GB1593687A - Process for influencing plant growth and 1-phenyl-2-(1,2,4-triazolyl-1) alkyl ethers for use therein - Google Patents

Description

(54) PROCESS FOR INFLUENCING PLANT GROWTH AND l-PHENYL-2-(1,2,4 TRIAZOLYL-I)ALKYL ETHERS FOR USE THEREIN (71) We, BASF AKTIENGESELLSCHAFT, a German Joint Stock Company of 6700 Ludwigshafen, Federal Republic of Germany, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- The present invention relates to the use of triazolylalkyl ethers for influencing plant growth and to novel compounds of this type.

It is known (U.S. Patent 3,156,544) that (2 - chloroethyl) trimethylammonium chloride has growth-regulating properties. It can, for instance, be used to influence plant growth, especially to inhibit vegetative growth in some cereals and other crops. However, the action of this compound is frequently insufficient, it can only be applied to a relatively small number of crop plants, and it is rapidly inactivated when applied to the soil over a fairly long vegetation period.

Copending U.K. Patent Application No. 44417/76 (Serial No. 1,512,918) describes and claims 1 - phenyl - 2 - triazolyl - ether derivatives of the formula

in which R represents halogen, alkyl, alkoxy, alkylthio, alkylsulphonyl, halogenoalkyl, nitro, cyano, optionally substituted phenyl or optionally substituted phenoxy and R' represents alkyl, alkenyl, alkynyl, optionally substituted phenyl, optionally substituted benzyl, or optionally substituted styryl and n is 0, 1, 2 or 3, the substituents K being selected independently of each other when n is 2 or 3, and their salts. These compounds are there said to be fungicides and bactericides.

We have now found that compounds of the general formula

where R1 denotes an unsubstituted or chloro-substituted unsaturated aliphatic hydrocarbon radical of 3 to 5 carbon atoms, 4-chlorobenzyl or 2,4-dichlorobenzyl, R2 denotes hydrogen or alkyl of 1 to 4 carbon atoms, R3 denotes fluoro, chloro, bromo, methyl, trifluoromethyl, phenyl or alkoxy of 1 to 3 carbon atoms, and n denotes 0, 1, 2 or 3, the radicals R3 being identical or different when n=2 or 3, and their salts, are excellently suited for influencing plant growth.

According to the invention therefore a method for influencing the growth of plants comprises treating the plants or the soil with a compound of the general formula I above.

The acid addition salts correspond to the general formula

where R', R2, R3 and n have the above meanings and HS denotes any organic or inorganic acid capable of forming salts with compounds of the formula 1. Examples of suitable acids are sulfuric acid, nitric acid, hydrochloric acid, hydrobromic acid, phosphoric acid, acetic acid, propionic acid, butyric acid, benzoic acid and dodecylbenzenesulfonic acid.

The salts of the formula II may be prepared by simple addition of the acids HS to the compounds of the formula I, if desired in a solvent.

The compounds inhibit the growth of unwanted plants better than the prior art (2 - chloroethyl) - trimethylammonium chloride, and are also effective in crops in which the prior art compound has no effect.

Those of the compounds which have the formula

where R3, R1 and n have the above meanings and R4 is alkyl of 1 to 4 carbon atoms, preferably methyl or n-butyl, and the salts thereof, are novel and are claimed per se herein.

