CN106518793A - 一种含1,2,3‑三唑环的酰胺类化合物及其制备方法与应用 - Google Patents
一种含1,2,3‑三唑环的酰胺类化合物及其制备方法与应用 Download PDFInfo
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- CN106518793A CN106518793A CN201610941300.9A CN201610941300A CN106518793A CN 106518793 A CN106518793 A CN 106518793A CN 201610941300 A CN201610941300 A CN 201610941300A CN 106518793 A CN106518793 A CN 106518793A
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- antibacterial
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- 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
- 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
- A01N25/12—Powders or granules
- A01N25/14—Powders or granules wettable
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Organic Chemistry (AREA)
- Toxicology (AREA)
- Dispersion Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明属于农业化学技术领域，特别涉及一种含1,2,3‑三唑环的酰胺类化合物及其制备方法与应用。本发明首先将R基羧酸与炔丙胺反应，得到端基炔烃化合物；将4’‑氯‑2‑硝基联苯还原得到4’‑氯‑2‑氨基联苯，后与氯乙酰氯反应，所得化合物再与叠氮化钠反应，得到叠氮化合物；然后将端基炔烃化合物与叠氮化合物进行点击反应，得到含1,2,3‑三唑环的酰胺类化合物CAU‑BC。所需原料便宜，反应路线简单。CAU‑BC对番茄灰霉病菌、瓜果腐霉病菌、花生褐斑病菌、马铃薯晚疫病菌、棉花立枯病菌、油菜菌核病菌具有一定的杀菌活性，对水稻稻瘟病菌具有良好的杀菌活性，绝大多数化合物对水稻稻瘟病菌的杀菌活性达到80％以上。
Description
技术领域
本发明属于农业化学技术领域，特别涉及一种含1,2,3-三唑环的酰胺类化合物及其制备方法与应用。
背景技术
杂环化合物，尤其是含氮杂环化合物，由于其具有生物活性高、环境相容性好、作用靶标新颖等特性，已成为农药创制中的研究热点。目前，国内外开发的杀菌剂品种主要是内吸性及选择性较好的杂环杀菌剂，又以三唑类和吡唑酰胺类杀菌剂为主。三唑类杀菌剂具有高效、长效、内吸性以及立体选择性等特点，其活性基团是三唑环，如近年来开发的对卵菌纲真菌有特效的辛唑嘧菌胺和吲唑磺菌胺，持效性强、耐雨水冲淋、对多种病害有稳定的效果。对小麦锈病和白粉病具有特效的戊唑醇、腈菌唑和用于防治果树、蔬菜及禾谷类作物真菌病害的酰胺唑都是三唑类杀菌剂的突出代表。酰胺类化合物作为杀菌剂约有50年历史，在杀菌剂中占有很大比例，并且一直有新颖结构的品种报道，长盛不衰，如主要用于防治白粉病、灰霉病、各种腐烂病等病害、并且无交互抗性的啶酰菌胺。近期开发的酰胺类杀菌剂共有8个，多为吡唑酰胺类杀菌剂：sedaxane、isopyrazam、penflufen、fluxapyroxad、Bixafen，可见杂环酰胺类化合物多具有良好的杀菌活性。
发明内容
