JP2012219052A - Method for reducing abiotic stress in plant - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method for reducing abiotic stress in plants.SOLUTION: The method for reducing abiotic stress in plants comprises treating a plant that has been or is to be exposed to abiotic stress with at least one compound selected from the group composed of compounds represented by formula (1) [wherein, Rdenotes 1-6C alkyl which may be substituted with halogen; Rdenotes 1-6C alkyl which may be substituted with halogen, 3-6C alkoxyalkyl which may be substituted with halogen, 3-6C alkenyl which may be substituted with halogen or 3-6C alkynyl which may be substituted with halogen; Rdenotes halogen or 1-6C alkyl which may be substituted with halogen; Rdenotes hydrogen, halogen, cyano or 1-6C alkyl which may be substituted with a halogen atom; Rdenotes hydrogen, halogen, cyano, 1-6C alkyl which may be substituted with halogen, 1-6C alkoxy which may be substituted with halogen, 1-6C alkylthio which may be substituted with halogen, 1-6C alkylsulfinyl which may be substituted with halogen or the like; and Rdenotes halogen or 1-6C alkyl which may be substituted with halogen].

Description

  The present invention relates to a method for reducing the effects of abiotic stress.

  When a plant encounters an abiotic stress environment, various physiological disorders may appear due to a gradual or rapid decline in cell physiology. Some chemical substances are known to have an effect of reducing the influence of abiotic stress by adjusting the physiological state of plants (see, for example, Non-Patent Document 1 and Non-Patent Document 2). . However, in reality, the effect is not enough.

"Amelioration of chilling injuries in cucumber seedlings by abscisic acid" Arnon Rikin and Amos E. Richmond, (1976) Physiologia Plantarum 38: pp. 95-97 "Chilling injury in Cotton (Gossypium hisutum L.): Light requirement for the reduction of injury and for the protective effect of abscisic acid" Arnon Rikin, Carlos Gitler and Dan Atsman (1981) Plant and Cell Physiology Volume 22, Issue 3 pp. 453-460

  An object of this invention is to provide the method etc. which reduce the abiotic stress of a plant.

  As a result of intensive studies, the present inventor has found that plants treated with a specific compound have an effect of mitigating the influence when exposed to abiotic stress, and have reached the present invention.

〔式中、Ｒ¹はハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基を表し、Ｒ²はハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基、ハロゲン原子で置換されていてもよいＣ３−Ｃ６アルコキシアルキル基、ハロゲン原子で置換されていてもよいＣ３−Ｃ６アルケニル基、またはハロゲン原子で置換されていてもよいＣ３−Ｃ６アルキニル基を表し、Ｒ³はハロゲン原子、またはハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基を表し、Ｒ⁴は水素原子、ハロゲン原子、シアノ基、またはハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基を表し、Ｒ⁵は水素原子、ハロゲン原子、シアノ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基、ハロゲン原子で置換されていてもよいＣ１−Ｃ６アルコキシ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキルチオ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキルスルフィニル基、またはハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキルスルホニル基を表し、Ｒ⁶はハロゲン原子、またはハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基を表す。〕
［２］
式（１）

で示される化合物が、下記化合物群Ａから選ばれる化合物である前項［１］記載の方法。
＜化合物群Ａ＞
（１）式（１）におけるＲ¹がエチル基、Ｒ²がメチル基、Ｒ³がブロモ基、Ｒ⁴がブロモ基、Ｒ^５がブロモ基、Ｒ^６がクロロ基である化合物
（２）式（１）におけるＲ¹がメチル基、Ｒ²がメチル基、Ｒ³がメチル基、Ｒ⁴がシアノ基、Ｒ^５がブロモ基、Ｒ^６がクロロ基である化合物
［３］
処理が、散布処理、土壌灌注処理、種子処理又は水耕処理である前項［１］又は［２］記載の方法。
［４］
処理が種子処理であって、種子処理における化合物の処理濃度が種子１００キログラムあたり５グラム以上５００グラム以下である前項［１］〜［３］記載の方法。
［５］
処理が種子処理であって、種子処理における化合物の処理濃度が種子１００キログラムあたり２５０グラム以上５００グラム以下である前項［１］〜［３］記載の方法。
［６］
植物がイネ、トウモロコシ又はコムギである前項［１］〜［５］記載の方法。
［７］
植物が遺伝子組換え植物である前項［１］〜［６］記載の方法。
［８］
非生物的ストレスが低温ストレスである前項［１］〜［７］記載の方法。
［９］
非生物的ストレスが乾燥ストレスである前項［１］〜［７］記載の方法。
［１０］
植物の非生物的ストレスによる影響の軽減が、以下の（１）〜（１４）に記載の少なくとも１つの植物表現型の変化により示されることを特徴とする前項［１］〜［９］記載の方法。
＜植物表現型＞
（１）発芽率
（２）苗立ち率
（３）葉の枯死率
（４）草丈
（５）植物重量
（６）葉面積
（７）葉色
（８）種子・果実の数又は重量
（９）収穫物の品質
（１０）着花率・着果率・結実率・種子充填率
（１１）クロロフィル蛍光収率
（１２）水分含量
（１３）葉面温度
（１４）蒸散能
［１１］
植物の非生物的ストレスによる影響を軽減するための、式（１）で示される化合物からなる群から選ばれる少なくとも一の化合物の使用。
式（１）

〔式中、Ｒ¹はハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基を表し、Ｒ²はハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基、ハロゲン原子で置換されていてもよいＣ３−Ｃ６アルコキシアルキル基、ハロゲン原子で置換されていてもよいＣ３−Ｃ６アルケニル基、またはハロゲン原子で置換されていてもよいＣ３−Ｃ６アルキニル基を表し、Ｒ³はハロゲン原子、またはハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基を表し、Ｒ⁴は水素原子、ハロゲン原子、シアノ基、またはハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基を表し、Ｒ⁵は水素原子、ハロゲン原子、シアノ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基、ハロゲン原子で置換されていてもよいＣ１−Ｃ６アルコキシ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキルチオ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキルスルフィニル基、またはハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキルスルホニル基を表し、Ｒ⁶はハロゲン原子、またはハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基を表す。〕
［１２］
植物の非生物的ストレスによる影響の軽減が、以下の（１）〜（１４）に記載の少なくとも１つの植物表現型の変化により示されることを特徴とする前項［１１］記載の使用。
＜植物表現型＞
（１）発芽率
（２）苗立ち率
（３）葉の枯死率
（４）草丈
（５）植物重量
（６）葉面積
（７）葉色
（８）種子・果実の数又は重量
（９）収穫物の品質
（１０）着花率・着果率・結実率・種子充填率
（１１）クロロフィル蛍光収率
（１２）水分含量
（１３）葉面温度
（１４）蒸散能 That is, the present invention has the following configuration.
[1] A method for reducing the effects of abiotic stress on a plant,
A method of treating a plant exposed to or likely to be exposed to abiotic stress with at least one compound selected from the group consisting of compounds represented by the following formula (1).
Formula (1)

[Wherein, R ¹ represents a C1-C6 alkyl group which may be substituted with a halogen atom, and R ² may be a C1-C6 alkyl group which may be substituted with a halogen atom, or may be substituted with a halogen atom. A C3-C6 alkoxyalkyl group, a C3-C6 alkenyl group which may be substituted with a halogen atom, or a C3-C6 alkynyl group which may be substituted with a halogen atom, and R ³ is a halogen atom or a halogen atom Represents a C1-C6 alkyl group that may be substituted with, R ⁴ represents a hydrogen atom, a halogen atom, a cyano group, or a C1-C6 alkyl group that may be substituted with a halogen atom, and R ⁵ represents a hydrogen atom. , A halogen atom, a cyano group, a C1-C6 alkyl group optionally substituted with a halogen atom, a C1-C6 atom optionally substituted with a halogen atom Lucoxy group, C1-C6 alkylthio group optionally substituted with a halogen atom, C1-C6 alkylsulfinyl group optionally substituted with a halogen atom, or C1-C6 alkylsulfonyl group optionally substituted with a halogen atom R ⁶ represents a halogen atom or a C1-C6 alkyl group which may be substituted with a halogen atom. ]
[2]
Formula (1)

