WO2018086508A1 - 萘磺酰胺类化合物在调节植物生长活性中的应用 - Google Patents

萘磺酰胺类化合物在调节植物生长活性中的应用 Download PDF

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WO2018086508A1
WO2018086508A1 PCT/CN2017/109690 CN2017109690W WO2018086508A1 WO 2018086508 A1 WO2018086508 A1 WO 2018086508A1 CN 2017109690 W CN2017109690 W CN 2017109690W WO 2018086508 A1 WO2018086508 A1 WO 2018086508A1
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plant growth
growth activity
tolerance
application
compound
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PCT/CN2017/109690
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French (fr)
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段留生
于春欣
刘少金
梁丽君
胡堂路
周于毅
李召虎
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中国农业大学
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings

Definitions

  • the invention belongs to the field of plant growth regulators, and in particular relates to the application of a naphthalenesulfonamide compound in regulating plant growth activity.
  • Abscisic acid is an important endogenous phytohormone with a sesquiterpene structure, which plays an important role in plant detachment, induction of dormancy, inhibition of germination, promotion of organ senescence and shedding, and enhancement of stress resistance. Therefore, the rational use of abscisic acid is of great significance for promoting crop yield increase, income increase and improvement of crop varieties.
  • abscisic acid functional analogues are one of the research hotspots in the field.
  • WO 2010093954 A2 discloses an abscisic acid analog, Pyrabactin, which has the function of inhibiting seed germination and regulating stomatal closure, and subsequent studies have shown that drought tolerance of corn and other crops can be improved and flowering time of citrus can be adjusted; WO 2013148339A1 discloses shedding.
  • Acid analog Quinabactin the compound can induce stomatal closure and improve the drought resistance of soybean and tomato;
  • CN102391147A discloses a class of arylcarboxamide cyclopropionic acid abscisic acid analogues, some of which have plant growth regulating activity inhibiting seed germination;
  • CN103435472A A class of highly active benzoisosuccinic acid analogs is disclosed, which have an inhibitory activity against Arabidopsis seed germination of about 14 times that of (+)-ABA;
  • CN102911041A discloses a 2,3-position cyclopropanation.
  • Abscisic acid analogs which have a photostability about 4 times that of abscisic acid; WO 2015113944 A1 discloses that phosphate-based Pyrabactin analogs have a similar function as abscisic acid, and some compounds have the effect of regulating stomatal closure and inhibiting seed germination.
  • the invention claims the use of at least one of the compounds of the formula I to formula VI for regulating plant growth activity:
  • X is F, Cl, Br or I.
  • the present invention also claims a plant growth activity modulator comprising at least one of the foregoing Formulae I to VI.
  • the present invention also claims a herbicide comprising at least one of the foregoing Formulas I to VI.
  • the present invention also claims a method of regulating plant growth activity, comprising: applying a plant to the plant using at least one of the compounds of Formulas I to VI above:
  • the present invention also claims a method of weeding, the method comprising: applying a herb to the grass using at least one of the compounds of Formulas I to VI above;
  • the present invention also claims a method for simultaneously regulating plant growth activity and weeding, the method comprising: applying the grass to the grass using at least one of the compounds of the above formula I to formula VI;
  • the invention also claims a plant growth activity modulator and a herbicide.
  • the present invention also claims a product capable of simultaneously regulating plant growth activity and weeding, wherein the product contains at least one of the foregoing Formulae I to VI.
  • the regulating plant growth activity is to improve at least one of cold tolerance, drought tolerance, salt tolerance and high temperature resistance of the plant;
  • the plant growth activity regulator is a regulator for improving at least one of cold tolerance, drought tolerance, salt tolerance and high temperature resistance of the plant.
  • the plant is a monocot or a dicot
  • the grass is a monocot or a dicot.
