CN114605344A - 一种噁二唑类化合物、制备方法及应用 - Google Patents
一种噁二唑类化合物、制备方法及应用 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
本发明属于病原菌控制技术领域,具体涉及一种噁二唑类化合物、制备方法及应用。本发明将不同的胺引入1,2,4‑噁二唑类化合物中,得到一类结构新颖的化合物。所述化合物的结构如式I所示:
Description
技术领域
本发明属于病原菌控制技术领域,具体涉及一种噁二唑类化合物、制备方法及应用。
背景技术
真菌引起的植物病害阻碍农业的优质生产,在现代农业发展中不断受到关注。苹果树腐烂病是一种发生范围广,危害程度重的果树病害,现有的商品化药剂无法对这种植物病原真菌的传播起到很好的预防作用。因此,迫切需要发明一种高效、低毒的新型多功能杀菌剂,以避免因长期大规模应用某些单一抗真菌剂而产生的抗药性和安全性问题(Yanget al,J.Agric.Food Chem.,2021,69,8347;Zhang et al,Ind.Crops Prod.,2021,171,113846)。
噁二唑作为一类普遍存在的含氮、氧杂环化合物,由于其独特结构特点,在医药和农业化学中发挥着不可替代的作用,此外,研究表明,在目标化合物中引入噁二唑环可以调整其极性、柔韧性和代谢稳定性,从而有效提高其生物活性。迄今为止,大量研究表明,各种取代的1,3,4-噁二唑具有良好杀虫、抑菌、除草及抗病毒的生物活性(Li et al,Chem.Biol.Drug Des.,2013,82,546;Zheng et al,Chin.Chem.Lett.,2017,28,253)。然而,据我们所知,1,2,4-噁二唑的农用活性尚未得到充分研究,为发现新型农用杀菌剂,发明人将不同胺类化合物引入1,2,4-噁二唑类化合物中,得到一类结构新颖的化合物,并发现它们具有良好的防治植物病原菌的作用。目前尚没有本发明中1,2,4-噁二唑类化合物的报道,为此,本发明公开了一类结构新颖的1,2,4-噁二唑酰胺衍生物化合物及其作为农用杀菌剂的应用。
发明内容
本发明的目的是提供一种噁二唑类化合物、制备方法及应用。
具体的:
本发明的噁二唑类化合物,为式Ⅰ所示的化合物;
式I中的取代基种类如下表所示:
一种噁二唑类化合物的制备方法,包括以下步骤:将式II所示化合物与式III所示
化合物或式IV所示化合物于有机溶剂中反应,得到式I所示化合物;
可选的,在所述的有机溶剂中混入添加物,添加物选自三乙胺、吡啶、二环己基碳二亚胺和4-二甲氨基吡啶中的一种;
有机溶剂选自二氯甲烷、氯仿、甲苯、乙酸乙酯和四氢呋喃中的一种。
所述的添加物的加入量与式II所示化合物的加入量相同。
可选的,所述反应的反应温度为-25~50℃,反应时间为5min~24h。
可选的,式II所示化合物与式III所示化合物的摩尔比为1:(1~1.2);式II所示化合物与式IV所示化合物的摩尔比为1:(1~1.2)。
本发明所述的噁二唑类化合物用于制备植物杀菌剂的应用。
本发明所述的制备方法制备得到的噁二唑类化合物用于制备植物杀菌剂的应用。
本发明所述的噁二唑类化合物用于制备防治水稻纹枯病、油菜菌核病、番茄灰霉病、苹果腐烂病或小麦全蚀病药物的应用。
本发明所述的制备方法制备得到的噁二唑类化合物用于制备防治水稻纹枯病、油菜菌核病、番茄灰霉病、苹果腐烂病或小麦全蚀病药物的应用。
本发明的有益效果为:
本发明将不同的胺类化合物引入到具有优良生物活性的噁二唑环中,所得到的化合物结构新颖,且具有良好的杀菌活性,尤其对水稻纹枯病、油菜菌核病、番茄灰霉病、苹果腐烂病或小麦全蚀病具有明显的抑制效果。
附图说明
附图是用来提供对本公开的进一步理解,并且构成说明书的一部分,与下面的具体实施方式一起用于解释本公开,但并不构成对本公开的限制。在附图中:
图1为本发明化合物I-01的氢谱图;
图2为本发明化合物I-06的氢谱图;
图3为本发明化合物I-27的氢谱图;
图4为本发明化合物I-40的氢谱图。
具体实施方式
以下结合具体实例对本发明作进一步说明,但本发明并不限于这些实施例。所述方法,如无特别说明,均为常规方法。所述材料,如无特别说明,均能从公开商业途径获得。
本发明公开的噁二唑类化合物,具有式I的结构通式;
更加详细的,见表1中所列数据:
表1
以下如无特殊说明,所用的试剂比值均为体积比。
实施例1:化合物4-(5-甲基-1,2,4-噁二唑-3-基)-N-苯基-N-(对甲苯基)苯甲酰胺(I-01)的制备
在25mL单口瓶中依次加入4-(5-甲基-1,2,4-噁二唑-3-基)苯甲酸(3mmol)、4-甲基-N-苯基苯胺(3mmol)以及二环己基碳二亚胺(3mmol),二氯甲烷为溶剂,室温过夜反应,柱层析纯化,干燥后得到白色固体,熔点106.2-106.9℃,1H NMR(500MHz,CDCl3)δ7.91(d,J=8.3Hz,2H),7.55(d,J=8.3Hz,2H),7.28(t,J=7.2Hz,2H),7.18(t,J=7.1Hz,3H),7.12–7.02(m,4H),2.63(s,3H),2.30(s,3H)。
化合物I-01的氢谱图见图1。
实施例2:化合物4-(5-甲基-1,2,4-噁二唑-3-基)-N-(3',4',5'-三氟-[1,1'-联苯]-2-基)苯甲酰胺(I-02)的制备
在25mL单口瓶中加入4-(5-甲基-1,2,4-噁二唑-3-基)苯甲酰氯(3mmol),在三乙胺(3mmol)的存在下在乙酸乙酯中与3',4',5'-三氟-[1,1'-联苯]-2-胺冰浴条件下过夜反应,柱层析纯化,干燥后得到白色固体,熔点179.3-180.1℃,1H NMR(500MHz,CDCl3)δ8.30(d,J=8.1Hz,1H),8.14(d,J=8.4Hz,2H),7.76(d,J=8.2Hz,3H),7.51–7.44(m,1H),7.27(d,J=4.2Hz,2H),7.11–7.07(m,2H),2.67(s,3H).
按照与上述制备化合物I-02相同的方法,用各种不同的胺进行替换,与4-(5-甲基-1,2,4-噁二唑-3-基)苯甲酰氯反应即可得相应产物I-03~I-04,化合物的外观、熔点及1HNMR谱数据如下所示。
化合物(3,4-二氢喹啉-1(2H)-基)(4-(5-甲基-1,2,4-噁二唑-3-基)苯基)甲酮(I-03):白色固体,熔点:126.7-127.3℃,1H NMR(500MHz,CDCl3)δ7.97(d,J=7.2Hz,2H),7.46(d,J=7.5Hz,2H),7.19–7.15(m,1H),7.00(t,J=6.9Hz,1H),6.85(t,J=7.6Hz,1H),6.77–6.59(m,1H),3.94(s,2H),2.87(s,2H),2.65(s,3H),2.08(s,2H).
化合物(3,4-二氢异喹啉-2(1H)-基)(4-(5-甲基-1,2,4-噁二唑-3-基)苯基)甲酮(I-04):白色固体,熔点:146.2-147.2℃,1H NMR(500MHz,CDCl3)δ8.14(d,J=6.4Hz,2H),7.57(d,J=5.4Hz,2H),7.28–6.85(m,4H),4.75(s,2H),3.83(s,2H),2.94(s,2H),2.67(s,3H).
