JPS63119402A - Agricultural and horticultural fungicide - Google Patents

Abstract

(57) [Abstract] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention]

The present invention relates to a fungicide useful for agriculture and horticulture and the use of the same to control fungal and bacterial infections in plants. The present invention uses the general formula (1) as an active ingredient (wherein R1 and R2 are each a hydrogen atom or 1 to
The present invention provides an agricultural and horticultural fungicide containing a thiophene derivative having an alkyl group having 4 carbon atoms, and X represents a methylene group or an oxygen atom, or an acid addition salt thereof. -II The alkyl group in the active ingredient of formula (I) is a straight-chain or branched alkyl group having 1 to 6, e.g. 1 to 4, carbon atoms, specific examples of which are methyl, ethyl, propyl. (n- or iso-propyl) and butyl (n-1sec-, iso- or t-butyl),
And methyl group is particularly preferred. The acid addition salts include salts with acids or organic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, oxalic acid, acetic acid, tartaric acid,
It may be a salt with 4-toluenesulfonic acid or methanesulfonic acid. A specific example of the active ingredient used in the fungicide of the present invention is 2-te.
rt-Butyl-5-(2-methyl-3-piperidinopropyl)thiophene, 2-tert-butyl-5-[2-
Methyl-3-(2-methylpiperidino)propylcothiophene, 2-tert-butyl-5-[2-methyl-3
-(3-methylpiperidino)propylcothiophene,
2-tert-butyl-5-(2-methyl-3-(4-
Methylpiperidino)propylcothiophene, 2-ter
t-Butyl-5-(3-(3,5-dimethylpiperidino)-2-methylpropylcothiophene, 2-tere-
Butyl-5-(2-methyl-3-morpholinopropyl)
Thiophene, 2-tert-butyl-5-[:3-(
Includes 2,6-dimethylmorpholino)-2-methylpropylcothiophene and acid addition salts thereof. Furthermore, use of the fungicide of the present invention is useful for controlling fungal and bacterial disease infections of plants. The thiophene derivative as an active ingredient can be prepared using the Clemensen method (E. L. Martin's Organic Rea).
ction Vol. 1, p. 155 (1942)] according to the general formula (■) (wherein R1 and R2 each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and X is a methylene group. or an oxygen atom) is easily produced by reduction of a thenyl ketone compound. The above Clemensen reduction reaction is usually carried out in hydrochloric acid as a solvent, and the concentration of hydrochloric acid used is in the range of 5-35%, preferably 20-30%. Preferably, the zinc amalgam used is prepared before use. 1 to 3 parts of zinc powder is used per 1 part of the raw material chenyl ketone compound (■). The reaction is preferably carried out by stirring the mixture at room temperature or solvent reflux temperature for 15 minutes to 48 hours. It is preferable to add 35% hydrochloric acid in about 1 to 5 portions at appropriate intervals. The produced thiophene derivative (1) can be isolated by a conventional method,
Purification is then achieved by vacuum distillation, recrystallization, chromatography and other methods. If necessary, the free base of the above derivatives can be replaced with an acid addition salt by standard methods. The chenyl ketone compound (II) used as a starting material in the above reduction reaction can be used, for example, in the Mannich reaction (F, F,
(See Organic Reaction, Vol. 1, p. 308 (1942) of the old 1cke) (III) (mV)
1, R2 and X represent the same atoms or groups as above)
This is a new compound that can be produced by This reaction is carried out according to the conventional Mannich reaction method, preferably using 2-tert-butyl-5-propionylthiophene (III), 35%
This is done by stirring and refluxing the formaldehyde solution and amine compound (IV) in ethanol for 1 to 10 hours. The produced chenyl ketone compound (■) can be separated and purified by conventional methods. The fungicide or composition of the present invention is effective against the following diseases and is therefore useful for controlling the following diseases. Wheat rust (Puccinia recondita)
, Puccinia striiiformis and other rusts), barley rust (Puccinia horde
P. ei, Puccinias triiformis and other rusts) and other host plant rusts such as coffee, fruit trees, especially apples, vegetables and ornamental plants; powdery mildew of barley and wheat (e.g. Powdery mildew (cucumber)
, and other powdery mildews on main plants of apples; radon mildew of cereals (肚膓帥錣陇冇工 and 肚膓帥幣 and Wang憇五上); Kappan disease of groundnuts (肚膓帥錣陁膇工)
arachidicola) as well as e.g. sugar beet,
Botrytis blight on bananas and soybeans, Botrytis blight on tomatoes, strawberries, grapes and other host plants;
Crohon disease of apples (Venturia sinensis)
. Certain active ingredient compounds of the present invention have also shown broad activity against fungi in vitro. They are effective against various post-harvest fruit diseases [e.g. orange green mold (r'enici)].
