CN1257407A - 杀真菌混合物 - Google Patents
杀真菌混合物 Download PDFInfo
- Publication number
- CN1257407A CN1257407A CN98805324A CN98805324A CN1257407A CN 1257407 A CN1257407 A CN 1257407A CN 98805324 A CN98805324 A CN 98805324A CN 98805324 A CN98805324 A CN 98805324A CN 1257407 A CN1257407 A CN 1257407A
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- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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)
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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:a1)式(Ⅰa)、(Ⅰb)或(Ⅰc)的苯基苄基醚衍生物,和/或a2)式(Ⅰd)的氨基甲酸酯或其盐或其加合物,其中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(Ⅱa)或(Ⅱb)的二硝基苯酚衍生物,其中n是0、1或2。
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:
和/或
a2)式Id的氨基甲酸酯或其盐或其加合物
其中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
其中n是0、1或2。
此外,本发明还涉及用式I(I.a、I.b或I.c)与II(II.a或II.b)化合物的混合物防治有害真菌的方法,以及化合物I与化合物II在制备这种混合物方面的应用。
式Ia-c的化合物、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、其制备以及它们的活性已由文献公开(WO-A93/15046,WO-A 96/01256和WO-A 96/01258)。
同样已知化合物II(II.a和II.b)的混合物(俗名:Dinocap)、其制备和它们抗有害真菌和蛛形纲动物的活性(US-A2,526,660;US-A2,810,767)。
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 |
I.16 | N | 2-CH(CH3)2 |
Nr. | X | Rn |
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 |
其中特别优选化合物I.12,I.23,I.32和I.38。
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。这些化合物中某些内吸地起作用,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、蕃茄、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(Septorianodorum)、草莓、蔬菜、观赏植物和葡萄上的灰霉菌(Botrytiscinera)、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(Phytophthora infestans)、葡萄上的葡萄生单轴霉(Plasmoparaviticola)、啤酒花和黄瓜上的Pseudocercosporella、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,撒播材料或颗粒剂的形式,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。通常将这种加工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。
应用实施例
本发明混合物的增效作用可以通过下面的试验来证明:
将活性成分分别或一起在包含70重量%环己酮,20重量%NekanilLN(LutensolAP6,基于乙氧基化烷基酚的湿润剂(具有乳化和分散作用))和10重量%EmulphorEL(EmulanEL,基于乙氧基化脂肪醇的乳化剂)的混合物中配制成10%浓度乳剂,加水稀释到所需浓度。
实施例1
对禾白粉菌(Weizenmehltau)的作用
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制剂喷雾盆栽小麦秧苗(品种:Fruehgold)的叶片至滴流点,并且在喷雾液层干燥后24小时,再用禾白粉菌(Erysiphe graminis formaspecialis tritici)的孢子喷粉。然后将试验植株置于温度为20-24℃和相对大气湿度为70至90%的的温室内。7天后,目测白粉病发展的程度,以总叶面面积的感染百分比计。
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。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情况下的作用效力,以未处理对照组的%表示。
抗禾白粉菌作用的结果列于下表中。
实施例 | 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 |
1V | 对照组(未处理) | (100%感染) | 0 |
2V | Ia | 0,60,3 | 00 |
3V | Ib | 0,60,3 | 1515 |
4V | 化合物I.32(Id) | 0,630,31 | 7540 |
5V | IIa | 12,56,33,1 | 1000 |
表3
*)采用Colby公式计算的
实施例 | 本发明的混合物 | 观察到的作用效力 | 预期作用效力 |
6 | 0,6ppm Ia+12,5ppm IIa | 40 | 10 |
7 | 0,3ppm Ia+12,5ppm IIa | 40 | 10 |
8 | 0,6ppm Ib+12,5ppm IIa | 85 | 23,5 |
9 | 0,3ppm Ib+12,5ppm IIa | 80 | 23,5 |
10 | 0,63ppm Id+6,3ppm IIa | 95 | 75 |
11 | 0,31ppm Id+3,1ppm IIa | 80 | 40 |
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 (9)
2.权利要求1所述的杀真菌混合物,其中化合物I与化合物II的重量比为10∶1-0.01∶1。
3.一种防治有害真菌的方法,该方法包括用权利要求1中所述的化合物I和权利要求1中所述的化合物II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。
4.权利要求3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通过同时,即一起或分别方式,或者先后方式施用。
5.权利要求3或4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。
