CN115403486A - 一种霜脲氰铜及其制备方法、应用 - Google Patents
一种霜脲氰铜及其制备方法、应用 Download PDFInfo
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- CN115403486A CN115403486A CN202211153015.2A CN202211153015A CN115403486A CN 115403486 A CN115403486 A CN 115403486A CN 202211153015 A CN202211153015 A CN 202211153015A CN 115403486 A CN115403486 A CN 115403486A
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- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 title claims abstract description 106
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 79
- 229910052802 copper Inorganic materials 0.000 title claims abstract description 79
- 239000010949 copper Substances 0.000 title claims abstract description 79
- 238000002360 preparation method Methods 0.000 title abstract description 18
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- 240000008067 Cucumis sativus Species 0.000 claims description 17
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- 238000000034 method Methods 0.000 claims description 15
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- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 2
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- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
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- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 abstract description 3
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- JJKSAEHNIHMQKQ-UHFFFAOYSA-N copper;quinoline Chemical compound [Cu].N1=CC=CC2=CC=CC=C21 JJKSAEHNIHMQKQ-UHFFFAOYSA-N 0.000 description 5
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
- C07C273/1863—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety from urea
-
- 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
- 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
- A01N47/08—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 the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/50—Y being a hydrogen or an acyclic carbon atom
