CN1130124C - 杀真菌混合物 - Google Patents
杀真菌混合物 Download PDFInfo
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- CN1130124C CN1130124C CN98805472A CN98805472A CN1130124C CN 1130124 C CN1130124 C CN 1130124C CN 98805472 A CN98805472 A CN 98805472A CN 98805472 A CN98805472 A CN 98805472A CN 1130124 C CN1130124 C CN 1130124C
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- compound
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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
- 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
-
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
Landscapes
- 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
本发明提供了一种杀真菌混合物，它包括增效有效量的活性成分：a)式(Ia)、(Ib)或(Ic)的苯基苄基醚衍生物，和/或(Id)的氨基甲酸酯或其盐或其加合物，式(Id)中x为CH或N，n为0，1或2，且R为卤素，C1-C4-烷基或C1-C4卤代烷基，如果n为2，各R基团可以不同，和b)式(II)的N-丙酮基苯甲酰胺或其盐或其加合物，其中R1和R3相互独立地是卤素或C1-C4-烷基；R2是氰基、C1-C4-烷基、C2-C4-链烯基、C2-C4-炔基或C1-C4-烷氧基；R4是氢或C1-C4-烷基；R5是C2-C4-烷基；R6是氰硫基、异氰硫基或卤素。
Description
本发明涉及杀真菌混合物，该混合物包括增效有效量的活性成分：
a)式I.a、I.b或I.c的苯基苄基醚衍生物和/或Id的氨基甲酸酯或其盐或其加合物：
式Id中X为CH或N，n为0，1或2，且R为卤素，C1-C4-烷基或C1-C4卤代烷基，如果n为2，各R基团可以不同，和
b)式II的N-丙酮基苯甲酰胺或其盐或其加合物：其中R1和R3相互独立地是卤素或C1-C4-烷基；R2是氰基、C1-C4-烷基、C2-C4-链烯基、C2-C4-炔基或C1-C4-烷氧基；
R4是氢或C1-C4-烷基；
R5是C2-C4-烷基；
R6是氰硫基、异氰硫基或卤素。
此外，本发明还涉及用式I(I.a、I.b或I.c)与II化合物的混合物防治有害真菌的方法，以及化合物I和化合物II在制备这种混合物方面的应用。
式Ia-c化合物、其制备以及它们抗有害真菌的活性已由文献公开(EP-A 253 213；EP-A 254 426；EP-A 398 692)。
式Id化合物、其制备以及它们抗有害真菌的活性已由文献公开(WO-A 93/15,046；WO-A 96/01,256和WO-A 96/01,258)。
同样已知化合物II与二硫代氨基甲酸盐类的增效混合物、其制备和它们抗有害真菌的活性(EP-A 753 258；US-A 5,304,572)。
本发明的目的是提供在减少活性成分施用总量的同时具有改进的抗有害真菌作用的混合物(增效混合物)，以便减少施用量，并改善已知化合物I和II的作用谱。
为此，我们已经发现，本发明的这一目的可由本文开头所述的混合物实现。此外，我们还发现，与单独施用单一化合物的情形相比，通过同时(即一起或分别)施用化合物I和化合物II，或者先后地施用化合物I和化合物II能够更好地防治有害真菌。
式Id特别表示其中取代基的组合对应于下表中一行的氨基甲酸酯：
| Nr. | X | Rn |
| I.1 | N | 2-F |
| I.2 | N | 3-F |
| I.3 | N | 4-F |
| I.4 | N | 2-Cl |
| I.5 | N | 3-Cl |
| I.6 | N | 4-Cl |
| I.7 | N | 2-Br |
| I.8 | N | 3-Br |