实施例3:化合物4-(5-(二氟甲基)-1,2,4-噁二唑-3-基)-N-苯基-N-(对甲苯基)苯甲酰胺(I-05)的制备
在25mL单口瓶中依次加入4-(5-(二氟甲基)-1,2,4-噁二唑-3-基)苯甲酸(3mmol)、4-甲基-N-苯基苯胺(3.6mmol)、二环己基碳二亚胺(3mmol)和4-二甲氨基吡啶(0.3mmol),氯仿为溶剂,50℃过夜反应,柱层析纯化,干燥后得到黄色固体,熔点143.6-144.3℃,1H NMR(500MHz,CDCl3)δ7.96(d,J=8.3Hz,2H),7.58(d,J=8.3Hz,2H),7.30–7.28(m,2H),7.20–7.17(m,3H),7.09–7.05(m,4H),6.83(t,J=52.2Hz,1H),2.30(s,3H).
按照与上述制备化合物I-05相同的方法,用各种不同的胺进行替换,与4-(5-二氟甲基-1,2,4-噁二唑-3-基)苯甲酸反应即可得相应产物I-06~I-09,化合物的外观、熔点及1HNMR谱数据如下所示。
化合物4-(5-(二氟甲基)-1,2,4-噁二唑-3-基)-N-(3',4',5'-三氟-[1,1'-联苯]-2-基)苯甲酰胺(I-06):白色固体,熔点:142.1-143.7℃,1H NMR(500MHz,CDCl3)δ8.28(d,J=8.1Hz,1H),8.20(d,J=8.3Hz,2H),7.80(d,J=8.4Hz,3H),7.52–7.45(m,1H),7.30–7.27(m,2H),7.09(t,J=7.1Hz,2H),6.88(t,J=52.1Hz,1H).化合物I-06的氢谱图见图2。
化合物(4-(5-(二氟甲基)-1,2,4-噁二唑-3-基)苯基)(3,4-二氢喹啉-1(2H)-基)甲酮(I-07):白色固体,熔点:117.2-118.1℃,1H NMR(500MHz,CDCl3)δ8.01(d,J=8.2Hz,2H),7.48(d,J=8.2Hz,2H),7.17(d,J=7.5Hz,1H),7.01(t,J=7.4Hz,1H),6.86(t,J=52.2Hz,1H),6.85(t,J=7.5Hz,1H),6.65(s,1H),3.94(t,J=6.6Hz,2H),2.87(t,J=6.6Hz,2H),2.08(p,J=6.6Hz,2H).
化合物(4-(5-(二氟甲基)-1,2,4-噁二唑-3-基)苯基)(3,4-二氢异喹啉-2(1H)-基)甲酮(I-08):白色固体,熔点:99.2-99.7℃,1H NMR(500MHz,CDCl3)δ8.19(d,J=7.8Hz,2H),7.61(d,J=6.8Hz,2H),7.23–6.90(m,4H),6.89(t,J=52.2Hz,1H),4.75(s,2H),3.84(s,2H),2.95(s,2H).
化合物4-(5-(二氟甲基)-1,2,4-噁二唑-3-基)-N-(3-甲氧基苯乙基)苯甲酰胺(I-09):白色固体,熔点:112.6-113.4℃,1H NMR(500MHz,CDCl3)δ8.15(d,J=8.4Hz,2H),7.82(d,J=8.3Hz,2H),7.29–7.23(m,1H),6.88(t,J=52.2Hz,1H),6.84–6.80(m,3H),6.22(s,1H),3.80(s,3H),3.75(dd,J=12.9,6.7Hz,2H),2.94(t,J=6.8Hz,2H).
