Month: October 2022

Lambert, William T.; Buysse, Ann M.; Wessels, Frank J. published the artcile< Discovery of novel insecticidal 3-aminopyridyl ureas>, Name: Pyridazin-4-amine, the main research area is aminopyridyl urea insecticidal synthesis activity; Bemisia tabaci; Myzus persicae; agrochemical discovery; commercial compounds; insecticidal spectrum; insecticide discovery; structure-activity relationship (SAR); urea.

Com. compound databases represent rich sources of potential starting points for pharmaceutical and agrochem. product development. Routine insecticidal screening of compounds ordered from these sources led to the identification of a 3-aminopyridyl urea with activity against Myzus persicae (Sulzer) (green peach aphid). Based on this activity and its structural novelty, further exploration of the chem. space around this hit was initiated. A series of ureas based on the structure of the initial hit were synthesized and screened for insecticidal activity. A broad range of tail groups derived from cyclic secondary amines were explored, and many of these compounds were found to be insecticidally active. However, only compounds featuring a 3-aminopyridine or 4-aminopyridazine head group exhibited significant insecticidal potency. Although activity against M. persicae was consistently observed, these ureas were largely inactive against another key sap-feeding insect pest, Bemisia tabaci (Glennadius) (sweetpotato whitefly). Follow-up of an insecticide hit identified from com. compound acquisition led to the discovery of a novel class of ureas with activity against M. persicae. Despite considerable effort to identify related compounds with addnl. insecticidal spectrum, however, activity on other important pests remains limited.

Pest Management Science published new progress about Bemisia tabaci. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Name: Pyridazin-4-amine.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Dong, Jianyang; Yue, Fuyang; Xu, Wentao; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin published the artcile< Visible-light-mediated Minisci C-H alkylation of heteroarenes with 4-alkyl-1,4-dihydropyridines using O2 as an oxidant>, Computed Properties of 64067-99-8, the main research area is alkylated heteroarene green preparation; heteroarene alkyl dihydropyridine alkylation iridium photocatalyst.

A protocol for direct visible-light-mediated Minisci C-H alkylation reactions of N-heteroarenes with 4-alkyl-1,4-dihydropyridines for synthesis of alkylated N-heteroarenes such as I at room temperature with mol. oxygen as an oxidant was reported. The protocol permitted efficient functionalization of various N-heteroarenes with a broad range of cyclic and acyclic primary, secondary and tertiary alkyl groups and was scalable to the gram level. This mild protocol used an inexpensive, green oxidant and was suitable for late-stage C-H alkylation of complex nitrogen-containing mols. Its utility was demonstrated by preparing or functionalizing several pharmaceuticals and natural products.

Green Chemistry published new progress about Dihydropyridines Role: RCT (Reactant), RACT (Reactant or Reagent). 64067-99-8 belongs to class pyridazine, and the molecular formula is C9H8ClN3O2, Computed Properties of 64067-99-8.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Moriya, Koichi; Shibuya, Katsuhiko; Hattori, Yumi; Tsuboi, Shinichi; Shiokawa, Kozo; Kagabu, Shinzo published the artcile< Imidacloprid and analogous insecticides. IV. 1-Diazinylmethyl-2-nitromethylene- and 2-nitroimino-imidazolidines as new potential insecticides>, Synthetic Route of 120276-59-7, the main research area is diazinylmethyl imidazolidine insecticide.

Eight 1-diazinylmethylimidazolidines were prepared and their insecticidal activities were studied. 1-(2-Chloro-5-pyrimidinyl)methyl-2-(nitroimino)imidazolidine (I) was as effective as imidacloprid against green rice leafhoppers on rice seedlings in spray applications. Seven 1-(diazinylmethyl)-2-(nitromethylene)imidazolidines with or without a Cl or Me substituent on the diazine ring were less effective than I.

Nippon Noyaku Gakkaishi published new progress about Insecticides. 120276-59-7 belongs to class pyridazine, and the molecular formula is C5H4Cl2N2, Synthetic Route of 120276-59-7.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Barlin, Gordon B. published the artcile< Methylation of aminopyridazines>, HPLC of Formula: 20744-39-2, the main research area is methylation aminopyridazine; pyridazine amino methylation; aminopyridazinium iodide UV NMR; acidity aminopyridazine.

Treatment of 3- and 4-amino- and 3,5-diaminopyridazine with MeI in MeOH gave mixtures of the corresponding 1- and 2-methyl iodides whereas 3,4-, 3,6-, and 4,5-diaminopyridazines gave only one methiodide, in the first case identified as 3,4-diamino-1-methylpyridazinium iodide. No ammonio compounds were detected. The ionization constants and uv and PMR spectra of the pyridazines, their methiodides, and related compounds were determined and discussed.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about Acidity. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, HPLC of Formula: 20744-39-2.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Deyrup, J. A.; Gingrich, H. L. published the artcile< Cycloadditions of 4-oxazolin-2-ones>, Product Details of C4H5N3, the main research area is oxazolinone cycloaddition cyclopentadiene anthracene; chloranil cycloaddition oxazolinone; tetrazine pyridyl cycloaddition oxazolinone.

The 4-oxazolin-2-ones I (R = H, Ac, R1 = H; R = Ac, R1 = Ph) underwent cycloaddition reactions with a variety of cyclic unsaturated compounds, e.g. cyclopentadiene, o-chloranil, anthracene. E.g., I (R = Ac, R1 = H) with anthracene in o-xylene at 144° for 72 h gave 87% adduct II. Hydrolysis of II in refluxing alc. aqueous NaOH gave 74% amino alc. III.

Tetrahedron Letters published new progress about Cycloaddition reaction. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Product Details of C4H5N3.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Qu, Ren-Yu; Nan, Jia-Xu; Yan, Yao-Chao; Chen, Qiong; Ndikuryayo, Ferdinand; Wei, Xue-Fang; Yang, Wen-Chao; Lin, Hong-Yan; Yang, Guang-Fu published the artcile< Structure-Guided Discovery of Silicon-Containing Subnanomolar Inhibitor of Hydroxyphenylpyruvate Dioxygenase as a Potential Herbicide>, Application of C4H5N3, the main research area is triketonequinazolinedione preparation hydroxyphenylpyruvate dioxygenase inhibitor herbicide; crop safety weed control wheat peanut MBQ derivative; 4-dione; herbicide; hydrophobic interaction; hydroxyphenylpyruvate dioxygenase; lead optimization; quinazoline-2.

4-Hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) has been recognized as one of the most promising targets in the field of herbicide innovation considering the severity of weed resistance currently. In a persistent effort to develop effective HPPD-inhibiting herbicides, a structure-guided strategy was carried out to perform the structural optimization for triketone-quinazoline-2,4-diones, a novel HPPD inhibitor scaffold first discovered in our laboratory Herein, starting from the crystal structure of Arabidopsis thaliana (At)HPPD complexed with 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-(o-tolyl)quinazoline-2,4(1H,3H)-dione (MBQ), three subseries of quinazoline-2,4-dione derivatives were designed and prepared by optimizing the hydrophobic interactions between the side chain of the core structure at the R1 position and the hydrophobic pocket at the active site entrance of AtHPPD. 6-(2-Hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-(3-(trimethylsilyl)prop-2-yn-1-yl)quinazoline-2,4(1H,3H)-dione (I) with the best inhibitory activity against AtHPPD was identified to be the first subnanomolar-range AtHPPD inhibitor (Ki = 0.86 nM), which significantly outperformed that of the lead compound MBQ (Ki = 8.2 nM). Further determination of the crystal structure of AtHPPD in complex with compound 60 (1.85 Å) and the binding energy calculation provided a mol. basis for the understanding of its high efficiency. Addnl., the greenhouse assay indicated that 6-(2-hydroxy-6-oxocyclohex-1-ene-1-carbonyl)-1,5-dimethyl-3-propylquinazoline-2,4(1H,3H)-dione (II) and compound I showed acceptable crop safety against peanut and good herbicidal activity with a broad spectrum. Moreover, compound II also showed superior selectivity for wheat at the dosage of 120 g ai/ha and favorable herbicidal efficacy toward the gramineous weeds at the dosage of as low as 30 g ai/ha. We believe that compounds II and I have promising prospects as new herbicide candidates for wheat and peanut fields.

Journal of Agricultural and Food Chemistry published new progress about Abutilon theophrasti. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Application of C4H5N3.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Yamagami, Chisako; Takao, Narao; Fujita, Toshio published the artcile< Hydrophobicity parameter of diazines. 1. Analysis and prediction of partition coefficients of monosubstituted diazines>, Synthetic Route of 20744-39-2, the main research area is hydrophobicity diazine LFER; partition coefficient diazine.

The octanol/water partition coefficient (P) of a number of monosubstituted diazines was measured. The composition of the π value of substituents, the increment in the log P value accompanying the introduction of substituents, was examined in terms of physicochem. substituent parameters and correlation anal. The diazine-π value of substituents was generally higher than the pyridine-π value of corresponding substituents, indicating that the intramol. electronic interactions between the ring-N atoms and substituent are more pronounced than those in substituted pyridines in governing the log P value of the mol. Except for 2-substituted pyrimidines, the π value of substituents in each series of monosubstituted diazines was in general nicely correlated with the π value of the corresponding substituents in substituted pyridines along with electronic parameter terms representing bidirectional electronic effects on the relative solvation of the ring-N atom(s) and the hydrogen-bondable substituents with partitioning solvents according to the procedure proposed previously for the anal. of the π value in disubstituted benzenes and monosubstituted pyridines. Keeping in mind that 2-pyrimidines substituted by hydrogen-bondable groups sometimes behave as outliers, the correlations were believed to be usable for prediction of log P values of monosubstituted diazines.