  • the monocot is wheat, rice or corn; the dicot is cotton; and/or
  • the monocotyledonous plant is valerian, goosegrass, maiden, crabgrass or medlar; the dicot is purslane;
  • the application site is a leaf surface
  • the application method is spray; specifically, spraying an aqueous solution of the compound;
  • the concentration of the aqueous solution of the compound is 0.001-200 ⁇ mol / L, specifically 50 ⁇ mol / L;
  • the application amount is 15-30 L of an aqueous solution of the compound per acre.
  • the compound of the formula I is a compound of the formula I1;
  • the compound of formula I is a compound of formula II1;
  • the compound of formula III is a compound of formula III1;
  • the compound of formula IV is a compound of formula IV1;
  • the compound of the formula V is a compound of the formula V1;
  • the compound represented by the formula VI is a compound of the formula VI1;
  • the high temperature is 28-38 ° C; more specifically, it is kept at 28-38 ° C for several days, such as 3-6 days; and in particular, it is kept at 38 ° C during the day and 28 ° C at night for several days. Such as 3-6 days.
  • the invention is further illustrated by the following specific examples, but the invention is not limited to the following examples.
  • the method is a conventional method unless otherwise specified.
  • the raw materials can be obtained from public commercial sources unless otherwise specified.
  • Example 1 Compounds for improving the biological activity of rice in cold tolerance of rice (Nipponbare, purchased from the Agricultural College of China Agricultural University)
  • Spray the seedling tray sprinkle a little vermiculite (water absorption, moisturizing) in the hole for paving, then spray water, sow, pay attention to the roots facing down, touch the bottom of the plate, the buds face up, and then scatter the stones to bury the seeds, each Treat 30 seeds and 5 replicates. Spray water again to keep it hydrated. Spread more vermiculite to prevent premature evaporation of water. After sowing, the bottom of the plate is covered with shallow water (30% by mass of nutrient solution, see Table 3 for specific ingredients). Sprinkle water on the seedling plate every day to keep it hydrated.
  • the seedling trays were cultured in an artificial greenhouse at 20-30 ° C, light for 16 h, dark for 8 h, and humidity of 70-80%.
  • the leaves When growing to the 3-leaf stage, the leaves were sprayed with water, 100 ⁇ M of ABA and the compound of formula I provided by the present invention. After spraying for 24 hours, they were placed under an artificial climate chamber (temperature was 5 ° C, relative humidity 70% - 80%, light 12h, dark 12h) was treated for 4d, then returned to normal temperature for 2d, and the survival rate of rice seedlings was determined.
  • an artificial climate chamber temperature was 5 ° C, relative humidity 70% - 80%, light 12h, dark 12h
  • ABA can increase the survival rate of rice seedlings, and the survival rate is as high as 80% or more.
  • Most of the compounds of formula I provided by the present invention have certain activities, and the activities of the compounds represented by formula VI are more active.
  • the survival rate of the rice seedlings is increased by more than 60%, wherein the survival rate of the rice seedlings treated with the compound represented by the formula VI is above 70%, indicating that the compounds involved in the present application have a good activity for inducing the low temperature resistance of the rice seedlings.
  • Example 2 Determination of biological activity of compounds for improving drought tolerance of maize
  • the nutrient solution was shown in Table 5. Nutrient solution Change every three days. When the seedlings grow to two leaves and one heart, the leaves are sprayed with water, 100 ⁇ M ABA and the compound of formula I provided by the present invention. After 24 hours of application, drought stress is applied, 20% PEG6000 is added, and whole corn is taken after 14 days, then It was placed in a blast drying oven at 105 ° C for 15 min, dried at 80 ° C to constant weight, and the dry weight of the corn was weighed.
  • Example 3 Determination of Biological Activity of Compounds to Improve Salt Tolerance of Cotton (CCSI41, purchased from Zhongmian Institute)
  • the seedlings with uniform growth were selected and transplanted into a plastic pot of 35 cm ⁇ 27 cm ⁇ 12 cm.
  • the pot contained 4L 1/2-Hogland nutrient solution.
  • the active ingredients of the nutrient solution are shown in Table 7.
