4-Amino(alkylamino)-5-chloro-2-substituted-3-oxo-2H-pyridazines and 5-amino(alkylamino, dialkylamino)-4-chloro-2-substituted-3-oxo-2H-pyridazines have been prepared by nucleophilic substitution reactions of 4,5-dichloro-2-substituted-3-oxo-2H-pyridazines with amines in aprotic solvent. Structure of the compounds prepared has been proved by IR and UV spectra. Fungicidal and herbicidal activity of the compounds prepared have been tested. None of the compounds prepared exceeds the standard Vitavax in the fungicidal activity tests. Compounds VIII and XII show equal or better activity on the Hill reaction as compared with the standard pyrazone.
The crystal structure was solved by direct methods and refined by the least squares method in a 9 x 9 block diagonal approximation using the anisotropic temperature parameters. The R-factor was decreased to a final value of 5.6% for 970 observed reflextions. The crystals are monoclinic with a space group of P21/c and lattice parameters of a = 1.1056(11), b = 0.8913(11), c = 1.2023(16) nm, β = 96.32°, and Z = 4. The crystal structure consists of discrete molecules between which hydrogen interactions of the N-H...O and C-H...O type were observed. The lengths of the N1-C3 (0.1432 nm) and C3-O1 (0.1203 nm) bonds and valence angles, C3-N1-C1 (119.9°), N1-C3-O1 (126.5°), indicate considerable delocalization of the π-electrons and participation of the lone electrone pair on N1 nitrogen in the conjugation in the N1-C3-O1 molecular fragment. The CNDO/2 quantum chemical method was used to calculate the electron structure. Calculation for partial optimization of the dihedral angles, φ and ω, indicated that the most stable form is obtained for the values φ = 0°, ψ = 120-150°, 240-270° and ω = 150-210°, 330-30°.
This work deals with the synthesis of dithiocarbamate chelates of Cu(II) and Zn(II) with ligands derived from dimethyl-, diethyl-, dipropyl-, dibutyl- and methylisopropylamine, piperidine and morpholine and the electronic spectra of these substances in the UV and visible regions. The absorption spectra of the cupric (and zinc(II)) chelates contain a single analytically important band around 270 (260) nm, assigned to the π-π* transition within the ligand, that is affected by the substituent on the nitrogen atom and the solvent polarity. Lengthening of the alkyl chain leads to increased intensity of the bands and a red shift of their λmax; increased solvent polarity leads to increased intensity of the bands and a blue shift.
The crystal structure of N-(2,6-dimethylphenyl)chloromaleinimide solved by the heavy atom method was refined by the 9 x 9 block-diagonal matrix least-squares method to a final R value 0.08 for 1 147 observed diffractions. The compound crystallizes in the orthorhombic system with Pbca group and lattice parameters a = 13.622(4), b = 13.483(7), c = 12.768(6) Å, Z = 8. Monomeric units, between which interactions of type Cl···H-C and O···H-C occured, formed the crystal structure. Both moieties of the molecule, i.e. the phenyl and the five-membered maleinimide rings were found to be virtually planar and the central planes intersecting these rings form an angle 78.3°.
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