Design, Synthesis and Herbicidal Activity of Novel Uracil Compounds Containing Piperidine Moiety

doi:10.6023/cjoc202311019

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (5): 1592-1605.DOI: 10.6023/cjoc202311019 Previous Articles Next Articles

ARTICLES

新型含哌啶结构的脲嘧啶类化合物的设计合成与除草活性研究

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^,^*()

a 沈阳工业大学材料科学与工程学院沈阳 110870
b 沈阳化工大学功能分子研究所沈阳 110142
c 广西思钺生物科技有限责任公司南宁 530000
d 辽宁科技大学辽宁鞍山 114051

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:
†共同第一作者
基金资助:
南宁市科学研究与技术开发计划(20201043); 南宁市创新创业领军人才“邕江计划”创业(2020002-1)

Design, Synthesis and Herbicidal Activity of Novel Uracil Compounds Containing Piperidine Moiety

Hongyan Pei^a^,^b,†, Jialin Ye^b,†, Feng Wang^b, Dongdong Liu^b, Yukui Yu^c, Jing Zhang^b^,^c^,^d(), Lixin Zhang^a^,^b^,^c^,^d()

a School of Materials Science and Engineering, Shenyang University of Technology, Shenyang 110870
b Institute of Functional Molecules, Shenyang University of Chemical Technology, Shenyang 110142
c Metisa Biotechnology Co. Ltd., Nanning, 530000
d University of Science and Technology Liaoning, Anshan, Liaoning 114051

Received:2023-11-21 Revised:2024-01-04 Published:2024-01-18
Contact: *E-mail: zhang-jing@syuct.edu.cn; zhanglixin@syuct.edu.cn
About author:
†These authors contributed equally to this work.
Supported by:
Nanning Scientific Research and Technology Development Program(20201043); Nanning Innovation and Entrepreneurship Leading Talents “YongJiang Plan” Entrepreneurship Project(2020002-1)

1. .pdf(6350KB)

Abstract

To search the novel, efficient and environmentally friendly herbicide compounds, based on the principle of biologically active factor splicing, 26 uracil compounds with novel structures were designed and synthesized by using 2-fluoro-4-chloroaniline as raw material. The structures were confirmed by ¹H NMR, ¹³C NMR, and HRMS spectra. The results of post-seedling herbicidal activity test showed that the control effect of 5 compounds on broadleaved weeds (Zinnia elegans and Abutilon theophrasti) was 90%~100% at the concentration of 37.5 g/hm². At a concentration of 9.375 g/hm², there are still two compounds that have a control effect of 50%~90% on broadleaved weeds (Zinnia elegans and Abutilon theophrasti), and have no harmful effects on gramineous weeds (Echinochloa crus-galli and Setaria glauca). Molecular electrostatic potential showed that 2-chloro-N-((1-(cyclopropanecarbonyl)piperidin-4-yl)methyl)-4-fluoro-5-(3-methyl-2,6- dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl)benzenesulfonamide (8i) and saflufenacil have similar charge distributions, which may play an important role in the docking of the compound with its target receptor. The molecular docking results revealed that compound 8i has various interactions with protoporphyrinogen oxidase. The above results laid the foundation for further optimization of uracil compounds.

Key words: uracil, piperidine, herbicidal activity, molecular electrostatic potential, molecular docking

