N-Arylsulfonyl-N'-(4-mercaptomethyl-pyrimidinyl- and -triazinyl)-ureas of the formula ##STR1## (symbols in this formula defined below) and the salts of these compounds with amines, alkali metal bases or alkaline-earth metal bases or with ammonium bases, have good pre- and post-emergence-selective, herbicidal and growth-regulating properties.

The present invention relates to novel, herbicidally effective and 
plant-growth-regulating N-arylsulfonyl-N'-(4-mercaptomethyl-pyrimidinyl- 
and triazinyl)-urea derivatives, to processes for producing them, to 
compositions containing them as active ingredients, and to the use thereof 
for controlling weeds, in particular selectively, in crops of cultivated 
plants, or for regulating and inhibiting plant growth. Furthermore, the 
invention relates also the novel 2-amino-4-mercaptomethyl-pyrimidine and 
-triazine derivatives produced as intermediates. 
The N-arylsulfonyl-N'-(4-mercaptomethyl-pyrimidinyl- and -triazinyl)-ureas 
according to the invention correspond to the formula I 
##STR2## 
wherein E is nitrogen or --CH.dbd., 
X is oxygen, sulfur, --NR.sup.3 --, --N.dbd.CR.sup.3 --, --CH.dbd.CH-- or 
##STR3## 
Z is oxygen or sulfur, R.sup.1 is hydrogen, halogen, nitro, ethinyl, 
--NR.sup.16 R.sup.17, --CR.sup.6 --di--C.sub.1 -C.sub.4 -alkoxy, 
##STR4## 
--CW--R.sup.6, --SO.sub.2 --NR.sup.7 R.sup.8, --CO--R.sup.9, --Y.sub.m 
--R.sup.10, --SO.sub.2 --R.sup.11 or O--SO.sub.2 R.sup.12, in which m is 
zero or 1, 
R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 
-alkoxy, C.sub.1 -C.sub.4 -haloalkyl or nitro, 
R.sup.3 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkenyl or 
C.sub.1 -C.sub.4 -alkoxy, 
R.sup.4 is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 
-alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, 
C.sub.1 -C.sub.4 -alkylthio, C.sub.2 -C.sub.4 -alkoxyalkyl, C.sub.2 
-C.sub.4 -alkoxyalkoxy, cyclopropyl, NH.sub.2, C.sub.1 -C.sub.4 
-alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, or a saturated 5- to 
7-membered nitrogen heterocycle which is bound by way of the nitrogen atom 
and which can contain a further hetero atom, 
R.sup.5 is cyano, --CZ--R.sup.13, 
##STR5## 
or an unsaturated heterocycle unsubstituted or substituted by a radical 
selected from the group comprising: halogen, C.sub.1 -C.sub.4 -alkyl, 
C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -haloalkyl, 
R.sup.6 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, 
C.sub.3 -C.sub.6 -cycloalkyl, C.sub.4 -C.sub.7 -cycloalkylalkyl or C.sub.2 
-C.sub.4 -alkoxyalkyl, 
R.sup.7 and R.sup.16 independently of one another are hydrogen, C.sub.1 
-C.sub.4 -alkyl, C.sub.1 -C.sub.4 -cyanoalkyl or C.sub.1 -C.sub.4 -alkoxy, 
R.sup.8 and R.sup.17 independently of one another are hydrogen, C.sub.1 
-C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkenyl or C.sub.1 -C.sub.4 -alkoxy, or 
R.sup.7 and R.sup.8 as well as R.sup.16 and R.sup.17 independently of one 
another form, together with the nitrogen atom binding them, a 5- to 
7-membered saturated nitrogen heterocycle, which can contain a further 
hetero atom, 
R.sup.9 is C.sub.1 -C.sub.4 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 
-C.sub.6 -alkinyloxy, C.sub.2 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.4 
-cyanoalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.3 -C.sub.4 -alkenylthio, 
C.sub.3 -C.sub.4 -alkinylthio, C.sub.5 -C.sub.6 -cycloalkoxy, C.sub.4 
-C.sub.7 -cycloalkylalkoxy, --NR.sup.7 R.sup.8 or C.sub.2 -C.sub.6 
-alkoxyalkoxy, 
R.sup.10 is C.sub.3 -C.sub.4 -alkinyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.1 
-C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl mono- or polysubstituted by 
