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CN1923819A - compound containing aromatic ether and ditriazole and use thereof - Google Patents

compound containing aromatic ether and ditriazole and use thereof Download PDF

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Publication number
CN1923819A
CN1923819A CN200610140836.7A CN200610140836A CN1923819A CN 1923819 A CN1923819 A CN 1923819A CN 200610140836 A CN200610140836 A CN 200610140836A CN 1923819 A CN1923819 A CN 1923819A
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acid
aryl oxide
triazole compounds
agroforestry
fungal disease
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CN100451007C (en
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许良忠
吴华龙
胡志强
朱琪
于观平
毕文照
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Zhejiang Yulong Pharmaceutical Co ltd
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Qingdao University of Science and Technology
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Abstract

The invention discloses a diribavirin compound with aromatic ether and application, which possesses structural formula as formula (I) or antimer of formula (I), wherein R1, R2, R3, R4, R5, R6 is hydrogen, C1-4, trifluoromethyl, methoxyl, nitro group or halogen; the C1-4 alkyl is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, parabutyl or tert-butyl group; the atom is F, Cl, Br or I; the compound displays strong fungi inhibiting activity, which can prepare fungi inhibitor.

Description

Contain two triazole compounds of aryl oxide and uses thereof
Technical field
The present invention relates to agricultural and use the sterilant field, particularly a kind ofly contain the two triazole compounds of aryl oxide and acid salt thereof, metal-salt mixture, and the preparation method and as agricultural with sterilant in the purposes of preventing and treating on the agroforestry fungal disease.
Background technology
Endangering animals and plants and making the morbific harmful organism of animals and plants mainly is fungi, bacterium and virus.For plant, the main disease of plant is a fungal disease.The commercial sterilizing disease-preventing medicament overwhelming majority is a mycocide, and bactericide is then very few, and the diseases prevention toxic agent is very few for number.One of factor is exactly that fungal disease has general property, and harm that causes and loss are also maximum.In numerous fungal disease control agent, triazole bactericidal agent is typical fungicidal type.Over nearly 30 years, triazole bactericidal agent is efficient with it, low toxicity, wide spectrum and enjoy favor, and moreover, most triazole bactericidal agents have the plant biological regulatory function simultaneously.Triazole bactericidal agent is interior suction therapeutic type sterilant but then, and mechanism of action and action site are single, long-term frequent use, and disease has produced more serious resistance, and many kinds are because resistance problem has lost original high efficiency.As triazolone control powdery mildew of strawberry, the few preventive effect of consumption is low, and consumption greatly then easily produces poisoning, suppresses the strawberry growth.Thereby the triazole bactericidal agent of development of new just becomes the task of top priority.
English Patent GB2078719A discloses the two triazole compounds with fungicidal activity, but its substituting group of the disclosed compound of this patent does not comprise aryl ether group.The invention provides the new two triazole class sterilant of aryl oxide that contain, the part of compounds bacteriostatic activity is suitable with commercialization triazole bactericidal agent tebuconazole, Difenoconazole, has good commercialization prospect.
Summary of the invention
Technical problem to be solved by this invention be to provide a kind of have a high biological activity contain the two triazole compounds of aryl oxide and acid salt thereof, metal-salt mixture as agricultural with sterilant.
Another technical problem to be solved by this invention is to provide a kind of above-mentioned two triazole compounds of aryl oxide and acid salt thereof, metal-salt mixture of containing in the application that prevents and treats on the agroforestry fungal disease, these diseases are fungus-caused by a plurality of genus that are under the jurisdiction of Ascomycota, Basidiomycota, imperfect fungi door mostly, as Staphlosporonites, interlink spore genus, black star spore genus, Verticillium, reaping hook genus, spherical shell spore genus etc.For solving the problems of the technologies described above, the invention provides a kind of two triazole compounds of aryl oxide that contain, have following structural formula (I) or described structural formula (I) acceptable enantiomorph on agricultural pharmacology:
Wherein, R 1, R 2, R 3, R 4, R 5, R 6Be hydrogen, C 1~4Alkyl, trifluoromethyl, methoxyl group, nitro or halogen;
Described C 1~4Alkyl is methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl or the tertiary butyl;
Described halogen atom is fluorine, chlorine, bromine or iodine.
Described R 1, R 2, R 3, R 4, R 5, R 6Substituting group can be the same or different.
The acid of described acid salt can be in hydrochloric acid, Hydrogen bromide, nitric acid, sulfuric acid, phosphoric acid, hydroiodic acid HI, hydrofluoric acid, perchloric acid, tosic acid, methylsulfonic acid, acetate, citric acid, tartrate, oxysuccinic acid, oxalic acid, fumaric acid or the phthalic acid one or more.
