Derivatives epoxycyclohexane and plant growth regulators

 

(57) Abstract:

The invention relates to a plant growth regulator comprising as an active ingredient derived epoxycyclohexane represented by the General formula 1 in which R1represents a hydrogen atom, a C1-C6is an alkyl group or a C3-C6-cycloalkyl group, and R2and R3form together a C2-C3-polymethene group, as well as plant growth regulator, including derived epoxycyclohexane and brassinosteroid as active ingredients. Derivatives epoxycyclohexane show a strong effect of regulating the growth of plants, which is equivalent to or higher than the effect of abscisic acid and are useful as plant growth regulators, such as tools, which accelerate plant growth, germination and growth of seedlings, inhibiting transpiration and wilting, tools that enhance the cold resistance, accelerating growth, thickening or ripening fruits, roots and tubers, stems or bulbs and other Energeticheskiy effect is achieved by combining the derived epoxycyclohexane with brassinosteroids. 3 S. and 11 C.p. f-crystals, 11 PL.

The technical field

Absolu abscisic acid was found in 1963, steel is known for its physiological actions, including the formation of the separating layer, the induction of peace, the suppression of germination (education kidneys, suppression of flowering, the suppression of the yield in the arrow (development pedicels), suppression of transpiration, activation, aging, and resistance to stress (e.g., increased cold tolerance). Although I believe that abscisic acid usually manifests vast growth effect, as described above, it was recently revealed that, similar to other plant hormones, abscisic acid detects, as the promoting or activating and inhibitory effects depending on its concentration and, for example, at low concentrations it activates the growth of plants, increasing the harvest (Nacabori et al., Bulletin of the Aomori Agricultural Experiment Station in 1991 (1992)). Further known to use for promotion thickening (thickening) and fruit ripening (Japanese patent LOP publication NN 264005/1992, 264006/1992 and 264007/1992), prevention of flowers and immature fruits from falling (Japanese patent LOP publication N 139911/1993), activation of growth of agricultural products (Japanese patent LOP publication N 178705/1993) or activation of flowering (Japanese patent publication N 186303/1993).

However, abscisic the more high effects, and thus, abscisic acid is almost never used. Recently developed a method of obtaining abscisic acid natural type by culturing a microorganism of the genus Botrytis, but one can hardly say that this method is satisfactory (Japanese patent LOP NN 296696/1988, 296697/1988 and 60590/1990). There have been several reports of its organic synthesis, but there are still problems associated with a large number of stages, cost, stereoselectivity (Helv. Chim. Acta, 71, 931 (1988); J. Org. Chem., 54, 681 (1989); and (Japanese patent LOP publication N 184966/1991).

Of those compounds, which are plant growth regulators according to the present invention, a free carboxylic acid and metropolitaine derivative described in the above literature as intermediates for chemical synthesis, but they say nothing about the fact that these intermediate products have physiological actions such as abscisic acid.

On the one hand, brassinosteroids are a group of ubiquitous compounds present in plants, and have a specific physiological effect on growth, such as promotion or activation of ROS is talsania fruits and others, and promotion of germination or rooting seeds or cuttings.

However, it was not known that the mixture of abscisic acid or substances similar to abscisic acid and brassinosteroids has Energeticheskie effect on the regulation of plant growth.

Disclosure of the invention

The object of the present invention is the provision of a new and highly active substances exhibiting physiological actions such as abscisic acid and highly active plant growth regulator.

As a result of his tireless research, the present inventors have found that specific epoxycyclohexane derivatives exhibit excellent physiological actions such as abscisic acid, and the mixture of these compounds and brassinosteroid acts Energetichesky on plants, providing a strong regulatory effect on their growth, thereby completing the present invention.

In other words, the first invention of the present application relates to a plant growth regulator comprising as an active ingredient derived epoxycyclohexane represented by the General formula 1

< / BR>
in which R1represents the atom weegschaal independently C1-C6alkyl group or merged, forming a C2-C3polymethene group which may be substituted C1-C6alkyl group, and, in particular, to speed up growth of plants, the accelerator of growth of shoots, inhibitor transpiration and wilting, the amplifier cold tolerance, and speed up growth, thickening or ripening fruits, roots or tubers, stems or bulbs.