halogen, cyano, C.sub.1 -C.sub.4 -alkoxy or --SO.sub.n --C.sub.1 -C.sub.4 
-alkyl, or is C.sub.1 -C.sub.4 -alkyl mono- or polysubstituted by halogen, 
cyano, nitro, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, 
C.sub.1 -C.sub.4 -haloalkylthio, --SO.sub.n --C.sub.1 -C.sub.4 -alkyl, 
--T--CX--R.sup.18, 
##STR6## 
--CO--R.sup.6, --CO--R.sup.9 or --SO.sub.2 --NR.sup.7 R.sup.8, in which n 
is zero, 1 or 2, 
R.sup.11 is C.sub.2 -C.sub.4 -haloalkoxy, 
R.sup.12 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl or 
--NR.sup.16 R.sup.17, 
R.sup.13 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 
-C.sub.4 -alkylthio, phenyl, di-C.sub.1 -C.sub.4 -alkylamino, or a 
saturated, 5- to 7-membered nitrogen heterocycle which is bound by way of 
the nitrogen atom and which can contain a further hetero atom, 
R.sup.14 and R.sup.15 independently of one another are C.sub.1 -C.sub.4 
-alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.3 -C.sub.4 -alkoxyalkoxy, C.sub.3 
-C.sub.4 -alkenyloxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.4 
-alkylamino or di-C.sub.1 -C.sub.4 -alkylamino, 
R.sup.18 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 
-C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio or --NR.sup.16 R.sup.17, 
T is oxygen or sulfur, 
W is oxygen or .dbd.N--O--R.sup.3, and 
Y is oxygen, sulfur, --SO-- or --SO.sub.2 --; 
and the invention relates also to the salts of these compounds. 
Urea compounds, triazine compounds and pyrimidine compounds having 
herbicidal activity are in general known. Sulfonylurea compounds having a 
herbicidal and plant-growth-regulating action have been recently described 
for example in the European Patent Application Nos. 44807 and 44808. 
By alkyl in the definitions is meant straight-chain or branched-chain 
alkyl, for example: methyl, ethyl, n-propyl, i-propyl or the four isomeric 
butyl groups. 
And by alkoxy is meant: methoxy, ethoxy, n-propyloxy, i-propyloxy, the four 
isomeric butyloxy groups, n-amyloxy, i-amyloxy, 2-amyloxy or 3-amyloxy, 
especially however methoxy, ethoxy or i-propyloxy. 
Examples of alkylthio are: methylthio, ethylthio, n-propylthio, 
i-propylthio, n-butylthio or n-pentylthio, particularly methylthio or 
ethylthio. 
Examples of alkylsulfinyl are: methylsulfinyl, ethylsulfinyl, 
n-propylsulfinyl and n-butylsulfinyl, in particular methylsulfinyl and 
ethylsulfinyl. 
Examples of alkylsulfonyl are: methylsulfonyl, ethylsulfonyl or 
n-propylsulfonyl, especially methylsulfonyl and ethylsulfonyl. 
Halogen in the definitions themselves, as well as halogen as a moiety in 
haloalkoxy, haloalkyl or haloalkylthio, is fluorine, chlorine and bromine, 
preferably however fluorine or chlorine. 
The aryl moieties of the active substances of the formula I, which are 
bound to the sulfonyl bridge, are characterised by the following basic 
aromatic ring systems: thiophene, furan, pyridine, pyrrole, phenyl or 
naphthalene. The phenyl ring is preferred. 
Examples of the nitrogen heterocycles defined under R.sup.4 and R.sup.13 
are rings bound by way of the nitrogen atom of the following fundamental 
types: pyrrolidine, piperidine, morpholine, thiomorpholine or piperazine 
or hexamethyleneimine. 
The unsaturated heterocycles defined under R.sup.5 embrace, within the 
scope of the present invention, for example the following basic ring 
systems: imidazole, thiazole, pyridine, pyrimidine, thiazole, oxazole, 
thiadiazole, oxadiazole, pyridazine, thiophene or furan, as well as 
partially hydrogenated derivatives thereof. Preferred unsaturated 
heterocyclic substituents within the definition of R.sup.5 are 
4,5-dihydrothiazol-2-yl, 2H-1,2,4-triazol-3-yl, 1-methyl-imidazol-2-yl, 
2-pyridinyl and 2-pyrimidinyl. 
