CS274492B2 - Agent for plants' anthers sterilization - Google Patents

Abstract

The agent for sterilization of plant anthers, containing active substance in combination with diluter, where the derivates of the general formula A - COOR serve as active substance, where R stands for K, Na, NH4, alkyl with 1 to 6 carbon atoms, allyl.A stands for<IMAGE>,where R<1> is COOH, COOR, H, OH and R<2> is H, OH or their mixtures. Plant treatment with this agent is carried out in the fifth and/or sixth stage of organogenesis. The agent is used in cultivation and seed growing industry

Description

(57) A composition for the sterilization of roetlin powders comprising a diluent wherein the active compounds are carboxylic acid derivatives of the general formula:

A - COOR where R is K, Na, NH4, alkyl of 1 to 6 carbon atoms, allyl

R | is COOH,

R ₂ is H, OH or mixtures thereof

Treatment of plants with a sterilizing agent is performed at the fifth and / or sixth stages of organogenesis.

The composition comes for use in breeding and seed growing.

CS 274 492 B2

BACKGROUND OF THE INVENTION The present invention relates to biology and agriculture, and more particularly to a composition for sterilizing plant anthers that can be used in sowing and seed growing.

Ones ee addresses the challenge of intensifying agriculture worldwide, in particular increasing the profitability of cereals, kriviv, vegetables and technical cultures by the wide use of first generation hybrids. By means of hydridization, hybrids can be obtained, distinguishing! from parental forms to higher productivity (by 25 to 30%) and better product quality.

There is a method for producing new hybrids that corresponds to a system of cytoplasmic pollen sterility - regenerated fertility ”. The basis of this method is continuous (12 to 14 years) and complicated selection work, which includes obtaining sterile analogs, sterility fixators and fertility restorers. Especially promising are methods of sterilizing plant anthers with chemical sterilizing agents (gametocides). The use of gametocides is considerably more economical than using the system of cytoplasmic pollen sterility, since there is no need to develop such forms as sterile analogs, analogues for fixation of sterility in female forms and for regeneration of fertility in male forms. The seeds of the first generation hybrids can practically be obtained both during the breeding of the starting forms and also in the organization of their technical production.

There are currently found about 200 compounds having gametocidal activity and their chemical structure belongs to different classes of chemical compounds.

Gametocides in treated plants must result in complete sterility of the pollen while maintaining the ability of the egg cells to live and ensure a sufficiently high ability (at least 70% of control) to produce testicles under free pollination. Their phytotoxicity and toxicity to warm-blooded animals must be minimal.

Methods of sterilizing cereal anthers (L. Dzh. Nikell, Regulators Grow Growth) are known. Primenenie v selr.kom chozjajstva, Moscow, eds., Kolos, 1984, pp. 28-31; SU, A, 906457) sterilizing agents such as 2-chloroethylphosphonic acid (Ethrel), maleic hydrazide, di- (polyfluoroalkyl) phosphoric acid and its 9-ol salts and others. Treatment of plants with sterilizing agents is carried out in V or VI. stage of organogenesis (according to F.M. Kupermann).

In the V stage of organogenesis, the processes of formation and differentiation of flowers begin. At the end of this stage, neoplasms, sporogene archesporium tissues are formed. During this stage germs of sticks, pistils and petals form. Stage V differentiation occurs in the rod embryo in the rod and pate. Stadium VI. is characterized by the process of the formation of the flower (micro and macrosporoganoza). At this stage, separate nuclear nuclear pollen grains are formed (F.M. Kupermann, Morfofiziologija rastanij, Moscow, Higher School, 1973, pp. 30-36).

Further, a method for sterilizing grass anthers (GB. A, 1567153) is known which comprises treating the grasses with a sterilizing agent for a period between the appearance of the second stem and the ear. Haterocyclic compounds are used as the starter agent, the main representatives of which are 2-carboxy-3,4-methanpyrrolidine or 2-methoxycarbonyl-3,4-methanpyrrolidine. Said compounds are used in combination with diluents and surfactants.

SUMMARY OF THE INVENTION It is an object of the present invention to provide a new sterilizing agent which allows sterilization of anthers of plants in a wide variety of cultures with a high degree of sterilization while maintaining a high seed capacity for free pollination.

This object is achieved by carrying out the sterilization of the orstlin anthers in the fifth and / or sixth stages of organogenesis by treating with an anti-aging agent which, in conjunction with the diluent, contains carboxylic acid derivatives of the general formula

COOR

CS 274 492 B2 in which

R represents K, Na, NH, alkyl of 1 to 6 carbon atoms, allyl,

CH I ->

A denotes Λ. x

Where it represents

R | COOH, COOR, H, OH

R ₂ H, OH or their 9-month mixture.

The sterilizing agent may be used in conjunction with any known and suitable diluent. It is expedient to use it in combination with water as a 0.01-2% aqueous emulsion. The oak plants treated with said sterilizing agent preferably serve grasses or sunflowers.

The composition according to the invention makes it possible to achieve the sterility of male plants (98-100%) and to obtain a high percentage of seed formation (over 70%). In order to achieve a high sterilization degree of anthers under unfavorable climatic conditions, treatment of the plants with a sterilizing agent in the fifth and / or sixth stage of organogenesis (according to Kupermann) is repeated.