本发明的目的是提供一种含1,2,3-三唑环的酰胺类化合物及其制备方法与应用。
一种含1,2,3-三唑环的酰胺类化合物(CAU-BC)，其为式I所示化合物或其药学上可接受的盐；
其中，R为吡啶基、苯基或带有1～3个取代基的苯基。
优选地，所述带有1～3个取代基的苯基中的取代基选自卤素、甲基、甲氧基、硝基、三氟甲基、七氟异丙基中的一种及以上。
优选地，所述带有1～3个取代基的苯基，当苯基为单取代时，取代基为2位取代、3位取代或4位取代；当苯基为双取代时，取代基为2,3位双取代、2,4位双取代、3,4位双取代2,5位双取代或2,6位双取代；当苯基为三取代时，取代基为2,4,5位三取代。
一种含1,2,3-三唑环的酰胺类化合物的制备方法，包括如下步骤：
1)将式II所示化合物与炔丙胺反应，得到式III所示端基炔烃化合物；
2)将4’-氯-2-硝基联苯还原得到4’-氯-2-氨基联苯，后与氯乙酰氯反应得到式IV所示化合物，然后与叠氮化钠反应得到式V所示叠氮化合物；
3)式III所示端基炔烃化合物与式V所示叠氮化合物进行点击反应，得到式I所示化合物；
其中，式II所示化合物和式III所示化合物中R的定义同式I所示化合物。
一种含1,2,3-三唑环的酰胺类化合物在制备杀菌剂中的应用。
所述杀菌剂具体可用于杀灭下述至少一种病菌：番茄灰霉病菌、瓜果腐霉病菌、花生褐斑病菌、马铃薯晚疫病菌、棉花立枯病菌、油菜菌核病菌、水稻稻瘟病菌。
一种杀菌剂，其活性成分为权利要求1所述一种含1,2,3-三唑环的酰胺类化合物。
一种杀菌剂乳油，由下述质量百分含量的物质组成：
1％～10％的权利要求1所述一种含1,2,3-三唑环的酰胺类化合物；
5％～15％的乳化剂；
0.1％～1％的渗透剂；
余量为溶剂。
一种实施方式为，所述乳化剂为表面活性剂，如农乳0203B，0208，GFC，OP-10，吐温-60等；所述渗透剂为渗透剂JFC、渗透剂OE-35等；所述溶剂为甲苯、二甲苯等。
一种杀菌剂可湿性粉剂，由下述质量百分含量的物质组成：
15％～50％的权利要求1所述一种含1,2,3-三唑环的酰胺类化合物；
10％～20％的表面活性剂；
30％～75％的白碳黑。
一种杀菌剂组合物，其活性成分由a)和b)组成，
所述a)为权利要求1所述一种含1,2,3-三唑环的酰胺类化合物；
所述b)为下述至少一种杀菌剂：百菌清、异菌脲、多菌灵；
所述a)和b)的质量比为(1～90):(10～99)；
所述杀菌剂的剂型为可湿性粉剂或乳油。
本发明的有益效果为：
本发明根据活性亚结构拼接原理，将活性片段2-(4-氯苯基)苯胺和三唑环相结合，设计合成了一类结构新颖的含1,2,3-三唑环的酰胺类化合物。
本发明制备该结构新颖的含1,2,3-三唑环的酰胺类化合物(CAU-BC)所需原料便宜，反应路线简单。杀菌活性测定结果表明，CAU-BC对番茄灰霉病菌、瓜果腐霉病菌、花生褐斑病菌、马铃薯晚疫病菌、棉花立枯病菌、油菜菌核病菌具有一定的杀菌活性，对水稻稻瘟病菌具有良好的杀菌活性，绝大多数化合物对水稻稻瘟病菌的杀菌活性达到80％以上，其中化合物CAU-BC-2和化合物CAU-BC-8对水稻稻瘟病菌的杀菌活性分别达到91％和93％，对水稻稻瘟病具有良好的防治效果。
附图说明
图1为式CAU-BC-1所示的化合物的核磁共振氢谱图。
图2为式CAU-BC-1所示的化合物的核磁共振碳谱图。
具体实施方式
下面结合附图和具体实施方式对本发明做进一步说明。应该强调的是，下述说明仅仅是示例性的，而不是为了限制本发明的范围及其应用。
下述实施例中所述实验方法，如无特殊说明，均为常规方法；所述试剂和材料，如无特殊说明，均可从商业途径获得。
实施例1化合物CAU-BC-1(R＝苯基)的制备及结构鉴定。