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- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Engineering & Computer Science (AREA)
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- General Chemical & Material Sciences (AREA)
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- Agronomy & Crop Science (AREA)
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Abstract
本发明公开了一种霜脲氰铜及其制备方法、应用,通过在霜脲氰分子结构上引入络合铜离子,合成了一种新型的有机铜霜脲氰铜,该化合物具有杀菌谱广,霜脲氰铜不仅对卵菌有效,而且对细菌有效,可以同时防治真菌性和细菌性病害,持效期长且不易诱使病菌产生耐药性,霜脲氰铜可以单独使用,从而降低农药使用量和使用成本,对于卵菌,霜脲氰铜的防效好于霜脲氰。所提供的制备方法,所用试剂均为常见试剂,操作步骤简便。
Description
技术领域
本发明涉及化合物制备技术领域,尤其涉及一种霜脲氰铜及其制备方法、应用。
背景技术
霜脲氰是一种高效、低毒杀菌剂,其作用机理是通过抑制病原菌的细胞线粒体中的电子转移、使其氧化和磷酸化的作用停止,从而使病原菌细胞丧失能量来源而死亡。主要对真菌的类脂化合物的生物合成和细胞膜机能起作用,抑制孢子萌发、牙管伸长、附着胞和菌丝的形成。是触杀和预防性杀菌剂,对卵菌纲的霜霉、疫霉和单轴霉有效。
但是霜脲氰存在杀菌谱较窄的缺点,除卵菌外对其它真菌和细菌无效。此外,霜脲氰持效期短,且易诱使病菌产生耐药性。
因此,现有技术还有待于改进和发展。
发明内容
鉴于上述现有技术的不足,本发明的目的在于提供一种霜脲氰铜及其制备方法、应用,旨在解决现有霜脲氰作为杀菌剂杀菌谱窄的问题。
一种霜脲氰铜,其化学结构式如下:
一种上述所述的霜脲氰铜的制备方法,其中,包括步骤:
将霜脲氰分散在溶剂中,得到霜脲氰溶液;
加热所述霜脲氰溶液,并向加热后的所述霜脲氰溶液中依次加入铜盐和碱液,得到混合溶液;其中,所述碱液采用滴加的方式加入,滴加时间约30min。
将所述混合溶液在30-100℃温度条件下反应,得到霜脲氰铜;优选地,反应温度为50-60℃。具体来说,在滴加结束后在30-100℃保温2hr,趁热过滤,收集滤液回收部分溶剂后冷却到10-20℃结晶,过滤、干燥得到产品霜脲氰铜络合物。
可选地,所述的霜脲氰铜的制备方法,其中,所述溶剂选自甲醇、乙醇、异丙醇、丙酮和乙腈中的一种。
可选地,所述的霜脲氰铜的制备方法,其中,所述加热所述霜脲氰溶液,加热温度为30-100℃。优选地,加热温度为50-60℃
可选地,所述的霜脲氰铜的制备方法,其中,所述铜盐选自硫酸铜、氯化铜、醋酸铜和硝酸铜中的一种。
可选地,所述的霜脲氰铜的制备方法,其中,所述碱液包括;氢氧化钠溶液、氢氧化钾溶液;所述碱液的体积浓度为1-99%;优选地,所述碱液的体积浓度为20-30%。
一种采用上述所述的制备方法制备得到的霜脲氰铜在防治作物病害中的应用。
可选地,所述的霜脲氰铜在防治作物病害中的应用,其中,所述作物病害包括:真菌性病害和细菌性病害。
可选地,所述的霜脲氰铜在防治作物病害中的应用,其中,所述真菌性病害包括:马铃薯晚疫病、番茄晚疫病、葡萄霜霉病、黄瓜霜霉病、辣椒疫病、荔枝霜疫霉病、芋头疫病、玉米茎基腐病以及草莓根腐病;所述细菌性病害包括:水稻白叶枯病、水稻细菌性条斑病、柑橘溃疡病、黄瓜细菌性角斑病、番茄青枯病、大白菜软腐病以及桃树细菌性穿孔病。
可选地,所述的霜脲氰铜在防治作物病害中的应用,其中,所述作物包括:水稻、马铃薯、玉米、大豆、菜豆、蚕豆、柑橘、葡萄、芒果、荔枝、桃、黄瓜、西瓜、甜瓜、草莓、番茄、辣椒、茄子、姜、葱、蒜、大白菜以及芋头。
有益效果:与现有技术相比,本发明通过在霜脲氰分子结构上引入络合铜离子,合成了一种新型的有机铜霜脲氰铜。该化合物具有如下特点:
1)杀菌谱广,霜脲氰铜不仅对卵菌有效,而且对细菌有效,可以同时防治真菌性和细菌性病害。
