CN101795566A - 二甲嘧菌胺和二噻农的共晶 - Google Patents
二甲嘧菌胺和二噻农的共晶 Download PDFInfo
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- CN101795566A CN101795566A CN200880105848A CN200880105848A CN101795566A CN 101795566 A CN101795566 A CN 101795566A CN 200880105848 A CN200880105848 A CN 200880105848A CN 200880105848 A CN200880105848 A CN 200880105848A CN 101795566 A CN101795566 A CN 101795566A
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- pyrimethanil
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
Abstract
本发明涉及二甲嘧菌胺和二噻农的共晶,其在25℃下在X-射线粉末衍射谱图中显示至少3个如下反射:2θ=7.46±0.20,2θ=9.98±0.20,2θ=13.28±0.20,2θ=23.09±0.20,2θ=24.38±0.20,2θ=27.01±0.20,一种制备它们的方法及其在制备用于作物保护的组合物中的用途。
Description
本发明涉及二甲嘧菌胺(pyrimethanil)和二噻农(dithianon)的新的共晶,及其制备方法,以及该新的共晶在制备作物保护组合物中的用途。
二甲嘧菌胺已知为杀真菌剂且描述于DD-A 151 404中。
二噻农已知为杀真菌剂且描述于GB-A 857 383中。
WO 2004/004461描述了二甲嘧菌胺和二噻农协同增效混合物。所有生物实验以在丙酮和DMSO中的混合物溶液进行。在加入1%的乳化剂之后,将溶液与水混合以达到所需浓度。在该文献中并没有描述悬浮液浓缩物。
在制备二甲嘧菌胺和二噻农的悬浮液浓缩物(SC)的过程中,浓缩物颜色从棕色变为深绿色/黑色并且浓缩物固化且不可用于制备作物保护配制剂。
因此,本发明的目的是提供二甲嘧菌胺和二噻农的如下形式的混合物,该形式允许制备可流动且稳定的悬浮液浓缩物。
该目的通过下述的二甲嘧菌胺和二噻农的共晶实现。
因此,本发明涉及二甲嘧菌胺和二噻农的共晶,其在25℃下在X-射线粉末衍射谱图中显示至少3个,尤其是至少4个,优选所有的如下2θ值[°]:
2θ=7.46±0.20
2θ=9.98±0.20
2θ=13.28±0.20
2θ=23.09±0.20
2θ=24.38±0.20
2θ=27.01±0.20
二噻农和二甲嘧菌胺的深绿色或黑色单晶的结晶复合物的单晶结构分析显示为单斜晶系和空间群P2(1)/n。在-170℃下测量的重要晶胞参数示于表1。在该共晶中二噻农与二甲嘧菌胺的比例为1∶1。二噻农和二甲嘧菌胺之间的复合物经由二甲嘧菌胺的N-H基团和二噻农的一个羰基之间的强氢键(N-H...O,角度168.1°)形成。
图1:二噻农和二甲嘧菌胺共晶的单晶结构。
表1:在-170℃下,二噻农和二甲嘧菌胺的结晶复合物的晶体学数据。
参数 | |
晶系 | 单斜 |
空间群 | P-1 |
a | 717.0(1)pm |
b | 2278.5(2)pm |
c | 1381.3(2)pm |
α | 90° |
β | 97.069(5)° |
γ | 90° |
体积 | 2.2395(4)nm3 |
Z | 4 |
密度(计算) | 1.470g/cm3 |
R1,wR2 | 0.039,0.097 |
a,b,c=单位晶胞的边长
α,β,γ=单位晶胞角度
Z=单位晶胞中的二噻农和二甲嘧菌胺复合物(1∶1)的数目
表3:二甲嘧菌胺和二噻农的共晶的PXRD
2θ值[°] | d[nm] |
7.46±0.20 | 11.86±0.3 |
2θ值[°] | d[nm] |
9.98±0.20 | 8.87±0.2 |
13.28±0.20 | 6.67±0.1 |
14.90±0.20 | 5.95±0.06 |
18.6±0.20 | 4.77±0.05 |
20.30±0.20 | 4.38±0.03 |
23.09±0.20 | 3.85±0.03 |
24.38±0.20 | 3.65±0.02 |
27.01±0.20 | 3.30±0.02 |
29.94±0.20 | 2.99±0.02 |
根据TGA/DTA(并由高温热台显微镜测量证实),可以看出熔点为165-175℃,尤其是166-173℃,
在根据本发明所述实施方案的共晶中,二甲嘧菌胺和二噻农的摩尔比为2∶1-1∶2,尤其是约1∶1。
本发明结晶复合物可通过将二噻农和二甲嘧菌胺从含有这两种组分的溶液或浆料或熔体中共结晶而制备。化合物的比例并不关键,因为会形成1∶1的共晶,并剩下过量的完整的其他组分。同样可以通过在含水介质或基于植物油或矿物油的介质中混合或研磨二噻农和二甲嘧菌胺作为干化合物的混合物而制备本发明的结晶复合物。
本发明共晶适用于制备作物保护组合物,尤其用于制备含水悬浮液浓缩物。
因此,本发明还提供了用于作物保护的包含二甲嘧菌胺和二噻农的共晶以及载体和/或助剂的组合物。
合适的载体原则上为所有常用于作物保护组合物,尤其是用于杀真菌剂的固体物质。固体载体例如为矿土如硅胶、硅酸盐、滑石、高岭土、活性粘土(attaclay)、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,以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其它固体载体。
合适的液体载体原则上为水以及其中共晶具有低溶解度或不溶解的有机溶剂,如其中共晶在25℃和1013毫巴下的溶解度不超过1重量%,尤其是不超过0.1重量%,特别是不超过0.01重量%的那些。液体载体的实例包括水,植物油,如大豆油、玉米油、向日葵油、橄榄油,脂肪酸的酯如油酸甲酯或矿物油如轻石油醚,Bayol 85、Exxsol D 130、Exxsol D 140,Exxon Chemicals的合成异构烷油产品系列。
