松油烯基邻苯二甲酰亚胺衍生物的合成及其除草活性研究

doi:10.3969/j.issn.0253-2417.2024.02.014

Abstract

Abstract:

Using α-terpinene(1) as the starting material, dimethyl terpinylbutenedioate(2) was synthesized through its Alder-Rickert reaction with dimethyl butenedioate. Terpinyl phthalic anhydride(3) was subsequently synthesized by their ring-closing reaction. Afterwards, 13 novel terpinyl phthalimide derivatives(4a-4m) were synthesized by the substitution reactions of compound 3 with a series of aromatic amine compounds. The structures of the target compounds were characterized by IR, ESI-MS, ¹H NMR and ¹³C NMR, and the successful synthesis of the target compounds 4a-4m was confirmed. Preliminary herbicidal activity tests results showed that most synthetic compounds exhibited certain herbicidal activity against Echinochloa crusgalli(L.) Beauv, Digitaria sanguinalis(L.) Scop., Abutilon theophrasti Medicus and Amaranthus retroflexus when they were applied to the stems and leaves at a dosage of 1.5 kg/hm². Among them, compounds 4b(R=p-CH₃) and 4c(R=p-OCH₃) showed the highest inhibitory activity and reached grade B against A. theophrasti Medicus with the inhibition rates of 62.2% and 64.0%, respectively.

Key words: terpinene, phthalimide, herbicidal activity, synthesis

CLC Number:

TQ35

Yun ZHANG, Guangtong ZHU, Meifang ZHUO, Yanmin HUANG, Qijin MO. Synthesis and Herbicidal Activity of Terpinyl Phthalimide Derivatives[J]. Chemistry and Industry of Forest Products, 2024, 44(2): 103-110.

Figures/Tables 2

References 21

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化合物 compound	土壤处理pre-emergence treatment				茎叶处理post-emergence treatment
化合物 compound	苘麻 A.theophrasti	反枝苋 A.retroflexus	稗草 E.crusgali	马唐 D.sanguinalis	苘麻 A.theophrasti	反枝苋 A.retroflexus	稗草 E.crusgali	马唐 D.sanguinalis
4a	0	13.3	0	0	24.5	33.9	36.2	39.9
4b	3.3	0	14.6	4.2	62.2	15.1	29.2	9.6
4c	0	0	3.9	6.2	64.0	23.2	12.6	8.1
4d	3.3	3.2	0	0	28.8	54.1	23.7	27.8
4e	0.5	0	6.6	0	19.2	47.9	19.9	22.2
4f	24.2	32.3	0	0	56.1	38.5	28.7	28.3
4g	0	0	29.2	6.2	40.3	11.8	33.8	22.7
4h	0	0	37.9	0	14.8	47.9	28.8	32.8
4i	0	0	25.3	0	12.2	34.0	18.9	18.2
4j	0	26.7	28.2	4.2	38.5	17.4	31.5	27.3
4k	2.6	0	26.1	0	0	11.3	0	16.3
4l	0	0	3.6	0	0	0	0	10.5
4m	13.5	0	16.0	0	17.4	0	0	5.8
丙炔氟草胺 flumioxazin	100	100	100	100	100	100	100	100

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Synthesis and Herbicidal Activity of Terpinyl Phthalimide Derivatives

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