SU813921A1 - Sterile derivatives of imidazo (4,5-c) pyridiniodide possessing fungicide activ ity - Google Patents

Abstract

Styrilic imidazo f4,5-c] pyridine0-iodide of the general formula (^ J? Wherea) E ^ -CH3, ^ 2 ^ ^ s '^ ^ ^ "e' ^ * ~" ”b) c ^ -sn ^, R ^ and RJ-H, k'-n (c3). ,,; B) R ^ -CHj, Rfi and K ^ -H, R ^ -OCHj; 'd) R, -Ph, R ^ and R, -OCH.3, Rj-H; d) R, -Ph, R ^ and R ^ -H, RN (CH ^ \, possessing fungicidal activity.

Description

The invention relates to new chemical compounds, to sterile imidazo derivatives of 4,5-pyridinium iodide of the general formula RI ah -sx- -, where a), R and RJ-OCHj, Rj-H; b) R, -CH, R and R.-H, RJ-N (CHj), j c) K, -CH3,, Rj-OCH, d) R, -Ph, R-OCHj, Rj-H, SNS

where have the indicated meanings.

The resulting new compounds are colored solids soluble in water, alcohol, and acetone. The structure is confirmed by elemental analysis data.

Example 1. 1,2,5-Trimethyl-4- (n -N, N -dimethylaminostyryl) -imidazo 4,5-cj feast idinium-iodide (IU-6),

1.05 g (3.510 mol) of 1,2,4,5-tetramethylimidase, 5-c of pyridinium iodide and 0.7 g (4.5 mmol) of p- (dimethylamino) benzaldehyde are dissolved by heating in 30 mp n-butanol, 2 ml (2 mmol) of piperidine is added and boiled in an oil bath at a temperature of 135-145 ° C for 2 h. After cooling, the precipitated brick-red color is filtered and washed with ether, yield 1.45 g (96.7% ), so pl. 228-230C (N-butanol).

Found,%: C 52.7, - H 5.4; N 12.7

C ,, H N,.

Included,%: C 52.5 N 5.3, N 12.9.

An example. 1,2,5-Trimethyl-4- (2,5-dimethoxytryl) imidazo 4,5-c pyridium iodide (UU-5). 8139 5 10 15

Prepared analogously to example 1, starting from 1.05 g (3.5 mmol) of 1,2,4,5-tetramethylimidazo 4,5-c1 pyridinium iodide and 0.7 (4.2 mmol) of 2,5-dimethoxybenzaldehyde, yield 1.5 g (96%), so pl. 184-185 C (n-butanol).

Found,%: C 50.5, H 5.5; N 9.2.

..

Calculated,%: C 50.5, H 5.6, N9.3. Example 3. 1,2,5-Trimethyl-4- (p-methoxystyryl) imidazo 4,5-c1-pyridinium-iodide (UY-452).

Prepared analogously to example 1, starting from 1.05 g (3.5 mmol) of 1,2,4,5-tetramethylimidazo 4, 5-C7 pyridinium iodide and 0.51 ml (4.2 mmol) of p-methoxybenzaldehyde, yield 0 , 96 g

(63.3%), so pl. 235-236 0 (H 0), Found,%: N 10.5.

C18 “2 ° C ° Calculated,%: N 10.0.

Example 4. 1,5-Limethyl-2-phenyl-4- (2,5-dtsmethoxystyryl) imidazo 4, 5-c pyridine-iodide (IU-428). Prepared analogously to example 1, starting from 0.8 g (2.2 mmol) 1,4,5-trimethyl-2-phenylimidase, 5-c pyridine-iodide and 0.546 g (3.3 mmol) O 12 (d), Rj and, RN (CH), having fungicidal activity. This property allows us to assume the possibility of their use in agriculture. Known imidazo derivatives of 4, 5-c pyridin-2-one, which have anti-inflammatory activity. The purpose of the invention is to expand the range of fungicides. This goal is achieved by novel styrene imidazo derivatives with 4,5-cl pyridinium iodides of the above general formula, which are obtained by reacting 4-methyl imidazo 4, 5-с pyridinium iodides with aromatic aldehydes in the presence of piperidine as catalysis; torus, according to scheme 2 , 5-dimethoxybenzaldehyde, yield 0.85 g (71.2%), so pl. 233-234 ° C (N-butanol). Found,%: N 8.3. C24 14 ° 2 Calculated,%: N 8.2. Example 5. 1,5-Dimethyl-2-phenyl-4- (nN, N-dimethylaminostyryl) imidazo 4, 5-c pyridine-iodide (UY-431 Prepared analogously to example 1, starting from 0.8 g (2, 2 mmol) 1,4,5-trimethyl-2-phenylimidazo 4,5-c 7 pyri di-iodide and 0.448 g (3 mmol) pN, L-dimethylaminobenzaldehyde and yield 0.85 g (78.2%), so pl. 265-266 ° C (H-butanol). Found,%: C 57.7; H 5.2. Cj Hj N J. Calculated,%: C 58.0; H 5.1. Fungicidal activity is determined on the mycelium of fungi : Botrytis cinerea, Fusarium moniliforme, Venturia inaej: ualis, Aspergillus niger, Verticillium dahlick, and Xahthomonas malvacearum bacteria. The new substances are dissolved in acetone and, under sterile conditions, are introduced into the molten potato dextro agar, which is poured into Petri dishes. Tetramethyl thiuram disulfide (TMTD) is used as a reference. Active substance concentration is 0.003% .After 20–20 h after spilling and solidification, the agar plate is injected with pieces of mycelium, indicated. in concentration on aa 0.003% of 1 test objects and incubated for 4-5 days at a temperature of 22-25 C. After the specified period, the size of the colonies of the studied fungi is determined, and then the percentage of suppression (P) of the fungal mycelium is determined using the Abbot formula compared to benchmark: where a is the growth of the mycelium of fungi; in: contros, the growth of the mycelium of fungi according to the preparation. The test results are presented in the table. The compounds of the ciphers UY-452, IU-428, IU-5, IU-6 in fungicidal activity are superior or equivalent to the TMTD standard on the mycelium of the fungus Verticillium dahlial. Compounds UY-6 and UY-452 also have pronounced bactericidal activity. Compound UYU-5 has activity against the causative agent of gray mold of the fungus. In addition to high fungicidal activity, the claimed substances have a high selectivity of the effect on fungal diseases, and this, in turn, protects the environment from the excessive use of chemicals as a means of controlling parasitic organisms.

Claims (2)

Imidazo G4,5-c] pyridinium sterile derivatives (1-iodide of the general formula where a) E ^ -CH ₃ , E ' ₂ and E ^ -OCH ^, ϊΡ-Η, b) c ₎ -cn ₃ , E e ₅ -n, c'-c (cn ₃ ) ^; c) E ₁ -CH _} , Κ _ε and E ₄ -H, K * -0CH ₃ ; ' d) E, -Pb, E _g and E ₄ -OCH ₃ , K _e -H; JJ-PH, E _g AND E ₄ -H, Ε -Ν (0Η ₃ ) ₅ , possessing fungicidal activity. about 813921 one 813921 2