CN112616837A - 邻-羟基-对-甲氧基苯甲醛衍生物作为除草剂的用途 - Google Patents
邻-羟基-对-甲氧基苯甲醛衍生物作为除草剂的用途 Download PDFInfo
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- CN112616837A CN112616837A CN202011172195.XA CN202011172195A CN112616837A CN 112616837 A CN112616837 A CN 112616837A CN 202011172195 A CN202011172195 A CN 202011172195A CN 112616837 A CN112616837 A CN 112616837A
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- methoxybenzaldehyde
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- herbicide
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Abstract
本发明公开了邻‑羟基‑对‑甲氧基苯甲醛衍生物作为除草剂的用途。所述邻‑羟基‑对‑甲氧基苯甲醛衍生物，及其以所述邻‑羟基‑对‑甲氧基苯甲醛衍生物为组分的所述除草剂，用于防除田间作物生长场所、非耕作作物场所的杂草。
Description
技术领域
本发明属于农药技术领域，具体涉及一类具有除草活性的邻-羟基-对-甲氧基苯甲醛衍生物作为除草剂的用途，本发明给出了所述邻-羟基-对-甲氧基苯甲醛衍生物的合成工艺以及几种具体化学结构的化合物，本发明还给出了含有所述邻-羟基-对-甲氧基苯甲醛衍生物的除草组合物和混合制剂以及其应用。
背景技术
我国是农业大国，小麦、玉米、水稻等农作物种植面积广，咖啡、茶叶、橡胶、果树等经济作物亦有较大的种植面积。田间和非耕作作物场所杂草发生普遍，杂草种类繁多，主要有阔叶类杂草如反枝苋、藜、田旋花、龙葵、苍耳、鸭跖草、铁苋菜等；禾本科杂草如马唐、狗尾草、牛筋草、狗牙根等；莎草科杂草如香附子等。杂草与作物争夺水分、养分、光照和空间，影响作物正常生长，甚至会造成严重减产。
目前，化学除草剂仍是控制杂草最直接有效的方法。1980年时世界除草剂已占农药总销售额的41％，超过杀虫剂而跃居第一位。我国除草剂每年使用面积以约200万hm2递增。然而，随着化学除草剂的广泛使用，其负面效应也日益凸显，如残留、抗药性、对人畜的毒性、大量杀伤非靶标生物、破坏生态平衡等。近年来多项政策文件着重强调了要推行绿色生产方式，绿色农业以“绿色环境”、“绿色技术”、“绿色产品”为主体，促使过分依赖化学农药的农业向主要依靠生物农药的生态农业转变，用科技为农业重新贴上绿色、安全的标签。另外，目前市面上销售良好的百草枯因其毒性高而被禁用，草甘膦也因为杂草出现抗药性导致使用受限，故研发新型、高效、安全、与环境相容性好的植物源除草剂已是迫切需要解决的问题。
化学除草经济、有效、省力，但是由于大部分除草剂本身杀草谱有限，且长期使用容易造成杂草抗性的产生，因此，研发稳定性更高，除草活性更强，除草谱更广，毒副作用更小，更具实际应用价值的绿色农用除草剂，成为未来发展的必然趋势。此外，现有研究发现，将作用机理不同的除草剂混用，能够有效提高除草效果和杀草谱、延缓杂草抗性的产生。
