CN115124477B - 一类新型嘧啶水杨酸酚酯、其合成方法及作为除草剂的应用 - Google Patents
一类新型嘧啶水杨酸酚酯、其合成方法及作为除草剂的应用 Download PDFInfo
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- 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
- 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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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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Abstract
.一种通式(I)所示的嘧啶水杨酸酚酯其中P选自II‑V结构中一种：
Description
技术领域
本发明涉及除草剂的技术领域，具体是涉及一类新型嘧啶水杨酸酚酯、其合成方法，特别是除草剂在作物中选择性防治禾本科杂草和阔叶杂草的用途。
背景技术
嘧啶水杨酸类除草剂是上世纪90年代开发成功的乙酰乳酸合成酶(ALS)抑制剂，可防除多种难治性杂草，具有高效、安全、广谱、选择性高和环境友好等特点。它是在磺酰脲类除草剂结构优化基础上研究开发的，具有更好的杀草谱和活性，并克服了磺酰脲类除草剂造成的对杂草产生抗药性、残留对后茬农作物产生影响等潜在危害。嘧啶肟草醚(EP0658549)就属于嘧啶水杨酸类除草剂。药物阻止植物所必需的支链氨基酸的合成，最终导致植株死亡。然而，这些已知的化合物具有的除草活性不足(如对鸭舌草等杂草防效一般)或与作物的相容性不足(如对水稻易产生药害)。
发明内容
为了克服公知化合物的除草活性不足的问题，本发明的发明者们深入地研究了公知杂环化合物在生物活性化合物中往往表现出独特的性能，在专利EP0658549的基础上，通过引入不同取代苯环、环己烯酮、吡唑环、异恶唑环，以改进化合物的除草性能，进而实现本发明的目的，提供一类具有高除草活性的化合物，它特别适合用作除草剂。具体的说：
本发明的第一方面，是提供一类由通式(I)所示嘧啶水杨酸衍生物
其中P选自II-V结构中一种：
R是苯环上的取代基。在多取代的情形下，取代基可以相同或不同。这里的取代基是(C1～C5)-烷基、(C1～C5)-烷氧基，三氟甲基、三氟甲氧基、硝基、氰基、卤素(氟、氯、溴、碘)、(C1～C5)-烷硫基、甲磺酰基、三氟甲磺酰基、苯基、苯氧基，在多于两个碳原子的烷基时可以是直链或支链，这也同样适用于烷氧基；
R1取自下列基团中的一种：H、C1～C5直链或支链烷基、2-乙硫基丙基、3-硫杂环己基、4-氧杂环己基、2,4,6-三甲基苯基；
R2取自下列基团中的一种：H、甲基、乙基、二氟甲基、三氟甲基；
R3取自下列基团中的一种：H、C1～C8直链烷基、二氟甲基、三氟甲基；
在所有的下述通式中，取代基和符号具有与通式(I)中所描述的相同的定义，除非另有明确定义。
本发明的第二方面，是提供上述一类由通式(I)所示嘧啶水杨酸衍生物的制备方法，包括如下步骤：
以双草醚、取代酚通过酯化反应，得到式(Ⅰ)所示化合物。
本发明的第三方面，是提供含有一类由通式(I)所示嘧啶水杨酸衍生物的除草组合物。
本发明的除草组合物可以以常规剂型施用，所述常规剂型的形式有可湿性粉剂、乳油、颗粒剂或悬乳浓缩剂。
本发明的第四方面，是提供一类由通式(I)所示嘧啶水杨酸衍生物的用途。
本发明的通式(I)的化合物，由于其对有害植物具有优异的除草活性，因此，本发明的一类由通式(I)所示嘧啶水杨酸衍生物作为除草剂可用于作物中有害植物的防治。
具体实施方式
下面结合实施例对本发明做进一步介绍。
1.化学实施例
2,6-双((4,6-二甲氧基嘧啶-2-基)氧基)苯甲酸苯酯的合成(编号I-01)
步骤：
冰浴条件下，在100ml圆底烧瓶中加入2g双草醚，437.36mg苯酚，56.77mg 4-二甲氨基吡啶，30ml二氯甲烷，搅拌10min，待温度降下来，缓慢滴加1.15g二环己基碳二亚胺溶液。用TLC检测，原料反应完后(约10-18h)，过滤反应液中的白色固体。然后二氯甲烷和石油醚重结晶，得到白色固体2,6-双((4,6-二甲氧基嘧啶-2-基)氧基)苯甲酸苯酯1.76g，收率75％，熔点155～156℃。
本发明的所述的式I化合物具体可选自如下编号的化合物:
表1
2.制剂实施例
(1)粉剂将10％重量比的化合物(I)与90％重量比的滑石粉混合，将混合物在锤磨机中粉碎即得。
(2)可湿性粉剂将25％重量比的化合物(I)、64％重量比的高岭土、10％重量比的木质素磺酸钠和1％重量比的油酰基甲基牛磺酸你混合，在研磨机中研磨而得。
(3)水分散浓缩剂将20％重量比的化合物(I)、6％重量比的烷基苯酚聚乙二醇醚(Triton X207)、3％重量比的异十三烷醇聚乙二醇醚(8E0)和71％重量比的矿物油混合，并将混合物在球磨机中研磨至低于5微米的粒度。
(4)水分散颗粒剂将75％重量比的化合物(I)、10％重量比的木素磺酸钙、5％重量比的十二烷基硫酸钠、3％重量比的聚乙烯醇和7％重量比的高岭土混合，在研磨机中研磨，并在流化床中通过喷洒水而粒化该粉末。
(5)乳油将72％重量比的二甲苯、12％重量比的乳化剂2201加入到反应釜中，搅拌15分钟后加入5％重量比的化合物(I)和1％重量比的抗氧化剂BHT，搅拌1小时至全部溶解。
3.生物对照实施例
本发明的和已知的最接近的现有技术的化合物用于对照实施例：
表2.
