Arylsulphonyl-pyridinealdoxime derivatives of the formula (I) ##STR1## in which R, R.sup.1, R.sup.2, n and m have the meanings stated in the description, and their use as agents for combating pests. The new arysulphonyl-pyridinealdoxime derivatives of the formula (I) can be prepared from suitable arylsulphonyl-pyridinealdoximes and suitable carbonyl compounds.

The present invention relates to new arylsulfonyl-pyridinealdoxime 
derivatives, a process for their preparation and their use as agents for 
combating pests, in particular as fungicides. 
A number of aldoxime derivatives are already known. 
Arylsulphonylbenzaldoximes, such as 
.alpha.-phenylsulphonyl-2,6-dichlorobenzaldoxime, are, for example, known 
and their use as agents for combating pests, and above all their use in 
agents for combating wheat smut (cf. Swiss Patent No. 423,350). In 
addition, phenylpyridinealdoximes, such as, for example, 
phenyl-O-ethylcarbonylpyridinealdoxime, and their antihistaminic action, 
are known (cf. J. pharm. Sci. 56(1967) No. 10, pp. 1354-1357). 
New arylsulfonyl-pyridinealdoxime derivatives of the general formula (I) 
##STR2## 
have been found, in which R represents alkyl or alkoxy, 
R.sup.1 represents halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, 
halogenoalkoxy, halogenoalkylthio, nitro, alkoxycarbonyl or 
alkylcarbonylamino, 
R.sup.2 represents halogen or alkyl, 
n represents an integer 0, 1, 2, 3, 4 or 5 and 
m represents an integer 0, 1, 2, 3 or 4 
it being possible for the substituents in the rings to be identical or 
different. 
It has also been found that the arylsulphonyl-pyridinealdoxime derivatives 
of the general formula (I) 
##STR3## 
in which R represents alkyl or alkoxy, 
R.sup.1 represents halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, 
halogenoalkoxy, halogenoalkylthio, nitro, alkoxycarbonyl or 
alkylcarbonylamino, 
R.sup.2 represents halogen or alkyl, 
n represents an integer 0, 1, 2, 3, 4 or 5 and 
m represents an integer 0, 1, 2, 3 or 4, 
it being possible for the substituents in the rings to be identical or 
different, 
are obtained when arylsulphonyl-pyridinealdoximes of the general formula 
(II) 
##STR4## 
in which R.sup.1, R.sup.2, n and m have the above-mentioned meanings, 
are reacted with carbonyl compounds of the general formula (III) 
EQU X--CO--R (III) 
in which 
R has the above-mentioned meanings and 
X represents a halogen atom, preferably chlorine, or the radical --O--COR, 
if appropriate in the presence of a solvent or diluent and if appropriate 
in the presence of an acid-binding agent. 
The arylsulphonyl-pyridinealdoxime derivatives of the formula (I), 
according to the invention, exhibit powerful biological and above all 
fungicidal properties. 
Surprisingly, the compounds according to the invention display considerably 
more powerful, in particular fungicidal, activity than the compounds known 
from the prior art which are, from the point of view of their structure 
and/or action, very closely related compounds. 
The compounds of the formula (I), according to the invention, can be 
obtained as syn- or anti-isomers or as mixtures thereof of varying 
composition. The invention relates both to the pure isomers and to the 
mixtures of isomers. 
The alkyl radicals R, R.sup.1 and R.sup.2 and the alkyl parts in the alkoxy 
radicals in R and R.sup.1 can be straight-chain or branched and contain 
preferably in each case 1 to 6, and in particular 1 to 4 carbon atoms. 
Examples which may be mentioned are: methyl, ethyl, n-propyl, iso-propyl, 
n-butyl, sec.-butyl, iso-butyl, tert.-butyl, n-pentyl, isopentyl, 
sec.-pentyl, n-hexyl, sec.-hexyl, methoxy, ethoxy, n-propoxy, iso-propoxy, 
n-butoxy, iso-butoxy, sec.-butoxy, tert.-butoxy, n-pentoxy, iso-pentoxy, 
sec.-pentoxy, n-hexoxy and sec. hexoxy. 
