MD1721Z - Use of (Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-1-en-3-one as an active compound against Gloeosporium ampelophagum Sacc. fungus - Google Patents
Use of (Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-1-en-3-one as an active compound against Gloeosporium ampelophagum Sacc. fungus Download PDFInfo
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- MD1721Z MD1721Z MDS20220097A MDS20220097A MD1721Z MD 1721 Z MD1721 Z MD 1721Z MD S20220097 A MDS20220097 A MD S20220097A MD S20220097 A MDS20220097 A MD S20220097A MD 1721 Z MD1721 Z MD 1721Z
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- ampelophagum
- gloeosporium
- sacc
- dichlorophenyl
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- 241000901048 Elsinoe ampelina Species 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 title claims abstract description 8
- RHRSEZQUWLVSHO-NSIKDUERSA-N (z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1,2,4-triazol-1-yl)hex-1-en-3-one Chemical compound C1=NC=NN1/C(C(=O)CC(C)C)=C\C1=CC=C(Cl)C=C1Cl RHRSEZQUWLVSHO-NSIKDUERSA-N 0.000 title claims abstract description 6
- 241000233866 Fungi Species 0.000 title abstract description 4
- 239000000417 fungicide Substances 0.000 abstract description 6
- 235000014787 Vitis vinifera Nutrition 0.000 abstract description 4
- 240000006365 Vitis vinifera Species 0.000 abstract description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 abstract description 2
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- 239000002609 medium Substances 0.000 description 4
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000000843 anti-fungal effect Effects 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
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- 241000219094 Vitaceae Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
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- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LQDARGUHUSPFNL-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(COC(F)(F)C(F)F)CN1C=NC=N1 LQDARGUHUSPFNL-UHFFFAOYSA-N 0.000 description 1
- YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 description 1
- HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 description 1
- KWLVWJPJKJMCSH-UHFFFAOYSA-N 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide Chemical compound C1=C(OCC#C)C(OC)=CC(CCNC(=O)C(OCC#C)C=2C=CC(Cl)=CC=2)=C1 KWLVWJPJKJMCSH-UHFFFAOYSA-N 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
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- 239000005809 Metiram Substances 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Invenţia se referă la chimie şi agricultură, în special la utilizarea unui compus heterociclic, derivat al 1,2,4-triazolului, în calitate de remediu fungicid contra patogenului Gloeosporium ampelophagum Sacc., cu acţiune inhibitorie asupra germinării sporilor acestuia. The invention relates to chemistry and agriculture, in particular to the use of a heterocyclic compound, derivative of 1,2,4-triazole, as a fungicidal remedy against the pathogen Gloeosporium ampelophagum Sacc., with inhibitory action on the germination of its spores.
Din totalitatea bolilor ce provoacă daune semnificative viţei de vie, o însemnătate nu mai puţin importantă, o are şi antracnoza, o boală provocată de ciuperca Gloeosporium ampelophagum Sacc. Această boală, care îşi are originea din Europa, s-a răspândit în întreaga lume şi provoacă epidemii grave în timpul anotimpurilor calde şi umede. Of all the diseases that cause significant damage to the grapevine, anthracnose, a disease caused by the fungus Gloeosporium ampelophagum Sacc, is no less important. This disease, which originated in Europe, has spread throughout the world and causes serious epidemics during hot and humid seasons.
Agentul patogen al antracnozei, atacă organele aeriene ale viţei de vie şi este deosebit de patogen în primele faze de dezvoltare a viţei de vie, atunci când poate ataca lăstarii tineri, rahisul inflorescenţelor şi sistemul foliar ceea ce duce la crearea unui anumit deficit de hrană, stagnarea proceselor de maturare a lăstarilor, strugurilor şi ca urmare micşorarea recoltei. The pathogen of anthracnose attacks the aerial organs of the vine and is particularly pathogenic in the first stages of vine development, when it can attack the young shoots, the rachis of the inflorescences and the leaf system, which leads to the creation of a certain food deficit, the stagnation of the ripening processes of the shoots, grapes and as a result the reduction of the harvest.
