Synthesis and Herbicidal Activity of Novel Pyrimido[5,4-e]-[1,2,4]triazolo[1,5-c]pyrimidine Derivatives

doi:10.6023/cjoc202301008

Abstract

To discover N-containing fused heterocyclic compounds with novel structure and excellent herbicidal activity, forty-two pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives (Ι-1~Ι-42) were synthesied using 2-(alkylthio)-5- carbonitrile-6-(methylthio)pyrimidine-4-aminos as starting materials. Their structures were clearly confirmed by melting point, ¹H NMR, ¹³C NMR, infrared absorption spectroscopy (IR), and high-resolution mass spectra (HRMS). The preliminary bioassay indicated that many target compounds exhibited remarkable herbicidal activities against the monocotyledons (Triticum aestivum L., Echinochloa crusgalli, and Sorghum bicolor) and dicotyledons (Raphanus sativus, Brassica campestris, and Cucumis sativus) at the concentration of 100 mg/L. Especially, compounds Ι-13, Ι-14, Ι-23, Ι-25 and Ι-30~Ι-42 showed excellent herbicidal activities against the roots and stalks of the six test plant at 100 mg/L with 100% inhibition rates.

Key words: pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine, synthesis, herbicidal activity

Cite this article

Hai Lin, Huixiang Nie, Anlin Zhao, Tao Wang, Jin Luo. Synthesis and Herbicidal Activity of Novel Pyrimido[5,4-e]-[1,2,4]triazolo[1,5-c]pyrimidine Derivatives[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2462-2475.

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Entry	Catalyst	Solvent	T/℃	t/h	Yield^b/%
1	—	乙醇	80	5	0
2	氯化铜	乙醇	80	5	26
3	硫酸铜	乙醇	80	5	0
4	醋酸铜	乙醇	80	5	0
5	氯化亚铁	乙醇	80	5	18
6	氯化铁	乙醇	80	5	31
7	四氯化锆	乙醇	80	5	85
8	四氯化锆	二氯甲烷	80	5	46
9	四氯化锆	四氢呋喃	80	5	69
10	四氯化锆	丙酮	80	5	51
11	四氯化锆	乙腈	80	5	43
12	四氯化锆	乙醇	60	5	28
13	四氯化锆	乙醇	40	5	10
14	四氯化锆	乙醇	80	6	84
15	四氯化锆	乙醇	80	7	82
16	四氯化锆	乙醇	80	4	73

Entry	Catalyst	Solvent	T/℃	t/h	Yield^b/%
1	—	乙醇	80	5	0
2	氯化铜	乙醇	80	5	26
3	硫酸铜	乙醇	80	5	0
4	醋酸铜	乙醇	80	5	0
5	氯化亚铁	乙醇	80	5	18
6	氯化铁	乙醇	80	5	31
7	四氯化锆	乙醇	80	5	85
8	四氯化锆	二氯甲烷	80	5	46
9	四氯化锆	四氢呋喃	80	5	69
10	四氯化锆	丙酮	80	5	51
11	四氯化锆	乙腈	80	5	43
12	四氯化锆	乙醇	60	5	28
13	四氯化锆	乙醇	40	5	10
14	四氯化锆	乙醇	80	6	84
15	四氯化锆	乙醇	80	7	82
16	四氯化锆	乙醇	80	4	73

Compd.	R¹	R²	R³	浓度/(mg•L^－1)	油菜根/茎	稗草根/茎	黄瓜根/茎	小麦根/茎	高粱根/茎	萝卜根/茎
Ι-1	Et	3-CF₃	Et	100 10	100/100 76/－112	70/－25 54/－10	61/－10 45/30	52/20 29/2	69/16 80/27	100/100 35/－2
Ι-2	Et	3-CF₃	n-Pr	100 10	87/100 61/－141	45/－19 64/－34	46/20 58/5	40/14 22/2	64/22 68/28	100/100 100/100
Ι-3	Et	3-CF₃	n-Bu	100 10	100/100 100/100	73/11 64/－13	77/11 51/34	100/100 31/7	100/100 84/45	100/100 13/－5
Ι-4	n-Pr	3-CF₃	Et	100 10	100/100 91/－167	94/31 80/－20	100/100 58/19	100/100 69/7	100/100 85/2	100/100 100/100
Ι-5	n-Pr	3-CF₃	i-Pr	100 10	100/100 100/100	84/16 86/－26	69/32 43/10	66/－17 －20/－5	82/30 73/24	100/100 100/100
Ι-6	n-Pr	3-CF₃	i-Bu	100 10	100/100 78/－90	80/12 100/11	64/5 85/5	100/100 45/－5	90/27 48/6	100/100 100/100
Ι-7	n-Bu	3-CF₃	Me	100 10	100/100 100/100	90/－7 56/－30	100/100 54/36	100/100 27/24	100/100 75/33	100/100 37/11
Ι-8	n-Bu	3-CF₃	Et	100 10	100/100 84/－107	82/8 69/－1	100/100 49/20	100/100 46/2	92/61 83/30	100/100 36/－16
Ι-9	n-Bu	3-CF₃	n-Pr	100 10	100/100 84/－162	87/14 80/10	65/13 64/22	100/100 10/1	91/51 62/16	100/100 100/100
Ι-10	n-Bu	3-CF₃	n-Bu	100 10	100/100 81/－107	100/100 87/5	78/－13 45/39	100/100 2/7	100/100 67/25	100/100 63/59
Ι-11	n-Bu	3-CF₃	i-Pr	100 10	100/100 53/－183	84/5 80/19	100/100 37/34	100/100 13/－6	100/100 64/12	100/100 －52/－7
Ι-12	n-Bu	3-CF₃	i-Bu	100 10	100/100 64/－114	89/21 47/－33	100/100 64/37	100/100 42/0	100/100 57/19	100/100 58/－2
Ι-13	n-Bu	3-CF₃	n-C₅H₁₁	100 10	100/100 78/－135	100/100 71/－7	100/100 56/15	100/100 46/－1	100/100 57/－2	100/100 43/8
Ι-14	n-Bu	3-CF₃	n-C₆H₁₃	100 10	100/100 74/－107	100/100 79/44	100/100 69/－4	100/100 55/－5	100/100 58/16	100/100 43/－2
Ι-15	n-C₆H₁₃	3-CF₃	n-C₆H₁₃	100 10	80/－58 68/－135	85/－13 85/－43	63/－21 77/15	100/100 43/－15	77/27 100/100	100/100 100/100
Ι-16	n-C₇H₁₅	3-CF₃	Me	100 10	100/100 100/100	86/11 100/100	100/100 67/16	100/100 6/－19	100/100 60/8	100/100 45/2
Ι-17	n-C₇H₁₅	3-CF₃	Et	100 10	100/100 34/－114	86/－1 54/－19	66/36 86/29	100/100 48/6	100/100 67/28	100/100 24/2
Ι-18	n-C₇H₁₅	3-CF₃	n-Pr	100 10	62/－38 100/100	88/23 67/－1	62/51 61/1	100/100 25/－29	75/6 66/13	－19/31 49/35
Ι-19	n-C₇H₁₅	3-CF₃	n-Bu	100 10	100/100 33/57	38/－27 100/100	79/58 27/49	100/100 －58/4	100/100 51/39	100/100 100/6
Ι-20	n-C₇H₁₅	3-CF₃	i-Bu	100 10	100/100 39/－144	100/100 52/－42	100/100 54/2	100/100 48/11	81/45 43/16	100/100 －49/9
Ι-21	n-C₇H₁₅	3-CF₃	n-C₅H₁₁	100 10	44/－90 100/100	100/100 58/－42	100/100 59/40	100/100 19/10	22/22 100/100	88/83 －19/－31
