JP5285070B2 - Plant growth promoter - Google Patents

Description

The present invention relates to a plant growth promoter. More specifically, the present invention relates to a healthy seedling breeding agent for gramineous cereals containing a tetrazoyloxime derivative as an active ingredient, which improves the seedling quality of box seedlings.
This application claims priority on July 2, 2008 based on Japanese Patent Application No. 2008-173222 for which it applied to Japan, and uses the content here.

Conventionally, for the purpose of improving plant yield, plants have effects such as promoting rooting of plants, preventing lodging, improving yield, improving cold resistance, improving green color, raising healthy seedlings, increasing the number of divisions, promoting organ growth, etc. A growth promoter was used. For rice, which is the main grain among them, rice seedling breeding agents were used due to the spread of the box seedling method.
The rice box seedling method is super dense sowing for making seedlings suitable for rice transplanters. Also, depending on conditions such as temperature and humidity, rice seedlings are prone to poor growth and the seedling quality deteriorates. It was. In addition, when this seedling with reduced seed quality is transplanted to Honda, it is susceptible to pests and pathogens, and because it is poorly active, its resistance to changes in weather conditions is weak, so it took a great deal of cost and labor. However, there was a case where sales decreased. In view of this problem, rice seedling raising agents have been developed.
Patent Document 1 describes a composition for rooting and healthy seedling raising of rice containing cholines and hydroxyisoxazole. Patent Document 2 proposes a rice seedling growing agent containing 3-hydroxypyrazine or a derivative thereof as an active ingredient.
However, the substances in these patent documents are compounds having completely different structures from the tetrazoyloxime derivative of the present invention.

On the other hand, Patent Document 3 discloses that a tetrazoyl oxime derivative and an agrochemical containing this derivative as an active ingredient have a strong activity against various phytopathogenic fungi and are highly effective in preventing and treating plant diseases caused by phytopathogenic fungi. It is described that it exhibits an effect.
However, it is not described that the tetrazoyl oxime derivative of this document has a rice seedling raising effect and is effective as a rice seedling raising agent.

JP-A-61-212504 JP-A 62-167710 WO03 / 016303

  The present invention is to provide a plant growth promoter. In particular, it is an object to provide a healthy seedling-growing agent having excellent efficacy.

The present invention relates to the following.
(I) Formula (1)

[Wherein, X represents a halogen atom. n represents an integer of 0 to 2 , and when n is 2 or more, Xs may be the same or different from each other.
A is the formula (2):

(Wherein Y represents an alkyl group) or a tetrazoyl group represented by formula (3):

(Wherein Y represents an alkyl group).
Het is the formula (4):

{In the formula, R represents a halogen atom. m represents an integer of 0 to 3, and when m is 2 or more, Rs may be the same or different from each other. Z is the formula (5):
QC (= O) -NH- (5)
(Wherein Q represents a C1-8 alkyl group or a C1-8 alkoxy group). } A pyridine group represented by

It is shown. ] The plant growth promoter which contains the tetrazoyl oxime derivative represented by this as an active ingredient.

Tetrazolyl oxime derivative represented by formula (II) (1), A plant growth promoter having the constitution (I) that it is a tetrazolyl group represented by formula (2).

(III) The plant growth promoter according to (I) or (II) for the purpose of raising healthy seedlings of plants.
(IV) The plant growth promoter according to any one of (I) to (III), wherein the plant is a gramineous grain.

  According to the present invention, a plant growth promoting effect can be expected. Especially, it is a healthy seedling effect, and by applying it to the seedling before transplanting, rooting of the seedling is increased and transplantation is promoted after transplanting to Honda, and the number of divisions is also good, especially at low temperatures It is possible to demonstrate. Furthermore, the effect of preventing the generation of mussel seedlings can be significantly increased.

(Tetrazoyl oxime derivative represented by the formula (1))
Formula (1):

In the tetrazoyloxime derivative represented by general formula (I), X is not particularly limited in the substitution position, and is a halogen atom, alkyl group, alkoxy group, cyano group, methanesulfonyl group, nitro group, trifluoromethyl group or (alkyl group or halogen An aryl group substituted or unsubstituted by an atom. n shows the integer in any one of 0-5, and it is still more preferable that it is 0-2. When n is 2 or more, Xs may be the same or different.

Examples of the halogen atom represented by X include a chlorine atom, a bromine atom, an iodine atom, and a fluorine atom. Among these, a compound in which X is a chlorine atom or a fluorine atom is particularly preferable.
The alkyl group represented by X is preferably an alkyl group having 1 to 4 carbon atoms, specifically, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group. , And a tert-butyl group. Among these, a compound in which X is a methyl group or a tert-butyl group is particularly preferable.

Moreover, as an alkoxy group which X represents, a C1-C3 alkoxy group is preferable, and a methoxy group, an ethoxy group, a propoxy group, and an isopropoxy group are mentioned specifically ,. Among these, compounds in which X is a methoxy group or an ethoxy group are particularly preferable.
Examples of the alkyl group represented by X, or an aryl group substituted or unsubstituted with a halogen atom include a phenyl group, a 4-methylphenyl group, and a 4-chlorophenyl group. Among these, a compound in which X is a phenyl group is particularly preferable.

  Of the above, it is more preferable that n is 0 to 2 and X is a halogen atom.

  In the formula (1), A represents the formula (2):

Or formula (3):

The tetrazoyl group represented by these is represented. In the above formula, Y represents an alkyl group. Among the alkyl groups, an alkyl group having 1 to 3 carbon atoms is preferable, and examples thereof include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group. Among these, a compound in which Y is a methyl group or an ethyl group is particularly preferable.

  Het in the tetrazoyloxime derivative represented by the formula (1) is represented by the formula (4):

Or a pyridine group represented by formula (6):

Any one of thiazoyl groups represented by Z in the formulas (4) and (6) represents a hydrogen atom, an amino group, or the formula (5):
QC (= O) -NH- (5)
Represents a group represented by

R in the pyridine group represented by the formula (4) represents a halogen atom such as a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom. m represents an integer of 0 to 3, and when m is 2 or more, Rs may be the same or different from each other. Among these, a compound in which m is 0 and a compound in which R is a chlorine atom are particularly preferable.
R ′ in the thiazoyl group represented by the formula (6) represents a hydrogen atom or a halogen atom. Examples of the halogen atom include the same as the halogen atom for R.

  Q in the group represented by the formula (5) is a hydrogen atom, a C1-8 alkyl group, a C1-8 haloalkyl group, a C3-6 cycloalkyl group, a C1-8 alkoxy group, a C3-6 cycloalkyloxy group, benzyl. Oxy group, 2-phenylethyloxy group, C1-4 alkylthio group, C1-4 alkylthio C1-4 alkyl group, C1-4 alkoxy C1-2 alkyl group, C1-5 acylamino C1-6 alkyl group, C1-5 acylamino A C1-6 alkoxy group, a C1-8 alkylamino group, a C2-6 alkenyl group, an aralkyl group or a phenyl group;

  Examples of the “C 1-8 alkyl group” represented by Q include methyl group, ethyl group, n-propyl group, isopropyl group, 1,1-dimethylpropyl group, n-butyl group, isobutyl group, sec-butyl group, tert- Examples thereof include a butyl group, an isoamyl group, a 1-methylbutyl group, a 2-methylbutyl group, a neopentyl group, a 1-ethylpropyl group, an n-pentyl group, a hexyl group, a heptyl group, and an octyl group.

  The “C 1-8 haloalkyl group” represented by Q means a C 1-8 alkyl group substituted with a halogen atom, and specifically includes a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a difluoro Examples include chloromethyl group, pentafluoroethyl group, 3,3,3-trifluoro-n-propyl group, 1-chlorohexyl group and the like.

The “C 3-6 cycloalkyl group” represented by Q means a C 3-6 alkyl group having a cyclic moiety, and specifically includes a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclopropylmethyl group, a cyclopentyl group. A methyl group etc. are mentioned.
Examples of the “C1-8 alkoxy group” represented by Q include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a 1,1-dimethylpropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, Examples include isopentyloxy group, 1-methylbutoxy group, 2-methylbutoxy group, neopentyloxy group, 1-ethylpropoxy group, n-pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group and the like.

The “C 3-6 cycloalkyloxy group” represented by Q means a group in which a C 3-6 alkyl group having a cyclic portion and an oxygen atom are bonded, specifically, a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyl group. Examples thereof include an oxy group, a cyclohexyloxy group, and a cyclopropylmethyloxy group.
Examples of the “C1-4 alkylthio group” represented by Q include a methylthio group, an ethylthio group, a butylthio group, and the like.
Examples of the “C1-4 alkylthio C1-4 alkyl group” represented by Q include a methylthiomethyl group, an ethylthioethyl group, a butylthiomethyl group, and the like.

  Examples of the “C1-4 alkoxy C1-2 alkyl group” represented by Q include a methoxymethyl group, an ethoxymethyl group, an ethoxyethyl group, and a butoxymethyl group.

  The “C1-5 acylamino C1-6 alkyl group” represented by Q is a group in which a C1-5 acyl group in which a hydrogen atom or a C1-4 alkyl group is bonded to a carbonyl group is bonded to an amino C1-6 alkyl group, Specifically, formylaminomethyl group, acetylaminomethyl group, 2- (propionylamino) ethyl group, 3- (acetylamino) propyl group, 3- (propionylamino) propyl group, 3- (isopropionylamino) propyl group 3- (butyroylamino) propyl group, 3- (isobutyroylamino) propyl group, 3- (sec-butyroylamino) propyl group, 3- (tert-butyroylamino) propyl group, 4- (acetyl Examples include amino) butyl group, 5- (acetylamino) pentyl group, and 6- (acetylamino) hexyl group.

  Specific examples of the “C1-5 acylamino C1-6 alkoxy group” represented by Q include a formylaminomethoxy group, an acetylaminomethoxy group, a 2- (propionylamino) ethoxy group, a 3- (acetylamino) propoxy group, 3- (propionylamino) propoxy group, 3- (isopropionylamino) propoxy group, 3- (butyroylamino) propoxy group, 3- (isobutyroylamino) propoxy group, 3- (sec-butyroylamino) propoxy group Group, 3- (tert-butyroylamino) propoxy group, 4- (acetylamino) butoxy group, 5- (acetylamino) pentyloxy group and 6- (acetylamino) hexyloxy group.

  Specific examples of the “C1-8 alkylamino group” represented by Q include methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutylamino group, sec-butylamino group, tert. -Butylamino group, neopentylamino group, 1-ethylpropylamino group, n-pentylamino group, hexylamino group, heptylamino group, octylamino group and the like can be mentioned.

Specific examples of the “C2-6 alkenyl group” represented by Q include a vinyl group, an allyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 2-pentenyl group, and a 5-hexenyl group. It is done.
The “aralkyl group” represented by Q is a group in which an aryl group, preferably a C6-10 aryl group, and an alkyl group, preferably a C1-4 alkyl group, are bonded. Specifically, a benzyl group, phenethyl Groups and the like.

  Among these, Q is preferably a C1-8 alkyl group or a C1-8 alkoxy group.

  Specific examples of the compounds included in the present invention are shown in the table below.

  Of the compounds represented by the formula (1), preferred compounds include n = 0-2, X is a halogen atom, and A is a tetrazoyl group represented by the formula (2). , Het is a pyridine group represented by the formula (4), wherein Z is represented by the formula (5) (wherein Q represents a C1-8 alkyl group or a C1-8 alkoxy group). And tetrazoyl oxime derivatives which are the groups to be described.

  The oxime moiety present in the tetrazoylhydroxyimino derivative represented by the tetrazoyloxime derivative represented by the above formula (1) has three-dimensional structures (E) and (Z), and these two stereoisomers. And mixtures thereof are included in the present invention. Usually, the synthesized product is obtained only as the (Z) isomer or as a mixture of the (E) isomer and the (Z) isomer.

Two isomers can be isolated from the mixture of (E) and (Z) isomers by separation and purification.
In the tetrazoyl oxime derivative of the formula (1), the (Z) form is superior to the plant disease control activity than the (E) form. However, the (Z) body also tends to stabilize at a certain ratio as a mixture of the (E) body and the (Z) body due to the action of light or the like in the natural environment, and partly changes to the (E) body. Both compounds and mixtures thereof are also useful. In addition, since the stabilization ratio of (E) body and (Z) body changes with each compound, it cannot be specified unconditionally.