典型的助剂包括常用于作物保护组合物的表面活性剂,尤其是润湿剂和分散剂,还有粘度改性添加剂(增稠剂)、消泡剂、防冻剂、用于调节pH的试剂、稳定剂、防结块剂和生物杀伤剂(防腐剂)。
本发明尤其涉及呈含水悬浮液浓缩物(SC)形式的用于作物保护的组合物。该悬浮液浓缩物包含细碎颗粒形式的共晶,其中共晶颗粒悬浮在含水介质中。共晶颗粒的尺寸(即90重量%活性化合物颗粒不超过的尺寸)通常小于30μm,尤其是小于20μm。有利的是在本发明SC中,至少40重量%,尤其是至少60重量%的颗粒的直径小于2μm。
除了共晶外,悬浮液浓缩物通常含有表面活性剂以及合适的话消泡剂、增稠剂、防冻剂、稳定剂(生物杀伤剂)、用于调节pH的试剂和抗结块剂。
在该类SC中,共晶的量以及合适的话其它活性化合物基于该悬浮液浓缩物总重量通常为10-70重量%,尤其是20-50重量%。
优选表面活性剂为阴离子和非离子表面活性剂。合适的表面活性剂还包括保护胶体。表面活性剂的量基于本发明SC的总重量通常为0.5-20重量%,尤其是1-15重量%,特别优选1-10重量%。优选表面活性剂包括至少一种阴离子表面活性剂和至少一种非离子表面活性剂,并且阴离子表面活性剂与非离子表面活性剂的比例通常位于10∶1-1∶10的范围内。
阴离子表面活性物质(表面活性剂)的实例包括烷基芳基磺酸盐,苯基磺酸盐,烷基硫酸盐,烷基磺酸盐,烷基醚硫酸盐,烷基芳基醚硫酸盐,烷基聚乙二醇醚磷酸盐,聚芳基苯基醚磷酸盐,烷基磺基琥珀酸酯盐,烯烃磺酸盐,链烷磺酸盐,石油磺酸盐,氨基乙磺酸盐,肌氨酸,脂肪酸,烷基萘磺酸,萘磺酸,木素磺酸,磺化萘与甲醛的缩合产物,磺化萘与甲醛和苯酚以及合适的话脲的缩合产物以及苯酚磺酸与甲醛和脲的缩合产物,木素亚硫酸盐废液和木素磺酸盐,烷基磷酸盐,烷基芳基磷酸盐,例如三苯乙烯基磷酸盐,以及聚羧酸盐如聚丙烯酸盐,马来酸酐/烯烃共聚物(例如CP9,BASF),包括上述物质的碱金属、碱土金属、铵和胺盐。优选的阴离子表面活性物质是带有至少一个磺酸盐基团,尤其是其碱金属及其铵盐的那些。
非离子表面活性剂的实例包括烷基酚烷氧基化物,三苯乙烯基苯酚烷氧基化物(如Soprophor BSU),醇烷氧基化物,脂肪胺烷氧基化物,聚氧乙烯甘油脂肪酸酯,蓖麻油烷氧基化物,脂肪酸烷氧基化物,脂肪酸酰胺烷氧基化物,脂肪酸聚二乙醇酰胺,羊毛脂乙氧基化物,脂肪酸聚乙二醇酯,异十三烷醇,脂肪酰胺,甲基纤维素,脂肪酸酯,烷基聚糖苷,甘油脂肪酸酯,聚乙二醇,聚丙二醇,聚乙二醇/聚丙二醇嵌段共聚物(如Pluoronic PE 10500),聚乙二醇烷基醚,聚丙二醇烷基醚,聚乙二醇/聚丙二醇醚嵌段共聚物(聚氧乙烯/聚氧丙烯嵌段共聚物)及其混合物。优选的非离子表面活性剂是脂肪醇乙氧基化物、烷基聚糖苷、甘油脂肪酸酯、蓖麻油烷氧基化物、脂肪酸烷氧基化物、脂肪酸酰胺烷氧基化物、羊毛脂乙氧基化物、脂肪酸聚乙二醇酯和氧化乙烯/氧化丙烯嵌段共聚物及其混合物。
典型的保护胶体为水溶性两性聚合物。它们的实例为蛋白质和变性蛋白如酪蛋白,多糖如水溶性淀粉衍生物和纤维素衍生物,尤其是疏水改性的淀粉和纤维素,还有聚羧酸盐如聚丙烯酸、丙烯酸共聚物,聚乙烯醇,聚乙烯吡咯烷酮,乙烯基吡咯烷酮共聚物,聚乙烯基胺,聚乙烯亚胺和聚亚烷基醚。
本发明SC尤其包含至少一种改进植物部分被含水施用形式润湿的表面活性剂(润湿剂)和至少一种稳定活性化合物颗粒在SC中分散的表面活性剂(分散剂)。润湿剂的量基于SC总重量通常为0.5-10重量%,尤其是0.5-5重量%,特别是0.5-3重量%。分散剂的量基于SC的总重量通常为0.5-10重量%,尤其是0.5-5重量%。
优选润湿剂为阴离子和非离子性质的且例如选自萘磺酸,包括其碱金属盐、碱土金属盐、铵盐和胺盐,还有脂肪醇乙氧基化物、脂肪醇烷氧基化物(如Atplus 245)、碱金属磺基琥珀酸酯盐(如Lutensit A-BO)、烷基聚糖苷、甘油脂肪酸酯、蓖麻油烷氧基化物、脂肪酸烷氧基化物、脂肪酰胺烷氧基化物、脂肪酸聚二乙醇酰胺、羊毛脂乙氧基化物和脂肪酸聚乙二醇酯。
优选分散剂为阴离子和非离子性质的且例如选自聚乙二醇/聚丙二醇嵌段共聚物(如Pluoronic PE 10500)、聚乙二醇烷基醚、聚丙二醇烷基醚、聚乙二醇/聚丙二醇醚嵌段共聚物,烷基芳基磷酸盐,例如三苯乙烯基磷酸盐,木素磺酸(如Reax 910),磺化萘与甲醛或与甲醛和苯酚以及合适的话脲的缩合物(如Morwet 3 D 425),以及苯酚磺酸、甲醛和脲的缩合物,木素亚磺酸盐废液和木素磺酸盐,聚羧酸盐,如聚丙烯酸盐,马来酸酐/烯烃共聚物(例如CP9,BASF),包括上述物质的碱金属、碱土金属、铵和胺盐。
适用于本发明SC的粘度改性添加剂(增稠剂)尤其为赋予配制剂假塑性流动性能,即静止状态下高粘度和搅拌状态下低粘度的化合物。原则上合适的是所有在悬浮液浓缩物中用于该目的的化合物。例如可提及无机物质,如膨润土或硅镁土(例如Engelhardt),以及有机物质如多糖和杂多糖如Xanthan(Kelco的)、23(RhonePoulenc)或(R.T.Vanderbilt)。优选使用Xanthan-粘度改性添加剂的量基于SC的总重量通常为0.1-5重量%。
适用于本发明SC的消泡剂例如为对该目的已知的聚硅氧烷乳液(SRE,Wacker或Rhodia的)、长链醇、脂肪酸及其盐、含水蜡分散体类型的消泡剂、固体消泡剂(所谓的Compounds)和有机氟化合物及其混合物。消泡剂的量基于SC的总重量通常为0.1-1重量%。
也可加入防腐剂以稳定本发明悬浮液浓缩物。合适的防腐剂是基于异噻唑啉酮的那些,例如ICI的或者Thor Chemie的MBS或Rohm & Hass的MK。防腐剂的量基于SC的总重量通常为0.05-0.5重量%。
合适的防冻剂是液态多元醇,如脲,乙二醇、丙二醇或甘油。防冻剂的量基于悬浮液浓缩物的总重量通常为1-20重量%,尤其是5-10重量%。
合适的话,本发明的SC可以含有用于调节pH的缓冲剂。缓冲剂的实例是弱无机或有机酸如磷酸、硼酸、乙酸、丙酸、柠檬酸、富马酸、酒石酸、草酸和琥珀酸的碱金属盐。
常用于该类目的的所有染料和颜料都为合适的着色剂。微水溶性颜料和水溶性染料在这里都可用。作为实例可以提及以如下名称已知的染料和颜料:若丹明B、C.I.颜料红112和C.I.溶剂红1、颜料蓝15:4、颜料蓝15:3、颜料蓝15:2、颜料蓝15:1、颜料蓝80、颜料黄1、颜料黄13、颜料红48:2、颜料红48:1、颜料红57:1、颜料红53:1、颜料橙43、颜料橙34、颜料橙5、颜料绿36、颜料绿7、颜料白6、颜料棕25、碱性紫10、碱性紫49、酸性红51、酸性红52、酸性红14、酸性蓝9、酸性黄23、碱性红10、碱性红10和碱性红108。着色剂的量通常不超过配制剂的20重量%,优选基于配制剂的总重量为0.1-15重量%。