| I.9 | N | 4-Br· |
| I.10 | N | 2-CH3 |
| I.11 | N | 3-CH3 |
| I.12 | N | 4-CH3 |
| I.13 | N | 2-CH2CH3 |
| I.14 | N | 3-CH2CH3 |
| I.15 | N | 4-CH2CH3 |
| r.16 | N | 2-CH(CH3)2 |
| I.17 | N | 3-CH(CH3)2 |
| I.18 | N | 4-CH(CH3)2 |
| I.19 | N | 2-CF3 |
| I.20 | N | 3-CF3 |
| I.21 | N | 4-CF3 |
| I.22 | N | 2，4-F2 |
| I.23 | N | 2，4-Cl2 |
| I.24 | N | 3，4-Cl2 |
| I.25 | N | 2-Cl，4-CH3 |
| I.26 | N | 3-Cl，4-CH3 |
| I.27 | CH | 2-F |
| I.28 | CH | 3-F |
| I.29 | CH | 4-F |
| I.30 | CH | 2-Cl |
| I.31 | CH | 3-Cl |
| I.32 | CH | 4-Cl |
| I.33 | CH | 2-Br |
| I.34 | CH | 3-Br |
| I.35 | CH | 4-Br |
| I.36 | CH | 2-CH3 |
| I.37 | CH | 3-CH3 |
| Nr. | X | Rn |
| I.38 | CH | 4-CH3 |
| I.39 | CH | 2-CH2CH3 |
| I.40 | CH | 3-CH2CH3 |
| I.41 | CH | 4-CH2CH3 |
| I.42 | CH | 2-CH(CH3)2 |
| I.43 | CH | 3-CH(CH3)2 |
| I.44 | CH | 4-CH(CH3)2 |
| I.45 | CH | 2-CF3 |
| I.46 | CH | 3-CF3 |
| I.47 | CH | 4-CF3 |
| I.48 | CH | 2，4-F2 |
| I.49 | CH | 2，4-Cl2 |
| I.50 | CH | 3，4-Cl2 |
| I.51 | CH | 2-Cl，4-CH3 |
| I.52 | CH | 3-Cl，4-CH3 |
其中特别优选化合物I.12，I.23，I.32和I.38。
式II特别表示其中取代基的组合对应于下表中一行的N-丙酮基苯甲酰胺：
| Nr. | R1 | R2 | R3 | R4 | R5 | R6 |
| II.1 | Cl | CH3 | Cl | CH2CH3 | CH3 | Cl |
| II.2 | Cl | CH2CH3 | Cl | CH2CH3 | CH3 | Cl |
| II.3 | Cl | OCH3 | Cl | CH2CH3 | CH3 | Cl |
| II.4 | Cl | OCH2CH3 | Cl | CH2CH3 | CH3 | Cl |
| II.5 | Cl | CN | Cl | CH2CH3 | CH3 | Cl |
| II.6 | Br | CH3 | Br | CH2CH3 | CH3 | Cl |
| II.7 | Br | CN | Br | CH2CH3 | CH3 | Cl |
特别优选那些在EP-A 753 258中一般和特别优选的N-丙酮基苯甲酰胺。
考虑到它们包含的氮原子的碱性性质，化合物Id和II能够与无机或有机酸或与金属离子形成盐或加合物。
无机酸的实例包括氢卤酸例如氢氟酸、氢氯酸、氢溴酸和氢碘酸，硫酸、磷酸和硝酸。
合适的有机酸包括例如甲酸、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(含有1-20个碳原子的直链或支链烷基磺酸)，芳基磺酸或芳基二磺酸(其上连接有一个或两个磺基的芳基(如苯基和萘基))，烷基膦酸(具有1-20个碳原子的直链或支链烷基膦酸)，芳基膦酸或芳基二膦酸(其上连接有一个或两个磷酸残基的芳基(例如苯基和萘基))，其中的烷基或芳基还可携带其它取代基，例如，对-甲苯磺酸，十二烷基苯磺酸、水杨酸，对-氨基水杨酸，2-苯氧基苯甲酸，2-乙酰氧基苯甲酸等。
适当的金属离子尤为下列各族元素的离子：第一到第八副族元素(特别是铬，锰，铁，钴，镍，铜，锌)，以及第二主族元素(特别是钙和镁)，第三和第四主族元素(特别是铝，锡和铅)。这些金属可以以它们可能具有的各种价态存在。
