WO1995015690A1 - Utilisation d'amides d'acide phenylcarboxyliques comme inhibiteurs de la cristallisation - Google Patents

Utilisation d'amides d'acide phenylcarboxyliques comme inhibiteurs de la cristallisation Download PDF

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Publication number
WO1995015690A1
WO1995015690A1 PCT/EP1994/003932 EP9403932W WO9515690A1 WO 1995015690 A1 WO1995015690 A1 WO 1995015690A1 EP 9403932 W EP9403932 W EP 9403932W WO 9515690 A1 WO9515690 A1 WO 9515690A1
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WO
WIPO (PCT)
Prior art keywords
carbon atoms
formula
phenyl
benzyl
butyl
Prior art date
Application number
PCT/EP1994/003932
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German (de)
English (en)
Inventor
Wolfgang Wirth
Klaus Wangermann
Artur Botta
Karl Reizlein
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU12409/95A priority Critical patent/AU1240995A/en
Publication of WO1995015690A1 publication Critical patent/WO1995015690A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur

Definitions

  • the present invention relates to the new use of certain phenylcarboxylic acid derivatives to prevent crystallization when applying aqueous spray liquors based on certain fungicidal active ingredients.
  • filters and nozzles are present in sprayers which are usually used for the application of aqueous formulations of plant treatment agents.
  • suction filters between the suction part and tank pump and also pressure filters, which are arranged after the pump in the pressure area.
  • nozzle filters can be included, which are located directly in front of the spray nozzles. All of these filters, as well as the nozzles, can more or less easily become blocked by crystallizing active ingredient when applying aqueous spray liquors based on solid active ingredients.
  • N-alkyllactams and alkylcarboxylic acid dimethylamides can be used as crystallization inhibitors in the preparation and application of spray liquors of the active compounds mentioned (cf. EP-OS 0 391 168, EP-OS 0 453 915 and EP-OS 0 453 899).
  • N-octylpyrrolidone and / or a mixture which consists on average of 5% of hexanoic acid dimethylamide, 50% octanoic acid dimethyla ⁇ üd, 40% decanoic acid dimethylamide and 5% of dodecanoic acid dimethylamide can be used to which contain 1- (4-chlorophenyl) -4,4-dimethyl-3- (1,2,4-triazol-1-yl-methyl) -pentan-3-ol as active ingredient, this active ingredient crystallizes out in the sprayers prevent. If such spray liquors are applied for a longer period of time, the effectiveness of the crystallization inhibitors mentioned is not always satisfactory.
  • R 1 represents hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, benzyl, phenethyl, alkoxy having 1 to 6 carbon atoms, alkoxycarbonyl having 1 to 6 carbon atoms in the alkoxy part, phenoxy, phenoxycarbonyl or a radical of the formula in which
  • R 5 represents hydrogen, alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, cycloalkyl having 5 to 7 carbon atoms, phenyl or benzyl and
  • R 6 represents hydrogen, alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, cycloalkyl having 5 to 7 carbon atoms, phenyl or benzyl or
  • R 5 and R 6 together for an alkylene chain with 3 to 6 carbon atoms or for a group of the formula -CH 2 -CH 2 -O-CH 2 -CH 2 -,
  • R 2 represents hydrogen, alkyl having i to 6 carbon atoms, phenyl, benzyl, phenethyl, alkoxy having 1 to 6 carbon atoms or phenoxy,
  • R 3 represents hydrogen, alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, cycloalkyl having 5 to 7 carbon atoms, phenyl or benzyl and
  • R 4 represents alkyl with 1 to 8 carbon atoms, alkenyl with 2 to 8 carbon atoms, cycloalkyl with 5 to 7 carbon atoms, phenyl or benzyl or R 3 and R 4 together for an alkylene chain with 3 to 6 carbon atoms
  • R 8 represents tert-butyl
  • R 9 represents hydroxy, or b) R 7 represents 4-fluorophenyl
  • R 8 represents 2-fluorophenyl
  • R 9 represents hydroxy, or c) R 7 represents 2,4-dichlorophenyl,
  • R 8 represents n-butyl
  • R 9 represents hydroxy, or d) R 7 stands for
  • R 8 represents phenyl
  • R 9 represents cyano, or e) R 7 represents 4-chlorophenyl
  • R 8 stands for and
  • R 9 represents hydroxy, and / or at least one azole derivative of the formula
  • R 10 represents chlorine or phenyl
  • R 10 represents chlorine, and / or at least one azole derivative of the formula
  • R 11 represents hydrogen or chlorine, and / or
  • phenylcarboxylic acid amides of the formula (I) in aqueous formulations based on fungicidally active azole derivatives of the formulas (II) to (VI) has a number of advantages.