实施例4:化合物N-(2,6-二异丙基苯基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-10)的制备
在25mL单口瓶中依次加入4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酸(3mmol)、2,6-二异丙基苯胺(3mmol)以及4-二甲氨基吡啶(3mmol),甲苯为溶剂,室温过夜反应,柱层析纯化,干燥后得到白色固体,熔点:232.3-232.5℃,1H NMR(500MHz,CDCl3)δ8.24(d,J=8.3Hz,2H),8.05(d,J=8.3Hz,2H),7.47(s,1H),7.37(t,J=7.7Hz,1H),7.25(d,J=7.8Hz,2H),3.18–3.08(m,2H),1.23(d,J=6.8Hz,12H).
实施例5:化合物N-(2,6-二乙基-4-甲基苯基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-11)的制备
在25mL单口瓶中加入4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰氯(3mmol),在吡啶(3.6mmol)的存在下与2,6-二乙基-4-甲基苯胺反应,四氢呋喃为溶剂,冰浴条件下反应5分钟,柱层析纯化,熔点:239.6-240.5℃,1H NMR(500MHz,CDCl3)δ8.25(d,J=8.3Hz,2H),8.05(d,J=8.3Hz,2H),7.38(s,1H),6.99(s,2H),2.62(q,J=7.6Hz,4H),2.36(s,3H),1.21(t,J=7.6Hz,6H).
按照与上述制备化合物I-11相同的方法,用各种不同的胺进行替换,与4-(5-三氟甲基-1,2,4-噁二唑-3-基)苯甲酰氯反应即可得相应产物I-12~I-40,化合物的外观、熔点及1H NMR谱数据如下所示。
化合物N-苯基-4-(5-(三氟甲基)-1,2,4噁二唑3-基)苯甲酰胺(I-12):白色固体,熔点:182.3-183.1℃,1H NMR(500MHz,CDCl3)δ8.24(d,J=8.4Hz,2H),8.06(d,J=8.4Hz,2H),7.43(s,1H),6.95(s,2H),2.31(s,3H),2.26(s,6H).
化合物N-(3-异丙氧基苯基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-13):白色固体,熔点:134.2-134.5℃,1H NMR(500MHz,CDCl3)δ8.23(d,J=8.3Hz,2H),8.00(d,J=8.2Hz,2H),7.90(s,1H),7.41(s,1H),7.27–7.24(m,1H),7.09(d,J=7.7Hz,1H),6.72(dd,J=8.2,1.5Hz,1H),4.58(dq,J=11.9,6.0Hz,1H),1.35(d,J=6.0Hz,6H).
化合物N-(噻吩-2-基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-14):黄色固体,熔点:223.4-223.9℃,1H NMR(500MHz,CDCl3)δ8.26(d,J=8.4Hz,2H),8.18(s,1H),8.02(d,J=8.3Hz,2H),7.77(d,J=2.1Hz,1H),7.31(dd,J=5.1,3.2Hz,1H),7.15(d,J=5.4Hz,1H).
化合物N-(4-乙炔基苯基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-15):白色固体,熔点:218.2-219.1℃,1H NMR(500MHz,CDCl3)δ8.27(d,J=8.4Hz,2H),8.03(d,J=8.3Hz,2H),7.88(s,1H),7.65(d,J=8.5Hz,2H),7.53(d,J=8.6Hz,2H),3.08(s,1H).
化合物N-(3',4',5'-三氟-[1,1'-联苯]-2-基)-4-(5(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-16):白色固体,熔点:134.3-134.8℃,1H NMR(500MHz,CDCl3)δ8.19(s,1H),8.17(d,J=8.2Hz,2H),7.92(s,1H),7.79(d,J=8.3Hz,2H),7.46–7.43(m,1H),7.31–7.27(m,2H),7.06(t,J=6.9Hz,2H).
化合物N-(2-苯氧基苯基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-17):黄色固体,熔点:101.8-102.6℃,1H NMR(500MHz,CDCl3)δ8.60(d,J=7.4Hz,1H),8.53(s,1H),8.19(d,J=8.4Hz,2H),7.91(d,J=8.4Hz,2H),7.38(t,J=8.0Hz,2H),7.18(q,J=7.8Hz,2H),7.10–7.07(m,3H),6.92(dd,J=8.1,1.0Hz,1H).
