Chirality in synthetic agrochemicals: bioactivity and safety considerations

Kurihara, Norio; Miyamoto, J.; Paulson, GD; Zeeh, Bernd; Skidmore, MW; Hollingworth, RM; Kuiper, HA

doi:10.1002/(sici)1096-9063(199902)55:2<219::aid-ps820>3.0.co;2-0

Cited by 22 publications

(18 citation statements)

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“…There are many reports about the stereoselective bioactivity of triazole fungicides with two chiral carbons. (2 S ,3 R )‐Triadimenol, (2 S ,4 R )‐propiconazole, (2 S ,4 R )‐etaconazole, and (2 R ,3 R )‐paclobutrazol showed better activity than the other stereoisomers . Our results here and results from others indicate that the R configuration of chiral carbon atoms near the triazole heterocyclic ring plays a key role in biological activity in chiral triazole fungicides.…”

Section: Resultssupporting

confidence: 67%

“…The results here show that there were significant differences of stereoselective bioactivity among the four stereoisomers of bitertanol against eight phytopathogens ( Table 1) and (2R,3R)-paclobutrazol showed better activity than the other stereoisomers. [23][24][25][26] Our results here and results from others indicate that the R configuration of chiral carbon atoms near the triazole heterocyclic ring plays a key role in biological activity in chiral triazole fungicides.…”

Section: Bioactivity Test On Fungimentioning

confidence: 79%

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Stereoselective bioactivity, toxicity and degradation of the chiral triazole fungicide bitertanol

Gao

Wen

et al. 2019

Pest Management Science

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BACKGROUND The chiral pesticide bitertanol has been widely used in the prevention and treatment of fungal diseases on many crops. However, research on bitertanol at the stereoisomer level has not been reported. Here, we study the stereoselective bioactivity, toxicity, and degradation of this pesticide under laboratory and field conditions. RESULT (1S,2R)‐Bitertanol was the most effective stereoisomer, showing 4.3–314.7 times more potent bioactivity than other stereoisomers against eight target pathogenic fungi. (1S,2R)‐Bitertanol showed 10.2 times greater inhibition of Botrytis cinerea spore germination than (1R,2S)‐bitertanol. According to the receptor‐drug docking results, the distances from the nitrogen atom in the heterocycle of (1S,2R)‐, (1R,2S)‐, (1R,2R)‐, and (1S,2S)‐bitertanol to the central Fe + atoms in the ferriporphyrin were 2.5, 3.8, 2.6, and 3.8 Å, respectively. (1S,2S)‐Bitertanol was 1.6–2.7 times more toxic than (1R,2R)‐bitertanol to Chlorella pyrenoidosa. The half‐lives of (1R,2S)‐, (1S,2R)‐, (1R,2R)‐, and (1S,2S)‐bitertanol were 3.7, 4.1, 4.1, and 4.8 d, respectively, in tomato. CONCLUSION The stereoselective bioactivity, toxicity, and degradation for bitertanol were first studied here. (1S,2R)‐Bitertanol was a high efficiency and low toxicity stereoisomer. Moreover, the stereoselective bioactivity among all stereoisomers correlated with the binding distances and calculated energy differences between stereoisomers and the target protein. This study also provides a foundation for a systematic evaluation of bitertanol at the stereoisomer level. © 2019 Society of Chemical Industry

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Section: Resultssupporting

confidence: 67%

Section: Bioactivity Test On Fungimentioning

confidence: 79%

Stereoselective bioactivity, toxicity and degradation of the chiral triazole fungicide bitertanol

Gao

Wen

et al. 2019

Pest Management Science

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“…3 Thereinto, the (1S, 2R)-isomer is the highest in fungicidal activity (up to 1000-fold more active than the other three). 4 So, it is necessary to separate enantiomers of chiral pesticides for further researches on activity, toxicity, environmental fates, and more efficient agricultural applications.…”

Section: Introductionmentioning

confidence: 99%

Direct Enantioseparation of Nitrogen‐heterocyclic Pesticides on Amylose‐tris‐(5‐chloro‐2‐methylphenylcarbamate) by Reversed‐Phase High‐Performance Liquid Chromatography

et al. 2012

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In this study, 11 nitrogen-heterocyclic pesticides were stereoselectively separated on amylose-tris-(5-chloro-2-methylphenylcarbamate) chiral stationary phase, using reversed-phase high-performance liquid chromatography with diode array detector and optical rotation detector at 426 nm. The effects of mobile phase composition and column temperature (5-40 °C) on separation were investigated. When acetonitrile and water were used as mobile phase, satisfactory separations were obtained on amylose-tris-(5-chloro-2-methylphenylcarbamate) for four pesticides with elution orders of (+)/(-)-simeconazole (1), (-)/(+)-nuarimol (3), (-)/(+)-carfentrazone-ethyl (4), and (-)/(+)/(-)/(+)-bromuconazole (9) and part separations for three with elution orders of (-)/(+)-famoxadone (6), (+)/(-)-fenbuconazole (10), and (-)/(+)-triapenthenol (11). Only two chromatographic peaks on diode array detector were obtained for diclobutrazol (2), cyproconazole (5), etaconazole (7), and metconazole (8), although they should have four stereoisomers in theory because of presences of two chiral centers in molecules. The stereoisomeric optical signals of all pesticides did not reverse with temperature changes but would reverse with different solvent types for some pesticides. These results will be useful to prepare and analyze individual enantiomers of chiral pesticides.

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“…T he separation of enantiomers of chiral compounds continues to be of great interest due to their prevalence in the pharmaceuticals, agrochemicals, and food additives. [1][2][3] It is well recognised that enantiomers often exhibit different biological and pharmacological responses. Chiral separation remains challenging due to the identical physical and chemical properties of enantiomers in an achiral environment, and research on specialised separation techniques continues to be developed to resolve individual enantiomers.…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of racemic mandelic acid by simulated moving bed chromatography using Chiralcel‐OD column

et al. 2014

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The chiral separation of the racemic mandelic acid ((R,S)‐MA) by simulated moving bed chromatography with columns packed with Chiralcel‐OD stationary phase is investigated experimentally and numerically. The transport dispersion model combined with the modified Langmuir isotherm was applied to predict the dynamic behaviour and separation performance of the SMB process. The Triangle Theory was used to obtain the complete separation region of the SMB operation. The influences of the switching time, loading, extract flow rate and column configuration on the SMB performance were also studied. The online monitoring system consisting of circular dichroism (CD) and UV detector in series was employed to measure the composition and purity of the extract and raffinate streams. Good agreement between the experimental data and model predictions proved the efficiency and reliability of SMB modelling and the Triangle theory in the design and operation of SMB chromatography. Experimental results show that purity and recovery at extract and raffinate port can reach 99% although not at the same time.

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Chirality in synthetic agrochemicals: bioactivity and safety considerations

Cited by 22 publications

References 0 publications

Stereoselective bioactivity, toxicity and degradation of the chiral triazole fungicide bitertanol

Stereoselective bioactivity, toxicity and degradation of the chiral triazole fungicide bitertanol

Direct Enantioseparation of Nitrogen‐heterocyclic Pesticides on Amylose‐tris‐(5‐chloro‐2‐methylphenylcarbamate) by Reversed‐Phase High‐Performance Liquid Chromatography

Enantioseparation of racemic mandelic acid by simulated moving bed chromatography using Chiralcel‐OD column

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