CN1259014A - 杀真菌混合物 - Google Patents
杀真菌混合物 Download PDFInfo
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- CN1259014A CN1259014A CN98805753A CN98805753A CN1259014A CN 1259014 A CN1259014 A CN 1259014A CN 98805753 A CN98805753 A CN 98805753A CN 98805753 A CN98805753 A CN 98805753A CN 1259014 A CN1259014 A CN 1259014A
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 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
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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)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
一种杀真菌混合物,它包含以增效有效果的:a)式Ⅰ的氨基甲酸酯,其中,X为CH和N,n为0,1或2,R为卤素、C1-C4-烷基和C1-C4-卤代烷基;如果n为2时,则R可为不同基团,或其盐或加成物,和b)或Ⅱ的4,5-苯并-1-噻-2,3-二唑,其中,R’为CN,CO2H,CO2-C1-C4-烷基或CO-S-C1-C4-烷基,或其盐或加成物。
Description
本发明涉及一种杀真菌混合物,该混合物包含增效有效量的:
其中,X为CH和N,n为O,1或2,R为卤素、C1-C4-烷基和C1-C4-卤代烷基,如果n为2时,R可为不同基团,
和
b)式II的4,5-苯并-1-噻-2,3-二唑或其盐或加成物
其中,R′为CN,CO2H,CO2-C1-C4-烷基或CO-S-C1-C4-烷基。
其次,本发明涉及用化合物I和II的混合物控制有害真菌的方法,以及用化合物I和化合物II在制备该混合物中的应用。
式I化合物、其制备和其对有害真菌的活性在文献中已有描述(WO-A96/01,256;WO-A96/01,258)。
从文献(EP-A313512)中已知,式II化合物是对植物有增加免疫力(imusierenden)作用的活性化合物。另外,含有化合物II的增效混合物亦有报道(WO-A97/01,277)。
对有害真菌具有改进活性,并同时降低所用活性成份(增效混合物)总量,目的在于降低使用量和改进已知化合物I和II的活性谱。
我们发现此目的可通过开始所述及的混合物来实现。而且我们还发现,同时一起或同时分别施用化合物I和化合物II时,或者相继地使用化合物I和化合物II时,对有害真菌的控制效果要好于单一地使用单个的化合物所得到的效果。
式I特别是代表了这样的氨基甲酸酯,其中其取代基的组合对应于下表中的一行。
序号 | 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 |
特别优选的化合物为I.12,I.23,I.32和I.38。
式II特别是代表4,5-苯并-1-噻-2,3-二唑,其中R’对应于下表中的基团之一。
序号 | R′ |
II.1 | CN |
II.2 | CO2H |
II.3 | CO2CH3 |
II.4 | CO-SCH3 |
特别优选的化合物为II.4。
由于其氮原子的碱性特征,化合物I和II能与无机或有机酸或金属离子形成盐或加成物。
无机酸有氢卤酸,如氢氟酸、盐酸、氢溴酸和氢碘酸,以及硫酸、磷酸和硝酸。
