Sulphonyl compounds, method of preparing the new compounds, as well as aphicidal compositions on the basis of the new compounds

The invention relates to new sulphonyl compounds of the general formula ##STR1## wherein X is a halogen atom, a phenoxy group, or an alkyl group or alkoxy group having 1-4 carbon atoms and substituted, if desired, with halogen; PA1 R.sub.1 is a cyano group, and PA1 R.sub.2 is an amino group which, if desired, may be substituted with halogen, with one or two alkenyl groups or alkynyl groups having 2-6 carbon atoms or with one or two alkyl groups having 1-6 carbon atoms, which alkyl groups, together with the nitrogen atom to which they are bound, may form a saturated heterocyclic ring, which ring may also contain a second hetero atom selected from the group consisting of nitrogen, oxygen and sulphur, or which alkyl groups may be substituted with an alkoxy group, having 1-4 carbon atoms, or with a dialkylamino group having 2-6 carbon atoms the alkyl groups of which, together with the nitrogen atom to which they are bound, may form a saturated heterocyclic ring; or wherein PA1 R.sub.1 and R.sub.2 together form a S,S-dialkylsulphoximido group the alkyl groups of which comprise 1-4 carbon atoms, or a 1-amino-2-azavinylene group, of which the amino group is substituted, if desired, with a cycloalkylcarbamoyl group having 4-8 carbon atoms, an alkylcarbamoyl group having 2-5 carbon atoms, a dialkylamino group the alkyl group of which comprise 1-4 carbon atoms, or an alkyl group having 1-4 carbon atoms which alkyl group may be substituted with a hydroxy group or one or more halogen atoms; or wherein PA1 R.sub.1 and R.sub.2 together form a 1-imino-2-azaethylene group of which the ring nitrogen is substituted with an alkyl group or alkenyl group having 1-4 carbon atoms, and of which the imino group may be substituted with a substituted or non-substituted phenylcarbamoyl group, having aphicidal activity. After having been processed to compositions, the compounds may be used for the control of aphids in agriculture, horticulture and forestry in a dosage from 20 to 5,000 g of active substance per hectare.

The invention relates to new sulphonyl compounds, and to a method of 
preparing the new compounds. The invention also relates to aphicidal 
compositions on the basis of the new compounds and to the use of these 
compositions for the control of aphids in agriculture, horticulture and 
forestry. 
Japanese Patent Application No. 73/24735 discloses 
benzo[d]isothiazole-1,1-dioxides having fungicidal activity, for example 
3-amino-benzo[d]isothiazole-1,1-dioxide. 
German Patent Application ("Offenlegungsschrift") No. 1670797 discloses 
benzoisothiazole-1,1-dioxides, e.g. 
3-dimethyl-amino-6-chlorobenzoisothiazole-1,1-dioxide, and a method of 
preparing the compounds; it is stated that the prepared compounds are 
intermediates for the preparation of dyes and pesticides. In neither 
patent application mention is made of an insecticidal or aphicidal 
activity of the prepared compounds. 
It has now been found that new sulphonyl compounds of the general formula 
##STR2## 
wherein X is a halogen atom, a phenoxy group, or an alkyl group or alkoxy 
group having 1-4 carbon atoms and substituted, if desired, with halogen; 
R.sub.1 is a cyano group, and 
R.sub.2 is an amino group which, if desired, may be substituted with 
halogen, with one or two alkenyl groups or alkynyl groups having 2-6 
carbon atoms or with one or two alkyl groups having 1-6 carbon atoms, 
which alkyl groups, together with the nitrogen atom to which they are 
bound, may form a saturated heterocyclic ring, which ring may also contain 
a second hetero atom selected from the group consisting of nitrogen, 
oxygen and sulphur, or which alkyl groups may be substituted with an 
alkoxy group having 1-4 carbon atoms or with a dialkylamino group having 
2-6 carbon atoms the alkyl groups of which, together with the nitrogen 
atom to which they are bound, may form a saturated heterocyclic ring; 
or wherein 
R.sub.1 and R.sub.2 together form a S,S-dialkylsulphoximido group the alkyl 
groups of which comprise 1-4 carbon atoms, or a 1-amino-2-azavinylene 
group, of which the amino group is substituted, if desired, with a 
cycloalkylcarbamoyl group having 4-8 carbon atoms, an alkylcarbamoyl group 
having 2-5 carbon atoms, a dialkylamino group the alkyl groups of which 
comprise 1-4 carbon atoms, or an alkyl group having 1-4 carbon atoms which 
alkyl group may be substituted with a hydroxy group or one or more halogen 
atoms; 
or wherein 
R.sub.1 and R.sub.2 together form a 1-imino-2-azaethylene group of which 
the ring nitrogen is substituted with an alkyl group or alkenyl group 
having 1-4 carbon atoms, and of which the imino group may be substituted 
with a substituted or non-substituted phenylcarbamoyl group, 
have an aphicidal activity. 
The sulphonyl compound known from the above German patent application shows 
not any aphicidal activity, even at a concentration of 300 ppm. Although 
the compound known as a fungicide from the above-mentioned Japanese patent 
application proves to have a slight aphicidal activity, said aphicidal 
activity is well surpassed by that of chemically related sulphonyl 
compounds according to the invention, as will become apparent from the 
results hereinafter. These results have been obtained by testing the 
compounds on Aphis fabae according to the method described in Example IX. 
______________________________________ 
##STR3## 
Activity against Aphis fabae 
Conc. in mg of act. 
subst. per 1. 
compound A B 300 100 30 10 3 1 
______________________________________ 
known as intermediate 
6-Cl CH.sub.3 
- 
from German pat. 
appln. 1670797 
known as fungicide 
H H + .+-. - 
from Jap. pat. 
appln. 73/24735 
according to 4-Cl H + + + + .+-. 
- 
the invention 
______________________________________ 
The meaning of the symbols is as 
+ = 90-100% mortality 
.+-. = 50-90% mortality 
- = &lt; 50% mortality. 
Of the above-mentioned aphicidal compounds prove to be most active 
compounds of the general formula 
##STR4## 
wherein X' is fluorine atom or a chlorine atom, and 
R'.sub.5 is a hydrogen atom, a 2-chloroethyl group, or a 
cyclohexylcarbamoyl group, and also compounds of the general formula 
##STR5## 
wherein X' has the above meaning, and 
R'.sub.3 and R'.sub.4 are equal or different and represent hydrogen atoms 
or alkyl groups having 1-4 carbon atoms, 
and also compounds of the general formula 
##STR6## 
wherein X' has the above meaning, and 
R'.sub.6 is a methyl group or ethyl group. 
Examples of very suitable aphicidal compounds are: 
(1) 3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide, 
(2) 3-(3-cyclohexylureido)-4-chlorobenzo[d]isothiazole-1,1-dioxide, 
(3) 3-amino-4-fluorobenzo[d]isothiazole-1,1-dioxide, 
(4) 3-(2-chloroethyl)amino-4-chlorobenzo[d]isothiazole-1,1-dioxide, 
(5) 2-cyano-3-chlorobenzenesulphonamide, 
(6) 2-cyano-3-chloro-N-isopropylbenzenesulphonamide, 
(7) 2-cyano-3-fluoro-N,N-diethylbenzenesulphonamide, 
(8) 2-cyano-3-fluoro-N-isopropylbenzenesulphonamide, 
(9) 2-cyano-3-fluorobenzenesulphonamide, 
(10) 2-cyano-3-fluoro-N,N-dimethylbenzenesulphonamide, 
(11) 2-methyl-3-imino-4-chlorobenzo[d]isothiazoline-1,1-dioxide, 
(12) 2-methyl-3-imino-4-fluorobenzo[d]isothiazoline-1,1-dioxide, and 
(13) 2-ethyl-3-imino-4-fluorobenzo[d]isothiazoline-1,1-dioxide. Of the 
above compounds appeared to be excellently effective compound no. (1). 
Examples of other new sulphonyl compounds having aphicidal activity 
according to the invention are: 
(14) 3-(3-methylureido)-4-chlorobenzo[d]isothiazole-1,1-dioxide, 
(15) 3-n-butylamino-4-chlorobenzo[d]isothiazole-1,1-dioxide, 
(16) 2-cyano-3-chloro-N,N-diallylbenzenesulphonamide, 
(17) 2-cyano-3-fluoro-N,N-diallylbenzenesulphonamide, 
(18) 2-cyano-3-fluoro-N-(3-methyl-1-butyn-3-yl)benzenesulphonamide, 
(19) 1-(2-cyano-3-fluorophenyl)sulphonylpiperidine, 
(20) 1-(2-cyano-3-fluorophenyl)sulphonylmorpholine, 
(21) 2-cyano-3-methyl-N,N-dimethylbenzenesulphonamide, 
(22) 2-cyano-3-methyl-N,N-diallylbenzenesulphonamide, 
(23) 2-allyl-3-imino-4-chlorobenzo[d]isothiazoline-1,1-dioxide, 
(24) 
2-methyl-3-N-(4-ethoxyphenylcarbamoyl)imino-4-chlorobenzo[d]isothiazoline- 
1,1-dioxide, 
(25) 2-cyano-3-fluoro-N,N-dichlorobenzenesulphonamide, 
(26) S,S-dimethyl-N-(2-cyano-3-fluorophenylsulphonyl)sulphoximide, 
(27) 1-(2-cyano-3-fluorophenyl)sulphonylpyrrolidine, 
(28) 2-cyano-5-trifluoromethoxy-N,N-dimethylbenzenesulphonamide, 
(29) 2-cyano-5-chloro-N,N-dimethylbenzenesulphonamide, 
(30) 2-cyano-3-chloro-N-(2-methoxyethyl)benzenesulphonamide, 
(31) 3-(1-hydroxybutyl-2)amino-4-chlorobenzo[d]isothiazole-1,1-dioxide, 
(32) 3-amino-4-methylbenzo[d]isothiazole-1,1-dioxide, 
(33) 3-amino-4-methoxybenzo[d]isothiazole-1,1-dioxide, 
(34) 3-N',N'-dimethylhydrazino-4-chlorobenzo[d]isothiazole-1,1-dioxide, 
(35) 3-amino-4-phenoxybenzo[d]isothiazole-1,1-dioxide, 
(36) 2-allyl-3-imino-4-fluorobenzo[d]isothiazoline-1,1-dioxide, and 
(37) 2-methyl-3-imino-4-methoxybenzo[d]isothiazoline-1,1-dioxide. 
The substances according to the invention may be used for the control of 
aphids in agriculture, horticulture and forestry. 
For practical application the substances according to the invention are 
usually processed to compositions. In such compositions the active 
substance is mixed with solid carrier material or is dissolved or 
dispersed in liquid carrier material, if desired in combination with 
auxiliary substances such as emulsifiers, wetting agents, dispersing 
agents and stabilizers. 
Examples of compositions according to the invention are aqueous solutions 
and dispersions, oily dispersions, solutions in organic solvents, pastes, 
dusting powders, dispersing powders, miscible oils, granules, pellets, 
invert emulsions, aerosol compositions and fumigating candles. 
Dispersible powders, pastes and miscible oils are compositions in 
concentrate form which are diluted prior to or during use. 
The invert emulsions and solutions in organic solvents are mainly used in 
air application, namely when large areas are treated with a comparatively 
small quantity of composition. The invert emulsion can be prepared shortly 
before or even during spraying in the spraying apparatus by emulsifying 
water in an oily solution or an oily dispersion of the active substance. 
The solutions of the active substance in organic solvents may be provided 
with a phytotoxicity-reducing substance, for example, wool fat, wool fatty 
acid or wool fatty alcohol. 
A few forms of composition will be described in greater detail hereinafter 
by way of example. 
Granular compositions are prepared by taking up, for example, the active 
substance in a solvent or dispersing it in a diluent and impregnating the 
resulting solution/suspension, if desired in the presence of a binder, on 
granular carrier material, for example porous granules (for example pumice 
and attaclay), mineral non-porous granules (sand or ground marlow), 
organic granules (for example, dried coffee grounds, cut tobacco stems or 
ground corncobs). A granular composition can also be prepared by 
compressing the active substance together with powdered minerals in the 
presence of lubricants and binders and disintegrating the compressed 
product to the desired grain size and sieving it. Granular compositions 
can be prepared in a different manner by mixing the active substance in 
powder form with powdered fillers, and glomulating the mixture then to the 
desired particle size. 
Dusting powders can be obtained by intimately mixing the active substance 
with an inert solid powdered carrier material, for example, talcum. 
Dispersible powders are prepared by mixing 10 to 80 parts by weight of a 
solid inert carrier, for example kaolin, dolomite, gypsum, chalk, 
bentonite, attaclay, colloidal SiO.sub.2 or mixtures of these and similar 
substances, with 10 to 80 parts by weight of the active substance, 1 to 5 
parts by weight of a dispersing agent, for example the lignine sulphonates 
or alkylnaphthalene sulphonates known for this purpose, preferably also 
0.5 to 5 parts by weight of a wetting agent, for example, fatty alcohol 
sulphates, alkyl aryl sulphonates, fatty acid condensation products, or 
polyoxyethylene compounds, and finally, if desired, other additives. 
For the preparation of miscible oils the active compound is dissolved in a 
suitable solvent which preferably is poorly water-miscible, and one or 
more emulsifiers are added to this solution; these miscible oils are also 
called emulsifyable concentrates. Suitable solvents are, for example, 
xylene, toluene, petroleum distillates which are rich in aromates, for 
example, solvent naphtha, distilled tar oil and mixtures of these liquids. 
As emulsifiers may be used, for example, polyoxyethyelene compounds and/or 
alkyl aryl sulphonates. The concentration of the active compound in these 
miscible oils is not restricted to narrow limits and may vary, for 
example, between 2 and 50% by weight. In addition to a miscible oil may 
also be mentioned as a liquid and highly concentrated primary composition 
a solution of the active substance in a readily water-miscible liquid, for 
example, a glycol, a glycol ether, dimethylformamide, or 
N-methylpyrrolidone, to which solution a dispersing agent and, if desired, 
a surface-active substance has been added. When diluting with water 
shortly before or during spraying, an aqueous dispersion of the active 
substance is then obtained. 
An aerosol composition according to the invention is obtained in the usual 
manner by incorporating the active substance, if desired in a solvent, in 
a volatile liquid to be used as a propellant, for example, a mixture of 
chlorine-fluorine derivatives of methane and ethane, a mixture of lower 
hydrocarbons, dimethyl ether, or gases such as carbon dioxide, nitrogen 
and nitrous oxide. 
Fumigating candles or fumigating powders, i.e. compositions which, while 
burning, can generate a pesticidal smoke, are obtained by taking up the 
active substance in a combustible mixture which may contain as a fuel a 
sugar or a wood, preferably in a ground form, a substance to maintain 
combustion, for example, ammonium nitrate or potassium chlorate, and 
furthermore a substance to delay combustion, for example, kaolin, 
bentonite and/or colloidal silicic acid. 
In addition to the above-mentioned ingredients, the agents according to the 
invention may also contain other substances known for use in this type of 
agents. For example, a lubricant, for example, calcium stearate or 
magnesium stearate, may be added to a dispersible powder or a mixture to 
be granulated. "Adhesives", for example, polyvinylalcohol, cellulose 
derivatives or other colloidal materials, such as casein, may also be 
added so as to improve the adhesion of the pesticide to the crop. 
Furthermore, a substance may be added to reduce the phytotoxicity of the 
active substance, carrier material or auxiliary substance, for example, 
wool fat or wool fatty alcohol. 
Pesticidal compounds known per se may also be incorporated in the 
compositions according to the invention. As a result of this the activity 
spectrum of the composition is widened and synergism may occur. 
For use in such a combination composition are to be considered the 
following known insecticidal, acaricidal and fungicidal compounds. 
Insecticides, for example 
1. organic chlorine compounds, for example 
6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzo[e 
]-dioxathiepine-3-oxide; 
2. carbamates, for example: 2-dimethylamino-5,6-dimethylpyrimidin-4-yl 
dimethyl carbamate and 2-isopropoxyphenyl methyl-carbamate; 
3. di(m)ethylphosphates, for example, 
2-chloro-2-diethylcarbamoyl-1-methylvinyl-, 
2-methoxycarbonyl-1-methylvinyl-, 2-chloro-1-(2,4-dichlorophenyl)vinyl-, 
and 2-chloro-1(2,4,5-trichlorophenyl)vinyl di(m)ethyl phosphate; 
4. O,O-di(m)ethyl phosphorothioates, for example, O(S)-2-methylthioethyl-, 
S-2-ethylsulphinylethyl-, S-2-(1-methylcarbamoylethylthio)ethyl-, 
O-4-bromo-2,5-dichlorophenyl-, O-3,5,6-trichloro-2-pyridyl-, 
O-2-isopropyl-6-methylpyrimidin-4-yl-, and O-4-nitrophenyl O,O-di(m)ethyl 
phosphorothioate; 
5. O,O-di(m)ethyl phosphorodithioates, for example, 
S-methylcarbamoylmethyl-, S-2-ethylthioethyl-, 
S-(3,4-dihydro-4-oxobenzo[d]-1,2,3-triazin-3-ylmethyl-, 
S-1,2-di(ethoxycarbonyl)ethyl-, S-6-chloro-2-oxobenzoxazolin-3-ylmethyl-, 
and S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl 
O,O-di(m)ethyl phosphorodithioate; 
6. phosphonates, for example, dimethyl 
2,2,2-trichloro-1-hydroxyethylphosphonate; 
7. benzoylurea, for example, 
N-(2,6-difluorobenzoyl)-N'-(4-chlorophenyl)urea; 
8. natural and synthetic pyrethroids; 
9. amidines, for example, 
N'-(2-methyl-4-chlorophenyl)-N,N-dimethylformamidine; and 
10. microbial insecticides, such as Bacillus thuringiensis. 
Acaricides, for example 
1. organic tin compounds, for example, tricyclohexyl tin hydroxide and 
di[tri-(2-methyl-2-phenylpropyl)tin]oxide; 
2. organic halogen compounds, for example isopropyl 4,4'-dibromobenzilate, 
2,2,2-trichloro-1,1-di(4-chlorophenyl)ethanol and 
2,4,5,4'-tetrachlorodiphenyl sulphone; 
and furthermore: 3-chloro-.alpha.-ethoxyimino-2,6-dimethoxybenzyl benzoate 
and O,O-dimethyl S-methylcarbamoyl methyl phosphorothioate. 
Fungicides, for example 
1. organic tin compounds, for example, triphenyl tin hydroxide and 
triphenyl tin acetate; 
2. alkylene bisdithiocarbamates, for example, zinc 
ethylenebisdithiocarbamate and manganese ethylene bisdithiocarbamate; 3. 
1-acyl- or 1-carbamoyl-N-benzimidazole (-2) carbamates and 1,2-bis 
(3-alkoxycarbonyl-2-thiureido)benzene, and furthermore 
2,4-dinitro-6-(2-octylphenylcronotae), 
1-[bis(dimethylamino)phosphoryl]-3-phenyl-5-amino-1,2,4-triazole, 
N-trichloromethylthiophthalimide, 
N-trichloromethylthiotetrahydrophthalimide, 
N-(1,1,2,2-tetrachloroethylthio)-tetrahydrophthalimide, 
N-dichlorofluoromethylthio-N-phenyl-N,N'-dimethylsulphamide, 
tetrachloroisophthalonitrile, 2-(4'-thiazolyl)-benzimidazole, 
5-butyl-2-ethylamino-6-methylpyrimidine-4-yl-dimethylsulphamate, 
1-(4-chlorophenoxy)-3,3-dimethyl-1(1,2,4-triazole-1-yl)-2-butanone, 
.alpha.-(2-chlorophenyl)-.alpha.-(4-chlorophenyl)-5-pyrimidinemethanol, 
1-(isopropylcarbamoyl)-3-(3,5-dichlorophenyl)hydantoin, 
N-(1,1,2,2-tetrachloroethylthio)-4-cyclohexene-1,2-carboximide, 
N-trichloromethylmercapto-4-cyclohexene-1,2-dicarboximide, and 
N-tridecyl-2,6-dimethylmorpholine. 
The dosage of the composition according to the invention desired for 
practical applications will, of course, depend on various factors, for 
example, field of application, selected active substance, form of 
composition, nature and extent of the infection and the weather 
conditions. 
In general it holds that favourable results are obtained with a dosage 
which corresponds to 20 to 5,000 g of the active substance per hectare, 
preferably 100 to 500 g per hectare. 
As a particular aspect of the invention it was found that the compositions 
according to the invention have a considerably stronger aphicidal activity 
when, in addition to the above-mentioned ingredients, they contain one or 
more of the following substances: an aliphatic or naphtenic mineral oil, a 
vegetable oil, a glycol ether, an alkylated benzene, a polyoxyethylene 
compound, urea, a polymeric resin compound, and a surfactant such as a 
polyoxyethylene sorbitan ester, a fatty acid polyglycol ester, an 
alkylated phenol polyoxyethylene, a polyoxyethylene alkyl ether or a 
quaternary ammonium compound. 
As examples of additives suitable for this purpose may be mentioned the 
substances described in Example XIV. The additives to be used may, of 
course, cause no or at least no noticeable phytotoxicity. A small 
phytotoxicity of the additive need not be a drawback provided the 
composition also comprises a small quantity of a phytotoxicity-reducing 
substance, for example, wool fat, wool fatty alcohol, wool fatty acid or 
an ester of wool fatty alcohol or wool fatty acid. The quantity of the 
additive may vary within wide limits dependent on the application, and 
usually is between 10 and 10,000 ml per hectare. 
The compounds according to the invention are new substances which can be 
prepared in a manner known per se for the synthesis of related compounds. 
For example, compounds of the general formula 
##STR7## 
wherein X has the above meaning, and 
R.sub.3 and R.sub.4 are equal or different and represent hydrogen atoms, 
halogen atoms, alkenyl groups or alkynyl groups having 2-6 carbon atoms, 
alkyl groups having 1-6 carbon atoms, which alkyl groups may be 
substituted with an alkoxy group having 1-4 carbon atoms or with a 
dialkylamino group having 2-6 carbon atoms the alkyl groups of which, 
together with the nitrogen atom to which they are bound, may form a 
saturated heterocyclic ring, 
or wherein 
R.sub.3 and R.sub.4 together with the nitrogen atom to which they are 
bound, form a S,S-dialkylsulphoximido group the alkyl groups of which 
comprise 1-4 carbon atoms, or a saturated heterocyclic ring, which ring 
may comprise in addition a second hetero atom selected from the group 
consisting of nitrogen, oxygen and sulphur, 
can be prepared by reacting a compound of the general formula 
##STR8## 
with an amine of the general formula 
##STR9## 
In this reaction the starting amine is present in an at least bimolar 
quantity calculated on the acid chloride, so as to bind the HCl formed. 
The reaction is preferably carried out in a polar organic solvent which is 
inert with respect to the reaction components, for example an alcohol (for 
example, ethanol), an ether (for example, diethyl ether), dimethyl 
formamide, acetonitrile, or water (provided the acid chloride used is 
sufficiently resistent to hydrolysis under the reaction conditions used), 
or in a mixture of these solvents. The reaction is carried out at a 
temperature between 0.degree. C. and the boiling point of the solvent, 
preferably at a temperature between 0.degree. C. and room temperature. 
When ammonia or a primary amine is used as an amine, a reaction 
temperature of approx. 0.degree. C. is desired to reduce the possibility 
of undesired subsequent reactions. 
After the above reaction the compound obtained having the general formula 
##STR10## 
if desired, if R.sub.3 and R.sub.4 both represent hydrogen atoms, may be 
reacted with a hypochlorite of hypobromite to produce a compound in which 
R.sub.3 and R.sub.4 both are chlorine or bromine atoms, which compound, if 
desired, after conversion into the N-mono-alkalimetal derivative is 
reacted with a dialkylsulphoxide, the alkyl groups of which comprise 1-4 
carbon atoms, to produce a compound of the last formula, wherein R.sub.3 
and R.sub.4 together with the nitrogen atom to which they are bound form a 
S,S-dialkylsulphoximido group. The reaction with a hypochlorite or 
hypobromite, preferably an alkalimetal hypochlorite or hypobromite, e.g. 
sodium hypochlorite or hypobromite, is carried out in water or in a 
mixture of water and a water-miscible solvent, at a temperature between 
0.degree. C. and 100.degree. C. or the boiling point of the solvent, 
preferably at room temperature. The conversion into the N-mono-alkalimetal 
derivative, e.g. the sodium compound, is effected with an aqueous 
alkalimetalhydroxide solution at a temperature between room temperature 
and 100.degree. C. The reaction with a dialkylsulphoxide, e.g. 
dimethylsulphoxide, is carried out at a reaction temperature between room 
temperature and the boiling point of the solvent. Generally the 
dialkylsulphoxide used as a reactant, is also used as the solvent. The 
reaction can be catalyzed by a suitable catalyst, e.g. CuCl.sub.2. 
Compounds of the general formula 
##STR11## 
wherein X has the above meaning, and 
R.sub.5 is a hydrogen atom, a cycloalkylcarbamoyl group having 4-8 carbon 
atoms, an alkylcarbamoyl group having 2-5 carbon atoms, a dialkylamino 
group the alkyl groups of which comprise 1-4 carbon atoms, or an alkyl 
group having 1-4 carbon atoms which alkyl group may be substituted with a 
hydroxy group or one or more halogen atoms, can be prepared in two 
manners, namely 
(a) by reacting a compound of the general formula 
##STR12## 
with NH.sub.3, after which the resulting product of the general formula 
##STR13## 
is reacted, if desired, with a cycloalkylisocyanate having 4-8 carbon 
atoms, an alkylisocyanate having 2-5 carbon atoms, a N,N-dialkylhydrazine 
the alkyl groups of which comprise 1-4 carbon atoms, or an alkylamine the 
alkyl group of which has 1-4 carbon atoms and may be substituted with a 
hydroxy group or one or more halogen atoms, or 
(b) by reacting a compound of the general formula 
##STR14## 
wherein Hal is a halogen atom, with an amine of the general formula 
EQU R.sub.5 --NH.sub.2 
The reaction with NH.sub.3 mentioned in sub (a) is preferably carried out 
in a polar organic solvent, for example an ether (for example, diethyl 
ether or dioxane), an alcohol (for example, ethanol), dimethylformamide, 
acetonitrile or water, or in a mixture of a polar organic solvent in 
water, at room temperature or elevated temperature, for example, at the 
boiling point of the solvent used. The subsequent reaction with an amine 
or hydrazine described sub (a) is preferably carried out under the same 
reaction conditions. The subsequent reaction with isocyanate described sub 
(a) is preferably carried out in a polar organic solvent, for example, 
acetonitrile or an ether, for example, diethyl ether, in the presence of a 
strong organic base, for example, triethylamine, at a reaction temperature 
between 0.degree. C. and the boiling point of the solvent used. The 
reaction described sub (b) is preferably carried out in a polar organic 
solvent, for example, acetonitrile, dimethylformamide, an ether (for 
example, diethyl ether), an alcohol (for example, ether alcohol), or 
water, or in a mixture of these solvents, at a reaction temperature 
between 0.degree. C. and room temperature, preferably at approx. 0.degree. 
C. 
Compounds of the general formula 
##STR15## 
wherein X" is a phenoxy group or an alkoxy group having 1-4 carbon atoms 
and substituted, if desired, with halogen, and 
wherein 
R.sub.5 has the above meaning, may also be prepared by reacting a compound 
of the general formula 
##STR16## 
with phenol or an alcohol having 1-4 carbon atoms and substituted if 
desired, with halogen. This reaction is carried out in the presence of a 
suitable base, e.g. an alkalimetalphenoxide or -alkoxide, in an inert 
organic solvent, e.g. an alcohol or acetonitrile, at a reaction 
temperature between 0.degree. C. and the boiling point of the solvent 
used, preferably at an elevated temperature. 
Compounds of the general formula 
##STR17## 
Wherein X has the above meaning, 
R.sub.6 is an alkyl group or an alkenyl group having 1-4 carbon atoms, and 
R.sub.7 is a hydrogen atom or a substituted or non-substituted 
phenylcarbamoyl group, 
can be prepared by reacting a compound of the general formula 
##STR18## 
with an amine of the general formula 
EQU R.sub.6 NH.sub.2 
after which the resulting product of the general formula 
##STR19## 
is reacted, if desired, with a substituted or non-substituted 
phenylisocyanate, in which a product is obtained in which R.sub.7 is a 
substituted or non-substituted phenylcarbamoyl group; a halogen atom, an 
alkyl group having 1-4 carbon atoms, and an alkoxy group having 1-4 carbon 
atoms may be mentioned as suitable substituents for the phenylcarbamoyl 
group. The reaction with the amine is preferably carried out in a polar 
organic solvent, for example, an ether (for example, diethyl ether or 
dioxane), an alcohol (for example, ethyl alcohol), dimethylformamide, 
acetonitrile, or water (provided the acid chloride used is sufficiently 
resistent to hydrolysis under the reaction conditions used), or in a 
mixture of these solvents. The reaction is carried out at a temperature 
between 0.degree. C. and the boiling point of the solvent used, preferably 
at a temperature between 0.degree. C. and room temperature. The subsequent 
reaction with isocyanate described is preferably carried out in a polar 
organic solvent, for example, acetonitrile or an ether, for example, 
diethyl ether, at a reaction temperature between 0.degree. C. and the 
boiling point of the solvent, preferably at room temperature, if desired 
under the influence of a base, for example, triethyl amine or sodium 
hydride.

The invention will now be described in greater detail with reference to the 
following specific examples. 
EXAMPLE I 
Preparation of 2-cyano-3-fluoro-N-isopropylbenzenesulphonamide 
To a solution of 5.2 ml of isopropylamine in 50 ml of diethyl ether cooled 
in an ice bath, a solution of 4.4 g of 
2-cyano-3-fluorobenzenesulphonylchloride in 50 ml of diethylether was 
added dropwise while stirring; reaction temperature approx. 5.degree. C. 
After leaving to stand at room temperature for one hour, the reaction 
mixture was washed twice with ice water, dried on anhydrous Na.sub.2 
SO.sub.4, filtered and evaporated to dryness. The desired product was 
obtained in a yield of 4.16 g; melting-point 97.degree.-105.degree. C. 
The following compounds were prepared in a corresponding manner in which, 
if desired, ethanol or water was used as a solvent: 
2-cyano-3-chlorobenzenesulphonamide, m.p. 184.degree.-189.degree. C.; 
2-cyano-3-chloro-N-isopropylbenzenesulphonamide, m.p. 78.degree.-82.degree. 
C.; 
2-cyano-3-fluorobenzenesulphonamide, m.p. 163.degree. C.; 
2-cyano-3-chloro-N,N-diallylbenzenesulphonamide, m.p. 60.degree. C.; 
2-cyano-3-fluoro-N,N-diallylbenzenesulphonamide, m.p. 76.degree.-78.degree. 
C.; 
2-cyano-3-fluoro-N,N-dimethylbenzenesulphonamide, m.p. 
86.degree.-89.degree. C.; 
2-cyano-3-fluoro-N-(3-methyl-1-butyn-3-yl)benzenesulphonamide, m.p. 
118.5.degree.-120.degree. C.; 
1-(2-cyano-3-fluorophenyl)sulphonylpiperidine, m.p. 99.degree.-101.degree. 
C.; 
1-(2-cyano-3-fluorophenyl)sulphonylmorpholine, m.p. 
136.5.degree.-138.degree. C.; 
2-cyano-3-methyl-N,N-dimethylbenzenesulphonamide, m.p. 
74.degree.-77.degree. C.; 
2-cyano-3-methyl-N,N-diallylbenzenesulphonamide, m.p. 70.degree.-72.degree. 
