CN1281132C - 基于二噻农的杀真菌混合物 - Google Patents
基于二噻农的杀真菌混合物 Download PDFInfo
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- CN1281132C CN1281132C CNB038160501A CN03816050A CN1281132C CN 1281132 C CN1281132 C CN 1281132C CN B038160501 A CNB038160501 A CN B038160501A CN 03816050 A CN03816050 A CN 03816050A CN 1281132 C CN1281132 C CN 1281132C
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
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- 150000002790 naphthalenes Chemical class 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
Abstract
本发明涉及包含协同有效量的A)式(I)化合物和B)式(II)联苯基酰胺的杀真菌混合物,其中Z代表吡啶基环或5元杂芳基环,所述杂芳基环除了碳原子外还含有1或2个氮原子或1个氮原子和1个氧或硫原子,其中Z带有1-3个相同或不同的取代基,所述取代基选自卤素、甲基和三氟甲基,且X代表卤素。本发明还涉及一种使用化合物(I)和(II)的混合物防治寄生真菌的方法以及化合物(I)和(II)在制备这类混合物中的用途。
Description
本发明涉及杀真菌混合物,包含协同有效量的如下化合物:
A)式I化合物:
和
B)式II的联苯基酰胺:
其中Z为吡啶基环或5元杂芳基环,所述杂芳基环除了碳原子外还含有1或2个氮原子或1个氮原子和1个氧或硫原子,
其中Z带有1-3个相同或不同的取代基,所述取代基选自卤素、甲基和三氟甲基,且X为卤素。
此外,本发明还涉及使用化合物I和II的混合物防治有害真菌的方法,以及化合物I和II在制备该类混合物中的用途。
本发明的目的是提供对有害真菌具有改进的活性且活性化合物的总施用量降低的混合物(协同增效混合物),以降低施用率并拓宽已知化合物的活性谱。
我们发现该目的由开头所定义的混合物实现。此外,我们发现与仅使用单独的化合物可能获得的防治相比,同时,即一起或单独施用化合物I和II,或依次施用化合物I和II对有害真菌提供了更好的防治。
通常使用化合物I与一种联苯基酰胺II的混合物。然而,在某些情况下,化合物I与两种或更多种联苯基酰胺II的混合物可能是有利的。
式I化合物(通用名:二噻农)及其制备方法描述于DE-AS 1 060 655和GB-A 857 383中。
式II的联苯基酰胺、其制备及其对有害真菌的作用同样由文献已知[参见EP-A 545 099]。
在式II所给的定义中,卤素代表氟、氯、溴和碘,尤其是氟和氯。
在本发明混合物的优选实施方案中,式II尤其涉及如下化合物,其中Z为取代的3-吡啶基环,尤其是在2位被取代的3-吡啶基环。这些化合物对应于其中X为卤素且Y为三氟甲基或卤素的式IIA化合物:
优选其中X和Y相同或不同且为卤素,尤其是氟或氯的式IIA化合物。
适于本发明混合物的尤其是下列式IIA化合物:
化合物号 | Y | X |
II-1 | Cl | Cl |
II-2 | Cl | F |
II-3 | F | Cl |
II-4 | F | F |
II-5 | CF3 | Cl |
II-6 | CF3 | F |
特别优选二噻农I与化合物II-1(建议通用名:啶酰菌胺(boscalid))的混合物。
在本发明混合物的另一实施方案中,式II表示其中Z为5元杂芳基环的联苯基酰胺,该杂芳基除了碳原子外还含有1或2个氮原子或1个氮原子和1个氧或硫原子且带有1、2或3个选自卤素、甲基和三氟甲基的取代基。这些化合物对应于其中各变量如下所定义的式IIB:
D为碳或硫;
E为碳或氮;
G为氧、碳或氮;条件是变量D、E和G中至少一个不为碳;
R为卤素、甲基和卤代甲基,尤其是三氟甲基;
n为1、2或3,其中若n大于1,则基团R可以不同。
式IIB化合物、其制备及其杀真菌活性由文献已知(参见:WO-A 01/42223;DE-A 198 40 322;JP-A 07/145 156;JP-A 2001/302 605)。