  • the method of NaCl stress treatment was as follows: When the two cotyledons of the seedlings were completely unfolded, the seedlings were transferred to tap water for one day, and then cultured in a 1/4-Hogland nutrient solution for 10 days. On the last two days of the period, the leaves were sprayed with fresh water, 100 ⁇ M of ABA and the compound of formula I provided by the present invention. After 24 hours of application, NaCl was added to the nutrient solution, and the concentration of NaCl in the nutrient solution was increased by 50 mM every 12 hours, and finally reached a treatment concentration of 150 mM. A 1/2-Hogland nutrient solution containing the above concentration of NaCl was then employed. The nutrient solution was changed every 3 days, and a certain amount of deionized water was added every day to replenish the lost water. After 10 days of salt stress treatment, the cotton was in the three-leaf stage and was awaiting sampling.
  • 70 to 80 capsules per pot placed in an artificial climate incubator, normal temperature (20 ° C during the day) At night (15 ° C), light / dark (12h / 12h) culture.
  • the leaves are sprayed with water, 100 ⁇ M ABA and the compound of formula I provided by the invention, and after 24 hours of application, high temperature treatment is carried out at 38 ° C during the day and 28 ° C at night.
  • the number of normal seedlings was counted on 3d, 4d, 5d, and 6d, respectively, and the survival rate of seedlings was calculated.
  • the material was placed at normal temperature (20 ° C during the day, 15 ° C at night) for 7 days, and the number of normal seedlings was again counted to calculate the survival rate of the seedlings.
  • a solution of a compound of formula I to formula VI provided by the present invention (dissolving the compound first in DMSO)
  • the mother liquor was set to 25 mmol/L, and then diluted to 100 ⁇ mol/L with water.
  • the common weeds and crops were soaked in petri dishes and cultured in an incubator.
