Novel substituted N-sulfonyl-N'-pyrimidinylureas or N-sulfonyl-N'-triazinylureas of the formula I ##STR1## have good pre- and postemergence selective herbicidal and growth regulating properties. In this formula E is nitrogen or --CH.dbd., the group ##STR2## is a phenyl, naphthyl, furyl, thiophenyl, pyrrole or pyridinyl radical which is substituted in accordance with the definitions of PA1 R.sup.1 and R.sup.2, PA1 R.sup.3 and R.sup.4 are hydrogen, lower alkyl or lower alkoxy, or one of R.sup.3 and R.sup.4 may also be halogen, lower alkenyl, lower haloalkenyl, lower haloalkoxy, amino, lower alkylamino, --CH(OCH.sub.3).sub.2, a cyclised ketal group or a saturated 5- to 7-membered heterocycle which is bound through the nitrogen atom, PA1 R.sup.5 is hydrogen, lower alkyl, lower haloalkyl, or an unsubstituted or substituted phenyl, benzyl or naphthyl radical, and PA1 R.sup.6 is an alkyl, acyl or acylamido radical which is bound through sulfur or a sulfinyl or sulfonyl group and is as defined in the description, or is a 5- to 7-membered heterocyclic amino radical which is bound through the nitrogen atom. These compounds are particularly suitable for selectively controlling weeds in crops of cereals.

The present invention relates to novel substituted 
N-sulfonyl-N'-pyrimidinylureas and N-sulfonyl-N'-triazinylureas and salts 
thereof with herbicidal and plant growth regulating properties, to the 
preparation thereof, to compositions containing them and to the use 
thereof for controlling weeds, in particular selectively, in crops of 
useful plants, or for regulating and inhibiting plant growth. The 
invention further relates to novel pyrimidin-2-ylureas and 
triazin-ylalkylamines prepared as intermediates. 
The substituted N-sulfonyl-N'pyrimidinylureas and 
N-sulfonyl-N'-triazinylureas of this invention have the formula I 
##STR3## 
wherein E is nitrogen or --CH.dbd., 
X is oxygen, sulfur, --NR.sup.7, --N.dbd.CR.sup.7, --CH.dbd.CH-- or 
##STR4## 
Y is oxygen or an S(O).sub.m radical, m is 0 or an integer from 1 to 2, 
Z is oxygen or sulfur, 
R.sup.1 is hydrogen, halogen, nitro, C.sub.1 -C.sub.4 alkoxy, C.sub.1 
-C.sub.4 haloalkoxy, C.sub.2 -C.sub.4 alkenyloxy, C.sub.2 -C.sub.4 
haloalkenyloxy, C.sub.2 -C.sub.4 alkynyl, an amino group NR.sup.10 
R.sup.11, a ketal radical --CR.sup.7 (OC.sub.1 -C.sub.7 alkyl).sub.2 or 
##STR5## 
a tetrahydrofuran-2-yloxy or tetrahydropyran-2-yloxy radical, --OSO.sub.2 
R.sup.8, --COR.sup.8, 
##STR6## 
--SO.sub.2 NR.sup.10 R.sup.11, SO.sub.2 R.sup.8, YR.sup.8, phenyl, benzyl 
or phenoxy, wherein the phenyl nucleus can be substituted by one or more 
identical or different members selected from the group consisting of 
halogen, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or 
C.sub.1 -C.sub.4 alkoxy, 
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 and R.sup.4, each independently of the other, are 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 
5- to 7-membered nitrogen-containing heterocycle which is bound through 
the nitrogen atom and which may contain a further hetero atom, or are a 
--CH(OCH.sub.3).sub.2 or 
##STR7## 
radical, R.sup.5 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 
haloalkyl, or a phenyl, benzyl, furyl, thienyl or naphthyl radical, each 
of which is unsubstituted or substituted by one or more identical or 
different members selected from the group consisting of halogen, nitro, 