合适的增粘剂为所有常用于拌种的粘合剂。合适粘合剂的实例包括热塑性聚合物如聚乙烯基吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和纤基乙酸钠,以及聚丙烯酸酯、聚甲基丙烯酸酯、聚丁烯、聚异丁烯、聚苯乙烯、聚乙烯胺、聚乙烯酰胺、上述保护性胶体、聚酯、聚醚酯、聚酐、聚酯聚氨酯、聚酯酰胺,热塑性多糖,例如纤维素衍生物如纤维素酯、纤维素醚、纤维素醚酯,包括甲基纤维素、乙基纤维素、羟甲基纤维素、羧甲基纤维素、羟丙基纤维素及淀粉衍生物和改性淀粉、糊精、麦芽糖糊精、藻酸盐和脱乙酰壳多糖以及脂肪、油、蛋白质,包括酪蛋白、明胶和玉米蛋白、阿拉伯胶和紫胶。增粘剂优选是植物相容的,即它们不呈现显著的植物毒性作用(如果有的话)。增粘剂优选可生物降解。增粘剂的选择优选应使得它用作配制剂活性组分的基质。增粘剂的量通常不超过配制剂的40重量%,优选基于配制剂的总重量为1-40重量%,尤其是5-30重量%。
除了增粘剂外,配制剂还可以含有惰性填料。这些填料的实例是上述固体载体材料,尤其是细碎无机材料如粘土、白垩、膨润土、高岭土、滑石、珍珠岩、云母、硅胶、硅藻土、石英粉和蒙脱土,还有细颗粒有机材料如木粉、谷粉、活性炭等。填料量的选择优选应使得填料的总量基于配制剂的所有非挥发性组分的总重量不超过75重量%。填料的量基于配制剂的所有非挥发性组分的总重量通常为1-50重量%。
此外,配制剂还可以含有增加涂层的柔性的增塑剂。增塑剂的实例是低聚聚亚烷基二醇、甘油、邻苯二甲酸二烷基酯、邻苯二甲酸烷基苄基酯、乙二醇苯甲酸酯和类似化合物。增塑剂在涂层中的量基于配制剂的所有非挥发性组分的总重量通常为0.1-20重量%。
适用于制备二甲嘧菌胺和二噻农的共晶的方法如下所述。
如上所述,为制备共晶,将等摩尔量二甲嘧菌胺和二噻农在室温和搅拌下溶于极性溶剂,如DMSO、乙腈、DMF或丙酮中。将溶剂蒸发以得到二甲嘧菌胺和二噻农的共晶。
在制备共晶的另一方法中,将等摩尔量的二甲嘧菌胺和二噻农彻底混合并在任选的升高温度下干磨。
在制备共晶的另一方法中,将等摩尔量的二甲嘧菌胺和二噻农与液体载体如水、基于植物或矿物的油彻底混合,然后在任选的升高温度下研磨。
·制备二甲嘧菌胺和二噻农的共晶的稳定组合物的制备方法I:
通过在室温,任选在升高温度下,分别彻底混合水、分散剂、乳化剂、防冻剂、润湿剂、消泡剂和/或杀菌剂和二甲嘧菌胺或二噻农而制备两种分开的预混物。
将两种预混物(其并不是研磨的悬浮液)在烧杯中在搅拌下在20-100℃,优选20-70℃,最优选在约50℃下一起混合。在1小时之后,悬浮液从棕色变为深绿色。将悬浮液冷却至20℃,然后在玻璃珠磨机中研磨以得到80%<2μm的粒度分布(PSD)。产物粘度小于50mPas。粘度可通过加入增稠剂如黄原胶进一步调节。可在此阶段加入的其他添加剂包括但不限于生物杀伤剂、消泡剂和其他流变改性剂。产品在室温下保持不变化至少4个月。在此时间内粒度分布非常稳定。
·制备方法II:使含有二甲嘧菌胺和二噻农两者的预混物在升高温度下连续通过珠磨机。在半小时之后,整个悬浮液变为深绿色。将磨机冷却至20℃并继续研磨直至获得80%<2μm的PSD。粘度可通过加入增稠剂如黄原胶而进一步调节。可在此阶段加入的其他添加剂包括但不限于生物杀伤剂、消泡剂和其他流变改性剂。
·制备方法III:预混物通过将二甲嘧菌胺、水和分散剂以及其它配制添加剂彻底混合而制备。在搅拌下在该悬浮液预混物中加入计算量的二噻农。在加入所有二噻农之后,将混合物加热至50℃并维持1小时。悬浮液变为深绿色并且在将其冷却至20℃之后,将其在珠磨机上研磨获得80%的PSD<2μm。粘度可通过加入增稠剂如黄原胶而进一步调节。可在此阶段加入的其他添加剂包括但不限于生物杀伤剂、消泡剂和其他流变改性剂。
·制备方法IV:预混物通过将二噻农、水和分散剂以及其它配制添加剂彻底混合而制备。在搅拌下在该悬浮液预混物中加入计算量的二甲嘧菌胺。在加入所有二甲嘧菌胺之后,将混合物加热至50℃并维持1小时。悬浮液变为深绿色并且在将其冷却至20℃之后,将其在珠磨机上研磨获得80%的PSD<2μm。粘度可通过加入增稠剂如黄原胶而进一步调节。可在此阶段加入的其他添加剂包括但不限于生物杀伤剂、消泡剂和其他流变改性剂。
·制备方法V:用合适的分散剂和乳化剂将二噻农和二甲嘧菌胺一起悬浮于基于矿物或植物的油,如白油、Bayol 85、向日葵油、菜籽油、玉米油和油酸甲酯中。将OD(油分散体)预混物在搅拌下加热至50℃,直至悬浮液的颜色由棕色变为深绿色(1小时)。然后将预混物冷却并在珠磨机上研磨以获得80%<2μm的PSD。粘度可通过加入增稠剂如黄原胶而进一步调节。可在此阶段加入的其他添加剂包括但不限于生物杀伤剂、消泡剂和其他流变改性剂。
制备方法VI:在混合下制备二噻农和二甲嘧菌胺在极性溶剂,如DMSO、乙腈、DMF或丙酮中的溶液。将溶剂蒸发以得到共晶。将其悬浮于水和配制添加剂(与对悬浮液浓缩物所述的相同)并首先在PUC磨机上预研磨,然后在珠磨机上精磨以获得80%<2μm的PSD。粘度可通过加入增稠剂如黄原胶而进一步调节。可在此阶段加入的其他添加剂包括但不限于生物杀伤剂、消泡剂和其他流变改性剂。
制备方法VII:将干的二噻农和二甲嘧菌胺彻底混合并在搅拌下保持在50℃下。在数小时之后,粉末产物的颜色变为橄榄绿。在冷却的共晶预混物中加入对WG、WP和WDG配制剂典型的分散剂、消泡剂、润湿剂、辅助剂和填料。然后将预混物如下进一步加工:通过挤出得到WDG(水分散性颗粒)配制剂或在整理步骤之后作为WP(可湿性粉末)使用。也可将其悬浮于水中,然后喷雾干燥以得到水分散性颗粒。
制备方法VIII:二甲嘧菌胺和二噻农的悬浮液预混物如实施例号III所述制备。然后使该预混物通过珠磨机以得到80%的PSD<2μm。然后,将所得悬浮液喷雾干燥以得到WDG配制剂。
在组合物中,二甲嘧菌胺与二噻农的重量比为100∶1-1∶100,优选20∶1-1∶20,尤其是10∶1-1∶10,最优选2∶3。
二甲嘧菌胺和二噻农的共晶的显著之处在于对植物,尤其是豆科植物的活力和产量增加的作用以及对宽范围的尤其是选自子囊菌纲(Ascomycetes)、半知菌纲(Deuteromycetes)、担子菌纲(Basidiomycetes)和卵菌纲(Peronosporomycetes)(同义词卵菌纲(Oomycetes))的植物病原性真菌具有优异的效力。它们内吸有效且可以作为叶面杀真菌剂、拌种用杀真菌剂和土壤杀真菌剂用于作物保护中。
它们对在各种作物植物如香蕉、棉花、蔬菜(如黄瓜、菜豆和葫芦)、大麦、禾草、燕麦、咖啡、土豆、玉米、水果植物、稻、黑麦、大豆、西红柿、葡萄、小麦、观赏植物、甘蔗和大量种子防治大量真菌尤其重要。
它们有利地适用于防治如下植物病害:
●蔬菜、油籽油菜、糖用甜菜、水果和稻上的链格孢属(Alternaria),例如土豆和西红柿上的早疫链格孢(A.solani)或链格孢(A.alternata);
●糖用甜菜和蔬菜上的丝囊霉属(Aphanomyces);
●禾谷类和蔬菜上的壳二孢属(Ascochyta);
●玉米、禾谷类、稻和草坪中的平脐蠕孢属(Bipolaris)和内脐蠕孢属(Drechslera),例如玉米上的玉蜀黍平脐蠕孢(D.maydis);
●禾谷类上的禾白粉菌(Blumeria graminis)(白粉病);
●草莓、蔬菜、花卉和葡萄藤上的灰葡萄孢(Botrytis cinerea)(灰霉病),
●莴苣上的莴苣盘梗霉(Bremia lactucae),
●玉米、大豆、稻和糖用甜菜上的尾孢属(Cercospora);
●玉米、禾谷类、稻上的旋孢腔菌属(Cochliobolus),例如禾谷类上的禾旋孢腔菌(Cochliobolus sativus),稻上的宫部旋孢腔菌(Cochliobolusmiyabeanus);
●大豆和棉花上的剌盘孢属(Colletotricum);
●玉米、禾谷类、稻和草坪上的内脐蠕孢属(Drechslera)、核腔菌属(Pyrenophora),例如大麦上的大麦网斑内脐蠕孢(D.teres)或小麦上的D.tritci-repentis;
●由Phaeoacremonium chlamydosporium、Ph.Aleophilum和Formitiporapunctata(同义词斑孔木层孔菌(Phellinus punctatus))引起的葡萄藤上的埃斯卡(Esca);
●葡萄藤上的痂囊腔菌(Elsinoe ampelina),
●玉米上的突脐蠕孢属(Exserohilum),
●黄瓜上的二孢白粉菌(Erysiphe cichoracearum)和单丝壳白粉菌(Sphaerotheca fuliginea),
●各种植物上的镰孢霉属(Fusarium)和轮枝孢属(Verticillium),例如禾谷类上的禾本科镰孢(F.graminearum)或大刀镰孢(F.culmorum)或多种植物如西红柿上的尖镰孢(F.oxysporum);
●禾谷类上的禾顶囊壳(Gaeumanomyces graminis);
●禾谷类和稻上的赤霉属(Gibberella)(例如稻上的藤仓赤霉(Gibberellafujikuroi));
●葡萄藤和其它植物上的围小丛壳(Glomerella cingulata),
●稻上的革兰氏染色配合物(Grainstaining complex);
●葡萄藤上的葡萄球座菌(Guignardia budwelli),
●玉米和稻上的长蠕孢属(Helminthosporium);
●葡萄藤上的褐斑拟棒束孢(Isariopsis clavispora),
●禾谷类上的Michrodochium nivale;
●禾谷类、香蕉和花生上的球腔菌属(Mycosphaerella),例如小麦上的禾生球腔菌(M.graminicola)或香蕉上的斐济球腔菌(M.fijiensis);
●卷心菜和球茎植物上的霜霉属(Peronospora),例如卷心菜上的芸苔霜霉(P.brassicae)或洋葱上的大葱霜霉(P.destructor);
●大豆上的豆薯层锈菌(Phakopsora pachyrhizi)和山马蟥层锈菌(Phakopsara meibomiae);
●大豆和向日葵上的拟茎点霉属(Phomopsis),葡萄藤上的葡萄拟茎点霉(P.viticola);
●土豆和西红柿上的致病疫霉(Phytophthora infestans);
●各种植物上的疫霉属(Phytophthora),例如柿子椒上的辣椒疫霉(P.capsici);
●葡萄藤上的葡萄生单轴霉(Plasmopara viticola),
●苹果上的苹果白粉病菌(Podosphaera leucotricha),
●禾谷类上的小麦基腐病菌(Pseudocercosporella herpotrichoides),
●各种植物上的假霜霉属(Pseudoperonospora),例如黄瓜上的古巴假霜霉(P.Cubensis)或啤酒花上的葎草假霜(P.Humili);
●葡萄藤上的Pseudopezicula tracheiphilai,
●各种植物上的柄锈菌属(Puccinia),例如禾谷类上的小麦柄锈菌(P.triticina)、条形柄锈病(P.striformis)、大麦柄锈病(P.hordei)或禾柄锈菌(P.graminis),或芦笋上的天门冬属柄锈病(P.asparagi));
●稻上的稻瘟病菌(Pyricularia oryzae)、笹木伏革菌(Corticium sasakii)、帚梗柱孢属(Sarocladium oryzae)、稻叶鞘腐败病(S.attenuatum)、稻叶黑粉菌(Entyloma oryzae),
●草坪和禾谷类上的稻梨孢菌(Pyricularia grisea),
●草坪、稻、玉米、棉花、油籽油菜、向日葵、糖用甜菜、蔬菜和其他植物上的腐霉属(Pythium),例如各种植物上的终极腐霉菌(P.ultiumum),草坪上的瓜果腐霉(P.aphanidermatum);
●棉花、稻、土豆、草坪、玉米、油籽油菜、糖用甜菜、蔬菜和各种植物上的丝核菌属(Rhizoctonia),例如甜菜和各种植物上的立枯丝核病菌(R.solani);
●大麦、黑麦和黑小麦上的黑麦喙孢(Rhynchosporium secalis);
●油籽油菜和向日葵上的核盘菌属(Sclerotinia);
●小麦上的小麦壳针孢(Septoria tritici)和颖枯壳多孢(Stagonosporanodorum),
●葡萄藤上的葡萄钩丝壳(Erysiphe(同义词Uncinula)necator),
●玉米和草坪上的Setospaeria属,
●玉米上的丝轴黑粉菌(Sphacelotheca reilinia),
