CN109053431A - 阿魏酸或其衍生物在防治植物细菌病或真菌病中的应用 - Google Patents

阿魏酸或其衍生物在防治植物细菌病或真菌病中的应用 Download PDF

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CN109053431A
CN109053431A CN201811004820.2A CN201811004820A CN109053431A CN 109053431 A CN109053431 A CN 109053431A CN 201811004820 A CN201811004820 A CN 201811004820A CN 109053431 A CN109053431 A CN 109053431A
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carbon
ferulic acid
och
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alkoxy
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陈爱端
徐向荣
石伶俐
魏凤彪
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Beijing Kingbo Biotech Co Ltd
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Beijing Kingbo Biotech Co Ltd
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Abstract

本发明提供阿魏酸或其衍生物在防治植物细菌病或真菌病中的应用。本发明所述的阿魏酸或其衍生物的结构通式为(I)所示结构的化合物。

Description

阿魏酸或其衍生物在防治植物细菌病或真菌病中的应用
技术领域
本发明涉及农药技术领域,具体涉及阿魏酸或其衍生物在防治植物细菌病或真菌病中的应用。
背景技术
阿魏酸(ferulic acid(FA),化学名称为4-羟基-3-甲氧基苯丙烯酸)是普遍存在的一种酚酸,在植物细胞壁中与多糖和木质素交联构成细胞壁的一部分,是阿魏、当归、川芎、升麻等中药的有效成分之一,因其具有较强的抗氧化活性和防腐作用而已经被广泛应用于医药、保健品、化妆品原料和食品添加剂方面。近年来对其药理药效方面的广泛深入研究发现阿魏酸及其衍生物还具有很好的解热镇痛、抗血栓、降血脂、抗菌消炎、防癌、抗突变、增强免疫功能以及增强人体精子活力和运动性等生物活性,其毒性极低,几乎无副作用。
现有技术披露了阿魏酸及其衍生物用作新型抗植物病毒剂,能很好地抑制烟草花叶病毒、辣椒病毒、番茄病毒、马铃薯病毒和瓜类病毒及玉米矮花叶病毒等,可有效防治烟草、辣椒、番茄、瓜菜、粮食、蔬菜、豆类等多种作物的病毒病,尤其适合于防治烟草花叶病。目前,除了阿魏酸可作为食品、粮食防腐剂、抗病毒剂在农业上的相关应用以外,有关阿魏酸及其衍生物在农业上用于细菌和真菌性病害活性的研究实属空白。迄今尚未见以阿魏酸及其衍生物作为控制植物细菌和真菌病害的相关报道,也未见阿魏酸及其衍生物控制细菌和真菌病害的相关研究报道。
植物细菌性和真菌性病害多使用化学农药来防治,但这些化学农药存在污染大,与环境相容性差、病原菌容易产生抗药性等问题,因此,开发以天然植物活性物质为有效成分的高效、低毒的绿色杀菌剂农药新品种意义非常重大。
发明内容
本发明的目的是提供一种新型、高效、低毒的防治植物细菌性或真菌性病害的药物,也即提供了阿魏酸或其衍生物在防治植物细菌或真菌性病害中的新用途。
所述的阿魏酸或其衍生物的结构通式为(I)所示结构的化合物:
式中,R1,R2,R3分别代表氢、羟基、1-6碳烷氧基、卤素原子、甲酰基、羧基、1-4碳烷基羰基、1-4碳烷基羰氧基、1-4碳烷氧基羰氧基、硝基;或者R1和R2,R2和R3分别代表OCH2O,OCH2CH2O;R4代表氢、羟基、ONa、OK、ONH4、葡萄糖基、烃氧基、烃胺基、二烃胺基、1-6碳烃基、(3-6)碳烯基、(3-6)卤代碳烯基、(3-6)碳炔基、1-4碳卤代烷基、1-4碳烷氧烷基、1-4碳烷硫烷基、苯基、萘基、色满、2,3-二氢-1,4-苯并二噁嗪、4H-1,3-苯并二噁嗪、2,3-二氢-苯并呋喃、苯并呋喃、苯并噻唑、1,3-苯并噁唑、1,2-苯并异噁唑或苯并咪唑,各基团是未取代的,或是被一个或一个以上的下述基团取代:卤素、1-4碳烷基、1-4碳烷氧基、1-4碳卤代烷基、1-4碳卤代烷氧基、1-4碳烷氧烷基、1-4碳烷硫基、1-4碳烷基亚磺酰基、1-4碳烷基磺酰基、硝基、氰基、羟基、羧基、1-4碳烷基羰基、1-4碳烷氧基羰基或亚胺基;双键的构型为反式、或顺式、或顺反混合。
