Synthesis and characterization of a novel series of benzenesulfonylurea and thiourea derivatives of 2H-pyran and 2H-pyridine-2-ones as antibacterial, antimycobacterial and antifungal agents

Arylhydrazines reacted with dehydroacetic acid (1) to give the corresponding 2H-pyran-2-one hydrazones (2), which on treatment with hydrazine hydrate afforded the corresponding 1-amino-2H-pyridin-2-ones (3). Reaction of 3 with nitrous acid, aromatic aldehyde and substituted benzenesulfonyl chlorides yielded the corresponding 2H-pyridine-2-one derivatives. A series of urea and thiourea derivatives were also prepared. Some of these compounds have shown significant antibacterial and mild to moderate antimycobacterial and antifungal activities

(E)-2-Methyl-6-[(1-phenyl-1H-pyrazol-4-yl)methyl­idene]cyclo­hexa­none

The asymmetric unit of the title compound, C17H18N2O, contains two independent mol­ecules. In both, the cyclo­hexane ring adopts a flattened chair conformation, and the 3- and 4-methyl­ene C atoms as well as the methyl C atoms are disordered over two positions, the occupancy of the major component being 68 (1)% in one mol­ecule and 64 (1)% in the other. The phenyl and pyrazole rings in both mol­ecules are approximately coplanar, the r.m.s. deviations being 0.048 and 0.015 Å, respectively. Weak inter­molecular C—H⋯O hydrogen bonding is present in the crystal structure

4-{(4Z)-4-[(2Z)-3-(4-Fluoro­anilino)-1-hy­droxy­but-2-en-1-yl­idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}­benzene­sulfonamide

In the title compound, C20H19FN4O4S, the pyrazole and benzene­sulfonamide rings are coplanar [dihedral angle = 5.02 (15)°] but this planarity does not extend over the entire mol­ecule, the dihedral angle between the terminal six-membered rings being 33.24 (14)°. Intra­molecular hy­droxy–hy­droxy O—H⋯O and amine–hy­droxy N—H⋯O hydrogen bonds, as a well as a tight C—H⋯O(carbon­yl) inter­action, lead to a sequence of three fused S(6) rings. Supra­molecular chains along the a axis feature in the crystal packing; these chains are stabilized by amine–sulfonamide N—H⋯O and amine–pyrazole N—H⋯N hydrogen bonds

2-Amino-4-(3,4-dimeth­oxy­phen­yl)-5,6-dihydro­benzo[h]quinoline-3-carbo­nitrile–3-amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile (1/19)

The asymmetric unit of the 1:19 title co-crystal of 2-amino-4-(3,4-dimeth­oxy­phen­yl)-5,6-dihydro­benzo[h]quinoline-3-carbo­nitrile and 3-amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile, 0.05C22H19N3O2·0.95C24H19N3O2, has the atoms of the fused-ring system and those of the amino, cyano and dimeth­oxy­phenyl substitutents overlapped. The fused-ring system is buckled owing to the ethyl­ene linkage in the central ring with the two flanking aromatic rings being twisted by 31.9 (1)°. The ring of the dimeth­oxy­phenyl substituent is twisted by 72.4 (1)° relative to the amino- and cyano-bearing aromatic ring. In the crystal, mol­ecules are linked by duplex amine N—H⋯O(meth­oxy) hydrogen bonds in a cyclic association [graph-set R 2 2(7)], generating a helical chain structure extending along [201]

(2Z)-3-(4-Fluoro­anilino)-1-(5-hy­droxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one

The central carbonyl group in the title compound, C20H18FN3O2, forms amine–hy­droxy N—H⋯O and hy­droxy–hy­droxy O—H⋯O hydrogen bonds, leading to two S(6) rings. The N-bound phenyl ring is coplanar with the five-membered ring to which it is attached [dihedral angle = 6.27 (10)°], but an overall twist in the mol­ecule is evident, the dihedral angle between the terminal phenyl and benzene rings being 27.30 (10)°. Mol­ecules aggregate into a three-dimensional architecture via C—H⋯F, C—H⋯O and C—H⋯π inter­actions

4-(3-Methyl-5-phenyl-1H-pyrazol-1-yl)benzene­sulfonamide

With respect to the planar five-membered ring of the title compound, C16H15N3O2S, the phenyl ring is aligned at 47.0 (1)° and the phenyl­ene ring at 37.6 (1)°. The amino group has the N atom in a pyramidal geometry; the group is a hydrogen-bond donor to the sulfonyl O atom of one mol­ecule and to the pyrazole N atom of another mol­ecule, resulting in the formation of a layer parallel to the bc plane

4-[5-(Furan-2-yl)-3-trifluoro­methyl-1H-pyrazol-1-yl]benzene­sulfonamide

In the title compound, C14H10F3N3O3S, there are significant twists in the mol­ecule, as seen in the values of the dihedral angles between the pyrazole ring and each of the furan [31.1 (2)°] and benzene rings [55.58 (10)°]. The amino N atom occupies a position almost normal to the benzene ring [N—S—Car—Car (ar = aromatic) torsion angle = 83.70 (19)°]. One amino H atom forms a hydrogen bond to the tricoordinate pyrazole N atom and the other inter­acts with a sulfonamide O atom, forming a supra­molecular chain along [010]. The chains are consolidated into a supra­molecular layers via C—H⋯O inter­actions involving the second sulfonamide O atom; layers stack along [10-1]. The furan ring was found to be disordered over two diagonally opposite orientations of equal occupancy

Ethyl N-[4-(3-methyl-4,5-dihydro­benzo[g]indazol-1-yl)phenyl­sulfon­yl]thio­carbam­ate ethanol monosolvate

The title compound, C21H20N3O3S2·CH3CH2OH, comprises two independent organic mol­ecules and two ethanol solvent mol­ecules. The mol­ecules are related by pseudo-mirror symmetry. In both mol­ecules, the N-bound benzene ring is twisted out of the plane of the pyrazole ring [the dihedral angles are 51.4 (3) and 44.1 (3)°, respectively]. Similarly, the benzene ring of the 1,2-dihydro­naphthalene residue is inclined with respect to the five-membered ring [dihedral angles 18.3 (3) and 22.2 (3)°]. Overall, each mol­ecule has a flattened U shape. Dimeric aggregates mediated by O—H⋯N(pyrazole) and amide-N—H⋯O hydrogen bonds feature in the crystal packing, whereby the ethanol mol­ecules link the independent organic mol­ecules, leading to four-mol­ecule aggregates

4-(2,7-Dimethyl-4-oxo-1,3-thia­zolo[4,5-d]pyridazin-5-yl)benzene­sulfonamide

The thia­zole–pyridazine fused-ring system of the title compound, C13H12N4O3S2, is approximately planar (r.m.s. deviation = 0.037 Å); the benzene ring connected to the fused-ring system through the N atom is twisted by 39.3 (1)°. The amine group uses an H atom to form a hydrogen bond to the ketonic O atom of an inversion-related mol­ecule to generate a dimer; adjacent dimers are linked by an N—H⋯O hydrogen bond to form a linear chain

Introduction to 3d printing: techniques, materials and agricultural applications

The Production of complex products is easily possible with the help of additive manufacturing. By using additive manufacturing products may be mass-produced. Compared to traditional subtractive manufacturing, Additive manufacturing is advantageous in short design cycles, suitable for manufacturing complex structures, and high material utilization. Polymers and composites are frequently used in AM technologies, which have evolved into a variety of industrial and emerging applications. Among the many materials currently used in 3D printing are ceramics, metals, polymers, and concrete. ABS and PLA thermoplastics are the most often used materials for agricultural 3D printing since they are easy to print and relatively cheap. This article provides an overview of 3D printing technologies, materials, and applications in agriculture