当制备混合物时，优选采用纯活性成分I和II，其中可以进一步混入其它对有害真菌或其它害虫(如昆虫，蛛形纲动物或线虫)具有活性的成份，或者还可混入具有除草或植物生长调节活性的成份或肥料。
化合物I与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，它对广谱的植物病原真菌均有优异活性，特别是对属于子囊菌纲、担子菌纲、半知菌纲和藻状菌纲的真菌。这些化合物中某些具有内吸作用，因而可用作叶面和土壤杀真菌剂。
它们在防治各种作物如棉花，蔬菜类(如黄瓜，菜豆，番茄，马铃薯和葫芦科)，大麦，牧草，燕麦，香蕉，咖啡，玉米，水果类，稻，黑麦，大豆，葡萄，小麦，观赏植物，甘蔗以及这些作物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(Erysiphecichoracearum)和苍耳单丝壳菌(Sphaerotheca fuliginea)、苹果上的苹果白粉病菌(Podosphaera leucotricha)、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)、小麦上的颖枯病菌(Septoria nodorum)、草莓、蔬菜、观赏植物和葡萄上的灰霉菌(Botrytis cinerea)、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)、啤酒花和黄瓜上的假霜霉属(Pseudoperonospora)蔬菜和水果上的链格孢菌(Alternaria)，香蕉上的球腔菌(Mycosphaerella)，以及镰刀菌(Fusarium)和轮枝孢菌(Verticillium)。
而且，它们可用于保护材料(如保护木材)免遭例如宛氏拟青霉(Paecilomyces variotii)之类的真菌侵害。
化合物I与II可以同时，即一起施用或分别施用，或者先后施用。在分别施用的情形下，其施用次序一般对防治的结果没有任何影响。
化合物I与II之间通常以10∶1-0.01∶1，优选5∶1-0.05∶1，特别是1∶1-0.05∶1的重量比使用。
本发明混合物的施用量，特别是对于大田农作物的情况下，一般为0.01-8kg/ha，优选0.1-5kg/ha，尤为0.5-3.0kg/ha，这取决于所希望的效果。
就化合物I而言，施用量为0.01-2.5kg/ha，优选0.05-2.5kg/ha，特别是0.05-1.0kg/ha。
相应地，就化合物II来说，施用量一般为0.01-10kg/ha，优选0.05-5kg/ha，特别是0.1-2.0kg/ha。
对于种子的处理，混合物的施用量一般为0.001-250g/kg种子，优选0.01-100g/kg，特别是0.01-50g/kg。
如果要防治植物病原有害真菌，可以在植物播种之前或之后，或者在植物发芽之前或之后通过对种子、植物或土壤喷雾或撒粉方式分别或一起施用化合物I与II或化合物I与II的混合物。
本发明的杀真菌增效混合物，或化合物I和II，可以配制成例如即可使用喷雾溶液，粉剂和悬浮剂形式，或高浓度的水、油或其它悬浮液、分散液、乳液，油分散剂，糊剂，喷粉剂，撒播剂或颗粒剂的形式，并通过喷雾、弥雾、撒粉、撒播或浇泼使用。施用形式主要取决于使用的目的；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。
这些制剂采用本领域公知的方式如通过加入溶剂和/或载体制备。通常将这种制剂与惰性添加剂如乳化剂或分散剂混合。
合适的表面活性物质为下列酸的碱金属盐、碱土金属盐和铵盐：芳族磺酸例如木质素磺酸、苯酚磺酸、萘磺酸和二丁基萘磺酸，和脂肪酸，烷基-和烷芳基磺酸，烷基-、月桂基醚-和脂肪醇硫酸；以及硫酸化的十六烷基醇、十七烷基醇和十八烷基醇以及脂肪醇乙二醇醚的盐，磺化的萘及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，聚氧乙烯辛基苯酚醚，乙氧基化的异辛基苯酚、辛基苯酚或壬基苯酚，烷基苯酚聚乙二醇醚或三丁基苯基聚乙二醇醚，烷芳基聚醚醇，异十三烷基醇、脂肪醇/氧化乙烯缩合物，乙氧基化蓖麻油，聚氧乙烯烷基醚或聚氧丙烯烷基醚，十二烷基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、撒播剂和喷粉剂可以通过混合或一同研磨化合物I或II或化合物I和II的混合物与固体载体制备。
