Research on controllable degradation of sulfonylurea herbicides

Hua, Xuewen; Chen, Minggui; Zhou, Shuang-Shuang; Zhang, Dongkai; Liu, Ming; Liu, Jingbo; Lei, Kang; Song, Haibin; Li, Yonghong; Gu, Yu‐Cheng; Li, Zhengming

doi:10.1039/c5ra25765d

Cited by 13 publications

(32 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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]. 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: 72%

“…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%

“…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%

See 3 more Smart Citations

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

et al. 2022

Molecules

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Section: Compounds Nl101-nl108mentioning

confidence: 72%

“…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%

See 2 more Smart Citations

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

et al. 2022

Molecules

Self Cite

View full text Add to dashboard Cite

show abstract

“…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

Molecules

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Controllable Effect of Structural Modification of Sulfonylurea Herbicides on Soil Degradation

et al. 2016

Self Cite

View full text Add to dashboard Cite

The study of soil degradation behaviors of sulfonylurea herbicides in relation to their different structural attributes is utmost important for us to comprehend the development of new eco-friendly herbicides. It is postulated that the structural modification of the chemical structures could influence their degradation rates in soil. Nine devised structures were synthesized to study their herbicidal activity as well as their soil degradation behaviors respectively. The novel compounds I-3-I-7 were characterized by UV, 1 H NMR and 13 C NMR, MS and EA. Bioassays indicated that most of target compounds displayed superior herbicidal activities in comparison with Chlorsulfuron. Soil degradation results further confirmed our previous assumption that the introduction of electron-donating substituents at 5 th position of the benzene ring distinctly increased their degradation rates, among which dimethylamino and diethylamino groups can adjust the degradation rate to a more favorable status.

show abstract

Research on controllable degradation of sulfonylurea herbicides

Abstract: Through studying structure, bioassay and soil degradation tri-factor relationship, potential controllable degradation of SU was firstly explored and summarized.

Cited by 13 publications

References 24 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

Controllable Effect of Structural Modification of Sulfonylurea Herbicides on Soil Degradation

Contact Info

Product

Resources

About