CN1331562A - 杀真菌混合物 - Google Patents
杀真菌混合物 Download PDFInfo
- Publication number
- CN1331562A CN1331562A CN99814746A CN99814746A CN1331562A CN 1331562 A CN1331562 A CN 1331562A CN 99814746 A CN99814746 A CN 99814746A CN 99814746 A CN99814746 A CN 99814746A CN 1331562 A CN1331562 A CN 1331562A
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- Prior art keywords
- compound
- formula
- mixture
- acid
- fungicidal
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- 239000000203 mixture Substances 0.000 title claims abstract description 44
- -1 halogen alkane Chemical class 0.000 claims abstract description 20
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 12
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- 229910052802 copper Inorganic materials 0.000 claims abstract description 9
- 239000010949 copper Substances 0.000 claims abstract description 9
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 60
- 229940084434 fungoid Drugs 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
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- 238000000034 method Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
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- 239000002689 soil Substances 0.000 claims description 5
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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
- 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
-
- 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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/16—Heavy metals; Compounds thereof
- A01N59/20—Copper
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
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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)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
一种杀真菌混合物,包括协同增效量的a.1)式Ⅰ.a的氨基甲酸酯,其中X是CH或N,n是0、1或2以及R是卤素、C1－C4－烷基和C1－C4－卤代烷基,如果n=2,R可以是不同基团,和b)含铜杀真菌活性化合物(Ⅱ)。
Description
本发明涉及一种杀真菌混合物，其包括协同增效量的a.1)式I.a的氨基甲酸酯，
其中X是CH或N，n是0、1或2以及R是卤素、C1-C4-烷基或C1-C4-卤代烷基，如果n＝2，R可以是不同基团，和
b)含铜杀真菌活性化合物(II)。
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用于制备这种类型混合物的用途。
式I的化合物、其制备和抗有害真菌活性已公开于文献(WO-A96/01，256；WO-A 96/01，258)中。
含铜化合物用于控制有害真菌的用途类似地也已公开。
本发明的目的是提供具有提高的抗有害真菌活性并同时减少活性化合物使用总量的混合物(增效混合物)，以便减少施用量和扩大已知化合物I和II的杀菌活性谱。
