The present invention relates to novel, herbicidally active and plant 
growth-regulating N-phenylsulfonyl-N'-pyrimidinyl-, -N'-triazinyl- and 
-N'-triazolylureas and -thioureas, processes for their preparation, 
compositions containing them as active ingredients, and their use for 
control of weeds, in particular selectively in crops of useful plants, or 
for regulating and inhibiting plant growth. 
Urea compounds, triazine compounds and pyrimidine compounds having a 
herbicidal action are generally known. Such compounds are described, for 
example, in European Patent Applications 0 007 687, 0 030 138, 0 073 562 
and 0 126 711. 
Novel sulfonylureas and -thioureas having herbicidal and plant 
growth-regulating properties have now been found. 
The N-phenylsulfonyl-N'-pyrimidinyl-, -N'-triazinyl- and -N'-triazolylureas 
and -thioureas according to the invention are those of the formula I 
##STR4## 
in which X is oxygen, sulfur, SO or SO.sub.2 ; W is oxygen or sulfur; 
R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, 
bromine, iodine, (X).sub.n R.sub.3, NO.sub.2, NR.sub.4 R.sub.5, 
--C.tbd.CR.sub.6, 
##STR5## 
or cyano; n is the number 0 or 1; R.sub.3 is C.sub.1 -C.sub.4 alkyl or 
C.sub.1 -C.sub.4 alkyl which is substituted by 1-4 halogen atoms, C.sub.1 
-C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio; or C.sub.2 -C.sub.4 alkenyl 
or C.sub.2 -C.sub.4 alkenyl which is substituted by 1-4 halogen atoms; 
R.sub.4 is hydrogen, CH.sub.3 O, CH.sub.3 CH.sub.2 O or C.sub.1 -C.sub.3 
alkyl; R.sub.5 is hydrogen or C.sub.1 -C.sub.3 alkyl; R.sub.6 is hydrogen, 
methyl or ethyl; R.sub.7 is hydrogen or methyl; Z is 
##STR6## 
E is methine or nitrogen; R.sub.8 is C.sub.1 -C.sub.4 alkyl, C.sub.1 
-C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, 
C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, 
C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, 
C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; R.sub.9 is 
C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 
haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, 
C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, C.sub.2 
-C.sub.5 alkylthioalkyl or cyclopropyl; R.sub.10 is hydrogen, fluorine, 
chlorine, methyl, trifluoromethyl, CH.sub.3 O, CH.sub.3 CH.sub.2 O, 
CH.sub.3 S, CH.sub.3 SO, CH.sub.3 SO.sub.2 or cyano; R.sub.11 is methyl, 
ethyl, CH.sub.3 O, CH.sub.3 CH.sub.2 O, fluorine or chlorine; R.sub.12 is 
methyl, ethyl, CH.sub.3 O, CH.sub.3 CH.sub.2 O, fluorine or chlorine; 
R.sub.13 is C.sub.1 -C.sub. 3 alkyl; and R.sub.14 is C.sub.1 -C.sub.3 
alkyl, C.sub.1 -C.sub.3 alkoxy, chlorine or OCHF.sub.2 ; and the salts of 
these compounds; with the provisos that E is methine if R.sub.8 is 
halogen; and E is methine if R.sub.8 or R.sub.9 is OCHF.sub.2 or 
SCHF.sub.2. 
In the above definitions, halogen is to be understood as meaning fluorine, 
chlorine, bromine or iodine, preferably fluorine, chlorine or bromine. 
The alkyl groups in the substituent definitions can be straight-chain or 
branched and are, for example, methyl, ethyl, n-propyl, isopropyl, 
n-butyl, sec-butyl, isobutyl or tert-butyl. The alkyl groups occurring as 
or in the substituents preferably have 1-3 carbon atoms. 
Alkenyl is to be understood as meaning straight-chain or branched alkenyl, 
for example vinyl, allyl, methallyl, 1-methylvinyl or but-2-en-1-yl. 
Alkenyl radicals having a chain length of 2 to 3 carbon atoms are 
preferred. 
Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, 
chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 
2-fluoroethyl, 2-chloroethyl or 2,2,2-trichloroethyl; preferably 
trichloromethyl, difluorochloromethyl, trifluoromethyl or 
dichlorofluoromethyl. 
Alkoxy is, for example, methoxy, ethoxy, propyloxy, i-propyloxy, 
n-butyloxy, isobutyloxy, sec-butyloxy or tert-butyloxy; preferably methoxy 
or ethoxy. 
Haloalkoxy is, for example, difluoromethoxy, trifluoromethoxy, 
2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 
2-chloroethoxy or 2,2-difluoroethoxy; preferably difluoromethoxy, 
2-chloroethoxy or trifluoromethoxy. 
Alkylthio is, for example, methylthio, ethylthio, propylthio, 
isopropylthio, n-butylthio, iso-butylthio, sec-butylthio or 
tert-butylthio, preferably methylthio or ethylthio. 
Examples of alkoxyalkoxy are: methoxymethoxy, methoxyethoxy, 
methoxypropyloxy, ethoxymethoxy, ethoxyethoxy or propyloxymethoxy. 
Alkylamino is, for example, methylamino, ethylamino, n-propylamino or 
isopropylamino. Dialkylamino is, for example, dimethylamino, 
methylethylamino, diethylamino or n-propylmethylamino. 
The invention also relates to the salts which the compounds of the formula 
I can form with amines, alkali metal and alkaline earth metal bases or 
quaternary ammonium bases. 
Preferred alkali metal and alkaline earth metal hydroxides as salt-forming 
agents are the hydroxides of lithium, sodium, potassium, magnesium or 
calcium, in particular those of sodium or potassium. 
Examples of amines which are suitable for salt formation are primary, 
secondary and tertiary aliphatic and aromatic amines, such as methylamine, 
ethylamine, propylamine, isopropylamine, the four isomeric bytylamines, 
dimethylamine, diethylamine, diethanolamine, dipropylamine, 
diisopropylamine, di-n-butylamine, pyrrolidine, piperidine, morpholine, 
trimethylamine, triethylamine, tripropylamine, quinuclidine, pyridine, 
quinoline and isoquinoline, in particular ethyl-, propyl-, diethyl-or 
triethylamine, especially isopropylamine 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, the trimethylethylammonium cation or even the 
ammonium cation. 
Preferred compounds of the formula I are those in which W is oxygen, Z is 
preferably Z1, X is oxygen or sulfur, but particularly preferably oxygen, 
and E is nitrogen. 
A preferred group of compounds of the formula I is furthermore that in 
which Z is Z1 and X is oxygen or sulfur, particularly preferably oxygen, 
and E is methine. 
Compounds of these two groups of compounds of the formula I which are of 
particular interest are those in which R.sub.2 is hydrogen, fluorine, 
chlorine, OCH.sub.3, OCHF.sub.2, methyl, SCH.sub.3, methoxy, ethoxy or 
chloroethoxy; R.sub.8 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, 
C.sub.1 -C.sub.2 haloalkoxy, trifluoromethyl, CHF.sub.2, CH.sub.2 F, 
CH.sub.2 OCH.sub.3, fluorine, chlorine, NH.sub.2, NHCH.sub.3, 
N(CH.sub.3).sub.2, SCH.sub.3 or CH.sub.2 OCH.sub.3 ; and R.sub.9 is 
C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.2 
haloalkoxy or cyclopropyl. 
In particularly preferred compounds of this group, R.sub.2 is hydrogen; 
R.sub.8 is methyl, ethyl, OCH.sub.3, OC.sub.2 H.sub.5, OCHF.sub.2, 
OCH.sub.2 CF.sub.3, chlorine, NHCH.sub.3, N(CH.sub.3).sub.2 or CH.sub.2 
OCH.sub.3 ; and R.sub.9 is methyl, OCH.sub.3, OCHF.sub.2, OC.sub.2 H.sub.5 
or cyclopropyl. 
