• The Korean Journal of Pesticide Science
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• v.7 no.2
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• pp.117-122
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• 2003

Modeling and synthesis of novel hydroxyethyl 2-iminothiazolines were carried out through molecular modification of lead compound, 2-phenyliminothiazolines 1, for the purpose of development of new fungicidal agrochemicals. Oxygen atom of the hydroxyethyl group in 2-iminothiazolines 3 would locate in the proximity of the imino carbon at C-2 of 2-iminothiazoline moiety through neighboring group participation, and so that it would affect the biological activity of the molecule. Reaction of $\gamma$-chloroacetoacetanilides 5 with hydroxyethylureas 6 gave 29 kinds of new corresponding hydroxyethyl 2-iminothiazolines 3 in high yields.

• Applied Biological Chemistry
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• v.40 no.2
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• pp.139-143
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• 1997

This research aims at developing a new pesticide by means of synthesizing new 2-iminothiazoline derivatives and testing their bilolgical activity. In an effort to prepare 2-iminothiazolines, primary amines were treated to have reaction with isothiocyanate, followed by a treatment of ${\alpha}-halo$ ketone derivatives. Their antifungal activaty was tested against six different plant diseases. A compound that has a phenylimino group at C-2, methyl at C-3, phenylcarbamoylmethyl at C-4, and hydrogen at C-5 on the thiazoline skeleton was found to be most active.

• Bulletin of the Korean Chemical Society
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• v.34 no.10
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• pp.2861-2862
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• 2013

• Applied Biological Chemistry
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• v.41 no.6
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• pp.471-476
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• 1998

A synthesis and the screening of new 2-iminothiazolines (IV) of which structures are modified based on a lead compound, thiazoline for development of new agrochemical fungicide were described. Bromination of acetoacetanilides (I) which were prepared by the reaction of diketene with anilines gave the corresponding ${\gamma}-bromoacetoactanilide\;(II)$. Treatment of II with N-phenyl-N'-methyl thiourea (III) afforded IV, structure of which was confirmed by various spectroscopic methods. Antifungal activity of the new IV was tested against six kinds of typical plant diseases (in vivo). The IV with aromatic substituents showed remarkable activity against the Pyricuraria oryzae at 250 ppm in primary screening. The candidates with control value over 90% in primary screening were selected and further tested for second screening at lower concentrations. The IV which has an electron-withdrawing substituent such as halogen, especially fluorine in aryl group showed a higher activity as compared to those with electron-donating group and meta substituent was for optimal position.