The composition of the invention is used as follows.

Plants such as winter wheat and spring wheat, diploid and tetraploid rye, triticale, millet, sunflower and others are treated with a sterilizing agent using carboxylic acid derivatives as the agent.

The carboxylic acid derivatives can be used in conjunction with any suitable diluent. Conveniently, water is used as a crosslinker. Preferably, 0.01 to 2% of an aqueous emulsion of said compounds is used.

Suitable surfactants may be added to the ready-to-use solutions as desired. When applied to plants, any known adjuvants such as wetting agents, dispersants and adhesion enhancers are generally added to the ready-to-use solutions.

The sterilizing agent is applied to the plants by a variety of treatments such as liquid spraying and air spraying (aerosols).

Treatment of plants with a sterilizing agent is carried out in the fifth and / or sixth stage of organogenesis (according to Kupermann). The dosage of the sterilizing agent depends on the type of compound, the culture being treated, the stage of treatment and natural climatic factors. In order to ensure a high sterilization effect under adverse climatic conditions, repeated treatment of the plants in VI. stage of organogenesis. The total amount of sterilizing agent is 0.6 to 20 kg / ha.

All of the carboxylic acid derivatives of the present invention intended to be used as a sterilizing agent were tested for acute toxicity in animal experiments. The results of the tests showed that the compounds are slightly or moderately toxic.

For example, the LD50 ^for phthalic acid dibutyl ester is 2838 mg / kg animal weight for single-dose gastric administration and 6669 mg / kg animal weight for white rats, and 2-methyl-3-cyclohexenecarboxylic acid potassium salt for white rats.

7664 mg / kg animal weight.

The gametocidal activity of the 3terilizing agents according to the invention was determined by field experiments in different soil-climatic zones with partial areas of 10 m @ 3, in triplicate to four times. Each sterilizer has been tested for at least 5 years.

EN 274 492 82

The development of organogenesis stages is monitored cytologically. The plants are treated with a sterilizing agent at the beginning of the fifth stage of Kupermann's organogenesis.

After the ear growth, the insulation of the largest ears and others in parchment bags is carried out. For wheat and triticale, individual isolates are used. In rye, the ears of 5 to 7 different side-by-side plants are sealed in a single bag. For millet, each lath is isolated separately. The percent sterility (X) for wheat, rye, triticale and millet is determined by the formula

Number of seeds fertilized per isolate of treated plants

X η (1 - -). 100 ALIGN!

Number of seeds fertilized in one isolate of untreated control plants

The number of grains in the uninsulated spikes of control plants is taken as 100% seeded in free pollination.

In order to obtain reliable data, 20 to 25 wheat and triticale isolates, 10 to 15 rye and millet isolates are used each time.

To treat chemical sterilization of sunflower pollen, 45 treated plants were used for each compound, 15 plants were isolated for eamoopylening, 15 plants were pollinated with a mixture of pollen collected from 20-25 isolated dressings and 15 plants were left free to pollinate to control deposition of achenes in pollination of untreated plants.

The sterility of the pollen of sunflower plants is judged by the fertility of the pollen and the germination, the morphological peculiarities of the male germ cells and the ability of the pathogens to be deployed when pollinating the treated isolated plants with the pollen of the untreated plant. The viability of the egg cell is down! after seed formation in treated plants in free pollination.

It is desirable to treat plants in clear, windless weather.

All compounds enter the plant tissue within 4 hours. In case of rainfall during these 4 hours, the plants must be re-treated in VI. stage of organogenesis.

The carboxylic acid derivatives are prepared in a known manner.

Phthalic acid esters are obtained by the esterification of phthalic anhydride with the corresponding alcohol (N.I. Lebedev, Chlmiya and Technology Osnovnogo organiceskogo and Neftechimitskogo sinteza., Moscow, Khimija, 1981, p. 210). 2-Methyl-3-cyclohexylcarboxylic acid methyl ester is prepared by condensing piperylene (a product resulting from the chemical treatment of petroleum) with methyl acrylate (methyl acrylate used in the manufacture of plastics) in the presence of aluminum chloride (T. Snukai, Y. Kojima, 869 (1967).

By saponification of the above-mentioned ester with potassium, sodium or ammonium hydroxide, the corresponding salts of 2-methyl-3-cyclohexylcarboxylic acid are prepared. Potassium salt, sodium salt or ammonium salt of benzoic acid, p-hydroxybenzoic acid or sallcylic acid Neutralization with the appropriate hydroxides can be prepared.

In order to better understand the present invention, the following specific examples are set forth.

Example 1

Mironovskaya 808 winter wheat plants are sprayed with a 2% aqueous emulsion of the potassium salt of 2-methyl-3-cyclohexenecarboxylic acid with the aid of a portable sprayer in the V stage of organogenesis.

0.1% wt. J2 ^{C -} ^ 14 · kalciumalkylbenzensulfonátu

CS 274 492 B2

As adjuvant 9Θ, it adds 0.01 wt. dimethylformamide. The consumption of the product is 20 kg / ha.

