JP7429572B2 - plant activator - Google Patents

Description

The present invention relates to a plant activator.

Techniques for regulating plant growth have been developed with the aim of improving the supply efficiency of grain plants and garden plants. In addition to measures such as optimizing temperature and sunlight conditions and fertilization, methods have been reported for activating plants using plant activators that have plant growth regulating effects such as promoting growth, suppressing dormancy, and suppressing stress.

Patent Document 1 reports a plant activator characterized by containing an oxo fatty acid derivative or a salt or ester thereof as an active ingredient. Although the plant activator described in Patent Document 1 has excellent resistance-inducing effects and growth-promoting effects, it has a problem that it is very unstable and easily decomposes.

Although the decomposition is presumed to be due to oxidation, there is no effective means to suppress this decomposition, and a technology to prevent oxidation has been strongly desired.

International Publication No. 2018/168860

The plant activator produced by the method described in Patent Document 1 has a problem in that it is easily oxidized in the atmosphere. In order to stably exhibit the effect as a plant activator over a long period of time, there is a need for a plant activator that is not easily oxidized and can maintain its effect as a plant activator.

The present invention aims to provide a plant activator that contains an antioxidant to prevent oxidation and has excellent disease resistance and growth promoting effects.

The present invention provides an oxo fatty acid or a derivative thereof or a salt thereof;
Formula (I) and/or (II) below
HOOC-(R ¹ )-CH(OH)-CH(OH)-CH=CH-CH(OH)-R ² (I)
HOOC-(R ¹ )-CH(OH)-CH=CH-CH(OH)-CH(OH)-R ² (II)
(In the formula,
R ¹ is a straight-chain or branched hydrocarbon group containing from 4 to 12 carbon atoms, which may contain one or more double bonds and/or OH groups; If it contains a bond, the position of the double bond is not limited.
R ² is a straight-chain or branched hydrocarbon group containing from 2 to 8 carbon atoms, which may contain one or more double bonds and/or OH groups, If it contains a bond, the position of the double bond is not limited)
A hydroxylated fatty acid or a derivative thereof or a salt thereof having the structural formula;
The present invention relates to a plant activator characterized by containing at least one selected from a phenolic antioxidant, ascorbic acid, and tocopherol. Here, R ¹ is particularly preferably -(CH ₂ ) _n - (where n is an integer from 4 to 12).

The plant activator is preferably characterized in that the phenolic antioxidant is butylhydroxyanisole.

A plant activator in which at least one selected from the phenolic antioxidant, ascorbic acid and tocopherol is added in an amount of 1/2 to 5 times the weight of the active ingredient is preferred.

The hydroxylated fatty acid is a hydroxylated fatty acid in which the R ¹ hydrocarbon group of the hydroxylated fatty acid has 6 to 8 carbon atoms, and the R ² hydrocarbon group has 4 to 6 carbon atoms. Preferred are plant activators.

The hydroxylated fatty acid has a structure in which R ¹ of the hydroxylated fatty acid has a structure of -(CH ₂ ) _n - (n is an integer from 4 to 12), and R ² has a structure of C _n H _2n+1 -(n is an integer from 2 to 8), a plant activator that is a hydroxylated fatty acid is preferred.

In the hydroxylated fatty acid, R ¹ of the hydroxylated fatty acid is an alkylene group having 7 carbon atoms (-(CH ₂ ) ₇ --), and R ² is an alkyl group having 5 carbon atoms (CH ₃ CH ₂ CH ₂ Preferably, the plant activator is a hydroxylated fatty acid (CH ₂ CH ₂ -).

A plant activator in which the hydroxylated fatty acid is hydroxyoctadecaenoic acid is preferable.

A plant activator in which the hydroxylated fatty acid is 9,10,13-trihydroxy-11-octadecaenoic acid is preferred.

A plant activator in which the hydroxylated fatty acid is 9,12,13-trihydroxy-10-octadecaenoic acid is preferred.

In addition, "octadecaenoic acid" is a conventional notation (for example, JP-A-3-14539, etc.), and the above-mentioned "9,10,13-trihydroxy-11-octadecaenoic acid" is "9,10, It is also written as ``13-trihydroxyoctadec-11-enoic acid'' or ``9,10,13-trihydroxy-11-octadecenoic acid.'' Similarly, the above-mentioned "9,12,13-trihydroxy-10-octadecaenoic acid" is replaced by "9,12,13-trihydroxyoctadec-10-enoic acid" or "9,12,13-trihydroxy- It is also written as "10-octadecenoic acid". In addition, in the examples, the manufacturer's description is also written in parentheses. Furthermore, the above explanation applies to all "octadecaenoic acid" used in the present specification, claims, drawings, and abstract.