The second invention of the present application relates to a plant growth regulator comprising as active ingredients derived epoxycyclohexane represented by the General formula (1), and brassinosteroid, and, in particular, to speed up growth of seedlings, the amplifier cold tolerance and growth accelerator, thickening or ripening fruits, roots or tubers, stems or bulbs.

The third invention of the present application is related to the derived epoxycyclohexane represented by the General formula (3):

< / BR>
in which R1represents C2-C6alkyl group or a C3-C6cycloalkyl group, and R2and R3are independently C1-C6alkyl group or merged, forming a C2-C3polietileno the SUB>-C6the alkyl group represented by the symbol R1includes methyl group, ethyl group, through the group, isopropyl group, boutelou, isobutylene, terbutaline, tert-boutelou, pentelow, isopentanol, hexeline, second-hexoloy group and others Among them preferred by physiological action are C2-C4alkyl groups, especially through and isopropyl group.

In the General formula (3) C2-C6the alkyl group represented by the symbol R1includes ethyl group, through the group, isopropyl group, boutelou, isobutylene, second-boutelou, tert-boutelou, pentelow, isopentanol, hexeline, second-hexoloy group and others Among them, particularly preferred in connection with a stronger physiological effect are sawn and isopropyl group.

In the General formulas (1) and (3) C3-C6cycloalkyl groups represented by the symbols R1and R1include cycloalkyl group, cyclobutyl group and tsiklogeksilnogo group.

In the General formulas (1) and (3) C1-C6alkyl groups represented by the symbols R2and R3is predpochtitel group. C2-C3polymethene group which may be substituted C1-C6alkyl group include ethylene group, propylene group and others Among them ethylene group is preferred in view of the strong activity and ease of synthesis. Group Deputy, not necessarily present in the specified polymethene group includes the above-described C1-C6alkyl group.

Brassinosteroids used in the present second invention, include brassinolide and its analogues ("Shokubutsu No Depending Chosetsu" (Chemicai Regulation of Plant), 22[1], 10 - 17 (1987); "Yukagaku" (Oil Chemistry), 39[4], 227 - 235 (1990)). Analogs include compounds developed by some of the present inventors, which are represented by the General formula (2):

< / BR>
in which R4and R5submit C1-C6the lower alkyl groups ("Shokubutsu No Depending Chosetsu" 29[1], 23 - 30 (1994); Japanese patent LOP publication N 125396/1989).

C1-C6alkyl groups represented by the symbols R4and R5in the General formula (2) are preferably C1-C4alkyl group with a straight chain, and they include methyl, ethyl, sawn and boutelou group. Due to the high activity, in particular, suppose zestawienie General formula (1) and (3), work in General as follows: where R1R2and R3have the meanings given above.

Epoxycyclohexanecarboxylate (4), which is the starting material can be synthesized by the method described in the literature (Helv. Chim. Acta, 71, 931 (1988)). The conversion of compounds (4) carboxylic acid of the formula (1A) can be carried out according to the method described in the Japanese patent LOP publication N 184966/1991. These compounds represented by formula (3) can be obtained using complex esterification of carboxylic acids of the formula (1A), for example, by reaction with the appropriate alcohol in the presence of a condensing agent, such as carbodiimide. In the Japanese patent LOP publication N 184966/1991 describes that the compound (1b) of the formula (1) in which R1represents a methyl group, can be synthesized by exposure to the action of diazomethane on carboxylic acid (1A). However, this known method is limited to the synthesis of the methyl ester and cannot be used for synthesis of other esters.

The compounds of formula (2) used in the second invention is obtained usually as follows: where R4and R5have the meanings given above.

