JPH02221202A - Male sterility agent of plant - Google Patents

Abstract

PURPOSE:To readily and surely induce male sterility and produce seed of first filial generation without losing pollinating ability of female by obtaining male sterility agent containing specific threonine derivative as active ingredient and using said agent. CONSTITUTION:2-70wt.% compound expressed by the formula [R<1> is methyl or ethyl; R2 is H, lower alkyl or COR<4> (R<4> is lower alkyl, lower alkoxy, phenyl or amino, etc.); R<3> is OH, lower alkoxy or NHR<5> (R<5> is H, OH, lower alkyl or amino, etc.)] is contained in the subject agent and mixed with solid carrier, liquid carrier, surfactant or other auxiliary substance for formulation to afford a male sterility agent formulated as water dispersible powder, granule or water soluble powder, etc. As said formulation very simply and effectively induces male sterility and does not generate any effect harmful to pistil and therefore, seed of first filial generation is readily obtained by cross-fertilization.

Description

[Detailed description of the invention] <Industrial application field> The present invention relates to a male sterility agent for plants.

More specifically, general formula (1) % formula % (1) [wherein R' represents a methyl group or an ethyl group, R1
represents a hydrogen atom, a lower alkyl group, or a group represented by 2COR'. Here, R4 represents a lower alkyl group, a lower alkoxy group, a phenyl group, an amino group or a lower alkylamino group. R1 represents a hydroxyl group, a lower alkoxy group, or a group represented by the formula NHR'. Here, R' represents a hydrogen atom, a hydroxyl group, a lower alkyl group, an amino group or a lower alkylamino group. However, this excludes those in which the steric configuration is L and R1 is a methyl group, R1 is a hydrogen atom, and R1 is a hydroxyl group. ] A threonine derivative represented by [hereinafter referred to as compound (1)]. ) as an active ingredient, a method for sterilizing plants using the compound, and a method for producing first-generation hybrid seeds using the compound.

<Conventional technology> In recent years, the development of new plant varieties has become active, and in this context, the production of hybrid first-generation plants is attracting attention.

First generation hybrid plants are known to have many superior traits such as higher yields than their parent varieties due to their vigorous growth.

<Problem to be solved by the invention> In order to obtain first-generation hybrid seeds, it is necessary to prevent self-pollination of the female parent, and for this purpose, the stamens of the female parent must be removed.

Traditionally, this emasculation process was very labor-intensive, and since highly self-pollinating grains such as rice and wheat have stamens and pistils within their small flowers, emasculation was done manually to produce hybrids. It was almost impossible to produce first-generation seeds.

In addition, there are other methods, such as the use of cytoplasmic male sterility, but these also have problems such as requiring a long period of time to develop, and therefore do not cause male sterility without losing the female's ability to pollinate. The reality is that a simple and reliable method is desired.

Means for Solving the Problems In view of the above circumstances, the present inventors have made extensive studies and found that by treating plants with compound (I), it is possible to very easily and efficiently (cause male sterility). Find out what you can do,
The present invention has now been completed.

That is, the present invention uses compound (r) as an active ingredient.

The present invention provides a male sterility agent that uses the compound, and also provides a method for achieving male sterility and a method for producing first-generation hybrid seeds using the compound.

Examples of target plants for which compound (1) can be used as a male sterility agent include grains such as rice, wheat, barley, oats, rye, and corn, legumes such as soybeans, eggplants, tomatoes, and cabbage. Various cultivated plants can be mentioned, such as petals such as rapeseed, bechu, nia, zinnia, and morning glory. When compound (1) is used as a male sterility agent, sufficient male sterility can be caused without causing undesirable side effects on plants.

Furthermore, since the male sterility agent of the present invention does not have a harmful effect on the pistil, first-generation hybrid seeds can be easily obtained by cross-pollination.

When compound (1) is used as an active ingredient of a male sterility agent, it is usually mixed with a solid carrier, liquid carrier, surfactant, or other formulation auxiliary to form a wettable powder, granule, water-solvent, etc. Prepare and use.

These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 1 to 80%, preferably 2 to 70%.

Examples of solid carriers include kaolin clay buttabulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, walnut shell powder, urea,
Examples include fine powders or granules such as ammonium sulfate and synthetic hydrous silicon oxide. Examples of liquid carriers include alcohols such as isopropanol, ethylene glycol and cellosolve, ketones such as acetone, cyclohexanone and isophorone, dimethyl sulfoxide, N , N-dimethylformamide, acetonitrile, water and the like.

Examples of surfactants include alkyl sulfate salts, alkyl sulfonate salts, alkylaryl sulfonate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphate salts, etc. used for dispersion, wet layering, etc. Nonionic surfactants such as anionic surfactants, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters are included.

Other formulation auxiliaries include, for example, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose),
Examples include PAP (isopropyl acid phosphate).

Compound (1) is usually formulated and used, preferably after treatment with foliage, soil, or rice water from just before the start of reproductive growth until flowering.

