CN1064514C - 杀真菌混合物 - Google Patents
杀真菌混合物 Download PDFInfo
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- CN1064514C CN1064514C CN95193513A CN95193513A CN1064514C CN 1064514 C CN1064514 C CN 1064514C CN 95193513 A CN95193513 A CN 95193513A CN 95193513 A CN95193513 A CN 95193513A CN 1064514 C CN1064514 C CN 1064514C
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Classifications
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- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
公开了一种杀真菌混合物，其含有协同有效量的a)式Ia或Ib的肟醚羧酸酯
和b)1-(1，2，4-三唑-1-基)-2-氰基-2-(4-氯代苯基)己烷Ⅱ
Description
本发明涉及杀真菌混合物，其含有协同有效量的a)式Ⅰa或Ⅰb的肟醚羧酸酯和b)1-(1，2，4-三唑-1-基)-2-氰基-2-(4-氯代苯基)己烷Ⅱ
本发明另外涉及用化合物Ⅰ和Ⅱ的混合物灭杀有害真菌的方法，以及用化合物Ⅰ和化合物Ⅱ制备这种混合物的应用。
式Ⅰ(或Ⅰa或Ⅰb)化合物，其制备方法，和其抗有害真菌的作用在文献EP-A253213中已公开。化合物Ⅱ(通用名：腈菌唑)，其制备方法和其抗有害真菌的作用同样也是已知的。
着眼于降低已知化合物的应用量和提高、改善其作用谱，本发明以可降低的活性化合物的用量、具有提高的抗有害真菌作用的混合物(协同混合物)为基础。
因此发现了上文所定义的混合物。另外还发现，同时共同使用或分开使用化合物Ⅰ和化合物Ⅱ或接续使用化合物Ⅰ和化合物Ⅱ与单独使用各化合物相比，有害真菌能更好地被控制。
就C=N双键而论，式Ⅰ和Ⅱ化合物可以以E或Z构型存在(相对于羧酸功能基)。因此本发明混合物在各种情况下可以使用纯的E或Z异构体，或者是E／Z异构体混合物。优选使用E／Z异构体混合物或E-异构体，对于化合物Ⅰ来说，E异构体是特别优选的。
由于N基的碱性，化合物Ⅱ能与无机或有机酸或者与金属离子形成盐或加成产物。
无机酸的例子是氢卤酸，如氢氟酸，盐酸，氢溴酸和氢碘酸，硫酸，磷酸和硝酸。
合适的有机酸是，例如，甲酸，碳酸，链烷酸如乙酸，二氟乙酸，三氯乙酸和丙酸，也可以是羟基乙酸，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碳原子的直链或支链烷基的磺酸)，芳基磺酸或-二磺酸(芳香基团例如是带一个或两个磺酸基团的苯基和萘基)，烷基磷酸(带有1至20个碳原子的直链或支链烷基的磷酸)，芳基磷酸或-二磷酸(芳香基团如带一个或两个磷酸基团的苯基和萘基)，所述烷基和芳基可以进一步带有取代基，例如对甲苯磺酸，邻羟基苯甲酸，对氨基邻羟基苯甲酸，2-苯氧基苯甲酸，2-乙酰氧基苯甲酸，等等。
合适的金属离子特别是第二主族元素离子，特别是钙和镁，第三和第四主族的元素离子，特别是铝，锡，铅，以及第一至第八副族元素离子，特别是铬，锰，铁，钴，镍，铜，锌和其它元素的离子。特别优选第四周期副族元素的金属离子。这些金属可以以适于它们的不同价态而存在。
优选地，在混合物制剂中使用纯的活性化合物Ⅰ和Ⅱ，如果需要，其中可进一步混合有灭杀有害真菌或其它害虫如昆虫，蜘蛛或线虫的活性化合物，或者除草剂或生长调节活性化合物或肥料。
化合物Ⅰ和Ⅱ的混合物以及化合物Ⅰ和Ⅱ的同时共同或分开使用的应用以出色的抗广谱植物病原体真菌、特别是抗子囊菌纲和担子菌纲的作用为特征。在一些情况下，它们具有系统活性，因此也可用作叶和土壤杀真菌剂。
它们对各种农作物棉花，蔬菜植物(例如黄瓜，豆类和葫芦)，大麦，草坪，燕麦，咖啡、玉米，水果植物，稻，黑麦，大豆，葡萄，小麦，观赏植物，甘蔗和多种种子上的多种真菌的控制具有特别的重要性。