When (22E, 24S)-24-e catalytic amount of osmium tetroxide in an inert gas, such as nitrogen, argon, etc. in the presence of tert-butylhydroperoxide or N-methylmorpholin-N-oxide, its dihydroxypropane in alpha - and 3α-the provisions of the proceeds selectively in regulating the quantities of reagents, and Alfa, 3α-dihydroxy derivative can be obtained with high yield. This dihydroxy derivative (8) was dissolved in pyridine containing 4-dimethylaminopyridine, and subjected to reaction with an appropriate carboxylic anhydride (for example, propionic anhydride, butyric anhydride, and others), giving the compound (9). Then the compound (9) is dissolved in a chlorinated organic solvent stable to oxidation and oxidized organic peroxide, for example, adventurou acid, m-monochlorobenzene acid, m-monobromoacetic acid, monophthalmos acid, cryptanalyses acid or their sodium or potassium salts, giving the compounds of formula (2).

As the plant growth regulator according to the first invention specified derived epoxycyclohexane can be mixed with conventional carriers, diluents, etc. for application to plants or seeds of plants in the form of, for example, liquid, powder, emulsion, wettable powder, granules, etc. is s and bactericides, insecticides and acaricides and other Extras can be added such auxiliary agents, as the spreaders and stickers (i.e. respectively the agents contributing to the distribution and adhesion), emulsifier, wetting agent, dispersing agent, fixing agent disintegrity agent and other Data carriers, diluents, auxiliary agents, etc. are preferably chosen to optimize the regulating action on plant growth.

The amount of the plant growth regulator according to the first invention varies depending on the method of application and desired action. For application by spraying, for example, its concentration is preferably 1000 - 1 h/million, more preferably 100 to 5 hours/million For application by dipping or makanya seeds, etc. its concentration is preferably 1 to 0.001 PM/million, more preferably 0.1 - 0.01 h/million

As the plant growth regulator according to the second invention of the specified derivative epoxycyclohexane and brassinosteroid can be mixed with conventional carriers, diluents, etc. for application to plants or seeds of plants in water, for example, liquid, powder, emulsion, wettable powder, whether herbicides, fungicides and bactericides, insecticides and acaricides and other Extras can be added auxiliary agents, such as spreaders and stickers (i.e. respectively the agents contributing to the distribution and adhesion), emulsifier, wetting agent, dispersing agent, fixing agent and disintegrity agent. Data carriers, diluents, auxiliary agents, etc. are preferably chosen to optimize the regulating action on plant growth.

Number and ratio of mixing derived epoxycyclohexane and brassinosteroid in the plant growth regulator according to the second invention vary depending on method of application and desired action. For application by spraying, for example, it is preferable to mix the derived epoxycyclohexane within a 100 - 0.1 h/million brassinosteroids in the quantitative range of 0.1 - 0.001 h/million

Plants, to which are applied plant growth regulators according to the present first and second inventions include, but are not limited to, vegetable crops, such as spinach, Chinese cabbage, cucumbers, eggplant, Perilla long, cabbage, chrysanthemum Daisy chained, leeks and Lou who and corn, legumes such as soy beans, adzuki beans and peanuts, industrial crops such as sugar cane and hemp, fruit, such as grapes, persimmons, tangerines, apples, tomatoes, melon, pear, strawberries, peaches, bananas, pineapples and coffee, ornamental plants, such as rubber wood, Phoenix shrub and benzoin summer, and flowers, such as chrysanthemums, carnations, roses, bluebells, lilies and tulips.

The best way to embodiments of the invention

Hereinafter in this description of the present invention is described in detail with reference to examples and sample tests, which are however not intended to limit the present invention.