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 12

References 30

[1]	Xun, X.; Ni, Y.-D.; Li, J.-F.; Ding, Y.; Zhang, M.; Wang, Y.; Hu, L.-P.; Zhou, H.-Y.; Yang, B.; Shi, J.; Gao, L.; Dai, H. Chin. J. Org. Chem. 2020, 40, 1638 (in Chinese).
	( 荀校, 倪亚丹, 李金峰, 丁颖, 张敏, 王杨, 胡兰萍, 周环宇, 杨冰, 石健, 高磊, 戴红, 有机化学, 2020, 40, 1638.) doi: 10.6023/cjoc202002024
[2]	Wang, F.; Chen, Y.; Pei, H.-Y.; Zhang, J.; Zhang, L.-X. Chin. J. Org. Chem. 2023, 43, 2826 (in Chinese).
	( 王锋, 陈钰, 裴鸿艳, 张静, 张立新, 有机化学, 2023, 43, 2826.) doi: 10.6023/cjoc202212015
[3]	Ma, D.; Yin, Y.; Chen, Y.-L.; Yan, Y.-T.; Wu, J. RSC Adv. 2021, 11, 15380.
[4]	Ding, C.-R.; Pan, Y.-Y.; Tan, C.-X. Chin. J. Org. Chem. 2020, 40, 528 (in Chinese).
	( 丁成荣, 潘亚运, 谭成侠, 有机化学, 2020, 40, 528.) doi: 10.6023/cjoc201907034
[5]	Abdelshaheed, M.-M.; Fawzy, I.-M.; El-Subbagh, H.-I.; Youssef, K.-M. Future J. Pharm. Sci. 2021, 7, 1.
[6]	Li, J.-J.; Dai, L.-L.; Huang, W.-H.; Bi, Y.-L. Chin. J. Pestic. 2019, 58, 703 (in Chinese).
	( 李君君, 戴玲玲, 黄文化, 毕亚玲, 农药, 2019, 58, 703.)
[7]	Zhang, S.-L.; Pei, H.-Y.; Sheng, Z.-B.; Gao, Y.-X.; Zhang, J.; Zhang, L.-X. Mod. Agrochem. 2021, 20, 6 (in Chinese).
	( 张石磊, 裴鸿艳, 盛祝波, 高一星, 张静, 张立新, 现代农药, 2021, 20, 6.)
[8]	Wang, D. W.; Lu, L.; Xue, Z. Y.; Yu, S. Y.; Zhang, R. B.; Xia, W.; Han, X.; Xin, W.; Zhen, X. J. Agric. Food Chem. 2021, 69, 4081.
[9]	Park, J.; Ahn, Y. O.; Nam, J. W.; Hong, M. K.; Song, N.; Kim, T.; Yu, G. H.; Sung, S. K. Pestic. Biochem. Physiol. 2018, 152, 38.
[10]	Yang, S.; Tang, J. H.; Li, B. J.; Yao, G. K.; Peng, H. X.; Pu, C. M.; Zhao, C.; Xu, H. H. J. Agric. Food Chem. 2023, 71, 14221-14231.
[11]	Cha, J. Y.; Lee, D. Y.; Ali, I.; Jeong, S. Y.; Shin, B.; Ji, H.; Kim, J. S.; Kim, M. G.; Kim, W. Y. Plant Cell Rep. 2019, 38, 793.
[12]	Fukunaga, S.; Ogata, K.; Eguchi, A.; Matsunaga, K.; Sakurai, K., Abe, J.; Cohen, M.-C.; Asano, H. Regul. Toxicol. Pharmacol. 2022, 136, 105268.
[13]	Ivantsova, E.; Konig, I.; Lopez-Scarim, V.; English, C.; Charnas, S.-R.; Souders, C.-L.; Martyniuk, C.-J. Environ. Toxicol. Pharmacol. 2023, 98, 104084.
[14]	Li, P. S. WO 2022095816, 2022.
[15]	Qu, R. Y.; He, B.; Yang, J. F.; Yang, W. C.; Wu, Q. Y.; Li, Q. X.; Yang, G. F. Pest Manage. Sci. 2021, 77, 2620.
[16]	Tan, H.-J. World Pestic. 2022, 44(9), 1 (in Chinese).
