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CN105541632B - 一种降龙涎橙花酯杀菌剂 - Google Patents

一种降龙涎橙花酯杀菌剂 Download PDF

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CN105541632B
CN105541632B CN201510866407.7A CN201510866407A CN105541632B CN 105541632 B CN105541632 B CN 105541632B CN 201510866407 A CN201510866407 A CN 201510866407A CN 105541632 B CN105541632 B CN 105541632B
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CN105541632A (zh
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杨绍祥
刘永国
肖阳
李丽慧
郝颜峰
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Beijing Technology and Business University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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  • General Health & Medical Sciences (AREA)
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Abstract

本发明公开了一种新型化合物降龙涎橙花酯，具体化学结构式如下式所示：

Description

一种降龙涎橙花酯杀菌剂
技术领域
本发明涉及一种新型化合物以及该化合物在防治农业病菌中的应用。
背景技术
植物源天然产物农药具有对靶标生物选择性好、作用方式独特、对人、畜及天敌低毒等特点。但是由于多数天然产物活性不理想，且来源有限，严重限制了其在农业生产中的广泛应用。以植物源天然产物为先导进行结构优化，提高其生物活性，进而开发新型绿色农药，一直以来是新农药创制的一个重要方向。
香紫苏醇具有防治大豆锈病、小麦白粉病、调节植物生长和植物防御功能，是一个具有潜在开发价值的先导化合物。目前，国外仅见日本科学家将香紫苏醇开发为农药产品以外，还未见其衍生物研究开发成功的报道。基于以上原因，采用化学合成方法，合成一些香紫苏醇类似物，并对其杀菌活性、杀虫活性和除草活性进行较为系统的研究，力求从中发现活性更高的二次先导化合物，从而为进一步研究开发香紫苏醇奠定理论基础。
上式为香紫苏醇
发明内容
本发明的目的之一是公开化合物降龙涎橙花酯，结构如下所示：
本发明目的之二在于公开上述化合物在防治农业病菌中的应用。
实验证明，本发明的化合物具有明显的杀菌活性，对农业病菌有直接的化学防治效果，可以制备为农业病菌防治剂。
以本发明化合物为活性成分的防治农业病菌的药物也属于本发明的保护范围。
在需要的时候，在所述药物中还可以加入一种或多种农药制剂中可接受的载体，所述载体包括农药制剂中常规的稀释剂、赋形剂、填充剂、粘合剂、湿润剂、吸收促进剂、表面活 性剂、润滑剂、稳定剂等。制成的药物的剂型也是多样的，可以是粉剂、乳剂、水剂、颗粒剂等。
具体实施方式
实施例1.降龙涎橙花酯的制备
合成路线如下式所示：
将1.55g(5mmol)A乙酰羟基降龙涎酸与0.93g(6mmol)B橙花醇加入到50mL三口烧瓶中，再称取1.15g(6mmol)1-(3-二甲氨基丙基)-3-乙基碳二亚胺(EDCI)与0.12g(1mmol)4-二甲氨基吡啶(DMAP)加入到其中，加入20mL二氯甲烷，加热到40℃回流搅拌48h。后将温度将至室温，加入12mL 10％H2SO4溶液，分液，有机相依次用适量饱和NaHCO3、饱和NaCl溶液洗涤，旋蒸，柱层析分离纯化(石油醚∶乙酸乙酯＝15∶1)，得白色晶体1.92g，产率86.1％。
产物经过核磁氢谱及核磁碳谱表征。
1H NMR(300MHz，CDCl3)δ：0.76(6H，s，2Me-4)，4.53-4.55(2H，m，O-CH2)，4.98-5.07(1H，m，C＝CH)，5.31-5.36(1H，m，C＝CH).
13C NMR(75MHz，CDCl3)δ：173.8，169.5，141.9，131.7，123.1，118.8，85.8，60.6，54.7，54.5，41.1，38.5，38.2，38.1，32.8，32.6，31.7，30.0，26.2，25.2，23.0，22.2，20.9，19.5，19.3，17.8，17.2，15.2.
实施例2.本发明化合物对农业病菌的生物活性
无菌条件下，将阳性对照百菌清及实施例1所得化合物用1mL DMF溶解，加入灭菌自来水稀释至10mg/mL待用。
采用含毒介质法。
首先，制备含药培养基。取配置好的药液药剂各2mL，转入200mL灭过菌并且冷却到45℃左右的PDA培养基中，充分混匀，倒入培养皿中。每处理重复3次，以加入无菌水的培养基为对照。
其次，移接菌饼。用打孔器沿测试菌的菌落边缘打菌饼，用镊子或接菌针取菌饼，菌面向下接于含毒培养基中心，每皿一块。放入恒温箱中，然后置于24～16℃下，培养2天后选用十字交叉法测量、记录菌落直径，通过以下公式计算抑制率。
测试菌种：黄瓜灰霉病菌(Botrytis cinerea)、小麦赤霉病菌(Fusariumgraminearum)、水稻纹枯病菌(Rhizoctonia solani)、烟草赤星病菌(Alternariaalternata)。
百菌清对黄瓜灰霉病菌、小麦赤霉病菌、水稻纹枯病菌、烟草赤星病菌的抑制率均为100％；降龙涎橙花酯对黄瓜灰霉病菌、小麦赤霉病菌、水稻纹枯病菌、烟草赤星病菌的抑制率分别为50％、57.6％、43.2％、34.4％。
结果表明，在测试浓度下，本发明的化合物对农业病菌黄瓜灰霉病菌、小麦赤霉病菌、水稻纹枯病菌、烟草赤星病菌具有明显的抑制效果。初步活性测试结果表明，该化合物具有良好应用前景，有望成为一类新型农业病菌控制剂。

Claims (1)

1.一种化合物降龙涎橙花酯，具体化学结构式如下所示：
CN201510866407.7A 2015-12-03 2015-12-03 一种降龙涎橙花酯杀菌剂 Expired - Fee Related CN105541632B (zh)

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* Cited by examiner, † Cited by third party
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Gd(OTf)3-catalyzed synthesis of geranyl esters for the intramolecular radical cyclization of their epoxides mediated by titanocene(III);William H. Garcia Santos et al;《Organic & Biomolecular Chemistry》;20141118;第13卷;第1358-1366页 *
香紫苏醇衍生物的合成及其杀菌活性初步研究;白红进等;《西北农业学报》;20051231;第14卷(第2期);第64-68页 *

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