Primer. Synthesis of compound (3b)

To 308 mg (1.00 mmol) of 4,4-Ethylenedioxy-1-[4-(hydroxycarbonyl)-3-methyl-1,3-butadiene-1-yl] -1,2-oxo-2,6,6-trimethylcyclohexane (1A) (the product obtained in the same manner as in example 2 in Japanese patent LOP publication N 184966/1991) and 180 mg (224 μl, 3.00 mmole) propyl alcohol in dry dichloromethane (1.5 ml) was added 98 mg (0.80 mmole) of n-dimethylaminopyridine (DMAP), and to the mixture while cooling on ice was barotiwala argon gas, and the mixture was germetizirovany in argon atmosphere. With stirring under ice cooling to the mixture was dopaminemediated for 15 minutes under ice cooling, and then for 3 hours at room temperature. Addition was added 10 ml of diethyl ether to the reaction solution, which was accompanied by the formation of a huge number of white precipitation, and precipitation was removed by filtration. Addition was added diethyl ether, and was rinsed with a mixture of aqueous 2 M hydrochloric acid/saturated sodium chloride solution, then with aqueous saturated sodium bicarbonate solution, and saturated aqueous sodium chloride. Then Diethyleneamine layer was separated and dried over anhydrous sodium sulfate. The solvent was distilled, and the resulting crude oil, 385 mg, was purified using chromatography on silicagel column (16 g of Wako Gel C-200TM; hexane: ethyl acetate = 4: 1) to give 296 mg of 4,4-Ethylenedioxy-1-[4-(propoxycarbonyl)-3-methyl-1,3-butadiene-1-yl] -1,2-oxo-2,6,6-trimethylcyclohexane (3b) as a colorless oily substance (yield: 84%).

1H-NMR (CDCl3) (million USD) : 0.96 (3H, T., J=7.4), 1.00 (3H, s), 1.22 (3H, s), 1.25 (3H, s), 1.34 (1H, DD), J=2.1, 13.6), 1.68 (2H, DD., J=6.7, 7.4), 1.74 (1H, d , J=13.6), 2.01 (3H, d, J=1.3), 2.04 (1H, DD), J=2.1, 15.7), 2.28 (1H, d, J=15.7), 3.81-3.97(4H, m), 4.07 (2H, d, J=6.7), 5.71 (1H, Shir.C.), 6.27 (1H, DD), J=0.6, 16.1), 7.62 (1H, DD), J=0.7, 16.1).

LRMS m/z: 350 (M+), 291 (M+-C3H7O), 264 about 350.2103. []2D0= 10.22 (1.8, CHCl3).

Example 2. Synthesis of compound (3A)

Repeat the same procedure as in example 1, except that used was 138 mg (3.00 mmole) of ethyl alcohol instead of propyl alcohol, giving 264 mg of 4,4-Ethylenedioxy-1-[4-(etoxycarbonyl)-3-methyl-1,3-butadiene-1-yl]-1,2-oxo-2,6,6-trimethylcyclohexane (3A) (yield: 78.5%).

1H-NMR (CDCl3) (million$): 1.00 (3H, s), 1.22 (3H, s), 1.25 (3H, s), 1.38 (3H, T. , J=7.1), 1.34 (1H, DD), J=2.1, 13.7), 1.75 (1H, d, J=13.7), 2.01 (3H, d , J=1.3), 2.05 (1H, DD), J=2.1, 15.7), 2.28 (1H, d, J=15.7), 3.82-3.96 (4H, m), 4.17 (2H, square, J=7.1), 5.70 (1H, Shir.C.), 6.27 (1H, DD), J=0.6, 16.0), 7.63 (1H, DD), J=0.8, 16.0).

LRMS m/z: 336 (M+).

HRMS m/z: On theory ( in the form of C19H28O5) 336.1935; Found 336.1913.

Example 3. Synthesis of compound (3C)

Repeat the same procedure as in example 1, except that used was 180 mg (230 ml) of isopropyl alcohol instead of propyl alcohol, giving 282 mg of 4,4-Ethylenedioxy-1[4-(isopropoxycarbonyl)-3-methyl-1,3-butadiene-1-yl]-1,2-oxo-2,6,6-trimethylcyclohexane (3C) (yield: 81%).

1H-NMR (CDCl3) (mln.) : 1.00 (3H, s), 1.22 (3H, s), 1.25 (3H, s ), 1.26 (6N, d, J=6.3), 1.34 (1H, DD), J=2.1, 13.7), 1.74 (1H, d, J=13.7), 2.00 (3H, d , J=1.3), 2.04 (1H, DD, J=2.1, 15.8), 2.28 (1H, d, J=15.8), 3.81-3.94 (4H, M ), 5.06 (1H, Sept., J=6O), 264 (M+-C4H6O2). RMS m/z: On theory (in the form of C20H30O5) 350.2091; Found 350.2087. []2D0= 13.00 (1.8, CCl3).

Example 4. Synthesis of compound (3d)

Repeat the same procedure as in example 1, except that used was 227 mg (3.00 mmole) of butyl alcohol instead of propyl alcohol, giving 306 mg of 4,4-Ethylenedioxy-1-[4-(butoxycarbonyl)-3-methyl-1,3-butadiene-1-yl]-1,2-oxo-2,6,6-trimethylcyclohexane (3d) (yield: 84%).

1H-NMR (CDCl3) (mln.) : 0.94 (3H, T., J =7.4), 1.00 (3H, s), 1.22 (3H, s), 1.25 (3H, s), 1.34 (1H, DD), J=2.1, 13.7), 1.40 (2H, TCEs., J=7.4, 7.4), 1.64 (2H, t , J=6.7, 7.4), 1.74 (1H, d, J=13.7), 2.01 (3H, d, J= 1.2), 2.04 (1H, DD), J=2.1, 15.7), 2.28 (1H, d, J=15.7), 3.82-3.96 (4H, m ), 4.12 (2H, T. , J=6.7), 5.70 (1H, Shir.C.), 6.27 (1H, DD), J=0.5, 16.0), 7.63 (1H, DD), J=0.7, 16.0). LRMS m/z: 364 (M+).

HRMS m/z: On theory (in the form of C21H32O5) 364.2247; Found 364.2253.

Example 5. Synthesis of compound (3E)

Repeat the same procedure as in example 1, except that used was 258 mg (3.00 mmole) Cyclopentanol alcohol instead of propyl alcohol, giving 312 mg of 4,4-atiende-hydroxy-1-[4-(cyclopentanecarbonyl)-3-methyl-1,3-butadiene-1-yl] -1,2-oxo-2,6,6-trimethylcyclohexane (3E) (yield: 83%).

1H-NMR (CDCl3) (million (1H, DD., J=2.1, 15.7), 2.27 (1H, d, J=15.7), 3.82-3.96 (4H, m), 5.22 (1H, m), 5.67 (1H, Shir.C.), 6.26 (1H, DD), J=0.6, 16.0), 7.60 (1H, DD), J=0.6, 16.0).

LRMS m/z: 376 (M+). HRMS m/z: On theory (in the form of C22H32O5) 376.2247; Found 376.2226.

Example of synthesis 1. Synthesis of compound (2A)

Was carried out the same procedure that is described in the Japanese patent LOP publication N 125396/1989, giving (22R, 23R, 24S)-alpha,3α-dipropionate-22,23-epoxy-B-Homo-7-oxa-Alfa-stigmasta-6-he (2A) in the form of needle crystals.

So pl.: 147-148oC (from methanol)

1H-NMR (CDCl3) (millions of dollars): 0.72 (3H, s), 1.10 (3H, s), 1.18 (3H, s) 2.73 (1H, DD)), 3.00 (1H, DD)), 4.10 (2H, m), 4.89 (1H, m), 5.38 (1H, m). FD-MS m/z 589 (M++1).

Example of synthesis 2. Synthesis of compound (2d)

Was carried out the same procedure that is described in the Japanese patent LOP publication N 125396/1989, giving (22R, 23R, 24S)-alpha,3α-dibutyrate-22,23-epoxy-B-Homo-7-oxa-Alfa-stigmasta-6-he (2d). Condition: amorphous substance.

1H-NMR (CDCl3) (millions of dollars): 0.67 (3H, s), 0.99 (3H, s), 2.70 (1H, DD. ), 3.00 (1H, DD)), 4.10 (2H, m), 4.86 (1H, m), 5.36 (1H, m). FD-MS m/z: 617 (M++1).

