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含大体积取代基的吡唑并三嗪酮类化合物的合成及除草活性

古建 李晓涵 王桢学 陈烨烨 陈汐玥 李华斌

古建, 李晓涵, 王桢学, 陈烨烨, 陈汐玥, 李华斌. 含大体积取代基的吡唑并三嗪酮类化合物的合成及除草活性[J]. 农药学学报. doi: 10.16801/j.issn.1008-7303.2021.0071
引用本文: 古建, 李晓涵, 王桢学, 陈烨烨, 陈汐玥, 李华斌. 含大体积取代基的吡唑并三嗪酮类化合物的合成及除草活性[J]. 农药学学报. doi: 10.16801/j.issn.1008-7303.2021.0071
Jian GU, Xiaohan LI, Zhenxue WANG, Yeye CHEN, Xiyue CHEN, Huabin LI. Synthesis and herbicidal activity of 4H-pyrazolo[3,4-d][1,2,3]triazine-4-one with bulky substituents[J]. Chinese Journal of Pesticide Science. doi: 10.16801/j.issn.1008-7303.2021.0071
Citation: Jian GU, Xiaohan LI, Zhenxue WANG, Yeye CHEN, Xiyue CHEN, Huabin LI. Synthesis and herbicidal activity of 4H-pyrazolo[3,4-d][1,2,3]triazine-4-one with bulky substituents[J]. Chinese Journal of Pesticide Science. doi: 10.16801/j.issn.1008-7303.2021.0071

含大体积取代基的吡唑并三嗪酮类化合物的合成及除草活性

doi: 10.16801/j.issn.1008-7303.2021.0071
基金项目: 国家自然科学基金 (21102078);“国家级大学生创新创业训练计划”创新训练项目 (201810055101;201910055090);南开大学沧州渤海新区绿色化工研究院基金项目(NCC2020PY06)
详细信息
    作者简介:

    古建,男,本科生,E-mail:1610384@mail.nankai.edu.cn

    李晓涵,并列第一作者,女,本科生,E-mail:xiaohanli@ucsb.edu

    通讯作者:

    李华斌,通信作者 (Author for correspondence),男,助理研究员,主要从事新农药研究与开发工作,E-mail:lihuabinnk@163.com

  • 中图分类号: O626.21

Synthesis and herbicidal activity of 4H-pyrazolo[3,4-d][1,2,3]triazine-4-one with bulky substituents

  • 摘要: 以1-(取代)苯基-5-氨基-1H-吡唑-4-甲酸乙酯或1-叔丁基-5-氨基-1H-吡唑-4-甲酰氯和2-甲基-4-炔丙基-6-氨基-7-氟-2H-苯并[b][1,4]-噁嗪-3(4H)-酮为初始原料,分别通过不同的合成路线,得到22个未见文献报道的含大体积取代基的吡唑并三嗪酮类化合物,所有化合物结构均通过高分辨质谱(HRMS)和核磁共振氢谱(1H NMR)确证。初步生物活性测定表明:在375 g/hm2的处理剂量下,大部分目标化合物表现出一定的除草活性,其中化合物 4h4i4j 对反枝苋Amaranthus retroflexus生长的抑制率接近100%。
  • 1  目标化合物的设计思路

    1.  Design strategy of target compounds

    2  化合物4a~4f的合成路线

    2.  Synthetic route of compounds 4a-4f

    3  化合物4g~4n以及4′g~4′n的合成路线

    3.  Synthetic route of compounds 4g-4n and 4′g-4′n

    表  1  目标化合物4a~4n4’g~4’n的理化性质及高分辨质谱数据

    Table  1.   The analytical data and HRMS of the title compounds 4a-4n and 4’g-4’n