The oak control serves plants treated with a diluent without a sterilizing agent.

The results are shown in Table 1. Similar results are obtained in the treatment of winter wheat of the species Mlronovskaya B08 in VI. stage of organogenesis.

Examples 2 to 8

The process is carried out analogously to the process described in Example 1. Oako sterilizing agent uses a 2% aqueous emulsion of methyl 2-methyl-3-cyclohexenecarboxylic acid methyl ester, 2-methyl-3-cyclohexenecarboxylic acid ammonium salt, phthalic acid dihexyl ester, phthalic acid dibutyl ester, dipropyl ester phthalic acid, phthalic acid diisobutyl ester, phthalic acid diethyl ester.

The results are shown in Table 1.

Similar results are obtained in the treatment of wheat of the type Mlronovskaya 808 in VI. stage of organogenesis.

Table 1

Example Number of grains in Percent Number of grains in Percentage- number klasu u sterility cob at vol- sazeni zrn isolate pollination in free pollination Control 37.7 0.0 40.4 100.0 1 r 3.2 91.5 38.6 95.5 2 o.o 100.0 30.1 74.5 3 0.6 98.4 39.2 97.0 4 4.2 88.9 38.2 94.5 5 o.o 100.0 31.7 78.5 6 5.0 86.8 39.0 96.5 7 0.2 99.5 37.7 93.3 8 0.5 98.7 39.8 98.5

Examples 9 to 13

Polesskaja-70 winter wheat plants are sprayed with a 2% aqueous emulsion of phthalic acid diethyl ester, phthalic acid diallyl ester, phthalic acid dihexyl ether, potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, ammonium salts of 2- methyl-3-cyclohexenecarboxylic acid ·

The emulsion contains 0.01 wt. % tetrahydrofuran and 0.1 wt. ^C 12 ^C 14 calcium alkylbenzenesulfonate.

The consumption of the product is 16 kg / ha. A diluent-treated plant without sterile is used as a control.

The test results are shown in Table 2. Similar results are obtained when treating winter wheat of the Polesskaja-70 species in VI. stage of organogenesis.

CS 274 492 B2

Table 2

Example Number of grains Percent Number of grains in Percentage of deployment number in ear of isolate sterility cob in free pollination grains in free pollination Control 34.3 0.0 37.8 100.0 9 0.2 99.4 36.8 97.4 10 6.2 82.0 35.6 94.1 11 0.1 99.7 36.0 95.2 12 0.0 100.0 35.8 94.7 13 3.7 89.2 36.9 97.6

Examples 14 to 17 Plants of winter wheat of the Priboj species in V. a VI. stage of organogenesis (according to Kuper- manna) treat a 2% aqueous emulsion of the potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, methyl 2-methyl-3-cyclohexenecarboxylic acid, phthalic acid dipropylether, phthalic acid diisobutyl ester. The emulsion contains 0.01 benzenesulfonate. Consumption % wt. of dimethyl sulfide of the formulation is 12 kg / ha. and 0.1 wt. C ^ 2 ~ 0χ4 Calciumalkyl- □ as control serves plants treated with a diluent without sterilizing agent. The test results are: i in Table 3. Table 3 Example Number of grains in ear u number. isolate Percent sterility Number of grains in the ear in free pollination Percentage of grain deployment in free pollination Control 32.1 o.o 36.8 100.0 14 0,0 100.0 35.1 95.4 15 0,0 100.0 34.8 94.6 16 5,6 82.6 32.6 88.6 17 0,0 100.0 33.7 91.6

Examples 18 to 22

Plants of winter wheat of Kharkovskaya region 81 in V. and VI. at the organogenesis stage (according to Kupermann), treat a 2% aqueous emulsion of sodium 2-methyl-3-cyclohexenecarboxylic acid, phthalic acid dlexyl ester, 2-methyl-3-cyclohexenecarboxylic acid ammonium salt, phthalic dibutyl ester, phthalic diallyl ester. The emulsion contains 0.01 wt. % dodecyl sulfate and 0.1 wt. ^c] ^ 2 ^ 14 kalciumalkylbenzensulfonátu.

The consumption of the product is 12 kg / ha. The test results are shown in Table 4.

Rostliny plants treated analogously to Example 1 serve as a control.

CS 274 492

Table 4

Example number Number of grains in ear for isolate Percent sterility Number of grains in the ear in free pollination Percentage of grain deployment in free pollination Control 31.8 0.0 33.9 100.0 18 0.2 99.4 32.6 96.2 19 Dec 0.0 100.0 30.8 90.8 20 May o.o 100.0 31.7 93.5 21 0.0 100.0 28.6 84.4 22nd 3.1 90.3 30.6 90.3

Examples 23 to 29

Spring wheat plants of Moskovskaya 35 are treated with a 1% aqueous emulsion of the potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, methyl 2-methyl-3-cyclohexenecarboxylic acid, diethyl phthalic acid ester, dipropyl phthalic acid ester in V. 9th organogenesis (Kupermann), phthalic acid diallyl ester, phthalic acid diisobutyl ester, potassium salt of benzoic acid.

