CN110432274A - 3-溴-6-氯-2-吡啶甲酸在防除杂草方面的用途 - Google Patents

3-溴-6-氯-2-吡啶甲酸在防除杂草方面的用途 Download PDF

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CN110432274A
CN110432274A CN201910662334.8A CN201910662334A CN110432274A CN 110432274 A CN110432274 A CN 110432274A CN 201910662334 A CN201910662334 A CN 201910662334A CN 110432274 A CN110432274 A CN 110432274A
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bromo
chloro
formic acid
weeds
pyridyle
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李婉
冯珂
李美琳
张祎
姜若南
杨凯越
朱华结
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Hebei University
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Hebei University
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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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/803—Processes of preparation

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

Abstract

本发明提供了3‑溴‑6‑氯2‑吡啶甲酸在防除杂草方面的用途，3‑溴‑6‑氯2‑吡啶甲酸的结构式如下：(I)。该化合物在75g/hm2剂量下对小藜有较好的抑制活性，可作为除草剂的候选化合物。

Description

3-溴-6-氯-2-吡啶甲酸在防除杂草方面的用途
技术领域
本发明涉及一种化合物的新用途，具体是3-溴-6-氯-2-吡啶甲酸在防除杂草方面的用途。
背景技术
3-溴-6-氯-2-吡啶甲酸是医药行业抗肿瘤药物或者其他系统性用药的关键中间体，吡啶环上的氯比较活泼，可以发生取代或者偶联反应引入其他取代基，是医药的化合物的有效片段。
本发明提供的3-溴-6-氯-2-吡啶甲酸在除草方面的应用，目前没有报道。
发明内容
本发明的目的是提供3-溴-6-氯-2-吡啶甲酸的新用途，具体是在防除杂草方面的用途。
所述3-溴-6-氯-2-吡啶甲酸的结构式如下：
(I)。
3-溴-6-氯2-吡啶甲酸的制备方法，包括如下步骤：以3-溴-6-氯-吡啶-2-氰和无机酸为原料，一定温度下搅拌反应，经后处理得3-溴-6-氯-2-吡啶甲酸(I) 。
反应方程式如下：
。
3-溴-6-氯-吡啶-2-氰和无机酸的投料摩尔比为1:10。
所述的无机酸为90wt%硫酸或30wt%盐酸。
反应温度为160oC-180oC，优选170oC。
本发明所述的3-溴-6-氯-2-吡啶甲酸在防除杂草方面的用途是指在防除双子叶杂草，尤其是小藜方面的应用。
具体的使用方法为：
准确称量一定质量的 3-溴-6-氯-2-吡啶甲酸，加入1wt%-3wt%的丙酮水溶液溶解，后加入吐温，配制成75g/hm2剂量，然后将培养好的试材（小藜）于喷雾塔里，进行喷雾。
本发明还提供了一种除草农药组合物，其包括有效成分为3-溴-6-氯-2-吡啶甲酸或其药物学上可接受的盐，以及一种或多种药学上可接受的辅料。
本发明将3-溴-6-氯-2-吡啶甲酸用于防除杂草，其对双子叶杂草（例如小藜）具有较好的除草活性，可用于制备除草剂。
具体实施方式
下面结合实施例对本发明做进一步的阐述，下述实施例仅作为说明，并不以任何方式限制本发明的保护范围。
在下述实施例中未详细描述的过程和方法是本领域公知的常规方法，实施例中所用试剂均为分析纯或化学纯，且均可市购或通过本领域普通技术人员熟知的方法制备。
实施例1
目标化合物(I)的合成
于干燥100ml三口瓶中加入3-溴-6-氯-吡啶-2-氰5g和50 ml 90wt%硫酸，搅拌下升温至170℃，反应3.0 h，冷却，反应液倾入150 ml冰水中，搅拌下析出固体，抽滤，少量水洗涤，干燥后得3-溴-6-氯-吡啶-2甲酸，收率：89%，1H NMR (400 MHz, DMSO) δ:14.19(s,1H)，8.25(d,J=8.5Hz,1H)，7.61(d,J=8.5Hz,1H).。
实施例2
目标化合物(I)的合成
于干燥100ml三口瓶中加入3-溴-6-氯-吡啶-2-氰5g和50 ml 30wt%盐酸，搅拌下升温至170℃，反应8.0 h，冷却，反应液倾入150 ml冰水中，搅拌下析出固体，抽滤，少量水洗涤，干燥后得3-溴-6-氯-吡啶-2甲酸，收率：82%，1H NMR (400 MHz, DMSO) δ:14.19(s,1H)，8.25(d,J=8.5Hz,1H)，7.61(d,J=8.5Hz,1H).。
实施例 3
3-溴-6-氯-吡啶-2甲酸的生物活性测试
茎叶处理：小藜种子经催芽露白后播入塑料花盆中（直径10cm，深12cm，装入取自浙江杭州萧山荒地的壤土），每盆播种5粒，播种后覆土0.5cm。播种后的花盆从底部浸湿，在实验室内培养至3-5叶期，喷施待测化合物的乳液。
乳液的配制方法为：准确称量一定质量的原药（3-溴-6-氯-吡啶-2甲酸），加入1wt%-3wt%的丙酮水溶液溶解，后加入吐温，配制成75g/hm2剂量。
然后将培养好的试材（3-5叶期小藜）于喷雾塔里，进行喷雾。喷雾后将花盆搬回实验室，室温培养，根据需要浇水。实验设3次重复，以喷施含等量N,N-二甲基甲酰胺和1%吐温-80的乳液作为对照。施药后第26天取地上部分称量鲜重，计算鲜重抑制率。
普筛结果：剂量为75g a.i/ hm2时，茎叶喷雾，普筛结果列入表1。
表1 化合物(I)对双子叶杂草的除草活性(75g a.i/ hm2)
活性测试结果表明，3-溴-6-氯-吡啶-2甲酸在茎叶处理后，对小藜有一定抑制率，达20%；该类化合物对双子叶杂草有一定的防效，可作为除草剂的候选化合物。

Claims (6)

1.3-溴-6-氯-2-吡啶甲酸在防除杂草方面的用途。
2.根据权利要求1所述的用途，其特征在于：所述杂草为双子叶杂草。
3.根据权利要求1所述的用途，其特征在于：所述杂草为小藜。
4.根据权利要求1所述的用途，其特征在于：将3-溴-6-氯-2-吡啶甲酸配制成乳液，之后将乳液喷洒在杂草的茎叶上。
5.根据权利要求4所述的用途，其特征在于：乳液的配制包括如下步骤：使用1wt%-3wt%的丙酮水溶液溶解3-溴-6-氯-2-吡啶甲酸，然后加入吐温，配制成75g/hm2剂量。
6.一种除草农药组合物，其特征在于，其包括有效成分为3-溴-6-氯-2-吡啶甲酸或其药物学上可接受的盐，以及一种或多种药学上可接受的辅料。
CN201910662334.8A 2019-07-22 2019-07-22 3-溴-6-氯-2-吡啶甲酸在防除杂草方面的用途 Pending CN110432274A (zh)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114890942A (zh) * 2022-06-20 2022-08-12 凯美克(上海)医药科技有限公司 3-溴-6-氯吡啶-2-甲酸及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1003937A (en) * 1963-03-25 1965-09-08 Dow Chemical Co 3,6-dichloro - 2 - picolinic acid compounds
CN103058921A (zh) * 2011-10-21 2013-04-24 苏州滋康医药有限公司 一种3-溴-6-氯吡啶-2-甲酸的合成方法
CN107136114A (zh) * 2017-06-23 2017-09-08 浙江天丰生物科学有限公司 一种协同除草组合物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1003937A (en) * 1963-03-25 1965-09-08 Dow Chemical Co 3,6-dichloro - 2 - picolinic acid compounds
CN103058921A (zh) * 2011-10-21 2013-04-24 苏州滋康医药有限公司 一种3-溴-6-氯吡啶-2-甲酸的合成方法
CN107136114A (zh) * 2017-06-23 2017-09-08 浙江天丰生物科学有限公司 一种协同除草组合物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114890942A (zh) * 2022-06-20 2022-08-12 凯美克(上海)医药科技有限公司 3-溴-6-氯吡啶-2-甲酸及其制备方法

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