EP0000377B1 - Procédé de préparation de dérivés de chromone, nouveaux dérivés de chromone et leur utilisation comme agents protecteurs de plantes - Google Patents

Procédé de préparation de dérivés de chromone, nouveaux dérivés de chromone et leur utilisation comme agents protecteurs de plantes Download PDF

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Publication number
EP0000377B1
EP0000377B1 EP78100318A EP78100318A EP0000377B1 EP 0000377 B1 EP0000377 B1 EP 0000377B1 EP 78100318 A EP78100318 A EP 78100318A EP 78100318 A EP78100318 A EP 78100318A EP 0000377 B1 EP0000377 B1 EP 0000377B1
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EP
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Prior art keywords
carbon atoms
chromon
alkyl
carboxy
carboxymethyl
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EP78100318A
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German (de)
English (en)
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EP0000377A1 (fr
Inventor
Hans-Joachim Dr. Kabbe
Paul-Ernst Dr. Frohberger
Peter Dr. Roessler
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2

Definitions

  • the invention relates to a chemically unique process for the production of chromone derivatives, as well as chromone derivatives and their use as crop protection agents.
  • chromones can also be prepared from o-acylphenols and carboxylic acid derivatives in a ratio of 1: 1 [cf. P. Karrer, "Textbook of Organic Chemistry", 13th edition, page 584, Georg Thieme Verlag, Stuttgart (1959)]
  • the new compounds of formula la have fungicidal properties; they also inhibit the development of arthropods. They are therefore of interest as pesticides.
  • R, R 'and R 2 preferably represent hydrogen and optionally substituted, straight-chain or branched alkyl having up to 8, preferably up to 2 carbon atoms, furthermore straight-chain or branched alkenyl with one or more double bonds and up to 8 Carbon atoms, preferably up to 3 carbon atoms and a double bond.
  • alkyl or alkenyl radicals are: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, hexyl, butene- (3) -yl and 4-methyl-penten- (3) -yl .
  • R, R 1 and R 2 furthermore represent optionally substituted cycloalkyl and cycloalkenyl radicals having 3 to 8, preferably having 4 to 6, carbon atoms, such as, for example, cyclobutyl and in particular cyclopentyl and cyclohexyl.
  • R, R 1 and R 2 furthermore represent phenyl and naphthyl, preferably phenyl.
  • phenylalkyl and naphthylalkyl radicals are: benzyl, phenylethyl, phenylpropyl, phenylbutyl, naphthylmethyl and naphthylethyl, preferably benzyl.
  • alkoxy groups are those with up to 4 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy and tert-butoxy.
  • Preferred phenylalkoxy groups include benzyloxy, phenylethoxy, phenylpropoxy, phenylisopropoxy, phenylbutoxy, phenylisobutoxy and phenyl tert-butoxy.
  • Preferred alkoxycarbonyl groups are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl.
  • Dimethylamino, diethylamino and diisopropylamino may be mentioned as preferred dialkylamino groups. It is also possible for the two alkyl radicals of the dialkylamino group to be closed to form a ring, such as, for example, pyrrolidinyl, piperidinyl.
  • Halogens are fluorine, chlorine, bromine and iodine, preferably chlorine and bromine.
  • the radicals R and R 1 can form a carbocyclic or heterocyclic five- or six-membered ring with the two carbon atoms of the benzene ring on which they are located, such as, for example, a cyclopentene, cyclohexene, benzene, furan, dihydrofuran, thiophene , Dihydrothiophene, pyran, dihydropyran, pyridine or dioxole ring.
  • Substituents which do not change under the reaction conditions are suitable as substituents of the alkyl, cycloalkyl, aryl, aralkyl, alkoxy, aralkoxy, alkoxycarbonyl and dialkylamino groups of the radicals R to R 2 .
  • the halogens such as fluorine, chlorine, bromine and Called iodine and the cyano group, also the alkoxy and alkoxycarbonyl group with up to 4, and - if there are substituents on ring systems - still the alkyl and alkoxycarbonylalkyl group with up to 4 carbon atoms.
  • the dialkylamino group with a total of up to 6, preferably up to 2, carbon atoms may also be mentioned as further second substituents.
  • the glyoxylic acid derivatives of the formula 111 are also required as starting compounds.
  • Z stands for mono- or divalent cations of alkali and alkaline earth metals, as well as for the ammonium cation and the mono-, di- and trialkylammonium cations.
  • the alkyl radicals contain up to 2 carbon atoms.
  • Secondary amines are preferred as such, in particular cyclic amines such as pyrrolidine, piperidine, N-methylpiperazine and morpholine, but also open-chain amines such as dimethylamine and diethylamine.
  • Secondary amines are preferred as such, in particular cyclic amines such as pyrrolidine, piperidine, N-methylpiperazine and morpholine, but also open-chain amines such as dimethylamine and diethylamine.
  • the compounds mentioned are generally known.
  • the process according to the invention can be carried out with or without a solvent.
  • solvents which may be mentioned are: aliphatic or aromatic hydrocarbons, such as petroleum ether, benzene, toluene or xylene, aliphatic or aromatic halogenated hydrocarbons, such as carbon tetrachloride, chlorobenzene or dichlorobenzene, ethers, such as diethyl ether, tetrahydrofuran, dioxane or glycol dimethyl amide, dimethyethyl formamide, dimethylacetyl dimethyl amide, dimethylacetyl dimethyl amide, dimethylacetyl dimethyl amide, dimethylacetyl dimethyl amide, dimethylacetyl dimethyl amide, dimethylacetyl dimethyl amide, dimethylacetyl dimethyl amide, dimethylacetyl dimethyl amide, dimethylacetyl dimethyl amide, dimethylacetyl dimethyl amide, di