2)持效期长且不易诱使病菌产生耐药性,霜脲氰铜可以单独使用,从而降低农药使用量和使用成本。
3)对于卵菌,霜脲氰铜的防效好于霜脲氰。
附图说明
图1为本发明实施例中霜脲氰铜、喹啉铜对黄瓜角斑病细菌活性对比,其中,每列数据上为霜脲氰铜(10%),下为喹啉铜(33.5%);
图2为本发明实施例中霜脲氰铜、喹啉铜对水稻白叶枯病细菌活性对比,其中,每列数据上为霜脲氰铜(10%),下为喹啉铜(33.5%)。
具体实施方式
本发明提供一种霜脲氰铜及其制备方法、应用,为使本发明的目的、技术方案及效果更加清楚、明确,以下对本发明进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。
实施例1
将20g霜脲氰、100g甲醇加入反应瓶中,搅拌升温至55℃,加入12.5g五水硫酸铜,滴加13.5g液碱(30%氢氧化钠溶液),约30min滴完,然后保温2hr。趁热过滤,收集滤液回收部分溶剂后冷却到10~20℃结晶,过滤、干燥得到19.8g霜脲氰铜络合物,铜含量13.53%。
实施例2
将20g霜脲氰、100g乙腈加入反应瓶中,搅拌升温至55℃,加入15.5g五水硫酸铜,滴加16.7g液碱(30%氢氧化钠溶液),约30min滴完,然后保温2hr。趁热过滤,收集滤液回收部分溶剂后冷却到10~20℃结晶,过滤、干燥得到20.7g霜脲氰铜络合物,铜含量13.9%。
实施例3
将20g霜脲氰、100g乙醇加入反应瓶中,搅拌升温至55℃,加入13.5g氯化铜,滴加26.7g液碱(30%氢氧化钠溶液),约30min滴完,然后保温2hr。趁热过滤,收集滤液回收部分溶剂后冷却到10~20℃结晶,过滤、干燥得到18.7g霜脲氰铜络合物,铜含量13.6%。
制剂实施例1(霜脲氰铜悬浮剂)
在剪切釜中依次真空抽入三苯乙烯基苯酚聚氧乙烯醚磷酸酯0.50%-5.00%、萘磺酸钠甲醛缩合物0.50%-5.00%、辛基酚聚氧乙烯醚1.00%-3.00%、1,2-苯丙异噻唑啉-3-酮0.15%-0.30%、聚硅氧烷0.15%-0.30%、黄原胶0.05%-0.3%、丙二醇3.00%-20.00%等物料,水补充至100%,打开剪切釜放空阀。打开剪切釜的人孔盖,开启剪切机10分钟后将定量的霜脲氰铜原药投入剪切釜中,剪切1小时后关闭剪切机。打开剪切釜釜底阀,开启砂磨机冷却水阀并保持冷却水的畅通,开启砂磨机进行2次砂磨,砂磨后的物料转入剪切釜再次剪切1小时,检测合格后,放料过滤即得霜脲氰铜悬浮剂。
制剂实施例2(霜脲氰铜水分散粒剂)
在搅拌釜中依次投入定量的需霜脲氰铜、木质素磺酸钠1.0%-15.0%、烷基萘磺酸盐甲醛缩合物1.0%-15.0%、二异丙基萘磺酸钠0.5%-3.0%、硫酸钠5.0%-30.0%,高岭土补充至100%,打开搅拌,搅拌1-1.5小时至完全搅拌均匀,开启气流粉碎机进行粉碎;粉碎料再搅拌混合1-1.5小时。取样分析,合格后放料,物料转入流化床造粒机,开始造粒,造粒过程中观察颗粒均匀度,待成粒均匀后,取样检测合格即得霜脲氰铜水分散粒剂。
制剂实施例3(霜脲氰铜可湿性粉剂)
在搅拌釜中依次投入定量的霜脲氰铜、木质素磺酸钠1.0%-15.0%、烷基萘磺酸盐甲醛缩合物1.0%-15.0%、十二烷基硫酸钠0.5%-5.0%、白炭黑1.0%-10.0%,高岭土补充至100%,打开搅拌,搅拌1-1.5小时至完全搅拌均匀,开启气流粉碎机进行粉碎;粉碎料再搅拌混合1-1.5小时,取样检测合格即得霜脲氰铜可湿性粉剂。
生物测定实施例1(黄瓜细菌性角斑病)
试验方法:参照《中华人民共和国农业行业标准NY/T 1156.16-2008》,浊度法
供试药剂:霜脲氰铜10%悬浮剂、喹啉铜33.5%悬浮剂
试验结果如表1所示:霜脲氰铜对黄瓜细菌性角斑病的EC50值84.90ppm,防效好于防治该病的常用药喹啉铜EC50值144.97ppm。
表1各处理OD值及抑菌率表
生物测定实施例2(水稻白叶枯病)
试验方法:参照《中华人民共和国农业行业标准NY/T 1156.16-2008》,浊度法
供试药剂:霜脲氰铜10%悬浮剂、喹啉铜33.5%悬浮剂
试验结果如表2所示:霜脲氰铜、喹啉铜对水稻白叶枯病细菌(NJAU)的活性趋势一致,霜脲氰铜在20ppm、40ppm时没有活性,在80ppm时抑菌率超过50%,在320ppm时达到100%抑菌效果;喹啉铜在20ppm、40ppm时没有活性,在80ppm时抑菌率超过40%,在400ppm时达到100%抑菌效果;霜脲氰铜的EC50值=69.72ppm,喹啉铜的EC50值=93.94ppm,霜脲氰铜的活性高于喹啉铜。