C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 
alkoxy, 
R.sup.6 is an --S(O).sub.m R.sup.9 radical or a 5- to 7-membered 
heterocyclic radical which is bound through a nitrogen atom and may 
contain further hetero atoms in the ring and may be fused to a benzene 
ring and is unsubstituted or substituted by one or more identical or 
different members selected from the group consisting of nitro, halogen or 
C.sub.1 -C.sub.4 alkyl, 
R.sup.7 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, 
C.sub.5 -C.sub.6 6cycloalky, C.sub.4 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.4 
alkoxyalkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.2 -C.sub.4 haloalkenyl, 
C.sub.5 -C.sub.6 cycloalkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.1 -C.sub.4 
cyanoalkyl, C.sub.1 -C.sub.4 alkyl-NR.sup.9 R.sup.10, benzyl or benzyl 
which is substituted by halogen, 
R.sup.8 is C.sub.1 -C.sub.4 alkoxy or has the same meaning as R.sup.7 but 
is not hydrogen, 
R.sup.9 is a C.sub.1 -C.sub.4 alkyl radical which can be substituted by 
halogen, C.sub.2 -C.sub.4 alkoxy, carboxyl, C.sub.1 -C.sub.4 
alkoxycarbonyl or --CONR.sup.10 R.sup.11, or is a phenyl, benzyl or 
naphthyl radical, each of which can be substituted by one or more 
identical or different members selected from the group consisting of 
halogen, nitro, carboxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 
haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy, and in 
an --SR.sup.9 radical R.sup.9 can also be a radical selected from 
--CZ--C.sub.1 -C.sub.4 alkyl, --CZO--C.sub.1 -C.sub.4 alkyl, --CZNR.sup.10 
R.sup.11, --CZ--phenyl, CZ--benzyl or CZ--naphthyl, wherein the phenyl 
rings may be substituted as indicated above, 
R.sup.10 and R.sup.11, each independently of the other, are hydrogen, 
C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 
alkynyl, C.sub.1 -C.sub.4 cyanoalkyl, or one of R.sup.10 and R.sup.11 may 
also be C.sub.1 -C.sub.4 alkoxy or C.sub.2 -C.sub.4 alkoxyalkyl, phenyl or 
benzyl, and the phenyl ring may be substituted by one or identical or 
different members selected from the group consisting of halogen, nitro, 
C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 
alkoxy; or R.sup.10 and R.sup.11, together with the nitrogen atom to which 
they are attached, may also be a 5- to 7-membered saturated or partially 
saturated heterocycle which may contain a further nitrogen or sulfur atom 
in the ring and/or one or two further nitrogen atoms, and which may be 
substituted by halogen and/or C.sub.1 -C.sub.4 alkyl. 
The invention also relates to the salts of these sulfonylureas with organic 
and inorganic bases. 
Herbicidal ureas, triazines and pyrimidines are generally known in the art. 
Sulfonylureas with herbicidal and plant growth regulating properties have 
recently been described for example in European patent application Nos. 
44211, 44807 and 44808, and also in UK patent application Nos. 2 112 783 
and 2 112 784. 
Alkyl in the above definitions denotes straight chain or branched alkyl, 
for example methyl, ethyl, n-propyl, isopropyl or the 4 isomers of butyl. 
Alkoxy is methoxy, ethoxy, n-propoxy, isopropoxy, the 4 isomers of butoxy, 
n-amyloxy, isoamyloxy, 2-amyloxy or 3-amyloxy, with methoxy, ethoxy or 
isopropoxy being preferred. 
Halogen by itself or as moiety of haloalkoxy, haloalkyl or haloalkylthio 
denotes fluorine, chlorine and bromine, with fluorine and chlorine being 
preferred. 