    No.R外观
    Appearance
    产率
    Yield/%
    熔点
    m.p./℃
    高分辨质谱 HRMS [M+Na]+
    测定值 Found (计算值 Calcd.)
    4a H 黄色固体 Yellow solid 70 204-205 439.0928 (439.0925)
    4b 3-CH3 黄色固体 Yellow solid 18 203-204 453.1085 (453.1082)
    4c 3-F 白色固体 White solid 99 207-208 457.0835 (457.0831)
    4d 3-Cl 黄色固体 Yellow solid 48 202-204 473.0541 (473.0536)
    4e 2,4-Cl2 黄色固体 Yellow solid 40 266-268 507.0145 (507.0146)
    4f 3,4-Cl2 黄色固体 Yellow solid 94 174-175 507.0148 (507.0146)
    4g 3-F 黄色固体 Yellow solid 8 126-127 471.0993 (471.0988)
    4h 4-Cl 黄色固体 Yellow solid 7 143-145 487.0695 (487.0692)
    4i 2,4-F2 白色固体 White solid 14 140-142 489.0896 (489.0893)
    4j 3,4-F2 白色固体 White solid 11 142-143 489.0898 (489.0893)
    4k 2,6-F2 白色固体 White solid 14 201-203 489.0897 (489.0893)
    4l 3,5-F2 黄色固体 Yellow solid 10 219-220 489.0896 (489.0893)
    4m 2-F-4-Br 白色固体 White solid 10 141-142 549.0096 (549.0093)
    4n 4-CF3 黄色固体 Yellow solid 9 130-132 521.0960 (521.0956)
    4′g 3-F 白色固体 White solid 57 281-283 471.0992 (471.0988)
    4′h 4-Cl 白色固体 White solid 47 275-277 487.0696 (487.0692)
    4′i 2,4-F2 黄色固体 Yellow solid 53 208-209 489.0897 (489.0893)
    4′j 3,4-F2 白色固体 White solid 52 289-21 489.0897 (489.0893)
    4′k 2,6-F2 白色固体 White solid 53 241-242 489.0898 (489.0893)
    4′l 3,5-F2 黄色固体 Yellow solid 57 285-286 489.0898 (489.0893)
    4′m 2-F-4-Br 白色固体 White solid 49 278-279 549.0095 (549.0093)
    4′n 4-CF3 黄色固体 Yellow solid 46 302-304 521.0960 (521.0956)
    下载: 导出CSV

