CN1258192A - 杀真菌混剂 - Google Patents
杀真菌混剂 Download PDFInfo
- Publication number
- CN1258192A CN1258192A CN98805666A CN98805666A CN1258192A CN 1258192 A CN1258192 A CN 1258192A CN 98805666 A CN98805666 A CN 98805666A CN 98805666 A CN98805666 A CN 98805666A CN 1258192 A CN1258192 A CN 1258192A
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- CN
- China
- Prior art keywords
- compound
- salt
- benzimidazole
- adduct
- acid
- Prior art date
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- 238000004128 high performance liquid chromatography Methods 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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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)
Abstract
一种杀真菌混剂,包括协同增效量的a.1)结构式Ⅰ.a,Ⅰ.b或Ⅰ.c的苯基苄基醚衍生物,或a.1)结构式为Ⅰ.d的氨基甲酸酯,其中X是CH和N,n是0,1或2以及R是卤素,C1－C4－烷基和C1－C4－卤素烷基,如果n=2,R可以是不同基团,或它们的盐或加合物,和b)来自苯并咪唑或产生苯并咪唑的前体(Ⅱ)一类的杀真菌活性化合物。
Description
本发明涉及一种杀真菌混剂，其包括以协同增效量存在的
a.1)结构式I.a，I.b或I.c的苯基苄基醚衍生物，
或a.1结构式为I.d的氨基甲酸酯，
其中X是CH和N，n是0，1或2以及R是卤素，C1-C4-烷基和C1-C4-卤素烷基，如果n＝2，R可以是不同基团，或它们的盐或加合物，或
和b)来自苯并咪唑或产生苯并咪唑的前体(II)一类的杀真菌活性化合物。
特别是，本发明涉及杀真菌混剂，其含有作为苯并咪唑或产生苯并咪唑的前体的以下II.a至II.f化合物：
II.a：1-(丁基氨基甲酰基)苯并咪唑-2-基氨基甲酸甲基酯
II.b：苯并咪唑-2-基氨基甲酸甲基酯
II.c：乙基苯并咪唑-2-基氨基甲酸2-(2-乙氧基乙氧基)酯
II.d：2-(2’-呋喃基)苯并咪唑
II.e：2-(1，3-噻唑-4-基)苯并咪唑
II.f：4，4’-(邻-亚苯基)双(3-硫代脲基甲酸甲酯)
而且，本发明涉及使用化合物I和II的混合物控制有害真菌的方法，以及化合物I和II用于制备这些混剂的用途。
结构式I的化合物，其制备和抗有害真菌活性已公开于文献中(EP-A253 213；EP-A 254 426；EP-A 398 692；EP-A 477 631；WO-A 93/15,046；WO-A 96/01,256；WO-A 96/01,258)。
化合物II也已公开：
·II.a(通用名：苯菌灵)：US-A 3,631,176，CAS RN[17804-35-2]；
·II.b(通用名：多菌灵)：US-A 3,657,443，CAS RN[10605-21-7]；
·II.c(通用名：咪菌威)：CAS RN[62732-91-6]；
·II.d(通用名：麦穗宁)：CAS RN[3878-19-1]；
·II.e(通用名：噻菌灵)：US-A 3,017,415，CAS RN[148-79-8]，和
·II.f(通用名：甲基硫菌灵)：DE-A19 30 540，CAS RN[23564-05-8]。
本发明的目的是提供混剂，其可以增进抗有害真菌活性并同时减少活性成分使用总量(增效混剂)，以便减少施药比例和扩大已知化合物I和II的杀菌活性谱。
已发现前面描述的混剂达到了本发明目的。而且，发现同时应用化合物I和II，即一起或分开，或顺次施用化合物I和II，与使用单一化合物相比可以更好地控制有害真菌。
结构式II.d代表，特别是氨基甲酸酯，其中各取代基的组合相应于下表各行。
| No. | X | Rn |
| Id.1 | N | 2-F |
| Id.2 | N | 3-F |
| Id.3 | N | 4-F |
| Id.4 | N | 2-Cl |
| Id.5 | N | 3-Cl |
| Id.6 | N | 4-Cl |
| Id.7 | N | 2-Br |
| Id.8 | N | 3-Br |
| Id.9 | N | 4-Br |
| Id.10 | N | 2-CH3 |
| Id.11 | N | 3-CH3 |
| Id.12 | N | 4-CH3 |
| Id.13 | N | 2-CH2CH3 |
| Id.14 | N | 3-CH2CH3 |
| Id.15 | N | 4-CH2CH3 |
| Id.16 | N | 2-CH(CH3)2 |
| Id.17 | N | 3-CH(CH3)2 |
| Id.18 | N | 4-CH(CH3)2 |
| Id.19 | N | 2-CF3 |
| Id.20 | N | 3-CF3 |
| Id.21 | N | 4-CF3 |
| Id.22 | N | 2，4-F2 |
| Id.23 | N | 2，4-Cl2 |
| Id.24 | N | 3，4-Cl2 |
| Id.25 | N | 2-Cl，4-CH3 |
| Id.26 | N | 3-C1，4-CH3 |
| Id.27 | CH | 2-F |
| Id.28 | CH | 3-F |
| Id.29 | CH | 4-F |
| Id.30 | CH | 2-Cl |
| Id.31 | CH | 3-Cl |
| Id.32 | CH | 4-Cl |
| Id.33 | CH | 2-Br |
| Id.34 | CH | 3-Br |
| Id.35 | CH | 4-Br |
| Id.36 | CH | 2-CH3 |
| Id.37 | CH | 3-CH3 |
| Id.38 | CH | 4-CH3 |
| Id.39 | CH | 2-CH2CH3 |
| Id.40 | CH | 3-CH2CH3 |
| Id.41 | CH | 4-CH2CH3 |
| Id.42 | CH | 2-CH(CH3)2 |
| Id.43 | CH | 3-CH(CH3)2 |
| Id.44 | CH | 4-CH(CH3)2 |
| Id.45 | CH | 2-CF3 |
| Id.46 | CH | 3-CF3 |
| No. | X | Rn |
| Id.47 | CH | 4-CF3 |
| Id.48 | CH | 2，4-F2 |
| Id.49 | CH | 2，4-Cl2 |
| Id.50 | CH | 3，4-Cl2 |
| Id.51 | CH | 2-Cl，4-CH3 |
| Id.52 | CH | 3-Cl，4-CH3 |
特别优选化合物Id.12，Id.23，Id.32和Id.38。
由于氮原子的基本特性，化合物I和II可以与无机或有机酸或金属离子形成盐或加合物。
无机酸的例子包括氢卤酸如氢氟酸、盐酸、氢溴酸和氢碘酸、硫酸、磷酸和硝酸。
