TWI720975B - 碸嘧磺隆(rimsulfuron)之新穎形式,其製備方法及其用途 - Google Patents
碸嘧磺隆(rimsulfuron)之新穎形式,其製備方法及其用途 Download PDFInfo
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- TWI720975B TWI720975B TW105109626A TW105109626A TWI720975B TW I720975 B TWI720975 B TW I720975B TW 105109626 A TW105109626 A TW 105109626A TW 105109626 A TW105109626 A TW 105109626A TW I720975 B TWI720975 B TW I720975B
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- methyl
- susulfuron
- crystal form
- spp
- herbicidal composition
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- 239000005616 Rimsulfuron Substances 0.000 title claims abstract description 5
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
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- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
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Abstract
提供具有改善的溶解度和降低的黏度的晶型的碸嘧磺隆。此外,提供其製備方法。新的晶型特別適用於除草組成物並適用於控制不想要的植物生長。
Description
本發明涉及一種晶型的1-(4,6-二甲氧基嘧啶-2-基)-3-(3-乙基磺醯基-2-吡啶基磺醯基)脲(碸嘧磺隆(rimsulfuron)),本發明還涉及其製備方法以及其在農藥製備中的用途。
1-(4,6-二甲氧基嘧啶-2-基)-3-(3-乙基磺醯基-2-吡啶基磺醯基)脲(碸嘧磺隆)是一種強效除草劑,其具有高選擇性、高效率、低毒性以及其它所需的屬性。碸嘧磺隆的分子式為C14H17N5O7S2,其化學結構為:
其是使用於萌出後的作物上,例如玉米和馬鈴薯,以抵抗各種一年生和多年生草類和闊葉雜草。其對藻類具有較低的毒性,並且其通常對大多數其它野生動植物都具有較低毒性。
通常由EP0341011 A1中所述的方法製備的市售碸嘧磺隆以非晶形態存在。已發現非晶形態的碸嘧磺隆是高黏性的,不適用於製備具有噴灑設備清除性質的組成物或製劑。噴灑後,碸嘧磺隆殘留物留在噴灑設備中。充分的清除可能需要清洗步驟,這不僅耗時且也會導致廢水處理
問題。因此,需要提供一種溶解度增加且黏度降低的新形式的碸嘧磺隆。
因此,本發明提供了一種新穎晶型的碸嘧磺隆,稱為“晶型A”、其製備方法及其在農用化學組成物中的用途。有利的是,已發現所述新穎晶型A具有增加的溶解度、降低的黏度和改善的噴灑設備清除性。因此,本發明還提供用於控制不希望的植物(例如雜草)生長的組成物,該組成物包含晶型A的碸嘧磺隆本身,作為與助劑和載劑的混合物、以及作為與其它活性化合物的混合物。本發明還提供晶型A的碸嘧磺隆在控制不希望的植物生長中的用途以及其使用方法。