The method of the preceding item [1], wherein the compound represented by is a compound selected from the following compound group A.
<Compound group A>
(1) Compound (2) in which R ¹ in formula (1) is an ethyl group, R ² is a methyl group, R ³ is a bromo group, R ⁴ is a bromo group, R ⁵ is a bromo group, and R ⁶ is a chloro group Compound [3] wherein R ¹ in (1) is a methyl group, R ² is a methyl group, R ³ is a methyl group, R ⁴ is a cyano group, R ⁵ is a bromo group, and R ⁶ is a chloro group [3]
The method according to [1] or [2] above, wherein the treatment is spraying treatment, soil irrigation treatment, seed treatment or hydroponic treatment.
[4]
The method according to any one of [1] to [3] above, wherein the treatment is a seed treatment, and the treatment concentration of the compound in the seed treatment is 5 g or more and 500 g or less per 100 kg of seed.
[5]
The method according to any one of [1] to [3] above, wherein the treatment is a seed treatment, and the treatment concentration of the compound in the seed treatment is 250 g or more and 500 g or less per 100 kg of seed.
[6]
The method according to [1] to [5] above, wherein the plant is rice, corn or wheat.
[7]
The method according to [1] to [6] above, wherein the plant is a genetically modified plant.
[8]
The method according to [1] to [7] above, wherein the abiotic stress is low temperature stress.
[9]
The method according to [1] to [7] above, wherein the abiotic stress is drought stress.
[10]
(1) to [9], wherein the reduction of the effect of abiotic stress on the plant is indicated by a change in at least one plant phenotype described in (1) to (14) below: Method.
<Plant phenotype>
(1) Germination rate (2) Seedling establishment rate (3) Leaf death rate (4) Plant height (5) Plant weight (6) Leaf area (7) Leaf color (8) Number or weight of seeds and fruits (9) Harvest Product quality (10) Flowering rate, fruiting rate, fruiting rate, seed filling rate (11) Chlorophyll fluorescence yield (12) Water content (13) Leaf surface temperature (14) Transpiration capacity [11]
Use of at least one compound selected from the group consisting of compounds represented by formula (1) for reducing the effects of abiotic stress on plants.
Formula (1)

[Wherein, R ¹ represents a C1-C6 alkyl group which may be substituted with a halogen atom, and R ² may be a C1-C6 alkyl group which may be substituted with a halogen atom, or may be substituted with a halogen atom. A C3-C6 alkoxyalkyl group, a C3-C6 alkenyl group which may be substituted with a halogen atom, or a C3-C6 alkynyl group which may be substituted with a halogen atom, and R ³ is a halogen atom or a halogen atom Represents a C1-C6 alkyl group that may be substituted with, R ⁴ represents a hydrogen atom, a halogen atom, a cyano group, or a C1-C6 alkyl group that may be substituted with a halogen atom, and R ⁵ represents a hydrogen atom. , A halogen atom, a cyano group, a C1-C6 alkyl group optionally substituted with a halogen atom, a C1-C6 atom optionally substituted with a halogen atom Lucoxy group, C1-C6 alkylthio group optionally substituted with a halogen atom, C1-C6 alkylsulfinyl group optionally substituted with a halogen atom, or C1-C6 alkylsulfonyl group optionally substituted with a halogen atom R ⁶ represents a halogen atom or a C1-C6 alkyl group which may be substituted with a halogen atom. ]
[12]
The use according to [11] above, wherein the reduction of the effects of abiotic stress on the plant is indicated by changes in at least one plant phenotype described in (1) to (14) below.
<Plant phenotype>
(1) Germination rate (2) Seedling establishment rate (3) Leaf death rate (4) Plant height (5) Plant weight (6) Leaf area (7) Leaf color (8) Number or weight of seeds and fruits (9) Harvest Product quality (10) Flowering rate, fruiting rate, fruiting rate, seed filling rate (11) Chlorophyll fluorescence yield (12) Water content (13) Leaf surface temperature (14) Transpiration

  By using the method of the present invention, the influence of abiotic stress can be reduced.

  In the present invention, “abiotic stress” refers to stress such as temperature stress that is high-temperature stress or low-temperature stress, salt stress, drought stress, or moisture stress that is excessive moisture stress. When a plant is exposed to abiotic stress, the physiological function of the cell decreases, the physiological state of the plant deteriorates, and growth is inhibited. High temperature stress refers to stress that is experienced when exposed to a temperature that is higher than the optimum growth temperature or germination temperature of the plant. Specifically, the average cultivation temperature in the environment where the plant is cultivated is 25 ° C. or more, which is more severe. May be 30 ° C or higher, more strictly 35 ° C or higher. Low temperature stress refers to stress that is experienced when exposed to a temperature lower than the optimal growth temperature or germination temperature of the plant. Specifically, the average cultivation temperature in the environment where the plant is cultivated is 15 ° C. or less, more severely. May be 10 ° C. or less, and more strictly 5 ° C. or less. In addition, drought stress refers to the stress experienced when exposed to a water environment where the water content in the soil decreases due to a decrease in rainfall and irrigation, water absorption is inhibited and plant growth is inhibited, Specifically, the value may vary depending on the type of soil, but the moisture content of the soil where the plant is cultivated is 15% by weight or less, more strictly 10% by weight or less, and more strictly 7.5% by weight or less. Or a condition where the pF value of the soil where the plant is grown is 2.3 or more, strictly 2.7 or more, and more strictly 3.0 or more. Overhumidity stress refers to the stress experienced when exposed to a water environment where the water content in the soil becomes excessive and the growth of the plant is inhibited.Specifically, the value may vary depending on the type of soil. However, the soil moisture content in which plants are cultivated is 30% by weight or more, strictly 40% by weight or more, more strictly 50% by weight or more, or the pF value of soil in which plants are cultivated is 1.7. In the following, the conditions are strictly 1.0 or less, and more strictly 0.3 or less. The pF value of soil should be measured in accordance with the principle described in “PF value measurement method” on pages 61 to 62 of “Soil / Plant Nutrition / Environment Encyclopedia” (Taiyosha, 1994, Matsuzaka et al.). Can do. In addition, salt stress is an environment where growth is inhibited as a result of osmotic pressure rising due to accumulation of salts in the soil where the plant is cultivated or in the hydroponic solution and inhibiting water absorption by the plant. Specifically, the osmotic potential due to the salt in the soil or hydroponics is 0.2 Mpa (2,400 ppm at NaCl concentration) or more, strictly 0.25 MPa or more, and more strictly 0. The condition is 30 MPa. The osmotic pressure in the soil can be determined based on the following Raoul formula by diluting the soil with water and analyzing the salt concentration of the supernatant.

Raoul's formula: π (atm) = cRT
R = 0.082 (L · atm / mol · K)
T = absolute temperature (K)
c = ion molar concentration (mol / L)
1 atm = 0.1 MPa

The effects of plant abiotic stress are grasped by comparing plants not exposed to abiotic stress with exposed plants in the following changes in plant phenotype. That is, the plant phenotype serves as an indicator of plant abiotic stress.
<Plant phenotype>
(1) Germination rate (2) Seedling establishment rate (3) Number of healthy leaves (or rate)
(4) Plant height (5) Plant weight (6) Leaf area (7) Leaf color (8) Number or weight of seeds and fruits (9) Quality of harvest (10) Flowering rate, fruiting rate, fruiting rate, Seed filling rate (11) Chlorophyll fluorescence yield (12) Water content (13) Leaf temperature (14) Transpiration