化合物4-(4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰氨基)苯甲酸乙酯(I-18):白色固体,熔点:193.7-194.1℃,1H NMR(500MHz,CDCl3)δ8.28(d,J=8.3Hz,2H),8.09(d,J=8.6Hz,2H),8.04(d,J=8.3Hz,2H),8.02(s,1H),7.76(d,J=8.6Hz,2H),4.39(q,J=7.1Hz,2H),1.41(t,J=7.1Hz,3H).
化合物N-(2,6-二乙基苯基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-19):黄色固体,熔点:157.6-159.3℃,1H NMR(500MHz,CDCl3)δ8.27(d,J=8.3Hz,2H),8.07(d,J=8.3Hz,2H),7.43(s,1H),7.31–7.27(m,1H),7.19(d,J=7.6Hz,2H),2.67(q,J=7.5Hz,4H),1.23(t,J=6.6Hz,6H).
化合物N-(3-氯-4-(4-氯苯氧基)苯基)-4-(5(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-20):白色固体,熔点:183.4-184.2℃,1H NMR(500MHz,CDCl3)δ8.26(d,J=8.4Hz,2H),8.02(d,J=8.4Hz,2H),7.94–7.89(m,2H),7.52(dd,J=8.8,2.5Hz,1H),7.29(d,J=8.9Hz,2H),7.04(d,J=8.8Hz,1H),6.89(d,J=8.9Hz,2H).
化合物N-(萘-2-基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-21):黄色固体,熔点:240.7-241.2℃,1H NMR(500MHz,DMSO)δ10.70(s,1H),8.50(s,1H),8.27–8.23(m,3H),8.19–8.15(m,1H),7.93(d,J=8.9Hz,1H),7.89–7.87(m,3H),7.51(t,J=7.6Hz,1H),7.45(t,J=7.5Hz,1H).
化合物N-(4-溴代萘-1-基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-22):白色固体,熔点:247.4-247.7℃,1H NMR(500MHz,CDCl3)δ8.44–8.37(m,1H),8.34–8.26(m,2H),8.10–8.02(m,3H),7.98(s,1H),7.78(d,J=8.4Hz,1H),7.72(d,J=9.2Hz,1H),7.59(dd,J=19.8,8.3Hz,2H).
化合物N-(2,4-二氯萘-1-基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-23):白色固体,熔点:209.3-209.9℃,1H NMR(500MHz,CDCl3)δ8.32(d,J=8.6Hz,2H),8.24(s,1H),8.19(d,J=8.1Hz,2H),7.94(d,J=8.1Hz,1H),7.89(s,1H),7.71(s,1H),7.67–7.62(m,2H).
化合物N-(1H-吲哚-5-基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-24):白色固体,熔点:112.7-114.5℃.
化合物N-(苯并[d]噻唑-6-基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-25):黄色固体,熔点:130.8-132.2℃.
化合物N-(9-乙基-9H-咔唑-3-基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-26):黄色固体,熔点:128.9-129.5℃,1H NMR(500MHz,CDCl3)δ8.42(s,1H),8.22(d,J=7.8Hz,2H),8.13(s,1H),8.10–8.03(m,3H),7.65(d,J=8.3Hz,1H),7.47(t,J=7.6Hz,1H),7.41–7.35(m,2H),7.21(t,J=7.3Hz,1H),4.35(q,J=7.1Hz,2H),1.43(t,J=7.1Hz,3H).