    表  2  目标化合物的核磁共振氢谱数据

    Table  2.   The 1H NMR of the title compounds

    No.1H NMR(400 MHz, CDCl3), δ
    4a 8.44 (s, 1H, pyrazole), 8.14-8.12 (m, 2H, Ar-H), 7.61-7.57 (m, 2H, Ar-H), 7.50-7.46 (m, 1H, Ar-H), 7.31 (d, 1H, 4JF-H = 6.7 Hz, Ar-H), 6.99 (d, 1H, 3JF-H = 9.7 Hz, Ar-H), 4.74 (s, 2H, OCH2), 4.69 (d, 2H, J = 2.4 Hz, NCH2), 2.27 (t, 1H, J = 2.4 Hz, ≡CH)
    4b 8.43 (s, 1H, pyrazole), 7.95-7.89 (m, 2H, Ar-H), 7.47 (dd, J = 10.0, 6.4 Hz, 1H, Ar-H), 7.31 (dd, J = 9.9, 7.2 Hz, 2H, Ar-H), 7.00 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 4.75 (s, 2H, OCH2), 4.70 (d, J = 2.6 Hz, 2H, NCH2), 2.50 (s, 3H, CH3), 2.28 (t, J = 2.4 Hz, 1H), 1.26 (t, J = 7.1 Hz, 1H, ≡CH)
    4c 8.44 (s, 1H, pyrazole), 8.06 (dt, J = 8.3, 1.3 Hz, 1H, Ar-H), 8.00 (dt, J = 9.8, 2.3 Hz, 1H, Ar-H), 7.57 (td, J = 8.3, 6.1 Hz, 1H, Ar-H), 7.32 (d, 4JF-H = 6.7 Hz, 1H, Ar-H), 7.23-7.14 (m, 1H, Ar-H), 7.01 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 4.75 (s, 2H, OCH2), 4.71 (d, J = 2.5 Hz, 2H, NCH2), 2.29 (t, J = 2.5 Hz, 1H, ≡CH)
    4d 8.44 (s, 1H, pyrazole), 8.25 (t, J = 2.1 Hz, 1H, Ar-H), 8.14 (d, J = 8.1 Hz, 1H, Ar-H), 7.53 (t, J = 8.1 Hz, 1H, Ar-H), 7.45 (d, J = 8.1 Hz, 1H, Ar-H), 7.32 (d, 4JF-H = 6.7 Hz, 1H, Ar-H), 7.00 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 4.75 (s, 2H, OCH2), 4.70 (d, J = 2.5 Hz, 2H, NCH2), 2.29 (t, J = 2.6 Hz, 1H, ≡CH)
    4e 8.48 (s, 1H, pyrazole), 7.69 (d, J = 2.2 Hz, 1H, Ar-H), 7.56 (d, J = 8.5 Hz, 1H, Ar-H), 7.50 (dd, J = 8.5, 2.2 Hz, 1H, Ar-H), 7.31 (d, 4JF-H = 6.7 Hz, 1H, Ar-H), 6.99 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 4.74 (s, 2H, OCH2), 4.70 (d, J = 2.5 Hz, 2H, NCH2), 2.28 (t, J = 2.5 Hz, 1H, ≡CH)
    4f 8.44 (s, 1H, pyrazole), 8.40 (d, J = 2.6 Hz, 1H, Ar-H), 8.15 (dd, J = 8.8, 2.6 Hz, 1H, Ar-H), 7.66 (d, J = 8.8 Hz, 1H, Ar-H), 7.32 (d, 4JF-H = 6.7 Hz, 1H, Ar-H), 7.01 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 4.76 (s, 2H, OCH2), 4.70 (d, J = 2.6 Hz, 2H, NCH2), 2.29 (t, J = 2.5 Hz, 1H, ≡CH)
    4g 8.29 (s, 1H, pyrazole), 7.39-7.33 (m, 1H, Ar-H), 7.29 (d, 4JF-H = 6.7 Hz, 1H, Ar-H), 7.25 (d, J = 8.9 Hz, 1H, Ar-H), 7.16 (d, J = 9.2 Hz, 1H, Ar-H), 7.06 (td, J = 8.4, 2.2 Hz, 1H, Ar-H), 6.99 (d, 3JF-H = 9.6 Hz, 1H, Ar-H), 5.78 (s, 2H, NCH2), 4.74 (s, 2H, OCH2), 4.69 (d, J = 2.37 Hz, 2H, NCH2), 2.28 (t, J = 2.4 Hz, 1H, ≡CH)
    4h 8.26 (s, 1H, pyrazole), 7.43 (d, J = 8.3 Hz, 2H, Ar-H), 7.36 (d, J = 8.3 Hz, 2H, Ar-H), 7.28 (d, 4JF-H = 6.9 Hz, 1H, Ar-H), 6.98 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 5.76 (s, 2H, NCH2), 4.74 (s, 2H, OCH2), 4.69 (d, J = 2.5 Hz, 2H, NCH2), 2.28 (t, J = 2.5 Hz, 1H, ≡CH)
    4i 8.27 (s, 1H, pyrazole), 7.43 (td, J = 8.6, 6.3 Hz, 1H, Ar-H), 7.29 (d, 4JF-H = 6.7 Hz, 1H, Ar-H), 6.99 (d, 3JF-H = 9.6 Hz, 1H, Ar-H), 6.94-6.85 (m, 2H, Ar-H), 5.83 (s, 2H, NCH2), 4.74 (s, 2H, OCH2), 4.69 (d, J = 2.5 Hz, 2H, NCH2), 2.28 (t, J = 2.5 Hz, 1H, ≡CH)
    4j 8.27 (s, 1H, pyrazole), 7.35-7.30 (m, 1H, Ar-H), 7.28 (d, 4JF-H = 6.8 Hz, 1H, Ar-H), 7.24-7.12 (m, 2H, Ar-H), 6.99 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 5.74 (s, 2H, NCH2), 4.74 (s, 2H, OCH2), 4.69 (d, J = 2.5 Hz, 2H, NCH2), 2.28 (t, J = 2.5 Hz, 1H, ≡CH)
