Plant activator

Abstract

To provide a plant activator that resists oxidative degradation and is stabilized.SOLUTION: A plant activator contains an oxo fatty acid or a derivative thereof or a salt thereof, a hydroxylated fatty acid having the structural formula of HOOC-(R1)-CH(OH)-CH(OH)-CH=CH-CH(OH)-R2(I) and / or HOOC-(R1)-CH(OH)-CH=CH-CH(OH)-CH(OH)-R2(II) (R1 is a linear or branched hydrocarbon group having 4-12 carbon atoms, optionally including one or more double bond and / or OH group, where if a double bond is included, the position of it is not limited, and R2 is a linear or branched hydrocarbon group having 2-8 carbon atoms, optionally including one or more double bond and / or OH group, where if a double bond is included, the position of the double bond is not limited) 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

Technical Field

[0001] The present invention relates to a plant activator.

Background Art

[0002] Techniques for adjusting the growth of plants have been developed for the purpose of improving the supply efficiency of cereal plants and horticultural plants, etc. In addition to measures such as optimizing temperature conditions, sunlight conditions, and fertilization, methods for activating plants using a plant activator having a plant growth regulating action such as growth promotion, dormancy suppression, and stress suppression have been reported.

[0003] 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. The plant activator described in Patent Document 1 has excellent resistance induction effects and growth promotion effects, but has a problem that it is very unstable and decomposes immediately.

[0004] The 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.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0006] The plant activator produced by the method described in Patent Document 1 has a problem that it is easily oxidized in the air. In order to stably exhibit the effect as a plant activator for a long time, a plant activator that is not easily oxidized and can maintain the effect as a plant activator is required.

[0007] The present invention aims to provide a plant activator that contains an antioxidant for preventing oxidation and has excellent disease resistance and growth promotion effects.

Means for Solving the Problems

[0008] The present invention relates to an 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 linear or branched hydrocarbon group containing 4 to 12 carbon atoms, which may contain one or more double bonds and / or OH groups. When containing a double bond, the position of the double bond is not limited. R 2 is a linear or branched hydrocarbon group containing 2 to 8 carbon atoms, which may contain one or more double bonds and / or OH groups. When containing a double bond, the position of the double bond is not limited.) a hydroxylated fatty acid or its derivative or its salt having the structural formula of, and at least one selected from phenolic antioxidants, ascorbic acid, and tocopherol. In particular, R 1 is preferably -(CH 2 ) n -(where n is an integer of 4 to 12).

[0009] A plant activator characterized in that the phenolic antioxidant is butylhydroxyanisole is preferred.

[0010] A plant activator in which at least one selected from the phenolic antioxidant, ascorbic acid, and tocopherol is added in a ratio of 1 / 2 to 5 times the weight based on the effective ingredient amount is preferable.

[0011] The above-mentioned hydroxylated fatty acid, the R of the above-mentioned hydroxylated fatty acid 1 has a hydrocarbon group having 6 to 8 carbon atoms, and R 2 is a hydroxylated fatty acid having a hydrocarbon group having 4 to 6 carbon atoms is preferable as a plant activator.

[0012] The above-mentioned hydroxylated fat, the R of the above-mentioned hydroxylated fatty acid 1 is, -(CH 2 ) n -(n is an integer from 4 to 12), and R 2 is, C n H 2n+1 -(n is an integer from 2 to 8) is a hydroxylated fatty acid having a structure is preferable as a plant activator.

[0013] The above-mentioned hydroxylated fatty acid, the R of the above-mentioned hydroxylated fatty acid 1 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 CH 2 CH 2 -) is a hydroxylated fatty acid having a structure is preferable as a plant activator.

[0014] A plant activator in which the hydroxylated fatty acid is hydroxyoctadecaenoic acid is preferable.

[0015] A plant activator in which the hydroxylated fatty acid is 9,10,13-trihydroxy-11-octadecaenoic acid is preferable.

[0016] A plant activator in which the hydroxylated fatty acid is 9,12,13-trihydroxy-10-octadecaenoic acid is preferable.

[0017] Note that "octadecadienoic acid" is a conventional notation (for example, see Japanese Patent Application Laid-Open No. 3-14539 etc.). The above-mentioned "9,10,13-trihydroxy-11-octadecadienoic acid" is also denoted as "9,10,13-trihydroxyoctadeca-11-enoic acid" or "9,10,13-trihydroxy-11-octadecenoic acid". Similarly, the above-mentioned "9,12,13-trihydroxy-10-octadecadienoic acid" is also denoted as "9,12,13-trihydroxyoctadeca-10-enoic acid" or "9,12,13-trihydroxy-10-octadecenoic acid". In the examples, the notation of the manufacturer is also shown in parentheses. Also, the above explanation applies to all "octadecadienoic acid" used in this specification, the claims, the drawings, and the abstract.

