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WO2018137128A1 - 预防和/或治疗姜瘟的组合物、方法和噁二唑类化合物用于预防和/或治疗姜瘟的用途 - Google Patents

预防和/或治疗姜瘟的组合物、方法和噁二唑类化合物用于预防和/或治疗姜瘟的用途 Download PDF

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WO2018137128A1
WO2018137128A1 PCT/CN2017/072425 CN2017072425W WO2018137128A1 WO 2018137128 A1 WO2018137128 A1 WO 2018137128A1 CN 2017072425 W CN2017072425 W CN 2017072425W WO 2018137128 A1 WO2018137128 A1 WO 2018137128A1
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formula
compound
ginger
preventing
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郭庆春
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical

Definitions

  • the present invention relates to a composition, method, and use of an oxadiazole compound for preventing and/or treating ginger mites for preventing and/or treating ginger mites.
  • Ginger disease also known as ginger rot disease or bacterial bacterial wilt
  • Ginger disease is a common and widespread devastating bacterial disease in ginger production. It is a serious soil-borne disease. Pathogens are easily accessible from strains, roots and stems. The wound invades the plant, causing the disease of the plant, and the drug control effect of the ginger blast after the onset is not satisfactory. According to reports, the main ginger growing areas in China have lost 30% to 40% due to the damage of ginger rickets, and the loss of seriously ill fields is as high as 70%, which seriously affects the yield and quality of ginger. Therefore, there is an urgent need for drugs that have a good control effect on ginger rickets.
  • the present invention aims to provide a medicament which is particularly effective against ginger.
  • oxadiazole compound represented by the following formula (I) is particularly effective for the prevention and/or treatment of ginger mites.
  • R1 to R8 are each independently hydrogen, a C1-C6 alkyl group or a C1-C6 alkoxy group optionally substituted by a halogen atom, a halogen atom, and the halogen atom is fluorine, chlorine, bromine or Iodine; E is O or S.
  • PCT application WO 2009/023721 discloses an oxadiazole compound represented by the above formula (I), and describes the use of the compound for controlling nematodes.
  • the inventors of the present application unexpectedly found that the above compound has an excellent preventive and/or therapeutic effect on ginger mites, thereby obtaining the present invention.
  • the invention relates to:
  • a composition for preventing and/or treating ginger mites which comprises an oxadiazole compound represented by the above formula (I) as an active ingredient, and contains an auxiliary or auxiliary agent which is allowed to be used in a pesticide.
  • R1-R8 in the above formula (I) are each independently The ground is hydrogen, a halogen atom, an unsubstituted C1-C6 alkyl group or a C1-C6 alkoxy group.
  • R1 to R8 in the above formula (I) are each independently hydrogen or a C1-C6 alkyl group.
  • the compound of the above formula (I) is most preferably a compound represented by the following formula (II) or formula (III):
  • the compounds of the above formula (I), (II) and (III) of the present invention can be produced by the method described in WO2009/023721, and polymorphic forms thereof are included in the scope of the present invention.
  • the above compounds are applied in an amount of from 50 to 7500 g/hm, preferably from 450 to 2500 g/hm.
  • the above compound is applied in an amount of from 0.1 to 50 g per 100 kg of the seed, preferably from 0.5 to 5 g per 100 kg of the seed.
  • the above compounds may be allowed in combination with one or more agriculture as needed
  • auxiliaries such as stabilizers, binders, emulsifiers, antifoaming agents, viscosity modifiers, etc.
  • Known auxiliaries such as stabilizers, binders, emulsifiers, antifoaming agents, viscosity modifiers, etc.
  • emulsifiable concentrates suspending agents
  • wettable powders Water-dispersible granules, water emulsions, microemulsions, granules, microcapsules, water-based agents, and the like.
  • the pesticide preparation usually contains 0.1 to 95% by weight, preferably 5 to 80% by weight, based on the above compound.
  • the application frequency of the above-mentioned compound or pesticide preparation of the present invention depends on the degree of onset of the ginger mites, and may be administered once or multiple times.
  • the above compounds of the present invention can be administered in combination with other pesticides including bactericides, insecticides and the like.
  • administered in combination includes alternating application or mixing together to form a mixture.
  • a stock solution 2 was prepared by taking 2.0 g of a compound of the formula (III) dissolved in a mixture of 16 ml of cyclohexanone and 2.0 g of nonylphenol ethoxylate.
  • the stock solution 1, stock solution 2 and blank control stock solution 3 prepared above were diluted 1000 times with water, respectively, as reagent 1, reagent 2 and blank control reagent 3.
  • the reagent 1 treatment zone, the reagent 2 treatment zone, and the blank control reagent 3 treatment zone were set. Each treatment was repeated 5 times, and the random block group was arranged, and the cell area was 66.7 m 2 . The total area of each treatment zone was 667 m 2 , and the amount of ginger was 500 kg.
  • the seeds were soaked for 15 to 30 minutes with the entire amount of the above reagent 1, reagent 2 and blank control reagent 3, and then sown after 1 to 2 days. Daily management after sowing is the same as regular management in production.
  • Relative control effect (%) (incidence rate of Jiangyan in the blank control area - incidence rate of ginger in the treatment area) / blank The incidence of Jiangyan in the control area ⁇ 100%
  • a blank emulsifiable concentrate 3 containing no active ingredient is prepared in the same manner as the above emulsifiable concentrate except that the compound of the formula (II) and the formula (III) is not added.
  • the emulsifiable concentrate 1, the cream 2 and the cream 3 prepared above were each diluted with water to 400 L, and used as the reagent 4, the reagent 5, and the blank control reagent 6, respectively.
  • a reagent 4 treatment zone, a reagent 5 treatment zone, and a blank control reagent 6 treatment zone were set. Each treatment was repeated 4 times, and the random area was arranged. The area of the plot was 66.7 m 2 , and the cultivation density of ginger was 8,000 plants per mu. Daily management and regular management in production. The roots were irrigated once with the above reagents during the three-strand period of ginger, and the reagent amount per cell was 100L. When filling the roots, the sprayer with the spray head removed is applied so that the liquid penetrates into the root of the ginger.
  • the incidence of the reagent 4 treatment zone and the reagent 5 treatment zone is much lower than that of the blank control reagent 6 treatment zone, and the compound of the present invention has a good preventive and/or therapeutic effect on ginger mites. .
  • the stock solution 7, the stock solution 8, and the blank control stock solution 9 prepared above were each diluted with water to 60 L, and used as reagent 7, reagent 8, and control reagent 9, respectively.
  • the three cells were each rooted with the entire amount of the above reagent 7, reagent 8 and control reagent 9.
  • the rooting method is the same as described in Example 2.
  • the invention solves the problem of ginger mites which are common and difficult to prevent and/or treat in the ginger planting industry, and can greatly improve the yield and quality of ginger.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

