WO2017143892A1 - Sulfonic acid ester acaricide containing spiro rings - Google Patents

Sulfonic acid ester acaricide containing spiro rings Download PDF

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WO2017143892A1
WO2017143892A1 PCT/CN2017/071622 CN2017071622W WO2017143892A1 WO 2017143892 A1 WO2017143892 A1 WO 2017143892A1 CN 2017071622 W CN2017071622 W CN 2017071622W WO 2017143892 A1 WO2017143892 A1 WO 2017143892A1
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formula
compound
acaricide
acid ester
sulfonic acid
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PCT/CN2017/071622
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French (fr)
Chinese (zh)
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许良忠
吴华龙
王明慧
鞠光秀
徐姗姗
陈格新
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浙江博仕达作物科技有限公司
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring

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  • the invention claims the priority of the Chinese invention patent application whose application date is February 25, 2016 and the application number is CN 201610102604.6.
  • the present invention relates to the field of acaricides in pesticides, and in particular to a sulfonate acaricide containing a spiro ring.
  • Plant pests are highly resistant to acaricides due to their strong fertility and short life cycle, which can severely reduce the yield of various crops.
  • acaricides such as scorpion, oxazolidine, acetylene, ethpyrazole, snail ester, etc. gradually decrease in effectiveness, and the duration of effect is gradually shortened.
  • Developing new acaricide varieties is the best way to solve the problem of resistance.
  • Patent CN 102060818 B discloses the preparation of a series of spirodecyl ester derivatives by reacting a compound of formula II with an alkyl chloroformate, some of which have good acaricidal activity.
  • Patent CN 103664850 B discloses an acaricide as shown in Formula III, which can be used alone or in combination with another biologically active compound to have a better control effect on agricultural pests.
  • the spirocyclic sulfonate acaricide and its acaricidal activity as described in the present invention have not been publicly reported at home and abroad.
  • the invention provides a sulfonate acaricide containing a spiro ring, and the structure is as shown in formula I:
  • the compound of formula I can be prepared by the following reaction:
  • the compound of formula II is reacted with butylsulfonyl chloride in the presence of an acid binding agent to form a compound of the invention (Formula I) in a solvent.
  • the acid binding agent is selected from the group consisting of triethylamine, pyridine, picoline, sodium carbonate (potassium), sodium hydrogencarbonate (potassium);
  • the solvent is selected from the group consisting of toluene, xylene, ethyl acetate, dichloromethane, chloroform, 1,2- Dichloroethane; butylsulfonyl chloride is added dropwise, the temperature is controlled from 0 ° C to 5 ° C, the purification method is recrystallization, and the solvent is selected from isopropanol.
  • the compound of the formula I is subjected to an indoor acaricidal egg activity test, and its activity is higher than that of the spironolactone at a concentration of 1 ⁇ g/mL and 0.1 ⁇ g/mL. Therefore, the present invention also includes the use of the compound of the formula I for controlling agricultural pests. .
  • the corrected mortality of the spirocyclic sulfonate-containing compound of the present invention against the eggs of T. cinnabarinus at the concentrations of 1 ⁇ g/mL and 0.1 ⁇ g/mL was 95% and 75%, respectively, higher than the control agent. 88% and 33% of snail esters (see Table 1).
  • the compound of the invention has simple preparation process and mild reaction condition, and is a new acaricide with good industrialization prospect.
  • the compound of the present invention can be used alone or in combination with other active substances in order to improve the comprehensive function of the product.
  • the invention also includes acaricidal compositions of the crop active component of the compound of formula I, which comprise a compound of formula I and an agriculturally acceptable carrier.
  • composition of the present invention can be used in the form of a preparation: the compound of the formula I is dissolved or dispersed in a carrier or a solvent as an active ingredient, and an appropriate amount of a surfactant is added to prepare a liquid, an emulsifiable concentrate, a microemulsion, an aqueous emulsion, a suspending agent. , dispersible oil suspension agent, etc.
  • Example 5 The activity of the acaricidal egg was determined by the method of dipping and statistically correcting the mortality of the pest. The specific process is: diluting the test agent to the required concentration according to the active ingredient, and immersing the leaves carrying the eggs of the cinnabar leaf mites (the eggs normally reared by the indoor standardized method) into the liquid, and gently shaking for 5 s. take out.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A sulfonic acid ester acaricide containing spiro rings, the structure thereof being shown in formula I; the present compound has an inhibiting and killing effect on pest mites and mite eggs, and can be used as an acaricide for preventing and controlling agricultural mites.