C.; 
2-cyano-3-fluoro-N,N-diethylbenzenesulphonamide, m.p. 85.degree.-88.degree. 
C.; 
1-(2-cyano-3-fluorophenyl)sulphonylpyrrolidine, m.p. 96.degree. C.; 
2-cyano-5-trifluoromethoxy-N,N-dimethylbenzenesulphonamide, m.p. 
100.degree. C.; 
2-cyano-5-chloro-N,N-dimethylbenzenesulphonamide, m.p. 97.degree. C.; 
and 2-cyano-3-chloro-N-(2-methoxyethyl)benzenesulphonamide, m.p. 98.degree. 
C. 
EXAMPLE II 
Preparation of 2-cyano-3-fluoro-N,N-dichlorobenzenesulphonamide and 
S,S-dimethyl-N-(2-cyano-3-fluorophenylsulphonyl)sulphoximide. 
(a) 7.55 g of 2-cyano-3-fluorobenzenesulphonamide, prepared according to 
Example I, was added at room temperature to 90 ml of a 10% aqueous 
solution of NaOCl; the temperature rose from 22.degree. C. to 24.degree. 
C. After stirring at room temperature during 11/2 hour the reaction 
mixture was cooled in an ice bath and 16 ml of 96% acetic acid was added 
at approx. 10.degree. C. After 10 minutes the solid was sucked off, washed 
three times with water and dried in vacuo over P.sub.2 O.sub.5. 
2-Cyano-3-fluoro-N,N-dichlorobenzenesulphonamide was obtained in a yield 
of 6.15 g; m.p. 149.degree.-152.degree. C. 
(b) 5.4 g of 2-cyano-3-fluoro-N,N-dichlorobenzenesulphonamide was added in 
portions to 45 ml of 2 N sodiumhydroxide at 80.degree. C. while stirring; 
the temperature rose to 90.degree. C. After filtering the filtrate was 
cooled in a bath containing a mixture of ice and methanol to -10.degree. 
C. The 2-cyano-3-fluoro-N-chloro-N-sodiumbenzenesulphonamide obtained was 
sucked off, washed successively twice with a cold saturated NaCl solution 
and three times with isopropanol, and dried; yield 1.06 g. 1.0 g of 
2-cyano-3-fluoro-N-chloro-N-sodiumbenzenesulphonamide was added to a 
suspension of 0.1 g CuCl.sub.2 in 5 ml of dimethyl sulphoxide. After 
stirring at room temperature during 1 hour and subsequently heating on a 
steam bath during 1 hour the reaction mixture was poured into a mixture of 
30 ml water and 4 ml of a saturated solution of EDTA-Na.sub.2.2H.sub.2 O 
in water. After stirring for a short moment the solid was sucked off, 
washed three times with water and dried in vacuo over P.sub.2 O.sub.5, to 
yield 0,50 g of 
S,S-dimethyl-N-(2-cyano-3-fluorophenylsulphonyl)sulphoximide; m.p. 
184.degree. C. 
EXAMPLE III 
Preparation of 3-amino-4-chloro-benzo[d]isothiazole-1,1-dioxide. 
12.5 ml of 25% ammonia were added at approx. 60.degree. C. to a solution of 
11,8 g of 2-cyano-3-chlorobenzenesulphonylchloride in 20 ml of dioxane. 
After heating on a steam bath for 30 minutes the reaction mixture was 
cooled and diluted with water. The resulting crystalline product was 
sucked off, washed with water and dried. The desired product was obtained 
in a yield of 8.9 g. After recrystallization from ethanol, the product 
melted at 261.degree.-263.degree. C. 
The following compounds were prepared in a corresponding manner: 
3-amino-4-fluorobenzo[d]isothiazole-1,1-dioxide, m.p.&gt;260.degree. C.; 
3-amino-4-methylbenzo[d]isothiazole-1,1-dioxide, m.p. 265.degree. C.; 
3-amino-4-methoxybenzo[d]isothiazole-1,1-dioxide, m.p. 270.degree. C.; 
and 3-amino-4-phenoxybenzo[d]isothiazole-1,1-dioxide, m.p. 216.degree. C. 
The same products could also be prepared by leading gaseous ammonia through 
a solution of the sulphonyl chloride in dioxane, or by combining the 
sulphonyl chloride and ammonia in ice water and then causing it to react 
at room temperature. 
3-Amino-4-methoxybenzo[d]isothiazole-1,1-dioxide and 
3-amino-4-phenoxybenzo[d]isothiazole-1,1-dioxide could also be prepared by 
reacting 3-amino-4-fluorobenzo[d]isothiazole-1,1-dioxide with methanol and 
phenol respectively under the influence of a suitable base, e.g. a 
sodiumalkoxide or sodiumphenoxide, in an inert organic solvent, viz. 
acetonitrile, under reflux. 
EXAMPLE IV 
Preparation of 3-n-butylamino-4-chlorobenzo[d]isothiazole-1,1-dioxide. 
A solution of 2.17 g of the 3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide 
prepared according to Example II and 2 ml of n-butylamine in 15 ml of 
dioxane was boiled for approx. 2 hours, ammonia escaping. After distilling 
off the solvent, the residue was stirred with water, sucked off, washed 
successively with water and petroleum ether and dried. The desired product 
was obtained in a yield of 2.4 g, melting-point 136.degree.-138.degree. C. 
In a corresponding manner the following compounds were prepared: 
3-(2-chloroethyl)amino-4-chlorobenzo[d]isothiazole-1,1-dioxide m.p. 
184.degree.-185.degree. C.; and 
3-(1-hydroxybutyl-2)amino-4-chlorobenzo[d]isothiazole-1,1-dioxide, m.p. 
149.degree. C. 
EXAMPLE V 
Preparation of 
3-(3-cyclohexylureido)-4-chlorobenzo[d]isothiazole-1,1-dioxide. 
A solution of 2.17 g of the 3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide 
prepared according to Example II, 1.3 g of cyclohexylisocyanate and 0.3 ml 
of triethylamine in 20 ml of acetonitrile was refluxed for 4 hours. After 
cooling the bright solution, the desired product crystallized in a yield 
of 2.1 g; melting-point (decomposition) 192.degree. C. 
In a corresponding manner 
3-(3-methylureido)-4-chlorobenzo[d]isothiazole-1,1-dioxide was prepared; 
melting-point 182.degree. C. 
EXAMPLE VI 
Preparation of 3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide 
4.72 g of 3,4-dichlorobenzo[d]isothiazole-1,1-dioxide were added to 15 ml 
of 25% ammonia in 15 ml of ice water. After stirring at room temperature 
for two hours, the desired product was sucked off and dried; yield 4.20 g; 
melting-point 260.degree. C. 
In a corresponding manner 
3-N',N'-dimethylhydrazino-4-chlorobenzo[d]isothiazole-1,1-dioxide, m.p. 
218.degree. C., was prepared. 
EXAMPLE VII 
Preparation of 2-methyl-3-imino-4-chlorobenzo[d]isothiazoline-1,1-dioxide. 
7.1 g of 2-cyano-3-chlorobenzenesulphonylchloride were added to a solution 
of 9 ml of methylamine in approx. 15 ml of water cooled at 0.degree. C. 
After stirring at 0.degree.-10.degree. C. for 1 hour, the solid was sucked 
off, washed with water and dried in air. The desired product was obtained 
in a yield of 5,5 g; melting-point 140.degree.-142.degree. C. 
In a corresponding manner the following compounds were prepared: 
2-allyl-3-imino-4-chlorobenzo[d]isothiazoline-1,1-dioxide, m.p. 
92,5.degree.-95.degree. C.; 
2-methyl-3-imino-4-fluorobenzo[d]isothiazoline-1,1-dioxide, m.p. 
142.degree. C.; 
2-allyl-3-imino-4-fluorobenzo[d]isothiazoline-1,1-dioxide, m.p. 101.degree. 
C.; 
2-methyl-3-imino-4-methoxybenzo[d]isothiazoline-1,1-dioxide, m.p. 
138.degree. C.; 
and 2-ethyl-3-imino-4-fluorobenzo[d]isothiazoline-1,1-dioxide, m.p. 