    4k 8.25 (s, 1H, pyrazole), 7.38 (tt, J = 8.4, 6.5 Hz, 1H, Ar-H), 7.30 (d, 4JF-H = 6.7 Hz, 1H, Ar-H), 7.00 (d, J = 1.7 Hz, 1H, Ar-H), 6.99-6.96 (m, 2H, Ar-H), 5.90 (s, 2H, NCH2), 4.74 (s, 2H, OCH2), 4.70 (d, J = 2.5 Hz, 2H, NCH2), 2.28 (t, J = 2.5 Hz, 1H, ≡CH)
    4l 8.29 (s, 1H, pyrazole), 7.29 (d, 4JF-H = 6.7 Hz, 1H, Ar-H), 7.00 (s, 1H, Ar-H), 6.98 (dt, J = 5.0, 2.1 Hz, 2H, Ar-H), 6.80 (tt, J = 9.0, 2.3 Hz, 1H, Ar-H), 5.76 (s, 2H, NCH2), 4.74 (s, 2H, OCH2), 4.69 (d, J = 2.5 Hz, 2H, NCH2), 2.28 (t, J = 2.5 Hz, 1H, ≡CH)
    4m 8.27 (s, 1H, pyrazole), 7.34 (d, J = 1.8 Hz, 1H, Ar-H), 7.32-7.27 (m, 3H, Ar-H), 6.99 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 5.82 (s, 2H, NCH2), 4.74 (s, 2H, OCH2), 4.69 (d, J = 2.5 Hz, 2H, NCH2), 2.28 (t, J = 2.5 Hz, 1H, ≡CH)
    4n 8.28 (s, 1H, pyrazole), 7.65 (d, J = 8.1 Hz, 2H, Ar-H), 7.59 (d, J = 8.2 Hz, 2H, Ar-H), 7.29 (d, 4JF-H = 6.7 Hz, 1H, Ar-H), 6.99 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 5.85 (s, 2H, NCH2), 4.74 (s, 2H, OCH2), 4.69 (d, J = 2.5 Hz, 2H, NCH2), 2.28 (t, J = 2.5 Hz, 1H, ≡CH)
    4’g 8.22 (s, 1H, pyrazole), 7.44-7.38 (m, 1H, Ar-H), 7.30 (d, 4JF-H = 6.8 Hz, 1H, Ar-H), 7.18 (d, J = 7.7 Hz, 1H, Ar-H), 7.14-7.06 (m, 2H, Ar-H), 6.97 (d, 3JF-H = 9.5 Hz, 1H, Ar-H), 5.59 (s, 2H, NCH2), 4.73 (s, 2H, OCH2), 4.69 (d, J = 0.8 Hz, 2H, NCH2), 2.27 (t, J = 2.3 Hz, 1H, ≡CH)
    4’h 8.19 (s, 1H, pyrazole), 7.41 (d, J = 8.5 Hz, 2H, Ar-H), 7.34 (d, J = 8.5 Hz, 2H, Ar-H), 7.29 (d, 4JF-H = 6.8 Hz, 1H, Ar-H), 6.96 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 5.56 (s, 2H, NCH2), 4.72 (s, 2H, OCH2), 4.68 (d, J = 2.6 Hz, 2H, NCH2), 2.26 (t, J = 2.5 Hz, 1H, ≡CH)
    4’i 8.28 (s, 1H, pyrazole), 7.49 (td, J = 8.5, 6.1 Hz, 1H, Ar-H), 7.28 (d, 4JF-H = 6.8 Hz, 1H, Ar-H), 6.99-6.89 (m, 3H, Ar-H), 5.61 (s, 2H, NCH2), 4.72 (s, 2H, OCH2), 4.68 (d, J = 2.5 Hz, 2H, NCH2), 2.26 (t, J = 2.5 Hz, 1H, ≡CH)
    4’j 8.23 (s, 1H, pyrazole), 7.29 (d, 4JF-H = 6.8 Hz, 1H, Ar-H), 7.22 (dd, J = 9.9, 7.9 Hz, 2H, Ar-H), 7.15 (d, J = 8.9 Hz, 1H, Ar-H), 6.96 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 5.54 (s, 2H, NCH2), 4.72 (s, 2H, OCH2), 4.69 (d, J = 2.5 Hz, 2H, NCH2), 2.26 (t, J = 2.5 Hz, 1H, ≡CH)
    4’k 8.29 (s, 1H, pyrazole), 7.43 (tt, J = 8.4, 6.5 Hz, 1H, Ar-H), 7.28 (d, 4JF-H = 6.8 Hz, 1H, Ar-H), 7.02 (dd, J = 8.5, 7.4 Hz, 2H, Ar-H), 6.95 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 5.70 (s, 2H, NCH2), 4.71 (s, 2H, OCH2), 4.68 (d, J = 2.5 Hz, 2H, NCH2), 2.25 (t, J = 2.5 Hz, 1H, ≡CH)
    4’l 8.26 (s, 1H, pyrazole), 7.30 (d, 4JF-H = 6.7 Hz, 1H, Ar-H), 6.97 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 6.92-6.80 (m, 3H, Ar-H), 5.57 (s, 2H, NCH2), 4.72 (s, 2H, OCH2), 4.69 (d, J = 2.5 Hz, 2H, NCH2), 2.27 (t, J = 2.4 Hz, 1H, ≡CH)
    4’m 8.28 (s, 1H, pyrazole), 7.40-7.31 (m, 3H, Ar-H), 7.28 (d, 4JF-H = 6.8 Hz, 1H, Ar-H), 6.96 (d, 3JF-H = 9.7 Hz, 1H, Ar-H), 5.60 (s, 2H, NCH2), 4.71 (s, 2H, OCH2), 4.68 (d, J = 2.5 Hz, 2H, NCH2), 2.26 (t, J = 2.5 Hz, 1H, ≡CH)
    4’n 8.24 (s, 1H, pyrazole), 7.69 (d, J = 8.0 Hz, 2H, Ar-H), 7.51 (d, J = 8.0 Hz, 2H, Ar-H), 7.30 (s, 1H, Ar-H), 6.96 (d, 3JF-H = 9.5 Hz, 1H, Ar-H), 5.66 (s, 2H, NCH2), 4.72 (s, 2H, OCH2), 4.69 (d, J = 2.6 Hz, 2H, NCH2), 2.26 (t, J = 2.5 Hz, 1H, ≡CH)
    下载: 导出CSV

