Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or 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 to ring carbon atoms
  • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
  • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
  • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
• • 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
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
  • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings

Definitions

• the present invention relates to bactericidal agents and to a method for controlling Erwinia species by applying a compound of the formula I or its salts where X is hydrogen, fluorine or chlorine and R is a lower alkyl radical.
• the lower alkyl radical are methyl, ethyl, propyl, isopropyl, butyl, isobutyl and sec. Understand butyl.
• the salts are those of strong organic bases such as methylamine. Triethylamine, but especially to understand such inorganic alkali and alkaline earth metals and ammonia.
• E. carotovora E. atroseptica
• E. chrysanthemi E. amylovora
• pathogens of the E. carotovora group can also seed the field, e.g. Potato tubers to be destroyed before germination ("Seed Piece decay"). Potato plants can show the symptoms of black leg, beets, cabbage and Konnyaku can be damaged in a similar way.
• Na hypochlorite Na0C1
• spray applications with streptomycin carried out with insufficient success.
• X is hydrogen or chlorine and R is a lower alkyl radical, preferably ethyl, propyl and isopropyl.
• Chino.loncarboxylic acids are in general form as therapeutic agents in the GB-PS. 830,832 A plant bactericidal effect is not mentioned. The majority of the compounds mentioned there are completely ineffective against E. amylovora,
• the compounds of the formula I are prepared by reacting an aniline derivative of the formula II with an alkoxymethylene malonic acid ester with elimination of alkanol at 20 ° to 160 ° C. and ring closure of the anilinomethylene malonic acid ester of the formula III obtained at elevated temperature from 200 ° to 280 ° C. and splitting off the alcoholic part of one of the ester groups for the 4-hydroxyquinoline-3-carboxylic acid ester of the formula IV and subsequent introduction of a substituent R by conventional alkylation with, for example, an alkyl halide (such as alkyl bromide or alkyl iodide).
• an alkyl halide such as alkyl bromide or alkyl iodide
• the quinolonecarboxylic acid ester of the formula V obtained can be saponified with bases to give compounds of the formula I and is in the salt form from which it can, if desired, be converted into the free carboxylic acid by acidification: (alk and alk 'are any releasable alkyl residues)
• quinolonecarboxylic acids of the formula I are stable compounds which are insoluble in most organic solvents at normal temperature, partially soluble in water, but readily soluble when alkali or strong amines are added.
• acidifying with e.g. Mineral acids can be precipitated or stabilized as a colloidal solution.
• the invention also relates to the new compounds of the formula I in which X is fluorine or chlorine and R is a lower alkyl radical, or in which X is hydrogen and R is methyl, propyl, isopropyl, butyl, isobutyl and sec. Butyl means.
• Suitable carriers and additives can be solid or liquid and correspond to the substances commonly used in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers.
• the active substance content in commercially available agents is between 0.1 and 90%.
• the active compounds of the formula I of the present invention can be formulated, for example, as follows:
• Spray powder The following components are used to produce a) 40% and b) 10% spray powder:
• the active ingredients are intimately mixed with the additives in suitable mixers and ground on appropriate heaters and rollers.
• suitable mixers and ground on appropriate heaters and rollers.
• Emulsifiable concentrates The following substances are used to produce a 25% emulsifiable concentrate: Such concentrates can be used to produce emulsions of the desired concentration by dilution with water, which are particularly suitable for leaf application.
• test substances formulated as wettable powder
• the test substances are suspended in water and sprayed in various concentrations (1000 to 100 ppm AS) on annual Bartlett pear seedlings to the point of dripping wet.
• the trees are infected 24 hours later by spraying them with an aqueous suspension of a virulent strain of Erwinia amylovora.
• the plants are kept in a climate room at 25 ° C. and 100% rel. For 24 hours. Humidity set up. The further incubation then takes place in a conventional greenhouse. Seven days after infection, the trial is evaluated by determining the percentage of infected plants per treatment. 20 trees are used for each treatment. Streptomycin serves as the standard and only infected trees treated with water are used as controls.
• Potato tubers are cut in half. The halves are kept for 5 min. immersed in an aqueous suspension with 40 ppm or 10 ppm of active ingredient and allowed to dry on the surface of glass dishes. After 2 hours they are sprayed with a bacterial suspension from Erwinia carotovora. Unmerged tuber halves are also infected and serve as a control. All infected tubers are then incubated at approx. 26 ° C and 90 - 100% relative humidity. Four days after infection, the untreated tubers decomposed to a pulp, so the effect on treated tubers can be assessed visually.
• the compounds of formula I consistently showed protective effects at 40 ppm. Among others, compound No. 2 in particular showed this effect even at a concentration of 10 ppm.

Landscapes

• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Environmental Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Plant Pathology (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Quinoline Compounds (AREA)
• Plural Heterocyclic Compounds (AREA)

Applications Claiming Priority (4)

Publications (2)

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ID=25699309

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Cited By (4)

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Citations (2)

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• 1978
  • 1978-06-26 US US05/918,999 patent/US4264604A/en not_active Expired - Lifetime
  • 1978-06-29 DE DE7878100280T patent/DE2860810D1/de not_active Expired
  • 1978-06-29 EP EP78100280A patent/EP0000203B1/fr not_active Expired
  • 1978-06-29 IL IL55043A patent/IL55043A/xx unknown
  • 1978-06-30 IT IT7825237A patent/IT7825237A0/it unknown
  • 1978-06-30 SU SU782633445A patent/SU931089A3/ru active
  • 1978-06-30 AT AT478578A patent/AT361739B/de not_active IP Right Cessation
  • 1978-06-30 AU AU37675/78A patent/AU523882B2/en not_active Expired
  • 1978-07-01 JP JP8046678A patent/JPS5414978A/ja active Pending

Patent Citations (2)

Non-Patent Citations (1)

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