110.degree. C. 
EXAMPLE VIII 
Preparation of 
2-methyl-3-N-(4-ethoxyphenylcarbamoyl)imino-4-chlorobenzo[d]isothiazoline- 
1,1-dioxide. 
2.3 g of 2-methyl-3-imino-4-chlorobenzo[d]isothiazoline-1,1-dioxide were 
dissolved in 15 ml of acetonitrile, 1.6 ml of 4-ethoxyphenylisocyanate 
were added to this bright solution, after which the reaction mixture was 
left to stand overnight at room temperature. After evaporating the solvent 
under reduced pressure at 30.degree. C., the residue was suspended in 
ether. After sucking off, the desired product was obtained in a yield of 
1.0 g; melting-point 147.degree.-154.degree. C. 
EXAMPLE IX 
The compounds according to the invention were processed to compositions by 
suspending the compounds in water in the presence of a dispersing agent, 
such as lignine sulphonate, and/or a wetting agent, such as 
alkylnaphthalene sulphonate, an alkyl sulphate, an alkylbenzenesulphonate, 
an alkylpolyoxyethylene or an alkylarylpolyoxyethylene. A typical 
formulation comprises 25% by weight of active substance, 2% by weight of 
an alkyl naphthalene sulphonate, 5% by weight of a lignine sulphonate, and 
68% by weight of kaolin. Young broad bean plants, approx. 10 cm high, were 
headed on two pair of leaves and then sprayed with the composition thus 
obtained in various concentrations. After the plants had dried up, they 
were infected with Aphis fabae (black bean aphids) by placing 10 aphids on 
each plant. The plants were then stored in a climate cell at a temperature 
of 20.degree./15.degree. C., a light-dark cycle of 18/6 hours being 
maintained; relative humidity 65/70%. After 7 days the mortality of the 
aphids was established. Each experiment was carried out in quadruplicate. 
The results are recorded in the Table A below. The meanings of the symbols 
recorded in the table are as follows: 
+=90-100% mortality 
.+-.=50-90% mortality 
-=&lt;50% mortality. 
TABLE A 
______________________________________ 
Activity against Aphis fabae 
conc. in mg active substance per liter 
compound no. 
300 100 30 10 3 1 
______________________________________ 
blank - 
(1) + + + + .+-. 
- 
(2) + + + .+-. - 
(3) + + + - 
(4) + + + .+-. - 
(5) + + + .+-. - 
(6) + + + .+-. - 
(7) + + + .+-. - 
(8) + + + .+-. - 
(9) .+-. .+-. .+-. 
.+-. - 
(10) .+-. .+-. .+-. 
.+-. - 
(11) + + .+-. 
.+-. - 
(12) + + + - 
(13) + + + .+-. - 
(14) + + - 
(15) + + .+-. 
- 
(16) + + .+-. 
- 
(17) + .+-. .+-. 
- 
(18) + + .+-. 
- 
(19) .+-. .+-. .+-. 
- 
(20) + + .+-. 
- 
(21) + + .+-. 
- 
(22) + + .+-. 
- 
(23) + .+-. .+-. 
- 
(24) + + - 
(25) + + + 
(26) + + - 
(27) + + .+-. 
- 
(28) + 
(29) + 
(30) + 
(31) + + - 
(32) + + .+-. 
- 
(33) + 
(34) + 
(35) + 
(36) + + .+-. 
- 
(37) + 
______________________________________ 
EXAMPLE X 
Young broad bean plants of 15-20 cm high in plastic pots of approx. 12 cm 
diameter were headed on 3 fully developed leaves. The plants were then 
infected with Aphis fabae by placing pieces of broad bean plants fully 
infected with Aphis fabae on the leaves of the test plants. The aphids 
then move from the wilting infection material to the fresh test plants. 
After 24 hours, first the wilted stems were removed, after which the test 
plants were sprayed from below and from the top with the compositions 
obtained according to Example IX in various concentrations. After 6 days 
in the glasshouse at 20.degree.-24.degree. C. the mortality of the aphids 
was established. 
Three broad bean plants were used for each test. The average results are 
recorded in Table B below, in which the mortality percentage shown in 
corrected for the mortality of the aphids on untreated broad bean plants. 
TABLE B 
______________________________________ 
Activity against Aphis fabae (% mortality) 
conc. in mg of act. substance per liter 
compound no. 
100 30 10 3 1 
______________________________________ 
(1) 100 97 47 
(5) 100 91 13 0 
(6) 100 92 13 
(7) 100 85 10 
(10) 98 48 4 
(11) 100 84 10 
(16) 86 32 0 
(17) 93 16 0 
(18) 96 27 0 
(19) 100 78 2 
(21) 100 65 10 
______________________________________ 
EXAMPLE XI 
Young broad bean plants, 15-20 cm high in plastic pots of approx. 12 cm 
diameter were headed and then infected as described in Example X. After 
the infection the plants were sprayed with a composition obtained 
according to Example VIII which contained 
3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide (comp. No. 1) in various 
concentrations (three plants per concentration). The pots were placed in 
the open air and the mortality of the aphids was established after 3 and 7 
days. The results are recorded in Table C, in which the mortality 
percentage is corrected for the mortality of aphids on untreated broad 
bean plants. 
TABLE C 
______________________________________ 
Activity against Aphis fabae (% mortality) 
Number of days conc. in mg of act. substance per liter 
after spraying 100 30 10 3 
______________________________________ 
3 95 0 0 0 
7 100 95 70 0 
______________________________________ 
EXAMPLE XII 
The systemic activity of 3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide 
(compound no. 1) was determined as follows. Young broad bean plants of 
15-20 cm high, placed in pots of approx. 12 cm diameter (soil area per pot 
approx. 100 cm.sup.2), were treated in the glasshouse as follows. The soil 
in each pot was watered with 50 ml of water, to which a given quantity of 
the compound to be tested had been added. After infecting the plants as 
described in Example X, in which, however, the heading operation of the 
plants was omitted, the aphicidal activity of the active substance 
absorbed via the roots was established by evaluating the mortality 
percentage of the aphids 6 days after the infection: Table D (the results 
are corrected for the mortality on the untreated plants). As appears from 
Table D. an interesting residual activity was found when the infection was 
delayed to 5 and 7 weeks, respectively, after the treatment with the 
aphicidal composition. 
TABLE D 
______________________________________ 
Activity against Aphis fabae (% mortality) 
Number of weeks between 
dosage in mg of act. subst. per liter 
treatment and infection 
10 3 1 0.3 
______________________________________ 
0 100 96 80 20 
5 99 82 
7 92 20 
______________________________________ 
The found systemic activity was deemed of great importance by those skilled 
in the art. 
EXAMPLE XIII 
3-Amino-4-chlorobenzo[d]isothiazole-1,1-dioxide (comp. no. 1) was tested in 
small field trials against Aphis fabae on broad beans by bringing the 
compositions in the top layer of the soil; the active substance was used 
in the form of a suspension as described in Example IX. Six days after the 
infection the plants were evaluated, in which the corrected mortality 
percentages recorded in Table E were obtained (results are corrected for 
the mortality on the untreated plants). As appears from the Table, the 
infection could be delayed without objection to at least 7 weeks after the 
treatment. 
