CN101535277A - 2-氯-5-[3,6-二氢-3-甲基-2,6-二氧代-4-(三氟甲基)-1-(2h)嘧啶基]-4-氟-n-[[甲基(1-甲基乙基)氨基]磺酰基]苯甲酰胺的结晶形式 - Google Patents
2-氯-5-[3,6-二氢-3-甲基-2,6-二氧代-4-(三氟甲基)-1-(2h)嘧啶基]-4-氟-n-[[甲基(1-甲基乙基)氨基]磺酰基]苯甲酰胺的结晶形式 Download PDFInfo
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- CN101535277A CN101535277A CNA2007800409115A CN200780040911A CN101535277A CN 101535277 A CN101535277 A CN 101535277A CN A2007800409115 A CNA2007800409115 A CN A2007800409115A CN 200780040911 A CN200780040911 A CN 200780040911A CN 101535277 A CN101535277 A CN 101535277A
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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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
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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
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Abstract
本发明涉及2-氯-5-[3,6-二氢-3-甲基-2,6-二氧代-4-(三氟甲基)-1-(2H)嘧啶基]-4-氟-N-[[甲基(1-甲基乙基)氨基]磺酰基]苯甲酰胺的结晶形式。本发明还涉及一种制备该结晶形式的方法和包含该苯基尿嘧啶的结晶形式的作物保护配制剂。
Description
本发明涉及2-氯-5-[3,6-二氢-3-甲基-2,6-二氧代-4-(三氟甲基)-1-(2H)嘧啶基]-4-氟-N-[[甲基(1-甲基乙基)氨基]磺酰基]苯甲酰胺(在下文中也称做苯基尿嘧啶I)的结晶形式。本发明还涉及一种制备该结晶形式的方法和包含该苯基尿嘧啶的结晶形式的作物保护配制剂。
具有下式的苯基尿嘧啶I为除草活性物质:
其公开于WO 01/083459中。它的其它制备方法公开于WO 03/097589、WO 05/054208和WO 06/097589以及在先国际申请PCT/EP 2006/062414中。所有苯基尿嘧啶I的已知制备方法均提供了无定型物质。
委托公司的研究表明无定型苯基尿嘧啶I仅中度适用于制备包含作为固体的物质的配制剂。在多相配制剂的情况下,尤其会出现稳定性问题。
现在惊人地发现合适的方法产生不具有这些缺点的基本不含溶剂的苯基尿嘧啶I的结晶形式。此外,与目前已知的无定型形式的苯基尿嘧啶I相比,还惊人地发现该结晶形式具有更好的除草活性,并在一系列作物中具有更好的作物植物耐受性。本发明结晶形式也比目前的无定型形式更致密,并且在制备它时以离散晶体或微晶形式产生。因此可比形式I更容易地处理。
因此,本发明涉及基本不含溶剂的2-氯-5-[3,6-二氢-3-甲基-2,6-二氧代-4-(三氟甲基)-1-(2H)-嘧啶基]-4-氟-N-[[甲基(1-甲基乙基)氨基]磺酰基]苯甲酰胺的结晶形式。
为了区别本发明的基本不含溶剂的苯基尿嘧啶I的形式和已知的无定型形式(在下文中称作形式I),在下文中将前者也称作形式II。
对于形式II,术语“基本不含溶剂”是指本发明形式II不包含可检测量的掺入晶格中的溶剂,即晶格中的溶剂量基于苯基尿嘧啶I小于10mol%,尤其是不超过5mol%。
本发明形式II可借助X-射线粉末衍射基于其衍射谱图鉴别。因此,在25℃下使用Cu-Kα辐射记录的X-射线粉末衍射图显示表1中详述的至少2个,通常至少4个,经常至少6个,尤其是至少8个,特别是所有反射(在下文中作为2θ值,或作为晶面间距d):
表1:
在-170℃下研究形式II的单晶显示,基础晶体结构为单斜的。晶胞具有空间群P2(1)/c。形式II的晶体结构的特征数据汇集在表2中。
表2:形式2的晶体学特征(在-170℃下测量)
a,b,c=晶胞长度
α,β,γ=晶胞角度
Z=晶胞中的分子数
除X-射线粉末衍射和晶体学分析外,差示扫描量热法(DSC)也可用于鉴别形式II。
形式II显示了在170-200℃之间具有特征熔融峰的差示热分析图。峰顶点通常位于约180-190℃之间。此处显示的熔点指借助差示扫描量热法(DSC,坩锅材料铝,加热速率5K/min)测定的数据。
本发明的苯基尿嘧啶I的形式II通过从苯基尿嘧啶I在基本不含水的有机溶剂中的溶液中受控地结晶而成功制备。
为此,在第一步i)中提供苯基尿嘧啶I在基本不含水的有机溶剂中的溶液,然后在第二步中使苯基尿嘧啶I受控地结晶。
就此而言,基本不含水是指水在包含苯基尿嘧啶I的溶液中的浓度基于溶剂总量不超过10重量%,经常5重量%,尤其1重量%。
术语“受控地结晶”理解为指结晶总计进行至少1小时,经常至少2小时,尤其是至少3小时的延长时间。结晶也可进行长达数天,如1、2至3天的延长时间。然而,结晶时间通常不超过15小时。因此,结晶通常进行1-24小时,经常2-15小时,尤其是3-10小时。
原则上合适的溶剂为其中苯基尿嘧啶I可足以在升高温度下溶解,例如在50℃下的溶解度为至少100g/l的那些溶剂和溶剂混合物。
此外,优选沸点在大气压力下为50-160℃的溶剂和溶剂混合物。
合适的溶剂的实例尤其为下文详述的有机溶剂,在下文中也称作溶剂L1:
-C1-C6链烷醇,如甲醇、乙醇、丙醇、正丁醇、异丁醇、叔丁醇、1-戊醇或己醇,
-具有3-8个碳原子的无环酮,如丙酮、甲基乙基酮或3-甲基丁-2-酮(异丙基甲基酮),
-具有5-8个碳原子的环状酮,如环己酮或环庚酮,
-芳族烃和烃混合物,和芳族氯代烃,尤其是单-和二C1-C3烷基苯,如甲苯、二甲苯、氯苯和二氯苯,
-二C1-C6烷基醚,如乙醚、二异丙基醚和甲基叔丁基醚,
-5或6元脂环族醚如四氢呋喃(THF)或二噁烷,
-具有1-3个碳原子的硝基链烷烃如硝基甲烷,
-具有2-6个碳原子的烷基腈,如乙腈、丙腈、异丁腈和丁腈,
-脂族C1-C4羧酸的C1-C4烷基酯,尤其是乙酸的C1-C4烷基酯,如乙酸乙酯和乙酸丁酯,
-脂族C1-C4羧酸的N,N-二甲基酰胺,如二甲基甲酰胺和二甲基乙酰胺,和
-上述溶剂的混合物。
优选有机溶剂L1为:
-C2-C4链烷醇,如甲醇、乙醇、丙醇、正丁醇、异丁醇和叔丁醇,
-具有3-6个碳原子的无环酮,如丙酮、甲基乙基酮或3-甲基丁-2-酮(异丙基甲基酮),
-单C1-C3烷基苯,如甲苯,
-二-C1-C6烷基醚,如乙醚、二异丙基醚和甲基叔丁基醚,
-乙酸的C1-C4烷基酯,如乙酸乙酯和乙酸丁酯,
-5-或6元脂环族醚如四氢呋喃(THF),和
-上述溶剂的混合物。
特别优选的有机溶剂L1为单C1-C3烷基苯,特别是甲苯,和单C1-C3烷基苯,特别是甲苯与四氢呋喃的混合物。还优选的是,优选溶剂L1,尤其是单C1-C3烷基苯,特别是甲苯与甲醇的混合物,其中甚至少量甲醇(例如至多20体积%,尤其是至多10体积%)导致改进纯度的所得结晶物(crystallizate)。
原则上还合适的是上述有机溶剂L1与其它溶剂L2的混合物,其中溶剂L1通常占用于结晶的溶剂的主要量,尤其是占至少70重量%,特别是占至少90重量%。特别是,溶剂L1为仅有的溶剂或基于全部溶剂量包含小于5重量%的L1之外的有机溶剂。
其它有机溶剂L2尤其为:
-优选具有2-6个碳原子的碳酸酯,如碳酸二甲酯、碳酸二乙酯或碳酸亚乙酯,-脂族C1-C4羧酸的C1-C6烷基酯,如乙酸甲酯、乙酸乙酯、乙酸丙酯、异丁酸甲酯和乙酸异丁酯,
-羟基-C1-C4烷基芳族化合物和C1-C4烷基羰基芳族化合物如苄醇和苯乙酮,
-脂族氯代烃如二氯甲烷和二氯乙烷,
-优选具有2-6个碳原子的亚砜,如二甲亚砜
-优选具有2-6个碳原子的砜,如二甲砜和四亚甲基砜,和
-通常具有5-10个碳原子的脂族和脂环族烃,如己烷、环己烷、石油醚和石油醚(petroleum benzine)。
苯基尿嘧啶I在用于结晶的溶液中的浓度自然取决于溶剂类型和溶液温度且经常为50-800g/l。合适的条件可通过本领域熟练技术人员基于常规试验测定。
优选用于结晶的苯基尿嘧啶I溶液以至少85%,经常至少90%,尤其是至少95%的纯度包含苯基尿嘧啶I,即不为有机溶剂的有机杂质量基于以溶解于溶剂中的形式存在的苯基尿嘧啶I不超过15重量%,经常不超过10重量%,尤其是不超过5重量%。
包含苯基尿嘧啶I的溶液可例如通过如下方法提供:
(1)在基本不含水的溶剂中溶解苯基尿嘧啶I(其优选呈不同于形式II的形式);或
(2)通过化学反应制备苯基尿嘧啶I并将反应混合物(合适的话在除去反应试剂和/或副产物之后)转移入根据本发明适合的且基本不含水的有机溶剂中。
原则上,任何已知形式的苯基尿嘧啶I可用于通过溶解苯基尿嘧啶I而制备溶液。当然,使用不同于形式II的苯基尿嘧啶I的形式。适合于此的尤其为由现有技术已知的苯基尿嘧啶固体或液体熔体或无定型苯基尿嘧啶I。除形式I外,苯基尿嘧啶的合适形式还有溶剂化物,尤其是苯基尿嘧啶I的水合物或苯基尿嘧啶I的甲醇溶剂化物。还合适的是不同形式的苯基尿嘧啶的混合物。苯基尿嘧啶I的水合物是平行专利申请的主题,此处对其全部参考。
用于溶解苯基尿嘧啶I的溶剂通常采用上述有机溶剂L1之一的形式或不同溶剂L1的混合物形式或采用基于用于溶解的溶剂总量包含至少70重量%,特别是至少90重量%溶剂L1的溶剂混合物形式。
为了溶解不同于形式II的苯基尿嘧啶I的形式,通常将苯基尿嘧啶I以细的颗粒固体形式或作为熔体通过混合而掺入溶剂中,该方法在溶剂或溶剂混合物能够完全溶解苯基尿嘧啶I的温度下进行。
溶解无定型形式I通常在20-160℃的温度下进行。在本发明的优选实施方案中,苯基尿嘧啶I的溶解在升高温度,尤其是至少50℃,特别是至少80℃的温度下进行,当然,用于溶解的温度不超过溶剂沸点。溶解通常在50-140℃,尤其是80-120℃,特别优选95-115℃的温度下进行。
溶解于溶剂中的苯基尿嘧啶I的量当然取决于溶剂L1的性质和溶解温度并且通常为100-800g/l。合适的条件可由本领域熟练技术人员通过常规实验确定。
苯基尿嘧啶I溶液也可通过将由化学反应得到且包含苯基尿嘧啶I的反应混合物(合适的话在除去反应试剂和/或副产物之后)转移入基本不含水并根据本发明适合的有机溶剂中而提供。此处程序可如下进行,其中反应在适用于结晶的有机溶剂中或在至少部分包含,优选包含至少50重量%适用于结晶的溶剂的溶剂混合物中进行,以及合适的话进行后处理,其中除去可能存在的过量反应试剂和任何催化剂和可能存在的任何不合适的溶剂如水和/或甲醇。通过使合适的苯基尿嘧啶I前体化学反应而制备苯基尿嘧啶I溶液可类似于开头引用的现有技术(此处对其全部参考)中所述的方法进行。
在苯基尿嘧啶I的溶剂化物用于制备溶液的情况下,可能有利的是在溶解步骤之后但在结晶步骤之前例如借助蒸馏除去溶剂化物溶剂。
苯基尿嘧啶I的形式II的结晶可以常规方式进行,例如通过如下方式进行:
-冷却包含溶解形式的苯基尿嘧啶I的溶液,
-向包含溶解形式的苯基尿嘧啶I的溶液中加入降低溶解度的有机溶剂,尤其是加入无水非极性有机溶剂;
-浓缩包含溶解形式的苯基尿嘧啶I的溶液,或
-将上述措施组合。
通常而言,结晶进行至使得至少80重量%,优选至少90重量%的所用苯基尿嘧啶I结晶出。
在本发明的优选实施方案中,程序如下进行,其中在升高温度下,优选在至少50℃,例如50-150℃,优选80-120℃,特别优选100-115℃下制备包含溶解形式的苯基尿嘧啶I的溶液,随后,通过冷却以及合适的话浓缩溶液而使苯基尿嘧啶I结晶。优选将苯基尿嘧啶I溶液冷却至少20K,尤其是冷却30-60K而引发结晶。冷却程序可以受控方式进行,即在通常不超过20K/h,例如0.5-20K/h,经常1-15K/h的缓慢冷却速率下进行。有利的是,受控冷却作为结晶启动进行。然而,也可更快速冷却,此时在分离之前,结晶物会在母液中移动延长时间,即直至达到所需结晶时间。
为改进纯度,结晶可以如下方式进行,首先冷却苯基尿嘧啶溶液,直至部分或全部苯基尿嘧啶结晶出,然后再加热以早期溶解结晶物,但不完全溶解结晶物,随后再冷却溶液。对于温度和冷却速率,此处类似地适用上文所述内容。
形式II的结晶可通过用形式II的种晶加种晶,如通过在结晶工艺之前或之中加入形式II的种晶而促进或加速。
在结晶工艺中加入种晶的情况下,它们的量基于溶解的苯基尿嘧啶I通常为0.001-10重量%,经常0.005-5重量%,尤其是0.01-1重量%,特别是0.05-0.5重量%。
在形式II的种晶存在下进行结晶的情况下,这些种晶优选仅在各溶剂中的苯基尿嘧啶I达到饱和浓度的温度下加入,即在该温度或在该温度之下,在所述溶剂中的溶解量的苯基尿嘧啶I形成饱和溶液。在溶剂中的饱和浓度的温度依赖性可由本领域熟练技术人员在常规实验中测定。种晶经常在溶液温度不超过60℃时加入。在加入种晶之后,在将所得结晶材料从母液中分离以分离形式II的苯基尿嘧啶I之前,优选将溶液冷却至低于30℃,尤其是25℃或更低的温度,例如冷却至0-25℃的温度。在种晶存在下冷却可以受控方式在通常不超过30K/h,例如1-30K/h,经常2-20K/h,尤其是3-15K/h的冷却速率下进行,或以非受控方式进行。
如上所述,在再加热至早期溶解结晶物之后重新冷却可导致改进的产物纯度。
已证明有利的是在低于结晶温度的温度,如0-35℃下使结晶材料在母液中移动一段时间,如1-3小时,以确保完全结晶为形式II。从冷却工艺开始到通过分离母液而分离晶体的总时间因此在上述范围内。