Examples of cycloalkyl are: cyclopropyl, cyclobutyl, cyclopentyl and 
cyclohexyl, preferably however cyclopentyl and cyclohexyl. Preferred 
cycloalkylalkyl radicals are cyclopropylmethyl, cyclopentylmethyl and 
cyclohexylmethyl. Alkoxyalkyl groups are represented by: methoxymethyl, 
ethoxymethyl, methoxyethyl and ethoxyethyl, especially methoxyethyl. 
Alkoxyalkoxy groups within the scope of the present invention are: 
methoxymethoxy, ethoxymethoxy, methoxyethoxy and ethoxyethoxy. Preferred 
cyanoalkyl groups are cyanomethyl and cyanoethyl. Haloalkyl itself as 
substituent or as part of another substituent, such as haloalkoxy or 
haloalkylthio, is as a rule: chloromethyl, fluoromethyl, difluoromethyl, 
trifluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, 
1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 1,1,2-trifluoro-2-chloroethyl, 
2,2,2-trifluoro-1,1-dichloroethyl, pentachloroethyl, 
3,3,3-trifluoropropyl, 2,3-dichloropropyl or 1,1,2,3,3,3-hexafluoropropyl, 
particularly however fluoromethyl, chloromethyl, difluoromethyl and 
trifluoromethyl. 
The invention embraces likewise the salts which the compounds of the 
formula I can form with amines, alkali metal and alkaline-earth metal 
bases or quaternary ammonium bases. 
To be emphasised among alkali metal and alkaline-earth metal hydroxides as 
salt formers are the hydroxides of lithium, sodium, potassium, magnesium 
or calcium, in particular however those of sodium and potassium. 
Examples of amines suitable for forming salts are: primary, secondary and 
tertiary aliphatic and aromatic amines, such as methylamine, ethylamine, 
propylamine, i-propylamine, the four isomeric butylamines, dimethylamine, 
diethylamine, diethanolamine, dipropylamine, diisopropylamine, 
di-n-butylamine, pyrrolidine, piperidine, morpholine, trimethylamine, 
triethylamine, tripropylamine, quinuclidine, pyridine, quinoline and 
i-quinoline, especially ethyl-, propyl-, diethyl- or triethylamine, but 
particularly iso-propylamine and diethanolamine. 
Examples of quaternary ammonium bases are in general the cations of 
haloammonium salts, for example the tetramethylammonium cation, the 
trimethylbenzylammonium cation, the triethylbenzylammonium cation, the 
tetraethylammonium cation or the trimethylethylammonium cation, but also 
the ammonium cation. 
Preferred compounds of the formula I according to the invention are those 
in which 
(a) X is the ethenylene bridge --CH.dbd.CH--; or 
(b) Z is oxygen; or 
(c) R.sup.1 is C.sub.1 -C.sub.4 -alkoxycarbonyl, nitro, halogen, C.sub.1 
-C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy or di-C.sub.1 -C.sub.4 
-alkylsulfamoyl; or 
(d) R.sup.2 is hydrogen; or 
(e) R.sup.3 is hydrogen; or 
(f) R.sup.4 is halogen, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 
-alkyl; or 
(g) E is the methine bridge --CH.dbd.; or 
(h) R.sup.5 is C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 
-alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxythiocarbonyl, di-C.sub.1 -C.sub.4 
-alkylcarbamoyl, di-C.sub.1 -C.sub.4 -alkylthiocarbamoyl, di-C.sub.1 
-C.sub.4 -alkoxyphosphonyl, di-C.sub.1 -C.sub.4 -alkoxythiophosphonyl, 
N-pyrrolidinocarbonyl, N-pyrrolidinothiocarbonyl, 
N-morpholinothiocarbonyl, 2H-1,2,4-triazol-3-yl, 4,5-dihydrothiazol-2-yl, 
1-C.sub.1 -C.sub.4 -alkyl-imidazol-2-yl, 2-pyridinyl or 2-pyrimidinyl. 
A further preferred subgroup is formed by those compounds of the formula I 
in which X is the ethenylene bridge, Z is oxygen, R.sup.1 is C.sub.1 
-C.sub.4 -alkoxycarbonyl, nitro, halogen, C.sub.1 -C.sub.4 -haloalkyl, 
C.sub.1 -C.sub.4 -haloalkoxy or di-C.sub.1 -C.sub.4 -alkylsulfamoyl, and 
R.sup.2 and R.sup.3 are hydrogen. 
