Search

Quantitative Structure Activity Relationship (QSAR) model on a series of triazolinone derivatives acting as angiotensin II receptor using partial least squares regression analysis was performed to compute the relationship with 2D structure descriptors. The computational studies were performed with trial version V-life Molecular Design Suite software. The developed models were validated using an internal predic- tive power and predictivity for the external test set of 0.8653, and 0.7981 were obtained. The F test value shows the overall statistical significance level. Models developed in this study have potential application in the prediction of binding affinity for the newly synthesized compounds. [ABSTRACT FROM AUTHOR]

Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) catalyzes the oxidation of protoporphyrinogen IX to protoporphyrin IX, which is a key step in the synthesis of porphyrins in vivo. PPO inhibitors use protoporphyrinogen oxidase as the target and block the biosynthesis process of porphyrin by inhibiting the activity of the enzyme, eventually leading to plant death. In this paper, phenyl triazolinone was used as the parent structure, and the five-membered heterocycle with good herbicidal activity was introduced by using the principle of substructure splicing. According to the principle of bioisosterism, the sulfur atoms on the thiophene ring were replaced with oxygen atoms. Finally, 33 phenyl triazolinones and their derivatives were designed and synthesized, and their characterizations and biological activities were investigated. The in vitro PPO inhibitory activity and greenhouse herbicidal activity of 33 target compounds were determined, and compound D4 with better activity was screened out. The crop safety determination, field weeding effect determination, weeding spectrum determination, and crop metabolism study were carried out. The results showed that compound D4 showed good safety to corn, soybean, wheat, and peanut but poor selectivity to cotton. The field weeding effect of this compound is comparable to that of the commercial herbicide sulfentrazone. The herbicidal spectrum experiment showed that compound D4 had a wide herbicidal spectrum and a good growth inhibition effect on dicotyledonous weeds. Molecular docking results showed that compound D4 forms a hydrogen bond with amino acid residue Arg-98 in the tobacco mitochondria ( mt PPO)-active pocket and forms two π-π stacking interactions with Phe-392. This indicates that compound D4 has stronger PPO inhibitory activity. This indicates that compound D4 has wide prospects for development.

Hokko Chemical Industry Co., Ltd. found a novel triazolinone class herbicide regarded as 1-aryl-4-carbamoyl-1,2,4-triazolinone derivatives that shows high level of safety to paddy rice, and high activity and long residual activity against Echinochloa spp. and other weeds. We selected a new paddy rice herbicide ipfencarbazone as the optimum compound. Ipfencarbazone is a pre-emergence and early post-emergence rice herbicide that controls annual grass weeds, annual sedge weeds and some annual broadleaf weeds at a rate of 250 g a.i./ha. It inhibits the biosynthesis of fatty acids in plants (VLCFA). Two formulations con- taining ipfencarbazone, Winner® and Fighter®, have been registered in Japan since 2013 and various combinations have been launched. [ABSTRACT FROM AUTHOR]

The herbicide carfentrazone-ethyl ( 1) was prepared by a new and improved synthetic method. The common and inexpensive reagent ethyl acrylate was employed to replace commercially unavailable ethyl 3-hydroxy-2-methylenebutanoate, which was used in the synthetic route reported previously. Starting from iodination of 1-(4-chloro-2-fluorophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1 H-1,2,4-triazole ( 2), an intermediate 1-(4-chloro-2-fluoro-5-iodophenyl)-4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1 H-1,2,4-triazole ( 3) was afforded in an excellent yield. Then, an intermediate ethyl 3-[2-chloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1 H-1,2,4-triazol-1-yl)-4-fluorophenyl]-2-propenoate ( 4) was synthesized by Heck coupling of 3 with ethyl acrylate. Next, oxidative addition-elimination of 4 with OXONE/HCl-EtN in one pot produced ethyl 2-chloro-3-[2-chloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1 H-1,2,4-triazol-1-yl)-4-fluorophenyl]-2-propenoate ( 5). Finally, the target product 1 was obtained via reduction of 5 by H. This new synthetic method exhibits the advantages of mild conditions, atom economy, low-cost, and efficiency. [ABSTRACT FROM AUTHOR]

Abstract: The optimization of a novel series of non-nucleoside reverse transcriptase inhibitors (NNRTI) led to the identification of pyridone 36. In cell cultures, this new NNRTI shows a superior potency profile against a range of wild type and clinically relevant, resistant mutant HIV viruses. The overall favorable preclinical pharmacokinetic profile of 36 led to the prediction of a once daily low dose regimen in human. NNRTI 36, now known as MK-1439, is currently in clinical development for the treatment of HIV infection. [Copyright &y& Elsevier]