或者,也可通过加入无水非极性溶剂L2引起结晶,例如其基于用于溶解苯基尿嘧啶I的溶剂或溶剂混合物体积为5-60体积%,尤其是20-55体积%,特别是30-50体积%。优选加入非极性溶剂L2在延长时间内进行,例如进行30分钟至10小时,尤其是1-8小时。
尤其可以将加入非极性溶剂和加入种晶相互组合。加入非极性溶剂可以纯非极性溶剂形式或以非极性溶剂与上述溶剂L1之一的混合物,尤其是以与用于溶解工艺的溶剂的混合物形式进行。非极性溶剂的实例为脂族和脂环族烃如戊烷、己烷、环己烷、异己烷、庚烷、辛烷、癸烷,和卤代芳族化合物如氯苯、二氯苯或它们的混合物。
由结晶物得到形式II,即从母液中取出形式II通过常用于分离固体组分和液体的技术,如通过过滤、离心或滗析而成功完成。通常使用用于结晶的溶剂、水或用于结晶的有机溶剂和水的混合物洗涤分离的固体。洗涤可以一步或多步进行,最后的洗涤步骤通常用水进行。洗涤通常在低于30℃,经常低于25℃,尤其是低于20℃的温度下进行,以使目标产物的损失尽可能低。然后,可将所得形式II干燥,然后加工。然而,经常将洗涤之后得到的潮的活性成分,尤其是水-潮的活性成分直接加工。
本发明结晶产生苯基尿嘧啶I含量为至少94重量%,尤其是至少96重量%的形式II。形式II的含量基于苯基尿嘧啶I的总量通常为至少90%,经常至少95%,尤其是至少98%。
用作制备形式II的原料的2-氯-5-[3,6-二氢-2,6-二氧代-4-(三氟甲基)-1(2H)-嘧啶基]-4-氟-N-[[甲基(1-甲基乙基)氨基]磺酰基]苯甲酰胺的制备可经由WO01/083459、WO03/097589、WO 05/054208、WO 06/097589和PCT/EP 2006/062414中所述的方法进行,此处完全引入作为参考。
尤其优选通过如下方法制备苯基尿嘧啶I:
1)将2-氯-5-[3,6-二氢-2,6-二氧代-4-(三氟甲基)-1(2H)-嘧啶基]-4-氟苯甲酸转化为其酰氯或相应酸酐,随后用N-甲基-N-(1-甲基乙基)磺酰胺转化相应的活化酸衍生物,如:
该反应通常在20℃至反应混合物沸点的温度下在有机溶剂中在碱,以及合适的话催化剂存在下进行[例如参见WO 01/083459、WO 03/097589以及WO 04/039768]。
合适的溶剂为脂族烃如戊烷、己烷、环己烷和C5-C8链烷烃的混合物,芳族烃如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃如二氯甲烷、氯仿和氯苯,醚类如乙醚、二异丙基醚、叔丁基甲基醚、二噁烷、茴香醚和四氢呋喃,腈类如乙腈和丙腈,酮类如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,醇类如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,以及二甲亚砜、二甲基甲酰胺和二甲基乙酰胺。也可使用上述溶剂的混合物。
合适的碱通常为无机碱如碱金属和碱土金属氢氧化物如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属和碱土金属氧化物如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属氢化物如氢化锂、氢化钠、氢化钾和氢化钙,碱金属氨基化物如氨化锂、氨化钠和氨化钾,碱金属和碱土金属碳酸盐如碳酸锂、碳酸钾和碳酸钙,以及碱金属碳酸氢盐如碳酸氢钠,有机金属化合物,尤其是碱金属烷基化物如甲基锂、丁基锂和苯基锂,烷基镁卤化物如甲基氯化镁,以及碱金属和碱土金属醇盐如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾、叔戊醇钾和二甲氧基镁,还有有机碱,如叔胺,如三甲胺、三乙胺、二异丙基乙胺和N-甲基哌啶,吡啶,取代的吡啶如可力丁、卢剔啶和4-二甲氨基吡啶,和双环胺。
碱通常以催化量或等摩尔量使用,但它们也可以过量使用或合适的话用作溶剂。
原料通常以等摩尔量相互反应。可能有利的是过量使用一种原料。
2)用甲基化试剂C将2-氯-5-[3,6-二氢-2,6-二氧代-4-(三氟甲基)-1(2H)-嘧啶基]-4-氟-N-[[甲基(1-甲基乙基)氨基]磺酰基]苯甲酰胺(在下文中:“NH-尿嘧啶”)甲基化:
基团L1表示亲核离去基团,优选卤素如氯、溴或碘,C1-C6烷基硫酸根如甲基硫酸根,C1-C6烷基磺酰氧基如甲基磺酰基氧基,C1-C6卤代烷基磺酰氧基如三氟甲基磺酰基氧基或苯基磺酰氧基;非常优选C1-C6烷基硫酸根。
合适的甲基化试剂C为甲基卤如甲基碘、甲基溴、甲基氯,硫酸二甲酯,甲基C1-C6卤代烷基磺酸酯或甲基苯基磺酸酯,特别优选甲基卤和硫酸二甲酯;额外优选硫酸二甲酯。
基于NH-尿嘧啶,甲基化试剂C可以等摩尔量使用,以及低于化学计量或过量使用。
方法(2)通常在碱存在下进行,其中所有常用有机和无机碱是合适的,如在方法(1)中提及的碱。优选碱选自碱金属和碱土金属氢氧化物如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属和碱土金属氧化物如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属碳酸盐如碳酸锂、碳酸钠、碳酸钾和碳酸钙,以及碱金属碳酸氢盐如碳酸氢钠。在一个特别优选的实施方案中,将氢氧化钠或氢氧化钾用作碱。基于NH-尿嘧啶,碱通常以等摩尔量使用,但它们也可以催化量、过量使用或合适的话用作溶剂。
在非常优选的方法(2)的变型中,通过连续或分批加入碱而在所有反应中将pH保持为1-6。“分批加入碱”是指在转化过程中以数部分,即以至少2部分,或更多部分,直至许多部分或连续而加入碱。
为进行反应,可将NH-尿嘧啶、甲基化试剂C以及合适的话碱分开、同时或依次引入反应容器中并反应。
根据方法(2)的第一实施方案,用甲基化试剂C转化NH-尿嘧啶在有机溶剂中进行。
取决于温度范围,适合这些反应的溶剂为脂族、脂环族或芳族烃,如戊烷、己烷、环戊烷、环己烷、甲苯、二甲苯,氯代脂族和芳族烃如二氯甲烷、三氯甲烷、1,2-二氯乙烷、1,1,2,2-四氯乙烷、氯苯,1,2-、1,3-或1,4-二氯苯,氯甲苯,二氯甲苯,开链二烷基醚如乙醚、二正丙基醚、二正异丙基醚、甲基叔丁基醚,环状醚如四氢呋喃、1,4-二噁烷、茴香醚、甘醇醚如二甲基乙二醇醚、二乙基乙二醇醚、二甘醇二甲醚、二甘醇二乙醚,C1-C4醇如甲醇、乙醇、正丙醇、异丙醇、正丁醇,脂族羧酸的C1-C6烷基酯,如乙酸甲酯、乙酸乙酯或乙酸正丁酯;酮类如丙酮、甲基乙基酮、甲基异丙基酮、甲基异丁基酮、丁酮,碳酸酯如碳酸二乙酯和碳酸亚乙酯,N,N-二烷基酰胺如N,N-二甲基甲酰胺和N,N-二甲基乙酰胺,N-烷基内酰胺如N-甲基吡咯烷酮,亚砜如二甲亚砜,四烷基脲如四甲基脲、四乙基脲、四丁基脲、二甲基亚乙基脲、二甲基亚丙基脲,或这些溶剂的混合物。
优选溶剂为N,N-二烷基酰胺如N,N-二甲基甲酰胺,N-烷基内酰胺如N-甲基吡咯烷酮,酮类如丙酮,芳族烃如甲苯,氯代脂族和芳族烃如二氯甲烷或氯苯,环状醚如四氢呋喃,脂族羧酸的C1-C6烷基酯,如乙酸甲酯、乙酸丁酯,或这些溶剂的混合物。
NH-尿嘧啶的甲基化优选在-5℃至100℃的温度下进行。反应时间可通过熟练技术人员以本身已知的方式通过常规方法如薄层层析或HPLC确定。
在方法(2a)的另一变型中,转化也可在多相体系中进行。优选该变型。
对于甲基化试剂C、pH、碱、温度和压力,此处适用上文所述内容。
根据方法(2)的第二优选实施方案,NH-尿嘧啶与甲基化试剂C的反应在水-有机多相体系中在一种或多种相转移催化剂存在下进行。
相转移催化剂的实例为季铵盐、磷鎓盐、冠醚或聚乙二醇类。优选合适的季铵盐例如包括四(C1-C18)烷基卤化铵和N-苄基三(C1-C18)烷基卤化铵。优选合适的磷鎓盐例如包括C1-C18烷基三苯基磷鎓氯化物、C1-C18烷基三苯基磷鎓溴化物、C1-C18烷基三苯基磷鎓乙酸盐、四(C1-C18)烷基磷鎓氯化物或四(C1-C18)烷基磷鎓溴化物、四苯基磷鎓氯化物或四苯基磷鎓溴化物、苄基三苯基磷鎓氯化物或苄基三苯基磷鎓溴化物。优选合适的冠醚例如包括18-冠-6、二苯并-18-冠-6。优选合适的聚乙二醇类例如包括二甘醇二丁醚、四甘醇二甲醚、三甘醇二甲醚、聚乙二醇二甲醚。通常而言,相转移催化剂基于NH-尿嘧啶以至多20摩尔%的量使用。
多相体系包含水相和至少一个有机液体相。此外,也可存在固相。
水相优选为包含碱的溶液,尤其是碱金属或碱土金属氢氧化物(如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙)、碱金属或碱土金属碳酸盐(例如碳酸锂、碳酸钠、碳酸钾和碳酸钙)或碱金属碳酸氢盐(如碳酸氢钠)的水溶液。特别优选使用碱金属或碱土金属氢氧化物,非常优选氢氧化钠。
基于NH-尿嘧啶,碱通常以等摩尔量使用,但也可以催化量,过量使用或合适的话用作溶剂。优选基于NH-尿嘧啶使用至少等摩尔量的碱。
取决于温度范围,适用于有机相的溶剂优选为脂族、脂环族或芳族烃如戊烷、己烷、环戊烷、环己烷、甲苯、二甲苯,氯代脂族和芳族烃如二氯甲烷、三氯甲烷、1,2-二氯乙烷、1,1,2,2-四氯乙烷、氯苯,1,2-、1,3-或1,4-二氯苯,氯甲苯,二氯甲苯,开链二烷基醚如乙醚、二正丙基醚、二正异丙基醚、甲基叔丁基醚,环状醚如四氢呋喃(THF)和茴香醚,脂族羧酸的C1-C6烷基酯,如乙酸甲酯、乙酸乙酯或乙酸正丁酯或这些溶剂的混合物。优选用于有机相的溶剂为乙酸乙酯、乙酸正丁酯、氯苯、THF、甲苯或这些溶剂的混合物;非常优选乙酸乙酯,乙酸正丁酯,氯苯和THF混合物,以及甲苯和THF混合物。
例如当NH-尿嘧啶、甲基化试剂C、碱和/或相转移催化剂没有完全溶解时,可在转化过程中出现固相。
在优选实施方案中,多相体系中作为水相由氢氧化钠水溶液组成,和作为有机相由甲苯和四氢呋喃,或二氯甲烷和四氢呋喃,氯苯和四氢呋喃,或乙酸乙酯或乙酸正丁酯组成。
为进行转化,可将NH-尿嘧啶、甲基化试剂C、碱以及合适的话相转移催化剂分开、同时或依次引入反应容器中并在其中反应。
当使用两相体系时,在形式II结晶之前,所述相通常会分开。在进行结晶之前,特别优选通过本领域熟练技术人员已知的干燥方法,例如通过将水与部分有机溶剂一起共沸蒸出而干燥所得产物。
下文的图和实施例意欲阐述本发明而不是限制本发明。
图1显示了形式II的X-射线粉末衍射图。形式II的X-射线衍射谱图用购自Bruker-AXS的衍射仪型号D-5000使用Cu-Kα辐射在25℃下记录,反射几何角度2θ=4°—35°,步长为0.02°。所报导的晶面距d由所测的2θ值计算。
图2显示了形式II的IR光谱。IR谱借助购自Thermo Electron Corp./美国的FTIR光谱仪“Nicolet Magna 550”和“Nicolet Magna 750”在400-4000cm-1的波长范围内以4cm-1(32次扫描)的分辨率记录。测试样品为KBr压片。
熔点和熔化热经由DSC使用购自Mettler的Mettler Toledo DSC 25在5K/min的加热速率下在—5℃至+80℃的范围内测定。样品量为5-10mg。
形式II的结晶学数据(表1)使用购自Bruker(“Bruker P4”)的单晶衍射仪使用Cu-Kα辐射测定。
通过除去溶剂而使无定型形式I从有机溶剂中结晶而制备苯基尿嘧啶
I的形式II(通用程序)
在每种情况下,将1g无定型苯基尿嘧啶I在室温下溶解于25ml所述溶剂中。将所得溶液温热至表3详述的温度并放置在该温度下,使氮气流通过溶液以蒸发溶剂。在除去溶剂之后,将混合物冷却至环境温度,将结晶材料分离并借助DSC和/或借助X-射线粉末衍射(XRD)分析。在所有情况下得到形式II。
表3
实施例 | 溶剂 | T[℃] | XRD1) | DSC峰[℃] |
1 | 丙酮 | 35 | n.a. | 187 |
2 | 异丙醇 | 35 | + | 183,187 |
3 | 异丙醇 | 70 | n.a. | 190 |
4 | 甲苯 | 35 | + | 189 |
5 | 甲苯 | 80 | + | 189 |
6 | 甲基异丁基酮 | 100 | n.a. | 189 |
7 | 1-戊醇 | 50 | n.a. | 188 |
8 | 1-戊醇 | 120 | + | 178 |
9 | 硝基甲烷 | 40 | + | 186 |
1)X-射线粉末衍射图:+=测量;n.a.未测量
实施例10:将1g无定型苯基尿嘧啶I在室温下溶解于25ml乙腈中。将清澈溶液在室温下放置1周,并且不覆盖,在此期间大部分溶剂蒸发并剩下结晶的白色沉淀。位于187℃的DSC峰证实了形式II的存在。
实施例11:通过将苯基尿嘧啶I从丙酮中结晶而制备形式II
将0.2g无定型形式I在22℃和搅拌下溶解于10滴丙酮中。然后,持续搅拌3分钟,首先形成混浊,在接下来的30分钟内随着形成沉淀而增强。使沉淀沉降(30分钟),然后真空除去丙酮;这得到0.191g(理论值的96%)熔点为180-184℃的形式II。
实施例12:通过从反应溶液中结晶而制备苯基尿嘧啶I的形式II
将50.0g(0.098mol)2-氯-5-[3,6-二氢-2,6-二氧代-4-(三氟甲基)-1(2H)-嘧啶基]-4-氟-N-{[甲基(1-甲基乙基)氨基]磺酰基}苯甲酰胺、3.2g(0.0089mol)四丁基溴化铵(=TBAB)和15.1g(0.12mol)硫酸二甲酯在25℃下引入反应容器中的甲苯、水和THF的混合物中,并将混合物加热至40℃。然后通过加入浓度为10%的NaOH水溶液而在反应混合物中建立5.3-5.5的pH。在整个反应过程中,加入更多的浓度为10%的NaOH水溶液,以使pH在整个反应过程中恒定在预先建立的相同pH。在反应结束后,将反应混合物在40℃下持续搅拌3.5小时。随后分离相。
通过在大气压力下蒸馏而从所得溶液中除去55-60%的所用溶剂,得到标题化合物在甲苯中的热溶液。随后将溶液冷却至70℃,然后在5小时内以恒定的冷却速率冷却至20℃,并在20℃下持续搅拌3小时。将沉淀的固体吸滤并干燥。这得到42.6g(84.0%)活性成分含量为96.8%的作为形式II的标题化合物。
