WO1980002493A1 - Herbicides - Google Patents

Herbicides Download PDF

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Publication number
WO1980002493A1
WO1980002493A1 PCT/CH1980/000056 CH8000056W WO8002493A1 WO 1980002493 A1 WO1980002493 A1 WO 1980002493A1 CH 8000056 W CH8000056 W CH 8000056W WO 8002493 A1 WO8002493 A1 WO 8002493A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
radical
hydrogen atom
group
acid
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.)
Ceased
Application number
PCT/CH1980/000056
Other languages
German (de)
English (en)
French (fr)
Inventor
K Thiele
J Meyer
I Molnar
F Geissmann
W Schaeren
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.)
Siegfried AG
Original Assignee
Siegfried AG
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 Siegfried AG filed Critical Siegfried AG
Priority to DE8080900764T priority Critical patent/DE3064382D1/de
Publication of WO1980002493A1 publication Critical patent/WO1980002493A1/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • A01N33/18—Nitro compounds
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aliphatically bound aldehyde or keto groups, or thio analogues thereof; Derivatives thereof, e.g. acetals
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing aldehyde or keto groups, or thio analogues thereof, directly attached to an aromatic ring system, e.g. acetophenone; Derivatives thereof, e.g. acetals
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/48—Nitro-carboxylic acids; Derivatives thereof
    • 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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A01N39/04—Aryloxy-acetic acids; Derivatives thereof
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
    • C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
    • C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C243/30—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
    • C07C243/32—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
    • 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
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms

Definitions

  • acyl radical R 1 is the p- (p'-chlorobenzyl) phenoxyacetic acid described in DE-OS 2 '461'069 by the applicant as a lipid-lowering agent.
  • acids for the formation of the acyl radical R 1 by esterification of the ethanol compound (1) are the herbicidal acids described in the prior art mentioned at the outset, including the substituted benzoic acids, the (2,4-dichlorophenoxy) acetic acid, the substituted phenylacetic acids with known ones Plant growth activity and that not previously described as a herbicide
  • the acyl radical R can be described as one of a C 1 -C 6 alkanoic acid which preferably carries an aryl, aryloxy, aralkaryl or aralkaryloxy radical, it being possible for the aryl moieties to be additionally substituted by halogen and / or nitro.
  • R 5 represents the hydrogen atom, the amino group, an optionally substituted (for example by halogen and / or nitro) alkyl radical or a heterocyclic radical indicates; or (IV) an optionally substituted (for example by halogen and / or nitro) alkyl, aryl, alkaryl or aralkyl radical.
  • the separated enol salt is filtered off and washed with absolute diethyl ether.
  • the mother liquor is concentrated to 1/10 vol and filtered to obtain further enol salt.
  • the total yield of enol salt is about 70% by weight.
  • the enol salt is stirred for 1 hour in 1 liter of 0.5 N aqueous KOH solution.
  • the resulting dark brown solution is extracted twice with diethyl ether, then acidified with concentrated hydrochloric acid and extracted with diethyl ether.
  • the ether extract obtained in this way is dried and then evaporated.
  • the 2- (2-nitro-3-chlorophenyl) ethanol obtained according to Example 6 was esterified with [4- (4'-chlorobenzyl) phenoxy] acetic acid by boiling with benzene in the presence of a catalytic amount of p-toluenesulfonic acid (water separator).
  • the ester obtained has a melting point of 86-87 ° C. (yield 88%).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/CH1980/000056 1979-05-16 1980-05-08 Herbicides Ceased WO1980002493A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE8080900764T DE3064382D1 (en) 1979-05-16 1980-05-08 Use of chloronitrophenyl derivatives as selective herbicides and new chloronitrophenyl derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH4548/79 1979-05-16
CH454879 1979-05-16

Publications (1)

Publication Number Publication Date
WO1980002493A1 true WO1980002493A1 (fr) 1980-11-27

Family

ID=4278129

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CH1980/000056 Ceased WO1980002493A1 (fr) 1979-05-16 1980-05-08 Herbicides

Country Status (4)

Country Link
EP (1) EP0028609B1 (https=)
JP (1) JPS56500535A (https=)
DE (1) DE3064382D1 (https=)
WO (1) WO1980002493A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108935467A (zh) * 2018-07-09 2018-12-07 湖南省农业生物技术研究所 不同取代基苯酚酯类的除草化合物制备及应用

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3009806A (en) * 1958-08-13 1961-11-21 Hooker Chemical Corp Herbicidal compounds and method for controlling broadleaf and grassy weeds therewith
FR1291128A (fr) * 1960-05-16 1962-04-20 Velsicol Chemical Corp Composés herbicides et leur procédé de préparation
FR1568656A (https=) * 1967-06-14 1969-05-23 Bofors Ab
US3474090A (en) * 1966-12-22 1969-10-21 American Cyanamid Co 3-aminoalkyl-1,3-benzodiazepin-2-ones
US3547619A (en) * 1967-01-23 1970-12-15 Gulf Research Development Co Nitrophenylacetic acids and derivatives as selective herbicides
BE760968A (en) * 1970-12-29 1971-06-29 P R B En Neerlandais P R B N V Opt 2,3-subst phenyl acetic acid and derivpl
GB1246305A (en) * 1967-11-16 1971-09-15 Montedison Spa Fluorine-containing esters

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3009806A (en) * 1958-08-13 1961-11-21 Hooker Chemical Corp Herbicidal compounds and method for controlling broadleaf and grassy weeds therewith
FR1291128A (fr) * 1960-05-16 1962-04-20 Velsicol Chemical Corp Composés herbicides et leur procédé de préparation
US3474090A (en) * 1966-12-22 1969-10-21 American Cyanamid Co 3-aminoalkyl-1,3-benzodiazepin-2-ones
US3547619A (en) * 1967-01-23 1970-12-15 Gulf Research Development Co Nitrophenylacetic acids and derivatives as selective herbicides
FR1568656A (https=) * 1967-06-14 1969-05-23 Bofors Ab
GB1246305A (en) * 1967-11-16 1971-09-15 Montedison Spa Fluorine-containing esters
BE760968A (en) * 1970-12-29 1971-06-29 P R B En Neerlandais P R B N V Opt 2,3-subst phenyl acetic acid and derivpl

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Band 77, Nr. 3, 17. Juli 1972, Columbus, Ohio, US, CHAMBERLAIN V.H. u.a.: "Plant growth regulating substances, XXXIII Infleunce of ring substituents on the plant growth regulating activity of phenylacetic acid", Zusammenfassung Nr. 15433g seite 166, siehe das ganze Artikel. Ubereinstimmend mit Ann. App. Biol. Band 69, Nr. 1, 1971, Seiten 65-72 (In der Anmeldung angefuhrt). *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108935467A (zh) * 2018-07-09 2018-12-07 湖南省农业生物技术研究所 不同取代基苯酚酯类的除草化合物制备及应用

Also Published As

Publication number Publication date
EP0028609A1 (de) 1981-05-20
DE3064382D1 (en) 1983-09-01
JPS56500535A (https=) 1981-04-23
EP0028609B1 (de) 1983-07-27

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