The alkylthio radicals in R.sup.1 can be straight-chain or branched and 
certain preferably 1 to 6, in particular 1 to 4, and particularly 
preferably 1 to 3 carbon atoms. Examples which may be mentioned are: 
methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, 
iso-butylthio, sec.-butylthio, tert.-butylthio, n-pentylthio and 
n-hexylthio. 
The halogenoalkyl parts in R.sup.1 in the radicals halogenalkyl, 
halogenalkoxy and halogenalkylthio contain preferably in each case 1 to 6, 
in particular 1 to 4 and particularly preferably 1 or 2 carbon atoms and 
preferably 1 to 9, in particular 1 to 5, and particularly preferably 1 to 
4 identical or different halogen atoms. Examples which may be mentioned 
are: trichlormethyl, trifluormethyl, dichlorfluoromethyl, trichloroethyl, 
tetrachloroethyl, trichloromethoxy, trichloroethoxy, tetrachloroethoxy, 
trichloromethylthio, trifluoromethylthio, dichlorofluoromethylthio, 
trichloroethylthio and tetrachloroethylthio. 
Halogen in R.sup.1 and R.sup.2, as well as in the radicals such as 
halogenoalkyl, denotes fluorine, chlorine, bromine or iodine, in 
particular fluorine or chlorine, unless particularly defined elsewhere. 
Alkoxycarbonyl and alkylcarbonylamino in R.sup.1 contain in each case in 
the alkyl parts preferably 1 to 4, in particular 1 to 3 carbon atoms, and 
particularly preferably 1 or 2 carbon atoms. Examples which may be 
mentioned are: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 
iso-propoxycarbonyl, n-butoxycarbonyl, sec.-butoxycarbonyl, 
iso-butoxycarbonyl, tert.-butoxycarbonyl, methylcarbonylamino, 
ethylcarbonylamino, n-propylcrbonylamino, iso-propylcarbonylamino, 
n-butylcarbonylamino, iso-butylcarbonylamino, tert.-butylcarbonylamino and 
tert.-butylcarbonylamino. 
n preferably denotes 0, 1, 2, 3 or 4, in particular 0, 1, 2 or 3, and 
m preferably denotes 0, 1, 2 or 3, in particular 0 or 1. 
The arylsulphonyl-pyridinealdoxime derivatives are generally defined by the 
formula (I). 
Compounds of the formula (I) are preferred in which 
R represents straight-chain or branched alkyl with 1 to 6 carbon atoms or 
straight-chain or branched alkoxy with 1 to 6 carbon atoms, 
R.sup.1 represents halogen, alkyl or alkoxy with in each case 1 to 6 carbon 
atoms, alkylthio with 1 to 6 carbon atoms, halogenoalkyl, halogenoalkoxy 
or halogenoalkylthio with in each case 1 to 6 carbon atoms and in each 
case 1 to 9 identical or different halogen atoms, nitro, alkoxycarbonyl or 
alkylcarbonylamino with 1 to 4 carbon atoms in the alkoxy or alkyl part, 
R.sup.2 represents halogen or alkyl with 1 to 6 carbon atoms, 
n represents an integer 0, 1, 2, 3 or 4 and 
m represents an integer 0, 1, 2 or 3. 