优选地,所述的阿魏酸或其衍生物中R1,R2,R3分别代表H,OH,OCH3,OCH2CH3,OCOCH3,F,Cl,Br,CHO,CO2H,NO2;或者R1和R2,R2和R3分别代表OCH2O,OCH2CH2O;R4代表OH,OCH3,OCH2CH3,CH2CH=CH2,NEt2,p-Cl-C6H4NH,ONa,OK,ONH4,葡萄糖基。
表1部分阿魏酸及其衍生物的化学结构式和物理常数
所述的植物为农作物、蔬菜、果树。
所述的植物为黄瓜、辣椒、马铃薯、油菜、番茄、菠菜、苹果、梨、桃、小麦、大麦、水稻、小米、高粱、燕麦、花生、玉米、大豆、荞麦。
所述的细菌为假单孢杆菌、欧文氏杆菌、黄单孢杆菌、棒状杆菌。优选地,所述细菌为假单孢杆菌、欧文氏杆菌。
所述的真菌为疫霉菌、灰霉菌、菌核病菌、白粉菌、霜霉菌、锈病菌。
优选地,所述真菌为疫霉菌、霜霉菌、菌核病菌。
本发明提供了含有阿魏酸或其衍生物的用于防治植物细菌病或真菌病的制剂,所述制剂为农药或肥料。
进一步地,所述农药为喷施剂、种子包衣剂、土壤处理剂或种苗处理剂。
更进一步地,本发明提供一种阿魏酸制剂,是5%阿魏酸微乳剂,是由5%阿魏酸和20%乙醇、20%吐温80、5%十二烷基苯磺酸钙、50%水配置而成,该5%阿魏酸微乳剂稀释800倍后用于防治黄瓜霜霉病,平均防效达到78.8%,甚至在稀释1000倍后对黄瓜霜霉病的防治效果达到75.2%。该5%阿魏酸微乳剂稀释800倍后用于防治油菜菌核病,平均防效达到74.4%,远高于对照组25%多菌灵可湿性粉剂的防治效果。
本发明提供了上述5%阿魏酸微乳剂在防治植物细菌病或真菌病中的应用。
所述细菌病为为假单孢杆菌、欧文氏杆菌、黄单孢杆菌、棒状杆菌为病原的植物疾病。例如,黄瓜细菌性角斑病,白菜软腐病。
所述真菌病为疫霉菌、灰霉菌、菌核病菌、白粉菌、霜霉菌、锈病菌为病原的植物疾病。例如辣椒疫霉菌病,黄瓜霜霉病,油菜菌核病,普通白粉病。
本发明提供了阿魏酸或其衍生物在制备防治植物细菌病或真菌病的药物中的应用。
本发明的有益效果在于:阿魏酸或其衍生物化学结构简单,来源广泛,可有效防治多种作物的细菌病和真菌病,特别对黄瓜细菌性角斑病、辣椒疫霉病、黄瓜霜霉病、油菜菌核病的防控方面效果显著,且对环境污染小,对其他生物相对安全,具有良好的市场应用前景。
具体实施方式
以下实施例用于说明本发明,但并不用来限制本发明的范围。下述各实施例中,所使用的各类设备、试剂和材料若无特别说明,均为常规市售可得。
阿魏酸可以从米糠、谷壳以及阿魏等植物原料中按照常规方法提取获得也可以化学合成获得。本申请所涉及的阿魏酸购买于浙江得乐康食品股份有限公司,阿魏酸量为98%。5%阿魏酸微乳剂由5%阿魏酸和20%乙醇、20%吐温80、5%十二烷基苯磺酸钙、50%水配置而成。实施例中所用菌种来自中国农业科学院植物保护研究所。若无特殊说明,本申请的生化试剂均为市售。
为了更好地理解本发明,下面结合本发明的实施例,进一步来说明本发明的实质性内容,但本发明的内容并不局限于此。
实施例1阿魏酸对黄瓜细菌性角斑病活性测定
1、菌种:黄瓜细菌性角斑病菌(Pseudomonas syringae pv.lachrymans),属假单胞菌属,丁香假单胞菌黄瓜致病变种。
2、浓度设定:在无菌条件下将阿魏酸用NB培养基稀释成200,100,50,25,12.5,6.25和3.125ug/mL的系列含有阿魏酸的培养液,设不含药剂处理的空白对照,各处理重复4次。
3、试验方法:采用抑制细菌生长量试验浑浊度法进行测定。将生长在NA培养基斜面上的黄瓜细菌性角斑病菌菌种用灭菌水稀释为1×107个孢子/mL浓度的悬浮液,向各处理培养基中分别接种100uL菌液,置于28-30℃条件下震荡培养(120r/min)。
4、调查和计算:开始培养前分别测定各处理的浑浊度,待对照处理达到对数生长期时,测定并记载各处理的浑浊度,计算各处理细菌的生长抑制率和EC50值。
表2
阿魏酸对黄瓜细菌性角斑病菌生长的抑制中浓度EC50为26.57ug/mL说明阿魏酸对黄瓜细菌性角斑病表现抑制活性。
实施例2阿魏酸对辣椒疫病菌室内测定
试材准备:将辣椒疫霉菌(Phytophthora capsici Leonian)接入马铃薯葡萄糖琼脂培养基(PDA)上,置于(25±1℃)恒温培养箱中培养备用。锥形瓶、玻璃棒、移液管、培养皿、打孔器、接种器等灭菌后备用。