(1)在100ml圆底烧瓶中，将苯甲酸(0.50g，4.09mmol)溶于30ml干燥二氯甲烷。再将草酰氯(0.4ml，4.50mmol)用15ml干燥二氯甲烷稀释，于冰浴搅拌下，缓慢滴加入苯甲酸的二氯甲烷溶液中。滴加完毕后，撤去冰浴，加入2滴二甲基甲酰胺(DMF)，于室温下搅拌反应2h，减压旋蒸除DMF，得到苯甲酰氯的二氯甲烷溶液。将炔丙胺(0.4ml，5.32mmol)用10ml干燥二氯甲烷稀释，并加入三乙胺(0.6ml，4.50mmol)，于冰浴搅拌下，将制得的苯甲酰氯的二氯甲烷溶液缓慢滴加入炔丙胺的二氯甲烷溶液中，滴加完毕后，撤去冰浴，于室温下搅拌反应30min～60min。反应完毕后用甲醇淬灭，二氯甲烷萃取三次，合并有机相，无水硫酸钠干燥。浓缩后柱层析得苯甲酰炔丙胺0.60g，呈白色固体，收率92％。
(2)在1L圆底烧瓶中，加入4’-氯-2-硝基联苯(50.06g，214.25mmol)，溶解于500ml无水乙醇，充分溶解后加入125ml水，再加入氯化铵(25.91g，484.39mmol)，在充分搅拌下，缓慢分批加入铁粉(40.62g，727.31mmol)，95℃油浴回流下机械搅拌5h。TLC(石油醚:乙酸乙酯＝10:1)检测反应完全后，停止加热搅拌，趁热用硅藻土进行抽滤，先用水后用乙醇洗涤滤渣。再将所得滤液于55℃下减压旋蒸除乙醇，用二氯甲烷萃取三次，合并有机相，无水硫酸钠干燥。浓缩后柱层析，得到4’-氯-2-氨基联苯37.96g，呈橙黄色液体，产率为87％。
(3)在250ml圆底烧瓶中，加入4’-氯-2-氨基联苯(10.81g，53.08mmol)，用50ml干燥二氯甲烷溶解完全，加入三乙胺(14.7ml，106.16mmol)。将氯乙酰氯(4.4ml，58.39mmol)用30ml干燥二氯甲烷稀释，于冰浴搅拌下，用滴液漏斗缓慢滴加入反应瓶中。滴加完毕后，撤去冰浴，于室温下搅拌反应1h。TLC(石油醚:乙酸乙酯＝5:1)检测反应完全后，停止搅拌。用水淬灭，二氯甲烷萃取三次，合并有机相，无水硫酸钠干燥。浓缩后柱层析，得到式IV所示化合物12.34g，呈淡橙色固体，产率为83％。
(4)在250ml圆底烧瓶中，将式IV所示化合物(12.34g，44.05mmol)溶于100ml干燥DMF，加入叠氮钠(14.32g，220.25mmol)和碘化钾(8.19g，49.34mmol)，充分搅拌，于50℃下反应5h。TLC(石油醚:乙酸乙酯＝4:1)检测反应完全后，停止加热搅拌。用冰水淬灭，并用冰水水洗三次，乙酸乙酯萃取两次，合并有机相，无水硫酸钠干燥。浓缩后柱层析，再重结晶，得到式V所示化合物8.84g，呈淡黄色固体，产率为70％。
(5)将苯甲酰炔丙胺(0.60g，3.76mmol)和式V所示化合物(0.83g，2.89mmol)溶解于36ml叔丁醇，室温下搅拌。五水硫酸铜(0.36g，1.45mmol)充分溶解于4ml水，再加入抗坏血酸钠(0.57g，2.89mmol)，充分搅拌后加入反应液中，室温下反应12h。旋蒸除去叔丁醇，萃取干燥后重结晶，得到产物CAU-BC-1，0.71g，白色固体，熔点为194～196℃，产率为55％。
结构确认数据：
1H NMR(DMSO,300Hz)δ:9.78(s,1H,CONH),9.10(t,J＝5.6Hz,1H,CONH),7.94(s,1H,C＝CHN),7.91(dt,2H,J＝0.4Hz,1.7Hz,ArH),7.31～7.57(m,11H,ArH),5.18(s,2H,CH2),4.55(d,J＝5.6Hz,2H,CH2).13C NMR(DMSO,75MHz)δ:166.30,165.02,145.23,137.49,135.14,134.27,134.02,132.41,131.41,130.73,130.41,128.65,128.41,128.34,127.40,126.70,126.54,124.63,51.93,35.01。
其他通式为CAU-BC的系列化合物均按照上述方法制备得到。化合物编号，R对应的取代基团、理化数据见表1，结构鉴定的核磁共振氢谱、碳谱数据见表2。
实施例2化合物CAU-BC-1乳油的配制