Quantitative Structure-Activity Relationships published new progress about Hydrophobicity. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Synthetic Route of 20744-39-2.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Burton, Rebecca J.; Crowther, Mandy L.; Fazakerley, Neal J.; Fillery, Shaun M.; Hayter, Barry M.; Kettle, Jason G.; McMillan, Caroline A.; Perkins, Paula; Robins, Peter; Smith, Peter M.; Williams, Emma J.; Wrigley, Gail L. published the artcile< Highly regioselective Buchwald-Hartwig amination at C-2 of 2,4-dichloropyridine enabling a novel approach to 2,4-bisanilinopyridine (BAPyd) libraries>, Application of C4H5N3, the main research area is Buchwald Hartwig amination dichloropyridine bisanilinopyridine library.

The highly regioselective Buchwald-Hartwig amination at C-2 of the cheap and readily accessible reagent, 2,4-dichloropyridine with a range of anilines and heterocyclic amines is described. This new methodol. is robust and provides a facile access to 4-chloro-N-phenylpyridin-2-amines on 0.25 mol scale. These intermediates undergo a further Buchwald-Hartwig amination at higher temperature to enable rapid exploration of the chem. space at C-4 and to provide a library of 2,4-bisaminopyridines.

Tetrahedron Letters published new progress about Buchwald-Hartwig reaction. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Application of C4H5N3.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Tolmachova, Kateryna A.; Moroz, Yurii S.; Konovets, Angelika; Platonov, Maxim O.; Vasylchenko, Oleksandr V.; Borysko, Petro; Zozulya, Sergey; Gryniukova, Anastasia; Bogolubsky, Andrey V.; Pipko, Sergey; Mykhailiuk, Pavel K.; Brovarets, Volodymyr S.; Grygorenko, Oleksandr O. published the artcile< (Chlorosulfonyl)benzenesulfonyl Fluorides-Versatile Building Blocks for Combinatorial Chemistry: Design, Synthesis and Evaluation of a Covalent Inhibitor Library>, Product Details of C4H5N3, the main research area is chlorosulfonylbenzenesulfonyl fluoride preparation building block combinatorial chem; parallel synthesis trypsin inhibitor library preparation bioactivity evaluation; chemoselectivity; covalent fragments; parallel synthesis; serine protease inhibitors; sulfonamides; sulfonyl halides.

Multigram synthesis of (chlorosulfonyl)benzenesulfonyl fluorides is described. Selective modification of these building blocks at the sulfonyl chloride function under parallel synthesis conditions is achieved. It is shown that the reaction scope includes the use of (hetero)aromatic and electron-poor aliphatic amines (e.g., amino nitriles). Utility of the method is demonstrated by preparation of the sulfonyl fluoride library for potential use as covalent fragments, which is demonstrated by a combination of in silico and in vitro screening against trypsin as a model enzyme. As a result, several inhibitors were identified with activity on par with that of the known inhibitor.

ACS Combinatorial Science published new progress about Chemoselectivity. 20744-39-2 belongs to class pyridazine, and the molecular formula is C4H5N3, Product Details of C4H5N3.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem

Zhao, Hong; Jin, Jian published the artcile< Visible Light-Promoted Aliphatic C-H Arylation Using Selectfluor as a Hydrogen Atom Transfer Reagent>, COA of Formula: C9H8ClN3O2, the main research area is alkane heteroarene selectfluor hydrogen atom transfer light arylation; heteroaryl alkyl derivative preparation.

A mild, practical method for direct arylation of unactivated C(sp3)-H bonds with heteroarenes has been achieved via photochem. Selectfluor is used as a hydrogen atom transfer reagent under visible light irradiation A diverse range of chem. feedstocks, such as alkanes, ketones, esters, and ethers, and complex mols. readily undergo intermol. C(sp3)-C(sp2) bond formation. Moreover, a broad array of heteroarenes, including pharmaceutically useful scaffolds, can be alkylated effectively by the protocol presented here.

Organic Letters published new progress about Alkanes Role: RCT (Reactant), RACT (Reactant or Reagent). 64067-99-8 belongs to class pyridazine, and the molecular formula is C9H8ClN3O2, COA of Formula: C9H8ClN3O2.

Referemce:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem