CN117481120A - 一种防治镰刀菌引起的作物病害的杀菌剂组合物 - Google Patents
一种防治镰刀菌引起的作物病害的杀菌剂组合物 Download PDFInfo
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- CN117481120A CN117481120A CN202210874748.9A CN202210874748A CN117481120A CN 117481120 A CN117481120 A CN 117481120A CN 202210874748 A CN202210874748 A CN 202210874748A CN 117481120 A CN117481120 A CN 117481120A
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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Abstract
本发明公开了一种杀菌剂组合物及其在防治作物病害中的应用，属于植物病害防治技术领域。所述组合物的活性成分包括如式(Ⅰ)所示结构的化合物ZJS178与咪唑类杀菌剂，该杀菌剂组合物对由镰刀菌引起的作物病害有优异防效。化合物ZJS178与咪唑类杀菌剂在一定配比条件下复配具有增效作用，能显著提高抑菌活性和防治效果。本发明提供的组合物由不同作用机制的有效成分组成，能克服和延缓病菌的抗药性，对作物安全性好，符合农药减量增效的要求。
Description
技术领域
本发明涉及植物病害防治技术领域，具体涉及一种杀菌剂组合物及其在防治作物病害中的应用。
背景技术
镰刀菌是一类世界性分布的真菌，引起植物的根腐、茎腐、茎基腐、花腐和穗腐等多种病害，造成作物萎蔫死亡，影响产量和品质，是生产上难防病害之一。常见的病害有：水稻恶苗、小麦赤霉、瓜类枯萎、各种作物的根腐病等。尖孢镰刀菌(Fusarium oxysporum)是一种世界性分布的土传病原真菌，寄主范围广泛，可引起瓜类、茄科、香蕉、棉、豆科及花卉等100多种植物枯萎病。该病菌引起的西瓜枯萎病，是一种发生普遍的毁灭性土传和种传真菌性病害，一般发病田块产量下降30％～40％，重病地块减产80％以上，甚至造成绝收；尤其是保护地设施栽培西瓜，多年重茬栽培致使西瓜枯萎病愈发严重，给西瓜生产带来巨大威胁。近年来，随着我国辣椒种植面积的不断扩大及复种指数的不断提高，尖孢镰刀菌引起的辣椒枯萎病菌在田间逐年积累和蔓延，导致品质及产量日益下降，严重时可减产70％～80％，甚至绝产。因此，持续高效防控镰刀菌引起的作物病害对保障我国农产品有效供给及质量安全有重要意义。
当前由于缺乏高抗品种，化学防治在作物病害中发挥重要作用。
咪鲜胺(Prochloraz)，化学名称：N-丙基-N-[2-(2,4,6-三氯苯氧基)乙基]-咪唑-1-甲酰胺，是一种广谱杀菌剂，对多种作物由子囊菌和半知菌引起的病害具有明显的防效。
多菌灵(carbendazim)，化学名称：苯并咪唑-2-基氨基甲酸甲酯，属于广谱内吸性杀菌剂，主要干扰细胞的有丝分裂过程，对子囊菌纲的某些病原菌和半知菌类中的大多数病原真菌有效。
甲基硫菌灵(Thiophanate-Methyl)，化学名称：4，4’-(邻亚苯基)双(3-硫代脲基甲酸)二甲酯，属于广谱性内吸低毒杀菌剂，具有内吸传导特性；该药剂作用于病原真菌的β-微管蛋白，进而抑制病菌细胞分裂，达到抑制病菌生长的效果。
由于药剂长期使用导致病菌容易对上述药剂产生抗药性，影响药剂防效。为此，研发合适的药剂组合对持续防控作物病害有重要的现实意义。
发明内容
本发明的目的在于提供一种高效、低毒、环保杀菌剂组合物，对镰刀菌引起的作物病害有特效，同时能延缓药剂抗性，延长药剂使用寿命。
为实现上述目的，本发明采用如下技术方案：
本发明提供了一种杀菌组合物，所述组合物包括如式(Ⅰ)所示结构的化合物ZJS178和咪唑类杀菌剂，
上述化合物ZJS178为本发明课题组前期制备的新化合物，化学名称为2-氰基-3-氨基-3-[4-(N-乙基-N-甲基胺基)苯基]丙烯酸乙酯，合成路线如下：
该化合物是一种氰基丙烯酸酯类杀菌化合物，作用于镰刀菌的I型肌球蛋白(马达蛋白)，使病菌生长失去动力，导致病菌死亡。ZJS178结构新颖、作用方式独特，与咪唑类杀菌剂没有交互抗性。
优选的是，所述组合物中ZJS178与咪唑类杀菌剂的质量配比为60:1～1:60。
所述咪唑类杀菌剂包括但不限于：咪鲜胺、多菌灵、咪鲜胺锰盐、甲基硫菌灵等。
进一步优选的是，所述组合物中ZJS178与咪唑类杀菌剂的质量配比为20:1～1:20。
更进一步优选的是，所述组合物中ZJS178与咪唑类杀菌剂的质量配比为12:1～1:12。
更更进一步优选的是，所述组合物中ZJS178与咪唑类杀菌剂的质量配比为6:1～1:6。
最为优选的是，所述组合物中ZJS178与咪唑类杀菌剂的质量配比为3:1～1:3。
本发明提供的组合物，适合用于杀菌，特别适用用于农业杀菌。
优选的是，本发明提供的组合物适合用于防治由镰刀菌引起的病害。
进一步优选的是，所述镰刀菌是指植物致病镰刀菌，主要包括禾谷镰孢菌复合种(Fusarium graminearum complex)、藤仓镰刀菌复合种(Fusarium fujikuroi complex)、尖孢镰刀菌(Fusarium oxysporum)和串珠镰刀菌(Fusarium moniliforme)等。
更进一步优选的是，由镰刀菌引起的作物病害包括并不限于：瓜类枯萎病、番茄枯萎病、香蕉枯萎病、棉花枯萎病、草莓枯萎病、水稻恶苗病和小麦赤霉病等病害。
本发明提供的杀菌剂，所述杀菌剂以重量计含有0.5～90％的所述组合物。
进一步优选的是，所述杀菌剂以重量计含有5～80％的所述组合物。
本发明提供的杀菌剂，除所述组合物外，还可以进一步地包括农业上可接受的载体和助剂。
ZJS178与咪唑类杀菌剂的作用机制不同，本发明将ZJS178与两者进行复配，对镰刀菌引起的病害的防效显著高于单剂，减少单一药剂的施用量，有助于延缓病菌抗药性的产生，延长杀菌剂使用寿命。
研究表明，化合物ZJS178与咪唑类杀菌剂在一定配比条件复配，对抑制镰刀菌的生长具有协同增效作用。例如，化合物ZJS178与甲基硫菌灵以质量比3:1～1:3复配，对抑制尖孢镰刀菌的生长具有显著增效作用。
进一步的，所述杀菌剂还包括农药剂型所需要的辅助成分，组合物中活性成分的质量占比为0.5～90％。所述辅助成分为农药上常用的载体和助剂。
按照本领域技术人员公知的方法，本发明所述的杀菌剂组合物在实际应用时可配制成农业上允许的各种剂型，包括水分散粒剂、悬浮剂、种子处理悬浮剂。
对于水分散粒剂型，分散剂可选用聚羧酸盐、木质素磺酸盐、烷基萘磺酸盐；润湿剂选用烷基硫酸盐、烷基磺酸盐、萘磺酸盐；崩解剂选用硫酸铵、尿素、蔗糖、葡萄糖；粘结剂选用硅藻土、玉米淀粉、聚乙烯醇、羧甲基纤维素类；填料选用硅藻土、高岭土、白炭黑、轻钙、滑石粉、凹凸棒土、陶土等等。
