MD1591Z - Process for treating winter soft wheat grains - Google Patents
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- MD1591Z MD1591Z MDS20210031A MDS20210031A MD1591Z MD 1591 Z MD1591 Z MD 1591Z MD S20210031 A MDS20210031 A MD S20210031A MD S20210031 A MDS20210031 A MD S20210031A MD 1591 Z MD1591 Z MD 1591Z
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Invenţia se referă la agricultură şi chimie, şi anume la un procedeu de tratare a boabelor de grâu comun de toamnă pentru sporirea rezistenţei la acţiunea F. oxysporum şi D. sorokiniana. The invention relates to agriculture and chemistry, namely to a process for treating common winter wheat grains to increase resistance to the action of F. oxysporum and D. sorokiniana.
Tratarea seminţelor este o metodă de neutralizare a majorităţii agenţilor patogeni (fungici şi bacterieni) dăunători, care se răspândesc prin seminţe şi sol. Un astfel de procedeu protejează culturile de daune, contribuind la salvarea a până la 30-50% din recoltă. Productivitatea depinde de metoda de aplicare, calitatea aplicării şi de conţinutul de pesticide de pe suprafaţa seminţelor. În plus, utilizarea preparatelor prin astfel de procedee este mai rentabilă decât pulverizarea ulterioară cu fungicide şi insecticide în timpul cultivării plantelor (Протравливание семян: плюсы и минусы, 22.01.2020, Online, URL: https://lnzweb.com/ru/blog/plyusi-ta-minusi-protruyuvannya-nasinnya). Seed treatment is a method of neutralizing most of the harmful pathogens (fungal and bacterial), which spread through seeds and soil. Such a procedure protects crops from damage, helping to save up to 30-50% of the harvest. Productivity depends on the method of application, the quality of application and the content of pesticides on the surface of the seeds. In addition, the use of preparations by such procedures is more cost-effective than subsequent spraying with fungicides and insecticides during plant cultivation (Протравливание семян: плюсы и минусы, 22.01.2020, Online, URL: https://lnzweb.com/ru/blog/plyusi-ta-minusi-protruyuvannya-nasinnya).
Putregaiul de rădăcină la grâul comun de toamnă este o maladie larg răspândită în lume, inclusiv în Republica Moldova. Boala compromite semănăturile prin diverse manifestări dăunătoare care conduc la dezvoltarea plantelor neviguroase, pierderi de roadă, diminuarea calităţii boabelor. Putregaiul de rădăcină este cauzat de un complex fungic ce reprezintă diverse specii, dintre care Fusarium spp. şi Drechslera/Bipolaris spp. se evidenţiază prin incidenţă şi virulenţă înaltă. Este cunoscut faptul că aceste specii produc şi diminuarea masei plantelor (Thompson A.L., Mahoney A.K., Smiley R.W. et al. Resistance to Multiple Soil-Borne Pathogens of the Pacific Northwest, USA Is Colocated in a Wheat Recombinant Inbred Line Population. G3 Genes|Genomes|Genetics, v. 7, nr. 4, 2017, p. 1109-1116; Creswell T. Bipolaris sorokiniana (Common Root Rot and Spot Blotch of Barley and Wheat). https://wiki.bugwood.org/Bipolaris_sorokiniana_(Common_Root_Rot_and_Spot_Blotch_of_Barley_and_Wheat), criteriu care caracterizează rezistenţa la patogeni. Root rot of common winter wheat is a disease widespread in the world, including in the Republic of Moldova. The disease compromises crops through various harmful manifestations that lead to the development of weak plants, yield losses, and reduced grain quality. Root rot is caused by a fungal complex that represents various species, of which Fusarium spp. and Drechslera/Bipolaris spp. stand out for their high incidence and virulence. It is known that these species also cause a reduction in plant mass (Thompson A.L., Mahoney A.K., Smiley R.W. et al. Resistance to Multiple Soil-Borne Pathogens of the Pacific Northwest, USA Is Colocated in a Wheat Recombinant Inbred Line Population. G3 Genes|Genomes|Genetics, v. 7, no. 4, 2017, p. 1109-1116; Creswell T. Bipolaris sorokiniana (Common Root Rot and Spot Blotch of Barley and Wheat). https://wiki.bugwood.org/Bipolaris_sorokiniana_(Common_Root_Rot_and_Spot_Blotch_of_Barley_and_Wheat), a criterion that characterizes resistance to pathogens.
