MD1604Z - Process for treating common winter wheat grains - Google Patents
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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 fungilor F. oxysporum. The invention relates to agriculture and chemistry, namely to a process for treating common winter wheat grains to increase resistance to the action of the fungi F. oxysporum.
Tratarea seminţelor/boabelor 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/grain treatment is a method of neutralizing most pathogens (fungal and bacterial), pests that 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 este considerat una din cele mai răspândite boli la plantele de cultură, inclusiv la grâul comun de toamnă Triticum aestivum L (Kiecana I., Cegiełko M., Rachoń L. et al. The occurrence of fungi on roots and stem bases of Triticum aestivum ssp. spelta L. Thell. grown under two levels of chemical protection and harmfulness of Fusarium graminearum Schwabe to seedlings of selected genotypes. Acta Agrobot., 2016, 69(3), p. 1657). Root rot is considered one of the most widespread diseases in crop plants, including common winter wheat Triticum aestivum L (Kiecana I., Cegiełko M., Rachoń L. et al. The occurrence of fungi on roots and stem bases of Triticum aestivum ssp. spelta L. Thell. grown under two levels of chemical protection and harmfulness of Fusarium graminearum Schwabe to seedlings of selected genotypes. Acta Agrobot., 2016, 69(3), p. 1657).
Maladia este cauzată de diverşi patogeni din sol, printre care fungii Fusarium se remarcă cu incidenţă şi severitate avansată (Moya-Elizondo E.A., Rew L.J., Jacobsen B.J. et al. Distribution and Prevalence of Fusarium Crown Rot and Common Root Rot Pathogens of Wheat in Montana. Plant Disease, 2011, v. 95, nr. 9, p. 1099-1108). Aceşti patogeni reduc biomasa plantelor din cauza obstrucţionării pătrunderii apei şi substanţelor nutritive în plantă (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). Unele din cauzele managementului ineficient al rezistenţei plantelor la patogenii din sol care cauzează putregaiul de rădăcină sunt costul ridicat al fungicidelor chimice şi dezvoltarea rezistenţei la fungicide (Panth M., Hassler S.C., Baysal-Gurel F. Methods for Management of Soilborne Diseases in Crop Production. Agriculture, 2020, v. 10(1), 16). Din acest motiv este necesară identificarea noilor procedee eficiente pentru protejare de astfel de maladii. The disease is caused by various soil-borne pathogens, among which Fusarium fungi stand out with advanced incidence and severity (Moya-Elizondo E.A., Rew L.J., Jacobsen B.J. et al. Distribution and Prevalence of Fusarium Crown Rot and Common Root Rot Pathogens of Wheat in Montana. Plant Disease, 2011, v. 95, no. 9, p. 1099-1108). These pathogens reduce plant biomass by obstructing the penetration of water and nutrients into the plant (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). Some of the causes of ineffective management of plant resistance to soil-borne pathogens that cause root rot are the high cost of chemical fungicides and the development of fungicide resistance (Panth M., Hassler S.C., Baysal-Gurel F. Methods for Management of Soilborne Diseases in Crop Production. Agriculture, 2020, v. 10(1), 16). For this reason, it is necessary to identify new effective procedures for protection against such diseases.
Este cunoscut un procedeu de protecţie al plantelor de fungi fitopatogeni cu utilizarea compusului (E)-1-(2,4-diclorfenil)-4,4-dimetil-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ol (Diniconazol) [1]. Dezavantajul constă în aceea că procedeul nu conduce la o protecţie antifungică suficient de înaltă faţă de fungii F. oxysporum. A process for protecting plants from phytopathogenic fungi 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) is known [1]. The disadvantage is that the process does not lead to a sufficiently high antifungal protection against the fungus F. oxysporum.
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 care să asigure sporirea rezistenţei plantelor de grâu la acţiunea F. oxysporum. 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 ensure increased resistance of wheat plants to the action of F. oxysporum.
Procedeul, conform invenţiei, constă în tratarea boabelor de grâu comun de toamnă cu soluţie apoasă a compusului (Z)-1-(2,4-diclorfenil)-5-metil-2-(1H-1,2,4-triazol-1-il)hex-1-en-3-onă cu formula: The process, according to the invention, consists of treating common winter wheat grains with an aqueous solution of the compound (Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-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.
Avantajul invenţiei constă în aceea că utilizarea în procedeul revendicat a compusului (Z)-1-(2,4-diclorfenil)-5-metil-2-(1H-1,2,4-triazol-1-il)hex-1-en-3-onă contribuie la sporirea rezistenţei plantelor la acţiunea F. oxysporum în raport cu soluţia cea mai apropiată. The advantage of the invention lies in the fact that the use of the compound (Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-1-en-3-one in the claimed process contributes to increasing the resistance of plants to the action of F. oxysporum 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, comparativ cu cea mai apropiată soluţie 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 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-diclorofenil)-5-metil-2-(1H-1,2,4-triazol-1-il)hex-1-en-3-onă 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, compared to the closest solution and consists of using 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 conform invenţiei contribuie la sporirea masei uscate per plantă cu 9,99-30,47% 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 according to the invention contributes to increasing the dry mass per plant by 9.99-30.47% 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 2 genotipuri - L SBS şi L M/M3; 2) filtratul de cultură (FC) al fungilor Fusarium oxysporum; 3) derivaţii vinil-triazolici ((Z)-1-(2,4-diclorfenil)-5-metil-2-(1H-1,2,4-triazol-1-il)hex-1-en-3-ona) -invenţia şi (E)-1-(2,4-diclorfenil)-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%. FC F. oxysporum a fost pregătit prin inocularea miceliului fungic în mediul nutritiv lichid Cszapek (conform compoziţiei descrise în Tuite J. Plant Pathological methods (Fungi and Bacteria). Burgess Publishing Company, Minneapolis, 1969, 239 p.). The following materials were used for the research: 1) common winter wheat grains of 2 genotypes - L SBS and L M/M3; 2) culture filtrate (FC) of the fungus Fusarium oxysporum; 3) vinyl-triazole derivatives ((Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-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%. FC F. oxysporum was prepared by inoculating fungal mycelium into 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 ale compusului din inventie: (Z)-1-(2,4-diclorfenil)-5-metil-2-(1H-1,2,4-triazol-1-il)hex-1-en-3-onă şi al analogului proxim: (E)-1-(2,4-diclorfenil)-4,4-dimetil-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-ol 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, apoi clătite cu apă distilată şi plasate în cutii Petri între 2 foiţe de hârtie de filtru umectată cu apă distilată şi menţinute la temperatura de 19-20ºC timp de 6 zile. Wheat grains well selected based on uniformity and size were treated for 3 hours with emulsions of the compound of the invention: (Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-1-en-3-one and of the close analogue: (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol 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, then rinsed with distilled water and placed in Petri dishes between 2 sheets of filter paper moistened with distilled water and maintained at a temperature of 19-20ºC for 6 days.
Emulsiile preparatelor au fost obţinute prin adaugare 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. Experienţa a fost efectuată în 3 repetiţii, câte 30 de boabe în fiecare. În calitate de criteriu al rezistenţei/sensibilităţii 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. The experiment was carried out in 3 repetitions, 30 grains each. As a criterion of resistance/susceptibility 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.
Datele prezentate în Tabelul 1 relevă că FC F. oxysporum (Martor II) a contribuit la diminuarea semnificativă a masei uscate a plantelor de grâu L SBS în raport cu plantele dezvoltate din boabele tratate cu apă distilată (Martor I), ceea ce denotă virulenţa înaltă a tulpinii utilizate în calitate de agent patogen al putregaiului de rădăcină. The data presented in Table 1 reveal that FC F. oxysporum (Control II) contributed to a significant decrease in the dry mass of L SBS wheat plants compared to plants developed from grains treated with distilled water (Control I), which denotes the high virulence of the strain used as a root rot pathogen.
Este de menţionat că fungii F.oxysporum îsi manifestă potentialul său fitopatogen destul de semnificativ, biomasa uscată fiind cu 27,48% mai puţină decât în varianta Martor I. Conform datelor din Tabelul 1, compusul din invenţie îşi manifestă potenţialul său stimulator la un nivel mai înalt în comparaţie cu cel din cadrul celei mai apropiate soluţii pentru ambele concentraţii luate în studiu. În cazul concentraţiei de 0,01% sporul a constituit 20,37%, iar pentru varianta de 0,005% - 9,99%. It is worth mentioning that the fungi F.oxysporum manifests its phytopathogenic potential quite significantly, the dry biomass being 27.48% less than in the Control I variant. According to the data in Table 1, the compound of the invention manifests its stimulatory potential at a higher level compared to that of the closest solution for both concentrations studied. In the case of the 0.01% concentration, the sporulation constituted 20.37%, and for the 0.005% variant - 9.99%.
Tabelul 1 Table 1
Influenţa variantelor de studiu asupra biomasei uscate a plantulelor de grâu la interacţiunea acestora cu F. oxysporum (Linia SBS) Influence of study variants on dry biomass of wheat seedlings upon their interaction with F. oxysporum (SBS Line)
Nr. Variantă Biomasa uscată per plantă, mg Σ Raport la FC, % 1 H2O - Martor I 10,77±0,39 0,68 137,9 2 FC F. oxysporum - Martor II 7,81±0,23v 0,39 - 3 Compusul din cadrul celei mai apropiate soluţii - 0,01% + FC F. oxysporum 8,48±0,25 0,35 108,58 4 Compusul din cadrul celei mai apropiate soluţii - 0,005% + FC F. oxysporum 9,28±0,31 0,44 118,82 5 Compusul din invenţie - 0,01% + FC F. oxysporum 10,65±0,06* 0,10 136,36 6 Compusul din invenţie - 0,005% + FC F. oxysporum 10,31±0,04* 0,07 132,01No. Variant Dry biomass per plant, mg Σ Ratio to FC, % 1 H2O - Control I 10.77±0.39 0.68 137.9 2 FC F. oxysporum - Control II 7.81±0.23v 0.39 - 3 Compound from the closest solution - 0.01% + FC F. oxysporum 8.48±0.25 0.35 108.58 4 Compound from the closest solution - 0.005% + FC F. oxysporum 9.28±0.31 0.44 118.82 5 Compound from the invention - 0.01% + FC F. oxysporum 10.65±0.06* 0.10 136.36 6 Compound from the invention - 0.005% + FC F. oxysporum 10.31±0.04* 0.07 132.01
*- 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.
În ceea ce priveşte genotipul L M/M3 (Tabelul 2), s-a constatat că FC F. oxysporum (Martor II) a contribuit la diminuarea cu 46,38% a masei uscate a plantelor în raport cu plantele dezvoltate din boabele tratate cu apă distilată (Martor I), ceea ce denotă sensibilitatea înaltă a genotipului pentru tulpina utilizată în studiu. Regarding the L M/M3 genotype (Table 2), it was found that FC F. oxysporum (Control II) contributed to a 46.38% decrease in plant dry mass compared to plants developed from grains treated with distilled water (Control I), which denotes the high sensitivity of the genotype for the strain used in the study.
Conform datelor din Tabelul 2, compusul din invenţie îşi manifestă potenţialul său stimulator la un nivel mai înalt în comparaţie cu cel din cadrul celei mai apropiate soluţii pentru ambele concentraţii luate în studiu. În cazul concentraţiei de 0,01% sporul a constituit 27%, iar a concentraţiei de 0,005% - 30,47%. According to the data in Table 2, the compound of the invention manifests its stimulatory potential at a higher level compared to that of the closest solution for both concentrations studied. In the case of the 0.01% concentration, the increase was 27%, and in the case of the 0.005% concentration - 30.47%.
Tabelul 2 Table 2
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 dry biomass of wheat seedlings upon 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 11,29±0,64 1,12 127,00 5 Compusul din invenţie - 0,01% + FC F. oxysporum 13,72±0,69* 1,20 154,33 6 Compusul din invenţie - 0,005% + FC F. oxysporum 14,73±0,24* 0,41 165,69No. 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 11.29±0.64 1.12 127.00 5 Compound from the invention - 0.01% + FC F. oxysporum 13.72±0.69* 1.20 154.33 6 Compound from the invention - 0.005% + FC F. oxysporum 14.73±0.24* 0.41 165.69
*- 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.
Astfel, procedeul de tratare a boabelor de grâu comun de toamnă la liniile M/M3 şi SBS cu compusul (Z)-1-(2,4-diclorfenil)-5-metil-2-(1H-1,2,4-triazol-1-il)hex-1-en-3-onă în concentraţii de 0,005% şi 0,01% timp de 3 ore, în prezenţa fungilor F. oxysporum, a contribuit la sporirea masei uscate per plantă cu 9,99-30,47% în comparaţie cu cea mai apropiată soluţie. Thus, the treatment process of common winter wheat grains in the M/M3 and SBS lines with the compound (Z)-1-(2,4-dichlorophenyl)-5-methyl-2-(1H-1,2,4-triazol-1-yl)hex-1-en-3-one in concentrations of 0.005% and 0.01% for 3 hours, in the presence of F. oxysporum fungi, contributed to increasing the dry mass per plant by 9.99-30.47% compared to the closest solution.
1. MD 685 F1 1997.03.31 1. MD 685 F1 1997.03.31
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