NO844487L - E-TRIAZOLYL-PENTENOLS, PROCEDURE FOR THE PRODUCTION OF THESE AND BIOCIDES CONTAINING THESE - Google Patents

Description

The present invention relates to new E-triazolyl pentenols according to the preamble of claim 1, a method according to the preamble of claim 14 for producing these compounds as well as means according to the preamble of claims 19 and 23 containing these active substances.

Constitutionally analogous compounds with the same direction of action are previously known (DE-OS 3 010 560; DE-OS 3 148 742).

An aim of the present invention is to provide new active substances with superior properties.

According to the invention, this task is solved by the object specified in the characterizing part of the claims. Advantageous embodiments are described in the subclaims.

In comparison with the known constitutionally analogous active substances, the new compounds surprisingly exhibit a superior biocidal effect and a particularly beneficial growth-regulating effect for plants and thereby significantly enrich the state of the art in this area.

The growth-regulating effect is shown by different plant species such as, for example, cereal species, grass species, cotton, fruit trees and ornamental plants.

In the case of cereal species, a shortening of the straw is achieved, which leads to a greater resilience of the plant.

Grass species in lawns are inhibited in their growth so that

a mowing job is omitted.

In the case of cotton, the inhibition of growth causes a uniform ripening of the capsules and causes a higher yield.

In the case of fruit trees, the specified influence on the vegetative growth also leads to an increase in yield.

In the case of ornamental plants, the growth reduction has that effect

that more plants can be grown per surface unit.

The new compounds also have the advantage that, by special administration, they can inhibit the growth of unwanted species such as, for example, certain weeds, so that the beneficial plants achieve a growth advantage, with which a herbicidal effect is thus achieved. In the meantime, the inhibitory properties of the compounds can also be used to undercut the generative phase, for example with sugar beet which should not flower too early.

The new compounds are also surprisingly suitable for increasing stress resistance in useful plants such as cotton, rice, maize, soya, wheat and others.

The increase in drought resistance is particularly outstanding.

The new compounds can be used both pre-emergence and post-emergence. They exhibit a wide range of effects. The amount of application amounts to! suitable 0.001 to 5 kg of active ingredient/ha.

The period of use depends on the purpose of use and the climatic conditions.

The fungicidal effect of the new compounds is surprisingly directed against fungi of the most diverse systematic constellation. When treating above-ground plant parts, they protect against wind-borne disease agents. Against seed-borne pathogens, the compounds can be used for seed treatment.

In addition, these systems work, i.e. that after application to the seeds they are taken up by the roots of the plants and transported to the above-ground parts of the plant and protect these against disease-causing agents.

The new compounds also exhibit a bactericidal effect.

Due to the wide spectrum of action, the compounds are not only suitable for the protection of useful plants, but also for material protection and for combating human-pathogenic and animal-pathogenic microbes, whereby they provide very wide application possibilities.

The new compounds can also be used in the form of their acid addition salts. These acid addition salts can be obtained by usual salt formation methods, for example by dissolving a compound of formula I in a suitable solvent and adding the acid.

Both inorganic and organic acids come into consideration for the formation of acid addition salts. As examples can be mentioned: Hydrohalic acids such as for example hydrochloric acid and hydrobromic acid, further phosphoric acid, sulfuric acid, nitric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as for example acetic acid, maleic acid, oxalic acid, succinic acid, fumaric acid, tartaric acid , citric acid, salicylic acid, lactic acid as well as sulphonic acid,

such as, for example, p-toluenesulfonic acid and 1,5-naphthalenedi-sulfonic acid.

As compounds with outstanding biocide and growth-regulating action, E-1-(4-chlorophenyl)-4-methoxy-4-arethyl-2-(1,2,4-triazol-1-yl)-1-penten-3- beer,

E-1-(4-fluorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol and

E-4-methoxy-4-methyl-1-(4-methylphenyl)-2-(1,2,4-triazol-1-yl)-1-penten-3-ol.

The new compounds can be used either alone, in a mixture with each other or with other active substances. Optionally, other plant protection agents or pest control agents can be used depending on the desired purpose.