含有下式(I)所示的噁二唑类化合物的用于预防和/或治疗姜瘟的组合物、采用该化合物预防和/或治疗姜瘟的方法以及该化合物用于预防和/或治疗姜瘟的用途。式(I)中，R1-R8各自独立地为氢、任选被卤原子取代的C1-C6烷基或C1-C6烷氧基、卤原子；E为O或者S。

Description

预防和/或治疗姜瘟的组合物、方法和噁二唑类化合物用于预防和/或治疗姜瘟的用途 技术领域
本发明涉及用于预防和/或治疗姜瘟的组合物、方法、以及噁二唑类化合物用于预防和/或治疗姜瘟的用途。
背景技术
姜瘟病又称姜腐烂病或细菌性青枯病，是生姜生产中常见且普遍发生的一种毁灭性细菌病害，是一种严重的土传病害，病原菌极易从菌种、根系、茎部伤口侵入植株，引起植株染病，并且姜瘟病在发病后的药物防治效果不理想。据报道，中国主要生姜栽培区常年由于姜瘟病的危害而损失30％～40％，重病田损失高达70％以上，严重影响生姜的产量和品质。因此，亟需对姜瘟病具有好的防治效果的药物。
发明内容
本发明旨在提供一种对由姜瘟特别有效的药物。
本申请发明人进行研究后发现，下式(I)所示的噁二唑类化合物对姜瘟的预防和/或治疗特别有效。
Figure PCTCN2017072425-appb-000001
上式(I)中，R1-R8各自独立地为氢、任选被卤原子取代的C1-C6烷基或C1-C6烷氧基、卤原子，所述卤原子为氟、氯、溴或者碘；E为O或者S。
PCT申请WO2009/023721公开了上述式(I)所示的噁二唑类化合物，并记载了该化合物用于控制线虫的用途。而本申请发明人意外地发现上述化合物对姜瘟具有优异的预防和/或治疗效果，从而获得了本发明。
具体地，本发明涉及：
(1)用于预防和/或治疗姜瘟的组合物，该组合物含有上式(I)所示的噁二唑类化合物作为活性成分，并含有农药上允许使用的助剂或辅料。
(2)预防和/或治疗姜瘟的方法，该方法包括施用有效量的上式(I)所示的噁二唑类化合物。
(3)上式(I)所示的噁二唑类化合物用于预防和/或治疗姜瘟的用途。
具体实施方式
在本发明优选的实施方式中，上述式(I)中的R1-R8各自独立 地为氢、卤原子、未取代的C1-C6烷基或C1-C6烷氧基。
在本发明更优选的实施方式中，上述式(I)中的R1-R8各自独立地为氢或C1-C6烷基。
本发明中，上述式(I)的化合物最优选为下述式(II)或式(III)所示的化合物：
Figure PCTCN2017072425-appb-000002
本发明的上述式(I)、(II)和(III)的化合物可以通过WO2009/023721中记载的方法来制备，其多晶形式均包括在本发明范围之内。
在本发明优选的实施方式中，以50～7500g/hm、优选450～2500g/hm的量施用上述化合物。
在本发明其它优选的实施方式中，上述化合物以0.1～50g/100kg种子的量施用上述化合物，优选0.5～5g/100kg种子。
本发明中，上述化合物可以根据需要与一种或多种农业中允许 使用的公知助剂，例如稳定剂、粘合剂、乳化剂、消泡剂、粘度调节剂等，通过公知的方法制成各种农药制剂，包括但不限于乳油、悬浮剂、可湿性粉剂、水分散粒剂、水乳剂、微乳剂、颗粒剂、微胶囊剂、水剂等。农药制剂中，通常含有上述化合物0.1-95重量％，优选为5-80重量％。
本发明上述化合物或者农药制剂的施用频率根据姜瘟的发病程度而定，可以一次给药，也可以多次给药。
优选以液体制剂形式浸种、灌根或喷洒茎叶，一般在施用时稀释200～4000倍使用。这些可以由本领域技术人员视情况合理确定。
本发明上述化合物可以与其它农药一起联合施用，所述农药包括杀菌剂、杀虫剂等。术语“联合施用”包括分开交替施用或者一起混配制成混剂。
实施例
以下通过实施例更具体地说明本发明，但本发明不限于这些实施例。在不脱离本发明主旨范围内的任何变更均包括在本发明范围内。
按照WO2009/023721中记载的方法制备前述式(II)和式(III)所示的化合物。
实施例1
(1)取2.0g的式(II)化合物溶于16ml环己酮和2.0克壬基 酚聚氧乙烯醚的混合物中，制备储液1。
(2)取2.0g的式(III)化合物溶于16ml环己酮和2.0克壬基酚聚氧乙烯醚的混合物中，制备储液2。