表2各处理平均OD值及抑菌率表
生物测定实施例3(辣椒疫霉)
试验方法:平皿菌丝抑制法
供试药剂:霜脲氰铜10%悬浮剂(宁波三江益农化学有限公司)
对照药剂:霜脲氰250克/升悬浮剂(宁波三江益农化学有限公司)
试验结果:霜脲氰铜对辣椒疫霉菌丝的抑制活性明显高于霜脲氰,霜脲氰EC50值为26.40ppm,霜脲氰铜的EC50值为7.11ppm。
注:抑制率=[(对照菌落直径-处理菌落直径)/(对照菌落直径-菌碟直径)]×100%。本实验菌碟直径5mm。
田间试验实例1:黄瓜细菌性角斑病
试验时间:2021年7月-8月
试验地点:广西南宁市邕宁区蒲庙镇
试验作物:黄瓜,供试品种为当地主栽品种“广良3抗2”
防治对象:由Pseudomonas syringae侵染引起的黄瓜细菌性角斑病
供试药剂:霜脲氰铜80%水分散粒剂(宁波三江益农化学有限公司)、喹啉铜50%水分散粒剂(陕西汤普森生物科技有限公司)
施药方法:采用喷雾法施药。在黄瓜细菌性角斑病发生初期对植株茎叶施药,每隔7-10天施用1次,连续使用3次。
试验结果:第3次药后9天调查,霜脲氰铜80%水分散粒剂有效成分300克/公顷、375克/公顷、450克/公顷对黄瓜细菌性角斑病的防效分别为70.70%、73.30%、78.98%,与对照药剂喹啉铜50%水分散粒剂有效成分500克/公顷对黄瓜细菌性角斑病的防效71.72%无显著差异。
80%霜脲氰铜水分散粒剂第3次药后9天对黄瓜细菌性角斑病的防效
田间试验实例2:马铃薯晚疫病
试验时间:2021年5月-6月
试验地点:四川省汉源县马烈乡
试验作物:马铃薯/鄂薯5号
防治对象:由Phytophthora infestans侵染引起的马铃薯晚疫病。
供试药剂:霜脲氰铜45%悬浮剂(宁波三江益农化学有限公司)、霜脲·锰锌72%可湿粉剂(浙江禾本科技股份有限公司)
施药方法:在马铃薯晚疫病发病前期或初期使用,喷雾处理,共施药3次,施药间隔7天。
试验结果:霜脲氰铜45%悬浮剂对马铃薯晚疫病防效高于对照药剂霜脲·锰锌72%可湿性粉剂,在3次用药后13天仍能维持70%以上防效,持效期媲美霜脲·锰锌72%可湿性粉剂。
田间试验实例3:葡萄霜霉病
试验时间:2021年4月,第一次喷药在4月12日上午(葡萄花蕾期),第二次喷药在4月19日下午(葡萄开花前),第三次喷药在4月28日上午(葡萄初花期)
试验地点:浙江省金华市金东区赤松镇
试验作物:“巨峰”葡萄
防治对象:葡萄霜霉病
供试药剂:
施药方法:葡萄发病前或初期用霜脲氰铜80%水分散粒剂1500~3000倍喷雾,整株喷雾;45升/亩,葡萄正反面叶面均匀喷雾,以叶面湿润不滴液为准。
试验结果:霜脲氰铜80%WG对葡萄霜霉病防效在80%以上。
田间试验实例4:水稻白叶枯病
试验时间:2021年7月
试验地点:浙江省诸暨市枫桥镇
试验作物:水稻,中早39
防治对象:水稻白叶枯病
供试药剂:
王铜84%水分散粒剂(宁波三江益农作物保护有限公司)
吡唑·王铜40%悬浮剂(宁波三江益农化学有限公司)
霜脲氰铜80%水分散粒剂(宁波三江益农化学有限公司)
霜脲氰铜60%可湿性粉剂(宁波三江益农化学有限公司)
霜脲氰铜45%悬浮剂(宁波三江益农化学有限公司)
噻唑锌20%悬浮剂(浙江新农化工股份有限公司)
施药方法:白叶枯病发病初期,喷雾处理,连喷两次,间隔7天,器械采用大疆T16无人机,亩用水量1.5L
试验结果:霜脲氰铜制剂对水稻白叶枯病的防控效果好于常用药剂王铜84%水分散粒剂和吡唑·王铜40%悬浮剂,与噻唑锌20%悬浮剂基本相当。
综上所述,本发明提供的一种霜脲氰铜及其制备方法、应用,通过在霜脲氰分子结构上引入络合铜离子,合成了一种新型的有机铜霜脲氰铜,该化合物具有杀菌谱广,霜脲氰铜不仅对卵菌有效,而且对细菌有效,可以同时防治真菌性和细菌性病害,持效期长且不易诱使病菌产生耐药性,霜脲氰铜可以单独使用,从而降低农药使用量和使用成本,对于卵菌,霜脲氰铜的防效好于霜脲氰。所提供的制备方法,所用试剂均为常见试剂,操作步骤简便。
应当理解的是,本发明的应用不限于上述的举例,对本领域普通技术人员来说,可以根据上述说明加以改进或变换,所有这些改进和变换都应属于本发明所附权利要求的保护范围。
Claims (10)
2.一种权利要求1所述的霜脲氰铜的制备方法,其特征在于,包括步骤:
将霜脲氰分散在溶剂中,得到霜脲氰溶液;
加热所述霜脲氰溶液,并向加热后的所述霜脲氰溶液中依次加入铜盐和碱液,得到混合溶液;
将所述混合溶液在30-100℃温度条件下反应,得到霜脲氰铜。