适合的有机酸，例如，甲酸，碳酸和链烷酸，如乙酸、三氟乙酸、三氯乙酸和丙酸，还有乙醇酸、硫氰酸、乳酸、琥珀酸、柠檬酸、苯甲酸、肉桂酸、草酸、烷基磺酸(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(芳香基团，如苯基和萘基，带1或2个磺酸基团)、烷基膦酸(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(芳香基团，如苯基和萘基，带1或2个磷酸基团)，烷基或芳基可以进一步带有取代基，例如，对-甲苯磺酸、水杨酸、对-氨基水杨酸、2-苯氧基苯甲酸、2-乙酰氧基苯甲酸等。
适合的金属离子，特别是，第一至第八副族的元素离子，特别是铬、锰、铁、钴、镍、铜和锌，以及第二主族的元素，特别是钙和镁，和第三和第四主族元素，特别是铝、锡和铅。如适合，这些金属可以存在各种可接受的价态。
制备这些混剂时，优选使用纯活性成分I和II，并可以混合其它抗有害真菌或害虫如昆虫、蜘蛛或线虫的活性成分，或除草剂或植物生长调节活性成分或肥料。
化合物I和II的混剂，或化合物I和II同时，结合或分开使用，表现了对广谱的植物病原真菌的突出的杀菌作用，特别是来自子囊菌纲、担子菌纲，藻菌纲和半知菌纲的真菌。其中一些药剂是系统作用，因此也可作为叶面和土壤使用的杀菌剂。
控制各种农作物上的大量真菌是非常重要的，例如棉花、各种蔬菜(如黄瓜、蚕豆、番茄、马铃薯和葫芦)、大麦、草皮、燕麦、香蕉、咖啡、玉米、各种果树、水稻、黑麦、大豆、葡萄、小麦、观赏植物、甘蔗和各种种子。
特别适合控制以下植物病原真菌：禾谷类作物上的禾白粉菌(白粉菌)、葫芦上的二孢白粉菌和单丝壳白粉菌、苹果上的白叉丝单囊壳菌(苹果白粉菌)、葡萄上的葡萄钩丝壳菌、禾谷类作物上的柄锈菌属、棉花，水稻和草坪上的丝核菌属、禾谷类作物和甘蔗上的黑粉菌属、苹果黑星菌(斑点病)、禾谷类作物上的长蠕孢属、小麦的颍枯壳针孢菌(小麦颍枯病)、草莓，蔬菜，观赏植物和葡萄上的灰葡萄孢(灰霉病)、落花生尾孢(花生褐斑病)、小麦和大麦眼斑(基腐)病、稻梨孢菌、致病疫霉引起的马铃薯和番茄晚疫病、葡萄生单轴霉(葡萄霜霉病)、啤酒花和黄瓜上的假霜霉属、蔬菜和水果上的链格孢属、香蕉上的球腔菌属以及镰孢属和轮枝孢属真菌。
而且，这些混剂可以用来保护材料(如木材的保护)，例如抗多变拟青霉。
化合物I和II可以同时使用，或一起或分开或顺序使用，在分开使用时其顺序对防治效果没有任何影响。
一般化合物I和II使用重量比为10∶1-0.01∶1，优选5∶1-0.05∶1，特别是1∶1-0.05∶1。
依据预定效果的特性，本发明混剂的使用比例，特别是对农作物，为0.01-8kg/ha，优选0.1-5kg/ha，特别是0.5-3.0kg/ha。
就化合物I来说，使用比例是0.01-2.5kg/ha，优选0.05-2.5kg/ha，特别是0.1-1.0kg/ha。
相应地，就化合物II来说，使用比例是0.01-10kg/ha，优选0.05-5kg/ha，特别是0.05-2.0kg/ha。
用于种子处理时，一般混剂的使用比例是0.001-250g/kg种子，优选0.01-100g/kg，特别是0.01-50g/kg。
为控制有害植物病原真菌，化合物I和II的分开或结合使用或化合物I和II的混剂的使用通过喷雾或喷粉种子、播前或播后、或出苗前或出苗后的植物或土壤。
本发明杀真菌的协同增效混剂或化合物I和II，可以制成例如现配现喷溶液，粉剂和悬浮剂的形式或高度浓缩的水性、油性或其它悬浮剂、分散液、乳液、油分散液、糊剂、粉剂、撒施物或颗粒剂，并使用喷雾、雾化喷雾、喷粉、撒施或随水灌溉方法。使用剂型与应用目的有关；在任何情况下，都应该尽可能地使本发明混剂分布完全和均匀。
例如通过加入溶剂和/或载体，以已知方式制成制剂。通常在制剂中加入惰性添加物，如乳化剂或分散剂。
适合的表面活性剂是芳族磺酸，例如木素-、苯酚-、萘-和二丁基萘磺酸，和脂肪酸，烷基-和烷基芳基磺酸、烷基-、十二烷基醚和脂肪族醇硫酸的碱金属盐、碱土金属盐和铵盐以及硫酸化的十六-、十七-和十八碳醇或脂肪族醇乙二醇醚的盐、磺化萘和它的甲醛衍生物的缩合物、萘或萘磺酸与苯酚和甲醛的缩合物、聚氧乙烯辛基酚醚、乙氧基化异辛基-、辛基-或壬基苯酚、烷基苯酚聚乙二醇醚、三丁基苯基聚乙二醇醚、烷基芳基聚醚醇、异十三烷基醇、脂肪族醇/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，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。