优选如下式IIB化合物,其中基团
表示如下两个基团A和B之一:
其中#表示与羰基相连的键,
其中R1和R2如下所定义:
R1为氢、甲基或三氟甲基;和
R2为氢、甲基或卤素。
除了式IIA化合物外,下列化合物II尤其适于本发明的混合物:
化合物号 | Z | R1 | R2 | X |
II-7 | A | CF3 | H | Cl |
II-8 | A | CF3 | H | F |
II-9 | A | CH3 | F | Cl |
II-10 | A | CH3 | F | F |
II-11 | B | CF3 | H | Cl |
II-12 | B | CF3 | H | F |
II-13 | B | CF3 | CH3 | Cl |
II-14 | B | CF3 | CH3 | F |
由于其碱性特征,化合物II能够与无机或有机酸或金属离子形成盐或加合物。
无机酸的实例是氢卤酸如氢氟酸、盐酸、氢溴酸以及氢碘酸,此外还有硫酸、磷酸、碳酸和硝酸。
合适的有机酸例如是甲酸和链烷酸,如乙酸、三氟乙酸、三氯乙酸和丙酸,以及羟基乙酸、硫氰酸、乳酸、琥珀酸、柠檬酸、苯甲酸、肉桂酸、草酸、烷基磺酸(具有带有1-20个碳原子的直链或支化烷基的磺酸)、芳基磺酸或芳基二磺酸(芳族基团如苯基和萘基,其带有一个或两个磺基)、烷基膦酸(具有带有1-20个碳原子的直链或支化烷基的膦酸)、芳基膦酸或芳基二膦酸(芳族基团如苯基和萘基,其带有一个或两个膦酸基团),其中烷基或芳基可以带有其它取代基,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。
合适的金属离子尤其是第二主族元素的离子,尤其是钙和镁离子,第三和第四主族元素的离子,尤其是铝、锡和铅的离子,以及第一至第八过渡族元素的离子,尤其是铬、锰、铁、钴、镍、铜和锌的离子,以及其他。特别优选第四过渡族元素的金属离子。金属可以它们可能呈现的各种化合价存在。
在制备混合物时,优选使用纯的活性化合物I和II,根据需要,可以向其中混入其它对抗有害真菌或其它害虫如昆虫、蜘蛛或线虫的活性化合物,或具有除草作用或生长调节作用的活性化合物或肥料。
化合物I和II的混合物或同时联合或单独施用的化合物I和II对宽范围的植物病原性真菌具有显著的活性,所述真菌尤其选自子囊菌纲(Ascomycetes)、半知菌纲(Deuteromycetes)、卵菌纲(Oomycetes)和担子菌纲(Basidiomycetes)真菌。它们中的一些起内吸作用并因此也适于用作叶面和土壤作用杀真菌剂。
它们对在各种作物如棉花、蔬菜品种(例如黄瓜、豆类和葫芦科植物)、大麦、禾草、燕麦、咖啡、玉米、水果品种、稻、黑麦、大豆、葡萄藤、小麦、观赏植物、甘蔗以及各种种子中防治大量真菌尤其重要。
它们特别适于防治下列植物病原性真菌:葫芦科植物中的二孢白粉菌(Erysiphe cichoracearum)和单丝壳(Sphaerotheca fuliginea),苹果中的苹果白粉病菌(Podosphaera leucotricha),葡萄藤中的葡萄钩丝壳(Uncinulanecator),禾谷类中的柄锈菌(Puccinia)属,棉花、稻和草坪中的丝核菌(Rhizoctonia)属,禾谷类和甘蔗中的黑粉菌(Ustilago)属,苹果中的苹果黑星菌(Venturia inaequalis)(黑星病),禾谷类中的长蠕孢(Helminthosporium)属,小麦中的小麦颖枯病菌(Septoria nodorum),草莓、蔬菜、观赏植物和葡萄藤中的灰葡萄孢(Botrytis cinerea)(灰霉病),花生中的落花生尾孢(Cercospora arachidicola),小麦和大麦中的眼斑病菌(Pseudocercosporellaherpotrichoides),稻中的稻瘟病菌(Pyricularia oryzae),土豆和西红柿中的致病疫霉(Phytophthora infestans),葫芦科植物和啤酒花中的假霜霉(Pseudoperonospora)属,葡萄藤中的葡萄生单轴霉(Plasmopara viticola),蔬菜和水果中的链格孢(Alternaria)属以及镰孢霉(Fusarium)和轮枝孢(Verticillium)属。
此外,它们可以用于保护材料(如保护木材)例如以免遭拟青霉(Paecilomyces variotii)的损害。
化合物I和II可以同时,即一起或者单独施用或依次施用,在单独施用下的顺序通常对防治结果没有任何影响。