The following table contains examples of active ingredients of the formulae I and II: TABLE 1 No. R R (R ) HS m.p. ( C) 1 -CH2-CH=CH2 H 4-F HNO3 105-107 2 -CH2-CH=CH2 H 4-Cl HNO3 97-98 2a -CH2-CH=CH2 H 4-Cl HCl 133-135 3 -CH2-CH=CH2 H 4-Br HCl 142-145 4 -CH2-CH=CH2 H 4-Br HNO3 99-100 5 -CH2-CH=CH2 H 3-Br HNO3 119-120 6 -CH2-CH=CH2 H 2,4-Cl2 HNO3 129 7 -CH2-CH=CH2 H 2,4-Cl2 HCl 110-112 8 -CH2-CH=CH2 H 2,4-Cl2 - nD22=1.5568 9 -CH2-CH=CH2 H 2,4-Cl2 H25C12-C6H4-SO3H paste 10 -CH2-CH=CH2 H 2,4-Cl2 1/2 H2C2O4 102-103 11 -CH2-CH=CH2 H H NHO3 96-98 12 -CH2-CH=CH2 H 4-OCH3 HNO3 120-121 13 -CH2-CH=CH2 H 3,4,5-(OCH3)3 HNO3 135-136 14 -CH2-CH=CH2 H 2,3,4-(OCH3)2 HNO3 134-135 15 -CH2-CH=CH2 H 2,4-(OCH3)7 HNO3 126-127 16 -CH2-CH=CH2 -(CH2)3-CH3 4-Cl HNO3 132-133 17 -CH2-CH=CH2 -(CH2)3-CH3 4-Br HNO3 143-144 18 -CH2-CH=CH2 -CH3 4-Br - b.p.(0.08 mm) 19 -CH2-CH=CH2 -CH3 4-Br HNO3 97 20 -CH2-CH=CH2 -CH3 2,5-(OCH3)2 HNO3 115-116 21 -CH2-C#CH H 4-F HNO3 110-111 22 -CH2-C#CH H 4-Cl HNO3 109-110 23 -CH2-C#CH H 3-Br HNO3 113-114 24 -CH2-C#CH H 4-Br HNo3 119 - 120 25 -CH2-C#CH H 2,4-Cl2 HNO3 12ss 26 -CH2-C=CH H 2,4-(OCH3)2 HNO3 136 - 137 27 -CH2-C#CH H 2,3,4-(OCH3)3 HNO3 128 - 129 28 -CH2-C#CH H 3,4,5-(OCH3) HNO3 135 - 136 29 -CH2-C#CH CH3 4-OCH3 HNO3 134 - 135 30 -CH2-C#CH -(CH2)3-CH3 4-Cl HNO3 121 - 123 TABLE 1 (cont.).

No. R R (R )n HS m.p. ( C) 31 -CH2-CH=CH-CH3 H 4-F HNO3 111 - 112 32 -CH2-CH=CH-CH3 H 4-Cl HNO3 107 - 109 33 -CH2-CH=CH-CH3 H 3-Br HNO3 110 - 112 34 -CH2-CH=CH-CH3 H 2,4-Cl2 HNO3 115 35 -CH2-C#C-CH3 H 2,4-Cl2 HNO3 133 - 134

4-Br HUC 146 - 147 4-CH3 HNO3 122 - 123 4-Br HNO3 146 - 147 2,4-Cl2 HNO3 133 - 134 2,4-Cl2 HNO3 141 - 143 4-Cl The compounds of the formula I may easily be prepared by reaction of alkali metal salts of the general formula

where R2, R3 and n have the above meanings and M denotes sodium or potassium, with a compound of the formula X-R' IV where R' has the above meanings and X denotes chloro, bromo, iodo, methosulfate or toluenesulfonate, preferably chloro, bromo and iodo.

The alkali metal salts of the formula III are readily obtained from 1 - aryl 2 - triazolylalkanols of the formula

by reaction with strong bases such as alkali metal hydride and alkali metal amide, or with lower alkali metal alcoholates; in the latter case, the lower alcohols which form have to be removed by azeotropic distillation. It is generally not necessary to isolate the alkali metal salts of the formula III. They may be further reacted with compounds of the formula IV in an inert solvent, e.g., toluene, xylene, tetrahydrofuran or dimethylformamide, immediately after having been prepared.

The preparation of alcohols of the formula V is known (German Laid-Open Application DOS 2,431,407). Depending on the conditions under which the reactions are carried out, the compounds are obtained either in the form of the free bases I or their salts II. The salts may be converted in conventional manner into the free bases, e.g., by reaction with an alkali such as sodium or potassium hydroxide, sodium or potassium carbonate or ammonia. The compounds as bases may be converted into the valuable -- from the application point of view - aCid addition salts by reaction with acids, e.g., inorganic acids, such as hydrochloric acid, hydrobromic acid, hydriodic acid, sulfuric acid, nitric acid and phosphoric acid, or organic acids, such as acetic acid, propionic acid, butyric acid, glycolic acid, benzoic acid and toluenesulfonic acid, or higher alkylbenzencsulfonic acids such as dodecylbenzenesulfonic acid.

The following characteristic examples, in which all parts are by weight, are intended to illustrate the method of manufacture.

EXAMPLE 1 At 500C, a solution of 20 parts of I - (2,4 - dichlorophenyl) - 2 - 11',2',4' triazolyl - (1')] - ethanol in 50 parts of anhydrous dimethylformamide is dripped into a suspension of 5.2 parts of 80% sodium hydride in 110 parts of tetrahydrofuran. After refluxing for 2 hours while stirring, 15.8 parts of 3bromopropene is dripped in. After stirring for I hour at 500C, water is added and extraction carried out with ether. With ice cooling, 98% nitric acid is added dropwise to the extract. 19 parts of crystals precipitate out, which, when recrystallized from ethyl acetate, give 12 parts of 1 - (2,4 - dichlorophenyl) - I allyloxy - 2 - [1',2',4' - triazolyl - (1')] - ethane as hydronitrate; m.p.: 129"C.

EXAMPLE 2 2.7 parts of I - (4 - bromophenyl) - 2 - [1',2',4' - triazolyl - (1')l - ethanol and 0.5 part of sodium hydride are stirred with each other in dimethylformamide until no more gas evolves. With ice cooling, 0.7 part of allyl chloride in 20 parts of dimethylformamide is dripped in. After stirring for 1 hour at room temperature, water is added, the aqueous phase is extracted with ethyl acetate, the extract is concentrated and dissolved in ethanol, and a solution of hydrogen chloride in isopropyl ether is added. The solution which is obtained is concentrated, ether is added, and the precipitate is recrystallized from a mixture of isopropyl ether and isopropanol. There is obtained 1.6 parts of 1 - allyloxy - I - (4 - bromophenyl) 2 - [1',2',4' - triazolyl - (1')] - ethane as hydrochloride; m.p.: 1420--145"C.

The compounds of formula I influence plant growth. In particular, they may be used as growth regulators. The compounds have a particularly good action on Cruciferae, especially rape, and specifically winter rape.

The superior action of the compounds of formula I over the prior art compounds and their enrichment of the art is impressively demonstrated by the influence on the growth of winter rape.

Various winter rape varieties giving high-quality oils tend to lose prematurely in the fall - without the influence of cold - their inhibition to flower, and to enter the generative phase. Such plants are particularly sensitive to frost.

Furthermore, the vegetative development is neglected when the plant enters the generative phase, with the result that in the following spring too few leaves have developed; as a consequence, for example, photosynthesis suffers. The aim is therefore to keep the rape plants in the vegetative development stage before the winter frosts set in, in spite of the good supply of nutrients and favorable growth conditions. At the same time, the premature development of too luxuriant a foliage (which is destroyed anyway by frost) should be avoided.

We have now found that the compounds of formula I, especially compound No. 4 in the table above, enable the growth of the crop plant rape to be regulated in the abovementioned manner.

In other crops too, e.g., winter cereals, especially winter barley, it is advantageous for the plants, after treatment with the compounds of formula I, to be well tillered in the fall, but for them not to enter the winter with too luxuriant a growth. This is a prophylactic measure against the increased sensitivity to frost and - due to the relatively small amount of foliage - various diseases. The compounds of formula I are therefore preferably applied in the fall and winter.

Furthermore, growth-regulating effects have also been achieved in various other crops and also wild-growing species, and are described below.

1 - [p - aryl - fi - (alkenyloxy) - ethyl - imidazoles are known (German Laid-Open Application DOS 2,063,857) whose chemical structure is similar to that of the compounds of formula I, and which have fungicidal and bactericidal properties. Representatives of these compounds were synthesized and included in the examples for comparison purposes, even though the publication makes no mention of a growth-regulating action in higher plants. A prior art triazolyl derivative (German Laid-Open Application DOS 2,407,143) was also examined; however, as it contains a phenoxy radical and a

group its chemical structure differs considerably from that of the compounds to be employed in accordance with the invention.

TABLE 2 No. Prior art compounds

U.S. 3,156,544 German Laid-Open Application (DOS) 2,063,857 German Laid-Open Application (DOS) 2,063,857 German Laid-Open Application (DOS) 2,063,857 German Laid-Open Application (DOS) 2,407,143 The following examples, carried out in the greenhouse with at least partially controlled environmental conditions, and in the open, illustrate the use of the agents according to the invention.

A) Greenhouse Experiments Test Method a The test plants, separated by species, were shown in small paraffined paper cups having a volume of 200 cm3. The substrate was a minerally fertilized sandy loam containing 1.5 /O humus and having a pH of 5.8. In the pre-emergence treatment (PRE), the chemical substances were applied immediately after sowing to the still unswollen seeds which were only slightly covered with soil. In the postemergence treatment (POST) or leaf treatment, the test plants were first grown to a height of 3 to 10 cm, depending on the growth shape, before they were treated. The test substances were applied by means of atomizing nozzles in water as the distribution medium. Depending on the temperature requirements of the plants, the experiments were set up in the warmer or cooler part of the greenhouse. The experiments were carried out over a period of several weeks. The duration depended on the development of the individual species and their growth potential in the small containers. Assessment was visual, on a 0 to 100 scale, 0 denoting no change in growth, 100 denoting inhibition equivalent to destruction of the plants.

Growth height measurements are given in cm (cf. Tables 4 and 5).

Test Method b In a different method (Neubauer system) the test plants were sown in a peat substrate supplied with sufficient nutrients. The active ingredients were applied in aqueous solution or dispersion at various rates to the soil and to the foliage. In the soil treatment, the active ingredients were sprayed on to the surface of the soil on the day the seeds were sown; in the foliage treatment, the compounds were applied in conventional manner by spraying at a growth height of the plants of approx. 8 cm. During the growth period of 18 days, the plants treated with the compounds according to the invention exhibited a distinctly lower growth height compared with the untreated control, which was confirmed by subsequent measurements.

From each series, 100 plants were measured. The imidazole compounds used for comparison exhibited no action at all (cf. Tables 9 and 10).

B) Vegetation Experiment in Accordance With the Mitscherlich System To ascertain the effect of the treatment with the various agents according to the invention on monocotyledons under conditions approximating to those in the open, a vegetation experiment was carried out with spring barley in large (10 liter) vessels. The plants were grown in a sandy loam, fertilized with 1.5 g of N as ammonium nitrate and 1 g of P205 as secondary potassium phosphate. The active ingredients were applied as an aqueous solution or dispersion to the surface of the soil (after sowing) by means of a pipette. N - 2 - chloroethyl - N,N,N trimethylammonium chloride (No. 41) used as comparative agent was, however, applied to the foliage at a growth height of the plants of approx. 28 cm, as it is known of this compound when applied to the soil over a fairly long vegetation period that it is rapidly inactivated (cf. Table 11).

C) Experiments in the Open Small plots were laid out with the predominant aim of studying the development of winter rape varieties under the influence of an agent according to the invention. The agents were applied to the foliage a few weeks after sowing with the aid of a tractor-driven plot spray. Water was the carrier medium for the finely divided active ingredient. The observation period extended from the time of treatment through the winter and frost period up to commencement of flowering.

The development stage of the plants was recorded at various intervals (cf. Tables 12, 13 and 14).

Results The greenhouse experiments and those in the open show that the agents according to the invention, especially those containing active ingredient No. 4, have a growth-regulating action on numerous plant species from the most widely varying botanical families (Table 4). Visually, a reduction in growth height was recorded, the value of which must be interpreted individually from species to species.

The action of the closest comparative compound with regard to function, 2chloroethyl trimethylammonium chloride (No. 41), was equalled or exceeded. This applies particularly with respect to the large number of plant species which reacted to treatment with compounds of the formula 1, whereas they only reacted slightly, or not at all, to the comparative agent (Tables 4, 8, 9, 10, 11, 12, 13 and 14).

Other prior art compounds (Nos. 4245), employed because of their structure for comparison purposes, had an inferior action (Tables 5, 6 and 7). It should be pointed out that the compounds with an imidazolyl radical which are the closest with regard to chemical structure have not been described as plant growth regulators.

A particularly outstanding property of the compounds of formula I is their specific influence on the growth of winter rape. Vegetative growth was checked and premature entry into the generative stage prevented, thus ensuring better overwintering and yield chances for the plants. At the same time, unwanted plants occurring in rape crops were inhibited in their growth to such an extent that they were unable to outgrow the crop plants deliberately inhibited in their growth; they were thus insignificant as competitors.

The action on cereals was also noteworthy, as, inter alia, the experiment in Tables 4 and 11 (barley) shows.

TABLE 3 List of Plant Names Latin term English term Avena sativa Oats Echinochola crus-galli Barnyard grass Euphorbia geniculata South American member of the spurge family Galium aparine Catchweed bedstraw Hordeum vulgare Barley Lamium amplexicaule Hen bit Lolium muhiflorum Annula ryegrass Medicago sativa Alfalfa Secale cereale Rye Sinapis alba White mustard Solanum lycopersicum Stellaria media Chickweed Triticum aestivum Wheat TABLE 4 Influence on the Growth of Various Test Plants by Different Active Ingredients, Postemergence Treatment in the Greenhouse Amount of active ingredient Growth height in cm.

Species kg/ha Compound No. 4 Compound No. 41 Euphorbia 0+ 27 27 geniculata 1.0 24 25 2.0 25 28 4.0 24 25 Hordeum 0 16 16 vulgare 0.5 15 16 2.0 11 15 4.0 10 14 Medicago 0 27 27 sativa 0.5 25 26 1.0 21 25 2.0 18 24 4.0 15 22 Secale cereale 0 70 0.25 52 0.5 49 1.0 48 2.0 46 Triticum 0 31 31 aestivum 0.5 23 28 1.0 21 30 2.0 20 26 4.0 14 21 +=untreated control TABLE 5 Inhibition of the Growth of Various Test Plants by Various Imidazolyl and Triazolyl Derivatives in the Greenhouse Test plants and growth inhibition in % Application Compound rate Time of Avena Echinochloa Hordeum Lolium Sinapis No. kg/ha application sativa crus galli vulgare multifl. alba 42 3.0 PRE 20 - 20 20 20 3.0 POST 20 0 20 20 20 43 3.0 PRE 20 - 20 20 0 3.0 POST 20 0 0 0 0 44 3.0 PRE 20 - 20 20 0 3.0 POST 20 0 0 20 20 45 3.0 PRE 0 - 0 20 20 3.0 POST 20 20 0 20 20 4 3.0 PRE 40 - 20 20 40 3.0 POST 40 40 20 20 40 0=no inhibition.

100=plants destroyed.

TABLE 6 Influence on the Growth of Rape; Soil Treatment (Neubauer System) Application Compound rate Plant height No. kg/ha cm relative untreated - 17.8 100 42 3.00 17.8 100 12.00 17.8 100 43 3.00 17.7 100 12.00 17.8 100 44 3.00 17.8 100 12.00 17.8 100 4 3.0 15.5 87 12.00 13.9 78 38 3.00 16.4 92 12.00 14.0 79 TABLE 7 Influence on the Growth of Rape; Leaf Treatment (Neubauer System) Application Compound rate Plant height No. kg/ha cm relative untreated - 15.8 100 42 1.50 15.8 100 6.00 15.8 100 43 1.50 15.8 100 6.00 15.8 100 44 1.50 15.8 100 6.00 15.8 100 37 1.50 15.5 98 6.00 12.0 76 TABLE 8 Influence on the Growth of Mustard; Soil Treatment (Neubauer System) Application rate Plant height Compound No. kg/ha cm relative untreated - 15.0 100 41 3.00 14.5 97 12.00 13.0 87 2 3.00 15.0 100 12.00 11.5 77 2a 3.00 15.0 100 12.00 10.1 67 7 3.00 14.9 99 12.00 12.0 80 12 3.00 13.2 88 12.00 13.0 87 TABLE 9 Influence on the Growth Height of Oats; Soil Treatment (Neubauer System) Application rate Plant height Compound No. kg/ha cm relative untreated - 30.0 100 41 3.00 28.0 93 12.00 25.4 84 2 3.00 20.7 69 12.00 19.8 66 2a 3.00 23.4 78 12.00 18.9 63 12 3.00 24.0 80 12.00 18.9 63 TABLE 10 Influence on the Growth Height of Rye: Soil Treatment (Neubauer System) Application rate Plant height Compound No. kg/ha cm relative untreated - 32.0 100 41 3.00 32.0 100 12.00 29.9 93 2 3.00 29.5 92 12.00 25.5 90 2a 3.00 28.5 89 12.00 25.6 80 12 3.00 28.7 90 12.00 25.6 80 TABLE 11 Influence on the Growth Height of Barley; Vegetation Experiment - Soil Treatment (Mitscherlich System) Application rate Plant height Compound No. kg/ha cm relative untreated - 55 100 41+3 3.00 52 95 2 0.75 52 95 3.00 42 76 7 0.75 52 95 3.00 46 84 12 0.75 54 98 3.00 52 95 18 0.75 53 96 3.00 49 89 +) leaf treatment.

TABLE 12 Influence of Compound 4 on the Development of Various Winter Rape Varieties in the open I+); Postemergence Treatment Growth of the rape plants in % Untreated control=100 Days after treatment Variety Application rate 8 14 44 154 190 Diamant 0.5 95 90 90 95 100 1.0 92 80 75 95 100 2.0 85 70 70 85 95 4.0 75++ 65++ 55 80 90 Erra 0.5 95 95 85 100 100 1.0 90 80 80 100 100 2.0 85 75 60 95 95 4.0 70++ 60++ 45 90 90 Lesira 0.5 95 90 85 100 100 1.0 90 85 75 95 100 2.0 80 70 55 90 95 4.0 70++ 60++ 45 80 90 Treatment with Compound No. 41 Diamant 4.0 92 95 95 100 100 Erra 4.0 100 100 95 100 100 Lesira 4.0 100 100 95 100 100 +I=sown on Sept. 29, 1975, treated on Oct. 8, 1975.

++=necroses at edges of leaves.

Commencement of flowering normal for all varieties and application rates.

TABLE 13 Influence of Compound No. 4 on the Development of Various Winter Rape Varieties in the Open all+); Postemergence Treatment Growth of the rape plants in " Untreated control=100 Days after treatment Application rate Variety kg/ha 8 20 103 169 Diamant 0.5 95 90 100 100 1.0 90 85 95 100 2.0 85 78 95 100 4.0 80 65 90 100 Erra 0.5 95 88 100 100 1.0 90 80 95 100 2.0 85 75 95 100 4.0 80 65 88 100 Lesira 0.5 95 90 100 100 1.0 85 82 95 100 2.0 85 75 95 100 4.0 80 65 90 100 Treatment with compound No. 41 Diamant 4.0 95 95 100 100 Erra 4.0 100 95 100 100 Lesira 5.0 100 95 100 100 II+=sown on Sept. 22, 1975, treated on Oct. 29, 1975.

Flowering normal for all varieties and application rates.

TABLE 14 Inhibition of the Growth of Various Unwanted Broadleaved Plants by Compound No. 4 in the Open; Postemergence Treatment % inhibition (control=0) Days after treatment Application rate Species kg/ha 14 44 154 Galium aparine 2.0 8+ 20 3 4.0 25 32 12 Lamium amplexicaule 2.0 23 33 17 4.0 45 43 23 Stellaria media 2.0 22 37 15 4.0 48 47 23 Treatment with Compound No. 41 Galium aparine 4.0 0 0 0 Lamium amplexicaule 4.0 0 0 0 Stellaria media 4.0 0 0 0 +0=no inhibition, 100=plants destroyed.

The use of the compounds of formula I as growth regulators is not, however, limited to these examples.

The compounds of formula I may be used as conventional formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The forms of application depend entirely on the purpose for which the compounds are being used; in any case they should ensure a fine and uniform distribution of the active ingredient. The formulations are prepared in known manner, e.g., by extending the active ingredient with solvent and/or carriers, employing if desired emulsifiers and dispersants; if water is used as diluent, other organic solvents may also be employed as auxiliary solvents. The main additives which are suitable are solvents such as aromatics (e.g., xylene, benzene), chlorinated aromatics (e.g., chlorobenzenes), paraffins (e.g., petroleum fractions), alcohols (e.g., methanol, butanol), amines (e.g., ethanolamine, dimethylformamide), and water; carriers such as natural flours (e.g., kaolins, aluminas, talc, chalk) and synthetic rock flours (e.g., highly disperse silicic acid, silicates); emulsifiers such as non-ionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates), and dispersants such as lignin, sulfite waste liquors and methyl cellulose.

Generally, the formulations contain from 0.1 to 95, preferably from 0.5 to 90% by weight of active ingredient.

The formulations, or the ready-to-use preparations made therefrom (solutions, emulsions, suspensions, powders, dusts, pastes or granules), are employed in conventional manner, e.g., pre-emergence, postemergence or as seed dressings.

The application rates vary depending on the effect desired, and are from 0.2 to 5 or more, preferably, however, from 0.5 to 2, kg of active ingredient per hectare.

The compounds of formula I may, in these application forms, also be mixed and applied with other active ingredients, e.g., herbicides, insecticides, growth regulators and fungicides, and with fertilizers. When mixed with growth regulators, the spectrum of action is often increased. In the case of some growth regulator mixtures synergistic effects also occur, i.e., the effectiveness of the combination product is greater than the sum of the actions of its individual components.

EXAMPLE 3 90 parts by weight of compound 4 is mixed with 10 parts by weight of N methyl - a - pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

EXAMPLE 4 20 parts by weight of compound 2 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide to I mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 5 20 parts by weight of compound 3 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 6 20 parts by weight of compound 4 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210 and 280"C, and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

EXAMPLE 7 20 parts by weight of compound 5 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene - a - sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid obtained from a sulfite waste liquor, and 60 parts by weight of powdered silica gel, and triturated bn a hammer mill. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquid is obtained containing 0.1% by weight of the active ingredient.

EXAMPLE 8 3 parts by weight of compound 6 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

EXAMPLE 9 30 parts by weight of compound 7 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

EXAMPLE 10 40 parts by weight of compound 8 is intimately mixed with 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. Dilution in 100,000 parts by weight of water gives an aqueous dispersion containing 0.04 wt% of active

Claims (28)

WHAT WE CLAIM IS:

1. A process for influencing the growth of plants, wherein the plants or the soil are treated with a compound of the general formula

where R' denotes an unsubstituted or chloro-substituted unsaturated aliphatic hydrocarbon radical of 3 to 5 carbon atoms, 4-chlorobenzyl or 2,4-dichlorobenzyl, R2 denotes hydrogen or alkyl of 1 to 4 carbon atoms, R3 denotes fluoro, chloro, bromo, methyl, trifluoromethyl, phenyl or alkoxy of 1 to 3 carbon atoms, and n denotes 0, 1, 2 or 3, the radicals R3 being identical or different when n=2 or 3, or a salt thereof.

2. A process as claimed in Claim I, wherein R' denotes allyl, propargyl, 2butenyl, 2-butynyl, 2-methyl-2-butenyl, 4-chlorobenzyl or 2-chloro-2-butenyl, R2 denotes hydrogen, methyl or n-butyl, R3 denotes fluoro, chloro, bromo, methoxy or methyl and n denotes 0, 1, 2 or 3, the radicals R3 being identical when n=2 or 3.

3. A process as claimed in Claim 1 in which the combination of R', R2, R3 and n is as specified in any of compounds Nos. 1 to 39, 46 and 47.