  • the germination rate and the 7-day germination rate were counted for 3 days, and the degree of phytotoxicity was visually observed.
  • the bud length and root length of the seedlings were measured for 3 days and 7 days.
  • the herbicidal effect and safety of the compound soaking experiment were evaluated quantitatively. For each compound, The test was repeated 3 times, and the results obtained are shown in Table 9.
  • the naphthalenesulfonamide compound provided by the invention has excellent plant growth regulating activity, can improve cold tolerance, drought tolerance, salt tolerance, high temperature resistance and herbicidal activity of plants, and has important application value.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本发明公开了一种萘磺酰胺类化合物在调节植物生长活性中的应用。本发明要求保护一种化合物式I至式VI中至少一种在调节植物生长活性和/或除草中的应用。本发明还要求保护含有化合物式I至式VI中至少一种的植物生长活性调节剂和除草剂。所述调节植物生长活性为提高植物的耐冷性、耐旱性、耐盐性和耐高温性中至少一种；所述植物生长活性调节剂为提高植物的耐冷性、耐旱性、耐盐性和耐高温性中至少一种的调节剂。本发明提供的萘磺酰胺类化合物具有优良的植物生长调节活性，能够提高植物的耐冷性、耐旱性、耐盐性和耐高温性，并具有很好的除草活性，具有重要的应用价值。

Description

萘磺酰胺类化合物在调节植物生长活性中的应用 技术领域
本发明属于植物生长调节剂领域，具体涉及一种萘磺酰胺类化合物在调节植物生长活性中的应用。
背景技术
脱落酸是一种重要的内源性植物激素，具有倍半萜结构，在植物离层形成、诱导休眠、抑制发芽、促进器官衰老和脱落、增强抗逆性等植物生理过程中起着重要作用，因此，脱落酸的合理利用对促进农作物的增产、增收及改良作物品种等具有十分重要的意义。但是，由于生产成本较高，在植物体内快速代谢失活和侧链2-位顺式双键的光异构失活，脱落酸在农业生产中未能大面积推广应用。因此，脱落酸功能类似物是本领域内研究热点之一。
WO 2010093954A2公开了一种脱落酸类似物Pyrabactin，该化合物具有抑制种子萌发，调节气孔关闭的功能，后续研究表明还可以提高玉米等作物的耐旱性和调节柑橘的开花时间；WO 2013148339A1公开了脱落酸类似物Quinabactin，该化合物能够诱导气孔关闭，提高大豆和番茄的抗旱性；CN102391147A公开了一类芳甲酰胺基环丙酸脱落酸类似物，部分化合物具有抑制种子萌发的植物生长调节活性；CN103435472A公开了一类高活性苯并异脱落酸类似物，该类化合物对拟南芥种子萌发的抑制活性约为(+)-ABA的14倍；CN102911041A公开了一个2，3-位的环丙烷化脱落酸类似物，该化合物的光稳定性约为脱落酸的4倍；WO 2015113944A1公开了磷酸盐类Pyrabactin类似物具有脱落酸类似的功能，部分化合物具有可以调节气孔关闭和抑制种子萌发的作用。
因此，开发成本低廉、活性更高、稳定性更好的脱落酸类似物，对于加速该类植物生长调节剂在农业生产中的应用、提高农产品的质量和产量、维护环境安全等均具有非常重要的意义。
发明公开
本发明的目的是提供一种萘磺酰胺类化合物在调节植物生长活性中的应用。
本发明要求保护一种化合物式I至式VI所示化合物中至少一种在调节植物生长活性中的应用：
Figure PCTCN2017109690-appb-000001
Figure PCTCN2017109690-appb-000002
所述式I至式VI中，X为F、Cl、Br或I。
本发明还要求保护含有前述式I至式VI中至少一种的植物生长活性调节剂。