The emulsion contains 0.01 wt. % dimethylsulfoxide and 0.1 wt. ^C | 2 ^_C 14 Kalciumalkylbencensulfonátu. The consumption of the product is 10 kg / ha. The diluent-treated plants without the sterilizing agent serve as a control.

The test results are shown in Table 5. Similar results are obtained for the treatment of spring wheat of Moskovskaya 35 in VI. stage of organogenesis.

Table 5

Example number Number of grains in ear for isolate Percent sterility Number of grains in the ear in free pollination Percentage of grain seed in free pollination 1 2 3 4 5 Control 27.5 o.o 33.2 100.0 23 0.0 100.0 30.8 92.8 24 o.o 100.0 29.6 89.2 25 0.6 97.9 31.2 93.9 26 1,2 95.6 28.6 86.1 27 Mar: 0.3 98.9 31.1 94.0 28 0.0 100.0 31.8 95.8 29 7.2 73.8 33.0 99.4

CS 274 492 B2

Examples 30 to 33

Spring wheat plants of the Botanicheskaya 4 species are treated with a 1% aqueous emulsion of phthalic acid dibutyl ester, phthalic acid dipropylether, sodium salt of 2- (methyl-3-cyclohexenecarboxylic acid, methyl 2-methyl-3) -cyclohexene carboxylic acid.

The emulsion contains 0.01 wt. % tetrahydrofuran and 0.1 wt. θι ₂ - ^ε ΐ4 calcium alkylbenzenesulfone here. The consumption of the product is 8 kg / ha.

Plants treated with a diluent without sterilizing agent serve as a control.

The test results are shown in Table 6. Similar results are obtained for the treatment of spring wheat of the species Botanicheskaya V in VI. stage of organogenesis.

Table 6

Example number Number of grains in ear for isolate Percent sterility Number of grains in the ear in free pollination Percentage of grain deployment in free pollination Control 32.8 0.0 37.4 100.0 30 0.2 99.4 30.6 81.8 31 0.5 98.5 31.5 04.2 32 1.0 97.0 32.9 88.0 33 0.0 100.0 34.2 91.4

Examples 34 to 3G

Plants of spring wheat of the family Family in V. and VI. stage of organogenesis (according to Kupermann) treats a 1% aqueous emulsion of the ammonium salt of 2-methyl-3-cyclohexenecarboxylic acid, phthalic acid dihexyl ester, phthalic acid diisobutyl ester.

The emulsion contains 0.01 wt. % dodecylsulfate and 0.1 wt. C 1 -C 4 calcium alkylbenzenesulfonate.

The consumption of the product is 6 kg / ha. Plants treated with a diluent without sterilizing agent serve as a control.

CS 274 492

Test results These are given in Table 7.

Table 7

Example number Number of grains in ear for isolate Percent sterility Number of ear grains in free pollination Percentage of grain deployment in free pollination Control 30.3 0.0 36.6 100.0 34 o.o 100.0 30.8 84.1 35 0.0 100.0 33.6 91.8 36 o.o 100.0 31.7 86.6

Examples 37 to 42

In the V. stage of organogenesis (according to Kupermann), triticale of the PRAG-101 species are treated with a 1% aqueous emulsion of phthalic acid dibutyl ester, phthalic acid diethyl ester, phthalic acid dihexyl ester, phthalic acid diisobutyl ester, 2-methyl-3-cyclohexenecarboxylic acid potassium salt. 2-methyl-3-cyclohexenecarboxylic acid.

The emulsion contains 0.01 wt. % dimethylsulfoxide and 0.1 wt. ^C 12 ^-C 14 calcium alkylbenzenesulfonate. The consumption of the product is 10 kg / ha. The diluent-treated plants without sterilizing agent serve the Oako control.

Test results are shown in Table 8. Similar results are obtained when treating triticale of the PRAG-109 species in VI. stage of organogenesis.

Table 8

Example number Number of grains in ear for isolate Percent sterility Number of grains in the ear in free pollination Percentage of grain usage in free pollination Control 62.2 0.0 69.0 100.0 37 0.1 99.8 62.1 90.0 38 0.8 98.7 60.8 88.1 39 3.0 95.2 61.7 89.4 40 1.0 98.4 66.8 96.8 41 o.i 99.8 65.1 94.3 42 o.o 100.0 64.7 93.8

CS 274 492 B2

Examples 43 to 47

Amphidiploid 206 triticale plants are treated with a 1% aqueous emulsion of phthalic acid dipropyl ester, diisobutyl phthalic acid ester, potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, methyl 2-methyl-3-cyclohexenecarboxylate in V stage of organogenesis (Kupermanna). salts of 2-methyl-3-cyclohexenecarboxylic acid.

The emulsion contains 0.01 wt. % tetrahydrofuran and 0.1 wt. calcium alkylbenzenesulfonate. The consumption of the product is 6 kg / ha.

Oako control serves plants treated with diluent without sterilizing agent.

The test results are shown in Table 9. Similar results are obtained with the treatment of triticale of Amfidiploid 206 in VI. stage of organogenesis. Table 9 Example Number of grains Percent Number of grains in Percentage of deployment number in ear of isolate sterility cob in free pollination grains in free pollination Control 28.6 0.0 36.4 100.0 43 0.0 100.0 31.8 87.3 44 0.0 100.0 32.5 89.3 45 0.1 99.7 31.8 87.3 46 0.0 100.0 32.6 09.6 47 5.0 79.7 37.5 103.1

Examples 48 to 55

Plants of 3elta tetraploid rye are treated with 1% aqueous emulsion of potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, methyl 2-methyl-3-cyclohexenecarboxylic acid ester, phthalic acid butyl ester, phthalic acid dihexyl ester, in the V stage of organogenesis (Kupermann's) phthalic acid, phthalic acid diallyl ester, phthalic acid diisobutyl ester, potassium salts of p-hydroxy acid.

The emulsion contains 0.01 wt. % dimathyleulfoxide and 0.1 wt. C 1-4 ^- C 14 cation alkylsulfonate. The consumption of the product is 6 kg / ha.

Oako control serves plants treated with diluent without sterilizing agent.

The test results are shown in Table 10. Similar results are obtained when treating Delta tetraploid rye in VI. stage of organogenesis.

Table 10

Example Number of grains Percent Number of grains in Percentage of deployment number in ear of isolate sterility cob in free pollination grains in free pollination 1 2 3 4 5

Control

43.3 o.o 47.1 100.0 0.1 99.8 45.6 96.8 0.0 100.0 44.2 93.0

CS 274 492 S1

Table 10 - continued

1 2 3 4 5 50 0.0 100.0 43.1 91.5 51 0.2 99.5 45.9 97.4 52 o.o 100.0 40.8 86.6 53 0.3 99.7 41.6 88.3 54 0.0 100.0 40.4 85.8 55 2.8 93.5 56.2 119.2

Examples 56 to 59

Tstraploid rye plants of the Ukraine species are treated with a 1% aqueous emulsion of 2-methyl-3-cyclohexenecarboxylic acid ammonium salt, phthalic acid diethyl ester, benzoic acid potassium salt, phthalic acid diisobutyl ester in V. stage of organogenesis (Kupermann's).

The emulsion contains 0.01 wt. % dimethylformamide and 0.1 wt. C | ₂ "" 14 calcium alkylbenzenesulfonate. The consumption of the product is 6 kg / ha.

Oako control serves plants treated with diluent without sterilizing agent.

Results These are given in Table 11. Similar results are obtained with the treatment of tetraploid rye of the Ukrainian species in VI. stage of organogenesis.

Table 11

Example Number of grains Percent Number of grains in Percentage of deployment Number in ear of isolate sterility cob in free pollination grains in free pollination Control 28.0 0.0 36.8 100.0 56 0.0 100.0 32.1 87.2 57 0.0 ΐοο, ο 30.7 83.4 58 4.2 85.0 35.8 97.3 59 0.0 100.0 34.7 94, 2

Examples 60 to 67

In the V stage of organogenesis (Kupermann), diploid rye plants of the chulpan species are treated with a 1% aqueous emulsion of a potassium salt of 2-methyl-3-cyclohexenecarbaxylic acid, 2-methyl-3-cyclohexenecarboxylic acid methyl ester, salicylic potassium salt, diallyl phthalic acid phthalic acid diisobutyl ester, phthalic acid dipropyloster, phthalic acid dioxyloether, phthalic acid dibutyl ester.

The emulsion contains 0.01 wt. % tetrahydrofuran and 0.1 wt. C 1 -C 4 -alkyl alkylbenzonilphonate.

The consumption of the product is 8 kg / ha. Oako control serves plants treated with diluent boz sterilizer.

CS 274 492 B2

The test results are shown in Table 12. Similar results are obtained for the treatment of Culpan diploid rye in VI. stage of organogenesis.

Table 12

Example Number of grains Percent Number of grains in Percentage of deployment number in the ear of an isolate sterility cob in free pollination grains in free pollination Control 51.2 o.o 56.8 100.0 60 0.0 100.0 55.2 97.1 61 o.o 100.0 51.0 89.0 62 10.4 79.7 50.4 08.7 63 0.3 99.4 53.7 94.5 64 0.5 99.0 52.2 91.9 65 0.0 100.0 53.2 93.6 66 o.o 100.0 57.0 100.3 67 0.0 100.0 50.5 88.9 Examples 68 to 73 Diploid plants Rye of Kharkovskaya 55 in V. and VI. stage of organogenesis (according to Kupermann) treat 1% aqueous dibutyl acid ester emulsion phthalic, diisobutyl- phthalic acid ester, phthalic acid dlallyl ester, phthalic acid dihexyl ester. methyl ester 2-methyl-3-cyclohexenecarboxylic acid, sodium salts 2-methyl-3- -cyclohexene carboxylic acid. The emulsion contains 0.01 % wt. % dimethylformamide and 0.1 wt. 0 | 2θΐ4 calciumalkyl- bonzensulfonate. Consumption preparation is 6 kg / ha. 3 as a check serving plants treated with diluent without sterilizing agent. Results tests are listed in Table 13 Table 1 3 Example Number of grains Percent Number of grains in Percentage of deployment number in ear of isolate sterility cob in free pollination grains in free pollination 1 2 3 4 5 Control 47.4 0.0 52.4 100.0 60 0.0 100.0 40.6 92.7 69 0.2 99.6 50.0 96, 9 70 0.1 99.8 51.2 97.7 71 0.0 100.0 49.7 94.0 72 0.0 100.0 40.0 91.6 73 0.0 100.0 50.1 95.6