6.权利要求3-5中任一项的方法,其中权利要求1所述的化合物II的施用量为0.01-10kg/ha。
7.权利要求1的化合物I在制备权利要求1中所述的杀真菌活性增效混合物中的应用。
8.权利要求1的化合物II在制备权利要求1中所述的杀真菌活性增效混合物中的应用。
9.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。
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CN104054714A (zh) * | 2014-05-31 | 2014-09-24 | 海利尔药业集团股份有限公司 | 一种含有硝苯菌酯与粉唑醇的杀菌组合物 |
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US20050106192A1 (en) * | 2003-11-13 | 2005-05-19 | Parekh Prabodh P. | Synergistically-effective composition of zinc ricinoleate and one or more substituted monocyclic organic compounds and use thereof for preventing and/or suppressing malodors |
US7390925B2 (en) * | 2006-04-03 | 2008-06-24 | Bristol-Myers Squibb Company | Oxime-containing acyl guanidines as beta-secretase inhibitors |
US8012554B2 (en) | 2007-09-12 | 2011-09-06 | Pactiv Corporation | Bags having odor management capabilities |
JP5793883B2 (ja) * | 2010-03-03 | 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 |
KR102313759B1 (ko) | 2020-03-06 | 2021-10-18 | 키오스크코리아(주) | 공간 인식을 이용한 입체영상 제어 방법 및 이를 이용한 상품광고용 입체영상 디스플레이 장치 |
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US2526660A (en) * | 1946-07-06 | 1950-10-24 | Rohm & Haas | Capryldintrophenyl crotonate |
DE3623921A1 (de) * | 1986-07-16 | 1988-01-21 | Basf Ag | Oximether und diese enthaltende fungizide |
GB8617648D0 (en) | 1986-07-18 | 1986-08-28 | Ici Plc | Fungicides |
DE69029334T2 (de) * | 1989-05-17 | 1997-04-30 | Shionogi Seiyaku Kk | Verfahren zur Herstellung von Alkoxyiminoacetamid-Derivaten und ein Zwischenproduckt dafür |
NZ246603A (en) * | 1992-01-29 | 1996-10-28 | Basf Ag | Carbamate derivatives and fungicidal compositions thereof |
DE4423612A1 (de) * | 1994-07-06 | 1996-01-11 | Basf Ag | 2-[(Dihydro)pyrazolyl-3'-oxymethylen]-anilide, Verfahren zu ihrer Herstelung und ihre Verwendung |
DE4423613A1 (de) * | 1994-07-06 | 1996-01-11 | Basf Ag | 2-[1',2',4'-Triazol-3'yloxymethylen]-anilide, Verfahren zu ihrer Herstellung und ihre Verwendung |
NZ332076A (en) * | 1996-04-26 | 2000-02-28 | Basf Ag | Fungicide mixture containing a carbamate derivative and an oxime ether derivative or triazole derivative |
CZ294297B6 (cs) * | 1996-07-10 | 2004-11-10 | Basf Aktiengesellschaft | Fungicidní prostředek, způsob potírání škodlivých hub a použití účinných látek |
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Cited By (10)
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CN103931640A (zh) * | 2014-04-30 | 2014-07-23 | 海利尔药业集团股份有限公司 | 一种含有硝苯菌酯与吡唑醚菌酯的杀菌组合物 |
CN103947651A (zh) * | 2014-04-30 | 2014-07-30 | 海利尔药业集团股份有限公司 | 一种含有硝苯菌酯与苯醚甲环唑的杀菌组合物 |
CN104054709A (zh) * | 2014-05-31 | 2014-09-24 | 海利尔药业集团股份有限公司 | 一种含有硝苯菌酯与氟啶胺的杀菌组合物 |
CN104054713A (zh) * | 2014-05-31 | 2014-09-24 | 海利尔药业集团股份有限公司 | 一种含有硝苯菌酯与戊唑醇的杀菌组合物 |
CN104054728A (zh) * | 2014-05-31 | 2014-09-24 | 海利尔药业集团股份有限公司 | 一种含有硝苯菌酯与丙森锌的杀菌组合物 |
CN104054705A (zh) * | 2014-05-31 | 2014-09-24 | 海利尔药业集团股份有限公司 | 一种含有硝苯菌酯与醚菌酯的杀菌组合物 |
CN104054708A (zh) * | 2014-05-31 | 2014-09-24 | 海利尔药业集团股份有限公司 | 一种含有硝苯菌酯与螺环菌胺的杀菌组合物 |
CN104054714A (zh) * | 2014-05-31 | 2014-09-24 | 海利尔药业集团股份有限公司 | 一种含有硝苯菌酯与粉唑醇的杀菌组合物 |
CN104054733A (zh) * | 2014-06-30 | 2014-09-24 | 海利尔药业集团股份有限公司 | 一种含有硝苯菌酯与唑胺菌酯的杀菌组合物 |
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