本发明还要求保护含有前述式I至式VI中至少一种的除草剂。
本发明还要求保护一种调节植物生长活性的方法，该包括：利用前述式I至式VI所示化合物中至少一种对植物进行施药：
本发明还要求保护一种除草的方法，该方法包括：利用前述式I至式VI所示化合物中至少一种对草进行施药；
本发明还要求保护一种能同时调节植物生长活性和除草的方法，该方法包括：利用前述式I至式VI所示化合物中至少一种对草进行施药；
本发明还要求保护一种植物生长活性调节剂及除草剂。
本发明还要求保护一种能够同时调节植物生长活性并除草的产品，其中，所述产品含有前述式I至式VI中至少一种。
具体的，所述调节植物生长活性为提高植物的耐冷性、耐旱性、耐盐性和耐高温性中至少一种；
所述植物生长活性调节剂为提高植物的耐冷性、耐旱性、耐盐性和耐高温性中至少一种的调节剂。
所述植物为单子叶植物或双子叶植物；
所述草为单子叶植物或双子叶植物。
具体的，所述单子叶植物为小麦、水稻或玉米；所述双子叶植物为棉花；和/或，
所述草中，单子叶植物为稗草、牛筋草、看麦娘、马唐或藜；所述双子叶植物为马齿苋；
所述施药中，施药部位为叶面；
上述调节植物生长活性和除草中，施药方式均为喷施；具体为喷施所述化合物的水溶液；
所述化合物的水溶液的浓度为0.001-200μmol/L，具体为50μmol/L；
施药量为每亩地15-30L所述化合物的水溶液。
具体的，所述式I所示化合物为式I1所示化合物；
Figure PCTCN2017109690-appb-000003
所述式I所示化合物为式II1所示化合物；
Figure PCTCN2017109690-appb-000004
所述式III所示化合物为式III1所示化合物；
Figure PCTCN2017109690-appb-000005
所述式IV所示化合物为式IV1所示化合物；
Figure PCTCN2017109690-appb-000006
所述式V所示化合物为式V1所示化合物；
Figure PCTCN2017109690-appb-000007
所述式VI所示化合物为式VI1所示化合物；
Figure PCTCN2017109690-appb-000008
所述耐高温性中，高温为28-38℃；更具体为在28-38℃保持若干天，如3-6天；再具体为在白天38℃，夜间28℃的环境中保持若干天，如3-6天。
实施发明的最佳方式
下面结合具体实施例对本发明作进一步阐述，但本发明并不限于以下实施例。所述方法如无特别说明均为常规方法。所述原材料如无特别说明均能从公开商业途径获得。
实施例1、化合物提高水稻(日本晴，购于中国农业大学农学院水稻组)耐冷性的生物活性测定
将苗盘喷湿，在孔中撒少许蛭石(吸水、保湿)作铺垫，再喷水，播种，注意根朝下，接触盘底，芽朝上，再撒蛭石将种子埋住，每个处理30棵种子，5个重复。再喷水，以保持水分。多撒蛭石，防止水分过早蒸发。播种完后盘底覆以浅水(质量百分浓度30％的营养液，具体成分见表3)。每天在苗盘上喷水以保持水分。将苗盘至于20-30℃，光照16h，黑暗8h，湿度70-80％的人工温室中培养。生长至3叶期时，叶面分别喷施清水、100μM的ABA和本发明提供的式I所示化合物，喷施24h后，置于人工气候室下(温度为5℃，相对湿度70％～80％，光照12h，黑暗12h)处理4d，然后再置于常温下恢复2d，测定水稻幼苗的成活率。
将式I所示化合物替换为式II至式VI所示化合物，按照如上步骤进行试验，对于每种化合物，试验重复3次，所得结果见表2。
表2、低温胁迫下化合物对水稻幼苗成活率的影响
Figure PCTCN2017109690-appb-000009
表3、水稻水培营养液配方
Figure PCTCN2017109690-appb-000010
Figure PCTCN2017109690-appb-000011
由表2可知，低温胁迫下，ABA能够提高水稻幼苗的成活率，成活率高达80％以上，本发明提供的式Ⅰ所示大部分化合物都有一定的活性，式VI所示化合物的活性较好，提高水稻幼苗的成活率60％以上，其中，式VI所示化合物处理的水稻幼苗的成活率在70％以上，表明本申请所涉及化合物具有很好的诱导水稻幼苗抗低温的活性。
实施例2、化合物提高玉米耐旱性的生物活性测定
挑选大小整齐饱满的玉米(郑单958，购于北京思农种业有限公司)种子400粒，用300mL 10％的H2O2水溶液浸泡15min，消毒后用大量无菌水冲洗种子，以便去除残留的H2O2，用300mL无菌水浸泡24h催芽。将催芽后的玉米种子播种到石英砂中，用黑塑料袋罩住，定期补充水分。种子发芽后揭掉黑塑料袋，进行正常培养，培养条件为光照16h，黑暗8h，温度23～28℃，幼苗长至一叶一心时移苗进行水培，营养液成分见表5，营养液每三天更换一次。幼苗长至两叶一心时叶面分别喷施清水、100μM ABA和本发明提供的式Ⅰ所示化合物，施药24h后进行干旱胁迫，加入20％的PEG6000，处理14d后取整株玉米，然后置于105℃鼓风干燥箱中杀青15min，80℃烘干至恒重，称量玉米的干重。