[0018] The structural formula of "9,10,13-trihydroxy-11-octadecadienoic acid" is represented by the following structural formula (1).

[0019]

Chemical formula

[0020] The structural formula of "9,12,13-trihydroxy-10-octadecadienoic acid" is represented by the following structural formula (2).

[0021]

Chemical formula

[0022] The plant activator in which the oxo fatty acid is keto octadecadienoic acid is preferable.

[0023] The plant activator in which the oxo fatty acid is 13-oxo-9,11-octadecadienoic acid is preferable.

[0024] Incidentally, as derivatives of the oxo fatty acid and the hydroxylated fatty acid, esters of the oxo fatty acid and the hydroxylated fatty acid are each desirable. Further, as salts of the oxo fatty acid and the hydroxylated fatty acid, sodium salts, potassium salts, ammonium salts, etc. can be used.

[0025] It is preferable that the plant activator is a plant activator used as a spraying agent or an immersion agent that comes into contact with the foliage or roots of plants, or an agent for soil perfusion.

[0026] It is preferable that the plant activator is a plant activator used for plants selected from the plants of the Brassicaceae family, Poaceae family, Fabaceae family, Solanaceae family, Rosaceae family, Amaranthaceae family, or Malvaceae family.

Effects of the Invention

[0027] The plant activator of the present invention is excellent in the stability of the active ingredient and has excellent disease resistance and growth promoting effects.

Modes for Carrying Out the Invention

[0028] Plant activator The plant activator of the present invention is an oxo fatty acid or a derivative or a salt thereof 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 linear or branched hydrocarbon group containing 4 to 12 carbon atoms, which may contain one or more double bonds and / or OH groups, and when containing a double bond, the position of the double bond is not limited, R 2is a linear or branched hydrocarbon group containing 2 to 8 carbon atoms, which may contain one or more double bonds and / or OH groups, and when containing a double bond, the position of the double bond is not limited) a hydroxylated fatty acid having the structural formula of or a derivative thereof or a salt thereof, and characterized by containing at least one selected from phenolic antioxidants, ascorbic acid and tocopherols. In particular, R 1 is preferably -(CH 2 ) n -(wherein n is an integer of 4 to 12). Note that the oxo fatty acids and the compounds having the structural formulas represented by the above formulas (I) and / or (II) include all geometric isomers and stereoisomers thereof.

[0029] "Plant activation" in the present invention means adjusting in some way to activate or maintain the growth activities of plants, and includes growth promotion (a concept including the expansion of stems and leaves, the promotion of the growth of tubers and roots, etc.), dormancy inhibition, induction and imparting of resistance to plant stress (such as diseases, etc.), and a concept including plant growth regulating effects such as anti-aging.

[0030] The plant activator of the present invention contains an oxo fatty acid or a derivative thereof or a salt thereof and a hydroxylated fatty acid or a derivative thereof or a salt thereof as active ingredients for activating plants. For example, examples of the oxo fatty acid include keto octadecadienoic acid. For example, specific examples of keto octadecadienoic acid include 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, 11-oxo-9,12-octadecadienoic acid, 12-oxo-9,13-octadecadienoic acid and 14-oxo-9,12-octadecadienoic acid and their isomers, etc.

[0031] By inoculating a plant body with a hydroxylated fatty acid, its derivative, or its salt having a structural formula as shown in the above formula (I) and / or (II), in the plant body, compared with untreated plants, significant increases in leaf length and number, which are plant growth indices, as well as leaf and plant weight, an increase in the number of stems per plant, and promotion of tuber or tuberous root growth have been confirmed, and it has been found that a hydroxylated fatty acid, its derivative, or its salt having a structural formula as described above has an excellent plant activation effect. For example, hydroxylated fatty acids include hydroxyoctadecadienoic acid and the like. For example, specific examples of hydroxyoctadecadienoic acid include 9,10,13-trihydroxy-11-octadecadienoic acid, 9,12,13-trihydroxy-10-octadecadienoic acid, and their isomers and the like.