Compounds of the formula (I) in which 
R represents straight-chain or branched alkyl with 1 to 4 carbon atoms or 
straight-chain or branched alkoxy with 1 to 4 carbon atoms, 
R.sup.1 represents halogen, straight-chain or branched alkyl with 1 to 4 
carbon atoms, straight-chain or branched alkoxy with 1 to 4 carbon atoms, 
straight-chain or branched alkylthio with 1 to 4 carbon atoms, 
halogenoalkyl with 1 to 4 carbon atoms and 1 to 5 identical or different 
halogen atoms, halogenoalkoxy or halogenoalkylthio with in each case 1 to 
4 carbon atoms and in each case 1 to 5 identical or different halogen 
atoms, nitro, straight-chain or branched alkoxycarbonyl with 1 to 3 carbon 
atoms or alkylcarbonylamino with 1 to 3 carbon atoms in the alkyl part, 
R.sup.2 represents halogen or straight-chain or branched alkyl with 1 to 4 
carbon atoms, 
n represents an integer 0, 1, 2, 3 or 4 and 
m represents an integer 0, 1, 2 or 3, 
are particularly preferred. 
In particular compounds of the formula (I) may be mentioned in which 
R represents straight-chain or branched alkyl or alkoxy with in each case 1 
to 4 carbon atoms, 
R.sup.1 represents fluorine, chlorine, straight-chain or branched alkyl or 
alkoxy with in each case 1 to 4 carbon atoms, straight-chain or branched 
alkylthio with 1 to 3 carbon atoms, halogenoalkyl, halogenoalkoxy or 
halogenoalkylthio with in each case 1 or 2 carbon atoms and in each case 1 
to 4 identical or different fluorine and chlorine atoms, nitro, 
alkoxycarbonyl or alkylcarbonylamino with in each case 1 or 2 carbon atoms 
in the alkoxy or alkyl part, 
R.sup.2 represents fluorine, chlorine or straight-chain or branched alkyl 
with 1 to 4 carbon atoms, 
n represents an integer 0, 1, 2, 3 or 4 and 
m represents an integer 0, 1, 2 or 3. 
Compounds of the formula (I) in which 
R represents straight-chain or branched alkyl or alkoxy with in each case 1 
to 4 carbon atoms, 
R.sup.1 represents fluorine, chlorine, methyl, elthyl, n-propyl, 
iso-propyl, methoxy, ethoxy, methylthio, trifluoromethyl, 
trifluoromethoxy, trifluoromethylthio, nitro, methoxycarbonyl, 
ethoxycarbonyl, methylcarbonylamino or ethylcarbonylamino, 
R.sup.2 represents chlorine, methyl or ethyl, 
n represents an integer 0, 1, 2 or 3 and 
m represents an integer 0 or 1 
may be mentioned with very particular preference. 
If 4-methylphenylsulphonyl-2-pyridinealdoxime and ethyl-formate chloride 
are used as the starting compounds the course of the reaction of the 
process according to the invention can be illustrated by the following 
equation: 
##STR5## 
The arylsulphonyl-pyridinealdoximes required as starting compounds for 
carrying out the process according to the invention are defined by formula 
(II). These compounds are new and the subject of another application which 
has not yet been published. The compounds can, however, be prepared by 
analogous processes for example by reacting pyridinealdoximes of the 
formula (IV) 
##STR6## 
in which R.sup.2 and m have the above-mentioned meanings, with chlorine, 
to give the corresponding .alpha.-chloropyridinealdoximes and reacting the 
latter with arylsulphinic acids of the formula (V) 
##STR7## 
or their alkali metal compounds, in which R.sup.1 and n have the 
above-mentioned meanings, if appropriate in the presence of a solvent or 
diluent, such as, for example methanol, if appropriate in the presence of 
a base, such as for example triethylamine and if appropriate at elevated 
temperatures. 
The pyridinealdoximes of the formula (IV) and the arylsulphinic acids of 
the formula (V) are known compounds in organic chemistry. 
The carbonyl compounds also required as starting compounds are defined by 
formula (III). They are known compounds in organic chemistry. 