In another preferred sub-group of compounds of the formula I, W is oxygen; 
Z is Z1; X is sulfur; R.sub.2 is hydrogen, fluorine, chlorine, OCH.sub.3, 
OCHF.sub.2, methyl or methylthio; R.sub.8 is C.sub.1 -C.sub.3 alkyl, 
C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.2 haloalkoxy, CF.sub.3, CHF.sub.2, 
CH.sub.2 F, CH.sub.2 OCH.sub.3, fluorine, chlorine, NH.sub.2, NHCH.sub.3, 
N(CH.sub.3).sub.2, SCH.sub.3 or CH.sub.2 OCH.sub.3 ; and R.sub.9 is 
C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.2 
haloalkoxy or cyclopropyl. 
Compounds of the formula I from this group which are of interest are those 
in which W is oxygen; Z is Z1; X is sulfur; R.sub.2 is hydrogen; R.sub.8 
is methyl, ethyl, OCH.sub.3, OC.sub.2 H.sub.5, OCHF.sub.2, OCH.sub.2 
CF.sub.3, Cl, NHCH.sub.3, N(CH.sub.3).sub.2 or CH.sub.2 OCH.sub.3 ; and 
R.sub.9 is methyl, OCH.sub.3, OCHF.sub.2, OC.sub.2 H.sub.5 or cyclopropyl. 
Preferred individual compounds from the scope of formula I are: 
N-[2-(oxetan-3-oxycarbonyl)]phenylsulfonyl-N'-(4-methoxy-6-methyl-1,3,5-tri 
azinyl)urea; 
N-[2-(oxetan-3-oxycarbonyl)]phenylsulfonyl-N'-(4,6-dimethylpyrimidin-2-yl)u 
rea; 
N-[2-(oxetan-3-oxycarbonyl)]phenylsulfonyl-N'-(4-methoxy-6-methylpyrimidin- 
2-yl)urea; and 
N-[2-(oxetan-3-oxycarbonyl)]phenylsulfonyl-N'-(4,6-dimethoxypyrimidin-2-yl) 
urea. 
The compounds of the formula I can be prepared by either 
a) reacting a phenylsulfonamide of the formula II 
##STR7## 
in which R.sub.2 and X are as defined under formula I, with an 
pyrimidinyl-, triazolyl- or triazinylcarbamate or -thiocarbamate of the 
formula III 
##STR8## 
in which W, Z and R.sub.1 are as defined under formula I and R.sub.15 is 
phenyl or substituted phenyl, in the presence of a base, or 
b) reacting a sulfonylcarbamate or -thiocarbamate of the formula IV 
##STR9## 
in which R.sub.2, W, X and Z are as defined under formula I and R.sub.15 
is as defined under formula III, with an amine of the formula V 
EQU H.sub.2 N--Z (V) 
in which Z is as defined under formula I, in the presence of a base, or 
c) reacting a phenylsulfonamide of the formula II 
##STR10## 
in which R.sub.2 and X are as defined under formula I, with an 
pyrimidinyl-, triazolyl- or triazinyl isocyanate or isothiocyanate of the 
formula VII 
EQU Y.dbd.N.dbd.C--Z (VII) 
in which Z is as defined under formula I and Y is oxygen or sulfur, in the 
presence of a base. 
Compounds of the formula I can also be prepared by reacting a compound of 
the formula VIII with a compound of the formula V in the presence of an 
ammonium-, phosphonium-, sulfonium- or alkali metal cyanate salt of the 
formula X 
EQU M.sup.+ OCN.sup.- (X) 
wherein M is an alkali metal or the group R.sub.15 R.sub.16 R.sub.17 
R.sub.18 Q, in which R.sub.15 R.sub.16 R.sub.17 R.sub.18 independently 
from another is C.sub.1 -C.sub.18 -alkyl, benzyl oder phenyl, with the 
total number of C-atoms not greater than 36; and Q is nitrogen, sulfur or 
phosphorus. According to this method the compounds 
N-[2-(oxetan-3-oxycarbonyl)]phenylsulfonyl-N'-(4-methoxy-6-methyl-1,3,5-tr 
iazinyl)-urea; 
N-[2-(oxetan-3-oxycarbonyl)]phenylsulfonyl-N'-(4,6-dimethylpyrimidin-2-yl)u 
rea; 
N-[2-(oxetan-3-oxycarbonyl)]phenylsulfonyl-N'-(4-methoxy-6-methylpyrimidin- 
2-yl)urea; and 
N-[2-(oxetan-3-oxycarbonyl)]phenylsulfonyl-N'-(4,6-dimethoxypyrimidin-2-yl) 
urea can be prepared with advantage. Such reactions are described in Swiss 
Patent No. 662 348. 