对于悬浮剂型，可使用的助剂有：分散剂选用聚羧酸盐、木质素磺酸盐、烷基萘磺酸盐；润湿剂选用烷基酚聚氧乙烯聚基醚甲醛缩合物硫酸盐、烷基酚聚氧乙烯基醚磷酸酯、苯乙基酚聚氧乙烯基醚磷酸酯、烷基硫酸盐、烷基磺酸盐、萘磺酸盐；增稠剂选用黄原胶、聚乙烯醇、膨润土；防腐剂选用甲醛、苯甲酸、苯甲酸钠；消泡剂为有机硅类消泡剂；防冻剂选用乙二醇、丙二醇、甘油、尿素、无机盐类如氯化钠。
对于种子处理悬浮剂，可使用的助剂有：成膜剂可以是聚乙二醇、聚乙烯醇树脂、聚乙烯吡咯烷酮、羟乙基纤维素、均聚醋酸乙烯酯、羧甲基纤维素钠，阿拉伯胶，明胶，聚乙烯醇或聚丙烯酰胺或它们的混合物。技术人员可根据产品需要的粘度调整均聚醋酸乙烯酯的比例。
与现有技术相比，本发明具备的有益效果如下：
(1)本发明提供的杀菌剂组合物对镰刀菌引起的病害有优异防效，化合物ZJS178与甲基硫菌灵或咪鲜胺复配具有增效作用，能显著提高杀菌活性和防治效果。
(2)本发明提供的组合物由不同作用机制的有效成分组成，有利于克服和延缓病菌的抗药性，对作物安全性好，符合农药减量增效的要求。
具体实施方式
下面结合具体实施例对本发明做进一步说明。以下实施例仅用于说明本发明，不用来限制本发明的适用范围。在不背离本发明精神和本质的情况下，对本发明方法、步骤或条件所做的修改或替换，均属于本发明的范围。
下述实施例中所使用的试验方法如无特殊说明，均为常规方法；所使用的材料、试剂等，如无特殊说明，为可从商业途径得到的试剂和材料。
实施例1：化合物ZJS178的合成
步骤1：中间体b的合成
将7.0g原料a(CAS号：67710-36-5)、150mL二氯甲烷加入反应瓶中，冰浴下加入11.7g Boc酸酐，再缓慢加入6.0g三乙胺和3.3g DMAP，冰浴下继续搅拌0.5小时后升至室温，再搅拌5小时。反应结束后，向反应液中加入1M盐酸，分出有机相，有机相再用纯水和饱和食盐水各洗涤一次。有机相经无水Na2SO4干燥后浓缩，得到9.6g中间体b，该粗品未经进一步纯化直接投入下一步反应。
步骤2：中间体c的合成
将9.6g中间体b、120mL乙醇、24mL水加入反应瓶中，升温至90℃，加入3.7g铁粉和12mL饱和氯化铵溶液，继续反应4小时。反应结束后，加硅藻土过滤，滤液浓缩后加入水，乙酸乙酯萃取三次。合并有机相，浓缩后用柱层析分离(洗脱剂为乙酸乙酯与石油醚，体积比为1：2)，得到4.5g中间体c，收率51.1％。
步骤3：中间体d的合成
冰浴下将0.19g氢化钠加入20mL四氢呋喃中，再加入1.0g中间体c，升至室温后搅拌30分钟。再加入0.74g碘乙烷，室温搅拌过夜。反应结束后，加入水淬灭反应，再用乙酸乙酯萃取三次。合并有机相，浓缩后用柱层析分离(洗脱剂为乙酸乙酯与石油醚，体积比为1：5)，得到0.52g中间体d，收率48.0％。
步骤4：中间体e的合成
冰浴下将0.11g氢化钠加入10mL四氢呋喃中，再加入0.5g中间体d，升至室温后搅拌30分钟。再加入0.40g碘甲烷，室温搅拌过夜。反应结束后，加入水淬灭反应，再用乙酸乙酯萃取三次。合并有机相，浓缩后用柱层析分离(洗脱剂为乙酸乙酯与石油醚，体积比为1：5)，得到0.34g中间体e，收率65.5％。
步骤5：化合物ZJS178的合成
将0.34g中间体e、10mL四氢呋喃加入反应瓶中，通过浓硫酸滴加氯化钠制取氯化氢气体，缓慢通入反应液，1小时后停止通气，室温搅拌过夜。反应结束后，加入饱和碳酸氢钠水溶液，并用乙酸乙酯萃取两次。合并有机相，浓缩后用柱层析分离(洗脱剂为乙酸乙酯与石油醚，体积比为1：2)，得到0.22g化合物ZJS178，收率93.2％。
实施例2：ZJS178与甲基硫菌灵复配对西瓜枯萎病菌的室内毒力测定