化合物N-(1-苯乙基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-27):白色固体,熔点:147.6-148.2℃,1H NMR(500MHz,CDCl3)δ8.15(d,J=8.3Hz,2H),7.90(d,J=8.3Hz,2H),7.38(dt,J=15.1,7.6Hz,4H),7.29(t,J=7.1Hz,1H),6.56(d,J=7.5Hz,1H),5.35(p,J=7.0Hz,1H),1.63(d,J=6.9Hz,3H).化合物I-27的氢谱图见图3。
化合物N-(3-甲氧基苯乙基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-28):白色固体,熔点:124.6-125.1℃,1H NMR(500MHz,CDCl3)δ8.13(d,J=8.3Hz,2H),7.82(d,J=8.4Hz,2H),7.24(t,J=7.8Hz,1H),6.87–6.74(m,3H),6.44(t,J=5.1Hz,1H),3.78(s,3H),3.73(q,J=6.8Hz,2H),2.93(t,J=6.9Hz,2H).
化合物N-(喹啉-3-基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-29):白色固体,熔点:221.3-223.8℃
化合物N-(苯并[d]噻唑-5-基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-30):黄色固体,熔点:189.4-190.3℃
化合物N-((苄基氨基)甲基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-31):白色固体,熔点:113.4-115.5℃,1H NMR(500MHz,CDCl3)δ8.17(d,J=8.3Hz,2H),7.88(d,J=8.3Hz,2H),7.20(t,J=7.8Hz,2H),6.75(t,J=7.3Hz,1H),6.68(d,J=7.9Hz,2H),6.60(s,1H),3.75(dd,J=11.6,5.8Hz,2H),3.45(t,J=5.7Hz,2H).
化合物(3,4-二氢异喹啉-2(1H)-基)(4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯基)甲酮(I-32):白色固体,熔点:117.5-118.6℃,1H NMR(500MHz,CDCl3)δ8.20(d,J=7.4Hz,2H),7.61(s,2H),7.22–6.91(m,4H),4.75(s,2H),3.83(s,2H),2.95(s,2H).
化合物N-(6-溴代萘-2-基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-33):黄色固体,熔点:125.8-127.5℃.
化合物N-(萘-2-基)-N-苯基-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-34):棕色固体,熔点:107.3-108.1℃.
化合物N-甲基-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)-N-(4-(三氟甲基)苯基)苯甲酰胺(I-35):白色固体,熔点:226.4-226.7℃.
化合物(3-(羟甲基)-3,4-二氢异喹啉-2(1H)-基)(4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯基)甲酮(I-36):白色固体,熔点:217.5-219.2℃.
化合物(1-甲基-3,4-二氢异喹啉-2(1H)-基)(4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯基)甲酮(I-37):白色固体,熔点:96.2-96.7℃.
化合物(6-溴-3,4-二氢异喹啉-2(1H)-基)(4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯基)甲酮(I-38):白色固体,熔点:223.1-223.7℃.
化合物(3,4-二氢喹啉-1(2H)-基)(4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯基)甲酮(I-39):黄色固体,熔点:112.1-113.0℃,1H NMR(500MHz,CDCl3)δ8.03(d,J=8.2Hz,2H),7.48(t,J=7.8Hz,2H),7.18(d,J=7.5Hz,1H),7.02(t,J=7.4Hz,1H),6.85(t,J=7.5Hz,1H),6.64–6.58(m,1H),3.95(t,J=6.6Hz,2H),2.87(t,J=6.6Hz,2H),2.09(p,J=6.6Hz,2H).
