CN1193255A - 杀真菌混合物 - Google Patents
杀真菌混合物 Download PDFInfo
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Abstract
一种杀真菌混合物,包含增效活性量的a)式Ⅰ的肟醚羧酰胺,其中R是氢或卤素,和或者b.1)式Ⅱa的肟醚羧酸酯,b.2)式Ⅱb的肟醚羧酰胺,或b.3)式Ⅱc的甲氧基丙烯酸酯。
Description
而且,本发明涉及使用式I和式II化合物的混合物防治有害真菌的方法,以及涉及化合物I和化合物II制备这种混合物的应用。
式I化合物、其制备和其对有害真菌的活性公开于文献(WO-A 95/18,789)中。化合物IIa(EP-A 253213)、IIb(EP-A 477631)和化合物IIc(EP-A 382375)、其制备和其对有害真菌的作用同样是已知的。
本发明的目的是提供对有害真菌具有改进的作用且降低施用活性成分的总量的混合物(增效混合物),目的在于降低施用量和改进已知化合物的作用谱。
相应地,我们发现,此目的可通过开头定义的混合物实现。而且,我们发现,通过同时一起或分别施用化合物I和化合物II,或依次施用化合物I和化合物II,可以比使用单个化合物更好地防治有害真菌。
式I中的R是氢或卤原子如氟、氯、溴或碘,特别是氢、氟或氯,特别是氢或氟。
有关C=N双键,式I和式II化合物可以存在E或Z构形(相对于基团羧酸官能团)。因此,它们各可以以纯E或Z异构体或以E/Z异构体混合物形式用于本发明的混合物中。优选使用E/Z异构体混合物或E异构体,特别优选的是E异构体。
由于NH基团的碱性特点,化合物I能够与无机或有机酸或与金属离子形成盐或加成物。
在式I化合物侧链上的肟醚基团的C=N双键可以在每一种情况下存在纯E或Z异构体形式或E/Z异构体混合物形式。化合物I可以以异构体混合物或纯异构体用于本发明的混合物中。鉴于其应用,特别优选的化合物I是那些在侧链上的两个肟醚基团均为E构形的(E/E)的化合物。
无机酸的实例是氢卤酸(如氢氟酸、盐酸、氢溴酸和氢碘酸)、硫酸、磷酸和硝酸。
适合的有机酸是(例如)甲酸、碳酸和链烷酸(如乙酸、三氟乙酸、三氯乙酸和丙酸),以及乙醇酸、硫氰酸、乳酸、琥珀酸、柠檬酸、苯甲酸、肉桂酸、草酸、烷基磺酸(具有1至20个碳原子的直链或支链烷基基团的磺酸)、芳基磺酸或芳基二磺酸(芳族基团如苯基和萘基,它们具有一或二个连于之的磺基基团)、烷基膦酸(具有1至20个碳原子的直链或支链烷基基团的膦酸)、芳基膦酸或芳基二膦酸(芳族基团,如苯基和萘基,它们具有一或二个连于之的磷酸残基),对于烷基或芳基基团,也可能有另外的取代基连于之,例如对甲苯磺酸、水杨酸、对氨基水杨酸、2-苯氧基苯甲酸、2-乙酰氧基苯甲酸、十二烷基苯磺酸等。
适合的金属离子特别是第二主族的元素,特别是钙和镁,第三和第四主族的元素,特别是铝、锡和铅,第一至第八副族的元素,特别是铬、锰、铁、钴、镍、铜、锌及其它元素的离子。特别优选第四周期的副族元素的金属离子。这些金属可以以各种它们可能的价态存在。
当制备混合物时,优选的是采用纯的活性成份I和II,且如果需要的话,它们可以与其它的杀有害真菌或其它害虫如昆虫、蛛形纲动物或线虫耐活性成分,或是除草的或生长调节的活性成分或化肥混合。
化合物I和II的混合物,或同时一起或分别使用化合物I和II,其突出之处在于对广谱的植物病原真菌,特别是对子囊菌纲和担子菌纲有优异作用。它们中的一些有内吸作用,因此可以用来作为叶面和土壤杀真菌剂。
它们在防治各种作物如棉花、蔬菜(例如,黄瓜、菜豆和葫芦科)、大麦、草、燕麦、咖啡、玉米、水果、稻、黑麦、大豆、葡萄、小麦、观赏植物、甘蔗和许多的种子上的许多真菌方面特别重要。
它们特别适合于防治下列植物病原真菌:禾谷类上的禾白粉菌(Erysiphe graminis)、葫芦科上的二孢白粉菌(Erysiphe cichoracearum)和单丝壳菌(Sphaerotheca fuliginea)、苹果上的苹果白粉病菌(Podosphaeraleucotricha)、葡萄上的葡萄钩丝壳(Uncinula necator)禾谷类上的柄锈菌(Puccinia)、棉花、稻和草坪上的丝核菌(Rhizoctonia)、禾谷类和甘蔗上的黑粉菌(Ustilago)、苹果上的苹果黑星菌(Venturia inaequalis)、禾谷类上的长蠕孢菌(Helminthosporium)、小麦上的黑麦喙孢(RhynosporiumSecalis)、颖枯病菌(Septoria nodorum)、草莓和葡萄上的灰霉菌(Botrytiscinera)、花生上的花生尾孢菌(Cercospora arachidicola)、小麦和大麦上的眼斑病菌(Pseudocercosporella herpotrichoides)、稻上的稻梨孢(Pyricularia oryzae)、马铃薯和蕃茄上的致病疫霉(Phytophthorainfestans)、葡萄上的葡萄生单轴霉(Plasmopara viticola)、蔬菜和水果上的链格孢菌(Alternaria),以及镰刀菌(Fusarium)和轮枝孢菌(Verticillium)。
它们也可以用在材料的保护上(例如,木材防腐),例如,防治拟青霉(Paecilomyces variotii)。
化合物I和II可以同时一起或分别或依次施用,在分别施用时,顺序通常不影响防治的效果。
化合物I和II通常以重量比10∶1至0.1∶1,优选5∶1至0.2∶1,特别是3∶1至0.3∶1使用。
依据所需的效果的性质的不同,本发明混合物的使用量为0.02至1千克/公顷,优选0.05至1千克/公顷,特别是0.1至0.8千克/公顷。对于化合物I,施用量是0.005至0.5千克/公顷,特别是0.005至0.3千克/公顷,优选0.005至0.3千克/公顷。相应地,对于化合物II,施用量是0.01至0.5千克/公顷,优选0.01至0.5千克/公顷,特别是0.01至0.3千克/公顷。
处理种子时,混合物的施用量通常是0.001至50克/千克种子,优选0.01至10克/千克种子,特别是0.01至5克/千克种子。
如果意欲防治的是植物病原真菌,则通过向种子、植物或播种前或后或植物出芽前或后的土壤喷雾或喷粉,分别或一起施用化合物I或化合物I和II的混合物。
本发明的杀真菌增效混合物或化合物I和II可以加工成(例如)可直接喷雾溶液、粉末和悬浮液形式,或高浓度水悬剂、油悬剂或其它悬浮剂、分散液、乳液、油分散液、膏剂、粉剂、撒施剂或颗粒剂,并可通过喷雾、弥雾、喷粉、撒施或浇泼使用。施用形式取决于使用的目的;在每一种情况下,应确保本发明混合物的分散尽可能的细微和均匀。
制剂以其本身是已知的方式来生产,例如,通过添加溶剂和/或载体。惰性添加剂如乳化剂或分散剂通常用来与制剂混合。
适合的表面活性物质是芳族磺酸例如木素磺酸、苯酚磺酸、萘磺酸和二丁基萘磺酸以及脂肪酸的碱金属盐、碱土金属盐和铵盐,烷基磺酸盐和烷基芳基磺酸盐、烷基硫酸盐、月桂基醚硫酸盐和脂肪醇硫酸盐,以及硫酸化的十六-、十七-和十八醇或脂肪醇乙二醇醚的盐,磺化萘和其衍生物与甲醛的缩合产物,萘或萘磺酸与苯酚和甲醛的缩合产物,聚氧乙烯辛基酚醚、乙氧基化的异辛基-、辛基-或壬基酚、烷基苯酚-或三丁基苯基聚乙二醇醚,烷基芳基聚醚醇、异十三烷基醇、脂肪醇环氧乙烷缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚或聚氧丙烯,月桂醇聚乙二醇醚乙酸酯、山梨醇酯,木素亚硫酸盐废液或甲基纤维素。
粉剂、撒施剂和喷粉剂可以通过将化合物I或II或化合物I与II的混合物与固体载体一起混合或研磨而制备。
颗粒剂(例如,涂敷、浸渍或均质颗粒剂)通常是通过将一或多种活性化合物粘合到固体载体上而制备。
可以使用的填料和固体载体的实例是矿石土如硅胶、硅酸、硅胶、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、红玄武土、黄土、陶土、白云石、硅藻土、硫酸钙和硫酸镁、氧化镁、塑料粉、和化肥如硫酸铵、磷酸铵、硝酸铵、尿素和植物产物如谷粉、树皮粉、木粉和坚果壳粉、纤维素粉和其它固体载体。
制剂中通常含有0.1至95%(重量)、优选0.5至90%(重量)的化合物I或II、或化合物I与II的混合物。采用的活性成分纯度为90%至100%,优选95%至100%(根据NMR或HPLC谱)。
化合物I或II或混合物或相应的制剂,是通过使用杀真菌有效量的混合物、或(在分别施用的情况下)使用杀真菌有效量的化合物I和II,处理真菌或处理意欲使其免受有害真菌侵害的植物、种子、土壤、表面、材料或空间来施用的。使用可以在有害真菌侵染前或后进行。
可用下列实施例说明本发明杀真菌混合物的增效作用:
通过下列试验说明化合物和混合物的杀真菌作用:
将各活性物质单独或一起加工成在由70%(重量)的环己酮、20%(重量)的NekanilLN(LutensolAP6,以乙氧基化烷基酚为基础的具有乳化和分散作用的润湿剂)、10%(重量)的EmulphorEL(EmulanEL,以乙氧基化脂肪醇为基础的乳化剂)组成的混合物中的10%的乳剂,并用水稀释至所需浓度。
在确定感染的叶面积后,以百分率进行评价。将这些百分率转化成效率。活性成分的混合物的预期效率用Colby公式来计算[R.S.Colby,《杂草》[Weeds]15,20-22(1967)],并与观察的效率值作比较。Colby公式:
E=x+y-x·y/100E 当以浓度a和b使用活性成分A与B的混合物时的预期效率,以相对于未处理的对照物的%表示x 当以浓度a使用活性成分A时的效率,以相对于未处理的对照物的%表示y 当以浓度b使用活性成分B时的效率,以相对于未处理的对照物的%表示。效率为0时已处理的植物的真菌侵染与未处理的植物的相同;效率为100时已处理植物无真菌侵染。对隐匿柄锈菌(小麦叶锈病)的作用
将小麦苗(品种:Kanzler)的叶片用隐匿柄锈菌(Puccinia recondita)的孢子喷粉。然后将处理的植株在20-22℃和90-95%的相对湿度下培养24小时,随后用活性成分的含水制剂处理。再在20-22℃和65-70%的相对湿度下培养8天后,测定真菌的发展程度。用目测进行评价。
试验结果收集于下列表格中:分别施用时,活性成分的活性:
本发明增效混合物的活性:
对小麦变种禾白粉菌(Erysiphe graminis var.tritici)(小麦白粉病)的作用
活性成分 | 施用量[ppm] | 效率[%] |
I.1 (R=H) | 1641 | 10100 |
I.2 (R=F) | 41 | 00 |
II.a | 16 | 0 |
II.b | 1641 | 10100 |
II.c | 1 | 0 |
未处理的对照物 | -/- | 0 |
增效混合物 | 效率 | |||
活性成分 | ppm | 比率 | 观察值 | 计算值 |
I.1+II.a | 16+16 | 1/1 | 90 | 10 |
I.1+II.b | 16+16 | 1/1 | 80 | 19 |
4+4 | 1/1 | 95 | 19 | |
I.1+II.c | 1+1 | 1/1 | 98 | 0 |
I.2+II.b | 4+4 | 1/1 | 90 | 10 |
1+1 | 1/1 | 98 | 0 | |
I.2+II.c | 1+1 | 1/1 | 97 | 0 |
将小麦苗(品种:Frhgold)的叶片先用活性成分的含水制剂处理。大约24小时后,将植株用小麦变种禾白粉菌的孢子喷粉。然后将处理的植株在20-22℃和75-80%的相对湿度下培养7天。测定真菌的发展程度。分别施用时,活性成分的活性:
本发明增效混合物的活性:
活性成分 | 施用量[ppm] | 效率[%] |
I.1 (R=H) | 1 | 4 |
I.2 (R=F) | 1 | 89 |
II.c | 1 | 4 |
未处理的对照物 | -/- | 0 |
增效混合物 | 效率 | |||
活性成分 | ppm | 比率 | 观察值 | 计算值 |
I.1+II.c | 1+1 | 1/1 | 100 | 9 |
I.2+II.c | 1+1 | 1/1 | 98 | 90 |
Claims (11)
2.根据权利要求1的杀真菌混合物,包含增效活性量的权利要求1中所述的式I肟醚羧酰胺和权利要求1中所述的式IIa化合物。
3.根据权利要求1的杀真菌混合物,包含增效活性量的权利要求1中所述的式I肟醚羧酰胺和权利要求1中所述的式IIb化合物。
4.根据权利要求1的杀真菌混合物,包含增效活性量的权利要求1中所述的式I肟醚羧酰胺和权利要求1中所述的式IIc化合物。
5.根据权利要求1的杀真菌混合物,其中化合物I与化合物II的重量比是10∶1至0.1∶1。
6.防治有害真菌的方法,它包含用权利要求1中所述的式I化合物和一种权利要求1中所述的式IIa、IIb或IIc化合物或权利要求1所述的式I化合物处理有害真菌、其生存空间或意欲使其不受真菌侵染的植物、种子、土壤、表面、材料或空间。
7.根据权利要求6的方法,其中权利要求1中所述的化合物I和权利要求1中所述的式IIa、IIb或IIc化合物同时一起或分别或依次施用。
8.根据权利要求6的方法,其中用0.005至0.5千克/公顷的权利要求1的化合物I处理有害真菌、其生存空间或意欲使其不受真菌侵染的植物、种子、土壤、表面、材料或空间。
9.根据权利要求6的方法,其中用0.01至0.5千克/公顷的权利要求1所述的化合物IIa、IIb或IIc,处理有害真菌、其生存空间或意欲使其不受真菌侵染的植物、种子、土壤、表面、材料或空间。
10.根据权利要求1中所述的化合物I用于制备根据权利要求1中所述的杀真菌活性增效混合物的应用。
11.根据权利要求1中所述的化合物II用于制备根据权利要求1中所述的杀真菌活性增效混合物的应用。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE19530173 | 1995-08-17 | ||
DE19530173.0 | 1995-08-17 |
Publications (1)
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CN1193255A true CN1193255A (zh) | 1998-09-16 |
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CN96196332A Pending CN1193255A (zh) | 1995-08-17 | 1996-07-31 | 杀真菌混合物 |
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US (1) | US5968941A (zh) |
EP (1) | EP0844823B1 (zh) |
JP (1) | JPH11513024A (zh) |
KR (1) | KR19990037656A (zh) |
CN (1) | CN1193255A (zh) |
AR (1) | AR003293A1 (zh) |
AT (1) | ATE209857T1 (zh) |
AU (1) | AU6788196A (zh) |
BR (1) | BR9609926A (zh) |
CA (1) | CA2226745A1 (zh) |
CZ (1) | CZ36198A3 (zh) |
DE (1) | DE59608383D1 (zh) |
DK (1) | DK0844823T3 (zh) |
ES (1) | ES2169255T3 (zh) |
HU (1) | HUP9802842A2 (zh) |
IL (1) | IL122400A0 (zh) |
NZ (1) | NZ316404A (zh) |
PL (1) | PL324980A1 (zh) |
PT (1) | PT844823E (zh) |
SK (1) | SK20098A3 (zh) |
TW (1) | TW341493B (zh) |
WO (1) | WO1997006679A1 (zh) |
ZA (1) | ZA966955B (zh) |
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US6211236B1 (en) * | 1996-04-26 | 2001-04-03 | Basf Aktiengesellschaft | Fungicide mixtures |
HUP0002323A2 (hu) | 1997-05-30 | 2000-11-28 | Basf Aktiengesellschaft | Fungicid keverékek |
CO5040025A1 (es) * | 1997-05-30 | 2001-05-29 | Basf Ag | Mezclas fungicidas |
EA002404B1 (ru) | 1997-06-04 | 2002-04-25 | Басф Акциенгезельшафт | Фунгицидная смесь |
GB9718366D0 (en) * | 1997-08-29 | 1997-11-05 | Ciba Geigy Ag | Novel combinations |
CN1149924C (zh) * | 1998-03-24 | 2004-05-19 | 巴斯福股份公司 | 基于三(肟醚)衍生物和其它嗜球果伞素的杀真菌混合物 |
US6316452B1 (en) | 1998-05-18 | 2001-11-13 | Basf Aktiengesellschaft | Fungicidal mixture |
EP3047731A1 (en) | 2015-01-21 | 2016-07-27 | Basf Se | Method for combating soybean rust comprising treating soybean with (2E)-2-[3-substituted-2 [[(E)-[(2E)-2-alkoxyimino-1-methyl-2-phenyl-ethylidene]amino]oxymethyl]phenyl]-2-methoxy-imino-N-methyl-acetamides |
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CA1310267C (en) * | 1986-07-09 | 1992-11-17 | Yutaka Hirao | Process for heat treating chemically unmodified _-globulin |
GB8903019D0 (en) * | 1989-02-10 | 1989-03-30 | Ici Plc | Fungicides |
US5145856A (en) * | 1989-02-10 | 1992-09-08 | Imperial Chemical Industries Plc | Fungicides |
US5264440A (en) * | 1989-02-10 | 1993-11-23 | Imperial Chemical Industries Plc | Fungicides |
DE4030038A1 (de) * | 1990-09-22 | 1992-03-26 | Basf Ag | Ortho-substituierte phenylessigsaeureamide |
DE4309857A1 (de) * | 1993-03-26 | 1994-10-06 | Basf Ag | Fungizide Mischung |
US5436248A (en) * | 1993-07-02 | 1995-07-25 | Ciba-Geigy Corporation | Microbicides |
ES2094608T3 (es) * | 1993-09-24 | 1997-01-16 | Basf Ag | Mezclas fungicidas. |
EP0738260B2 (en) * | 1994-01-05 | 2006-12-13 | Bayer CropScience AG | Pesticides |
DE4420279A1 (de) * | 1994-06-10 | 1995-12-14 | Basf Ag | Fungizide Mischungen |
-
1996
- 1996-07-31 CN CN96196332A patent/CN1193255A/zh active Pending
- 1996-07-31 JP JP9508874A patent/JPH11513024A/ja active Pending
- 1996-07-31 IL IL12240096A patent/IL122400A0/xx unknown
- 1996-07-31 NZ NZ316404A patent/NZ316404A/xx unknown
- 1996-07-31 HU HU9802842A patent/HUP9802842A2/hu unknown
- 1996-07-31 PL PL96324980A patent/PL324980A1/xx unknown
- 1996-07-31 CA CA002226745A patent/CA2226745A1/en not_active Abandoned
- 1996-07-31 KR KR1019980701133A patent/KR19990037656A/ko not_active Application Discontinuation
- 1996-07-31 AT AT96928395T patent/ATE209857T1/de not_active IP Right Cessation
- 1996-07-31 SK SK200-98A patent/SK20098A3/sk unknown
- 1996-07-31 EP EP96928395A patent/EP0844823B1/de not_active Expired - Lifetime
- 1996-07-31 BR BR9609926A patent/BR9609926A/pt not_active Application Discontinuation
- 1996-07-31 DE DE59608383T patent/DE59608383D1/de not_active Expired - Lifetime
- 1996-07-31 ES ES96928395T patent/ES2169255T3/es not_active Expired - Lifetime
- 1996-07-31 DK DK96928395T patent/DK0844823T3/da active
- 1996-07-31 WO PCT/EP1996/003359 patent/WO1997006679A1/de not_active Application Discontinuation
- 1996-07-31 US US09/000,076 patent/US5968941A/en not_active Expired - Fee Related
- 1996-07-31 PT PT96928395T patent/PT844823E/pt unknown
- 1996-07-31 AU AU67881/96A patent/AU6788196A/en not_active Abandoned
- 1996-07-31 CZ CZ98361A patent/CZ36198A3/cs unknown
- 1996-08-08 TW TW085109613A patent/TW341493B/zh active
- 1996-08-16 ZA ZA9606955A patent/ZA966955B/xx unknown
- 1996-08-16 AR ARP960104027A patent/AR003293A1/es unknown
Also Published As
Publication number | Publication date |
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MX9709804A (es) | 1998-03-29 |
DK0844823T3 (da) | 2002-03-04 |
AR003293A1 (es) | 1998-07-08 |
CA2226745A1 (en) | 1997-02-27 |
JPH11513024A (ja) | 1999-11-09 |
ES2169255T3 (es) | 2002-07-01 |
NZ316404A (en) | 1998-12-23 |
ATE209857T1 (de) | 2001-12-15 |
SK20098A3 (en) | 1998-10-07 |
EP0844823B1 (de) | 2001-12-05 |
AU6788196A (en) | 1997-03-12 |
IL122400A0 (en) | 1998-06-15 |
US5968941A (en) | 1999-10-19 |
ZA966955B (en) | 1998-02-16 |
KR19990037656A (ko) | 1999-05-25 |
PL324980A1 (en) | 1998-06-22 |
BR9609926A (pt) | 1999-06-29 |
EP0844823A1 (de) | 1998-06-03 |
TW341493B (en) | 1998-10-01 |
CZ36198A3 (cs) | 1998-06-17 |
PT844823E (pt) | 2002-05-31 |
DE59608383D1 (de) | 2002-01-17 |
WO1997006679A1 (de) | 1997-02-27 |
HUP9802842A2 (hu) | 1999-03-29 |
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