Synthesis and fungitoxic activity of 5-aryl-1-formyl-4,5-dihydro-3-(2- hydroxyphenyl)-1H-pyrazoles and their complexes

Pest Management Science

Volumn 56, Issue 3, 2000, Pages 284-288

  Singh, Nisha ^a   Sangwan, Naresh K ^a   Dhindsa, Kuldip S ^a  

^a CCS HARYANA AGRICULTURAL UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

FUNGICIDE; PYRAZOLE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; COMPLEX FORMATION; CYCLIZATION; FUNGUS; INFRARED SPECTROSCOPY; MOLECULAR WEIGHT; NONHUMAN; REACTION ANALYSIS; SYNTHESIS;

EID: 0034093606     PISSN: 1526498X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1526-4998(200003)56:3<284::AID-PS128>3.0.CO;2-M     Document Type: Article

References (34)

1. Sengupta AK, Gupta MM and Gupta AA, Synthesis and in vitro antibacterial activity of substituted phenoxyacetic acid hydrazides. J Indian Chem Soc. 61:643-644 (1984).
2. Malik MS, Pal V, Sangwan NK, Dhindsa KS, Verma KK and Bhatti DS, Nematicidal efficacy of substituted phenols, phenoxyacetic acid esters and hydrazides: A structure-activity relationship study. Nematologica 35:366-370 (1989).
3. Sangwan NK, Verma BS and Dhindsa KS, 2,4-bis(Substituted cinnamoyl/pyrazol-3-yl)phenoxyacetic acid esters and hydrazides as potential antimicrobial agents. Indian J Chem 25B:672-674 (1986).
4. Malhotra R, Malik MS, Singh JP and Dhindsa KS, Synthesis, characterization, and antimicrobial activity of α-methyl-(2-thiophenomethylene)aryloxyacetic acid hydrazides and their metal complexes. J Inorg Biochem 45:269-275 (1992).
5. Malhotra R, Kumar S and Dhindsa KS, Ligational behavior of substituted acid hydrazides towards transition metals and potentiation of their microbiocidal activity. Proc Nat Acad Sci India 64A:21-28 (1994).
6. Frigola J, Colombo A, Pares J, Martinez L, Sagarra R and Roser R, Synthesis, structure and inhibitory effects on cyclooxygenase, thromboxane synthetase and platelet aggregation of 3-amino-4,5-dihydro-1H-pyrazole derivatives. Eur J Med Chem 24:435-445 (1989).
7. Kornis G, Pyrazoles, pyrazolines, pyrazolones, in Encyclopedia of Chemical Technology, 3rd edn, Vol 19, John Wiley & Sons, New York, pp 436-453 (1982).
8. Mishriky N, Asaad FM, Ibrahim YA and Girgis AS, New 2-pyrazolines of anticipated molluscicidal activity. Indian J Chem 35B:935-940 (1996).
9. Ead HA, Hassaneen HM, Abdallah MA and Mousa HAH, Synthesis and biological activities of some pyrolopyrazoles and 2-pyrazolines. Arch Pharm 324:35-37 (1991).
10. Sangwan NK, Verma BS and Dhindsa KS, Synthesis and antifungal activity of 1,3-bis[2 or 4-(substituted cinnamoyl or 1-acyl-4,5-dihydro-5-substituted phenyl-1H-pyrazol-3-yl)-phenoxy]-2-propanois and related compounds. Indian J Chem 31B:590-594 (1992).
11. Rowberg KA, Even M, Martin E and Hopfinger AJ, QSAR and molecular shape analysis of three series of 1-(phenylcarbamoyl)-2-pyrazoline insecticides. J Agric Food Chem 42:374-380 (1994).
12. Nishimura K, Tada T, Shimizu R and Ohoka A, Effects of alkyl groups attached to the carbamoyl nitrogen atom of N-arylcarbamoylpyrazolines on insecticidal activity. Pestic Sci 55:446-451 (1999).
13. Hasan R, Nishimura K, Okada M, Akamatsu M, Inoue M, Veno T and Taga T, Stereochemical basis for insecticidal activity of carbamoylated and acylated pyrazolines. Pestic Sci 46:105-112 (1996).
14. Eusen JHH, Thus JLG, Wellinga K and Stork B, 2-Pyrazolines with herbicidal activity. Pestic Sci 29:101-108 (1990).
15. Tomlin CDS (ed). The Pesticide Manual, 11th edn, British Crop Protection Council, Farnham, Surrey, UK. pp 781-782 (1997).
