CN108366565A - 新的植物保护组合物及其应用 - Google Patents
新的植物保护组合物及其应用 Download PDFInfo
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- CN108366565A CN108366565A CN201680068822.0A CN201680068822A CN108366565A CN 108366565 A CN108366565 A CN 108366565A CN 201680068822 A CN201680068822 A CN 201680068822A CN 108366565 A CN108366565 A CN 108366565A
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Classifications
-
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
-
- 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
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cultivation Of Plants (AREA)
- Protection Of Plants (AREA)
Abstract
本发明涉及一种植物保护组合物或农用杀虫剂,包含:选自包括聚(烷基)胍、聚(烷基)双胍、聚鸟嘌呤或奥替尼啶的组中的物质,或者该组中的物质的任意共混物。在优选实施方式中,所述选自包括聚(烷基)胍、聚(烷基)双胍、聚鸟嘌呤或奥替尼啶的组中的物质,或者该组中的物质的任意共混物,以与显示出针对农业病虫害的活性的至少一种其他组分的组合存在。所述显示出针对农业病虫害的活性的至少一种其他组分可代表市场上已知的杀虫剂的至少一种活性剂。本发明的另一方面涉及一种保护植物免受植物病原体侵害的方法,所述方法包括施用上述农用杀虫剂组合物。
Description
技术领域
本发明涉及一种基于化学活性剂或化学活性剂的组合物的植物保护剂或组合物。
植物保护剂通常被定义为尤其用于保护植物的杀虫剂和除草剂,更具体地为用于以下目的的化学剂或生物剂和组合物:
1)保护植物和植物产品免受病原生物侵害或防止它们的作用;
2)以一些其它方式(例如生长调节剂)影响植物的生命/活力;
3)保存植物产品(例如种子保护剂);
4)破坏不需要的植物或植物部分,或者抑制或防止植物的任何不希望的生长(除草剂)。
本发明尤其涉及根据上述组1所述的基于化学剂或化学剂的组合物的植物保护剂。相应的病原生物常常被称作植物病原体。
背景技术
现有技术中已知组1的各种植物保护剂。
这些已知的且市场上可买到的农用杀虫剂中的一部分,由于它们对例如鱼类资源、动物、其他生物、土壤中的植物等具有毒性,而只能以相对低的剂量且在严格受控的条件下施用。
许多市售的农用杀虫剂的问题还在于很多病原微生物抗性的发展。因此,仍然非常需要具有针对植物病原体的活性的另外的化学剂或化学组合物,这通过正在进行的研究和开发工作反映出来。
本发明的主要目的是提供植物保护剂或农用杀虫剂,其有效抵抗植物病原体,同时在作为植物保护剂的预期应用所需的浓度范围内对其他植物或生物体没有或几乎没有毒性。
这些目的通过具有权利要求1或权利要求4的特征的农用杀虫剂来实现。本发明的另外的方面和更具体的实施方式是另外的权利要求的主题。
发明内容
根据权利要求1所述的农用杀虫剂包含:来自聚(烷基)胍(或者被表示或称为聚(亚烷基)胍)、聚(烷基)双胍(或聚(亚烷基)双胍)、聚鸟嘌呤或奥替尼啶(octenidin)的组的物质,或该组的物质的任意共混物。
这些物质的优点在于,它们显示出抗微生物活性,但至少在作为植物保护剂的预期应用所需的浓度范围内对人和动物没有毒性。
具体而言,根据本发明使用的物质在植物病原体领域显示出针对细菌、真菌和病毒的广谱效果。
这些物质,尤其是聚(六亚甲基)胍(PHMG)和聚(六亚甲基)双胍(PHMB),的有利的广谱效果是特别令人惊讶的,因为先前仅仅知道这样的聚(烷基)胍或聚(烷基)双胍对某些特定细菌,尤其是人类病原细菌如金黄色葡萄球菌(Staphylococcus aureus)、铜绿假单胞菌(Pseudomonas aeruginosa)和猪霍乱沙门氏菌(Salmonella choleraesuis)具有抗菌效果。
在本文中,例如在以下出版物(Joumal of Medical Microbiology(2008),57,1523-1528:“Polyhexamethylene guanidine hydrochloride-based disinfectant;anovel tool to fight meticillin-resistant staphylococcus aureus and nosocomialinfections”,Mathias K.Oulé等)中,描述了阳离子聚合物聚(六亚甲基)胍-盐酸盐(PHMGH)在医源性感染方面,对人病原微生物的抗菌活性。具体而言,出版物“MathiasK.Oulé等”解决了作为对抗具有甲氧西林抗性的人病原金黄色葡萄球菌的新工具的PHMGH的抗微生物功效。
在本发明的上下文中,术语“植物病原体(plant-pathogen)”指起到不利于植物或植物产品的病原生物体作用的微生物,尤其是细菌、真菌和病毒。
很多植物病原体,例如真菌,是形成孢子的生物体。特别令人惊讶的是,已经发现根据本发明的农用杀虫剂显示出针对各种各样的形成孢子的生物体的高抗微生物活性。