已發現,本發明晶型A的碸嘧磺隆在溶解度上具有顯著的增加並在黏度上具有顯著降低,這大大減少殘留污染,改善噴灑設備清除性。此外,已發現與根據EP0341011 A1所述的方法製備的非晶形碸嘧磺隆相比,晶型A的碸嘧磺隆更易於粉碎或研磨。這樣可以製備市售製劑,例如懸浮劑(SC)、油基懸浮劑(OD)、水分散粒劑(WG)和可溶粒劑(SG)。因此,可製備晶型A的碸嘧磺隆的任何製劑,這在下文中公開。
利用其高溶解度和低黏度,晶型A的碸嘧磺隆非常適用於製備用於控制不需要的雜草的組成物。
根據本發明的第一方面,提供晶型A的碸嘧磺隆,其在25℃下使用Cu-Kα輻射記錄的X-射線粉末衍射圖中顯示以下以2θ值表示的反射中的至少3個:2θ=10.868±0.2 (1)
2θ=12.248±0.2 (2)
2θ=12.845±0.2 (3)
2θ=14.249±0.2 (4)
2θ=15.039±0.2 (5)
2θ=16.120±0.2 (6)
2θ=17.434±0.2 (7)
2θ=18.010±0.2 (8)
2θ=19.699±0.2 (9)
2θ=21.801±0.2 (10)
2θ=22.568±0.2 (11)
2θ=26.567±0.2 (12)。
本發明的晶型A的碸嘧磺隆之特徵在於具有上述反射中的至少三個之X-射線粉末衍射圖。優選地,晶型A具有上述反射中的至少四個,更優選地,具有至少五個、六個或七個或八個該等反射。晶型A的碸嘧磺隆的X-射線粉末衍射圖如圖1所示,這將在下文中詳細描述。
根據優選的具體實施例,晶型A具有以下反射中的至少3個、4個或5個或全部:2θ=10.868±0.2 (1)
2θ=12.248±0.2 (2)
2θ=12.845±0.2 (3)
2θ=16.120±0.2 (6)
2θ=21.801±0.2 (10)
2θ=26.567±0.2 (12)
根據本發明的晶型A的碸嘧磺隆可進一步用紅外(IR)光譜特徵化。晶型A的IR光譜在圖2中顯示,其在3257.17cm-1和2943.91cm-1顯示特徵帶。
製備非晶形碸嘧磺隆的方法為本領域熟知。非晶形碸嘧磺隆是在商業規模上生產並供應。用於製備非晶形碸嘧磺隆的特別適用的方法是說明於EP0341011 A1中。
根據本發明,晶型A的碸嘧磺隆可藉由以下方法得到:將非晶形態的碸嘧磺隆溶解,且隨後從溶劑中結晶。
在一個方面,本發明提供一種製備晶型A的碸嘧磺隆的方法,其包括以下步驟:i)在溶劑中製備非晶形碸嘧磺隆的溶液;ii)使碸嘧磺隆從所述溶液中結晶以得到固體沉澱物;以及iii)分離所述固體沉澱物。
用於製備碸嘧磺隆晶型A的合適溶劑包括鹵代烴(例如氯苯、溴苯、二氯苯、氯甲苯和三氯苯)、醚(例如乙基丙基醚、正丁基醚、苯甲醚、苯乙醚、環己基甲基醚、二甲醚、二乙醚、二甲基乙二醇、二苯醚、二丙醚、二異丙醚、二正丁醚、二異丁醚、二異戊醚、乙二醇二甲基醚、異丙基乙基醚、甲基第三丁基醚、四氫呋喃、甲基四氫呋喃、二烷、二氯二乙醚、甲基四氫呋喃、環氧乙烷和/或環氧丙烷的聚醚)、硝化的烴(例如硝基甲烷、硝基乙烷、硝基丙烷、硝基苯、氯硝基苯和鄰硝基甲苯)、脂
族烴、脂環族烴或芳烴(例如戊烷、正己烷、正庚烷、正辛烷、壬烷)、甲基異丙基苯、沸點為70-190℃的石油餾分、環己烷、甲基環己烷、石油醚、石油英、辛烷、苯、甲苯和二甲苯)、酯(例如丙二酸酯、乙酸正丁基酯(乙酸正丁酯)、乙酸甲酯、乙酸乙酯、乙酸異丁酯、碳酸二甲酯、碳酸二乙酯、碳酸二丁酯和碳酸亞乙酯)和脂肪醇(例如甲醇、乙醇、正丙醇、異丙醇、正丁醇和第三戊醇)。