4. A process as claimed in Claim 1, wherein the compound is 1 - alloyloxy 1 - (4 - bromophenyl - 2 - (1,2,4 - triazolyl - 1) - ethane or a salt thereof

5. A process as claimed in Claim 1, wherein the compound is 1 - allyloxy 1 - (4 - chlorophenyl) - 2 - (1,2,4 - triazolyl - 1) - ethane or a salt thereof.

6. A process as claimed in Claim 1, wherein the compound is 1 - allyloxy 1 - (2,4 - dichlorophenyl) - 2 - (1,2,4 - triazolyl - 1) - ethane or a salt thereof.

7. A process as claimed in Claim 1, wherein the compound is 1 - allyloxy 1 - (4 - methoxyphenyl) - 2 - (1,2,4 - triazolyl - 1) - ethane or a salt thereof.

8. A process as claimed in Claim 1, wherein the compound is 1 - allyloxy 1 - (4 - bromophenyl) - 2 - (1,2,4 - triazolyl - 1) - propane or a salt thereof.

9. A process as claimed in Claim 1, wherein the compound is 1 - allyloxy 1 - (p - tolyl) - 2 - (1,2,4 - triazolyl - 1) - ethane or a salt thereof.

10. A process as claimed in Claim 1, wherein the compound is I - (4 chlorobenzyloxy) - 1 - (4 - bromophenyl) - 2 - (1,2,4 - triazolyl - 1) - n - hexane or a salt thereof.

11. A process as claimed in any of Claims 1 to 10, wherein the compound is applied as a seed dressing.

12. A process as claimed in any of Claims 1 to 10, wherein the compound is applied postemergence.

13. A process as claimed in any of Claims 1 to 12, wherein the plants whose growth is to be influenced are rape plants.

14. A process as claimed in any of Claims 1 to 12, wherein the plants whose growth is to be influenced are winter cereal plants.

15. A compound of the formula

where R', R3 and n have the meanings given in Claim 1 and R4 denotes alkyl of 1 to 4 carbon atoms, or a salt thereof.

16. A compound as claimed in Claim 15, wherein R', R3 and n have the meanings given in Claim 2 and R4 denotes methyl or n-butyl.

17. 1 - Allyloxy - 1 - (4 - bromophenyl) - 2 - (1,2,4 - triazolyl - 1)propane or a salt thereof.

18. 1 - Allyloxy - 1 - (4 - bromophenyl) - 2 - (1,2,4 - triazolyl - 1) - ethane or a salt thereof.

19. 1 - Allyloxy - 1 - (4 - bromophenyl) - 2 - (1,2,4 - triazolyl - 1) - ethane nitric acid salt.

20. A process for the manufacture of a compound as claimed in Claim 15, wherein 1 - aryl - 2 - triazolylalkanol of the formula

where R3, R4 and n have the meanings given in Claim 15 or 16, is reacted with an alkali metal hydride, amide or alcoholate and the resulting alkali metal salt is reacted with a compound of the formula X-R1, where R' has the meaning given in Claim 15 or 16 and X denotes chloro, bromo, iodo, methosulfate or toluene sulfonate.

21. A compound as claimed in Claim 15 when manufactured by a process as claimed in Claim 20.

22. A composition for influencing the growth of plants, comprising a solid or liquid carrier and a compound as claimed in any of Claims 15 to 19 or 21 as active ingredient.

23. A composition as claimed in Claim 22 in the form of a solution, emulsion or dispersion in an organic solvent.

24. A composition as claimed in Claim 22 as an aqueous formulation containing a dispersant or emulsifier.

25. A composition as claimed in Claim 22 in the form of dust, powder, paste or granules.

26. A composition as claimed in any of Claims 22 to 25 additionally containing a herbicide, insecticide, fungicide, other growth regulator and/or fertilizer.

27. A composition as claimed in Claim 13 and substantially as described in any of the foregoing Examples 3 to 11.

28. A process for preparing a composition for influencing the growth of plants, wherein a solid or liquid carrier is mixed with a compound as claimed in any of Claims 15 to 19 or 21.