The process according to the invention can, if appropriate, be carried out 
in the presence of a solvent or diluent. In principle all inert organic 
solvents can be used as such. Hydrocarbons, which are optionally 
chlorinated, such as for example benzene, toluene, xylene, methylene 
chloride, chloroform, carbon tetrachloride, chlorobenzene and 
dichlorobenzene, as well as ethers such as diethyl and dibutyl ether, 
glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and 
dioxane, also ketones such as acetone, methyl ethyl, methyl isopropyl and 
methyl isobutyl ketone, in addition esters, such as methyl and ethyl 
acetate, as well as nitriles, such as for example acetonitrile and 
propionitrile, benzonitrile, glutaric acid nitrile, and furthermore 
amides, such as for example dimethyl formamide, are preferably used. 
Customary inorganic or organic acid binders can be used as the acid-binding 
agents for the process according to the invention. Those which may be 
mentioned are: for example tert.-amines such as triethylamine, pyridine 
and triethylenediamine etc. 
The reaction temperature of the process according to the invention can be 
varied within a relatively large temperature range. In general a 
temperature of between 0.degree. C. and 120.degree. C., preferably between 
20.degree. C. and 70.degree. C. is used. 
The reaction is normally carried out under normal pressure. When carrying 
out the process according to the invention the compounds of the formula 
(II) are generally initially introduced in a solvent with equimolar 
quantities of the acid binder and the carbonyl compounds of the formula 
(III) are added, preferably also in equimolar quantities. Working up is 
carried out according to generally customary methods. 
A particular embodiment must also be mentioned. If X has the meaning 
--O--COR, which therefore means that carbocyclic acid anhydrides of the 
formula (III) are used, the reaction is carried out without any solvent 
and with a high excess of the anhydride, which then serves both as 
starting compound and a solvent. Working up is also carried out by 
customary methods. 
The active compounds according to the invention exhibit a powerful 
microbicidal action and can be employed in practice for combating 
undesired microorganisms. The active compounds are suitable for use as 
plant protection agents. 
Fungicidal agents in plant protection are employed for combating 
Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, 
Ascomycetes, Basidiomycetes and Deuteromycetes. 
Bactericidal agents are employed in plant protection for combating 
Pseudomonoadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae 
and Streptomyceteae. 
Some causative organisms of fungal and bacterial diseases included under 
the above-mentioned main headings, are mentioned below as non-limiting 
examples: 
Xanthomonas species, such as, for example, Xanthomonas campestris pv. 
oryzae; 
Pseudomonas species, such as, for example, Pseudomonas syringae pv. 
lachrymans; 
Erwinia species, such as, for example, Erwinia amylovora; Pythium species, 
such as, for example, Pythium ultimum; Phytophthora species, such as, for 
example, Phytophthora infestans; 
Pseudoperonospora species, such as, for example, Pseudoperonospora 
cubensis; 
Plasmopara species, such as, for example, Plasmopara viticola; 
Peronospora species, such as, for example, Peronospora pisi or P. 
brassicae; 
Erysiphe species, such as, for example, Erysiphe graminis; 
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea; 
Podosphaera species, such as, for example, Podosphaera leucotricha; 
Venturia species, such as, for example, Venturia inaequalis; 
Pyrenophora species, such as, for example, Pyrenophora teres or P. 
graminea; 
(Conidial form: Drechlera, Synonym: Helminthosporium); Cochliobolus 
species, such as, for example, Cochliobolus sativus; 
(Conidial form: Drechslera, Synonym: Helminthosporium); Uromyces species, 
such as, for example, Uromyces appendiculatus; 
Puccinia species, such as, for example, Puccinia recondita; 
Tilletia species, such as, for example, Tilletia caries; 
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae; 
Pellicularia species, such as, for example, Pellicularia sasakii; 
Pyricularia species, such as, for example, Pyricularia oryzae; 
Fusarium species, such as, for example, Fusarium culmorum; 
Botrytis species, such as, for example, Botrytis cinerea; 
Septoria species, such as, for example, Septoria nodorum; 
Leptosphaeria species, such as, for example, Leptophaeria nodorum; 
Cercospora species, such as, for example, Cercospora canescens; 
Alternaria species, such as, for example, Alternaria brassicae; 
Pseudocercosporella species, such as, for example, Pseudocercosporella 
herpotrichoides. 