優選的溶劑是醚、芳族烴(例如苯、甲苯、二甲苯、氯苯)、酯和脂肪醇和它們的混合物。特別優選的溶劑或溶劑混合物是異丙醇、甲苯、甲基四氫呋喃、碳酸二乙酯、氯苯、乙酸正丁酯、乙酸異丁酯、正丁醇、乙醇、丙二酸乙酯、甲基第三丁基醚,以及甲苯和丁醇的混合物、甲苯和乙酸正丁酯的混合物、丙二酸乙酯和甲基第三丁基醚的混合物、以及乙酸丁酯和甲基第三丁基醚的混合物。本發明也考慮多於2種或3種或4種組分的溶劑混合物。
在本發明中,優選地,所述溶劑包含至少一種醇,更優選地包含至少一種直鏈或支鏈C1-C8脂肪醇,更優選地包含至少一種直鏈或支鏈C1-C4脂肪醇,更優選地包含甲醇和乙醇。
根據另一個優選的具體實施例,所述溶劑基本由上述醇或它們的混合物組成。
因此,根據優選的具體實施例,在步驟(i)中,將非晶形碸嘧磺隆溶解在含有醇的溶劑中。在優選的具體實施例中,所述溶劑基本由甲醇和/或乙醇組成。
在所述方法的步驟(ii)中,碸嘧磺隆從所述溶液中結晶。使碸嘧磺隆從所述溶液中結晶的技術對於本領域技術人員來說是已知的。例如,在一個具體實施例中,步驟(i)中的溶液在升高的溫度下形成,可
藉由將所述溶液冷卻至室溫或環境溫度來完成結晶。在一個優選的具體實施例中,藉由將在所述方法的步驟(i)中形成的溶液濃縮來完成結晶。或者,或此外,可將晶種,特別是前述晶型A的碸嘧磺隆的晶種加入到步驟(i)中形成的溶液中,以促進和/或提高結晶。
優選地,用溶劑清洗在結晶階段中回收的碸嘧磺隆的固體沉澱物一次或多次。優選地,在清洗階段使用的溶劑由如上所述用於形成步驟(i)溶液的溶劑中的一種或多種組分組成。醇類,優選為甲醇和乙醇,是特別適用於清洗回收的固體碸嘧磺隆的溶劑。
本發明還涉及包含晶型A的碸嘧磺隆的組成物。晶型A的碸嘧磺隆的量少於所述組成物的75重量%,優選少於所述組成物的50重量%,更優選少於所述組成物的30重量%,更優選為所述組成物的約25重量%。
碸嘧磺隆作為除草劑之用途是本領域眾所周知的並且在商業規模上應用。晶型A的碸嘧磺隆在控制不想要的植物生長(例如雜草)時也具有活性。配製和施用碸嘧磺隆的技術在本領域是已知的,例如在本文之前討論的現有技術文件中所揭示的技術。本發明晶型A的碸嘧磺隆可以類似的方式配製和施用。
因此,在另一方面,本發明提供一種包含如上文定義的晶型A的碸嘧磺隆的除草組成物。
因此,本發明還提供使用晶型A的碸嘧磺隆製備用於控制不想要的植物生長的組成物的方法。
晶型A的碸嘧磺隆可使用合適的助劑、載劑和溶劑,以已知的方式摻入常規配製劑中,例如水懸劑(SC)、油基水懸劑(OD)、水溶性粒劑(SG)、水分散性乳劑(DC)、乳劑(EC)、拌種乳劑(emulsion seed
dressings)、拌種懸浮劑(suspension seed dressings)、顆粒劑(GR)、微粒劑(MG)、懸乳劑(SE)和水分散粒劑(WG)。
在本文中,晶型A的碸嘧磺隆可以混合物總重量的約0.1至約50重量%的濃度存在,即以足夠獲得所需劑量的量存在。例如藉由將晶型A的碸嘧磺隆以水、溶劑和載劑增量,並使用(如果合適)乳化劑和/或分散劑和/或其它助劑來製備配製劑。
以已知的方式藉由將晶型A的碸嘧磺隆與常規添加劑,例如液體稀釋劑、固體稀釋劑、潤濕劑、分散劑、增稠劑和其它製劑成分混合來製備這些配製劑。