Likewise preferred are the compounds of the formula I in which R.sup.4 is 
halogen, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkyl, E is the 
methine bridge, and R.sup.5 is C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 
-C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxythiocarbonyl, di-C.sub.1 
-C.sub.4 -alkylcarbamoyl, di-C.sub.1 -C.sub.4 -alkylthiocarbamoyl, 
di-C.sub.1 -C.sub.4 -alkoxyphosphonyl, di-C.sub.1 -C.sub.4 
-alkoxythiophosphonyl, N-pyrrolidinocarbonyl, N-pyrrolidinothiocarbonyl, 
N-morpholinothiocarbonyl, 2H-1,2,4-triazol-3-yl, 4,5-dihydrothiazol-2-yl, 
1-C.sub.1 -C.sub.4 -alkyl-imidazol-2-yl, 2-pyridinyl or 2-pyrimidinyl. 
A particularly preferred subgroup of compounds of the formula I is formed 
by those in which X is the ethenylene bridge, Z is oxygen, R.sup.1 is 
C.sub.1 -C.sub.4 -alkoxycarbonyl, nitro, halogen, C.sub.1 -C.sub.4 
-haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy or di-C.sub.1 -C.sub.4 
-alkylsulfamoyl, and R.sup.2 and R.sup.3 are hydrogen, halogen, C.sub.1 
-C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkyl, E is the methine bridge, and 
R.sup.5 is C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 
-alkoxycarbonyl, C.sub.1 -C.sub.4 -alkoxythiocarbonyl, di-C.sub.1 -C.sub.4 
-alkylcarbamoyl, di-C.sub.1 -C.sub.4 -alkylthiocarbamoyl, di-C.sub.1 
-C.sub.4 -alkoxyphosphonyl, di-C.sub.1 -C.sub.4 -alkoxythiophosphonyl, 
N-pyrrolidinocarbonyl, N-pyrrolidinothiocarbonyl, 
N-morpholinothiocarbonyl, 2H-1,2,4-triazol-3-yl, 4,5-dihydrothiazol-2-yl, 
1-C.sub.1 -C.sub.4 -alkyl-imidazol-2-yl, 2-pyridinyl or 2-pyrimidinyl. 
To be mentioned as preferred individual compounds are: 
N-(2-methoxycarbonylphenyl-sulfonyl)-N'-(4-methoxy-6-acetylthiomethyl-pyrim 
idin-2-yl)-urea, 
N-(2-methoxycarbonylphenyl-sulfonyl)-N'-(4-methoxy-6-methoxythiocarbonylthi 
omethyl-pyrimidin-2-yl)-urea, 
N-(2-nitrophenyl-sulfonyl)-N'-[4-methoxy-6-(4,5-dihydrothiazol-2-yl-thiomet 
hyl)-pyrimidin-2-yl]-urea, 
N-(2-methoxycarbonylphenyl-sulfonyl)-N'-(4-methoxy-6-dimethoxythiophosphony 
lthiomethyl-pyrimidin-2-yl)-urea, 
N-(2-nitrophenyl-sulfonyl)-N'-(4-methoxy-6-diethoxyphosphonylthiomethyl-pyr 
imidin-2-yl)-urea, and 
N-(2-methoxycarbonylphenyl-sulfonyl)-N'-(4-methoxy-6-di-n-butyloxythiophosp 
honylthiomethyl-pyrimidin-2-yl)-urea. 
The compounds of the formula I are produced in general by the following 
methods. 
One process for obtaining the compounds of the formula I comprises reacting 
an arylsulfonylisocyanate or arylsulfonylisothiocyanate of the formula II 
##STR7## 
wherein R.sup.1, R.sup.2, X and Z have the meanings defined under the 
formula I, with an aminopyrimidine or aminotriazine of the formula III 
##STR8## 
wherein R.sup.3, R.sup.4, R.sup.5 and E have the meanings defined under 
the formula I. 
A further process for obtaining the compounds of the formula I comprises 
reacting an N-arylsulfonylcarbamate of the formula IV 
##STR9## 
wherein R.sup.1, R.sup.2, X and Z have the meanings defined under the 
formula I, and R is phenyl, alkyl or substituted phenyl, with an 
aminopyrimidine or aminotriazine of the formula III. 