适合的有机酸是:如甲酸、碳酸和烷酸如乙酸、三氟乙酸、三氯乙酸和丙酸,以及乙醇酸、硫氰酸、2-羟基丙酸、丁二酸、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(芳香基团如带有1或2个磺基的苯基、萘基),烷基磷酸(具有1-20个碳原子的直链或支链烷基磷酸),芳基磷酸或芳基二磷酸(芳基如带有1或2个磷酸基的苯基、萘基)。烷基或芳基可以带有更多的取代基,如对甲苯磺酸、水杨酸、对氨基水杨酸、2-苯氧基苯甲酸、2-乙酸基苯甲酸等。
适合的金属离子是:特别是第一到第八副族元素的离子,优选铬、锰、铁、钴、镍、铜、锌,以及第二主族元素的离子,优选钙和镁,和第三、第四主族元素的离子,优选铝、锡、铅。这些金属可以它们所能出现的不同价态存在。
化合物II.2的盐特别为碱金属和碱土金属盐(优选锂盐、钠盐、钾盐、镁盐和钙盐),和有机盐,尤其是与铵离子、或者伯、仲、叔胺(优选三甲胺、三乙胺、N,N-二甲基苯胺、吡啶、三乙醇胺、哌啶、吗啉)离子所成的盐。
在制备混合物时,优选用纯的活性成分I和II,其它防治有害真菌或防治别的有害生物如昆虫、蜘蛛和线虫的活性成分、以及具有除草或生长调节活性的成分、或者肥料均可以混合进去。
化合物I和II的混合物、或者同时一起施用或同时分别施用的化合物I和II对许多植物病原真菌、尤其是对子囊菌纲、担子菌纲、藻菌纲和半知菌类有优异的防治活性。其中有些具内吸性能,可因此用做叶面-或土壤处理杀真菌剂。
它们对防治不同作物上的许多真菌尤其重要。这些作物如棉花、蔬菜(如:黄瓜、菜豆、马铃薯、西红柿和葫芦)、大麦、草坪、燕麦、香蕉、咖啡、玉米、水果类、水稻、黑麦、大豆、葡萄藤、小麦、观赏植物、甘蔗和各类种子。
它们尤其适用于防治下列植物病原真菌:谷类植物上的白粉菌(白粉病),葫芦上的二孢白粉菌和单丝壳菌,苹果上的苹果白粉菌,葡萄藤上的葡萄钩丝壳菌,谷类植物上的柄锈菌属,棉花、水稻和草坪上的丝核菌属种类,谷类植物和甘蔗上的黑粉菌属,苹果上的苹果黑星菌,谷类植物和草坪上的长蠕孢属种类,小麦上的小麦颖枯病菌,草莓、蔬菜、观赏植物和葡萄藤上的灰葡萄孢(灰霉病),油菜籽和草地上的核盘菌属,花生上的花生尾孢菌,小麦、大麦上的柔毛假小尾孢菌(Pseudocercosporella herpotrichoides),水稻上的稻梨孢菌,马铃薯和西红柿上的马铃薯晚疫菌,观赏植物、蔬菜、草坪上的腐霉属,葡萄藤上的葡萄霜霉病菌,忽布、黄瓜上的假霜霉属,蔬菜、水果上的交链孢属的种类,香蕉上的球腔菌属和镰刀菌属、轮枝孢属的种类。
另外,它们可用于材料的保护(如木材保护),例如可防治拟青霉。
化合物I和II可以同时一起或同时分别使用,或者按顺序接连使用。在它们分开使用时,一般没有任何防治效果。
化合物I和II通常以10∶1至0.01∶1的重量比使用,优选5∶1至0.05∶1,特别是1∶1至0.05∶1。
根据期望效果的种类,本发明混合物的使用量、尤其是在农作物上的用量为0.01至8kg/公顷,优选0.1到5kg/公顷,特别是0.5至3.0kg/公顷。
化合物I的使用量为0.01至1.0kg/公顷,优选0.05到0.8kg/公顷,特别是0.05至0.5kg/公顷。
相应地,化合物II的使用量为0.001至1.0kg/公顷,优选0.01到0.5kg/公顷,特别是0.01至0.3kg/公顷。
对于种子处理,每千克种子混合物的用量一般为0.001至250克,优选0.01至100克,特别是0.01到50克。
如果要控制植物有害病原真菌,那么应在植物播种前或后,或者植物发芽前或后,分别或一起使用化合物I和II或化合物I和II的混合物,对种子、植物或土壤进行喷雾或喷粉处理。
本发明的杀真菌内吸性混合物,或者说化合物I和II,可以加工成各种剂型,例如,直接喷雾用溶液,粉剂和悬浮剂,或高浓缩型水剂、油剂,或其它悬浮液、可分散液剂、乳油、油分散剂、糊剂、粉剂,用于撒施的材料或颗粒剂。用于喷雾、弥雾、喷粉、撒施或浇水。使用方式取决于预计的目的;无论怎样,依据本发明应保证混合物尽可能细和大小一致,以使其分布均匀。