例如,根据本发明的农用杀虫剂已经显示出对植物病原体,如细菌梨火疫菌(Erwinia amylovora)(火疫病),真菌马铃薯晚疫病菌(Phytophthora infestans)(晚疫病),苹果黑星菌(Venturia inaequalis)(苹果黑星病)和镰孢菌属的子囊菌特别有效。然而,所要求保护的农用杀虫剂的应用绝不局限于这些生物体,下面公开了各种另外的目标病原体。
在本发明的优选方面中,农用杀虫剂指这样的组合物,在所述组合物中,选自包括聚(烷基)胍、聚(烷基)双胍、聚-胍或奥替尼啶的组中的物质,或者这些组中的物质的任意共混物,以与显示出针对农业病虫害的活性的至少一种其他组分的组合存在。
更具体地,所述显示出针对农业病虫害的活性的其他组分指市场上已知或可以买到的杀虫剂,或者市场上已知或可以买到的杀虫剂的至少一种活性剂。
已经发现利用这样的组合,多种市售的杀虫剂的剂量可以降低高达90%,且不损失抗微生物的有效性。
此外,甚至已经证明,对于许多市售的农用杀虫剂来说,在仍然应用这些杀虫剂的相同剂量的同时可以实现抗微生物活性的增加(虽然与权利要求1的物质组合)。这是特别有利的,因为由于严格的法规限制,仅通过增加商业杀虫剂的剂量来提高这些商业杀虫剂的抗微生物活性通常是不可能的。
这些市售的农用杀虫剂,特别是属于上述组1)的植物保护剂的那些,可根据它们的化学性质和它们的活性的相应机制或模式被分类成例如以下类别(根据杀菌剂抗性活性委员会(Fungicide Resistance Activity Committee,FRAC)):
A)唑类(商品名:Opus Top、Input、Agent、Caramba);
B)苯并咪唑氨基甲酸酯类(商品名:Duett Ultra、Don-Q、Paroli、Topsin);
C)羧酰胺类(商品名:Input Xpro、Variano Xpro、Aviafor Xpro、Champion、Adexar);
D)胺类(商品名:Input Xpro、Rubin TT、pronto Plus、Input Classic、Ceralo、Prolectus);
E)甲氧基丙烯酸酯类(Strobulines)(商品名:Amistar、Ortiva、Stroby、Discus、Acanto、Flint);
F)作为接触剂的应用(商品名:Delan、Infinito、Acrobat Plus、Tatto、Tridex、Revus、MZ、Ridomil Gold)。
根据FRAC,除了这些类别之外的其他商业产品是Vegas、Dynali、Capalo、Fleity、Vivando。分类“接触剂(contact agent)”是基于借助于接触植物表面的施用形式。
典型地,在根据本发明的农用杀虫剂中,所述显示出针对农业病虫害的活性的至少一种其他组分选自包括以下物质的化合物的组:唑类,尤其是二唑、***、苯并咪唑和吡唑;氨基甲酸酯,尤其是苯并咪唑氨基甲酸酯和二硫代氨基甲酸酯;羧酰胺;二甲酰亚胺;酰替苯胺;烟酰胺;胺和铵化合物,包括螺噁茂胺(spiroketalamine)和杂环化合物例如嘧啶、吡啶、哌啶、吗啉、吡咯,尤其是苯基吡咯、二嗪;甲氧基丙烯酸酯类;腈,尤其是氯代腈;肉桂酸。
在更具体的实施方式中,所述显示出针对农业病虫害的活性的至少一种其他组分选自包括以下化合物的组:丙基-3-(二甲氨基)丙基-氨基甲酸酯盐酸盐(也称为霜霉威盐酸盐)、8-叔丁基-1,4-二氧螺环[4.5]癸烷-2-基甲基-(乙基)(丙基)胺(螺环菌胺)、(RS)-2-(4-氯苯基)-N-[3-甲氧基-4-(丙-2-炔氧基)苯乙基]-2-(丙-2-炔氧基)乙酰胺(双炔酰菌胺(Mandipropamide))、N-甲氧基乙酰基)-N-2,6-二甲苯基-D-丙氨酸甲酯(精甲霜灵(Metalaxyl-M))、N-丙基-N-[2-2,4,6-三氯苯氧基)乙基]咪唑-1-羧酰胺(咪鲜胺(Prochloraz))、N-4,6-二甲基嘧啶-2-基)苯胺(嘧霉胺)、(E)-3-甲氧基-2-{2-6-(三氟甲基)吡啶-2-基氧基甲基]-苯基}丙烯酸甲酯(啶氧菌酯(Picoxystrobin))、(E)-{2-[6-(2-氯苯氧基)-5-氟嘧啶-4-基氧基]苯基}(5,6-二氢-1,4,2-二噁嗪-3-基)甲酮(氟嘧菌酯(Fluoxastrobin))、3-(二氟甲基)-1-甲基-N-(3`,4`,5`-三氟联苯-2-基)吡唑-4-羧酰胺(Fluoxapyroxad)、5-氨基-2,3-二氢-2-异丙基-3-氧代-4-(邻甲苯基)吡唑-1-硫代甲酸-S-烯丙酯(胺苯吡菌酮)、四氯间苯二腈(百菌清)、3-(3,5-二氯苯基)-N-异丙基-2,4-二氧代咪唑烷-1-羧酰胺(扑海因(Iprodion))、N-(3`,4`-二氯-5-氟联苯-2-基)-3-(二氟甲基)-1-甲基吡唑-4-羧酰胺(联苯吡菌胺(Bixafen))、二甲基4,4`-(邻亚苯基)双(3-硫脲基甲酸酯)(甲基托布津(Thiophanate-methyl))、2-氯-N-(4`-氯联苯-2-基)烟酰胺(啶酰菌胺)、5,10-二氢-5,10-二氧萘并[2,3-b]-1,4-二硫杂环-2,3-二腈(5,10-dihydro-5,10-dioxonaphtho[2,3-b]-1,4-dithi-in-2,3-dicarbonitrile)(二噻农)、(E)-2-{2[6-(2-氰基苯氧基)嘧啶-4-基氧基)苯基}3-甲氧基丙烯酸甲酯(嘧菌酯)、(E,E)-甲氧亚氨基-{2-[1-(3-三氟甲基-苯基)-亚乙基氨基氧基甲基]-苯基}-乙酸甲酯(肟菌酯)、2,6-二氯-N-[3-氯-5-(三氟甲基)-2-吡啶基甲基)苯甲酰胺(氟吡菌胺(Fluopicolide))、(+/-)-顺式-4-[3-(4-叔丁基苯基)-2-甲基丙基]-2,6-二甲基吗啉(丁苯吗啉)、(E,Z 4-[3-(4-氯苯基)-3-(3,4-二甲氧基苯基)-丙烯酰基]-吗啉(烯酰吗啉)、(RS)-1-[3-(4-叔丁基苯基)-2-甲基丙基)哌啶(苯锈啶(Fenpropidine))、(RS)-1-对氯-苯基-4,4-二甲基-3-(1H-1,2,4-***-1-基甲基)戊-3-醇(戊唑醇)、(1RS,2RS,1RS,2SR)-1-(4-氯苯氧基)-3,3-二甲基-1-(1h-1,2,4-***-1-基)丁-2-醇(***醇)、1-(2,4-二氯-β-丙基苯乙基)-1H-1,2,4-***(戊菌唑)、(1RS,5RS,1RS,5SR)-5-(4-氯苄基)-2,2-二甲基-1-(1H-1,2,4-***-基甲基)环戊醇(叶菌唑)、(RS)-2-[2-(1-氯环丙基)-3-[2-氯苯基)-2-羟丙基]-2,4-二氢-1,2,4-***-3-硫酮(丙硫菌唑)、(2RS,3RS)-1-[3-(2-氯苯基)-2-(4-氟-苯基)环氧乙烷-2-基甲基]-1H-1,2,4-***(氟环唑)、(+/-)-(E)-5+(4-氯亚苄基)-2-2-二甲基-1-(1H-1,2,4-***-1-甲基)环戊醇(灭菌唑)、(+/-)-1-[2-(2,4-二氯苯基)-4-丙基-1,3-二氧戊环-2-基甲基]-1H-1,2,4-***(丙环唑)、乙撑双-(二硫代氨基甲酸锰)与锌盐的配位聚合物(代森锰锌)、(E)-2-甲氧亚氨基-(2)-邻甲基苯氧基-甲基(苯基)乙酸甲酯(醚菌酯(Kresoxim-methyl))。
根据本发明的农用杀虫剂包含选自包括聚(烷基)胍、聚(烷基)双胍、聚鸟嘌呤或奥替尼啶的组中的物质,或该组物质的任意共混物,其可以以总组合物的10ppm至500000ppm,优选10ppm至200000ppm,更优选20ppm至40000ppm的比例存在于水性制剂中。
例如,当聚(烷基)胍,尤其是PHMG,以水性制剂施用时,通常它以10ppm至200000ppm,更优选20ppm至40000ppm的比例被包含在其中。
下表1中汇集了基于作为聚(烷基)胍代表的PMHG的示例性组合物的优选范围:
表1
优选地,将根据本发明的农用杀虫剂的pH值被调节至3~8的范围。
如上所述,在本发明的一个优选方面,农用杀虫剂指这样的组合物,在所述组合物中,选自包括聚(烷基)胍、聚(烷基)-双胍、聚胍或奥替尼啶的组中的物质,或这些组的物质的任意共混物,以与显示出针对农业病虫害的活性的至少一种其他组分的组合存在。
在这种情况中,选自包括聚(烷基)胍、聚(烷基)双胍、聚鸟嘌呤或奥替尼啶的组中的物质,或该组的物质的任意共混物,典型地以总组合物的10ppm至200000ppm,优选20ppm至8000ppm的比例存在。
例如,PHMG典型地以优选10至200000ppm,更优选20至8000ppm,与市售农用杀虫剂的活性剂联合包含在制剂中。
在这样的组合物中,显示出针对农业病虫害的活性的至少一种其他组分典型地以总组合物的5ppm至20000ppm,优选10ppm至5000ppm的比例存在。
在根据本发明的农用杀虫剂中,聚(烷基)胍、聚(烷基)双胍或聚鸟嘌呤可具有500至100000道尔顿范围,例如500或1000至400000道尔顿,优选500或1000至10000道尔顿、500至6000道尔顿或1000至4000道尔顿的分子量。
在根据本发明的农用杀虫剂中,聚(烷基)胍或聚(烷基)-双胍可以具有C2至C20范围,优选C2至C14范围的单体的烷基(亚烷基)链长度,并且聚合度n(聚合物中单体亚烷基单元的数量)为5至600的范围,优选在5至300的范围。
具体地,聚(烷基)胍可选自包括聚(四亚甲基)胍、聚(六亚甲基)胍(PHMG)、聚(八亚甲基)-胍、聚(十亚甲基)胍、聚(十二-亚甲基)胍或其共混物的组。
根据本发明的农用杀虫剂的一些具体实施方式是如下的水性组合物,该水性组合物包含:20~8000ppm的量的聚(六亚甲基)胍;和各自为10~1000ppm的量的、选自包括2,6-二氯-N-[3-氯-5-(三氟-甲基)-2-吡啶基甲基)苯甲酰胺、5,10-二氢-5,10-二氧萘并[2,3-b]-1,4-二硫杂环-2,3-二腈、(E)-2-{2[6-(2-氰基苯氧基)嘧啶-4-基氧基)苯基}3-甲氧基丙烯酸甲酯、丙基-3-(二甲氨基)丙基氨基甲酸酯盐酸盐的组中的一种或多种化合物;和余量的水。
基于PHMG与来自“接触剂”类别的市售杀虫活性剂二噻农(Bayer)的共混物的、根据本发明的活性剂的示例性组合物的优选范围是:
表2
基于PHMG与来自“接触剂”类别的市售活性剂氟吡菌胺(Fluopicolid)/霜霉威盐酸盐(Propamocarb-hydrochlorid)(Bayer)的共混物的、根据本发明的活性剂的示例性组合物的优选范围是:
表3
基于PHMG与来自甲氧基丙烯酸酯类(Strobilurines)类别的市售杀虫剂剂嘧菌酯(Azoxystrobin)(Syngenta)的共混物的、根据本发明的活性剂的示例性组成的优选范围为:
表4
下表5中,汇集了PHMG与市售杀虫剂的活性剂的另外的合适的共混物。
给定的比例指通常以10001/ha的量施用的喷雾混合物。
在下表6中,汇集了适于与聚(烷基)胍,特别是PHMG,在根据本发明的组合物中共混的许多市售的杀虫剂,以及在喷雾混合物中的合适的比例。
根据本发明的农用杀虫剂可以表现出针对任何种类的农业病虫害的活性,典型地农业病虫害是微生物,尤其是选自包括细菌、真菌和病毒的组的微生物。