Within the scope of this invention, the radicals defined for R.sup.6 
comprise for example the following radicals: 
__________________________________________________________________________ 
--S--C.sub.1 -C.sub.4 alkyl 
--S--CH.sub.2 COOC.sub.1 -C.sub.4 alkyl 
phenylthio --SCH.sub.2 COOH 
--SO--C.sub.1 -C.sub.4 alkyl 
--S--CH.sub.2 CONHC.sub.1 -C.sub.4 alkyl 
benzylthio --SCH(CH.sub.3)COOH 
--SO.sub.2 C.sub.1 -C.sub.4 alkyl 
--S--CH.sub.2 CON(C.sub.1 -C.sub.4 alkyl).sub.2 
benzoylthio 
--S--CO--C.sub.1 -C.sub.4 alkyl 
--S--CS--OC.sub.1 -C.sub.4 alkyl 
--SCSN(C.sub.1 -C.sub.4 alkyl).sub.2 
__________________________________________________________________________ 
as well as the following heterocyclic amino radicals: 1,2,4-triazolyl, 
1,2,3,4-tetrazol-1-yl, pyrazol-1-yl, imidazol-1-yl, benztriazol-1-yl, 
benzimidazol-1-yl, indol-1-yl, indadzol-1-yl, pyrimidin-1-yl, 
pyridazin-1-yl, pyrazin-1-yl, which rings may be substituted by one to 
three members selected from nitro, halogen, preferably chlorine or 
bromine, and/or C.sub.1 -C.sub.4 alkyl, preferably methyl. 
The 5- to 7-membered saturated or partially saturated heterocyclic radicals 
falling within the definition of the amino radical NR.sup.10 R.sup.11 
comprise for example the following radicals: pyrrolidino, piperidino, 
morpholino, thiomorpholino, azepino, imidazol-1-yl, triazol-1-yl, 
1,3-oxazol-3-yl, 1,3-thiazol-1-yl, piperazin-1-yl, which radicals may be 
unsubsituted or substituted by halogen, preferably chlorine or bromine 
and/or by C.sub.1 -C.sub.4 alkyl, preferably methyl. 
Alkoxyalkyl radicals are methoxymethyl, ethoxymethyl, methoxyethyl and 
ethoxyethyl, with methoxyethyl being preferred. Within the scope of this 
invention, alkoxyalkyl radicals are methoxymethoxy, ethoxymethoxy, 
methoxyethoxy and ethoxyethoxy. Haloalkyl by itself or as moiety of 
another substituent such as haloalkoxy or haloalkylthio is usually 
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, and 
1,1,2,3,3,3-hexafluoropropyl. Fluoromethyl, chloromethyl, difluoromethyl 
and trifluoromethyl are preferred. 
Preferred compounds of formula I are those wherein either 
Z is an oxygen atom, 
the 
##STR8## 
radical is a phenyl radical which is substituted in the ortho-position by 
R.sup.1, 
R.sup.6 is an --S(O).sub.m R.sup.8 radical, 
R.sup.6 is a 5- to 7-membered heterocycle which is bound through the 
nitrogen atom and may contain further hetero atoms in the ring, and may be 
fused to a benzene ring and may be unsubstituted or substituted by one or 
more members selected from the group consisting of nitro, halogen and/or 
C.sub.1 -C.sub.4 alkyl. 
Preferred compounds are for example those of the formula Ic 
##STR9## 
wherein E, R.sup.1, R.sup.3, R.sup.4 and R.sup.6 are as defined for 
formula I; and those of the general formula Id 
##STR10## 
wherein E, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.8 are as defined 
for formula I. 
The compounds of formula I are prepared for example by the following 
methods. 
A first process comprises reacting a sulfonyl isocyanate of formula II 
##STR11## 
wherein R.sup.1, R.sup.2, X and Z are as defined for formula I, with the 
equivalent amount of a 2-aminopyrimidine or 2-aminotriazine of formula III 
##STR12## 
wherein E, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as defined for 
formula I, in an inert organic solvent or diluent, and, if desired, 
isolating the resultant urea in the form of a salt or converting it into a 
salt with an inorganic or organic base. 
A second process for obtaining the compounds of formula I comprises 
reacting a sulfonylamide of formula IV 
##STR13## 
wherein R.sup.1, R.sup.2 and X are as defined for formula I, with the 
equivalent amount of a 2-pyrimidinyl- or 2-triazinylcarbamoylhalide of 
formula V 
##STR14## 
wherein Hal is a halogen atom, preferably chlorine or bromine, and E, 
R.sup.3, R.sup.4, R.sup.5, R.sup.6 and Z are as defined for formula I, in 
an inert solvent or diluent and in the presence of a base, and, if 
desired, isolating the resultant urea in the form of a salt or converting 
it into a salt with an inorganic or organic base. 