Finally, the compounds of the formula I can be produced also by reacting a 
compound of the formula V 
##STR10## 
wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, X and Z have the meanings 
defined under the formula I, and Hal is chlorine or bromine, with a sulfur 
salt of the formula VI 
EQU M.sup..sym..crclbar. S--R.sup.5 (VI) 
wherein R.sup.5 has the meaning defined under the formula I, and 
M.sup..sym. is an alkali metal cation, alkaline-earth metal cation or 
ammonium cation. 
The resulting ureas of the formula I can if desired be converted, by means 
of amines, alkali metal hydroxides or alkaline-earth metal hydroxides or 
quaternary ammonium bases, into addition salts. This is effected for 
example by reaction with the equimolar amount of a base, and removal of 
the solvent by evaporation. 
The reactions to give compounds of the formula I are performed 
advantageously in aprotic, inert organic solvents. Such solvents are: 
hydrocarbons, such as benzene, toluene, xylene or cyclohexane, chlorinated 
hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride 
or chlorobenzene, ethers, such as diethyl ether, ethylene glycol dimethyl 
ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, 
nitriles, such as acetonitrile or propionitrile, amides, such as 
dimethylformamide, diethylformamide or N-methylpyrrolidine. The reaction 
temperatures are preferably between -20.degree. and +120.degree. C. The 
reactions of the coupling processes proceed in general slightly 
exothermically, and can be performed at room temperature. For the purpose 
of shortening the reaction time or for initiating the reaction, it is 
advantageous to apply heat for a short time up to the boiling point of the 
reaction mixture. The reaction times can advantageously be shortened if 
desired also by the addition of a few drops of a base as a reaction 
catalyst. Suitable bases are in particular tertiary amines, such as 
trimethylamine, triethylamine, quinuclidine, 
1,4-diazabicyclo-(2,2,2)-octane, 1,5-diazabicyclo(4,3,0)-non-5-ene or 
1,5-diazabicyclo(5,4,0)undec-7-ene. The bases used can however also be 
inorganic bases, such as hydrides, for example sodium or calcium hydride, 
hydroxides, such as sodium and potassium hydroxide, carbonates, such as 
sodium and potassium carbonate, or hydrogen carbonates, such as potassium 
and sodium bicarbonate. 
The final products of the formula I can be isolated by concentration by 
evaporation and/or by removal of the solvent by evaporation, and purified 
by recrystallisation or trituration of the solid residue in solvents in 
which the products are not readily soluble, such as ethers, aromatic 
hydrocarbons or chlorinated hydrocarbons. 
The intermediates of the formulae II, IV, V and VI are known, or they can 
be produced by methods analogous to known methods. 
The aminopyrimidines and -triazines of the formula III are novel, and were 
specially developed and produced as intermediates for producing the active 
substances according to the invention. These intermediates thus form 
further subject matter of the present invention. 
The novel aminopyrimidines and -triazines of the formula III are produced 
by reacting a compound of the formula VII 
##STR11## 
wherein R.sup.3, R.sup.4 and E have the meanings defined under the formula 
I, and Hal is chlorine or bromine, with a sulfur salt of the formula VI. 
This reaction is performed under reaction conditions which are the ame as 
those for the reaction of the compounds V and VI. 
The active substances of the formula I are stable compounds, and the 
handling of them requires no special precautions. 
In smaller applied amounts, the compounds of the formula I are 
characterised by good selective growth-inhibiting and selective herbicidal 
properties, which render the compounds excellently suitable for use in 
crops of useful plants, especially in crops of cereals, cotton, soya-bean, 
maize and rice. Also destroyed in some cases are weeds which hitherto 
could be dealt with only by the use of total herbicides. 
The mode of action of these active substances is unusual. Many are capable 
of being translocated, that is to say, they are taken up by the plant and 
transported to other locations, where they produce the desired effect. It 
is thus possible for example by surface treatment of perennial weeds to 
destroy them at the roots. The novel compounds of the formula I are 
effective in applied amounts which are very small compared with the 
amounts required to obtain the same effect using other herbicides and 
plant-growth regulators. 
The compounds of the formula I have excellent properties also for 
regulating plant growth, especially for inhibiting plant growth. Both 
monocotyledons and dicotyledons are impaired in their growth. 
Thus, for example, the leguminosae frequently planted as cover crops in 
agriculture in tropical regions can be selectively inhibited in their 
growth by the compounds of the formula I, the result being that soil 
erosion between the cultivated plants is prevented, without the cover 
crops being able to compete with the main cultivated crop. 