The index can be measured as follows.
(1) Germination rate Plant seeds are sown and germinated on soil, filter paper, agar medium, sand, etc., and the ratio of the germination number to the number of seeds is investigated.
(2) Seedling establishment rate Plant seeds are sown on soil, filter paper, agar medium, sand, etc., and cultivated for a certain period of time. Investigate the percentage of seedlings that survived after temperature stress during all or part of the cultivation.
(3) Number of healthy leaves (or rate)
Count the number of healthy leaves for each plant and investigate the total number of healthy leaves. Alternatively, the ratio of the number of healthy leaves to the number of all leaves of the plant is investigated.
(4) Plant height For each plant, measure the length from the root of the stem on the ground part to the branch at the tip.
(5) Plant weight The above-ground part of each plant is cut out and measured to determine the fresh weight of the plant, or the dried sample is dried and then the weight is measured to determine the dry plant weight.
(6) Leaf area A plant is photographed with a digital camera, and the area of the green portion of the photograph is quantified with image analysis software such as Win ROOF (manufactured by Mitani Corporation) to determine the leaf area of the plant.
(7) The leaf color is obtained by sampling the leaves of the leaf color plant and measuring the amount of chlorophyll using a chlorophyll meter (for example, SPAD-502, manufactured by Konica Minolta). Also, the area of the green part of the plant is obtained by photographing the plant with a digital camera and extracting and quantifying the area of the green part of the photograph with image analysis software such as Win ROOF (manufactured by Mitani Corporation). .
(8) Number or weight of seeds or fruits After the plants are cultivated until the seeds or fruits bear fruit or ripen, the number of fruits per plant is measured or the total fruit weight per plant is measured. In addition, after cultivating until the seed ripens, the yield components such as the number of ears, ripening rate, and 1000 grain weight are investigated.
(9) Quality of harvested crops After planting until the seeds or fruits have matured, measure the sugar content of the ripe fruit using, for example, a saccharimeter, or measure the content of proteins and lipids by component analysis To assess the quality of the harvest.
(10) Flowering rate, fruiting rate, fruiting rate, seed filling rate After cultivating until the plant has reached fruiting, count the number of flowers and the number of fruiting, and the fruiting rate% (number of fruiting / number of flowers x 100 ) After seed ripening, the number of seeds and the number of seed fillings are counted, and the seeding rate (number of seeding / number of flowers × 100) and seed filling rate% (number of seed filling / number of seeds × 100) are obtained.
(11) Chlorophyll fluorescence yield Using a pulse-modulated chlorophyll fluorescence measuring device (eg, IMAGING-PAM, manufactured by WALZ), the chlorophyll fluorescence yield is determined by measuring the chlorophyll fluorescence value (Fv / Fm) of the plant. .
(12) Moisture content In each growth stage of the plant, according to the method described in the above (5) Plant weight, the plant fresh weight and the plant dry weight were obtained, and the value obtained by subtracting the plant dry weight from the plant fresh weight was Calculated as the water content of Moreover, the moisture content of a plant is measured nondestructively by irradiating near infrared light and measuring the absorption amount (transmission amount) of this specific wavelength. The water content is measured using a scanner riser (for example, manufactured by Remnac Corp.).
(13) Leaf surface temperature At each growth stage of the plant, the leaf surface temperature is monitored using thermography (for example, scanner riser, manufactured by Remnac Corp.).
(14) Transpiration ability At each growth stage of the plant, transpiration of water from the leaf surface is measured using a porometer (for example, AP4, manufactured by Delta T).

  In the present specification, abiotic stress can be quantified by “stress intensity” represented by the following equation.

    “Strength of stress” = 100 × “any one plant phenotype in a plant not exposed to abiotic stress” / “any one plant phenotype in a plant exposed to abiotic stress”

  The method of the present invention is exposed to or exposed to abiotic stress whose “stress intensity” represented by the above formula is 105 to 200, preferably 110 to 180, more preferably 120 to 160. Applies to any plant.

When a plant is exposed to abiotic stress, an effect is observed on at least one of the phenotypes. That is,
(1) Decrease in germination rate (2) Decrease in seedling establishment rate (3) Decrease in the number of healthy leaves (or rate) (4) Decrease in plant height (5) Decrease in plant weight (6) Decrease in increase in leaf area (7) Leaf color Fading (8) Decrease in number or weight of seeds or fruits (9) Deterioration of harvest quality (10) Decrease in flowering rate, fruiting rate, fruiting rate, seed filling rate (11) Decrease in chlorophyll fluorescence yield (12) Decrease in water content (13) Increase in leaf surface temperature (14) Decrease in transpiration ability, etc. is observed, and the magnitude of abiotic stress in plants can be measured using this as an index.

The present invention provides a method for reducing the above-mentioned effects of abiotic stress on a plant that has been or will be exposed to abiotic stress by treating the compound of formula (1) with the plant. is there. The effect of reducing the influence of abiotic stress is obtained by comparing the indicator after the plant is exposed to abiotic stress between the plant treated with the compound represented by formula (1) and the non-treated plant. Can be evaluated.
When the present compound is treated into a plant in the method of the present invention, the whole plant or a part thereof (stems, buds, flowers, fruits, ears, seeds, bulbs, tubers, roots, etc.) may be used. Various stages of plant growth (before sowing, at sowing, before and after sowing, germination period such as before and after emergence, seedling transplanting, seedling transplanting, cutting or cutting seedling, long-term vegetative growth such as after planting, before flowering, During flowering, after flowering, it may be a reproductive growth period such as just before heading or heading time, before harvesting, before planning maturation, or harvesting time such as fruit coloring start time). Here, the bulb means a bulb, a bulb, a rhizome, a tuberous root, and a root support body. The seedlings include cuttings, seed pods and the like.

  The growth stages in which the target plant in the present invention can be exposed to abiotic stress include all stages including germination, seedling, nutritional long-term, reproductive long-term, and harvest.

〔式中、Ｒ¹はハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基を表し、Ｒ²はハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基、ハロゲン原子で置換されていてもよいＣ３−Ｃ６アルコキシアルキル基、ハロゲン原子で置換されていてもよいＣ３−Ｃ６アルケニル基、またはハロゲン原子で置換されていてもよいＣ３−Ｃ６アルキニル基を表し、Ｒ³はハロゲン原子、またはハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基を表し、Ｒ⁴は水素原子、ハロゲン原子、シアノ基、またはハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基を表し、Ｒ⁵は水素原子、ハロゲン原子、シアノ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基、ハロゲン原子で置換されていてもよいＣ１−Ｃ６アルコキシ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキルチオ基、ハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキルスルフィニル基、またはハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキルスルホニル基を表し、Ｒ⁶はハロゲン原子、またはハロゲン原子で置換されていてもよいＣ１−Ｃ６アルキル基を表す。〕
で示される化合物からなる群から選ばれる少なくとも一の化合物である。（以下、「本化合物」と記す場合がある。） The compound according to the present invention has the following formula (1)
Formula (1)

[Wherein, R ¹ represents a C1-C6 alkyl group which may be substituted with a halogen atom, and R ² may be a C1-C6 alkyl group which may be substituted with a halogen atom, or may be substituted with a halogen atom. A C3-C6 alkoxyalkyl group, a C3-C6 alkenyl group which may be substituted with a halogen atom, or a C3-C6 alkynyl group which may be substituted with a halogen atom, and R ³ is a halogen atom or a halogen atom Represents a C1-C6 alkyl group that may be substituted with, R ⁴ represents a hydrogen atom, a halogen atom, a cyano group, or a C1-C6 alkyl group that may be substituted with a halogen atom, and R ⁵ represents a hydrogen atom. , A halogen atom, a cyano group, a C1-C6 alkyl group optionally substituted with a halogen atom, a C1-C6 atom optionally substituted with a halogen atom Lucoxy group, C1-C6 alkylthio group optionally substituted with a halogen atom, C1-C6 alkylsulfinyl group optionally substituted with a halogen atom, or C1-C6 alkylsulfonyl group optionally substituted with a halogen atom R ⁶ represents a halogen atom or a C1-C6 alkyl group which may be substituted with a halogen atom. ]
And at least one compound selected from the group consisting of compounds represented by: (Hereafter, it may be described as “the present compound”.)

Next, the compound represented by the formula (1) according to the present invention will be described.
As each group shown by R < ¹ > -R < ⁶ > in Formula (1), the following group is mentioned.

  As a halogen atom, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned, for example.

  Examples of the C1-C6 alkyl group optionally substituted with a halogen atom include a methyl group, a trifluoromethyl group, a trichloromethyl group, a chloromethyl group, a dichloromethyl group, a fluoromethyl group, a difluoromethyl group, an ethyl group, Pentafluoroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, propyl group, isopropyl group, heptafluoroisopropyl group, butyl group, isobutyl group, sec-butyl group, tert- A butyl group, a pentyl group, a hexyl group, etc. are mentioned.