lliun+ Salmon Pμ Dianmei) and blue mold disease (Peni
It has activity against banana stem rot (Cillium italium) and banana stem rot (Oeos musarum). Some of the active ingredient compounds of the present invention can be used as seed dressings to combat cereal diseases and diseases. Tiletia cloud (i.e. smut,
A disease that occurs on wheat seeds), Ustilag Oβ. Rhi: xocon
5o1ani) and rice sheath blight (Corticiun).
+5asak, Lj). The active ingredient compound of the present invention can move atopically within the plant tissue. Furthermore, the compound may be sufficiently volatile to be active in the vapor phase against fungi on plants. The active compounds of the invention may also be useful as industrial fungicides (as opposed to agricultural), for example for protecting wood, hides, leather and especially paint coatings from attack by fungi. The active ingredient compound of the present invention may also be used, for example, to treat the disease Xantho.
The plant exhibits antibacterial activity against Monas eu (rice blight), and therefore the present invention encompasses a method of treating plants to control the bacterial disease. Although the active ingredient compounds of the present invention can be used as such for fungicidal applications, it is more convenient to formulate them into compositions for use in such applications. Accordingly, the present invention provides a fungicide composition or a plant growth regulator composition comprising a compound of general formula (1) or an acid addition salt as defined above. The active ingredient compounds of the present invention and their acid addition salts can be applied in various ways. For example, the compounds can be formulated or applied directly to plant leaves without formulation, or they can be applied to shrubs and trees, to seeds,
or the compounds can be applied to or sprayed onto other media in which plants or trees are grown or planted. They can be sprinkled or applied as cream or pellet formulations, or the compounds can be applied as vapors or as slow-release granules. Application to any part of the plant, shrub or tree. It can be applied, for example, to the leaves, stems, branches or roots, or to the soil around the roots, or to the seeds before sowing, or to the soil in general, to the water of rice fields or to hydroponic cultivation systems. The active ingredient compounds of the invention can also be injected into heads or trees and can also be sprayed onto plants using electric spraying methods. The term "plant" as used in the specification includes seedlings, shrubs and trees.Furthermore, the sterilization method of the present invention includes preventive, protective and eradication treatments.The active ingredient compound of the present invention is preferably 5 horticultural use in the form of a composition. The type of composition used will vary depending on the particular purpose intended. The composition of the invention comprises the active ingredient and a solid diluent or It may be in the form of a dispersible powder or granules consisting of a carrier and fillers such as kaolin, bentonite dolomite, calcium carbonate, talc, powdered magnesia, Fuller's earth, gypsum, herite, diatomaceous earth and china clay. Such granules The granules may be hand-formed granules suitable for application to the soil without further treatment. These granules may be made by impregnating filler pellets with the active ingredient or by combining the active ingredient with a powdered filler. The composition for seed dressings may contain, for example, an agent that promotes the adhesion of the composition to the seeds (e.g., mineral oil); it may also contain an organic solvent (e.g., N −
The active ingredient can be formulated for seed dressing using methylpyrrolidone, or dimethylformamide). The compositions of the invention may also be in the form of wettable powders or water-dispersible granules containing a wetting agent to facilitate the dispersion of the powder or granules in a liquid; such powders or granules may further include It may contain fillers and suspending agents. Aqueous dispersions or emulsions are prepared by dissolving one or more active ingredients in an organic solvent which may optionally contain one or more wetting agents, dispersing agents or emulsifying agents, and then dispersing this mixture with one or more wetting agents. It can be prepared by adding to water which may contain agents or emulsifiers. Suitable organic solvents include ethylene dichloride, isopropyl alcohol, propylene glycol, diacetone alcohol, toluene, kerosene, methylnaphthalene, xylenes, trichloroethylene, furfuryl alcohol, tetrahydrofurfuryl alcohol and glycol ethers such as 2-ethoxyethanol and -butoxetanol). Compositions of the invention for use as spray liquids may also be in the form of aerosols, which are formulations held in a container under pressure in the presence of a propellant, such as fluorotrigloromethane or diglorodifluoromethane. The active ingredient compounds of the present invention can also be mixed in the dry state with a carpenter's mixture to form a composition suitable for generating smoke containing the compound in a confined space. Alternatively, the active ingredient compounds of the invention can be used in microencapsulated form. They can also be formulated into biodegradable polymeric formulations to provide slow and controlled release of the