Description

一种含螺环的磺酸酯类杀螨剂Sulfonic ester acaricide containing spiro ring
本发明请求申请日为2016年02月25日、申请号为CN 201610102604.6的中国发明专利申请为优先权。The invention claims the priority of the Chinese invention patent application whose application date is February 25, 2016 and the application number is CN 201610102604.6.
技术领域 本发明属于农药中杀螨剂领域，具体涉及一种含螺环的磺酸酯类杀螨剂。TECHNICAL FIELD The present invention relates to the field of acaricides in pesticides, and in particular to a sulfonate acaricide containing a spiro ring.
背景技术 植物害螨因繁殖力强、生命周期短，极易对杀螨剂产生抗性，可使多种农作物严重减产。常用的杀螨剂如哒螨灵、唑螨酯、炔螨特、乙螨唑、螺螨酯等防效逐渐下降、持效期逐渐变短。开发新的杀螨剂品种是解决抗性问题的最好途径。BACKGROUND OF THE INVENTION Plant pests are highly resistant to acaricides due to their strong fertility and short life cycle, which can severely reduce the yield of various crops. Commonly used acaricides such as scorpion, oxazolidine, acetylene, ethpyrazole, snail ester, etc. gradually decrease in effectiveness, and the duration of effect is gradually shortened. Developing new acaricide varieties is the best way to solve the problem of resistance.
专利CN 102060818 B公布了一种用式II化合物与氯甲酸烷基酯反应制备出系列螺螨酯衍生物，其中部分化合物具有较好的杀螨活性。专利CN 103664850 B公布了一种如式III所示的杀螨剂，单一使用或与另外的生物活性化合物组合使用，对农业害螨有较好防治效果。在现有技术中，如本发明所述的含螺环的磺酸酯类杀螨剂及其杀螨活性在国内外未见公开报道。Patent CN 102060818 B discloses the preparation of a series of spirodecyl ester derivatives by reacting a compound of formula II with an alkyl chloroformate, some of which have good acaricidal activity. Patent CN 103664850 B discloses an acaricide as shown in Formula III, which can be used alone or in combination with another biologically active compound to have a better control effect on agricultural pests. In the prior art, the spirocyclic sulfonate acaricide and its acaricidal activity as described in the present invention have not been publicly reported at home and abroad.
Figure PCTCN2017071622-appb-000001
Figure PCTCN2017071622-appb-000001
发明内容Summary of the invention
本发明的目的是提供一种结构新颖、高效的螺螨磺酸酯类杀螨剂。It is an object of the present invention to provide a novel and highly efficient snail sulfonate acaricide.
本发明的技术方案如下：The technical solution of the present invention is as follows:
本发明提供了一种含螺环的磺酸酯类杀螨剂，结构如式I所示：The invention provides a sulfonate acaricide containing a spiro ring, and the structure is as shown in formula I:
Figure PCTCN2017071622-appb-000002
Figure PCTCN2017071622-appb-000002
式I化合物可由下列反应制得：The compound of formula I can be prepared by the following reaction:
Figure PCTCN2017071622-appb-000003
Figure PCTCN2017071622-appb-000003
式II化合物与丁基磺酰氯在缚酸剂存在下，于溶剂中反应生成本发明化合物(式I)。The compound of formula II is reacted with butylsulfonyl chloride in the presence of an acid binding agent to form a compound of the invention (Formula I) in a solvent.
缚酸剂选自三乙胺、吡啶、甲基吡啶、碳酸钠(钾)、碳酸氢钠(钾)；溶剂选自甲苯、二甲苯、乙酸乙酯、二氯甲烷、氯仿、1，2-二氯乙烷；丁基磺酰氯以滴加方式加入，控制温度为0℃-5℃，提纯方法为重结晶，溶剂选用异丙醇。The acid binding agent is selected from the group consisting of triethylamine, pyridine, picoline, sodium carbonate (potassium), sodium hydrogencarbonate (potassium); the solvent is selected from the group consisting of toluene, xylene, ethyl acetate, dichloromethane, chloroform, 1,2- Dichloroethane; butylsulfonyl chloride is added dropwise, the temperature is controlled from 0 ° C to 5 ° C, the purification method is recrystallization, and the solvent is selected from isopropanol.
式II化合物的制备方法见US 6436988 B1。For the preparation of the compounds of formula II, see US 6,436,988 B1.
将式I化合物进行室内杀螨卵活性试验，在1μg/mL和0.1μg/mL浓度下，其活性皆高于螺螨酯，因此，本发明还包括式I化合物用于防治农业害螨的用途。The compound of the formula I is subjected to an indoor acaricidal egg activity test, and its activity is higher than that of the spironolactone at a concentration of 1 μg/mL and 0.1 μg/mL. Therefore, the present invention also includes the use of the compound of the formula I for controlling agricultural pests. .