药剂配置及处理:用小量丙酮溶解阿魏酸原药,根据试验设计需求,再用0.1%的吐温80水溶液稀释成5个系列浓度梯度待用(分别为4、2、1、0.5、0.25mg/L)。在无菌操作条件下,根据试验处理将预先融化的灭菌培养基定量加入无菌锥形瓶中,从低浓度到高浓度依次定量吸取药液,分别加入上述锥形瓶中,充分摇匀。然后等量倒入3个直径为9cm的培养皿中,制成相应的含药平板。
接种与调查:将培养好的病原菌在无菌条件下,用直径5cm的灭菌打孔器自菌落边缘切取菌饼,用接种器将菌饼接种于含药平板中央,菌丝面朝上,盖上皿盖,置于(28±1)℃恒温培养箱中培养。每处理4次重复,并设不含药剂但含有相应有机溶液和0.1%吐温80的水溶液处理作对照。根据空白对照培养皿中菌丝生长情况调查病原菌菌丝生长情况。用卡尺测量菌落直径,单位mm。每个菌落用十字交叉法垂直测量直径各一次,取其平均值。根据调查数据,计算各处理浓度对供试靶标菌的菌丝生长抑制率。计算方法如下:
孢子萌发率(%)=孢子萌发数/调查的孢子总数×100
处理校正孢子萌发率(%)=处理孢子萌发率/空白对照孢子萌发率×100
孢子萌发相对抑制率(%)=(空白对照孢子萌发率-处理校正的孢子萌发率)/空白对照孢子萌发率×100
结果与分析:阿魏酸对辣椒疫病的EC50为10.5mg/L,EC90为25.84mg/L,毒力回归方程为Y=4.9940+1.8806x。室内生测结果表明,阿魏酸对辣椒疫病有很高的抑制率。
实施例3阿魏酸衍生物对辣椒疫霉病菌室内测定
试材准备:将辣椒疫霉菌(Phytophthora capsici Leonian)接入马铃薯葡萄糖琼脂培养基(PDA)上,置于(25±1℃)恒温培养箱中培养备用。锥形瓶、玻璃棒、移液管、培养皿、打孔器、接种器等灭菌后备用。
药剂配置及处理:用小量丙酮溶解阿魏酸衍生物(表3中衍生物编号对应表1中阿魏酸衍生物编号),根据试验设计需求,再用0.1%的吐温80水溶液配置各个衍生物浓度为500ug/mL,在无菌操作条件下,根据试验处理将预先融化的灭菌培养基定量加入无菌锥形瓶中,将各个衍生物药液,分别加入上述锥形瓶中,充分摇匀。然后等量倒入3个直径为9cm的培养皿中,制成相应的含药平板。
接种与调查:将培养好的病原菌在无菌条件下,用直径5cm的灭菌打孔器自菌落边缘切取菌饼,用接种器将菌饼接种于含药平板中央,菌丝面朝上,盖上皿盖,置于(28±1)℃恒温培养箱中培养。每处理4次重复,并设不含药剂但含有相应有机溶液和0.1%吐温80的水溶液处理作对照。根据空白对照培养皿中菌丝生长情况调查病原菌菌丝生长情况。用卡尺测量菌落直径,单位mm。每个菌落用十字交叉法垂直测量直径各一次,取其平均值。根据调查数据,计算各处理浓度对供试靶标菌的菌丝生长抑制率。计算方法如下:
孢子萌发率(%)=孢子萌发数/调查的孢子总数×100
处理校正孢子萌发率(%)=处理孢子萌发率/空白对照孢子萌发率×100
孢子萌发相对抑制率(%)=(空白对照孢子萌发率-处理校正的孢子萌发率)/空白对照孢子萌发率×100
结果与分析:阿魏酸衍生物对辣椒疫病的抑制率见下表3:
表3
实施例4 5%阿魏酸微乳剂在防治黄瓜霜霉病上的田间应用
1试验目的
验证内蒙古清源保生物科技有限公司生产的5%阿魏酸微乳剂(5%阿魏酸和20%乙醇、20%吐温80、5%十二烷基苯磺酸钙、50%水配置而成)防治黄瓜霜霉病的效果,以确定适宜的使用方法和剂量。
2试验条件
2.1试验对象、作物和品种的选择
黄瓜霜霉病(Pseudoperonospora cubensis),黄瓜,品种为德瑞特。
2.2作物栽培及环境条件
试验在中国农业科学院植物保护研究所试验基地进行,试验设在北京市昌平区北庄户蔬菜大棚中,大棚宽度10米,黄瓜株距10厘米,行距100厘米,试验地土壤肥力中等,地力均匀,栽培管理条件好,植株长势良好。
3试验设计和安排
3.1药剂
3.1.1试验药剂5%阿魏酸微乳剂
3.1.2对照药剂1.5%多抗霉素可湿性粉剂,陕西美邦农药有限公司。
3.1.3药剂用量与处理编号
表4供试药剂试验设计
3.2小区安排
3.2.1小区排列如下
A1 A2 B A3 CK A2 B A3 CK A1 A3 B A2 A1 CK A3 B A2 A1 CK
A1:5%阿魏酸微乳剂 稀释1200倍
A2:5%阿魏酸微乳剂 稀释1000倍
A3:5%阿魏酸微乳剂 稀释800倍
B:1.5%多抗霉素可湿性粉剂520克/亩
CK:空白对照
3.2.2小区面积和重复 小区面积:8平方米;重复次数:4次
3.3施药方法
3.3.1使用方法
在黄瓜霜霉病发病前期,试验药剂用水稀释,用背负手动喷雾器针对黄瓜植株均匀喷雾。
3.3.2施药器械
采用DFH-16A型背负手动喷雾器,喷头为孔径1.3mm的圆锥雾喷头,采用喷雾压力为0.2~0.4MPa.。
3.3.3施药时间和次数
于发病前喷药,主要看药的保护效果,以后每隔七天施药一次,连续施药三次。第一次喷雾在2017年4月27日,第二次喷雾在5月4日,第三次喷雾在5月11日。