3.根据权利要求2所述的霜脲氰铜的制备方法,其特征在于,所述溶剂选自甲醇、乙醇、异丙醇、丙酮和乙腈中的一种。
4.根据权利要求2所述的霜脲氰铜的制备方法,其特征在于,所述加热所述霜脲氰溶液,加热温度为30-100℃。
5.根据权利要求2所述的霜脲氰铜的制备方法,其特征在于,所述铜盐选自硫酸铜、氯化铜、醋酸铜和硝酸铜中的一种。
6.根据权利要求2所述的霜脲氰铜的制备方法,其特征在于,所述碱液包括;氢氧化钠溶液、氢氧化钾溶液;所述碱液的体积浓度为1-99%。
7.一种采用权利要求2-6任一所述的制备方法制备得到的霜脲氰铜在防治作物病害中的应用。
8.根据权利要求7所述的霜脲氰铜在防治作物病害中的应用,其特征在于,所述作物病害包括:真菌性病害和细菌性病害。
9.根据权利要求8所述的霜脲氰铜在防治作物病害中的应用,其特征在于,所述真菌性病害包括:马铃薯晚疫病、番茄晚疫病、葡萄霜霉病、黄瓜霜霉病、辣椒疫病、荔枝霜疫霉病、芋头疫病、玉米茎基腐病以及草莓根腐病;所述细菌性病害包括:水稻白叶枯病、水稻细菌性条斑病、柑橘溃疡病、黄瓜细菌性角斑病、番茄青枯病、大白菜软腐病以及桃树细菌性穿孔病。
10.根据权利要求8所述的霜脲氰铜在防治作物病害中的应用,其特征在于,所述作物包括:水稻、马铃薯、玉米、大豆、菜豆、蚕豆、柑橘、葡萄、芒果、荔枝、桃、黄瓜、西瓜、甜瓜、草莓、番茄、辣椒、茄子、姜、葱、蒜、大白菜以及芋头。
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CH664562A5 (de) * | 1985-07-10 | 1988-03-15 | Stepan Safronovich Kukalenko | Zink- und kupferkomplexsalze der aethylen-bis-dithiokarbamidsaeure und des n-(benzimidazolyl-2)-karbamidsaeuremethylesters, verfahren zur herstellung und anwendung derselben. |
JPH08325111A (ja) * | 1995-05-29 | 1996-12-10 | Otsuka Chem Co Ltd | 農園芸用殺菌剤 |
US20050159482A1 (en) * | 2002-03-05 | 2005-07-21 | Friedrich Franke | Biologically active copper-organic agents |
CN101069514A (zh) * | 2007-06-19 | 2007-11-14 | 广东省昆虫研究所 | 一种含葡萄糖酸铜的杀菌剂 |
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2022
- 2022-09-21 CN CN202211153015.2A patent/CN115403486A/zh active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH664562A5 (de) * | 1985-07-10 | 1988-03-15 | Stepan Safronovich Kukalenko | Zink- und kupferkomplexsalze der aethylen-bis-dithiokarbamidsaeure und des n-(benzimidazolyl-2)-karbamidsaeuremethylesters, verfahren zur herstellung und anwendung derselben. |
JPH08325111A (ja) * | 1995-05-29 | 1996-12-10 | Otsuka Chem Co Ltd | 農園芸用殺菌剤 |
US20050159482A1 (en) * | 2002-03-05 | 2005-07-21 | Friedrich Franke | Biologically active copper-organic agents |
CN101069514A (zh) * | 2007-06-19 | 2007-11-14 | 广东省昆虫研究所 | 一种含葡萄糖酸铜的杀菌剂 |
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