CN107400136A - 2-取代苯氧亚甲基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶及其制备方法 - Google Patents

2-取代苯氧亚甲基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶及其制备方法 Download PDF

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CN107400136A
CN107400136A CN201610344856.XA CN201610344856A CN107400136A CN 107400136 A CN107400136 A CN 107400136A CN 201610344856 A CN201610344856 A CN 201610344856A CN 107400136 A CN107400136 A CN 107400136A
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pyrimidine
triazols
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methylthiopyrimidines
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CN107400136B (zh
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王涛
熊更明
吴小盛
赵安林
余维洁
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Jiangxi Normal University
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Abstract

2‑取代苯氧亚甲基嘧啶并[5,4‑e]‑1,2,4‑三唑并[1,5‑c]嘧啶及其制备方法，其结构通式为：式中，R1表示正烷基；R2表示取代氯；R3表示烷基。本发明具有结构通式Ⅰ的化合物对单子叶或双子叶植物的生长具有显著的抑制作用，可用作除草剂的有效成分。

Description

2-取代苯氧亚甲基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶及其制备方法
技术领域
本发明涉及具有除草活性的2-取代苯氧亚甲基-5-烷基-4,6-二氢-8-烷硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶及其制备方法，以及它作为除草剂的生物活性。
背景技术
嘧啶(C4H4N2，1,3-二氮杂苯)是一种杂环化合物。由2个氮原子取代苯分子间位上的2个碳形成，是一种二嗪。和吡啶一样，嘧啶保留了芳香性。其四个碳上均可以发生取代而生成嘧啶的衍生物。嘧啶的特殊结构使得其具备其他结构所不具备的生物活性，如抗虫抗菌，杀鼠除草等。嘧啶还经常作为合成其他化合物的中间体，有着十分广泛的运用前景。
嘧啶类化合物和其衍生物在生物体内起着重要作用,是一类具有良好生物活性的杂环化合物。嘧啶作为中间体被广泛应用于抗生素,镇静催眠药以及新型喷陡系超高效除草剂的合成。近些年来人们又发现了一些含有嘧啶环的药物具有抗肿瘤的活性,如:硝酸嘧啶氮芥类抗肿瘤药物,具有抗癌谱广、选择性高、毒性低等优点,并在临床上得到了广泛的应用。含嘧啶环的硫脲类化合物常被用于杀菌剂。硫脲类化合物由于结构中存在不同取代的肽键(CONH),因此具有广谱的抗菌性和杀虫性
嘧啶结构运用前景广阔，所以找到快捷简便的合成嘧啶的方法非常有意义。嘧啶及其衍生物是杂环化合物中重要的一类,是多种药物、农药、香料及有机合成的中间体,嘧啶合成方法的优化和改进将大大促进相关产业的发展。嘧啶和芳环取代嘧啶的合成方法有很多报道,其中后者的合成方法主要分为两类,一类是经过环合反应生成嘧啶,另一类是在己有嘧啶结构的化合物上直接引入所需官能团或在嘧啶衍生物上交换官能团。
发明内容
本发明的目的是提供一种2-取代苯氧亚甲基-5-烷基-4,6-二氢-8-烷硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶及其制备方法，探索具有新结构并具有除草活性的多取代嘧啶衍生物。
为实现本发明的目的采取的技术方案是:
(1)所述2-取代苯氧亚甲基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶结构通式如Ⅰ：
式中：R1表示乙基，正丙基，正丁基；R2表示邻氯，对氯，邻对二氯；R3表示甲基，乙基，正丙基，异丙基，正丁基，异丁基。
(2)所述2-取代苯氧亚甲基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶制备方法是：用通式为Ⅱ的三唑联嘧啶与脂肪醛反应生成通式为Ⅰ的化合物，乙醇作为溶剂进行制备；
以通式Ⅰ表示的化合物的合成路线如下：
通式为Ⅱ的R1、R2的定义与权利要求中1的所述的结构通式Ⅰ中R1、R2的定义相同。
上述反应式中的Ⅱ与脂肪醛摩尔比为1:1.2，在乙醇中回流反应3-4小时，即可得到较好的产率。
本发明的有益效果：2-取代苯氧亚甲基-5-烷基-4,6-二氢-8-烷硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶对单子叶和双子叶植物的生长具有显著的抑制作用，可作为除草剂的有效成分。
具体实施方式
下面通过实例来具体地说明本发明的式工化合物的制备方法,这些实施例仅仅对本发明进行说明,而不是对本发明进行限制。
实施例1化合物1的制备
2-苯氧亚甲基-5-甲基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
将嘧三唑联嘧啶化合物取2.5mmol(约1g)，催化剂四氯化锆1.25mmol(50mol％)，取20mL无水乙醇溶解，向体系中加入3mmol(1:1.2)脂肪醛。整个反应过程搅拌回来3-4小时。反应过程中，会有淡黄色固体沉淀析出，该固体即是我们需要的嘧啶并嘧啶带三氮唑骨架的化合物。产率为75％，m.p.212-223℃。
C18H20N6OS2
IR(KBr,υ/cm-1)：2962，2931，1529，1452，681
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,5H),5.24(s,2H),3.16–3.05(m,2H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,4H),0.99(t,J＝7.3Hz,3H).