Un impediment serios în eficientizarea măsurilor de protecţie a plantelor de agenţii cauzali ai putregaiului de rădăcină constă în preţul de cost înalt al fungicidelor şi dezvoltarea rezistenţei patogenilor la fungicide (Panth M., Hassler S.C., Baysal-Gurel F. Methods for Management of Soilborne Diseases in Crop Production. Agriculture, 2020, 10(1), 16), motiv pentru care identificarea noilor procedee care ar include utilizarea compuşilor cu activitate protectoare este un important subiect de actualitate în sistemul de protecţie a plantelor de această maladie. A serious impediment to the efficiency of plant protection measures against root rot causative agents is the high cost of fungicides and the development of pathogen resistance to fungicides (Panth M., Hassler S.C., Baysal-Gurel F. Methods for Management of Soilborne Diseases in Crop Production. Agriculture, 2020, 10(1), 16), which is why the identification of new processes that would include the use of compounds with protective activity is an important current topic in the plant protection system against this disease.
Este cunoscut un procedeu de protecţie al plantelor de fungi fitopatogeni cu utilizarea compusului (E)-1-(2,4-dichlorofenil)-4,4-dimetil-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ol (Diniconazol) [1]. Avantajul lui constă în aceea că este utilizat pentru conferirea plantelor a unei protecţii de acţiunea nocivă a fungilor fitopatogeni, de asemenea compusul utilizat în cadrul acestui procedeu nu este toxic. A process for protecting plants from phytopathogenic fungi is known using the compound (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (Diniconazole) [1]. Its advantage is that it is used to provide plants with protection from the harmful effects of phytopathogenic fungi, and the compound used in this process is not toxic.
Dezavantajul constă în aceea că procedeul nu conduce la o protecţie antifungică suficient de înaltă faţă de F. oxysporum şi D. sorokiniana. The disadvantage is that the process does not lead to sufficiently high antifungal protection against F. oxysporum and D. sorokiniana.
Problema rezolvată de invenţie constă în extinderea gamei de procedee de tratare a boabelor de grâu comun de toamnă cu compuşi din clasa 1,2,4-triazolilor pentru sporirea rezistenţei plantelor de grâu la acţiunea fungilor F. oxysporum şi D. sorokiniana. The problem solved by the invention consists in expanding the range of procedures for treating common winter wheat grains with compounds from the 1,2,4-triazole class to increase the resistance of wheat plants to the action of the fungi F. oxysporum and D. sorokiniana.
Procedeul, conform invenţiei, constă în tratarea boabelor de grâu comun de toamna cu soluţie apoasă a compusului (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ona cu formula: The process, according to the invention, consists of treating common winter wheat grains with an aqueous solution of the compound (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one with the formula:
, ,
în concentraţie de 0,005-0,01%, timp de 3 ore. in a concentration of 0.005-0.01%, for 3 hours.
Avantajele invenţiei constau în aceea că utilizarea în procedeul revendicat a compusului (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ona contribuie la sporirea rezistenţei plantelor de grâu la acţiunea F. oxysporum şi D. sorokiniana în raport cu soluţia cea mai apropiată. The advantages of the invention consist in the fact that the use in the claimed process of the compound (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one contributes to increasing the resistance of wheat plants to the action of F. oxysporum and D. sorokiniana in relation to the closest solution.
De asemenea, compusul din invenţie are un preţ de cost redus faţă de cel din cadrul soluţiei celei mai apropiate, deoarece sinteza lui se desfaşoară într-o etapă faţă de 3 etape, caracteristic celui din cadrul celei mai apropiate soluţii şi constă în utilizarea cetonei: 4-metil-1-(1H-1,2,4-triazol-1-il)pentan-2-one. Procedeul de sinteză prevede interacţiunea cetonei menţionate anterior cu 2,4-diclorbenzaldehida în benzen în prezenţa piperidinei şi acidului acetic (cantităţi catalitice), care conduce la formarea unui singur izomer - (Z)-1-(2,4-dichlorofenil)-5-metil-2-(1H-1,2,4-triazol-1-il)hex-1-en-3-ona cu temperatura de topire de 92-93°С (Stingaci E., Zveaghinteva M., Pogrebnoi S., Lupascu L., Valica V., Uncu L., Smetanscaia A., Drumea M., Petrou A., Ciric A., Glamoclija J., Sokovic M., Kravtsov V., Geronikaki A., Macaev F. New vinyl-1,2,4-triazole derivatives as antimicrobial agents: Synthesis, biological evaluation and molecular docking studies. Bioorganic and Medicinal Chemistry Letters, 2020, 30(17), 127368). Also, the compound of the invention has a reduced cost compared to that of the closest solution, because its synthesis takes place in one step compared to 3 steps, characteristic of the closest solution, and consists in the use of the ketone: 4-methyl-1-(1H-1,2,4-triazol-1-yl)pentan-2-one. The synthesis process involves the interaction of the aforementioned ketone with 2,4-dichlorobenzaldehyde in benzene in the presence of piperidine and acetic acid (catalytic amounts), which leads to the formation of a single isomer - (Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-1-en-3-one with a melting point of 92-93°С (Stingaci E., Zveaghinteva M., Pogrebnoi S., Lupascu L., Valica V., Uncu L., Smetanscaia A., Drumea M., Petrou A., Ciric A., Glamoclija J., Sokovic M., Kravtsov V., Geronikaki A., Macaev F. New vinyl-1,2,4-triazole derivatives as antimicrobial agents: Synthesis, biological evaluation and molecular docking studies. Bioorganic and Medicinal Chemistry Letters, 2020, 30(17), 127368).
Rezultatul tehnic al invenţiei constă în aceea că tratarea boabelor de grâu comun de toamnă din cadrul liniei Moldova x Moldova 3 (L M/M3), în prezenţa fungilor F. oxysporum şi D. sorokiniana, cu compusul (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ona în concentraţiile de 0,005% şi 0,01% timp de 3 ore contribuie la sporirea masei uscate per plantă cu 10,49…35,09% în cazul F. oxysporum şi cu 14,21…25,81% în cazul D. sorokiniana, în comparaţie cu cea mai apropiată soluţie. The technical result of the invention consists in the fact that the treatment of common winter wheat grains from the Moldova x Moldova 3 line (L M/M3), in the presence of the fungi F. oxysporum and D. sorokiniana, with the compound (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one in concentrations of 0.005% and 0.01% for 3 hours contributes to the increase in dry mass per plant by 10.49…35.09% in the case of F. oxysporum and by 14.21…25.81% in the case of D. sorokiniana, compared to the closest solution.
Exemplu de realizare a invenţiei Example of embodiment of the invention
În calitate de material pentru cercetare au servit: 1) boabe de grâu comun de toamnă a genotipului L M/M3; 2) filtrate de culturi (FC) ale fungilor Fusarium oxysporum şi Drechslera sorokiniana; 3) derivaţii vinil-triazolici: (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ona (invenţia) şi (E)-1-(2,4-diclorofenil)-4,4-dimetil-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ol (soluţia cea mai apropiată) în concentraţii de 0,005% şi 0,01%. Filtratele de culturi au fost pregătite prin inocularea miceliului fungului la mediul nutritiv lichid Cszapek (conform compoziţiei descrise în Tuite J. Plant Pathological methods (Fungi and Bcteria). Burgess Publishing Company, Minneapolis, 1969, 239 p.). The following materials were used for the research: 1) grains of common winter wheat of the L M/M3 genotype; 2) culture filtrates (FC) of the fungi Fusarium oxysporum and Drechslera sorokiniana; 3) vinyl-triazole derivatives: (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one (the invention) and (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (the closest solution) in concentrations of 0.005% and 0.01%. Culture filtrates were prepared by inoculating the fungal mycelium to Cszapek liquid nutrient medium (according to the composition described in Tuite J. Plant Pathological methods (Fungi and Bacteria). Burgess Publishing Company, Minneapolis, 1969, 239 p.).