  Examples of the C3-C6 alkoxyalkyl group optionally substituted with a halogen atom include a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-isopropyloxyethyl group, and the like.

  Examples of the C3-C6 alkenyl group which may be substituted with a halogen atom include 2-propenyl group, 3-chloro-2-propenyl group, 2-chloro-2-propenyl group, and 3,3-dichloro-2- A propenyl group, 2-butenyl group, 3-butenyl group, 2-methyl-2-propenyl group, 3-methyl-2-butenyl group, 2-pentenyl group, 2-hexenyl group and the like can be mentioned.

  Examples of the C3-C6 alkynyl group optionally substituted with a halogen atom include 2-propynyl group, 3-chloro-2-propynyl group, 3-bromo-2-propynyl group, 2-butynyl group, and 3-butynyl. Groups and the like.

  Examples of the C1-C6 alkoxy group optionally substituted with a halogen atom include a methoxy group, an ethoxy group, a 2,2,2-trifluoroethoxy group, a propoxy group, an isopropyloxy group, a butoxy group, an isobutyloxy group, Examples thereof include a sec-butoxy group and a tert-butoxy group.

  Examples of the C1-C6 alkylthio group optionally substituted with a halogen atom include a methylthio group, a trifluoromethylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, a sec-butylthio group, and a tert. -A butylthio group, a pentylthio group, a hexylthio group, etc. are mentioned.

  Examples of the C1-C6 alkylsulfinyl group optionally substituted with a halogen atom include a methylsulfinyl group, a trifluoromethylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, an isobutylsulfinyl group, A sec-butylsulfinyl group, a tert-butylsulfinyl group, a pentylsulfinyl group, a hexylsulfinyl group and the like can be mentioned.

  Examples of the C1-C6 alkylsulfonyl group optionally substituted with a halogen atom include a methylsulfonyl group, a trifluoromethylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, an isobutylsulfonyl group, Examples include sec-butylsulfonyl group, tert-butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group and the like.

  As an aspect of this compound, the following compounds are mentioned, for example.

In the formula (1), R ¹ is a methyl group, an ethyl group or an isopropyl group, R ² is a methyl group or an ethyl group, R ³ is a halogen atom or a methyl group, and R ⁴ is a halogen atom or a cyano group. Wherein R ⁵ is a halogen atom or a trifluoromethyl group, and R ⁶ is a halogen atom.

In the formula (1), R ¹ is a methyl group, R ² is a methyl group, R ³ is a chlorine atom, a bromine atom or a methyl group, R ⁴ is a chlorine atom, a bromine atom or a cyano group, A compound in which R ⁵ is a chlorine atom, a bromine atom or a trifluoromethyl group, and R ⁶ is a chlorine atom.

In the formula (1), R ¹ is an ethyl group, R ² is a methyl group, R ³ is a chlorine atom, a bromine atom or a methyl group, R ⁴ is a chlorine atom, a bromine atom or a cyano group, A compound in which R ⁵ is a chlorine atom, a bromine atom or a trifluoromethyl group, and R ⁶ is a chlorine atom.

Specific examples of the compound include compounds 1 to 26 in which R ^{1 to} R ⁶ in the formula (1) are groups shown in [Table 1].

In addition, when the compound has at least one acidic group, the compound may be a salt with a base. For example, these salts are the following:
Metal salts such as alkali metal salts, alkaline earth metal salts (for example, sodium, potassium, or magnesium salts); salts with ammonia; morpholine, piperidine, pyrrolidine, mono-lower alkylamine, di-lower alkylamine, tri -Salts with organic amines such as lower alkyl amines, mono-hydroxy lower alkyl amines, di-hydroxy lower alkyl amines, tri-hydroxy lower alkyl amines.
This compound may have stereoisomers such as optical isomers based on asymmetric carbon atoms, and isomers such as tautomers. In the present invention, any isomer may be used alone or in any form. It can be used in an isomer ratio.

  This compound is a compound described in JP2007-182422A. These compounds can be produced, for example, by the method described in International Publication Pamphlet No. 2008/12893.

  When used in the method of the present invention, the present compound can be used alone, but can be formulated and used with various inactive ingredients as described later.

  Examples of solid carriers used in formulation include kaolin clay, attapulgite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob flour, walnut shell powder, etc. Natural organic materials, synthetic organic materials such as urea, salts such as calcium carbonate and ammonium sulfate, fine powders or granular materials made of synthetic inorganic materials such as synthetic hydrous hydrated silicon, etc., and examples of liquid carriers include xylene, alkylbenzene, methyl Aromatic hydrocarbons such as naphthalene, alcohols such as 2-propanol, ethylene glycol, propylene glycol and ethylene glycol monoethyl ether, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, petroleum fats Group hydrocarbons, Ester include dimethyl sulfoxide, acetonitrile and water.

  Examples of the surfactant include anions such as alkyl sulfate ester salts, alkyl aryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphates, lignin sulfonates, naphthalene sulfonate formaldehyde polycondensates and the like. Nonionic surfactants such as surfactants, polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters, and cationic surfactants such as alkyltrimethylammonium salts.

  Examples of other adjuvants for preparation include water-soluble polymers such as polyvinyl alcohol and polyvinylpyrrolidone, gum arabic, alginic acid and salts thereof, polysaccharides such as CMC (carboxymethylcellulose) and xanthan gum, inorganic substances such as aluminum magnesium silicate and alumina sol. , Preservatives, colorants, and stabilizers such as PAP (isopropyl acid phosphate) and BHT.

The method of the present invention is usually carried out by treating an effective amount of the present compound on a plant or its growing place. Plants to be treated include foliage, buds, flowers, fruits, ears, seeds, bulbs, tubers, roots, seedlings, and the like. Here, the bulb means a bulb, a bulb, a rhizome, a tuberous root, and a root support body. Moreover, as a seedling, in this specification, a cutting, a seed pod, etc. shall be included. Examples of the place where the plant grows include soil before planting or after planting.
In the case of treating a plant or plant growth place, the compound is treated once or a plurality of times on the target plant.

  Specific examples of the treatment method in the present invention include, for example, treatment of plant foliage, flower vases or ears such as foliage spraying, treatment of plant cultivation areas such as soil treatment, seed disinfection, seed soaking, and seeds. Examples include a treatment for seeds such as a coat, a treatment for seedlings, and a treatment for bulbs.

  Specific examples of the treatment of plant foliage, flower vases or ears in the method of the present invention include methods of treating the surface of plants such as foliage spray and trunk spray. Moreover, the method of spraying the vase or the whole plant in the flowering time including before flowering, during flowering, and after flowering is mentioned. Moreover, in the case of cereals, a method of spraying on the head of the heading season or the whole plant can be mentioned.

  Examples of the soil treatment method in the method of the present invention include application to the soil, soil mixing, and chemical irrigation (chemical irrigation, soil injection, chemical drip) to the soil. Strips, near planting holes, near crops, the entire area of the plantation area, plant borders, between stocks, under trunks, trunk trunks, soil, seedling boxes, seedling trays, seedlings, etc. The treatment time is before sowing, sowing Time, immediately after sowing, seedling growing season, before planting, at the time of planting, and the growing season after planting. In the above soil treatment, a plurality of the present compounds may be simultaneously treated on a plant, or solid fertilizers such as paste fertilizers containing the present compounds may be treated on the soil. In addition, the present compound may be mixed with an irrigation liquid, for example, injection into an irrigation facility (irrigation tube, irrigation pipe, sprinkler, etc.), mixing into a streak water solution, mixing into a hydroponic liquid, etc. . In addition, the irrigation solution and the present compound can be mixed in advance and treated using an appropriate irrigation method such as the above-mentioned irrigation method or other watering or flooding.

