MXPA98001536A - Separation of butanol and eter of dibutile with aid of distillation of double pres - Google Patents
Separation of butanol and eter of dibutile with aid of distillation of double presInfo
- Publication number
- MXPA98001536A MXPA98001536A MXPA/A/1998/001536A MX9801536A MXPA98001536A MX PA98001536 A MXPA98001536 A MX PA98001536A MX 9801536 A MX9801536 A MX 9801536A MX PA98001536 A MXPA98001536 A MX PA98001536A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- acid
- salts
- compounds
- adducts
- Prior art date
Links
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 title 2
- 238000004821 distillation Methods 0.000 title 1
- 238000000926 separation method Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 241000233866 Fungi Species 0.000 claims abstract description 17
- 230000000855 fungicidal Effects 0.000 claims abstract description 12
- 239000011780 sodium chloride Substances 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 230000002195 synergetic Effects 0.000 claims abstract description 7
- CRQQGFGUEAVUIL-UHFFFAOYSA-N Chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 40
- -1 surfaces Substances 0.000 claims description 10
- 239000000417 fungicide Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 3
- FEVYAAHIKWPJNV-TYDMEHBZSA-N 1-[[(2S,3R)-3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]-1,2,4-triazole;1-[[(2R,3S)-3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]-1,2,4-triazole Chemical compound C1=CC(F)=CC=C1[C@@]1(CN2N=CN=C2)[C@H](C=2C(=CC=CC=2)Cl)O1.C1=CC(F)=CC=C1[C@]1(CN2N=CN=C2)[C@@H](C=2C(=CC=CC=2)Cl)O1 FEVYAAHIKWPJNV-TYDMEHBZSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 abstract description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 1H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 12
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
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- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- 125000004432 carbon atoms Chemical group C* 0.000 description 2
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- 150000007522 mineralic acids Chemical class 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000003032 phytopathogenic Effects 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical group OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 235000021307 wheat Nutrition 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2R,3R,4S,5R,6S)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2R,3R,4S,5R,6R)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- QZEDXQFZACVDJE-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 QZEDXQFZACVDJE-UHFFFAOYSA-N 0.000 description 1
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(Z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
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- 239000004254 Ammonium phosphate Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N Ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N tin hydride Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000009369 viticulture Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Abstract
Fungicidal mixture containing a) (2RS, 3SR) -1- [2- (2-chlorophenyl-2,3, -epoxy-2- (4-fluorophenyl) propyl] -1H, 1,2,4-triazole ( See Formula) one of its salts or adducts, and b) tetrachloroisophthalonitrile II (See Formula) in an active synergistic amount, as well as its use to combat fungi nociv
Description
Description
The present invention relates to a fungicidal mixture containing
a) (2RS, 3SR) -l- [3- (2-chlorophenyl) -2,3-epoxy-2- (4-fluorophenyl) ro-pil] -lH-1, 2,4-triazole
one of its salts or adducts, and
b) tetrachloroisophthalonitrile II
in an active synergetic quantity.
In addition, the invention relates to a method for combating harmful fungi with mixtures of compounds I and II and to the use of compound I and compound II for obtaining such mixtures.
The compound of formula I and its preparation and action against harmful fungi are known from EP-A 196 038 and "The Pesticide Manual", 10th Edition, The British Crop Protection Council and The Royal Society of Chemistry, 1994 - hereinafter called "Pesticide Manual" - page 67: BAS 480 F, proposed name; Epoxy -conazole). Compounds II (common ñame: Chlorothalonil), their preparation and their action against harmful fungi are also known (see "Pesticide Manual", page 193).
spectrum of action of the compound and known, the present invention had as its object to find mixtures, which with a lower total amount of the applied active substances have a better action against harmful fungi (synergistic mixtures).
Therefore, the mixture defined above was found. In addition, it was found that by simultaneously applying the compound I and the compound II together or separately or by applying the compound I and the compound II in succession, it is possible to fight better harmful fungi than with the compounds I or II alone.
Thanks to its basic character of the 1, 2, 4-triazole ring, compound I is capable of forming salts with inorganic or organic acids or with metal ions.
Examples of inorganic acids are the hydrohalic acids, such as hydrochloric acid, hydrochloric acid, hydrobromic acid and hydroiodic acid, sulfuric acid, phosphoric acid and nitric acid.
Suitable organic acids are, for example, formic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, as well as glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid. , benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids with linear or branched alkyl radicals with 1 to 20 carbon atoms), arylsulfonic or aryldisulfonic acids (aromatic radicals, such as phenyl and naphthyl bearing one or two sulphonic acid groups), alkylphosphonic acids (phosphonic acids with linear or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic or arylphosphonic acids (aromatic radicals, such as phenyl and naphthyl carrying one or two phosphoric acid radicals, and the alkyl or aryl radicals carry more substituents, eg p-toluenes acid ulphonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.
As metal ions are appropriate, especially the ions of the elements of the first to octac group main, especially corm, manganese, iron, cobalt, nickel, copper, zinc, and in addition to the second main group, especially calcium and magnesium, the third and fourth main body, especially aluminum, tin and lead. The metals may be present in the. different valences that correspond to him.
Pure I and II, to which can be added, if necessary, other active substances against harmful fungi or other parasites, such as insects, arachnids, nematodes, or also herbicidal active substances or growth regulators or fertilizers.
The mixtures of compounds I and II or the combined or separate use of compounds I and II provide an excellent effect against a broad spectrum of phytopathogenic fungi, especially of the class of Ascomycetes, Basidiomycetes, Phycomycetes and Deuteromycetes. In part they have systemic action, so they can also be used as foliar and soil fungicides.
They are especially important for combating countless fungi in different crop plants, such as cotton, legumes (eg cucumbers, beans and cucurbits), barley, turf, oats, coffee, corn, rice, rye, soybeans, vine, barley, ornamental plants, sugar cane and countless seeds.
They are especially suitable for combating the following phytopathogenic fungi: Erysiphe graminis (mildew) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbitáces, Podosphaera leucotricha in apples, Puccinia species in cereals, Rhizoctonia species in cotton and grass, Ustilago species in cereals and sugar cane, Venturia inaequalis in apples, Helminthosporium species in cereals, Septoria nodorum in wheat, Botrytis ciñera (gray rot) in strawberries and vine, Cercospora arachidicola in peanuts, Pseudocercosporella herpotrichoides in wheat and barley, Pyricularia oryzae in rice, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticulture on the vine, Alternaria species on legumes and fruits, as well as Fusarium and Verticillium species.
In addition, they can be used in the protection of materials (eg preservation of wood), for example against Paecilomyces variotii.
The compounds I and II can be applied simultaneously together or separately or successively; in the separate application, generally, the order in which the compounds are applied has no effect on the success of the treatment.
Compounds I and II are usually used in a weight ratio of 10: 1 to 0.05: 1, preferably 5: 1 to 0.1: 1, especially 3: 1 to 0.2: 1.
varies, especially in agricultural areas, depending on the desired effect of 0.01 to 3 kg / ha, preferably 0.1 to 1.5 kg / ha, especially 0.1 to 1.0 kg / ha, the application rates for compounds I being increased to 0.01 to 0.5 kg / ha, preferably 0.05 to 0.5 kg / ha, especially 0.05 to 0.4 kg / ha. The amounts of application in the case of the compounds II vary correspondingly from 0.01 to 2 kg / ha, preferably 0.05 to 1 kg / ha, especially 0.05 to 0.5 kg / ha.
In the treatment of the seeds, application amounts of the mixture are generally used from 0.001 to 50 g / kg of seeds, preferably 0.01 to 10 g / kg, especially 0.01 to 8 g / kg.
When it is desired to combat pathogenic noxious fungi in plants, compounds I and II are applied separately or mixtures of compounds I, II by spraying or spraying seeds, plants or the. soil, before or after sowing the plants, or before or after the emergence of the plants.
The synergistic fungicidal mixtures of the invention or compounds I and II can be used in the form of solutions, powders, suspensions or dispersions, emulsions, oil dispersions, spraying agents, sprays, directly sprayable granules, by spraying nebulization, atomization , sprayed or watered. The forms of application depend entirely on the respective application purposes; in all cases, the finest possible distribution of the mixtures of the invention should be ensured.
The formulations are prepared in known manner, eg by the addition of snts and / or support substances. The formulations are usually added inert additives, such as emulsifiers or dispersants.
Suitable surfactants are: alkali metal, alkaline earth metal, ammonium salts of lignin sulphonic acid, naphthalenesulfonic acid, phenylsulfonic acid and dibutylnaphthalene sulfonic acid, alkylaryl sulphonates, alkyl sulfates, alkyl sulphonates, fatty alcohol sulfates, and acids fatty acids, alkaline and alkaline-earth metal salts, sulfated fatty alcohol glycol ethers, naphthalene-naphthalene condensates and naphthalene derivatives with formaldehyde, naphthalene condensates or naphthalene sulfonic acid with phenol and formaldehyde, polyoxyethylene phenylphenol alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, condensates of fatty alcohol, ethylene oxide, ethoxylated castor oil, polyoxyethylene alkyl ethers, polyoxypropylene, polyglycol ether acetal of lauryl alcohol, sorbitol esters , the residues lyes sulphites and methylcellulose
The powders, spraying and spraying agents can be obtained by mixing or milling together the compounds I or II or the mixture from the compounds I and II with a solid support.