●大豆和棉花上的根串珠霉属(Thievaliopsis),
●禾谷类上的腥黑粉菌属(Tilletia),
●禾谷类、玉米和甘蔗上的黑粉菌属(Ustilago),例如玉米上的玉蜀黍黑粉菌(U.maydis);
●苹果和梨上的黑星菌属(Venturia)(黑星病),例如苹果上的苹果黑星病(V.inaequalis)。
二甲嘧菌胺和二噻农的共晶还适于防治有害真菌以保护材料(如木材、纸张、漆分散体、纤维或织物)和保护储藏的产品。在木材保护中,特别应注意下列有害真菌:子囊菌纲真菌,如线嘴壳属(Ophiostoma spp.),长喙壳属(Ceratocystis spp.),出芽短梗霉(Aureobasidium pullulans),Sclerophoma spp.,毛壳属(Chaetomium spp.),腐质霉属(Humicola spp.),彼得壳属(Petriella spp.),毛束霉属(Trichurus spp.);担子菌纲真菌,如粉孢革菌属(Coniophora spp.),革盖菌属(Coriolus spp.),粘褶菌属(Gloeophyllum spp.),香菇属(Lentinus spp.),侧耳属(Pleurotus spp.),卧孔属(Poria spp.),干朽菌属(Serpula spp.)和干酪菌属(Tyromyces spp.),半知菌纲真菌,如曲霉属(Aspergillus spp.),枝孢属(Cladosporium spp.),青霉属(Penicillium spp.),木霉属(Trichoderma spp.),链格孢属(Alternariaspp.),拟青霉属(Paecilomyces spp.)和接合菌纲(Zygomycetes)真菌,如毛霉属(Mucor spp.),此外在材料保护中应注意下列酵母:假丝酵母属(Candida spp.)和酿酒酵母(Saccharomyces cerevisae)。
在某些情况下,可能有利的是在二甲嘧菌胺和二噻农的共晶中加入一种或多种其它活性化合物。
本发明化合物可以与其结合使用的下列杀真菌剂用来说明可能的组合但不限制它们:
唑类
-三唑类:双苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、噁醚唑(difenoconazole)、烯唑醇(diniconazole)、烯菌灵(enilconazole)、腈苯唑(fenbuconazole)、氟硅唑(flusilazole)、喹唑菌酮(fluquinconazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、酰胺唑(imibenconazole)、环戊唑醇(ipconazole)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、唑菌醇(triadimenol)、三唑酮(triadimefon)、戊叉唑菌(triticonazole);
-咪唑类:氰霜唑(cyazofamid)、烯菌灵(imazalil)、稻瘟酯(pefurazoate)、丙氯灵(prochloraz)、氟菌唑(triflumizole);
-苯并咪唑类:苯菌灵(benomyl)、多菌灵(carbendazim)、麦穗宁(fuberidazole)、涕必灵(thiabendazole);
-其他:噻唑菌胺(ethaboxam)、氯唑灵(etridiazole)、土菌消(hymexazole);
嗜球果伞素类(Strobilurins)
-腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、烯肟菌酯(enestroburin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、啶氧菌酯(picoxystrobin)、唑菌胺酯(pyraclostrobin)、肟菌酯(trifloxystrobin)、肟醚菌胺(orysastrobin)、(2-氯-5-[1-(3-甲基苄氧亚氨基)乙基]苄基)氨基甲酸甲酯、(2-氯-5-[1-(6-甲基吡啶-2-基甲氧基亚氨基)乙基]苄基)氨基甲酸甲酯、2-(邻-((2,5-二甲基苯氧基亚甲基)苯基)-3-甲氧基丙烯酸甲酯;
羧酰胺类
-羧酰苯胺类:苯霜灵(benalaxyl)、麦锈灵(benodanil)、啶酰菌胺(boscalid)、萎锈灵(carboxin)、丙氧灭绣胺(mepronil)、呋菌胺(fenfuram)、环酰菌胺(fenhexamid)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)、噁霜灵(oxadixyl)、氧化萎锈灵(oxycarboxin)、吡噻菌胺(penthiopyrad)、溴氟唑菌(thifluzamide)、噻酰菌胺(tiadinil)、N-(4′-溴联苯-2-基)-4-二氟甲基-2-甲基噻唑-5-甲酰胺、N-(4′-三氟甲基联苯-2-基)-4-二氟甲基-2-甲基噻唑-5-甲酰胺、N-(4′-氯-3′-氟联苯-2-基)-4-二氟甲基-2-甲基噻唑-5-甲酰胺、N-(3′,4′-二氯-4-氟联苯-2-基)-3-二氟甲基-1-甲基吡唑-4-甲酰胺、N-(2-氰基苯基)-3,4-二氯异噻唑-5-甲酰胺;
-羧酸吗啉化物:烯酰吗啉(dimethomorph)、氟吗啉(flumorph);
-苯甲酰胺类:氟联苯菌(flumetover)、fluopicolide(氟吡菌胺(picobenzamid))、苯酰菌胺(zoxamide);
-其他羧酰胺:氯环丙酰胺(carpropamid)、双氯氰菌胺(diclocymet)、双炔酰菌胺(mandipropamid)、N-(2-(4-[3-(4-氯苯基)丙-2-炔氧基]-3-甲氧基苯基)乙基)-2-甲烷磺酰基氨基-3-甲基丁酰胺、N-(2-(4-[3-(4-氯苯基)丙-2-炔氧基]-3-甲氧基苯基)乙基)-2-乙烷磺酰基氨基-3-甲基丁酰胺;
含氮杂环基化合物
-吡啶类:啶斑肟(pyrifenox)、3-[5-(4-氯苯基)-2,3-二甲基异噁唑烷-3-基]吡啶;
-嘧啶类:磺嘧菌灵(bupirimate)、嘧菌腙(ferimzone)、异嘧菌醇(fenarimol)、嘧菌胺(mepanipyrim)、氟苯嘧啶醇(nuarimol)、二甲嘧菌胺(pyrimethanil);