3.3.4使用容量 喷雾用药,施药液量为900升/公顷
3.3.5防治其他病虫害的药剂资料试验期间,未喷洒其他农药。
4调查、记录和测量方法
4.1土壤资料 试验地土质为中性土壤,肥水管理中等。
4.2调查方法、时间和次数
4.2.1调查时间和次数 当对照明显发病时开始调查,2017年5月18日调查防治效果。
4.2.2调查方法
每小区随机五点取样,每点调查两株,每株调查全部叶片。以每片叶上的病斑面积占整个叶面积和百分率来分级。末次药后7天调查病情指数和防效。防治效果显著性测定采用邓肯氏新复极差(DMRT)法。
0级:无病斑
1级:病斑面积占整个叶面积的5%以下;
3级:病斑面积占整个叶面积的6%-10%;
5级:病斑面积占整个叶面积的11%-25%;
7级:病斑面积占整个叶面积的26%-50%;
9级:病斑面积占整个叶面积的50%以上。
4.2.3药效计算方法
a.
b.
4.3对作物的直接影响 未观察到黄瓜叶片的药害现象。
4.4产品的产量和质量 试验期间未发现对产品的质量和产量的影响。
4.5对其他生物影响
4.5.1对其他病虫害的影响 试验期间未发生其他病虫害。
4.5.2对其他非靶标生物的影响 试验期间未发现试验药剂对其它非靶标生物的影响。
5结果与分析
表5 5%阿魏酸微乳剂防治黄瓜霜霉病试验结果
表6 5%阿魏酸微乳剂防治黄瓜霜霉病方差分析结果
变异来源 平方和 自由度 均方值 F值 F<sub>0.05</sub> F<sub>0.01</sub>
处理间 157.566 3 52.522 12.593 3.49 5.95
处理内 50.0498 12 4.1708
总变异 207.6158 15
5%阿魏酸微乳剂防治黄瓜霜霉病试验,结果详见表5。5%阿魏酸微乳剂防治黄瓜霜霉病在药量为稀释1200倍时,达到70.0%的防治效果;5%阿魏酸微乳剂防治黄瓜霜霉病在药量为稀释1000倍时,达到75.3%的防治效果。
5%阿魏酸微乳剂防治黄瓜霜霉病在药量为稀释800倍时,能达到78.8%的防治效果。在5%差异显著水平上,5%阿魏酸微乳剂防治黄瓜霜霉病在药量为稀释800倍时,防治效果要优于稀释1000倍及1200倍的防治效果,5%阿魏酸微乳剂防治黄瓜霜霉病在药量为稀释1000倍与对照药剂1.5%多抗霉素可湿性粉剂520克/亩相比,防治效果无显著性差异,但均优于5%阿魏酸微乳剂稀释1200倍时的防治效果。
在1%差异显著水平上,5%阿魏酸微乳剂防治黄瓜霜霉病在药量为稀释800倍与稀释1000倍相比,防治效果无显著性差异。5%阿魏酸微乳剂防治黄瓜霜霉病在药量为稀释1000倍时与1.5%多抗霉素可湿性粉剂520克/亩防治效果相比,无显著性差异。
综合考虑防治效果和用药成本,采用5%阿魏酸微乳剂防治黄瓜霜霉病,稀释1000倍~800倍(有效成分用量50.00克—62.50毫克/千克),对黄瓜霜霉病有较好的防治效果。
实施例5 5%阿魏酸微乳剂在防治油菜菌核病上的田间应用
1试验目的验证5%阿魏酸微乳剂防治油菜菌核病的效果,以确定适宜的使用方法和剂量。
2试验条件
2.1试验对象、作物和品种的选择 油菜菌核病(Sclerotinia sclerotiorum(Lib.)de Bary),油菜品种为秦油7号。
2.2作物栽培及环境条件 试验在江苏省通州事植保站试验基地进行,大棚宽度10米,油菜株距10厘米,行距80厘米,试验地土壤肥力中等,地力均匀,栽培管理条件好,植株长势良好。
3试验设计和安排
3.1药剂
3.1.1试验药剂 5%阿魏酸微乳剂。
3.1.2对照药剂 25%多菌灵可湿性粉剂,江西中旭农化有限公司。
3.1.3药剂用量与处理编号
表7供试药剂试验设计
3.2小区安排
3.2.1小区排列
表8
CK B C D A
A C CK B D
B CK A D C
D C CK B A
A:5%阿魏酸微乳剂 稀释1200倍
B:5%阿魏酸微乳剂 稀释1000倍
C:5%阿魏酸微乳剂 稀释800倍
D:25%多菌灵可湿性粉剂 300克/亩
CK:空白对照
3.2.2小区面积和重复 小区面积:8平方米;重复次数:4次
3.3施药方法
3.3.1使用方法 4月6日,在油菜主茎开花株率达95%~100%时用药,每亩兑水75kg,用背负手动喷雾器针对油菜植株均匀喷雾。
3.3.2防治其他病虫害的药剂资料试验期间,未喷洒其他农药。
4调查、记录和测量方法
4.1土壤资料 试验地土质为砂壤土,肥水管理中等。
4.2调查方法、时间和次数
4.2.1调查时间和次数 在油菜菌核病发病基本定居时(5月28~30日),调查各小区的发病情况。
