JP2021095384A - Plant activator - Google Patents

Abstract

To provide a stabilized plant activator that resists oxidative degradation.SOLUTION: A plant activator contains an oxo fatty acid or a derivative thereof or a salt thereof, and at least one selected from a phenolic antioxidant, ascorbic acid and tocopherol.SELECTED DRAWING: None

Description

The present invention relates to a plant activator.

Techniques for adjusting the growth of plants have been developed for the purpose of improving the supply efficiency of grain plants and horticultural plants. In addition to measures such as optimization of temperature conditions and sunshine conditions and fertilization, a method of activating plants using a plant activator having a plant growth regulating action such as growth promotion, dormancy suppression, and stress suppression has been reported.

Patent Document 1 reports a plant activator containing an oxo fatty acid derivative or a salt or ester thereof as an active ingredient. The plant activator described in Patent Document 1 has an excellent resistance-inducing effect and a growth-promoting effect, but has a problem that it is very unstable and decomposes immediately.

Decomposition is presumed to be due to oxidation, but there is no effective means for suppressing this decomposition, and a technique for preventing oxidation has been strongly desired.

International Publication No. 2018/168860

The plant activator produced by the method described in Patent Document 1 contains an oxo fatty acid derivative or a salt or ester thereof as an active ingredient, and therefore has a problem that it is easily oxidized in the air. In order to stably exhibit the effect as a plant activator over a long period of time, there is a demand for a plant activator that is not easily oxidized and can maintain the effect as a plant activator.

It is an object of the present invention to provide a plant activator which contains an antioxidant for preventing oxidation but has excellent disease resistance and growth promoting effect.

The present invention relates to a plant activator comprising oxo fatty acid or a derivative thereof or a salt thereof and at least one selected from a phenolic antioxidant, ascorbic acid and tocopherol.

More specifically, the present invention
The following formula:
HOOC- (R ¹ ) -CH = CH-C (= O) -R ² (I)
(During the ceremony
R ¹ : A linear or branched, saturated or unsaturated hydrocarbon group containing 6 to 12 carbon atoms.
R ² : Alkyl group having 2 to 8 carbon atoms, which may contain one or more branches and / or double bonds)
The present invention relates to a plant activator comprising oxo fatty acid or a derivative thereof or a salt thereof having the structural formula of the above, and at least one selected from a phenolic antioxidant, ascorbic acid and tocopherol.

A plant activator characterized in that the phenolic antioxidant is butylhydroxyanisole is preferable.

A plant activator in which at least one selected from the phenolic antioxidants, ascorbic acid and tocopherol is added at a ratio of 1/2 to 5 times by weight with respect to the amount of the active ingredient is preferable.

A plant activator in which the oxo fatty acid is an oxo fatty acid in which ^{the hydrocarbon group of R 1} of the oxo fatty acid has 8 to 10 carbon atoms and ^{the alkyl group of R 2 has 4 to 6 carbon atoms is preferable.}

^{A plant activator in which the oxo fatty acid is an oxo fatty acid containing a double bond in which R 1 of the} oxo fatty acid forms a double bond and a conjugated double bond between α and β carbons of the carbonyl group in the formula (I). Is preferable.

^{It is preferable that the oxo fatty acid is a plant activator in which R 1 of the} oxo fatty acid is a linear hydrocarbon group having 9 carbon atoms and R ² is an oxo fatty acid which is an alkyl group having 5 carbon atoms.

A plant activator in which the oxo fatty acid is 13-oxo-9,11-octadecadienoic acid is preferable.

As the derivative of the oxo fatty acid, an ester of the oxo fatty acid is desirable. Further, as the salt of the oxo fatty acid, a sodium salt, a potassium salt, an ammonium salt and the like can be used.

It is preferable that the plant activator is a spray agent or a dipping agent that comes into contact with the foliage or roots of a plant, or a plant activator used as a soil irrigation agent.

It is preferable that the plant activator is a plant activator used for cruciferous plants.

The plant activator of the present invention has excellent stability of the active ingredient, and has excellent disease resistance and growth promoting effect.

Plant Activator The plant activator of the present invention is characterized by containing an oxo fatty acid or a derivative thereof or a salt thereof, and at least one selected from a phenolic antioxidant, ascorbic acid and tocopherol.

More specifically, the plant activator of the present invention
The following formula:
HOOC- (R ¹ ) -CH = CH-C (= O) -R ² (I)
(During the ceremony
R ¹ : A linear or branched, saturated or unsaturated hydrocarbon group containing 6-12 carbon atoms.
R ² : Alkyl group having 2 to 8 carbon atoms, which may contain one or more branches and / or double bonds)
It is characterized by containing an oxo fatty acid having the structural formula of (1) or a derivative thereof or a salt thereof, and at least one selected from a phenolic antioxidant, ascorbic acid and tocopherol. The oxo fatty acid and the compound having the structural formula represented by the above formula (I) include all geometric isomers and stereoisomers thereof.

The term "plant activation" in the present invention means to adjust the growth activity of a plant to be activated or maintained in some way, and includes promotion of growth (expansion of foliage, promotion of tuberous roots, etc.). It is a concept that induces and imparts resistance to plant stress (for example, disease), suppresses dormancy, and includes plant growth-regulating actions such as anti-aging.

The plant activator of the present invention contains an oxo fatty acid or a derivative thereof or a salt thereof as an active ingredient for activating a plant. For example, examples of the oxo fatty acid include ketooctadecadienoic acid. For example, as ketooctadecadienoic acid, specifically, 9-oxo-10,12-octadecadienoic acid (9-oxoODA), 13-oxo-9,11-octadecadienoic acid (13-oxoODA). , 5-oxo-6,8-octadecadienoic acid, 6-oxo-9,12-octadecadienoic acid, 8-oxo-9,12-octadecadienoic acid, 10-oxo-8,12-octadeca Examples thereof include dienoic acid, 11-oxo-9,12-octadecadienoic acid, 12-oxo-9,13-octadecadienoic acid, 14-oxo-9,12-octadecadienoic acid and isomers thereof. .. As used herein, the term "active ingredient" means such an oxo fatty acid. Oxofatty acids such as ketooctadecazienoic acid have the property of activating plant growth, and therefore the plant activator of the present invention containing oxofatty acid or a derivative thereof or a salt thereof as an active ingredient can be applied to the foliage or root of a plant. By contacting a part of the plant, a growth promoting effect can be imparted to the plant. In addition, since this oxo fatty acid can activate the salicylic acid pathway involved in the induction of resistance, resistance can be induced in the plant by applying it to the plant.

As the derivative of the oxo fatty acid, an ester is desirable. Further, as the salt of the oxo fatty acid, a sodium salt, a potassium salt, an ammonium salt and the like can be used.

At least one selected from the phenolic antioxidants, ascorbic acid and tocopherol contained in the plant activator of the present invention acts as an antioxidant that suppresses the decomposition of the active ingredient in the plant activator. As a result, the plant activator of the present invention is stabilized. That is, by containing such an antioxidant, it is possible to prevent a decrease in the activation effect and a decrease in storage stability with respect to the treatment, distribution and storage of the plant activator at the time of formulation, and the plant activator. Effectiveness as a plant activator at the time of application is ensured. Preferred examples of antioxidants that contribute to the stabilization of plant activators are phenolic antioxidants, ascorbic acid (vitamin C) and tocopherol (vitamin E), as described above. However, it is not limited to tocopherols, and other vitamin Es such as natural or synthetic vitamin E analogs, various derivatives and related compounds of vitamin E having antioxidant activity may also be used. In addition, the ascorbic acid (vitamin C) of the present invention contains an oxidized form or an isomer of ascorbic acid. Further, examples of the phenolic antioxidant include butylhydroxyanisole. However, other phenolic antioxidants with antioxidant properties can also be used.