	( 谭海军, 世界农药, 2022, 44(9), 1.)
[17]	Yang, S.; Tang, J. H.; Li, B. J.; Yao, G. K.; Peng, H. X.; Pu, C. M.; Zhao, C.; Xu, H. H. J. Agric. Food Chem. 2023, 71, 14221.
[18]	Yu, J. J.; Jiang X. F. Adv. Agrochem. 2023, 2, 3.
[19]	Luan, T.; Cui, S.-J.; Sui, L.-L.; Sun, C.-Y.; Zhang, D.-J. Chem. J. Chin. Univ. 2023, 44, 20230098 (in Chinese).
	( 栾天, 崔思娇, 隋丽丽, 孙驰宇, 张大军, 高等学校化学学报, 2023, 44, 20230098.) doi: 10.7503/cjcu20230098
[20]	Wen, Y.-P.; Zhang, S.; Hou, G.-F.; Yu, Y.-H.; Gao, J.-S. Chin. J. Org. Chem. 2016, 36, 642 (in Chinese).
	( 温彦鹏, 张爽, 侯广峰, 于颖慧, 高金胜, 有机化学, 2016, 36, 642.) doi: 10.6023/cjoc201508008
[21]	Li, K.-M.; Li, Y.-S.; Yi, Y.-J.; Xu, L.-T.; Ye, J.; Ou, X.-M.; Li, J.-M.; Hu, A.-X. Chem. J. Chin. Univ. 2020, 41, 716 (in Chinese).
	( 李康明, 李延赛, 易阳杰, 徐雷涛, 叶姣, 欧晓明, 李建明, 胡艾希, 高等学校化学学报, 2020, 41, 716.) doi: 10.7503/cjcu20190504
[22]	Singh, I.; Al-Wahaibi, L. H.; Srivastava, R.; Prasad, O.; Pathak, S. K.; Kumar, S.; Parveen, S.; Banerjee, M.; El-Emam, A. A.; Sinha, L. ACS Omega 2020, 5, 46.
[23]	Yang, J. C.; Wu, E. M.; Jin, S. Z.; Wu, J.; Ying, J. W.; Yang, F.; Liu, C. L. CN 108570041, 2018.
[24]	Lee, K.; Kuk, J.; Ahn, Y.; Lee, J. WO 2018128387, 2018.
[25]	Liu, A.-C.; Fang, Q.; Wu, Z. H.; Xu, Y.-L.; Chen, D.-F. World Pestic. 2023, 45(09), 19 (in Chinese).
	( 刘安昌, 方强, 吴子豪, 徐婴兰, 陈典富, 世界农药, 2023, 45(09), 19.)
[26]	Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V..; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H.; Pizmaylov, A.; Fbloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J.J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J.J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision D.01, Gaussian, Inc., Wallingford, CT, 2013.
[27]	Chen, W.; Lei, S.-M.; Lan, Y.-X.; Xu, H.-J.; Yu, P.-B.; Zhang, R.; Wu, R.; Chen, Y. Chin. J. Org. Chem. 2022, 42, 2164 (in Chinese).
	( 陈伟, 雷思敏, 兰雨欣, 许豪键, 余坪槟, 张锐, 吴润, 陈阳, 有机化学, 2022, 42, 2164.) doi: 10.6023/cjoc202201020
[28]	Ibrahim, S.; Ghabi, A.; Amiri, N.; Mtiraoui, H.; Hajji, M.; Bel-Hadj-Tahar, R.; Msaddek, M. Monatsh. Chem. 2021, 152, 523.
[29]	Koch, M.; Breithaupt, C.; Kiefersauer, R.; Freigang, J.; Huber, R.; Messerschmidt, A. EMBO J. 2004, 23, 1720.
[30]	Gao, W.; Li, X.; Ren, D.; Sun, S.; Huo, J.; Wang, Y.; Chen, L.; Zhang, J. Molecules 2019, 24, 4363.