液體稀釋劑包括但不限於水、N,N-二甲基甲醯胺、二甲基亞碸、N-烷基吡咯烷酮、乙二醇、聚丙二醇、碳酸亞丙酯、二元酯、石蠟、烷基苯、烷基萘、甘油、三乙酸甘油酯、橄欖油、蓖麻油、亞麻籽油、芝麻油、玉米油、花生油、棉籽油、大豆油、菜籽油和椰油;酮類,例如環己酮、2-庚酮、異佛爾酮和4-羥基-4-甲基-2-戊酮;乙酸酯,例如乙酸己酯、乙酸庚酯和乙酸辛酯;和醇類,例如甲醇、環己醇、癸醇、苯甲醇和四氫糠醇。
固體稀釋劑可以是水溶性或非水溶性的。水溶性固體稀釋劑包括但不限於:鹽類,例如鹼金屬磷酸鹽(如磷酸二氫鈉)、鹼土金屬磷酸鹽、鈉、鉀、鎂和鋅的硫酸鹽、氯化鈉和氯化鉀、乙酸鈉、碳酸鈉和苯甲酸鈉、以及糖和糖衍生物,例如山梨糖醇、乳糖、蔗糖和甘露醇。非水溶性固體稀釋劑的例子包括但不限於:黏土、合成氧化二矽和矽藻土二氧化矽、矽酸鈣和矽酸鎂、二氧化鈦、鋁、鈣和氧化鋅。
潤濕劑包括但不限於:烷基磺基琥珀酸酯、月桂酸酯、烷基硫酸酯、磷酸酯、炔二醇(acetylenic diols)、乙氧基氟化醇、乙氧基化的矽酮、烷基苯酚乙氧基化物、苯磺酸酯、烷基取代的苯磺酸酯、烷基α-烯烴磺酸酯、萘磺酸酯、烷基取代的萘磺酸酯、萘磺酸酯和烷基取代的萘磺酸酯與甲醛的縮合物、醇的乙氧基化物。烷基萘磺酸酯、鈉鹽特別適用于本發明的組成物。
分散劑包括但不限於:木質素磺酸的(任選聚乙氧基化的)鈉鹽、鈣鹽和銨鹽;馬來酸酐共聚物的鈉鹽和銨鹽;縮合的苯酚磺酸的鈉鹽;萘磺酸酯-甲醛縮合物。木質素磺酸鹽,例如木質素磺酸鈉特別優選用於本發明的組成物。萘磺酸酯-甲醛縮合物例如萘磺酸,與甲醛的聚合物以及鈉鹽特別適用於本發明的組成物。
增稠劑包括但不限於:瓜爾膠、果膠、酪蛋白、角叉菜膠、黃原膠、藻酸鹽、甲基纖維素、羥乙基纖維素、羥丙基纖維素和羧甲基纖維素。合成的增稠劑包括前述種類的衍生物,還包括聚乙烯醇、聚丙烯醯胺、聚乙烯基吡咯烷酮、各種聚醚和它們的共聚物以及聚丙烯酸和它們的鹽。烷基聚乙烯基吡咯烷酮特別適用於本發明的組成物。
可在本發明中使用其它配製劑成分,例如染料、消泡劑、乾燥劑等。這些成分為本領域技術人員熟知。
根據本發明的晶型A的碸嘧磺隆可以配製劑和其使用的形式存在,其使用形式由這些製劑製備,以及作為與其它活性化合物(例如殺蟲劑、引誘劑、殺菌劑、殺細菌劑、殺蟎劑、殺線蟲劑、殺真菌劑、生長調節物質、除草劑、安全劑、肥料和化學資訊素)的混合物形式存在,或作為與用於改善植物性質的試劑的混合物。
當用作除草劑時,根據本發明的晶型A的碸嘧磺隆還可以配製劑和其使用的形式存在,其使用形式由這些製劑製備,並作為與抑制劑
的混合物,所述抑制劑在其應用於植物的環境、植物部分的表面或植物組織中之後減少活性化合物的降解。
可根據本發明處理所有植物和植物部分。在本發明文本中,植物應理解為是指所有植物和植物種群,例如需要和不需要的野生植物或作物植物(包括天然的作物植物)。作物植物可以是藉由常規培育和優化方法、藉由生物技術和基因工程方法、或通過這些方法的組合得到的植物,包括能被植物育種權(plant breeders' rights)保護或不能被保護的轉殖基因植物和植物栽培變種。應理解植物部分指的是地上和地下的所有植物部分和器官,例如枝條、葉、針葉、莖、幹、花、子實體、果實、種子、根、塊莖和根莖。還包括收穫的材料,以及無性繁殖材料和有性繁殖材料,例如,插枝、塊莖、分生組織、根莖、側枝、種子、單植物細胞和多植物細胞,以及任何其它植物組織。
在本文中,術語“約”與數值或數值範圍結合使用時,表示略大於或略小於所述數值或數值範圍,與所述數值或數值範圍端點的偏差為±10%。
本文所用的“周圍”指的是所述植物生長的地點,所述植物的植物繁殖材料播種的地點,或者所述植物的植物繁殖材料將被播種的地點。