-哌嗪类:嗪氨灵(triforine);
-吡咯类:氟噁菌(fludioxonil)、拌种咯(fenpiclonil);
-吗啉类:4-十二烷基-2,6-二甲基吗啉(aldimorph)、吗菌灵(dodemorph)、丁苯吗啉(fenpropimorph)、克啉菌(tridemorph);
-二羧酰亚胺类:异丙定(iprodione)、杀菌利(procymidone)、烯菌酮(vinclozolin);
-其他:噻二唑素(acibenzolar-S-methyl)、敌菌灵(anilazine)、克菌丹(captan)、敌菌丹(captafol)、棉隆(dazomet)、哒菌清(diclomezine)、氰菌胺(fenoxanil)、灭菌丹(folpet)、苯锈啶(fenpropidin)、噁唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、异噻菌酮(octhilinone)、噻菌灵(probenazole)、丙氧喹啉(proquinazid)、咯喹酮(pyroquilon)、喹氧灵(quinoxyfen)、三环唑(tricyclazole)、5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮、N,N-二甲基-3-(3-溴-6-氟-2-甲基吲哚-1-磺酰基)-[1,2,4]三唑-1-磺酰胺;
氨基甲酸盐和二硫代氨基甲酸盐
-二硫代氨基甲酸盐类:福美铁(ferbam)、代森锰锌(mancozeb)、代森锰(maneb)、代森联(metiram)、威百亩(metam)、甲基代森锌(propineb)、福美双(thiram)、代森锌(zineb)、福美锌(ziram);
-氨基甲酸盐类:乙霉威(diethofencarb)、flubenthiavalicarb、异丙菌胺(iprovalicarb)、百维灵(propamocarb)、3-(4-氯苯基)-3-(2-异丙氧羰基氨基-3-甲基丁酰氨基)丙酸甲酯、N-(1-(1-(4-氰基苯基)乙烷磺酰基)丁-2-基)氨基甲酸4-氟苯基酯;
其他杀真菌剂
-胍类:多果定(dodine)、双胍辛醋酸盐(iminoctadine)、双胍盐(guazatine);
-抗生素类:春雷素(kasugamycin)、多氧霉素(polyoxins)、链霉素(streptomycin)、井冈霉素(validamycin A);
-有机金属化合物类:三苯锡基盐;
-含硫的杂环基化合物:稻瘟灵(isoprothiolane)、二噻农(dithianon);
-有机磷化合物:克瘟散(edifenphos)、藻菌磷(fosetyl)、乙膦铝(fosetyl-aluminum)、异稻瘟净(iprobenfos)、定菌磷(pyrazophos)、甲基立枯磷(tolclofos-methyl)、亚磷酸及其盐;
-有机氯化合物:甲基托布津(thiophanate-methyl)、百菌清(chlorothalonil)、抑菌灵(dichlofluanid)、对甲抑菌灵(tolylfluanid)、磺菌胺(flusulfamide)、四氯苯酞(phthalide)、六氯苯(hexachlorobenzene)、戊菌隆(pencycuron)、五氯硝基苯(quintozene);
-硝基苯基衍生物:乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton);
-无机活性化合物:波尔多液(Bordeaux混合物)、醋酸铜、氢氧化铜、王铜、碱式硫酸铜、硫;
其他:螺噁茂胺(spiroxamine)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、苯菌酮(metrafenone)。
需要的话,其它活性化合物以20∶1-1∶20的比例加入二甲嘧菌胺和二噻农的共晶中。
取决于化合物类型和所需效果,本发明共晶的施用率为5g/ha-2000g/ha,优选50-900g/ha,尤其是50-750g/ha。
例如通过撒粉、包衣或浸泡而用于种子处理的共晶的施用率通常为1-1000g/100kg种子,优选1-750g/100kg种子,尤其是5-500g/100kg种子。
当用于材料或储存产品的保护时,共晶的施用量取决于施用区域和所需效果。常用于材料保护的用量例如为每立方米处理材料0.001g-2kg,优选0.005g-1kg活性化合物。
防治有害真菌的方法通过在植物播种之前或之后或者植物出苗之前或之后对种子、植物或土壤喷雾或撒粉施用共晶而进行。
下述图和实施例用于阐述本发明而不应理解为限制本发明。
图1:通过在粘土盘上过夜干燥配制剂而由第16页上的对比例配制剂得到的共晶的X-射线粉末衍射谱图。
图2:二甲嘧菌胺和二噻农的共晶的光学显微图
分析:
X-射线粉末衍射谱图的照片使用购自Siemens的D-5000衍射仪在25℃下以2θ=4°-35°的反射几何角度和0.02°的增量使用Cu-Kα辐射得到。将所得2θ值用于计算所述晶面间距d。
晶型II和IV的晶体学数据(表1和2)在购自Siemens的单晶衍射仪上使用Cu-Kα辐射测量。
熔点测量使用Mettler Toledo热台显微镜在5℃/分钟的加热速率下进行。
悬浮液浓缩物中的粒度使用购自Malvern Instruments GmbH的Mastersizer 2000测定。
对比例
将65g尿素,43g Reax 910、2g Lutensit A-BO、20g Morwet 3D 425、2g Acticide MBS和250g去离子水在搅拌下均化直至获得清澈溶液。将305.21g二甲嘧菌胺工业级活性成分(TGAI)和318.1g二噻农TGAI加入该溶液中。将所得悬浮液在玻璃珠磨机中研磨以获得80%<2μm的粒度分布。在研磨过程中,温度升至约35℃并且悬浮液颜色由棕色变为深绿色。加入所需量的软化水以得到所需浓度的活性成分。此时的粘度低于100mPas。在制备1天之后,悬浮液具有稠膏的稠度。数天之后,悬浮液完全固化并且不再可倒出容器。
实施例1:
制备两种分开的预混物
预混物A:
将35g 1,2-丙二醇、10g Soprophor BSU、15g Pluronic PE 10500、5gAtplus 245、1g Acticide MBS和125g去离子水的混合物在搅拌下均化直至获得清澈溶液。将300g二甲嘧菌胺加入该溶液中。将所得悬浮液在玻璃珠磨机中研磨以获得80%<2μm的粒度分布。