A third process for obtaining the compounds of formula I comprises reacting 
a sulfonylurea of formula VI 
##STR15## 
wherein E, R.sup.1, R.sup.2, R.sup.3, R.sup.4, X and Z are as defined for 
formula I, with the equivalent amount of a methyl halide of formula VII 
##STR16## 
wherein Hal is a halogen atom, preferably a chlorine or bromine atom, and 
R.sup.5 and R.sup.6 are as defined for formula I, in an inert solvent or 
diluent and in the presence of a base, and, if desired, isolating the 
resultant urea in the form of a salt or converting it into a salt with an 
inorganic or organic base. 
If desired, the ureas of formula I can be converted into basic addition 
salts with amines, alkali metal hydroxides or alkaline earth metal 
hydroxides or with quaternary ammonium bases. This is done for example by 
reacting the urea with the equimolar amount of base and removing the 
solvent by evaporation. Such reactions are known and are described for 
example in U.S. Pat. Nos. 2,834,757 and 3,410,887. 
It is convenient to carry out these reactions for obtaining compounds of 
formula I in aprotic, inert organic solvents. 
Examples of 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 dioxan; nitriles such as acetonitrile or propionitrile; 
amides such as dimethylformamide, diethylformamide or 
N-methylpyrrolidinone. 
The reaction temperatures are preferably in the range from -20.degree. to 
+120.degree. C. The coupling reactions are normally slightly exothermic 
and can be carried out at room temperature. To shorten the reaction time 
or also to initiate the reaction it is expedient to heat the reaction 
mixture briefly to boiling point. The reaction times can also be shortened 
by addition of a few drops of a base or isocyanate as catalyst. Preferred 
bases are tertiary amines such as trimethylamine, triethylamine, 
quinuclidine, 1,4-diazabicyclo[2,2,2]octane, 
1,5-diazabicyclo[4,3,0]-non-5-en or 1,8-diazabicyclo[5,4,0]undec-7-ene. 
However, the bases employed may also be inorganic bases, e.g. hydrides 
such as sodium hydride or calcium hydride, hydroxides such as sodium 
hydroxide or potassium hydroxide, carbonates such as sodium or potassium 
carbonate, or bicarbonates such as potassium or sodium bicarbonate. 
The final products of formula I can be isolated by concentrating the 
reaction mixture and/or removing the solvent by evaporation, and by 
recrystallisation or by triturating the solid residue in a solvent in 
which it is poorly soluble, such as an ether, an aromatic hydrocarbon or a 
chlorinated hydrocarbon. 
In addition to these general methods of preparing the compounds of formula 
I, and depending on the meanings of the substituents R.sup.5 and R.sup.6, 
further synthesis paths, each of which is suitable only for one specific 
group of final products, are also possible. Such syntheses are illustrated 
in the following schemes. In the formulae below, E, m, R.sup.1, R.sup.2, 
R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.8, X and Z are as defined for 
formula I. The Roman numerals I, II and IV denote the formulae so numbered 
above. 
##STR17## 
A 2-aminopyridine or a 2-amino-1,3,5-triazine of formula VIII is condensed 
with an aldehyde to give the Schiff's base, which is reacted in situ with 
the mercapto compound. The reaction is carried out at elevated 
temperature, for example at the boiling point of the reaction mixture in 
an organic solvent or mixture of solvents, e.g. an alkanol and/or an 
aromatic hydrocarbon. A small amount of catalyst is added to accelerate 
the reaction. Example 1 describes the preparation of a compound of the 
formula IIIa and further compounds are listed in Table 1. These 
intermediates are novel and constitute an object of the invention. The 
condensates of formula IIIa are then reacted, in accordance with the first 
preparatory process, with a sulfonyl isocyanate of formula II, as 
described in Examples 9-11. 