4.2.2调查方法 每小区棋盘式10点调查,每点调查5株(50株/小区),调查时注意不要在边行取样。记载发病株和严重度,计算发病株,病情指数和防病效果,收获时各小区取20株,测定千粒重和平均单株产量。并对试验数据进行统计分析。
0级:无病
1级:轻微发病,发病面积占主茎表面积的5%以下;
3级:轻度发病,发病面积占主茎表面积的6%~15%;
5级:中等发病,发病面积占主茎表面积的16%~30;
7级:高度发病,发病面积占主茎表面积的31%~50%以下;
9级:严重发病,发病面积占主茎表面积的50%以上。
4.2.3药效计算方法
病情指数=(各级病株数×相对级数值)调查总株数×9×100
防治效果(%)=1-CK0×PT1CK1×PT0×100
试中:CK0—空白对照区施药前病情指数
CK1—空白对照区施药后病情指数
PT0—药剂处理区施药前病情指数
PT1—药剂处理区施药后病情指数
4.3对作物的直接影响 未观察到油菜叶片的药害现象。
4.4产品的产量和质量 试验期间未发现对产品的质量和产量的影响。
4.5对其他生物影响
4.5.1对其他病虫害的影响 试验期间未发生其他病虫害。
4.5.2对其他非靶标生物的影响 试验期间未发现试验药剂对其它非靶标生物的影响。
5结果与分析
表9 5%阿魏酸微乳剂防治油菜菌核病试验结果
药剂评价:田间试验结果表明,5%阿魏酸微乳剂防治油菜菌核病A、B、C处理3种不同使用剂量的防效分别为57.07%、65.60%、74.40%,对照药剂D处理的防效为67.73%。在5%显著水平上,对剂量间差异进行分析,结果显示,A处理与B、C处理间,B处理与C处理间防效差异显著;与对照药剂D处理进行比较,A、C处理与D处理间防效差异显著,B处理与D处理间防效差异不显著。在试验剂量范围内,供试药剂对作物安全。
实施例6 5%阿魏酸微乳剂在防治白菜软腐病上的田间应用
1试验目的 验证5%阿魏酸微乳剂防治白菜软腐病的效果,以确定适宜的使用方法和剂量。
2试验条件
2.1试验对象、作物和品种的选择
白菜软腐病由欧文氏杆菌侵染后引起腐烂,白菜品种为农大78。
2.2作物栽培及环境条件
试验在山东菏泽曹县生态园中进行,土质为壤土,中性,肥力较好。
3试验设计和安排
3.1药剂
3.1.1试验药剂 5%阿魏酸微乳剂。
3.1.2对照药剂 3%中生菌素可湿性粉剂,福建凯立生物制品有限公司。3.1.3药剂用量与处理编号
表10供试药剂试验设计
3.2小区安排
3.2.1小区排列
表11
D B B D C
A C CK A D
C CK D CK C
A B CK A B
A:5%阿魏酸微乳剂 稀释1200倍
B:5%阿魏酸微乳剂 稀释1000倍
C:5%阿魏酸微乳剂 稀释800倍
D:3%中生菌素可湿性粉剂 稀释800倍
CK:空白对照
3.2.2小区面积和重复 小区面积:8平方米;重复次数:4次
3.3施药方法
3.3.1使用方法
在白菜移栽后第15天第一次喷药,以后间隔10天再喷一次,用背负手动喷雾器针对白菜植株均匀喷雾。
3.3.2防治其他病虫害的药剂资料 试验期间,未喷洒其他农药。
4调查、记录和测量方法
4.1调查方法、时间和次数
4.1.1调查时间和次数 在第二次喷药后调查各小区的发病情况。
4.1.2调查方法 每小区调查全部菜株。记载发病株,计算防病效果。
4.1.3药效计算方法
防治效果=(空白对照区病株数-处理区病株数)/空白对照区病株数×100
4.2对作物的直接影响 未观察到油菜叶片的药害现象。
4.3产品的产量和质量 试验期间未发现对产品的质量和产量的影响。
4.4对其他生物影响
4.4.1对其他病虫害的影响试验期间未发生其他病虫害。
4.4.2对其他非靶标生物的影响
试验期间未发现试验药剂对其它非靶标生物的影响。
5结果与分析
表12 5%阿魏酸微乳剂防治白菜软腐病试验结果
药剂评价:田间试验结果表明,5%阿魏酸微乳剂防治白菜软腐病A、B、C处理3种不同使用剂量的防效分别为67.11%、75.63%、79.38%,对照药剂D处理的防效为73.93%。在5%显著水平上,对剂量间差异进行分析,结果显示,A处理与B、C处理间,B处理与C处理间防效差异显著;与对照药剂D处理进行比较,A、C处理与D处理间防效差异显著,B处理与D处理间防效差异不显著。在试验剂量范围内,供试药剂对作物安全。
实施例7 5%阿魏酸微乳剂在防治葡萄白粉病上的田间应用
1试验目的
了解该产品对葡萄白粉病的实际防治效果和安全性,(5%阿魏酸和20%乙醇、20%吐温80、5%十二烷基苯磺酸钙、50%水配置而成)
2试验条件
2.1试验对象、作物和品种的选择葡萄白粉病(Uncinula necator),葡萄,品种为“巨峰”
2.2环境条件
本试验选在湖北省孝感市孝南区祝站镇堰河村进行。试验地块土质为沙壤土,pH值7.0,有机质含量较高。
3试验设计和安排.