  The treatment of the seed in the method of the present invention is, for example, a method of treating the present compound on seeds, bulbs and the like of a plant to be protected from temperature stress. Specifically, for example, a suspension of the present compound is used. A small amount of water is added to the seed surface or bulb surface, sprayed onto the seed surface or bulb surface, or a small amount of water is added to the wettable powder, emulsion, or flowable agent of this compound, or it is applied to the seed or bulb as it is. Examples of the treatment include immersion treatment in which the seed is immersed in the solution of the present compound for a certain period of time, film coating treatment, and pellet coating treatment.

  Examples of the treatment for the seedling in the method of the present invention include, for example, a spraying treatment for spraying a diluted solution prepared by diluting the present compound with water to an appropriate active ingredient concentration over the entire seedling, an immersion treatment for immersing the seedling in the diluted solution, and a powder. An application treatment for adhering the compound prepared in the above to the entire seedling is mentioned. The treatment of the soil before or after planting the seedling includes, for example, a diluted solution prepared by diluting the present compound with water to an appropriate active ingredient concentration, and the seedling and surrounding soil after planting the seedling. And a method of spraying the present compound prepared in a solid preparation such as a granule or a granule to surrounding soil after planting seedlings.

In addition, when the present compound is treated in a plant or a plant growing place, the treatment amount can be changed depending on the kind of plant to be treated, formulation form, treatment time, weather conditions, etc., but as an effective amount per 1000 m ² , It is in the range of 0.1 to 1000 grams, preferably 0.5 to 50 grams.

  Emulsions, wettable powders, flowables, microcapsules and the like are usually treated by diluting with water and spraying. In this case, the concentration of the present compound is usually in the range of 1 to 10,000 ppm, preferably 10 to 300 ppm. Powders, granules, etc. are usually processed without dilution.

  In the treatment of seeds, the amount of the present compound relative to 100 kilograms of seed is usually 1 to 1000 grams, preferably 5 to 500 grams, and more preferably 250 to 500 grams.

In the treatment of seedlings, the amount of the present compound per seedling is usually in the range of 0.1 to 50 milligrams, preferably 0.5 to 50 milligrams. In the treatment of the soil before or after planting seedlings, the amount of the present compound per 1000 m ² is usually in the range of 0.1 to 100 grams, preferably 0.5 to 50 grams.

  In the treatment to the cultivation nutrient solution, the concentration of the present compound in the cultivation nutrient solution is in the range of 0.1 to 1000 ppm, preferably 5 to 500 ppm.

The method of the present invention can be carried out for any agricultural land such as a field, paddy field, lawn, orchard or non-agricultural land.
Examples of plants that can reduce temperature stress according to the present invention include the following.

  Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, oilseed rape, sunflower, sugar cane, tobacco, hop, etc.

  Vegetables: Solanum vegetables (eggplants, tomatoes, potatoes, peppers, peppers, etc.), cucurbits (cucumbers, pumpkins, zucchini, watermelon, melons, cucumbers, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage) , Cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus, etc.), celery family vegetables (carrot, parsley, celery, American Bow Fu etc.), Rubiaceae vegetables (spinach, chard, etc.), Lamiaceae vegetables (silla, mint, basil etc.), legumes (peas, kidney beans, azuki bean, broad beans, chickpea etc.), strawberries, sweet potatoes, yam, taro , Konjac, ginger, ok Etc..

  Fruit trees: fruits (apples, pears, pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, umes, sweet cherry, apricots, prunes, etc.), citrus (citrus oranges, oranges, lemons, limes, grapefruits) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.

  Trees other than fruit trees: tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, snapdragon, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, blackfish, Japanese amberjack, moths, pine, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi, etc.

Lawn: Shiba (Nasis, Pleurotus, etc.), Bermudagrass (Neurodonidae, etc.), Bentgrass (Oleoptera, Hykonukagusa, Odonoptera, etc.), Bluegrass (Nagahagusa, Oosuzunokatabira, etc.), Fescue (Oonishi nokegusa, Drosophila, etc.) , Grass, etc.), ryegrass (rat, wheat, etc.), anemonefish, and blue whale.
Other: Flowers (Rose, Carnation, Chrysanthemum, Eustoma, Gypsophila, Gerbera, Marigold, Salvia, Petunia, Verbena, Tulip, Aster, Gentian, Lily, Pansy, Cyclamen, Orchid, Lily of the valley, Lavender, Stock, Habutton, Primula, Poinsettia, gladiolus, cattleya, daisy, symbidium, begonia, etc.), biofuel plants (Jatropha, safflower, Amanas, switchgrass, miscanthus, kusayoshi, dangiku, kenaf, cassava, willow, etc.), houseplants, etc.

  More preferable plants that can reduce abiotic stress according to the present invention include rice, corn, and wheat.

  The above-mentioned “plants” include 5-hydroxyphenylpyruvate dioxygenase inhibitors such as isoxaflutole, acetolactate synthase (hereinafter abbreviated as ALS) inhibitors such as imazetapyr and thifensulfuronmethyl, glyphosate and the like 5 -Enol pyruvyl shikimate-3-phosphate synthase (hereinafter abbreviated as EPSPS) inhibitor, glutamine synthetase inhibitor such as glufosinate, acetyl CoA carboxylase inhibitor such as cetoxidim, protoporphyrinogen oxidase inhibitor such as flumioxazin Plants to which resistance to auxinic herbicides such as herbicides, dicamba and 2,4-D, and herbicides such as bromoxynil have been imparted by classical breeding methods or genetic recombination techniques are also included.

  Examples of “plants” that have been given resistance by classical breeding methods include oilseed rape, wheat, sunflower, and rice that are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazetapil. The trade name of Clearfield (registered trademark) Already on sale. Similarly, there are soybeans that are resistant to sulfonylurea ALS-inhibiting herbicides such as thifensulfuron methyl by classical breeding methods, and are already sold under the trade name of STS soybeans. Similarly, SR corn and the like are examples of plants to which tolerance has been imparted to acetyl CoA carboxylase inhibitors such as trion oxime and aryloxyphenoxypropionic acid herbicides by classical breeding methods. Plants that have been rendered tolerant to acetyl-CoA carboxylase inhibitors are the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci). USA), 1990, 87, p. 7175-7179.

  Examples of “plants” that have been rendered resistant by genetic recombination techniques include glyphosate-resistant maize, soybean, cotton, rapeseed, and sugar beet varieties having EPSPS genes that are resistant to EPSPS inhibitors. RoundupReady < Have already been sold under trade names such as registered trademark>, Agrisure <registered trademark> GT, Gly-Tol. Similarly, there are corn, soybean, cotton, and oilseed rape varieties that are resistant to glufosinate by gene recombination technology, and are already sold under trade names such as LibertyLink (registered trademark). Similarly, bromoxynyl-resistant cotton by gene recombination technology is already sold under the trade name BXN. Similarly, there are corn and soybean varieties that are resistant to both glyphosate and ALS inhibitors, and the trade name of Optimum <(R)> GAT <(R)> has been published. In addition, the brand name of Cultivans (Cultivance (registered trademark)), a soybean variety resistant to imazapyr by genetic recombination technology, is disclosed.

  Further, mutant acetyl CoA carboxylase resistant to acetyl CoA carboxylase inhibitors has been reported in Weed Science, 53, 728-746 (2005), etc., and such mutant acetyl CoA carboxylase gene can be transferred to plants by gene recombination technology. A plant resistant to an acetyl-CoA carboxylase inhibitor can be produced by introducing a mutation associated with introduction or resistance imparting into a crop acetyl-CoA carboxylase. Furthermore, a nucleic acid introduced with a base substitution mutation represented by chimera plastic technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.) By introducing a site-specific amino acid substitution mutation into the ALS gene, a plant resistant to an acetyl CoA carboxylase inhibitor or an ALS inhibitor can be produced.

In addition, a gene encoding a dicamba monooxygenase containing dicamba monooxygenase isolated from Pseudomonas maltophilia can be introduced to produce a crop such as soybean resistant to dicamba. (Behrens et al. 2007. Dicamba Resistance: Enlarging and Preserving Biotechnology-Based Weed Management Strategies. Science 316: 1185-1188).
Introducing a gene encoding aryloxyalkanoate dioxygenase, phenoxy herbicides such as 2,4-D, MCPA, dicloprop, mecoprop, pyridineoxyacetic acid systems such as fluroxypyr, triclopyr; Of aryloxyphenoxypropionic acid herbicides such as quizalofop-P-ethyl, haloxyhop-P-methyl, fluazihop-P-butyl, dicloholop, phenoxaprop-P-ethyl, metamihop, cyhalohop-butyl, clodinafop-propargyl, It is possible to produce crops that are resistant to both herbicide lines (WO2005 / 107437, WO2007 / 053482, WO2008 / 141154), D It is called HT crop.