active substance. Different compositions can be better adapted to different applications by including suitable additives, such as additives to improve spreadability, adhesion and amphoteric resistance to the surface to be treated. The active compounds according to the invention can be used in mixtures with fertilizers (for example nitrogen-, potassium- or phosphorus-containing fertilizers). Compositions consisting only of fertilizer granules containing the active ingredient compounds, for example by coating, are preferred. Suitably such granules contain up to 25% by weight of the active ingredient compound. Accordingly, the present invention also provides fertilizer compositions containing a compound of general formula (I) or a salt thereof. The compositions of the invention are generally aqueous dispersions or emulsions containing the active ingredient in the presence of one or more surfactants, such as wetting agents, dispersing agents, emulsifying agents or suspending agents, or by electric spraying. It may be in the form of a solvent to be used as a dip or spray liquid, which is a propellant of a type suitable for use in. The agents may be cationic, anionic or nonionic active agents. Suitable cationic activators are quaternary ammonium compounds such as cetyltrimethylammonium bromide. Suitable anionic active agents include soaps, salts of aliphatic monoesters of sulfuric acid (e.g. sodium lauryl sulfate-1.
), salts of sulfonated aromatic compounds (e.g. sodium
dodecylbenzenesulfonate, sodium, calcium or ammonium lignosulfonate, butylnaphthalenesulfonate and a mixture of the sodium salts of diisopropyl and triisopropylnaphthalenesulfonic acids). Suitable nonionic surfactants are condensation products of ethylene oxide with aliphatic alcohols such as oleyl alcohol or cetyl alcohol or alkyl phenols such as octylphenol, nonylphenol or octyl cresol. Other nonionic surfactants are partial esters derived from long chain fatty acids and hexitol anhydride, condensation products of the partial esters with ethylene oxide, and lecithin. Suitable suspending agents are hydrophilic colloids (eg polyvinylpyrrolidone and sodium carboxymethylcellulose) and vegetable gums (eg acacia and tragacanth). Compositions used in the form of aqueous dispersions or emulsions are usually supplied in the form of concentrates containing a high proportion of the active ingredient and are diluted with water before use. Such concentrates often can withstand long-term storage and, when diluted with water after such long-term storage, form an aqueous formulation that remains homogeneous for a sufficient period of time to be applied with conventional powered spray equipment. It is necessary. Such concentrates conveniently contain up to 95% by weight, preferably 10-85% by weight, such as 25-60% by weight.
may contain active ingredients. These concentrates suitably contain an organic G (for example an alkanol sulfonic acid such as xylene sulfonic acid or dodecylbenzenesulfonic acid). This is because the presence of such acids can increase the solubility of the active ingredient in the polar solvents often used for concentrates. The concentrates also suitably contain a high proportion of surfactants so as to obtain emulsions that are sufficiently stable in water. After dilution to make aqueous formulations, such formulations may contain varying amounts of one or more active ingredients depending on their intended use, but from o,oos to 0.01% by weight of active ingredients. Aqueous formulations containing 10% by weight can be used. The compositions of the invention may also contain one or more other biologically active compounds, such as compounds with similar or supplementary fungicidal or plant growth activity or compounds with plant growth regulating, herbicidal or insecticidal activity. It can also be contained. Other fungicidal compounds are used to combat ear diseases of cereals (e.g. wheat), seed and soil-borne diseases such as 7fll, Gibberella spp. and 匡HA side 彷nami Lu situm, as well as downy mildew and powdery mildew of grapes and apples. It may be a compound that can control powdery mildew and rot, such as. Mixtures of these fungicides have the general formula (
It may have a broader range of activity than the compound of general formula (1) alone, and furthermore, other fungicides may have a synergistic effect on the fungicidal activity of the compound of general formula (1). Specific examples of other fungicidal compounds include carpendazim, benomyl, thiophanate methyl, thiabendazole, fubelidazole, 1-ridazole, diglofluanid, cymoxanil, oxaxyl, offrace, metalaxyl, fluaraxyl, benaraxyl, phosethylaluminum, fenarimol, iprodione, procymidone. ,
Vincloprine, Penconazole, Myclobutanil, R
O151297, Virasifuos, Ethyrimol, Citalimfos, Tridemorph, Trifoline, Nuarimol, Triazbutyl, Guazatine, Triacetate salt of 1,1'-iminodi(octamethylene)diguanidine, Propiconazole, Prochloraz, Flutriafol, Hexaconazole i.e. 1- (1,2.4-triazol-1-yl)-2-(2,4-diglorophenyl)hexan-2-ol, (2-RS, 3-RS)-2
- (4-chlorophenyl)-3-cyclopropyl-1
-(ill-1.2.4-triazol-l-yl)butan-2-ol(RS)-1-(4-chlorophenyl)-4.4-dimethyl-3-(111-1.2.4-
Triazole-1-1' /I/ methyl)pentan-3-ol, DPX 116573 (1-[(bis-4-fluorophenyl)methylsilyl]-methyl)I
H-1.2.4-triazole, triadimetuone, triadimenol, diclobutrazol, fenpropimorph, fenpropidine, chlorosilinate, diniconazole, imazalil, fenflam, carboxin, oxycarboxin, metofloxam, dobumorph, B.A.