Granules (eg coated, impregnated or homogenous granules) are prepared, usually by joining the active substance or the active substances with a solid support.
As solids or solid supports, for example, mineral earths, such as silica gel, silicic acid, silica gel, silicates, talc, kaolin, limestone, lime, bolus, loess, clay, dolomite, diatomaceous earth, sulphate calcium and magnesium sulfate, magnesium oxide, ground plastics, as well as fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and mineral products, such as cereal flour, bark powder, wood and of nut casings, cellulose powders or other solid supports.
The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds I or II, or of the mixture of the compounds I and II. The active substances are used here in a purity of 90 to 100%, preferably 95 to 100% (according to NMR / HPLC spectrum).
The compounds I or II, or the mixtures or the corresponding formulations are used, treating the harmful fungi, their living space, or the plants, the seeds, the floors, the surfaces, the materials or the enclosures to keep free of them , with an active fungicidal quantity of the mixture, or of the compounds I and II in the separate application.
The compounds I or II, the mixtures or the corresponding formulations are used in such a way that the harmful fungi, their living space or the plants, seeds, floors, materials or enclosures to be kept free of them, are treated with an amount Fungicidal active of the mixture or of compounds I and II, when applied separately.
by the NGOs noc vos.
Examples of the synergistic action of the mixtures according to the invention against harmful fungi
The fungicidal action of the compounds and mixtures can be checked by means of the following tests:
The active substances are prepared separately or together as a 10% emulsion in a mixture from 70% by weight of ci-clohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, emulsifying action moisturizer and dispersant based on alkylphenol - the ethoxylates) and 10% by weight of Emulphor® (Emulan® EL, emulsifier based on ethoxylated fatty alcohols), and diluted with water according to the desired concentration.
For the evaluation, the percentage of infected leaf surfaces is determined. These percentages are converted into degrees of action (observed). The theoretical degrees of action expected from the active substance mixtures are determined according to the formula of Colby [R.S. Colby, Weeds 15, 20-22 (1967)] and compared with the observed degrees of action.
Colby's formula:
E = x + y - x-y / 100
E signifies the expected degree of action, translated in% of the untreated control, by using the mixture from the active substances A and B in the concentrations a and b;
is the degree of action, translated in% of the untreated control, by using the active substance A in the concentration a;
and it is the degree of action, translated in% of the untreated control, by using the active substance B in the concentration b.
Given a degree of action equal to O, the infestation of the treated plants is equivalent to that of the untreated control plants; in the case of a 100% action grade, the treated plants do not show any infestation.
Claims (4)
1. Fungicide mixture containing a) (2RS, 3SR) -1- [3- (2-chlorophenyl) -2,3-epoxy-2- (4-fluorophenyl) propyl] -1H-1,2,4-triazole one of its salts or adducts, and b) tetrachloroisophthalonitrile II in an active synergetic quantity.
2. Fungicide mixture according to claim 1, characterized in that the weight ratio between the compound I its salt or adduct and the compound II amounts to 10: 1 to 0.05.-23.
Procedure for combating harmful fungi, characterized in that the harmful fungi, their living space or the plants, seeds, soils, surfaces, materials or enclosures to be kept free thereof are treated, with the compound of the formula I, one of their salts or adducts according to claim 1 and the compound of the formula II according to claim 1.
4. Process according to claim 3, characterized in that the compound I, one of its salts or adducts according to claim 1 and the compound II are simultaneously applied together or separately. Claim 1 is applied in an amount of 0.01 to 0.5 kg / ha. Process according to claims 3 to 5, characterized in that the compound II according to claim 1 is used in an amount of 0.01 to 2 kg / ha. Use of the compound I according to claim 1 for the preparation of a synergistically active fungicidal mixture according to claim 1. Use of the compound II according to claim 1 for obtaining a synergistically active fungicidal mixture according to claim 1. Fungicide mixture containing a) (2RS, 3SR) -1- [3- (2-chlorophenyl) -2,3-epoxy-2- (4-fluorophenyl) propyl] -1H-1,2,4-triazole one of its salts or adducts, and b) tetrachloroisophthalonitrile II in an active synergetic quantity, as well as its use to combat harmful fungi.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19531787.4 | 1995-08-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
MXPA98001536A true MXPA98001536A (en) | 1999-10-14 |
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