Appropriately, the new active substances or mixtures thereof are used in the form of preparations such as powders, flow agents, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid carriers, respectively diluents and possibly wetting agents, binding agents, emulsifiers and/ or dispersing aids.

Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethylsulfoxide, dimethylformamide and further mineral oil fractions and plant oils.

Suitable solid carriers are minerals, such as clay, silica gel, talc, kaolin, attapulgite clay, limestone, silicic acid and plant products, such as flour.

Examples of surfactants include calcium lignin sulfonate, polyoxyethylene alkyl phenyl ether, naphthalene sulfonic acids and their salts, phenol sulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates as well as substituted benzene sulfonic acids and their salts.

If the active substance is to be used for seed staining, dyes can also be mixed to give the stained seed a distinct colour.

The proportion of the active substance in the different preparations can vary within wide limits. For example, the agent contains 10 to 90% by weight of active substance, 90 to 10% by weight of liquid or solid carriers as well as possibly up to 20% by weight of surfactant.

Application of the agent can be done in the usual way, for example with water carrying spray quantities of 100 to 1000 litres/ha. Application of the agent in the so-called "low-volume-^ or "ultra-low-volume method" is also possible, as well as application in the form of so-called microgranules.

For the preparation of the preparations, for example, the following ingredients are used:

a) 80% by weight active substance

15% by weight kaolin

5% by weight surfactant based on a mixture of the calcium salt of ligninsulfonic acid with alkyl-phenol polyglycol ether

b) 45% by weight active ingredient

5% by weight sodium aluminum silicate

15% by weight of cetyl polyglycol ether with 8 mol of ethylene oxide

2% by weight spindle oil

10% by weight polyethylene glycol

2 3 parts water

c) 20% by weight active ingredient

35% by weight montmorillonite

35% by weight silicic acid

8% by weight cell pitch

2% by weight sodium salt of N-methyl-N-oleyltaurine

d) 20% by weight active ingredient

15% by weight cyclohexanone

60% xylene by weight

5% by weight of a mixture of nonylphenylpolyoxyethylene or calciuradodecylbenzenesulfonate.

The new compounds can, for example, be prepared by reducing compounds of general formula in solvents with metal hydrides or metal hydride complexes to the desired process product.

The E-triazolyl pentone of general formula II can be reduced directly by means of a suitable metal hydride or metal hydride complex in a suitable solvent. Lithium aluminum hydride or sodium borohydride in a suitable solvent is suitable for this reduction. When using these metal hydride complexes, depending on the course of the reaction, varying amounts of unwanted by-products can be formed.

The formation of these by-products can be surprisingly reduced by using, according to the invention, electrophilic reducing agents in a suitable solvent. Examples of such agents are, for example: Alurainium hydride in tetrahydrofuran or ether, zinc borohydride in methoxyethane and, in particular, diisobutylaluminum hydride in toluene, hexane and other inert solvents. With the help of this process technique, a regioselective reduction of the keto group is made possible.

The E-triazolyl-pentenones used as starting compounds can conveniently be prepared from the corresponding Z-isomers by photochemical rearrangement.

Thereby, the Z-isomer is irradiated in a suitable solvent with rays from UV or xenon lamps or sunlight. Suitable solvents are alcohols such as methanol, ethanol or propanol, ethers such as diethylether, tetrahydrofuran or dioxane, ketones such as acetone or methylisobutyl ketone, and hydrocarbons such as hexane, cyclohexane, petroleum ether, benzene, toluene or xylene. The photoisomerization takes place preferably at temperatures of from 0 to 100° C, and can also be carried out with the addition of sensitizers such as acetophenone, propions or benzophenone. After the isomerization, the E-isomer formed is purified by recrystallization or column chromatography.

The preparation of the E-triazolyl-pentenones of general formula II used as starting compounds takes place using the corresponding, per se known triazolyl-butanones of general formula

which condenses with compounds of general formula

optionally dissolved in a suitable solvent, and in the presence of a catalyst, and the reaction product is separated into the desired E-isomer by column chromatography.