S454, plasticidin S, kasugamycin, nidifenfos, xylene P, cycloheximide, phthalide, probenazole, isobrothiolane, tridiclazole, pyroquilone, 4-chloro-N-(cyano(technical)
xy)methyl]benzamide, chlorbenzthiacin,
Neoalazine, polyoxin D, validamycin A, mepronil, flutolanil, benziclon, diclomedine, phenazine oxide, nickel dimethyl dithiocarbamate, tecroftalam, bittertanol, bupirimate, etaconazole, streptomycin, ciproflam, pyroxazole, quinomethionate, dimethylimole, 1-(2-cyano -2-methoxy-iminoacetyl)
-3-ethyl urea, fenapanil, triclofos-
Methyl, biloxiflu, polyram, maneb, manconeb, cabtafur, chlorothalonil, anisidine, thiram, cabtan, folpet, zineb, propineb, sulfur, dinocap, binapacryl, nitrotal-isopropyl, dodine, dithianone, fentin hydroxide, fentin acetate , technazene, quintozene, dichlorane, copper-containing compounds such as copper oxychloride and copper sulfate, and Bordeaux mixture, and organomercury compounds. General formula (

The compounds [) can be mixed with soil, peat or other root media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases. Suitable insecticides that can be incorporated into the compositions of the invention are pirimicarb, dimethoate, demeton-S-methyl. formothion, carb aryl, isoprocarb,
XMC, BPMC, carbofuran, carbosulfan,
Includes diazinon, fenthion, fenitrothion, phen 1-ate, chlorpyrifos, isoxathion, propafos, monocrotophas, buprofezin, nitroproxyfen and cycloprothrin. Suitable plant growth regulating compounds modulate weed or seed head formation, or control less desirable plants (e.g. grasses).
It is a compound that selectively regulates the growth of. Examples of suitable plant growth regulating compounds for use with the active ingredient compounds of the present invention include gibberellin (e.g. GA,
GA4 or GA, ), auxins (e.g. indoleacetic acid, indolebutyric acid, naphthoxyacetic acid or naphthylacetic acid), cytokinins (e.g. kinetin, diphenylurea, benzimidazole, benzyladenine or benzylaminopurine), phenoxyacetic acid (e.g. 2.4
-D or MCPA), substituted benzoic acids (e.g. triiodobenzoic acid), morphactin (e.g. chlorofluoroechol), maleic hydrazide, glyphosate,
glyfosine, long chain fatty alcohols and fatty acids, zigaglac, balobdrazole, flurpyrimidol,
Fluorideamide, mefluidide, substituted quaternary ammonium and phosphonium compounds (e.g. chloromequat, chlorphonium or mepiquat chloride), ethephon, carbetamide, methyl-3°6-cycloanisate, daminozide, aslam. Abscisic acid, isopyrimole, 1-(4-chlorophenyl-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid, hydroxybenzonitrile (e.g. bromoxynil), dipenzocort, benzoylprop-ethyl, 3 , 6-dichloropicolinic acid, fenpentezole, inabenfide, triabentenol and technazene.The present invention is illustrated by the following examples. The formulation of the active ingredient compounds used is illustrated. Examples 8 to 17 illustrate compositions according to the invention. Example 18 illustrates the sterilization method. (
2,94g), 3,5-dimethylpiperidine hydrochloride (3
, 34 g), 35% formaldehyde aqueous solution (3,81
A mixture of 3 g ), ethanol (5 mQ) and 1 drop of concentrated hydrochloric acid was refluxed for 6 hours with stirring. After the reaction was completed, the mixture was cooled with ice-cold water, and the precipitated white solid was filtered and washed with a small amount of water. The obtained white solid was diluted with hexane.