TABLE E 
______________________________________ 
Activity against Aphis fabae (% mortality) 
Dosage in mg of 
act. substance 
Number of weeks between treatm. and inf. 
per 0.25 m.sup.2 
0 1 2 3 4 5 6 7 
______________________________________ 
2000 90 98 100 98 100 100 100 100 
1000 87 90 100 90 100 96 93 100 
500 90 90 100 100 100 97 99 99 
______________________________________ 
EXAMPLE XIV 
The effect of the addition of mineral oils like the aliphatic hydrocarbon 
Sunoil 7 N (a) and the naphthenic hydrocarbon Sunoil 91 N (b), of a 
vegetable oil like a cotton seed oil (c), of a glycolether like trioxitol 
(d), of an alkylbenzene like Dobane (e), of a polyoxyethylene sorbitan 
ester, like the polyoxyethylene sorbitan mono-oleate Tween 80 (f), the 
polyoxyethylene sorbitan monolaurate Tween 21 (v) and the polyoxyethylene 
sorbitan monolaurate Tween 22 (w), of a fatty acid polyglycolester like 
Emulsogen EL (g), of alkylated phenol polyoxyethylene compounds like the 
isooctylphenol polyoxyethylene Citowett (h), the nonylphenyl 
polyoxyethylene Agral LN (i), Arkopal N 060 (j), Arkopal N 090 (k), 
Arkopal N 130 (1) and Arkopal N 150 (m), the tributylphenol 
polyoxyethylene Sapogenat T 060 (n) and Sapogenat T 180 (o), of a 
polyoxyethylene alkyl ether like the polyoxyethylene laurylether Brij 30 
(p), of a polyethylglycol compound like Carbowax 600 (q), of ureum (r), of 
a quaternary ammonium compound like Aliquat 221 (s), of a mixture of a 
mineral oil and surfactant like Atplus 411 F (t), and of a polymeric resin 
with coupling agents like Atplus 536 (u), on the aphicidal activity of 
3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide (comp. no. 1) was tested 
according to the method described in Example X. The results recorded in 
Table F (% mortality) were obtained when 1 (6) days after the treatment 
the plants were evaluated. 
TABLE F 
______________________________________ 
Aphicidal activity (% mortality) 
Conc. in mg of act. subst. per liter 
additive 
mg/l 30 10 3 1 
______________________________________ 
None -- 21(92) 11(43) 0(7) -- 
5000 47(100) 40(100) 
5(98) -- 
(a) 
2500 43(100) 27(100) 
17(95) 
8(77) 
(b) 500 -- 3(96) 0(67) 0(20) 
(c) 500 -- 23(98) 0(60) 0(20) 
(d) 5000 37(99) 17(97) 2(62) -- 
(e) 2500 88(100) 80(99) 63(98) 
-- 
(f) 500 -- 43(100) 
7(33) -- 
(g) 500 -- 27(100) 
3(10) -- 
(h) 500 -- 73(98) 13(47) 
0(7) 
500 -- 57(99) 3(37) -- 
(i) 
1000 -- 70(99) 20(50) 
-- 
(j) 500 -- 96(100) 
30(90) 
0(23) 
(k) 500 -- 93(100) 
2(87) 0(17) 
(l) 500 -- 80(100) 
3(90) 0(7) 
(m) 500 -- 75(100) 
0(90) -- 
(n) 500 -- 98(100) 
43(80) 
3(7) 
(o) 500 -- 92(100) 
33(82) 
0(7) 
(p) 500 -- 87(100) 
57(63) 
20(20) 
(q) 500 -- 0(96) 0(13) -- 
(r) 500 -- 3(67) -- -- 
(s) 500 -- 90(99) 33(47) 
-- 
(t) 500 -- 80(99) 27(77) 
0(20) 
(u) 500 -- 90(96) 20(27) 
-- 
(v) 500 -- 47(99) 10(27) 
-- 
(w) 500 -- 33(100) 
0(27) -- 
______________________________________ 
In the absence of the tested aphicidal compound, the following additives as 
such, namely 5000 ppm Sunoil 7 N, 2500 ppm Sunoil 7 N, 5000 ppm Trioxitol, 
2500 ppm Dobane, and 500 ppm Arkopal N090, gave 5(23), 0(7), 0(0), 0(0) 
and 0(0)% mortality, respectively, upon evaluation after 1(6) days. 
EXAMPLE XV 
The effect of smaller additions of Sunoil 7 N on the aphicidal activity 
against Aphis fabae of 3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide 
(comp. no. 1) was tested according to the method described in Example XI. 
The results recorded in table G (% mortality) were obtained when the 
plants were evaluated 6 days after the treatment. 
TABLE G 
______________________________________ 
Aphicidal activity (% mortality) 
Conc. in mg of act. substance per liter 
Additive in mg/l 
30 10 3 1 
______________________________________ 
None 100 94 23 
Sunoil 7 N, 2500 
100 100 100 90 
Sunoil 7 N, 500 
100 100 94 37 
Sunoil 7 N, 100 
100 99 93 57 
______________________________________ 
EXAMPLE XVI 
Young potato plants, approx. 15 cm high, were infected with Myzus persicae 
in the same way as described in Example X for the infection with Aphis 
fabae. After infection the test plants were sprayed from below and from 
the top with a composition obtained according to Example IX in various 
concentrations (three plants per concentration), which composition 
comprised 3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide (comp. no. 1) as 
the active substance. After 6 days in the glasshouse at 
20.degree.-24.degree. C. the mortality of the aphids was determined. The 
average results are presented in table H below, in which the mortality 
percentage shown is corrected for the mortality of the untreated potato 
plants. 
The effect of several additives on the aphicidal activity of the above 
active substance was also tested. The results are presented in table H. 
The letters used for the additives in table H correspond to the letters 
used in Example XIV. 
TABLE H 
______________________________________ 
Aphicidal activity against Myzus persicae (% mortality) 
Conc. in mg active subst. per liter 
additive mg/l 30 10 3 
______________________________________ 
none -- 95 70 -- 
(k) 500 100 97 40 
(l) 500 100 99 40 
(i) 1000 100 99 43 
(h) 500 100 100 67 
(p) 500 100 100 80 
______________________________________ 
EXAMPLE XVII 
In the same way as described in Example XI the aphicidal activity of 
3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide (compound no. 1) against 
Aphis fabae was investigated; the tests were carried out on broad bean 
plants in the open air as described in Example XI. The effect of several 
additives (see Examples XIV and XVI) was determined. The results presented 
in table K were obtained when 6 days after the treatment the plants were 
examined to determine the mortality of the aphids. The letters used for 
the additives in table K correspond to the letters used in Example XIV. 
TABLE K 
______________________________________ 
Activity; % mortality after 6 days 
Conc. in mg act. per liter 
additive mg/l 30 10 3 
______________________________________ 
none -- 100 99 63 
(p) 250 100 91 
(m) 250 100 83 
(h) 250 100 89 
(a) 250 100 97 
______________________________________ 
EXAMPLE XVIII 
The aphicidal activity of 3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide 
(compound no. 1) against Aphis fabae was tested in several formulations in 
the same way as described in Example X. 
The formulations were prepared according to known formulation techniques as 
described in the specification. The formulations used are defined as 
follows: Suspension A comprises 7 parts by wt. of a lignine sulphonate, 3 
parts by wt. of an alkylnaphthalene sulphonate and 30 parts by wt. of 
active substance, diluted with water up to the desired concentration. 
Liquid B comprises 10% by wt. of active substance, 20% by wt. of an 
alkylphenolpolyoxyethylene, and 70% by wt. of dimethylformamide. Liquid C 
comprises 10% by wt. of active substance, 20% by wt. of an 
alkylphenolpolyoxyethylene, and 70% by wt. of N-methylpyrrolidone. 
Wettable powder D comprises 25% by wt. of active substance, 2% by wt. of 
an alkylnaphthalene sulphonate, 5% by wt. of a lignine sulphonate, and 68% 
by wt. of kaolin. After 6 days in the glasshouse the mortality of the 
aphids was determined. The results are presented in table L below. 
TABLE L 
______________________________________ 
Aphicidal activity; % Mortality after 6 days 
Conc. in mg active per liter 
formulation 30 10 3 
______________________________________ 
suspension A 97 47 7 
liquid B 100 97 0 
liquid C 100 96 17 
wettable powder D 
97 67 17 
______________________________________ 
EXAMPLE XIX 
The aphicidal activity of 3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide 
(compound no. 1) against Aphis fabae was tested in some formulations in 
the open air in the same way as described in Example XI. 
The formulations used are defined as follows: Wettable powder F comprises 
25% by wt. of active substance, 2% by wt. of an alkylnaphthalene 
sulphonate, 5% by wt. of a lignine sulphonate, and 68% by wt. of kaolin. 
Liquid G comprises 10% by wt. of active substance, 20% by wt. of an 
alkylphenolpolyoxyethylene, and 70% by wt. of dimethylformamide. 
After 6 days in the open air the mortality of the aphids was determined. 