MS(EI，m/z，％)：400(M+)；Anal.Calcd.(％)for C16H20N6OS2:C,53.98；H,5.03；N,20.98；found:C,53.96；H,5.02；N,20.99
下列53个化合物按化合物1类似的方法制得,其结构鉴定数据如下:
化合物2
2-苯氧亚甲基-5-乙基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率78％，m.p.235-236℃
C19H22N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,5H),5.24(s,2H),3.16–3.05(m,4H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,4H),0.99(t,J＝7.3Hz,3H).
MS(EI，m/z，％)：414(M+)；Anal.Calcd.(％)for C19H22N6OS2:C,55.05；H,5.35；N,20.27；found:C,55.03；H,5.34；N,20.29
化合物3
2-苯氧亚甲基-5-正丙基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率76％，m.p.242-243℃
C20H24N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,5H),5.24(s,2H),3.16–3.05(m,6H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,4H),0.99(t,J＝7.3Hz,3H).
MS(EI，m/z，％)：428(M+)；Anal.Calcd.(％)for C20H24N6OS2:C,56.05；H,5.64；N,19.61；found:C,56.07；H,5.63；N,19.60
化合物4
2-苯氧亚甲基-5-异丙基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率81％，m.p.232-233℃
C20H24N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,5H),5.24(s,2H),3.16–3.05(m,6H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,4H),0.99(t,J＝7.3Hz,3H).
MS(EI，m/z，％)：428(M+)；Anal.Calcd.(％)for C20H24N6OS2:C,56.05；H,5.64；N,19.61；found:C,56.06；H,5.62；N,19.62
化合物5
2-苯氧亚甲基-5-正丁基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率72％，m.p.256-258℃
C21H26N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,5H),5.24(s,2H),3.16–3.05(m,8H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,4H),0.99(t,J＝7.3Hz,3H).
MS(EI，m/z，％)：442(M+)；Anal.Calcd.(％)for C21H26N6OS2:C,56.99；H,5.92；N,18.99；found:C,56.97；H,5.93；N,19.01；
化合物6
2-苯氧亚甲基-5-异丁基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率77％，m.p.251-253℃
C21H26N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,5H),5.24(s,2H),3.16–3.05(m,5H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,4H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：442(M+)；Anal.Calcd.(％)for C21H26N6OS2:C,56.99；H,5.92；N,18.99；found:C,56.98；H,5.94；N,19.00；
化合物7
2-对氯苯氧亚甲基-5-甲基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率72％，m.p.261-262℃
C18H19ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,4H),5.24(s,2H),3.16–3.05(m,1H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,2H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：434(M+)；Anal.Calcd.(％)for C18H19ClN6OS2:C,49.70；H,4.40；N,19.32；found:C,49.73；H,4.41；N,19.28
化合物8
2-对氯苯氧亚甲基-5-乙基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率75％，m.p.267-269℃
C19H21ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,4H),5.24(s,2H),3.16–3.05(m,1H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,4H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：448(M+)；Anal.Calcd.(％)for C19H21ClN6OS2:C,50.83；H,4.71；N,18.72；found:C,50.85；H,4.70；N,18.70
化合物9
2-对氯苯氧亚甲基-5-正丙基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率77％，m.p.272-273℃
C20H23ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,4H),5.24(s,2H),3.16–3.05(m,1H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,6H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：462(M+)；Anal.Calcd.(％)for C20H23ClN6OS2:C,51.88；H,5.01；N,18.15；found:C,51.89；H,5.00；N,18.17
化合物10
2-对氯苯氧亚甲基-5-异丙基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率87％，m.p.263-264℃
C20H23ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,4H),5.24(s,2H),3.16–3.05(m,1H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,9H).