如形式I,形式II适合用作除草剂,但就活性而言优于前者。因此,本发明还涉及包含结晶形式II和常用于配制植物保护组合物的辅助剂的植物保护组合物,尤其是呈含水或非水性悬浮液浓缩物形式的植物保护组合物。本发明还涉及一种防治不希望的植物生长的方法,其包括使苯基尿嘧啶的形式II,优选作为合适的活性物质制剂作用于植物、其环境和/或种子。
包含形式II的除草组合物尤其在高施用率下非常良好的防治非作物区域的植物生长。它们可以在诸如小麦、稻、玉米、大豆和棉花的作物中非常良好地防治阔叶杂草和禾本科杂草,而不损害作物植株。尤其在低施用率下也观察到该作用。
取决于所述施用方法,形式II或包含它的除草组合物可以额外用于许多其他作物植物中以消除不希望的植物。合适的作物实例如下:洋葱(Allium cepa)、凤梨(Ananas comosus)、落花生(Arachis hypogaea)、石刁柏(Asparagus officinalis)、甜菜(Beta vulgaris spp.altissima)、甜菜(Betavulgaris spp.rapa)、欧洲油菜(Brassica napus var.napus)、芜青甘蓝(Brassica napus var.napobrassica)、芜青(Brassica rapa var.silvestris)、大叶茶(Camellia sinensis)、红花(Carthamus tinctorius)、美国山核桃(Caryaillinoinensis)、柠檬(Citrus limon)、甜橙(Citrus sinensis)、小果咖啡(Coffeaarabica)(中果咖啡(Coffea canephora)、大果咖啡(Coffea liberica))、黄瓜(Cucumis sativus)、狗牙根(Cynodon dactylon)、Daucus carota、油棕(Elaeisguineensis)、欧洲草莓(Fragaria vesca)、大豆(Glycine max)、陆地棉(Gossypium hirsutum)(树棉(Gossypium arboreum)、草棉(Gossypiumherbaceum)、Gossypium vitifolium)、向日葵(Helianthus annuus)、Heveabrasiliensis、大麦(Hordeum vulgare)、啤酒花(Humulus Iupulus)、甘薯(Ipomoea batatas)、核桃(Juglans regia)、兵豆(Lens culinaris)、亚麻(Linumusitatissimum)、番茄(Lycopersicon lycopersicum)、苹果属(Malus spp.)、Manihot esculenta、紫苜蓿(Medicago sativa)、芭蕉属(Musa spp.)、烟草(Nicotiana tabacum)(黄花烟草(N.rustica))、油橄榄(Olea europaea)、稻(Oryza sativa)、金甲豆(Phaseolus lunatus)、菜豆(Phaseolus vulgaris)、黑挪威云杉(Picea abies)、松属(Pinus spp.)、豌豆(Pisum sativum)、杏桃仁油(Prunus armeniaca)、欧洲甜樱桃(Prunus avium)、殴洲酸樱桃(Prunuscerasus)、扁桃(Prunus dulcis)、Prunus domesticua、桃(Prunus persica)、西洋梨(Pyrus communis)、Ribes sylvestre、蓖麻(Ricinus communis)、甘蔗(Saccharum officinarum)、黑麦(Secale cereale)、马铃薯(Solanumtuberosum)、两色蜀黍(Sorghum bicolor)(蜀黍(s.vulgare))、可可树(Theobroma cacao)、红车轴草(Trifolium pratense)、普通小麦(Triticumaestivum)、硬粒小麦(Triticum durum)、蚕豆(Vicia faba)、葡萄(Vitisvinifera)和玉蜀黍(Zea mays)。
此外,形式II或包含它的除草组合物还可以用于因包括基因工程方法在内的育种而耐受除草剂作用的作物。
此外,形式II或包含它的除草组合物还可以用于因包括基因工程方法在内的育种而耐受昆虫或真菌侵袭的作物。
此外,已经发现形式II还适于植物部分的脱叶和/或干燥,对此合适的是作物植株如棉花、土豆、油籽油菜、向日葵、大豆或蚕豆,尤其是棉花。就此而言,已经发现用于植物干燥和/或脱叶的组合物、制备这些组合物的方法以及使用形式II干燥和/或脱叶植物的方法。
作为干燥剂,形式II特别适于干燥作物植株如土豆、油籽油菜、向日葵和大豆以及禾谷类的地面上部分。这使得这些重要作物植株的完全机械化收获成为可能。还具有经济益处的是促进柑橘类水果、橄榄和其它品种的仁果、核果和坚果的收获,这通过在一定时间期限内集中裂开或降低对树的粘附而成为可能。相同的机理,即促进水果部分或叶部分与植物的枝部分之间发生脱离对于有用植物,尤其是棉花的受控脱叶也是必不可少的。此外,各棉花植株成熟的时间间隔缩短导致收获后的纤维质量提高。
此外,还发现形式II还适用于防治针叶树,尤其是自然生长的针叶树秧苗,特别用于防治自然生长的松树秧苗。
形式II还适用于在作物植株如大豆、棉花、油菜、亚麻、小扁豆、稻、糖用甜菜、向日葵、烟草和禾谷类如玉米或小麦中防治杂草。
形式II或包含它的除草组合物例如可以以即喷水溶液,粉末,悬浮液以及高度浓缩的水性、油性或其它悬浮液,油悬浮液,糊,粉剂,撒播用粉末或颗粒的形式通过喷雾、雾化、撒粉、撒播或浇灌施用。使用形式取决于意欲的目的;在任何情况下都应确保本发明活性物质最佳可能地分布。
除草组合物包含除草有效量的形式II和常用于配制植物保护产品的助剂和载体。
合适的载体原则上为所有常用于植物保护产品,尤其是除草剂的所有固体物质。固体载体的实例为矿土如硅胶、硅酸盐、滑石、高岭土、活性粘土、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁和氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵和脲类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。
在形式II的液体配制剂的情况下,组合物具有液相。适合作为液相的原则上为水和其中形式II不可溶解或仅微溶的那些有机溶剂,例如在25℃和1013毫巴下苯基尿嘧啶I的形式II在其中的溶解度不超过1重量%,尤其是不超过0.1重量%,特别是不超过0.01重量%的那些有机溶剂。
优选液相尤其为水和含水溶剂,即除了水之外还基于水和溶剂总重量包含至多30重量%,但优选不超过10重量%的一种或多种水溶混性有机溶剂的溶剂混合物,所述水溶混性有机溶剂例如为水溶混性醚如四氢呋喃、甲基乙二醇、甲基二甘醇,链烷醇如甲醇、乙醇、异丙醇,或多元醇如乙二醇、甘油、二甘醇、丙二醇等。