The results are presented in table M. 
TABLE M 
______________________________________ 
Aphicidal activity; % mortality after 6 days 
Conc. in mg active per liter 
formulation 30 10 3 
______________________________________ 
wettable powder F 
100 99 63 
liquid G 100 100 63 
______________________________________ 
EXAMPLE XX 
The systemic activity of several formulations comprising 
3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide (compound no. 1) against 
Aphis fabae was determined as described in Example XII by mixing the 
composition through the soil. 2 Weeks after the treatment of the soil the 
plants were infected as described in Example X. 6 Days after the infection 
the mortality of the aphids was determined. After each week the infection 
was repeated; evaluation at each time 6 days after the infection. 
The formulations used are defined as follows: Suspension H comprises 1 part 
by wt. of a polyoxyethylenated sorbitan monooleate, 2 parts by wt. of a 
lignine sulphonate and 7 parts by wt. of active substance, diluted with 
water up to the desired concentration. Wettable powder I comprises 25% by 
wt. of active substance, 2% by wt. of an alkylnaphthalene sulphonate, 5% 
by wt. of a lignine sulphonate, and 68% by wt. of kaolin. Granule J 
comprises 2.5% by wt. of active substance, 7.5% by wt. of kaolin, 6.7% by 
wt. of a lignine sulphonate, and 83.3% by wt. of a granular silicate. 
Granule K comprises 2.5% by wt. of active substance, 7.5% by wt. of 
kaolin, 5% by wt. of polyvinylacetate, and 85% by wt. of a granular 
silicate. Granule L comprises 2.5% by wt. of active substance, 7.5% by wt. 
of kaolin, 5% by wt. of sodium-silicate and 85% by wt. of a granular 
silicate. The results are presented in table N. 
TABLE N 
__________________________________________________________________________ 
Aphicidal activity; % mortality at (re)-infection in . . . weeks after 
treatment of the soil and subsequent evaluation after 6 days. 
mg act. 
weeks 
composition 
per pot 
2 3 4 5 6 7 8 9 10 
11 
12 
13 
__________________________________________________________________________ 
Suspension H 
1 100 
100 
100 
100 
100 
100 
98 85 63 
33 
0 
Suspension H 
3 100 
100 
100 
100 
100 
100 
100 
100 
94 
91 
77 
52 
W.P. I 1 100 
100 
99 99 100 
98 95 73 53 
23 
10 
W.P. I 3 100 
100 
100 
100 
100 
100 
100 
99 96 
93 
85 
63 
Granule J 
1 100 
100 
100 
100 
100 
100 
99 70 40 
23 
7 
Granule J 
3 100 
100 
100 
100 
100 
100 
100 
100 
99 
98 
90 
75 
Granule K 
1 100 
100 
100 
99 99 99 97 80 67 
37 
7 
Granule K 
3 100 
100 
100 
100 
100 
100 
100 
99 96 
93 
83 
50 
Granule L 
1 100 
100 
100 
100 
100 
99 99 83 70 
53 
20 
Granule L 
3 100 
100 
100 
100 
100 
100 
100 
99 94 
93 
88 
70 
__________________________________________________________________________ 
EXAMPLE XXI 
The investigations described in Example XX were repeated in field trials. 
The trials were carried out on broad bean plants against Aphis fabae; 
active substance 3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide (compound 
no. 1). After each visual evaluation and before the next (re-) infection 
the plants were freed from aphids. The soil was treated by 10 cm deep 
spadeing of the composition into the soil. 
The results are presented in table O. It should be remarked, that during 
these trials the weather conditions were very bad: it was extremely wet. 
TABLE O 
______________________________________ 
Aphicidal activity; % mortality at (re-)-infection in . . . weeks 
after treatment of the soil and subsequent evaluation after 
6 days. 
kg active 
subst. per 
weeks 
composition 
hectare 1 3 5 
______________________________________ 
W.P. I 10 99 100 83 
W.P. I 3 99 63 10 
W.P. I 1 27 27 0 
Granule J 10 100 100 88 
Granule J 3 98 63 13 
Granule J 1 50 30 0 
______________________________________ 
EXAMPLE XXII 
Young cotton plants, approx. 10 cm high, were infected with Aphis gossypii 
(cotton aphid) in the same way as described in Example X for the infection 
with Aphis fabae. After infection the test plants were sprayed from below 
and from the top with a composition obtained according to Example IX in 
various concentrations, which composition comprised 
3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide (compound no. 1) as the 
active substance and an additive. After 6 days in a climate room at 
20.degree. C. the mortality of the aphids was determined. The results are 
presented in table P. As in all further experiments the results are 
corrected for the mortality on the untreated plants. The letters used for 
the additives in table P correspond to the letters used in Example XIV. 
TABLE P 
______________________________________ 
Activity against Aphis gossypii; % mortality 
conc. in mg active per liter 
additive mg/l 100 30 10 3 
______________________________________ 
(h) 250 100 100 100 100 
(i) 250 100 100 100 70 
______________________________________ 
EXAMPLE XXIII 
Young broad bean plants, approx. 10 cm high, were infected with 
Acyrthosiphon pisum (bean aphid) in the same way as described in Example 
X, and subsequently treated as described in Example XXII. Active 
substance: 3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide (compound no. 
1). After 5 days in a climate room at 20.degree. C. the mortality of the 
aphids was determined. The results are presented in table Q. 
TABLE Q 
______________________________________ 
Activity against Acyrthosiphon pisum; % mortality 
conc. in mg active per liter 
additive mg/l 30 10 3 
______________________________________ 
none -- 28 20 8 
Agral LN 250 97 74 60 
Arkopal N150 250 97 57 0 
______________________________________ 
Agral LN and Arkopal N 150 as such in the above amounts caused 5 and 0% 
mortality respectively after 5 days. 
EXAMPLE XXIV 
Young oat plants, approx. 15 cm high, were infected with Sitobion avenae 
(small corn aphid) in the same way as described in Example X, and 
subsequently treated as described in Example XXII. Active substance: 
3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide (compound no. 1). 
After 6 days in a climate room at 20.degree. C. the mortality of the aphids 
was determined. The results are presented in table R. 
TABLE R 
______________________________________ 
Activity against Sitobion avenae; % Mortality 
Conc. in mg active per liter 
additive mg/l 100 30 10 3 
______________________________________ 
Agral LN 250 100 100 100 71 
Citowett 250 92 97 100 55 
______________________________________ 
Agral LN and Citowett as such in the above amounts caused 6 and 11% 
mortality respectively after 6 days. 
EXAMPLE XXV 
Young Brussels sprout plants, approx. 10 cm high, were infected with 
Brevicoryne brassicae (mealy cabbage aphid) in the same way as described 
in Example X, and subsequently treated as described in Example XXII. 
Active substance: 3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide 
(compound no. 1). After 6 days in a climate room at 20.degree. C. the 
mortality of the aphids was determined. The results are presented in table 
S. 
TABLE S 
______________________________________ 
Activity against Brevicoryne brassicae; 
% mortality after 6 days 
conc. in mg active per liter 
additive mg/l 100 30 10 3 1 
______________________________________ 
Citowett 250 92 58 39 23 5 
______________________________________ 
EXAMPLE XXVI 
Young potato plants, approx. 15 cm high, were infected with Myzus persicae 
in the same way as described in Example XVI. The aphicidal activity was 
determined in the open air as described in Example X. Active compound: 
3-amino-4-chlorobenzo[d]isothiazole-1,1-dioxide (compound No. 1). The 
effect of several additives, specified in previous Examples, was tested. 
The results, presented in Table T, were obtained when 6 days after the 
treatment the plants were examined to determine the mortality of the 
aphids. The letters used for the additives in table T correspond to the 
letters used in Example XIV. 
TABLE T 
______________________________________ 
Activity against Myzus persicae; 
% mortality after 6 days 
conc. in mg active per liter 
additive mg/l 30 10 3 
______________________________________ 
none -- 96 92 53 
(p) 250 -- 98 85 
(m) 250 -- 99 63 
(h) 250 -- 96 87 
(a) 250 -- 99 60 
______________________________________