CN1179080A - 环己烯酮肟醚类除草剂的稳定固态制剂 - Google Patents
环己烯酮肟醚类除草剂的稳定固态制剂 Download PDFInfo
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- CN1179080A CN1179080A CN 96192809 CN96192809A CN1179080A CN 1179080 A CN1179080 A CN 1179080A CN 96192809 CN96192809 CN 96192809 CN 96192809 A CN96192809 A CN 96192809A CN 1179080 A CN1179080 A CN 1179080A
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- alkali metal
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- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
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- 150000001447 alkali salts Chemical class 0.000 abstract description 7
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
含有通式Ⅰ所示环己烯酮肟醚类和一种PKs大于5的酸形成的水溶性碱式盐、但碱金属氢氧化物和碱金属碳酸盐除外的植物保护活性化合物的制剂,以及它们的制备和作为除草剂的应用,通式Ⅰ中,基团R1－R6具有如下含意:R1是乙基或丙基;R2是氢或一个当量的农业上可利用的阳离子;R3是2－(硫代乙基)丙基、四氢噻喃－3－基、四氢噻喃－4－基、四氢吡喃－3－基、四氢吡喃－4－基、1－(甲硫基)环丙基、5－(异丙基)异噁唑－3－基、2,5－二甲基吡唑－3－基、2,4,6－三甲基苯基或2,4,6－三甲基－3－丁酰基苯基;R4和R5相互独立是氢、甲基或甲氧羰基;Alk是CH2CH2、CH2CH(CH3)、CH2CH=CH、CH2CH=(C(Cl)或CH2CH2CH=CH;R6是氢、苯基、卤代苯基、二卤代苯基、苯氧基、卤代苯氧基或二卤代苯氧基。
Description
本发明涉及含有一种通式I所示环己烯酮肟醚类和一种PKs大于5的酸形成的水溶性碱式盐的植物保护活性化合物的制剂，以及它们的制备和作为除草剂的应用，
通式I中，基团R1-R6具有如下含意：
R1是乙基或丙基；
R2是氢或一个当量的农业上可利用的阳离子；
R3是2-(硫代乙基)丙基、四氢噻喃-3-基、四氢噻喃-4-基、四氢吡喃-3-基、四氢吡喃-4-基、1-(甲硫基)环丙基、5-(异丙基)异恶唑-3-基、2，5-二甲基吡唑-3-基、2，4，6-三甲基苯基或2，4，6-三甲基-3-丁酰基苯基；
R4和R5相互独立是氢、甲基或甲氧羰基；
Alk是CH2CH2、CH2CH(CH3)、CH2CH＝CH、CH2CH＝C(Cl)或CH2CH2CH＝CH；
R6是氢、苯基、卤代苯基、二卤代苯基、苯氧基、卤代苯氧基或二卤代苯氧基。
通式I所示环己烯酮肟醚类作为除草剂已经有相当长的时间。而且，它们少量使用时具有生长调节剂的活性。