为进一步拓展邻-羟基-对-甲氧基苯甲醛衍生物在农业领域的应用，发明人合成了系列具有近似化学结构的邻-羟基-对-甲氧基苯甲醛衍生物，结合生测试验数据得出，邻-羟基-对-甲氧基苯甲醛衍生物是一种优良环境友好类除草剂用于防除田间作物生长场所、非耕作作物场所的杂草。依据发明人检索的现有文献获知，目前还未见邻-羟基-对-甲氧基苯甲醛衍生物用作除草剂的报道。
发明内容
在前期试验的基础上，本申请提供邻-羟基-对-甲氧基苯甲醛衍生物作为除草活性组分的新用途，以及含有邻-羟基-对-甲氧基苯甲醛衍生物的除草组合物或混合制剂的新用途。邻-羟基-对-甲氧基苯甲醛衍生物结构简单、性质稳定、毒性低合成路线短、成本低廉，具有更好的开发利用价值，推广应用前景巨大。
邻-羟基-对-甲氧基苯甲醛衍生物作为除草剂的用途，所述除草剂的组分包含邻-羟基-对-甲氧基苯甲醛衍生物1-15中的任一种，
本发明所述邻-羟基-对-甲氧基苯甲醛衍生物可以通过常规的烷基化以及酰基化合成方法合成，上述化合物1-15的谱图数据如下。
化合物1，MS(m/z):179.1(M+H)+，白色固体；1H NMR(600MHz,CDCl3-d1)δ11.50(s,1H),9.74(s,1H),7.46(d,J＝9.0Hz,1H),6.59(dd,J＝8.4,2.4Hz,1H),6.46(d,J＝1.8Hz,1H),6.06-6.03(m,1H),5.47-5.44(m,1H),5.37-5.35(m,1H),4.62-4.61(m,2H)。
化合物2，MS(m/z):219.1(M+H)+，白色固体；1H NMR(600MHz,CDCl3-d1)δ10.38(s,1H),7.84(d,J＝8.4Hz,1H),6.58(dd,J＝8.4,1.8Hz,1H),6.49(d,J＝2.4Hz,1H),6.08-6.03(m,2H),5.49-5.46(m,2H),5.37-5.35(m,2H),4.65-4.61(m,4H)。
化合物3，MS(m/z):193.1(M+H)+，白色固体；1H NMR(600MHz,CDCl3-d1)δ10.38(s,1H),7.86(d,J＝9.0Hz,1H),6.59(dd,J＝8.4,1.2Hz,1H),6.47(d,J＝1.8Hz,1H),6.10-6.07(m,1H),5.50-5.47(m,1H),5.37-5.36(m,1H),4.66-4.65(m,2H),3.89(s,3H)。
化合物4，MS(m/z):167.1(M+H)+，白色固体；1H NMR(600MHz,CDCl3-d1)δ11.49(s,1H),9.70(s,1H),7.42(d,J＝8.4Hz,1H),6.53(dd,J＝8.4,2.4Hz,1H),6.41(d,J＝2.4Hz,1H),4.10-4.06(m,2H),1.44(t,J＝7.2Hz,3H)。
化合物5，MS(m/z):195.1(M+H)+，白色固体；1H NMR(600MHz,CDCl3-d1)δ10.32(s,1H),7.79(d,J＝8.4Hz,1H),6.51(dd,J＝9.0,1.8Hz,1H),6.41(d,J＝1.8Hz,1H),4.13-4.07(m,4H),2.04-1.25(m,6H)。
