Herbicidal activity of 1,3,4-thiadiazole derivatives

Kubo, Hiroshi; Sato, R.; Hamura, I.; Ohi, T.

doi:10.1021/jf60167a005

Cited by 35 publications

(17 citation statements)

References 3 publications

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“…Substituted 1,2,4-and 1,3,4-thiadiazoles have been reported to possess herbicidal activity (5,10). In the case of 1,3,4-thiadiazoles, this activity was found to be strongly associated with the 5-(1,1-dimethylethyl)-1,3,4-thiadiazole nucleus of the molecule (10). At present two derivatives are marketed commercially as herbicides for industrial weed control under the common names buthidazole and tebuthiuron (Fig.…”

Section: Micromolar Inhibition Of Pbotosystem I-mediated Transfer Ofmentioning

confidence: 99%

Inhibition of Photosynthetic Electron Transport in Isolated Spinach Chloroplasts by Two 1,3,4-Thiadiazolyl Derivatives

Hatzios¹,

Penner²,

Bell³

1980

Plant Physiol.

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Buthidazole (3-15-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yll 4-hydroxy-1-methyl-2linidinone) and tebuthiuron (N-15-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-ylI-N,N-dimethylurea) are two new promising herbicides for selective weed control in corn (Zea nays L.) and sugarcane (Sacchan officiaum L.), respectively. The effects of these two compounds on various pbotochemical reactions of isolated spinach (Spinacia okracea L.) chwooplasts were studied at concentrations of 0, 0.05, 0.5, 5, and 500 micromolar. Bu le and tebuthiuron at concentrations higher than 0.5 miromolar inhibited uncoupled electron transport from water to ferricyanide or to methyl viologen very strongly. Photosystem lI-mediated transfer of electrons from water to oxidzed diamonodurene, with 2,5-dlbromo-3-methyl-Kisopropyl-p-benzoquinone (DBMIB) Substituted 1,2,4-and 1,3,4-thiadiazoles have been reported to possess herbicidal activity (5, 10). In the case of 1,3,4-thiadiazoles, this activity was found to be strongly associated with the 5-(1,1-dimethylethyl)-1,3,4-thiadiazole nucleus of the molecule (10). At present two derivatives are marketed commercially as herbicides for industrial weed control under the common names buthidazole and tebuthiuron (Fig. 1). Those two herbicides have also shown promise for agricultural uses. Buthidazole (3-[5-(l,l-dimethyl- Inhibition of photosynthesis appears to be involved in the action of 1,3,4-thiadiazolyl herbicides. Buthidazole inhibited corn photosynthesis in vivo following either pre-or postemergence application (8). Prevention of starch accumulation in bundle sheath chloroplasts and some ultrastructural disruption of mesophyl chloroplasts of corn plants treated with buthidazole applied postemergence were also observed in the previous study (8). Phytotoxicity symptoms suggested that inhibition of photosynthesis is also the mode of action of tebuthiuron (1).Interference with photoinduced electron transport and coupled phosphorylation reactions mediated by isolated chloroplasts has been studied extensively (12) and used as a means to explain the mechanism of action of many structurally diverse herbicides known to act as photosynthetic inhibitors (7). Electron transport and photophosphorylation were found to be inhibited by 1,2,4-and 1,3,4-thiadiazole derivatives in assays with isolated chloroplasts (5,15,17). The purpose of this study was to examine the effects of buthidazole and tebuthiuron on the electron transport chain of isolated spinach chloroplasts and to locate the site of the inhibition by segmenting the photosynthetic electron transport pathway. MATERIALS AND METHODSChloroplast Isolation. Chloroplasts were isolated from commercial spinach (Spinacia oleracea L.) obtained from a local market. Leaves were washed with cold distilled H20 and ground in a Waring Blendor for 5 s in a medium containing 0.3 M NaCl, 30 mM Tricine-NaOH (pH 7.8), 3 mm MgCl2, and 0.5 mm EDTA. The homogenate was filtered through eight layers of cheesecloth and the chloroplasts were sedimented at 2,500g for 2 min. The chlor...

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Section: Micromolar Inhibition Of Pbotosystem I-mediated Transfer Ofmentioning

confidence: 99%

Inhibition of Photosynthetic Electron Transport in Isolated Spinach Chloroplasts by Two 1,3,4-Thiadiazolyl Derivatives

Hatzios¹,

Penner²,

Bell³

1980

Plant Physiol.