Furthermore, a gene encoding HPPD showing resistance to an HPPD inhibitor can be introduced to produce a plant resistant to the HPPD inhibitor (US2004 / 0058427). Even if HPPD is inhibited by an HPPD inhibitor, a gene that can synthesize homogentisic acid, which is a product of HPPD, by another metabolic pathway is introduced, and as a result, a plant that is resistant to the HPPD inhibitor is created. (WO02 / 036787). A gene that overexpresses HPPD is introduced, and even in the presence of an HPPD inhibitor, HPPD is produced in an amount that does not affect the growth of the plant. As a result, a plant that is resistant to the HPPD inhibitor is produced. Can be produced (WO 96/38567). In addition to the introduction of a gene that overexpresses HPPD described above, a gene encoding prephenate dehydrogenase was introduced to increase the amount of p-hydroxyphenylpyruvic acid that is a substrate of HPPD, thereby inhibiting HPPD Plants exhibiting resistance to agents can be produced (Rippert P et.al. 2004. Engineering plant shikimate pathway for production of tocotrienol and improving herbicide resistance. Plant Physiol. 134: 92-100).
The “plant” includes a plant imparted with resistance to nematodes and aphids by a classic breeding method. As an example, soybean introduced with a RAG1 (Resistance Aphid Gene 1) gene that imparts resistance to aphids can be mentioned.

  The “plant” includes a plant which can synthesize, for example, a selective toxin known in the genus Bacillus using a gene recombination technique.

  Examples of toxins expressed in such genetically modified plants include insecticidal proteins derived from Bacillus cereus and Bacillus popilie; Insecticidal proteins such as δ-endotoxin, VIP1, VIP2, VIP3 or VIP3A; nematode-derived insecticidal proteins; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plants Lectin; agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; lysine, corn-RIP, abrin, ruffin, saporin, bryodin, etc. Ribosome inactivating protein (RIP); steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-CoA reductase; sodium channel, calcium channel inhibitor, etc. Ion channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.

  Further, as toxins expressed in such a genetically modified plant, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab or the like δ-endotoxin proteins, VIP1, VIP2, VIP3 or VIPA, etc. Insecticidal protein hybrid toxins, partially defective toxins, and modified toxins are also included. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted.

  Examples of these toxins and recombinant plants capable of synthesizing these toxins are described in EP-A-0374753, WO93 / 07278, WO95 / 34656, EP-A-0427529, EP-A-451878, WO03 / 052073 and the like. Are listed.

  Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera pests, Diptera pests, Lepidoptera pests and nematodes.

  In addition, genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known and some are commercially available. Examples of these transgenic plants include YieldGard® (a corn variety that expresses Cry1Ab toxin), YieldGard Rootworm® (a corn variety that expresses Cry3Bb1 toxin), YieldGard Plus® (Cry1Ab toxin) Corn varieties expressing Cry3Bb1 toxin), Herculex I® (corn varieties expressing Cry1Fa2 toxin and phosphinotricin N-acetyltransferase (PAT) to confer resistance to glufosinate), NuCOTN33B ( (Registered trademark) (cotton variety expressing Cry1Ac toxin), Bollgard I (registered trademark) (cotton variety expressing Cry1Ac toxin), Bollgard II (registered trademark) (Trademark) (cotton variety expressing Cry1Ac toxin and Cry2Ab toxin), VIPCOT (registered trademark) (cotton variety expressing VIP toxin), NewLeaf (registered trademark potato variety expressing Cry3A toxin), NatureGard (registered trademark) ) Agurisure (registered trademark) GT Advantage (GA21 glyphosate resistant trait), Agrisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), Protecta (registered trademark), and the like.

The “plant” includes those imparted with an ability to produce an anti-pathogenic substance having a selective action using a gene recombination technique.
As examples of anti-pathogenic substances, PR proteins and the like are known (PRPs, EP-A-0392225). Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191, and the like.

  Examples of anti-pathogenic substances expressed in such genetically modified plants include, for example, sodium channel inhibitors, calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.). Ion channel inhibitor; stilbene synthase; bibenzyl synthase; chitinase; glucanase; PR protein; peptide antibiotics, antibiotics having heterocycles, protein factors involved in plant disease resistance (referred to as plant disease resistance gene, WO03 / 000906)) and other anti-pathogenic substances produced by microorganisms. Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0392225, WO95 / 33818, EP-A-0353191, and the like. In addition, there is a recombinant papaya variety into which a coat protein gene of papaya ring spot virus (PRSV) has been introduced, which has already been sold under the trade name of Rainbow Papaya (registered trademark).

  The above “plant” includes plants imparted with useful traits such as oil component modification and amino acid content enhancing traits using genetic recombination techniques. Examples include VISTIVE (registered trademark) (low linolenic soybean with reduced linolenic content) or high-lysine (high-oil) corn (corn with increased lysine or oil content).

  Furthermore, for the above-mentioned classic herbicide tolerance traits or herbicide tolerance genes, insecticidal pest resistance genes, antipathogenic substance production genes, oily ingredient modification and amino acid content enhancement traits, etc. Multiple types of stacks are also included.

  Hereinafter, the present invention will be described in more detail with formulation examples, treatment examples, and test examples, but the present invention is not limited to the following examples. In the following examples, parts are parts by weight unless otherwise specified.

Formulation Example 1
3.75 parts of any one of the compounds 1 to 26 shown in Table 1 are mixed well with 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 76.25 parts of xylene. To obtain an emulsion.

Formulation Example 2
75 parts of any one of compounds 1 to 26 shown in Table 1, 15 parts of propylene glycol (manufactured by Nacalai Tesque), 15 parts of Soprophor FLK (manufactured by Rhodia Nikka), 0.6 of anti-form C emulsion Parts (manufactured by Dow Corning) and ion-exchanged water at a ratio of 120 parts, and then the slurry is wet-pulverized to obtain a wet-pulverized slurry. Add 0.3 parts of Kelzan S (manufactured by Kelco), 0.6 parts of Veegum granules (manufactured by RT Vanderbilt) and 0.6 parts of Proxel GXL (manufactured by Arch Chemicals) to 72.9 parts of ion-exchanged water, and increase A viscous aqueous solution is obtained. 75.2 parts of the obtained wet pulverized slurry and 24.8 parts of a thickener aqueous solution are added and mixed to obtain a flowable preparation.

Formulation Example 3
15 parts of any one of compounds 1 to 26 shown in Table 1 are mixed with 28.5 parts of an aqueous solution containing 1.5 parts of sorbitan trioleate and 2 parts of polyvinyl alcohol. Then, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added to this, and 10 parts of propylene glycol is further added and stirred to mix the flowable preparation. obtain.

Formulation Example 4
45 parts of any one of compounds 1 to 26 shown in Table 1, 5 parts of propylene glycol (manufactured by Nacalai Tesque), 5 parts of Soprophor FLK (manufactured by Rhodia Nikka), 0.2 of anti-form C emulsion Part (manufactured by Dow Corning), 0.3 part of proxel GXL (manufactured by Arch Chemical), and 49.5 parts of ion-exchanged water are mixed to prepare a base slurry. 150 parts of glass beads (Φ = 1 mm) are added to 100 parts of the slurry, and pulverized for 2 hours while cooling with cooling water. After grinding, the glass beads are removed by filtration to obtain a flowable formulation.

Formulation Example 5
50.5 parts of any one of compounds 1 to 26 shown in Table 1, 38.5 parts of NN kaolin clay (manufactured by Takehara Chemical Industries), 10 parts of Morwet D425, 1.5 parts of Morwer EFW ( Mixing at a ratio of Akzo Nobel) to obtain an AI premix. The premix is pulverized with a jet mill to obtain a powder.