MS(EI，m/z，％)：462(M+)；Anal.Calcd.(％)for C20H23ClN6OS2:C,51.88；H,5.01；N,18.15；found:C,51.86；H,5.04；N,18.19
化合物11
2-对氯苯氧亚甲基-5-正丁基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率74％，m.p.287-289℃
C21H25ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,4H),5.24(s,2H),3.16–3.05(m,3H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,6H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：476(M+)；Anal.Calcd.(％)for C21H25ClN6OS2:C,52.87；H,5.28；N,17.62；found:C,52.89；H,5.29；N,17.60
化合物12
2-对氯苯氧亚甲基-5-异丁基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率79％，m.p.277-279℃
C21H25ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,4H),5.24(s,2H),3.16–3.05(m,3H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,9H).
MS(EI，m/z，％)：476(M+)；Anal.Calcd.(％)for C21H25ClN6OS2:C,52.87；H,5.28；N,17.62；found:C,52.90；H,5.29；N,17.57
化合物13
2-(2,4-二氯苯氧亚甲基)-5-甲基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率63％，m.p.272-274℃
C18H18Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,2H),3.16–3.05(m,3H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,3H).
MS(EI，m/z，％)：468(M+)；Anal.Calcd.(％)for C18H18Cl2N6OS2:C,46.06；H,3.87；N,17.90；found:C,46.08；H,3.89；N,17.85
化合物14
2-(2,4-二氯苯氧亚甲基)-5-乙基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率66％，m.p.279-280℃
C19H20Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,2H),3.16–3.05(m,4H),2.51(s,4H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,3H).
MS(EI，m/z，％)：482(M+)；Anal.Calcd.(％)for C19H20Cl2N6OS2:C,47.20；H,4.17；N,17.38；found:C,47.23；H,4.20；N,17.32
化合物15
2-(2,4-二氯苯氧亚甲基)-5-正丙基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率72％，m.p.287-289℃
C20H22Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,2H),3.16–3.05(m,4H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,3H).
MS(EI，m/z，％)：496(M+)；Anal.Calcd.(％)for C20H22Cl2N6OS2:C,48.29；H,4.46；N,16.89；found:C,48.26；H,4.43；N,16.93
化合物16
2-(2,4-二氯苯氧亚甲基)-5-异丙基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率82％，m.p.280-282℃
C20H22Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,2H),3.16–3.05(m,4H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,3H).
MS(EI，m/z，％)：496(M+)；Anal.Calcd.(％)for C20H22Cl2N6OS2:C,48.29；H,4.46；N,16.89；found:C,48.24；H,4.46；N,16.93
化合物17
2-(2,4-二氯苯氧亚甲基)-5-正丁基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率77％，m.p.293-295℃
C21H24Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,4H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,3H).
MS(EI，m/z，％)：510(M+)；Anal.Calcd.(％)for C21H24Cl2N6OS2:C,49.31；H,4.73；N,16.43；found:C,49.34；H,4.75；N,16.40
化合物18
2-(2,4-二氯苯氧亚甲基)-5-异丁基-4,6-二氢-8-乙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率81％，m.p.288-289℃
C21H24Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,4H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：510(M+)；Anal.Calcd.(％)for C21H24Cl2N6OS2:C,49.31；H,4.73；N,16.43；found:C,49.36；H,4.72；N,16.43
化合物19
2-苯氧亚甲基-5-甲基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率69％，m.p.258-259℃
C19H22N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,2H),3.16–3.05(m,4H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：414(M+)；Anal.Calcd.(％)for C19H22N6OS2:C,55.05；H,5.35；N,20.27；found:C,55.03；H,5.33；N,20.30
化合物20
2-苯氧亚甲基-5-乙基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率74％，m.p.262-263℃
C20H24N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,4H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：428(M+)；Anal.Calcd.(％)for C20H24N6OS2:C,56.05；H,5.64；N,19.61；found:C,56.01；H,5.60；N,19.69
化合物21
2-苯氧亚甲基-5-正丙基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率77％，m.p.269-271℃
C21H26N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,6H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：442(M+)；Anal.Calcd.(％)for C21H26N6OS2:C,56.99；H,5.92；N,18.99；found:C,56.97；H,5.91；N,19.02
化合物22
2-苯氧亚甲基-5-异丙基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率86％，m.p.259-261℃
C21H26N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,6H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：442(M+)；Anal.Calcd.(％)for C21H26N6OS2:C,56.99；H,5.92；N,18.99；found:C,56.97；H,5.91；N,19.02
化合物23
2-苯氧亚甲基-5-正丁基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率79％，m.p.＞300℃
C22H28N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,6H),3.16–3.05(m,6H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：456(M+)；Anal.Calcd.(％)for C21H26N6OS2:C,57.87；H,6.18；N,18.40；found:C,57.89；H,6.14；N,18.45；
化合物24
2-苯氧亚甲基-5-正丁基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率83％，m.p.＞300℃
C22H28N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,6H),3.16–3.05(m,6H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：456(M+)；Anal.Calcd.(％)for C21H26N6OS2:C,57.87；H,6.18；N,18.40；found:C,57.89；H,6.14；N,18.45；
化合物25
2-对氯苯氧亚甲基-5-甲基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率62％，m.p.＞300℃
C19H21ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,4H),5.24(s,2H),3.16–3.05(m,3H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：448(M+)；Anal.Calcd.(％)for C19H21ClN6OS2:C,50.83；H,4.71；N,18.72；found:C,50.80；H,4.70；N,18.76
化合物26
2-对氯苯氧亚甲基-5-乙基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率63％，m.p.＞300℃
C20H23ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,3H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：462(M+)；Anal.Calcd.(％)for C20H23ClN6OS2:C,51.88；H,5.01；N,18.15；found:C,51.86；H,5.00；N,18.18
化合物27
2-对氯苯氧亚甲基-5-正丙基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率73％，m.p.＞300℃
C21H25ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,4H),5.24(s,6H),3.16–3.05(m,3H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：476(M+)；Anal.Calcd.(％)for C21H25ClN6OS2:C,52.87；H,5.28；N,17.62；found:C,52.89；H,5.26；N,17.60
化合物28
2-对氯苯氧亚甲基-5-异丙基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率83％，m.p.＞300℃
C21H25ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,4H),5.24(s,6H),3.16–3.05(m,3H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,2H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：476(M+)；Anal.Calcd.(％)for C21H25ClN6OS2:C,52.87；H,5.28；N,17.62；found:C,52.89；H,5.26；N,17.60
化合物29
2-对氯苯氧亚甲基-5-正丁基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率78％，m.p.＞300℃
C22H27ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,4H),5.24(s,6H),3.16–3.05(m,4H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：490(M+)；Anal.Calcd.(％)for C22H27ClN6OS2:C,53.81；H,5.54；N,17.11；found:C,53.83；H,5.56；N,17.10