The addition of the antioxidant of the present invention does not reduce or lose the excellent disease resistance and growth promoting effect of the plant activator containing the oxo fatty acid or its derivative or a salt thereof. In addition, the addition of antioxidants does not adversely affect the plant to which it is applied. Therefore, by adding the antioxidant of the present invention, the excellent activating effect of the plant activating agent containing the oxo fatty acid or its derivative or a salt thereof is maintained, and the decomposition of the active ingredient in the plant activating agent is suppressed. , Maintenance of stable activation effect over a long period of time in plant activators can be achieved.

In the present invention, the antioxidant can be added at a ratio of about 5 times or less by weight with respect to the amount of the active ingredient in the plant activator. The preferable concentration of the antioxidant that can be contained in the plant activator of the present invention may depend on the plant species to be applied and its condition, but if the ratio exceeds 5 times, it causes phytotoxicity to the applied plant. May occur. The lower limit of the concentration of the antioxidant is not particularly limited, but it is preferably about 1/2 times or more by weight with respect to the amount of the active ingredient. In a preferred embodiment of the present invention, the ratio of the antioxidant is 1/2 to 5 times the amount of the active ingredient by weight.

Here, the amount of the active ingredient in the present invention indicates the amount of an oxo fatty acid or a derivative thereof or a salt thereof contained in the plant activator of the present invention. For example, the amount of the active ingredient of the plant activator of the present invention is about 0.01 to 0.2 g / L. The plant activator of the present invention contains an antioxidant which is 1/2 to 5 times the amount of such an active ingredient by weight. By adding an antioxidant of this degree, the decomposition of the active ingredient in the plant activator is remarkably suppressed, and the activating effect can be maintained for a long period of time.

If necessary, the plant activator of the present invention may contain a compatible surfactant and / or a diluent or carrier suitable for use as a plant activator. These additive components are not particularly limited as long as they are agriculturally acceptable drugs. In addition, components other than surfactants, diluents, and carriers, which are usually used in pesticide preparations, may be further contained.

Further, in the plant activator of the present invention, in addition to oxofat or a derivative thereof or a salt thereof as an active ingredient, jasmonic acid precursor 12 / 10-oxo-phytodienoic acid that induces the expression of a resistance gene of the jasmonic acid pathway (12 / 10-OPDA) may be included. In the applied plant, both the salicylic acid pathway and the jasmonic acid pathway are mutually complementaryly activated, and a plant activator having a higher activating effect can be obtained.

The plant activator of the present invention can be applied to a plant by any method. For example, it can be used as a spray or dipping agent in contact with the foliage or roots of a plant, or as a soil irrigation agent. Further, the plant activator of the present invention may be contained in a porous structure or a capsule, or impregnated in a sheet or the like, and may be used as a sustained release agent. In the applied plant, the plant activator of the present invention imparts a plant growth promoting effect and resistance to stress such as diseases.

The plant to which the plant activator of the present invention can be applied is not particularly limited and can be satisfactorily used for plants in general, but preferred plants include cruciferous plants. However, it can also be applied, for example, to plants of the Gramineae, Leguminosae, Solanaceae, Rosaceae, Amaranthaceae, or Malvaceae families. Further, the plant to be applied is not limited to the wild type plant, and may be, for example, a mutant or a transformant. Moreover, the variety of each plant is not particularly limited.

Further, it has been found that the plant activator of the present invention can be used as a plant activator showing a strong resistance-inducing effect, and exhibits an effect of promoting the growth of various plants, an effect of increasing the yield of fruits, and an effect of suppressing diseases. I know. For example, specific examples that are effective in controlling diseases include gray mold disease on leaves of Cucurbitaceae such as cucumber, watermelon, melon, and pumpkin, vine rot, vine blight, downy mildew, tomato, eggplant, and potato. Blight, wilt, half-body wilt, wilt, brown root rot, cruciferous plants such as roses and strawberries, scab, gray mold, charcoal, and downy mildew, It is effective for black rot of Brassicaceae such as Chinese cabbage, cabbage and Komatsuna, soft rot, spot bacterial disease, lysoctonia disease, white silk disease of Cucurbitaceae such as carrot, and blast of rice plant.

