A series of 2-substituted-4,5-diphenyl imidazoles 1a-j were synthesized by refluxing benzil with different substituted aldehydes in the presence of ammonium acetate and glacial acetic acid. ...Structures of the synthesized compounds were confirmed on the basis of IR, 1H NMR and mass spectral data. Compounds 1a-j were screened for anthelmintic activity. Test results revealed that compounds showed paralysis time of 0.24 to 1.54 min and death time of 0.39 to 4.40 min while the standard drugs albendazole and piperazine citrate showed paralysis time of 0.54 and 0.58 min and death time of 2.16 and 2.47 min, respectively, at the same concentration of 1% (m/V). Five compounds, 2-2-hydroxyphenyl-4,5-diphenyl imidazole (1b), 2-3-methoxyphenyl-4,5-diphenyl imidazole (1c), 2-2-phenylethenyl-4,5-diphenyl imidazole (1e), 2-4-fluorophenyl-4,5-diphenyl imidazole (1g) and 2-3-nitrophenyl-4,5-diphenyl imidazole (1h) showed significant anthelmintic activity compared to the standard drugs.
Refluksiranjem benzila s različitim supstituiranim aldehidima u prisutnosti amonijeva acetata i ledene octene kiseline sintetizirana je serija 2-supstituiranih-4,5-difenil imidazola (1a-j). Strukture sintetiziranih spojeva potvrđene su IR, 1H NMR i masenom spektroskopijom. U testovima na anthelmintičko djelovanje određeno je vrijeme paralize 0,24 do 1,54 min i vrijeme smrti 0,39 do 4,40 min, dok standarni lijekovi albendazol i piperazin citrat imaju vrijeme paralize 0,54 i 0,58 min, a vrijeme smrti 2,16, odnosno 2,47 min pri istim koncentracijama (1%, m/V). Pet spojeva, 2-2-hidroksifenil-4,5-difenil imidazol (1b), 2-3-metoksifenil-4,5-difenil imidazol (1c), 2-2-feniletenil-4,5-difenil imidazol (1e), 2-4-fluorofenil-4,5-difenil imidazol (1g) i 2-3-nitrofenil-4,5-difenil imidazol (1h) pokazuju značajno anthelmintičko djelovanje u odnosnu na standardne lijekove.
A series of 1-substituted imidazoles 1a-d and 2a-d were synthesized and screened for antispasmodic and antidiarrheal activities. Antispasmodic activity was tested at various concentrations on ...isolated tissue preparations; concentration-response curves were plotted and compared with atropine. All compounds were found to inhibit contraction of the guinea pig ileum. Castor oil-induced diarrhea model in rats was used for evaluation of antidiarrheal activity. Parameters such as intestinal transit and volume of intestinal fluid were measured for antidiarrheal activity at 40 mg kg-1 dose and compared with the standard drug loperamide at 6 mg kg-1 dose. Defecation frequency in the test group was found to be significantly lower (p < 0.01) compared to the control group and comparable with that of the standard. The present study reveals that the compounds exert antidiarrheal activity through possible inhibition of intestinal movement and reduction of capillary permeability in the abdominal cavity.
U radu je opisana sinteza serije novih 1-supstituiranih imidazola 1a-d i 2a-d te evaluacija njihovog spazmolitskog i antidijaretskog djelovanja. Spazmolitsko djelovanje različ ith koncentracija ispitivanih spojeva (10, 50 i 100 μg mL-1) ispitano je na izoliranim tkivnim preparatima; krivulje ovisnosti djelovanja o koncentraciji uspoređene su s djelovanjem atropina. Svi ispitivani spojevi inhibirali su kontrakcije ileuma zamorca. Dijarea inducirana ricinusovim uljem u štakora korištena je za vrednovanje antidijaretskog djelovanja. Intestinalni prijenos i volumen intestinalne tekućine mjereni su pri dozi od 40 mg kg-1 i uspoređeni s učinkom standarda loperamida (doza 6 mg kg-1). Učestalost defekacije u testiranoj skupini bila je značajno niža (p < 0,01) u usporedbi s kontrolnom skupinom i standardom. Provedena ispitivanja pokazuju da antidijaretsko djelovanje ispitivanih spojeva može biti posljedica inhibicije intestinalnih pokreta i redukcije kapilarne permeabilnosti u abdominalnoj šupljini.
Refluksiranjem benzila s različitim supstituiranim aldehidima u prisutnosti amonijeva acetata i ledene octene kiseline sintetizirana je serija 2-supstituiranih-4,5-difenil imidazola (1a-j). Strukture ...sintetiziranih spojeva potvrđene su IR, 1H NMR i masenom spektroskopijom. U testovima na anthelmintičko djelovanje određeno je vrijeme paralize 0,24 do 1,54 min i vrijeme smrti 0,39 do 4,40 min, dok standarni lijekovi albendazol i piperazin citrat imaju vrijeme paralize 0,54 i 0,58 min, a vrijeme smrti 2,16, odnosno 2,47 min pri istim koncentracijama (1 % m/V). Pet spojeva, 2-2-hidroksifenil-4,5-difenil imidazol (1b), 2-3-metoksifenil-4,5-difenil imidazol (1c), 2-2-feniletenil-4,5-difenil imidazol (1e), 2-4-fluorofenil-4,5-difenil imidazol (1g) i 2-3-nitrofenil-4,5-difenil imidazol (1h) pokazuju značajno anthelmintičko djelovanje u odnosnu na standardne lijekove.
U radu je opisana sinteza serije novih 1-supstituiranih imidazola 1a-d i 2a-d te evaluacija njihovog spazmolitskog i antidijaretskog djelovanja. Spazmolitsko djelovanje različith koncentracija ...ispitivanih spojeva (10, 50 i 100 µg mL1) ispitano je na izoliranim tkivnim preparatima; krivulje ovisnosti djelovanja o koncentraciji uspoređene su s djelovanjem atropina. Svi ispitivani spojevi inhibirali su kontrakcije ileuma zamorca. Dijarea inducirana ricinusovim uljem u štakora korištena je za vrednovanje antidijaretskog djelovanja. Intestinalni prijenos i volumen intestinalne tekućine mjereni su pri dozi od 40 mg kg1 i uspoređeni s učinkom standarda loperamida (doza 6 mg kg1). Učestalost defekacije u testiranoj skupini bila je značajno niža (p < 0,01) u usporedbi s kontrolnom skupinom i standardom. Provedena ispitivanja pokazuju da antidijaretsko djelovanje ispitivanih spojeva može biti posljedica inhibicije intestinalnih pokreta i redukcije kapilarne permeabilnosti u abdominalnoj šupljini.
The compound (C
) crystallizes in the monoclinic space group
with
= 13.640(3) Å,
= 4.692(1) Å,
= 11.299(3) Å,
= 93.09(1)°, (
= 722.1(3) Å
;
= 2;
= 1.487 Mgm
,
(Mo
) = 0.7107 Å,
= 0.11 mm
,
(000) = ...340,
= 293 K). The structure was solved by direct methods and refined by full matrix least squares method to a final
= 0.039 (
= 0.040). The furano ring adopts a perfect envelope E
conformation with the substituent C71 in equatorial and O6 in axial position. The imidazolidine ring is planar and the substituents O2,O31 and C11 are at 0.028, −0.041 and −0.200 Å from this plane. The mean planes of furano and imidazolidine rings make an angle of 108.6(1)°. The pertinent dihedral angles are 7.5(1)° (phenyl-imidazoline); 115.9(1)° (phenyl-furane), and 7.1(3)° (imidazoline-amide). The molecules are stakked along the
axis forming two infinite chains through an intermolecular H-bond O71 … O6.
Adsorption of imidazolinone herbicides on soil surfaces Negre, M; Leone, P; Boero, V. (Turin Univ. (Italy). Dipartimento di Valorizzazione e Protezione delle Risorse Agroforestali) ...
Atti delle Giornate Fitopatologiche (Italy),
(2000)
Conference Proceeding
Imizapyr (IMZ), imazethapyr (IMZT) and imazaquin (IMZQ) are imidazolinone herbicides which have the same structure except for the nature of the substituent of the nicotinic acid group. In order to ...point out the effect of these structural differences on the affinity of these herbicides with the soil surfaces, we compared their adsorption isotherms at 25 deg C on ten different soils. We observed that the order of adsorption on soil was IMZ = IMZQ IMZT and that adsorption was promoted by the presence of high concentrations of organic matter and/or amorphous iron oxides. In order to investigate on the role of these soil components, we tested the absorption capacity of a soil humic acid and of a synthetical ferrhydrite. Adsorption on humic acid increased as the decreasing polarity of the herbicides: IMZ IMZT IMZQ, while adsorption of ferrihydrite was not significantly influenced by their chemical structure. Adsorption on each sorbent was also dependent on pH, which affected the ionisation state of both adsorbing surface and adsorbate
Imizapyr (IMZ), imazethapyr (IMZT) e imazaquin (IMZQ) sono erbicidi imidazolinonici che presentano la medesima struttura di base, eccetto che per la natura del sostituente dell'acido nicotinico. Allo scopo di evidenziare l'effetto di queste differenze strutturali sull'affinita' di questi erbicidi con le superfici del terreno, abbiamo confrontato le loro isoterme di adsorbimento a 25 gradi C su dieci suoli diversi. Abbiamo riscontrato che l'ordine di adsorbimento sul suolo era IMZ = IMZQ IMZT e che l'adsorbimento aumentava in presenza di concentrazioni elevate di sostanza organica e/o ossidi di ferro amorfi. Allo scopo di studiare il ruolo di questi componenti del terreno, abbiamo misurato la capacita' di adsorbimento di un acido umico del suolo e di una ferridrite sintetica. L'adsorbimento sull'acido umico aumentava al diminuire della polarita' degli erbicidi: IMZ IMZT IMZQ, mentre l'adsorbimento della ferridrite non era influenzato significativamente dalla loro struttura chimica. L'adsorbimento di ogni adsorbente dipendeva pure dal pH, che influenzava lo stato di ionizzazione sia della superficie assorbente, sia del prodotto assorbito
The potent alpha-adrenergic agonist DPI, which has also been claimed to be a selective dopaminergic agonist, was shown to reduce rat striatal dopamine (DA) synthesis, DA utilization and DA metabolism ...following intraperitoneal administration (25 mumol/kg). An analytical procedure for the determination of DPI was developed and its application showed that DPI did not penetrate into the brain in substantial amounts. The possibility of a direct stimulatory action upon striatal presynaptic DA receptors was excluded by the demonstration that DPI lacked effectiveness both in the gamma-butyrolactone model and following intrastriatal administration. The selective alpha-adrenergic agonists phenylephrine (alpha 1) and tramazoline (alpha 2) decreased and increased DA metabolism, respectively, the yohimbine-induced increase being antagonized by DPI. The carbon-bridge analogue (3,4-dihydroxybenzyl)-2-imidazoline (DHBI) had about the same activity as DPI, whereas the potential DPI metabolite (4-hydroxy-3-methoxyphenylimino)-2-imidazolidine (HMPI) was without effect upon striatal DA metabolism. The results are discussed in relation to the remarkable resemblance with the literature data concerning clonidine. It is concluded that the DPI-elicited attenuation of striatal DA turnover is, in all likelihood, the result of a stimulation of alpha 2-adrenoceptors possibly located within the central nervous system. The results cast some doubt on the designation of DPI as a selective DA-inhibitory receptor agonist.
Potato tuber storage is a crucial phase of the production cycle. Storage techniques rely essentially on physical (low temperatures, controlled atmosphere) and chemical (treatments with sprout ...suppressant products) factors, often applied simultaneously, and may change depending on crop destination. Tubers from food crops are stored at temperatures not lower than 7 deg C, to prevent sweetening and blackening of parenchymatous tissues; chemical treatments are needed to achieve a stronger and more prolonged inhibition of bud development. Lower temperatures (3-4 deg C) may be applied for seed tuber conservation, but often they do not warrant an effective and prolonged control of sprout growth, thus chemicals are needed also in this case. Two main problems may arise when using chemical sprout suppressants: the build up of potentially toxic residues on food tubers and the residual phytotoxic activity which may negatively affect, or completely hamper, bud outgrowth of seed tubers. Research has recently highlighted the interesting features of two molecules. The first one is a herbicide belonging to the class of imadazolinones. Thanks to its low toxicity for mammalians, it is particularly suitable for food tuber treatments, while it cannot be used on seed tubers. The latter should be treated only with a chemical whose effects should be easily relieved at the end of the storage period. This is the reason why on seed tubers the use of carvone, a monoterpene whose inhibition activity rapidly terminates when treatments are interrupted, is particularly advisable
La conservazione dei tuberi di patata e' una fase molto delicata nella filiera produttiva di questa coltura. Le tecniche di immagazzinamento si basano essenzialmente su fattori fisici (basse temperature, atmosfera controllata) e chimici (trattamenti con prodotti antigermoglianti), spesso in combinazione fra loro, e variano a seconda del prodotto della coltura. I tuberi destinati all'alimentazione sono conservati a temperature non inferiori a 7 gradi C, per evitare l'addolcimento e l'annerimento, e necessitano di trattamenti chimici per ottenere un piu' efficace e prolungato blocco del germogliamento. I tuberi seme possono essere conservati a temperature piu' basse, ma anche in questo caso e' necessario ricorrere al mezzo chimico. I problemi che derivano dall'impiego di sostanze antigermoglianti sono la presenza di residui potenzialmente tossici sui tuberi da consumo e gli effetti negativi che questi trattamenti hanno nei confronti dello sviluppo delle gemme dei tuberi seme. La sperimentazione ha messo in risalto le positive caratteristiche di due principi attivi in particolare. Uno di essi e' un diserbante della classe degli imidazolinoni. Grazie alla sua bassa tossicita', questo principio attivo e' particolarmente adatto per i trattamenti ai tuberi da consumo, mentre non puo' essere utilizzato sui tuberi seme. Per questi ultimi e' auspicabile l'introduzione dell'uso del carvone, un monoterpene che possiede l'indispensabile requisito di inibire il germogliamento in modo reversibile ed i cui effetti terminano rapidamente dopo l'interruzione del trattamento
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