试验对象：田间分离获得西瓜枯萎病菌(F.oxysporum f.sp.niveum)，测试菌株经形态和致病性鉴定后，由本研究室保存备用。
试验药剂：ZJS178由实施例1合成,甲基硫菌灵由浙江省化工研究院提供。
试验方法：参考《中华人民共和国农业行业标准NY/T 1156.2－2006》菌丝生长速率法。每个药剂按有效成分含量分别设5个剂量处理，其对病菌生长抑制率在10％-90％之间，将上述西瓜枯萎病菌接种在PDA培养基上，待菌落长满培养皿2/3时，用直径5mm的打孔器在菌落边缘打成菌块，用接种针将菌块移至预先配制成的含药培养基平板中央，然后置于25℃培养箱内培养3天后，采用十字交叉法用卡尺测量各处理菌落直径，求出校正抑制百分率；进而利用抑制率的机率值和系列浓度的对数值之间的线性回归分析，计算各药剂的EC50值，每处理重复4次。ZJS178设为标准药剂，按下列公式计算共毒系数(CTC)。
实际毒力指数(ATI)＝(标准药剂的EC50/供试药剂的EC50)×100；
理论毒力指数(TTI)＝标准药剂毒力指数×标准药剂在混合组配中所占的百分比+供试药剂毒力指数×供试药剂在混合组配中所占的百分比；
共毒系数(CTC)＝(ATI/TTI)×100％；
CTC值小于80，表明该药剂组合为拮抗作用；80-120之间为相加作用；大于120为增效作用。
测试结果如表1所示。
表1：ZJS178与甲基硫菌灵复配对西瓜枯萎病室内毒力测定结果
由表1所示，ZJS178与甲基硫菌灵质量百分比为6:1～1:3时对西瓜枯萎病菌生长的抑菌效果具有显著增效作用；其他配比具有相加作用。
实施例3：ZJS178与咪鲜胺复配对小麦赤霉病的室内毒力测定
试验对象：小麦赤霉病(Fusarium graminearum)由本试验室菌种室保存。
试验方法：参考《中华人民共和国农业行业标准NY/T 1156.2－2006》菌丝生长速率法。每个药剂按有效成分含量分别设5个剂量处理，将上述小麦赤霉病病原菌用PDA培养基培养，待菌落长满培养皿2/3时，用直径5mm的打孔器在菌落边缘打成菌块，用接种针将菌块移至预先配制成的含毒PDA培养基中央，然后置于25℃培养箱内培养，每处理重复4次。视CK菌落生长情况，采用十字交叉法用卡尺量取各处理菌落直径cm，求出校正抑制百分率。通过抑制率的机率值和系列浓度的对数值之间的线性回归分析，求出各药剂的EC50值，再根据孙云沛法计算共毒系数(CTC)。
药效计算：每个菌落十字交叉测两个直径，以其平均数代表菌落大小。按下式求出菌落生长抑制率：菌落生长抑制率％＝(空白对照菌落增长直径-药剂处理菌落增长直径)×100/空白对照菌落增长直径。
表2：ZJS178与咪鲜胺复配对小麦赤霉病的室内毒力测定结果
| 药剂 | EC50(μg/mL) | ATI | TTI | 共毒系数CTC |
| ZJS178(A) | 0.0379 | 100.00 | / | / |
| 咪鲜胺(B) | 0.3191 | 11.88 | / | / |
| A+B(1：20) | 0.2214 | 17.12 | 16.08 | 106.48 |
| A+B(1：15) | 0.1788 | 21.20 | 17.39 | 121.91 |
| A+B(1：12) | 0.1587 | 23.88 | 18.66 | 127.99 |
| A+B(1：8) | 0.1224 | 30.96 | 21.67 | 142.88 |
| A+B(1：6) | 0.1067 | 35.52 | 24.47 | 145.17 |