A reduction of the vegetative growth enables in the case of many cultivated 
plants the crop density to be increased, so that higher yields for the 
same area of land can be achieved. 
An additional factor contributing to the increase in yield with the use of 
growth inhibitors is that the formation of blossom and fruit benefits to a 
greater extent from the nutritive substances, because the vegetative 
growth is restricted. 
With larger applied amounts of active substance, all the tested plants are 
impaired in their development to the extent that they wither. 
The invention relates also to herbicidal and plant-growth regulating 
compositions containing a novel active ingredient of the formula I, and 
also to processes for the pre- and post-emergence controlling of weeds, 
and for the reduction in growth of monocotyledonous and dicotyledonous 
plants, particularly that of grasses, tropical cover crops and side shoots 
of tobacco plants. 
The compounds of the formula I are used either in an unmodified form or 
preferably in compositions, together with auxiliaries customarily employed 
in formulation practice, and are thus processes, in a known manner, for 
example into the form of emulsion concentrates, directly sprayable or 
dilutable solutions, diluted emulsions, wettable powders, soluble powders, 
dusts or granulates, and also encapsulations in for example polymeric 
substances. The application processes, such as spraying, atomising, 
dusting, scattering or pouring, and likewise the type of composition, are 
selected to suit the objects to be achieved and the given conditions. 
The formulations, that is to say, the compositions or preparations 
containing the active ingredient of the formula I and optionally a solid 
or liquid additive, are produced in a known manner, for example by the 
intimate mixing and/or grinding of the active ingredients with extenders, 
such as with solvents, solid carriers and optionally surface-active 
compounds (tensides). 
Suitable solvents are: aromatic hydrocarbons, preferably the fractions 
C.sub.8 to C.sub.12, such as xylene mixtures or substituted naphthalenes, 
phthalic esters, such as dibutyl- or dioctylphthalate, aliphatic 
hydrocarbons, such as cyclohexane or paraffins, alcohols and glycols, as 
well as ethers and esters thereof, such as ethanol, ethylene glycol, 
ethylene glycol monomethyl or -ethyl ethers, ketones, such as 
cyclohexanone, strongly polar solvents, such as N-methyl-2-pyrrolidone, 
dimethylsulfoxide or dimethylformamide, as well as optionally epoxidised 
vegetable oils, such as epoxidised coconut oil or soybean oil; or water. 
The solid carriers used, for example for dusts and dispersible powders, are 
as a rule natural mineral fillers, such as calcite, talcum, kaolin, 
montmorillonite or attapulgite. In order to improve the physical 
properties, it is also possible to add highly dispersed silicic acid or 
highly dispersed absorbent polymers. Suitable granulated adsorptive 
carriers are porous types, for example pumice, ground brick, sepiolite or 
bentonite; and suitable nonsorbent carriers are materials such as calcite 
or sand. There can also be used a great number of pre-granulated materials 
of inorganic or organic nature, such as in particular dolomite or ground 
plant residues. 
Suitable surface-active compounds are, depending on the nature of the 
active substance of the formula I to be formulated, nonionic, cationic 
and/or anionic tensides having good emulsifying, dispersing and wetting 
properties. By `tensides` are also meant mixtures of tensides. 
Suitable anionic tensides are both so-called water-soluble soaps as well as 
water-soluble, synthetic, surface-active compounds. 
Soaps which are applicable are the alkali metal, alkaline-earth metal or 
optionally substituted ammonium salts of higher fatty acids (C.sub.10 
-C.sub.22), for example the Na or K salts of oleic or stearic acid, or of 
natural fatty acid mixtures, which can be obtained for example from 
coconut oil or tallow oil, Also to be mentioned are the fatty 
acid-methyl-taurine salts. 
So-called synthetic tensides are however more frequently used, particularly 
fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or 
alkylarylsulfonates. The fatty sulfonates or sulfates are as a rule in the 
form of alkali metal, alkaline-earth metal or optionally substituted 
ammonium salts, and contain an alkyl group having 8 to 22 C atoms, `alkyl` 
including also the alkyl moiety of acyl groups, for example the Na or Ca 
salt of ligninsulfonic acid, of dodecylsulfuric acid ester or of a fatty 
alcohol sulfate mixture produced from natural fatty acids. Included among 
these are also the salts of sulfuric acid esters and sulfonic acids of 
fatty alcohol ethylene oxide adducts. The sulfonated benzimidazole 
derivatives preferably contain 2 sulfonic acid groups and a fatty acid 
group having 8-22 C atoms. Alkylarylsulfonates are for example the Na, Ca 
or triethanolamine salts of dodecylbenzenesulfonic acid, of 
dibutylnaphthalenesulfonic acid or of a naphthalenesulfonic 
acid-formaldehyde condensation product. Also suitable are corresponding 
phosphates, for example salts of the phosphoric ester of a 
p-nonylphenol-(4-14)-ethylene oxide adduct, and phospholipides. 
Suitable nonionic tensides are in particular polyglycol ether derivatives 
of aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty 
acids and alkylphenols, which can contain 3 to 10 glycol ether groups and 
8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 
carbon atoms in the alkyl moiety of the alkylphenols. 
Further suitable nonionic tensides are the water-soluble polyethylene oxide 
adducts, which contain 20 to 250 ethylene glycol ether groups and 10 to 
100 propylene glycol ether groups, with polypropylene glycol, 
ethylenediaminopolypropylene glycol and alkylpolypropylene glycol having 1 
to 10 carbon atoms in the alkyl chain. The compounds mentioned usually 
contain 1 to 5 ethylene glycol units per propylene glycol unit. Examples 
of nonionic tensides which may be mentioned are: 
nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, 
polypropylene/polyethyleneoxy adducts, tributylphenoxypolyethoxyethanol, 
polyethylene glycol and octylphenoxypolyethoxyethanol. Suitable also are 
fatty acid esters of polyoxyethylenesorbitan, such as 
polyoxyethylenesorbitan-trioleate. 
In the case of the cationic tensides, they are in particular quaternary 
ammonium salts which contain as N-substituents at least one alkyl group 
having 8 to 22 C atoms and, as further substituents, lower, optionally 
halogenated alkyl, benzyl or lower hydroxyalkyl groups. The salts are 
preferably in the form of halides, methyl sulfates or ethyl sulfates, for 
example stearyltrimethylammonium chloride or 
benzyldi(2-chloroethyl)ethylammonium bromide. 
The tensides customarily used in formulation practice are described, inter 
alia, in the following publications: 
"Mc Cutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., 
Ridgewood, N.J., 1981; 
H. Stache, "Tensid-Taschenbuch" (Tenside Handbook), 2nd Edition, C. Hanser 
Verlag, Munich, Vienna, 1981; 
M and J. Ash, "Encyclopedia of Surfactants", Vol. I-III, Chemical 
Publishing Co., New York, 1980-1981. 
The agrochemical preparations contain as a rule 0.1 to 95%, especially 0.1 
to 80%, of active ingredient of the formula I, 1 to 99.9% of a solid or 
liquid additive, and 0 to 25%, particularly 0.1 to 25%, of a tenside. 
Preferred formulations are made up in particular as follows (%=percent by 
weight): 
Emulsifiable concentrates 
active ingredient: 1 to 20%, preferably 5 to 10% 
surface active agent: 5 to 30%, preferably 10 to 20% 
liquid carrier 50 to 94%, preferably 70 to 85%. 
Dusts 
active ingredient: 0.1 to 10%, preferably 0.2 to 1% 
solid carrier: 99.9 to 90%, preferably 99.9 to 99%. 
Suspension concentrates 
active ingredient: 5 to 75%, preferably 10 to 50% 
water: 94 to 25%, preferably 90 to 30% 
surface-active agent: 1 to 40%, preferably 2 to 30%. 
Wettable powders 
active ingredient: 0.5 to 90%, preferably 1 to 80% 
surface-active agent: 0.5 to 20%, preferably 1 to 15% 
solid carrier: 5 to 95%, preferably 15 to 90%. 
Granulates 
active ingredient: 0.5 to 30%, preferably 3 to 15% 
solid carrier: 99.5 to 70%, preferably 97 to 85%. 
Whereas commercial products are preferably in the form of concentrated 
compositions, the preparations employed by the end-user are as a rule 
diluted. The preparations can for application be diluted down to 0.001% of 
active ingredient. The applied amounts are usually 0.01 to 10 kg, 
preferably 0.025 to 5 kg, of active ingredient per hectare. 
The compositions can also contain further additives, such as stabilisers, 
antifoaming agents, viscosity regulators, binders and adhesives, as well 
as fertilisers or other active ingredients for obtaining special effects.