 
5-Cl 1 
______________________________________ 
TABLE 12 
__________________________________________________________________________ 
##STR23## 
No. R.sup.1 
X R.sup.2 
R.sup.3 
R.sup.5 
n mp (.degree.C.) 
__________________________________________________________________________ 
12.001 
H -- F 3-F CH.sub.3 
0 
12.002 
H -- Cl 3-F CH.sub.3 
0 
12.003 
H -- F 3-F CH.sub.3 
1 
12.004 
H -- Cl 3-F CH.sub.3 
1 
12.005 
H O CH.sub.3 
3-F CH.sub.3 
0 96-98 
12.006 
H O CH.sub.3 
3-F CH.sub.3 
1 85-86 
12.007 
H O CH.sub.3 
5-Cl 
CH.sub.3 
0 
12.008 
H O CH.sub.3 
5-Cl 
CH.sub.3 
1 
12.009 
H -- F 5-Cl 
CH.sub.3 
0 
12.010 
H -- F 5-Cl 
CH.sub.3 
1 
12.011 
H -- Cl 5-Cl 
CH.sub.3 
0 
12.012 
H -- Cl 5-Cl 
CH.sub.3 
1 
12.013 
H -- F 6-CH.sub.3 
CH.sub.3 
0 
12.014 
H -- F 6-CH.sub.3 
CH.sub.3 
1 
12.015 
H -- Cl 6-CH.sub.3 
CH.sub.3 
0 
12.016 
H -- Cl 6-CH.sub.3 
CH.sub.3 
1 
12.017 
H O CH.sub.3 
6-CH.sub.3 
CH.sub.3 
0 
12.018 
H O CH.sub.3 
6-CH.sub.3 
CH.sub.3 
1 
12.019 
H NH CH.sub.3 
6-CH.sub.3 
CH.sub.3 
0 
12.020 
H NH CH.sub.3 
6-CH.sub.3 
CH.sub.3 
1 
12.021 
CH.sub.3 
NH CH.sub.3 
6-CH.sub.3 
CH.sub.3 
0 
12.022 
H NH CH.sub.3 
6-CH.sub.3 
CH.sub.3 
0 Na salt 
12.023 
H -- CF.sub.3 
-- CH.sub.3 
0 135-137 decomp. 
12.024 
H -- CF.sub.3 
-- CH.sub.3 
0 137 decomp. 
Na salt 
12.025 
CH.sub.3 
-- CF.sub.3 
-- CH.sub.3 
0 
12.026 
H -- CF.sub.3 
-- CH.sub.3 
1 
12.027 
H NCH.sub.3 
CH.sub.3 
-- CH.sub.3 
0 198 decomp. 
12.028 
H NCH.sub. 3 
CH.sub.3 
-- CH.sub.3 
0 160 decomp. 
Na salt 
12.029 
H NCH.sub.3 
CH.sub.3 
3-CH.sub.3 
CH.sub.3 
0 160-165 decomp. 
12.030 
H NCH.sub.3 
CH.sub.3 
6-CH.sub.3 
CH.sub.3 
1 
12.031 
H NCH.sub.3 
CH.sub.3 
-- CH.sub.3 
1 185 decomp. 
Na salt 
12.032 
H NCH.sub.3 
CH.sub.3 
-- CH.sub.3 
1 178 decomp. 
12.033 
H O C.sub.2 H.sub.5 
-- CH.sub.3 
0 141-144 
12.034 
H O C.sub.2 H.sub.5 
-- CH.sub.3 
0 160 decomp. 
Na salt 
12.035 
H O C.sub.2 H.sub.5 
-- CH.sub.3 
1 127-130 
12.036 
CH.sub.3 
O C.sub.2 H.sub.5 
-- CH.sub.3 
1 Na salt 
12.037 
H O C.sub.2 H.sub.5 
6-CH.sub.3 
CH.sub.3 
0 
12.038 
H O C.sub.2 H.sub.5 
5-Cl 
CH.sub.3 
0 139-142 
12.039 
CH.sub.3 
O C.sub.2 H.sub.5 
5-Cl 
CH.sub.3 
0 
12.040 
H O C.sub.2 H.sub.5 
5-Cl 
CH.sub.3 
1 
12.041 
H O CH.sub.3 
-- C.sub.2 H.sub.5 
0 
12.042 
H O CH.sub.3 
-- C.sub.2 H.sub.5 
0 Na salt 
12.043 
H O CH.sub.3 
-- C.sub.2 H.sub.5 
1 
12.044 
H O C.sub.2 H.sub.5 
4-Cl 
CH.sub.3 
0 153 decomp. 
Na salt 
12.045 
H O CH.sub.3 
6-Cl 
CH.sub.3 
0 173-175 
12.046 
H O CH.sub.3 
3-Cl 
CH.sub.3 
0 Na salt 
12.047 
H O CH.sub.3 
5-Cl 
CH.sub.3 
0 144-145 
12.048 
H O CH.sub.3 
4-Cl 
CH.sub.3 
0 Na salt 
12.049 
H O CH.sub.3 
3-Cl 
CH.sub.3 
0 160 decomp. 