已发现前面描述的混合物达到了本发明目的。而且，发现同时施用化合物I和II，例如一起或分开施用，或依次施用化合物I和II，与使用单一化合物相比可以更好地控制有害真菌。
式I.a代表，特别是，对应于下表中所列取代基的氨基甲酸酯：
| No. | 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 |
| I.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 |
| 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 |
特别优选化合物I.12、I.23、I.32和I.38。
由于其中所含氮原子的碱性，化合物I可以与无机或有机酸或金属离子形成盐或加合物。
无机酸例如是氢卤酸如氢氟酸、盐酸、氢溴酸和氢碘酸、硫酸、磷酸和硝酸。
适合的有机酸例如是甲酸，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1-20个碳原子的直链或支链烷基磺酸)、芳基磺酸或芳基二磺酸(芳基，如苯基和萘基，带有1或2个磺酸基)、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(芳基，如苯基和萘基，带有1或2个磷酸基)，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(subgroup)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，第三和第四主族元素，特别是铝、锡和铅。如适合，这些金属可以各种合适的价态存在。
适合的含铜杀真菌活性化合物(II)通常是已知的市场上可购得的杀菌剂。其中特别适合的含铜杀真菌剂选自氢氧化铜、氧化铜、磺王铜、硫酸铜、喹啉酮、双(3-苯基水杨酸)铜(水杨铜)、灭菌铜(copperdihydrazinium disulfate)、dicopper chloride trihydroxide和tricopper dichloride dimethydithiocarbamate。
制备这些混合物时，优选使用纯的活性化合物I和II，并且还可以混合其它抗有害真菌或害虫如昆虫、蜘蛛纲(arachnids)或线虫的活性化合物，或除草剂或植物生长调节活性化合物或肥料。
化合物I和II的混合物及化合物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。在一些情况下，它们是系统作用，因此也可作为叶面和土壤使用的杀菌剂。
它们对于控制各种农作物上的大量真菌是非常重要的，这些农作物例如是棉花、各种蔬菜(如黄瓜、菜豆、番茄、马铃薯和葫芦)、大麦、禾草、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、甘蔗以及各种种子。
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)、葫芦科植物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，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(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(Pseudocercosporella herpotrichoides)、稻梨孢菌、致病疫霉引起的马铃薯和番茄晚疫病、葡萄的葡生单轴霉(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)，例如抗拟青霉。
化合物I和II可以同时施用，确切地说一起或分开施用，或依次施用，分开使用时的顺序对防治效果通常没有影响。
一般化合物I和II使用重量比为1∶1-1∶1000，优选1∶1-1∶100，特别是1∶3-1∶10。
依据所需作用方式，本发明混剂的施用量，特别是在农作物栽培领域，为0.01-5kg/ha，优选0.05-3.5kg/ha，特别是0.1-2.0kg/ha。
就化合物I来说，施用量为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，施用量为0.1-10kg/ha，优选0.5-5kg/ha，特别是0.5-2.0kg/ha。
用于种子处理时，一般混剂的使用量为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，将化合物I和II或化合物I和II的混剂分别或结合施用，用以喷雾或喷粉种子、播前或播后、或苗前或苗后的植物或土壤。
本发明新的杀真菌的协同增效混合物或化合物I和II，可以制成例如直接可喷雾的溶液，粉剂和悬浮剂形式或高渡度的水剂、油剂或其它悬浮剂、分散剂、乳剂、油分散剂、糊剂、粉剂、撒施剂或颗粒剂，并可通过喷雾、弥雾、喷粉、撒施或随水浇施的方法施用。依据所需用途使用不同的剂型；在任何情况下，都应该尽可能地使本发明混合物分散精细和均匀。
例如可通过加入溶剂和/或载体，以已知方式制备制剂。通常在制剂中加入惰性添加剂，如乳化剂或分散剂。