EN 274 492 82

Examples 74 to 75

Plants of diploid rye of the species 8elorus3kaja 23 are in V. and VI. stage of organogenesis (according to Kupermann) treat a 1% aqueous emulsion of dibutyl ester of phthalic acid, the potassium salt of 2-methyl-3-cyclohexanecarboxylic acid.

The emulsion contains 0.01 wt. % dodecyl sulfate and 0.1 wt. C ₂ -C ₄ calcium alkylbenzenesulfonate.

The consumption of the product is 6 kg / ha. Diluent-treated plants without sterilizing agent serve as a control.

The test results are shown in Table 14.

Table 14

Example number Number of grains in ear for isolate Percent sterility Number of grains in the ear in free pollination Percentage of grain deployment in free pollination 1 2 3 4 5 Control 40.7 0.0 44.8 100.0 74 0.0 100.0 42.5 94.9 75 0.0 100.0 43.0 95.0

Examples 76 to 81 Diploid plants Rye of Voschod 2 se in stage V of organogenesis (according to Kuper- manna) treat 1% aqueous emulsion of phthalic acid diothyl ester, phthalic acid diisobutyl ester, 2-methyl-3-cyclohexanecarboxylic acid potassium salt, 2-methyl-3-cyclohexenecarboxylic acid ammonium salt, 2-methyl-3-cyclohexenecarboxylic acid methyl ester, diallyl ester . The emulsion contains 0.01 wt. % dodecylsulfate and 0.1 wt. zensulfonate. The consumption of the product is 10 kg / ha. Serve as a control without a sterilizing agent. -C14 calcium alkylbenzenes treated with dilutions Test results These are diploid rye species listed in Table 15. Entrance 2 in VI. stage Similar results organogenesis · get profit- Table 1 5 Example Number of grains Y, τ of ears in cialo. insulator Percent sterility Number of ear grains in free pollination Percentage of grain seed in free pollination Control 49.8 0.0 54.6 100.0 76 0.2 99.6 53.4 97.8 77 0.0 100.0 52.8 96.7 78 0,1 99.8 52.2 95.6 79 0.0 100.0 51.7 95.0 80 0,0 100.0 50.2 91.9 81 0.8 98.4 53.5 97.9

CS 274 492 B2

Examples 02 _o ž 08

Plants of diploid rye of the species Gibrid 18G1 / 79 are treated with a 1% aqueous emulsion of diisobutyl phthalic acid ester, potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, methyl 2-methyl-3-cyclohexenecarboxylate in the V stage of organogenesis (Ku permanna), ammonium salts of 2-methyl-3-cyclohexenecarboxylic acid, diallyl phthalic acid ester, dihexyl phthalic acid ester, ammonium salts of p-hydroxybenzoic acid.

The emulsion contains 0.01 wt. % dimethylsulfoxide and 0.1 wt. Cj ₂ -C 1 ₄ calcium alkylbenzenesulfonate. The consumption of the product is 6 kg / ha.

Plants treated with a diluent without sterilizing agent serve as a control. The test results are shown in Table 16. Similar results are obtained for the treatment of diploid rye of Gibrid 1861/79 in VI. stage of organogenesis.

Table 16

Example Number of grains Percent Number of grains Percentage of deployment number ears in insulator sterility ears in free pollination grains in free pollination Control 54.0 0.0 62.8 100.0 82 0.6 98.9 57.1 90.9 83 0.2 99.7 56.7 90.2 84 0.0 100.0 51.2 81.5 85 o.o 100.0 57.8 92.0 86 o, o 100.0 59.6 95.0 87 o.o 100.0 56.4 89.8 88 0.8 98.5 68.9 109.7

Examples 89 to 96

Mironovskoe 94 millet plants are treated with 1% aqueous emulsion of potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, methyl ester of 2-methyl-3-cyclohexenecarboxylic acid, dihaxylastar phthalic acid, dibutylestar phthalic acid, dipropylester in V. stage of organogenesis (Kupermann) phthalic acid, sodium p-hydroxybenzoic acid soles, phthalic acid diethyl ester, phthalic acid diallyl ester.

The emulsion contains 0.01 wt. % dimethylformamide and 0.1 wt. C ₂ -C ₄ calcium alkyl carbonene sulfonate. The consumption of the product is 10 kg / ha.

As a control, the plants treated with the diluent base of the sterilizing agent.

The test results are shown in Table 17. Similar results are obtained for the treatment of millet Mironovskoe 94 in VI. stage of organogenesis.

Table 17

Example number Number of slats in the insulator Percent sterility Number of grains in free pollination Percentage of grain seed in free pollination 1 2 3 4 5

Control

320.5

0.0

379.5

100.0

CS 274 492 B2

Table 17 - continued 1 2 3 4 5 89 0.0 100.0 304.3 80.2 90 0.0 100.0 327.6 86.3 91 0.0 100.0 311.5 82.1 92 0.0 100.0 351.4 92.6 93 0.0 100.0 308.7 81.3 94 0.0 100.0 400.7 105.6 95 0.0 100.0 352.5 92.9 96 0.0 100.0 335.2 88.3 Examples 97 to 102 Millet plants of the species K-9693 Kormovce I are treated in the V stage of organogenesis (according to Kupermann treated with a 1% aqueous ammonium emulsion of 2-methyl-3-cyclohexenecarboxylic acid, dipropyl phthalate, dlbutyl phthalate, diisobutyl phthalate, methyl 2-methyl) -3-Cyclohexene carboxylic acid, phthalic acid dihexyl ester. The emulsion contains 0.01 wt. dodecyl sulfate sulfonate. The consumption of the product is 8 kg / ha. and 0.1 wt. C 1 -C 14 calcium alkylbenzene Rostliny the treated plants serve as a control with a sterilizing agent without a sterilizing agent. Test results are shown in Table 18. Similar results were obtained with millet K-9693 Kormovoe in VI, stage of organogenesis. gain during treatment T a b u 1 k a 1 8 Example nr lo Number of slats in the insulator Percent sterility Number of grains in free pollination Percentage of seed grain in free pollination Control 125.0 0.0 146.7 100.0 97 0.0 100.0 121.6 82.9 98 0.0 100.0 130.7 89.1 99 0.0 100.0 127.9 07.9 100 ALIGN! 0.0 100.0 110.4 75.3 101 0.0 100.0 127.8 07.1 102 0.0 100.0 136.6 93.1 Examples 103 to 116 Plants sunflower kind Peredovik se v V. stage of organogenesis (by Kupermann)

treat with 0.5% aqueous emulsion of dibutyl phthalic acid ester, diethyl phthalic acid ester, potassium salt of 2-methyl-3-cyclohexonecarboxylic acid, sodium salt of 2-methyl-3-cyclooxycarboxylic acid and 0.05% aqueous emulsion of methyl kyeolin 2-methyl- 3-cyclohexenecarboxylic acid.

CS 274 492 B2

The emulsion contains 0.01 wt. % dimethylsulfoxide and 0.1 wt. calcium alkylbenzenesulfonate.

Sunflower line VK-119 is treated with 0.2% aqueous phthalic acid dibutyl ester emulsion, 0.1% phthalic acid diethyl ester aqueous emulsion, 2-methyl-3-cyclohexenecarboxylic acid potassium salt, 1% aqueous 2-methyl-3 sodium salt emulsion -cyclohexene carboxylic acid and 0.01% aqueous emulsion of 2-methyl-3-cyclohexene carboxylic acid methyl ester. The emulsion contains 0.01 wt. % dimethylformamide and 0.1 wt. C 1 -C 4 -alkylcyclobenzenesulfonate.

Sunflower Line 8K-373 is treated with 0.2% aqueous emulsion of phthalic acid dibutyl ester, 0.1% aqueous emulsion of potassium salt of 2-methyl-3-cyclohexenecarboxylic acid, 0.01% aqueous emulsion of 2-methyl-3-cyclohexenecarboxylic acid methyl ester, and 0.2% aqueous phthalic acid diethyl ester emulsion. The emulsion contains 0.01 wt. % dodecyl sulfate and 0.1 wt. C ₂ -C ₄ -C ₄ calcium alkylbenzenesulfonate.

Rostliny in all cases, plants treated with a diluent without sterilizing agent serve as a control.

The test results are shown in Table 19. Similar results are obtained when treating sunflowers of the listed species in VI. stage of organogenesis.

Table 19

Example number Percent sterility Deposition of achenes in free pollination Mass 1000 samples in g Oil content of achenes in% Peredovik Control 0.2 85.0 84.0 54.7 103 100.0 82.3 82.3 53.4 104 100.0 80.0 80.6 54.0 105 100.0 85.0 81.6 53.7 106 100.0 84.1 82.3 51.9 107 100.0 83.8 83.7 54.0 Line BK-119 Control 2.0 85.0 60.0 51.0 106 100.0 83.5 59.0 51.2 109 100.0 82.5 55.0 51.2 110 100.0 85.5 61.9 51.5 111 íoo.o 85.0 61.1 53.4 112 100.0 85.0 54.0 55.1 Line BK-373 Control 0.4 70.4 58.1 49.8 113 100.0 61.5 55.8 45.9 114 100.0 62.9 57.8 48.8 115 100.0 65.7 57.6 49.3 116 100.0 64.6 57.4 46.8

CS 274 492 B2

Table 19 - continued

Example Growth Preparation Consumption number energy % in mass % preparation kg / ha Peredovik Control 100.0 - - 103 100.0 1.0 6.0 104 100.0 1.0 6.0 105 100.0 1.0 6.0 106 100.0 1.0 6.0 107 100.0 Line BK-119 0.05 0.3 Control 100.0 - - 108 100.0 0.2 1,2 109 100.0 0.1 0.6 110 100.0 0.1 0.6 111 100.0 1.0 6.0 112 100.0 Line BK-373 0.01 0.06 Control 100.0 - - 113 100.0 0.2 1.2 114 100.0 0.1 0.6 115 100.0 0.01 0.06 116 100.0 0.2 1,2

Examples 117-126

Mironovskaya 808 winter wheat bean crops are treated with a 2% aqueous emulsion of a mixture of diethyl phthalic acid / potassium salt of salicylic acid (ratio 1: 1), a 2% aqueous emulsion of a mixture of dipropyl phthalic acid / potassium salt of water in V stage of organogenesis (Kupermann) benzoic acid (1: 1 ratio), a 2% aqueous emulsion of a mixture of dibutyl ether of phthalic acid and the potassium salt of p-hydroxybenzoic acid (1: 1 ratio).

The emulsion contains 0.01 wt. % of tetrahydrofuran and 0.1 wt. C ₂ -C ₄ calcium alkylbenzenesulfonate. The consumption of the product is 12 kg / ha.

Spring wheat Moscow plants were treated with a 1.0% aqueous emulsion of a mixture of isobutyl phthalic acid ester and a potassium salt of benzoic acid (1: 1 ratio), a 1.0% aqueous emulsion of a mixture of dihexyl phthalic acid ester and a potassium salt of p-hydroxybenzoic acid (1: 1 ratio) ), A 1.0% aqueous emulsion of a mixture of a diallyl phthalic acid ester and a potassium salt of benzoic acid.

The emulsion contains 0.01 wt.% Of dimethylsulfoxide and 0.1 wt. ^C 12 ^_C 14 kalciumalkylbenzensulf sulfonate. The consumption of the product is 6 kg / ha.

EN 274 492 62

Plants of Diploid Rye Plants are treated with a 1% aqueous emulsion of a mixture of dihexyl phthalic acid ester and a potassium salt of p-hydroxybenzoic acid, 1% aqueous emulsion of a mixture of diallyl phthalic acid ester and a potassium salt of salicylic acid (1: 1 ratio) and potassium salts of benzoic acid (1: 1 ratio), 1% aqueous emulsion of a mixture of diisobutyl phthalic acid ester and diethyl phthalic acid ester (1: 1 ratio).

The emulsion contains 0.01 wt. % tetrahydrofuran and 0.1 wt. ΐΐΐ- ^{'alkylalkylalkylalkylalkylalkylalkylalkylalkylalkylalkylalkylalkylalkylalkyl} . The consumption of the product is 6 kg / ha.

Plants of triticale of the PRAG-109 type are treated with 1% aqueous emulsion of a mixture of dibutyl phthalic acid ester and potassium salt of salicylic acid (1: 1 ratio), 1% aqueous emulsion of a mixture of dihexyl phthalic acid ester and potassium benzoic acid salt (1: 1 ratio), 1% aqueous emulsion of phthalic acid diallyl ester and potassium salt of p-hydroxybenzoic acid (1: 1 ratio).

The emulsion contains 0.01 wt. % tetrahydrofuran and 0.1 wt. calcium alkylbenzenesulfonate. Consumption of the product is 8 kg / ha.

In all cases, it serves as a control of the diluent-treated plant without the sterilizing agent. The test results are shown in Table 20. Similar results are obtained when treating the named plants in VI. stage of organogenesis.

Table 20

Example number Number of ear grains in the insulator Percent sterility Number of ear grains in free pollination Percentage of grain deployment in free pollination 1 2 3 4 5 Control 38.3 Winter wheat 0.0 Mironovskaja 808 41.0 100.0 117 o, o 100.0 39.2 95.6 118 o, o 100.0 38.8 94.6 119 o, o 100.0 40.7 99.2

Wheat Oils Moskovskaya 35

Control 27.1 o.o 27.5 100.0 120 0.0 100.0 24.8 90.1 121 0.0 100.0 26.8 97.5 122 0.0 100.0 27.0 98.1 Diploid rye slug Control 57.1 0.0 64.7 100.0 123 o.o 100.0 60.2 93.0 124 0.0 100.0 61.4 94.9 125 0.0 100.0 59.7 92.3 126 o.o 100.0 58.6 90.6

CS 274 492 B2

Table 20 - continued

1 2 3 4 5 Control 62.2 Triticale PRAG-109 0.0 69.0 ΐοο, ο 127 0.0 100.0 62.7 90.9 128 0.0 100.0 66.5 96.4 129 0.0 100.0 67.0 97.1

Claims (2)

SUBJECT OF THE INVENTION A composition for the sterilization of anthers of plants comprising a diluent, characterized in that it contains as active ingredient carboxylic acid derivatives of the general formula: A - COOR in which R represents K, Na, NH4, alkyl of 1 to 6 carbon atoms, allyl, R 6 represents COOH, COOR, H, OH, R ₂ denotes H, OH or mixtures thereof. 2. A composition according to claim 1, which contains water as a crosslinking agent, characterized in that the concentration of active ingredient is 0.01 to 2% by weight. in the form of an aqueous suspension.