化合物6，MS(m/z):209.1(M+H)+，白色固体；1H NMR(600MHz,CDCl3-d1)δ11.23(s,1H),9.87(s,1H),7.59(d,J＝8.4Hz,1H),6.80(dd,J＝8.4,1.8Hz,1H),6.76(d,J＝2.4Hz,1H),2.84-2.82(m,1H),1.34(d,J＝7.2Hz,6H)。
化合物7，MS(m/z):253.1(M+H)+，淡黄色油状物；1H NMR(600MHz,CDCl3-d1)δ11.44(s,1H),9.73(s,1H),7.46(d,J＝8.4Hz,1H),6.59(dd,J＝9.0,2.4Hz,1H),6.38(d,J＝1.8Hz,1H),4.56(s,2H),1.49(s,9H)。
化合物8，MS(m/z):239.1(M+H)+，淡黄色油状物；1H NMR(600MHz,CDCl3-d1)δ11.42(s,1H),9.71(s,1H),7.44(d,J＝9.0Hz,1H),6.55(dd,J＝8.4,2.4Hz,1H),6.34(d,J＝2.4Hz,1H),4.82-4.78(m,1H),4.25-4.2(m,2H),1.64(d,J＝6.6Hz,3H),1.28(t,J＝7.2Hz,3H)。
化合物9，MS(m/z):177.0(M+H)+，白色油状物；1H NMR(600MHz,CDCl3-d1)δ11.46(s,1H),9.75(s,1H),7.48(d,J＝8.4Hz,1H),6.63(dd,J＝9.0,2.4Hz,1H),6.54(d,J＝1.8Hz,1H),4.75(d,J＝2.4Hz,2H),2.59(t,J＝2.4Hz,1H)。
化合物10，MS(m/z):207.1(M+H)+，白色固体；1H NMR(600MHz,CDCl3-d1)δ11.23(s,1H),9.87(s,1H),7.60(d,J＝8.4Hz,1H),6.84(dd,J＝8.4,1.8Hz,1H),6.80(d,J＝2.4Hz,1H),6.37(s,1H),5.82(t,J＝1.8Hz,1H),2.07(s,3H)。
化合物11，MS(m/z):297.1(M+H)+，淡黄色油状物；1H NMR(600MHz,CDCl3-d1)δ11.40(s,1H),9.75(s,1H),7.49(dd,J＝8.4,1.2Hz,1H),6.65-6.64(m,1H),6.42(d,J＝2.4Hz,1H),5.25(s,1H),4.33-4.30(m,4H),1.31-1.28(m,6H)。
化合物12，MS(m/z):239.1(M+H)+，淡黄色油状物；1H NMR(600MHz,CDCl3-d1)δ11.48(s,1H),9.73(s,1H),7.45(d,J＝9.0Hz,1H),6.56(dd,J＝8.4,2.4Hz,1H),6.46(d,J＝2.4Hz,1H),5.10(t,J＝4.2Hz,1H),4.20(t,J＝6.6Hz,2H),4.02(t,J＝1.8Hz,2H),3.91(t,J＝6.6Hz,2H),2.22-2.19(m,2H)。
化合物13，MS(m/z):211.1(M+H)+，白色油状物；1H NMR(600MHz,CDCl3-d1)δ11.47(s,1H),9.72(s,1H),7.44(d,J＝8.4Hz,1H),6.56(dd,J＝8.4,2.4Hz,1H),6.45(d,J＝2.4Hz,1H),4.14(t,J＝6.0Hz,2H),3.57(t,J＝6.0Hz,2H),3.37(s,3H),2.10-2.06(m,2H)。