  • the phenylcarboxylic acid amides of the formula (I) are substances which are easy to handle and are also available in larger quantities. Furthermore, the use of the substances of the formula (I) prevents the spraying of aqueous formulations which contain the active compounds of the formulas (II) to (VI) from clogging both the filters and the nozzles of the spraying devices. It is also advantageous that phenylcarboxamides of the formula (I) have no undesirable side effects in crop protection.
  • the phenylcarboxylic acid amides which can be used according to the invention are generally defined by the formula (I).
  • R 1 preferably represents hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, phenyl, benzyl, phen-2-ethyl, phen-1-ethyl, straight-chain or branched alkoxy having 1 to 4 carbon atoms, straight-chain or branched alkoxycarbonyl having 1 to 4th
  • R 5 preferably represents hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched alkenyl having 2 to 6 carbon atoms, cyclopentyl, cyclohexyl, cycloheptyl, phenyl or benzyl.
  • R 6 preferably represents hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched alkenyl having 2 to 6 carbon atoms, cyclopentyl, cyclohexyl, cycloheptyl, phenyl or benzyl.
  • R 5 and R 6 also preferably together represent an alkylene chain having 3 to 6 carbon atoms or a group of the formula -CH 2 -CH 2 -O-CH 2 -CH 2 -,
  • R 2 preferably represents hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, phenyl, benzyl, phen-2-ethyl, phen-1-ethyl, straight-chain or branched alkoxy having 1 to 4 carbon atoms or phenoxy.
  • R 3 preferably represents hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched alkenyl having 2 to 6 carbon atoms, cyclopentyl, cyclohexyl, cycloheptyl, phenyl or benzyl
  • R 4 preferably represents straight-chain or branched alkyl having 1 to 6 Carbon atoms, straight-chain or branched alkenyl having 2 to 6 carbon atoms, cyclopentyl, cyclohexyl, cycloheptyl, phenyl or benzyl.
  • R 3 and R 4 together also preferably represent an alkylene chain having 3 to 6 carbon atoms or a group of the formula
  • R 1 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, phenyl, benzyl, phen-2ethyl, phen-1-ethyl, Methoxy, ethoxy, ethoxycarbonyl, methoxycarbonyl,
  • R 5 particularly preferably represents hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkenyl having 2 to 4 carbon atoms, cyclopentyl, cyclohexyl, cycloheptyl, phenyl or benzyl.
  • R 6 particularly preferably represents hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, straight-chain or branched alkenyl having 2 to 4 carbon atoms, cyclopentyl, cyclohexyl, cycloheptyl, phenyl or benzyl.
  • R 5 and R 6 together also particularly preferably represent one
  • R 2 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, phenyl, benzyl, phen-2-ethyl, phen-1 - ethyl, methoxy, ethoxy or phenoxy.
  • R 3 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, vinyl, allyl, but-2-ene yl, cyclopentyl, cyclohexyl, cycloheptyl, phenyl or benzyl.
  • R 4 particularly preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, vinyl, allyl, but-2-en-yl, cyclopentyl , Cyclohexyl, cycloheptyl, phenyl or benzyl.
  • R 3 and R 4 together also particularly preferably represent an alkylene chain having 3 to 6 carbon atoms or a group of the formula
  • phenylcarboxamides of the formula (I) are known or can be prepared in a simple manner by known methods (cf. Houben-Weyl "Methods of Organic Chemistry", Georg Thieme Verlag, Stuttgart 1985, Volume E5, page 934 ff).
  • azole derivatives contained in the aqueous spray liquors which can be used according to the invention are defined by the formulas (II) to (VI). Single or also several or following azole derivatives can be contained.
  • the active compounds of the formulas (II) to (VI) and their use for controlling phytopathogenic fungi are known (cf. EP-OS 0 040 345, US Pat. No. 4,551,469, EP-PS 0 015 756, EP-OS 0 068 813 , DE-OS 3 406 993, DE-PS 2 324 010, DE-PS 2 201 063, DE-OS 2 838 847, DE-OS 3 010 560, DE-OS 2 821 971 and EP-OS 0 196 038) .
  • the active compounds of the formulas (II) to (VI) can be used in customary formulations. The application is preferably carried out in the form of aqueous spray liquors.
  • the spray liquors which can be used according to the invention may also contain one or more further active compounds.
  • Compounds with fungicidal properties are preferred. The following may be mentioned as examples of such additional active substances: N, N-dimethyl-N'-phenyl- (N'-fluorodichloromethylthio) sulfamide (dichlofluanid),
  • Suitable additives which can be present in the spray liquors which can be used according to the invention are surface-active substances, organic diluents, acids, cold stabilizers and adhesives.
  • Nonionic, anionic, cationic and zwitterionic emulsifiers are suitable as surface-active substances.
  • These substances include reaction products of fatty acids, fatty acid esters, fatty alcohols, fatty amines, alkylphenols or alkylarylphenols with ethylene oxide and / or propylene oxide, and their sulfuric acid esters, phosphoric acid monoesters and phosphoric acid di-esters, furthermore reaction products of ethylene oxide with propylene oxide, furthermore alkyl sulfonates, Alkyl sulfates, aryl sulfates, tetra-alkyl ammonium halides, trialkylaryl ammonium halides and alkyl amine sulfonates.
  • the emulsifiers can be used individually or in a mixture.
  • the emulsifiers from the group of alkylaryl polyglycol ethers used in practice are often mixtures of several compounds.
  • these are mixtures of substances which differ in the degree of substitution on the phenyl ring connected to the oxyethylene unit and the number of oxyethylene units.
  • fractional numbers are also calculated as mean values for the number of substituents on the phenyl ring. Examples include substances for which the following average compositions result:
  • Ketones such as methyl isobutyl ketone and cyclohexanone, and also amides, such as dime, are preferred thylformamide further cyclic compounds, such as N-methyl-pyrrolidone, N-octyl-pyrrolidone, N-dodecyl-pyrrolidone, N-octyl-caprolactam, N-dodecyl-caprolactam and ⁇ -butyrolactone, and also strongly polar solvents, such as dimethyl sulfoxide, furthermore aromatic hydrocarbons, such as xylene, also esters, such as propylene glycol monomethyl ether acetate, adipic acid dibutyl ester, acetic acid hexyl ester, acetic acid heptyl este
  • Acids which can be used in the spray liquors which can be used according to the invention are all inorganic and organic acids which can normally be used for such purposes. Aliphatic and aromatic hydroxycarboxylic acids such as citric acid, salicylic acid, tartaric acid and ascorbic acid are preferred.
  • Cold stabilizers which can be used in the spray liquors which can be used according to the invention are all substances which are customarily suitable for this purpose. Urea, glycerol and propylene glycol are preferred.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and also synthetic phospholipids are preferred.
  • Other additives can be mineral and vegetable oils.
  • the spray liquors which can be used according to the invention each contain water.
  • the active substance concentrations can be varied within a certain range in the spray liquors which can be used according to the invention. In general, the active substance concentrations are between 0.0001 and 5 percent by weight, preferably between 0.001 and 3 percent by weight.
  • the ratio of active ingredient of the formulas (II) to (VI) to phenylcarboxylic acid amide of the formula (I) can also be varied within a certain range. In general, the weight ratio of active ingredient from group (A) to phenylcarboxylic acid amide of the formula (I) is between 1: 0.2 and 1: 5, preferably between 1: 0.6 and 1: 2.
  • the amounts of further active ingredients or additives can be varied within a substantial range in the spray liquors which can be used according to the invention. They are of the order of magnitude which is usually the case in such aqueous spray liquors.
  • the spray liquors which can be used according to the invention are prepared by customary methods. In general, the procedure is that a concentrate is first prepared by combining the required components in any order at temperatures between 10 ° C. and 30 ° C. and mixing them homogeneously and, if necessary, filtering the resulting mixture. To prepare the ready-to-use spray liquors, the concentrated formulation is mixed with the desired amount of water, if appropriate with stirring and / or pumping, in such a way that the formulation is uniformly and finely dispersed in water.
  • phenylcarboxylic acid amides of the formula (I) in aqueous spray liquors based on active compounds of the formulas (II) to (VI) means that the active compound crystallizes out both in the concentrated, commercially available formulation and when the aqueous spray prepared therefrom is applied brew in the filters and outlet openings of the sprayers either completely prevented or prevented so far that the application of the spray liquors is not impaired.
  • CIPAC-C water water containing 4 mmol calcium chloride
  • a spray liquor is prepared from the concentrate thus obtained by mixing it with water of defined hardness (CBPAC-C water, see Example I), in which the concentrate is contained in a concentration of 0.5% by weight.
  • a spray liquor is prepared from the concentrate thus obtained by mixing it with water of defined hardness (CIPAC-C water; see Example I), in which the concentrate is contained in a concentration of 0.5% by weight.
  • CIPAC-C water defined hardness

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

On peut utiliser des amides d'acide phénylcarboxylique de formule (I), dans laquelle R?1, R2, R3 et R4¿ ont la signification indiquée dans la description, pour éviter, lors de la pulvérisation de bouillies aqueuses contenant A) certains dérivés d'azole ayant tendance à cristalliser et B), le cas échéant, une ou plusieurs autres substances actives ainsi que des additifs, une cristallisation, dans les pulvérisateurs, de ces substances actives ayant tendance à cristalliser.
PCT/EP1994/003932 1993-12-09 1994-11-28 Utilisation d'amides d'acide phenylcarboxyliques comme inhibiteurs de la cristallisation WO1995015690A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU12409/95A AU1240995A (en) 1993-12-09 1994-11-28 Use of phenyl carboxilic acid amides as crystalisation inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4331416A DE4331416A1 (de) 1993-12-09 1993-12-09 Verwendung von Phenylcarbonsäure-amiden als Kristallisationsinhibitoren
DEP4331416.3 1993-12-09

Publications (1)

Publication Number Publication Date
WO1995015690A1 true WO1995015690A1 (fr) 1995-06-15

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Application Number Title Priority Date Filing Date
PCT/EP1994/003932 WO1995015690A1 (fr) 1993-12-09 1994-11-28 Utilisation d'amides d'acide phenylcarboxyliques comme inhibiteurs de la cristallisation

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AU (1) AU1240995A (fr)
DE (1) DE4331416A1 (fr)
IL (1) IL111889A0 (fr)
WO (1) WO1995015690A1 (fr)
ZA (1) ZA949788B (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999031979A1 (fr) * 1997-12-18 1999-07-01 Basf Aktiengesellschaft Melanges fongicides a base de composes amide et d'azoles
US6268387B1 (en) 1997-12-23 2001-07-31 Warner-Lambert Company Thiourea and benzamide compounds, compositions and methods of treating or preventing inflammatory diseases and atherosclerosis
WO2003029219A1 (fr) * 2001-09-25 2003-04-10 Basf Aktiengesellschaft Hydrates cristallins de derives de nicotinanilide et de benzanalide
WO2011010082A3 (fr) * 2009-07-24 2012-02-16 Syngenta Limited Formulations
CN106212457B (zh) * 2011-01-24 2019-03-08 辛根塔有限公司 配制品组分

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2043446A2 (fr) * 2006-02-08 2009-04-08 Phibro-Tech Inc. Concentres d'emulsion d'azole biocide ayant une teneur elevee en substance active
WO2008069822A1 (fr) * 2006-02-21 2008-06-12 Phibro-Tech Inc. Concentrés d'émulsions d'azoles biocides ayant une teneur en ingrédient actif élevée
EP2327302B1 (fr) * 2009-11-17 2015-04-29 Cognis IP Management GmbH Compositions biocides contenant des carbamates

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2361604A1 (de) * 1973-12-11 1975-06-19 Eszakmagyar Vegyimuevek Verfahren zur herstellung von n,ndisubstituierten carbonsaeureamiden
DE2610798A1 (de) * 1976-03-15 1977-09-29 Basf Ag Treibstoffe fuer ottomotoren
EP0453899A1 (fr) * 1990-04-27 1991-10-30 Bayer Ag Utilisation de diméthyl-amides alkylcarboxyliques comme inhibiteurs de cristallisation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2361604A1 (de) * 1973-12-11 1975-06-19 Eszakmagyar Vegyimuevek Verfahren zur herstellung von n,ndisubstituierten carbonsaeureamiden
DE2610798A1 (de) * 1976-03-15 1977-09-29 Basf Ag Treibstoffe fuer ottomotoren
EP0453899A1 (fr) * 1990-04-27 1991-10-30 Bayer Ag Utilisation de diméthyl-amides alkylcarboxyliques comme inhibiteurs de cristallisation

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 84, no. 5, 2 February 1976, Columbus, Ohio, US; abstract no. 30606d, A.YU. NAUMOV ET AL.: "Synthesis of insect repellents from substituted N,N-dialkylbenzamides according to the Friedel-Crafts reaction" *
ZH. OBSHCH. KHIM., vol. 45, no. 9, 1975, pages 2065 - 2068 *

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100536150B1 (ko) * 1997-12-18 2005-12-14 바스프 악티엔게젤샤프트 아미드 화합물 및 아졸 기재의 살진균성 혼합물
US6350765B1 (en) 1997-12-18 2002-02-26 Basf Aktiengesellschaft Fungicidal mixtures based on amide compounds and azoles
AU750310B2 (en) * 1997-12-18 2002-07-18 Basf Se Fungicide mixtures based on amide compounds and azoles
WO1999031979A1 (fr) * 1997-12-18 1999-07-01 Basf Aktiengesellschaft Melanges fongicides a base de composes amide et d'azoles
US6268387B1 (en) 1997-12-23 2001-07-31 Warner-Lambert Company Thiourea and benzamide compounds, compositions and methods of treating or preventing inflammatory diseases and atherosclerosis
US6528528B2 (en) 1997-12-23 2003-03-04 Warner-Lambert Company Thiourea and benzamide compounds, compositions and methods of treating or preventing inflammatory diseases and atherosclerosis
EA007780B1 (ru) * 2001-09-25 2007-02-27 Басф Акциенгезельшафт Кристаллические гидраты производных анилида никотиновой кислоты
US7087239B2 (en) 2001-09-25 2006-08-08 Basf Aktiengesellschaft Crystalline hydrates of anilide derivatives
WO2003029219A1 (fr) * 2001-09-25 2003-04-10 Basf Aktiengesellschaft Hydrates cristallins de derives de nicotinanilide et de benzanalide
KR100949627B1 (ko) * 2001-09-25 2010-03-26 바스프 에스이 니코틴산 아닐리드 및 벤조일 아닐리드 유도체의 결정질수화물
WO2011010082A3 (fr) * 2009-07-24 2012-02-16 Syngenta Limited Formulations
US20120184438A1 (en) * 2009-07-24 2012-07-19 Syngenta Crop Protection, Llc Formulations
CN102740690A (zh) * 2009-07-24 2012-10-17 先正达有限公司 苯甲酰胺衍生物及其制备和用途
JP2013500249A (ja) * 2009-07-24 2013-01-07 シンジェンタ リミテッド 製剤
CN106212457B (zh) * 2011-01-24 2019-03-08 辛根塔有限公司 配制品组分

Also Published As

Publication number Publication date
AU1240995A (en) 1995-06-27
DE4331416A1 (de) 1995-06-14
ZA949788B (en) 1995-01-01
IL111889A0 (en) 1995-03-15

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