Alkoxycarbonyl-substituted hydroxythiophene-carboxamides, fungicidal compositions and use

Alkoxycarbonyl-substituted hydroxythiophenecarboxamides of the formula ##STR1## in which R.sup.1 represents alkyl, alkoxyalkyl, alkylthioalkyl, fluoroalkyl, cyanoalkyl, alkenyl or alkinyl or represents cycloalkyl, PA0 R.sup.2 represents alkyl or optionally substituted phenyl, PA0 R.sup.3 represents alkyl, alkoxyalkyl, alkylthioalkyl, cyanoalkyl, fluoroalkyl, alkenyl, alkinyl, cycloalkyl or alkoxy and PA0 R.sup.4 represents hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, fluoroalkyl, cyanoalkyl, alkenyl, alkinyl or cycloalkyl, or PA0 R.sup.3 and R.sup.4, together with the nitrogen atom, represent a heterocyclic radical which is optionally substituted by alkyl and can be further substituted in the alkylene chain by oxygen, sulphur or nitrogen, are useful as fungicides and intermediates.

The present invention relates to new alkoxycarbonyl-substituted 
hydroxythiophene-carboxamides, a process for their preparation and their 
use as fungicides and as intermediate products. 
It is already known that 
2,5-bis-(alkoxycarbonyl)-3,4-bis-(acyloxy)-thiophenes and 
2,5-bis-(alkoxycarbonyl)-3-alkyl-4-acyloxythiophenes have fungicidal 
properties (compare European Pat. No. 32,784 and European Pat. No. 
93,384). 2,5-Bis-(isopropoxycarbonyl)-3-methyl-4-(3-methylbenzoyloxy)-thio 
phene, which is known from T. Wada et al, Proceedings of the 10th Intern. 
Congress of Plant Protection, Nov. 20-25, 1983, Brighton, Volume 1, 
400-407, may be mentioned here in particular. 
New alkoxycarbonyl-substituted hydroxythiophene-carboxamides of the general 
formula (I) 
##STR2## 
in which R.sup.1 represents alkyl, alkoxyalkyl, alkylthioalkyl, 
fluoroalkyl, cyanoalkyl, alkenyl or alkinyl or represents cycloalkyl, 
R.sup.2 represents alkyl or optionally substituted phenyl, 
R.sup.3 represents alkyl, alkoxyalkyl, alkylthioalkyl, cyanoalkyl, 
fluoroalkyl, alkenyl, alkinyl, cycloalkyl or alkoxy and 
R.sup.4 represents hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, 
fluoroalkyl, cyanoalkyl, alkenyl, alkinyl or cycloalkyl, or 
R.sup.3 and R.sup.4, together with the nitrogen atom, represent a 
heterocyclic radical which is optionally substituted by alkyl and can be 
further substituted in the alkylene chain by oxygen, sulphur or nitrogen, 
have been found. 
It has furthermore been found that the new alkoxycarbonyl-substituted 
hydroxythiophene-carboxamides of the formula (I) 
##STR3## 
in which R.sup.1 represents alkyl, alkoxyalkyl, alkylthioalkyl, 
fluoroalkyl, cyanoalkyl, alkenyl or alkinyl or represents cycloalkyl, 
R.sup.2 represents alkyl or optionally substituted phenyl, 
R.sup.3 represents alkyl, alkoxyalkyl, alkylthioalkyl, cyanoalkyl, 
fluoroalkyl, alkenyl, alkinyl, cycloalkyl or alkoxy and 
R.sup.4 represents hydrogen, alkyl, alkoxyalkyl, alkylthioalkyl, 
fluoroalkyl, cyanoalkyl, alkenyl, alkinyl or cycloalkyl, or 
R.sup.3 and R.sup.4, together with the nitrogen atom, represent a 
heterocyclic radical which is optionally substituted by alkyl and can be 
further substituted in the alkylene chain by oxygen, sulphur or nitrogen, 
are obtained by a process in which a carboxylic acid derivative of the 
formula (II) 
##STR4## 
in which R.sup.1 and R.sup.2 have the abovementioned meanings, 
is reacted with an amine of the formula (III) 
##STR5## 
in which R.sup.3 and R.sup.4 have the abovementioned meanings, 
if appropriate in the presence of a solvent or diluent and if appropriate 
in the presence of a tertiary organic base. 
It has furthermore been found that the new alkoxycarbonyl-substituted 
hydroxythiophene-carboxamides of the formula (I) have fungicidal 
properties and are also suitable as intermediate products for the 
synthesis of active compounds. 
Surprisingly, the alkoxycarbonyl-substituted hydroxythiophene-carboxamides 
of the formula (I) according to the invention exhibit a better fungicidal 
activity than the 
2,5-bis-(isopropoxycarbonyl)-3-methyl-4-(3-methylbenzoyloxy)-thiophene 
known from the prior art. 
Formula (I) provides a general definition of the alkoxycarbonyl-substituted 
hydroxythiophene-carboxamides according to the invention. Preferred 
compounds of the formula I are those 
in which 
R.sup.1 represents alkyl with 1 to 5 carbon atoms, or represents 
alkoxyalkyl or represents alkylthioalkyl with 1 to 5 carbon atoms per 
alkyl part, or represents fluoroalkyl with in each case up to 5 fluorine 
and carbon atoms, or represents cyanoalkyl with 1 to 5 carbon atoms in the 
alkyl part, or represents alkenyl with 3 or 4 carbon atoms, or represents 
alkinyl with 3 to 5 carbon atoms, or represents cycloalkyl with 4 to 6 
carbon atoms, 
R.sup.2 represents alkyl with 1 to 4 carbon atoms or optionally mono- to 
independently penta-substituted phenyl, substituents being alkyl with 1 to 
4 carbon atoms, alkoxy or alkylthio with 1 to 4 carbon atoms in each case, 
halogen, nitro, halogenalkyl, halogenoalkoxy or halogenoalkylthio with 1 
to 4 carbon atoms and 1 to 5 halogen atoms in each case (halogen means 
fluoro, chloro, bromo and iodo, preferably fluoro and chloro), 
R.sup.3 represents alkyl with 1 to 5 carbon atoms, or represents 
alkoxyalkyl or alkylthioalkyl with in each case 1 to 5 carbon atoms per 
alkyl part, or represents cyanoalkyl with 1 to 5 carbon atoms in the alkyl 
part, or represents fluoroalkyl with up to 3 fluorine atoms and up to 5 
carbon atoms, or represents alkenyl or alkinyl with 3 to 5 carbon atoms, 
or represents cycloalkyl with 3 to 6 carbon atoms, or represents alkoxy 
with 1 to 5 carbon atoms and 
R.sup.4 represents hydrogen or alkyl with 1 to 5 carbon atoms, or 
represents alkoxyalkyl or alkylthioalkyl with in each case 1 to 5 carbon 
atoms per alkyl part, or represents cyanoalkyl with 1 to 5 carbon atoms in 
the alkyl part, or represents fluoroalkyl with up to 3 fluorine atoms and 
up to 5 carbon atoms, or represents alkenyl or alkinyl with 3 to 5 carbon 
atoms, or represents cycloalkyl with 3 to 6 carbon atoms, or 
R.sup.3 and R.sup.4, together with the nitrogen atom, represent a 5-, 6- or 
7-membered heterocyclic ring which can contain aza, oxa or thia elements 
and can optionally be substituted by alkyl groups. 
Particularly preferred compounds of the formula (I) are those 
in which 
R.sup.1 represents methyl, ethyl, n- or iso-propyl, 2,2-dimethylpropyl, 
2-methoxyethyl, 2-ethoxyethyl, 2-methylthioethyl, 2-ethylthioethyl, 
2,2,2-trifluoroethyl, cyanomethyl, cyanoethyl, allyl, methallyl, 
2-propinyl, 1,1-dimethyl-2-propinyl, cyclopentyl or cyclohexyl, 
R.sup.2 represents methyl, ethyl, n-propyl, iso-propyl, n-butyl, 
sec.-butyl, iso-butyl, tert.-butyl, phenyl or halogenophenyl, 
R.sup.3 represents methyl, ethyl, n- or iso-propyl, 2,2-dimethylpropyl, 
2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 3-methoxypropyl, 
3-ethoxypropyl, 3-butoxypropyl, 2-methylthioethyl, 2-ethylthioethyl, 
2,2,2-trifluoroethyl, 2-cyanoethyl, 1-methyl-1-cyanoethyl, 
.omega.-cyanopentyl, allyl, methallyl, 2-propinyl, 
1,1-dimethyl-2-propinyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 
methoxy, ethoxy, n-propyloxy, n-butyloxy, sec.-butyloxy or n-pentyloxy, 
and 
R.sup.4 represents hydrogen, methyl, ethyl, n- or iso-propyl, 
2,2-dimethylpropyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 
3-methoxypropyl, 3-ethoxypropyl, 3-butoxypropyl, 2-methylthioethyl, 
2-ethylthioethyl, 2,2,2-trifluoroethyl, 2-cyanoethyl, 
1-methyl-1-cyanoethyl, .omega.-cyanopentyl, allyl, methallyl, 2-propinyl, 
1,1-dimethyl-2-propinyl, cyclopropyl, cyclobutyl, cyclopentyl or 
cyclohexyl, or 
R.sup.3 and R.sup.4, together with the nitrogen atom, represent 
pyrrolidine, piperidine, 2-methylpiperidine, 3-methylpiperidine, 
4-methylpiperidine, hexahydro-1H-azepine, morpholine, 
2,6-dimethylmorpholine, thiazolidine, N.sup.1 -methylpiperazine or N.sup.1 
-propylpiperazine. 