12.050 
H O CH.sub.3 
4-Cl 
CH.sub.3 
0 130-133 
12.051 
H O C.sub.2 H.sub.5 
-- CH.sub.3 
1 155 decomp. 
Na salt 
12.052 
H NCH.sub.3 
CH.sub.3 
6-CH.sub.3 
CH.sub.3 
0 
12.053 
H NCH.sub.3 
CH.sub.3 
3-CH.sub.3 
CH.sub.3 
1 150 decomp. 
12.054 
H O C.sub.2 H.sub.5 
-- C.sub.2 H.sub.5 
0 139-143 decomp. 
12.055 
H NH CH.sub.3 
3-CH.sub.3 
CH.sub.3 
0 149-155 
12.056 
H NH CH.sub.3 
3-CH.sub.3 
CH.sub.3 
1 149-155 
12.057 
H NCH.sub.3 
CH.sub.3 
4-Cl 
CH.sub.3 
0 165-169 
12.058 
H NCH.sub.3 
CH.sub.3 
4-Cl 
CH.sub.3 
0 159 decomp. 
Na salt 
12.059 
H NCH.sub.3 
CH.sub.3 
6-CH.sub.3 
CH.sub.3 
0 
12.060 
H O C.sub.2 H.sub.5 
4-Cl 
CH.sub.3 
0 139-143 
12.061 
H O C.sub.2 H.sub.5 
4-Cl 
CH.sub.3 
0 154 decomp. 
Na salt 
12.062 
CH.sub.3 
O CH.sub.3 
4-Cl 
CH.sub.3 
0 103-106 
12.063 
CH.sub.3 
O CH.sub.3 
4-Cl 
CH.sub.3 
0 217 decomp. 
Na salt 
12.064 
H O CH.sub.3 
3-Cl 
CH.sub.3 
0 155 decomp. 
Na salt 
12.065 
H O CH.sub.3 
4-Cl 
CH.sub.3 
0 137 decomp. 
Na salt 
__________________________________________________________________________ 
TABLE 13 
______________________________________ 
##STR24## 
No. A R.sup.1 
n mp (.degree.C.) 
______________________________________ 
13.001 CF.sub.3 H l 179-82 
13.002 CF.sub.3 H 1 144 Na salt 
13.003 CF.sub.3 H 0 162-166 
13.004 CF.sub.3 H 0 107 Na salt 
13.005 Br H 0 138-142 
13.006 Br H 0 149 decomp. 
Na salt 
______________________________________ 
USE EXAMPLES 
A Herbicidal Action 
The herbicidal action of the sulfonylureas of the formula I is demonstrated 
in greenhouse experiments. 
The vessels employed were plastic flowerpots having a volume of 300 
cm.sup.3 and filled with a sandy loam containing about 3.0% humus. The 
seeds of the test plants were sown separately, according to species. 
For the preemergence treatment, the formulated active ingredients were 
applied to the surface of the soil immediately after the seeds had been 
sown. The compounds were emulsified or suspended in water as vehicle, and 
sprayed through finely distributing nozzles. 
After the agents had been applied, the vessels were lightly 
sprinkler-irrigated to induce germination and growth. Transparent plastic 
covers were then placed on the vessels until the plants had taken root. 
The cover ensured uniform germination of the plants, insofar as this was 
not impaired by the active ingredients. 
For the postemergence treatment, the plants were grown, depending on growth 
form, to a height of 3 to 15 cm before being treated with the compounds, 
suspended or emulsified in water. The application rate for post-emergence 
treatment was 0.015 kg/ha. 
The pots were kept in the greenhouse according to the requirements of their 
species, either at from 20.degree. to 35.degree. C., or 10.degree. to 
25.degree. C. The experiments were run for from 2 to 4 weeks. During this 
period the plants were tended and their reactions to the various 
treatments assessed. The assessment scale was 0 to 100, 100 denoting 
nonemergence or complete destruction of at least the visible plant parts, 
and 0 denoting no damage or normal growth. 
The plants used in the experiments were Amaranthus retroflexus, Polygonum 
persicaria and Triticum aestivum. 
Active ingredient 6.019, applied postemergence at a rate of 0.015 kg/ha, 
combated unwanted broadleaved plants very well, and was tolerated by 
wheat. 
B Bioregulatory Action 
The comparative agents used in the examples were 
2-chloroethyltrimethylammonium chloride (CCC)="A" 
6,7-dihydrodipyridol-(1,2-.alpha.:2',1'-c)-pyridilium ion as dibromide 
monohydrate salt (diquat)="B" 
Example B.1 
Investigation of the Growth-Regulating Effect in Rice Seedlings 
Young rice seedlings (Bahia variety) were cultivated in a nutrient solution 
containing varying concentrations of the active ingredients. After the 
plants had been grown for 6 days at 25.degree. C. under continuous light, 
the active ingredient concentration was determined which reduced the 
length of the second leaf sheath by 50% (=KI.sub.50). 
(Details given in W. Rademacher and J. Jung, Berichte aus dem Fachgebiet 
Herbologie, no. 24, pp. 127-134, Hohenheim University, 1983.) 