颗粒剂(例如包衣颗粒，浸渍颗粒和均质颗粒)通常通过将活性成分粘合到固体载体上来制备。
填料或固体载体是例如矿质土类如硅胶、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、硫酸镁、氧化镁、研碎的合成物质、肥料如硫酸铵、磷酸铵、硝酸铵、尿素，以及植物源产物如谷类作物粉末、树皮、木材和坚果壳粉，纤维素粉末或其它固体载体。
制剂通常包括0.1至95重量％，优选0.5至90重量％化合物I或II中的一种或化合物I和II的混合物。所用活性成分的纯度为90％-100％，优选95％-100％(根据NMR谱或HPLC测定)。
化合物I或II，或其混合物，或相应的制剂通过用杀真菌有效量的混合物，或化合物I和II(在分别施用情形下)处理有害真菌，其聚集地，或处理欲使其免受这些真菌侵染的植物、种子、土壤、表面，材料或空间的方式施用。
施用可以在有害真菌侵染前或侵染后进行。
本发明混合物的增效作用可以通过下面的试验来证明：
应用实施例1-抗蕃茄上的致病疫霉(Phytophthora infestans)活性
使用包含10％活性成分、63％环己酮和27％乳化剂的储备溶液制备的含水悬浮液喷雾盆栽植物(栽培品种“Grosse Fleischtomate”)的叶片至滴流。第二天，用致病疫霉的游动孢子的含水悬浮液感染叶片。之后将该植物放置在水蒸气饱和的温度为16至18℃的培养室中。6天后，未处理的但已感染的对照植物的凋萎病已发展到可以目测评价疾病感染水平(％)的程度。
通过测定感染叶面面积的百分数进行评价。这些百分数被换算成作用效力。作用效力(W)采用下述Abbot公式计算：
W＝(1-α)·100/βα表示处理植物的真菌感染，以％计，和β表示未处理(对照组)植物的真菌感染，以％计
效力0表示处理植物的感染程度与未处理对照植物感染程度相当；效力100表示处理植物未被感染。
采用Colby公式[R.S.Colby，
杂草(Weeds)，15，20-22(1967)]测定活性成分混合物的预期作用效力并与观测到的作用效力加以比较。
Colby公式：
E＝x+y-x·y/100其中：
E表示使用浓度分别为a和b的活性成分A和B的混合物的情况下的预期作用效力，以未处理对照组的％表示
x表示使用浓度为a的活性成分A的情况下的作用效力，以未处理对照组的％表示
y表示使用浓度为b的活性成分B的情况下的作用效力，以未处理对照组的％表示。
结果列于下表2和3中。
表2
| 活性成份 | 活性成份在喷雾液中的浓度(ppm) | 作用效力，以未处理对照组的％表示 |
| 对照组(未处理) | (100％感染) | 0 |
| Ia | 10,50,25 | 000 |
| Ib | 0,25 | 0 |
| 化合物I.32 | 0,25 | 70 |
| 化合物II.1 | 0,50,25 | 200 |
表3
*)采用Colby公式计算的
| 本发明的混合物 | 观察到的作用效力 | 预期作用效力 |
| 1ppm Ia+0,25ppm II.1 | 30 | 0 |
| 0,5ppm Ia+0,5ppm II.1 | 50 | 20 |
| 0,25ppm Ia+0,5ppm II.1 | 40 | 20 |
| 0,25 Ib+0,5ppm II.1 | 60 | 20 |
| 0,25ppm I.32+0,5ppm II.1 | 97 | 76 |
试验结果表明，对于所有的混合比例，所观察的效力均超过采用Colby公式计算的效力。
Claims (6)
1.一种杀真菌混合物，该混合物包括增效有效量的活性成分：
a)Id的氨基甲酸酯或其盐或其加合物：
式Id中X为CH，n为0，1或2，且R为卤素，C1-C4-烷基或
C1-C4卤代烷基，如果n为2，各R基团可以不同，和
b)式II的N-丙酮基苯甲酰胺或其盐或其加合物：
其中
R1和R3相互独立地是卤素或C1-C4-烷基；
R2是氰基、C1-C4-烷基、C2-C4-链烯基、C2-C4-炔基或C1-C4-烷氧基；
R4是氢或C1-C4-烷基；
R5是甲基；
R6是卤素；
其中化合物I与化合物II或其盐或加合物的重量比为10∶1-0.01∶1。
2.一种防治有害真菌的方法，该方法包括用权利要求1中所述的混合物处理有害真菌、它们的聚集地，或处理欲使其免受这些真菌侵染的植物、种子、土壤、表面，材料或空间。