文献报道了具有除草活性的通式I所示环己烯酮肟醚类，特别如DE-A 24 39 104，DE-A 28 22 304，DE-A 3808 072，DE-A 38 38 309，EP-A 046860，EP-A 066 195，EP-A 071 707，EP-A 088 299，EP-A 088 301，EP-A 115808，EP-A 125 094，EP-A 137 174，EP-A 142 741，EP-A 177 913，EP-A 228598，EP-A 230 235，EP-A 230 260，EP-A 238 021，EP-A 243 313，EP-A 254514，EP-A 319 835，EP-A 456 068，EP-A 456 069，EP-A 456 112，EP-A 456118，U.S.4440566，JP-A 54/191 945和英国作物保护大会-杂草论文集，1985，卷1，93-98页。
环己烯酮肟醚类的金属盐文献也有报道，如见较早的德国专利申请19545 212.7中。
这些化合物通常以可湿性粉剂(WP)或水分散性粒剂(WG)以及乳油(EC)的形式使用。这类物质的一些化合物以水溶性制剂销售，它们的活性化合物以碱金属盐形式存在。乳油的一个缺点是，在使用时除活性化合物本身之外，还施用大量的有机溶剂。另外，这些活性化合物已显示出在乳化剂或微量水存在下的有机溶剂中不稳定和分解(参见如EP-A 394 847和EP-A 266 068)。
水分散性固态制剂(WP或WG)避免了有机溶剂的使用，但是需要制剂制备的高费用。通常低熔点或液态活性化合物必须吸附在载体材料上，以便易于进行必要的精细研磨。辅助剂和载体的加入导致制剂中的活性化合物的含量肯定降低，从而导致增加包装和运输成本。特别在EP-A 488 645中报道这些制剂的例子。
水溶性制剂以前也有报道。在这些报道中也可见，环己烯酮肟醚类的化学不稳定性阻碍了形成一种实用的溶液。例如曾在JP 62089 635中报道的一种锂盐。
在不同专利申请中，报道了不同的盐的制备，其中过渡金属的盐通过复分解反应制备。实用中，因为最终达不到足够的稳定性，这个制备方法被认为是不适宜的(JP 59 1633 63，JP 8144 384,US 47 41 768,DE3941160)。
制备碱金属盐的较好方式是，用一种碱金属氢氧化物的水溶液从有机溶剂中对活性化合物进行萃取(例如DE 3941160)。
本发明的任务是开发通式I所示环己烯酮肟醚类的、贮存稳定的固态制剂和提供它们的制备方法。
我们发现，这个任务通过在本文开头描述的植物保护活性化合物制剂已经令人惊讶地完成了。
在本发明的定义里，环己烯酮肟醚类是弱有机酸，其PKs值在4～5之间。它们在中性水溶液中较低的溶解性在碱性pH值下有明显增加。通过环己烯酮与碱性水溶性物质(酸受体)适宜的组合，可能得到水溶性混合物。
除了文献中提及的碱金属氢氧化物和碱金属碳酸盐外，适合于这个目的的碱性水溶性物质是指那些PKs值大于5的酸所形成的碱金属盐。最好检测一个各个环己烯酮的PKs值，再选择一种碱性物质，其PKs值大于该环己烯酮的PKs值。
预期下面反应在有水的存在下开始进行：
然后形成透明溶液的前提条件是，生成的共轭酸HX也是水溶性的。
除了水溶性外，本发明由环己烯酮和水溶性碱式盐(酸受体)形成的制剂在较高温度下的贮存稳定性有明显的改善，例如，比游离的活性化合物或由环己烯酮与碱金属氢氧化物或碱金属碳酸盐反应得到的碱金属盐的贮存稳定性有明显的改善。
足够的贮存稳定性是可进入商业市场和可登记作为植物保护剂的基本特点。降低活性化合物本身的分解也具有经济效益。
达到上述活性化合物水溶性和贮存稳定性要求的适宜水溶性碱式盐有：偏硼酸盐、磷酸盐、磷酸氢盐、焦磷酸盐、正硅酸盐、原硅酸盐、四硼酸盐、亚硫酸盐、三聚磷酸盐、多磷酸盐、偏磷酸盐、柠檬酸盐、乙二胺四乙酸四钠、次氮基三乙酸三钠、乙酸胍、碳酸胍，和这些盐的混合物。
优选下面碱式水溶性盐：铵-和碱金属的偏硼酸盐、四硼酸盐、正硅酸盐、原硅酸盐、磷酸盐、磷酸氢盐、焦磷酸盐、三聚磷酸盐、多磷酸盐、亚硫酸盐、柠檬酸盐、乙二胺四乙酸四钠、次氮基三乙酸三钠、碳酸胍和乙酸胍。这些盐以无水形式和水合物形式使用。
特别优选的是：碱金属偏硼酸盐、碱金属四硼酸盐、碱金属和铵正硅酸盐、三碱金属和三铵磷酸盐、碱金属和铵磷酸氢盐、碱金属焦磷酸盐、碱金属三聚磷酸盐、碱金属亚硫酸盐、碱金属柠檬酸盐、乙二胺四乙酸四钠、次氮基三乙酸三钠、碳酸胍和乙酸胍。这些盐可能以无水形式或水合物形式存在。
以钠和钾盐为优选。
焦磷酸四钠、磷酸氢二钾、碳酸胍、乙二胺四乙酸四钠、次氮基三乙酸三钠和特别是偏硼酸钠、正硅酸钠和磷酸三钠证明是特别适合的，正硅酸钠也特别突出。
优选的环己烯酮除草剂有：
2-(N-乙氧基亚氨基丁基)-5-(2-乙硫基丙基)-3-羟基-2-环己烯-1-酮(稀禾定)，
2-(1-烯丙氧基亚氨基丁基)-4-甲氧羰基-5，5-二甲基-3-氧代环己烯醇(禾草灭)
2-(N-乙氧基亚氨基丁基)-5-(2-苯硫基丙基)-3-羟基-2-环己烯-1-酮，
5-(2，4，6-三甲基苯基)-3-羟基-2-[1-(乙氧基亚氨基)丙基]-环己-2-烯-1-酮(三苯草酮)，
2-(N-乙氧基亚氨基丁基)-3-羟基-5-(四氢吡喃-3-基)环己烯-1-酮，
1-[1-乙氧基亚氨基丁基]-3-羟基-5-(四氢噻喃-3-基)-2-环己烯-1-酮(噻草酮)，
2-[1-[(E)-3-氯烯丙氧基]亚氨基丙基]-5-(2-乙硫基丙基)-3-羟基环己-2-烯酮(烯草酮)，
2-(1-(3-氯烯丙氧基亚氨基丁基)-5-(2-乙硫基)丙基)-3-羟基环己-2-烯酮(cloproxydim)，
2-(1-(3-氯烯丙氧基)亚氨基丙基)-5-(1，3-二甲基吡唑-5-基)-3-羟基环己-2-烯酮，
2-(1-(3-氯烯丙氧基)亚氨基丙基)-5-(1-甲硫基环丙基)-3-羟基环己-2-烯酮，
2-(1-乙氧基亚氨基丙基)-5-(2，4，6-三甲基-3-丁酰苯基)-3-羟基环己-2-烯酮(butroxydim)，
2-(1-(3-氯烯丙氧基)亚氨基丙基)-5-(四氢吡喃-4-基)-3-羟基环己-2-烯酮，
2-(1-(2-对氯苯氧丙氧基)亚氨基丁基)-5-(四氢噻喃-3-基)-3-羟基环己-2-烯酮，或它们的混合物。
特别优选的环己烯酮除草剂是：
稀禾定、噻草酮、烯草酮、三苯草酮、butroxydim、2-(1-(3-氯烯丙氧基)亚氨基丙基)-5-(四氢吡喃-4-基)-3-羟基环己-2-烯酮、2-(1-(2-对氯苯氧丙氧基)亚氨基丁基)-5-(四氢噻喃-3-基)-3-羟基环己-2-烯酮或它们的混合物。
通式I所示环己烯酮肟醚类可在制备异构体混合物过程中得到，E/Z异构体混合物和旋光异构体或非对映异构体混合物这两者都有可能。如有必要，为了这个目的，异构体混合物可通过常规方法分离，例如用色谱法和重结晶法。
通式I所示环己烯酮肟醚类能够以几个互变异构体形式存在，这些都在本发明范围之内。
本发明包括固态的水溶性制剂，以粉状或粒状形式为优选，其中除草剂成分包括环己烯酮肟醚类和水溶性碱式盐。以环己烯酮肟醚类和碱式盐的总量计，环己烯酮肟醚类的比例为5％到95％，优选10％到85％，碱式盐的比例为5％到95％，优选15％到90％。
为了保证适用，必须另外添加制剂辅助剂。例如，包括除草有效成分、解毒剂、水溶性盐、分散剂、润湿剂、粘结剂、润滑剂、吸附性载体、消泡剂、防腐剂、着色剂、染料或其他在农业上常规使用的助剂或表面活性剂。
添加的水溶性盐可以是：氯化钠、氯化钾、硫酸铵、硫酸钠、硫酸钾、碳酸钾和碳酸钠。
其他的除草活性化合物可以是：
2，4-滴、2，4-滴丁酸、乙草胺、三氟羧草醚、苯草醚、甲草胺、二丙烯草胺、莠灭津、amidosulfuron、杀草强、莎稗磷、磺草灵、莠去津、azimsulfuron、叠氮净、燕麦灵、草除灵、乙丁氟灵、呋草黄、苄嘧磺隆、地散磷、灭草松、吡草酮、benzofluor、新燕灵、苯噻隆、甲羧除草醚、bisalafos、除草定、溴丁酰草胺、溴酚肟、溴苯腈、buminafos、丁草胺、抑草磷、丁烯草胺、草噻咪、仲丁灵、炔草隆、丁草敌、cafenstrole、双酰草胺、氨基二氯苯甲酸、氯溴隆、氯炔灵、伐草克、杀草敏、氯嘧磺隆、草枯醚、燕麦酯、枯草隆、氯苯胺灵、氯磺隆、氯酞酸甲酯、氯硫酰草胺、氯麦隆、磺庚草醚、醚磺隆、clodinafop、异恶草松、稗草胺、三氯吡啶酸、cumyluron、氰草津、环草敌、cyclosulfamuron、环莠隆、cyhalofop、牧草快、环丙津、环唑草胺、茅草枯、甜菜安、敌草净、燕麦敌、甲氧二氯苯甲酸、敌草腈、2，4-滴丙酸、高2，4-滴丙酸、禾草灵、乙酰甲草胺、枯莠隆、燕麦枯、吡氟酰草胺、dimefuron、二甲草胺、异戊净、dimethenamid、氨氟灵、地乐酚、特乐酚、双苯酰草胺、异丙净、故草快、氟硫草定、敌草隆、二硝酚、香草隆、甘草津、茵多杀、茵草敌、戊草丹、乙丁烯氟灵、胺苯磺隆、磺噻隆、乙嗪草酮、乙氧呋草黄、ethoxyfen、etobenzanid、2，4，5-涕丙酸、恶唑禾草灵、精恶唑禾草灵、噻唑禾草灵、非草隆、麦草氟、啶嘧磺隆、吡氟禾草灵、精吡氟禾草灵、氯乙氟灵、flumetsulam、flumiclorac、flumioxazin、flumipropyn、氟草隆、fluorbentranil、氟咯草酮、三氟硝草醚、乙羧氟草醚、氟胺草唑、flupropacil、氟啶酮、氯氟吡氧乙酸、呋草酮、氟磺胺草醚、杀木膦、呋氧草醚、草铵膦、草甘膦、halosulfuron、吡氟氯禾灵、精吡氟氯禾灵、环嗪酮、咪草烟、咪唑烟酸、咪唑喹啉酸、imazethabenz、咪唑乙烟酸、imazosulfuron、辛溴碘苯腈、丁咪隆、异丙乐灵、异丙隆、异恶酰草胺、异恶草醚、特胺灵、乳氟禾草灵、环草定、利谷隆、抑芽丹、2甲4氯、2甲4氯丁酸、2甲4氯丙酸、精2甲4氯丙酸、苯噻酰草胺、氟磺酰甲胺、苯嗪草酮、吡唑草胺、甲基苯噻隆、灭草唑、metobenzuron、异丙甲草胺、metosulam、甲氧隆、嗪草酮、甲磺隆、minoterb、禾草敌、酰草胺、绿谷隆、灭草隆、敌草胺、萘丙胺、萘胺苯甲酸、唑醚磺隆、草不隆、烟嘧磺隆、氟氯草唑、甲磺乐灵、除草醚、nitrofluorfen、氟草敏、坪草丹、氨磺乐灵、oxadiargyl、恶草酮、乙氧氟草醚、百草枯、克草敌、二甲戊灵、黄草伏、棉胺宁、甜菜宁、胺氯吡啶酸、哌草磷、氟酯肟草醚、丙草胺、氟嘧磺隆、环丙氰津、氨氟乐灵、环丙氟灵、扑灭通、扑草净、戊炔草胺、毒草胺、敌稗、喹禾戊酯、扑灭津、苯胺灵、苄草丹、prosulfuron、丙炔草胺、吡唑特、吡嘧磺隆、苄草唑、稗草丹、哒草特、pyrithiobac、二氯喹啉酸、氯甲喹啉酸、喹禾灵、精喹禾灵、rimsulfuron、仲丁通、环草隆、西玛津、西草净、sulcotrione、菜草畏、sulfentrazone、甲嘧磺隆、草硫膦、丁噻隆、特草定、特草灵、特丁草胺、特丁通、特丁津、特丁净、thiazopyr、thidiazimin、噻酚磺隆、禾草丹、仲草丹、野麦畏、醚苯磺隆、triazofenamid、苯磺隆、三氯吡氧乙酸、灭草环、草达津、氟乐灵、triflusulfuron、三甲异脲、灭草敌、二甲苯草胺或它们的混合物。复合除草剂可以是水溶性的或不溶于水。
对于不溶于水的化合物，它们以微细粉末存在。把这些化合物制备为水可分散性颗粒形式的制剂也是可能的。对于水溶性复合除草剂，它们可以游离酸或其盐的形式存在。
可用的分散剂或润湿剂主要有：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、多芳基苯基醚磷酸盐、烷基磺酸琥珀酸盐、烯烃磺酸盐、链烃磺酸盐、石蜡烃磺酸盐、牛磺酸盐、肌氨酸盐、脂肪酸、烷基萘磺酸、萘磺酸、木质素磺酸、磺化萘和甲醛的缩合物、或磺化萘与甲醛和苯酚的缩合物、木质素亚硫酸废液，以上包括它们的碱金属盐、碱土金属盐、铵-和胺盐；烷氧基化的烷基苯酚、烷氧基化的醇、烷氧基化的脂肪胺、聚氧乙烯脂肪酸甘油酯、烷氧基化蓖麻油、烷氧基化的脂肪酸、烷氧基化的脂肪酸酰胺、脂肪酸聚二乙醇胺、乙氧基化的羊毛脂、乙氧基/丙氧基嵌段共聚物、脂肪酸聚乙二醇酯、异十三醇、脂肪酸酰胺、甲基纤维素、脂肪酸酯、硅油、烷基聚糖苷、甘油脂肪酸酯、烷基磷酸酯、季胺化合物、氧化胺、三甲铵内酯和它们的混合物。分散剂和润湿剂是已知的物质并有很详细的描述，例如，McCutcheons：乳化剂和清洗剂，MC分部，Glen Rock NJ；Stache，表面活性剂手册，Hanser出版社.
可用的粘结剂有：
聚乙烯基吡咯烷酮、聚乙烯醇、羧甲基纤维素、淀粉、乙烯基吡咯烷酮/乙烯基乙酸酯共聚物和它们的混合物。
可用的润滑剂有：
硬脂酸镁、硬脂酸钠、滑石、聚乙烯乙二醇和它们的混合物。
可用的吸附性载体材料有：
天然矿物材料如硅酸、硅胶、硅酸盐、滑石、高岭土、吸附粘土、石灰石、白垩、胶块粘土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁，合成矿物材料，化学肥料如硫酸铵、磷酸铵、硝酸铵、尿素，和植物源产品如谷物粉、树皮粉、木屑和坚果壳粉、纤维素粉，硅镁土、montmorillonite、云母、蛭石、合成硅酸、合成硅酸钙和它们的混合物。
适合的消泡剂，如硅油乳剂、高级醇、脂肪酸、有机氟化合物和它们的混合物。
可用的制剂辅助剂在植物保护活性化合物制剂中的含量按重量计为从0到95％。如果它们是制剂的组份，按重量计从5到95％是适合的。
添加的其他植物保护活性化合物的含量，按重量计，为从0到90％。如果它们是制剂的组份，按重量计从10到90％是适合的。上述的重量百分数以植物保护活性化合物制剂的总重量计。
本发明的固态制剂以专业人员原则上已知的类型和方式制备。
适合的制剂是粉剂、粒剂、块剂、片剂和类似的固态制剂。粉剂、粒剂又是特别适合的。粉剂可加工成水溶性的或水分散性的粉剂。粒剂可加工成水溶性或水分散性粒剂，作为喷雾使用或直接撒粒使用。粒剂的平均粒径为从200微米到2毫米。
由于这些制剂通常是吸湿性的物质，或为了保护使用者的目的，例如，制剂可用水溶性薄膜袋包装。较佳的包装是另加一层阻止水蒸气浸透的外包装如聚乙烯薄膜、聚乙烯与纸或铝箔压合的薄膜。
适合的水溶性薄膜由以下材料组成：聚乙烯醇、纤维素衍生物如甲基纤维素或羧甲基纤维素。
用具有除草活性剂量的植物保护活性化合物制剂施用于作物植株、它的生长场所和/或它的种子来除灭不希望存在的植物。
下面的制备方法适用于本发明的制剂。
a)活性化合物是固态
1)使活性化合物、碱式盐和添加的助剂混合，若有必要，进行粉碎，并随后进行附聚。
适宜的附聚方法如挤压造粒、盘式造粒、流化床造粒。如果适当，制成的粒剂随后进行干燥。
2)使活性化合物、碱式盐和添加的助剂混合，如有必要，进行粉碎，并随后进行附聚。