Recrystallized from acetone solution to give 2-tert-butyl-5
-[3-(3,5-dimethylpiperidino)-2-methylpropionylcothiophene hydrochloride with a melting point of 188 to [90
Obtained as white plate-like crystals (3.84 g) at °C (decomposed). By using the same procedure as in Example 1 except that a new starting material was used in Examples 2 to 7 instead of 3,5-dimethylpiperidine hydrochloride, the following table ( The following table (Table ■) shows the main signals obtained by NMR and mass spectrometry of the compounds of Examples 1 to 7. Table II Freshly prepared zinc amalgam [Zinc End (2.13g)
and 25% hydrochloric acid (4 mffi) by adding mercuric chloride (0.21 g) while stirring the mixture, and when the mixture separated into two layers after a while, the supernatant liquid was gently poured]. Mix with 2-tert-butyl-5-(3-3,5-dimethylpiperidino)-2-methylpropionylcothiophene hydrochloride (1,79 g) obtained in Example 1 and 25% hydrochloric acid (8 mQ). The mixture was then refluxed for 24 hours with stirring. During the reaction, 35% hydrochloric acid (2 ml
2) was added twice at 8 hour intervals. After the reaction is complete, dilute the reaction solution with water, add caustic soda to make it alkaline,
Then it was extracted with benzene. Wash the benzene layer with water. Dry over anhydrous sodium sulfate and evaporate the benzene to give an oily 2-tert-butyl-5-(3-(3,5-
Dimethylpiperidino)-2-methylpropylcothiophene (1.29 g) was obtained. The resulting oil was dissolved in carbon tetrachloride. Dry hydrogen chloride gas was bubbled through it. The precipitated white solid was filtered and recrystallized from an acetone-hexane mixture to give 2-tert-butyl-5-(3-(3,
5-dimethylpiperidino)-2-methylpropylcothiophene hydrochloride was obtained as white plate-like crystals with a melting point of 192-195°C. A new starting material was used in place of 2-tert-butyl-5-(3-(3,5-dimethylpiperidino)-2-methylpropylcothiophene hydrochloride in Examples 2A to 7A). The compounds shown in the following table (Table+n) were obtained by using the same procedure as in Example IA, except that the main signals obtained by NMR and mass spectrometry of the compounds of Examples IA-7A are An emulsion was prepared by mixing the following components and stirring the mixture until all the components were dissolved. Compound of Example 1 10% Ethylene dichloride 40 % Calcium Dodecylbenzenesulfonate 5% "Lubrol" L 10% "Aromazol JFt 35% 1" Man Liquid by grinding the first three ingredients together in the presence of added water and then mixing in sodium acetate The composition was prepared in the form of granules that were easily dispersed in the IB. The resulting mixture was dried and sieved using a British Standard Sieve, size 44-10
0 to obtain granules of desired size. Compound of Example 2 50% "Dispersol" T 25% "Lubrol JA P N 5 1.5
% Sodium acetate 23.5
% Example 10 The following ingredients were all ground together to produce a powder easily dispersible in liquid. Compound of Example 3 45% "Dispersol JT 5%"
Lisa Paul JNX O,5
% "Cerophas J B 600
2% sodium acetate 4
The active ingredient was dissolved in a solvent and the resulting liquid was sprayed onto the surface of fine particles of china clay. The solvent was then evaporated to produce a granule composition. Compound of Example 4 5% china clay
A composition suitable for use as a seed dressing was prepared by mixing up to 0.01 U of the three components. Compound of Example 5 50% mineral oil 2% china clay 48% A powder was prepared by mixing the active ingredient with talc. Compound of Example 6 5% Talc 95% O
A dispersion (col) formulation was prepared by ball milling the ingredients listed below and then forming an aqueous suspension of the ground mixture and water. Compound of Example 7 40% "Dispersol" T 10% "Lubrol JAPN5 1% Water
49% Dog Week 11115 A wettable powder was prepared by mixing together the ingredients listed below and then grinding the mixture until all were thoroughly mixed. Compound of Example IA 25% "Aerosol" ○T/B 2%