    表  3  目标化合物除草活性测试结果 (抑制率/%)(剂量:375 g/hm2)

    Table  3.   The herbicidal activity of the title compounds (Inhibition rate/%)(Dosage: 375 g/hm2)

    No.土壤处理
    pre-emergence
    茎叶处理
    postemergence
    油菜
    Brassica campestris
    苋菜
    Amaranthus retroflexus L.
    稗草
    Echinochloa
    crus-galli
    马唐
    Digitaria sanguinalis
    (L.)Scop
    油菜
    Brassica campestris
    苋菜
    Amaranthus retroflexus L.
    稗草
    Echinochloa
    crus-galli
    马唐
    Digitaria sanguinalis
    (L.) Scop
    4a 0 0 0 0 0 0 0 0
    4b 0 0 0 3.2 0 88.0 0 0
    4c 28.4 29.3 0 0 0 93.0 0 33.8
    4d 25.4 25.8 0 4.3 15.3 90.0 0 17.6
    4e 1.9 0 0 0 0 70.0 0 0
    4f 12.2 0 11.2 17.4 18.8 80.0 0 0
    4g 0 0 0 0 0 100 17.5 0
    4h 8.6 100 23.4 55.0 48.7 100 24.1 6.3
    4i 2.5 100 30.5 33.3 5.2 92.0 26.6 0
    4j 34.8 100 30.0 37.1 30.9 95.5 16.5 0.8
    4k 39.4 27.0 30.6 30.4 23.7 18.0 40.5 0
    4l 6.3 90.7 32.1 43.8 5.4 82.7 21.6 1.1
    4m 11.0 78.9 40.3 15.8 6.0 5.0 23.5 0
    4n 20.4 94.7 24.6 36.3 13.9 0 24.6 5.7
    4′g 0 0 0 0 0 0 0 0
    4′h 32.7 0 21.5 30.4 37.5 28.1 26.5 19.6
    4′i 31.7 14.1 26.9 12.7 8.3 13.4 1.5 0
    4′j 32.1 0 26.2 28.6 32.2 7.4 37.3 0
    4′k 30.7 0 0 37.7 0.7 0 0 0
    4′l 7.2 2.7 21.6 22.8 0 0 10.9 0
    4′m 34.6 11.3 31.8 21.7 19.5 0 22.4 2.9
    4′n 24.2 7.2 26.5 23.9 32.0 15.2 0 7.6
    A 100 100 97.3 100 100 83.5 43.5 4.2
    下载: 导出CSV
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  • 收稿日期:  2020-11-22
  • 录用日期:  2021-03-07
  • 网络出版日期:  2021-03-16

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