Compounds of the formula (I) which may be mentioned in particular are those 
in which 
R.sup.1 represents methyl, ethyl, isopropyl, n-propyl, sec.-butyl, 
cyclopentyl or cyclohexyl, 
R.sup.2 represents methyl, ethyl, isopropyl, tert.-butyl or phenyl, 
R.sup.3 represents methyl, butyl, or .omega.-cyanopentyl and R.sup.4 
represents hydrogen, or 
R.sup.3 and R.sup.4, together with the nitrogen atom, represent 
pyrrolidine, piperidine or morpholine. 
If, for example, 
2,5-bis-(cyclopentyloxycarbonyl)-3-methyl-4-hydroxythiophene and 
2-methoxyethylamine are used as starting compounds for the preparation of 
the compounds of the formula (I) according to the invention, the course of 
the reaction can be represented by the following equation: 
##STR6## 
4-Hydroxythiophene derivatives, of which formula (II) provides a general 
definition, are required as starting substances for the reactions to give 
the compounds according to the invention. The starting compounds of the 
formula (II) are known to some cases, but can also be prepared by 
generally known processes, thus, for example, from thiodiacetic acid 
esters and 2-oxocarboxylic acid esters under alkaline conditions, for 
example under the action of potassium tert.-butylate, and after the 
condensation, the product is treated with an acid (compare European Pat. 
No. 93,384 and DAS (German Published Specification) No. 1,020,641). The 
reaction can be illustrated by the following equation: 
##STR7## 
Compounds which may be mentioned specifically are: 
3-methyl-4-hydroxy-thiophene-2,5-dicarboxylic acid methyl, ethyl, 
isopropyl, 1-methylpropyl, 2,2-dimethylpropyl, cyanomethyl, 2-cyanoethyl, 
1-cyano-1-methylethyl, 2,2,2-trifluoroethyl, 2-methoxyethyl, 
2-butylthioethyl, 2-ethylthioethyl, allyl, methallyl, propargyl, 
1,1-dimethylpropargyl, cyclobutyl, cyclopentyl and cyclohexyl ester; and 
4-hydroxy-3-ethyl-, -3-propyl-, -3-isopropyl-, -3-butyl-, -3-phenyl- and 
-3-tert.-butyl-thiophene-2,5-dicarboxylic acid 2,2,2-trifluoroethyl ester. 
Primary and secondary amines of the formula (III), which are known from the 
literature, for example methylamine, dimethylamine, ethylamine, 
diethylamine, n-propylamine, di-n-propylamine, iso-propylamine, 
sec.-butylamine, iso-butylamine, n-butylamine, di-n-butylamine, amylamine, 
N-methylamylamine, 2-methoxyethylamine, 2-ethoxyethylamine, 
N-methyl-2-methoxyethylamine, 3-methoxypropylamine, 3-butoxypropylamine, 
2-methylthioethylamine, 2-butylthioethylamine, 
N-methyl-3-butylthiopropylamine, 2-cyanoethylamine, 
1-cyano-1-methylethylamine, .omega.-cyanopentylamine, 
2,2-difluoroethylamine, 2,2,2-trifluoroethylamine, 
3,3,3-trifluoropropylamine, 2,2-difluorobutylamine, 
4,4,4-trifluorobutylamine, 1-trifluoromethylethylamine, allylamine, 
diallylamine, methallylamine, propargylamine, N-methylpropargylamine, 
cyclopropylamine, cyclobutylamine, cyclopentylamine, cyclohexylamine, 
N-methylcyclohexylamine, N-butoxyamine, N-methyl-N-butoxyamine, 
pyrrolidine, piperidine, 2-, 3- or 4-methylpiperidine, 2-ethylpiperidine, 
morpholine, 2,6-dimethylmorpholine, N.sup.1 -methylpiperazine, N.sup.1 
-propylpiperazine, thiazolidine and hexahydro[1H]-azepine, are furthermore 
required for the reaction to give the compounds according to the 
invention. 
