Substituted Amides of 2,2'-Diphenic Acid and Their Insecticidal Activity
Abstract Generated abstract
This study extends prior work on biologically active derivatives of 2,2′-diphenic acid by synthesizing thirteen previously undescribed substituted monoamides. The compounds were prepared by acylating a range of amines with diphenic anhydride in dry xylene, then isolated through salt formation, acid precipitation, and recrystallization, with melting points, crystal appearance, and nitrogen analyses reported. Insecticidal activity was tested against flies and rice weevils, and the monoamide formed from 2-aminothiazole showed the highest activity among the compounds examined.
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PROCEEDINGS
OF THE TOMSK ORDER OF THE RED BANNER OF LABOR POLYTECHNIC
INSTITUTE named after S. M. KIROV
Vol. 136 1965
SUBSTITUTED AMIDES OF 2,2′-DIPHENIC ACID AND THEIR INSECTICIDAL ACTIVITY
L. P. KULEV, G. M. STEPNOVA, P. F. TABINSKAYA
(Submitted by the organic section of the scientific seminar
of the Chemical-Technological Faculty)
The substituted monoamides of 2,2′-diphenic acid obtained by us earlier [1, 2] exhibited high herbicidal and insecticidal activity. In order to search for new biologically active preparations, another 13 compounds of this series were synthesized. Substituted monoamides of 2,2′-diphenic acid were obtained by acylation of amines with diphenic anhydride according to the reaction equation
$$ \begin{aligned} &\text{diphenic anhydride} + \mathrm{H_2N{-}Ar}\ (Alk) \longrightarrow \text{2,2′-diphenic acid monoamide} \\ &\qquad\qquad\qquad\qquad \mathrm{-CO{-}NH{-}Ar}\ (Alk),\quad \mathrm{-COOH}. \end{aligned} $$
The compounds described are crystalline substances, insoluble in water but soluble in ordinary organic solvents. Monoamides give readily water-soluble salts with alkali metals. For all the compounds obtained, insecticidal activity was determined (A. V. Kovalenok, Tomsk State University) on flies and rice weevils. The most active proved to be the amide obtained by acylation of 2-aminothiazole with diphenic anhydride.
Experimental Part
0.05 mole of amine, 0.05 mole of diphenic anhydride, and 50 ml of dry xylene are placed in a flask fitted with a reflux condenser and a stirrer, and heated in an oil bath at a temperature of 135–140° for three hours. The precipitate that separates after cooling of the reaction mixture is filtered off, dried, and dissolved in a 10% aqueous solution of soda. The solution is filtered and the monoamide is precipitated with acid. Recrystallization of the monoamides is carried out from alcohol, xylene, or chlorobenzene. The characteristics of the compounds obtained are given in Table 1.
Conclusions
Thirteen substituted monoamides of 2,2′-diphenic acid not described in the literature have been synthesized. Their insecticidal activ-
activity. The amide obtained by acylation of 2-aminothiazole with diphenic anhydride has the highest insecticidal properties.
Table 1
| Acylated amine | M.p. | Crystal color | % nitrogen, found | % nitrogen, calculated |
|---|---|---|---|---|
| Methylamine | 209 | colorless | 5.67 | 5.49 |
| Dimethylamine | 157 | colorless | 5.27 | 5.20 |
| Diethylamine | 178 | colorless | 4.66 | 4.71 |
| 3-Toluidine | 187 | colorless | 4.22 | 4.23 |
| 1,3,4-Xylidine | 177 | colorless | 5.23 | 5.30 |
| 2-Aminobenzoic acid | 188 | colorless | 3.89 | 3.88 |
| 3-Aminobenzoic acid | 247 | colorless | 3.94 | 3.88 |
| 4-Aminobenzoic acid | 137 | colorless | 4.00 | 3.88 |
| 4-Aminoanisole | 166 | colorless | 4.24 | 4.03 |
| 4-Aminoazobenzene | 182 | orange | 9.87 | 9.97 |
| 2-Naphthylamine | 186 | colorless | 3.82 | 3.81 |
| Piperidine | 167 | colorless | 4.63 | 4.53 |
| 2-Aminothiazole | 236 | colorless | 8.80 | 8.61 |
LITERATURE
- L. P. Kulev, G. M. Stepnova. Derivatives of diphenic acid. 1. Substituted amides of 2,2′-diphenic acid. Izv. TPI, 111, 16, 1961.
- L. P. Kulev, G. M. Stepnova. Derivatives of diphenic acid. 2. Esters of substituted monoamides of 2,2′-diphenic acid. Izv. TPI, 111, 20, 1961.