化合物30
2-对氯苯氧亚甲基-5-异丁基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率82％，m.p.＞300℃
C22H27ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,4H),5.24(s,6H),3.16–3.05(m,4H),2.51(s,3H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：490(M+)；Anal.Calcd.(％)for C22H27ClN6OS2:C,53.81；H,5.54；N,17.11；found:C,53.83；H,5.56；N,17.10
化合物31
2-(2,4-二氯苯氧亚甲基)-5-甲基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率75％，m.p.＞300℃
C19H20Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,2H),3.16–3.05(m,3H),2.51(s,2H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：482(M+)；Anal.Calcd.(％)for C19H20Cl2N6OS2:C,47.20；H,4.17；N,17.38；found:C,47.22；H,4.19；N,17.35
化合物32
2-(2,4-二氯苯氧亚甲基)-5-乙基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率71％，m.p.＞300℃
C20H22Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,3H),2.51(s,2H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：496(M+)；Anal.Calcd.(％)for C20H22Cl2N6OS2:C,48.29；H,4.46；N,16.89；found:C,48.31；H,4.48；N,16.87
化合物33
2-(2,4-二氯苯氧亚甲基)-5-正丙基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率78％，m.p.＞300℃
C21H24Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,3H),2.51(s,4H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：510(M+)；Anal.Calcd.(％)for C21H24Cl2N6OS2:C,49.31；H,4.73；N,16.43；found:C,49.34；H,4.70；N,16.42
化合物34
2-(2,4-二氯苯氧亚甲基)-5-异丙基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率82％，m.p.＞300℃
C21H24Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,3H),2.51(s,4H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：510(M+)；Anal.Calcd.(％)for C21H24Cl2N6OS2:C,49.31；H,4.73；N,16.43；found:C,49.34；H,4.70；N,16.42
化合物35
2-(2,4-二氯苯氧亚甲基)-5-正丁基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率75％，m.p.＞300℃
C22H26Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,6H),3.16–3.05(m,3H),2.51(s,4H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：524(M+)；Anal.Calcd.(％)for C22H26Cl2N6OS2:C,50.28；H,4.99；N,15.99；found:C,50.26；H,4.98；N,16.02
化合物36
2-(2,4-二氯苯氧亚甲基)-5-异丁基-4,6-二氢-8-丙硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率79％，m.p.＞300℃
C22H26Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,6H),3.16–3.05(m,3H),2.51(s,4H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：524(M+)；Anal.Calcd.(％)for C22H26Cl2N6OS2:C,50.28；H,4.99；N,15.99；found:C,50.26；H,4.98；N,16.02
化合物37
2-苯氧亚甲基-5-甲基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率67％，m.p.＞300℃
C20H24N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,3H),2.51(s,4H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：428(M+)；Anal.Calcd.(％)for C20H24N6OS2:C,56.05；H,5.64；N,19.61；found:C,56.04；H,5.63；N,19.62
化合物38
2-苯氧亚甲基-5-乙基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率71％，m.p.＞300℃
C21H26N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,3H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：442(M+)；Anal.Calcd.(％)for C21H26N6OS2:C,56.99；H,5.92；N,18.99；found:C,56.98；H,5.94；N,18.97
化合物39
2-苯氧亚甲基-5-正丙基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率76％，m.p.＞300℃
C22H28N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,6H),3.16–3.05(m,3H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：456(M+)；Anal.Calcd.(％)for C22H28N6OS2:C,57.87；H,6.18；N,18.40；found:C,57.86；H,6.16；N,18.44
化合物40
2-苯氧亚甲基-5-异丙基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率72％，m.p.＞300℃
C22H28N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,6H),3.16–3.05(m,3H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：456(M+)；Anal.Calcd.(％)for C22H28N6OS2:C,57.87；H,6.18；N,18.40；found:C,57.86；H,6.16；N,18.44
化合物41
2-苯氧亚甲基-5-正丁基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率79％，m.p.＞300℃
C23H30N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,6H),3.16–3.05(m,3H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：470(M+)；Anal.Calcd.(％)for C23H30N6OS2:C,58.69；H,6.42；N,17.86；found:C,58.66；H,6.43；N,17.88
化合物42
2-苯氧亚甲基-5-正丁基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率80％，m.p.＞300℃