本发明的优点和积极效果：Advantages and positive effects of the present invention:
随着螺螨酯等常规杀螨剂的大量和频繁使用，害螨对常规杀螨剂产生了不同程度的抗药性。同等试验浓度下，本发明的含螺环的磺酸酯类化合物在1μg/mL和0.1μg/mL浓度下对朱砂叶螨螨卵的校正死亡率分别是95％和75％，高于对照药剂螺螨酯的88％和33％(见表1)。本发明化合物制备工艺简单、反应条件温和，是具有良好产业化前景的新杀螨剂。With the large and frequent use of conventional acaricides such as snail esters, mites produce varying degrees of resistance to conventional acaricides. At the same test concentration, the corrected mortality of the spirocyclic sulfonate-containing compound of the present invention against the eggs of T. cinnabarinus at the concentrations of 1 μg/mL and 0.1 μg/mL was 95% and 75%, respectively, higher than the control agent. 88% and 33% of snail esters (see Table 1). The compound of the invention has simple preparation process and mild reaction condition, and is a new acaricide with good industrialization prospect.
本发明化合物在防治害螨时，可单独使用，也可与其它活性物质组合使用，以利于提高产品的综合功能。本发明还包括式I化合物作物活性组分的杀螨组合物，该组合物中包括式I化合物以及农业上可接受的载体。The compound of the present invention can be used alone or in combination with other active substances in order to improve the comprehensive function of the product. The invention also includes acaricidal compositions of the crop active component of the compound of formula I, which comprise a compound of formula I and an agriculturally acceptable carrier.
本发明的组合物可以以制剂的形式使用：式I化合物作为活性组分溶于或分散于载体或溶剂中，添加适量的表面活性剂制成水剂、乳油、微乳剂、水乳剂、悬浮剂、可分散油悬浮剂等。The composition of the present invention can be used in the form of a preparation: the compound of the formula I is dissolved or dispersed in a carrier or a solvent as an active ingredient, and an appropriate amount of a surfactant is added to prepare a liquid, an emulsifiable concentrate, a microemulsion, an aqueous emulsion, a suspending agent. , dispersible oil suspension agent, etc.
应明确的是，在本发明的权利要求所限定的范围内，可进行各种变换和改动。It is to be understood that various modifications and changes can be made within the scope of the appended claims.
具体实施方式detailed description
下列合成实例、制剂实例及生测试验结果可用来进一步说明本发明，但不意味着限制本发明。The following synthetic examples, formulation examples, and bioassay results can be used to further illustrate the invention, but are not meant to limit the invention.
合成实例Synthesis example
实例1、式I化合物的制备Example 1, Preparation of a compound of formula I
在250mL三口烧瓶中依次加入100mL乙酸乙酯、15.7g(0.05mol)3-(2，4-二氯苯基)-2-氧代-1-氧杂螺[4，5]-癸-3-烯-4-醇、6.1g(0.06mol)三乙胺，搅拌溶解后，用冰水浴控温0℃-5℃，搅拌下滴加由9.40g(0.06mol)丁基磺酰氯和30mL乙酸乙酯组成的溶液，滴毕，室温搅拌反应2h～3h，TLC监测反应。反应结束后将反应液倒入饱和NaHCO3溶液(pH 8左右)，搅拌十分钟，分液，用40mL～60mL水洗涤有机层，有机相用无水Na2SO4干燥，减压旋蒸除去溶剂乙酸乙酯得到红棕色粘稠状液体，用50mL异丙醇重结晶，得到19.6g白色晶体，收率90.3％，熔点：85℃-87℃。100 mL of ethyl acetate and 15.7 g (0.05 mol) of 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4,5]-indole-3 were sequentially added to a 250 mL three-necked flask. - ene-4-ol, 6.1 g (0.06 mol) of triethylamine, stirred and dissolved, and then temperature-controlled from 0 ° C to 5 ° C with an ice water bath, and 9.40 g (0.06 mol) of butylsulfonyl chloride and 30 mL of acetic acid were added dropwise with stirring. A solution consisting of ethyl ester was added dropwise, and the reaction was stirred at room temperature for 2 h to 3 h, and the reaction was monitored by TLC. After completion of the reaction the reaction mixture was poured into saturated NaHCO 3 solution (pH about 8), stirred for ten minutes, liquid separation, the organic layer was washed with 40mL ~ 60mL of water, the organic phase was dried over anhydrous Na 2 SO 4, rotary evaporated under reduced pressure to remove The solvent ethyl acetate gave a reddish brown viscous liquid, which was recrystallized from 50 mL of isopropyl alcohol to give 19.6 g of white crystals, yield: 90.3%, mp.