在100mL容量瓶中加入1～10g化合物CAU-BC-1，0.1～1g渗透剂，5～15g乳化剂，然后用溶剂如甲苯、二甲苯等定容得化合物CAU-BC-1的质量含量为1％～10％的乳油。其中，所述乳化剂为如农乳0203B，0208，GFC，OP-10，吐温-60等表面活性剂；所述渗透剂为渗透剂JFC，渗透剂OE-35等。
其他通式为CAU-BC的化合物的乳油均可按照上述方法制备得到。
实施例3化合物CAU-BC-1可湿性粉剂的配制
取15～50g化合物CAU-BC-1，10～20g表面活性剂(如表面活性剂NNO等)，30～75g白碳黑，经混合粉碎后得化合物CAU-BC-1的质量含量为15％～50％的可湿性粉剂。
其他通式为CAU-BC的化合物的可湿性粉剂均可按照上述方法制备得到。
实施例4通式为CAU-BC的化合物的杀菌活性的测定
测定方法：采用生长速率测定法，即将不同浓度的药液与融化的培养基混合，制成带毒培养基平面，在平面上接种病原菌，以病菌生长速率的快慢来判定药剂毒力的大小。通式为CAU-BC的化合物的杀菌活性见表3。
下述为供试靶标：
1)棉花立枯病：病原有性态[Thanatephorus cucumeris(Frank)Donk.]
2)花生褐斑病：病原[Cercospora arachidicola Hori]
3)油菜菌核病：病原[Sclerotinia sclerotiorum(Lib.)de Bary]
4)马铃薯晚疫病：病原[Phytophthora infestans(Mont.)de Bary]
5)瓜果腐霉病：病原[Pythium aphanidermatum(Edson)Fitzpatrick]
6)番茄灰霉病：病原[Botrytis cinerea Pers.ex]
7)水稻稻瘟病：病原[Magnaporthe grisea]
以上菌种均为中国农业科学院植物保护研究所保存菌种，扩繁后备用。
表1 CAU-BC系列化合物的编号、取代基团、理化数据
表2 CAU-BC系列化合物的核磁共振氢谱、碳谱数据
表3 CAU-BC系列化合物50mg/L浓度下对植物病原菌的生长抑制率(％)
从表3可以看出，化合物CAU-BC对番茄灰霉病、瓜果腐霉病、花生褐斑病、马铃薯晚疫病、棉花立枯病、油菜菌核病原菌具有一定的杀菌活性，特别是对水稻稻瘟病原菌有良好的杀菌活性，绝大多数化合物对水稻稻瘟病的杀菌活性达到80％以上，其中化合物CAU-BC-2和化合物CAU-BC-8对水稻稻瘟病的杀菌活性分别达到91％和93％，对水稻稻瘟病具有良好的防治效果。
Claims (10)
1.一种含1,2,3-三唑环的酰胺类化合物，其特征在于，所述含1,2,3-三唑环的酰胺类化合物为式I所示化合物或其药学上可接受的盐；
其中，R为吡啶基、苯基或带有1～3个取代基的苯基。
2.根据权利要求1所述一种含1,2,3-三唑环的酰胺类化合物，其特征在于，所述带有1～3个取代基的苯基中的取代基选自卤素、甲基、甲氧基、硝基、三氟甲基、七氟异丙基中的一种及以上。
3.根据权利要求1所述一种含1,2,3-三唑环的酰胺类化合物，其特征在于，所述带有1～3个取代基的苯基，
当苯基为单取代时，取代基为2位取代、3位取代或4位取代；
当苯基为双取代时，取代基为2,3位双取代、2,4位双取代、3,4位双取代、2,5位双取代或2,6位双取代；
当苯基为三取代时，取代基为2,4,5位三取代。
4.权利要求1所述一种含1,2,3-三唑环的酰胺类化合物的制备方法，其特征在于，包括如下步骤：
1)将式II所示化合物与炔丙胺反应，得到式III所示端基炔烃化合物；
2)将4’-氯-2-硝基联苯还原得到4’-氯-2-氨基联苯，后与氯乙酰氯反应得到式IV所示化合物，然后与叠氮化钠反应得到式V所示叠氮化合物；
3)式III所示端基炔烃化合物与式V所示叠氮化合物进行点击反应，得到式I所示化合物；
其中，式II所示化合物和式III所示化合物中R的定义同式I所示化合物。
5.权利要求1所述一种含1,2,3-三唑环的酰胺类化合物在制备杀菌剂中的应用。
6.根据权利要求5所述的应用，其特征在于，所述杀菌剂用于杀灭下述至少一种病菌：番茄灰霉病菌、瓜果腐霉病菌、花生褐斑病菌、马铃薯晚疫病菌、棉花立枯病菌、油菜菌核病菌、水稻稻瘟病菌。
7.一种杀菌剂，其特征在于，其活性成分为权利要求1所述一种含1,2,3-三唑环的酰胺类化合物。
8.一种杀菌剂乳油，其特征在于，由下述质量百分含量的物质组成：
1％～10％的权利要求1所述一种含1,2,3-三唑环的酰胺类化合物；
5％～15％的乳化剂；
0.1％～1％的渗透剂；
余量为溶剂。
9.一种杀菌剂可湿性粉剂，其特征在于，由下述质量百分含量的物质组成：
15％～50％的权利要求1所述一种含1,2,3-三唑环的酰胺类化合物；
10％～20％的表面活性剂；
30％～75％的白碳黑。
10.一种杀菌剂组合物，其特征在于，其活性成分由a)和b)组成，
所述a)为权利要求1所述一种含1,2,3-三唑环的酰胺类化合物；
所述b)为下述至少一种杀菌剂：百菌清、异菌脲、多菌灵；
所述a)和b)的质量比为(1～90):(10～99)；
所述杀菌剂的剂型为可湿性粉剂或乳油。
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| CN106614786A (zh) * | 2016-11-28 | 2017-05-10 | 东莞市联洲知识产权运营管理有限公司 | 一种用于瓜果种植中的杀菌剂组合物的制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140005231A1 (en) * | 2012-06-29 | 2014-01-02 | E I Du Pont De Nemours And Company | Fungicidal heterocyclic carboxamides |
| WO2014004064A1 (en) * | 2012-06-29 | 2014-01-03 | E. I. Du Pont De Nemours And Company | Fungicidal heterocyclic carboxamides |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140005231A1 (en) * | 2012-06-29 | 2014-01-02 | E I Du Pont De Nemours And Company | Fungicidal heterocyclic carboxamides |
| WO2014004064A1 (en) * | 2012-06-29 | 2014-01-03 | E. I. Du Pont De Nemours And Company | Fungicidal heterocyclic carboxamides |
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| Title |
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| 王振军 等: "1-取代-1H-1,2,3-三唑-4-甲酰胺类化合物的设计合成与生物活性", 《有机化学》 * |
| 苏娜 等: "点击化学合成1,2,3-三唑类杀菌剂及其生物活性", 《中国化工学会农药专业委员会第十三届年会论文集》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106614786A (zh) * | 2016-11-28 | 2017-05-10 | 东莞市联洲知识产权运营管理有限公司 | 一种用于瓜果种植中的杀菌剂组合物的制备方法 |
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