将式I所示化合物替换为式II至式VI所示化合物，按照如上步骤进行试验，对于每种化合物，试验重复3次，所得结果见表4。
表4、干旱胁迫下化合物对玉米干重的影响
Figure PCTCN2017109690-appb-000012
表5、玉米水培营养液配方
Figure PCTCN2017109690-appb-000013
由表4可知，干旱胁迫能降低玉米的生物量，喷施ABA和式II所示化合物后能明显提高玉米的生物量，喷施ABA的玉米干重为33.113g，活性最好，喷施式II所示化合物的玉米干重为28.069，活性次之，表明本发明所涉及化合物具有很好的诱导玉米抗旱的活性。
实施例3、化合物提高棉花(CCSI41，购于中棉所)耐盐性的生物活性测定
所有试验均在中国农业大学西校区转基因基地光照培养室完成，采用温室水培试验，随机区组排列，共5个处理，重复5次。培养室培养条件为光照14h(30℃)，黑暗10h(25℃)，光强450μmol m-2s-1。棉花种子经浓硫酸脱绒后，用10％的H2O2水溶液浸泡消毒15min。消毒后的种子温室条件下在灭菌水中浸泡12h，在经过预先高温杀菌的沙子中萌发出苗。待两片子叶完全展开(6d)，挑选生长一致的幼苗移栽到35cm×27cm×12cm的塑料盆中，盆中含有4L1/2-Hogland营养液，营养液有效成分见表7。
NaCl胁迫处理的方法如下：当幼苗的两片子叶完全展开时，将幼苗转移到自来水中适应一天，然后在1/4-Hogland营养液培养10d。在这一时期的后两天时，叶面分别喷施清水、100μM的ABA和本发明提供的式Ⅰ所示化合 物，施药24h后，向营养液中添加NaCl，营养液中NaCl的浓度每12h增加50mM，最终达到150mM的处理浓度。随后采用含有上述浓度NaCl的1/2-Hogland营养液。每隔3d更换一次营养液，每天添加一定量的去离子水补充蒸发失去的水分。盐胁迫处理10d后，棉花处于三叶期等待取样测定。
将式I所示化合物替换为式II至式VI所示化合物，按照如上步骤进行试验，对于每种化合物，试验重复3次，所得结果见表6。
表6、盐胁迫下化合物对棉花干重的影响
Figure PCTCN2017109690-appb-000014
表7、棉花水培营养液配方
Figure PCTCN2017109690-appb-000015
由表6可知，盐胁迫能降低棉花的生物量，喷施ABA和化合物后能明显提高玉米的生物量，喷施ABA的玉米干重为0.66g，活性最好，式III和式IV所示化合物的活性次之，分别为0.60g、0.55g，表明本发明所涉及化合 物具有很好的诱导棉花抗盐的活性。
实施例4、化合物提高小麦(济麦22，购于山东省农业科学院作物研究所)耐高温的生物活性测定
将小麦种子播种在口径16cm，高13cm的花盆中，采用混合基质(基质:土＝1:2)培养，每盆70～80粒，置于人工气候培养箱中，正常温度(白天20℃，夜间15℃)下，光照/黑暗(12h/12h)培养。当幼苗长到二叶一心期时，叶面分别喷施清水、100μM的ABA和本发明提供的式Ⅰ所示化合物，施药24h后，白天38℃，夜间28℃进行高温处理，于处理后3d，4d，5d，6d分别统计正常幼苗数，计算幼苗存活率。于第7d将材料置于正常温度(白天20℃，夜间15℃)下恢复7d，再次统计正常幼苗数，计算幼苗存活率。
将式I所示化合物替换为式II至式VI所示化合物，按照如上步骤进行试验，对于每种化合物，试验重复3次，所得结果见表8。
表8、恢复7d后小麦幼苗的存活率
Figure PCTCN2017109690-appb-000016
由表8可知，高温胁迫下，ABA能够提高小麦幼苗的成活率，成活率为52.3％，本发明多设计的大部分化合物都有一定的活性，其中式V所示化合物的活性较好，提高小麦幼苗的成活率为47.1％，表明本申请所涉及化合物具有很好的诱导小麦抗高温的活性。
实施例5、化合物除草活性的测定
将两层滤纸置于直径6厘米的一次性培养皿底部，每个皿中加入2mL试剂，以蒸馏水为对照。每个培养皿内均匀放置25粒饱满且大小均一的植物种子，在培养箱(光照条件，60％；白天：18h，25℃；黑夜：6h，20℃)中培养。