化合物N-苯基-N-(对甲苯基)-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯甲酰胺(I-40):白色固体,熔点111.2-111.7℃,1H NMR(500MHz,CDCl3)δ7.97(d,J=7.8Hz,2H),7.59(d,J=7.8Hz,2H),7.33–7.03(m,5H),2.30(s,3H).HRMS Calcd.for C23H16F3N3O2[M+H]+:424.1267,Found:424.1252.化合物I-40的氢谱图见图4。
实施例6:式I化合物对5种植物病原菌的抑制活性
式I化合物杀菌活性测定采用菌丝生长速率法进行。供试菌种为水稻纹枯病菌、油菜菌核病菌、番茄灰霉病菌、苹果腐烂病菌和小麦全蚀病菌。
分别称取式I化合物,用二甲基亚砜配制成浓度为10000mg/L的母液,分别用移枪吸取上述制备好的10000mg/L的母液,加入到已灭菌、冷却的马铃薯葡萄糖琼脂(PDA)培养基中,混匀后,制备成50mg/L带药培养基,倒入直径为9cm的培养皿中,每皿15mL,每个药剂4次重复。待皿中带药培养基冷凝后,制成带药PDA平板。设二甲基亚砜为溶剂空白对照。将培养好的病原菌平板,沿菌落边缘用打孔器制备成直径0.5cm的菌饼,分别接种于带药和空白对照PDA平板中,置于25℃培养箱中黑暗培养。等空白对照PDA平板中菌落充分生长后,以十字交叉法测量各处理的菌落直径,取其平均值。
用以下公式计算菌丝生长抑制率:
化合物离体杀菌活性数据见表2。
表2式I化合物的离体杀菌活性结果(抑制率%)
从上表可以看出,本发明提供的式Ⅰ化合物对所测试的5种植物病原菌均具有一定的抑制活性。其中,多个化合物对苹果树腐烂病菌、油菜菌核病菌和番茄灰霉病菌的抑制率超过80%。化合物I-03、I-04、I-08、I-21、I-32和I-38对苹果腐烂病菌的抑制率均大于80%,其中I-08和I-32的抑制率分别为95%和93%;化合物I-04对油菜菌核病菌的抑制率为80%;化合物I-08对番茄灰霉病菌的抑制率为84%。
数据表明,式Ⅰ化合物对苹果腐烂病菌、番茄灰霉病菌具有较好的抑制作用,可以作为杀菌剂用于上述植物病原菌的防治。
以上详细描述了本公开的优选实施方式,但是,本公开并不限于上述实施方式中的具体细节,在本公开的技术构思范围内,可以对本公开的技术方案进行多种简单变型,这些简单变型均属于本公开的保护范围。
另外需要说明的是,在上述具体实施方式中所描述的各个具体技术特征,在不矛盾的情况下,可以通过任何合适的方式进行组合,为了避免不必要的重复,本公开对各种可能的组合方式不再另行说明。
此外,本公开的各种不同的实施方式之间也可以进行任意组合,只要其不违背本公开的思想,其同样应当视为本公开所公开的内容。
Claims (10)
3.根据权利要求2所述的噁二唑类化合物的制备方法,其特征在于,还在所述的有机溶剂中混入添加物;
所述的添加物选自三乙胺、吡啶、二环己基碳二亚胺和4-二甲氨基吡啶中的一种;
所述的有机溶剂选自二氯甲烷、氯仿、甲苯、乙酸乙酯和四氢呋喃中的一种。
4.根据权利要求3所述的噁二唑类化合物的制备方法,其特征在于,所述的添加物的加入量与式II所示化合物的加入量相同。
5.根据权利要求2、3或4所述的噁二唑类化合物的制备方法,其特征在于,所述反应的反应温度为-25~50℃,反应时间为5min~24h。
6.根据权利要求2、3或4所述的噁二唑类化合物的制备方法,其特征在于,式II所示化合物与式III所示化合物的摩尔比为1:(1~1.2);
式II所示化合物与式IV所示化合物的摩尔比为1:(1~1.2)。
7.权利要求1中任一所述的噁二唑类化合物用于制备植物杀菌剂的应用。
8.权利要求2-6任一所述的噁二唑类化合物的制备方法制备得到的噁二唑类化合物用于制备植物杀菌剂的应用。
9.权利要求1任一所述的噁二唑类化合物用于制备防治水稻纹枯病、油菜菌核病、番茄灰霉病、苹果腐烂病或小麦全蚀病药物的应用。
10.权利要求2-6任一所述的噁二唑类化合物的制备方法制备得到的噁二唑类化合物用于制备防治水稻纹枯病、油菜菌核病、番茄灰霉病、苹果腐烂病或小麦全蚀病药物的应用。
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