更具体地,所述农业病虫害选自以下的组:植物病原真菌,包括交链孢属(Alternaria)菌种、曲霉属(Aspergillus)菌种、布氏白粉菌属(Blumeria)菌种、葡萄孢属(Botrytis)菌种、长喙壳属(Ceratocystis)菌种、毛皮伞属(Crinipellis)菌种、头孢藻属(Cephaleuros)菌种、刺盘孢属(Colletotrichum)菌种、弯孢属(Curvularia)菌种、白粉菌科(Erysiphaceae)菌种、镰孢菌属(Fusaria)菌种、盘长孢属(Gloeosporium)菌种、小丛壳属(Glomerella)菌种、栅锈菌属(Melampsora)菌种、球腔菌属(Mycosphaerella)菌种、Moniliophthora菌种、稻痕菌属(Magnaporthe)菌种、Odium菌种、青霉属(Penicillium)菌种、单轴霉属(Plasmopara)菌种、柄锈菌属(Puccinia)菌种、层锈菌属(Phakopsora)菌种、叉丝单囊壳属(Podosphaera)菌种、腐霉属(Pythium)菌种、疫霉属(Phytophora)菌种、根霉属(Rhizopus)菌种、毛球腔菌属(Setosphaeria)菌种、Sclerophtora菌种、黑粉菌属(Ustilago)菌种、黑星菌属(Venturia)菌种、轮枝孢菌属(Verticillium)菌种;植物病原细菌,包括醋杆菌属(Acetobacter)菌种、土壤杆菌属(Agrobacterium)菌种、棒形杆菌属(Clavibacter)菌种、韧皮部杆菌属(Candidatus Liberibacter)菌种、短小杆菌属(Curtobacterium)菌种、迪基氏菌属(Dickeya)菌种、欧文氏菌属(Erwinia)菌种、泛菌属(Pantoea)菌种、果胶杆菌属(Pectobacterium)菌种、假单胞菌属(Pseudomonas)菌种、雷尔氏菌属(Ralstonia)菌种、黄单胞菌属(Xanthomonas)菌种;植物病原病毒,包括烟草花叶病毒(TMV)、番茄斑萎病毒(TSWV)、番茄黄化曲叶病毒(TYLCV)、黄瓜花叶病毒(CMV)、马铃薯Y病毒(PVY)、花椰菜花叶病毒(CaMV)、非洲木薯花叶病毒(ACMV)、李痘病毒(PPV)、雀麦草花叶病毒(BMV)、香蕉束顶病毒(BBTV)、香蕉条纹病毒(BSV)、大麦黄矮病黄矮病毒组复合体(Barley yellow dwarf disease luteovirus complex)、玉米条纹病毒(MSV)、玉米矮花叶病毒(Maize dwarfmosaic potivirus)、水稻东格鲁病毒复合体(Rice tungro diseasevirus complex)、水稻黄斑驳病毒(Rice yellow mottle sobemovirus,RYMV)、甘蔗花叶病毒(Sucarcane mosaic potivirus)、甘薯羽状斑驳病毒(SPFMV)。
在仍然更具体的实施方式中,所述农业病虫害选自下组:植物病原真菌,包括交链孢属菌种(例如感染果树)、黄曲霉(Aspergillus flavus)(例如感染菠萝;干腐病)、禾本科布氏白粉菌(Blumeria graminis)(例如感染农作物)、灰葡萄孢菌(Botrytis cinerea)(灰霉病)、可可球二孢(Botryodiplodia theobromae)(例如感染荔枝)、奇异长喙壳(Ceratocystis paradoxa)(例如感染菠萝;软腐病)、可可丛枝病菌(Crinipellisperniciosa)(例如感染可可;丛枝病)、头孢藻属菌种(例如感染芒果)、胶孢炭疽菌(Colletotrichum gloeosporioides)(例如感染荔枝)、疣状弯孢霉(Curvulariaverucculosa)(例如感染菠萝;干腐病)、白粉菌科菌种(白粉病)、尖孢镰刀菌(Fusariumoxysporum)、禾谷镰刀菌(Fusarium graminearum)(农作物)、尖孢镰刀菌古巴专化型(Fusarium oxysporum f.sp.Cubense type)1-4(例如感染香蕉;枯萎病)、盘长孢属菌种(储存的水果;收获后锈病(rost))、毛盘孢菌(Glomerella Tucumanensis)(甘蔗)、亚麻锈菌(Melampsora lini)、禾生球腔菌(Mycosphaerella graminicola)、香蕉褐条斑小球壳菌(Mycosphaerella musicola)(香蕉;黄叶斑病)、香蕉黑条叶斑病菌(Mycosphaerellafijiensis)(香蕉;黑叶斑病)、可可链疫孢荚腐病菌(Moniliophthora Roreri)(可可;黑斑病(frosty pod))、稻瘟病菌(Magnaporthe oryzae)、Odium lycopersicum(番茄;霉病)、棒形青霉(Penicillium claviforme)(菠萝;干腐病)、指状青霉(Penicillium digitatum)(柑橘类水果;蓝和绿霉腐病)、葡萄霜霉菌(Plasmopara viticola)(葡萄藤;霜霉病)、柄锈菌亚门(Pucciniomycotina)(小麦;褐锈病)、玉米锈病菌(Puccinia sorghi)(玉米;玉米锈病)、蟥层锈菌(Phakopsora meibomiae)、大豆锈菌(Phakopsora pachyrizi)(大豆;大豆锈病)、白叉丝单囊壳(Podosphaera leucotricha)(苹果;苹果白粉病)、草莓白粉病菌(Podosphaera aphanis)(草莓)、月季白粉病菌(Podosphaera pannosa)(蔷薇;粉状蔷薇白粉病)、腐霉属菌种、马铃薯晚疫病菌(Phytospora infestans)(马铃薯;晚疫病)、疫霉属荚果腐病菌(Phytophtora Pod Rot)(可可;黑荚果病)、匍枝根霉(Rhizopus stolonifer)(菠萝;软腐病)、米根霉(Rhizopus oryzae)(菠萝;软腐病)、玉米大斑病菌(Setosphaeriaturcica)(玉米;大斑病(turcicum leaf spots))、玉蜀黍黑粉菌(Ustilago maydis)(玉米;玉米黑粉病)、黑白轮枝菌(Verticillium albo-atrum)(芒果)、苹果黑星菌(苹果;苹果黑星病)、嗜果黑星菌(Venturia carpophila)(桃;桃黑星病);和植物病原细菌,包括过氧化醋杆菌(Acetobacter peroxydans)(例如感染菠萝;大理石病(marble disease))、纹膜醋酸杆菌(Acetobacter aceti)(菠萝;赤腐病)、根癌农杆菌(Agrobacteriumtumefaciens)、密执安棒状杆菌(Clavibacter michiganensis)、环腐棒形菌(Clavibactersepedonicus)、柑橘黄龙病菌亚洲种(Candidatus Liberibacter asiaticus)、萎蔫短小杆菌(Curtobacterium flaccumfaciens)、甘薯茎腐病菌(Dickeya dadantii)、马铃薯黑胫病菌(Dickeya solani)、菠萝欧文氏菌(Erwinia ananas)(菠萝;大理石病)、梨火疫菌(ErwiniaAmylovora)(果树;火疫病)、成团泛菌(Pantoea agglomerans)(菠萝;赤腐病)、胡萝卜软腐果胶杆菌(Pectobacterium carotovorum)、黑腐果胶杆菌(Pectobacteriumatrosepticum)、丁香假单胞菌(Pseudomonas syringae pathovars)、萨氏假单胞菌(Pseudomonas savastanoi)、青枯雷尔氏菌(Ralstonia solanacearum)、稻白叶枯黄杆菌(Xanthomonas oryzae)、黄单胞杆菌致病变种(Xanthomonas campestris pathovars)、黄单胞菌大豆致病变种(Xanthomonas axonopodis pathovars)、稻黄单胞菌水稻致病变种(Xanthomonas oryzae,pv.Oryzae)。
本发明的另一方面涉及一种保护植物(尤其是栽培植物)免受病虫害侵害的方法,该方法包括:使要保护的植物和/或所述植物在其中生长的土壤或营养培养基,与足以防止或抑制所述病虫害对要保护的植物产生有害作用的量的、如上定义的农用杀虫剂接触预定时间。
典型地,在该方法中,所述杀虫剂制剂以每公顷土壤或营养培养基100~5000l,优选500~1500l的量施用至少一次。
具体实施方式
实施例1
体外针对灰葡萄孢菌的活性
在琼脂上培养灰葡萄孢菌分离菌株BC 271(它对甲氧基丙烯酸酯、苯氨基嘧啶、氢化酶抑制剂、环酰菌胺(Fenhexamide)有抗性,且对咯菌腈的敏感性降低),直到开始产生孢子。使用1x 105分生孢子/ml的孢子浓度进行测试。
在测试的每一重复中,将各分析物(参见汇集各种测试的分析物和标准品的表7)加入到所需浓度的孢子悬浮液中,并将10μl(含有1000个分生孢子)放置在琼脂平板(麦芽提取物)上,随后在20℃孵育平板。每一测试重复4次。在2天和3天后检查真菌在琼脂平板上的生长(表8)。
表7
表8
图1显示了在20℃孵育3天后,未经处理的对照(上四分之一),10%Kat P 2500(右),0.1%Switch(下)和0.01%Switch(左)的结果(4次重复中的2次)。
总结:
将葡萄孢属的分生孢子施加在琼脂平板上后,孢子在对照中以及含Switch(0.1%和0.01%)、BasD30(10%)、ByIn312(10%)和SynAm200(10%)的混合物中萌发,在2天后产生可见的菌丝体,在3天后产生气生菌丝体。3天后,未经处理的对照菌落已经生长至直径大约为4cm的尺寸。0.1%的Switch使部分抗性的葡萄孢属菌株的生长减少至大约1cm,而0.01%的Switch使其减少至1.5~1.8cm。(敏感性葡萄孢属菌株在琼脂上的生长被0.1%的Switch完全抑制)。
分析物KAT P 2500、KAT P 1250、KAT P 625、TM PD 1250、TM PD 625、TM PI1250、TM PI 625、TM PA 1250和TM PA 625(各进行10%的稀释)完全抑制了葡萄孢属分离菌株Bc 271的发育。
实施例2
体外针对苹果黑星菌的活性
将已经冷冻保存的苹果树(Jonagold;最初在康斯坦茨大学的植物园中收获并在温室中进一步繁殖)的受感染叶子解冻并用水漂洗。将得到的分生孢子悬浮液与各种分析物(参见汇集各种测试分析物的表7)混合,以便使分析物以1∶10稀释,即以10%的浓度使用。将40μl的各混合物施加至琼脂水溶液,并将这些板在20℃孵育24小时。随后,对于各测试批次,使用显微镜评估了至少200个分生孢子的萌发,并计算了萌发的分生孢子的比例(百分比)(表9)。测试是以双重测定完成的,并重复一次。
表9
总结:
在未经处理的对照中,分生孢子的平均萌发率为36.3%。ByIn312不能抑制孢子萌发。其他每种分析物均显示对该病原体的有效度高于98.5%。参考标准品Delan WG(二噻农)在以0.05%的推荐浓度施用时,使萌发降低了99.7%,而以0.0005%的浓度施用时,使萌发降低98.7%。
实施例3
体外针对黄色镰刀菌(Fusarium culmorum)的活性
在琼脂上培养黄色镰刀菌分离菌株,直到开始产生孢子。使用1x 105分生孢子/ml的孢子浓度进行测试。
在测试的每一重复中,将所需浓度的各分析物(参见汇集各测试分析物的表7)添加到孢子悬浮液中,并将10μl(含1000个分生孢子)放置在琼脂平板(麦芽提取物)上。随后在20℃孵育平板。每一测试重复4次。在2天和3天后检查真菌在琼脂平板上的生长(表10)。
表10
总结:
将镰刀菌属(Fusarium)的分生孢子施加到琼脂平板上后,孢子在对照中,以及在含BasD30(10%)、ByIn312(10%)和SynAm200(10%)的混合物中萌发,在2天后产生可见的菌丝体,3天后产生可测量的菌落。未经处理的对照的菌落在孵育3天后已长到2.9cm大小。在含0.005%Geoxe的混合物中,萌发和菌丝体生长被延迟但没有被完全抑制。
参照标准品0.05%Geoxe以及分析物KAT P 2500、KAT P 1250、KAT P 625、TM PD1250、TM PD 625、TM PI 1250、TM PI 625、TM PA 120和TM PA 625(均以10%稀释)完全抑制了菌丝体的形成。
在YBA琼脂上,另外测试含嘧菌酯的制剂SynAm200、TMPA 1250和TMPA 625。在此,SynAm200也不抑制菌丝体生长,而Geoxe(0.05%)以及TM PA 1250和TM PA 625(10%稀释)完全抑制了黄色镰刀菌菌丝体的生长。
Claims (18)
1.一种农用杀虫剂,其包含:选自包括聚(烷基)胍、聚(烷基)双胍、聚鸟嘌呤或奥替尼啶的组中的物质,或者该组中的物质的任意共混物。
2.根据权利要求1所述的农用杀虫剂,其中,所述聚(烷基)胍或聚(烷基)双胍具有在C2-C14范围的单体的烷基链长度。
3.根据权利要求1或2所述的农用杀虫剂,其中,所述聚(烷基)胍选自包括以下的组:聚(四亚甲基)胍、聚(六亚甲基)胍(PHMG)、聚(八亚甲基)胍、聚(十亚甲基)胍、聚(十二亚甲基)胍。
4.根据权利要求1至3中任一项所述的农用杀虫剂,其中,所述选自包括聚(烷基)胍、聚(烷基)双胍、聚鸟嘌呤或奥替尼啶的组中的物质,或者该组中的物质的任意共混物,以与显示出针对农业病虫害的活性的至少一种其他组分的组合存在。
5.根据权利要求1至4中任一项所述的农用杀虫剂,其中,所述显示出针对农业病虫害的活性的至少一种其他组分代表市场上已知的杀虫剂的至少一种活性剂。
6.根据权利要求4或5所述的农用杀虫剂,其中,所述显示出针对农业病虫害的活性的至少一种其他组分是在与植物接触时起作用的杀虫剂。
7.根据权利要求4至6中任一项所述的农用杀虫剂,其中,所述显示出针对农业病虫害的活性的至少一种其他组分选自包括以下的化合物的组:唑类,尤其是二唑、***、苯并咪唑和吡唑;氨基甲酸酯,尤其是苯并咪唑氨基甲酸酯和二硫代氨基甲酸酯;羧酰胺;二甲酰亚胺;酰替苯胺;烟酰胺;胺和铵化合物,包括螺噁茂胺;和杂环化合物例如嘧啶、吡啶、哌啶、吗啉、吡咯,尤其是苯基吡咯、二嗪;甲氧基丙烯酸酯类;腈,尤其是氯代腈;肉桂酸。
8.根据权利要求7所述的农用杀虫剂,其中,所述显示出针对农业病虫害的活性的至少一种其他组分选自包括以下的组:丙基-3-(二甲氨基)丙基氨基甲酸酯盐酸盐、8-叔丁基-1,4-二氧螺环[4.5]癸烷-2-基甲基-(乙基)(丙基)胺、(RS)-2-4-氯苯基)-N-[3-甲氧基-4-(丙-2-炔氧基)苯乙基]-2-(丙-2-炔氧基)乙酰胺、N-甲氧基乙酰基)-N-2,6-二甲苯基-D-丙氨酸甲酯、N-丙基-N-[2-2,4,6-三氯苯氧基)-乙基]咪唑-1-羧酰胺、N-4,6-二甲基嘧啶-2-基)苯胺、(E)-3-甲氧基-2-{2-6-(三氟-甲基)吡啶-2-基氧基甲基]-苯基}丙烯酸甲酯、(E,E)-甲氧基亚氨基-{2-[1-(3-三氟甲基-苯基)-亚乙基氨基氧基甲基]-苯基}-乙酸甲酯、(E)-{2-[6-(2-氯苯氧基)-5-氟嘧啶-4-基氧基]苯基}(5,6-二氢-1,4,2-二噁嗪-3-基)甲酮、3-(二氟甲基)-1-甲基-N-(3`,4`,5`-三氟-联苯-2-基)吡唑-4-羧酰胺、5-氨基-2,3-二氢-2-异丙基-3-氧代-4-(邻甲苯基)吡唑-1-硫代甲酸-S-烯丙酯、(E,Z 4-[3-(4-氯苯基)-3-(3,4-二甲氧基苯基)丙烯酰基]吗啉、四氯间苯二腈、3-(3,5-二氯苯基)-N-异丙基-2,4-二氧代-咪唑烷-1-羧酰胺、N-(3`,4`-二氯-5-氟联苯-2-基)-3-(二氟甲基)-1-甲基吡唑-4-羧酰胺、二甲基4,4`-(邻亚苯基)双(3-硫脲基甲酸酯)、2-氯-N-(4`-氯联苯-2-基)烟酰胺、5,10-二氢-5,10-二氧萘并[2,3-b]-1,4-二硫杂环-2,3-二腈、(E,Z 4-[3-(4-氯苯基)-3-(3,4-二甲氧基苯基)-丙烯酰基]吗啉、(E)-2-{2[6-(2-氰基苯氧基)嘧啶-4-基氧基)苯基}3-甲氧基丙烯酸甲酯、2,6-二氯-N-[3-氯-5-(三氟甲基)-2-吡啶基甲基)苯甲酰胺、(+/-)-顺式-4-[3-(4-叔丁基苯基)-2-甲基丙基]-2,6-二甲基吗啉、(RS)-1-[3-(4-叔丁基苯基)-2-甲基丙基)-哌啶、(RS)-1-对氯苯基-4,4-二甲基-3-(1H-1,2,4-***-1-基甲基)戊-3-醇、(1RS,2RS,1RS,2SR)-1-(4-氯苯氧基)-3,3-二甲基-1-(1h-1,2,4-***-1-基)丁-2-醇、1-(2,4-二氯-β-丙基苯乙基)-1H-1,2,4-***、(1RS,5RS,1RS,5SR)-5-(4-氯苄基)-2,2-二甲基-1-(1H-1,2,4-***-基甲基)环戊醇、(RS)-2-[2-(1-氯环丙基)-3-[2-氯苯基)-2-羟丙基]-2,4-二氢-1,2,4-***-3-硫酮、(2RS,3RS)-1-[3-(2-氯苯基)-2-(4-氟苯基)-环氧乙烷-2-基甲基]-1H-1,2,4-***、(+/-)-(E)-5+(4-氯亚苄基)-2-2-二甲基-1-(1H-1,2,4-***-1-甲基)环戊醇、(+/-)-1-[2-(2,4-二氯苯基)-4-丙基-1,3-二氧戊环-2-基甲基]-1H-1,2,4-***、乙撑双-(二硫代氨基甲酸锰)与锌盐的配位聚合物、(E)-2-甲氧亚氨基-(2)-邻甲基苯-氧基甲基-(苯基)乙酸甲酯。
9.根据权利要求1至8中任一项所述的农用杀虫剂,其中,所述选自包括聚(烷基)胍、聚(烷基)双胍、聚鸟嘌呤或奥替尼啶的组中的物质,或者该组中的物质的任意共混物,以总组合物的10ppm和200000ppm之间,优选20ppm和40000ppm之间的比例存在于水性制剂中。
10.根据权利要求4至9中任一项所述的农用杀虫剂,其中,所述选自包括聚(烷基)胍、聚(烷基)双胍、聚鸟嘌呤或奥替尼啶的组中的物质,或者该组中的物质的任意共混物,以总组合物的10ppm和200000ppm之间,优选20ppm和8000ppm之间的比例存在。
11.根据权利要求4至10中任一项所述的农用杀虫剂,其中,所述显示出针对农业病虫害的活性的至少一种其他组分,以总组合物的5ppm和20000ppm之间,优选10ppm和5000ppm之间的比例存在。
12.根据权利要求1至11中任一项所述的农用杀虫剂,其中,所述聚(烷基)胍、聚(烷基)双胍或聚鸟嘌呤具有在500至100000道尔顿,优选500至40000道尔顿,尤其是1000至10000道尔顿范围的分子量。
13.根据权利要求1至12中任一项所述的农用杀虫剂,所述农用杀虫剂是包含以下物质的水性组合物:20~8000ppm的量的聚(六亚甲基)胍;和选自包括以下的组的一种或多种化合物:2,6-二氯-N-[3-氯-5-(三氟甲基)-2-吡啶基甲基)苯甲酰胺、5,10-二氢-5,10-二氧萘并[2,3-b]-1,4-二硫杂环-2,3-二腈、(E)-2-{2[6-(2-氰基苯氧基)-嘧啶-4-基氧基)-苯基}3-甲氧基丙烯酸甲酯、丙基-3-(二甲氨基)丙基氨基甲酸酯盐酸盐,所述化合物的量各自为10~1000ppm;以及余量的水。
14.根据权利要求1至13中任一项所述的农用杀虫剂,其中,农业病虫害是微生物,尤其是选自包括细菌、真菌和病毒的组中的微生物。
15.根据权利要求14所述的农用杀虫剂,其中,所述农业病虫害选自以下的组:植物病原真菌,包括交链孢属(Alternaria)菌种、曲霉属(Aspergillus)菌种、布氏白粉菌属(Blumeria)菌种、葡萄孢属(Botrytis)菌种、长喙壳属(Ceratocystis)菌种、毛皮伞属(Crinipellis)菌种、头孢藻属(Cephaleuros)菌种、刺盘孢属(Colletotrichum)菌种、弯孢属(Curvularia)菌种、白粉菌科(Erysiphaceae)菌种、镰孢菌属(Fusaria)菌种、盘长孢属(Gloeosporium)菌种、小丛壳属(Glomerella)菌种、栅锈菌属(Melampsora)菌种、球腔菌属(Mycosphaerella)菌种、Moniliophthora菌种、稻痕菌属(Magnaporthe)菌种、Odium菌种、青霉属(Penicillium)菌种、单轴霉属(Plasmopara)菌种、柄锈菌属(Puccinia)菌种、层锈菌属(Phakopsora)菌种、叉丝单囊壳属(Podosphaera)菌种、腐霉属(Pythium)菌种、疫霉属(Phytophora)菌种、根霉属(Rhizopus)菌种、毛球腔菌属(Setosphaeria)菌种、Sclerophtora菌种、黑粉菌属(Ustilago)菌种、黑星菌属(Venturia)菌种、轮枝孢菌属(Verticillium)菌种;植物病原细菌,包括醋杆菌属(Acetobacter)菌种、土壤杆菌属(Agrobacterium)菌种、棒形杆菌属(Clavibacter)菌种、韧皮部杆菌属(CandidatusLiberibacter)菌种、短小杆菌属(Curtobacterium)菌种、迪基氏菌属(Dickeya)菌种、欧文氏菌属(Erwinia)菌种、泛菌属(Pantoea)菌种、果胶杆菌属(Pectobacterium)菌种、假单胞菌属(Pseudomonas)菌种、雷尔氏菌属(Ralstonia)菌种、黄单胞菌属(Xanthomonas)菌种;植物病原病毒,包括烟草花叶病毒(TMV)、番茄斑萎病毒(TSWV)、番茄黄化曲叶病毒(TYLCV)、黄瓜花叶病毒(CMV)、马铃薯Y病毒(PVY)、花椰菜花叶病毒(CaMV)、非洲木薯花叶病毒(ACMV)、李痘病毒(PPV)、雀麦草花叶病毒(BMV)、香蕉束顶病毒(BBTV)、香蕉条纹病毒(BSV)、大麦黄矮病黄矮病毒组复合体、玉米条纹病毒(MSV)、玉米矮花叶病毒、水稻东格鲁病毒复合体、水稻黄斑驳病毒(RYMV)、甘蔗花叶病毒、甘薯羽状斑驳病毒(SPFMV)。
16.根据权利要求15所述的农用杀虫剂,其中,所述农业病虫害选自以下的组:植物病原真菌,包括交链孢属菌种、黄曲霉(Aspergillus flavus)、禾本科布氏白粉菌(Blumeriagraminis)、灰葡萄孢菌(Botrytis cinerea)、可可球二孢(Botryodiplodia theobromae)、奇异长喙壳(Ceratocystis paradoxa)、可可丛枝病菌(crinipellis,perniciosa)、头孢藻属菌种、胶孢炭疽菌(Colletotrichum gloeosporioides)、疣状弯孢霉(Curvulariaverucculosa)、白粉菌科菌种、尖孢镰刀菌(Fusarium oxysporum)、禾谷镰刀菌(Fusariumgraminearum)、尖孢镰刀菌古巴专化型(Fusarium oxysporum f.sp.Cubense type)1-4、盘长孢属菌种、毛盘孢菌(Glomerella Tucumanensis)、亚麻锈菌(Melampsora lini)、禾生球腔菌(Mycosphaerella graminicola)、香蕉褐条斑小球壳菌(Mycosphaerella musicola)、香蕉黑条叶斑病菌(Mycosphaerella fijiensis)、可可链疫孢荚腐病菌(MoniliophthoraRoreri)、稻瘟病菌(Magnaporthe oryzae)、Odium lycopersicum、棒形青霉(Penicilliumclaviforme)、指状青霉(Penicillium digitatum)、葡萄霜霉菌(Plasmopara viticola)、柄锈菌亚门(Pucciniomycotina)、玉米锈病菌(Puccinia sorghi)、蟥层锈菌(Phakopsorameibomiae)、大豆锈菌(Phakopsora pachyrizi)、白叉丝单囊壳(Podosphaeraleucotricha)、草莓白粉病菌(Podosphaera aphanis)、月季白粉病菌(Podosphaerapannosa)、腐霉属菌种、马铃薯晚疫病菌(Phytospora infestans)、疫霉属荚果腐病菌(Phytophtora Pod Rot)、匍枝根霉(Rhizopus stolonifer)、米根霉(Rhizopus oryzae)、玉米大斑病菌(Setosphaeria turcica)、玉蜀黍黑粉菌(Ustilago maydis)、黑白轮枝菌(Verticillium albo-atrum)、苹果黑星菌(Venturia inaequalis)、嗜果黑星菌(Venturiacarpophila);和、植物病原细菌,包括过氧化醋杆菌(Acetobacter peroxydans)、纹膜醋酸杆菌(Acetobacter aceti)、根癌农杆菌(Agrobacterium tumefaciens)、密执安棒状杆菌(Clavibacter michiganensis)、环腐棒形菌(Clavibacter sepedonicus)、柑橘黄龙病菌亚洲种(Candidatus Liberibacter asiaticus)、萎蔫短小杆菌(Curtobacteriumflaccumfaciens)、甘薯茎腐病菌(Dickeya dadantii)、马铃薯黑胫病菌(Dickeyasolani)、菠萝欧文氏菌(Erwinia ananas)、梨火疫菌(Erwinia Amylovora)、成团泛菌(Pantoea agglomerans)、胡萝卜软腐果胶杆菌(Pectobacterium carotovorum)、黑腐果胶杆菌(Pectobacterium atrosepticum)、丁香假单胞菌(Pseudomonas syringaepathovars)、萨氏假单胞菌(Pseudomonas savastanoi)、青枯雷尔氏菌(Ralstoniasolanacearum)、稻白叶枯黄杆菌(Xanthomonas oryzae)、黄单胞杆菌致病变种(Xanthomonas campestris pathovars)、黄单胞菌大豆致病变种(Xanthomonasaxonopodis pathovars)、稻黄单胞菌水稻致病变种(Xanthomonas oryzae,pv.Oryzae)。
17.一种保护植物,尤其是栽培植物,免受病虫害侵害的方法,所述方法包括:使要保护的植物和/或所述植物在其中生长的土壤或营养培养基,与足以防止或抑制所述病虫害对要保护的植物产生有害作用的量的、根据权利要求1至16中任一项所述的农用杀虫剂接触,达预定时间。
18.根据权利要求17所述的方法,其中,每公顷土壤或营养培养基,施用至少一次100~5000l,优选500~1500l的量的所述杀虫剂制剂。
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CN115594641B (zh) * | 2022-12-12 | 2023-05-02 | 中国农业大学 | 一类含苄基1,2,3-***结构的化合物及其作为杀菌剂的应用 |
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- 2016-09-21 AU AU2016325202A patent/AU2016325202A1/en not_active Abandoned
- 2016-09-21 WO PCT/EP2016/001578 patent/WO2017050428A1/en active Application Filing
- 2016-09-21 MX MX2018003635A patent/MX2018003635A/es unknown
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CN111264543A (zh) * | 2020-01-09 | 2020-06-12 | 山东农业大学 | 一种嘌呤碱植物免疫诱抗剂及其应用 |
CN111264543B (zh) * | 2020-01-09 | 2021-05-04 | 山东农业大学 | 一种嘌呤碱植物免疫诱抗剂及其应用 |
CN115956573A (zh) * | 2022-12-15 | 2023-04-14 | 江苏维尤纳特精细化工有限公司 | 一种含有百菌清的新型杀菌组合物 |
Also Published As
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CA2999793A1 (en) | 2017-03-30 |
WO2017050428A9 (en) | 2018-07-19 |
BR112018005903A2 (pt) | 2018-10-16 |
AU2016325202A1 (en) | 2018-05-17 |
US20180263243A1 (en) | 2018-09-20 |
EA201890813A1 (ru) | 2018-09-28 |
WO2017050428A1 (en) | 2017-03-30 |
EP3352571A1 (en) | 2018-08-01 |
MX2018003635A (es) | 2019-04-25 |
JP2018529699A (ja) | 2018-10-11 |
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