HU180206B - Compositions controlling growth of plants,containing triasolyl-alkohols as active agents,and process for producing gamma-asolyl-alkoholos - Google Patents

Abstract

The invention relates to growth-regulating agents comprising a solid or liquid carrier and a gamma-azolyl alcohol compound of the general formula (formula) in which R exp 1 and r exp 2 are identical or different and alkyl having up to 5 atoms, cycloalkyl, furanyl, thiophenyl , Naphthyl or phenyl, where the phenyl radical may be substituted by halogen, alkyl, alkoxy, alkenyloxy, hydroxy, nitro or trifluoromethyl and Az is an imidazolyl, pyrazole, 1,2,4-triazolyl radical.

Description

Plant growth regulating agents containing triazolyl alcohols and process for the preparation of 7-azolyl alcohols

The present invention relates to plant growth regulators containing triazolyl alcohols as active ingredients and to processes for the preparation of [alpha] -azolyl alcohols.

Agents containing 2-chloroethyltrimethylammonium chloride (chlorocholine chloride, CCC) are known to be used as active ingredients to influence the growth of plants. Biol. Chem. 235. 475/1960/3.

Plant growth regulators, for example, can reduce the length of plants, cause germination and flowering. they can increase frost tolerance or stimulate or inhibit the formation of side shoots. '

Growth regulators play a particularly important economic role in delaying the harvesting of cereals before harvest.

In practice, hitherto used and proven growth regulators have little effect on cereals, where growth retardation is required to delay ripening.

We have found that the triazolyl alcohols of formula (I) are in this formula

R ¹ is C 1 -C 4 alkyl or phenyl optionally substituted with halo;

R 1 is C 1 -C 4 alkyl or phenyl substituted with furanyl or optionally substituted with up to two halogen atoms, one C 1 -C 4 alkyl; and

Agents containing the 1,2,4-triazolyl group have very good plant growth regulating activity.

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Agents containing the triazolyl alcohols of the present invention are useful in controlling the growth of a number of plants, and this effect is primarily manifested in the reduction of length growth. The effect of the new agents is superior to the known agents.

The agents of the invention are particularly useful for controlling the development of cereals, such as corn, barley, rye, rice and oats, and dicotyledonous plants, such as sunflower, tomato, grape, cotton, rape, or ornamental plants, such as walleye and hibiscus. Treated plants have a lower height and darker leaf discoloration.

New agents can be introduced into crop plants through the soil, i.e. by spraying the roots or leaves. The new substances are very well tolerated by plants, so the amount used may vary widely depending on the desired effect; in general, 0.25 to 12 kg of active ingredient per hectare proved to be effective.

The process of the present invention provides Qr-azolyl alcohols of formula (I) wherein

R is phenyl substituted with 1 to 6 carbon atoms, furanyl, thienyl or naphthyl, or optionally substituted with up to two halogens, or a phenyl, (C1-C4) alkyl, or (C1-C4) alkoxy;

R is C 1-6 alkyl, thienyl, pyridyl or naphthyl, or furanyl optionally substituted with C 1-4 alkyl, or optionally substituted with up to two halogen atoms and / or C 1-4 alkoxy, or a hydroxy, nitro, or C 1-4 alkyl group. substituted phenyl; and

It is imidazolyl or 1,2,4-triazolyl.

These compounds are also useful as active ingredients in plant growth regulators.

In the formula (1), R ^{1 is,} for example, methyl, isopropyl, η-butyl, sec-butyl, isobutyl, tert-butyl, furanyl, thienyl, naphthyl, biphenyl, phenyl, ρ- tolyl, m- and p-methoxyphenyl, p-fluorophenyl, p-chlorophenyl or 2,4-dichlorophenyl; Examples of R are tert-butyl, furanyl, 2-methylfuranyl, thienyl, pyridyl, naphthyl, phenyl, p-telyl, p-isopropylphenyl, o- and p-methoxy. phenyl, 2,3-dimethoxyphenyl, o-hydroxyphenyl, p-chlorophenyl, m- and ρ-bromophenyl, 2,4-dichlorophenyl,

It may be 2,4-dibromophenyl or p-nitrophenyl.