预混物B:
将35g 1,2-丙二醇、10g Soprophor BSU、15g Pluronic PE 10500、5gAtplus 245、1g Acticide MBS和125g去离子水的混合物在搅拌下均化直至获得清澈溶液。将300g二噻农加入该溶液中。将所得悬浮液在玻璃珠磨机中研磨以获得80%<2μm的粒度分布。
将两种预混物A和B在烧杯中在50℃和搅拌下一起混合。在1小时之后,悬浮液从棕色变为深绿色。将悬浮液冷却至20℃,然后在玻璃珠磨机中研磨以得到80%<2μm的粒度分布(PSD)。产物粘度小于50mPas。产品在室温下保持不变化至少4个月。在此时间内粒度分布非常稳定。
实施例2:
使预混物A和B在升高温度下连续通过珠磨机。在半小时之后,整个悬浮液变为深绿色。将磨机冷却至20℃并继续研磨直至获得80%<2μm的PSD。
实施例3:
将70g 1,2-丙二醇、20g Soprophor BSU、30g Pluronic PE 10500、10gAtplus 245、2g Acticide MBS和250g去离子水的混合物在搅拌下均化直至获得清澈溶液。将300g二甲嘧菌胺加入该溶液中。将所得悬浮液在玻璃珠磨机中研磨以获得80%<2μm的粒度分布。在搅拌下向该悬浮液预混物中加入300g二噻农。在加入所有二噻农之后,将混合物加热至50℃并维持1小时。悬浮液变为深绿色并且在将其冷却至20℃之后,将其在珠磨机上研磨获得80%的PSD<2μm。
实施例4:
将70g 1,2-丙二醇、20g Soprophor BSU、30g Pluronic PE 10500、10gAtplus 245、2g Acticide MBS和250g去离子水的混合物在搅拌下均化直至获得清澈溶液。将300g二噻农加入该溶液中。将所得悬浮液在玻璃珠磨机中研磨以获得80%<2μm的粒度分布。在搅拌下向该悬浮液预混物中加入300g二甲嘧菌胺。在加入所有二甲嘧菌胺之后,将混合物加热至50℃并维持1小时。悬浮液变为深绿色并且在将其冷却至20℃之后,将其在珠磨机上研磨获得80%的PSD<2μm。
实施例5:
用合适的分散剂和乳化剂将二噻农和二甲嘧菌胺一起悬浮于基于矿物或植物的油,(如白油、Bayol 85、向日葵油、菜籽油、玉米油和油酸甲酯)中。将OD(油分散体)预混物在搅拌下加热至50℃,直至悬浮液的颜色由棕色变为深绿色(1小时)。然后将预混物冷却并在珠磨机上研磨以获得80%<2μm的PSD。
实施例6:
制备296.3g二噻农和199.4g二甲嘧菌胺在极性溶剂如DMSO、乙腈、DMF或丙酮中的溶液。将溶液混合并蒸发溶剂以得到495.6g共晶。将它们悬浮于水+配制添加剂(与对悬浮液浓缩物所述的相同)中并首先在PUC磨机上预研磨,然后在珠磨机上精磨以获得80%<2μm的PSD。
实施例7:
将干的二噻农和二甲嘧菌胺彻底混合并在搅拌下保持在50℃下。在数小时之后,粉末产物的颜色变为橄榄绿。在冷却的共晶预混物中加入对WG、WP和WDG配制剂典型的分散剂、消泡剂、润湿剂、辅助剂和填料。然后将预混物如下进一步加工:通过挤出得到WDG(水分散性颗粒)配制剂或在整理步骤之后作为WP(可湿性粉末)使用。也可将其悬浮于水中,然后喷雾干燥以得到水分散性颗粒。
施例8:
二甲嘧菌胺和二噻农的悬浮液预混物如实施例号3所述制备。然后使该预混物通过珠磨机以得到80%的PSD<2μm。然后,将所得悬浮液喷雾干燥以得到WDG配制剂。
Claims (15)
1.二甲嘧菌胺和二噻农的共晶,其在25℃下在X-射线粉末衍射谱图中显示至少3个如下反射:
2θ=7.46±0.20
2θ=9.98±0.20
2θ=13.28±0.20
2θ=23.09±0.20
2θ=24.38±0.20
2θ=27.01±0.20。
2.根据权利要求1的共晶,其具有165-175℃的熔点。
3.一种制备根据权利要求1的共晶的方法,其包括如下步骤:
i)将等摩尔量二甲嘧菌胺和二噻农在室温和搅拌下溶于极性有机溶剂,
ii)将溶剂蒸发以形成共晶。
4.一种制备根据权利要求1的共晶的方法,其包括如下步骤:
i)将等摩尔量的二甲嘧菌胺和二噻农干混以形成预混物,
ii)将预混物干磨以形成共晶。
5.一种制备根据权利要求1的共晶的方法,其包括如下步骤:
i)将等摩尔量的二甲嘧菌胺和二噻农与液体载体混合以形成预混物,
ii)研磨预混物以在载体上形成共晶,
iii)从载体中分离共晶。
6.一种用于作物保护的组合物,其包含根据权利要求1的共晶和载体和/或助剂。
7.根据权利要求6的组合物,其呈含水或水基悬浮液浓缩物形式。
8.根据权利要求6的组合物,其呈含水或基于植物或矿物油的悬浮液浓缩物形式。
9.一种制备含水悬浮液浓缩物的方法,其包括如下步骤:
i)将二甲嘧菌胺加入含有一种或多种分散剂和任选其他助剂的水中以形成预混物A,
ii)将二噻农加入含有一种或多种分散剂和任选其他助剂的水中以形成预混物B,
iii)将预混物A和B在20-150℃的温度和搅拌下一起混合以形成根据权利要求1的共晶的深绿色悬浮液,
iv)研磨如此获得的悬浮液至80%<2μm的粒度分布。
10.一种制备含水悬浮液浓缩物的方法,其包括如下步骤:
i)将二甲嘧菌胺加入含有一种或多种分散剂和任选其他助剂的水中以形成预混物A,
ii)将预混物A和二噻农在20-150℃的温度和搅拌下一起混合以形成根据权利要求1的共晶的深绿色悬浮液,
iii)研磨如此获得的悬浮液至80%<2μm的粒度分布。
11.一种制备含水悬浮液浓缩物的方法,其包括如下步骤:
i)将二噻农加入含有一种或多种分散剂和任选其他助剂的水中以形成预混物B,
ii)将预混物B和二甲嘧菌胺在20-150℃的温度和搅拌下一起混合以形成根据权利要求1的共晶的深绿色悬浮液,
iii)研磨如此获得的悬浮液至80%<2μm的粒度分布。
12.根据权利要求9的方法,其中步骤iii)中的温度为40-60℃。
13.根据权利要求9的方法,其中步骤iv)中的温度为20-30℃。
14.一种含水悬浮液浓缩物,其包含根据权利要求1的二甲嘧菌胺和二噻农的共晶、水和助剂。
15.根据权利要求6的组合物在防治植物病原性真菌中的用途。
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PCT/EP2008/061000 WO2009047043A1 (en) | 2007-09-07 | 2008-08-22 | Co-crystals of pyrimethanil and dithianon |