化合物I和II通常以100∶1-1∶50,优选50∶1-1∶50,尤其是10∶1-1∶10的重量比施用。
相应地,化合物I的施用率通常为5-2000g/ha,优选10-1000g/ha,尤其是50-750g/ha。
取决于所需的效果,本发明混合物的施用率对化合物II而言为5-500g/ha,优选50-500g/ha,尤其是50-200g/ha。
对于种子处理,该混合物的施用率通常为0.001-1g/kg种子,优选0.01-0.5g/kg,尤其是0.01-0.1g/kg。
若要防治植物病原性有害真菌,则化合物I和II的单独或联合施用或化合物I和II的混合物的施用通过在植物播种之前或之后或在植物出苗之前或之后对种子、植物或土壤喷雾或撒粉而进行。
本发明的杀真菌协同增效混合物或化合物I和II例如可以配制成即喷溶液、散剂和悬浮乳剂形式或高度浓缩的水性、油性或其它悬浮乳剂,分散体,乳剂,油分散体,糊,粉剂,撒播用材料或粒剂的形式,且可以通过喷雾、雾化、撒粉、撒播或浇灌而施用。使用形式取决于意欲的目的;在各种情况下都应确保本发明混合物尽可能精细和均匀地分布。
配制剂通过本身已知的方式制备,例如通过加入溶剂和/或载体制备。通常将惰性添加剂如乳化剂或分散剂与配制剂混合。
合适的表面活性剂为芳族磺酸如木素-、苯酚-、萘-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-和烷基芳基磺酸盐,烷基、月桂基醚和脂肪醇硫酸盐以及硫酸化十六-、十七-和十八烷醇或脂肪醇乙二醇醚的盐,磺化萘及其衍生物与甲醛的缩合物,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基苯基醚,乙氧基化异辛基-、辛基-或壬基酚,烷基苯基聚乙二醇醚,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,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。
散剂、撒播用材料和粉剂可以通过将化合物I和II或化合物I和II的混合物与固体载体混合或一起研磨而制备。
粒剂(例如涂层粒剂、浸渍粒剂或均相粒剂)通常通过将活性化合物与固体载体粘附而制备。
填料或固体载体例如为矿土如硅胶、硅酸、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁;磨碎的合成材料;肥料如硫酸铵、磷酸铵、硝酸铵、尿素;植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉;纤维素粉或其它固体载体。
配制剂通常包含0.1-95重量%,优选0.5-90重量%的化合物I和II之一,或化合物I和II的混合物。活性化合物以90-100%,优选95-100%的纯度(根据NMR光谱或HPLC)使用。
化合物I和II,混合物或对应的配制剂通过用杀真菌有效量的混合物或在单独施用的情况下用化合物I和II处理有害真菌或想要防治有害真菌的植物、种子、土壤、区域、材料或空间而施用。施用可以在有害真菌侵染之前或之后进行。
包含活性化合物的该类制剂的实例如下:
I.90重量份活性化合物与10重量份N-甲基吡咯烷酮的溶液;该溶液适于以微滴形式使用;
II.20重量份活性化合物、80重量份二甲苯、10重量份的8-10mol氧化乙烯与1mol油酸N-单乙醇酰胺的加合物、5重量份十二烷基苯磺酸钙、5重量份的40mol氧化乙烯与1mol蓖麻油的加合物的混合物;通过将该溶液精细分布于水中得到分散体;
III.20重量份活性组分、40重量份环己酮、30重量份异丁醇、20重量份的40mol氧化乙烯与1mol蓖麻油的加合物的水分散体;
IV.20重量份活性组分、25重量份环己醇、65重量份沸点为210-280℃的矿物油馏分和10重量份的40mol氧化乙烯与1mol蓖麻油的加合物的水分散体;
V.80重量份活性化合物、3重量份二异丁基萘-1-磺酸钠、10重量份来自亚硫酸盐废液的木素磺酸钠和7重量份粉状硅胶在锤磨机中研磨的混合物;通过将该混合物精细分布于水中得到喷雾混合物;
VI.3重量份活性组分和97重量份细碎高岭土的均匀混合物;该粉剂包含3重量%活性化合物;
VII.30重量份活性组分、92重量份粉状硅胶和8重量份喷雾于该硅胶表面上的石蜡油的均匀混合物;该配制剂赋予活性化合物以良好的粘附性能;
VIII.40重量份活性化合物、10重量份苯酚磺酸/脲/甲醛缩合物的钠盐、2重量份硅胶和48重量份水的稳定水分散体,该分散体可以进一步稀释;
