CN105669614A - 含二芳胺基的呋喃甲酰胺类化合物及其在农药中的应用 - Google Patents
含二芳胺基的呋喃甲酰胺类化合物及其在农药中的应用 Download PDFInfo
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Abstract
本发明公开了一类如通式(I)的含二芳胺基的呋喃甲酰胺类化合物及其在农药中的用途。通过对此类化合物的室内活性测定，发现此类化合物可以应用于真菌引起的植物病害的防治，这为植物病害的防治提供一种新的选择。
Description
技术领域
本发明涉及含二芳胺基的呋喃甲酰胺类化合物及其在农药中的应用，特别是它在防治真菌引起的植物病害的应用。
背景技术
植物病害是农业生产的大敌，据联合国粮农组织(FAO)统计每年因植物遭受病害造成的减产平均损失为总产量的10％～15％。由于防治困难，给农业生产造成了极大的损失。
琥珀酸脱氢酶抑制剂是一类作用于病原菌琥珀酸脱氢酶而抑制其呼吸作用的杀菌剂，目前该类已开发的杀菌剂在化学结构方面都含有酰胺基(-CONH-)，如甲呋酰胺、啶酰菌胺、噻呋酰胺、呋吡菌胺和氟吡菌酰胺(李良孔等，琥珀酸脱氢酶抑制剂类(SDHIs)杀菌剂及其抗性研究进展农药,2011,3，165-172)。为了得到抗菌活性更高、抗菌谱更广且结构新颖的化合物，本实验室以杀菌剂甲呋酰胺为先导化合物，采用活性亚结构拼接方法，将具有杀菌活性的二芳胺基类结构引入其中。到目前为此，还未见此类化合物作为农用杀菌剂的应用报道。
发明内容
本发明的目的是提供一种含二芳胺基的呋喃甲酰胺类化合物，它可应用于真菌引起的植物病害的防治。
本发明是下述结构式(I)的化合物:
其中，
R1为甲基；
R2为氢原子，甲基；
R3为氢原子，甲基；
R4为氢原子，氟原子，氯原子，溴原子，甲基，甲氧基，二氟甲基，三氟甲基，三氟甲氧基，环丙烷基；
R5为氢原子，氟原子，氯原子，溴原子，甲基，甲氧基，二氟甲基，三氟甲基，三氟甲氧基，环丙烷基；
R6为氢原子，甲基，乙基，丙基，异丙基。
所述的含二芳胺基的呋喃甲酰胺类化合物应用，其特征是它在防治真菌引起的植物病害的应用。
所述的含二芳胺基的呋喃甲酰胺类化合物是防治真菌引起的植物病害的应用，其特征是真菌为稻瘟病菌、水稻纹枯病菌、玉米纹枯病菌、小麦纹枯病菌、小麦赤霉病菌、玉米小斑病菌、马铃薯晚疫病菌、烟草炭疽病菌、白粉病菌、番茄灰霉病菌、苹果腐烂病菌、葡萄黑痘病菌和油菜菌核病菌。
本发明含二芳胺基的呋喃甲酰胺类化合物易于合成，成本低，对植物真菌具有较好的抑制作用，且结构新颖，在目前已知的对植物真菌有较好抑制作用的化合物中未见有报道。
以下通过具体实施方式，对本发明的上述内容再作进一步的详细说明。但不应将此理解为是对本发明的限制。
具体实施方式
以下实施例的含二芳胺基呋喃甲酰胺类化合物均来源于四川大学农药与作物保护研究所，供试植物病原菌来源于四川大学、中国普通微生物菌种保藏中心和四川农业大学。
实施例1化合物1的制备
2-甲基-3-呋喃甲酰氯的合成方法见参考文献(周国萍等，新型酰胺类化合物的合成及抗植物病原真菌活性研究，四川大学学报(自然科学版)，2012,49,7,871-878.)。
2-氨基二苯胺的合成方法见参考文献(SunQetal.SynthesisandBiologicalEvaluationofAnaloguesofAKT(ProteinKinaseB)Inhibitor-IV.JournalofMedicinalChemistry,2011,54(5):1126-1139.)
将2-氨基二苯胺20mmol放于三口瓶中，然后向里分别加入25mL无水二氯甲烷、5mL三乙胺，于冰浴下搅拌，然后将2-甲基-3-呋喃甲酰氯转入恒压漏斗中缓慢滴加到三口瓶中，30min滴完，随后自然升温至室温，约3h反应完毕，抽滤除去生成的盐，合并有机相，然后分别用饱和NaHCO3溶液洗涤3次，清水洗涤3次，分液，无水Na2SO4干燥，旋蒸除去溶剂得到油状液体粗品，过常压硅胶柱(洗脱剂为：石油醚：乙酸乙酯＝50:1(V/V))得到化合物1。
1HNMR(400MHz,DMSO-d6):δ9.24(s,1H),7.53-7.57(m,2H),7.43(s,1H),7.28-7.31(m,1H),7.14-7.21(m,3H),6.98-7.02(m,1H),6.86-6.90(m,3H),6.76-6.80(m,1H),2.52(s,3H).
实施例2化合物2的制备
化合物2的制备方法如同化合物1的合成方法。
1HNMR(400MHz,DMSO-d6):δ9.22(s,1H),7.55-7.59(m,2H),7.31(d,1H),7.14-7.21(m,2H),7.07-7.11(t,1H),6.86(d,1H),6.79-6.82(d,2H),6.74-6.76(m,1H),2.52(s,3H).