[0032] As used herein, the "active ingredient" means such oxo fatty acids and hydroxylated fatty acids. Oxo fatty acids such as keto octadecadienoic acid and hydroxylated fatty acids such as hydroxyoctadecadienoic acid have excellent properties for activating plant growth. Therefore, by bringing the plant activator of the present invention containing an oxo fatty acid, its derivative, or its salt and a hydroxylated fatty acid, its derivative, or its salt into contact with the foliage or a part of the root of a plant, a very high plant growth promoting effect can be imparted to the plant.

[0033] In addition, as derivatives of the oxo fatty acid and the hydroxylated fatty acid, esters are desirable. As salts of the oxo fatty acid and the hydroxylated fatty acid, sodium salts, potassium salts, ammonium salts, etc. can be used.

[0034] However, hydroxylated fatty acids are oxidized in the atmosphere. In addition, oxo fatty acids react with oxygen and water in the atmosphere and change into hydroxylated fatty acids. Since the rate at which oxo fatty acids change into hydroxylated fatty acids is faster than the rate at which hydroxylated fatty acids are oxidized, as a result, when both coexist, over time, the amount of hydroxylated fatty acids increases.

[0035] At least one selected from phenolic antioxidants, ascorbic acid, and tocopherols contained in the plant activator of the present invention acts as an antioxidant that suppresses the decomposition of oxo fatty acids or their derivatives or their salts and hydroxy fatty acids or their derivatives or their salts, which are active ingredients in the plant activator. As a result, the plant activating material of the present invention is stabilized. That is, by containing such an antioxidant, a decrease in the activation effect and a decrease in storage stability are prevented during the processing, distribution, and storage of the plant activator during formulation, and the effectiveness of the plant activator as a plant activator during application is ensured. For example, preferred examples of antioxidants that contribute to the stabilization of the plant activator are phenolic antioxidants, ascorbic acid (vitamin C), and tocopherol (vitamin E). However, it is not limited to tocopherol, and other vitamin E, such as natural or synthetic vitamin E homologs, various derivatives and related compounds of vitamin E having antioxidant activity, can also be used. Further, the ascorbic acid (vitamin C) of the present invention includes oxidized forms and isomers of ascorbic acid. Further, an example of the phenolic antioxidant is butylhydroxyanisole. However, other phenolic antioxidant substances having antioxidant properties can also be used.

[0036] Also, due to the addition of the antioxidant of the present invention, the excellent growth promoting effect of the plant activator containing oxo fatty acids or their derivatives or their salts and hydroxy fatty acids or their derivatives or their salts will not be reduced or lost. Furthermore, the addition of the antioxidant does not have an adverse effect on the plant body to which it is applied. Therefore, by adding the antioxidant of the present invention, the excellent activation effect of the plant activator containing oxo fatty acids or their derivatives or their salts and hydroxy fatty acids or their derivatives or their salts remains as it is, and by suppressing the decomposition of the active ingredients in the plant activator, it is possible to achieve the maintenance of a stable activation effect over a long period in the plant activator.

[0037] In the present invention, the antioxidant can be added at a ratio of about 5 times or less by weight based on the amount of the active ingredient in the plant activator. The preferred 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 state, but if the ratio exceeds 5 times, there is a risk of phytotoxicity to the plant body to be applied. The lower limit of the concentration of the antioxidant is not particularly limited, but a ratio of about 1 / 2 times or more by weight based on the amount of the active ingredient is preferred. In a preferred embodiment of the present invention, the ratio of the antioxidant is 1 / 2 to 5 times by weight based on the amount of the active ingredient.

[0038] Here, the amount of the active ingredient in the present invention refers to the total amount of oxo fatty acids, hydroxylated fatty acids or their derivatives or their salts 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 0.2 to 2.0 g / L. The plant activator of the present invention contains an antioxidant at a ratio of 1 / 2 to 5 times by weight with respect to such an amount of the active ingredient. By adding an antioxidant of this degree, the decomposition of the active ingredient in the plant activator is significantly suppressed, and its activation effect can be maintained for a long period.

[0039] The plant activator of the present invention may contain, if necessary, a surfactant and / or a diluent or carrier having compatibility suitable for use as a plant activator. These additive components are not particularly limited as long as they are agriculturally acceptable agents. Further, components usually used in agricultural chemical formulations other than surfactants, diluents, and carriers may be further contained.

[0040] The plant activator of the present invention can be applied to plants by any method. For example, it can be used as a spray agent or an immersion agent that contacts the stems, leaves or roots of plants, or as a soil perfusion 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 used as a sustained-release agent. In the applied plant, the plant activator of the present invention imparts a plant growth promoting effect.