IX.20重量份活性化合物、2重量份十二烷基苯磺酸钙、8重量份脂肪醇聚乙二醇醚、20重量份苯酚磺酸/脲/甲醛缩合物的钠盐和88重量份链烷烃矿物油的稳定油分散体。
化合物和混合物的杀真菌活性可以由下列试验证实:
将活性化合物单独制成在丙酮或DMSO中包含0.25重量%活性化合物的储备溶液。将1重量%的乳化剂UniperolEL(基于乙氧基化烷基酚的润湿剂,具有乳化和分散作用)加入该溶液中,并用水稀释该混合物至所需浓度。
应用实施例:对由早疫病菌(Alternaria solani)引起的番茄早疫病的活性
将栽培品种为“Groβe Fleischtomate St.Pierre”的盆载植物的叶子用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。第二天将叶子用早疫病菌(Alternaria solani)在2%生物麦芽溶液中的含水游动孢子悬浮液(密度为0.17×106个孢子/ml)侵染。然后在20-22℃的温度下将植物置于水蒸气饱和的室中。5天后未处理但侵染的对照植物叶子上的侵染发展到可以以%肉眼测定侵染的程度。
通过以%测定侵染叶面积而进行评价。将这些百分数转化成效力。
使用Abbot公式按如下计算效力(E):
E=(1-α/β)·100
α对应于处理植物的真菌侵染百分数,和
β对应于未处理(对照)植物的真菌侵染百分数。
效力为0表示处理植物的侵染水平对应于未处理对照植物的侵染水平;效力为100表示处理植物未受侵染。
活性化合物混合物的预期效力使用Colby公式[S.R.Colby,Weeds(杂草)15,20-22(1967)]确定并与观测到的效力比较。
Colby公式:E=x+y-x·y/100
E为使用浓度为a和b的活性化合物A和B的混合物时的预期效力,以未处理对照的%表示,
x为活性化合物A以浓度a使用时的效力,以未处理对照的%表示,
y为活性化合物B以浓度b使用时的效力,以未处理对照的%表示。
表A-单独的活性化合物
实施例 | 活性化合物 | 活性化合物在喷雾液中的浓度[ppm] | 效力,未处理对照的% |
1 | 对照(未处理) | (82%侵染) | 0 |
2 | I(二噻农) | 6331168 | 632700 |
3 | II-1(啶酰菌胺) | 6331168 | 88827663 |
4 | II-2 | 63 | 88 |
31168 | 273927 |
表B-本发明的组合
实施例 | 活性化合物混合物/浓度/混合比 | 观察到的效力 | 计算的效力*) |
5 | I+II-1/63+8ppm/8∶1 | 100 | 87 |
6 | I+II-1/31+31ppm/1∶1 | 100 | 87 |
7 | I+II-1/16+16ppm/1∶1 | 100 | 76 |
8 | I+II-1/8+8ppm/1∶1 | 100 | 63 |
9 | I+II-1/8+63ppm/1∶8 | 99 | 88 |
10 | I+II-2/63+8ppm/8∶1 | 100 | 73 |
11 | I+II-2/31+31ppm/1∶1 | 99 | 46 |
12 | I+II-2/16+16ppm/1∶1 | 99 | 39 |
13 | I+II-2/8+8ppm/1∶1 | 100 | 27 |
14 | I+II-2/8+63ppm/1∶8 | 100 | 88 |
*)使用Colby公式计算的效力
试验结果表明对于所有混合比,观察到的效力高于使用Colby公式预期的效力。
Claims (7)
3.一种杀真菌组合物,包含固体或液体载体和如权利要求1或2所要求的混合物。
4.一种防治有害真菌的方法,包括用如权利要求1所述的式I化合物和式IIA化合物处理有害真菌、其栖息地或需要防治它们的植物、种子、土壤、区域、材料或空间,其中化合物I与化合物IIA的重量比为100∶1-1∶10。
5.如权利要求4所要求的方法,包括用5-2000g/ha的如权利要求1所述的化合物I处理有害真菌、其栖息地或需要防治它们的植物、种子、土壤、区域、材料或空间。
6.如权利要求4所要求的方法,包括用5-500g/ha的至少一种如权利要求1所述的化合物IIA处理有害真菌、其栖息地或需要防治它们的植物、种子、土壤、区域、材料或空间。
7.如权利要求1所述的式I和IIA化合物在制备如权利要求1所要求的混合物中的用途。
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