化合物14，MS(m/z):181.1(M+H)+，白色固体；1H NMR(600MHz,CDCl3-d1)δ11.47(s,1H),9.69(s,1H),7.41(d,J＝3.0Hz,1H),6.51(dd,J＝9.0,2.4Hz,1H),6.40(d,J＝2.4Hz,1H),4.64-4.60(m,1H),1.37(d,J＝6.6Hz,6H)。
化合物15，MS(m/z):209.1(M+H)+，土黄色油状物；1H NMR(600MHz,CDCl3-d1)δ11.50(s,1H),9.73(s,1H),7.44(d,J＝9.0Hz,1H),6.56(dd,J＝8.4,2.4Hz,1H),6.44(d,J＝1.8Hz,1H),4.03(t,J＝6.6Hz,2H),1.84-1.80(m,2H),1.46-1.40(m,4H),0.96(t,J＝7.2Hz,3H)。
研究发现，所述邻-羟基-对-甲氧基苯甲醛衍生物，及其以所述邻-羟基-对-甲氧基苯甲醛衍生物为组分的所述除草剂，用于防除田间作物生长场所、非耕作作物场所的杂草。杂草经药剂处理后的症状为萎蔫、干枯、死亡。通过试验获知，与现有除草剂相比，所述邻-羟基-对-甲氧基苯甲醛衍生物具有较高的除草活性，可用于防治对现有除草剂产生抗性的杂草，尤其适用于防治对ALS抑制剂、PSII抑制剂、ACCase抑制剂以及EPSP抑制剂类除草剂产生抗性的杂草。
在本发明中，所述杂草应具有最为广泛或较为广泛的含义，包括在不希望的地方生长的所有类型的植物种类。本发明将所述“不希望的地方”分为田间作物生长场所和非耕作作物场所。田间作物生长场所是指通常意义上的田间或大田。非耕作作物场所是指除田间作物生长场所之外的，不希望杂草生长的地方，包括葡萄园、苹果园、柑橘园、香蕉培育场、咖啡种植场、茶叶种植场、橡胶种植场、油棕种植场、椰子种植场等场所。
所述邻-羟基-对-甲氧基苯甲醛衍生物，及其以所述邻-羟基-对-甲氧基苯甲醛衍生物为组分的所述除草剂，可以用于防除生长于下述作物田间的下述杂草。
双子叶植物纲中的作物属：棉属，大豆属，甜菜属，菜豆属，豌豆属，茄属，亚麻属，番茄属，落花生属，芸苔属，莴苣属，香瓜属，南瓜属等。
单子叶植物纲中的作物属：稻属，玉蜀黍属，小麦属，大麦属，燕麦属，稷属，甘蔗属，凤梨属，天门冬属，葱属等。
双子叶植物纲的杂草属：白芥属，芥属，猪殃殃属，繁缕属，藜属，地肤属，荨麻属，千里光属，苋属，马齿苋属，苍耳属，番薯属，蓼属，豚草属，蓟属，苦苣菜属，茄属，婆婆纳属，曼陀罗属，堇菜属，罂粟属，矢车菊属，牛腾菊属，节节菜属，母草属，田菁属，车轴草属，苘麻属，野芝麻属，母菊属，蒿属，牵牛属等。
单子叶植物纲的杂草属：稗属，狗尾草属，稷属，马唐属，梯牧草属，早熟禾属，羊毛属，黑麦草属，雀麦属，燕麦属，莎草属，蜀黍属，冰草属，雨久花属，飘拂草属，慈姑属，藨草属，雀稗属，鸭嘴草属，剪股颖属，看买年属，狗牙根属，鸭跖草属，臂形草属，千金子属等。
进一步地，所述邻-羟基-对-甲氧基苯甲醛衍生物，及其以所述邻-羟基-对-甲氧基苯甲醛衍生物为组分的所述除草剂，可以用于防除下述代表性的农田杂草。所述农田杂草包括：稗草、眼子菜、鸭舌草、异型莎草、扁秆蔗草、千金子、野燕麦、马唐、蟋蟀草、狗尾草、看麦娘、播娘蒿、荠菜、独行菜、葎草、萹蓄、田旋花、卷茎蓼、香附子、藜、酸模叶蓼、反枝苋、马齿苋、凹头苋、菟丝子、苘麻、猪殃殃、鱧肠、苍耳、狗牙根、白茅、龙葵、牛繁缕、飞机草、盛红蓟、圆叶节节菜、艾蒿、蒲公英、一年蓬、泥胡菜、茵陈、苦荬菜、小蓟、大蓟、香薷、水苏、铁苋菜等。