1H NMR(500MHz，DMSO-d6)，δ(ppm)：0.81-0.84(m，3H)，1.27-1.33(m，2H)， 1.58-1.62(m，6H)，1.76-1.90(m，4H)，1.85-1.94(m，2H)，3.51-3.54(m，2H)，7.32-7.33(d，1H)，7.44-7.45(d，1H)，7.75(s，1H)。 1 H NMR (500 MHz, DMSO-d6), δ (ppm): 0.81-0.84 (m, 3H), 1.27-1.33 (m, 2H), 1.58-1.62 (m, 6H), 1.76-1.90 (m, 4H) ), 1.85-1.94 (m, 2H), 3.51-3.54 (m, 2H), 7.32-7.33 (d, 1H), 7.44-7.45 (d, 1H), 7.75 (s, 1H).
制剂实例Formulation example
实例2、5％式I化合物微乳剂的制备Example 2, Preparation of 5% Formula I Compound Microemulsion
向250mL烧杯中分别加入5g式I化合物和20g乙酸乙酯，搅拌溶解，加入10g农乳1601#和15gNP-7，搅拌均匀后加入50g水，充分搅拌0.5h，得5％式I化合物微乳剂。Add 5g of the compound of formula I and 20g of ethyl acetate to a 250mL beaker, stir and dissolve, add 10g of agricultural milk 1601# and 15gNP-7, stir evenly, add 50g of water, stir well for 0.5h, 5% of formula I compound microemulsion .
实例3、25％式I化合物悬浮剂的制备Example 3, Preparation of 25% Compound Suspending Agent of Formula I
向250mL烧杯中分别加入25g式I化合物、5g Morwet D-500、7g吐温80、2g白炭黑、15g0.1％的黄原胶水溶液、4g乙二醇和42g水，搅拌均匀，转入砂磨机中充分研磨3h，得25％式I化合物悬浮剂。25 g of the compound of the formula I, 5 g of Morwet D-500, 7 g of Tween 80, 2 g of white carbon black, 15 g of a 0.1% aqueous solution of xanthan gum, 4 g of ethylene glycol and 42 g of water were respectively added to a 250 mL beaker, stirred uniformly, and transferred to sand. Grinding well for 3 h in a mill gave 25% suspension of the compound of formula I.
实例4、25％式I化合物可分散油悬浮剂的制备Example 4 Preparation of 25% Compound Dispersible Oil Suspension of Formula I
向250mL烧杯中分别加入25g式I化合物，15g SP-OF3404、5g EL-40，3g有机膨润土，52g油酸甲酯，搅拌均匀，转入砂磨机中充分研磨3h，得25％式I化合物可分散油悬浮剂。25 g of the compound of the formula I, 15 g of SP-OF3404, 5 g of EL-40, 3 g of organic bentonite, 52 g of methyl oleate were added to a 250 mL beaker, stirred uniformly, and transferred to a sand mill for 3 h to obtain 25% of the compound of the formula I. Dispersible oil suspension concentrate.
生物活性测定Biological activity assay
实例5、采用浸渍法和统计校正害虫死亡率的方法测定杀螨卵活性。具体过程是：将供试药剂按有效成分分别稀释至所需浓度，将载有朱砂叶螨螨卵(螨卵按室内标准化方法正常饲养的群体)的叶片浸入药液中，轻轻振荡5s后取出。吸去叶片上多余的药液，置于铺有润湿滤纸的培养皿内，用保鲜膜覆盖，以不含药剂的处理做空白对照，将培养皿放在(25±1)℃恒温培养箱内饲养和观察，待对照卵孵化并发育至弱螨阶段时调查孵化数，统计死亡率。每处理3次重复，结果取平均值，试验结果见表1。Example 5. The activity of the acaricidal egg was determined by the method of dipping and statistically correcting the mortality of the pest. The specific process is: diluting the test agent to the required concentration according to the active ingredient, and immersing the leaves carrying the eggs of the cinnabar leaf mites (the eggs normally reared by the indoor standardized method) into the liquid, and gently shaking for 5 s. take out. Absorb the excess liquid on the blade, place it in a petri dish covered with moist filter paper, cover with plastic wrap, use a non-pharmaceutical treatment as a blank control, and place the culture dish in a (25 ± 1) °C constant temperature incubator In-line feeding and observation, when the control eggs hatched and developed to the weak stage, the hatching number was investigated and the mortality was counted. Each treatment was repeated 3 times, and the results were averaged. The test results are shown in Table 1.
表1 本发明化合物(式I)对朱砂叶螨螨卵的活性Table 1 Activity of the compound of the present invention (Formula I) on eggs of T. cinnabarinus
Figure PCTCN2017071622-appb-000004
Figure PCTCN2017071622-appb-000004
由表1试验数据可见，在相同剂量下，本发明式I化合物对朱砂叶螨螨卵的活性均高于或同于螺螨酯。 It can be seen from the test data of Table 1 that the activity of the compound of the formula I of the present invention against the eggs of the cinnabarinus is higher than or identical to the snail ester at the same dose.

