Design, Synthesis and Insecticidal, Acaricidal Activities of Novel Pyrrole-2-carboxylic Acid and Their Derivatives

doi:10.6023/cjoc202211010

Abstract

To discover new pyrrole pesticide candidates with good biological activity, based on the chemical structure of the highly efficient insecticidal and acaricidal agent chlorfenapyr, three key intermediates pyrrole-2-carboxylic acid and 26 new pyrrole compounds were designed and synthesized by active substructure splicing method. The effects of different substituents on the biological activity of pyrrole compounds were explored by changing the N substituents of pyrrole ring. The bioassay results showed that most of the compounds showed good insecticidal activity against Plutella xylostella and Spodoptera exigua Hiibner, and some compounds showed a certain degree of acaricidal activity against Tetranychus cinnabarinus. 3-Bromo-1- (butoxymethyl)-5-(4-chlorophenyl)-4-cyano-N-(2,4-dimethylphenyl)-1H-pyrrole-2-carboxamide (6r), 3-bromo-5-(4-chloro- phenyl)-4-cyano-1-ethyl-N-(2-methyl-4-(perfluoropropan-2-yl)phenyl)-1H-pyrrole-2-carboxamide (6v), and 3-bromo-5-(4-ch- lorophenyl)-4-cyano-N-(2,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)phenyl)-1-ethyl-1H-pyrrole-2-carboxamide (6z) are insecticidal at a concentration of 100 mg•L^－1. The effect is similar to that of diflubenzuron, which was lower than the insecticidal acaricidal activity of chlorfenapyr, and the acaricidal effect was better than that of the commercial acaricide propargite.

Key words: pyrrole, chlorfenapyr, new pesticide, biological activity

Cite this article

Mingjia Guang, Shuo Jiang, Baoyu Zhu, Rusong Zhang, Kunpeng Wang, Minghui Wang, Liangzhong Xu. Design, Synthesis and Insecticidal, Acaricidal Activities of Novel Pyrrole-2-carboxylic Acid and Their Derivatives[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2895-2904.

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Compd.	y=ax＋b	LC₅₀/(mg•L^－1)	R
6q	y=1.86x＋2.65	18.34	0.97
6r	y=1.62x＋2.97	17.91	0.97
6v	y=1.52x＋3.01	20.38	0.96
6z	y=1.69x＋2.83	19.23	0.98
C-2	y=1.80x＋3.04	12.27	0.98
C-3	y=2.37x＋4.21	2.15	0.97

Compd.	y=ax＋b	LC₅₀/(mg•L^－1)	R
6q	y=1.86x＋2.65	18.34	0.97
6r	y=1.62x＋2.97	17.91	0.97
6v	y=1.52x＋3.01	20.38	0.96
6z	y=1.69x＋2.83	19.23	0.98
C-2	y=1.80x＋3.04	12.27	0.98
C-3	y=2.37x＋4.21	2.15	0.97

Compd.	y=ax＋b	LC₅₀/(mg•L^－1)	R
6q	y=1.51x＋3.24	14.64	0.98
6r	y=1.54x＋3.18	15.20	0.97
6v	y=1.74x＋2.96	14.87	0.97
6z	y=1.61x＋3.09	15.36	0.98
C-2	y=1.72x＋3.29	9.86	0.97
C-3	y=2.11x＋4.27	2.21	0.96

Compd.	y=ax＋b	LC₅₀/(mg•L^－1)	R
6q	y=1.51x＋3.24	14.64	0.98
6r	y=1.54x＋3.18	15.20	0.97
6v	y=1.74x＋2.96	14.87	0.97
6z	y=1.61x＋3.09	15.36	0.98
C-2	y=1.72x＋3.29	9.86	0.97
C-3	y=2.11x＋4.27	2.21	0.96

Compd.	y=ax＋b	LC₅₀/(mg•L^－1)	R
6i	y=1.30x＋3.76	8.99	0.95
6j	y=1.20x＋3.92	7.94	0.97
6r	y=1.29x＋3.83	8.07	0.96
6v	y=1.31x＋3.80	8.24	0.97
6z	y=1.20x＋4.05	6.19	0.96
C-1	y=1.29x＋3.44	16.19	0.96
C-3	y=1.01x＋4.73	1.85	0.96

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