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EP0000112A1 - Dérivés soufrés substitués par le triazol, leur préparation et utilisation comme fongicides - Google Patents

Dérivés soufrés substitués par le triazol, leur préparation et utilisation comme fongicides Download PDF

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Publication number
EP0000112A1
EP0000112A1 EP78100044A EP78100044A EP0000112A1 EP 0000112 A1 EP0000112 A1 EP 0000112A1 EP 78100044 A EP78100044 A EP 78100044A EP 78100044 A EP78100044 A EP 78100044A EP 0000112 A1 EP0000112 A1 EP 0000112A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
phenyl
numbers
triazole
radical
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
EP78100044A
Other languages
German (de)
English (en)
Other versions
EP0000112B1 (fr
Inventor
Ernst-Heinrich Dr. Pommer
Friedrich Dr. Linhart
Ernst Dr. Buschmann
Bernd Dr. Zeeh
York Dr. Hartleben
Klaus Dr. Gutsche
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Publication of EP0000112A1 publication Critical patent/EP0000112A1/fr
Application granted granted Critical
Publication of EP0000112B1 publication Critical patent/EP0000112B1/fr
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present invention relates to new valuable triazole-substituted sulfur compounds and their salts and metal complex salts with good fungicidal activity, to processes for their preparation and to fungicides which contain these compounds as active compounds.
  • imidazole-substituted sulfur compounds as fungicides for controlling phytopathogenic fungi (DE-OS 25 41 833).
  • they often only act against a certain fungus or against a certain class of fungus, or cause damage to the crop plants or, when used as a mordant, cause germination delays and damage to the emergence, so that their general and broad application are subject to strict limits.
  • the salts have the general formula II in which R 1 , R 2 , n and k have the meanings given above and HS denotes any organic or inorganic acid which, however, must not be phytotoxic at the application rates used and must be able to form salts with the compounds of the formula I. to build.
  • Particularly suitable acids are sulfuric acid, nitric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, trichloroacetic acid, dichloropropionic acid, oxalic acid, toluenesulfonic acid, dodecylbenzenesulfonic acid.
  • the compounds of the formula II can be prepared by simply adding the acids HS to the compounds of the formula I, if appropriate in a solvent.
  • the metal complex salts have the general formula in which R 1 , R 2 , n and k have the meanings given above, p and q are the numbers 1 to 4, Y ° is an equivalent of an anion of an inorganic or organic acid and Me is a metal from I., II. and IV. to VIII. Subgroup and from the II. and IV. Main group of the periodic system.
  • Such metals are for example: copper, iron, zinc, tin.
  • the metal complex salts can be prepared by reacting a metal salt with a compound of the formula I in a solvent.
  • the compounds of the formula I can be reacted with 2-haloethyl-2,2,4-triazoles of the formula III in which R 1 and n have the meaning given above and X is chlorine, bromine or iodine, with a mercaptide of the general formula IV in which R 2 has the meaning given above, in a solvent.
  • the mercaptide is prepared from the associated mercaptan by reaction with a base before or during the reaction.
  • the compounds of the formula I in which k represents the numbers 1 or 2 are obtained from compounds of the formula I in which k represents the number 0 by oxidation with an oxygen-donating reagent according to the customary, generally known methods of oxidizing sulfides. Sulfoxides and sulfones manufactured.
  • the new fungicidal compounds are obtained either in the form of the free bases or their salts.
  • the salts can be converted to the free bases in the usual manner, e.g. by reaction with alkali such as sodium or potassium hydroxide, sodium or potassium carbonate, ammonia or similar alkalis.
  • alkali such as sodium or potassium hydroxide, sodium or potassium carbonate, ammonia or similar alkalis.
  • the compounds in base form can be reacted with suitable acids, e.g.
  • inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, organic acids such as trichloroacetic acid, dichloropropionic acid, oxalic acid, toluenesulfonic acid or higher alkylbenzenesulfonic acids such as dodecylbenzenesulfonic acid can be converted into the salts which are valuable in terms of application technology.
  • the triazole-substituted sulfur compounds according to the invention and their salts and metal complex salts are distinguished by an outstanding activity against a broad spectrum of phytopathogenic fungi. Some of them are systemically effective and can be used as foliar and soil fungicides, but also as mordants and as technical fungicides.
  • the fungicidal compounds are particularly interesting for controlling a large number of fungi on different crop plants.
  • crops in In this context in particular wheat, rye, barley, oats, rice, corn, cotton, soybeans, coffee, sugar cane, fruit and ornamental plants in horticulture, and also vegetables such as cucumbers, beans and pumpkin plants.
  • the substances according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the application forms * depend entirely on the purposes; in any case, they should ensure a fine and uniform distribution of the active substance.
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if appropriate using emulsifiers and dispersants, where - if used - water as a diluent, other organic solvents can also be used as auxiliary solvents.
  • auxiliaries whose compounds according to the invention.
  • Solvents such as aromatics (e.g. xylene, benzene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), amines (e.g.
  • Ethanolamine, dimethylformamide) and water such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, S. silicates.); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene - fatty alcohol - ether, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin, sulfite liquors and methyl cellulose.
  • Carriers such as natural stone powder (e.g. kaolins, clays, talc, chalk) and synthetic stone powder (e.g. highly disperse silica, S. silicates.); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene - fatty alcohol - ether, alkyl sulfonates and aryl sulfonates) and dispers
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • formulations or the ready-to-use preparations produced therefrom, such as solutions, emulsions, suspensions, powders, dusts, pickles, pastes or granules, are used in a known manner.
  • the application rates are between 0.01 and 3, but preferably between 0.01 and 1 kg of active ingredient per hectare.
  • the agents according to the invention can also be present together with other active ingredients, such as Herbicides, insecticides, growth regulators and fungicides. Or mixed with fertilizers and applied. When mixed with fungicides you get in many. Cases an increase in the fungicidal spectrum of activity; a number of these fungicide mixtures also have synergistic effects, i.e. the fungicidal activity of the combination product is greater than that of the added activity of the individual components.
  • active ingredients such as Herbicides, insecticides, growth regulators and fungicides.
  • fertilizers When mixed with fungicides you get in many. Cases an increase in the fungicidal spectrum of activity; a number of these fungicide mixtures also have synergistic effects, i.e. the fungicidal activity of the combination product is greater than that of the added activity of the individual components.
  • Eluciter_von barley seedlings grown in pots are sprayed with aqueous emulsions of 80% (wt.%) Active ingredient and 20% emulsifier and, after the spray coating has dried on, are dusted with (spores) of the barley powdery mildew (Erysiphe graminis var. Hordei).
  • the test plants are then placed in a greenhouse at temperatures between 20 and 22 ° C and 75 to 80% relative humidity. After 10 days, the extent of the development of mildew is determined.
  • Leaves of potted wheat seedlings of the "Jubilar” variety are sprayed with aqueous emulsions of 80% (weight percent) active ingredient and 20% emulsifier and, after the spray coating has dried on, are dusted with oidia (spores) of the powdery mildew (Erysiphe graminis var. Tritici) .
  • the test plants are then placed in a greenhouse at temperatures between 20 and 22 ° C and 75 to 80% relative humidity. The extent of mildew development is determined after 10 days. 0 no infection, graded to 5 total infection.
  • Leaves of potted wheat seedlins of the "Caribo" variety are dusted with spores of the brown rust (Puccinia recondita).
  • the pots are then placed in a chamber with high humidity (90 to 95%) at 20 to 22 ° C for 24 hours. During this time, the spores germinate and the germ tubes penetrate the leaf tissue.
  • the infected plants are then sprayed to runoff point with 0.05%, 0.025 and 0.012% (wt.%) Aqueous spray liquors which contain 80% active ingredient and 20% lignin sulfonate in the dry substance. After the spray coating has dried on, the test plants are placed in the greenhouse at temperatures between 20 and 22 ° C. and 65 to 70% relative atmospheric humidity. After 8 days, the extent of the rust fungus development on the leaves is determined.
  • compound 2 20 parts by weight of compound 2 are mixed. dissolved, which consists of 80 parts by weight of xylene, 10 parts by weight of the adduct, from 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dädecylbenzenesulfonic acid and 5 parts by weight of the additive of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
  • 20 parts by weight of active ingredient 2 are mixed well with 3 parts by weight of the sodium salt of diiaebutylnaphthalene- ⁇ -sulfonic acid, 17 parts by weight of the sodium salt of lignin sulfonic acid from a Su.lfit waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill.
  • a spray mixture is obtained which contains 0.1% by weight of the active ingredient.
  • active ingredient 1 40 parts by weight of active ingredient 1 are intimately mixed with 10 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. Dilution with 100,000 parts by weight of water gives an aqueous dispersion which contains 0.04% by weight of active ingredient.
  • 20 parts of the compound 2 is lfonTalkre with 2 parts of calcium salt 'of the Dodecylbenzolsu', 8 parts of fatty alcohol polyglycol ether, 2 parts of sodium salt of a Phen'olsulfonklare- urea-formaldehyde condensate and 68 parts of a paraffinic mineral intimately mixed.
  • a stable oily dispersion is obtained.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP78100044A 1977-06-01 1978-06-01 Dérivés soufrés substitués par le triazol, leur préparation et utilisation comme fongicides Expired EP0000112B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2724684 1977-06-01
DE19772724684 DE2724684A1 (de) 1977-06-01 1977-06-01 Triazolsubstituierte schwefelverbindungen

Publications (2)

Publication Number Publication Date
EP0000112A1 true EP0000112A1 (fr) 1978-12-20
EP0000112B1 EP0000112B1 (fr) 1981-09-09

Family

ID=6010391

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100044A Expired EP0000112B1 (fr) 1977-06-01 1978-06-01 Dérivés soufrés substitués par le triazol, leur préparation et utilisation comme fongicides

Country Status (2)

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EP (1) EP0000112B1 (fr)
DE (2) DE2724684A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0022531A1 (fr) * 1979-07-17 1981-01-21 Bayer Ag 1-(2,4-Dichlorophényl)-1-(2,6-dihalogéno benzylmercapto)-2-(1,2,4 triazol 1-yl)-éthanes, procédé pour leur préparation et leur utilisation comme fongicides
EP0059894A1 (fr) * 1981-03-07 1982-09-15 Bayer Ag Triazolylalkylthio éthers, procédé pour leur préparation et leur application comme agent régulateur de la croissance des plantes et comme agent fongicide
EP0146755A1 (fr) * 1983-11-23 1985-07-03 Bayer Ag Utilisation du 1-(2,4-dichlorophénnyl)-1-(4-chlorobenzylthio)-2-(1,2,4-triazol-1-yl)-éthane pour régler la croissance des plantes
EP0061789B1 (fr) * 1981-03-27 1985-10-23 Janssen Pharmaceutica N.V. Dérivés du triazole à activité antimicrobienne
WO1993011118A1 (fr) * 1991-12-04 1993-06-10 Agrevo Uk Limited Herbicides et fongicides derives de pyrole
WO1994008978A1 (fr) * 1992-10-09 1994-04-28 Uniroyal Chemical Company, Inc. Derives d'azole substitues fongicides
WO2003055850A1 (fr) * 2001-12-27 2003-07-10 Daiichi Pharmaceutical Co., Ltd. Inhibiteurs de la production/secretion de la proteine amyloide-$g(b)
US7932271B2 (en) 2003-06-30 2011-04-26 Daiichi Pharmaceutical Co., Ltd. Heterocyclic methyl sulfone derivative

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7710992A (nl) * 1976-10-08 1978-04-11 Bayer Ag Werkwijze voor het bereiden van (1-fenyl-2- -triazolyl-ethyl)thioether-derivaten, alsmede de toepassing ervan als fungiciden en middelen voor het regelen van de groei.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7710992A (nl) * 1976-10-08 1978-04-11 Bayer Ag Werkwijze voor het bereiden van (1-fenyl-2- -triazolyl-ethyl)thioether-derivaten, alsmede de toepassing ervan als fungiciden en middelen voor het regelen van de groei.

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0022531A1 (fr) * 1979-07-17 1981-01-21 Bayer Ag 1-(2,4-Dichlorophényl)-1-(2,6-dihalogéno benzylmercapto)-2-(1,2,4 triazol 1-yl)-éthanes, procédé pour leur préparation et leur utilisation comme fongicides
EP0059894A1 (fr) * 1981-03-07 1982-09-15 Bayer Ag Triazolylalkylthio éthers, procédé pour leur préparation et leur application comme agent régulateur de la croissance des plantes et comme agent fongicide
US4507141A (en) * 1981-03-07 1985-03-26 Bayer Aktiengesellschaft Triazolylalkyl-thioether plant growth regulators and fungicides
EP0061789B1 (fr) * 1981-03-27 1985-10-23 Janssen Pharmaceutica N.V. Dérivés du triazole à activité antimicrobienne
EP0146755A1 (fr) * 1983-11-23 1985-07-03 Bayer Ag Utilisation du 1-(2,4-dichlorophénnyl)-1-(4-chlorobenzylthio)-2-(1,2,4-triazol-1-yl)-éthane pour régler la croissance des plantes
WO1993011118A1 (fr) * 1991-12-04 1993-06-10 Agrevo Uk Limited Herbicides et fongicides derives de pyrole
WO1994008978A1 (fr) * 1992-10-09 1994-04-28 Uniroyal Chemical Company, Inc. Derives d'azole substitues fongicides
WO2003055850A1 (fr) * 2001-12-27 2003-07-10 Daiichi Pharmaceutical Co., Ltd. Inhibiteurs de la production/secretion de la proteine amyloide-$g(b)
US7399775B2 (en) 2001-12-27 2008-07-15 Daiichi Pharmaceutical Co., Ltd. β-amyloid protein production/secretion inhibitor
US7932271B2 (en) 2003-06-30 2011-04-26 Daiichi Pharmaceutical Co., Ltd. Heterocyclic methyl sulfone derivative

Also Published As

Publication number Publication date
DE2861048D1 (en) 1981-11-26
DE2724684A1 (de) 1978-12-14
EP0000112B1 (fr) 1981-09-09

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