Controllable Effect of Structural Modification of Sulfonylurea Herbicides on Soil Degradation

Hua, Xuewen; Zhou, Shuang-Shuang; Chen, Minggui; Wei, Wei; Liu, Ming; Lei, Kang; Zhou, Sha; Li, Yonghong; Wang, Baolei; Li, Zhengming

doi:10.1002/cjoc.201600438

Cited by 11 publications

(20 citation statements)

References 22 publications

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“…The synthetic procedure of 5-dialkylamino-substituted compounds is shown in Figure 3 , which was reported in our previous papers [ 11 , 12 , 13 ].…”

Section: Methodsmentioning

confidence: 99%

“…The structure of 5-substituted chlorsulfuron compounds is shown in Figure 2. The synthetic procedure of 5-dialkylamino-substituted compounds is shown in Figure 3, which was reported in our previous papers [11][12][13].…”

Section: Compounds Nl101-nl108mentioning

confidence: 99%

“…In our previous study, we found that 5-substituents on the benzene ring of chlorsulfuron had a critical influence on their degradation rates in soils. In 2016, Li firstly concluded that electron-donating substituents accelerated the degradation, while the electron-withdrawing ones prolonged the degradation time in acidic soil [ 11 , 12 ]. In order to further study the substitute-degradation relationship, Ma and Li introduced various N-methylamido and dialkylamino substituents on the 5-position of the benzene ring in chlorsulfuron and studied the structure-DT 50 relationship in soil with pH 5.52 [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

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Degradation of 5-Dialkylamino-Substituted Chlorsulfuron Derivatives in Alkaline Soil

et al. 2022

Molecules

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Sulfonylurea herbicides are widely used as acetolactate synthase (ALS) inhibitors due to their super-efficient activity. However, some sulfonylurea herbicides show toxicity under crop rotation due to their long degradation time, for example, chlorsulfuron. Our research goal is to obtain chlorsulfuron-derived herbicides with controllable degradation time, good crop safety and high herbicidal activities. Based on our previously reported results in acidic soil, we studied the degradation behaviors of 5-dialkylamino-substituted chlorsulfuron derivatives (NL101–NL108) in alkaline soil (pH 8.39). The experimental data indicate that addition of the 5-dialkylamino groups on the benzene ring of chlorsulfuron greatly accelerated degradation in alkaline soil. These chlorsulfuron derivatives degrade 10.8 to 51.8 times faster than chlorsulfuron and exhibit excellent crop safety on wheat and corn (through pre-emergence treatment). With a comprehensive consideration of structures, bioassay activities, soil degradation and crop safety, it could be concluded that 5-dialkylamino-substituted chlorsulfuron derivatives are potential green sulfonylurea herbicides for pre-emergence treatment on both wheat and corn. The study also provides valuable information for the discovery of new sulfonylurea herbicides for crop rotation.

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“…The synthetic procedure of 5-dialkylamino-substituted compounds is shown in Figure 3 , which was reported in our previous papers [ 11 , 12 , 13 ].…”

Section: Methodsmentioning

confidence: 99%

Section: Compounds Nl101-nl108mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Degradation of 5-Dialkylamino-Substituted Chlorsulfuron Derivatives in Alkaline Soil

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“…The synthesis of intermediates 7, 10 and 13 has been reported in previous work [ 11 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 ].…”

Section: Methodsmentioning

confidence: 99%

“…Our group has been working on the problem of the long degradation times of sulfonylurea herbicides. In our previous study, we found that the 5th substituted groups on the benzene ring in chlorsulfuron has a great influence on its degradation rate in acidic soils and concluded for the first time that electron-donating substituents could accelerate degradation rates in acidic soil ( Figure 1 ) [ 11 , 12 ]. Li et al found that 5-dialkylamino-substituted groups on the benzene ring of chlorsulfuron could greatly accelerate degradation under alkaline conditions [ 13 , 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Herbicidal Activity, Crop Safety and Soil Degradation of Pyrimidine- and Triazine-Substituted Chlorsulfuron Derivatives

et al. 2022

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Chlrosulfuron, a classical sulfonylurea herbicide that exhibits good safety for wheat but causes a certain degree of damage to subsequent corn in a wheat–corn rotation mode, has been suspended field application in China since 2014. Our previous study found that diethylamino-substituted chlorsulfuron derivatives accelerated the degradation rate in soil. In order to obtain sulfonylurea herbicides with good crop safety for both wheat and corn, while maintaining high herbicidal activities, a series of pyrimidine- and triazine-based diethylamino-substituted chlorsulfuron derivatives (W102–W111) were systematically evaluated. The structures of the synthesized compounds were confirmed with 1H NMR, 13C NMR, and HRMS. The preliminary biological assay results indicate that the 4,6-disubstituted pyrimidine and triazine derivatives could maintain high herbicidal activity. It was found that the synthesized compounds could accelerate degradation rates, both in acidic and alkaline soil. Especially, in alkaline soil, the degradation rate of the target compounds accelerated more than 22-fold compared to chlorsulfuron. Moreover, most chlorsulfuron analogs exhibited good crop safety for both wheat and corn at high dosages. This study provided a reference for the further design of new sulfonylurea herbicides with high herbicidal activity, fast degradation rates, and high crop safety.

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Synthesis, herbicidal activity and soil degradation of novel 5‐substituted sulfonylureas as AHAS inhibitors

Zhou

Zhao

Meng

et al. 2022

Pest Management Science

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BACKGROUND Chlorsulfuron, metsulfuron‐methyl and ethametsulfuron can damage sensitive crops in rotation pattern as a result of their long persistence in soil. To explore novel sulfonylurea (SU) herbicides with favorable soil degradation rates, four series of SUs were synthesized through a structure‐based drug design (SBDD) strategy. RESULTS The target compounds, especially Ia, Id and Ie, exhibited prospective herbicidal activity against dicotyledon oil seed rape (Brassica campestris), amaranth (Amaranthus retroflexus), monocotyledon barnyard grass (Echinochloa crusgalli) and crab grass (Digitaria sanguinalis) at a concentration of 15 a.i. g ha−1. Additionally, Ia, Id and Ig displayed excellent inhibitory effects against AtAHAS, with Kapp i values of 59.1, 34.5 and 71.8 μm, respectively, which were much lower than that of chlorsulfuron at 149.4 μm. The π‐π stack and H‐bonds between the Ia conformation and AtAHAS in the molecular docking results confirmed the series of compounds to be conventional AHAS inhibitors. In alkaline soil (pH = 8.46), compounds Ia–Ig revealed various degrees of acceleration in the degradation rate compared with chlorsulfuron. Besides, compound Ia showed considerable wheat and corn safety under postemergence at the concentration of 30, 60 and even 120 a.i. g ha−1. CONCLUSION Overall, based on the synthetic procedure, herbicidal activity, soil degradation and crop safety, the Ia sulfonylureas series were chosen to be investigated as prospective AHAS inhibitors. The 5‐dimethylamino group on SUs accelerated the degradation rate at different levels in alkaline soils which seems to be controllable in conventional cropping systems in their further application. © 2022 Society of Chemical Industry.

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Controllable Effect of Structural Modification of Sulfonylurea Herbicides on Soil Degradation

Cited by 11 publications

References 22 publications

Degradation of 5-Dialkylamino-Substituted Chlorsulfuron Derivatives in Alkaline Soil

Degradation of 5-Dialkylamino-Substituted Chlorsulfuron Derivatives in Alkaline Soil

Synthesis, Herbicidal Activity, Crop Safety and Soil Degradation of Pyrimidine- and Triazine-Substituted Chlorsulfuron Derivatives

Synthesis, herbicidal activity and soil degradation of novel 5‐substituted sulfonylureas as AHAS inhibitors

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