[0041] The plants to which the plant activator of the present invention can be applied are not particularly limited and can be generally used well for plants. For example, plants of the Poaceae, Fabaceae, Solanaceae, Rosaceae, Amaranthaceae, Malvaceae or Brassicaceae families can be mentioned. For example, as plants of the Poaceae family, for example, turfgrass, rice, wheat, corn, etc., as plants of the Fabaceae family, for example, soybean, broad bean, kidney bean, licorice, etc., as plants of the Solanaceae family, for example, tomato, eggplant, pepper, green pepper, potato, etc., as plants of the Rosaceae family, for example, strawberry, etc., as plants of the Amaranthaceae family, for example, spinach, etc., as plants of the Malvaceae family, for example, cotton, okra, etc., as plants of the Brassicaceae family, for example, Komatsuna, Mizuna, etc., the growth of these plants is effectively promoted. Further, the plants to be applied are not limited to wild-type plants, and may be, for example, mutants or transformants. Also, the varieties of each plant are not particularly limited.

[0042] In addition, the plant activator of the present invention has been found to be utilizable as a plant activator showing a strong resistance induction effect, and it has been found that it shows a growth promotion effect, a fruit yield increase effect, and a disease suppression effect on various plants. For example, specific examples effective for disease suppression include gray mold, vine cracking disease, vine blight, Phytophthora blight of the leaves of Cucurbitaceae such as cucumber, watermelon, melon, pumpkin, etc., bacterial wilt, wilt disease, half wilt disease, damping-off, brown root rot of Solanaceae such as tomato, eggplant, potato, powdery mildew, scab, gray mold, anthracnose of Rosaceae such as rose and strawberry, Phytophthora blight of Amaranthaceae such as spinach, black rot, soft rot, spot bacterial disease, Rhizoctonia disease of Brassicaceae such as Chinese cabbage, cabbage, Komatsuna, sclerotium blight of Apiaceae such as carrot, and rice blast of Poaceae plants.

Examples

[0043] The present invention will be described based on examples, but the present invention is not limited only to the examples.

[0044] Example 1 Preparation of plant activator As the hydroxylated fatty acid, 9,10,13-trihydroxy-11-octadecenoic acid (manufactured by Larodan Fine Chemicals, 9(S),10(S),13(S)-trihydroxy-11(E)-octadecenoic acid (in English notation: 9(S),10(S),13(S)-trihydroxy-11(E)-octadecenoic acid), 200 mg / L ethanol solution)), and a mixture of 9,12,13-trihydroxy-10-octadecenoic acid (manufactured by Larodan Fine Chemicals, 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid (in English notation: 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid), 200 mg / L ethanol solution)) mixed at a ratio of 2:1 were used to prepare an aqueous solution containing hydroxylated octadecenoic acid. That is, 9(S),10(S),13(S)-trihydroxy-11(E)-octadecenoic acid was dissolved in 1 L of water with 75 mL of the ethanol solution to a concentration of 15 mg / L, and then 35 mL of the ethanol solution of 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acid was dissolved in this aqueous solution to adjust the concentration to 7 mg / L. To 778 mL of this aqueous solution, 222 mL of 13-oxo-9,11-octadecadienoic acid (13-oxoODA) ((9Z,11E)-13-oxo-9,11-octadecadienoic acid, manufactured by Cayman Chemical, 100 μg / 100 μL ethanol solution) was added, and the resulting solution was used as a plant activator for testing.

[0045] Addition of Vitamin C and Vitamin E and Accelerated Test To 1 L of the test plant activator obtained above (active ingredient content: 239 mg), 680 mg of vitamin C (manufactured by Kanto Chemical Co., Inc.) and 480 mg of vitamin E (manufactured by Nacalai Tesque, Inc.) were added. The resulting solution was subjected to an accelerated test at 54°C using a Bioshaker (registered trademark) (BR-23UM manufactured by Taitec Co., Ltd.) and left standing for 5 weeks (equivalent to about 2 years at 25°C; refer to "Stability of Pharmaceuticals" by Sumie Yoshioka). The active ingredient concentration was measured by UV before and after the accelerated test, and the ratio of the active ingredient concentration after the accelerated test to the active ingredient concentration before the accelerated test (active ingredient concentration change %) was calculated from the area ratio of the UV before and after the accelerated test.