Claims (3)

  1. 一种含螺环的磺酸酯类杀螨剂，结构如式I所示：A sulfonate acaricide containing a spiro ring, the structure is as shown in formula I:
    Figure PCTCN2017071622-appb-100001
    Figure PCTCN2017071622-appb-100001
  2. 根据权利要求1所述的一种含螺环的磺酸酯类杀螨剂，其特征在于式I化合物可作为杀螨剂用于防治农业害螨。A spirocyclic sulfonate acaricide according to claim 1, wherein the compound of the formula I is useful as an acaricide for controlling agricultural pests.
  3. 一种杀螨组合物，含有权利要求1所述的式I化合物作为活性组分和农业或林业上可接受的载体。 A acaricidal composition comprising a compound of formula I as claimed in claim 1 as an active ingredient and an agricultural or forestry acceptable carrier.
PCT/CN2017/071622 2016-02-25 2017-01-19 Sulfonic acid ester acaricide containing spiro rings WO2017143892A1 (en)

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CN105646421B (en) * 2016-02-25 2018-06-15 浙江博仕达作物科技有限公司 A kind of sulfonic acid esters acaricide containing loop coil
CN107602515A (en) * 2017-10-13 2018-01-19 南开大学 One kind 5A5B6CTricyclic spiro lactone derivatives and its production and use

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