The reactions to give compounds of the formula I are advantageously carried 
out 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, and amides, such as 
dimethylformamide, diethylformamide or N-methylpyrrolidone. The reaction 
temperatures are preferably between -20.degree. and +120.degree. C. 
The reactions in general proceed slightly exothermically and can be carried 
out at room temperature. The mixture is advantageously heated to the 
boiling point of the reaction mixture for a short time for the purpose of 
shortening the reaction time or to start the reaction. The reaction times 
can also be shortened by addition of a few drops of 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. However, inorganic bases such as 
hydrides, such as sodium hydride or calcium hydride, hydroxides, such as 
sodium hydroxide and potassium hydroxide, carbonates, such as sodium 
carbonate and potassium carbonate, or bicarbonates, such as potassium 
bicarbonate and sodium bicarbonate, can also be used as bases. 
The end products of the formula I can be isolated by concentrating the 
mixture and/or evaporating off the solvent and purified by 
recrystallisation or trituration of the solid residue in solvents in which 
they are not readily soluble, such as ethers, aromatic hydrocarbons or 
chlorinated hydrocarbons. 
In the preparation procesess described above for compounds of the formula 
I, R.sub.15 is preferably phenyl which can be substituted by C.sub.1 
-C.sub.4 alkyl or halogen, especially preferably phenyl. 
The phenylsulfonamides of the formula II are novel compounds which have 
been developed and prepared specifically for the preparation of the active 
ingredients of the formula I. The present invention thus also relates to 
them. They can be prepared from the corresponding phenylsulfonyl chlorides 
of the formula VIII 
##STR11## 
in which R.sub.2 and X are as defined under formula I, by reaction with 
ammonia. Such reactions are known and familiar to the expert. 
The phenylsulfonyl chlorides of the formula VIII are novel compounds which 
have been developed and prepared specifically for the preparation of the 
active ingredients of the formula I. The present invention therefore 
likewise relates to them. The phenylsulfonyl chlorides of the formula VIII 
are prepared by reacting the correspondingly substituted 
2-chlorosulfonyl-benzoyl chlorides (cf., for example, D. Davis, J. Chem 
Soc. 2042, 2044 (1932)) with a compound of the formula IX 
##STR12## 
in which X is as defined under formula I, in the presence of a base. Such 
reactions are known and familiar to the expert. 
Phenylsulfonyl chlorides of the formula VIII in which X is oxygen can also 
be prepared by reacting 2-isopropylthiobenzoic acid (cf., for example, H. 
Gilman, F. J. Webb, J. Am. J. Chem Soc. 71, 4062-4063) with thionyl 
chloride to give the corresponding benzoyl chloride, which is then 
converted into the corresponding oxetan-3-yl 2-isopropylthiobenzoate with 
3-hydroxyoxetane in the presence of a base, to give finally the 
sulfonylchloride of the formula VIII by reaction with chlorine. Such 
reactions are known and familiar to the expert. 
Compounds of the formula IX and their preparation are known (cf., for 
example, B. Lamm et al., Acta Chem. Scand. 28, 701 (1974) or J. Org. Chem. 
48, 2953-2956 (1983)). 