| A+B(1：4) | 0.0789 | 48.04 | 29.50 | 162.81 |
| A+B(1：3) | 0.0725 | 52.28 | 33.91 | 154.16 |
| A+B(1：2) | 0.0599 | 63.27 | 41.25 | 153.37 |
| A+B(1：1) | 0.0422 | 89.81 | 55.94 | 160.55 |
| A+B(2：1) | 0.0322 | 117.70 | 70.63 | 166.65 |
| A+B(3：1) | 0.0311 | 121.86 | 77.97 | 156.30 |
| A+B(4：1) | 0.0301 | 125.91 | 82.38 | 152.85 |
| A+B(6：1) | 0.0293 | 129.35 | 87.41 | 147.98 |
| A+B(8：1) | 0.0301 | 125.91 | 90.21 | 139.58 |
| A+B(12：1) | 0.0314 | 120.70 | 93.22 | 129.48 |
| A+B(15：1) | 0.0342 | 110.82 | 94.49 | 117.28 |
| A+B(20：1) | 0.0365 | 103.84 | 95.80 | 108.38 |
由表2所示，ZJS178与咪鲜胺质量百分比为1:15～12:1时对小麦赤霉病菌生长的抑菌效果具有显著增效作用；其他配比具有相加作用。
实施例4：ZS178与咪鲜胺锰盐复配对草莓枯萎病的室内毒力测定
试验对象：草莓枯萎病(Fusarium oxysporum)由本试验室菌种室保存。生测方法参照生测实施例3。
表3：ZJS178与咪鲜胺锰盐复配对草莓枯萎病的室内毒力测定结果
由表3所示，ZJS178与咪鲜胺锰盐质量百分比为1:12～15:1时对草莓枯萎病菌生长的抑菌效果具有显著增效作用；其他配比具有相加作用。
实施例5：田间药效试验
一、制剂配制
所有制剂配比中百分含量均为质量百分比。
(1)20％ZJS178·甲基硫菌灵悬浮剂
称取10％ZJS178、10％甲基硫菌灵、2％TERSPERSE 2500、3％TERSPERSE 2425、0.2％黄原胶、3％白炭黑、5％乙二醇、0.3％苯甲酸、0.5％有机硅消泡剂，去离子水加至100％质量份。
按配方比例，以水为介质，将原药、分散剂、助悬剂和防冻剂等加入到配料釜中混合均匀，经球磨机或高速剪切分散30min，用砂磨机砂磨后制成悬浮剂。
(2)46％ZJS178·咪鲜胺悬浮剂
称取23％ZJS178、23％咪鲜胺、2％NNO、2％TERSPERSE 2500、1％乳化剂T-60、3％农乳700#、0.1％黄原胶、3％白炭黑、5％丙二醇、0.5％甲醛、0.5％有机硅消泡剂，去离子水加至100％质量份。
按配方比例，以水为介质，将原药、分散剂、助悬剂和防冻剂等加入到配料釜中混合均匀，经球磨机或高速剪切分散30min，用砂磨机砂磨后制成悬浮剂。
二、田间试验
2.1防治小麦赤霉病田间药效试验
防治小麦赤霉病参照“NY/T1464.15-2007农药田间药效试验准则——杀菌剂防治小麦赤霉病”的规定进行，小麦抽穗扬花初期施药1次，乳熟期调查结果，每试验小区采用对角线5点取样，每点调查100～200穗，以枯穗面积占整个穗面积的百分率来分级，记录各级病穗数和总穗数。病害分级标准如下：
0级：全穗无病；
1级：枯穗面积占全穗面积1/4以下；
3级：枯穗面积占全穗面积1/4～1/2；
5级：枯穗面积占全穗面积1/2～3/4；
7级：枯穗面积占全穗面积3/4以上。
药效计算方法：根据调查结果，按照下面(1)、(2)公式计算病情指数和防效。试验数据采用邓肯氏新复极差法(DMRT)进行统计分析。
式中：CK1为空白对照区药后病情指数；PT1为药剂处理区药后病情指数。
表4：防治小麦赤霉病田间药效试验结果
*同列数据后不同小写字母表示在P＜0.05水平差异显著。
表4结果表明：46％ZJS178·咪鲜胺悬浮剂在有效成分5克/亩～15克/亩的剂量下对小麦赤霉病有良好的防效，防效达91.31％～97.88％，优于对照单剂的防效。试验药剂对试验作物安全。
2.2防治番茄枯萎病霉病的田间药效试验
试验点设在绍兴市东浦镇，试验地土壤类型为壤土，肥力中等，pH值呈中性；品种为浙粉202。番茄移苗定植后，药液灌根处理，药剂种类及用量见表5；第一次用药一周后再灌根一次；药剂处理后21天调查番茄枯萎病发生情况：每处理随机5点取样，各点调查5平方米，每点分别调查番茄总株数和病株数。计算病株率和防效。
防治效果(％)＝((对照病株率－处理病株率)/对照病株率)×100
试验结果如表5所示。
表5：ZJS178与甲基硫菌灵复配剂对番茄枯萎病田间药效试验结果
*同列数据后不同小写字母表示在P＜0.05水平差异显著。
表5结果表明，在相同有效剂量情况下，ZJS178·甲基硫菌灵复配组合能有效防治番茄枯萎病，防效显著优于单剂。试验药剂对试验作物安全。
综合上述，室内生测和田间药效试验结果表明：本发明组合物组分合理，治疗加保护作用，杀菌效果好，减少用药次数，用药成本低，且其活性和杀菌效果不是各组分活性的简单叠加，而是有显著的增效作用，组合物由不同作用机制的有效成分组成，作用位点增加，有利于克服和延缓病菌抗药性的产生，对试验作物均无明显不良影响，叶色、长势等都正常，安全性好，符合农药制剂的安全性要求。本发明对由镰刀菌引起的病害有优异防效。
Claims (11)
1.一种杀菌剂组合物，其特征在于，所述组合物的活性组分包括如式(Ⅰ)所示结构的化合物ZJS178和咪唑类杀菌剂：
2.按照权利要求1所述的杀菌剂组合物，其特征在于：所述咪唑类杀菌剂选自咪鲜胺、多菌灵、咪鲜胺锰盐或甲基硫菌灵中的至少一种。
3.按照权利要求1所述的杀菌剂组合物，其特征在于：所述组合物中ZJS178与咪唑类杀菌剂的质量配比为60:1～1:60。
4.按照权利要求3所述的杀菌剂组合物，其特征在于：所述组合物中ZJS178与咪唑类杀菌剂的质量配比为20:1～1:20。
5.按照权利要求4所述的杀菌剂组合物，其特征在于：所述组合物中ZJS178与咪唑类杀菌剂的质量配比为12:1～1:12。
6.按照权利要求5所述的杀菌剂组合物，其特征在于：所述组合物中ZJS178与咪唑类杀菌剂的质量配比为6:1～1:6。
7.按照权利要求6所述的杀菌剂组合物，其特征在于：所述组合物中ZJS178与咪唑类杀菌剂的质量配比为3:1～1:3。
8.如权利要求1-7任一项所述的杀菌剂组合物，其特征在于，所述杀菌剂组合物还包括农药剂型所需要的辅助成分，组合物中活性成分的质量占比为0.5～90％。
9.如权利要求1-7任一项所述的杀菌剂组合物在防治由镰刀菌引起的作物病害中的应用。
10.如权利要求9所述的应用，其特征在于，所述镰刀菌为禾谷镰孢菌复合种、藤仓镰刀菌复合种、尖孢镰刀菌、串珠镰刀菌。
11.如权利要求10所述的应用，其特征在于，所述作物病害包括：瓜类枯萎病、番茄枯萎病、香蕉枯萎病、棉花枯萎病、草莓枯萎病、水稻恶苗病和小麦赤霉病。
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