The structural formula of "9,10,13-trihydroxy-11-octadecaenoic acid" is shown by the following structural formula (1).

The structural formula of "9,12,13-trihydroxy-10-octadecaenoic acid" is shown by the following structural formula (2).

A plant activator in which the oxo fatty acid is ketooctadecadienoic acid is preferred.

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

Note that as the oxo fatty acid and hydroxylated fatty acid derivatives, esters of oxo fatty acid and hydroxylated fatty acid are desirable, respectively. Further, as the salts of the oxo fatty acids and hydroxylated fatty acids, sodium salts, potassium salts, ammonium salts, etc. can be used.

It is preferable that the above-mentioned plant activator is a plant activator used as a spray or immersion agent that is brought into contact with the leaves or roots of a plant, or as a soil irrigation agent.

The plant activator is preferably a plant activator used for plants selected from Brassicaceae, Poaceae, Fabaceae, Solanaceae, Rosaceae, Amaranthaceae, or Malvaceae.

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

Plant activator The plant activator of the present invention is
Oxo fatty acid or its derivative or its salt and the following formula (I) and/or (II)
HOOC-(R ¹ )-CH(OH)-CH(OH)-CH=CH-CH(OH)-R ² (I)
HOOC-(R ¹ )-CH(OH)-CH=CH-CH(OH)-CH(OH)-R ² (II)
(In the formula,
R ¹ is a straight-chain or branched hydrocarbon group containing from 4 to 12 carbon atoms, which may contain one or more double bonds and/or OH groups; If it contains a bond, the position of the double bond is not limited.
R ² is a straight-chain or branched hydrocarbon group containing from 2 to 8 carbon atoms, which may contain one or more double bonds and/or OH groups, If it contains a bond, the position of the double bond is not limited)
A hydroxylated fatty acid or a derivative thereof or a salt thereof having the structural formula;
It is characterized by containing at least one selected from phenolic antioxidants, ascorbic acid, and tocopherols. In particular, R ¹ is preferably -(CH ₂ ) _n - (where n is an integer from 4 to 12). Note that the oxo fatty acid and the compound having the structural formula represented by the above formula (I) and/or (II) include all geometric isomers and stereoisomers thereof.

In the present invention, "plant activation" means adjusting the growth activity of a plant in some way to activate or maintain it, and includes growth promotion (including expansion of stems and leaves, promotion of growth of tubers, etc.). This concept encompasses plant growth regulating effects such as suppressing dormancy, inducing and imparting plant resistance to stress (eg, diseases, etc.), and anti-aging.

The plant activator of the present invention contains an oxo fatty acid, a derivative thereof, or a salt thereof, and a hydroxylated fatty acid, a derivative thereof, or a salt thereof, as active ingredients for activating plants. For example, the oxo fatty acid includes ketooctadecadienoic acid. For example, the ketooctadecadienoic acid specifically includes 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-octadecadienoic acid Examples include dienoic acid, 11-oxo-9,12-octadecadienoic acid, 12-oxo-9,13-octadecadienoic acid, 14-oxo-9,12-octadecadienoic acid, and isomers thereof. .

The present inventors inoculated plants with a hydroxylated fatty acid or a derivative thereof or a salt thereof having a structural formula as shown in the above formula (I) and/or (II), thereby inoculating the plant with an unsaturated fatty acid. Compared to treated plants, significant increases in plant growth indicators such as leaf length and number as well as leaf and plant weight, an increase in the number of stems per plant, and promotion of tuber or tuber growth were confirmed. It has been discovered that hydroxylated fatty acids, derivatives thereof, or salts thereof having the above-mentioned structural formula have an excellent plant activating effect. For example, the hydroxylated fatty acid includes hydroxyoctadecaenoic acid. For example, specific examples of hydroxyoctadecaenoic acid include 9,10,13-trihydroxy-11-octadecaenoic acid, 9,12,13-trihydroxy-10-octadecaenoic acid, and isomers thereof. It will be done.

The term "active ingredient" as used herein refers to such oxo fatty acids and hydroxylated fatty acids. Oxo-fatty acids such as keto-octadecadienoic acid and hydroxylated fatty acids such as hydroxyoctadecenoic acid have excellent properties to activate plant growth, and therefore oxo-fatty acids or their derivatives or their salts and hydroxylated fatty acids By bringing the plant activator of the present invention containing a fatty acid, a derivative thereof, or a salt thereof as an active ingredient into contact with a portion of the stems, leaves, or roots of a plant, a very high plant growth promoting effect can be imparted to the plant.

Note that esters are desirable as the derivatives of the oxo fatty acids and hydroxylated fatty acids. Further, as the salts of the oxo fatty acids and hydroxylated fatty acids, sodium salts, potassium salts, ammonium salts, etc. can be used.

However, hydroxylated fatty acids are oxidized in the atmosphere. Additionally, oxo fatty acids change into hydroxylated fatty acids when they react with oxygen and water in the atmosphere. Since the rate at which oxo fatty acids change to hydroxylated fatty acids is faster than the rate at which hydroxylated fatty acids are oxidized, as a result, when both coexist, the amount of hydroxylated fatty acids increases over time. It's put away.

At least one selected from the phenolic antioxidant, ascorbic acid and tocopherol contained in the plant activator of the present invention is combined with oxo fatty acid or its derivative or its salt and hydroxylated fatty acid or It acts as an antioxidant that suppresses the decomposition of its derivatives or its salts. As a result, the plant activating material of the present invention is stabilized. In other words, by containing such an antioxidant, a decrease in the activation effect and a decrease in storage stability can be prevented during processing, distribution, and storage during formulation of the plant activator. The effectiveness as a plant activator during application is ensured. For example, preferred examples of antioxidants that contribute to stabilizing the plant activator are phenolic antioxidants, ascorbic acid (vitamin C), and tocopherol (vitamin E). However, without being limited to tocopherols, other vitamin E may also be used, such as natural or synthetic vitamin E homologues, various derivatives and analogues of vitamin E having antioxidant activity. Furthermore, ascorbic acid (vitamin C) of the present invention includes oxidized forms and isomers of ascorbic acid. Furthermore, an example of the phenolic antioxidant includes butylhydroxyanisole. However, other phenolic antioxidants with antioxidant properties can also be used.

Even with the addition of the antioxidant of the present invention, the excellent growth promoting effect of the plant activator containing oxo fatty acid or its derivative or its salt and hydroxylated fatty acid or its derivative or its salt may be reduced or lost. You will not be disappointed. Furthermore, the addition of antioxidants does not have an adverse effect on the plants to which they are applied. Therefore, by adding the antioxidant of the present invention, the excellent activating effect of the plant activator containing oxo fatty acid or its derivative or its salt and hydroxylated fatty acid or its derivative or its salt can be maintained in the plant activator. By suppressing the decomposition of the active ingredient in the plant activator, it is possible to maintain a stable activating effect over a long period of time in the plant activator.

In the present invention, the antioxidant may be added in a weight ratio of about 5 times or less to the amount of active ingredient in the plant activator. The preferred concentration of the antioxidant that can be included in the plant activator of the present invention may depend on the plant species to which it is applied and its condition, but if the ratio exceeds 5 times the amount, it may cause phytotoxicity to the plants to which it is applied. There is a possibility that this may occur. The lower limit of the concentration of the antioxidant is not particularly limited, but it is preferably about 1/2 or more times the amount of the active ingredient by weight. In a preferred embodiment of the present invention, the proportion of the antioxidant is 1/2 to 5 times the amount of the active ingredient by weight.

Here, the amount of active ingredient in the present invention refers to the total amount of oxo fatty acids and hydroxylated fatty acids, derivatives thereof, or salts thereof contained in the plant activator of the present invention. For example, the amount of active ingredient in the plant activator of the present invention is about 0.2 to 2.0 g/L. The plant activator of the present invention contains an antioxidant in an amount of 1/2 to 5 times the weight of the active ingredient. By adding this amount of antioxidant, the decomposition of the active ingredient in the plant activator is significantly suppressed, and the activating effect can be maintained for a long period of time.

The plant activator of the present invention may optionally contain a compatible surfactant and/or diluent or carrier suitable for use as a plant activator. These additive components are not particularly limited as long as they are agriculturally acceptable agents. In addition, components other than surfactants, diluents, and carriers that are commonly used in agricultural chemical formulations may be further contained.

The plant activator of the present invention can be applied to plants by any method. For example, it can be used as a spray or immersion agent for contacting the leaves or roots of plants, or as a soil irrigation agent. Further, the plant activator of the present invention may be included in a porous structure or capsule, or impregnated into a sheet or the like, and used as a sustained release drug. The plant activator of the present invention imparts a plant growth promoting effect to the plants to which it is applied.