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.	∆E_Total/a.u.	∆E_LUMO/a.u.	∆E_HOMO/a.u.	∆E^a/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.	∆E_Total/a.u.	∆E_LUMO/a.u.	∆E_HOMO/a.u.	∆E^a/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

新型含哌啶结构的脲嘧啶类化合物的设计合成与除草活性研究

Design, Synthesis and Herbicidal Activity of Novel Uracil Compounds Containing Piperidine Moiety

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 12

References 30

Related Articles 15

Recommended Articles

Metrics

Comments

Compd.	百日草(ZE)		苘麻(AT)		金色狗尾草(SG)		稗草(EC)
Compd.	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

[1]	Simin Wu, Jiaxin Tang, Yujia Zhou, Xuetao Xu, Haoxing Zhang, Shaohua Wang. α-Glucosidase Inhibition Research of Derivatives Based on 2β-Acetoxyferruginol Scaffold Excluding Acetic Acid Group [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 613-621.
[2]	Feng Wang, Yu Chen, Hongyan Pei, Jing Zhang, Lixin Zhang. Design, Synthesis and Antifungal Activities of Novel 1,2,4-Oxadiazole Derivatives Containing Piperidine [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2826-2836.
[3]	Min Liu, Dongyan Yang, Yumei Xiao, Wangcang Su, Fenghai Zhao, Qin Zhaohai .. Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2790-2799.
[4]	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.
[5]	Huan Xu, Hongfei Wu, Xiaoming Zhang, Xingxing Lu, Tengda Sun, Yue Qi, Yufan Lin, Xinling Yang, Li Zhang, Yun Ling. Design, Synthesis and Bioactivity of Sulfonyl Hydrazides and Hydrazides Containing Fragment 1,2,3,4-Tetrahydroisoquinoline [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 725-733.
[6]	Lei Wang, Shujing Yu, Na Yang, Baolei Wang. Studies on the Synthesis and Biological Activities of Novel Dihydroquinazolinone-Containing Caffeine Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 299-307.
[7]	Changxing Sun, Fuhao Zhang, Huan Zhang, Penghui Li, Lin Jiang. Design, Synthesis, Fungicidal Activity and Molecular Docking Study of Novel 2-(1-Methyl-1H-pyrazol-4-yl)pyrimidine-4-carboxamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 229-235.
[8]	Wei Chen, Simin Lei, Yuxin Lan, Haojian Xu, Pingbin Yu, Rui Zhang, Run Wu, Yang Chen. Design, Synthesis and Antifungal Activities of Novel Quinazolinone Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2164-2171.
[9]	Changkai Wang, Tengda Sun, Xuebo Zhang, Xinling Yang, Xingxing Lu, Huan Xu, Fasheng Shi, Li Zhang, Yun Ling. Design, Synthesis and Bioactivity of Novel Fluoropyrazole Hydrazides [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1527-1536.
[10]	Xiu Wang, Wengui Duan, Guishan Lin, Baoyu Li, Wenjing Zhang, Fuhou Lei. Synthesis, Antifungal Activity, Three-Dimensional Quantitative Structure-Activity Relationship and Molecular Docking Study of 4-Acyl-3-amino-1,2,4-triazole-thioether Derivatives Containing Natural Pinene Structure [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 871-883.
[11]	Yuanfang Kong, Bin Yang, Yan Zhuang, Jingyu Zhang, Demei Sun, Chunhong Dong. Research Progress on the Synthesis and Structure-Activity Relationship of Five Hypoglycemic Active Heterocycles Based on Dipeptidyl Peptidase 4 (DPP-4) Target Design [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 770-784.
[12]	Yucheng Cui, Meihua Chen, Guishan Lin, Wengui Duan, Qingmin Li, Renxuan Zou, Bo Cen. Synthesis, Antifungal Activity and Molecular Docking Study of 1,3,4-Thiadiazole-Urea Compounds Containing gem-Dimethylcyclopropane Ring Structure [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3784-3797.
[13]	Yingjun Li, Ledi Lin, Jihong Liu, Lixin Gao, Li Sheng, Kun Jin, Xuejie Liu, Hongjing Yang, Jia Li. Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel N-Acylhydrazone Derivatives Containing Carbazole and Aromatic Ring/Aromatic Fused Heterocycle [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3593-3607.
[14]	Yingjun Li, Ledi Lin, Kun Jin, Lixin Gao, Li Sheng, Jihong Liu, Jia Li. Synthesis and Protein Tyrosine Phosphatase 1B (PTP1B) Inhibitory Activity Evaluation of Novel Arylaminoacetylhydrazone Derivatives Containing Carbazole Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3157-3170.
[15]	Chengfei Li, Bo Cen, Wengui Duan, Guishan Lin, Xiu Wang, Baoyu Li. Synthesis, Herbicidal Activity and Three-Dimensional Quantitative Structure-Activity Relationship (3D-QSAR) Study of 4-Methyl- 1,2,4-triazole-thioether Compounds Containing Natural Styrene Structure [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2485-2495.