Ι-22	n-C₇H₁₅	3-CF₃	n-C₆H₁₃	100 10	100/100 100/100	75/－71 49/－68	100/100 53/27	100/100 －16/2	100/100 69/46	100/100 100/100
Ι-23	Et	4-F	Et	100 10	100/100 65/7	100/100 15/－51	100/100 11/15	100/100 48/22	100/100 －31/－20		100/100 32/21
Ι-24	Et	4-F	n-Pr	100 10	100/100 －12/1	100/100 22/－88	100/100 －12/1	100/100 30/－4	100/100 －6/－38		82/75 －11/30
Ι-25	Et	4-F	n-Bu	100 10	100/100 49/11	100/100 9/－45	100/100 39/－6	100/100 40/－2	100/100 －5/－21		100/100 3/4
Ι-26	Et	4-F	n-C₅H₁₁	100 10	100/100 48/－14	64/－47 －1/－30	100/100 48/－14	100/100 58/－16	100/100 －13/－22		100/100 77/32
Ι-27	Et	4-F	n-C₆H₁₃	100 10	40/－19 37/－37	75/20 13/－91	100/100 9/37	100/100 －1/－1	39/44 －2/－32		100/100 69/14
Ι-28	n-Pr	4-F	Et	100 10	63/28 22/－38	38/－42 －13/－23	63/28 22/－38	44/12 15/－18	－2/－4 －45/22		100/100 45/7
Ι-29	n-Pr	4-F	n-Bu	100 10	100/100 44/－48	60/－11 35/－252	100/100 15/－41	100/100 9/－14	100/100 29/－2		100/100 9/5
Ι-30	n-Pr	4-F	n-C₅H₁₁	100 10	100/100 26/－11	100/100 24/－54	100/100 40/－15	100/100 －9/27	100/100 －82/－67		100/100 55/－2
Ι-31	n-Pr	4-F	n-C₆H₁₃	100 10	100/100 25/－22	100/100 －16/－91	100/100 －20/－28	100/100 －61/－28	100/100 －76/－94		100100 －5/14
Ι-32	n-Bu	4-F	Me	100 10	100/100 70/1	100/100 13/－67	100/100 44/－31	100/100 18/－22	100/100 －52/－6		100/100 38/19
Ι-33	n-Bu	4-F	Et	100 10	100/100 68/23	100/100 24/－42	100/100 －21/－38	100/100 －30/－12	100/100 －130/－14		100/100 35/－4
Ι-34	n-Bu	4-F	n-Pr	100 10	100/100 48/－12	100/100 20/－98	100/100 17/－12	100/100 32/－2	100/100 －45/－56		100/100 13/9
Ι-35	n-Bu	4-F	n-Bu	100 10	100/100 25/7	100/100 38/－85	100/100 100/100	100/100 38/2	100/100 －32/－29		100/100 100/100
Ι-36	n-C₅H₁₁	4-F	Et	100 10	100/100 48/22	100/100 43/59	100/100 30/－20	100/100 53/－10	100/100 －10/－11		100/100 35/－6
Ι-37	n-C₅H₁₁	4-F	n-Pr	100 10	100/100 53/44	100/100 56/－11	100/100 100/100	100/100 61/－14	100/100 －41/－57		100/100 100/100
Ι-38	n-C₅H₁₁	4-F	n-Bu	100 10	100/100 64/7	100/100 38/－73	100/100 －7/－14	100/100 100/100	100/100 100/100		100/100 35/14
Ι-39	n-C₅H₁₁	4-F	n-C₅H₁₁	100 10	100/100 64/33	100/100 60/－5	100/100 44/－31	100/100 40/－6	100/100 15/17		100/100 56/14
Ι-40	n-C₅H₁₁	4-F	n-C₆H₁₃	100 10	100/100 61/－23	100/100 42/－30	100/100 42/－31	100/100 43/－18	100/100 －52/－46		100/100 17/－11
Ι-41	n-C₆H₁₃	4-F	n-Bu	100 10	100/100 80/15	100/100 31/－73	100/100 34/21	100/100 43/－9	100/100 －19/－28		100/100 64/51
Ι-42	n-C₇H₁₅	4-F	n-C₅H₁₁	100 10	100/100 37/4	100/100 56/－79	100/100 32/－48	100/100 30/－22	100/100 －15/56		100/100 49/－11
唑嘧磺草胺				100 10	84/62 62/47	97/89 70/8	92/73 82/61	95/83 83/60	93/86 90/84		90/85 83/77