______________________________________ 
Active ingredient no. 
KI.sub.50 (molar) 
______________________________________ 
1.001 8.6 .times. 10.sup.-6 
3.001 2.2 .times. 10.sup.-6 
"A" 1.5 .times. 10.sup.-2 
______________________________________ 
Example B.2 
To determine the growth-regulating properties of the candidate compounds, 
test plants were grown in a soil provided with sufficient nutrients in 
plastic pots about 12.5 cm in diameter. 
The candidate compounds were sprayed onto the plants postemergence as 
aqueous formulations. The growth-regulating action observed was confirmed 
at the end of the experiment by measuring the height of the plants. The 
figures obtained were compared with the growth height of the untreated 
plants. The compound used for comparison purposes was CCC ("A"). 
The reduction in growth height was also accompanied by a deeper leaf 
coloration. The increased chlorophyll content is indicative of an 
increased rate of photosynthesis, making for bigger yields. 
The individual data are given in the following tables. 
TABLE B.2.1 
______________________________________ 
Spring barley, "Aramir" 
Postemergence treatment 
No. of chemical 
Conc. Growth height 
examples mg ai/vessel 
rel. 
______________________________________ 
untreated -- 100 
"A" 0.025 100 
0.1 100 
0.38 96.3 
1.5 93.3 
3.001 0.025 100 
0.1 100 
0.38 100 
1.5 100 
5.001 0.025 56.3 
0.1 47.4 
0.38 41.5 
1.5 38.5 
5.003 0.025 74.1 
0.1 59.3 
0.38 47.4 
1.5 41.5 
5.019 0.025 62.2 
0.1 47.4 
0.38 41.5 
1.5 41.5 
2.001 0.025 100 
0.1 100 
0.38 100 
1.5 100 
1.003 0.025 100 
0.1 100 
0.38 85.9 
1.5 56.3 
3.003 0.025 100 
0.1 100 
0.38 97.8 
1.5 81.5 
______________________________________ 
TABLE B.2.2 
______________________________________ 
Spring wheat, "Ralle" 
Postemergence treatment 
No. of chemical 
Conc. Growth height 
examples mg ai/vessel 
rel. 
______________________________________ 
untreated -- 100 
"A" 0.025 100 
0.1 91.9 
0.38 87.4 
1.5 81.4 
3.001 0.025 100 
0.1 100 
0.38 100 
1.5 94.9 
5.001 0.025 51.2 
0.1 48.2 
0.38 48.2 
1.5 48.2 
5.003 0.025 63.3 
0.1 51.2 
0.38 48.2 
1.5 48.2 
5.019 0.025 51.2 
0.1 48.2 
0.38 48.2 
1.5 48.2 
2.001 0.025 100 
0.1 100 
0.38 100 
1.5 100 
1.003 0.025 100 
0.1 100 
0.38 93.4 
1.5 57.3 
3.003 0.025 100 
0.1 100 
0.38 100 
1.5 85.9 
______________________________________ 
TABLE B.2.3 
______________________________________ 
Spring barley, "Aramir" 
Postemergence treatment 
No. of chemical 
Conc. Growth height 
examples mg ai/vessel 
rel. 
______________________________________ 
untreated -- 100 
"A" 0.025 100 
0.1 100 
0.38 96.3 
1.5 93.3 
1.003 0.025 100 
0.1 100 
0.38 100 
1.5 66.1 
3.003 0.025 100 
0.1 100 
0.38 100 
1.5 83.3 
12.032 0.025 86.0 
0.1 47.6 
0.38 39.7 
1.5 37.0 
______________________________________ 
TABLE B.2.4 
______________________________________ 
Spring wheat, "Ralle" 
Postemergence treatment 
No. of chemical 
Conc. Growth height 
examples mg ai/vessel 
rel. 
______________________________________ 
untreated -- 100 
"A" 0.025 100 
0.1 91.9 
0.38 87.4 
1.5 81.4 
1.003 0.025 100 
0.1 100 
0.38 87.0 
1.5 48.5 
3.003 0.025 100 
0.1 100 
0.38 82.7 
1.5 59.9 
12.032 0.025 88.4 
0.1 44.2 
0.38 42.8 
1.5 42.8 
______________________________________ 
Example B.3 
Young cotton plants (variety: Stoneville 825, development stage: 5 to 6 
developed true leaves) were grown under greenhouse conditions (day/night 
temperature: 25.degree./18.degree. C., relative humidity 50 to 70%), and 
the leaves were sprayed to runoff with aqueous formulations of the 
candidate compounds (with the addition of 0.15 wt % of the fatty alcohol 
alkoxylate Plurafac.RTM. LF 700, based on the spray liquor). The amount of 
water used was equivalent to 1,000 liters/ha. The number of cast leaves 
was determined 6 days after application of the active ingredients and the 
degree of defoliation is stated in %, compared with the control. No leaves 
were cast from the untreated control plants. 
______________________________________ 
No. of chemical 
Appl. rate equivalent to 
examples kg/ha % defoliation 
______________________________________ 
5.003 0.5 33 
5.019 0.5 32 
"B" 0.5 47 
______________________________________