b)活性化合物是油状物或固态
1)用碱式盐水溶液将溶于有机溶剂的环己烯酮肟醚萃取进水相中，然后分离出水层。
适合的有机溶剂是不混溶于水、或仅部分混溶于水的溶剂，如烃类、芳烃类、卤代脂肪烃或卤代芳烃类、醚类、羧酸酯、羧酸酰胺、酮类和醇类。
适合于水挥发的例子如喷雾干燥、真空干燥、流化床干燥和冷冻干燥。
以这种方法制得的固体随后可进行下面a)的过程。
此外，如此制得的水溶液通过喷雾或混合随后施加在吸附载体材料上。例如，以这种方法可制得撒施粒剂。
配制实施例
a)检验方法
在所有情况下，制剂的活性化合物含量通过高效液相色谱法定量测定，并以百分数表示。
贷架寿命实验
为了调查货架寿命，个别制剂样品在特定的时间，特定的标明温度下密封贮存在玻璃容器中。然后检测样品，并与贮存开始时的对照值(零值)比较。基于零值(以百分数表示)计算的活性化合物含量表示为相对比值。
不溶解行为实验
取2克制剂，一次加入到100毫升CIPAC标准水D中，同时用每分钟约100转的磁力搅拌器搅拌。直到整个固态产品已经崩解或不再溶解时为止。
b)制剂实验
下面化合物被用于制剂实验：
化合物A：稀禾定
化合物B：噻草酮
化合物C：2-(1-(3-氯烯丙氧基)亚氨基丙基)-5-(四氢吡喃-4-基)-3-
羟基环己-2-烯酮
化合物D：2-(1-(2-对氯苯氧丙氧基)亚氨基丁基)-5-(四氢噻喃-3-
基)-3-羟基环己烯酮
对照实施例1：
51.4克化合物C(含量97％)与1份碳酸钠和1份碳酸氢钠(48.6克)，用一种IKA实验室研磨机(型号M 20)研磨60秒，进行混合。混合物在水中5分钟之内溶解。活性化合物含量49.3％。
实施例1：
51.4克化合物C(含量97％)与正硅酸钠(48.6克)用一种IKA实验室研磨机(型号M 20)研磨60秒进行混合。混合物在水中5分钟之内溶解，得到一种透明溶液。活性化合物含量42％。
实施例2：
51.4克化合物C与磷酸三钠十二水合物48.6克按实施例1描述的操作步骤进行混合。活性化合物含量46％。
在室温下对贮存稳定性进行3个月的观察和比较
| 贮存后化合物C的相对含量1个月[％] 3个月[％] | ||
| 对照实施例1实施例1实施例2 | 9110099 | 689578 |
对照实施例2：
500克活性化合物C溶于1000克甲苯中。该溶液与58.5克氢氧化钠溶于650克水中的溶液混合1小时。液相分离后，分离出水层，然后在进气温度为120℃的干燥空气中用实验室流化床造粒机干燥并造粒。活性化合物含量86.8％。粒剂投入水中迅速并完全溶解。
对照实施例3：
92.3克活性化合物D溶于90克甲苯中。该溶液与7.66克氢氧化钠溶于100克水中的溶液混合1小时。液相分离后，分离出水层，用甲基叔丁基醚洗涤，并用真空干燥器在40℃下干燥，得到固态产品。产品中活性化合物含量87.1％。产品投入水中迅速并完全溶解。
对照实施例4：
30％活性化合物D的甲苯溶液用2.5％氢氧化钠溶液萃取。收集水相用真空干燥器在70℃下干燥。制得活性化合物含量84.6％的固体，它可在2分钟之内溶于水，得到一种透明溶液。
实施例3：
50％化合物A的叔丁基甲基醚溶液用10.2克正硅酸钠溶于50毫升水中的溶液振荡。分离出水相后，醚相用30毫升水洗涤，合并水相并用蒸发器在70℃下真空蒸发，制得的残留固体是水溶性的，在水中2分钟之内得到透明的溶液。活性化合物含量70％。
实施例4：
50毫升噻草酮(化合物B)在一种芳烃溶剂Solvesso 150(430克/升)中的溶液用17.7克正硅酸钠溶于85毫升水中的溶液萃取。分离出水相后，有机相用30毫升水洗涤，合并水相并用蒸发器在70℃下真空蒸发，制得的残留固体是水溶性的，在水中2分钟之内得到透明的溶液。活性化合物含量57％。