再者，本发明提供一种组合物作为农用除草剂的用途，其所述组合物中的除草组分含有所述的邻-羟基-对-甲氧基苯甲醛衍生物，所述组合物还包括农业上接受的载体。关于所述组合物的在农业上的使用方法，发明人通过试验获知，采用苗前土壤处理或苗后茎叶喷雾的方法施于土壤或杂草上，可以获得较好的除草效果。
为获得理想的除草效果，所述的邻-羟基-对-甲氧基苯甲醛衍生物用量因各种因素而改变，例如所用化合物、欲保护的作物、欲防治的杂草、杂草生长程度、气候条件、施药方法、采用的剂型等。
还有，本发明提供一种混合制剂作为农用除草剂的用途。这种混合制剂的除草活性组分包括所述的邻-羟基-对-甲氧基苯甲醛衍生物，还包括作为乙酰辅酶A羧化酶抑制剂、乙酰乳酸合成酶抑制剂、生长素除草剂、类胡萝卜素生物合成抑制剂、光合作用抑制剂、细胞壁生物合成抑制剂的除草组分，所述除草组分与所述N-苄基苯甲酰胺类化合物或其盐混合使用或表现出复配增效作用。
本领域技术人员应当知晓，本发明所提供的组合物作为农用除草剂的用途，以及混合制剂作为农用除草剂的用途，所述组合物或混合制剂通常以制剂的形式在农业上使用，其还包括农业上可接受的载体。所述邻-羟基-对-甲氧基苯甲醛衍生物，或与其复配的其它除草活性组分，作为活性组分溶解或分散于载体中或配制成制剂以便作为除草剂使用时更易于分散。这些化学制剂可被制成可湿性粉剂、水分散粒剂、水乳剂、可分散油悬浮剂、乳油或悬浮剂中的任何一种剂型，但并不限定于此。对制剂加工领域的技术人员来说，可以选用一种或多种适宜的载体或助剂。
本发明的有益效果或优点：
本发明给出了所述邻-羟基-对-甲氧基苯甲醛衍生物在除草方面的新用途，拓展了所述邻-羟基-对-甲氧基苯甲醛衍生物在农业领域的应用。所述邻-羟基-对-甲氧基苯甲醛衍生物用于防除田间作物生长场所、非耕作作物场所的杂草，除草活性高，并可用于防治对现有除草剂产生抗性的杂草，尤其适用于防治对ALS抑制剂、PSII抑制剂、ACCase抑制剂以及EPSP抑制剂类除草剂产生抗性的杂草。
本发明还给出了所述邻-羟基-对-甲氧基苯甲醛衍生物的合成制备工艺，原料来源价格低廉，合成路线短，收率高，大规模工厂化合成易于实现。
本发明还进一步明确了含有所述邻-羟基-对-甲氧基苯甲醛衍生物以及混合制剂，对田间作物生长场所、非耕作作物场所的杂草同样表现出较好的防除效果，这充分说明所述邻-羟基-对-甲氧基苯甲醛衍生物具有很大的开发潜力，为开发新的绿色化学农药提供了一种新的思路。含有所述邻-羟基-对-甲氧基苯甲醛衍生物的组合物以及混合制剂，可以配制成符合农业生产需求的悬浮剂、水分散粒剂、可湿性粉剂或可分散油悬浮剂剂型等多种剂型，且对作物安全性好，符合农药制剂的安全性要求。本发明丰富了现有除草剂品种，可以带来可观的市场效益。
附图说明
图1是本发明所述邻-羟基-对-甲氧基苯甲醛衍生物1-15的除草活性图。
具体实施方式
为了便于理解本发明的目的、技术方案及其效果，现结合实施例对本发明的技术方案做进一步详细阐述。
1、邻-羟基-对-甲氧基苯甲醛衍生物的合成
本发明所述邻-羟基-对-甲氧基苯甲醛衍生物1-15可以通过常规的烷基化以及酰基化合成方法合成，具体的合成路线及方法简述如下。
将2,4-二羟基苯甲醛(2.0g,14.48mmol)，无水碳酸钾(4.0g,28.96mmol)，碘化钾(0.24g,1.448mmol)溶于适量的丙酮中，加入卤代物(11.58mmol)；加热至回流反应。TCL监控反应，待反应结束后，冷却至室温，过滤，浓缩滤液，柱层析(PE/EA＝30:1-15:1 or DCM/EA＝10:1-5:1)得产品。邻-羟基-对-甲氧基苯甲醛衍生物7-9和11-15参照该方法制备。