Example test 1. Evaluation of the suppression of transpiration and the promoting effect on the growth.

Seeds of beans Mangbean were planted in vermiculite and grown Kadysheva) sheets (length of the epicotyl or nudemadonna knee 2 cm) primordial leaves and epicotyl was sprayed uniformly with a solution for processing each of the test compounds. The solution for treatment were prepared by dissolving each of the test compounds in a small amount EtollTMand diluting it with water at a given concentration.

Seven seedlings per group were grown in the same manner as described above, in a vessel with 100 ml of water containing liquid fertilizer (HyponexTM).

Four days after treatment, i.e., when growth in the length of their epicotyl is completed, transpiration was determined in each group of treatment (reducing the amount of water in each vessel) and their average weight and was expressed as the percentage of indicators in the group without treatment (%). The results are shown in tables 1 and 2.

As can be seen from the above results, the compounds of the present invention showed activity, which is almost equivalent to or higher than the activity of abscisic acid natural type. In particular, compound (3b) and (3c) showed a 10-fold or higher activity than the activity of abscisic acid natural type.

Example of test 2. Evaluation of germination and the promoting effect on the growth (1)
oC under continuous illumination at 15000 Lux.

When this was given liquid fertilizer (HyponexTM).

In stage 4 of the sheet 10 well-grown seedlings were taken from each tray (2nd tray in each group, a total of 20 seedlings), and determined the average weight of seedlings, including roots, and was expressed as percentage based on the indicators in the group without treatment. The results are shown in table 3.

As can be seen from the above results, the compounds of the present invention showed activity, which is almost equivalent to or higher than the activity of abscisic acid natural type.

Example of test 3. Evaluation of germination and the promoting effect on the growth (2).

Carrot seed (type: Koyo No 2) was immersed overnight in a solution of the test compound in a mixture of ethanol/water (50:50) at a given concentration. Immediately after treatment the treated seeds were dried in air, and the next day they were planted and grown in a vinyl greenhouse at a temperature of at night 13oC or more.

After the pole is the group without treatment. The results are shown in table 4.

As can be seen from the above results, the compounds of the present invention showed activity, which is almost equivalent to or higher than the activity of abscisic acid natural type.

Example of test 4. Evaluation of the promoting action on ripening

Kind of Kyoho grapes, grown in the open air (outdoors) for 20 years, were treated with compound (3c) of the present invention or abscisic acid natural type. When the processing of each test compound was dissolved in 80% ethanol at a given concentration, and 5 ml of the solution was sprayed on each cluster during the creation of the painting. After seventeen days after spraying to harvest the fruit, and were checking their quality. The results are shown in table 5.

As can be seen from the above results, the activity is 50 part./million connections (3c) according to the present invention is comparable with the activity of 300 frequent. /million abscisic acid natural type that indicates that the first compound showed activity, about 5 times higher than the activity of the latter.

Example 5 tests. Assessment thickening of the roots (to the sprinkled test compound, I had started the thickening of its roots. Liquid for spraying (spray) were prepared as follows: 95 parts by weight of a solvent consisting of 60 parts of xylene, 20 parts of isophorone and 20 parts of surfactant, was mixed with 5 parts by weight of the tested compounds, giving emulsion preparation. It was diluted with water to a given concentration and then used for spraying in the amount of 100 liters 1000 m2.

After 15 days of spraying was determined by the average weight of roots of plants in each group and expressed in percent per weight in the group without treatment. The results are shown in table 6.

As can be seen from the above results, the compounds of the present invention showed activity, which is almost equivalent to or higher than the activity of abscisic acid natural type.

Example test 6. Assessment actions that increase the cold resistance

Plants Benjamin with 150 - 200 leaves grown in trays in the greenhouse were sprayed each test compound. Liquid for spraying was prepared as follows: 95 parts by weight of a solvent consisting of 60 parts of xylene, 20 parts of isophorone and 20 parts of the surface-antibalas water at a given concentration. Sprinkled the entire surface of the leaves, which are evenly specialise test solution.