16. Sangwan NK and Rastogi SN, Studies in antifertility agents: Part XXXII -Synthesis and stereochemistry of 3,3a-trans and cis-2(H)-acetyl-3-aryl-3,3a-dihydropyrazolo[4,3-c][2H]chromenes, pyrazolo[3,4-a]benzocycloalk-1-enes and 3,3a-trans and cis-2(H)-acetyl-3-aryl-8-methoxy-5-tosyl-3,3a,4,5-tetrahydropyrazolo[4,3-c] quinolines. Indian J Chem 208:135-139 (1981).
17. Singh N, Sangwan NK and Dhindsa KS, Synthesis of novel coordination compounds of 5-aryl-4,5-dihydro-3-(2-hydroxyphenyl)pyrazoles as potential fungicides. Synth React Inorg Metal-Org Chem 29:673-685 (1999).
18. Batra T, Singh RV, Sangwan NK, Malik MS and Malik OP, Studies on pesticides based on coumarin IV: Synthesis and antifungal activity of twelve (4-substituted phenoxy)methyl-6-methyl coumarins. Pestic Sci 25:53-58 (1989).
19. Sangwan NK, Verma BS, Verma KK and Dhindsa KS, Nematicidal activity of essential plant oils. Pestic Sci 28:331-335 (1990).
20. Sangwan NK, Dhindsa KS, Malik OP and Malik MS, 1-Acyl-3-(mono/disubstituted phenyl)-4-(H or methyl)-5-aryl-4,5-dihydropyrazoles as potential antimicrobial agents. Chim Acta Turc 11:65-72 (1983).
21. 1H NMR chemical shifts to differentiate diastereoisomeric [1]benzopyrano[4,3-c]pyrazoles, pyrazolo[4,3-c]quinolines, and related compounds. J Chem Res (S), pp 22-23 (1987).
22. Elguero J and Fruchier A, NMR studies in the heterocyclic series. Part 33. Proton NMR spectra of 2-pyrazolines. J Chem Res (S), pp 200-201 (1990).
23. Natarajan C and Tharmaraj P, Synthesis and characterization of copper(II), nickel(II), cobalt(II) and zinc(II) complexes of 3-(1-hydroxy-2-naphthyl)-5-(4-X-phenyl)pyrazoles. Indian J Chem 29A:666-669 (1990).
24. Natarajan C and Tharmaraj P, Synthesis and characterization of copper(II), nickel(II), cobalt(II) complexes of 3-(2-hydroxyphenyl)-5-(4-x-phenyl)pyrazoles. Indian J Chem 30A:722-723 (1991).
25. Pin Y and Xiaoping Z, Synthesis and characterization of new chromium (III) vanadium(IV) and titanium(III) complexes with biologically active isonicotinic acid hydrazide. J Inorg Biochem 37:61-68 (1989).
26. Nakamoto K, Infrared Spectra of Inorganic and Coordination Compounds, Wiley Interscience, New York (1970).
27. Greenwood NN and Earnshaw A, Chemistry of the Elements, Pergamon Press, New York (1989).
28. Meek DW, Drago RS and Piper TS, Spectrochemical studies of dimethyl sulfoxide, tetramethylene sulfoxide, and pyridine N-oxide as ligands with nickel (II), chromium (III), and cobalt(II). Inorg Chem 1:285-289 (1962).
29. Rao NR, Rao PV, Reddy GV and Ganorkar MC, Metal chelates of new physiologically active O:N:S tridentate Schiff's bases. Indian J Chem 26A:887-890 (1987).
30. Patel MM, Patel HR and Patel KC, Synthesis, structural studies and antimicrobial activities of some useful complexes derived from 7-(α-phenyl-α-o/m-chloroanilinomethyl)-8-quinolinol. J Indian Chem Soc 74:1-4 (1997).
31. Shriver DF, Atkin PW and Langfold CK, Inorganic Chemistry, Oxford University Press, Oxford (1980).
32. Rana AK and Shah JR, Copper(II), nickel(II), cobalt(II), manganese(II), iron(II), zinc(II), chromium (III), oxovanadium(II) and dioxouranium(II) complexes of 4-benzoylsemicarbazone-1-phenyl-3-methyl-2-pyrazolin-5-one. J Indian Chem Soc 63:281-283 (1986).
33. Lever ABP, Inorganic Electron Spectroscopy. Elsevier, Amsterdam (1984).
34. Srivastava SK, Gupta A and Verman A, Complexes of Co(II), Ni(II), Cu(II), Mn(II), Zn(II) and Fe(III) with benzothiozole sulfonamide morpholide. Chim Acta Turc 11:99-106 (1983).