ES2557597T3 - Producto que comprende diamidas, método de preparación y usos - Google Patents
Producto que comprende diamidas, método de preparación y usos Download PDFInfo
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- ES2557597T3 ES2557597T3 ES09783247.1T ES09783247T ES2557597T3 ES 2557597 T3 ES2557597 T3 ES 2557597T3 ES 09783247 T ES09783247 T ES 09783247T ES 2557597 T3 ES2557597 T3 ES 2557597T3
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- 150000001470 diamides Chemical class 0.000 title abstract description 4
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract description 2
- 239000005977 Ethylene Substances 0.000 abstract description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- -1 propyl (n-propyl) Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 21
- 239000013078 crystal Substances 0.000 description 15
- YDGMGEXADBMOMJ-LURJTMIESA-N N(g)-dimethylarginine Chemical compound CN(C)C(\N)=N\CCC[C@H](N)C(O)=O YDGMGEXADBMOMJ-LURJTMIESA-N 0.000 description 8
- YDGMGEXADBMOMJ-UHFFFAOYSA-N asymmetrical dimethylarginine Natural products CN(C)C(N)=NCCCC(N)C(O)=O YDGMGEXADBMOMJ-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 3
- 230000006911 nucleation Effects 0.000 description 3
- 238000010899 nucleation Methods 0.000 description 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- 239000005944 Chlorpyrifos Substances 0.000 description 2
- 239000005947 Dimethoate Substances 0.000 description 2
- 239000005906 Imidacloprid Substances 0.000 description 2
- 239000005591 Pendimethalin Substances 0.000 description 2
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 0.000 description 2
- 239000005846 Triadimenol Substances 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229940056881 imidacloprid Drugs 0.000 description 2
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 2
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 2
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 239000005877 Alpha-Cypermethrin Substances 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- CNFYAHXVPQFCLC-UHFFFAOYSA-N S(=O)(Cl)Cl.C(CCC(=O)O)(=O)O Chemical compound S(=O)(Cl)Cl.C(CCC(=O)O)(=O)O CNFYAHXVPQFCLC-UHFFFAOYSA-N 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5004—Organic solvents
- C11D7/5013—Organic solvents containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/43—Thickening agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/16—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
- C10M133/56—Amides; Imides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/43—Solvents
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/32—Organic compounds containing nitrogen
- C11D7/3263—Amides or imides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5036—Azeotropic mixtures containing halogenated solvents
- C11D7/5068—Mixtures of halogenated and non-halogenated solvents
- C11D7/5095—Mixtures including solvents containing other heteroatoms than oxygen, e.g. nitriles, amides, nitroalkanes, siloxanes or thioethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/08—Amides [having hydrocarbon substituents containing less than thirty carbon atoms]
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/28—Amides; Imides
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Producto que comprende al menos dos compuestos de diamida elegidos entre los compuestos de diamida de las fórmulas (la), (Ib) y (Ic) siguientes: R2R3NOC-Aa-CONR4R5 (Ia) R2R3NOC-Ab-CONR4R5 (Ib) R2R3NOC-Ac-CONR4R5 (Ic) en las que: - R2, R3, R4 y R5, idénticos o diferentes, se eligen entre los grupos metilo, etilo, propilo (n-propilo), isopropilo, nbutilo, isobutilo, n-pentilo, amilo, isoamilo, hexilo, ciclohexilo, hidroxietilo, morfolina, piperazina o piperidina ; - Aa es el grupo de la fórmula siguiente -CH2-CH2- (etileno) - Ab es el grupo de la fórmula siguiente -CH2-CH2-CH2- (n-propileno), y - Ac es el grupo de la fórmula siguiente -CH2-CH2-CH2-CH2- (n-butileno).
Description
5
15
25
35
45
ejemplo en el depósito de un dispositivo destinado a propagar la composición. No se excluye que el agricultor añada otros productos fitosanitarios, por ejemplo fungicidas, herbicidas, pesticidas, insecticidas, fertilizantes. Por lo tanto, la formulación se puede usar para preparar una composición del producto fitosanitario activo diluida en agua, por mezcla de al menos una parte en peso de formulación concentrada con al menos 10 partes de agua, preferentemente menos de 1000 partes. La tasa de dilución y las cantidades a aplicar en el campo dependen por lo general del producto fitosanitario y de la dosis que se desea para tratar el campo; esto lo puede determinar el agricultor.
A la vista de los ejemplos que siguen a continuación, podrán aparecer otros detalles o ventajas, sin carácter limitante.
Ejemplos
Se preparan mezclas de diamidas a partir de mezclas de diácido. Para la preparación se realizan los procedimientos generales siguientes (en las fórmulas A representa una mezcla de Aa = etileno, Ab = n, propileno, Ac = n-butileno).
Procedimiento A: Formación de dicloruros de ácido (en mezcla)
La mezcla de diácidos y el cloruro de tionilo se mezclan a temperatura ambiente. La mezcla de reacción se puede calentar a reflujo para completar la reacción. Las especies volátiles se retiran por destilación a presión reducida para obtener el producto en bruto que por lo general se usa tal que sin otra forma de purificación.
