Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (5): 1592-1605.DOI: 10.6023/cjoc202311019 Previous Articles Next Articles
ARTICLES
裴鸿艳a,b,†, 叶家麟b,†, 王锋b, 刘东东b, 余裕奎c, 张静b,c,d,*(), 张立新a,b,c,d,*()
收稿日期:
2023-11-21
修回日期:
2024-01-04
发布日期:
2024-01-18
作者简介:
基金资助:
Hongyan Peia,b,†, Jialin Yeb,†, Feng Wangb, Dongdong Liub, Yukui Yuc, Jing Zhangb,c,d(), Lixin Zhanga,b,c,d()
Received:
2023-11-21
Revised:
2024-01-04
Published:
2024-01-18
Contact:
*E-mail: About author:
Supported by:
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Hongyan Pei, Jialin Ye, Feng Wang, Dongdong Liu, Yukui Yu, Jing Zhang, Lixin Zhang. Design, Synthesis and Herbicidal Activity of Novel Uracil Compounds Containing Piperidine Moiety[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1592-1605.
Entry | Base | Solvent | Temperature | Yield/% |
---|---|---|---|---|
1 | Pyridine | CH2Cl2 | r.t. | 35.9 |
2 | Pyridine | CH3CN | r.t. | 38.8 |
3 | Pyridine | Toluene | r.t. | 1.2 |
4 | Et3N | CH2Cl2 | r.t. | 72.8 |
5 | Et3N | CH3CN | r.t. | 47.7 |
6 | Et3N | Toluene | r.t. | 2.6 |
7 | DIPEA | CH2Cl2 | r.t. | 70.5 |
8 | DIPEA | CH3CN | r.t. | 51.7 |
9 | DIPEA | Toluene | r.t. | 3.9 |
10 | NaHCO3 | CH2Cl2 | r.t. | 53.5 |
11 | NaHCO3 | CH3CN | r.t. | 56.9 |
12 | NaHCO3 | Toluene | r.t. | 5.2 |
13 | Et3N | CH2Cl2 | Reflux | 63.6 |
Entry | Base | Solvent | Temperature | Yield/% |
---|---|---|---|---|
1 | Pyridine | CH2Cl2 | r.t. | 35.9 |
2 | Pyridine | CH3CN | r.t. | 38.8 |
3 | Pyridine | Toluene | r.t. | 1.2 |
4 | Et3N | CH2Cl2 | r.t. | 72.8 |
5 | Et3N | CH3CN | r.t. | 47.7 |
6 | Et3N | Toluene | r.t. | 2.6 |
7 | DIPEA | CH2Cl2 | r.t. | 70.5 |
8 | DIPEA | CH3CN | r.t. | 51.7 |
9 | DIPEA | Toluene | r.t. | 3.9 |
10 | NaHCO3 | CH2Cl2 | r.t. | 53.5 |
11 | NaHCO3 | CH3CN | r.t. | 56.9 |
12 | NaHCO3 | Toluene | r.t. | 5.2 |
13 | Et3N | CH2Cl2 | Reflux | 63.6 |
Compd. | 百日草(ZE) | 苘麻(AT) | 金色狗尾草(SG) | 稗草(EC) | |||||||
---|---|---|---|---|---|---|---|---|---|---|---|
150 g/hm2 | 37.5 g/hm2 | 150 g/hm2 | 37.5 g/hm2 | 150 g/hm2 | 37.5 g/hm2 | 150 g/hm2 | 37.5 g/hm2 | ||||
8a | 100 | 100 | 90 | 90 | 80 | 20 | 60 | 20 | |||
8b | 30 | 20 | 80 | 50 | 0 | 0 | 0 | 0 | |||
8c | 95 | 40 | 98 | 60 | 0 | 0 | 0 | 0 | |||
8d | 90 | 40 | 80 | 50 | 0 | 0 | 0 | 0 | |||
8e | 10 | 10 | 20 | 0 | 0 | 0 | 0 | 0 | |||
8f | 100 | 70 | 100 | 70 | 0 | 0 | 0 | 0 | |||
8g | 90 | 70 | 100 | 30 | 0 | 0 | 0 | 0 | |||
8h | 95 | 40 | 95 | 40 | 0 | 0 | 0 | 0 | |||
8i | 100 | 100 | 100 | 100 | 80 | 20 | 30 | 20 | |||
8j | 10 | 0 | 10 | 0 | 0 | 0 | 0 | 0 | |||
8k | 5 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | |||
8l | 100 | 50 | 100 | 50 | 0 | 0 | 0 | 0 | |||
8m | 80 | 40 | 85 | 30 | 0 | 0 | 0 | 0 | |||
8n | 70 | 20 | 80 | 25 | 0 | 0 | 0 | 0 | |||
8o | 100 | 80 | 80 | 60 | 0 | 0 | 0 | 0 | |||
8p | 95 | 50 | 100 | 90 | 0 | 0 | 0 | 0 | |||
8q | 100 | 50 | 100 | 90 | 0 | 0 | 0 | 0 | |||
8r | 90 | 70 | 95 | 80 | 0 | 0 | 0 | 0 | |||
8s | 50 | 10 | 30 | 10 | 0 | 0 | 0 | 0 | |||
8t | 90 | 30 | 90 | 20 | 0 | 0 | 0 | 0 | |||
8u | 80 | 20 | 70 | 20 | 0 | 0 | 0 | 0 | |||
8v | 30 | 20 | 30 | 20 | 0 | 0 | 0 | 0 | |||