In general, 1 mol of the butanones is thereby reacted with

1 to 2 moles of the aldehyde, optionally using a suitable solvent, and in the presence of a catalyst. The catalyst can for example be: Alkali or alkaline earth metal hydroxides such as sodium, potassium or calcium hydroxide, alkali metal alcoholates such as sodium methylate, sodium ethylate or potassium methylate, carbonate such as sodium or potassium carbonate, acetates such as sodium or potassium acetate, secondary amines such as diethylamine, dipropylamine, pyrrolidine, piperidine or morpholine and tertiary amines such as triethylamine, tributylamine, pyridine, picoline or dimethylaniline. The catalyst is used in an amount of from 0.001 to 0.5 mol. Applicable solvents are, for example, alcohols such as methanol or ethanol, aromatic hydrocarbons such as benzene, toluene or xylene, ethers such as diethylether, tetrahydrofuran or dioxane, water and mixtures thereof. The reaction conveniently takes place in the range from 0° C to the boiling point of the solvent used.

When an acetate, for example sodium or potassium acetate, a carbonate such as sodium or potassium carbonate or a tertiary amine is used as a catalyst, it can be used as a reaction solvent. glacial acetic acid or acetic anhydride is used.

The reaction product can be present as a Z, E-isomer mixture or also as pure Z or E components, whereby in the first case a column chromatographic separation is carried out to form the desired E-isomer. Optionally, the Z, E isomer mixture can also first be reduced and then column chromatographically separated.

The following examples illustrate the preparation of the new compounds.

Example 1

E-1-(4-chlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol

1.53 g of E-1-(4-chlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)-1-penten-3-one was dissolved in 15 ml of tetrahydrofuran and was brought to -60° C. Under nitrogen, 6 ml of diisobutylaluminum hydride in toluene (approx. 1.2 m solution) was added dropwise with stirring. The reaction is exothermic. The reaction mixture was brought to room temperature, 2 drops of toluene were added and then 15 ml of 10% hydrochloric acid was added. The reaction mixture was well stirred, poured into a separatory funnel and shaken twice with 50 ml of acetic acid. After drying the organic phase with MgSO4, this was filtered, and after rotary evaporation in vacuum, 1.48 was obtained

g solid product with melting point 139° C. This was crystallized from isopropanol.

Yield: 1.02 g = 70% of theoretical

Melting point: 146° C

In an analogous manner, the following compounds were prepared:

The new compounds dissolve poorly in water and more or less well in polar organic solvents such as alcohols, for example methanol, ethanol and the like as well as acetic acid ethyl ester, diethyl ether, diisopropyl ether, acetonitrile and N,N-dimethylformamide.

They dissolve well in organic solvents such as chloroform, methylene chloride, toluene and xylene.

The following examples illustrate the preparation of the starting compounds.

Example 12

Z-1-(4-Chlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)-1-penten-3-one

29.66 g (0.211 mol) of 4-chlorobenzylaldehyde, 1.7 ml of piperidine and 5.6 ml of glacial acetic acid. The reaction mixture was boiled for 5 hours with stirring and using a water separator (bath temperature 150° C.). After cooling to room temperature, the reaction solution was diluted with 200 ml of acetic acid and was then washed once with 200 ml of water and twice, each time with 200 ml of 10% sodium disulfite solution, and two more times with 200 ml of water each time. The reaction product was dried over MgSO 4 , was filtered and evaporated in vacuo (20 Torr, 50° C). It was obtained approx. 60 g of dark red, semi-crystalline oil which was recrystallized from diisopropyl ether. 34.2 g (57% of theoretical) of pale yellow crystals with melting point 104 - 106° C were obtained.

Example 13

E-1-(4-chlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)-1-penten-3-one

339.3 g (1.109 mol) of Z-1-(4-chlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)-1-penten-3-one was dissolved in 3 liters of acetone and was irradiated in a Falling film reactor for 21 hours with a mercury lamp (700 watts, 254 nm). The solution now contained a Z,E mixture. The reaction mixture was evaporated to dryness and the semi-crystalline residue was added to 1 liter of pentane. During ice bath cooling, the residue was triturated with pentane and then the solid product was separated which still contained Z-isomers. 318 g of the product were dissolved in 3 liters of diisopropyl ether while heating, and the undissolved components were filtered off. The solution was crystallized overnight at -5° C. The 242 g now obtained were again recrystallized from 3 liters of diisopropyl ether. The reaction solution was allowed to reach room temperature and the crystallized substance was separated.

Yield: 115.7 g = 34% of theoretical

Melting point: 118 - 119° C.

The following examples illustrate the possibility of use for the new compounds in the form of the previously indicated preparations.

Example 14

Growth reduction in various beneficial plants

Maize, rice, soya, wheat and sugar beet were treated in the pre-emergence method (VA) and in the post-emergence method (NA) with aqueous emulsions of investigated compounds in quantities of 0.5 kg of active substance/ha and were cultivated. 12 days after the treatment, the above-ground plant growth was determined: the stem of dicotyledonous plants was measured to the vegetation point. In the case of monocotyledonous plants, the length of straw in the pre-emergence experiment was measured to the deflection of the first leaf spread, in the post-emergence experiment to the deflection of the second leaf spread.

The data thus obtained were determined in relation to the control, and the percentage growth inhibition was determined.

The results clearly show that the new compounds are either superior in several cultures to the comparator in one of the two application methods or exhibit a stronger effect in at least one culture or one application method, but however lead to growth inhibition in the other cultures.

Example 15

Growth reduction and stress tolerance in different useful plants

Cotton, corn, rice, soy and wheat were treated and evaluated as described in Example 14.

After the length measurement, i.e. on the 12th day, the plants were no longer watered in these experiments. After 2 days, the degree of wilting of cotton, maize and soybeans was determined according to the following four steps: 0 = plants completely turgid 1 = hint of wilting

2 = withered leaf

3 = severely wilted leaf

4 = dry leaves, papery

It turned out that the new compounds clearly increased the stress tolerance compared to the comparison agent and the control, moreover, the growth-inhibiting effect with several treatments is stronger than the comparison agent.

Example 16

Growth reduction of maize

On maize, the compounds indicated in the following table were applied as aqueous emulsions in amounts of 0.1 and 0.5 kg of active substance/ha by the pre-emergence method.

After 12 days, the length of the stem to the deflection of the first leaf (as described in Example 14) was measured and determined in relation to the untreated control. The percentage growth inhibition was then determined.

The results show that the new compounds exhibit an effect more than twice as strong as the comparison agent. The treated plants were compressed and dark-green.

Example 17

Effect of prophylactic foliar treatment against Erysiphe graminis on barley plants in greenhouses

Young barley plants were sprayed dripping wet with 0.025% active ingredient concentration. After drying the spray coating, the treated as well as the untreated plants were inoculated by spreading infested plants over the test plants so that condiospores of rysiphe graminis were transferred dry. The test plants were then incubated in greenhouses at 20 to 22° C. After 1 week, the percentage attack of the leaves was determined. Based on the results obtained, the fungicide effect was calculated as follows:

The compounds were available as 20% formulations.

Example 18

Effect of prophylactic treatment against Puccinia hordei (dwarf rust) on barley plants in greenhouses

Young barley plants were sprayed with dripping wet

0.025% active substance concentration. After drying of the spray coating, the treated as well as the untreated plants were inoculated dry, while plants infested with dwarf gravel were spread over the experimental plants. The experimental plants were then incubated at 15° C and high humidity in a greenhouse.

After a week and a half, the percentage of the infested leaf surface was noted. The fungicidal effect was calculated as follows:

The compounds were available as 20% formulations.

Example 19

Seed treatment against Tilletia caries in field trials

With 5 g of spores from the caries pathogen Tilletia caries, 1 kg of wheat grain1 was artificially contaminated, and untreated or treated grain with the compounds indicated in the table was sown in open fields. The investigated compounds were used as emulsion concentrates in 1 liter of water per 100 kg of seed. After approx. 4 months (for summer wheat) the diseased ears were counted and the effect was calculated.

Amount of active ingredient: 20 g/100 kg seed.

The comparator proved to be highly phytotoxic as the wheat was damaged to a degree of 60%

in relation to the wheat treated according to the invention.

Example 2 0

Seed treatment against Helminthosporium gramineum on summer barley in open fields

Barley seed with natural attack by Helminthosporium gramineum (causing stripe disease) was left untreated or after treatment with the compounds listed in the table sown in open fields. The investigated compounds were used as emulsion concentrates in 1 liter of water per 100 kg of seed. After 3 months, the attacked plants were counted and the effect was calculated.

Amount of active ingredient: 20 g/100 kg seed

The barley plants were completely destroyed by the comparator so that an assessment of the fungicidal effect was not possible.

Example 21

Seed treatment against Ustilago avenae on oats in field trials

Oat seed grains were moistened in a suspension of spores of Ustilago avenae and in a vacuum desiccator several times exposed to an alternation between normal and negative pressure. After drying the seeds, these were treated with the compounds indicated in the following table, which were used as an emulsion concentrate in 1 liter of water per 100 kg of seed. 10 weeks after sowing treated seed as well as untreated infected seed as a control, the diseased ears were dried and the effect was calculated.

Amount of active ingredient: 50 g/100 kg seed

The oats were damaged to an extent of 30% by the comparator.

Example 22

Effect of prophylactic foliar treatment against Botrytis cinerea on tomato plants in greenhouses

Young tomato plants were sprayed dripping wet with spray liquid containing 0.025% active ingredient. After drying the spray coating, the treated plants as well as untreated plants as controls were inoculated. In this way, a suspension of spores (approx. 1 million per milliliter of fruit juice solution) of the gray mold promoter Botrytis cinerea was sprayed on as inoculum. The plants were then incubated in greenhouses at approx. 2 0° C and higher humidity. After collapse of the untreated plants (= 100% attack), the degree of attack on the treated plants was determined and the fungicidal effect was calculated.

The new compound E-1-(4-chlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol limited in 10% formulation intercepted with 80 %.

Example 2 3

Effect of prophylactic and curative treatment against apple scab (Venturia inaegualis) in open fields.

Shoots of growing apple plants were sprayed dripping wet with a spray liquid containing 300 ppm active substance. After drying the spray coating, these shoots as well as further shoots as untreated controls or for the curative treatment inoculated. A suspension of 345,000 spores per milliliters of 3% glucose solution in distilled water while excluding dripping from the leaves. The inoculated shoots were thus wrapped in polyethylene bags. After 2 days the bag was taken away. 1 week after inoculation, the healing treatment was carried out on inoculated, previously untreated shoots. 3 1/2 weeks after inoculation, the percentage of scab affected leaf surface was determined and the fungicidal effect of the treatment was calculated.

Example 24

Effect of prophylactic foliar treatment against Cochliobolus

on rice plants in greenhouses

Young rice plants were sprayed dripping wet with 250 ppm active substance concentration. After drying the spray coating, the treated plants as well as untreated control plants were inoculated by spraying a suspension of spores (approx. 250,000/ml) of the fungus Cochliobolus miyabeanus and were inoculated at 24 to 26° C in moisture-saturated air in a greenhouse. After 5 days, the percentage of the leaf area destroyed by the fungus was determined.

Example 25

Effect of prophylactic foliar treatment against Piricularia oryzae on rice plants in greenhouses

Young rice plants were sprayed dripping wet with 250 ppm active substance concentration. After drying the spray coating, the treated plants as well as untreated control plants were inoculated by spraying a suspension of spores (approx. 200,000/ml) of the leaf spot pathogen Piricularia oryzae and were incubated moist at 25 to 27° C in a greenhouse.

After 5 days, it was determined what percentage of the leaf surface was attacked.

Example 26

Effect of prophylactic foliar treatment against Helminthosporium teres (=Pyrenophora teres), net spot disease on barley in greenhouses

Young barley plants in the first leaf stage were sprayed dripping wet with 250 ppm active ingredient concentration. After drying the spray coating, the treated plants and untreated control plants were sprayed with a suspension of conidiospores of Helminthosporium teres and were incubated in a humidity chamber in the greenhouse for 2 days at 20 to 22° C. Then the plants were grown in a greenhouse at 20 to 22 ° C. One week after inoculation, the percentage attack of the leaf surface was determined.

Example 2 7

Effect of prophylactic foliar treatment against Erysiphe cichoracearum on pumpkin plants in greenhouses

Pumpkin plants were sprayed dripping wet with the specified effective concentration and, after drying the spray coating, were inoculated by dusting dry powdery mildew spores of Erysiphe cichoracearum. The plants were incubated in greenhouses at 24° C. After one week, the affected leaf area was calculated as a percentage of the total leaf area. The fungicidal effect was calculated as follows:

The compounds were available as 10% or 20% formulations.

The addition "s" means systemic effect, which is important for the protection of the untreated growth of the plants.

Example 2 8

Effect of prophylactic foliar treatment against Uromyces appendiculatus on beans in greenhouses

Bean plants in the first primary leaf stage were sprayed dripping wet with 4 ppm active substance concentration. After drying the spray coating, the treated plants as well as the untreated control plants were sprayed with a suspension of bean rust spores (400,000 per milliliter) and were kept for 3 days in humidified air at 22° C. The plants were then placed in greenhouses. 20 days after inoculation, the percentage of the infested leaf area was determined. At the same time, any phytotoxic damage was determined.

The fungicidal effect was calculated as follows:

The compounds were available as 10% emulsion concentrates.

Example 2 9

Microbiocidal activity in vitro against Pseudomonas phaseolicola and Mucor spee

Pseudomonas phaseolicola is known to cause the fatty spot disease in beans. Mucor spee. was isolated from diseased soybean tissue.

Aqueous active substance preparations were mixed with sterilized liquid agar nutrient medium (2% biomalt,

2% agar) at 45° C in such a way that the mixture contained 250 ppm active substance. The mixture was poured into polystyrene petri dishes with a diameter of 8.5 cm and a height of 5 mm. After cooling the nutrient medium, a suspension of Pseudomonas phaseolicola in distilled water was placed in the middle of the petrosal dish using a 5 mm inoculation scoop, or a 5 mm inoculation piece with Mucor. For each treatment and organism, 2 dishes and 4 untreated dishes were inoculated. After 5 days (Mucor) or after 3 weeks (Pseudomonas) incubation at 20 to 22°C in the dark, the colony diameter was determined, and after subtraction of the inoculum size, the inhibitory effect was calculated as follows:

The compounds were present as 10 or 20% dispersed formulations in water.

Example 30

In greenhouses, the indicated plants were treated after germination with the new compound and with the comparator in an amount of 3 kg/ha. For this purpose, the compounds were applied to the plants as a suspension with 500 liters of water/ha evenly over them. 2 weeks after the treatment, the plants were assessed according to the following assessment criteria:

0 = Destruction of the plants

1 - 4 = Very strong inhibition of the plants

5 - 7 = Strong inhibition of the plants

8 - 9 = Weak inhibition of the plants

10 = Normal growth of the plants

From the table it appears that many weeds in particular are completely inhibited in their development by the new compound so that these can be ruled out as food competitors.

This effect can be used for weed control. The comparator did not show an equally good effect.

Example 31

In greenhouses, the indicated plants were treated before germination with the new compound E-I-(4-chlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)-1-penten-3 -ol in a quantity of 0.3 kg of active substance/ha.

For this purpose, the compound was placed evenly on the plants as a suspension with 500 liters of water/ha. 2 weeks after the treatment, the plants were assessed according to the following assessment form:

0 = Destruction of the plants

1 - 4=Very strong inhibition of the plants

5 - 7 = Strong inhibition of the plants

8 - 9 = Weak inhibition of the plants

10 = Normal growth of the plants

The table shows that many weeds are inhibited in their development by the new compound, so that they can be eliminated as competitors.

This effect can be used for weed control.

Claims (10)

1. E-triazolyl pentenols of general formula in which R denotes a C-^-C^Q -alkyl radical or a C3-C8-alkenyl radical and R-^ denotes an unsubstituted or substituted aromatic hydrocarbon residue which is substituted with one or more, the same or different substituents selected from halogen, G1-C4 -alkyl, C1-C4~ alkoxy, C-^-Cj-alkyl thio, trifluoromethyl or a nitro group, or a heterocyclic hydrocarbon residue, and acid addition salts thereof with inorganic and organic acids. 2. E-triazolyl pentenols according to claim 1, characterized in that R equals methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, isopropyl, 2,2-dimethylpropy1-1, 3,3-dimethylbutyl-2, 2-buten-l-yl, 3 -methyl-2-buten-1-yl, hexenyl, heptenyl or octenyl, and R-j^ equals 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl, 3-bromophenyl-4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4 -iodophenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 3- ethylphenyl, 4-ethylphenyl, 2-propylphenyl, 3-propylphenyl, 4-propylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 2-butylphenyl, 3-butylphenyl, 4-butylphenyl, 2-sec-butylphenyl, 3-sec-butylphenyl, 2-tert-butylphenyl, 3 -tert-butylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 2-ethylthiophenyl, 3-ethylthiophenyl, 4-ethylthiophenyl, 2-trifluoromethyl phenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 3-fluoro-4-methoxyphenyl, 2-chloro-5-nitrophenyl, 4-chloro-2 -fluorophenyl, 3,4,5-tri-methoxyphenyl, 5-chloro-2-nitrophenyl, pyridiyl, thienyl or furyl. 3. Eptriazolyl pentenols according to claims 1-2, characterized in that these are E-1-(4-chlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)-1- penten-3-ol, or E-1-(2,4-dichlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol, or E-1-(4-fluorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol, or E-4-methoxy-4-methyl -1-(4-methylphenyl)-2-(1,2,4-triazol-1-yl)-1-penten-3-ol, or E-4-ethoxy-1-(4-fluorophenyl)-4- methyl-2-(1,2,4-triazol-1-yl)-l-penten-3-ol, or E-1-(4-bromophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol, or E-4-ethoxy-1-(2-fluorophenyl)-4-methyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol, or E-4-ethoxy-1 -(4-bromophenyl)-4-methyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol, or E-4-ethoxy-1-(4-chlorophenyl)- 4-methyl-2-(1,2,4-triazol-1-yl)-l-penten-3-ol, or E-4-ethoxy-4-methyl-1-(4-methylphenyl)-2-( 1,2,4-triazol-1-yl)-1-penten-3-ol, or E-1-(2-chlorophenyl)-4-methoxy-4-methyl-2-(1,2,4-triazol-1 -yl)-1-penten-3-ol 4. Process for the production of E-triazolyl-pentenols according to claims 1-2, characterized in that E-triazolyl-pentenones of general formula are reduced in solvent with metal hydrides or metal hydride complexes. 5. Method according to claim 4, characterized in that an electrophilic reducing agent is used, preferably aluminum hydride, zinc borohydride or diisobutylaluminum hydride. 6. Process according to claim 4, characterized in that the E-triazolyl-pentenone used is obtained from Z-triazolyl-pentenones of general formula II by photochemical rearrangement. 7. Method according to claim 6, characterized in that the rearrangement is carried out with the help of UV rays at temperatures of from 0 to 100° C in solvents, optionally with the addition of sensitizers. 8. Process according to claim 4, characterized in that E-triazolyl-pentenones of general formula II are used which are prepared by triazolyl-butanone of general formula is condensed with compounds of general formula optionally dissolved in a solvent and in the presence of a catalyst, and that the reaction product is optionally separated by column chromatography into the desired E-isomer. 9. Biocidal agent, characterized in that it contains at least one compound according to claims 1-2. 10. Growth regulator for plants, characterized in that it contains at least one compound according to claims 1-2.