用本发明提供的式Ⅰ至式VI所示化合物的溶液(先用DMSO溶解化合物 配置成25mmol/L的母液，再用水稀释至100μmol/L)对常见杂草和作物进行培养皿浸种，在培养箱中培养。统计3天发芽势和7天发芽率，同时目测药害程度，测量其幼苗3天和7天的芽长和根长，初步定量评价化合物浸种实验的除草效果和安全性，对于每种化合物，试验重复3次，所得结果见表9。
表9、100μmol/L化合物溶液浸种7d后稗草种子发芽率
Figure PCTCN2017109690-appb-000017
由表9可知，ABA对稗草没有除草活性，而本发明所提供的化合物部分具有除草活性，其中式III所示化合物的活性最好，稗草种子的发芽率为25.32％，表明本申请所涉及化合物具有很好的除草活性。
工业应用
本发明提供的萘磺酰胺类化合物具有优良的植物生长调节活性，能够提高植物的耐冷性、耐旱性、耐盐性、耐高温性和除草活性，具有重要的应用价值。

Claims (15)

  1. 式I至式VI所示化合物中至少一种在调节植物生长活性和/或除草中的应用：
    Figure PCTCN2017109690-appb-100001
    Figure PCTCN2017109690-appb-100002
    所述式I至式VI中，X为F、Cl、Br或I。
  2. 一种调节植物生长活性的方法，包括：利用式I至式VI所示化合物中至少一种对植物进行施药：
    Figure PCTCN2017109690-appb-100003
    Figure PCTCN2017109690-appb-100004
    所述式I至式VI中，X为F、Cl、Br或I。
  3. 一种除草的方法，包括：用式I至式VI所示化合物中至少一种对植物进行施药：
    Figure PCTCN2017109690-appb-100005
    Figure PCTCN2017109690-appb-100006
    所述式I至式VI中，X为F、Cl、Br或I。
  4. 一种能同时调节植物生长活性和除杂草的方法，包括：利用式I至式VI所示化合物中至少一种对植物进行施药：
    Figure PCTCN2017109690-appb-100007
    Figure PCTCN2017109690-appb-100008
    所述式I至式VI中，X为F、Cl、Br或I。
  5. 根据权利要求2-4中任一所述的方法，其特征在于：所述施药中，施药部位为叶面。
  6. 根据权利要求2-5中任一所述的方法，其特征在于：所述施药中，施药方式为喷施；具体为喷施化合物的水溶液。
  7. 根据权利要求6所述的方法，其特征在于：所述化合物的水溶液的浓度为0.001-200μmol/L或50μmol/L。
  8. 根据权利要求2-7中任一所述的方法，其特征在于：所述施药中，施药量为每亩地施药15-30L化合物的水溶液。
  9. 含有式I至式VI中至少一种的植物生长活性调节剂：
    Figure PCTCN2017109690-appb-100009
    Figure PCTCN2017109690-appb-100010
    所述式I至式VI中，X为F、Cl、Br或I。
  10. 含有式I至式VI中至少一种的除草剂：
    Figure PCTCN2017109690-appb-100011
    Figure PCTCN2017109690-appb-100012
    所述式I至式VI中，X为F、Cl、Br或I。
  11. 一种能够同时调节植物生长活性并除草的产品，其特征在于：所述产品含有式I至式VI中至少一种：
    Figure PCTCN2017109690-appb-100013
    Figure PCTCN2017109690-appb-100014
    Figure PCTCN2017109690-appb-100015
    所述式I至式VI中，X为F、Cl、Br或I。
  12. 根据权利要求1-11中任一所述的应用或方法或植物生长活性调节剂或产品，其特征在于：所述调节植物生长活性为提高植物的耐冷性、耐旱性、耐盐性和耐高温性中至少一种。
  13. 根据权利要求9所述的植物生长活性调节剂，其特征在于：所述植物生长活性调节剂为提高植物的耐冷性、耐旱性、耐盐性和耐高温性中至少一种的调节剂。
  14. 根据权利要求1-13中任一所述的应用或方法或植物生长活性调节剂或除草剂或产品，其特征在于：所述植物为单子叶植物或双子叶植物。
  15. 根据权利要求14所述的应用或方法或植物生长活性调节剂或除草剂或产品，其特征在于：所述单子叶植物为小麦、水稻或玉米；和/或，
    所述双子叶植物为棉花。
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