The plants to which the plant activator of the present invention can be applied are not particularly limited, and it can be successfully used for plants in general, but examples include Poaceae, Fabaceae, Solanaceae, Rosaceae, Examples include plants of the family Malvaceae or Brassicaceae. For example, plants of the Poaceae family, such as grass, rice, wheat, and corn; plants of the Leguminosae family, such as soybeans, broad beans, kidney beans, and licorice; plants of the Solanaceae family, such as tomatoes, eggplants, chili peppers, and bell peppers; Plants of the Rosaceae family such as potatoes, such as strawberries, plants of the Amaranthaceae family such as spinach, plants of the Malvaceae family such as cotton, okra, etc., plants of the Brassicaceae family such as Komatsuna, mizuna, etc. Growth is effectively promoted. Moreover, the plants to be applied are not limited to wild-type plants, and may be, for example, mutants or transformants. Moreover, the variety of each plant is not particularly limited.

Furthermore, it has been discovered that the plant activator of the present invention can be used as a plant activator that exhibits a strong resistance-inducing effect, and has been shown to exhibit growth-promoting effects, fruit yield-increasing effects, and disease-suppressing effects on various plants. I have knowledge. For example, specific examples of effective disease control include gray mold on the leaves of cucurbits, such as cucumbers, watermelons, melons, and pumpkins; bacterial wilt, wilt, half-wilt, damping-off, brown root rot, powdery mildew of plants of the Rosaceae family, such as roses and strawberries, scab, gray mold, anthracnose, downy mildew of plants of the Amaranthaceae family, such as spinach, It is effective against black rot, soft rot, bacterial spot disease, Rhizoctonia disease in Brassicaceae such as Chinese cabbage, cabbage, and komatsuna, white silk disease in Apiaceae such as carrots, and blast in Poaceae plants.

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

Example 1
Preparation of plant activator Hydroxylated fatty acids include hydroxyoctadecaenoic acid, 9,10,13-trihydroxy-11-octadecaenoic acid (manufactured by Lalaudan Fine Chemicals, 9(S), 10(S), 13( S)-trihydroxy-11(E) -octadecenoic acid (9(S),10(S),13(S)-trihydroxy-11(E)-octadecenoic acid in English), 200mg/L ethanol solution), and 9,12,13-trihydroxy-10-octadecaenoic acid (manufactured by Lalaudan Fine Chemicals, 9(S),12(S),13(S)-trihydroxy-10(E) -octadecaenoic acid ) Using a 2:1 mixture of senic acid (9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid), 200 mg/L ethanol solution) , an aqueous solution containing hydroxyoctadecaenoic acid was prepared. That is, 9(S),10(S),13(S)-trihydroxy-11(E) -octadecenoic acid was prepared by dissolving 75 mL of ethanol solution in 1 L of water to give a concentration of 15 mg/L, and then In this aqueous solution, 35 mL of an ethanol solution of 9(S), 12(S), 13(S)-trihydroxy-10(E) -octadecenoic acid was dissolved, and the concentration was adjusted to 7 mg/L. To 778 mL of this aqueous solution was added 13-oxo-9,11-octadecadienoic acid (13-oxoODA) ((9Z,11E)-13-oxo-9,11-octadecadienoic acid, manufactured by Cayman Chemical Co., Ltd., 100 μg/100 μL ethanol. Solution) was added in an amount of 222 mL, and the resulting solution was used as a test plant activator.

Addition of vitamin C and vitamin E and accelerated test To 1 L of the test plant activator obtained above (active ingredient amount 239 mg), 680 mg of vitamin C (manufactured by Kanto Kagaku Co., Ltd.) and 480 mg of vitamin E (manufactured by Nacalai Tesque) were added. 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 Taitec Co., Ltd.) and left for 5 weeks (equivalent to about 2 years at 25°C. Sumie Yoshioka) (Refer to "Stability of Pharmaceutical Products" by the author). Measure the active ingredient concentration before and after the accelerated test using UV, and calculate the ratio of the active ingredient concentration after the accelerated test to the active ingredient concentration before the accelerated test (% change in active ingredient concentration), and calculate the UV area ratio before and after the accelerated test. Calculated from.