  • the process according to the invention is carried out at a temperature of from -30 to + 150 ° C., preferably from 20 to 80 ° C.
  • the o-hydroxyacetophenones (11) and the salt of glyoxylic acid (111) are generally used in stoichiometric amounts, ie in a ratio of 1: 2.
  • a small excess of a component, in particular the glyoxylic acid salt is used (e.g. up to a molar ratio of 1: 2.5).
  • the amount of the amine used is not critical. In general, 0.05 to 1.5, preferably 0.1 to 1 mol of the amine, based on 1 mol of the o-hydroxycarbonyl compound, is used. If the o-hydroxyacetophenones are caused by acidic groups such as e.g. Carboxy groups, are substituted, it may be expedient to neutralize the acid groups by an excess of the amine.
  • the esterification of the dicarboxylic acids thus obtained can be carried out, for example, in a customary manner by stirring the dicarboxylic acid in a 4 to 100, preferably 10 to 50, molar amount of alcohol of the formula R 3 -OH, with an acid such as conc. Added sulfuric acid or saturated with hydrogen chloride gas and warmed to temperatures from 60 to 120 ° C for a few hours.
  • the mixture of the dicarboxylic acid with the alcohol can also be mixed with at least twice the molar amount, based on the dicarboxylic acid, of a dehydrating agent, such as inorganic acid halides, for example thionyl chloride or phosphorus oxychloride.
  • salts of the dicarboxylic acids can also be reacted with at least twice the molar amount of an alkyl halide in a solvent, such as dimethyl sulfoxide or dimethylformamide.
  • the active compounds according to the invention have a good fungitoxic effect. They do not damage crops in the concentrations necessary to control fungi. For these reasons, they are suitable for use as crop protection agents for combating fungi. Fungitoxic agents in crop protection are used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Bsidiomycetes, Deuteromycetes.
  • the active compounds according to the invention can be used against parasitic fungi and bacteria which attack above-ground parts of plants or attack the plants from the ground, and against seed-borne pathogens.
  • the good tolerance to plants allows use against fungal plant diseases by treating the standing crop or individual parts of it or the seed or the crop soil.
  • the active ingredients are particularly effective against powdery mildew.
  • the active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, pastes and granules. These are known in the. Prepared in this way, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • liquid solvents aromatics, such as xylene, toluene, benzene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or Glycol and their ethers and esters, ketones such as acetone, methyl ethylene ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water; liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as dichlorodifluoromethane or trichlorofluoromethane; as solid carriers: natural rock flour, such as
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds as such in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and. Granules can be applied. They are used in the usual way, e.g. by spraying, spraying, misting, scattering, dusting, pouring, dry pickling, slurry pickling (slurry pickling), wet pickling and wet pickling.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 100% by weight of active substance, preferably between 0.01 and 10% by weight.
  • active compound in the case of dressing, amounts of active compound of 10 mg to 10 g, preferably 100 mg to 3 g, are generally used per kilogram of seed.
  • active substance concentrations in the case of soil treatment, which can be carried out over the entire surface, in strips or in a punctiform manner, active substance concentrations of 1 to 1000 g of active substance per m 3 of soil, preferably 10 to 200 g per m3 , are required at the location of the expected action .
  • the compounds according to the invention inhibit the development of arthropods (arthrophodes).
  • the tests given below show the arthropod metamorphosis-inhibiting activity of the compounds according to the invention, without wishing to carry out any restriction with regard to the range of action of these compounds.
  • the morphological changes such as half pupated animals, incompletely hatched larvae or caterpillars, defective wings, puppal cuticles in adults and the death rate are assessed.
  • the sum of the morphological malformations and the mortality during development are rated.
  • active compound 2 parts by weight of active compound are mixed with the stated amount of solvent, emulsifier and enough water to form a 1% mixture which is diluted with water to the desired concentration.
  • test animals are fed leaves of the forage plants, which are provided with a uniform spray coating of the active compound mixture of the selected concentration, so that an amount of active compound in ppm ("parts per million") is obtained on the leaves until the development of the Imago.
  • active compound 0.25 part by weight of active compound is taken up in 25 parts by weight of dimethylformamide and 0.06 part by weight of emulsifier (alkylaryl polyglycol ether), and 975 parts by weight of water are added.
  • emulsifier alkylaryl polyglycol ether
  • the concentrate is diluted with water to the desired final concentration of the spray mixture.
  • the stocking of the plants with mildew pustules is evaluated.
  • the degree of infestation is expressed as a percentage of the infestation of the untreated control plants. 096 means no infection and 100% the same degree of infection as for the untreated control. The lower the mildew infestation, the more effective the active ingredient.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (6)

