EP0000112B1 - 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
EP0000112B1
EP0000112B1 EP78100044A EP78100044A EP0000112B1 EP 0000112 B1 EP0000112 B1 EP 0000112B1 EP 78100044 A EP78100044 A EP 78100044A EP 78100044 A EP78100044 A EP 78100044A EP 0000112 B1 EP0000112 B1 EP 0000112B1
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Prior art keywords
triazole
ethyl
parts
dichlorophenyl
carbon atoms
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EP78100044A
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German (de)
English (en)
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EP0000112A1 (fr
Inventor
Ernst-Heinrich Dr. Pommer
Friedrich Dr. Linhart
Ernst Dr. Buschmann
Bernd Dr. Zeeh
York Dr. Hartleben
Klaus Dr. Gutsche
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BASF SE
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BASF SE
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    • 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 invention relates to valuable triazole-substituted sulfur compounds, 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 specific fungus or against a specific class of fungus, or cause damage to the crop plants or, when used as a mordant, cause germination delays and damage caused by emergence, so that their general and broad application are subject to strict limits.
  • the salts have the general formula II in which R ', 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 react with the compounds of the general formula 1 To form salts.
  • Particularly suitable acids are sulfuric acid, nitric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, trichloroacetic acid, dichloropropionic acid, oxalic acid, toluenesulfonic acid and dodecylbenzenesulfonic acid.
  • the compounds of the general formula II can be prepared by simply adding the acids HS to the compounds of the general formula I, if appropriate in a solvent.
  • the metal complex salts have the general formula Ila 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 the 1st, 11th and IV. To VIII. Subgroup and from de II. And IV. Main group of the periodic system.
  • Such metals are: copper, iron, zinc and tin.
  • the metal complex salts can be prepared by reacting a metal salt with a compound of the general formula I in a solvent.
  • the compounds of the general formula can be reacted with 2-haloethyl-1,2,4-triazoles of the general 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 general formula I in which k represents the numbers 1 or 2, are converted from compounds of general 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 fungicidal compounds according to the invention 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.
  • 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.
  • Hydrogen chloride is gassed into the extract, 25.9 parts of 1 - [2-butylmercapto-2 - (2,4-dichlorophenyl) - ethyl - (1)] 1,2,4-triazole hydrochloride precipitate out, which after recrystallization from ethyl acetate melt at 143 ° C.
  • the triazole-substituted sulfur compounds according to the invention and their salts and metal complex salts are notable for excellent 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 to mean, 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 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 e.g. Herbicides, insecticides, growth regulators and fungicides or also mixed with fertilizers and applied.
  • active ingredients such as e.g. Herbicides, insecticides, growth regulators and fungicides or also mixed with fertilizers and applied.
  • the fungicidal spectrum of activity is enlarged; 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.
  • Leaves of barley seedlings grown in pots are sprayed with aqueous emulsions of 80% (% by weight) active ingredient and 20% emulsifier and, after the spray coating has dried on, are dusted with oidia (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 mildew development 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.
  • leaves of pots of oat seed of the "Flämings Krone" variety are dusted with spores of the oat crown rust (Puccinia coronata) and placed in a chamber with high atmospheric humidity.
  • the infected plants are then sprayed to runoff point with 0.05% (by weight) aqueous spray liquors which contain 80% active ingredient and 20% lignin sulfonate in the dry matter.
  • the test plants are grown in the greenhouse at temperatures between 20 and 22 ° C. and 65 to 70% rel. Humidity set up. After 8 days, the extent of the rust fungus development on the leaves is determined.
  • active ingredient 2 20 parts by weight of active ingredient 2 are mixed well with 3 parts by weight of the sodium acid of diisobutylnaphthalene-a-sulfonic acid, 17 parts by weight of the sodium salt of lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill.
  • a spray liquor 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.
  • active ingredient 2 20 parts are intimately mixed with 2 parts of calcium salt of dodecylbenzenesulfonic acid, 8 parts of fatty alcohol polyglycol ether, 2 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. 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)

Claims (17)

1. Composés soufrés à substituant triazole, de formule générale 1
Figure imgb0020
dans laquelle
R' représente hydrogène, fluor, chlore, brome, un reste alkyle en C1 à C5, un groupe trifluorométhyle, phényle ou alcoxy en C1 à C3
n représente un des nombres 1 à 3, sous réserve que, si n est égal à 2 ou 3, les restes R' peuvent être identiques ou différents,
R2 représente un reste alkyle linéaire ou ramifié en C1 à C14 qui, dans le cas du reste alkyle ramifié, contient plus de deux atomes de carbone, un reste phényle de formule
Figure imgb0021
ou encore un reste benzyle de formule
Figure imgb0022
R4 représente hydrogène, fluor, chlore, brome, un reste alkyle en C1 à C5, un groupe trifluorométhyle-, phényle- ou alcoxy en C1 à C3,
R5 représente hydrogène, fluor, chlore, brome, un reste alkyle en C1 à C5, un groupe trifluorométhyle-, phényle- ou alcoxy en C1 à C3
m est un nombre de 1 à 3, sous réserve que, si m est égal à 2 ou 3, les restes R4 peuvent être identiques ou différents,
/ représente un nombre de 1 à 3, sous réserve que, si / est égal à 2 ou 3, les restes R5 peuvent être identiques ou différents,
k représente les nombres 0, 1, 2, et les sels et sels complexes métalliques des dits composés.
2. Fongicide contenant un composé soufré substitué par un triazole, de formule générale I selon la revendication 1.
3. Procédé pour lutter contre les champignons, caractérisé par le fait que l'on traite les objets à protéger contre les dégâts des champignons avec un composé soufré, substitué par un triazole, de formule générale I selon la revendication 1.
4. 1-[2-(4-bromophényl)-2-(4-chlorophénylmercapto)-éthyl-(1)]-1,2,4-triazole.
5. 1-[2-(4-bromophényl)-2-(4-chlorobenzylmercapto)-éthyl-(1 )]-1,2,4-triazole.
6. 1-[2-(3-bromophényl)-2-(4-chlorophénylmercapto)-éthyl-(1)]-1,2,4-triazole.
7. 1-[2-(3-bromophényl)-2-(4-chlorobenzylmercapto)-éthyl-(1)]-1,2,4-triazole.
8. 1-[2-(4-chlorophényl)-2-(4-chlorophénylmercapto)-éthyl-(1)]-1,2,4-triazole.
9. 1-[2-(4-chlorobenzylmercapto)-2-(4-chlorophényl)-éthyl-(1)]-1,2,4-triazole.
10. 1-[2-(4-chlorophénylmercapto)-2-(2,4-dichlorophényl)-éthyl-(1)]-1,2,4-triazole.
11. 1-[2-(4-chlorophénylmercapto)-2-(2,4-dichlorophényl)-éthyl-(1)]-1,2,4-triazoloxyde.
12. 1-[2-(4-chlorophénylmercapto)-2-(2,4-dichlorophényl)-éthyl-(1)]-1,2,4-triazoldioxyde.
13. 1-[2-(4-chlorobenzylmercapto)-2-(2,4-dichlorophényl)-éthyl-(1)]-1,2,4-triazole.
14. 1-[2-(2,4-dichlorobenzylmercapto)-2-(2,4-dichlorophényl)-éthyl-(1)]-1,2,4-triazole.
15. 1-[2-14-tert.butylphényl)-2-(2,4-dichlorobenzylmercapto)-éthyl-(1)]-1,2,4-triazole.
16. 1-[2-butylmercapto-2-(2,4-dichlorophényl)-éthyl-(1)]-1,2,4-triazole.
17. 1-[2-(2,4-dichlorophényl)-2-dodécylmercaptoéthyl-(1)]-1,2,4-triazole.
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 EP0000112A1 (fr) 1978-12-20
EP0000112B1 true EP0000112B1 (fr) 1981-09-09

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Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2928768A1 (de) * 1979-07-17 1981-02-12 Bayer Ag 1-(2,4-dichlorphenyl)-1-(2,6- dihalogenbenzylmercapto)-2-(1,2,4- triazol-1-yl)-ethane, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE3108770A1 (de) * 1981-03-07 1982-09-16 Bayer Ag, 5090 Leverkusen Triazolylalkyl-thioether, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenwachstumsregulatoren und fungizide
CA1179678A (fr) * 1981-03-27 1984-12-18 Elmar Sturm Derive de triazole microbicide
DE3342310A1 (de) * 1983-11-23 1985-05-30 Bayer Ag, 5090 Leverkusen Verwendung von 1-(2,4-dichlorphenyl)-1-(4-chlorbenzylmercapto)-2-(1,2,4-triazol-1-yl)-ethan zur regulierung des pflanzenwachstums
GB9125791D0 (en) * 1991-12-04 1992-02-05 Schering Agrochemicals Ltd Herbicides
PL308350A1 (en) * 1992-10-09 1995-07-24 Uniroyal Chem Co Inc Fungicidal substituted azole derivatives
RU2304140C2 (ru) * 2001-12-27 2007-08-10 Дайити Фармасьютикал Ко., Лтд. ИНГИБИТОРЫ ПРОДУЦИРОВАНИЯ / СЕКРЕЦИИ β-АМИЛОИДНОГО БЕЛКА
RU2336270C2 (ru) 2003-06-30 2008-10-20 Дайити Фармасьютикал Ко., Лтд. Гетероциклические метилсульфоновые производные

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2645496A1 (de) * 1976-10-08 1978-04-13 Bayer Ag (1-phenyl-2-triazolyl-aethyl)-thioaether-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide und wachstumsregulatoren

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DE2724684A1 (de) 1978-12-14
EP0000112A1 (fr) 1978-12-20
DE2861048D1 (en) 1981-11-26

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