(Production method)
The tetrazoyl oxime derivative represented by the formula (1) can be produced by the method described in Patent Document 3 (WO 03/016303). However, the production method of the tetrazoyloxime derivative of the present invention is not limited to this production method.

(Plant growth promoter)
The plant growth promoter of the present invention only needs to contain the above-described tetrazoyloxime derivative as an active ingredient, and other ingredients, carriers and the like can be appropriately blended.
Although the tetrazoyl oxime derivative of the present invention can be used alone as a plant growth promoter, it is usually used as a conventional solid carrier, liquid carrier, dispersant, or the like used in a preparation containing the tetrazoyl oxime derivative as an active ingredient. Mix with adjuvants such as diluents, emulsifiers, spreading agents, and thickeners, and use it in dosage forms such as wettable powders, liquids, oils, powders, granules or sols (flowable). Can do.

  Examples of the solid carrier or liquid carrier include talc, clay, bentonite, kaolin, diatomaceous earth, montmorillonite, mica, vermiculite, gypsum, calcium carbonate, white carbon, wood powder, starch, alumina, silicate, sugar polymer, Waxes, water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, ethylene glycol, benzyl alcohol, etc.), petroleum fractions (petroleum ether, kerosene, solvent naphtha, etc.), fat Aromatic or alicyclic hydrocarbons (n-hexane, cyclohexane, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, chlorobenzene, cumene, methylnaphthalene, etc.), halogenated hydrocarbons (chloroform, dichloromethane) ), Ethers (isopropyl ether, ethylene oxide, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyl ketone, etc.), esters (ethyl acetate, butyl acetate, ethylene glycol acetate, amyl acetate, etc.), Acid amides (dimethylformamide, dimethylacetanilide, etc.), nitriles (acetonitrile, propionitrile, acrylonitrile, etc.), sulfoxides (dimethylsulfoxide, etc.), alcohol ethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, etc.), Etc.

  Examples of auxiliary agents include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkyl esters, polyoxyethylene alkyl phenyl ethers, polyoxyethylene sorbitan alkyl esters, sorbitan alkyl esters, etc.), anionic interfaces Activators (alkyl benzene sulfonate, alkyl sulfosuccinate, polyoxyethylene alkyl sulfate, aryl sulfonate, etc.), cationic surfactants (alkyl amines, polyoxyethylene alkyl amines, quaternary ammonium salts, etc.) Amphoteric surfactants (alkylaminoethylglycine, alkyldimethylbetaine, etc.), polyvinyl alcohol, hydroxypropylcellulose, carboxymethylcellulose, gum arabic, tiger Ntogamu, xanthan gum, polyvinyl acetate, gelatin, casein, sodium alginate, and the like.

  Furthermore, the tetrazoyl oxime derivative of the present invention can be used by mixing with various well-known and commonly used agricultural and horticultural fungicides, plant growth regulators, insecticides, acaricides and the like, fertilizers and the like. The content of the tetrazoyl oxime derivative of the present invention in the plant growth promoter varies depending on the preparation form, application method, and other conditions, but is preferably 0.5 to 95% by mass, and 2 to 70% by mass. Particularly preferred.

  The plant to be applied is not particularly limited, but for example, gramineous grains such as rice, barley, wheat, millet, corn, millet; pumpkin, turnip, cabbage, radish, Chinese cabbage, spinach, green pepper, tomato, etc. Vegetables; Flowers such as chrysanthemum, gerbera, pansy, orchid, peony, tulip; beans such as azuki bean, green beans, soybean, peanut, broad bean, pea; potatoes such as potato, sweet potato, taro, yam, taro; Onions such as onion and rakkyo are listed.

  Examples of the method for applying the plant growth promoter of the present invention include application to plants (spreading of leaves and leaves), application to growing soil (soil application), application to paddy water (application to water surface), application to seeds (seed Processing) is possible.

  The application rate of the plant growth promoter of the present invention varies depending on the applied plant and the like, but in the case of foliage spraying, the active ingredient concentration is in the range of 1 to 10000 ppm, preferably 10 to 1000 ppm in 50 to 10 ares. It is preferable to apply 300 L, and in the case of soil application and water surface application, it is preferable to apply 0.1 to 1000 g, particularly preferably 10 to 100 g per 10 ares as the amount of active ingredient. In the case of seed treatment, it is preferable to apply 0.001 to 50 g of an active ingredient to 1 kg of seed.