Although the present invention will be described based on examples, the present invention is not limited to the examples.

Example 1
Preparation of plant activator 18 g of potassium carbonate (Fujifilm Wako Pure Chemical Industries, Ltd., special grade) and 23.3 g of dipotassium hydrogen phosphate were added to 1 L of water to prepare a basic aqueous solution. Then, as the oxo fatty acid, 13-oxo-9,11-octadecadienoic acid (13-oxoODA) ((9Z, 11E) -13-oxo-9,11-octadecadienoic acid, which is ketooctadecadienoic acid, 222 mL of 100 μg / 100 μL ethanol solution manufactured by Cayman Chemical Co., Ltd.) was added to 788 mL of a basic aqueous solution to prepare an aqueous solution containing 0.022% of 13-oxo-9,11-octadecazienoic acid. The obtained solution was used as a test plant activator.

Addition and Acceleration Test of Vitamin C and Vitamin E 680 mg of Vitamin C (manufactured by Kanto Kagaku Co., Ltd.) and 480 mg of Vitamin E (Nacalai Tesque) in 1 L (active ingredient amount 222 mg) of the test plant activator obtained above. Co., Ltd.) was added. The obtained solution was subjected to an accelerated test at 54 ° C. using a bioshaker (registered trademark) (BR-23UM manufactured by Tietech Co., Ltd.) and left for 5 weeks (equivalent to about 2 years at 25 ° C. See "Pharmaceutical Stability"). The active ingredient concentration is measured by UV before and after the accelerated test, and the ratio of the active ingredient concentration after the accelerated test (active ingredient concentration change%) to the active ingredient concentration before the accelerated test is the area ratio of UV before and after the accelerated test. Calculated from.

Example 2
Butylated hydroxyanisole (manufactured by Kishida Chemical Co., Ltd.), which is a phenolic antioxidant, was added to 1 L (active ingredient amount 222 mg) of the test plant activator obtained above in an amount of 480 mg. The obtained plant activator was subjected to an accelerated test at 54 ° C. using a bioshaker (registered trademark) (BR-23UM manufactured by Tietech Co., Ltd.) and left for 5 weeks (equivalent to about 2 years at 25 ° C.). See Sumie Yoshioka, "Pharmaceutical Stability"). The active ingredient concentration is measured by UV before and after the accelerated test, and the ratio of the active ingredient concentration after the accelerated test (active ingredient concentration change%) to the active ingredient concentration before the accelerated test is the area ratio of UV before and after the accelerated test. Calculated from.

Example 3
1110 mg of vitamin C was added to 1 L of the test plant activator obtained above (the amount of the active ingredient was 222 mg). The obtained solution was subjected to an accelerated test at 54 ° C. using a bioshaker (registered trademark) (BR-23UM manufactured by Tietech Co., Ltd.) and left for 5 weeks (equivalent to about 2 years at 25 ° C.) Sumie Yoshioka. See "Pharmaceutical Stability"). The active ingredient concentration is measured by UV before and after the accelerated test, and the ratio of the active ingredient concentration after the accelerated test (active ingredient concentration change%) to the active ingredient concentration before the accelerated test is the area ratio of UV before and after the accelerated test. Calculated from.

Example 4
480 mg of vitamin E was added to 1 L (active ingredient amount 222 mg) of the test plant activator obtained above. The obtained solution was subjected to an accelerated test at 54 ° C. using a bioshaker (registered trademark) (BR-23UM manufactured by Tietech Co., Ltd.) and left for 5 weeks (equivalent to about 2 years at 25 ° C.) Sumie Yoshioka. See "Pharmaceutical Stability"). The active ingredient concentration is measured by UV before and after the accelerated test, and the ratio of the active ingredient concentration after the accelerated test (active ingredient concentration change%) to the active ingredient concentration before the accelerated test is the area ratio of UV before and after the accelerated test. Calculated from.