The metal-salt mixture of the two triazole compounds of described aryl oxide is characterized in that having following structural formula (II):
Figure A20061014083600052
Wherein, R 1, R 2, R 3, R 4, R 5, R 6Be hydrogen, C 1~4Alkyl, trifluoromethyl, methoxyl group, nitro or halogen;
Described C 1~4Alkyl is methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl or the tertiary butyl;
Described halogen atom is fluorine, chlorine, bromine or iodine;
Described M is the period of element Table II A, IV A, I B, II B, VI B, VII BOr the positively charged ion of VIII family;
Described Y is the negatively charged ion of neutralizing cation M electric charge.
Described contain the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease.
Described contain the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease, described agroforestry fungal disease is fungus-caused by the one or more genus that are under the jurisdiction of Ascomycota, Basidiomycota, imperfect fungi door.
Described contain the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease, described agroforestry fungal disease be by Staphlosporonites, interlink spore genus, black star spore genus, Verticillium, reaping hook belongs to or one or more of spherical shell spore genus are fungus-caused.
The described acid salt that contains the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease.
The metal-salt mixture of the two triazole compounds of described aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease.
Compound provided by the invention not only has higher biological activity, and low with the analogous products comparative cost of production, is the disinfectant use in agriculture new variety that application prospect is arranged very much.
Embodiment
The present invention contains the two triazole class fungicide compounds (I) of aryl oxide and agricultural goes up acceptable acid salt and metal-salt mixture, and general formula is:
Wherein, R 1, R 2, R 3, R 4, R 5, R 6Be H, C 1~4Alkyl, trifluoromethyl, methoxyl group, nitro or halogen, R 1, R 2, R 3, R 4, R 5, R 6Can be identical or different;
Above-mentioned C 1~4Alkyl is methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl, the tertiary butyl; Above-mentioned halogen atom is fluorine, chlorine, bromine, iodine.
In table 1 triazole class compounds of the present invention The chemical structure of group for example
Routine number R 1 R 2 R 3 R 4 R 5 R 6
1 H H H H H H
2 H H Cl H H 6-Cl
3 Cl H Cl H H H
4 H H Cl H H H
5 H Cl H 5-Cl H H
6 H Cl H 6-Cl H H
7 H Cl H H H H
8 H Br H H H H
9 H H CH 3 H H H
10 CH 3 H CH 3 H H H
11 F H H H H H
12 H F H H H H
13 H H F H H H
14 Br H H H H H
15 H H Br H H H
16 C 2H 5 H H H H H
17 H H C 4H 9-t H H H
18 OCH 3 H H H H H
19 H H NO 2 H H H
20 CF 3 H H H H H
21 H H CF 3 H H H
22 Br H Br H H H
23 Br H Cl H H H
24 Cl H Br H H H
25 H Cl Cl 6-Cl H H
26 CH 3 H Cl H H H
27 NO 2 H CF 3 H H H
28 NO 2 H NO 2 6-CF 3 H H
29 Cl Cl H H H H
30 CH 3 H H H 2-CH 3 H
31 H H Cl H 2-CH 3 H
32 Cl H CF 3 H H H
33 Cl H CF 3 H H 6-Cl
34 H H Cl H 2-CH 3 H
35 H F H H 2-CH 3 H
36 CH 3 H H H 2-CH 3 H
37 H H OCH 3 H 2-CH 3 H
38 H H F H 2-CH 3 H
39 OCH 3 H H H 2-Cl H
40 H H F H 2-OCH 3 H
41 H H Cl H 3-Cl H
42 H H Cl H 2-C 2H 5 H
43 H H H H 2-CH 3 H
44 H H H H 2-Cl H
45 H H H H 3-CH 3 H
46 H H H H 2-CH 3 5-CH 3
47 H H H H 2-C 2H 5 H
48 H H CF 3 H 3-Cl H
49 H H F H H 6-Cl
50 H H F H H 6-F
Title compound (I) can be directly with the preparation disinfectant use in agriculture, also can the agriculture form that goes up the acceptable acid salt prepare disinfectant use in agriculture, acid comprises hydrochloric acid, Hydrogen bromide, nitric acid, sulfuric acid, phosphoric acid, hydroiodic acid HI, hydrofluoric acid, perchloric acid, tosic acid, methylsulfonic acid, acetate, citric acid, tartrate, oxysuccinic acid, oxalic acid, fumaric acid and phthalic acid.
Another embodiment of the present invention is the metal-salt mixture (II) of formula (I):
Figure A20061014083600081
R wherein 1, R 2, R 3, R 4, R 5And R 6Definition cotype (I), M is for being selected from the period of element Table II A, IV A, I B, II B, VI B, VII BWith the positively charged ion of VIII family, Y is used for the negatively charged ion of the electric charge of neutralizing cation M for selection.
The typical positively charged ion of the present invention is magnesium, copper, nickel, zinc, iron, cobalt, calcium, tin, chromium, mercury, barium etc.
The typical negatively charged ion of the present invention is chlorine, bromine, iodine, fluorine, thiocyanate ion, sulfate radical, bisulfate ion, perchlorate, nitrate radical, nitrite anions, phosphate radical, carbonate, bicarbonate radical, oxalate, tartrate anion, malate, horse Lay acid group, fumaric acid radical, tosic acid root, methanesulfonate etc.
Having of greater activity arranged among the present invention:
Compound 2 α-(2-chloro-4-(4-chlorophenoxy) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2,4-triazol-1-yl ethanol
Figure A20061014083600091
Compound 33 α-(2-chloro-4-(2-chloro-4-4-trifluoromethylphenopendant) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2,4-triazol-1-yl ethanol
Figure A20061014083600092
Compound 32 α-(4-(2-chloro-4-4-trifluoromethylphenopendant) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2,4-triazol-1-yl ethanol
Compound 50 α-(2-fluoro-4-(4-fluorophenoxy) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2,4-triazol-1-yl ethanol
Compound with structural formula (I) of the present invention can be made as follows:
R in the formula 1, R 2, R 3, R 4, R 5And R 6Implication is same as above.
Reaction by ether ketone be raw material through bromo, azanylization, epoxidation is last reacts open loop with triazole and get target compound.Concrete reaction conditions is as follows:
Example I: α-(2-chloro-4-(4-chlorophenoxy) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2, the preparation of 4-triazol-1-yl alcoholic acid
2-bromo-1-(2-chloro-4-(4-chlorophenoxy) phenyl) ethyl ketone
In the 500mL four-necked bottle, add 280g (1.0mol) 2-chloro-4-(4-chlorophenoxy) methyl phenyl ketone, 200mL hexanaphthene, stirring at room, drip 192g (1.2mol) bromine, add 2~3 earlier, solution takes on a red color, wait redness to take off after, more remaining bromine is dripped into, the control rate of addition, about 3h drips off.Keep temperature of reaction and continue to stir 2h to color fade, stopped reaction.Reaction solution is poured in the 500mL separating funnel, washed with water, branch vibration layer is washed to organic phase repeatedly and is neutral, tells organic phase, spends the night with anhydrous magnesium sulfate drying.Elimination sal epsom removes hexanaphthene under reduced pressure, gets faint yellow solid, and recrystallization gets white crystal 335.2g, yield 93.1%.Fusing point: 50~51 ℃.
The preparation of 2-(1H-1,2,4-triazol-1-yl)-1-(2-chloro-4-(4-chlorophenoxy) phenyl) ethyl ketone
In the 500mL four-necked bottle, add 180g (0.5mol) 2-bromo-1-(2-chloro-4-(4-chlorophenoxy) phenyl) ethyl ketone, 51.8g (0.75mol) triazole, 103.5g (0.75mol) potassium carbonate powder and 200mL ethyl acetate respectively, heating reflux reaction 6h, filter, filtrate subtracts steaming, get light yellow solid, recrystallization gets white solid 117.2g, yield 67.3%, fusing point: 151~154 ℃.
1-[2-(2-chloro-4-(4-chlorophenoxy) phenyl)-2, the 3-epoxypropyl]-1H-1,2, the preparation of 4-triazole mesylate
Get 2-(1H-1,2, the 4-triazol-1-yl)-and 1-(2-chloro-4-(4-chlorophenoxy) phenyl) ethyl ketone 34.8g (0.1mol), iodate trimethylammonium oxygen sulphur 26.4g (0.12mol), trimethylammonium hexadecyl brometo de amonio 0.3g and toluene 100mL put into the 250mL three-necked bottle, be warming up to 60 ℃, stir the sodium hydroxide solution 80mL of dropping 20% down, 2h drips off, and is incubated 60 ℃ and continues to stir 3 hours, isolate toluene layer, be concentrated into 25mL.Debris adds the dilution of 15mL ethyl acetate, 0 ℃ drips down and is dissolved with the ethyl acetate solution 5mL of 9.6g methylsulfonic acid, adds the ethyl acetate dilution again, 0 ℃ was stirred one hour down, get faint yellow precipitation 1-[2-(2-chloro-4-(4-chlorophenoxy) phenyl)-2, the 3-epoxypropyl]-1H-1,2,4-triazole mesylate, the crude product recrystallization is got faint yellow solid 32.2g, yield 70.2%, fusing point: 130~134 ℃.