实施例3化合物3的制备
化合物3的制备方法如同化合物1的合成方法。
1HNMR(400MHz,CDCl3):δ8.04(d,1H),7.89(s,2H),7.22(d,1H),7.10-7.21(m,3H),6.90-6.95(m,2H),6.75-6.79(m,2H),2.58(s,3H).
实施例4化合物4的制备
化合物4的制备方法如同化合物1的合成方法。
1HNMR(400MHz,CDCl3):δ8.10(d,1H),7.12-7.24(m,4H),6.83-6.95(m,1H),6.64-6.78(m,2H),6.33(s,1H),5.69(s,1H),2.58(s,3H).
实施例5化合物5的制备
化合物5的制备方法如同化合物1的合成方法。
1HNMR(400MHz,CDCl3):δ8.24(d,1H),7.90(s,1H),7.37(d,1H),7.30-7.32(m,1H),7.24-7.25(m,1H),7.14-7.18(m,1H),7.00-7.03(m,1H),6.54(d,1H),6.28(d,1H),6.04(s,1H),2.58(s,3H).
实施例6化合物6的制备
化合物6的制备方法如同化合物1的合成方法。
1HNMR(400MHz,DMSO-d6):δ9.10(s,1H),7.66-7.69(m,1H),7.56(d,1H),7.48(d,1H),7.27-7.31(m,1H),7.17(t,2H),6.98-6.73(m,1H),6.72-6.79(m,4H),2.51(s,3H).
实施例7化合物7的制备
化合物7的制备方法如同化合物1的合成方法。
1HNMR(400MHz,DMSO-d6):δ9.24(s,1H),7.62(d,1H),7.58(d,2H),7.28(d,1H),7.16-7.20(m,2H),6.04-7.09(t,2H),6.93-6.96(m,2H),6.89(d,1H),2.53(s,3H).
实施例8化合物8的制备
化合物8的制备方法如同化合物1的合成方法。
1HNMR(400MHz,DMSO-d6):δ9.24(s,1H),7.67(d,1H),7.61(s,1H),7.57(d,1H),7.28(d,1H),7.16-7.23(m,3H),6.92(d,2H),6.84-6.86(m,2H),2.53(s,3H).
实施例9化合物9的制备
化合物9的制备方法如同化合物1的合成方法。
1HNMR(400MHz,DMSO-d6):δ9.13(s,1H),7.62-7.66(m,1H),7.57(s,1H),7.45(s,1H),7.21-7.25(m,1H),6.96-7.04(m,3H),6.78-6.82(m,3H),2.52(s,3H).
实施例10含二芳胺基的呋喃甲酰胺类化合物对植物病原真菌的杀菌活性测定
1.供试植物病原真菌
水稻纹枯病菌(Rhizoctoniasolani)、小麦纹枯病菌(Rhizoctoniacerealis)、油菜菌核病菌(Sclerotiniasclerotiorum)。
2.实验方法
含毒培养基法测定菌丝相对抑制率(％)：
首先把含二芳胺基的呋喃甲酰胺类化合物用无菌水稀释后再和PDA培养基混匀，含二芳胺基的呋喃甲酰胺类化合物的最终浓度采用二倍稀释法,制成一系列厚薄均匀的一系列含药平板，用无菌水作为空白对照，每处理重复3次。等培养基凝固后，把植物病原真菌供试菌饼接在凝固的培养基上，在27-28℃培养3-5天，菌饼直径为0.4cm，用十字交叉法测量菌落直径，计算菌丝生长抑制率。
3.实验结果
含二芳胺基的呋喃甲酰胺类化合物对植物病原真菌的抑制活性测定结果(见表1)。由表1结果可知，含二芳胺基的呋喃甲酰胺类化合物对植物病原真菌也具有较好的抑制作用。
表1化合物1-9在20mg/L对植物病原真菌的相对抑制率(％)
综上所述，本发明的含二芳胺基的呋喃甲酰胺类化合物对植物病原真菌具有较好的广谱杀菌活性，将其开发成为具有高效的新型绿色化学农药，具有广阔前景。
Claims (3)
1.一种含二芳胺基的呋喃甲酰胺类化合物，其特征在于它是结构(I)的化合物:
其中，
R1为甲基；
R2为氢原子，甲基；
R3为氢原子，甲基；
R4为氢原子，氟原子，氯原子，溴原子，甲基，甲氧基，二氟甲基，三氟甲基，三氟甲氧基，环丙烷基；
R5为氢原子，氟原子，氯原子，溴原子，甲基，甲氧基，二氟甲基，三氟甲基，三氟甲氧基，环丙烷基；
R6为氢原子，甲基，乙基，丙基，异丙基。
2.根据权利要求1所述的含二芳胺基的呋喃甲酰胺类化合物应用，其特征是它在防治真菌引起的植物病害的应用。
3.根据权利要求2所述的含二芳胺基的呋喃甲酰胺类化合物是防治真菌引起的植物病害的应用，其特征是真菌为稻瘟病菌、水稻纹枯病菌、玉米纹枯病菌、小麦纹枯病菌、小麦赤霉病菌、玉米小斑病菌、马铃薯晚疫病菌、烟草炭疽病菌、白粉病菌、番茄灰霉病菌、苹果腐烂病菌、葡萄黑痘病菌和油菜菌核病菌。
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