实施例5：
偏硼酸钠水合物(48.6克)和化合物C(51.4克)的混合物用IKA通用研磨机(型号M 20)研磨混合，然后陆续用7.2毫升水处理。而后得到的物料用篮状挤压台器具(Fitzpatrick欧洲公司产，型号KAR 75)挤压，并用0.8毫米的筛子过筛。制得的粒剂在60℃下干燥。活性化合物含量55％。该粒剂在水中少于4分钟完全溶解。
实施例6：
磷酸三钠十二水合物(58.9克)和化合物C(41.1克)的混合物，用实施例5描述的操作步骤研磨和挤压，但加入的水量为3.8毫升水。活性化合物含量52％。该粒剂在水中3分钟之内成为透明溶液。
实施例7：
正硅酸钠(48.6克)和化合物C(51.4克)的混合物用实施例5描述的操作步骤研磨和挤压，但加入的水量为25毫升水。活性化合物含量45％。该拉剂在2分钟之内溶于水，成为透明溶液。
实施例8：
化合物C(72％)和正硅酸钠(28％)的混合物用IKA型号M 20通用研磨机研磨混合，加入总量22.5克的水，制成糊状。物料用实施例5描述的操作步骤研磨和挤压，制得的粒剂在60℃下干燥。活性化合物含量64％。该粒剂在2分钟之内溶于水，成为透明溶液。
实施例9：
217.5克活性化合物C溶于200克甲苯中。该溶液与82.5克正硅酸钠溶于300克水中的溶液混合1小时。用分液漏斗进行液相分离后，分离出水层，在进气温度为120℃的干燥空气中、用实验室流化床造粒机(CombiCoater，Niro Aeromatic)干燥并造粒。活性化合物含量64.2％。该拉剂投入水中迅速并完全溶解。
实施例10：
16.0克正硅酸钠和84.82克活性化合物C在100克水中混合和反应，形成水溶液。该水溶液用真空干燥器在70℃下干燥，得到固态产品。活性化合物含量73.7％。该固体产品投入水中迅速并完全溶解。
实施例11：
79.8克活性化合物D溶于100克甲苯中。该溶液与20.8克正硅酸钠溶于100克水中的溶液混合和反应1小时。保持静止后，形成三相状态。用分液漏斗分离出底下两层水相，用真空干燥器在70℃下干燥，制得固态产品，其活性化合物含量78.7％。该固体产品投入水中迅速并完全溶解。
实施例12：
88.75克活性化合物D溶于100克甲苯中。该溶液与11.6克正硅酸钠溶于100克水中的溶液混合和反应1小时。保持静止后，形成三相状态。用分液漏斗分离出底下两层水相，用真空干燥器在干燥温度70℃下干燥，制得固态产品，其活性化合物含量88.4％。该固体产品投入水中迅速并完全溶解。
实施例13：
化合物C(7.6克)和灭草松钠盐(84.7克，含量约85％)密切混合，与正硅酸钠(7.7克)一起，用IKA通用研磨机研磨，然后用8.5毫升水弄湿。得到物料挤压成型后，制得1分钟之内溶于水、成为透明溶液的粒剂。活性化合物含量(化合物C)6.8％。
实施例14：
84.7克灭草松钠、7.6克化合物C、7.7克偏硼酸钠和6毫升水混合，用实施例13描述的操作步骤研磨和挤压。制得的粒剂1分钟之内溶于水，成为透明溶液。活性化合物含量(化合物C)6.5％。
表：制剂中活性化合物在特定的温度和30天贮存时间、货架寿命试验的结果。相对活性化合物含量(％)按指出的起始含量计算。
| 20℃ 30℃ 40℃ 50℃ | |
| 对照实施例号234 | 100 99 88 42100 98 88 40100 96 80 19 |
| 实施例号456789101112 | 100 100 96 96100 100 98 83100 99 99 87100 100 100 99100 100 100 100100 100 100 78100 100 99 7799 99 99 8599 99 99 90 |