3.1药剂
3.1.1试验药剂 5%阿魏酸微乳剂(内蒙古清源保生物科技有限公司)
3.1.2对照药剂 5%己唑醇悬浮剂(浙江威尔达化工有限公司)
3.1.3药剂用量与处理编号
表13供试药剂试验设计
处理编号 药剂 施药剂量(制剂量) 施药量(有效成分量)
A 5%阿魏酸微乳剂 1200倍液 41.66毫克/千克
B 5%阿魏酸微乳剂 1000倍液 50.0毫克/千克
C 5%阿魏酸微乳剂 800倍液 62.5毫克/千克
D 5%已唑醇悬浮剂 1000倍液 50毫克/千克
E 清水
3.2小区安排
3.2.1小区排列 小区随机排列,四周设保护行。
表14
重复1 C A D B E
重复2 A C B E D
重复3 B E A D C
重复4 D C B E A
3.2.2小区面积和重复
小区面积:各处理小区面积30㎡,小区间及四周设保护行。
重复次数:试验设有5个处理,每处理重复4次,共计20个小区。
3.3施药方法
3.3.1使用方法
常规方法喷雾,按每亩用水量50升计算小区用水量,先喷清水对照,然后喷试验药剂。喷施试验药剂时按浓度由低到高的顺序进行,换药时要清洗干净喷雾器。
3.3.2施药器械
施药器械为浙江市下喷雾器化工有限公司“市下牌SX-MD5DA”电动喷雾器。
3.3.3施药时间和次数
于2017年5月6日第一次施药。第一次施药后间隔7天于5月13日第二次施药。第一次施药时葡萄白粉病发病初期。
3.3.4使用容量 每亩用药液量50升。
3.3.5防治其它病虫害的药剂资料
无。
4调查、记录和测量方法
4.1土壤资料
试验田土壤为沙壤土,pH值7.0,有机质含量较高,土壤肥沃。
4.2调查方法、时间和次数
4.2.1调查时间和次数
第二次施药后10天,田间病情基本稳定,于5月23日调查一次。
4.2.2调查方法
随机5点取样,每点调查20片叶,每小区共调查100片叶,记录病叶数与病级数,分别计算各处理病情指数与相对防效。病情分级标准:
0级:无病斑;
1级:病斑面积占整个叶面积的5%以下;
3级:病斑面积占整个叶面积的6%-25%;
5级:病斑面积占整个叶面积的26%-50%;
7级:病斑面积占整个叶面积的51%-75%;
9级:病斑面积占整个叶面积的76%以上。
4.2.3药效计算方法
4.3对作物的直接影响
整个试验过程未发现供试药剂对葡萄生长发育产生不良影响。
4.4产品的产量和质量:无。
4.5对其它生物影响
4.5.1对其它病虫害的影响:无。
4.5.2对其它非靶标生物的影响:无。
5结果与分析
表15 5%阿魏酸微乳剂防治葡萄白粉病药后10天试验结果
生物统计方法:应用邓肯新复极差法对试验数据进行统计分析。
药剂评价:田间试验结果表明,第二次施药后10天,内蒙古清源保生物科技有限公司生产的5%阿魏酸微乳剂防治葡萄白粉病A、B、C处理3种不同使用剂量的防效分别为62.55%、69.09%、76.00%,对照药剂D处理的防效为66.18%。在5%显著水平上,对剂量间差异进行分析,结果显示,A处理与B、C处理间,B处理与C处理间均防效差异显著;与对照药剂D处理进行比较,C处理与D处理间防效差异显著,A、B处理与D处理间防效差异不显著。在试验剂量范围内,供试药剂对作物安全。
虽然,上文中已经用一般性说明、具体实施方式及试验,对本发明作了详尽的描述,但在本发明的基础上,可以对之作一些修改或改进,这对本领域技术人员而言是显而易见的。因此,在不偏离本发明精神的基础上所做的这些修改或改进,均属于本发明要求保护的范围。

Claims (10)

1.阿魏酸或其衍生物在防治植物细菌病或真菌病中的应用,其特征在于,所述阿魏酸的结构通式为(I)所示结构的化合物:
式中,R1,R2,R3分别代表氢、羟基、1-6碳烷氧基、卤素原子、甲酰基、羧基、1-4碳烷基羰基、1-4碳烷基羰氧基、1-4碳烷氧基羰氧基、硝基;或者R1和R2,R2和R3分别代表OCH2O,OCH2CH2O;R4代表氢、羟基、ONa、OK、ONH4、葡萄糖基、烃氧基、烃胺基、二烃胺基、1-6碳烃基、(3-6)碳烯基、(3-6)卤代碳烯基、(3-6)碳炔基、1-4碳卤代烷基、1-4碳烷氧烷基、1-4碳烷硫烷基、苯基、萘基、色满、2,3-二氢-1,4-苯并二噁嗪、4H-1,3-苯并二噁嗪、2,3-二氢-苯并呋喃、苯并呋喃、苯并噻唑、1,3-苯并噁唑、1,2-苯并异噁唑或苯并咪唑,各基团是未取代的,或是被一个或一个以上的下述基团取代:卤素、1-4碳烷基、1-4碳烷氧基、1-4碳卤代烷基、1-4碳卤代烷氧基、1-4碳烷氧烷基、1-4碳烷硫基、1-4碳烷基亚磺酰基、1-4碳烷基磺酰基、硝基、氰基、羟基、羧基、1-4碳烷基羰基、1-4碳烷氧基羰基或亚胺基;双键的构型为反式、或顺式、或顺反混合。