特别是，它们适于控制下面植物病原体真菌：谷类植物上的禾白粉菌(Erysiphe graminis)(粉状霉病)，葫芦上的二孢白粉菌(Erysiphecichora cearum)和苍耳单丝壳菌(Sphaerotheca fuliginea)，苹果上的苹果白粉病(Podosphaera Leucotricha)，葡萄藤上的葡萄白粉病钩丝壳霉(Uncinula necator)，谷类植物上的柄锈菌属(Puccinia)的种，棉花和草坪上的丝核菌属(Rhizoctonia)的种，谷类植物和甘蔗上的黑粉菌属(Ustilago)的种，苹果上的苹果黑星菌(Venturia inaequalis)(Scab)，谷类植物上的助壶菌属(Helminthosporium)的种，小麦上的颖枯壳针孢(Septoria nodorum)，草莓和葡萄藤上的灰色葡萄孢(Botrytis cinerea)(灰色霉菌)，落花生上的花生尾孢(Cercosporaarachidicola)，小麦和大麦上的Pseuolocercosporella herpotri choides，稻上的稻瘟病，马铃薯和番茄上的蔓延疫霉(Phytophthorainfestans)，葡萄藤上的葡萄生单轴霉(Pla smopara viticola)，蔬菜和水果上的链格孢属(Alter naria)的种，以及镰孢属(Fusarium)和轮枝孢属(Vertici llium)的种。
另外它们能用于材料的保护例如，木材防腐，例如杀宛氏拟青霉。
化合物Ⅰ和Ⅱ能同时共同地或分开或接续使用，分开应用情况下的次序一般对控制成效没有影响。
化合物Ⅰ和Ⅱ通常以重量比10∶1至0．1∶1施用，优选5∶1至0．2∶1，特别是5∶1至1∶1。
根据所需作用的类型，本发明混合物施用比例是0．01至3kg／ha，优选0．1至1．5kg／ha，特别是0．1至1，0kg／ha。化合物Ⅰ的施用率是0．01至0．5kg／ha，优选0．05至0．5kg／ha，特别是0．05至0．4kg／ha。化合物Ⅱ的施用率相应地为0．01至0．5kg／ha，优选从0．05至0．5kg／ha，特别是0．05至0．4kg／ha。
在对种子的处理中，一般使用的混合物的施用率是0．001至50g／kg种子，优选0．01至10g／kg，特别是0．01至8g／kg。
如果要控制使植物发病的有害真菌，化合物Ⅰ和Ⅱ分开或共同施用、或者施用化合物Ⅰ和Ⅱ的混合物是在植物播种前后或者植物发芽前后将种子、植物或土壤喷雾或撒上粉剂而实施。
本发明杀真菌协同混合物或化合物Ⅰ和Ⅱ能制备成例如可直接喷雾的溶液，粉剂和悬浮剂形式，或高百分比水溶液、油或其它悬浮剂形式，分散剂，乳油，油分散剂，糊状制剂，粉末组合物，撒播组合物或颗粒剂，并能通过喷雾，喷洒，撒播，播散或润湿来施用。施用的形式取决于所需要的用途；每种情况下应保证本发明混合物的分散剂应尽可能细且均匀。
本发明制剂用先前已知的方法制备，例如通过加入溶剂和／或载体。隋性添加剂如乳化剂或分散剂常规上要混入制剂中。
合适的表面活性物质是芳香磺酸，例如木质素磺酸，苯酚磺酸，萘磺酸和二丁基萘磺酸，以及脂肪酸，烷基-和烷芳基磺酸，烷基-月桂醚和脂肪醇的硫酸酯的碱金属盐，碱土金属盐或铵盐，也可以是硫酸化的十六一，十七一和十八醇的盐，或者是脂肪醇甘醇醚，磺酰化萘和其衍生物与醛的缩合产物，萘与苯酚和甲醛的缩合产物或者萘磺酸与苯酚和甲醛的缩合产物，聚氧乙烯辛基苯酚醚，乙氧基化的异辛基，辛基或壬基苯酚，烷基苯酚或三丁基苯酚聚乙二醇醚，烷基芳基聚醚醇，异十三烷基醇，脂肪醇-亚乙基氧化物缩合物，乙氧化的蓖麻油，聚氧乙烯或聚氧丙烯烷基醚，月桂醇聚乙二醇醚乙酸酯，山梨醇酯，木素亚磺酸废液或甲基纤维素。
粉剂，撒播和播散剂能通过将化合物Ⅰ和Ⅱ，或化合物Ⅰ和Ⅱ的混合物与固体载体一起混合或共同研磨而制备。
颗粒剂(例如包衣，浸渍或同质颗粒)常规上通过将一种活性化合物或两种活性化合物结合到固体载体上而制备。
使用的填料或固体载体是，例如，矿物如硅胶，硅酸，硅酸盐，滑石，高岭土，石灰石，石灰，白垩，粘土，黄土，白土，白云石，硅藻土，硫酸钙和硫酸镁，氧化镁，磨碎的塑料，和化肥如硫酸铵，磷酸铵，硝酸铵，尿素和植物产品如谷物植物的糠，树皮末，木屑和栗壳末，纤维素粉末或其它固体载体。
本发明制剂一般含有0．1至95％重量、优选0．5至90％重量的一种化合物Ⅰ或Ⅱ或化合物Ⅰ和Ⅱ的混合物。这种情况下，活性化合物的使用纯度是90％至100％，优选95％至100％(根据NMR谱或HPLC谱)。
通过用杀真菌有效量的混合物，或在分开施用的情况下用杀真菌有效量的化合物Ⅰ和Ⅱ来处理有害真菌，或者处理植物，种子，土壤，地表，材料或场地，使其不受有害真菌的侵害，如此来应用本发明化合物Ⅰ或Ⅱ以及其混合物或相应的制剂。施用可以在受有害真菌侵扰前或后进行。