将2,4-二羟基苯甲醛(2.0g,14.48mmol)溶于适量的二氯甲烷中，加入三乙胺(4-6ml,28.96-43.44mmol)，在-5℃下加入酰卤(11.58mmol)；室温反应，TCL监控反应，待反应结束后，加入适量二氯甲烷，水洗，无水硫酸钠干燥有机相，浓缩，柱层析(PE/EA＝30:1-15:1 or DCM/EA＝10:1-5:1)得产品。邻-羟基-对-甲氧基苯甲醛衍生物1-2、4-6和10参照该方法制备。
将2-羟基-4-甲氧基苯甲醛(2.0g,13.14mmol)，无水碳酸钾(5.45g,39.43mmol)，溶于适量的丙酮中，加入卤代物(11.58mmol)；20℃反应。TCL监控反应，待反应结束后，加入适量的水，乙酸乙酯提取，合并有机相，干燥，浓缩，柱层析(PE/EA＝30:1-15:1 or DCM/EA＝10:1-5:1)得产品。邻-羟基-对-甲氧基苯甲醛衍生物3参照该方法制备。
2、邻-羟基-对-甲氧基苯甲醛衍生物的除草活性
采用叶片涂抹法测试邻-羟基-对-甲氧基苯甲醛衍生物1-15的除草活性。将化合物溶解在丙酮中，配制成相关浓度的化合物，具体地，化合物3的浓度为0.625mg/ml，化合物5的浓度为10mg/ml，其余化合物浓度均为2.5mg/ml。
选取贵州省贵阳市白云区沙文镇野外生长的葎草壮龄叶为测试叶。用一个软毛刷均匀的把药液涂抹在所选测试叶的表面，以丙酮为对照，每样重复3次。24h后观察测试叶的变化情况，记录并拍照，参见图1。如图1所示，邻-羟基-对-甲氧基苯甲醛衍生物1-15具有明显的除草活性。
叶片受试后约4h，叶片即变为褐色，继而萎蔫失绿，1d后干枯，但一直未掉落。受试叶片出现中毒症状，但同株植物的其他未受试样品并未出现中毒症状，推测药剂在叶片间不能相互传导。
以上所述，实施例仅仅是对本发明的优选实施方式进行描述，并非对本发明的范围进行限定，在不脱离本发明技术思路的前提下，本领域普通技术人员对本发明的技术方案作出的各种变形和改进，均应落入本发明权利要求书确定的保护范围内。
Claims (5)
1.邻-羟基-对-甲氧基苯甲醛衍生物作为除草剂的用途，其特征在于，所述除草剂的组分包含邻-羟基-对-甲氧基苯甲醛衍生物1-15中的任一种，
2.根据权利要求1所述的用途，其特征在于，所述邻-羟基-对-甲氧基苯甲醛衍生物，及其以所述邻-羟基-对-甲氧基苯甲醛衍生物为组分的所述除草剂，用于防除田间作物生长场所、非耕作作物场所的杂草。
3.根据权利要求3所述的用途，其特征在于，所述杂草为葎草。
4.一种组合物作为农用除草剂的用途，其特征在于，所述组合物中的除草组分为根据权利要求1所述的用途中的邻-羟基-对-甲氧基苯甲醛衍生物，所述组合物还包括农业上接受的载体。
5.一种混合制剂作为农用除草剂的用途，其特征在于，所述组合物包括根据权利要求1所述的用途中的邻-羟基-对-甲氧基苯甲醛衍生物，还包括作为乙酰辅酶A羧化酶抑制剂、乙酰乳酸合成酶抑制剂、生长素除草剂、类胡萝卜素生物合成抑制剂、光合作用抑制剂、细胞壁生物合成抑制剂的除草组分，所述除草组分与所述邻-羟基-对-甲氧基苯甲醛衍生物混合使用或表现出复配增效作用。
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