(3)取20ml环己酮和2.0克壬基酚聚氧乙烯醚的混合物作为空白对照储液3。
田间效果测试
从地窖中取出姜种，将其晾晒一天。凉完后，用软毛刷去除姜种表面泥土，注意尽量不要伤害姜种表皮。
即将使用前，将上述制备的储液1、储液2和空白对照储液3分别用水稀释1000倍，分别作为试剂1、试剂2和空白对照试剂3。
设置试剂1处理区、试剂2处理区和空白对照试剂3处理区。每个处理重复5次，随机区组排列，小区面积66.7m2。每个处理区总面积为667m2，种姜用量为500kg，分别用全部量的上述试剂1、试剂2和空白对照试剂3浸种15～30分钟后，凉1～2天后播种。播种后的日常管理同生产上的常规管理。
分别在三股杈时期和大培土时期各调查一次，调查各处理区的姜瘟发病率和相对防效。将出现叶子萎焉、发黄，叶边缘卷曲、叶片干枯，拔出后发现茎基部发生腐烂等典型姜瘟症状的株定为姜瘟发病株。
姜瘟发病率(％)＝姜瘟发病株数/总株数×100％
相对防效(％)＝(空白对照区姜瘟发病率-处理区姜瘟发病率)/空白 对照区姜瘟发病率×100％
结果如下表1所示。
表1
Figure PCTCN2017072425-appb-000003
由上表中的结果可知，试剂1处理区和试剂2处理区的发病率远远低于空白对照处理区，本发明所述的化合物对姜瘟具有很好的预防效果。
实施例2
(1)取20g的式(II)化合物溶于160g的二甲苯中，加入十二烷基苯磺酸钙和壬基酚聚氧乙烯醚各10g，得到含式(II)化合物的乳油1。
(2)取20g的式(III)化合物溶于160g的二甲苯中，加入十二烷基苯磺酸钙和壬基酚聚氧乙烯醚各10g，得到含式(III)化合物的乳油2。
(3)除了不加入式(II)和式(III)的化合物，与上述乳油同法制备不含活性成分的空白乳油3。
田间效果测试
将上述制备的乳油1、乳油2和乳油3分别加水稀释至400L，分别作为试剂4、试剂5和空白对照试剂6。
设置试剂4处理区、试剂5处理区和空白对照试剂6处理区。每个处理重复4次，随机区排列，小区面积66.7m2，生姜的栽培密度为每亩8000株。日常管理同生产上的常规管理。在生姜三股杈时期用上述试剂灌根1次，每小区试剂用量为100L。灌根时用去掉喷头的喷雾器灌施，以便药液渗入生姜根部。
在灌根后第15天和第30天各调查一次，按照与实施例1中相同的方法调查各处理区的姜瘟发病率和相对防效。
结果如表2所示
表2
Figure PCTCN2017072425-appb-000004
由上表中的结果可知，试剂4处理区和试剂5处理区的发病率远远低于空白对照试剂6处理区，本发明所述的化合物对姜瘟具有很好的预防和/或治疗效果。
实施例3
(1)取5g的式(II)化合物溶于环己酮(40ml)和壬基酚聚氧乙烯醚(5g)的混合物中，得到含式(II)化合物的储液7。
(2)取5g的式(III)化合物溶于环己酮(40ml)和壬基酚聚氧乙烯醚(5g)的混合物中，得到含式(III)化合物的储液8。
(3)用环己酮(50ml)和壬基酚聚氧乙烯醚(5g)的混合物作为空白对照储液9。
田间效果测试
选取已经有姜瘟发病的种姜地200m2，均分为三个小区，施药前按照与实施例1中同样的病株定义标准分别计数各区已经发病的株数。
将上述制备的储液7、储液8和空白对照储液9分别加水稀释至60L，分别作为试剂7、试剂8和对照试剂9。
将三个小区分别用全部量的上述试剂7、试剂8和对照试剂9灌根。灌根方法同实施例2中所述。
在施药后第30天调查各区姜瘟病株数，计算病株增减数和增减率。
结果如表3所示
表3
处理 施药前病株数 施药后病株数 施药后病株增减率
试剂7 162 122 －24.7％
试剂8 145 104 －28.3％
空白对照试剂9 154 265 +72.1％
由上表中的结果可知，空白对照试剂9处理区的姜瘟病株数量在30天的时间里显著增加，而试剂7处理区和试剂8处理区的姜瘟病株数量显著减少，表明本发明所述的噁二唑类化合物对已发的姜 瘟病具有很好的治疗效果。
工业实用性
本发明解决了生姜种植产业中普遍并且难以预防和/或治疗的姜瘟问题，从而能够大幅提高生姜产量和质量。