本发明混合物灭杀有害真菌的协同作用的实施例
下面的试验证明本发明化合物和其混合物的杀真菌作用：
分别或共同制备本发明活性化合物在70％重量的环己酮，20％重量的Nekanil LN(Lutensol AP6，以乙氧化烷基苯酚为基础的、具有乳化剂和分散剂作用的湿润剂)和10％重量的Emulphor EL(Emulan EL，以乙氧化脂肪醇为基础的乳化剂)的混合物中的20％浓度的乳油，并随后用水稀释至所需浓度。
通过测定受侵害叶面积的百分比来进行评定。这些百分值被转换成有效系数。
用Colby公式[R．S．Colby，Weeds 15(1967)，20-22]计算预期的活性化合物混合物的有效系数，并与实测的有效系数相比较。Colby公式：
E=X+Y-X×Y／100E 当使用浓度a和b的活性化合物A和B的混合物时，以未处理对照物百分比表示的所预期的有效系数X 当使用浓度a的活性化合物A时，以未处理对照物百分比表示的有效系数Y 当使用浓度b的活性化合物B时，以未处理对照物百分比表示的有效系数
有效系数是0的情况下，被处理植物上真菌的侵害程度相当于未处理的对照植物；有效系数100％的情况下，被处理植物没有受到真菌侵害。杀灰色葡萄孢(灰色霉菌)的活性
用活性化合物制剂对4-5叶期的辣椒籽苗(品种：NeusiedlerIdeal Elite)喷雾，直至叶湿淋淋的液滴滴落。干后，对植物喷雾真菌灰色葡萄孢分生菌丝悬浮液，并在高环境湿度、在22-24℃下保持5天。目测进行评估。
在这一试验中，化合物Ⅰa和Ⅱ的1∶1混合物(总的混合物施用率是5ppm或2．5ppm)实测有效系数分别是100或90％，期望有效系数分别是88或76％。未处理对照植物受侵害程度为90％。
Claims (5)
1．杀真菌混合物，其含有协同有效量的
a)式Ⅰa或Ⅰb的肟醚羧酸酯和
b)1-(1，2，4-三唑-1-基)-2-氰基-2-(4-氯代苯基)己烷Ⅱ
其中化合物Ⅰa或Ⅰb与化合物Ⅱ的重量比是10∶1至0．1∶1。
2．按权利要求1的杀真菌混合物的使用方法，包括用按权利要求1的杀真菌混合物处理有害真菌、它们的环境或处理植物、种子、土壤、地表、材料或场地，使其不受真菌的侵害。
3．权利要求2的方法，其中将按权利要求1的化合物Ⅰa或Ⅰb和权利要求1的化合物Ⅱ同时共同地或分开地施用，或接续施用。
4．权利要求2的方法，其中用0．01至0．5kg／公顷按权利要求1的化合物Ⅰa或Ⅰb处理有害真菌、它们的环境或处理植物、种子、土壤、地表、材料或场地，使其不受真菌侵害。
5．权利要求2的方法，其中用0．01至0．5kg／公顷按权利要求1的化合物Ⅱ处理有害真菌、它们的环境、或处理植物、种子、土壤、地表、材料或场地，使其不受真菌侵害。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4420278.4 | 1994-06-10 | ||
| DE4420278 | 1994-06-10 |
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| Publication Number | Publication Date |
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| CN1150379A CN1150379A (zh) | 1997-05-21 |
| CN1064514C true CN1064514C (zh) | 2001-04-18 |
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| CN95193513A Expired - Fee Related CN1064514C (zh) | 1994-06-10 | 1995-05-27 | 杀真菌混合物 |
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| US (1) | US5827861A (zh) |
| EP (1) | EP0763975B1 (zh) |
| JP (1) | JP3722838B2 (zh) |
| KR (1) | KR100380339B1 (zh) |
| CN (1) | CN1064514C (zh) |
| AT (1) | ATE184153T1 (zh) |
| AU (1) | AU690287B2 (zh) |
| CA (1) | CA2192492C (zh) |
| CZ (1) | CZ290569B6 (zh) |
| DE (1) | DE59506802D1 (zh) |
| DK (1) | DK0763975T3 (zh) |
| ES (1) | ES2135745T3 (zh) |
| GR (1) | GR3031311T3 (zh) |
| HU (1) | HU221026B1 (zh) |
| IL (1) | IL113994A (zh) |
| NZ (1) | NZ288221A (zh) |
| PL (1) | PL181281B1 (zh) |
| RU (1) | RU2152154C2 (zh) |
| SK (1) | SK281657B6 (zh) |
| TW (1) | TW369401B (zh) |
| UA (1) | UA46735C2 (zh) |
| WO (1) | WO1995034203A1 (zh) |
| ZA (1) | ZA954768B (zh) |
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| JP2000509054A (ja) * | 1996-04-26 | 2000-07-18 | ビーエーエスエフ アクチェンゲゼルシャフト | 殺菌剤混合物 |
| WO1998053685A1 (de) * | 1997-05-30 | 1998-12-03 | Basf Aktiengesellschaft | Fungizide mischungen |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4999042A (en) * | 1986-07-18 | 1991-03-12 | Imperial Chemical Industries Plc | Phenyl oximino-acetate fungicides |
| GB2267644A (en) * | 1992-06-10 | 1993-12-15 | Schering Ag | Mixed class synergistic fungicide based on pyrimethanil |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3623921A1 (de) * | 1986-07-16 | 1988-01-21 | Basf Ag | Oximether und diese enthaltende fungizide |
| US4999802A (en) * | 1989-01-13 | 1991-03-12 | International Business Machines Corporation | Floating point arithmetic two cycle data flow |
| DE4130298A1 (de) * | 1991-09-12 | 1993-03-18 | Basf Ag | Fungizide mischungen |
| GB9210830D0 (en) * | 1992-05-21 | 1992-07-08 | Ici Plc | Fungicidial composition |
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1995
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- 1995-05-27 UA UA97010108A patent/UA46735C2/uk unknown
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- 1995-05-27 DK DK95922489T patent/DK0763975T3/da active
- 1995-05-27 ES ES95922489T patent/ES2135745T3/es not_active Expired - Lifetime
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- 1995-05-27 AU AU27367/95A patent/AU690287B2/en not_active Ceased