According to Article 12 of Regulation (EC) No 396/2005, the European Food Safety Authority (EFSA) has reviewed the Maximum Residue Levels (MRLs) currently established at European level for the pesticide active substance carfentrazone-ethyl. In order to assess the occurrence of carfentrazone-ethyl residues in plants, processed commodities, rotational crops and livestock, EFSA considered the conclusions derived in the framework of Directive 91/414/EEC as well as the European authorisations reported by Member States (incl. the supporting residues data). Based on the assessment of the available data, MRL proposals were derived and a consumer risk assessment was carried out. Although no apparent risk to consumers was identified, some information required by the regulatory framework was found to be missing. Hence, the consumer risk assessment is considered indicative only and all MRL proposals derived by EFSA still require further consideration by risk managers.

A series of novel triazolinones were synthesized and their structures were characterized by 1H NMR, elemental analysis and single-crystal X-ray diffraction analysis. The herbicidal activities were evaluated against Echinochloa crusgalli (L.) Beauv., Digitaria adscendens, Brassica napus and Amaranthus retroflexus. The herbicidal activity data indicated that the title compounds had higher activities with substituted benzyl group moieties than with other groups such as sulfonyl, alkyl, etc. To further investigate the structure–activity relationship, comparative molecular field analysis was performed on the basis of herbicidal activity data. Both the steric and electronic field distributions of comparative molecular field analysis are in good agreement in this work. The results showed that a bulky and electronegative group around the ortho- or para-positions of the benzene ring would possibly lead to higher activity. Based on the comparative molecular field analysis, compound I-23 was designed and synthesized, which display as good herbicidal activities as the commercial herbicide, carfentrazone-ethyl. The activity against Digitaria adscendens is 66.1% under pre-emergence at 300 g of a.i./ha. [ABSTRACT FROM AUTHOR]

Sorption-desorption interactions of pesticides with soil determine the availability of pesticides in soil for transport, plant uptake and microbial degradation. These interactions are affected by the physical and chemical properties of the pesticide and soil and, for some pesticides, their residence time in the soil. While sorption-desorption of many herbicides has been characterised, very little work in this area has been done on herbicide metabolites. The objective of this study was to characterise sorption-desorption of two sulfonylaminocarbonyltriazolinone herbicides, flucarbazone and propoxycarbazone, and their benzenesulfonamide and triazolinone metabolites in two soils with different physical and chemical properties. Kf values for all four chemicals were greater in clay loam soil, which had higher organic carbon and clay contents than loamy sand. Kf-oc ranged from 29 to 119 for the herbicides and from 42 to 84 for the metabolites. Desorption was hysteretic in every case. Lower desorption in the more sorptive system might indicate that hysteresis can be attributed to irreversible binding of the molecules to soil surfaces. These data show the importance of characterisation of both sorption and desorption of herbicide residues in soil, particularly in the case of prediction of herbicide residue transport. In this case, potential transport of sulfonylaminocarbonyltriazolinone herbicide metabolites would be overpredicted if parent chemical soil sorption values were used to predict transport. [ABSTRACT FROM AUTHOR]

ABSTRACT: Sulfentrazone is a pre-emergence herbicide that inhibits protoporphyrinogen oxidase (Protox). Its use has emphasis on areas like soybeans planted in lowlands, soybean, and sugarcane in areas of cerrado, and also in the implementation of eucalyptus afforestation. The use of sulfentrazone into resistant weed management programs mainly to glyphosate and acetolactate synthase (ALS) inhibitors has been successful. However, the information on the environmental behavior of this herbicide is limited, even more restricted when it refers to the lowland areas where problems are frequently observed regarding the selectivity of sulfentrazone, due to the soil and climatic peculiarities of this environment. In this context, the present review aims to describe the main characteristics of sulfentrazone to its environmental dynamics.

Hokko Chemical Industry Co., Ltd. found a novel triazolinone class herbicide regarded as 1-aryl-4-carbamoyl-1,2,4-triazolinone derivatives that shows high level of safety to paddy rice, and high activity and long residual activity against Echinochloa spp. and other weeds. We selected a new paddy rice herbicide ipfencarbazone as the optimum compound. Ipfencarbazone is a pre-emergence and early post-emergence rice herbicide that controls annual grass weeds, annual sedge weeds and some annual broadleaf weeds at a rate of 250 g a.i./ha. It inhibits the biosynthesis of fatty acids in plants (VLCFA). Two formulations containing ipfencarbazone, Winner® and Fighter®, have been registered in Japan since 2013 and various combinations have been launched.