Procedimiento B: Formación de diamida (en mezcla) por reacción con una dialquilamina
Se cargan tolueno y trietilamina y se refrigeran a -10 ºC. La dialquilamina se carga a continuación en forma líquida. El dicloruro de ácido (en mezcla), diluido en tolueno, se añade a continuación lentamente siempre manteniendo la temperatura por debajo de +10 ºC. A continuación, la mezcla se agita durante dos horas a temperatura ambiente. Las sales formadas durante la reacción se filtran a continuación y se lavan con acetato de etilo. El filtrado obtenido de este modo se evapora en el rotavapor para obtener la parte bruta de la reacción. Por último, el producto final se obtiene después de la destilación a presión reducida.
Ejemplo 1.1 Preparación de un producto que comprende una mezcla de los compuestos siguientes:
Me2NOC-CH2-CH2-CONMe2 Me2NOC-CH2-CH2-CH2-CONMe2, y Me2NOC-CH2-CH2-CH2-CH2-CONMe2
Etapa 1
Materias primas
- mezcla de ácido adípico, ácido glutárico y ácido succínico
- Cloruro de tionilo
- 500 g; 3,82 mol; Pm: medio 132
- 1127 ml; 15,30 moles; Pm: 118,97; 4 eq
El dicloruro de ácido (en mezcla) se obtiene con el Procedimiento A. Producto en bruto = 631 g Etapa 2 Materias primas
11
-el agente activo, en cantidad en peso (de material activo) indicada en la tabla que sigue a continuación, -10 % en peso del tensioactivo Alkamuls® RC, comercializado por Rhodia -y, como disolvente, el resto del compuesto de los ejemplos.
5 Los ejemplos 2 son ejemplos comparativos en los que como disolvente se usa el producto Rhodiasolv® ADMA10, Rhodia (zona de Asia Pacífico): Disolvente de alquildimetilamida.
Se realizan los ensayos siguientes:
10 -Observación visual a 25 ºC -Se anota el aspecto de la formulación y opcionalmente se identifica la presencia de cristales -Observación visual a 0 ºC -La formulación se coloca durante 7 días para 0 ºC y se observa el aspecto de la formulación y se identifica opcionalmente la presencia de cristales (ensayo CIPAC MT39) -Observación visual a 0 ºC con nucleación: Se introduce un cristal del material activo en la formulación habiendo 15 pasado 7 días a 0 ºC para nucleación, y la formulación se coloca de nuevo durante 7 días a 0 ºC. Se observa el aspecto de la formulación y opcionalmente se identifica la presencia de cristales.
- Ejemplo
- Disolvente Agente activo Aspecto a 25 ºC Aspecto a 0 ºC Aspecto a 0 ºC con nucleación
- 2.1C
- Rhodiasolv® ADMA 10 Alacloro -48 % Transparente Cristales Cristales
- 2.6C
- Rhodiasolv® ADMA 10 Pendimetalina -33 % Transparente Cristales Cristales
- 2.8C
- Rhodiasolv® ADMA 10 Triadimenol -23 % Transparente Transparente Cristales
- 2.10C
- Rhodiasolv® ADMA 10 Difenconazol -25 % Transparente Transparente Cristales
- 2.11C
- Rhodiasolv® ADMA 10 Imidacloprid -20 % No soluble No soluble No soluble
- 2.12C
- Rhodiasolv® ADMA 10 Dimetoato -40 % Turbio Turbio Cristales
- 2.13C
- Rhodiasolv® ADMA 10 Oxifluorfen -22 % Transparente Transparente Cristales
- 2.14C
- Rhodiasolv® ADMA 10 Propoxur -20 % Transparente Transparente Cristales
- 3.1
- Ejemplo 1.1 Alacloro -48 % Transparente Transparente Transparente
- 3.2
- Ejemplo 1.1 Clorpirifós -40 % Transparente Transparente Transparente
- 3.5
- Ejemplo 1.1 Propanil -36 % Transparente Transparente Transparente
- 3.6
- Ejemplo 1.1 Pendimetalina -33 % Transparente Transparente Cristales
- 3.11
- Ejemplo 1.1 Imidacloprid -20 % Transparente Transparente Transparente
- 3.12
- Ejemplo 1.1 Dimetoato -40 % Transparente Transparente Cristales
- 4.1
- Ejemplo 1.2 Alacloro -48 % Transparente Transparente Transparente
- 4.2
- Ejemplo 1.2 Clorpirifós -40 % Transparente Transparente Transparente
- 4.3
- Ejemplo 1.2 Alfa-Cipermetrina -10 % Transparente Transparente Transparente
- 4.5
- Ejemplo 1.2 Propanil -36 % Transparente Transparente Transparente
- 4.7
- Ejemplo 1.2 Tebuconazol -23 % Transparente Transparente Transparente
- 4.8
- Ejemplo 1.2 Triadimenol -23 % Transparente Transparente Transparente
- 4.10
- Ejemplo 1.2 Difenconazol -25 % Transparente Transparente Transparente
- 4.13
- Ejemplo 1.2 Oxifluorfen -22 % Transparente Transparente Transparente