此外,优选液相为在25℃和1013毫巴下苯基尿嘧啶I的形式II在其中的溶解度不超过1重量%,尤其是不超过0.1重量%,特别是不超过0.01重量%的非水性有机溶剂。这些尤其包括脂族和脂环族烃和油,尤其是植物来源的那些,还有饱和或不饱和脂肪酸或脂肪酸混合物的C1-C4烷基酯,尤其是甲基酯,例如油酸甲酯、硬脂酸甲酯、菜子油甲酯,以及链烷矿物油等。
典型的助剂包括表面活性物质,尤其是常用于植物保护组合物的润湿剂和分散剂/分散助剂,还有改变粘度的添加剂(增稠剂),消泡剂,防冻剂,pH调节剂,稳定剂,抗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)形式的用于植物保护的组合物。这类悬浮液浓缩物包含呈细碎颗粒形式的苯基尿嘧啶I的形式II,其中形式II的颗粒悬浮于水相中。活性物质颗粒的尺寸(即90重量%的活性物质颗粒不超过的尺寸)通常低于30μm,尤其低于20μm。有利的是本发明SC配制剂中至少40重量%,尤其是至少60重量%的颗粒的直径低于2μm。
除了活性物质之外,含水悬浮液浓缩物通常包含表面活性物质以及合适的话消泡剂、增稠剂、防冻剂、稳定剂(生物杀伤剂)、pH调节剂和抗结块剂。
在这类SC中活性物质的量,即形式II的苯基尿嘧啶以及合适的话其它活性物质的总量基于悬浮液浓缩物的总重量通常为10-70重量%,尤其是20-50重量%。
合适的表面活性物质优选为阴离子和非离子表面活性剂。其它合适的表面活性物质为保护胶体。表面活性物质的量基于本发明含水SC的总重量通常为0.5-30重量%,尤其是1-20重量%。优选表面活性物质包含至少一种阴离子表面活性物质和至少一种非离子表面活性物质,其中阴离子表面活性物质与非离子表面活性物质的重量比通常为10:1-1:10。
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、烯烃磺酸盐、链烷磺酸盐、石油醚磺酸盐、氨基乙磺酸盐、肌氨酸盐、脂肪酸、烷基萘磺酸、萘磺酸、木素磺酸、磺化萘与甲醛或与甲醛和苯酚以及合适的话脲的缩合物,以及苯酚磺酸、甲醛和脲的缩合物,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,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(如CP9,BASF),包括上述物质的碱金属盐、碱土金属盐、铵盐和胺盐。优选阴离子表面活性物质为含有至少一个磺酸根基团那些,尤其是它们的碱金属盐及其铵盐。
非离子表面活性物质的实例包括烷基酚烷氧基化物、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、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。优选非离子表面活性物质为脂肪醇乙氧基化物、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。
保护胶体通常为水溶性两性聚合物。实例为蛋白质和变性蛋白质如酪蛋白,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,还有聚羧酸化物如聚丙烯酸和丙烯酸共聚物,聚乙烯醇,聚乙烯基吡咯烷酮,乙烯基吡咯烷酮共聚物,聚乙烯胺,聚乙烯亚胺和聚亚烷基醚。
适用于本发明含水SC的粘度改性添加剂(增稠剂)尤其为赋予配制剂改变的流动行为如静止状态下高粘度和运动状态下低粘度的化合物。合适的化合物原则上是为此用于悬浮浓缩物所有那些。应提及的物质例如为无机物质,如层状硅酸盐和有机改性的层状硅酸盐如膨润土或凹凸棒土(例如购自Engelhardt的和有机物质如多糖和杂多糖如Xanthan(Kelco的), 23(Rhone Poulenc)或(购自R.T.Vanderbilt),优选使用粘度改性添加剂的量基于SC的总重量通常为0.1-5重量%。
适用于本发明含水SC的消泡剂实例是为此已知的聚硅氧烷乳液(如Wacker的 SRE,或Rhodia的),长链醇,脂肪酸,脂肪酸盐,蜡水分散体类型的消泡剂,固体消泡剂(已知为配混物)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%。
也可将防腐剂加入本发明悬浮液浓缩物中以稳定它们。合适的防腐剂为基于异噻唑啉酮(isothiazolone)的那些,例如购自ICI的或购自Thor chemie的 RS或购自Rohm & Haas的 MK。防腐剂的量基于SC的总重量通常为0.05-0.5重量%。
合适的防冻剂为液体多元醇,例如乙二醇、丙二醇或甘油,以及脲。防冻剂的量基于含水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,本发明含水SC可包含缓冲剂以调节pH。缓冲剂的实例为无机或有机弱酸如磷酸、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。
如果形式II的晶型的配制剂用于处理种子,则它们可进一步包含常用于种子处理如拌种或种子涂覆中的成分。除了上述成分外,它们尤其包括着色剂、粘合剂、填料和增塑剂。
合适的着色剂为所有常用于此的所有染料和颜料。微溶于水的颜料和溶于水的染料均可使用。可以提到的实例是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,以及颜料蓝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108。着色剂的量通常不超过配制剂的20重量%且优选基于配制剂的总重量为0.1-15重量%。
合适的粘合剂为可用于拌种产品的所有常规粘合剂。合适的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,还有聚丙烯酸酯、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,上述保护胶体,聚酯,聚醚酯,聚酐,聚酯型聚氨酯,聚酯酰胺,热塑性多糖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、羟丙基纤维素和淀粉衍生物和改性淀粉,糊精,麦芽糊精,藻酸盐和壳聚糖,还有脂肪、油、蛋白质,包括酪蛋白、明胶和玉米蛋白,阿拉伯树胶,紫胶。优选粘合剂被植物耐受,即它们没有或基本没有植物毒性作用。粘合剂优选为生物可降解的。优选选择粘合剂,以使它们起配制剂的活性组分的基质的作用。粘合剂的量通常不超过配制剂的40重量%且基于配制剂的总重量优选为1-40重量%,尤其是5-30重量%。