Example 2
To 1 L of the test plant activator obtained above (active ingredient amount 239 mg), 480 mg of butyl hydroxyanisole (manufactured by Kishida Chemical Co., Ltd.), a phenolic antioxidant, was added, and the plant activator of Example 1 was combined with the plant activator of Example 1. did. The obtained plant activator was subjected to an accelerated test at 54°C using a Bioshaker (registered trademark) (BR-23UM manufactured by Taitec Co., Ltd.) and left for 5 weeks (corresponding to about 2 years at 25°C). (Refer to "Stability of Pharmaceutical Products" by Sumie Yoshioka). Measure the active ingredient concentration before and after the accelerated test using UV, and calculate the ratio of the active ingredient concentration after the accelerated test to the active ingredient concentration before the accelerated test (% change in active ingredient concentration), and calculate the UV area ratio 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 (active ingredient amount 239 mg). The obtained solution was subjected to an accelerated test at 54°C using a Bioshaker (registered trademark) (BR-23UM manufactured by Taitec Co., Ltd.) and left for 5 weeks (equivalent to about 2 years at 25°C. Sumie Yoshioka) (Refer to "Stability of Pharmaceutical Products" by the author). Measure the active ingredient concentration before and after the accelerated test using UV, and calculate the ratio of the active ingredient concentration after the accelerated test to the active ingredient concentration before the accelerated test (% change in active ingredient concentration), and calculate the UV area ratio before and after the accelerated test. Calculated from.

Example 4
120 mg of vitamin E was added to 1 L of the test plant activator obtained above (active ingredient amount 239 mg). The obtained solution was subjected to an accelerated test at 54°C using a Bioshaker (registered trademark) (BR-23UM manufactured by Taitec Co., Ltd.) and left for 5 weeks (equivalent to about 2 years at 25°C. Sumie Yoshioka) (Refer to "Stability of Pharmaceutical Products" by the author). Measure the active ingredient concentration before and after the accelerated test using UV, and calculate the ratio of the active ingredient concentration after the accelerated test to the active ingredient concentration before the accelerated test (% change in active ingredient concentration), and calculate the UV area ratio before and after the accelerated test. Calculated from.

Comparative example 1
1L of the test plant activator obtained above (active ingredient amount 239mg) was subjected to an accelerated test at 54°C using a Bioshaker (registered trademark) (BR-23UM manufactured by Taitec Co., Ltd.) and left for 5 weeks. (equivalent to about 2 years at 25°C; see "Stability of Pharmaceuticals" by Sumie Yoshioka). Measure the active ingredient concentration before and after the accelerated test using UV, and calculate the ratio of the active ingredient concentration after the accelerated test to the active ingredient concentration before the accelerated test (% change in active ingredient concentration), and calculate the UV area ratio before and after the accelerated test. Calculated from.

The results of % 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 acids in the plant activator decreased significantly after 5 weeks of the accelerated test. It can be seen that it has almost completely disassembled. Along with this, the concentration of hydroxylated fatty acids increased approximately twice after the accelerated test compared to before the accelerated test, indicating that oxo fatty acids were decomposed and changed to hydroxylated fatty acids. 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 acids 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 significantly suppressed by the addition of the antioxidant. Further, in Examples 1 to 4, only a small increase in the concentration of hydroxylated fatty acids was observed, that is, the decomposition of oxo fatty acids and the change to hydroxylated fatty acids were suppressed. This result shows that the plant activator containing the antioxidant of the present invention has an excellent effect on stabilizing oxo fatty acids and hydroxylated fatty acids, which are active ingredients for activating plants.

The above results show that the plant activator containing at least one selected from the phenolic antioxidant, ascorbic acid, and tocopherol of the present invention has a remarkable effect on stabilizing the active ingredient.

Claims (4)

13-oxo-9,11-octadecadienoic acid or a salt thereof ;
At least one selected from 9,10,13-trihydroxy-11-octadecenoic acid or a salt thereof , and 9,12,13-trihydroxy-10-octadecenoic acid or a salt thereof,
A plant activator characterized by containing at least one selected from phenolic antioxidants, ascorbic acid, and tocopherols. The plant activator according to claim 1, wherein the phenolic antioxidant is butylhydroxyanisole. The plant activator according to claim 1 or 2 , which is used as a spray or immersion agent that is brought into contact with the leaves or roots of plants, or as a soil irrigation agent. The plant activator according to any one of claims 1 to 3 , wherein the plant activator is used for plants selected from Brassicaceae, Poaceae, Fabaceae, Solanaceae, Rosaceae, Amaranthaceae, or Malvaceae. The plant activator described.