Boabele de grâu bine selectate în baza uniformităţii şi mărimii au fost tratate timp de 3 ore cu emulsii de: (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ona (invenţia) şi (E)-1-(2,4-diclorofenil)-4,4-dimetil-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ol (soluţia cea mai apropiată) în concentraţii de 0,005% şi 0,01%, după care s-au uscat în aer liber la temperatură de cameră, timp de 48 ore. Ulterior boabele au fost menţinute pentru 18 ore în FC F. oxysporum şi D. sorokiniana, apoi clătite cu apă distilată şi plasate în cutii Petri între 2 foiţe de hârtie de filtru umectată în apă distilată şi menţinute la temperatura de 19-20ºC timp de 5 zile. Wheat grains well selected based on uniformity and size were treated for 3 hours with emulsions of: (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one (the invention) and (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol (the closest solution) in concentrations of 0.005% and 0.01%, after which they were dried in the open air at room temperature for 48 hours. Subsequently, the grains were maintained for 18 hours in FC F. oxysporum and D. sorokiniana, then rinsed with distilled water and placed in Petri dishes between 2 sheets of filter paper moistened in distilled water and maintained at a temperature of 19-20ºC for 5 days.
Emulsiile preparatelor au fost obţinute prin adăugare de dimetilsulfoxid de 9%, emulgator TWIN-80 de 20% şi etanol de 70% la compusul din invenţie şi cel din cadrul soluţiei apropiate, luaţi în concentraţie de 1%. The emulsions of the preparations were obtained by adding 9% dimethyl sulfoxide, 20% TWIN-80 emulsifier and 70% ethanol to the compound of the invention and that of the related solution, taken in a concentration of 1%.
În calitate de martor I au servit boabele muiate timp de 18 ore în apă distilată, iar martor II - boabele muiate timp de 18 ore în FC F. oxysporum şi D. sorokiniana. Experienţa a fost efectuată în 3 repetiţii, câte 30 de boabe fiecare. În calitate de criteriu al rezistenţei la patogen a servit masa uscată în aer liber per plantă (mg), stabilită prin cântărire. Datele au fost prelucrate statistic în pachetul de soft STATISTICA 8. As control I, the grains soaked for 18 hours in distilled water were used, and control II - the grains soaked for 18 hours in FC F. oxysporum and D. sorokiniana. The experiment was carried out in 3 repetitions, 30 grains each. As a criterion of resistance to the pathogen, the dry mass in the open air per plant (mg), established by weighing, served. The data were statistically processed in the STATISTICA 8 software package.
Conform datelor din tabelul 1, s-a constatat că FC F. oxysporum a afectat negativ acumularea de biomasă. Astfel, masa uscată per plantă în varianta cu ciupercă a constituit 53,62% din varianta martor I, ceea ce denotă impactul negativ puternic al acesteia asupra creşterii şi dezvoltării plantelor de grâu. According to the data in Table 1, it was found that FC F. oxysporum negatively affected biomass accumulation. Thus, the dry mass per plant in the fungus variant constituted 53.62% of the control variant I, which denotes its strong negative impact on the growth and development of wheat plants.
Tabelul 1 Table 1
Influenţa variantelor de studiu asupra biomasei uscate a plantulelor de grâu la interacţiunea acestora cu F. oxysporum (Linia M/M3) Influence of study variants on the dry biomass of wheat seedlings during their interaction with F. oxysporum (Line M/M3)
Nr. Variantă Biomasa uscată per plantă, mg Σ Raport la FC, % 1 H2O - Martor I 16,58±0,53 0,92 186,50 2 FC F. oxysporum - Martor II 8,89±0,69v 0,97 - 3 Compusul din cadrul celei mai apropiate soluţii - 0,01% + FC F. oxysporum 10,80±0,98 1,70 121,49 4 Compusul din cadrul celei mai apropiate soluţii - 0,005% + FC F. oxysporum 11,62±0,31* 0,54 130,71 6 Compusul din invenţie - 0,01% + FC F. oxysporum 14,59±0,31* 0,44 164,12 7 Compusul din invenţie - 0,005% + FC F. oxysporum 12,84±0,39* 0,68 144,43No. Variant Dry biomass per plant, mg Σ Ratio to FC, % 1 H2O - Control I 16.58±0.53 0.92 186.50 2 FC F. oxysporum - Control II 8.89±0.69v 0.97 - 3 Compound from the closest solution - 0.01% + FC F. oxysporum 10.80±0.98 1.70 121.49 4 Compound from the closest solution - 0.005% + FC F. oxysporum 11.62±0.31* 0.54 130.71 6 Compound from the invention - 0.01% + FC F. oxysporum 14.59±0.31* 0.44 164.12 7 Compound from the invention - 0.005% + FC F. oxysporum 12.84±0.39* 0.68 144.43
*- diferenţă statistic semnificativă în raport cu FC F. oxysporum, p≤0,05. *- statistically significant difference compared to FC F. oxysporum, p≤0.05.
v- diferenţă statistic semnificativă în raport cu Martor I, p≤0,05. v- statistically significant difference compared to Control I, p≤0.05.