除了粘合剂外,种子处理配制剂还可包含惰性填料。实例为上述固体载体,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、蒙脱土,以及细碎有机材料如木粉、谷粉、活性炭等。优选选择填料量,以使填料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,种子处理配制剂也可包含增加涂层柔性的增塑剂。增塑剂的实例为低聚亚烷基二醇、甘油、邻苯二甲酸二烷基酯、烷基苄基邻苯二甲酸酯、乙二醇苯甲酸酯和相当的化合物。在涂层中,增塑剂的量基于配制剂的非挥发性组分的总重量经常为0.1-20%。
本发明尤其涉及非水性悬浮浓缩物形式的植物保护组合物。这类悬浮液浓缩物包含细碎颗粒形式的苯基尿嘧啶I的形式II,其中形式II的颗粒悬浮在非水相中。活性物质颗粒的尺寸(即90重量%的活性物质不超过的尺寸)通常低于30μm,尤其是低于20μm。有利的是在非水性SC中至少40重量%,尤其是至少60重量%的颗粒具有低于2μm的直径。
除了活性物质之外,非水性悬浮液浓缩物通常包含表面活性物质以及合适的话消泡剂、增稠剂、防冻剂、稳定剂(生物杀伤剂)、pH调节剂和抗结块剂。
在这类非水性SC中,活性物质的量,即形式II的苯基尿嘧啶I以及合适的话其它活性物质的总量基于非水性悬浮液浓缩物的总重量通常为10-70重量%,尤其是20-50重量%。
合适的表面活性物质优选为上述阴离子和非离子表面活性剂。通常而言,表面活性物质的量基于本发明非水性SC配制剂的总重量为1-30重量%,尤其是2-20重量%。优选表面活性物质包含至少一种阴离子表面活性物质和至少一种非离子表面活性物质,其中阴离子表面活性物质与非离子表面活性物质的重量比通常为10:1-1:10。
本发明形式II也可配制为粉末,包括撒播用粉末和粉剂。这类配制剂可通过将形式II与固体载体以及合适的话其它助剂混合或一起研磨而制备。
本发明形式II也可配制成颗粒,如涂覆颗粒、浸渍颗粒和均质颗粒。这类配制剂可通过将活性物质粘附于固体载体而制备。合适的载体为矿土如硅石、硅胶、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、磨碎的合成物质,肥料如硫酸铵、磷酸铵、硝酸铵、尿素和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。
形式II在即用制剂中的浓度可在宽范围内变化。配制剂基于总重量通常包含约11-98重量%,优选10-95重量%活性物质。
下面的配制剂实例阐述如何制备这类制剂:
I.将20重量份形式II与3重量份二异丁基萘磺酸钠、17重量份来自亚硫酸盐废液的木素磺酸钠盐和60重量份粉状硅胶彻底混合并将混合物在锤磨机中研磨。这产生包含形式II的水分散性粉末。将该混合物精细分散于20,000重量份水中,得到包含0.1重量%形式II的喷雾混合物
II.将3重量份形式II与97重量份细碎高岭土混合。得到包含3重量%形式II的粉剂。
III.将20重量份形式II与2重量份十二烷基苯磺酸钙盐、8重量份脂肪醇聚乙二醇醚、2重量份苯酚磺酸/脲/甲醛缩合物的钠盐和68重量份链烷烃矿物油均匀混合。得到形式II的稳定的非水性悬浮液浓缩物。
IV.将10重量份形式II在如下溶液中配制为悬浮液浓缩物:17重量份聚乙二醇/丙二醇嵌段共聚物、2重量份苯酚磺酸/甲醛缩合物和约1重量份其它助剂(增稠剂、消泡剂)在7重量份丙二醇和63重量份水的混合物中的溶液。
除非配制剂为即用的,形式II或包含它的除草组合物的施用以含水喷雾混合物的形式进行。这些含水喷雾混合物通过用水稀释包含形式II的苯基尿嘧啶I的上述配制剂而制备。喷雾混合物也可包含溶解、乳化或悬浮形式的其它成分,例如肥料,其它除草或生长调节活性物质组的活性物质,其它活性物质如防治动物害虫或植物病原真菌或细菌的活性物质,还有用于消除营养和痕量元素缺乏的无机盐,植物非毒性油或油浓缩物。通常在稀释本发明配制剂之前、之中或之后将这些成分加入喷雾混合物中。
形式II或包含它的除草组合物可以出苗前或出苗后方法施用。若苯基尿嘧啶I不能被某些作物植株良好地耐受,则可以使用其中借助喷雾设备喷雾除草组合物以使它们理想地接触敏感作物植株的叶子,而活性物质到达生长在下面的不希望的植物的叶子或裸露的土壤表面的施用技术(后引导,最后耕作程序)。
取决于防治措施目标、季节、目标植物和生长阶段,形式II的施用率为每公顷0.001-3.0kg活性物质(a.s.),优选0.01-1.0kg活性物质。
为了拓宽活性谱并获得协同增效作用或增加选择性,可以将形式II与大量其它除草或生长调节活性成分组的代表性物质和/或安全剂混合并可与这些物质一起施用。形式II可类似于苯基尿嘧啶I与除草剂、生长调节剂和/或安全剂的混合物而使用或施用,该混合物描述于WO 2003/024221、WO 2004/080183、WO 2006/097509和WO 2007/042447。
合适的混合搭配物例如是1,2,4-噻二唑、1,3,4-噻二唑、酰胺、氨基磷酸及其衍生物、氨基三唑、N-酰苯胺、芳氧基/杂芳氧基链烷酸及其衍生物、苯甲酸及其衍生物、苯并噻二嗪酮、2-芳酰基/杂芳酰基-1,3-环己二酮、杂芳基芳基酮、苄基异噁唑烷酮、间-CF3-苯基衍生物、氨基甲酸酯、喹啉羧酸及其衍生物、乙酰氯苯胺、环己酮肟醚衍生物、二嗪、二氯丙酸及其衍生物、二氢苯并呋喃、二氢呋喃-3-酮、二硝基苯胺、二硝基苯酚、二苯基醚、联吡啶、卤代羧酸及其衍生物、脲、3-苯基尿嘧啶、咪唑、咪唑啉酮、N-苯基-3,4,5,6-四氢邻苯二甲酰亚胺、噁二唑、环氧乙烷类、酚类、芳氧基-和杂芳氧基苯氧基丙酸酯、苯基乙酸及其衍生物、2-苯基丙酸及其衍生物、吡唑、苯基吡唑、哒嗪、吡啶羧酸及其衍生物、嘧啶基醚、磺酰胺、磺酰脲、三嗪、三嗪酮、三唑啉酮、三唑羧酰胺和尿嘧啶。合适的安全剂的实例为(喹啉-8-氧基)乙酸、1-苯基-5-卤代烷基-1H-1,2,4-三唑-3-甲酸、1-苯基-4,5-二氢-5-烷基-1H-吡唑-3,5-二甲酸、4,5-二氢-5,5-二芳基-3-异噁唑甲酸、二氯乙酰胺、α-肟基苯基乙腈、苯乙酮肟、4,6-二卤代-2-苯基嘧啶、N-[[4-(氨基羰基)苯基]磺酰基]-2-苯甲酰胺、1,8-萘二甲酸酐、2-卤代-4-(卤代烷基)-5-噻唑甲酸、硫代磷酸酯和N-烷基-O-苯基氨基甲酸酯及其可农用盐(条件是它们具有酸功能),它们的可农用衍生物如酰胺、酯和硫酯。
此外还可能有利的是单独或与其它除草剂和/或安全剂结合或以与其它作物保护试剂的混合物形式一起施用形式II,例如与防治害虫或植物病原性真菌或细菌的试剂一起施用。还令人感兴趣的是与无机盐溶液的溶混性,所述溶液用于治疗营养和痕量元素缺乏。还可以加入非植物毒性的油和油浓缩物。
应用实施例
形式II的除草活性由下列温室试验证实:
所用栽培容器为塑料花盆,所述盆装有土壤(例如含约3.0%腐殖土的壤质砂)作为基质。对每一品种单独播种试验植物的种子。
在出苗前处理的情况下,直接在播种之后借助精细分布的喷嘴施加悬浮于水中的活性物质。温和灌溉容器以促进发芽和生长,随后用透明塑料罩覆盖,直到植物生根。该覆盖导致试验植物均匀发芽,除非这受到活性物质的不利影响。