适合的表面活性剂是芳基磺酸的碱金属盐、碱土金属盐和铵盐，例如木素-、苯酚-、萘-和二丁基萘磺酸的上述盐，和脂肪酸的上述盐，烷基-和烷芳基磺酸盐、烷基、十二烷基醚和脂肪族醇硫酸盐以及六-、七-和十八醇硫酸盐或脂肪族醇乙二醇醚、磺化的萘和它的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物、聚氧乙烯辛基苯基醚、乙氧基化的异辛基-、辛基-或壬基苯酚、烷基苯基或三丁基苯基聚乙二醇醚、烷芳基聚醚醇、异十三烷基醇、脂肪族醇-环氧乙烷缩合物、乙氧基化的蓖麻油、聚氧乙烯或聚氧丙烯烷基醚，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。
通过将化合物I或II或化合物I和II的混合物与固体载体混合或联合研磨可制备粉剂、撒施剂和粉剂。
通过将一种活性化合物或多种活性化合物粘附到固体载体上通常可制备颗粒剂(例如包衣、浸渍或均一颗粒剂)。
使用的填料或固体载体例如是矿物土，如硅胶、硅酸、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、硫酸钙和硫酸镁、氧化镁、磨碎的合成材料和肥料，如硫酸铵、磷酸铵、硝酸铵、尿素和植物性来源产品，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的混合物。在此情况下，采用的活性化合物纯度为90％-100％，优选95％-100％(根据核磁共振光谱或高压液相色谱确定)。
施用化合物I或II、其混合物或相应制剂，以杀真菌有效量的所述混合物或在分开使用情况下杀菌有效量的化合物I和II来处理有害真菌、它们的栖生场所或植物、种子、土壤、区域、材料或空间使之免受这些真菌的侵害。
可在有害真菌侵染前或侵染后进行施用。
应用实施例
以下试验可显示本发明混合物的增效作用：
以分别或结合方式将活性化合物制成于63％重量环己酮和27％重量乳化剂中的10％浓度乳油的形式，并用水稀释至所需浓度。
对致病疫霉(番茄晚疫病(tomato blight))的活性
使用由含有10％活性化合物、63％环己酮和27％乳化剂的储备溶液制成的水悬浮剂喷施品种为“Groβe Fleischtomate”的盆栽植物叶片至滴湿。第二天，用致病疫霉的游动孢子水悬液侵染叶片。然后将植物放在水蒸汽饱和的16-18℃的培养室中。6天后，未处理的侵染对照植物上的番茄晚疫病发展的严重程度足以用肉眼观察确定，以％表示。
评估是以侵染叶片面积百分比为标准。将这些百分比数值转换成杀菌效果。根据下面的Abbot公式计算杀菌效果(W)：
W＝(1－α/β)·100
α对应于经处理的植物的真菌侵染程度％和
β对应于未处理(对照)植物的真菌侵染程度％
如果杀菌效果为0，则表示处理的植物受真菌侵染的情况相当于未处理对照植物的侵染水平；如果杀菌效果为100。则表示处理的植物未波侵染。
根据Colby公式[R.S.Colby，《杂草》Weeds15，20-22(1967)]计算活性化合物的混合物的预期杀菌效果，并与观察到的杀菌效果相比较。
Colby公式：E＝X＋Y－X·Y/100
E当使用浓度分别为a和b的活性化合物A和B的混合物时的预期杀菌效果，以未处理对照％表示
X当使用浓度为a的活性化合物A时的杀菌效果，以未处理对照％表示
Y当使用浓度为b的活性化合物B时的杀菌效果，以未处理对照％表示
试验结果列于表2和3中。
表2
| 实施例 | 活性化合物 | 喷雾液中活性化合物浓度ppm | 相对于未处理对照的杀菌效果％ |
| 1V | 对照(未处理) | (100％侵染) | 0 |
| 2V | 化合物I.32 | 210.50.25 | 8030300 |
| 3V | II.1＝Cuproxate三碱硫酸铜(tribasiccoppersulfate) | 100502512.5 | 10000 |
表3
| 实施例 | 本发明混合物 | 观察到的杀菌效果 | 计算的杀菌效果*) |
| 4 | 1ppm I.32＋100ppm II.1(混合物1∶100) | 95 | 37 |
| 5 | 0.5ppm I.32＋50ppm II.1(混合物1∶100) | 80 | 30 |
| 6 | 0.25ppm I.32＋25ppm II.1(混合物1∶100) | 50 | 0 |
| 7 | 2ppm I.32＋100ppm II.1(混合物1∶50) | 97 | 82 |
| 8 | 1ppm I.32＋50ppm II.1(混合物1∶50) | 95 | 30 |
| 9 | 0.5ppm I.32＋25ppm II.1(混合物1∶50) | 93 | 30 |
| 10 | 2ppm I.32＋50ppm II.1(混合物1∶25) | 100 | 80 |
| 11 | 1ppm I.32＋25ppm II.1(混合物1∶25) | 97 | 30 |
| 12 | 0.5ppm I.32＋12.5ppm II.1(混合物1∶25) | 97 | 30 |
*)根据Colby公式计算
试验结果显示在所有混合比例中观察到的杀菌效果都高于根据Colby公式计算的预期杀菌效果。
W＝(1－α/β)·100
应用实施例2--对番茄上的致病疫霉(phytophthora infestans)的活性