##STR18## 
In this process also the 2-aminopyridine or 2-aminotriazine of formula VIII 
is reacted with a cyclic secondary amine. The reaction is conducted in the 
presence of a small amount of acid in an organic solvent. Examples 5-8 
describe such reactions to give compounds of the formula IIIb. These 
compounds can then be further reacted with a sulfonyl isocyanate of 
formula II to give an urea of formula I, as described in Examples 12 and 
13. 
##STR19## 
The 2-aminopyrimidine or 2-aminotriazine of formula VIII and a sulfinic 
acid are charged to an organic solvent or diluent and the mixture is 
heated to give the aldehyde. The condensate can be precipitated by 
diluting the reaction mixture with water. Such a reaction is described in 
Example 2. Further compounds are listed in Table 2. The intermediates of 
formula IIIc likewise constitute an object of this invention. The further 
reaction of the compound of formula IIIc with a sulfonyl isocyanate of 
formula II to give the urea of formula I is performed in known manner. 
A compound of formula IIIa can also be converted by oxidation into a 
compound of formula IIIc 
##STR20## 
wherein n is 1 or 2. 
The oxidation is carried out in an inert solvent or diluent in the 
temperature range from 0.degree. C. to the boiling point of the reaction 
mixture. Suitable oxidising agents are hydrogen peroxide, an organic 
peracid such as perbenzoic acid or peracetic acid, or also potassium 
permanganate or chromium oxide. The duration of the oxidation and the 
amount of oxidising agent to be used depend on the desired oxidation step 
of the compound of formula IIIa. 
##STR21## 
This scheme corresponds more or less to the above described second process 
for the preparation of the sulfonylureas of formula I, except that first a 
(2-pyrimidinyl)-N-methylcarbamoyl halide or 
N-(2-triazinyl)-N-methylcarbamoyl halide of the formula Va is prepared in 
a preliminary step, in an inert organic solvent, by condensing the 
compound of formula III with a carbonyl dihalide (phosgene), and then 
reacting the compound of formula Va with the sulfonamide of formula IV to 
give an urea of formula I. 
##STR22## 
A sulfonyl halide of formula IV is reacted with a methyl halide, in an 
inert organic solvent and in the presence of a base, to give an urea of 
formula I. The reaction takes place at room temperature and can be speeded 
up by heating briefly to the boiling point of the reaction mixture. 
##STR23## 
This schema is the same as scheme 1, except that a sulfonylurea of formula 
XI is used as starting material. This sulfonylurea is then reacted with an 
aldehyde and a mercaptan in an inert organic solvent or diluent and in the 
presence of a small amount of acid. The resultant sulfonylurea of formula 
Ia can be oxidised to give the corresponding sulfinyl or sulfonyl compound 
of formula Ib by an oxidation similar to that described after scheme III. 
##STR24## 
This scheme is similar to scheme 2, except that the starting material 
employed is a sulfonylurea of formula IX, which is then reacted, in an 
inert solvent or diluent, with an aldehyde and a cyclic secondary amine, 
in the presence of a small amount of acid and at elevated temperature, to 
give an sulfonylurea of formula I. 
The final products can be isolated by concentrating the reaction mixture 
and/or evaporating off the solvent, and purified by recrystallising or 
triturating the solid residue in solvents in which they are not readily 
soluble, e.g. in an ether, an aromatic hydrocarbon or a chlorinated 
hydrocarbon. 
The compounds of formula I are stable compounds, and no protective measures 
are required for handling them. 
When used at low rates of application, the compounds of formula I have good 
selective growth inhibiting and selective herbicidal properties which make 
them most suitable for use in crops of useful plants, especially in 
cereals, cotton, soybeans, maize and rice. In some cases damage is also 
caused to weeds which have only been controlled up to now with total 
herbicides. 
The mode of action of these compounds is unusual. Many are translocatable, 
i.e. they are absorbed by the plant and transported to other parts of it 
where they then exert their action. Thus, for example, it is possible to 
damage perennial weeds to the roots by surface treatment. Compared with 
other herbicides and growth regulators, the novel compounds of the formula 
I are effective even when used at very low rates of application. 