Claims (13)
1.含有一种通式I所示环己烯酮肟醚类和一种PKs大于5的酸形成的水溶性碱式盐、但碱金属氢氧化物和碱金属碳酸盐除外的植物保护活性化合物的制剂，
通式I中，基团R1-R6具有如下含意：
R1是乙基或丙基；
R2是氢或一个当量的农业上可利用的阳离子；
R3是2-(硫代乙基)丙基、四氢噻喃-3-基、四氢噻喃-4-基、四氢吡喃-3-基、四氢吡喃-4-基、1-(甲硫基)环丙基、5-(异丙基)异恶唑-3-基、2，5-二甲基吡唑-3-基、2，4，6-三甲基苯基或2，4，6-三甲基-3-丁酰基苯基；
R4和R5相互独立是氢、甲基或甲氧羰基；
Alk是CH2CH2、CH2CH(CH3)、CH2CH＝CH、CH2CH＝C(Cl)或CH2CH2CH＝CH；
R6是氢、苯基、卤代苯基、二卤代苯基、苯氧基、卤代苯氧基或二卤代苯氧基。
2.根据权利要求1的植物保护活性化合物的制剂，该制剂含有一种选自稀禾定、噻草酮、烯草酮、三苯草酮、butroxydim、2-(1-(3-氯烯丙氧基)亚氨基丙基)-5-(四氢吡喃-4-基)-3-羟基环己-2-烯酮、2-(1-(2-对氯苯氧丙氧基)亚氨基丁基)-5-(四氢噻喃-3-基)-3-羟基环己-2-烯酮或它们的混合物的环己烯酮肟醚类作为植物保护活性化合物。
3.根据权利要求1或2的植物保护活性化合物制剂，该制剂含有作为水溶性盐的一种偏硼酸盐、磷酸盐、磷酸氢盐、焦磷酸盐、正硅酸盐、原硅酸盐、四硼酸盐、亚硫酸盐、三聚磷酸盐、多磷酸盐、偏磷酸盐或柠檬酸盐、乙二胺四乙酸四钠、次氮基三乙酸三钠、乙酸胍、碳酸胍或它们的混合物。
4.根据权利要求1～3的植物保护活性化合物制剂，该制剂含有作为水溶性碱式盐的一种碱金属偏硼酸盐、碱金属四硼酸盐、碱金属-和铵正硅酸盐、三碱金属-和三铵磷酸盐、碱金属-和铵磷酸氢盐、碱金属焦磷酸盐、碱金属三聚磷酸盐、碱金属亚硫酸盐、碱金属多磷酸盐、碱金属柠檬酸盐、乙二胺四乙酸四钠、次氮基三乙酸三钠、碳酸胍、乙酸胍或它们的混合物。
5.根据权利要求1～4的植物保护活性化合物制剂，该制剂还含有配制辅助剂。
6.根据权利要求1～5的植物保护活性化合物制剂，该制剂含有其他植物保护活性化合物。
7.根据权利要求1～5的植物保护活性化合物制剂，该制剂按重量计含有
5～95％通式I所示一种环己烯酮肟醚；
5～95％水溶性碱式盐；
0～95％配制辅助剂；
0～90％其他植物保护活性化合物。
8.根据权利要求1～7的植物保护活性化合物制剂的制备方法，该方法包括，使通式I所示一种环己烯酮肟醚、水溶性碱式盐、如有必要，配制辅助剂和如有必要，其他植物保护活性化合物进行混合，如有必要，进行粉碎，随后进行附聚或挤压成型。
9.根据权利要求1～7的植物保护活性化合物制剂的制备方法，该方法包括，使通式I所示一种环己烯酮肟醚溶于有机溶剂，用水溶性碱式盐的水溶液萃取，随后除去水。
10.根据权利要求9的制备方法，其中，植物保护活性化合物制剂在除去水后，如有必要，进行粉碎，随后进行附聚或挤压成型。
11.根据权利要求8或10的制备方法，其中挤压造粒、盘式造粒、流化床造粒或混合造粒被用于附聚过程。
12.根据权利要求1～7的植物保护活性化合物制剂的用途，用于控制不需要的植物。
13.控制不需要植物的方法，该方法包括，施用除草活性剂量的、根据权利要求1～7的植物保护活性化合物制剂于作物植株、它的生长场所和/或它的种子上。
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