The sulfonylcarbamates and -thiocarbamates of the formula IV are novel and 
the present invention relates to them. They can be obtained, for example, 
by reaction of the sulfonamides of the formula II with diphenyl carbamate 
or thiocarbamate in the presence of a base. Such reactions are known and 
familiar to the expert. 
The amines of the formula V are described in European Patent Applications 0 
007 687, 0 030 138, 0 073 562 and 0 126 711, and in U.S. Pat. No. 4 579 
584. 
Processes for the preparation of N-pyrimidinyl- and N-triazinylcarbamates 
are described, for example, in EP-A-0 101 670. N-Triazolylcarbamates can 
be prepared analogously. 
The active ingredients of the formula I are as a rule employed successfully 
at rates of application of 0.001 to 2 kg/ha, in particular 0.005 to 1 
kg/ha. The doses required for the desired action can be determined by 
experiments. It depends on the nature of the action, the development stage 
of the crop plant and of the weed and on the application conditions 
(location, time, method) and can, as a result of these parameters, be 
varied within wide ranges. 
The compounds of the formula I are distinguished by growth-inhibiting and 
herbicidal properties which render them excellent for use in crops of 
useful plants, in particular in cereals, cotton, soya, rape, maize and 
rice, use in soya crops and cereals being especially preferred. Control of 
the weeds in soya crops is preferably postemergence. The compounds of the 
formula I are distinguished in particular by their good degradability. 
The invention also relates to herbicidal and plant growth-regulating 
compositions which comprise a novel active ingredient of the formula I, 
and methods for inhibition of plant growth. 
Plant growth regulators are substances which cause agronomically desirable 
biochemical and/or physiological and/or morphological changes in/on the 
plants. 
The active ingredients present in the compositions according to the 
invention influence plant growth in various ways depending on the time of 
application, dosage, mode of application and environmental conditions. 
Plant growth regulators of the formula I can, for example, inhibit the 
vegetative growth of plants. This type of action is of interest on lawn 
areas, in the growing of ornamentals, in fruit plantations, on road 
embankments and on sports fields and industrial premises, and also for 
controlled inhibition of secondary shoots, such as on tobacco. In 
agriculture, inhibition of the vegetative growth of cereals leads to 
reduced lodging via strengthening of the stem, and similar agronomic 
actions are achieved in rape, sunflowers, maize and other crop plants. The 
number of plants per unit area can moreover be increased by inhibition of 
the vegetative growth. Another field of use of growth inhibitors is 
selective control of ground-covering plants in plantations or wide-row 
crops by severe inhibition of growth, without killing these 
ground-covering plants, so that competition against the main crop is 
excluded, but the agronomically positive effects, such as prevention of 
erosion, nitrogen bonding and loosening of the soil, are retained. 
A method for inhibition of plant growth is to be understood as meaning 
control of the natural plant development without changing, in the sense of 
mutation, the life-cycle of the plants determined by genetic properties. 
The method of growth regulation is used at a point in time of the 
development of the plants which is to be determined in the individual 
case. The active ingredients of the formula I can be applied before or 
after emergence of the plants, for example even to the seeds or the 
seedlings, to roots, tubors, stems, leaves, flowers or other plant parts. 
This can be effected, for example, by applying the active ingredient 
itself or in the form of a composition to the plants and/or by treatment 
of the nutrient medium of the plants (soil). 
Various methods and techniques are suitable for use of the compounds of the 
formula I or compositions containing them for regulating plant growth, for 
example the following: 
i) Seed dressing 
a) Dressing the seeds with an active ingredient formulated as a wettable 
powder by shaking in a vessel until the active ingredient is distributed 
uniformly over the seed surface (dry dressing). Up to 4 g of active 
ingredient of the formula I (in the case of a 50% formulation: up to 8.0 g 
of wettable powder) are used here per kg of seed. 
b) Dressing of the seeds with an emulsion concentrate of the active 
ingredient or with an aqueous solution of the active ingredient of the 
formula I formulated as a wettable powder by method a) (wet dressing). 
c) Dressing by dipping the seed in a mixture containing up to 1000 ppm of 
active ingredient of the formula I for 1 to 72 hours and if appropriate 
subsequent drying of the seed (seed soaking). 
Dressing of the seed and treatment of the germinated seedling are of course 
the preferred methods of application, because the treatment with the 
active ingredient is directed completely toward the target crop. As a rule 
0.001 g to 4.0 g of active substance are used per kg of seed, it being 
possible to deviate upwards or downwards from the limit concentrations 
stated (repeat dressing) depending on the method, which also allows the 
addition of other active ingredients or micronutrients. 
ii) Controlled release of the active ingredient 
The active ingredient is absorbed in solution onto mineral granule carriers 
or polymerised granules (urea/formaldehyde) and allowed to dry. If 
appropriate, a coating which allows the active ingredient to be released 
in metered form over a certain period of time can be applied (coated 
granules). 
The compounds of the formula I are employed in unchanged form, as 
obtainable from the synthesis, or preferably with the auxiliaries 
customary in formulation technology, and are therefore processed, for 
example, to emulsifiable concentrates, directly sprayable or dilutable 
solutions, dilute emulsions, wettable powders, soluble powders, dusts, 
granules and also capsules in, for example, polymeric substances in a 
known manner. The methods of use, such as spraying, misting, dusting, 
wetting, sprinkling or pouring, are, like the nature of the compositions, 
chosen according to the effects required and the given circumstances. 
The formulations, i.e. the compositions, formulations or preparations 
comprising the active ingredient of the formula I and if appropriate one 
or more solid or liquid additives, are prepared in a known manner, for 
example by intimate mixing and/or grinding of the active ingredients with 
extenders, for example with solvents, solid carriers and if appropriate 
surface-active ingredients (surfactants). 
Possible solvents are: aromatic hydrocarbons, in particular the fractions 
C.sub.8 to C.sub.12, such as mixtures of alkylbenzenes, for example xylene 
mixtures, or alkylated naphthalenes; aliphatic and cycloaliphatic 
hydrocarbons, such as paraffins, cyclohexane or tetrahydronaphthalene; 
alcohols, such as ethanol, propanol or butanol; glycols and ethers and 
esters thereof, such as propylene glycol or dipropylene glycol ether; 
ketones, such as cyclohexanone, isophorone or diacetone alcohol; strong 
polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or 
water; vegetable oils and esters thereof, such as rape, castor or soya 
oil; and if appropriate also silicone oils. 
Solid carriers which are used, for example for dusts and dispersible 
powders, are as a rule natural rock powders, such as calcite, talc, 
kaolin, montmorillonite or attapulgite. Highly disperse silicic acid or 
highly disperse absorbent polymers can also be added to improve the 
physical properties. Granular, adsorbent granule carriers are porous 
types, for example pumice, crushed brick, sepiolite or bentonite, and 
non-sorbent carrier materials are, for example, calcite or sand. A wide 
range of pregranulated materials of inorganic or organic nature, such as, 
in particular, dolomite or comminuted plant residues, can moreover be 
used. 
Surface-active ingredients are nonionic, cationic and/or anionic 
surfactants having good emulsifying, dispersing and wetting properties, 
depending on the nature of the active ingredient of the formula I to be 
formulated. Surfactants is also to be understood as meaning surfactant 
mixtures. 
Suitable anionic surfactants can be either so-called water-soluble soaps or 
water-soluble synthetic surface-active ingredients. 
Soaps are the alkali metal, alkaline earth metal or substituted or 
unsubstituted ammonium salts of higher fatty acids (C.sub.10 -C.sub.22), 
for example the sodium or potassium salts of oleic or stearic acid, or of 
naturally occurring fatty acid mixtures, which can be obtained, for 
example, from coconut oil or tallow oil. The fatty acid methyltaurine 
salts may furthermore also be mentioned. 
More often, however, so-called synthetic surfactants are used, in 
particular fatty alcohol sulfonates, fatty alcohol sulfates, sulfonated 
benzimidazole derivatives or alkylarylsulfonates. 