The compounds of formula I have in addition pronounced growth-regulating, 
especially growth-inhibiting, properties. The growth of both monocots and 
dicots is inhibited. Thus, for example, the compounds of formula I 
selectively inhibit the growth of leguminosae which are frequently planted 
as cover crops in tropical regions, so that, while soil erosion between 
cultivated plants is prevented, the cover crops cannot compete with the 
cultivated plants. 
Inhibition of the vegetative growth of many cultivated plants permits more 
plants to be sown in a crop area, so that a higher yield may be obtained 
per unit of area. A further mechanism of yield increase using growth 
regulators resides in the fact that nutrients are able increasingly to 
promote flower formation and fruiting, whilst vegetative growth is 
inhibited. 
At higher rates of application, all tested plants are so severely damaged 
in their development that they die. 
The invention also relates to herbicidal and growth-regulating compositions 
which contain a novel compound of the formula I, and also to methods of 
controlling weeds pre- and postemergence and of inhibiting the growth of 
monocots and dicots, especially grasses, tropical cover crops and tobacco 
plant suckers. 
The compounds of the formula I are used in unmodified form or, preferably, 
together with the adjuvants conventionally employed in the art of 
formulation, and are therefore formulated in known manner to emulsifiable 
concentrates, coatable pastes, directly sprayable or dilutable solutions, 
dilute emulsions, wettable powders, soluble powders, dusts, granulates, 
and also encapsulations in e.g. polymer substances. As with the nature of 
the compositions, the methods of applications, such as spraying, 
atomising, dusting, scattering or pouring, are chosen in accordance with 
the intended objectives and the prevailing circumstances. 
The formulations, i.e. the compositions containing the compound (active 
ingredient) of the formula I and, where appropriate, a solid or liquid 
adjuvant, are prepared in known manner, e.g. by homogeneously mixing 
and/or grinding the active ingredients with extenders, e.g. solvents, 
solid carriers and, where appropriate, surface-active compounds 
(surfactants). 
Suitable solvents are: aromatic hydrocarbons, preferably the fractions 
containing 8 to 12 carbon atoms, e.g. xylene mixtures or substituted 
naphthalenes, phthalates such as dibutyl phthalate or dioctyl phthalate, 
aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols and 
glycols and their ethers and esters, such as ethanol, ethylene glycol, 
ethylene glycol monomethyl or monoethyl ether, ketones such as 
cyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone, 
dimethylsulfoxide or dimethylformamide, as well as epoxidised vegetable 
oils such as epoxidised coconut oil or soybean oil; or water. 
The solid carriers used e.g. for dusts and dispersible powders are normally 
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, broken brick, sepiolite or bentonite; and 
suitable nonsorbent carriers are materials such as calcite or sand. In 
addition, a great number of pregranulated materials of inorganic or 
organic nature can be used, e.g. especially dolomite or pulverised plant 
residues. 
Depending on the nature of the compound of the formula I to be formulated, 
suitable surface-active compounds are nonionic, cationic and/or anionic 
surfactants having good emulsifying, dispersing and wetting properties. 
The term "surfactants" will also be understood as comprising mixtures of 
surfactants. 
Suitable anionic surfactants can be both water-soluble soaps and 
water-soluble synthetic surface-active compounds. 
Suitable soaps are the alkali metal salts, alkaline earth metal salts or 
unsubstituted or substituted ammonium salts or higher fatty acids 
(C.sub.10 -C.sub.22), e.g. the sodium or potassium salts of oleic or 
stearic acid, or of natural fatty acid mixtures which can be obtained e.g. 
from coconut oil or tallow oil. Mention may also be made of fatty acid 
methyltaurin salts. 
More frequently, however, so-called synthetic surfactants are used, 
especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole 
derivatives or alkylarylsulfonates. 