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4999042A (en) * | 1986-07-18 | 1991-03-12 | Imperial Chemical Industries Plc | Phenyl oximino-acetate fungicides |
| GB2267644A (en) * | 1992-06-10 | 1993-12-15 | Schering Ag | Mixed class synergistic fungicide based on pyrimethanil |
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL ABSTRACTS VOL118 NO23 ABSTRACT NO228112 1993.7.1 E AMMERMANN ET AL BAS490F A BRODD SPECTRUM FUNGICIDE WITH A NEW NLODE OF ACTTON * |
| RESEARCH DISCLOSURE NO338 1992.1.1 DISCLOSED ANONYMOUSLY DISCLOSURE 33893 MIXTURE OF FUNGICIDES AND INSEDICDES * |
Also Published As
| Publication number | Publication date |
|---|---|
| CZ355196A3 (en) | 1997-05-14 |
| US5827861A (en) | 1998-10-27 |
| UA46735C2 (uk) | 2002-06-17 |
| CZ290569B6 (cs) | 2002-08-14 |
| ES2135745T3 (es) | 1999-11-01 |
| CA2192492A1 (en) | 1995-12-21 |
| GR3031311T3 (en) | 1999-12-31 |
| PL181281B1 (pl) | 2001-07-31 |
| ZA954768B (en) | 1996-12-09 |
| KR100380339B1 (ko) | 2004-05-20 |
| CA2192492C (en) | 2007-03-06 |
| NZ288221A (en) | 1997-12-19 |
| ATE184153T1 (de) | 1999-09-15 |
| KR970703702A (ko) | 1997-08-09 |
| SK281657B6 (sk) | 2001-06-11 |
| EP0763975A1 (de) | 1997-03-26 |
| AU2736795A (en) | 1996-01-05 |
| HUT76142A (en) | 1997-07-28 |
| SK155996A3 (en) | 1997-09-10 |
| AU690287B2 (en) | 1998-04-23 |
| RU2152154C2 (ru) | 2000-07-10 |
| EP0763975B1 (de) | 1999-09-08 |
| IL113994A0 (en) | 1995-10-31 |
| PL317535A1 (en) | 1997-04-14 |
| DK0763975T3 (da) | 1999-12-20 |
| JP3722838B2 (ja) | 2005-11-30 |
| DE59506802D1 (de) | 1999-10-14 |
| JPH10501249A (ja) | 1998-02-03 |
| HU221026B1 (hu) | 2002-07-29 |
| HU9603400D0 (en) | 1997-02-28 |
| TW369401B (en) | 1999-09-11 |
| CN1150379A (zh) | 1997-05-21 |
| WO1995034203A1 (de) | 1995-12-21 |
| IL113994A (en) | 2000-08-31 |
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