C23H30N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,6H),3.16–3.05(m,3H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：470(M+)；Anal.Calcd.(％)for C23H30N6OS2:C,58.69；H,6.42；N,17.86；found:C,58.66；H,6.43；N,17.88
化合物43
2-对氯苯氧亚甲基-5-甲基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率80％，m.p.＞300℃
C20H23ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,2H),3.16–3.05(m,2H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：462(M+)；Anal.Calcd.(％)for C20H23ClN6OS2:C,51.88；H,5.01；N,18.15；found:C,51.86；H,5.00；N,18.17
化合物44
2-对氯苯氧亚甲基-5-乙基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率71％，m.p.＞300℃
C21H25ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,2H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：476(M+)；Anal.Calcd.(％)for C21H25ClN6OS2:C,52.87；H,5.28；N,17.62；found:C,52.86；H,5.27；N,17.65
化合物45
2-对氯苯氧亚甲基-5-正丙基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率71％，m.p.＞300℃
C22H27ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,2H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：490(M+)；Anal.Calcd.(％)for C22H27ClN6OS2:C,53.81；H,5.54；N,17.11；found:C,53.80；H,5.52；N,17.15
化合物46
2-对氯苯氧亚甲基-5-异丙基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率73％，m.p.＞300℃
C22H27ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,2H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：490(M+)；Anal.Calcd.(％)for C22H27ClN6OS2:C,53.81；H,5.54；N,17.11；found:C,53.80；H,5.52；N,17.15
化合物47
2-对氯苯氧亚甲基-5-正丁基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率78％，m.p.＞300℃
C23H29ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,4H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：504(M+)；Anal.Calcd.(％)for C23H29ClN6OS2:C,54.69；H,5.79；N,16.64；found:C,54.66；H,5.78；N,16.69
化合物48
2-对氯苯氧亚甲基-5-异定基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率78％，m.p.＞300℃
C23H29ClN6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,4H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：504(M+)；Anal.Calcd.(％)for C23H29ClN6OS2:C,54.69；H,5.79；N,16.64；found:C,54.66；H,5.78；N,16.69
化合物49
2-(2,4-二氯苯氧亚甲基)-5-甲基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率79％，m.p.＞300℃
C20H22Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,2H),3.16–3.05(m,3H),2.51(s,4H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：496(M+)；Anal.Calcd.(％)for C20H22Cl2N6OS2:C,48.29；H,4.46；N,16.89；found:C,48.28；H,4.45；N,16.92
化合物50
2-(2,4-二氯苯氧亚甲基)-5-乙基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率81％，m.p.＞300℃
C21H24Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,3H),2.51(s,4H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：510(M+)；Anal.Calcd.(％)for C21H24Cl2N6OS2:C,49.31；H,4.73；N,16.43；found:C,49.33；H,4.75；N,16.40
化合物51
2-(2,4-二氯苯氧亚甲基)-5-正丙基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率77％，m.p.＞300℃
C22H26Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,3H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：524(M+)；Anal.Calcd.(％)for C22H26Cl2N6OS2:C,50.28；H,4.99；N,15.99；found:C,50.26；H,4.97；N,16.02
化合物52
2-(2,4-二氯苯氧亚甲基)-5-异丙基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率79％，m.p.＞300℃
C22H26Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,4H),3.16–3.05(m,3H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：524(M+)；Anal.Calcd.(％)for C22H26Cl2N6OS2:C,50.28；H,4.99；N,15.99；found:C,50.26；H,4.97；N,16.02
化合物53
2-(2,4-二氯苯氧亚甲基)-5-正丁基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率75％，m.p.＞300℃
C23H28Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,6H),3.16–3.05(m,3H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：538(M+)；Anal.Calcd.(％)for C23H28Cl2N6OS2:C,51.20；H,5.23；N,15.58；found:C,51.22；H,5.25；N,15.54
化合物54
2-(2,4-二氯苯氧亚甲基)-5-正丁基-4,6-二氢-8-丁硫基-10-甲硫基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶
所得纯品为黄色固体，收率75％，m.p.＞300℃
C23H28Cl2N6OS2
1H NMR(400MHz,DMSO)δ8.67(s,1H),7.41-7.84(q,J＝8.6Hz,3H),5.24(s,6H),3.16–3.05(m,3H),2.51(s,6H),1.68(dd,J＝18.0,6.6Hz,3H),0.99(t,J＝7.3Hz,6H).