Dipersol JAC 5% Ceramic clay 28% Silica 40%'1
1j This example describes the preparation of a hydrating powder. The following ingredients were mixed and the mixture was then ground in a pulverizing mill. Compound of Example 2A 25% Perminal JBX 1% Dispersol JT 5% Polyvinylpyrrolidone 10% Silica 25% Ceramic clay
A wettable powder was prepared by mixing the ingredients listed below and then grinding the ingredients. Compound of Example 3A 25% Aerosol JOT/B 2% Dispersol JA 5% china clay 68% In Examples 8-17 the proportions of the given components are by weight. In Examples 1-7 and IA-7A All of the compounds listed were similarly formulated as detailed in Examples 8 to 17. Descriptions of the compositions or materials designated by the various trademarks and trade names mentioned above are as follows: 2. Condensate of nonylphenol (1 mol) and ethylene oxide (13 mol) Aromasol H: Solvent mixture of alkylbenzenes Dispersol T and AC: Mixture of sodium sulfate and a condensate of formaldehyde and sodium naphthalene sulfonate Lubrol APN5: Nonylphenol Condensate of (1 mol) and naphthalene oxide (5.5 mol) Cellophas B600: Sodium carboxymethyl cellulose thickener Lisapol NX: Condensate of nonylphenol (1 mol) and ethylene oxide (8 mol) Aromasol○T/B: Dioctyl Sodium Sulfosuccinate Perminal BX: Sodium Alkylnaphthalene Sulfonate Damage 1111 The active ingredient compound of the present invention was tested against leaf diseases of various plants.The method used was as follows. Grown in John Innes potting compost (Nnl or Na2) in mini-pots. Test compounds were bead milled with an aqueous Dispersol T solution or prepared at the desired concentration immediately before use. The formulation was prepared as an acetone or acetone/ethanol solution diluted with
It was applied to the roots of plants through the soil. The spray solution was applied for maximum retention and the roots were soaked to a final 91 degrees equivalent to approximately 40 ppm active ingredient dry soil. Ttveen 20 was added to the spray solution so that the final concentration was 0.05% when sprayed on grains. For most of the tests, the active ingredient compounds of the invention were applied to the soil (roots) and leaves (by spraying) one or two days before inoculating the plants with the pathogen. Only in the test against powdery mildew (Erysiphe graminis), spraying was performed 24 hours after inoculation with the pathogen. Leaf-causing bacteria were sprayed as a spore suspension onto the leaf surfaces of test plants. After inoculation with the pathogen, the plants were transferred to a suitable environment to allow the infection to progress, and were then infected until the disease could be evaluated. The period from inoculation to evaluation varied between 4 and 14 days depending on the disease and environment. Disease control rates were recorded according to the following grades. 4=No disease outbreak

Claims (1)

[Claims] 1. General formula as an active ingredient: ▲ Numerical formula, chemical formula, table, etc. ▼ (I) (In the formula, R^1 and R^2 are each a hydrogen atom or 1 to 4 carbon atoms and X represents a methylene group or an oxygen atom) or an acid addition salt thereof. 2. The active ingredient is 2-tert-butyl-5-
The fungicide according to claim 1, which is (2-methyl-3-piperidinopropyl)thiophene. 3. The fungicide according to claim 1, wherein the active ingredient is 2-tert-butyl-5-[2-methyl-3-(2-methylpiperidino)propyl]thiophene. 4. The fungicide according to claim 1, wherein the active ingredient is 2-tert-butyl-5-[2-methyl-3-(3-methylpiperidino)propyl]thiophene. 5. The fungicide according to claim 1, wherein the active ingredient is 2-tert-butyl-5-[2-methyl-3-(4-methylpiperidino)propyl]thiophene. 6. The active ingredient is 2-tert-butyl-5-[3-(3
, 5-dimethylpiperidino)-2-methylpropyl]thiophene. 7. The fungicide according to claim 1, wherein the active ingredient is 2-tert-butyl-5-(2-methyl-3-morpholinopropyl)thiophene. 8. The active ingredient is 2-tert-butyl-5-[3-(2
, 6-dimethylmorpholino)-2-methylpropyl]thiophene.