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“…Several studies have shown that two or three heterogeneous atoms such as nitrogen and sulfur are expected to have antimicrobial activities . In addition, many 1,3,4‐thiadiazoles are used as fungicides, bactericides, and herbicides in the agricultural field . Acid hydrazides are reactive substances and have been used as useful synthons of various heterocyclic rings with one or several heteroatoms.…”

Section: Introductionmentioning

confidence: 99%

New 1,3,4‐Thiadiazole Derivatives: Synthesis, Characterization, and Antimicrobial Activity

Abo‐Bakr

Hashem

2019

Journal of Heterocyclic Chem

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In the present study, 2,5‐bis(mercapto‐acetichydrazide)‐1,3,4‐thiadiazole (1) was utilized by different reagents, namely, ethoxymethylene malononitrile, ethoxymethylene ethyl cyanoacetate, triethyl orthoformate, phenyl isothiocyanate, carbon disulfide, isatin, acetophenone, cyclohexanone, different aldehydes, and different anhydrides, to yield a new series of 2,5‐disubstituted‐1,3,4‐thiadiazoles 2–18. The chemical structure of these products was characterized by the spectral data IR, 1H‐NMR, 13C‐NMR, MS, and elemental analysis. All the synthesized compounds were screened for their antibacterial activity.

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“…As one of important five-membered heterocyclic chemical nematicides, fluensulfone has been put on the market successfully with broad spectrum of nematicidal activities, and tioxazafen has been served as seed treatment and plays a crucial part of the protection of vegetables and fruits. [17,18] Meanwhile, 1,3,4-oxadiazole/thiadiazole are two known important class of five-membered heterocyclic active groups, with high efficiency and broad spectrum of biological activities, such as insecticidal, [19,20] antifungal, [21,22] herbicidal, [23] and anticancer activities. [24] The novel 1,3,4-oxadiazole/thiadiazole thioether derivatives containing trifluorobuten moiety with good nematicidal activities have been reported in our previous work, [25] and we found that some 1,3,4-oxadiazole/thiadiazole derivatives showed good inhibitory activities against Caenorhabditis elegans, but the featureless activity was exhibited against T. semipenetrans.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Nematicidal Activity, and 3D‐QSAR of Novel 1,3,4‐Oxadiazole/ Thiadiazole Thioether Derivatives

Chen

Gan

et al. 2018

Chin. J. Chem.

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Forty one novel 1,3,4‐oxadiazole/thiadiazole thioether derivatives containing phenoxy moiety were designed and synthesized. Bioassay demonstrated that some of them showed remarkable activities against Tylenchulus semipenetrans in vitro and in vivo. Compounds 20, 21, 35 and 39 showed excellent lethal activities after treatment for 48 h in vitro, with LC50 values of 13.4 ± 1.8, 11.7 ± 2.5, 13.7 ± 2.4 and 13.3 ± 1.1 mg·L–1, respectively, which were obviously superior to fosthiazate (49.1 ± 2.8 mg·L–1) and avermectin (26.6 ± 2.3 mg·L–1). Compound 21 can effectively control the citrus nematode disease caused by T. semipenetrans at 200 mg·L–1 in vivo with (68 ± 3)% inhibitory effect, which was even better than that of avermectin ((63 ± 2)%). The CoMFA and CoMSIA models of three‐dimensional quantitative structure‐activity relationships (3D‐QSARs) were established. The compound 33 was designed based on the 3D‐QSAR models with more vigorous nematicidal activities in vitro (LC50 = 9.8 ± 1.4 mg·L–1) and in vivo ((70 ± 5)%). These results demonstrated that compound 33 can be considered as a potential nematicide.

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Herbicidal activity of 1,3,4-thiadiazole derivatives

Cited by 35 publications

References 3 publications

Inhibition of Photosynthetic Electron Transport in Isolated Spinach Chloroplasts by Two 1,3,4-Thiadiazolyl Derivatives

Inhibition of Photosynthetic Electron Transport in Isolated Spinach Chloroplasts by Two 1,3,4-Thiadiazolyl Derivatives

New 1,3,4‐Thiadiazole Derivatives: Synthesis, Characterization, and Antimicrobial Activity

Synthesis, Nematicidal Activity, and 3D‐QSAR of Novel 1,3,4‐Oxadiazole/ Thiadiazole Thioether Derivatives

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