Possible diluents for the process are all the organic solvents which are 
inert towards the reaction partners; polar solvents are preferably used. 
Examples which are to be mentioned here are: acetonitrile, 
dimethylacetamide, dimethylformamide, dimethylsulphoxide, 
N-methylpyrrolidone, dioxane, chlorobenzene, benzonitrile, 
ethyldiisopropylamine, triethylamine, tributylamine, 
dimethylcyclohexylamine, ethyldicyclohexylamine, dimethylbenzylamine, 
pyridine, picoline and quinoline, or the amine of the formula (III) to be 
reacted is used as the solvent. 
The reaction temperatures and the reaction time are determined by the 
activity of the starting substances. In general, the reaction is carried 
out between about 20.degree. and 180.degree. C., preferably between 
40.degree. and 150.degree. C. 
In the case of reaction of low-boiling amines, it can be advantageous to 
carry out the reaction under pressure. 
Depending on the operating conditions, the compounds according to the 
invention precipitate as crystals or remain dissolved in the organic 
solvent, and, after distilling off excess amine, which should be recovered 
as completely as possible, for economic reasons, and after washing with 
water and dilute acid, they can be isolated, during which they are 
deposited from their solutions, if appropriate, by addition of solvents of 
low polarity, such as cyclohexane, dibutyl ether or carbon tetrachloride. 
The active compounds according to the invention exhibit a powerful 
fungicidal action and can be employed in practice for combating undesired 
fungi. 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. 
Some pathogens of fungal diseases which fall within the generic names 
listed above may be mentioned as examples but not by way of limitation: 
Pythium species, such as, for example, Pythium ultimum; Phytophthora 
species, such as, for example, Phytophthora infestans; Pseudoperonospora 
species, such as, for example, Pseudoperonospora humuli or 
Pseudoperonospora cubense; Plasmopara species, such as, for example, 
Plasmopara viticola; Peronospora species, such as, for example, 
Peronospora pisi 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 (conidia form: Drechslera, syn: Helminthosporium); 
Cochliobulus species, such as, for example, Cochliobolus sativus (conidia 
form: Drechslera, syn: 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, 
Leptosphaeria nodorum; Cercospora species, such as, for example, 
Cercospora canescens; Alternaria species, such as, for example, Alternaria 
brassicae; and 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 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, and 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 
dimethyl sulphoxide, 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 their 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, corn 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, alkyl sulphonates, alkyl sulphates, aryl sulphonates as 
well as albumin hydrolysis 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 
alcohol and polyvinyl acetate, as well as natural phospholipids, such as 
cephalins and lecithins, and synthetic phospholipids, can be used in the 
formulations. Other 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 phthal-ocyanine dyestuffs, 
and trace nutrients such as salts of iron, manganese, boron, copper, 
cobalt, molybdenum and zinc. 
The formulations 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, as well as in 
mixtures with fertilizers and growth regulators. 
The active compounds can be used as such or in the form of their 
formulations or the use forms prepared therefrom by further dilution, such 
as ready-to-use 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, atomizing, scattering, dusting, foaming, brushing and the like. 
It is furthermore possible to apply the active compounds by the ultra-low 
volume method or to inject the active compound formulation or the active 
compound itself into the soil. The seed of the plants can also be treated. 
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, between 1 and 0.0001% by weight, preferably between 0.5 and 
0.001%. 
In the treatment of seed, amounts of active compound of 0.001 to 50 g per 
kilogram of seed, preferably 0.01 to 10 g, are generally required. 
For the treatment of soil, active compound concentrations of 0.00001 to 
0.1% by weight, preferably 0.0001 to 0.02%, are required at the place of 
action. 
The compounds according to the invention can be used as intermediate 
products for the preparation of active secondary products.

PREATION EXAMPLES 
Example 1 
##STR8## 
10 g of 2,5-bis-(methoxycarbonyl)-3-methyl-4-hydroxythiophene and 100 ml of 
benzonitrile are heated to 130.degree. C. and a weak stream of methylamine 
is passed in for 15 hours. 
The solvent is stripped off in vacuo. The residue is diluted with ethyl 
acetate and washed twice with 5% strength ice-cold sulphuric acid and 
twice with water. The mixture is dried over sodium sulphate and evaporated 
in vacuo and the evaporation residue is crystallized from 20 ml of 
methanol. 
Yield: 1 g of 
2-methoxycarbonyl-3-methyl-4-hydroxy-5-methylaminocarbonylthiophene 
Melting point: 190.degree. C. (decomposition); 
H.sup.1 -NMR; 80 MHz, CDCl.sub.3 +d-DMSO (.delta.ppm): 3H, s, 2.38 
(CH.sub.3); 3H, s, 3.88 (CH.sub.3 OOC--) and 3H, d 2.87 (CH.sub.3 --NH--). 
EXAMPLE 2 
##STR9## 
90 g of 2,5-bis-(isopropoxycarbonyl)-3-methyl-4-hydroxythiophene and 450 g 
of morpholine are heated at 124.degree. C. for 91/2 hours. The excess 
morpholine is evaporated off in vacuo. The evaporation residue is 
dissolved in 600 ml of methylene chloride and the solution is washed twice 
with ice-cold diluted sulphuric acid and once with water. It is dried with 
sodium sulphate. After evaporating off the solvent, the residue is 
triturated with a little diisopropyl ether, separated off and dried at 
60.degree. C./1 mbar. Yield: 78.9 g of 
2-isopropoxycarbonyl-3-methyl-4-hydroxy-5-(1-aza-4-oxacyclohex-1-ylcarbony 
l)-thiophene of melting point 123.degree. C. 
The compounds of the formula (I) are obtained in the same manner: 
__________________________________________________________________________ 
##STR10## (I) 
Example 
R.sup.1 R.sup.2 
R.sup.3 R.sup.4 
Melting point [.degree.C.] 
__________________________________________________________________________ 
3 H.sub.5 C.sub.2 
H.sub.3 C 
C.sub.2 H.sub.4OC.sub.2 H.sub.4 
131 
4 n-H.sub.7 C.sub.3 
" " 126 
5 C.sub.2 H.sub.5 (CH.sub.3)CH 
" " 99 
6 (CH.sub.3).sub.2 CH 
" C.sub.5 H.sub.10 
86 
7 " " C.sub.4 H.sub.8 
134 
8 " " (CH.sub.2).sub.5 CN 
H 94 
9 " " C.sub.6 H.sub.11 
H 124 
10 H.sub.3 C 
(CH.sub.3).sub.2 CH 
C.sub.2 H.sub.4OC.sub. 2 H.sub.4 
115 
11 
##STR11## 
H.sub.3 C 
" 123 
12 C.sub.2 H.sub.5 (CH.sub.3)CH 
H.sub.3 C 
C.sub.5 H.sub.10 
viscous 
13 " " C.sub.2 H.sub.4 OCH.sub.3 
H 79 
14 H.sub.3 C 
" " " 99 
15 H.sub.5 C.sub.2 
" C.sub.5 H.sub.10 
89 
16 n-H.sub.7 C.sub.3 
" C.sub.5 H.sub.10 
74 
__________________________________________________________________________ 
USE EXAMPLE 
The compound shown below is employed as the comparison substance in the use 
example which follows: 
##STR12## 
Example A 
Pyricularia test (rice)/protective 
Solvent: 12.5 parts by weight of acetone 
Emulisifier: 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 the 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 off, 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. 
Thereafter, the plants remain in a greenhouse at a temperature of 
25.degree. C. and a relative atmospheric humidity of 100% until they are 
evaluated. 
Evaluation of the disease infestation is carried out 4 days after the 
inoculation. 
In this test, for example, a clearly superior activity compared with the 
prior art is shown by the compound according to preparation Example 1. 
It will be understood that the specification and examples are illustrative 
but not limitative of the present invention and that other embodiments 
within the spirit and scope of the invention will suggest themselves to 
those skilled in the art.