Cu toate ca în ultimii ani antracnoza nu are o dezvoltare semnificativă, trebuie de ţinut cont că ponderabilitatea bolii poate fi distrugătoare atât pentru recolta de struguri, cât şi pentru viţa de vie, urmările fiind nematurizarea coardelor şi incapacitatea de rezistenţă la condiţiile iernilor geroase. Dezvoltarea şi răspândirea antracnozei poate produce pagube importante de recoltă în viile în care nu se respectă tehnologia de cultură şi de protecţie a plantelor. Atunci când condiţiile sunt favorabile, atacul acestei boli poate fi foarte grav, ducând la pagube importante, fiind afectată nu numai producţia anului respectiv, ci şi a anilor următori. Intensitatea apariţiei bolii este mai pronunţată în timpul creşterii lăstarilor şi înfloririi viţei de vie, dar infectarea e posibilă pe parcursul întregii perioade de vegetaţie, deoarece numărul de generaţii al ciupercii poate ajunge până la 30 şi chiar 40 în anii epifitotici. În lipsa tratamentelor daunele provocate de antracnoză pot duce la pierderi de recoltă chiar şi până la 80 % [Mirică I., Mirică A. Antracnoza viţei de vie şi combaterea ei. Studiu monografic, Editura Ceres 1981, pag. 5-134]. Although in recent years anthracnose has not had a significant development, it must be taken into account that the severity of the disease can be destructive both for the grape harvest and for the vine, the consequences being the immaturity of the vines and the inability to withstand the conditions of frosty winters. The development and spread of anthracnose can cause significant crop damage in vineyards where cultivation and plant protection technology is not respected. When the conditions are favorable, the attack of this disease can be very serious, leading to significant damage, affecting not only the production of the respective year, but also of the following years. The intensity of the appearance of the disease is more pronounced during the growth of shoots and the flowering of the vine, but infection is possible during the entire vegetation period, because the number of generations of the fungus can reach up to 30 and even 40 in epiphytic years. In the absence of treatments, the damage caused by anthracnose can lead to crop losses even up to 80% [Mirică I., Mirică A. Anthracnose of the vine and its control. Monographic study, Ceres Publishing House 1981, page 5-134].
Pentru germinarea sporilor agentului patogen sunt necesare condiţii de umiditate şi temperatură a aerului de doar +3°C . Perioada de incubaţie depinde de temperatură (10...12°C - 12 zile, 24...25°C - 3...5 zile), precum şi de vârsta frunzei, de aceea foarte important este să nu fie ratat termenul de aplicare a primelor tratamente. Primele tratamente se fac cu fungicide chimice pe bază de cupru anorganic, mancozeb, metiram, iar mai târziu cu preparate sistemice. For the germination of the spores of the pathogen, conditions of humidity and air temperature of only +3°C are necessary. The incubation period depends on the temperature (10...12°C - 12 days, 24...25°C - 3...5 days), as well as the age of the leaf, therefore it is very important not to miss the deadline application of the first treatments. The first treatments are made with chemical fungicides based on inorganic copper, mancozeb, metiram, and later with systemic preparations.
În calitate de preparat fungicid standard în viticultură este utilizat preparatul comercial pe bază de cupru cu denumirea de marcă - cuproxat [1]. Acesta reprezintă un preparat de natură anorganică, protejat prin know-how de producătorul din UE. Deşi posedă o activitate destul de înaltă, cuproxatul are dezavantajul că trebuie utilizat în doze relative înalte (de 1%), totodată, datorită naturii sale anorganice, el nu se descompune şi poate duce la poluare cu metalul greu cupru. As a standard fungicide preparation in viticulture, the copper-based commercial preparation with the brand name - cuproxat [1] is used. This is a preparation of an inorganic nature, protected by know-how by the EU manufacturer. Although it has a fairly high activity, cuproxate has the disadvantage that it must be used in relatively high doses (of 1%), at the same time, due to its inorganic nature, it does not decompose and can lead to pollution with the heavy metal copper.
Un efect bun inhibitor împotriva antracnozei îl au şi fungicidele din grupa triazolilor (de ex. Revus Top; Quadris Top; Inspire Super (Horus+Scor); Sistan, Riley (miclobutanil) şi Talendo (tetraconazol) [https://vinograd.info/spravka/slovar/antraknoz-vinograda.html]. Din aceste fungicide este folosit pe larg preparatul triazolic cu denumirea chimică IUPAC 1-[[2-(2,4-diclorfenil)-4-propil-1,3-dioxolan-2-il]metil]-1,2,4-triazol, cunoscut sub denumirile comerciale propiconazol, Tilt, ş. a. [2]. Dezavantajele acestui fungicid constau în aceea că activitatea lui nu este destul de înaltă pentru combaterea antracnozei. Totodată, există riscul de apariţie a rezistenţei la metoda chimică de control, dacă nu se alternează preparatele de contact cu cele sistemice, precum şi substanţele active din diferite clase. Identificarea noilor compuşi contra antracnozei cu activitate antifungică, eficienţă sporită şi toxicitate redusă, atât asupra culturii, cât şi asupra mediului prezintă un interes practic în sistemul de protecţie a viţei de vie. Fungicides from the triazole group also have a good inhibitory effect against anthracnose (e.g. Revus Top; Quadris Top; Inspire Super (Horus+Scor); Sistan, Riley (myclobutanil) and Talendo (tetraconazole) [https://vinograd.info /spravka/slovar/antraknoz-vinograda.html] Of these fungicides, the triazole preparation with the IUPAC chemical name 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolane-2] is widely used -yl]-triazole, known as propiconazole, etc. The disadvantages of this fungicide are that its activity is not high enough to combat anthracnose. there is a risk of resistance to the chemical control method, if contact preparations are not alternated with systemic ones, as well as active substances from different classes.Identification of new compounds against anthracnose with antifungal activity, increased efficiency and reduced toxicity, both on the culture, as well as the environment presents a practical interest in the vine protection system.
Problema rezolvată de invenţie constă în extinderea gamei de preparate din clasa triazolilor cu activitate fungitoxică ridicată care ar putea fi utilizate cu succes în agricultură pentru combaterea antracnozei provocată de Gloeosporium ampelophagum Sacc. The problem solved by the invention consists in expanding the range of preparations from the class of triazoles with high fungitoxic activity that could be successfully used in agriculture to combat anthracnose caused by Gloeosporium ampelophagum Sacc.
Esenţa invenţiei constă în aceea că în calitate de compus activ cu acţiune inhibitorie asupra germinării sporilor ciupercii fitopatogene din specia Gloeosporium ampelophagum Sacc., agentul patogen al antracnozei viţei de vie, se propune (Z)-1-(2,4-diclorfenil)-5-metil-2-(1H-1,2,4-triazol-1-il)hex-1-en-3-ona în concentraţie optimă activă de 0,05%. The essence of the invention is that (Z)-1-(2,4-dichlorophenyl)- 5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-1-en-3-one in optimal active concentration of 0.05%.
Avantajale invenţiei constau în aceea că compusul (Z)-1-(2,4-diclorfenil)-5-metil-2-(1H-1,2,4-triazol-1-il)hex-1-en-3-onă contribuie la sporirea activităţii fungitoxice pentru agentul cauzal al antracnozei viţei de vie şi poate fi folosit ca substanţă activă în combaterea acestei boli, astfel lărgind gama de produse din clasa triazolilor. The advantages of the invention consist in the fact that the compound (Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-1-en-3- it contributes to increasing the fungitoxic activity for the causative agent of grapevine anthracnose and can be used as an active substance in combating this disease, thus expanding the range of products from the triazole class.
De asemenea, costul producerii compusului din invenţie este unul relativ redus şi se obţine conform brevetului MD1604 Y, unde este descrisă şi activitatea antifungică a compusului menţionat faţă de Fusarium oxysporum. Also, the cost of producing the compound of the invention is relatively low and it is obtained according to patent MD1604 Y, where the antifungal activity of the mentioned compound against Fusarium oxysporum is also described.
(Z)-1-(2,4-diclorfenil)-5-metil-2-(1H-1,2,4-triazol-1-il)hex-1-en-3-ona a fost testată in vitro pentru determinarea activităţii antifungice împotriva ciupercii Gloeosporium ampelophagum. Activitatea a fost comparată în testele de inhibare in vitro cu cea a preparatelor comerciale, şi anume, cu analogul proxim triazolic după structură şi activitate Tilt şi preparatul standard utilizat în viticultură - cuproxat. (Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-1-en-3-one was tested in vitro for determination of the antifungal activity against the fungus Gloeosporium ampelophagum. The activity was compared in the in vitro inhibition tests with that of the commercial preparations, namely, with the proximate triazole analog according to structure and activity Tilt and the standard preparation used in viticulture - cuproxate.
Exemplu de realizare a invenţiei Example of realization of the invention
Izolarea agentului patogen a fost efectuată conform metodei [Недов П.Н. Новые методы фитопатологических и иммунологических исследований в виноградарстве. Кишинев «Штиинца», 1985, стр. 9-52]. Pentru izolarea Gloeosporium ampelophagum Sacc. se colectează din câmp frunze, lăstari şi boabe ale viţei de vie ce prezintă simptome de antracnoză. În condiţii de laborator materialul colectat se spală sub apă curgătoare, apoi în apă distilată sterilă, după care se iau bucăţi de ţesut afectat şi se transferă în cutii Petri pe mediu nutritiv agarizat (cartof-dextroză-agar) în condiţii sterile. Cutiile Petri ce conţin inoculul ciupercii, sunt transferate în termostat la temperatura de 24...26°C. Creşterea miceliului începe în a doua - a treia zi după inoculare. Peste 10-15 zile culturile izolate pot fi transferate în alte cutii Petri pe mediu nutritiv, pentru obţinerea culturii pure a ciupercii. Isolation of the pathogen was carried out according to the method [Недов П.Н. New methods of phytopathological and immunological studies in viticulture. Chişinău «Shtiintsa», 1985, str. 9-52]. For the isolation of Gloeosporium ampelophagum Sacc. leaves, shoots and grapes of vines showing symptoms of anthracnose are collected from the field. In laboratory conditions, the collected material is washed under running water, then in sterile distilled water, after which pieces of affected tissue are taken and transferred to Petri dishes on agarized nutrient medium (potato-dextrose-agar) under sterile conditions. The Petri dishes containing the mushroom inoculum are transferred to the thermostat at a temperature of 24...26°C. Mycelium growth begins on the second - third day after inoculation. After 10-15 days, the isolated cultures can be transferred to other Petri dishes on nutrient medium, to obtain the pure culture of the fungus.
Preparatul din invenţie a fost obţinut într-o singură etapă, conform brevetului de scurtă durată MD1604 Y, prin condensarea stereospecifică a 2,4-diclorobenzaldehidei cu triazolilpentanona respectivă. The preparation of the invention was obtained in a single step, according to the short-lived patent MD1604 Y, by the stereospecific condensation of 2,4-dichlorobenzaldehyde with the respective triazolylpentanone.