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Cited By (3)
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CN103764632A (zh) * | 2011-08-30 | 2014-04-30 | 巴斯夫欧洲公司 | 环丙嘧啶和二噻农的共晶 |
CN104250229A (zh) * | 2010-04-15 | 2014-12-31 | 先正达有限公司 | 嘧霉胺或嘧菌环胺的共晶 |
CN105557695A (zh) * | 2014-10-16 | 2016-05-11 | 江苏龙灯化学有限公司 | 一种活性成分组合物 |
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GB0817976D0 (en) * | 2008-10-01 | 2008-11-05 | Syngenta Ltd | Co-crystals |
KR20120115492A (ko) * | 2009-11-06 | 2012-10-18 | 바스프 에스이 | 4―히드록시 벤조산 및 선택된 살충제의 결정질 복합체 |
CN102763657B (zh) * | 2012-08-13 | 2014-09-17 | 江苏辉丰农化股份有限公司 | 具有增效作用的杀菌组合物 |
EP2964033A1 (en) | 2013-03-07 | 2016-01-13 | Basf Se | Co-crystals of pyrimethanil and selected dithiine tetracarboximide |
US10226426B2 (en) | 2015-03-02 | 2019-03-12 | Takeda Pharmaceutical Company Limited | Suspension containing nano-cocrystal and manufacturing method |
GB201801544D0 (en) * | 2018-01-31 | 2018-03-14 | Johnson Matthey Plc | Co-crystals |
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DD151404A1 (de) | 1980-06-13 | 1981-10-21 | Friedrich Franke | Fungizide mittel |
NZ537091A (en) * | 2002-07-08 | 2007-09-28 | Basf Ag | Fungicidal mixtures based on dithianon |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104250229A (zh) * | 2010-04-15 | 2014-12-31 | 先正达有限公司 | 嘧霉胺或嘧菌环胺的共晶 |
CN104250229B (zh) * | 2010-04-15 | 2017-05-03 | 先正达有限公司 | 嘧霉胺或嘧菌环胺的共晶 |
CN103764632A (zh) * | 2011-08-30 | 2014-04-30 | 巴斯夫欧洲公司 | 环丙嘧啶和二噻农的共晶 |
CN103764632B (zh) * | 2011-08-30 | 2017-05-17 | 巴斯夫欧洲公司 | 环丙嘧啶和二噻农的共晶 |
CN105557695A (zh) * | 2014-10-16 | 2016-05-11 | 江苏龙灯化学有限公司 | 一种活性成分组合物 |
CN105557695B (zh) * | 2014-10-16 | 2018-02-27 | 江苏龙灯化学有限公司 | 一种活性成分组合物 |
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MA31756B1 (fr) | 2010-10-01 |
PT2197278E (pt) | 2013-07-09 |
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ES2413859T3 (es) | 2013-07-17 |
PL2197278T3 (pl) | 2013-10-31 |
DK2197278T3 (da) | 2013-08-26 |
UA99146C2 (ru) | 2012-07-25 |
KR20100061719A (ko) | 2010-06-08 |
BRPI0816376A2 (pt) | 2014-09-30 |
EA016391B1 (ru) | 2012-04-30 |
JP5398717B2 (ja) | 2014-01-29 |
EP2197278B1 (en) | 2013-05-29 |
MX2010001705A (es) | 2010-03-11 |
EA201000434A1 (ru) | 2010-10-29 |
CN101795566B (zh) | 2014-04-16 |
ZA201002381B (en) | 2011-06-29 |
CY1114374T1 (el) | 2016-08-31 |
SI2197278T1 (sl) | 2013-07-31 |
CR11332A (es) | 2010-05-19 |
EP2197278A1 (en) | 2010-06-23 |
JP2010538037A (ja) | 2010-12-09 |
AU2008309828A1 (en) | 2009-04-16 |
US20100184792A1 (en) | 2010-07-22 |
RS52806B (en) | 2013-10-31 |
US8324233B2 (en) | 2012-12-04 |
ECSP10010078A (es) | 2010-04-30 |
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