3.权利要求2的方法，其中权利要求1所述的化合物I和权利要求1所述的化合物II或其盐或其加合物通过分开或一起的同时方式，或者先后方式施用。
4.权利要求2或3的方法，其中权利要求1所述的化合物I的施用量为0.01-2.5kg/ha。
5.权利要求2-4中任一项的方法，其中权利要求1所述的化合物II或其盐或其加合物的施用量为0.01-10kg/ha。
6.权利要求1的组合物，该组合物被调整成两部分，其中一部分包括在固体或液体载体中的权利要求1所述的式I化合物，而另一部分则包括在固体或液体载体中的权利要求1所述的式II化合物或其盐或其加合物。
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| JP2011201856A (ja) * | 2010-03-03 | 2011-10-13 | Sumitomo Chemical Co Ltd | 植物病害防除組成物及び植物病害防除方法 |
| CN103210907A (zh) * | 2013-03-24 | 2013-07-24 | 广东中迅农科股份有限公司 | 苯酰菌胺水悬浮剂及其制备方法 |
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| US5304572A (en) * | 1992-12-01 | 1994-04-19 | Rohm And Haas Company | N-acetonylbenzamides and their use as fungicides |
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| ATE145891T1 (de) | 1989-05-17 | 1996-12-15 | Shionogi & Co | Verfahren zur herstellung von alkoxyiminoacetamid-derivaten und ein zwischenproduckt dafür |
| WO1993015046A1 (de) | 1992-01-29 | 1993-08-05 | Basf Aktiengesellschaft | Carbamate und diese enthaltende pflanzenschutzmittel |
| DE4423612A1 (de) | 1994-07-06 | 1996-01-11 | Basf Ag | 2-[(Dihydro)pyrazolyl-3'-oxymethylen]-anilide, Verfahren zu ihrer Herstelung und ihre Verwendung |
| US5650973A (en) | 1994-09-27 | 1997-07-22 | Micrel, Inc. | PCMCIA power multiplexer integrated circuit with programmable decode |
| ES2179330T3 (es) | 1996-04-26 | 2003-01-16 | Basf Ag | Mezcla fungicida. |
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| IL128121A (en) * | 1996-08-30 | 2001-12-23 | Basf Ag | Fungicide mixture containing derivatives -2 [1 ', 2', 4 ', - triazole-3'-isloxymethylene] - anilides and carboxanilide derivatives |
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| US5304572A (en) * | 1992-12-01 | 1994-04-19 | Rohm And Haas Company | N-acetonylbenzamides and their use as fungicides |
| CN1145722A (zh) * | 1995-07-12 | 1997-03-26 | 罗姆和哈斯公司 | 控制植物病原菌的方法 |
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