Formulation Example 6
5 parts of any one of the compounds 1 to 26 shown in Table 1, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite, and 62 parts of kaolin clay are thoroughly pulverized and mixed with water. In addition, after kneading well, granulation is dried to obtain granules.

Formulation Example 7
Each powder is obtained by thoroughly pulverizing and mixing 3 parts of any one of compounds 1 to 26 shown in Table 1, 87 parts of kaolin clay, and 10 parts of talc.

Formulation Example 8
By thoroughly pulverizing and mixing 22 parts of any one of compounds 1 to 26 shown in Table 1, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 73 parts of synthetic hydrous silicon oxide, Get.

Seed treatment example 1
By subjecting the flowable formulation prepared according to Formulation Example 2 or 3 to 10 kilograms of dried oilseed rape seeds using a rotary seed treatment machine (seed dresser, Hans-Ulrich Hege GmbH), 120 ml is smeared. Obtain treated seeds.

Seed treatment example 2
The flowable formulation produced according to Formulation Example 3 is subjected to 200 ml smearing treatment for 10 kg of dried corn seeds using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH). obtain.

Seed treatment example 3
5 parts of a flowable preparation prepared according to Preparation Example 4, 5 parts of Pigment BPD6135 (manufactured by Sun Chemical), and 35 parts of water are mixed to prepare an admixture. The mixture is subjected to 600 ml smearing treatment using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH) on 10 kg of dry cotton seeds to obtain treated seeds.

Seed treatment example 4
Treated seeds are obtained by subjecting the powder prepared in accordance with Formulation Example 5 to 50 g of powder for 10 kg of dried corn seeds.

Seed treatment example 5
The powder produced according to Formulation Example 7 is treated with 9 kilograms of powder for 100 kilograms of dried rice seeds to obtain treated seeds.

Seed treatment example 6
The flowable formulation produced according to Formulation Example 2 is subjected to 180 ml smearing treatment for 10 kg of dried soybean seeds using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH). obtain.

Seed treatment example 7
The flowable formulation produced according to Formulation Example 3 is subjected to 180 ml smearing treatment on 10 kg of dried wheat seeds using a rotary seed treatment machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH). obtain.

Seed treatment example 8
5 parts of a flowable preparation prepared according to Formulation Example 4, 5 parts of Pigment BPD6135 (manufactured by Sun Chemical) and 35 parts of water are mixed, and 10 kg of sunflower seeds are mixed with a rotary seed treatment machine (seed dresser, Hans- A treated seed is obtained by smearing 600 ml using (Ulrich Hege GmbH).

Seed treatment example 9
Treated seeds are obtained by subjecting the powder prepared in accordance with Formulation Example 5 to 50 grams of powdered seeds for 10 kilograms of dried sugar beet seeds.

Application example 1
5 parts of a flowable preparation prepared according to Formulation Example 4, 5 parts of Pigment BPD6135 (manufactured by Sun Chemical), and 35 parts of water are mixed, and a rotary seed processing machine (seed dresser, Hans) is added to 10 kg of potato tubers. -Treated tuber pieces are obtained by 1000 ml smearing treatment using (Ulrich Hege GmbH).

Test Example 1 Low temperature stress reduction evaluation test by corn seed treatment (plant weight)
(Test plant)
Corn (variety: black rice cake)
(Seed treatment method)
Blank slurry solution containing 5% (V / V) color coat red (Becker Underwood, Inc.), 5% (V / V) CF-Clear (Becker Underwood, Inc.), 0.4% Maxim XL (manufactured by Syngenta) Was prepared. Compound 1 and Compound 6 shown in Table 1 were each dissolved in a blank slurry solution so as to be 250 to 1000 grams per 100 kilograms of corn seeds (variety: black rice cake) to obtain slurry solutions. In a 50 ml centrifuge tube (manufactured by Nippon BD Co., Ltd.), 0.48 ml of the slurry solution per 20 grams of corn seed (variety: black rice cake) was added and stirred until the slurry solution was dry to coat the seeds. As a control, seeds coated with a blank slurry solution were used as untreated seeds.
(Low-temperature stress treatment method)
After seed treatment, corn seeds are sown 2 times each in a culture soil (Aina) in a plastic pot (diameter 55 mm x height 58 mm), under conditions of temperature: 27 ° C, illuminance: about 5,000 lux, day length of 16 hours Cultivated for 10 days and used for testing.
A pot on the 10th day after sowing was placed in an artificial meteorograph set to the following temperature conditions, and stress treatment was carried out for 7 days.
Temperature: 3 ± 2 ℃, day length 16 hours, illuminance: about 5,000 lux, humidity: 35-80%
(Evaluation method)
After the low temperature stress treatment, the fresh weight of the above-ground part was weighed after cultivation for 4 days under the conditions of temperature: 27 ° C., humidity: 50-75%, illuminance: about 5,000 lux, and day length of 16 hours. Four replicates were taken for each treatment condition and averaged to determine the average weight per individual.
As a result, in the treated group of Compound (1), the decrease in fresh weight due to low temperature stress was alleviated in the treated group of 250 grams per 100 kilogram seeds and 500 grams per 100 kilogram seeds, compared with the untreated group.

Test Example 2 Low temperature stress reduction evaluation test immediately after germination by corn seed treatment (plant weight)
(Test plant)
Corn (variety: black rice cake)
(Seed treatment method)
Blank slurry solution containing 5% (V / V) color coat red (Becker Underwood, Inc.), 5% (V / V) CF-Clear (Becker Underwood, Inc.), 0.4% Maxim XL (manufactured by Syngenta) Was prepared. Compound 1 and Compound 6 shown in Table 1 were each dissolved in a blank slurry solution so as to be 250 to 1000 grams per 100 kilograms of corn seeds (variety: black rice cake) to obtain slurry solutions. A 50 ml centrifuge tube (manufactured by Nippon BD) was charged with 0.48 ml of slurry solution per 20 kg of corn seed (variety: Kuromochi) and stirred until the slurry solution was dry to coat the seeds. As a control, seeds coated with a blank slurry solution were used as untreated seeds.
(Low-temperature stress treatment method)
After seed treatment, corn seeds are sown 2 times each in a culture soil (Aina) in a plastic pot (diameter 55 mm x height 58 mm), under conditions of temperature: 27 ° C, illuminance: about 5,000 lux, day length of 16 hours Cultivated for 4 days and used for testing.

A pot on the fourth day after sowing was placed in an artificial meteorograph set to the following temperature conditions, and stress treatment was carried out for 7 days.
Temperature: 3 ± 2 ℃, day length 16 hours, illuminance: about 5,000 lux, humidity: 35-80%
(Evaluation method)
After the low-temperature stress treatment, the fresh weight of the above-ground part was weighed after cultivation for 7 days under the conditions of temperature: 27 ° C., humidity: 50-75%, illuminance: about 5,000 lux, and day length of 16 hours. Eight replicates were taken for each treatment condition and averaged to determine the average weight per individual.
As a result, in the Compound 1 treatment group and the Compound 6 treatment group, a decrease in fresh weight on the ground due to low temperature stress was alleviated as compared with the untreated group.