8w | 20 | 10 | 30 | 20 | 0 | 0 | 0 | 0 | |||
8x | 20 | 10 | 20 | 10 | 0 | 0 | 0 | 0 | |||
8y | 50 | 20 | 80 | 30 | 0 | 0 | 0 | 0 | |||
8z | 20 | 10 | 20 | 10 | 0 | 0 | 0 | 0 | |||
Fomesafen | 100 | 90 | 40 | 20 | 0 | 0 | 0 | 0 | |||
Saflufenacil | 100 | 100 | 100 | 100 | 100 | 80 | 80 | 50 |
Compd. | 百日草(ZE) | 苘麻(AT) | 金色狗尾草(SG) | 稗草(EC) | |||||||
---|---|---|---|---|---|---|---|---|---|---|---|
150 g/hm2 | 37.5 g/hm2 | 150 g/hm2 | 37.5 g/hm2 | 150 g/hm2 | 37.5 g/hm2 | 150 g/hm2 | 37.5 g/hm2 | ||||
8a | 100 | 100 | 90 | 90 | 80 | 20 | 60 | 20 | |||
8b | 30 | 20 | 80 | 50 | 0 | 0 | 0 | 0 | |||
8c | 95 | 40 | 98 | 60 | 0 | 0 | 0 | 0 | |||
8d | 90 | 40 | 80 | 50 | 0 | 0 | 0 | 0 | |||
8e | 10 | 10 | 20 | 0 | 0 | 0 | 0 | 0 | |||
8f | 100 | 70 | 100 | 70 | 0 | 0 | 0 | 0 | |||
8g | 90 | 70 | 100 | 30 | 0 | 0 | 0 | 0 | |||
8h | 95 | 40 | 95 | 40 | 0 | 0 | 0 | 0 | |||
8i | 100 | 100 | 100 | 100 | 80 | 20 | 30 | 20 | |||
8j | 10 | 0 | 10 | 0 | 0 | 0 | 0 | 0 | |||
8k | 5 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | |||
8l | 100 | 50 | 100 | 50 | 0 | 0 | 0 | 0 | |||
8m | 80 | 40 | 85 | 30 | 0 | 0 | 0 | 0 | |||
8n | 70 | 20 | 80 | 25 | 0 | 0 | 0 | 0 | |||
8o | 100 | 80 | 80 | 60 | 0 | 0 | 0 | 0 | |||
8p | 95 | 50 | 100 | 90 | 0 | 0 | 0 | 0 | |||
8q | 100 | 50 | 100 | 90 | 0 | 0 | 0 | 0 | |||
8r | 90 | 70 | 95 | 80 | 0 | 0 | 0 | 0 | |||
8s | 50 | 10 | 30 | 10 | 0 | 0 | 0 | 0 | |||
8t | 90 | 30 | 90 | 20 | 0 | 0 | 0 | 0 | |||
8u | 80 | 20 | 70 | 20 | 0 | 0 | 0 | 0 | |||
8v | 30 | 20 | 30 | 20 | 0 | 0 | 0 | 0 | |||
8w | 20 | 10 | 30 | 20 | 0 | 0 | 0 | 0 | |||
8x | 20 | 10 | 20 | 10 | 0 | 0 | 0 | 0 | |||
8y | 50 | 20 | 80 | 30 | 0 | 0 | 0 | 0 | |||
8z | 20 | 10 | 20 | 10 | 0 | 0 | 0 | 0 | |||
Fomesafen | 100 | 90 | 40 | 20 | 0 | 0 | 0 | 0 | |||
Saflufenacil | 100 | 100 | 100 | 100 | 100 | 80 | 80 | 50 |
Compd. | 百日草(ZE) | 苘麻(AT) | 金色狗尾草(SG) | 稗草(EC) |
---|---|---|---|---|
8a | 80 | 60 | 0 | 0 |
8c | 10 | 20 | 0 | 0 |
8f | 10 | 20 | 0 | 0 |
8g | 10 | 10 | 0 | 0 |
8h | 10 | 20 | 0 | 0 |
8i | 90 | 50 | 0 | 0 |
8l | 20 | 20 | 0 | 0 |
8p | 30 | 50 | 0 | 0 |
8q | 20 | 60 | 0 | 0 |
8r | 30 | 40 | 0 | 0 |
Saflufenacil | 100 | 100 | 10 | 20 |
Compd. | 百日草(ZE) | 苘麻(AT) | 金色狗尾草(SG) | 稗草(EC) |
---|---|---|---|---|
8a | 80 | 60 | 0 | 0 |
8c | 10 | 20 | 0 | 0 |
8f | 10 | 20 | 0 | 0 |
8g | 10 | 10 | 0 | 0 |
8h | 10 | 20 | 0 | 0 |
8i | 90 | 50 | 0 | 0 |
8l | 20 | 20 | 0 | 0 |
8p | 30 | 50 | 0 | 0 |
8q | 20 | 60 | 0 | 0 |
8r | 30 | 40 | 0 | 0 |
Saflufenacil | 100 | 100 | 10 | 20 |
Compd. | ∆ETotal/a.u. | ∆ELUMO/a.u. | ∆EHOMO/a.u. | ∆Ea/a.u. |
---|---|---|---|---|
8a | -2627.46164409 | -0.10851 | -0.24428 | 0.13577 |
8i | -2510.73775329 | -0.10789 | -0.23744 | 0.12955 |
Saflufenacil | -2510.72139594 | -0.11012 | -0.26993 | 0.15981 |
Compd. | ∆ETotal/a.u. | ∆ELUMO/a.u. | ∆EHOMO/a.u. | ∆Ea/a.u. |
---|---|---|---|---|
8a | -2627.46164409 | -0.10851 | -0.24428 | 0.13577 |
8i | -2510.73775329 | -0.10789 | -0.23744 | 0.12955 |
Saflufenacil | -2510.72139594 | -0.11012 | -0.26993 | 0.15981 |
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