根據本發明用本發明的組成物或配製劑處理植物和植物部分是直接進行、或藉由常規處理方法使所述組成物或配製劑作用在植物和植物部分周圍、生長地或儲存空間來進行。這些常規處理方法的例子包括浸沒、噴灑、蒸發、霧化、撒施、塗覆(如果是繁殖材料),以及施塗一種或多種包衣(特別是種子的情況)。
本發明的組成物或配製劑可用於控制雙子葉雜草,例如:檾麻屬(Abutilon spp.)、豚草屬(Ambrosia spp.)、莧屬(Amaranthus spp.)、
藜屬(Chenopodium spp.)、糖芥屬(Erysimum spp.)、大戟屬(Euphorbia spp.)、蔓蓼屬(Fallopia spp.)、豬殃殃屬(Galium spp.)、天胡荽屬(Hydrocotyle spp.)、番薯屬(Ipomoea spp.)、野芝麻屬(Lamium spp.)、苜蓿屬(Medicago spp.)、酢漿草屬(Oxalis spp.)、車前屬(Plantago spp.)、蓼屬(Polygonum spp.)、墨苜蓿屬(Richardia spp.)、金午時花屬(Sida spp.)、歐白芥屬(Sinapis spp.)、輪螺屬(Solarium spp.)、繁縷屬(Stellaria spp.)、蒲公英屬(Taraxacum spp.)、車軸草屬(Trifolium spp.)、婆婆納屬(Veronica spp.)、堇菜屬(Viola spp.)和蒼耳屬(Xanthium spp.)。
本發明的組成物或配製劑還可用於控制單子葉雜草,例如剪股穎屬(Agrostis spp.)、看麥娘屬(Alopecurus spp.)、阿披拉草屬(Apera spp.)、燕麥屬(Avena spp.)、臂形草屬(Brachiaria spp.)、雀麥屬(Bromus spp.)、馬唐屬(Digitaria spp.)、稗草屬(Echinochloa spp.)、椮屬(Eleusine spp.)、野黍屬(Eriochloa spp.)、千金子屬(Leptochloa spp.)、毒麥屬(Lolium spp.)、露籽草屬(Ottochloa spp.)、黍屬(Panicum spp.)、雀稗屬(Paspalum spp.)、虉草屬(Phalaris spp.)、早熟禾屬(Poa spp.)、筒軸茅屬(Rottboellia spp.)、狗尾草屬(Setaria spp.)、蜀黍屬(Sorghum spp.),任何這些草類雜草的本質上敏感的生物型以及耐受(例如耐受ACC酶和/或ALS)的生物型,以及闊葉單子葉雜草,例如鴨蹠草屬(Commelina spp.)、雨久花屬(Monochoria spp.)、慈姑屬(Sagittaria spp.)和莎草科植物(sedges),例如莎草屬(Cyperus spp.)和藨草屬(Scirpus spp.)。
當將除草組成物施用於去除有用植物的生長作物中的雜草時最能看出本發明的益處,所述有用植物的生長作物例如玉蜀黍(玉米),包括飼料玉米、爆粒種玉米和甜玉米、棉、小麥、稻、燕麥、馬鈴薯、甜菜、種植作物(例如香蕉、果樹、橡膠樹、樹木苗圃)、葡萄藤、蘆筍、漿
果(例如藍莓)、蔓越莓、蔓越橘、亞麻、高粱、秋葵、薄荷、大黃、留蘭香和甘蔗。在本發明中,更多考慮玉米和馬鈴薯。
藉由以下實施例說明本發明的具體實施例,這些實施例僅用於說明目的,而不會限制公開內容的範圍。
除非另外說明,否則所有百分比都是重量%。
圖1為晶體變形的碸嘧磺隆之X-射線粉末衍射圖(XRD)。
圖2為晶體變形的碸嘧磺隆之紅外線(IR)光譜。
圖3為非晶形的碸嘧磺隆產物之X-射線粉末衍射圖(XRD)。
向0.60g(0.0024mol)3-乙基磺醯基-2-吡啶磺醯胺和0.90g(0.0034mol)苯基(4,6-二甲氧基嘧啶-2-基)胺基甲酸酯在5ml乙腈中的攪拌懸浮液中加入0.52g(0.0034mol)1,8-二氮雜雙環[5.4.0]十一碳-7-烯(DBU)並攪拌15分鐘。用水稀釋所述溶液並用鹽酸酸化。收集得到的固體沉澱物並用水和醚清洗以得到0.70g(70%)的標題化合物:熔點為160-162℃。
如圖3中所示,得到的碸嘧磺隆產物的X-射線粉末衍射圖不具有明顯的信號峰,這表明根據EP0341011 A1揭示的內容製備的碸嘧磺隆產品是非晶形的。
將10ml甲醇裝入反應器中以在攪拌下溶解在實施例1中製備的粗製碸嘧磺隆。該過程在室溫下持續2小時,且出現白色固體沉澱物。然後將所述混合物冷卻至0-5℃並保持1小時以使其完全結晶。隨後,離心所述混合物。用甲醇清洗所述濾餅。在高真空下乾燥得到的固體以得到技術級的純碸嘧磺隆晶體(純度:98%)。
用IR光譜和X-射線粉末衍射將晶體特徵化為晶型A的碸嘧磺隆。
晶型A的碸嘧磺隆的IR光譜在圖2中顯示。IR光譜在3257.17cm-1和2943.91cm-1顯現特徵峰。
晶型A的碸嘧磺隆的X-射線粉末衍射圖在圖1中顯示,其反射列舉在表1中。
將10ml乙醇裝入反應器中以在攪拌下溶解在實施例1中製備的粗製碸嘧磺隆。該過程在室溫下持續2小時,出現白色固體沉澱物。將所述混合物冷卻至0-5℃並保持1小時以使其完全結晶。隨後,離心所述混合物。用一些乙醇清洗所述濾餅。在高真空下乾燥得到的固體以得到技術級的純碸嘧磺隆晶體(純度:98%)。
如實施例2所述,用IR光譜和X-射線粉末衍射將晶體特徵化為晶型A的碸嘧磺隆。
將下述表2中所列的所有組分混合均勻,並用Dyno-Mill(由威利A.巴霍芬公司(Willy A.Bachofen AG)生產)研磨以得到油基水懸劑。
將下述表3中所列的所有組分混合,在高速旋轉磨機中摻混並研磨。加入足量的水以得到可擠出的糊料。通過模具或篩擠出該糊料以形成擠出物。在70℃下在真空烘箱中乾燥該濕擠出物,隨後用0.71-2mm的篩篩分以得到產物顆粒。
將下述表4中所列的所有組分混合,在高速旋轉磨機中摻混並研磨。加入足量的水以得到可擠出的糊料。通過模具或篩擠出該糊料以形成擠出物。在70℃下在真空烘箱中乾燥該濕擠出物,隨後用0.71-2mm的篩篩分以得到產物顆粒。
通過在磷酸二氫鉀水溶液(0.1M,250mL)中加入氫氧化鈉水溶液(0.1M,145mL),隨後加入足量的蒸餾水以將最終體積調節至500mL來製備pH 7的母液緩衝溶液。在測試溫度下(例如20℃)將飽和所需的碸嘧磺隆量的至少1倍且至多約5倍量的碸嘧磺隆加入到含有母液緩衝溶液的混合容器中。在黑暗中磁力攪拌所述混合物並保持在測試溫度下。定期移出樣品用於分析。用高速溫控離心機在測試溫度下以12000 G對樣品進行離心約20分鐘以去除懸浮的顆粒。選取每個上層清液的等分樣用於分析。
藉由具有反相層析柱和UV檢測的高壓液相層析(HPLC)測定上層清液中碸嘧磺隆的濃度。所述方法應包括使用線性回歸分析的基於至少三個標準樣品的最佳擬合校準曲線的發展。連續將樣品從混合容器中取出並分析直到三個連續樣品在濃度上顯示極少量變化或沒有變化。優選
重複該測試以保證準確性。
藉由將樣品分散在水中以產生通常用於當施用除草劑時的