Σ - deviaţia standard. Σ - standard deviation.
Se atestă şi în acest caz că masa uscată per plantă în varianta cu ciupercă a constituit 82% din varianta martor I, ceea ce denotă impactul negativ al acesteia asupra creşterii şi dezvoltării plantelor de grâu (Tabelul 2). It is also shown in this case that the dry mass per plant in the variant with fungus constituted 82% of the control variant I, which denotes its negative impact on the growth and development of wheat plants (Table 2).
Tabelul 2 Table 2
Influenţa variantelor de studiu asupra biomasei uscate a plantulelor de grâu la interacţiunea acestora cu D. sorokiniana (Linia M/M3) Influence of study variants on the dry biomass of wheat seedlings in their interaction with D. sorokiniana (Line M/M3)
Nr. Variantă Biomasa uscată per plantă, mg Σ Raport la FC, % 1 H2O - Martor I 10,56±0,59 1,01 121,94% 2 FC D. sorokiniana - Martor II 8,66±0,14v 0,23 - 3 Compusul din cadrul celei mai apropiate soluţii - 0,01% + FC D. sorokiniana 7,05±0,66 1,14 81,41 4 Compusul din cadrul celei mai apropiate soluţii - 0,005% + FC D. sorokiniana 9,08±0,28* 0,48 104,85 6 Compusul din invenţie - 0,01% + FC D. sorokiniana 8,87±0,44 0,76 102,43 7 Compusul din invenţie - 0,005% + FC D. sorokiniana 10,37±0,12* 0,21 119,75No. Variant Dry biomass per plant, mg Σ Ratio to FC, % 1 H2O - Control I 10.56±0.59 1.01 121.94% 2 FC D. sorokiniana - Control II 8.66±0.14v 0.23 - 3 Compound from the closest solution - 0.01% + FC D. sorokiniana 7.05±0.66 1.14 81.41 4 Compound from the closest solution - 0.005% + FC D. sorokiniana 9.08±0.28* 0.48 104.85 6 Compound from the invention - 0.01% + FC D. sorokiniana 8.87±0.44 0.76 102.43 7 Compound from the invention - 0.005% + FC D. sorokiniana 10.37±0.12* 0.21 119.75
*- diferenţă statistic semnificativă în raport cu FC D. sorokiniana, p≤0,05. *- statistically significant difference compared to FC D. sorokiniana, p≤0.05.
v- diferenţă statistic semnificativă în raport cu Martor I, p≤0,05. v- statistically significant difference compared to Control I, p≤0.05.
Σ - deviaţia standard. Σ - standard deviation.
Datele obţinute denotă că tratarea boabelor de grâu comun de toamnă din cadrul liniei Moldova x Moldova 3 (L M/M3), în prezenţa fungilor F. oxysporum şi D. sorokiniana, cu compusul (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ona în concentraţii de 0,005% şi 0,01% timp de 3 ore contribuie la sporirea masei uscate per plantă cu 10,49…35,09% în cazul F. oxysporum şi cu 14,21…25,81% în cazul D. sorokiniana, în comparaţie cu cea mai apropiată soluţie, ceea ce denotă că preparatul contribuie la sporirea rezistenţei grâului la aceşti patogeni şi prezintă o oportunitate de utilizare a acestuia în măsurile de protecţie a grâului comun de toamnă de agenţii cauzali ai putregaiului de rădăcină. The obtained data show that the treatment of common winter wheat grains from the Moldova x Moldova 3 line (L M/M3), in the presence of the fungi F. oxysporum and D. sorokiniana, with the compound (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-one in concentrations of 0.005% and 0.01% for 3 hours contributes to the increase of dry mass per plant by 10.49…35.09% in the case of F. oxysporum and by 14.21…25.81% in the case of D. sorokiniana, compared to the closest solution, which indicates that the preparation contributes to the increase of wheat resistance to these pathogens and presents an opportunity for its use in the protection measures of common winter wheat from the causative agents of root rot. root.
1. MD 685 F1 1997.03.31 1. MD 685 F1 1997.03.31
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