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根据使用剂量分别称取各化合物，加入40ul的DMF溶解，用0.1％吐温-80水溶液定容至所需浓度。以不含药剂的DMF水溶液为空白对照。杂草生长至2-3叶期时，使用Hcl-500A智能生测喷雾塔进行茎叶喷雾处理(压力2.5kpa，每盆用药量5ml)，自然晾干后移至玻璃温室进行培养(平均温度30～35℃，相对湿度60％～80％，约14h光照)，每处理重复3次，每盆为一个重复，每盆30株，药后14天秤取各处理稗草地上部分鲜重(g)，按公式(1)计算鲜重抑制率(％)。
表3.
如表3所示，在50mg/L的浓度下11个化合物对6种不同靶标鲜重抑制率都在90％以上，有超过对照药嘧啶肟草醚的除草效果。具有进一步研究开发成除草剂的潜力。
作物相容性试验：
采用芽后除草活性测定相同的方法对水稻、小麦和烟草进行试验，目测观察药害情况：0＝植株生长完全正常；1＝叶片轻微发黄；2＝叶片发黄比较严重；3＝个别叶片严重发黄变枯；4＝植株生长受到严重抑制；5＝植株完全死亡。结果见表4.
如表4所示，进一步测试11个化合物对三种代表性作物相容性试验：水稻、小麦、烟草。在20AI/ha和60AI/ha下，11个化合物相比于对照药嘧啶肟草醚有更好的作物安全性，具有进一步研究开发成除草剂的潜力。
Claims (8)
1.一种通式(I)所示嘧啶水杨酸酚酯
其中P选自II-V结构中一种：
R取自下列基团中的一种：H、(C1～C5)-烷基、(C1～C5)-烷氧基、硝基、F、Cl、Br、三氟甲基；
R1取自下列基团中的一种：H、C1～C5直链或支链烷基、2-乙硫基丙基、3-硫杂环己基、4-氧杂环己基或2,4,6-三甲基苯基；
R2取自下列基团中的一种：H、甲基、乙基、二氟甲基或三氟甲基；
R3取自下列基团中的一种：H、C1～C8直链烷基、二氟甲基或三氟甲基。
2.根据权利要求1所述的嘧啶水杨酸酚酯，其中
R是H、4-甲基、4-氟、2-硝基或4-三氟甲基；
R1是H、甲基、2-乙硫基丙基、3-硫杂环己基或4-氧杂环己基；
R2是H、甲基、二氟甲基或三氟甲基；
R3是H、甲基、二氟甲基或三氟甲基。
3.一种权利要求1或2所述的通式(I)所示嘧啶水杨酸酚酯的制备方法，包括如下步骤：
以双草醚与II'-V'结构的-OH化合物中一种的酯化反应，得到式(Ⅰ)所示化合物，
所述的II'-V'结构的-OH化合物为：
其中，R、R1、R2、R3与权利要求1所示取代基相同。
4.一种除草组合物，其包含有效除草剂量的至少一种权利要求1或2所述通式(I)的嘧啶水杨酸酚酯。
5.根据权利要求4所述的除草组合物，其与制剂助剂混合。
6.根据权利要求4或5所述的除草组合物，其包含至少一种其它的选自杀虫剂、除草剂、杀真菌剂、安全剂或生长调节剂的农药活性化合物。
7.根据权利要求6所述的除草组合物，所述的杀虫剂为杀螨剂。
8.权利要求1或2所述的通式(I)的嘧啶水杨酸酚酯用于防治杂草的用途。
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