On the same day after spraying (early November) the plant was placed in conditions of ambient temperature in an open field. After 25 days, we determined the percentage of fallen leaves. The results are shown in table 7.

As can be seen from the above results, the compounds of the present invention showed activity to prevent leaves from falling off due to damage by cold, which is almost equivalent to or higher than the activity of abscisic acid natural type.

Example test 7. Evaluation of germination and the promoting effect on the growth (combined with brassinosteroids) (1) Untreated husked rice seeds (variety: Nihon Bare ) was immersed in water at 15oC for 1 day, and then immersed in an aqueous solution of each test compound at a given concentration [handling one connection: 0.01 ppm million connections; and processing the mixture:0.01 ppm million compounds (1a, 1b, 3a - 3e), or 0.01 ppm million abscisic acid natural type, plus 0.01 ppm million compounds (2a)] for 24 hours. Fifteen seeds were planted in each tray (diameter: 10 cm) filled with vermiculite, and exp Suite. When this was given liquid fertilizer (HyponexTM).

In stage 4 of the sheet 10 well-grown seedlings were taken from each tray (2nd tray in each group, a total of 20 seedlings), and determined the average weight of seedlings, including roots, and was expressed as percentage based on the indicators in the group without treatment. The results are shown in table 8.

As can be seen from the above results, the processing of the mixture showed Energeticheskie a synergistic effect on germination and growth. In particular, the combination of compound (2a) from compound (3b) or (3c) showed a strong effect.

Example test 8. Evaluation of germination and the promoting effect on the growth (Combined with brassinosteroids) (2)

Carrot seed (type: Koyo No 2) was immersed overnight in a solution of the test compound in a mixture of ethanol/water (50:50) at a given concentration [handling one connection: 0.1 ppm million compounds (1a, 1b, 3a - 3e) or abscisic acid natural type; and processing the mixture: 0.1 frequent. /million compounds (1a, 1b, 3a - 3e), or 0.1 ppm million abscisic acid natural type, plus 0.01 ppm million compounds (2a)]]. Immediately after treatment the treated seeds were dried in air, and the next day they were planted and grown in Winnie delalla the average weight of their roots and was expressed as a percentage of per weight in the group without treatment. The results are shown in table 9.

As can be seen from the above results, the processing of the mixture showed Energeticheskie effect on growth.

Example 9 testing. Assessment thickening of the roots (the roots) and the promoting effect on the growth (Combined with brassinosteroids)

Radish (early variety Akamaru-commet) were grown in the field and sprinkled feel a connection when started thickening of its roots. Liquid for spraying was prepared as follows: 95 parts by weight of a solvent consisting of 60 parts of xylene, 20 parts of isophorone and 20 parts of surfactant, was mixed with 5 parts by weight of the tested compounds, giving emulsion preparation. It was diluted with water to a given concentration [handling one connection: 5 ppm million compounds (1a, 1b, 3a - 3e) or abscisic acid natural type, or 0.01 frequent. /million compounds (2a); and processing the mixture of: 5 ppm million compounds (1a, 1b, 3a - 3e), or 5 ppm million abscisic acid natural type, plus 0.01 ppm million compounds (2a)], and then used for spraying in the amount of 100 liters per 1000 m2.

15 days after spraying is determined by the average weight of roots in each group and introduced the from the above results, processing the mixture showed Energeticheskie effect on growth.

Example test 10. Assessment of validity exceeding cold resistance (Combined with brassinosteroids)

Plants with Benjamin 150-200 leaves grown in trays in the greenhouse were sprayed test connection. Liquid for spraying was prepared as follows: 95 parts by weight of a solvent consisting of 60 parts of xylene, 20 parts of isophorone and 20 parts of surfactant, was mixed with 5 parts by weight of the tested compounds, giving emulsion preparation. It was diluted with water to a given concentration [handling one connection: 10 ppm million compounds (1a, 1b, 3a - 3e) or abscisic acid natural type, or 0.01 ppm million compounds (2a); and treatment with a mixture of 10 ppm million compounds (1a, 1b, 3a-3e), or 10 ppm million abscisic acid natural type, plus 0.01 ppm million compounds (2a)]. Sprinkled the entire surface of the leaves, which are evenly specialise test solution.