1. Procédé pour la préparation de dérivés de chromone de formule générale
Figure imgb0022
dans laquelle
R, R1 et R2 peuvent être identiques ou différents et représentent l'hydrogène ou un groupe alkyle, cycloalkyle, alcényle, cycloalcényle, chacun jusqu'en Ce, les restes alkyle ou cycloalkyle pouvant être éventuellement substitués par des halogènes ou des groupes cyano, alkoxy ou alkoxycarbonyle jusqu'en C4; en outre, un groupe phényle, naphtyle, phénylalkyle et naphtylalkyle, le reste alkyle ayant 1 à 4 atomes de carbone; les restes aromatiques mentionés pouvant être substitués par des halogènes ou des groupes cyano, alkyle, alkoxy, alcoxycarbonyle et alkoxycarbonylalkyle jusqu'en C4 et des groupes dialkylamino ayant au total jusqu'à 6 atomes de carbone; en outre, des groupes alkoxy jusqu'en C4 éventuellement substitués par des halogènes ou des groupes cyano; ensuite des groupes phénoxy, naphtoxy et phényl-alkoxy jusqu'en C4; encore des halogènes, des groupes cyano ou hydroxy; et enfin des groupes alkoxycarbonyle jusqu'en C4 et di(alkyl jusqu'en C3)amino, les deux restes alkyle pouvant aussi former avec l'atome d'azote du groupe amino un noyau hétérocyclique; et, en outre, deux restes R et R1 pouvant former avec deux atomes de carbone du noyau benzénique un noyau carbocyclique ou hétérocyclique à 5 ou 6 chaînons, et R3 représente l'hydrogène ou un groupe alkyle jusqu-en C4, ce dernier pouvant être substitué par des halogènes ou des groupes méthoxy, en outre un groupe allyle, cyclopentyle, cyclohexyle, benzyle, chlorobenzyle ou phényléthyle, caractérisé en ce que l'on fait réagir des o-hydroxyacéto- phénones de formule générale
Figure imgb0023
dans laquelle
R, R' et R2 ont la signification indiquée ci-dessus, avec des dérivés d'acide glyoxylique de formule générale
Figure imgb0024
dans laquelle
Z représente des cations mono- ou divalents de métaux alcalins et alcalino-terreux, ainsi que le cation ammonium, mono-, di- et trialkylammonium, les restes alkyle ayant chacun jusqu'à 2 atomes de carbone,