濃度(25%的碸嘧磺隆)來進行清除測試。在400mL燒杯中將所述樣品加入到自來水(300mL)中並磁力攪拌2分鐘。隨後將所述混合物攪拌2分鐘,然後將得到的分散體分成三個100mL的等分樣加入到4盎司(118mL)的聚乙烯瓶中。將所述瓶子蓋緊,倒轉兩次並讓其靜置過夜。
靜置過夜後,將每個單獨的瓶子倒轉兩次,隨後將液體內容物倒出。加入自來水(10mL)並將所述瓶子倒轉直到所有沉澱重新懸浮,然後將內容物倒出。加入自來水(100mL)並將所述瓶子倒轉兩次,隨後使其靜置10分鐘。將所述瓶子再倒轉兩次,將內容物倒出。在所述瓶子中加入乙腈(10mL)以萃取任何剩餘的材料。用具有UV檢測的反相液相層析分析所述乙腈溶液。清除率(在乙腈溶液中碸嘧磺隆除草劑的濃度)以%表示,列在下述表6中。與較高的清除率相比,較低的清除率表示更有效的清除。
表6中的結果證明,與已知的非晶形碸嘧磺隆製品相比,晶
型A的碸嘧磺隆具有顯著優異的清除性。
Claims (12)
- 一種碸嘧磺隆(rimsulfuron)的晶型A,其在25℃下使用Cu-Kα輻射記錄的X-射線粉末衍射圖中顯示以下反射中的至少三個:2θ=10.868±0.2 (1) 2θ=12.248±0.2 (2) 2θ=12.845±0.2 (3) 2θ=14.249±0.2 (4) 2θ=15.039±0.2 (5) 2θ=16.120±0.2 (6) 2θ=17.434±0.2 (7) 2θ=18.010±0.2 (8) 2θ=19.699±0.2 (9) 2θ=21.801±0.2 (10) 2θ=22.568±0.2 (11) 2θ=26.567±0.2 (12)。
- 如請求項1所述的碸嘧磺隆的晶型A,其在25℃下使用Cu-Kα輻射記錄的X-射線粉末衍射圖中顯示以下反射中的至少3個:2θ=10.868±0.2 (1) 2θ=12.248±0.2 (2) 2θ=12.845±0.2 (3) 2θ=16.120±0.2 (6) 2θ=21.801±0.2 (10) 2θ=26.567±0.2 (12)。
- 如請求項1或2所述的碸嘧磺隆的晶型A,其顯示該等反射中的至少四個。
- 如請求項1或2中任一項所述的碸嘧磺隆的晶型A,其顯示該等反射中的至少五個。
- 如請求項1或2中任一項所述的碸嘧磺隆的晶型A,其紅外光譜顯示在3257.17cm-1和2943.91cm-1的特徵帶。
- 一種製備如請求項1至5中任一項所述的碸嘧磺隆的晶型A的方法,該方法包括:i)在溶劑中製備無定形碸嘧磺隆的溶液,其中該溶劑是甲醇和/或乙醇;ii)使碸嘧磺隆從該溶液中結晶以得到固體沉澱物;以及iii)分離該固體沉澱物。
- 一種除草組成物,其包含如請求項1至5中任一項所述的碸嘧磺隆的晶型A和至少一種助劑。
- 如請求項7所述的除草組成物,其是以以下形式存在:水懸劑(SC)、油基水懸劑(OD)、水溶性粒劑(SG)、水分散性乳劑(DC)、乳劑(EC)、拌種乳劑、拌種懸浮劑、顆粒劑(GR)、微粒劑(MG)、濃懸乳劑(SE)或水分散粒劑(WG)。
- 如請求項7或8所述的除草組成物,其中該助劑選自溶劑、稀釋劑、潤濕劑、分散劑和增稠劑中的一種或多種。
- 如請求項7或8所述的除草組成物,其中該組成物包含小於75重量%之量的碸嘧磺隆的晶型A。
- 一種如請求項1至5中任一項所述的碸嘧磺隆的晶型A之用途,其用於控 制不想要的植物生長。
- 一種如請求項7至10中任一項所述的除草組成物之用途,其用於控制不想要的植物生長。
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