α-(2-chloro-4-(4-chlorophenoxy) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2, the preparation of 4-triazol-1-yl alcoholic acid
In 50mL single port flask, add 1-[2-(2-chloro-4-(4-chlorophenoxy) phenyl)-2, the 3-epoxypropyl]-1H-1,2,4-triazole mesylate 4.6g (0.01mol), triazole 0.8g (0.012mol), potassium carbonate powder 1.4g (0.01mol) and N, dinethylformamide 20mL, back flow reaction 6h pours reaction solution in the water into, and the adularescent solid is separated out, suction filtration gets α-(2-chloro-4-(4-chlorophenoxy) phenyl)-α-(1H-1,2,4-triazol-1-yl methyl)-1H-1,2,4-triazol-1-yl ethanol crude product, recrystallization gets white crystal 1.8g, yield 41.5%, 141~143 ℃ of fusing points.
1H NMR:8.12(2H,s,2triazole C5-H),7.89(2H,s,2triazoleC3-H),6.74-7.57(7H,m,Ar-H),5.50(1H,s,OH),5.08-5.10(2H,d,CH2),4.59-4.61(2H,d,CH2).
All the other target compounds are synthesis material with different replacement aryl ether ketones, and are listed as table 1, repeat the step in the example I, just can synthesize the required two triazole compounds of aryl oxide that contain.
Synthetic of the present invention contains the two triazole compounds of aryl oxide and has the effect of the fungi of inhibition, sets forth its living experimental result of surveying below.
Experimental technique: adopt the Plating that exsomatizes
Materials and methods
(1) test strain
Agriculture frequently seen plants fungal disease in the table 2 is selected in this experiment for use, these diseases are fungus-caused by a plurality of genus that are under the jurisdiction of Ascomycota, Basidiomycota, imperfect fungi door, for example Staphlosporonites, interlink spore genus, black star spore genus, Verticillium, reaping hook belong to, the spherical shell spore belongs to or the like, have represented the panoramic plant pathogenic fungi of nature.
(2) test method
Reagent agent is diluted to desired concn respectively by effective constituent, under aseptic condition, respectively draws the 1mL soup and inject in the culture dish, add the 9mL substratum more respectively, make 5 μ g/mL pastille flat boards after shaking up, do blank with the flat board that adds the 1mL aqua sterilisa.Punch tool with diameter 4mm cuts the bacterium dish along the mycelia outer rim, moves on the pastille flat board every processing triplicate.Culture dish is placed on cultivation in 24 ± 1 ℃ of constant incubators.The 72h " Invest, Then Investigate " is respectively handled bacterium dish expansion diameter, averages, and relatively calculates relative bacteriostasis rate with blank.
Figure A20061014083600121
Experimental result
The part of compounds bacteriostatic experiment the results are shown in Table 2, table 3:
Table 2: fungicidal activity (5 μ g/mL), %
The fungi title Fungicidal activity (5 μ g/mL), %
Difenoconazole Tebuconazole Compound 2
Sugar beet leaf spot bacteria 100.0 100.0 100.0
Fusarium moniliforme 100.0 100.0 100.0
Cucumber fusarium axysporum 80.9 99.0 80.9
Peanut Cercospora bacteria 100.0 100.0 100.0
Asparagus stem wilt bacteria 100.0 100.0 100.0
Tomato early blight bacterium 84.2 84.2 84.2
Fusarium graminearum 100.0 100.0 100.0
The ring rot of apple bacterium 94.5 91.0 91.0
The rice green smut bacterium 100.0 100.0 100.0
Dosporium cucumerinumand its 94.5 91.0 91.0
Botrytis cinerea pers 99.0 99.0 99.0
Sclerotinia sclerotiorum 99.0 99.0 99.0
Apple zonate spot bacterium 99.0 99.0 99.0
Valsa mali 99.0 99.0 99.0
Glorosprium musarum Cookeet Mass 100.0 100.0 100.0
The brown edge germ of banana 86.5 86.5 83.8
Watermelon anthrax bacteria 99.0 88.5 99.0
Apple anthrax bacteria 100.0 99.0 100.0
Cucumber anthracnose 100.0 100.0 100.0
The pears alternaria 99.0 99.0 99.0
The root rotof flax bacterium 99.0 99.0 99.0
The miliary damping-off germ 99.0 95.0 99.0
Cereal silk nuclear germ 99.0 99.0 99.0
Cotton-wilt fusarium 76.2 90.5 80.9
Verticillium dahliae 92.3 92.3 92.3
Southern corn leaf blight 99.0 99.0 99.0
Table 3: fungicidal activity (1 μ g/mL), %
The fungi title Fungicidal activity (1 μ g/mL), %
Difenoconazole Tebuconazole Compound 2
Fusarium graminearum 73.9 86.9 82.6
Tomato early blight bacterium 95 65.5 58.6
Cucumber fusarium axysporum 53.1 65.6 62.5
The ring rot of apple bacterium 69.7 68.2 90.3
Sclerotinia sclerotiorum 56.7 91 88.1
The miliary damping-off germ 94.7 94.7 94.7
Cereal silk nuclear germ 93 93 93
Biological activity is with killing or suppressing percentage and represent in table 2, the table 3
Active classification: +++〉=90%; ++ 〉=70%-89%; + 〉=50%-69%;-<50%.
26 kind of plant pathogenic fungi biomass growth rate restraining effect are found that The compounds of this invention has suppress the agricultural fungal diseases activity preferably, under 5.0ug/mL concentration, the mycothallus growth for examination there is the good restraining effect, the inhibiting rate overwhelming majority is more than 80%, even reach 100.0%, with the Zui Hao of current fungistatic effect De Difenoconazole (difenoconazole), tebuconazole (difenoconazole) is suitable; Under 1.0ug/mL concentration, the mycothallus growth for examination also there is the good restraining effect, the inhibiting rate overwhelming majority is more than 80%, its effect slightly is inferior to 5.0ug/mL concentration, but its concentration is low, residual quantity is little, substantially reach the inhibition effect, also can with the Zui Hao of current fungistatic effect De Difenoconazole (difenoconazole), tebuconazole (difenoconazole) is suitable.

Claims (10)

1, a kind of two triazole compounds of aryl oxide that contain is characterized in that having following structural formula (I) or described structural formula (I) acceptable enantiomorph on agricultural pharmacology:
Wherein, R 1, R 2, R 3, R 4, R 5, R 6Be hydrogen, C 1~4Alkyl, trifluoromethyl, methoxyl group, nitro or halogen;
Described C 1~4Alkyl is methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl or the tertiary butyl;
Described halogen atom is fluorine, chlorine, bromine or iodine.
2, the two triazole compounds of aryl oxide that contain as claimed in claim 1 is characterized in that described R 1, R 2, R 3, R 4, R 5, R 6In the substituting group, have at least two substituting groups different.
3, the two triazole compounds of aryl oxide that contain as claimed in claim 1 is characterized in that described R 1, R 2, R 3, R 4, R 5, R 6In the substituting group, have at least two substituting groups identical.
4, the acid salt that contains the two triazole compounds of aryl oxide as claimed in claim 1, it is characterized in that the acid of described acid salt is one or more in hydrochloric acid, Hydrogen bromide, nitric acid, sulfuric acid, phosphoric acid, hydroiodic acid HI, hydrofluoric acid, perchloric acid, tosic acid, methylsulfonic acid, acetate, citric acid, tartrate, oxysuccinic acid, oxalic acid, fumaric acid or the phthalic acid.
5, the metal-salt mixture of the two triazole compounds of aryl oxide according to claim 1 is characterized in that having following structural formula (II):
Wherein, R 1, R 2, R 3, R 4, R 5, R 6Be hydrogen, C 1~4Alkyl, trifluoromethyl, methoxyl group, nitro or halogen;
Described C 1~4Alkyl is methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, sec-butyl or the tertiary butyl;
Described halogen atom is fluorine, chlorine, bromine or iodine;
Described M is the period of element Table II A, IV A, I B, II B, VI B, VII BOr the positively charged ion of VIII family;
Described Y is the negatively charged ion of neutralizing cation M electric charge.
6, as among the claim 1-3 any one described contain the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease.
7, as claimed in claim 6 contain the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease, it is characterized in that described agroforestry fungal disease is fungus-caused by the one or more genus that are under the jurisdiction of Ascomycota, Basidiomycota, imperfect fungi door.
8, as claimed in claim 7 contain the two triazole compounds of aryl oxide as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease, it is characterized in that, described agroforestry fungal disease be by Staphlosporonites, interlink spore genus, black star spore genus, Verticillium, reaping hook belongs to or the spherical shell spore belongs to, and one or more are fungus-caused.
9, the acid salt that contains the two triazole compounds of aryl oxide as claimed in claim 4 as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease.
10, the metal-salt mixture of the two triazole compounds of aryl oxide as claimed in claim 5 as agricultural with sterilant in the application that prevents and treats on the agroforestry fungal disease.
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