The good toleration, by plants, of the active compounds, at the 
concentrations required for combating plant diseases, permits treatment of 
above-ground parts of plants, of vegetative propagation stock and seeds, 
and of the soil. 
The active compounds according to the invention can be used very 
successfully for combating vegetable and fruit diseases, caused for 
example by Venturia inaequalis or Botrytis cinerea, for combating rice 
diseases caused, for example, by Pyricularia oryzae and for combating 
cereal diseases caused, for example, by Puccinia condita. 
The active compounds can be converted to the customary formulations, such 
as solutions, emulsions, suspensions, powders, foams, pastes, granules, 
aerosols, very fine capsules in polymeric substances and in coating 
compositions for seed, as well as ULV formulations. 
These formulations are produced in known manner, for example by mixing the 
active compounds with extenders, that is, liquid solvents, liquefied gases 
under pressure, and/or solid carriers, optionally with the use of 
surface-active agents, that is, emulsifying agents and/or dispersing 
agents, and/or foam-forming agents. In the case of the use of water as an 
extender, organic solvents can, for example, also be used as auxiliary 
solvents. As liquid solvents, there are suitable in the main: aromatics, 
such as xylene, toluene or alkyl naphthalenes, chlorinated aromatics or 
chlorinated aliphatic hydrocarbons, such as chlorobenzenes, 
chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as 
cyclohexane or paraffins, for example mineral oil fractions, alcohols, 
such as butanol or glycol as well as their ethers and esters, ketones, 
such as acetone, methyl ethyl ketone, methyl isobutyl ketone or 
cyclohexanone, strongly polar solvents, such as dimethylformamide and 
dimethylsulphoxide, as well as water. By liquefied gaseous extenders or 
carriers are meant liquids which are gaseous at normal temperature and 
under normal pressure, for example aerosol propellants, such as 
halogenated hydrocarbons as well as butane, propane, nitrogen and carbon 
dioxide. As solid carriers there are suitable: for example, ground natural 
minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, 
montmorillonite or diatomaceous earth, and ground synthetic minerals, such 
as highly-dispersed silicic acid, alumina and silicates. As solid carriers 
for granules there are suitable: for example, crushed and fractionated 
natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as 
well as synthetic granules of inorganic and organic meals, and granules of 
organic material such as sawdust, coconut shells, maize, cobs and tobacco 
stalks. As emulsifying and/or foam-forming agents, there are suitable: for 
example, non-ionic and anionic emulsifiers, such as polyoxyethylene-fatty 
acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylaryl 
polyglycol ethers, alkylsulphonates, alkyl-sulphates, arylsulphonates as 
well as albumin hydrolysation products. As dispersing agents there are 
suitable: for example, lignin-sulphite waste liquors and methylcellulose. 
Adhesives such as carboxymethylcellulose and natural and synthetic polymers 
in the form of powders, granules or latices, such as gum arabic, polyvinyl 
alcohols and polyvinyl acetate, as well as natural phospholipids, such as 
cephalins and lecithins, and synthetic phospholipids, can be used in the 
formulations. Further additives can be mineral and vegetable oils. 
It is possible to use colorants such as inorganic pigments, for example 
iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such 
as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, 
and trace nutrients such as salts or iron, manganese, boron, copper, 
cobalt, molybdenum and zinc. 
The formulation in general contain between 0.1 and 95 percent by weight of 
active compound, preferably between 0.5 and 90%. 
The active compounds according to the invention can be present in the 
formulations as a mixture with other known active compounds, such as 
fungicides, insecticides, acaricides and herbicides, and also as mixtures 
with fertilisers and other growth regulators. 