Claims (15)

  1. 用于预防和/或治疗姜瘟的组合物，其含有下式(I)所示的噁二唑类化合物作为活性成分，并含有农药上允许使用的助剂或辅料，
    Figure PCTCN2017072425-appb-100001
    上式(I)中，
    R1-R8各自独立地为氢、任选被卤原子取代的C1-C6烷基或C1-C6烷氧基、卤原子，所述卤原子为氟、氯、溴或者碘；
    E为O或者S。
  2. 权利要求1所述的组合物，其中R1-R8各自独立地为氢或C1-C6烷基。
  3. 权利要求1所述的组合物，其中，上述式(I)所示的噁二唑类化合物为下述式(II)或式(III)所示的化合物：
    Figure PCTCN2017072425-appb-100002
    Figure PCTCN2017072425-appb-100003
  4. 权利要求1至3中任意一项所述的组合物，该组合物的施用量按照上述式(I)、式(II)或式(III)的化合物计为50～7500g/hm，或者是0.1～50g/100kg种子。
  5. 权利要求4所述的组合物，该组合物的施用量按照上述式(I)、式(II)或式(III)的化合物计为450～2500g/hm，或者是0.5～5g/100kg种子
  6. 下式(I)所示的噁二唑类化合物用于预防和/或治疗姜瘟的用途，
    Figure PCTCN2017072425-appb-100004
    上式(I)中，
    R1-R8各自独立地为氢、任选被卤原子取代的C1-C6烷基或C1-C6烷氧基、卤原子，所述卤原子为氟、氯、溴或者碘；
    E为O或者S。
  7. 权利要求6所述的用途，其中R1-R8各自独立地为氢或C1-C6烷基。
  8. 权利要求6所述的用途，其中，上述式(I)的化合物为下述式(II)或式(III)所示的化合物：
    Figure PCTCN2017072425-appb-100005
  9. 权利要求6至8中任意一项所述的用途，其中上述式(I)、式(II)或式(III)的化合物的用量为50～7500g/hm，或者是0.1～50g/100kg种子。
  10. 权利要求9所述的用途，其中上述式(I)、式(II)或式(III)的化合物的用量为450～2500g/hm，或者是0.5～5g/100kg种子。
  11. 预防和/或治疗姜瘟的方法，该方法包括使用有效量的下式(I)所示的噁二唑类化合物，
    Figure PCTCN2017072425-appb-100006
    上式(I)中，
    R1-R8各自独立地为氢、任选被卤原子取代的C1-C6烷基或C1-C6烷氧基、卤原子，所述卤原子为氟、氯、溴或者碘；
    E为O或者S。
  12. 权利要求11所述的方法，其中，R1-R8各自独立地为氢或C1-C6烷基。
  13. 权利要求11所述的方法，其中，上述式(I)的化合物为下述式(II)或式(III)所示的化合物：
    Figure PCTCN2017072425-appb-100007
  14. 权利要求11至13中任意一项所述的方法，其中上述式(I)、式(II)或式(III)的化合物的用量为50～7500g/hm，或者是0.1～50g/100kg种子。
  15. 权利要求14所述的方法，其中上述式(I)、式(II)或式(III)的化合物的用量为450～2500g/hm，或者是0.5～5g/100kg种子。
PCT/CN2017/072425 2017-01-24 2017-01-24 预防和/或治疗姜瘟的组合物、方法和噁二唑类化合物用于预防和/或治疗姜瘟的用途 Ceased WO2018137128A1 (zh)

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CN101820761A (zh) * 2007-08-13 2010-09-01 达沃股份有限公司 用于控制线虫的组合物和方法
CN104488911A (zh) * 2014-12-18 2015-04-08 广西田园生化股份有限公司 一种含甲磺酰菌唑的杀虫杀菌组合物及制剂
CN104936451A (zh) * 2012-12-04 2015-09-23 孟山都技术公司 杀线虫水性悬浮浓缩组合物
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US5633271A (en) * 1992-05-26 1997-05-27 E. I. Du Pont De Nemours And Company Arthropodicidal oxazolines and thiazolines
US5912243A (en) * 1994-03-10 1999-06-15 Zeneca Limited (4,4-difluorobut-3-enylthio)-substituted heterocyclic or carbocyclic ring compounds having pesticidal activity
CN101820761A (zh) * 2007-08-13 2010-09-01 达沃股份有限公司 用于控制线虫的组合物和方法
CN104936451A (zh) * 2012-12-04 2015-09-23 孟山都技术公司 杀线虫水性悬浮浓缩组合物
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