en présence de composés basiques dans un domaine de températures de -30 à +150aC, et l'on transforme encore éventuellement en esters correspondants, de manière connue, les acides carboxyliques ainsi obtenus après acidification.
2. Procédé selon la revendication 1, caractérisé en ce que l'on utilise comme composés basiques des amines secondaires.
3. Procédé selon la revendication 1, caractérisé en ce que l'on effectue la réaction dans un domaine de températures de +20 à +80°C.
4. Dérivés de chromone de formule générale (la)
Figure imgb0025
dans laquelle
R' représente l'hydrogène, le chlore ou un groupe méthoxy, et
R" représente l'hydrogène ou un groupe méthyle.
5. Fongicides et agents inhibant le développement des arthropodes, caractérisés en ce qu'ils contiennent au moins un dérivé de chromone selon la revendication 4.
6. Utilisation des dérivés de chromone selon la revendication 4 pour la lutte contre les champignons et l'inhibition du développement des arthropodes.
EP78100318A 1977-07-13 1978-07-06 Procédé de préparation de dérivés de chromone, nouveaux dérivés de chromone et leur utilisation comme agents protecteurs de plantes Expired EP0000377B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772731566 DE2731566A1 (de) 1977-07-13 1977-07-13 Verfahren zur herstellung von neuen chromon-derivaten, sowie ihre verwendung als pflanzenschutzmittel
DE2731566 1977-07-13

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EP0000377A1 EP0000377A1 (fr) 1979-01-24
EP0000377B1 true EP0000377B1 (fr) 1981-01-21

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Country Status (8)

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US (3) US4189498A (fr)
EP (1) EP0000377B1 (fr)
JP (1) JPS5419981A (fr)
BR (1) BR7804502A (fr)
DE (2) DE2731566A1 (fr)
DK (1) DK314078A (fr)
IL (1) IL55112A (fr)
IT (1) IT7825578A0 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IN164232B (fr) * 1986-04-11 1989-02-04 Hoechst India
AU7738298A (en) * 1996-12-19 1998-07-15 Agrevo Uk Limited Chromones useful as fungicides
BR0206513A (pt) * 2001-01-16 2004-01-06 Astrazeneca Ab Composição, métodos de tratamento de um ser humano ou animal que sofre de depressão, ansiedade generalizada, distúrbios da alimentação, demência, distúrbio do p nico, distúrbios do sono, distúrbios gastrointestinais, distúrbios motores, distúrbios endócrinos, vasoespasmo e disfunção sexual, uso de qualquer um dos compostos, composição farmacêutica, e, processo para preparar compostos
WO2002055012A2 (fr) 2001-01-16 2002-07-18 Astrazeneca Ab Composes heterocycliques therapeutiques
SE0103646D0 (sv) * 2001-11-01 2001-11-01 Astrazeneca Ab Therapeutic chroman compounds
SE0103647D0 (sv) * 2001-11-01 2001-11-01 Astrazeneca Ab Therapeutic chromone compounds
JP4561245B2 (ja) * 2004-08-31 2010-10-13 住友化学株式会社 クロモン化合物及びその用途

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3879427A (en) * 1972-11-24 1975-04-22 Warner Lambert Co Derivatives of polycyclic gamma-pyrones
US3862143A (en) * 1972-12-04 1975-01-21 Warner Lambert Co Substituted chromone-3-carbonitriles, carboxamides and carboxylic acids

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Publication number Publication date
BR7804502A (pt) 1979-03-20
EP0000377A1 (fr) 1979-01-24
IT7825578A0 (it) 1978-07-11
US4189498A (en) 1980-02-19
US4307020A (en) 1981-12-22
IL55112A0 (en) 1978-09-29
DE2731566A1 (de) 1979-02-01
IL55112A (en) 1983-02-23
JPS5419981A (en) 1979-02-15
DE2860356D1 (en) 1981-03-12
DK314078A (da) 1979-01-14
US4285965A (en) 1981-08-25

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