Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
  • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
  • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
  • C07C211/45—Monoamines
  • C07C211/48—N-alkylated amines
• • 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
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
  • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C233/00—Carboxylic acid amides
  • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
  • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals

Definitions

• the present invention relates to new phenylbenzamides, a process for their production and their use for controlling undesirable microorganisms.
• phenylbenzamides have fungicidal properties (see e.g. EP-A 0 545 099).
• the phenylbenzamides N- (2-hexylphenyl) -2- (trifluoromethyl) benzamide and N- (2-hexylphenyl) -2-iodobenzamide are already known from EP-A 0 545 099, data for their biological activity not being included in the patent application mentioned are.
• R 1 represents trifluoromethyl, chlorine, bromine or iodine and R 2 represents hydrogen or methyl, R 2 also represents ethyl.
• R 2 represents hydrogen or methyl
• R 2 also represents ethyl
• R • represents hydrogen or methyl
• R 2 also represents ethyl
• the phenylbenzamides of the formula (I) according to the invention have a significantly better fungicidal activity than the constitutionally most similar, known active substances of the same activity.
• the phenylbenzamides according to the invention are generally defined by the formula (I).
• aniline required as starting materials in carrying out the process according to the invention in the first step and the alkenes of the formula (II), namely 4-methyl-1-pentene, 4,4-dimethyl-1-pentene and 4,4-dimethyl-1 -hexene, are generally known synthetic chemicals and are commercially available.
• alkylphenylamine derivatives of the formula (Tu) obtained in the first step (a) of the process according to the invention are new and likewise the subject of the present invention
• the base used in carrying out the first step (a) of the process according to the invention is all of the inorganic and organic compounds customary for such reactions. see bases into consideration.
• Aluminum granules are preferably used (cf. DE-OS 27 30 620).
• Amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU). Potassium carbonate is particularly preferably used.
• Suitable diluents for carrying out the second step (b) of the process according to the invention are all customary inert, organic solvents.
• Halogenated aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Chlorobenzene, dichlorobenzene,
• reaction temperatures can be varied over a wide range when carrying out the first step (a) of the process according to the invention.
• the procedure is generally in each case under increased pressure from 1 bar to 250 bar. Is preferably carried out under increased pressure of 50 bar to 150 bar.
• the substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.
• Erwinia species such as, for example, Erwinia amylovora
• Pythium species such as, for example, Pytbium ultimum
• the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.
• Microorganisms of the following genera may be mentioned, for example:
• emulsifiers and / or foaming agents are: e.g. nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyefhylene fatty alcohols, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
• nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyefhylene fatty alcohols, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
• natamycin natamycin
• nicobifen Nitrofhal-isopropyl
• Noviflumuron nuarimol
• propamocarb Propanosin sodium; propiconazole; propineb; proquinazid; Prostioconazole; pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; pyroquilon;
• simeconazole spiroxamine; Sulfur; tebuconazole; tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole;
• Thicyofen Thifluzamide; Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl;
• naphthenate copper oxychloride; Copper sulfate; Cufraneb; copper; mancopper; Oxine-copper.
• Bactericides bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin,
• Insecticides / acaricides / nematicides Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb,
• Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Indoxacarb, Isazofos, Isofenphos, Isoxathion, Ivermectin, Kernpolyederviruses, Lambda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Methaldehydro methamide, methaldehyde methacrylate Methoprene, methomyl,
• Me hoxyfenozide Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Milbe mycin, Monocrotophos,
• Pirimiphos M Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothoat, Pymetrozine, Pyraclofos, Pyresmethrin, Pyrethrum, Pyridaben, Pyridathion, Pyrimidifen, Pyriproxyfen, Quinalphos, Ribavirin, Salithion, Sebodosofofenos .
• the compounds of the formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antifungal effects, especially against dermatophytes and shoot fungi, mold and diphasic fungi (e.g. against Candida species such as Candida albicans,
• Candida glabrata and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
• the list of these fungi in no way represents a restriction of the detectable mycotic spectrum, but is only of an explanatory nature.
• the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.
• the application rates can be varied within a relatively wide range, depending on the type of application.
• the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha.
• the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed.
• the application rates of active ingredient generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
• plants and their parts can be treated.
• plant species and plant cultivars which occur wildly or are obtained by conventional organic breeding methods, such as crossing or protoplast fusion, and parts thereof are treated.
• transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods are treated.
• Organisms and their parts treated.
• the term “parts” or “parts of plants” or “parts of plants” was explained above.
• Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
• Plant cultivars are understood to mean plants with new properties (“traits”) which have been cultivated by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, breeds, bio- and genotypes.
• the treatment according to the invention can also result in superadditive (“synergistic”) effects.
• superadditive for example, reduced application rates and / or widening of the activity spectrum and or an intensification the effect of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased blooming, easier harvesting, acceleration of ripening, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the effects to be actually expected.
• the preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the crop products, higher storability and / or workability of the Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or vire n and an increased tolerance of the plants to certain herbicidal active ingredients.
• transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted.
• the properties (“traits”) are particularly emphasized of the plants' increased defense against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the
• Bt plants Gene Cry ⁇ A (a), Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylJIA, CryIJIB2, Cry9c Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”.
• Bt plants The increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins are also particularly emphasized as properties (“traits”).
• twins are also particularly emphasized the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazoline, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene).
• the genes imparting the desired properties (“traits”) can also be found in combinations with one another in the transgenic plants.
• “Bt plants” are maize varieties, cotton varieties, soy varieties and carcasses called potato varieties that are marketed under the trade names YIELD GARD ® (e.g. corn, cotton, soy), KnockOut ® (e.g. corn), StarLink ® (e.g.
• herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready ® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link ® (tolerance to phosphinotricin, e.g. rape), IMI ® (tolerance to Imidazolinone) and STS ® (tolerance to sulfonylureas such as maize).
• Herbicide-resistant plants (bred conventionally for herbicide tolerance) plants also sold under the name Clearfield ® varieties (eg maize) are mentioned. Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
• reaction solution is mixed with 200 ml of water and that
• reaction solution is mixed with 100 ml of water and the mixture is extracted with ethyl acetate. The organic phases are dried with sodium sulfate and concentrated. The residue is chromatographed on silica gel (gradient cyclohexane 100% to cyclohexane / ethyl acetate 1: 4).
• logP (pH 2.3) 4.63]
• the logP values given in the manufacturing examples were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.
• the calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive ones
• dimethylacetamide emulsifier 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
• Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
• dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
• the plants are then placed in a greenhouse at approx. 21 ° C and a relative humidity of approx. 90%.
• Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
• Botrytis test (bean) / protective
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
• Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
• Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Dentistry (AREA)
• Wood Science & Technology (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Agronomy & Crop Science (AREA)
• General Health & Medical Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Preparation Of Compounds By Using Micro-Organisms (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

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• 2002
  • 2002-07-02 DE DE10229595A patent/DE10229595A1/de not_active Withdrawn
• 2003
  • 2003-06-20 CN CNB038208121A patent/CN1324005C/zh not_active Expired - Fee Related
  • 2003-06-20 BR BRPI0312407-0A patent/BR0312407B1/pt not_active IP Right Cessation
  • 2003-06-20 EP EP03738073A patent/EP1519913A1/de not_active Withdrawn
  • 2003-06-20 JP JP2004518548A patent/JP4520299B2/ja not_active Expired - Fee Related
  • 2003-06-20 UA UAA200500915A patent/UA78340C2/uk unknown
  • 2003-06-20 MX MXPA05000114A patent/MXPA05000114A/es active IP Right Grant
  • 2003-06-20 AU AU2003245975A patent/AU2003245975A1/en not_active Abandoned
  • 2003-06-20 US US10/518,446 patent/US7314958B2/en not_active Expired - Fee Related
  • 2003-06-20 KR KR1020047021497A patent/KR101025742B1/ko not_active IP Right Cessation
  • 2003-06-20 WO PCT/EP2003/006512 patent/WO2004005242A1/de active Application Filing
  • 2003-06-20 EA EA200500037A patent/EA009884B1/ru not_active IP Right Cessation
  • 2003-06-20 PL PL03374466A patent/PL374466A1/xx not_active Application Discontinuation
  • 2003-06-20 CA CA002491368A patent/CA2491368A1/en not_active Abandoned
  • 2003-06-25 AR ARP030102277A patent/AR039743A1/es unknown
  • 2003-07-01 TW TW092117901A patent/TW200413284A/zh unknown
• 2004
  • 2004-12-22 IL IL165925A patent/IL165925A/en not_active IP Right Cessation
• 2005
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