The compounds / 1 / are novel and can be prepared by / 11 / general-képletűp azöli1 ketones - reduction - you risk, in which R \ R ² and Az are as defined above. The reduction may be effected, for example, by the following methods;

α complex with hydrides such as sodium borohydride in a polar solvent such as methanol or lithium alanate in tetrahydrofuran at 0 to 30 ° C and the product is hydrolyzed with e.g. aqueous base or acid or b / hydrogen in a catalyst such as platinum or Raney- in the presence of nickel in a polar solvent such as methanol, ethanol or isopropanol at 40 to 60 ° C and at a pressure of 1 to 100 bar, or

-2180206 c / aluminum isopropylate in an inert solvent at 40 to 120 DEG C. and the products are hydrolyzed, for example with aqueous hydrochloric acid.

The resulting compounds of formula (I) may be isolated and optionally purified by conventional means.

The starting compounds of formula (11) can be prepared as follows.

For the preparation of the β- (1,2.4-triazol-1-yl), N-imick azolyl and 3-pyrazolyl ketones ¹ of the general formula (11), the appropriately substituted O (-unsaturated ketones) are solubilized with the desired azoles. or in the presence of a diluent at 20 to 80 ° C, or in place of the azo, A-unsaturated ketones, the corresponding aldehydes and ketones are reacted with the corresponding azoles, optionally in the presence of a basic catalyst and optionally diluent.

The following example illustrates the preparation of starting compounds of the formula fTLf.

Example A To a solution of g / 0.11 mol / 3,3-dimethylbutan-2-one and 14 g / 0.1 mol / p-chlorobenzaldehyde in 120 ml of ethanol was added 10 ml of 20% aqueous sodium hydroxide solution and stirred for 2 hours at 50 ° C. The reaction mixture is then added

13.8 g / 0.2 mole / of 1,2,4-triazole and the mixture was stirred for 8 hours at 5O ^she C. The solvent was distilled off and the resulting residue was partitioned between water (300 mL) and ether (300 mL). The ethereal solution was dried over calcium sulfate, filtered, and dry hydrogen chloride gas was added to the solution at 5-10 ° C.

24.3 g (74%) of 1- (1,2,4-triazol-1-yl) -1- (4-chlorophenyl) -4,4-dimethylpentan-3-one are obtained in the form of its hydrochloride; the white crystals have a melting point of 139-141 ° C.

The following Table I describes the compounds of formula (Ha) which may be used as starting materials.

Table I

Serial - R ¹ number R ² X Y Z Op. ° c Op.C.HCl 1 tert-butyl 4-chlorophenyl N N CH 139-141 Second methyl tert-butyl N N CH Third isopropyl furan-2-yl N N CH 53-55 4th isopropyl 4-chlorophenyl N N CH 118-120 5th sec-butyl furan-2-yl N N CH 41-43 6th isobutyl furan-2-yl N N CH 163-166 7th tert-butyl furan-2-yl N N CH 69-71 8th tert-butyl 2-methylfuran-5-yl N N CH 69-51 9th tert-butyl thiophen-2-yl N N CH 118-120 10th sec-butyl naphthyl N N CH resin 11th isobutyl naphthyl N N CH 167-169 1 '* tert-butyl naphthyl N N CH 162-164 * 13 tert-butyl naphthyl N CH CH 68-69 14th 4-chlorophenyl tert-butyl CH N N 130-132 * 15 tert-butyl 4-chlorophenyl CH N CH 89-91 16th tert-butyl 4-chlorophenyl N CH CH 65-67

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Line number R ² X Y Z Op. ° c ° p , ° C, HC1 17th tert-butyl 4-bromophenyl N N CH 142-145 18th tert-butyl 2,4-dichlorophenyl N N CH 154-156 19th tert-butyl 2,4-dichlorophenyl CH N CH 75-77 20th tert-butyl 4-methylphenyl N N CH 153-155 21st tert-butyl 4-methylphenyl CH N CH 98-100 22nd tert-butyl phenyl N N CH 141-143 23rd tert-butyl 4,4-diethyl yl-phenyl N N CH 155-157 24th tert-butyl 4-methoxyphenyl N N CH 158-161 25th tert-butyl 2,4-dibrómfeni1 N N CH 104-106 * 26 tert-butyl 4-nitrophenyl N N CH 164-167 * 27 f uran-2-yl 2-methoxyphenyl N N CH 106 28th furan-2-yl 2-hydroxyphenyl N N CH 142-144 29th furan-2-yl 2,3-dimethoxyphenyl N N CH 101-102 30th phenyl · 2-methoxyphenyl N N CH 95-97 31st 4-methoxyphenyl 2-methoxyphenyl N N CH 134-135 32nd 4-chlorophenyl 4-methylphenyl N N CH 81-82 33rd furan-2-yl 4-methoxyphenyl N N CH 126-128 34th phenyl furan-2-yl N N CH 126 35th 3-methoxyphenyl furan-2-yl N N CH 130-133 36th 4-methoxyphenyl furan-2-yl N N CH 112-114 * 37 tert-butyl pyrid-2-yl N N CH 76-79 38th furan-2-yl tert-butyl N N CH 104-106 39th thiophen-2-yl tert-butyl N N CH 125-127 40th naphthyl tert-butyl N N CH 136-138 41st 4-methylphenyl tert-butyl N N CH 128-130 42nd 4-fluorophenyl tert-butyl N N CH 100-102 * 43 4-phenyl-kl6r tert-butyl N N CH 113-115 44th 4-chlorophenyl tert-butyl CH N CH 121-124 45th 2,4-dichloro-phenylpent tert-butyl N N CH 70-72 46th 3-bromophenyl tert-butyl N N CH 114-116 47th biphenyl tert-butyl N N CH 127-128 48th tert-butyl tert-butyl N N CH 98-99 49th furan-2-yl phenyl N N CH 106-108 50th furan-2-yl 3-Bromo-2-methoxyphenyl N N CH 146-148 51st tert-butyl 2-methoxyphenyl N N CH 92-95 52nd 2-methoxyphenyl furan-2-yl N N CH 53rd phenyl pyrid-2-yl N N CH * 54 4-chlorophenyl pyrid-2-yl N N CH 78-81 55th 4-methoxy- pyrid-2-yl N N CH 108-110

phenyl

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The following example illustrates the preparation of the γ-azolyl alcohols of formula ^(I ).

Example 1 a / 29.1 g of 1- [1,2,4-triazol-1-yl] -1- (4'-chlorophenyl) -4,4-dimethylpentan-1-one with J00 ml methanol To the solution of the crude product was added in portions with stirring and ice-cooling at 3-8 ° C, 5.9 g of sodium borohydride. The reaction mixture was stirred at room temperature for 8 hours and then concentrated. The resulting residue was stirred in 150 ml of 4% sodium hydroxide solution for 1 hour and then extracted with 250 ml of methylene chloride. The organic layer was dried over sodium sulfate and concentrated in vacuo. The resulting solid colorless residue was washed with petroleum ether (40 mL) and filtered off with suction. 26.1 g (89%) of 1- (1,2,4-triazol-1-yl) -1- (4'-chlorophenyl) -4,4-dimethylpentan-3-ol are obtained; mp 104-106 ° C.

b) 29.1 g of 1- [1,2,4-triazol-1-yl] -1- (4'-chlorophenyl) -4,4-dimethylpentan-3-one are dissolved in 100 ml of anhydrous ether. This solution is slowly added dropwise 5 »? g of lithium alanate in 200 ml of anhydrous ether suspension. The mixture was refluxed for 3 hours and 150 ml of ice water was added dropwise with ice-cooling. The reaction mixture was then mixed with 200 mL of 20% aqueous sodium hydroxide solution and extracted with 3 mL of 105 mL of ether. The organic layer was dried over sodium sulfate and concentrated in vacuo. The partially crystalline precipitate is mixed with light petroleum and washed. 24-9 g (85%) of 1- (1,2,4-triazol-1-yl) -1- (4 * -chlorophenyl) -4,4-dimethylpentan-3-ol are obtained; mp 104-106 ° C.

In a similar manner, the compound of formula II can be prepared. Compounds of formula (I) shown in Table II. .

Agents containing the compounds of Formula (I) include, for example, directly sprayable solutions and powders, suspensions - high-strength aqueous, oily or other suspensions in the form of dispersions, emulsions, oily dispersions, pastes, dusts, sprays or granules and may also be sprayed, sprayed, sprayed, or by watering. The application forms are adapted to the intended use, but in any case they must ensure the most even distribution of the active substances.

Medium and high boiling petroleum fractions, such as kerosene or gas oil, as well as coal and petroleum oils, aliphatic, cyclic and aromatic hydrocarbons and their derivatives, e.g. alcohols such as methanol, butanol; amines such as ethanolamine, dimethylformamide and valamine in water. Suitable carriers are natural mineral grinds, such as kaolin clay, talc, chalk, and synthetic mineral grinds, such as highly dispersed silica, silicates; non-ionic and anionic emulsifiers such as polyoxyethylene / fatty alcohol ether, alkylsulfonates and arylsulfonates as emulsifiers; as dispersants, for example, lignin, sulphite impurities and methylcellulose.

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

Other pesticides for the agents of the invention,

For example, -5180206 can be mixed with and used with, for example, herbicides, insecticides, growth regulators and fungicides.

The use of the growth regulators of the present invention is that they are utilized when geographic, weather and plant development conditions are best suited.

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-10180206

The following examples illustrate the effects of the growth regulators of the present invention and their potential applications, without excluding further applications.

Example 2 The biological efficacy of the new agents was tested in a greenhouse. The test plants were seeded in plastic containers of 12.5 cm diameter filled with peat medium containing sufficient nutrients. Treatment with an aqueous solution containing various amounts of active ingredient / 5. example / or dispersion / 7. example / was sprayed directly on the soil on the day of sowing. During the 18-day development period, the length of the plants treated with the agents of the invention was significantly less than that of the untreated control plants. 100-100 plants were used for each series of assays.

The known agent containing (2-chloroethyl) -trimethylammonium chloride (A) had a weaker effect.

The results are reported in III.-V. are summarized in Table.

III. spreadsheet

Effect on wheat growth

agent Rate of application, kg / ha Plant cm its length is relative Untreated control - 29.5 100 THE 3.0 21.1 71.5 12.0 19.3 65.4 7th 3.0 12.0 25.5 17.0 86.4 57.6 43rd 3.0 21.3 72.2 12.0 16.0 54.2

ARC. spreadsheet

Effect on length of barley

agent Amount used, kg / h Plant cm its length is relative Untreated control - 28.5 100 THE 3.0 23.3 81.8 12.0 21.5 75.4 ' 19th 3, Q 23.5 82.5 12.0 21.5 75.4 First 3.0 23.5 82.5. 12.0 20.0 70.2 43rd 3.0 25.7 90.0 12.0 18.4 64.7

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Table V.

Effect on length of rapeseed

agent Amount used, kg / h Plant cm its length is relative control - 16.0 100 THE 3.0 16.0 100 12.0 16.0 100 7th 3.0 15.0 93.8 12.0 10.5 65.6 First 3.0 15.0 93.8 12.0 11.0 68.8 19th 3.0 15.0 93.8 12.0 11.5 71.9 23rd 3.0 15.0 93.8 12.0 12.0 75.0 21st 3.0 15.0 93.8 12.0 12.0 75.0 35th 3.0 14.7 92.0 12.0 11.4 71.4

Example J sr. 7 · compound was mixed with 10 sr. N-methyl-O-C-pyrrolidone and thus a solution containing 90% by weight of the active ingredient can be used in the form of small droplets.

Example 4 a - sr. Compound 43 was dissolved in 90 µl. xylene, 8-10 mol of ethylene oxide and 1 mol of oleic acid N- / monoethanol / Tamid in 10 parts by weight, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of 5 parts of ethylene oxide and 1 mol of castor oil. The resulting solution was 100,000 sr. poured into water and uniformly distributed to give an aqueous dispersion of 0.02% active ingredient.

Example 5 · sr. Compound 1 was dissolved in 40 µl cyclohexanone, 30 µl. isobutanol, 7 "of ethylene oxide and 1 mol of isooctylphenol in 20 parts by weight of addition product and 40 mol of ethylene oxide and 1 mol of castor oil in 10 parts by weight of addition product. The solution was diluted 100,000. poured into water and evenly distributed to give an aqueous dispersion of 0.02% active ingredient.

Example 6 sr. Compound 19 was dissolved in 25 sr. cyclohexanol, 65 sr. 210-280 ° C in a mixture of a petroleum fraction boiling in the range of boiling point and 40 moles of ethylene oxide and 1 mole of castor oil in 10 parts by weight of addition product. The solution was diluted 100,000. poured into water and uniformly distributed to give an aqueous dispersion of 0.02% active ingredient. 7 · example · sr. Compound 23 was thoroughly mixed with 3 volumes. with diisobutylnaphthalene-oC-sulphonic acid, sodium sulphite impurities

-12180206 from 17 sr. lignin sulfonic acid sodium salt and 60 sr. powdered silica gel and blend in a hammer mill. The mixture was added at 20,000 sr. uniformly distributed in water to give a spray liquid containing 0.1% active ingredient.

Example 8

3rd sr. Compound 21 was thoroughly mixed with 97 l. powdered kaolin. A powder containing 3% by weight of active ingredient is obtained.

Example 9 sr. Compound 7 was thoroughly mixed with 92 sr. powdered silica gel and previously sprayed on silica gel with 8 sr. kaolin. A good adhesive is obtained.

Example 10.

sr. Compound 1 was thoroughly mixed with 10 µl. sodium salt of phenolsulfonic acid urea formaldehyde condensate, 2 sr. silica gel and 48 sr. water. A stable aqueous dispersion is obtained. This is 100,000 sr. diluted with water to give an aqueous dispersion of 0.04% active ingredient.

Example 11 sr. Compound 43 was thoroughly mixed with 2 sr. calcium salt of dodecylbenzenesulfonic acid, 8 sr. fatty alcohol poly (glycol ether), phenolsulfonic acid urea formaldehyde condensate 2 sr. sodium salt and 68 sr; with paraffinic mineral oil. A stable, oily dispersion is obtained.

Claims (2)

Patent claims A plant growth regulator, characterized in that it contains from 0.1 to 95% by weight of the active ingredient triazolyl alcohol of the formula (I) R ¹ is C 1 -C 4 alkyl or phenyl optionally substituted with halo; R is C 1-4 alkyl or furanyl, or optionally with up to two halogens or one Phenyl substituted with C 1-4 alkyl; and It is a 1,2,4-triazolyl group, a solid and liquid carrier, preferably with at least one of natural and artificial mineral ground, petroleum fraction, aliphatic and aromatic hydrocarbons and surfactant additives, preferably anionic and nonionic dispersants, emulsifiers and wetting agents. together. 2. A process for the preparation of zolyl alcohols of the formula I in this formula R ¹ is C 1 -C 6 alkyl, furanyl, thienyl or naphthyl optionally substituted with up to two halogens, or one phenyl, C 1 -C 4 alkyl; or phenyl substituted with C 1-4 alkoxy; R is C 1 -C 6 alkyl, pyridyl, thienyl or naphthyl, or furanyl optionally substituted with C 1 -C 4 alkyl, or optionally with up to two halogen atoms and / or C 1 -C 4 alkoxy or one hydroxy, nitro group Phenyl substituted with -13180206 or C1-C4 alkyl, and Az is imidazolyl or 1,2,4-triazolyl group - characterized in that a ketone -azolil / 11 / general formula: - wherein R ^1, R ² and Az are as defined above - is reduced.