MS(EI，m/z，％)：538(M+)；Anal.Calcd.(％)for C23H28Cl2N6OS2:C,51.20；H,5.23；N,15.58；found:C,51.22；H,5.25；N,15.54
采用上述类似的方法，可以制备其他的化合物。表1中所列的为本发明合成的化合物。
合成的化合物
本发明式1的化合物制成粒剂、水合剂、乳剂、可流动剂来使用。也可与其它除草剂、杀菌剂、杀虫剂、杀瞒剂、植物生长调节剂、肥料以及土壤改良剂混合使用或同时并用。
实施例2
除草活性实验
实验材料
电子天平一台、烧杯、滴管、移液管、洗耳球、培养皿、圆形滤纸、刻度尺、蒸馏水、DMF、乳化剂(吐温-80)、待测样品。
供试植物为、萝卜[Radish，单叶子杂草(Monocotyledonous weeds)]、油菜[Rape，双子叶杂草(Dicotyledonous weeds)]。
测试方法
采用离体培养皿测试除草活性。
用电子天平称量3-5mg待测样品，加入0.5mL DMF溶解，滴加1滴乳化剂(吐温-80)，加3-5mL蒸馏水(样品多少毫克，就加多少毫升蒸馏水)配成1000mg/L的溶液，取此溶液1mL加蒸馏水稀释到10mL，即配成100mg/mL的试样溶液，同样取1mL 100mg/mL的试样溶液加蒸馏水稀释到10mL，即配成10mg/mL的试样溶液。用直径为9cm的培养皿，内置两层滤纸及15-20粒油菜、萝卜的种子，分别加入100mg/mL(100ppm)和10mg/mL(10ppm)的试样溶液作培养液。用上述方法，不用药样溶液，直接用蒸馏水作培养液，作空白对照，盖好培养皿上盖。将培养皿水平放置在人工培养箱中培养，温度为25℃，培养三天后，每天光照8小时，处理8天后调查测试情况。测定植株根及茎的长度，取其中10株的平均值计算结果。结果为正说明药剂具有抑制作用，为负值说明药剂具有促进作用。
效果＝[(空白平均长度-处理平均长度)/空白平均长度]*100
活性标准：A级：≥90％B级：≥70％C级：≥50％D级：<50％
测试结果如下：
化合物对单、双子叶植物的抑制活性数据
化合物对单、双子叶植物的抑制活性数据(培养皿法)。

Claims (2)

1.2-取代苯氧亚甲基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶,其特征是:
所述2-取代苯氧亚甲基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶结构通式如Ⅰ：
式中：R1表示乙基，正丙基，正丁基；R2表示邻氯，对氯，邻对二氯；R3表示甲基，乙基，正丙基，异丙基，正丁基，异丁基。
2.2-取代苯氧亚甲基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶的制备方法,其特征是:用通式为Ⅱ的三唑联嘧啶与脂肪醛反应生成通式为Ⅰ的化合物，乙醇作为溶剂进行制备；
以通式Ⅰ表示的化合物的合成路线如下：
通式为Ⅱ的R1、R2的定义与权利要求中1的所述的结构通式Ⅰ中R1、R2的定义相同；
上述反应式中的Ⅱ与脂肪醛摩尔比为1:1.2，在乙醇中回流反应3-4小时。
CN201610344856.XA 2016-05-22 2016-05-22 2-取代苯氧亚甲基嘧啶并[5,4-e]-1,2,4-三唑并[1,5-c]嘧啶及其制备方法 Active CN107400136B (zh)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102399226A (zh) * 2011-11-28 2012-04-04 江西师范大学 具有除草活性的3-取代苯甲酰胺基-3,4-二氢-4-亚胺-5-甲硫基-7-烷硫基嘧啶并[4,5-d]嘧啶及其制备方法
CN102399225A (zh) * 2011-11-28 2012-04-04 江西师范大学 具有除草活性的3-含氟取代苯甲酰胺基-3,4-二氢-4-亚胺-5-甲硫基-7-乙硫基嘧啶并[4,5-d]嘧啶及其制备方法
CN102491977A (zh) * 2011-11-28 2012-06-13 江西师范大学 具有除草活性的1-取代苯氧亚甲基-8-烷硫基-10-甲硫基嘧啶并[5,4-e]-1,2,三唑并[1,5-c]嘧啶及制备方法

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Publication number Priority date Publication date Assignee Title
CN102399226A (zh) * 2011-11-28 2012-04-04 江西师范大学 具有除草活性的3-取代苯甲酰胺基-3,4-二氢-4-亚胺-5-甲硫基-7-烷硫基嘧啶并[4,5-d]嘧啶及其制备方法
CN102399225A (zh) * 2011-11-28 2012-04-04 江西师范大学 具有除草活性的3-含氟取代苯甲酰胺基-3,4-二氢-4-亚胺-5-甲硫基-7-乙硫基嘧啶并[4,5-d]嘧啶及其制备方法
CN102491977A (zh) * 2011-11-28 2012-06-13 江西师范大学 具有除草活性的1-取代苯氧亚甲基-8-烷硫基-10-甲硫基嘧啶并[5,4-e]-1,2,三唑并[1,5-c]嘧啶及制备方法

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