Comparative Example 1
1 L (active ingredient amount 222 mg) of the test plant activator obtained above was subjected to an accelerated test at 54 ° C. using a bioshaker (registered trademark) (BR-23UM manufactured by Tietech Co., Ltd.) and left for 5 weeks. (Equivalent to about 2 years at 25 ° C. Refer to "Pharmaceutical Stability" by Sumie Yoshioka). The active ingredient concentration is measured by UV before and after the accelerated test, and the ratio of the active ingredient concentration after the accelerated test (active ingredient concentration change%) to the active ingredient concentration before the accelerated test is the area ratio of UV before and after the accelerated test. Calculated from.

The results of the% change in active ingredient concentration obtained in Examples 1 to 4 and Comparative Example 1 are shown in Table 1 below.

As shown in Table 1, in Comparative Example 1 in which no antioxidant was added, the concentration of oxo fatty acid, which is an active ingredient in the plant activator, decreased after 5 weeks of the accelerated test as compared with before the accelerated test. It can be seen that the oxo fatty acid is decomposed by the accelerated test. On the other hand, in the plant activators of Examples 1 to 4 to which the antioxidant of the present invention was added, the concentration of oxo fatty acid was well maintained even after 5 weeks of the accelerated test. This indicates that in Examples 1 to 4, the decomposition of oxo fatty acids was remarkably suppressed by the addition of the antioxidant. From this result, it can be seen that the plant activator containing the antioxidant of the present invention shows an excellent effect on the stabilization of oxo fatty acid, which is an active ingredient for activating plants.

From the above results, it can be seen that the plant activator containing at least one selected from the phenolic antioxidant, ascorbic acid and tocopherol of the present invention shows a remarkable effect on the stabilization of the active ingredient.

Claims (10)

A plant activator comprising oxo fatty acid or a derivative thereof or a salt thereof and at least one selected from a phenolic antioxidant, ascorbic acid and tocopherol. The following formula:
HOOC- (R ¹ ) -CH = CH-C (= O) -R ² (I)
(During the ceremony
R ¹ : A linear or branched, saturated or unsaturated hydrocarbon group containing 6 to 12 carbon atoms.
R ² : Alkyl group having 2 to 8 carbon atoms, which may contain one or more branches and / or double bonds)
The plant activator according to claim 1, which comprises an oxo fatty acid having the structural formula of the above, a derivative thereof, or a salt thereof, and at least one selected from a phenolic antioxidant, ascorbic acid and tocopherol. The plant activator according to claim 1 or 2, wherein the phenolic antioxidant is butylhydroxyanisole. Any one of claims 1 to 3 in which at least one selected from the phenolic antioxidant, ascorbic acid and tocopherol is added at a ratio of 1/2 to 5 times by weight with respect to the amount of the active ingredient. The plant activator according to item 1. The plant activator according to any one of claims 2 to 4, wherein the oxo fatty acid is used.
The hydrocarbon group of R ¹ has 8 to 10 carbon atoms and has 8 to 10 carbon atoms.
The alkyl group of R ² has 4 to 6 carbon atoms. The plant activator according to any one of claims 2 to 5, wherein the oxo fatty acid is used.
R ¹ comprises a double bond forming a conjugated double bond with a double bond between the α and β carbons of the carbonyl group in formula (I). The plant activator according to claim 6, which comprises the oxo fatty acid.
R ¹ is a linear hydrocarbon group having 9 carbon atoms.
R ² is an alkyl group having 5 carbon atoms. The plant activator according to claim 1 or 7, wherein the oxo fatty acid is 13-oxo-9,11-octadecadienoic acid. The plant activator according to any one of claims 1 to 8, which is used as a spraying agent or a dipping agent for contacting the foliage or root of a plant, or as a soil irrigation agent. The plant activator according to any one of claims 1 to 9, which is used for cruciferous plants.