对于出苗后处理,首先使试验植物生长至高3-15cm,这取决于植物习性,仅在此时用悬浮于水中的活性物质处理。为此,将试验植物或者直接播种并在相同容器中生长,或者将它们首先单独作为秧苗生长,然后在处理前几天转移到试验容器中。
取决于品种,将植物分别保持在10-25℃或20-35℃的温度下。试验期为2-4周。在此期间照料植物并评价它们对各处理的响应。
评价使用0-100的得分进行。100意指植物没有出苗或至少地面以上部分完全损坏,而0意指没有损害,或生长过程正常。
上述方法用于在温室测试中比较本发明的形式II和作为对比化合物的公开于WO01/83459中的形式I,在每种情况下配制为含水悬浮液浓缩物(SC;100g/l)合适的话加入1l/ha Rustica。悬浮液浓缩物具有如下组成:
苯基尿嘧啶I 100g/l
1,2-丙二醇 70g/l
分散剂I 167g/l
分散剂II 20g/l
黄原胶 3g/l
生物杀伤剂 1.8g/l
水加至1L
分散剂I:EO/PO嵌段共聚物
分散剂II:苯酚磺酸/甲醛缩合物
用于温室试验的植物属于如下品种:
学名 | 英文名 |
豚草(Ambrosia elatior) | 豚草 |
荠(Capsella bursa-pasto ris) | 荠 |
藜(Chenopodium album) | 藜 |
白苞猩猩草(Euphorbia heterophylla) | 大戟属植物 |
原拉拉藤(Galium aparine) | 八仙草 |
大豆(Glycine max) | 大豆 |
向日葵(Helianthus annuus) | 向日葵 |
大麦(Hordeum vulgare) | 冬大麦 |
地肤(Kochia scoparia) | 柳兰 |
紫叶野芝麻(Lamium purpureum) | 紫叶野芝麻 |
三肋果(Matricaria inodora) | 不香母菊 |
一年生山靛(Mercurialis annua) | 一年生山靛 |
虞美人(Papaver rhoeas) | 虞美人 |
圆叶牵牛(Pharbitis purpurea) | 圆叶牵牛 |
卷茎蓼(Polygonum convolvulus) | 荞麦蔓 |
刺沙蓬(Salsola kali ssp.Ruthenica) | 籽蒿 |
黑麦(Secale cereale) | 冬黑麦 |
刺金午时花(Sida spinosa) | prickly mellow |
新疆白芥(Sinapis arvensis) | 野田芥 |
繁缕(Stellaria media) | 繁缕 |
菥蓂(Thlas pi arvense) | 菥 |
普通小麦(Triticum aestivum) | 春小麦 |
阿拉伯婆婆纳(Veronica persicaria) | 阿拉伯婆婆纳 |
耕地堇菜(Viola arvensis) | 耕地堇菜 |
表4 比较形式II和公开于WO 01/83459中的形式I的除草活性,出苗前施用(温室)
表6 比较形式II和公开于WO 01/83459中的形式I的除草活性,出苗后施用(温室)
测试结果清楚显示,与已知的形式I相比,本发明的形式II具有显著改进的除草活性,同时显示相同或更好的作物植株耐受性。
Claims (14)
1.一种基本不含溶剂的2-氯-5-[3,6-二氢-3-甲基-2,6-二氧代-4-(三氟甲基)-1-(2H)-嘧啶基]-4-氟-N-[[甲基(1-甲基乙基)氨基]磺酰基]苯甲酰胺的结晶形式II。
2.根据权利要求1的结晶形式II,其在25℃和Cu-Kα辐射下的X-射线粉末衍射图中显示至少2个以2θ值给出的下列反射:6.3±0.3°、9.4±0.3°、10.9±0.3°、11.9±0.3°、12.6±0.3°、15.0±0.3°、15.8±0.3°、17.1±0.3°、20.0±0.3°、20.4±0.3°、24.7±0.3°、25.2±0.3°、26.2±0.3°。
3.根据权利要求1或2的结晶形式II,其熔融峰位于170-200℃,峰顶点位于180-190℃。
4.根据前述权利要求中任一项的结晶形式II,其中2-氯-5-[3,6-二氢-3-甲基-2,6-二氧代-4-(三氟甲基)-1-(2H)-嘧啶基]-4-氟-N-[[甲基(1-甲基乙基)氨基]磺酰基]苯甲酰胺的含量为至少94重量%。
5.一种2-氯-5-[3,6-二氢-3-甲基-2,6-二氧代-4-(三氟甲基)-1-(2H)-嘧啶基]-4-氟-N-[[甲基(1-甲基乙基)氨基]磺酰基]苯甲酰胺,其基本由基本不含溶剂的结晶形式II组成。
6.一种制备根据权利要求1-4中任一项的结晶形式II的方法,包括:
i)提供2-氯-5-[3,6-二氢-3-甲基-2,6-二氧代-4-(三氟甲基)-1-(2H)-嘧啶基]-4-氟-N-[[甲基(1-甲基乙基)氨基]磺酰基]苯甲酰胺在基本不含水的有机溶剂中的溶液,
ii)使2-氯-5-[3,6-二氢-3-甲基-2,6-二氧代-4-(三氟甲基)-1-(2H)-嘧啶基]-4-氟-N-[[甲基(1-甲基乙基)氨基]磺酰基]苯甲酰胺结晶至少1小时。
7.根据权利要求4的方法,其中有机溶剂选自C1-C6链烷醇、具有3-8个碳原子的无环酮、具有5-8个碳原子的环状酮、单C1-C3烷基苯、氯苯、二氯苯、二C1-C6烷基醚、5或6元脂环族醚、具有1-3个碳原子的硝基链烷烃、脂族C1-C4羧酸的C1-C4烷基酯、具有2-6个碳原子的烷基腈、脂族C1-C4羧酸的N,N-二甲基酰胺及其混合物。
8.根据权利要求6或7的方法,其中通过冷却和/或浓缩步骤1中提供的溶液而引起结晶。
9.根据权利要求6-8中任一项的方法,其中通过加入降低溶解度的溶剂而引起结晶。
10.根据权利要求6-9中任一项的方法,其中结晶在形式II的种晶存在下进行。
11.一种植物保护组合物,包含根据权利要求1-5中任一项的结晶形式II和常用于配制植物保护组合物的助剂。
12.根据权利要求11的植物保护组合物,其呈含水悬浮液浓缩物形式。
13.根据权利要求11的植物保护组合物,其呈非水性悬浮液浓缩物形式。
14.一种防治不希望的植物生长的方法,其中使根据权利要求1-5中任一项的形式II作用于植物、其环境和/或种子。
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102655748A (zh) * | 2009-12-09 | 2012-09-05 | 巴斯夫欧洲公司 | 含有嘧啶肟草醚的液体悬浮浓缩物配制剂 |
CN102655748B (zh) * | 2009-12-09 | 2015-11-25 | 巴斯夫欧洲公司 | 含有苯嘧磺草胺的液体悬浮浓缩物配制剂 |
CN113185467A (zh) * | 2021-04-20 | 2021-07-30 | 江苏乾元生物科技有限公司 | 一种苯嘧磺草胺的制备方法 |
CN113185467B (zh) * | 2021-04-20 | 2022-03-08 | 江苏乾元生物科技有限公司 | 一种苯嘧磺草胺的制备方法 |
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