CN109232550A - 一种含3-氯-5-三氟甲基吡啶基-1,3,4-噁二唑-2-酮类化合物及其应用 - Google Patents
一种含3-氯-5-三氟甲基吡啶基-1,3,4-噁二唑-2-酮类化合物及其应用 Download PDFInfo
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
Abstract
本发明公开了一种含3‑氯‑5‑三氟甲基吡啶基‑1,3,4‑噁二唑‑2‑酮类化合物,其结构通式如I所示:通式I中R选自:
Description
技术领域 本发明属于农用杀虫、杀螨剂领域,涉及一种含3-氯-5-三氟甲基吡啶基-1,3,4-噁二唑-2-酮类化合物及其应用。
背景技术 农业上的害虫导致作物减产及品质下降,目前其防治技术主要依赖化学农药。由于化学农药长期大量频繁的使用,有害生物对其产生了严重抗药性,导致防效降低、防治成本升高。开发新型不同作用机制的杀虫药剂,是克服或延缓有害生物抗药性的重要手段。1,3,4-噁二唑-2-酮类化合物属于五元杂环类化合物,具有广泛的生理和生物活性,不仅在医药的研究和开发中具有抗炎、降压、降血脂等生理活性,在新农药的研究和开发中也具有杀虫、杀菌、除草等生物活性。CN 105646393 A公开了如下具有生物活性的化合物(KC)。
该化合物(KC)属于二取代噁二唑类化合物,全新的化学结构赋予其新的作用机理和杰出的产品性能,用于农作物线虫的防治具有低剂量、长持效及低公害等特点。在现有技术中如本发明所述的通式I化合物及其在农药中的应用性能未见公开。
发明内容 本发明的目的在于提供一种结构新颖的含3-氯-5-三氟甲基吡啶基-1,3,4-噁二唑-2-酮类化合物,它可用于农业或林业常见的虫害、螨害的有效防治。
本发明的技术方案如下:
一种含3-氯-5-三氟甲基吡啶基-1,3,4-噁二唑-2-酮类化合物,化学结构如通式I所示:
通式I中R选自:
本发明通式I化合物可通过如下反应制备,反应式中各基团定义同前。
中间体A在溶剂乙酸乙酯中,以三乙胺做催化剂,滴加溶在乙酸乙酯中的固体光气,常温反应2h,制得本发明化合物(通式I)。中间体A和的通式I化合物的制法见本说明书合成实施例。表1列出了通式I化合物的结构和物理性质。
表1通式I化合物的结构和物理性质
本发明的优点及积极效果:噁二唑杂环化合物是当前新农药开发的热点,成为在新农药创制中提高生物活性及治理抗药性的重要手段。本发明化合物(通式I)具有结构新颖、合成方法简单、杀虫杀螨效果优异的优点。本发明化合物(通式I)具有一药多治、降低防治成本、克服或延缓有害生物体抗药性等意想不到的综合性能。本发明化合物为氮杂环类化合物,具有对人、畜及有益生物低毒性、易降解、环境相容性好的特点,作为新农药创制品种,具有十分广阔的开发及应用前景。因此,本发明还包括通式I化合物用于控制农业虫害、螨害的用途。
本发明化合物在防治虫、螨害时,可根据实际需要既可以单独使用,也可以与其他杀虫、杀螨剂等活性物质组合使用,以提高产品的综合性能。
本发明还包括以通式I化合物作为活性组分的杀虫、杀螨组合物,其中活性组分在组合物的重量百分含量为1~99%。该组合化合物还包括农业上可接受的载体。
本发明的组合物可以制剂的形式施用。通式I化合物作为活性组分溶解或分散于载体或溶剂中,添加适当的表面活性剂配制成乳油、悬浮剂、微乳剂或可湿性粉剂等。
应明确的是,本发明的权利要求限定的范围内,可进行各种变换和改动。
具体实施方式:
以下合成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。
合成实例
实例1、化合物Ia的制备:
(1)3-氯-2-肼基-5-(三氟甲基)吡啶的合成:
在250mL反应瓶中,加入21.6g(0.1mol)2,3-二氯-5-(三氟甲基)吡啶,100mL乙醇和12.5g(0.2mol)质量分数80%的水合肼,搅拌,升温至50℃,控温反应2h,TLC监测至反应完全。旋蒸除去溶剂乙醇,得白色固体20.8g,收率98.3%。
(2)2-(三氟甲基)苯甲酰氯的合成:
向250mL的三口烧中依次加入2-(三氟甲基)苯甲酸9.5g(0.05mol),甲苯100mL,氯化亚砜7.14g(0.06mol),加热至80℃,控温反应3h。反应完毕,蒸出甲苯和氯化亚砜,得2-(三氟甲基)苯甲酰氯10.29g,收率98.7%。
(3)3-氯-5-(三氟甲基)-2-(2-(2-(三氟甲基)苯基)肼基)吡啶的合成:
在250mL反应瓶中,加入3-氯-5-(三氟甲基)-2-(2-(2-(三氟甲基)苯基)肼基)吡啶16.92g(0.08mol),120mL乙腈和9.7g(0.096mol)缚酸剂三乙胺,搅拌,冰浴下滴加18.34g(0.088mol)邻三氟苯甲酰氯。冰浴条件下,反应1h,TLC监测至反应完全。加入适量冰水,大量白色固体析出,抽滤得白色固体26.5g,收率93.18%。
(4)化合物Ia的合成:
在250mL反应瓶中,加入17.77g(0.05mol)3-氯-5-(三氟甲基)-2-(2-(2-(三氟甲基)苯基)肼基)吡啶,70mL乙酸乙酯,15.15g(0.15mol)三乙胺,搅拌,用50mL乙酸乙酯溶解14.85g(0.05mol)固体光气,常温下滴加到反应瓶中,反应4h。TLC监测至反应完全,过滤除去三乙胺盐酸盐,滤液旋蒸,得淡黄色油状物,经柱层层析纯化得白色固体13.4g,收率65.4%。熔点100-102℃。1H NMR(500MHz,DMSO-d6)δ9.08(d,J=2.0Hz,1H),8.87(d,J=2.0Hz,1H),7.83(d,J=8.5Hz,2H),7.63(d,J=8.5Hz,2H),1.32(s,9H)。
按照以上方法,以代替可以制备化合物Ib或Ic。
其他化合物的核磁数据如下:
化合物Ib:1H NMR(500MHz,DMSO-d6)δ(ppm):8.81(s,1H),8.20(d,J=2.0Hz,1H),8.01–7.95(m,1H),7.92–7.86(m,1H),7.78–7.71(m,2H)。
化合物Ic:1H NMR(500MHz,DMSO-d6)δ(ppm):9.03(d,J=2.0Hz,1H),8.82(d,J=2.0Hz,1H),6.83(d,J=9.4Hz,1H),2.62(d,J=8.6Hz,1H),2.40(t,J=9.0Hz,1H),1.36(s,3H),1.24(s,3H)。
生物活性测定
实例2、杀虫活性测定
(1)杀小菜蛾活性测试方法:本发明化合物对小菜蛾活性测定采用国际抗性行动委员会(IRAC)提出的浸叶法。用配制好的待测药液,用直头眼科镊子浸渍甘蓝叶片,时间3~5秒,甩掉余液,每次1片,每个样品共3片,按照样品标记的顺序依次放在处理纸上。待药液干后,放入具有标记的10cm长的直型管内,接入2龄小菜蛾幼虫30头,用纱布盖好管口。将试验处置于标准处理室内,48h检查结果以拔针轻触虫体,不动者为死亡。计算死亡率。(试验做3次重复,取平均值)
在浓度为50ppm时,化合物Ia、Ib、Ic对小菜蛾的致死率均为100%;在10ppm时,化合物Ib、Ic对小菜蛾的致死率在90%以上;按照以上方法,选取化合物Ic与已知化合物KC进行杀小菜蛾活性平行测定。试验结果见表2。
表2杀小菜蛾活性测试结果
实例3、杀螨活性测定
杀朱砂叶螨活性测定采用国际抗性委员会(IRAC)提出的喷雾法。将菜豆幼叶叶片用打孔器打成直径2厘米的叶碟,用Airbrush喷雾处理,一定浓度的测试化合物在每叶碟正反面喷雾,喷雾量为0.5毫升,阴干后每处理接入20头试虫(3龄)。处理后放入24℃、相对湿度60%~70%、无光照的室内培养,48小时后调查存活虫数,计算死亡率。(试验做3次重复,取平均值)
在浓度为50ppm时,化合物Ia、Ib、Ic对朱砂叶螨的致死率在90%以上;在10ppm时,化合物Ic对朱砂叶螨的致死率高于90%;按照以上方法,选取化合物Ic与已知化合物KC进行杀小菜蛾活性平行测定。试验结果见表3。
表3杀朱砂叶螨活性测试结果
由试验结果可见,本发明化合物有优良的杀虫和杀螨活性。
Claims (3)
1.一种含3-氯-5-三氟甲基吡啶基-1,3,4-噁二唑-2-酮类化合物,结构如通式I所示:
通式I中R选自:
2.根据权利要求1所述的一种含3-氯-5-三氟甲基吡啶基-1,3,4-噁二唑-2-酮类化合物的用途,其特征在于通式I化合物用作农业或林业杀虫杀螨剂,防治农业或林业上的害虫、害螨。
3.一种杀虫、杀螨组合物,含有权利要求1所述的通式I化合物为活性组分和农业、林业上可接受的载体。
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CN114716487A (zh) * | 2022-02-24 | 2022-07-08 | 四川农业大学 | 一种呋喃双酯类化合物及其制备方法和应用 |
WO2023277014A1 (ja) * | 2021-06-29 | 2023-01-05 | 住友化学株式会社 | 複素環化合物及びそれを含有する有害節足動物防除組成物 |
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WO2023277014A1 (ja) * | 2021-06-29 | 2023-01-05 | 住友化学株式会社 | 複素環化合物及びそれを含有する有害節足動物防除組成物 |
CN114716487A (zh) * | 2022-02-24 | 2022-07-08 | 四川农业大学 | 一种呋喃双酯类化合物及其制备方法和应用 |
CN114716487B (zh) * | 2022-02-24 | 2024-03-08 | 四川农业大学 | 一种呋喃双酯类化合物及其制备方法和应用 |
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