The fatty alcohol sulfonates or sulfates are as a rule in the form of 
alkali metal, alkaline earth metal or substituted or unsubstituted 
ammonium salts and contain an alkyl radical having 8 to 22 C atoms, alkyl 
also including the alkyl moiety of acyl radicals, for example the sodium 
or calcium salt of ligninsulfonic acid, of dodecylsulfate or of a fatty 
alcohol sulfate mixture prepared from naturally occurring fatty acids. 
These also include 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 
radical having 8-22 C atoms. Alkylarylsulfonates are, for example, the Na, 
Ca or triethanolamine salts of dodecylbenzenesulfonic acid, 
dibutylnaphthalenesulfonic acid or a naphthalenesulfonic acid-formaldehyde 
condensation product. 
Corresponding phosphates, for example salts of the phosphoric acid ester of 
a p-nonylphenol-(4-14)-ethylene oxide adduct, or phospholipids are 
furthermore also suitable. 
Nonionic surfactants are in particular polyglycol ether derivatives of 
aliphatic or cycloaliphatic alcohols, saturated or unsaturated fatty acids 
and alkylphenols, which can contain 3 to 30 glycol ether groups and 8 to 
20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon 
atoms in the alkyl radical of the alkylphenols. 
Other suitable nonionic surfactants are the water-soluble polyethylene 
oxide adducts, containing 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 surfactants are nonylphenol polyethoxyethanols, castor 
oil polyglycol ether, polypropylene-polyethylene oxide adducts, 
tributylphenoxypolyethoxyethanol, polyethylene glycol and 
octylphenoxypolyethoxyethanol. 
Fatty acid ester of polyoxyethylenesorbitan, such as 
polyoxyethylenesorbitan trioleate, are furthermore also suitable. 
The cationic surfactants are in particular quaternary ammonium salts which 
contain at least one alkyl radical having 8 to 22 C atoms as the 
N-substituent and lower halogenated or unhalogenated alkyl, benzyl or 
lower hydroxyalkyl radicals as further substituents. The salts are 
preferably in the form of halides, methylsulfates or ethylsulfates, for 
example stearyltrimethylammonium chloride or 
benzyldi(2-chloroethyl)ethylammonium bromide. 
The surfactants customary in formulation technology are described, inter 
alia, in the following publications: 
"McCutcheon's Detergents and Emulsifiers Annual", Mc Publishing Corp., Glen 
Rock, N.J., 1988. 
M. and J. Ash, "Encyclopedia of Surfactants", Vol.I-III, Chemical 
Publishing Co., New York, 1980-1981. 
Dr. Helmut Stache "Tensid-Taschenbuch" (Surfactant Handbook), Carler Hanser 
Verlag, Munich/Vienna 1981. 
The pesticidal compositions as a rule comprise 0.1 to 99%, in particular 
0.1 to 95%, of active ingredient of the formula I, 1 to 99% of a solid or 
liquid additive and 0 to 25%, in particular 0.1 to 25%, of a surfactant. 
While concentrated compositions are more preferable as commercial goods, 
the end user as a rule uses dilute compositions. 
The compositions can also contain other additives, such as stabilisers, for 
example epoxidised or unepoxidised vegetable oils (epoxidised coconut oil, 
rape oil or soya oil), foam suppressants, for example silicone oil, 
preservatives, viscosity regulators, binders, tackifiers and fertilisers, 
or other active ingredients to achieve specific effects. 
Preferred formulations have, in particular, the following composition: (% 
=per cent by weight) 
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Emulsifiable concentrates: 
Active ingredient: 
1 to 20%, preferably 5 to 10% 
Surface-active agent: 
5 to 30%, preferably 10 to 20% 
Liquid carrier: 
15 to 94%, preferably 70 to 85% 
Dusts: 
Active ingredient: 
0.1 to 10%, preferably 0.1 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 24%, preferably 88 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% 
Granules: 
Active ingredient: 
0.5 to 30%, preferably 3 to 15% 
Solid carrier: 99.5 to 70%, preferably 97 to 85% 
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