[0046] Example 2 To 1 L of the test plant activator obtained above (active ingredient content: 239 mg), 480 mg of butylhydroxyanisole, a phenolic antioxidant (manufactured by Kishida Chemical Co., Ltd.), was added to obtain the plant activator of Example 1. The resulting 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 standing for 5 weeks (equivalent to about 2 years at 25°C; refer to "Stability of Pharmaceuticals" by Sumie Yoshioka). The active ingredient concentration was measured by UV before and after the accelerated test, and the ratio of the active ingredient concentration after the accelerated test to the active ingredient concentration before the accelerated test (active ingredient concentration change %) was calculated from the area ratio of the UV before and after the accelerated test.

[0047] Example 3 To 1 L of the test plant activator obtained above (active ingredient content: 239 mg), 1110 mg of vitamin C was added. The resulting solution was subjected to an accelerated test at 54°C using a Bioshaker (registered trademark) (BR-23UM manufactured by Taitec Co., Ltd.) and left standing for 5 weeks (equivalent to about 2 years at 25°C; refer to "Stability of Pharmaceuticals" by Sumie Yoshioka). The active ingredient concentration was measured by UV before and after the accelerated test, and the ratio of the active ingredient concentration after the accelerated test to the active ingredient concentration before the accelerated test (active ingredient concentration change %) was calculated from the area ratio of the UV before and after the accelerated test.

[0048] Example 4 120 mg of vitamin E was added to 1 L of the test plant activator obtained above (active ingredient content: 239 mg). The resulting 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 approximately 2 years at 25°C; refer to "Stability of Pharmaceuticals" written by Yoshioka Sumie). The active ingredient concentration was measured by UV before and after the accelerated test, and the ratio of the active ingredient concentration after the accelerated test to the active ingredient concentration before the accelerated test (active ingredient concentration change %) was calculated from the area ratio of the UV before and after the accelerated test.

[0049] Comparative Example 1 1 L of the test plant activator obtained above (active ingredient content: 239 mg) 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 approximately 2 years at 25°C; refer to "Stability of Pharmaceuticals" written by Yoshioka Sumie). The active ingredient concentration was measured by UV before and after the accelerated test, and the ratio of the active ingredient concentration after the accelerated test to the active ingredient concentration before the accelerated test (active ingredient concentration change %) was calculated from the area ratio of the UV before and after the accelerated test.

[0050] The results of the active ingredient concentration change % obtained in Examples 1 to 4 and Comparative Example 1 are shown in Table 1 below.

[0051] [Table 1]

[0052] As shown in Table 1, in Comparative Example 1 where no antioxidant was added, the concentration of oxo fatty acids in the plant activator significantly decreased after 5 weeks of the accelerated test, indicating that the oxo fatty acids were almost decomposed after the accelerated test. Accordingly, the concentration of hydroxylated fatty acids increased by about 2 times after the accelerated test compared to before the accelerated test, indicating that the oxo fatty acids 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 shows 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 slight 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. From this result, it can be seen that the plant activator containing the antioxidant of the present invention exhibits an excellent effect on the stabilization of oxo fatty acids and hydroxylated fatty acids, which are active ingredients for activating plants.

[0053] 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 exhibits a remarkable effect on the stabilization of the active ingredient.

Claims

1. Ketooctadecadienoic acid or a salt thereof, The following formula (I) and / or (II) P.S. 1 )-CH(OH)-CH(OH)-CH=CH-CH(OH)-R 2 (I) P.S. 1 )-CH(OH)-CH=CH-CH(OH)-CH(OH)-R 2 (II) (In the formula, R 1 is an alkylene group having 7 carbon atoms (-(CH 2 ) 7 -), R 2 is an alkyl group having 5 carbon atoms (CH 3 CH 2 CH 2 CH 2 CH 2 --) or a salt thereof, A plant activator comprising at least one member selected from the group consisting of a phenolic antioxidant, ascorbic acid and tocopherol.

2. 2. The plant activator according to claim 1, wherein the phenolic antioxidant is butylhydroxyanisole.

3. 2. The plant activator according to claim 1, wherein the ketooctadecadienoic acid is 13-oxo-9,11-octadecadienoic acid.

4. 4. The plant activator according to claim 1, which is used as a spray or immersion agent to be brought into contact with the stems, leaves or roots of a plant, or as a soil drench agent.

5. The plant activator according to any one of claims 1 to 4, which is used for a plant selected from the Brassicaceae, Poaceae, Leguminosae, Solanaceae, Rosaceae, Amaranthaceae, and Malvaceae families.

Images