On the same day after spraying (early November) the plant was placed in conditions of ambient temperature in the open field. After 25 days, determined by the percentage of fallen leaves. The results are shown in table 11.

Industrial applicability

Epoxycyclohexane derivatives of the present invention exhibit a strong effect on the regulation of plant growth, which is equivalent to or higher than the effect of abscisic acid, such as action, promoting plant growth, growth with the emergence of seedlings, the effect of preventing transpiration and wilting, action, manifested in enhancement of cold resistance (prevention of damage due to low temperatures), and the effect of promoting the growth and thickening of plants, and are useful as plant growth regulators, such as accelerators of growth of plants, accelerators germination and germination inhibitors transpiration and wilting, amplifiers cold tolerance, and growth accelerators, thickening or ripening fruits, roots or tubers, stems or bulbs. They are also useful as plant growth regulators, such as the regulator movement of immature fruits, buds blooming inhibitor or ejection of the peduncle, the fuse cut flowers, an inhibitor of flowering and others, which are known for the application of abscisic acid. In addition, they are applicable for fermentation to improve the quality and reduce the cost of brewing. Amoxicillih quantities as needed.

The plant growth regulator according to the second present invention, which includes epoxycyclohexane derived and brassinosteroid as active inhibitors, has Energeticheskie effect on the growth of plants, such as action, promoting the germination and emergence of seedlings, the effect of that increase cold resistance (prevent from low temperature damage), and action, promoting thickening and growth of the plants, and such combinations are useful as plant growth regulators, such as accelerators germination and growth of seedlings, amplifiers cold tolerance, growth accelerators, thickening or ripening fruits, roots, stems or bulbs, accelerators, rooting of cuttings and other

1. The plant growth regulator comprising an active ingredient and conventional carriers, diluents, auxiliary agents, characterized in that as the active ingredient it includes derived epoxycyclohexane General formula 1

< / BR>
where R1represents a hydrogen atom, a C1- C6is an alkyl group or a C3- C6-cycloalkyl group;

R2and R3together form an ethylene group,

in an amount corresponding to the concentration about is that as an active ingredient contains a compound of formula 1, in which R1is sawn or ISO-propyl group, and R2and R3together form an ethylene group.

3. The regulator under item 1, with the property stimulator of plant growth.

4. The regulator under item 1, with the property stimulant seed germination and seedling emergence.

5. The regulator under item 1, with the property inhibitor transpiration and wilting.

6. The regulator under item 1, having the property of improving the cold tolerance of plants.

7. The regulator under item 1, having the property of growth, thickening or ripening fruits, roots, stems or bulbs.

8. The plant growth regulator comprising an active ingredient, a common carrier, diluent, auxiliary agents, wherein the active ingredient includes derived epoxycyclohexane General formula 1

< / BR>
where R1represents a hydrogen atom, a C1- C6is an alkyl group or a C3- C6-cycloalkyl group;

R2and R3together form an ethylene group,

and brassinosteroid General formula 2

< / BR>
where R4and R5is independently C1- C6is an alkyl group,

at a concentration of brassinosteroid General formula (2) 0,001-0,1 h/million

9. The regulator under item 8, characterized in that the quality of the derived epoxycyclohexane formula 1 contains a derivative in which R1is sawn or ISO-propyl group, and R2and R3together form an ethylene group.

10. The regulator under item 8, having the property stimulator germination and emergence.

11. The regulator under item 8, having the property of improving the cold tolerance of plants.

12. The regulator under item 8, having the property of growth, thickening or ripening fruits, roots, stems or bulbs.

13. Derived epoxycyclohexane represented by General formula 3

< / BR>
where R1represents C2- C6is an alkyl group or a C3- C6-cycloalkyl group;

R2and R3United, forming a C2- C3-polymethene group.

14. Derivatives under item 13, in which R1is sawn or ISO-propyl group.

 

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