将由10％活性化合物、63％环己酮和27％乳化剂的储备溶液制成的水悬浮剂喷施品种为“Groβe Fleischtomate St.Pierre”的盆栽植物叶片至滴湿。第二天，用冷却的浓度为0.25×106孢子/ml的致病疫霉游动孢子水悬液侵染叶片。然后将植物放在水蒸汽饱和的18-20℃的培养室中。6天后，未处理的侵染对照植物上的番茄晚疫病发展的严重程度足以用肉眼观察确定，以％表示。
将受侵染叶片面积百分比的肉眼观测值以相对未处理对照的形式转换成杀菌效果％。杀菌效果0表示与未处理对照植物的侵染程度相同；杀菌效果100表示0％被侵染。根据Colby公式计算活性化合物的混合物的预期杀菌效果(Colby，S.R.除草组合物的增效和拮抗作用的计算”，《杂草》(Weeds)15，第20-22页，1967)，并与观察到的杀菌效果相比较。
对于组分II，使用三碱硫酸铜3Cu(OH)2×CuSO4(商品名为三碱硫酸铜(Cuproxat))。
试验结果列于表4和5中。
表4
| 实施例 | 活性化合物 | 浓度ppm | 相对于未处理对照的杀菌效果％ |
| 13V | 未处理 | (87％侵染) | 0 |
| 14V | 化合物I.23 | 210.50.250.125 | 80080 |
| 15V | 化合物I.38 | 210.5 | 008 |
| 16V | 化合物II | 200100502512.5 | 88880 |
表5
| 实施例 | 本发明混合物(浓度ppm) | 观察到的杀菌效果 | 计算的杀菌效果* |
| 17 | 2ppm I.23＋200ppm II | 54 | 15 |
| 18 | 1ppm I.23＋100ppm II | 42 | 8 |
| 19 | 0.125ppm I.23＋12.5ppm II | 31 | 0 |
| 20 | 2ppm I.23＋100ppm II | 31 | 15 |
| 21 | 2ppm I.38＋200ppm II | 77 | 8 |
| 22 | 1ppm I.38＋100ppm II | 42 | 8 |
| 23 | 2ppm I.38＋100ppm II | 77 | 8 |
| 24 | 1ppm I.38＋50ppm II | 31 | 8 |
| 25 | 2ppm I.38＋50ppm II | 65 | 8 |
| 26 | 1ppm I.38＋25ppm II | 54 | 8 |
| 27 | 0.5ppm I.38＋12.5ppm II | 29 | 8 |
*)根据Colby公式计算
试验结果显示在所有混合比例中观察到的杀菌效果都高于使用Colby公式计算的预期杀菌效果。
Claims (10)
1.一种杀真菌混合物，包括协同增效量的a.1)式I.a的氨基甲酸酯，
其中X是CH或N，n是0、1或2以及R是卤素、C1-C4-烷基或C1-C4-卤代烷基，如果n＝2，R可以是不同基团，和
b)含铜杀真菌活性化合物(II)。
2.根据权利要求1的杀真菌混合物，其中含有式I.a的氨基甲酸酯。
3.根据权利要求1的杀真菌混合物，其中化合物I、其盐或加合物与化合物II的重量比是1∶1-1∶1000。
4.一种防治有害真菌的方法，包括用权利要求1中所述的式I化合物、其盐或加合物和权利要求1中所述的式II化合物处理有害真菌、它们的栖生场所或植物、种子、土壤、区域、材料或空间使之免受这些真菌的侵害。
5.根据权利要求3的方法，其中权利要求1中所述的化合物I、其盐或加合物与权利要求1中所述的化合物II同时施用，确切地说是结合起或分开施用，或依次施用。
6.根据权利要求3或4的方法，其中权利要求1中所述的化合物I、其盐或加合物的施用量为0.01-2.5kg/ha。
7.根据权利要求3-5任一项的方法，其中权利要求1中所述的化合物II的施用量为0.1-10kg/ha。
8.权利要求1中所述的化合物I、其盐或加合物在制备权利要求1的杀真菌协同增效混合物上的用途。
9.权利要求1中所述的化合物II在制备权利要求1的杀真菌协同增效混剂上的用途。
10.权利要求1的组合物，其包装成两部分，一部分包含于固体或液体载体中的权利要求1中所述的式I化合物，另一部分包含于固体或液体载体中的权利要求1中所述的式II化合物。
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| TW200524530A (en) * | 2003-10-17 | 2005-08-01 | Basf Ag | Use of basic amino acids in copper-containing fungicidal formulations |
| KR101163242B1 (ko) * | 2003-10-31 | 2012-07-05 | 이시하라 산교 가부시끼가이샤 | 살균제 조성물 및 식물 병해의 방제 방법 |
| US20050112393A1 (en) * | 2003-11-20 | 2005-05-26 | Fliermans Carl B. | Antifungal preservative composition for an environmentally friendly process |
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