制备药粉，撒施物和粉剂可以通过混合或联合研磨化合物I或II或化合物I和II与固体载体的混合物。
颗粒(例如包衣颗粒，浸渍颗粒或均一颗粒)的制备是通过将活性成分粘合在固体载体上。
填料或固体载体包括例如矿物质土，如硅胶、硅酸、硅胶、硅酸盐、滑石粉、高岭土、石灰石、石灰、白垩、细粘土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁、研磨的合成材料和肥料，如硫酸铵、磷酸铵、硝酸铵、尿素和植物性的来源产品，如谷粉、树皮粉、木粉和坚果壳粉，纤维素粉或其它固体载体。
一般，制剂中含有0.1-95％重量，优选0.5-90％重量的化合物I或II或化合物I和II的混剂。使用的活性成分纯度为90％-100％，优选95％-100％(根据NMR或HPLC谱)。
化合物I或II，混剂或相应制剂的应用方式为，用其杀菌有效量的混剂或分开使用的化合物I和II来处理有害真菌，它们的活动场所或它们可到达的植物、种子、土壤、地区、材料或空间。
有害真菌侵染前后施用此混剂都有效果。
使用实例
通过以下试验证实本发明混剂的增效作用：
对竦椒上的灰葡萄孢的杀菌活性
由含有10％活性化合物，63％环己酮和27％乳化剂的储备溶液制成的活性成分水剂喷施绿色辣椒花盘至全部润湿。药膜干燥后2小时，用灰葡萄孢的孢子悬浮液接种果盘，其在2％强Biomalz溶液中含有1.7×106孢子/mL。随后将接种的果盘孵育在潮湿的培养箱中，18℃ 4天。然后肉眼观察发病果盘上灰葡萄孢的侵染。
评估是以侵染叶片面积百分比为标准。将这些百分比转换成杀菌效果。使用Abbot公式计算杀菌效果(E)：
E＝(1-α)·100/β
α等于处理后的植物受真菌侵染％和
β等于未处理(对照)植物的真菌侵染％
杀菌效果0表示相当于未处理对照植物的侵染水平；杀菌效果100表示处理植物并未被侵染。
使用Colby公式计算活性成分混剂的预期杀菌效果，并与观察的杀菌效果相比较[R.S.Colby，Weeds 15(1967)，20-22]。
Colby公式：E＝X+Y-X·Y/100
E预期杀菌效果，当使用活性成分A和B的混剂，浓度为a和b时，
以未处理对照％表示
X杀菌效果，当使用活性成分A，浓度为a时，以未处理对照％表示
Y杀菌效果，当使用活性成分B，浓度为b时，以未处理对照％表示试验结果列于表2和3中。表2
表3
| 实例 | 活性成分 | 在喷雾液中活性成分的浓度ppm | 未处理对照的杀菌效果％ |
| 1C | 对照(未处理) | (100％ 侵染) | 0 |
| 2C | 化合物 Ia | 502512.56.3 | 50303020 |
| 3C | 化合物 Ic | 2512.5 | 8050 |
| 4C | 表1的化合物Id.32(＝Id.1) | 502512.5 | 504030 |
| 5C | 化合物IIa(苯菌灵) | 12.56.3 | 2010 |
| 6C | 化合物IIf(甲基硫菌灵) | 502512.5 | 2000 |
| 实例 | 本发明混剂 | 观察的杀菌效果 | 计算的杀菌效果*) |
| 7 | 12.5 ppm Ia+12.5 ppm IIa | 85 | 44 |
| 8 | 6.3 ppm Ia+6.3 ppm IIa | 80 | 28 |
| 9 | 50 ppm Ia+50 ppm IIf | 95 | 60 |
| 10 | 25 ppm Ia+25 ppm IIf | 85 | 30 |
| 11 | 12.5 ppm Ia+12.5 ppm IIf | 60 | 30 |
| 12 | 25 ppm Ic+25 ppm IIf | 95 | 80 |