Test Example 3 Dry stress reduction evaluation test (plant weight) by rice seed treatment
(Seed treatment)
Prepare blank slurry solution containing 5% (V / V) color coat red (Becker Underwood, Inc.), 5% (V / V) CF-Clear (Becker Underwood, Inc.), 0.4% Maxim XL (Syngenta) did. Compound 1 and Compound 6 shown in Table 1 were each dissolved in a blank slurry solution so as to be 250 to 1000 grams per 100 kilograms to prepare slurry solutions. A 50 mL centrifuge tube (manufactured by Nippon BD) was charged with 0.48 ml of the slurry solution per 20 grams of rice seed (variety: Nipponbare) and stirred until the slurry solution was dry to coat the seeds. As a control, seeds coated with a blank slurry solution were used as untreated seeds.
As a control, seeds coated with a blank slurry solution instead of the slurry solution were used as untreated seeds.
(Test plant)
A filter paper was placed in the hole of the 406-hole plug tray, and the seed-treated rice seeds were sown on the filter paper. Using Kimura B hydroponic solution diluted twice (Plant Science 119: 39-47 (1996)), temperature: 28 ° C / night 23 ° C, illuminance: 8,500 lux, day length 12 hours, 14 days Cultivated and used as a test plant.
(Dry stress and recovery treatment)
Each test plant was placed in an empty 35 ml flat-bottomed test tube (made by Assist / Sarstedt) and left to stand for 2 days without a lid, and subjected to drought stress. As test plots not subjected to drought stress, the test plants were placed in 50 mL centrifuge tubes containing 10 ml of 2-fold diluted Kimura B hydroponic solution, and allowed to stand for 2 days without a lid. Transplant 5 plants into a plastic pot (N-71-130G, manufactured by Toagokogyo Co., Ltd.) containing field soil that has been sterilized after standing for 2 days. Cultivation was carried out for 14 days under the conditions of ℃ / night 23 ℃, illuminance: 8,500 lux, day length 12 hours.
(Evaluation)
After the drought stress treatment, five test plants in each test group were collected, the fresh weight on the ground was measured, and the value of each test group was determined. The results are shown in Table 3. As a result, the above-ground fresh weight of the test group of the present invention was clearly larger than that of the untreated group, and drought stress was reduced.

Test Example 4 High temperature stress reduction evaluation test (plant weight) by wheat seed treatment
(Test plant) Wheat (Cultivar Apogee)
(Seed treatment method)
Prepare blank slurry solution containing 5% (V / V) color coat red (Becker Underwood, Inc.), 5% (V / V) CF-Clear (Becker Underwood, Inc.), 0.4% Maxim XL (Syngenta) To do. Any one compound of Compound 1 to Compound 26 shown in Table 1 is dissolved in a blank slurry solution so as to be 0.05 to 0.25 milligram per gram of seed (variety: Apogee) to obtain a slurry solution. Using a seed treatment machine (HEGE11, manufactured by Hans-Ulrich Hege), 1.3 ml of the slurry solution is mixed per 50 grams of wheat seeds to coat the seeds, and then the seeds are spread and dried. As a control, seeds coated with the blank slurry solution are used as untreated seeds. 5 seeds of coated wheat seeds are sown on a soil (Aina) in a plastic pot (diameter 55 mm x height 58 mm), cultivated at 18 ° C for 3 weeks, and 3 individuals that grew well Select by thinning out.
(High temperature stress treatment method)
Plants 3 weeks after sowing were cultivated for 7 days under conditions of temperature: 36 ° C / 32 ° C, humidity: 60-70%, illuminance: about 6,000 lux, and length of 12 hours. Do. Subsequently, cultivation is performed for one week at a temperature of 18 ° C., an illuminance of about 6,000 lux, and a day length of 16 hours.
(Evaluation method)
Then, the fresh weight of the above-ground part is investigated by repeating 3 strains / pot 8 times. In the treated area of this compound, a decrease in the reduction in fresh weight due to high temperature stress was observed compared to the untreated area.

  By using the method of the present invention, the influence of abiotic stress can be reduced.

Claims (12)

A method for reducing the effects of abiotic stress on a plant,
A method of treating a plant exposed to or likely to be exposed to abiotic stress with at least one compound selected from the group consisting of compounds represented by the following formula (1).
Formula (1)

[Wherein, R ¹ represents a C1-C6 alkyl group which may be substituted with a halogen atom, and R ² may be a C1-C6 alkyl group which may be substituted with a halogen atom, or may be substituted with a halogen atom. A C3-C6 alkoxyalkyl group, a C3-C6 alkenyl group which may be substituted with a halogen atom, or a C3-C6 alkynyl group which may be substituted with a halogen atom, and R ³ is a halogen atom or a halogen atom Represents a C1-C6 alkyl group that may be substituted with, R ⁴ represents a hydrogen atom, a halogen atom, a cyano group, or a C1-C6 alkyl group that may be substituted with a halogen atom, and R ⁵ represents a hydrogen atom. , A halogen atom, a cyano group, a C1-C6 alkyl group optionally substituted with a halogen atom, a C1-C6 atom optionally substituted with a halogen atom Lucoxy group, C1-C6 alkylthio group optionally substituted with a halogen atom, C1-C6 alkylsulfinyl group optionally substituted with a halogen atom, or C1-C6 alkylsulfonyl group optionally substituted with a halogen atom R ⁶ represents a halogen atom or a C1-C6 alkyl group which may be substituted with a halogen atom. ] Formula (1)

The method according to claim 1, wherein the compound represented by the formula (I) is a compound selected from the following compound group A.
<Compound group A>
(1) Compound (2) in which R ¹ in formula (1) is an ethyl group, R ² is a methyl group, R ³ is a bromo group, R ⁴ is a bromo group, R ⁵ is a bromo group, and R ⁶ is a chloro group A compound in which R ¹ in (1) is a methyl group, R ² is a methyl group, R ³ is a methyl group, R ⁴ is a cyano group, R ⁵ is a bromo group, and R ⁶ is a chloro group   The method according to claim 1 or 2, wherein the treatment is spraying treatment, soil irrigation treatment, seed treatment or hydroponic treatment.   The method according to claims 1 to 3, wherein the treatment is a seed treatment, and the treatment concentration of the compound in the seed treatment is 5 g or more and 500 g or less per 100 kg of seed.   The method according to claims 1 to 3, wherein the treatment is a seed treatment, and the treatment concentration of the compound in the seed treatment is 250 g or more and 500 g or less per 100 kg of seed.   The method according to claim 1, wherein the plant is rice, corn or wheat.   The method according to claim 1, wherein the plant is a genetically modified plant.   The method according to claim 1, wherein the abiotic stress is low-temperature stress.   The method according to claim 1, wherein the abiotic stress is drought stress. The method according to claim 1, wherein the reduction of the influence of the abiotic stress on the plant is indicated by a change in at least one plant phenotype described in the following (1) to (14).
<Plant phenotype>
(1) Germination rate (2) Seedling establishment rate (3) Leaf death rate (4) Plant height (5) Plant weight (6) Leaf area (7) Leaf color (8) Number or weight of seeds and fruits (9) Harvest Product quality (10) Flowering rate, fruiting rate, fruiting rate, seed filling rate (11) Chlorophyll fluorescence yield (12) Water content (13) Leaf surface temperature (14) Transpiration Use of at least one compound selected from the group consisting of compounds represented by formula (1) for reducing the effects of abiotic stress on plants.

Formula (1)

[Wherein, R ¹ represents a C1-C6 alkyl group which may be substituted with a halogen atom, and R ² may be a C1-C6 alkyl group which may be substituted with a halogen atom, or may be substituted with a halogen atom. A C3-C6 alkoxyalkyl group, a C3-C6 alkenyl group which may be substituted with a halogen atom, or a C3-C6 alkynyl group which may be substituted with a halogen atom, and R ³ is a halogen atom or a halogen atom Represents a C1-C6 alkyl group that may be substituted with, R ⁴ represents a hydrogen atom, a halogen atom, a cyano group, or a C1-C6 alkyl group that may be substituted with a halogen atom, and R ⁵ represents a hydrogen atom. , A halogen atom, a cyano group, a C1-C6 alkyl group optionally substituted with a halogen atom, a C1-C6 atom optionally substituted with a halogen atom Lucoxy group, C1-C6 alkylthio group optionally substituted with a halogen atom, C1-C6 alkylsulfinyl group optionally substituted with a halogen atom, or C1-C6 alkylsulfonyl group optionally substituted with a halogen atom R ⁶ represents a halogen atom or a C1-C6 alkyl group which may be substituted with a halogen atom. ] Use according to claim 11, characterized in that the reduction of the effects of abiotic stress on the plant is indicated by a change in at least one plant phenotype as described in (1) to (14) below.
<Plant phenotype>
(1) Germination rate (2) Seedling establishment rate (3) Leaf death rate (4) Plant height (5) Plant weight (6) Leaf area (7) Leaf color (8) Number or weight of seeds and fruits (9) Harvest Product quality (10) Flowering rate, fruiting rate, fruiting rate, seed filling rate (11) Chlorophyll fluorescence yield (12) Water content (13) Leaf surface temperature (14) Transpiration