2.根据权利要求1所述的应用,其特征在于,所述的阿魏酸或其衍生物中R1,R2,R3分别代表H,OH,OCH3,OCH2CH3,OCOCH3,F,Cl,Br,CHO,CO2H,NO2;或者R1和R2,R2和R3分别代表OCH2O,OCH2CH2O;R4代表OH,OCH3,OCH2CH3,CH2CH=CH2,NEt2,p-Cl-C6H4NH,ONa,OK,ONH4,葡萄糖基。
3.根据权利要求1所述的应用,其特征在于,所述的植物为农作物、蔬菜、果树。
4.根据权利要求3所述的应用,其特征在于,所述的植物为黄瓜、辣椒、马铃薯、油菜、番茄、菠菜、苹果、梨、桃、小麦、大麦、水稻、小米、高粱、燕麦、花生、玉米、大豆、荞麦。
5.根据权利要求1-4任一所述的应用,其特征在于,所述的细菌为假单孢杆菌、黄单孢杆菌、欧文氏杆菌、棒状杆菌。
6.根据权利要求1-4任一所述的应用,其特征在于,所述的真菌为疫霉菌、灰霉菌、菌核病菌、白粉菌、霜霉菌、锈病菌。
7.含有阿魏酸或其衍生物的用于防治植物细菌病或真菌病的制剂,所述制剂为农药或肥料,所述阿魏酸的结构通式为(I)所示结构的化合物:
式中,R1,R2,R3分别代表氢、羟基、1-6碳烷氧基、卤素原子、甲酰基、羧基、1-4碳烷基羰基、1-4碳烷基羰氧基、1-4碳烷氧基羰氧基、硝基;或者R1和R2,R2和R3分别代表OCH2O,OCH2CH2O;R4代表氢、羟基、ONa、OK、ONH4、葡萄糖基、烃氧基、烃胺基、二烃胺基、1-6碳烃基、(3-6)碳烯基、(3-6)卤代碳烯基、(3-6)碳炔基、1-4碳卤代烷基、1-4碳烷氧烷基、1-4碳烷硫烷基、苯基、萘基、色满、2,3-二氢-1,4-苯并二噁嗪、4H-1,3-苯并二噁嗪、2,3-二氢-苯并呋喃、苯并呋喃、苯并噻唑、1,3-苯并噁唑、1,2-苯并异噁唑或苯并咪唑,各基团是未取代的,或是被一个或一个以上的下述基团取代:卤素、1-4碳烷基、1-4碳烷氧基、1-4碳卤代烷基、1-4碳卤代烷氧基、1-4碳烷氧烷基、1-4碳烷硫基、1-4碳烷基亚磺酰基、1-4碳烷基磺酰基、硝基、氰基、羟基、羧基、1-4碳烷基羰基、1-4碳烷氧基羰基或亚胺基;双键的构型为反式、或顺式、或顺反混合。
8.根据权利要求7所述的农药,其特征在于,所述农药为5%阿魏酸微乳剂,其由5%阿魏酸、20%乙醇、20%吐温80、5%十二烷基苯磺酸钙、50%水配置而成,所述%为质量百分比。
9.阿魏酸或其衍生物在制备防治植物细菌病或真菌病的药物中的应用,所述阿魏酸的结构通式为(I)所示结构的化合物:
式中,R1,R2,R3分别代表氢、羟基、1-6碳烷氧基、卤素原子、甲酰基、羧基、1-4碳烷基羰基、1-4碳烷基羰氧基、1-4碳烷氧基羰氧基、硝基;或者R1和R2,R2和R3分别代表OCH2O,OCH2CH2O;R4代表氢、羟基、ONa、OK、ONH4、葡萄糖基、烃氧基、烃胺基、二烃胺基、1-6碳烃基、(3-6)碳烯基、(3-6)卤代碳烯基、(3-6)碳炔基、1-4碳卤代烷基、1-4碳烷氧烷基、1-4碳烷硫烷基、苯基、萘基、色满、2,3-二氢-1,4-苯并二噁嗪、4H-1,3-苯并二噁嗪、2,3-二氢-苯并呋喃、苯并呋喃、苯并噻唑、1,3-苯并噁唑、1,2-苯并异噁唑或苯并咪唑,各基团是未取代的,或是被一个或一个以上的下述基团取代:卤素、1-4碳烷基、1-4碳烷氧基、1-4碳卤代烷基、1-4碳卤代烷氧基、1-4碳烷氧烷基、1-4碳烷硫基、1-4碳烷基亚磺酰基、1-4碳烷基磺酰基、硝基、氰基、羟基、羧基、1-4碳烷基羰基、1-4碳烷氧基羰基或亚胺基;双键的构型为反式、或顺式、或顺反混合。
10.权利要求7-9任一所述的应用,其特征在于,所述的阿魏酸或其衍生物中R1,R2,R3分别代表H,OH,OCH3,OCH2CH3,OCOCH3,F,Cl,Br,CHO,CO2H,NO2;或者R1和R2,R2和R3分别代表OCH2O,OCH2CH2O;R4代表OH,OCH3,OCH2CH3,CH2CH=CH2,NEt2,p-Cl-C6H4NH,ONa,OK,ONH4,葡萄糖基。
CN201811004820.2A 2018-08-30 2018-08-30 阿魏酸或其衍生物在防治植物细菌病或真菌病中的应用 Pending CN109053431A (zh)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110407681A (zh) * 2019-08-12 2019-11-05 海南大学 一种脱氢姜酮衍生物、其制备方法及应用
CN110786374A (zh) * 2019-11-11 2020-02-14 中国农业大学 一种含阿魏酸酯的果蔬杀菌保鲜剂
CN112106774A (zh) * 2019-06-21 2020-12-22 中国农业大学 二羧酸类化合物在防治植物病害中的应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004051485A (ja) * 2002-05-27 2004-02-19 Yutaka Pharmacy:Kk ケイ皮酸誘導体を有効成分とする農業用抗菌・殺菌剤