剂型可由已知的方法制备,例如通过加入溶剂和/或载体。通常在剂型中混入惰性填料如乳化剂或分散剂。
适合的表面活性剂有芳香磺酸如木素磺酸、苯酚磺酸、萘磺酸、二丁基萘磺酸,和脂肪酸、烷基磺酸和烷芳基磺酸盐,烷基-、月桂基醚和脂肪醇硫酸的碱金属盐、-碱土金属盐和-铵盐,硫酸化的十六-、十七-和十八醇的盐,或脂肪醇乙二醇醚的盐,磺化萘和它的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,脂肪醇-环氧乙烷缩合物。乙氧基化蓖麻油,聚氧乙烯烷基醚或聚环氧丙烷,十二烷基醇聚乙二醇醚乙酸酯,山梨醇酯,木素亚硫酸废液或甲基纤维素。
粉剂、撒施材料和喷粉剂可通过使化合物I和II或者化合物I和II的混合物与固体载体混合或一起研磨来制备。
颗粒剂(如涂敷颗粒剂、浸渍颗粒剂或均相颗粒剂)通常通过将活性成分或活性成分物与固体载体结合而制备。
填料或固体载体有例如矿物质如硅胶、硅石、硅胶体、硅酸盐、滑石、高岭土、石灰岩、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,土壤合成原料和肥料,如硫酸铵、磷酸铵、硝酸铵、尿素,以及植物源产品,如谷粉、树皮屑、木屑、坚果壳粉、纤维素粉或其它固体载体。
剂型中一般包含按重量计为0.1到95%、优选在0.5到90%的化合物I和II或化合物I和II的混合物之一,活性成分的纯度在90%到100%之间,优选在95%到100%之间(依据NMR或HPLC谱)。
化合物I和II、或它们的混合物、或相应的剂型,以混合物或化合物I和II分别使用时的对真菌有效剂量来处理有害真菌,使其寄主、或植物、种子、土壤、空地、原料或环境不受它的影响。
在有害真菌侵染前或侵染后可成功地使用。
实施例1——对小麦白粉病的保护作用活性。
向栽培品种为″frühgold″的盆栽小麦幼苗叶面喷施含活性成分的溶液,该溶液由含有10%活性成分,63%环己酮和27%乳化剂的母液制备。在温度20-24℃、相对湿度为60-90%的温室中栽培7天后,将植物用小麦白粉菌孢子(Erysiphe graminis forma specialis tritici)喷粉。将供试植物继续放置于温度为20-24℃、相对湿度为60-90%的温室中,接种7天后,目测白粉病的发病情况,以整个叶片上的感染程度%计。
通过以百分数测定受感染叶面来进行效果评价,这些百分数值转化为效果,效果(E)用下面的Abbot公式计算:
E=(1-α).100/β
α对应于已处理的植物的真菌感染(以%计)
β对应于对照植物的真菌感染(以%计)
0效果表示已处理的植物的感染程度与对照植物的感染程度相当,100效果表示处理植物没有被感染。
活性成分混合物的期望效果用Colby公式[R.S.Colby,杂草,15,20-22(1967)]计算,并与观察到的效果进行比较。
Colby公式:E=x+y-x.y/100
E:在浓度a和b下使用活性成分A和B的混合物时的期望效果,用相对于对照样的%表示。
x:在浓度a下使用活性成分A时的效果,用相对于对照样的%表示。
y:在浓度b下使用活性成分B时的效果,用相对于对照样的%表示。
结果见表3和表4。
表3
实施例号 | 活性成分 | 活性成分喷施液浓度(ppm) | 相对于空白对照样的效果(%) |
1V | 对照样(未处理) | (100%感染) | 0 |
2V | 化合物I.32 | 10.25 | 7010 |
3V | 化合物II.4 | 102.5 | 3010 |
表4
实施例号 | 本发明的混合物 | 观测效果 | 计算效果*) |
4 | 1 ppm I.32+10 ppm II.4 | 95 | 79 |
5 | 0.25 ppm I.32+2.5 ppm II.4 | 40 | 19 |
实施例2——对番茄马铃薯晚疫菌保护作用活性。