  When the plant growth promoter of the present invention is applied, healthy growth of various plants becomes possible. In particular, it is effective in promoting rooting of plants, raising healthy seedlings, and increasing the number of divisions, and an increase in yield can be expected.

  Next, although an example and a test example explain the present invention, the present invention is not limited to these.

(Example 1) Flowable agent Compound (1-13) described in Table 1 10 parts Polyoxyethylene aryl phenyl ether ether 2 parts Dialkylsulfosuccinate sodium salt 0.5 part Glycerin 5 parts Xanthan gum 0.3 part Water 82. 2 parts or more were mixed and wet pulverized until the particle size became 3 microns or less to obtain a flowable agent having an active ingredient of 10%.

(Example 2)
A flowable agent was obtained in the same manner as in Example 1 except that the compound (1-31) shown in Table 1 was used instead of the compound (1-13).

(Example 3)
A flowable agent was obtained in the same manner as in Example 1 except that the compound (2-13) shown in Table 2 was used instead of the compound (1-13).

(Test Example 1) Rice healthy seedling effect test Each of the flowable agents obtained in Example 1 or 2 in a small nursery box (15 × 10 × 4 cm) filled with floor soil in advance was at a concentration of 100 ppm as an active ingredient. The solution was diluted with water and approximately 80 ml of these drug solutions were uniformly irrigated per small nursery box. About 12 g of rice seeds (variety Koshihikari) made into a pigeon breast state by soaking treatment were sown in this seedling box as dry straw per seedling box. The seedlings were germinated at 30 ° C. for 3 days, and then subjected to low temperature stress at 4 ° C. for 3 days. Thereafter, seedlings were managed in a glass greenhouse. The longest root length of 30 seedlings per each seedling box was measured 21 days after sowing.
The results are shown in the following table.

(Test Example 2)
"Wheat seedling effect"
10 g of each flowable agent obtained in Examples 1 to 3 and 1 kg of dried seeds of wheat (variety: Norin 61) were placed in a plastic bag and mixed, and the seed surface was smeared. From this smearing treatment, the active ingredient treatment amount per kg of dried seed was 1 g. 20 seeds of the above-mentioned treated seeds were sown in a No. 4 pot. After sowing, seedlings were managed in a glass greenhouse. 21 days after sowing, the germination rate and the dry weight of the root of the seedling were examined. The test was conducted in triplicate.
The results are shown in the following table.

  From the above test results, the treatment of each compound showed a significant increase in average longest root length in rice, and an improvement in budding rate and an increase in average root dry weight in wheat.

  According to the plant growth promoter of the present invention, plant growth can be promoted. In particular, the effect of healthy seedlings is achieved, and by applying to seedlings before transplanting, rooting of seedlings is increased and transplantation is promoted after transplanting to Honda, and the number of divisions is also good, especially at low temperatures It is possible to exert a growth promoting effect. Furthermore, the effect of preventing the generation of mussel seedlings can be significantly increased.

Claims (4)

Formula (1):
[Wherein, X represents a halogen atom. n represents an integer of 0 to 2 , and when n is 2 or more, Xs may be the same or different from each other.
A is the formula (2):
(Wherein Y represents an alkyl group) or a tetrazoyl group represented by formula (3):
(Wherein Y represents an alkyl group).
Het is the formula (4):
{In the formula, R represents a halogen atom. m represents an integer of 0 to 3, and when m is 2 or more, Rs may be the same or different from each other. Z is the formula (5):
QC (= O) -NH- (5)
(Wherein Q represents a C1-8 alkyl group or a C1-8 alkoxy group ). } The pyridine group represented by this is shown. ] The plant growth promoter which contains the tetrazoyl oxime derivative represented by this as an active ingredient. Characterized that, the plant growth promoting agent according to claim 1 that is a tetrazolyl group tetrazoyloxime derivative, A is represented by the formula (2) represented by the formula (1).   The plant growth promoter according to claim 1 or 2, wherein the plant growth promoter is intended for growing healthy seedlings of plants.   The plant growth promoter according to any one of claims 1 to 3, wherein the plant is a gramineous grain.