KR20130138596A (ko) * 2012-06-11 2013-12-19 안동대학교 산학협력단 벤질리덴아세톤 유도체를 이용한 식물 병해충 방제 조성물 및 방제 방법
US20150313221A1 (en) * 2014-05-02 2015-11-05 Wisconsin Alumni Research Foundation Antimicrobial ferulic acid derivatives and uses thereof
CN105638783A (zh) * 2014-11-15 2016-06-08 张福民 一种防治黄瓜霜霉病的植物源杀菌剂
US20180049444A1 (en) * 2016-08-12 2018-02-22 The United States Of America, As Represented By The Secretary Of Agriculture Xenorhabdus szentirmaii metabolites, trans-cinnamic acid, and analogs thereof as enhancers of fungicidal activity

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004051485A (ja) * 2002-05-27 2004-02-19 Yutaka Pharmacy:Kk ケイ皮酸誘導体を有効成分とする農業用抗菌・殺菌剤
KR20130138596A (ko) * 2012-06-11 2013-12-19 안동대학교 산학협력단 벤질리덴아세톤 유도체를 이용한 식물 병해충 방제 조성물 및 방제 방법
US20150313221A1 (en) * 2014-05-02 2015-11-05 Wisconsin Alumni Research Foundation Antimicrobial ferulic acid derivatives and uses thereof
CN105638783A (zh) * 2014-11-15 2016-06-08 张福民 一种防治黄瓜霜霉病的植物源杀菌剂
US20180049444A1 (en) * 2016-08-12 2018-02-22 The United States Of America, As Represented By The Secretary Of Agriculture Xenorhabdus szentirmaii metabolites, trans-cinnamic acid, and analogs thereof as enhancers of fungicidal activity

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
A. S. GHANEKAR: "The involvement of phenolics and phytoalexins in resistance of potato to soft rot", 《POTATO RESEARCH》 *
TIAN GEILIN: "Phenolic acids in the plow layer soil of strawberry fields and their effects on the occurrence of strawberry anthracnose", 《EUROPEAN JOURNAL OF PLANT PATHOLOGY》 *
刘佳: "三种中药对植物病原真菌抑制作用研究", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 *
张龙: "《绿色化学》", 31 August 2014, 华中科技大学出版社 *
胡元森: "酚酸物质对黄瓜幼苗及枯萎病菌菌丝生长的影响", 《生态学杂志》 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112106774A (zh) * 2019-06-21 2020-12-22 中国农业大学 二羧酸类化合物在防治植物病害中的应用
CN110407681A (zh) * 2019-08-12 2019-11-05 海南大学 一种脱氢姜酮衍生物、其制备方法及应用
CN110407681B (zh) * 2019-08-12 2023-05-02 海南大学 一种脱氢姜酮衍生物、其制备方法及应用
CN110786374A (zh) * 2019-11-11 2020-02-14 中国农业大学 一种含阿魏酸酯的果蔬杀菌保鲜剂

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