Compd.	R¹	R²	R³	浓度/(mg•L^－1)	油菜根/茎	稗草根/茎	黄瓜根/茎	小麦根/茎	高粱根/茎	萝卜根/茎
Ι-1	Et	3-CF₃	Et	100 10	100/100 76/－112	70/－25 54/－10	61/－10 45/30	52/20 29/2	69/16 80/27	100/100 35/－2
Ι-2	Et	3-CF₃	n-Pr	100 10	87/100 61/－141	45/－19 64/－34	46/20 58/5	40/14 22/2	64/22 68/28	100/100 100/100
Ι-3	Et	3-CF₃	n-Bu	100 10	100/100 100/100	73/11 64/－13	77/11 51/34	100/100 31/7	100/100 84/45	100/100 13/－5
Ι-4	n-Pr	3-CF₃	Et	100 10	100/100 91/－167	94/31 80/－20	100/100 58/19	100/100 69/7	100/100 85/2	100/100 100/100
Ι-5	n-Pr	3-CF₃	i-Pr	100 10	100/100 100/100	84/16 86/－26	69/32 43/10	66/－17 －20/－5	82/30 73/24	100/100 100/100
Ι-6	n-Pr	3-CF₃	i-Bu	100 10	100/100 78/－90	80/12 100/11	64/5 85/5	100/100 45/－5	90/27 48/6	100/100 100/100
Ι-7	n-Bu	3-CF₃	Me	100 10	100/100 100/100	90/－7 56/－30	100/100 54/36	100/100 27/24	100/100 75/33	100/100 37/11
Ι-8	n-Bu	3-CF₃	Et	100 10	100/100 84/－107	82/8 69/－1	100/100 49/20	100/100 46/2	92/61 83/30	100/100 36/－16
Ι-9	n-Bu	3-CF₃	n-Pr	100 10	100/100 84/－162	87/14 80/10	65/13 64/22	100/100 10/1	91/51 62/16	100/100 100/100
Ι-10	n-Bu	3-CF₃	n-Bu	100 10	100/100 81/－107	100/100 87/5	78/－13 45/39	100/100 2/7	100/100 67/25	100/100 63/59
Ι-11	n-Bu	3-CF₃	i-Pr	100 10	100/100 53/－183	84/5 80/19	100/100 37/34	100/100 13/－6	100/100 64/12	100/100 －52/－7
Ι-12	n-Bu	3-CF₃	i-Bu	100 10	100/100 64/－114	89/21 47/－33	100/100 64/37	100/100 42/0	100/100 57/19	100/100 58/－2
Ι-13	n-Bu	3-CF₃	n-C₅H₁₁	100 10	100/100 78/－135	100/100 71/－7	100/100 56/15	100/100 46/－1	100/100 57/－2	100/100 43/8
Ι-14	n-Bu	3-CF₃	n-C₆H₁₃	100 10	100/100 74/－107	100/100 79/44	100/100 69/－4	100/100 55/－5	100/100 58/16	100/100 43/－2
Ι-15	n-C₆H₁₃	3-CF₃	n-C₆H₁₃	100 10	80/－58 68/－135	85/－13 85/－43	63/－21 77/15	100/100 43/－15	77/27 100/100	100/100 100/100
Ι-16	n-C₇H₁₅	3-CF₃	Me	100 10	100/100 100/100	86/11 100/100	100/100 67/16	100/100 6/－19	100/100 60/8	100/100 45/2
Ι-17	n-C₇H₁₅	3-CF₃	Et	100 10	100/100 34/－114	86/－1 54/－19	66/36 86/29	100/100 48/6	100/100 67/28	100/100 24/2
Ι-18	n-C₇H₁₅	3-CF₃	n-Pr	100 10	62/－38 100/100	88/23 67/－1	62/51 61/1	100/100 25/－29	75/6 66/13	－19/31 49/35
Ι-19	n-C₇H₁₅	3-CF₃	n-Bu	100 10	100/100 33/57	38/－27 100/100	79/58 27/49	100/100 －58/4	100/100 51/39	100/100 100/6
Ι-20	n-C₇H₁₅	3-CF₃	i-Bu	100 10	100/100 39/－144	100/100 52/－42	100/100 54/2	100/100 48/11	81/45 43/16	100/100 －49/9
Ι-21	n-C₇H₁₅	3-CF₃	n-C₅H₁₁	100 10	44/－90 100/100	100/100 58/－42	100/100 59/40	100/100 19/10	22/22 100/100	88/83 －19/－31
Ι-22	n-C₇H₁₅	3-CF₃	n-C₆H₁₃	100 10	100/100 100/100	75/－71 49/－68	100/100 53/27	100/100 －16/2	100/100 69/46	100/100 100/100
Ι-23	Et	4-F	Et	100 10	100/100 65/7	100/100 15/－51	100/100 11/15	100/100 48/22	100/100 －31/－20		100/100 32/21
Ι-24	Et	4-F	n-Pr	100 10	100/100 －12/1	100/100 22/－88	100/100 －12/1	100/100 30/－4	100/100 －6/－38		82/75 －11/30
Ι-25	Et	4-F	n-Bu	100 10	100/100 49/11	100/100 9/－45	100/100 39/－6	100/100 40/－2	100/100 －5/－21		100/100 3/4
Ι-26	Et	4-F	n-C₅H₁₁	100 10	100/100 48/－14	64/－47 －1/－30	100/100 48/－14	100/100 58/－16	100/100 －13/－22		100/100 77/32
Ι-27	Et	4-F	n-C₆H₁₃	100 10	40/－19 37/－37	75/20 13/－91	100/100 9/37	100/100 －1/－1	39/44 －2/－32		100/100 69/14
Ι-28	n-Pr	4-F	Et	100 10	63/28 22/－38	38/－42 －13/－23	63/28 22/－38	44/12 15/－18	－2/－4 －45/22		100/100 45/7
Ι-29	n-Pr	4-F	n-Bu	100 10	100/100 44/－48	60/－11 35/－252	100/100 15/－41	100/100 9/－14	100/100 29/－2		100/100 9/5
Ι-30	n-Pr	4-F	n-C₅H₁₁	100 10	100/100 26/－11	100/100 24/－54	100/100 40/－15	100/100 －9/27	100/100 －82/－67		100/100 55/－2
Ι-31	n-Pr	4-F	n-C₆H₁₃	100 10	100/100 25/－22	100/100 －16/－91	100/100 －20/－28	100/100 －61/－28	100/100 －76/－94		100100 －5/14
Ι-32	n-Bu	4-F	Me	100 10	100/100 70/1	100/100 13/－67	100/100 44/－31	100/100 18/－22	100/100 －52/－6		100/100 38/19
Ι-33	n-Bu	4-F	Et	100 10	100/100 68/23	100/100 24/－42	100/100 －21/－38	100/100 －30/－12	100/100 －130/－14		100/100 35/－4
Ι-34	n-Bu	4-F	n-Pr	100 10	100/100 48/－12	100/100 20/－98	100/100 17/－12	100/100 32/－2	100/100 －45/－56		100/100 13/9
Ι-35	n-Bu	4-F	n-Bu	100 10	100/100 25/7	100/100 38/－85	100/100 100/100	100/100 38/2	100/100 －32/－29		100/100 100/100
Ι-36	n-C₅H₁₁	4-F	Et	100 10	100/100 48/22	100/100 43/59	100/100 30/－20	100/100 53/－10	100/100 －10/－11		100/100 35/－6
Ι-37	n-C₅H₁₁	4-F	n-Pr	100 10	100/100 53/44	100/100 56/－11	100/100 100/100	100/100 61/－14	100/100 －41/－57		100/100 100/100
Ι-38	n-C₅H₁₁	4-F	n-Bu	100 10	100/100 64/7	100/100 38/－73	100/100 －7/－14	100/100 100/100	100/100 100/100		100/100 35/14
Ι-39	n-C₅H₁₁	4-F	n-C₅H₁₁	100 10	100/100 64/33	100/100 60/－5	100/100 44/－31	100/100 40/－6	100/100 15/17		100/100 56/14
Ι-40	n-C₅H₁₁	4-F	n-C₆H₁₃	100 10	100/100 61/－23	100/100 42/－30	100/100 42/－31	100/100 43/－18	100/100 －52/－46		100/100 17/－11
Ι-41	n-C₆H₁₃	4-F	n-Bu	100 10	100/100 80/15	100/100 31/－73	100/100 34/21	100/100 43/－9	100/100 －19/－28		100/100 64/51
Ι-42	n-C₇H₁₅	4-F	n-C₅H₁₁	100 10	100/100 37/4	100/100 56/－79	100/100 32/－48	100/100 30/－22	100/100 －15/56		100/100 49/－11
唑嘧磺草胺				100 10	84/62 62/47	97/89 70/8	92/73 82/61	95/83 83/60	93/86 90/84		90/85 83/77

新型嘧啶并[5,4-e][1,2,4]三唑并[1,5-c]嘧啶衍生物的合成与除草活性