In the case of rice field water treatment, it is necessary to separate male and female plants with plastic corrugated plates or the like to prevent chemicals from being absorbed by male plants planted next to each other.

When treating the foliage and soil, it is necessary to prevent the male plants from being exposed to chemicals.

When compound (I) is used as the active ingredient of a male sterility agent, the amount to be treated will vary depending on weather conditions, formulation form, treatment time, method, location, target crop, target variety, etc., but is usually 50g per hectare. ~10,000 g, preferably ioo g ~5,000 g, and the predetermined amount of hydrating agents, water solvents, etc. is usually 100 liters to 1,000 liters per hectare (if necessary, auxiliary agents such as spreading agents are added). It is treated by diluting it with water, and granules and the like are usually treated as they are without any dilution.

Examples of the spreading agent include, in addition to the above-mentioned surfactants, polyoxyethylene resin acid (ester) lignin sulfonate, abietate, dinaphthylmethane disulfonate, paraffin, and the like.

It can also be used in combination with plant growth regulators, herbicides, insecticides, acaricides, nematicides, fungicides, fertilizers, soil conditioners, and the like. Moreover, the same plant body can be treated with compound (1) several times at different treatment times.

For example, the following method is suitable for obtaining a large amount of first-generation hybrid seeds.

In other words, the two parents to be crossed are planted alternately. At this time, the number of rows, width, etc. of each parent vary depending on the target crop, target variety, environmental conditions, etc. Then, the female plant is treated with the present male sterility agent, and the female plant that has become male sterile is pollinated with pollen from the male plant carried by wind or insects, and hybrid seeds are obtained.

In addition, compound (1) can be manufactured by a known method as follows.

Generally, 0-alkylthreonine is tetrahedron (
Tetrahedron) Volume 39, Page 475, 198
It can be produced according to the method described in 2003. Further, N-acyl derivatives can be produced by acylating 0-alkylthreonines under Schotten-Baumann conditions. Furthermore, N-carbamoyl derivatives can be produced by reacting O-alkylthreonines and incyanates in the presence of an amine.

Table 1 shows some of the compounds (I) that can be produced in this way.

Table 1 OR'CHICHCHCOR" (1) NHR" Table 2 <Examples> The present invention will be explained in more detail below using formulation examples and test examples, but the present invention is not limited only to these examples. .

The compounds used in the following examples are represented by compound numbers shown in Table 2 below.

In Table 2, the compound (11 is Tetrahedron Vol. 39, 47
Compounds (2), (3) and (6) were produced by reacting 0-methylthreonine with an acylating reagent in an alkaline aqueous solution. be. Compound (7) is obtained by esterifying 0-methylthreonine using thionyl chloride in ethanol, and compounds (4) and (5) are obtained by acylating compound (7) in the same manner as compound (2). Or it is ureated.

Compound (8) is published in Tetrahedron Vol. 39, p. 475, 19
It was produced from D-allo-0-methylthreonine according to the method described in 1983.

First, a formulation example will be shown. Parts represent parts by weight.

Formulation Example 1 50 parts each of Compounds (1) to (8), 3 parts of calcium lignosulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder.

Formulation Example 2 Compound (4), (5) or +71 i 0 parts, polyoxyethylene styrylphenyl ether 14 parts, calcium dodecylbenzenesulfonate 6 parts and xylene 7
Mix 0 parts thoroughly to obtain an emulsion.

Formulation Example 3 Compound + 2 parts each of 1) to (8), 1 part of synthetic hydrous silicon oxide
1 part, 2 parts of calcium lignin sulfonate, 30 parts of bentonite, and 65 parts of kaolin clay were thoroughly ground and mixed.
After adding water and kneading well, the mixture is granulated and dried to obtain granules.

Formulation Example 4 25 parts of compound (4), (5) or (7), 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 69 parts of water were mixed and wet-pulverized until the particle size became 5μ or less. Obtain a clouding agent.

Formulation Example 5 3 parts each of Compounds (1) to (8), 1 part of polyoxyethylene styrylphenyl ether, and 96 parts of water are mixed to obtain a liquid preparation.

Next, test examples using wheat and rice will demonstrate that compound (1) is useful as an active ingredient of a male sterility agent.

Test Example 1 Wheat (variety: Norin No. 61) was sown in a plastic pot with a capacity of 200 d filled with artificial soil, and grown under greenhouse conditions with a day temperature of 7°C and a night temperature of 20°C and a 15-hour day length. I let it happen. Then, 15 days before the beginning of heading, the test compound was formulated into a liquid formulation according to Formulation Example 5, a predetermined amount of which was diluted with water containing a spreading agent, and a small sprayer was applied at a liquid volume of 10 liters per are. The foliage was treated from above the plant.

After ripening, four panicles were harvested per pot, and the number of spikelets and seeds were investigated. The test was conducted with one bot per treatment area.

The sterility rate was calculated using the following formula.

A = Number of seeds per spikelet in untreated plot B = Number of seeds per spikelet in treated plot Sterility rate (%) = (1--)
Shown in the table. All of the test compounds showed 100% or close to 100% sterility. In addition, drug damage was not a problem.

A liquid preparation was prepared, and a predetermined amount of the solution was diluted with water containing a spreading agent, and the foliage was treated from above the plant body using a small sprayer at a liquid volume of 10 liters per are.

After earing and flowering, four panicles from the pot that were thought to be sterile were pollinated by hand using pollen obtained from panicles that had not been treated with chemicals.

After ripening, 4 free ears and 4 artificially pollinated ears were harvested per pot, and the number of spikelets and seeds were investigated. The exam is l
The sterility rate and fertility rate in the treated pots were calculated using the following formula.

A = Number of seeds per spikelet in the untreated area B = Number of seeds per spikelet in the treated area Test Example 2 Wheat was cultivated in the same manner as Test Example 1, and the total number of seeds 22 days, 15 days, and 8 days before the beginning of heading was The test compound was added to the same pot three times according to Formulation Example 5, and the results are shown in Table 4. The test compound showed a complete sterility effect at 1000 g/ha in left-handed panicles, and a large number of seeds were produced in artificially pollinated panicles, indicating that the compound had female fertility at a dose that caused male sterility. Ta.

*In the untreated area, manual emasculation was performed.

Test Example 3 Rice was sown in a plastic pot with a capacity of 220 d filled with artificial beds, and the temperature was increased to 27°C and the night temperature was 20°C.
Grown under greenhouse conditions with hourly photoperiod. After flooding in the middle of the day, 14 days before the beginning of heading, prepare the test compound in an aqueous solution, dilute the prescribed amount with water containing a spreading agent, and use a small sprayer at a liquid volume equivalent to 10 liters per are. The foliage was treated from the top of the plant. After ripening, four panicles were harvested per pot, and the number of flowers and seeds were investigated. The test was conducted with 1 pot per 1 treatment.

The sterility rate was calculated using the following formula.

A=Number of seeds per number of fleas in the untreated area B=Number of seeds per number of fleas in the treated area Sterility rate (%)=(1-)X100 The results are shown in Table 5. All of the test compounds showed a sterility rate of 100% or close to 100%. In addition, the chemical damage was of a non-problematic level.

Test Example 4 Rice was cultivated in the same manner as in Test Example 3, and the test compound was formulated into a liquid formulation according to Formulation Example 5 in the same pot three times, 21 days before, 14 days before, and 7 days before the beginning of heading. A fixed amount was diluted with water containing a spreading agent, and the foliage was treated from above the plant using a small sprayer at a volume of 10 liters per are.

After earing and flowering, four panicles from the pot that were thought to be sterile were pollinated by hand using pollen obtained from panicles that had not been treated with chemicals.

After ripening, 4 free ears and 4 artificially pollinated ears were harvested per pot, and the number of spikelets and seeds were investigated. The exam is l
process! I did it in a pot.

The sterility rate and fertility rate were calculated using the following formulas.

A = Number of seeds per spikelet in the non-treated area B = Number of seeds per spikelet in the treated area The pollinated panicle has a large number of seeds, and it is possible that it is female fertile at a dose that causes male sterility. Admitted.

Table 6 *In the untreated area, manual emasculation was performed.

<Effects of the Invention> The compound has an excellent male sterility effect and does not cause any problematic drug damage, and is therefore useful as a male sterility agent.

Claims (3)

[Claims] (1) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R^1 represents a methyl group or an ethyl group, and R
^2 represents a hydrogen atom, a lower alkyl group, or a group represented by the formula COR^4. Here, R^4 is a lower alkyl group,
Represents a lower alkoxy group, phenyl group, amino group or lower alkylamino group. R^2 represents a hydroxyl group, a lower alkoxy group, or a group represented by the formula NHR^5. Here, R^5 represents a hydrogen atom, a hydroxyl group, a lower alkyl group, an amino group or a lower alkylamino group. However, this excludes those in which the configuration is L-form, R^1 is a methyl group, R^2 is a hydrogen atom, and R^3 is a hydroxyl group. ] A male sterility agent for plants, characterized by containing a threonine derivative represented by the following as an active ingredient. (2) General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R^1 represents a methyl group or an ethyl group, and R
^2 represents a hydrogen atom, a lower alkyl group, or a group represented by the formula COR^4. Here, R^4 is a lower alkyl group,
Represents a lower alkoxy group, phenyl group, amino group or lower alkylamino group. R^3 represents a hydroxyl group, a lower alkoxy group, or a group represented by the formula NHR^5. Here, R^5 represents a hydrogen atom, a hydroxyl group, a lower alkyl group, an amino group or a lower alkylamino group. However, this excludes those in which the configuration is L-form, R^1 is a methyl group, R^2 is a hydrogen atom, and R^3 is a hydroxyl group. ] A method for male sterility of a plant using a threonine derivative shown in the following. (3) A method for producing first-generation hybrid seeds using the male sterility agent for plants according to claim (1).