Fungitoxic derivatives of salicylaldehyde. II. Chlorinated and brominated derivatives of salicylideneaniline and related compounds as eradicants of cucumber powdery mildew was written by Smith, R. J.;Read, W. H.. And the article was included in Annals of Applied Biology in 1961.Safety of 3-Chloro-2-hydroxy-5-methylbenzaldehyde The following contents are mentioned in the article:
Halogenated derivatives of salicylideneaniline were prepared by condensation between salicylaldehyde. or its appropriate derivative, and aniline, or the appropriate monochlorinated aniline, in warm EtOH. The most promising compounds for eradicating Erysiphe cichoracearum were 3-bromo- and 3-chlorosalicylideneaniline. Although more effective at 0.08-0.10% than Karathane sprays on a com. scale, these compounds showed phytotoxic effects on mature cucumber plants. Their toxicity to certain other fungi was also reported. The salicylidene substituents, aniline substituents, derivative, crystalline form, recrystallization solvent, and m.p. were given: 3-Cl, -, pale orange needles, EtOH (I), 59.5-60.0°; 3-Cl, 2-Cl, golden yellow needles, 80% I, 142.0-2.5°; 3-Cl, 3-Cl, deep-yellow prisms, 80% I, 104°; 3-Cl, 4-Cl, orange prisms, I, 108-9° 4-Cl, -, deep-yellow needles, 80% I, 69.5°; 5-Cl, -, orange needles, I, 109.0-9.5°; 5-Cl, 4-Cl, deep-yellow platelets, AcOH-C6H6-ligroine, 147-8°; 3,5-Cl2, -, orange, I, 102-3°; 3,5-Cl2, 4-Cl, red-orange needles, 90% AcOH, 139-40°; 3,5-ClMe, -, tangerine needles, 90% I, 51.0-2.5°; 3-Br, -, orange needles, 80% I, 70.5°; 3,5-BrCl, -, deep-orange, I, 86-7°; 3,5-Br2, -, orange-red needles, 95% I, 90.0-90.5°; 3,5-BrMe, -, orange needles, 95% I, 62° (softening at 60°); 3-Cl (Cu compound) -, -, -, 198-200°; 3-MeO, -, orange-red needles or prisms, 75% I, 84.0-4.5°. The following aniline derivatives were also prepared (same data given): 2-hydroxynaphthylideneaniline, golden-yellow needles, 70% I, 93.0-3.5°; 3-chloro-4-hydroxybenzylideneaniline, glistening yellow-ochre needles, 50% I, 167-8°; benzylidene-4-chloro-2-hydroxyaniline silver plates, 50% I, 108°. This study involved multiple reactions and reactants, such as 3-Chloro-2-hydroxy-5-methylbenzaldehyde (cas: 89938-53-4Safety of 3-Chloro-2-hydroxy-5-methylbenzaldehyde).
3-Chloro-2-hydroxy-5-methylbenzaldehyde (cas: 89938-53-4) belongs to organic chlorides. Chlorinated organic compounds are found in nearly every class of biomolecules and natural products including alkaloids, terpenes, amino acids, flavonoids, steroids, and fatty acids. The haloform reaction, using chlorine and sodium hydroxide, is also able to generate alkyl halides from methyl ketones, and related compounds. Chloroform was formerly produced thus.Safety of 3-Chloro-2-hydroxy-5-methylbenzaldehyde
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics