Safening activity and metabolism of the safener cyprosulfamide in maize and wheat

Giannakopoulos, George; Dittgen, Jan; Schulte, Wolfgang; Zoellner, Peter; Helmke, Hendrik; Lagojda, Andreas; Edwards, Robert

doi:10.1002/ps.5801

Cited by 19 publications

(24 citation statements)

References 38 publications

(42 reference statements)

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“…26,27 It was shown that subtle modifications to the structure of CSA can affect its bioactivity, identifying the retention of the benzenesulphonamide group as a chemical feature required for its safener activity. 28 Scaffold hopping and active substructure combination play an important role in drug discovery techniques which are beneficial to the discovery of potential agrochemicals. Scaffold hopping creates new opportunities by incorporating novel scaffolds into known molecules in search of active compounds.…”

Section: Introductionmentioning

confidence: 99%

“…Using herbicides composed of IXF and CSA is a successful path for weed control in conventional and herbicide‐tolerant corn production system 26,27 . It was shown that subtle modifications to the structure of CSA can affect its bioactivity, identifying the retention of the benzenesulphonamide group as a chemical feature required for its safener activity 28 …”

Section: Introductionmentioning

confidence: 99%

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Fragments recombination, design, synthesis, safener activity and CoMFA model of novel substituted dichloroacetylphenyl sulfonamide derivatives

Wang

Zhao

et al. 2020

Pest Management Science

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BACKGROUND Isoxaflutole (IXF), as a kind of 4‐hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor, has been widely used in many kinds of plants. IXF can cause injury in corn including leaf and stem bleaching, plant height reduction or stunting, and reduced crop stand. Safeners are co‐applied with herbicides to protect crops without compromising weed control efficacy. With the ultimate goal of addressing Zea mays injury caused by IXF, a series of novel substituted dichloroacetylphenyl sulfonamide derivatives was designed on the basis of scaffold hopping and active substructure splicing. RESULTS A total of 35 compounds were synthesized via acylation reactions. All the compounds were characterized by infrared (IR), proton and carbon‐13 nuclear magnetic resonance (1H‐NMR and 13C‐NMR), and high‐resolution mass spectrometry (HRMS). The configuration of compound II‐1 was confirmed by single crystal X‐ray diffraction. The bioassay results showed that all the title compounds displayed remarkable protection against IXF via improved content of carotenoid. Especially compound II‐1 which possessed better glutathione transferases (GSTs) activity and carotenoid content than the contrast safener cyprosulfamide (CSA). All the satisfied parameters suggested that the Comparative Molecular Field Analysis (CoMFA) model was reliable and stable [with a cross‐validated coefficient (q2) = 0.527, r2 = 0.995, r2 pred = 0.931]. The molecular docking simulation indicated that the compound II‐1 and CSA could compete with diketonitrile (DKN) at the active site of HPPD, which is a hydrolyzed product of IXF in plants, causing the herbicide to be ineffective. CONCLUSIONS The present work revealed that the compound II‐1 deserves further attention as the candidate structure of safeners. © 2020 Society of Chemical Industry

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Fragments recombination, design, synthesis, safener activity and CoMFA model of novel substituted dichloroacetylphenyl sulfonamide derivatives

Wang

Zhao

et al. 2020

Pest Management Science

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“…Many sulfonamides are bioactive and have applications as antibiotics in mammals and as safeners in plants [44]. The safeners metcamifen and cyprosulfonamide used in monocot crops, for example, induce the expression of cytochrome P450s and glutathione transferases, which likely catalyze the detoxification of the herbicide clodinafop-propargyl [45,46]. Quinabactin, which activates the ABA receptors PYR1, PYL 1-3, and PYL5 and confers drought tolerance in Arabidopsis and soybean, also contains a sulfonamide group [47,48].…”

Section: Discussionmentioning

confidence: 99%

Chemical Genetics Approach Identifies Abnormal Inflorescence Meristem 1 as a Putative Target of a Novel Sulfonamide That Protects Catalase2-Deficient Arabidopsis against Photorespiratory Stress

Meer

Verlee

Willems

et al. 2020

Cells

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Alterations of hydrogen peroxide (H2O2) levels have a profound impact on numerous signaling cascades orchestrating plant growth, development, and stress signaling, including programmed cell death. To expand the repertoire of known molecular mechanisms implicated in H2O2 signaling, we performed a forward chemical screen to identify small molecules that could alleviate the photorespiratory-induced cell death phenotype of Arabidopsisthaliana mutants lacking H2O2-scavenging capacity by peroxisomal catalase2. Here, we report the characterization of pakerine, an m-sulfamoyl benzamide from the sulfonamide family. Pakerine alleviates the cell death phenotype of cat2 mutants exposed to photorespiration-promoting conditions and delays dark-induced senescence in wild-type Arabidopsis leaves. By using a combination of transcriptomics, metabolomics, and affinity purification, we identified abnormal inflorescence meristem 1 (AIM1) as a putative protein target of pakerine. AIM1 is a 3-hydroxyacyl-CoA dehydrogenase involved in fatty acid β-oxidation that contributes to jasmonic acid (JA) and salicylic acid (SA) biosynthesis. Whereas intact JA biosynthesis was not required for pakerine bioactivity, our results point toward a role for β-oxidation-dependent SA production in the execution of H2O2-mediated cell death.

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“…In these cases, safener treatments may induce transcriptional activation of specific GST genes and enhance the glutathione S-transferase (GST) expression of the respective enzymes that catalyze the conjugation of herbicides with glutathione (GSH) in crop plants to detoxify them [28]. Besides, detoxifying enzymes, including superoxide dismutase (SOD) and peroxidase (POD), are also involved in the detoxification of some herbicides [18,29].…”

Section: Introductionmentioning

confidence: 99%

New Lead Discovery of Herbicide Safener for Metolachlor Based on a Scaffold-Hopping Strategy

et al. 2020

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The use of herbicide safeners can significantly alleviate herbicide injury to protect crop plants and expand the application scope of the existing herbicides in the field. Sanshools, which are well known as spices, are N-alkyl substituted compounds extracted from the Zanthoxylum species and have several essential physiological and pharmacological functions. Sanshools display excellent safener activity for the herbicide metolachlor in rice seedlings. However, the high cost of sanshools extraction and difficulties in the synthesis of their complicated chemical structures limit their utilization in agricultural fields. Thus, the present study designed and synthesized various N-alkyl amide derivatives via the scaffold-hopping strategy to solve the challenge of complicated structures and find novel potential safeners for the herbicide metolachlor. In total, 33 N-alkyl amide derivatives (2a–k, 3a–k, and 4a–k) were synthesized using amines and saturated and unsaturated fatty acids as starting materials through acylation and condensation. The identity of all the target compounds was well confirmed by 1H-NMR, 13C-NMR, and high-resolution mass spectrometry (HRMS). The primary evaluation of safener activities for the compounds by the agar method indicated that most of the target compounds could protect rice seedlings from injury caused by metolachlor. Notably, compounds 2k and 4k displayed excellent herbicide safener activities on plant height and demonstrated relatively similar activities to the commercialized compound dichlormid. Moreover, we showed that compounds 2k and 4k had higher glutathione S-transferase (GST), superoxide dismutase (SOD), catalase (CAT), peroxidase (POD), and polyphenol oxidase (PPO) activities in rice seedlings, compared to the metolachlor treatment. In particular, 2k and 4k are safer for aquatic organisms than dichlormid. Results from the current work exhibit that compounds 2k and 4k have excellent crop safener activities toward rice and can, thus, be promising candidates for further structural optimization in rice protection.

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Safening activity and metabolism of the safener cyprosulfamide in maize and wheat

Cited by 19 publications

References 38 publications

Fragments recombination, design, synthesis, safener activity and CoMFA model of novel substituted dichloroacetylphenyl sulfonamide derivatives

Fragments recombination, design, synthesis, safener activity and CoMFA model of novel substituted dichloroacetylphenyl sulfonamide derivatives

Chemical Genetics Approach Identifies Abnormal Inflorescence Meristem 1 as a Putative Target of a Novel Sulfonamide That Protects Catalase2-Deficient Arabidopsis against Photorespiratory Stress

New Lead Discovery of Herbicide Safener for Metolachlor Based on a Scaffold-Hopping Strategy

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