Testarea preparatului din invenţie a fost efectuată conform metodei [Голышин Н.М., Смирнова А.А., Зильберминц И.В. Методические указания по определению устойчивости вредителей и возбудителей болезней сельскохозяйственных культур и энтомофагов к пестицидам. Типография ВАСХНИЛ, Москва 1984, стр. 56-61]. Din cultura pură se pregăteşte suspensia de spori ai patogenului care se lasă la temperatura camerei pentru 1,5...2 ore, ca sporii să se disperseze. Se pregătesc lamelele de sticlă, se dezinfectează, apoi în condiţii sterile se acoperă cu mediu nutritiv agarizat. Pentru testarea preparatului, acesta se aplică sub formă de soluţii în DMSO, prin pulverizare pe suprafaţa lamelei acoperite cu mediu nutritiv, după care peste 30 min - 1 oră se aplică suspensia de spori ai patogenului. Ulterior lamelele de sticlă se transferă în cutii Petri aşternute cu hârtie de filtru umezită pentru o asigurare a umidităţii de 100%. Lucrările se efectuază în condiţii sterile, în boxa prealabil dezinfectată cu ajutorul unui bec bactericid UV. Experienţa va conţine varianta control (suspensie de spori fără preparat), varianta standard cu preparatul cuproxat şi varianta cu analogul proxim cu preparatul Tilt. Cutiile Petri cu conţinutul cercetat au fost menţinute în camera climatică la temperatura de 24°C. Peste 24 ore lamelele de sticlă au fost examinate la microscopul optic pentru evaluare şi determinarea germinării sporilor. Studierea sporilor s-a realizat sub obiectivul cu puterea de mărire x45 al microscopului optic Meopta, în diferite locuri pe lamelă, numărând în câmpul de vedere toţi sporii, atât cei germinaţi, cât şi cei negerminaţi. Au fost număraţi în total câte 50 de spori pentru fiecare variantă în patru repetiţii, determinând procentul de spori germinaţi în raport cu cei negerminaţi. Testing of the preparation of the invention was carried out according to the method [Голышин Н.М., Смирнова А.А., Зильберминц И.В. Methodical guidelines for determining the stability of pests and diseases of agricultural crops and entomophages to pesticides. Типография ВАСХНИЛ, Москва 1984, стр. 56-61]. A suspension of pathogen spores is prepared from the pure culture, which is left at room temperature for 1.5...2 hours, so that the spores disperse. Glass slides are prepared, disinfected, then under sterile conditions they are covered with agarized nutrient medium. To test the preparation, it is applied in the form of solutions in DMSO, by spraying on the surface of the slide covered with nutrient medium, after which the pathogen's spore suspension is applied over 30 min - 1 hour. Afterwards, the glass slides are transferred to Petri dishes lined with moistened filter paper to ensure 100% humidity. The work is carried out under sterile conditions, in a previously disinfected box with the help of a UV bactericidal bulb. The experience will contain the control version (spore suspension without the preparation), the standard version with the proximate preparation and the version with the close analogue with the Tilt preparation. The Petri dishes with the researched content were kept in the climatic chamber at a temperature of 24°C. Over 24 hours, the glass slides were examined under an optical microscope for evaluation and determination of spore germination. The study of the spores was carried out under the objective with the x45 magnification power of the Meopta optical microscope, in different places on the coverslip, counting in the field of view all the spores, both the germinated and the non-germinated ones. A total of 50 spores were counted for each variant in four repetitions, determining the percentage of germinated spores in relation to non-germinated ones.
Rezultatul acţiunii preparatului se calculează folosind formula Abbott: The result of the action of the preparation is calculated using the Abbott formula:
T T
unde T - rezultatul acţiunii preparatului (%) where T - the result of the action of the preparation (%)
Pc - procentul sporilor germinaţi în varianta control (%) Pc - the percentage of germinated spores in the control version (%)
Pe - procentul sporilor germinaţi în varianta experimentală (%) On - the percentage of germinated spores in the experimental version (%)
Tabel Table
Acţiunea preparatelor asupra germinării sporilor Gloeosporium ampelophagum Sacc. The action of preparations on the germination of Gloeosporium ampelophagum Sacc.
Denumirea preparatului Doza, (%) Nr. repetiţiei Nr. de spori cercetaţi Nr. de spori germinaţi din totalul celor cercetaţi Procentul de spori germinaţi (%) Acţiunea preparatului, T (%) Media acţiunii preparatului (%) Invenţia (Z)-1-(2,4-diclorfenil)-5-metil-2-(1H-1,2,4-triazol-1-il)hex-1-en-3-onă 0,05 1 2 3 4 50 50 50 50 0 0 1 0 0 0 2 0 100 100 98 100 99,5 Tilt, 1-[[2-(2,4-diclorfenil)-4-propil-1,3-dioxolan-2-il]metil]-1,2,4-triazol 0,05 1 2 3 4 50 50 50 50 43 41 44 50 86 82 88 100 6,52 0 12 0 4,63 Cuproxat (standard) 1,0 1 2 3 50 50 50 33 42 43 66 84 86 19,5 16 14 16,5 Martor - 1 2 3 4 50 50 50 50 46 41 50 50 92 82 100 100 - - - - - Name of the preparation Dose, (%) No. rehearsal No. of researched spores No. of germinated spores from the total of those investigated Percentage of germinated spores (%) Action of the preparation, T (%) Average action of the preparation (%) Invention (Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H -1,2,4-triazol-1-yl)hex-1-en-3-one 0.05 1 2 3 4 50 50 50 50 0 0 1 0 0 0 2 0 100 100 98 100 99.5 Tilt, 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1,2,4-triazole 0.05 1 2 3 4 50 50 50 50 43 41 44 50 86 82 88 100 6.52 0 12 0 4.63 Approximate (standard) 1.0 1 2 3 50 50 50 33 42 43 66 84 86 19.5 16 14 16.5 Witness - 1 2 3 4 50 50 50 50 46 41 50 50 92 82 100 100 - - - - -
Conform rezultatelor prezentate, se atestă o acţiune inhibitorie în valoare de 99,5% a compusului din invenţie în concentraţie de 0,05%, asupra germinării sporilor Gloeosporium ampelophagum Sacc. Este clar pentru un specialist în domeniu că aceasta nu exclude utilizarea preparatului din invenţie şi la concentraţii rezonabile mai mari decât intervalul indicat. Dar această utilizare nu este justificată economic având în vedere că deja la concentraţia de 0,05 % se atinge o acţiune practică foarte înaltă. According to the presented results, an inhibitory action worth 99.5% of the compound of the invention in a concentration of 0.05%, on the germination of Gloeosporium ampelophagum Sacc spores, is attested. It is clear to a specialist in the field that this does not exclude the use of the preparation of the invention at reasonably higher concentrations than the indicated range. But this use is not economically justified considering that already at a concentration of 0.05% a very high practical action is reached.
1. Ministerul Agriculturii şi Industriei Alimentare al Republicii Moldova. Serviciul de Stat „Centrul de Stat pentru Atestarea şi Omologarea Produselor de Uz Fitosanitar şi a Fertilizanţilor". Registrul de stat, data înregistrării cuproxatului în registru 20.02.2019, <https://www.pesticide.md/registrul-de-stat/> 1. Ministry of Agriculture and Food Industry of the Republic of Moldova. State Service "State Center for Attestation and Homologation of Phytosanitary Products and Fertilizers". State register, date of registration of the agent in the register 20.02.2019, <https://www.pesticide.md/registrul-de-stat/ >
2. L. Toribio et al. Chiral separation of some triazole pesticides by supercritical fluid chromatography. J. Chromatography A, 2004, 1046, p. 249-253 2. L. Toribio et al. Chiral separation of some triazole pesticides by supercritical fluid chromatography. J. Chromatography A, 2004, 1046, p. 249-253
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| Application Number | Priority Date | Filing Date | Title |
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| MDS20220097A MD1721Z (en) | 2022-11-30 | 2022-11-30 | Use of (Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-1-en-3-one as an active compound against Gloeosporium ampelophagum Sacc. fungus |
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| MDS20220097A MD1721Z (en) | 2022-11-30 | 2022-11-30 | Use of (Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-1-en-3-one as an active compound against Gloeosporium ampelophagum Sacc. fungus |
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| MDS20220097A MD1721Z (en) | 2022-11-30 | 2022-11-30 | Use of (Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-1-en-3-one as an active compound against Gloeosporium ampelophagum Sacc. fungus |
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