- 4.14
- Ejemplo 1.2 Propoxur -20 % Transparente Transparente Transparente
13
Claims (1)
-
imagen1 imagen2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0805188 | 2008-09-22 | ||
| FR0805188A FR2936129B1 (fr) | 2008-09-22 | 2008-09-22 | Produit comprenant des diamides, procede de preparation et utilisations |
| PCT/EP2009/062208 WO2010031867A1 (fr) | 2008-09-22 | 2009-09-21 | Produit comprenant des diamides, procede de preparation et utilisations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2557597T3 true ES2557597T3 (es) | 2016-01-27 |
Family
ID=40568776
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09783247.1T Active ES2557597T3 (es) | 2008-09-22 | 2009-09-21 | Producto que comprende diamidas, método de preparación y usos |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20120029092A1 (es) |
| EP (1) | EP2328862B1 (es) |
| AR (1) | AR075276A1 (es) |
| ES (1) | ES2557597T3 (es) |
| FR (1) | FR2936129B1 (es) |
| WO (1) | WO2010031867A1 (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2364591A1 (en) * | 2010-03-09 | 2011-09-14 | Cognis IP Management GmbH | Biocide compositions comprising dicarboxylic acid alkylamides |
| EP3440050A1 (en) | 2016-04-06 | 2019-02-13 | Rhodia Operations | N-alkyldiamide compounds and gels comprising the same |
| WO2019068913A1 (en) | 2017-10-05 | 2019-04-11 | Rhodia Operations | FORMULATIONS COMPRISING BIOLOGICALLY ACTIVE PRINCIPLES |
| EP3466398A1 (en) | 2017-10-05 | 2019-04-10 | Rhodia Operations | N-hydrocarbyldiamide composition with gelating properties |
| WO2019068914A1 (en) | 2017-10-05 | 2019-04-11 | Rhodia Operations | FORMULATIONS COMPRISING SURFACTANTS, ORGANIC LIQUIDS AND VISCOSITY IMPROVERS |
| CN117986145A (zh) * | 2022-10-31 | 2024-05-07 | 中国石油化工股份有限公司 | 一种双酰胺衍生物的合成方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3632783A (en) * | 1969-05-27 | 1972-01-04 | Hall Co C P | Treatment of mosquito bites employing certain tetraalkyl diamides |
| JPS57154102A (en) * | 1981-03-19 | 1982-09-22 | Takako Mori | Insecticidal method |
| EP0080758B1 (en) * | 1981-11-07 | 1985-07-24 | Siegfried Aktiengesellschaft | Method of controlling a broad spectrum of weeds in a crop area and composition for the method |
| EP0143303A3 (de) | 1983-10-29 | 1986-04-30 | Bayer Ag | Verfahren zur Herstellung von substituierten Bernsteinsäureamiden |
| CA1294981C (en) | 1984-11-29 | 1992-01-28 | Robert A. Dubbert | 1,6 hexanediamides from 3-pentenamides |
| DE4404222A1 (de) * | 1994-02-10 | 1995-08-17 | Bayer Ag | Verwendung von Dicarbonsäure-bis-dimethylamiden als Kristallisationsinhibitoren |
| UA52701C2 (uk) * | 1996-10-11 | 2003-01-15 | Басф Акцієнгезельшафт | Твердий засіб захисту рослин та спосіб його одержання, спосіб боротьби з небажаним ростом рослин, спосіб боротьби з шкідливими грибами і тваринами-шкідниками та спосіб регулювання росту рослин |
| US6391451B1 (en) * | 1999-09-07 | 2002-05-21 | Basf Aktiengesellschaft | Surface-treated superabsorbent polymer particles |
| FR2872824B1 (fr) * | 2004-07-06 | 2006-09-22 | Rhodia Chimie Sa | Procede pour epaissir un milieu liquide concentre en agents tensioactifs |
| FR2910000B1 (fr) * | 2006-12-19 | 2009-10-16 | Rhodia Recherches & Tech | Nouveaux composes bis(dialkylamides), procede de preparation et utilisations. |
-
2008
- 2008-09-22 FR FR0805188A patent/FR2936129B1/fr not_active Expired - Fee Related
-
2009
- 2009-09-21 US US13/120,374 patent/US20120029092A1/en not_active Abandoned
- 2009-09-21 ES ES09783247.1T patent/ES2557597T3/es active Active
- 2009-09-21 WO PCT/EP2009/062208 patent/WO2010031867A1/fr not_active Ceased
- 2009-09-21 EP EP09783247.1A patent/EP2328862B1/fr active Active
- 2009-09-22 AR ARP090103625A patent/AR075276A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010031867A1 (fr) | 2010-03-25 |
| AR075276A1 (es) | 2011-03-23 |
| US20120029092A1 (en) | 2012-02-02 |
| EP2328862B1 (fr) | 2015-10-21 |
| FR2936129B1 (fr) | 2012-10-12 |
| EP2328862A1 (fr) | 2011-06-08 |
| FR2936129A1 (fr) | 2010-03-26 |
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