| 13 | 12.5 ppm Ic+12.5 ppm IIf | 70 | 50 |
| 14 | 12.5 ppm Id.1+12.5 ppm IIa | 70 | 44 |
| 15 | 50 ppm Id.1+50 ppm II.f | 95 | 60 |
| 16 | 25 ppm Id.1+25 ppm II.f | 60 | 40 |
*)使用Colby公式计算
试验结果显示在所有混合比例中观察的杀菌效果都高于使用Colby公式预先计算的杀菌效果。
Claims (10)
1.一种杀真菌混剂，包括协同增效量的
a.1)结构式I.a，I.b或I.c的苯基苄基醚衍生物，
或a.1)结构式为I.d的氨基甲酸酯，
其中X是CH和N，n是0，1或2以及R是卤素，C1-C4-烷基和C1-C4-卤素烷基，如果n＝2，R可以是不同基团，或它们的盐或加合物，或
和b)来自苯并咪唑或产生苯并咪唑的前体(II)一类的杀真菌活性化合物。
2.根据权利要求1的杀真菌混剂，其中苯并咪唑或产生苯并咪唑的前体(II)选自以下化合物
II.a：1-(丁基氨基甲酰基)苯并咪唑-2-基氨基甲酸甲基酯
II.b：苯并咪唑-2-基氨基甲酸甲基酯
II.c：苯并咪唑-2-基氨基甲酸2-(2-乙氧基乙氧基)乙基酯
II.d：2-(2’-呋喃基)苯并咪唑
II.e：2-(1，3-噻唑-4-基)苯并咪唑
II.f：4，4’-(邻-亚苯基)双(3-硫代脲基甲酸甲酯)
3.根据权利要求1或2的杀真菌混剂，其中化合物I或它的盐或加合物与化合物II的重量比是10∶1-0.01∶1。
4.一种控制有害真菌的方法，其包括用权利要求1的结构式I化合物或它的盐或加合物与权利要求1或2的结构式II化合物，来处理有害真菌，它们的活动场所或它们可到达的植物、种子、土壤、地区、材料或空间。
5.根据权利要求4的方法，其中权利要求1的化合物I或它的盐或加合物与权利要求1的化合物II同时使用，一起或分开，或顺次使用。
6.根据权利要求4或5的方法，其中权利要求1的化合物I或它的盐或加合物，使用量为0.01-2.5kg/ha。
7.根据权利要求4-6中的任一项的方法，其中权利要求1或2的化合物II，使用量为0.01-10kg/ha。
8.权利要求1的化合物I或它的盐或加合物用于制备权利要求1的杀真菌协同增效混剂的用途。
9.权利要求1或2的化合物II用于制备权利要求1的杀真菌协同增效混剂的用途。
10.一种如权利要求1的组合物，其由两部分组成，一部分是包括结在固体或液体载体中的权利要求1的结构式I化合物，另一部分是包括在固体或液体载体中的权利要求1或2的化合物II。
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| JP5793896B2 (ja) * | 2010-10-07 | 2015-10-14 | 住友化学株式会社 | 植物病害防除組成物及び植物病害防除方法 |
| CN104886143A (zh) * | 2015-05-12 | 2015-09-09 | 柳州市耕青科技有限公司 | 多肉植物虹之玉的专用抗腐烂药剂 |
| CN104938510B (zh) * | 2015-07-08 | 2017-10-10 | 安徽省农业科学院植物保护与农产品质量安全研究所 | 一种含吡唑醚菌酯和噻菌灵的杀菌组合物 |
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| WO1997015189A1 (de) * | 1995-10-25 | 1997-05-01 | Basf Aktiengesellschaft | Fungizide mischungen von oximethercarbonsäureestern mit kupferhaltigen fungiziden |
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