The fatty sulfonates or sulfates are usually in the form of alkali metal 
salts, alkaline earth metal salts or unsubstitued or substituted ammonium 
salts and contain a C.sub.8 -C.sub.22 alkyl radical which also includes 
the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of 
lignosulfonic acid, of dodecylsulfate or of a mixture of fatty alcohol 
sulfates obtained from natural fatty acids. These compounds also comprise 
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 one fatty acid radical 
containing 8 to 22 carbon atoms. Examples of alkylarylsulfonates are the 
sodium, calcium or triethylanolamine salts of dodecylbenzene sulfonic 
acid, dibutylnaphthalenesulfonic acid, or of a naphthalenesulfonic 
acid/formaldehyde condensation product. Also suitable are corresponding 
phosphates, e.g. salts of the phosphoric acid ester of an adduct of 
p-nonylphenol with 4 to 14 moles of ethylene oxide, or phospholipids. 
Non-ionic surfactants are preferably polyglycol ether derivatives of 
aliphatic or cycloaliphatic alcohols, or saturated or unsaturated fatty 
acids and alkylphenols, said derivatives containing 3 to 30 glycol ether 
groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 
6 to 18 carbon atoms in the alkyl moiety of the alkylphenols. 
Further suitable non-ionic surfactants are the water-soluble adducts of 
polyethylene oxide with polypropylene glycol, ethylenediamine propylene 
glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in 
the alkyl chain, which adducts contain 20 to 250 ethylene glycol ether 
groups and 10 to 100 propylene glycol ether groups. These compounds 
usually contain 1 to 5 ethylene glycol units per propylene glycol unit. 
Representative examples of non-ionic surfactants are 
nonylphenolpolyethoxyethanols, castor oil polyglycol ethers, 
polypropylene/polyethylene oxide adducts, 
tributylphenoxypolyethoxyethanol, polyethylene glycol and 
octylphenoxyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan 
and polyoxyethylene sorbitan trioleate are also suitable non-ionic 
surfactants. 
Cationic surfactants are preferably quaternary ammonium salts which 
contain, as N-substituent, at least one C.sub.8 -C.sub.22 alkyl radical 
and, as further substituents, lower unsubstituted or halogenated alkyl, 
benzyl or lower hydroxyalkyl radicals. The salts are preferably in the 
form of halides, methylsulfates or ethylsulfates, e.g. 
stearyltrimethylammonium chloride or benzyldi(2-chloroethyl)ethylammonium 
bromide. 
The surfactants customarily employed in the art of formulation are 
described e.g. in the following publications: 
"McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., 
Ridgewood, N.J., 1981; H. Stache, "Tensid-Taschenbuch", 2nd Edition, C. 
Hanser Verlag, Munich & Vienna, 1981; M. and J. Ash, "Encyclopedia of 
Surfactants", Vol. I-III, Chemical Publishing Co., New York, 1980-81. 
The pesticidal compositions usually contain 0.1 to 95%, preferably 0.1 to 
80%, of a compound of the formula I, 1 to 99.9%, of a solid or liquid 
adjuvant, and 0 to 25%, preferably 0.1 to 25%, of a surfactant. 
Preferred formulations are composed in particular of the following 
constituents (%=percentage by weight): 
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Emulsifiable concentrates 
active ingredient: 
1 to 20%, preferably 5 to 10% 
surfactant: 5 to 30%, preferably 10 to 20% 
liquid carrier: 
50 to 94%, preferably 70 to 85% 
Dusts 
active ingredient: 
0.1 to 10%, 
preferably 0.1 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 25%, preferably 90 to 30% 
surfactant: 1 to 40%, preferably 2 to 30% 
Wettable powders 
active ingredient: 
0.5 to 90%, 
preferably 1 to 80% 
surfactant: 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%. 
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Whereas commercial products will be preferably formulated as concentrates, 
the end user will normally employ dilute formulations. The formulations 
can be diluted to a concentration as low as 0.001% The rates of 
application are normally from 0.01 to 10 kg a.i./ha, preferably from 0.025 
to 5 kg a.i./ha. 
The compositions may also contain further ingredients such as stabilisers, 
antifoams, viscosity regulators, binders, tackifiers, as well as 
fertilisers and other compounds for obtaining special effects. 
The invention is illustrated by the following Examples.