WO1994024868A1 - Agents nematicides a base de 2-dichloromethyl-1,3,4-oxadiazoles - Google Patents

Agents nematicides a base de 2-dichloromethyl-1,3,4-oxadiazoles Download PDF

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Publication number
WO1994024868A1
WO1994024868A1 PCT/EP1994/001195 EP9401195W WO9424868A1 WO 1994024868 A1 WO1994024868 A1 WO 1994024868A1 EP 9401195 W EP9401195 W EP 9401195W WO 9424868 A1 WO9424868 A1 WO 9424868A1
Authority
WO
WIPO (PCT)
Prior art keywords
optionally substituted
dichloromethyl
carbon atoms
substituents
formula
Prior art date
Application number
PCT/EP1994/001195
Other languages
German (de)
English (en)
Inventor
Udo Kraatz
Wolfgang Krämer
Jürgen Hartwig
Christoph Erdelen
Original Assignee
Bayer Aktiengesellschaft
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 Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to JP6522518A priority Critical patent/JPH08509214A/ja
Priority to EP94914397A priority patent/EP0696171A1/fr
Priority to AU78799/94A priority patent/AU7879994A/en
Publication of WO1994024868A1 publication Critical patent/WO1994024868A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • R 1 represents alkyl, cycloalkyl, aryl, aralkyl, heteroaryl, which may optionally be substituted
  • R 2 represents optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted hetaryl or R 1 and R 2 together with the nitrogen atom to which they are attached form a cycle
  • Examples of optionally substituted methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl and undecyl- may be mentioned.
  • Unsubstituted or substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl may be mentioned as examples.
  • Preferred heteroatoms are oxygen,
  • the optionally substituted radicals of the general formulas can carry one or more, preferably 1 to 3, in particular 1 or 2 identical or different substituents.
  • Examples of preferred substituents are:
  • Halogen preferably fluorine, chlorine and bromine, iodine, especially fluorine, chlorine and bromine; Haloalkoxy and haloalkylthio, and their oxides, preferably having 1 to 4, in particular 1 or 2, carbon atoms and preferably 1 to 9, in particular 1 to 5, halogen atoms, the halogen atoms being the same or different and, as halogen atoms, preferably fluorine, chlorine or bromine, in particular fluorine are such as trifluoromethoxy, trifluoroethoxy, difluoromethoxy, pentafluoroethoxy, tetrafluoroethoxy, trifluorochloroethoxy, trifluoromethylthio; Alkoxy preferably having 1 to 4, in particular 1 or 2, carbon atoms, such as methoxy, ethoxy, n- and i-propyloxy and n-, i-, see- and t-butyloxy; Alkylthio
  • substituents for cycloalkyl which may be mentioned are: alkyl, alkoxy, alkylthio which may be substituted, unsubstituted or substituted aryl, aryloxy or arylthio.
  • Formula (I) provides a general definition of the 2-dichloromethyl-1,3,4-oxadiazoles to be used according to the invention.
  • Preferred compounds of the formula (I) are those X stands for a direct bond or for one of the following groupings: -O-, -S-, -S (O) -, -SO 2 -, -NH- or -NR 2 - R 1 represents optionally substituted C 1 -C 15 Alkyl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted phenyl or optionally substituted heteroaryl,
  • R 1 for methyl, ethyl, n-propyl, i-propyl, n-butyl, sec.-butyl, i-butyl, t.-butyl, i-pentyl, hexyl, undecyl, methoxy, ethoxy, methylthiomethyl, trifluoromethyl, cyclopropyl , Cyclohexyl, 9-dodecenyl, undecenyl; furthermore for unsubstituted or single, double or triple, identically or differently substituted by chlorine or methoxy-substituted phenoxymethyl, phenoxyethyl or 2-phenoxyethyl; further for phenyl, benzyl, phenyl, furyl, pyridyl, imidazolyl or benzimidazolyl or substituted by methyl, ethyl, t-butyl, chlorine, trifluoromethyl, methoxy,
  • the active compounds according to the invention also show leaf-insecticidal activity.
  • the active compounds according to the invention can be applied both before and after emergence of the plants.
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • the active ingredient preparation is intimately mixed with the soil that is heavily contaminated with the test nematodes.
  • the treated soil is poured into pots, lettuce is sown and the pots are kept at a greenhouse temperature of 25 ° C.
  • the active ingredients 1, 2, 3, 7, 8, 10 and 15 showed an efficiency of at least 95% at an active ingredient concentration of 20 ppm.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

L'invention concerne l'utilisation comme insecticides, nématicides et acaricides, de 2-dichlorométhyl-1,3,4-oxadiazoles, dont certains sont déjà connus, de la formule générale (I) dans laquelle X désigne une liaison simple ou un des groupements suivants: -O-, -S-, -S(O)-, -SO2-, -NH- ou -NR2-, R1 désigne alkyle, cycloalkyle, aryle, aralkyle, hétéroalkyle qui peuvent éventuellement être substitués, R2 désigne alkyle éventuellement substitué, cycloalkyle éventuellement substitué, aryle éventuellement substitué ou hétaryle éventuellement substitué ou R1 et R2 forment conjointement un cycle avec l'atome d'azote auquel ils sont liés. L'invention concerne en outre de nouveaux 2-dichlorométhyl-1,3-4-oxadiazoles et leur préparation.
PCT/EP1994/001195 1993-04-29 1994-04-18 Agents nematicides a base de 2-dichloromethyl-1,3,4-oxadiazoles WO1994024868A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP6522518A JPH08509214A (ja) 1993-04-29 1994-04-18 ２−ジクロロメチル−１，３，４−オキサジアゾールをベースとする殺線虫剤組成物
EP94914397A EP0696171A1 (fr) 1993-04-29 1994-04-18 Agents nematicides a base de 2-dichloromethyl-1,3,4-oxadiazoles
AU78799/94A AU7879994A (en) 1993-04-29 1994-04-18 Nematicidal agents based on 2-dichloromethyl-1,3,4-oxadiazoles

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19934314037 DE4314037A1 (de) 1993-04-29 1993-04-29 Nematizide Mittel auf Basis von 2-Dichlormethyl-1,3,4-oxadiazolen
DEP4314037.8 1993-04-29

Publications (1)

Publication Number Publication Date
WO1994024868A1 true WO1994024868A1 (fr) 1994-11-10

Family

ID=6486675

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1994/001195 WO1994024868A1 (fr) 1993-04-29 1994-04-18 Agents nematicides a base de 2-dichloromethyl-1,3,4-oxadiazoles

Country Status (5)

Country Link
EP (1) EP0696171A1 (fr)
JP (1) JPH08509214A (fr)
AU (1) AU7879994A (fr)
DE (1) DE4314037A1 (fr)
WO (1) WO1994024868A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103864769A (zh) * 2012-12-14 2014-06-18 上海工程技术大学 一种噁二唑化合物及其制备方法
EA034172B1 (ru) * 2007-08-13 2020-01-14 Монсанто Текнолоджи Ллс Способы (варианты) контроля нематод

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0097126A2 (fr) * 1982-06-16 1983-12-28 Ciba-Geigy Ag 2-(3-Pyridyl)-1,3,4-oxadiazoles, leur procédé de préparation et leur application comme biocides
US4488897A (en) * 1983-09-06 1984-12-18 Stauffer Chemical Company Dichloromethyl oxadiazole herbicide antidotes
EP0263066A2 (fr) * 1986-09-26 1988-04-06 Ciba-Geigy Ag Dérivés de 2-mercapto-oxadiazole et -thiadiazole, procédé pour leur préparation et nématicides les contenant

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0097126A2 (fr) * 1982-06-16 1983-12-28 Ciba-Geigy Ag 2-(3-Pyridyl)-1,3,4-oxadiazoles, leur procédé de préparation et leur application comme biocides
US4488897A (en) * 1983-09-06 1984-12-18 Stauffer Chemical Company Dichloromethyl oxadiazole herbicide antidotes
EP0263066A2 (fr) * 1986-09-26 1988-04-06 Ciba-Geigy Ag Dérivés de 2-mercapto-oxadiazole et -thiadiazole, procédé pour leur préparation et nématicides les contenant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
J. C. LANCELOT, D. MAUME & M. ROBBA: "Pyrrolo(1,2-d)triazines-1,2,4. I. Dérivés Pyrroliques.", J. HETEROCYCLIC CHEM., vol. 17, no. 4, June 1980 (1980-06-01), pages 625 - 629 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EA034172B1 (ru) * 2007-08-13 2020-01-14 Монсанто Текнолоджи Ллс Способы (варианты) контроля нематод
CN103864769A (zh) * 2012-12-14 2014-06-18 上海工程技术大学 一种噁二唑化合物及其制备方法
CN103864769B (zh) * 2012-12-14 2016-11-02 上海工程技术大学 一种噁二唑化合物及其制备方法

Also Published As

Publication number Publication date
DE4314037A1 (de) 1994-11-03
JPH08509214A (ja) 1996-10-01
EP0696171A1 (fr) 1996-02-14
AU7879994A (en) 1994-11-21

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