The active compounds can be used as such, in the form of their formulations 
or as the use forms prepared therefrom, such as ready-to-luse solutions, 
emulsifiable concentrates, emulsions, foams, suspensions, wettable 
powders, pastes, soluble powders, dusting agents and granules. They are 
used in the customary manner, for example by watering, spraying, 
atomising, scattering, dusting, foaming, coating and the like. 
Furthermore, it is possible to apply the active compounds in accordance 
with the ultra-low volume process or to inject the active compound 
preparation or the active compound itself into the soil. It is also 
possible to treat the seeds of plants. 
In the treatment of parts of plants, the active compound concentrations in 
the use forms can be varied within a substantial range. They are, in 
general, from 1 to 0.0001% by weight, preferably from 0.5 and 0.001%. 
For the treatment of seed, amounts of active compound of 0.001 to 50 g, 
especially 0.01 to 10 g, are generally employed per kilogram of seed. 
For the treatment of soil, active compound concentrations, at the point of 
action, of 0.00001 to 0.1% by weight, especially of 0.0001 to 0.02%, are 
generally employed.

Preparative examples 
EXAMPLE 1 
Initial Product 
##STR8## 
40.6 g (0.333 m) of pyridine-4-aldoxime are dissolved in 350 ml of 
methylene chloride and chlorine (dried) is introduced at -15.degree. C. 
until saturation is reached. The reaction mixture is allowed to reach room 
temperature overnight and is then filtered by suction. The reaction 
product is washed with methylene chloride and then with acetone and is 
subsequently rinsed with ether. 60 g (93.4% of theory) of the required 
substance with a melting point of 203.degree. C. (decomposition) are 
obtained. 
##STR9## 
19.3 g (0.1 m) of .alpha.-chloro-pyridine-4-aldoximehydrochloride are 
dissolved in 250 ml of methanol and 18.7 g (0.105 m) of sodium 
4-methylphenylsulphinate are added, 14 ml (0.1 m) of triethylamine are 
also added in order to liberate the .alpha.-chloropyridine-4-aldoxime. The 
reaction proceeds in a slightly exothermic manner. The reaction mixture is 
kept at room temperature and stirring is continued overnight at this 
temperature. The mixture is then poured onto about 1 l of ice water and 
the precipitate formed by stirring is filtered by suction, washed and 
dried. The reaction product is recrystallised from isopropanol. 8.1 g (29% 
of theory) of the required compound with a melting point of 138.degree. C. 
are obtained. 
End Product 
##STR10## 
13.8 g (0.05 m) of .alpha.-(4-methylphenylsulphonyl)pyridine-4-aldoxime are 
dissolved in 150 ml of acetonitrile and 7 ml (0.05 m) of triethylamine and 
5.5 g (0.05 m) of ethyl chloroformate are added. The reaction proceeds 
exothermically. 
The reaction mixture is stirred overnight at room temperature and then 
poured onto 750 ml of water and the precipitate formed by stirring is 
filtered by suction, washed and dried. The reaction product is 
recrystallised from isopropanol. 7.4 g (43% of theory) of the required 
compound with a melting point of 126.degree. C. are obtained. 
The compounds of the formula (I) can be prepared according to examples 1 
and 9: 
______________________________________ 
##STR11## (I) 
Physical 
position 
Data 
of the (Melting 
Example pyridine 
point in 
No. R R.sup.1 R.sup.2 
n m ring .degree.C.) 
______________________________________ 
2 CH.sub.3 4-CH.sub.3 
-- 1 0 4 184 
3 OC.sub.2 H.sub.5 
-- -- 0 0 4 108 
4 OC.sub.2 H.sub.5 
4-Cl -- 1 0 4 129 
5 OC.sub.2 H.sub.5 
4-Cl -- 1 0 3 43 
6 OC.sub.2 H.sub.5 
-- -- 0 0 3 148 
7 OC.sub.2 H.sub.5 
4-CH.sub.3 
-- 1 0 3 133 
8 OCH.sub.3 
4-CH.sub.3 
-- 1 0 2 138 
______________________________________ 
EXAMPLE 9 
##STR12## 
100 ml of acetic anhydride are added to 27.6 g (0.1 m) of 
.alpha.-(4-methyl-phenylsulphonyl)-pyridine-2-aldoxime and the mixture is 
stirred at 50.degree. C. overnight. The reaction solution is filtered, the 
filtrate is evaporated in a rotary evaporator and the residue remaining is 
recrystallised from isopropanol. Yield: 23.2 g=73% of theory; melting 
point: 88.degree. C. 
__________________________________________________________________________ 
Position 
Physical 
of the 
Data 
Example pyridine 
(Melting 
No. R R.sup.1 
R.sup.2 
n m ring point in .degree.C.) 
__________________________________________________________________________ 
10 --OC.sub.2 H.sub.5 
4-CH.sub.3 
3-CH.sub.3 
1 1 2 91 
11 --OC.sub.2 H.sub.5 
-- 3-CH.sub.3 
0 1 2 57 
12 --OCH.sub.3 
4-Cl -- 1 0 2 75 
13 --OC.sub.2 H.sub.5 
4-Cl -- 1 0 2 125 
14 --OC.sub.3 H.sub.7 --i 
4-Cl -- 1 0 2 82 
15 --OC.sub.3 H.sub.7 --i 
4-CH.sub.3 
-- 1 0 3 133-34 
16 --OCH.sub.3 
4-Cl -- 1 0 4 142 
17 --OCH.sub.3 
-- -- 0 0 4 140 
18 --OC.sub.4 H.sub.9 --i 
4-CH.sub.3 
-- 1 0 3 145 
19 --OC.sub.2 H.sub.5 
4-CH.sub.3 
-- 1 0 2 80 
20 --OCH.sub.3 
4-Cl -- 1 0 3 147 
21 --OC.sub.3 H.sub.7 --i 
4-CH.sub.3 
-- 1 0 2 98 
22 --OCH.sub.3 
4-CH.sub.3 
3-CH.sub.3 
1 1 2 119 
23 --OCH.sub.3 
-- 3-CH.sub.3 
0 1 2 101 
24 --OCH.sub.3 
4-CH.sub.3 
-- 1 0 3 161 
25 --OCH.sub.3 
-- -- 0 0 3 94 
26 --OC.sub.4 H.sub.9 --i 
4-CH.sub.3 
-- 1 0 2 84 
27 --OC.sub.4 H.sub.9 --i 
-- -- 0 0 3 92 
28 --OCH.sub.3 
-- -- 0 0 2 113 
29 --OC.sub.2 H.sub.5 
-- -- 0 0 2 92 
30 --OC.sub.4 H.sub.9 --i 
-- -- 0 0 2 53 
31 --OCH.sub.3 
4-CH.sub.3 
-- 1 0 4 150 
32 --OC.sub.4 H.sub.9 --i 
4-Cl -- 1 0 2 95 
33 --OC.sub.4 H.sub.9 --i 
4-Cl -- 1 0 3 145 
34 -- OC.sub.4 H.sub.9 --i 
4-CH.sub.3 
-- 1 0 4 125 
35 --OC.sub.4 H.sub.9 --i 
4-Cl -- 1 0 4 112 
36 --OC.sub.4 H.sub.9 --i 
-- -- 0 0 4 83 
37 --OC.sub.4 H.sub.9 --i 
4-CH.sub.3 
3-CH.sub.3 
1 1 2 100 
38 --OC.sub.4 H.sub.9 --i 
-- 3-CH.sub.3 
0 1 2 86 
39 --OC.sub.3 H.sub.7 --i 
4-CH.sub.3 
3-CH.sub.3 
1 1 2 
40 --OC.sub.3 H.sub.7 --i 
-- -- 0 0 2 
41 --OC.sub.3 H.sub.7 --i 
-- -- 0 0 2 
42 --OC.sub.3 H.sub.7 --i 
4-Cl -- 1 0 3 
43 --OC.sub.3 H.sub.7 --i 
-- -- 0 0 3 
44 --OC.sub.3 H.sub.7 --i 
4-CH.sub.3 
-- 1 0 4 
45 --OC.sub.3 H.sub.7 --i 
4-Cl -- 1 0 4 
46 --OC.sub.3 H.sub.7 --i 
-- -- 0 0 4 
47 --OC.sub. 3 H.sub.7 --i 
4-CH.sub.3 
3-CH.sub.3 
1 1 2 
48 --OC.sub.3 H.sub.7 --i 
-- 3-CH.sub.3 
0 1 2 
__________________________________________________________________________ 
EXAMPLE 
Pyricularia test (rice)/protective 
Solvent: 12.5 parts by weight of acetone 
Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amount of solvent, and the 
concentrate is diluted with water and th stated amount of emulsifier to 
the desired concentration. 
To test for protective activity, young rice plants are sprayed with the 
preparation of active compound until dripping wet. After the spray coating 
has dried on, the plants are inoculated with an aqueous spore suspension 
of Pyricularia oryzae. The plants are then placed in a greenhouse at 100% 
relative atmospheric humidity and 25.degree. C. 
Evaluation of the disease infestation is carried out 4 days after the 
inoculation. 
The compounds according to the invention exhibit powerful activity at a 
concentration of active compound of 0.025%. 
TABLE 
______________________________________ 
Pyricularia-Test (rice)/protective 
Active Disease 
com- infesta- 
pound tion of the 
concen- untreated 
tration control in 
Active compounds in % % 
______________________________________ 
##STR13## 0,025 22 
##STR14## 0,025 11 
##STR15## 0,025 0 
##STR16## 0,025 0 
______________________________________ 
EXAMPLE 
Phytophthora test (tomato)/protective 
Solvent: 4.7 parts by weight acetone 
Emulsifier: 0.3 parts by weight alkylarylpolyglycolether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amounts of solvent and 
emulsifier, and the concentrate is diluted with water to the desired 
concentration. 
To test for protective activity, young plants are sprayed with the 
preparation of active compound until dripping wet. After the spray coating 
has dried on, the plants are inoculated with an aqueous spore suspension 
of Phytophthora infestans. 
The plants are placed in an incubation cabin at 100% relative atmospheric 
humidity and at about 20.degree. C. 
Evaluation is carried out 3 days after the inoculation. 
The compounds according to the invention exhibit powerful activity. 
EXAMPLE 
Venturia test (apple)/protective 
Solvent: 4.7 parts by weight acetone 
Emulsifier: 0.3 parts by weight of alkylarylpolyglycolether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amounts of solvent and 
emulsifier, and the concentrate is diluted with water to the desired 
concentration. 
To test for protective activity, young plants are sprayed with the 
preparation of active compound until dripping wet. After the spray coating 
has dried on, the plants are inoculated with an aqueous conidia suspension 
of the apple scab causative organism (Venturia inaequalis) and then remain 
in an incubation cabin at 20.degree. C. and 10% relative atmospheric 
humidity for 1 day. 
The plants are then placed in a greenhouse at 20.degree. C. and a relative 
atmospheric humidity of about 70%. 
Evaluation is carried out 12 days after the inoculation. 
EXAMPLE 
Botrytis test (beans)/protective 
Solvent: 4.7 parts by weight of acetone 
Emulsifier: 0.3 parts by weight of alkylarylpolyglycolether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amounts of solvent and 
emulsifier, and the concentrate is diluted with water to the desired 
concentration. 
To test for protective activity, young plants are sprayed with the 
preparation of active compound until dripping wet. After the spray coating 
has dried on, 2 small pieces of agar covered with Botrytis cinerea are 
placed on each leaf. The inoculated plants are placed in a darkened 
humidity chamber at 20.degree. C. 3 days after the inoculation, the size 
of the infected spots on the leaves is evaluated. 
The compounds according to the invention exhibit powerful activity.