向栽培品种为“Groβe Fleischtomate”的盆栽马铃薯植物叶面喷施含水悬浮液,该溶液由含有10%活性成分,63%环己酮和27%乳化剂的母液制备。7天后,向叶面上接种马铃薯晚疫菌游动孢子水悬浮液。将供试植物紧接着放置于温度为16-18℃的水蒸气饱和的室内。接种6天后,未处理的但感染的番茄枯萎,但经处理了的植物能够生长,并可以目测感染情况(以%计)。
效果评价按实施例1所描述的来进行。
结果见下面表5和表6。表5
实施例号 | 活性成分 | 活性成分喷施液浓度(ppm) | 相对于空白样的对照效果(%) |
6V | 对照(未处理) | (97%感染) | 0 |
7V | 化合物I.32 | 10.25 | 6048 |
8V | 化合物II.4 | 102.5 | 2817 |
表6
实施例号 | 本发明的混合物 | 观测效果 | 计算效果*) |
9 | 1 ppmI.32+10 ppm II.4 | 98 | 71 |
10 | 0.25 ppm I.32+2.5 ppm II.4 | 84 | 57 |
*)用Colby公式计算
实验结果表明,在所有的混合比例中观测效果均高于预先用Colby公式计算得到的效果。
Claims (9)
2.根据权利要求1要求的一种杀真菌混合物,其特征在于化合物I或其盐或加成物与化合物II的重量比为10∶1到0.01∶1。
3.一种控制有害真菌的方法,其特征在于用权利要求1所述的式I化合物或其盐或加成物与权利要求1所述的式II化合物来处理有害真菌,使其寄主、或植物、种子、土壤、空地、材料或环境不受它的影响。
4.根据权利要求3要求的方法,其中权利要求1所述的化合物I或其盐或加成物与权利要求1所述的化合物II同时一起或同时分开施用,或者相继施用。
5.根据权利要求3或4要求的方法,其中权利要求1所述的化合物I或其盐或加成物以0.01到1.0kg/公顷的用量施用。
6.根据根据权利要求3-5的方法,其中权利要求1所述的化合物II以0.001到1.0kg/公顷的用量施用。
7.权利要求1所述的化合物I或其盐或加成物在制备权利要求1的具有杀真菌活性的增效混合物中的应用。
8.权利要求1所述的化合物II在制备权利要求1的具有杀真菌活性的增效混合物中的应用。
9.权利要求1的混合物,它包含两部分,一部分包含存在于固体或液体载体上的权利要求1所述的式I化合物,另一部分包含存在于固体或液体载体上的权利要求1所述的式II化合物。
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AR014101A1 (es) | 2001-02-07 |
PL337230A1 (en) | 2000-08-14 |
ZA984755B (en) | 1999-12-03 |
WO1998054968A1 (de) | 1998-12-10 |
HUP0004224A3 (en) | 2002-11-28 |
BR9809721A (pt) | 2000-07-11 |
KR20010013339A (ko) | 2001-02-26 |
CO5040018A1 (es) | 2001-05-29 |
CA2291753A1 (en) | 1998-12-10 |
SK162399A3 (en) | 2000-06-12 |
NZ500985A (en) | 2002-07-26 |
HUP0004224A2 (hu) | 2001-04-28 |
US6344469B1 (en) | 2002-02-05 |
EA001940B1 (ru) | 2001-10-22 |
EA199901069A1 (ru) | 2000-06-26 |
EP0986305A1 (de) | 2000-03-22 |
TW533057B (en) | 2003-05-21 |
AU8105398A (en) | 1998-12-21 |
JP2002501538A (ja) | 2002-01-15 |
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