EP0000176B1 - Pyridyloxy-phenoxy-alkancarbonsäurederivate, Verfahren zu deren Herstellung, und deren Verwendung als Herbizide oder als pflanzenwachstumsregulierende Mittel - Google Patents

Pyridyloxy-phenoxy-alkancarbonsäurederivate, Verfahren zu deren Herstellung, und deren Verwendung als Herbizide oder als pflanzenwachstumsregulierende Mittel Download PDF

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Publication number
EP0000176B1
EP0000176B1 EP78100209A EP78100209A EP0000176B1 EP 0000176 B1 EP0000176 B1 EP 0000176B1 EP 78100209 A EP78100209 A EP 78100209A EP 78100209 A EP78100209 A EP 78100209A EP 0000176 B1 EP0000176 B1 EP 0000176B1
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EP
European Patent Office
Prior art keywords
alkyl
formula
halogen
radical
substituted
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.)
Expired
Application number
EP78100209A
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German (de)
English (en)
French (fr)
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EP0000176A1 (de
Inventor
Hermann Dr. Rempfler
Werner Dr. Föry
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of EP0000176A1 publication Critical patent/EP0000176A1/de
Application granted granted Critical
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Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/83—Thioacids; Thioesters; Thioamides; Thioimides
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3

Definitions

  • the invention relates to pyridyloxy - phenoxy - alkane carboxylic acid derivatives which have a herbicidal and plant growth regulating action, processes for their preparation, furthermore compositions which contain these compounds as active compounds, and the use of the active compounds or the compositions containing them for the selective control of weeds and to regulate plant growth.
  • the alkyl radicals in this formula can be branched or unbranched and contain the stated number of carbon atoms.
  • the radicals R 5 and R 6 are preferably hydrogen and C 1 -C 4 alkyl radicals.
  • the active compounds of the formula I according to the invention have herbicidal activity, especially in the case of postemergent use and can be used as weed agents in mono- and dicotyledon crops.
  • the compounds according to the invention are not very toxic to warm-blooded animals and their application does not pose any problems.
  • the application rate is between 0.1 and 5 kg per hectare.
  • the compounds of the formula I are prepared by methods known per se.
  • an optionally substituted halopyridine of the formula II wherein C, D, E and n have the meaning given under formula I and Hal represents a halogen atom, preferably chlorine or bromine, with a hydroxyphenoxyalkane carboxylic acid derivative of the formula III wherein A, C, D, R 1 and R z have the meaning given under formula I in the presence of an acid-binding agent.
  • the pyridyloxy-phenoxy-alkanecarboxylic acid derivatives of the formula I are prepared by using a pyridyloxy-hydroxyphenyl ether of the formula IV wherein C, D, E and n have the meaning given under formula I, with an a-halocarboxylic acid derivative of the formula V.
  • A, R 1 and R 2 have the meaning given under formula I and Hal represents a halogen atom, preferably chlorine or bromine, in the presence of an acid-binding agent.
  • the reactions mentioned can be carried out in the presence or absence of solvents or diluents which are inert to the reactants.
  • Polar organic solvents such as methyl ethyl ketone, acetonitrile, dimethylformamide, dimethyl sulfoxide etc. are preferred.
  • the reaction temperatures are between 0 and 200 ° C. and the reaction time is between 1/4 hour and several days, depending on the reaction temperature and solvent chosen. You usually work at normal pressure or a slight excess pressure.
  • Acid-binding agents for the reaction are inorganic, such as NaOH, KOH, NaOCH 3 , NaH, K z C0 3 , NaC0 3 or potassium tert. butylate but also organic bases.
  • Substituted 2-halopyridine according to formula II can i.a. can be easily prepared from the corresponding 2-pyridinols, some of which are known.
  • Starting materials of formula III can be prepared by e.g. reacting a monobenzyl ether of hydroquinone, resorcinol or catechol with an ⁇ -halogenocarboxylic acid derivative, preferably an ester of the formula V, and cleaving the benzylphenyl ether bond by catalytic hydrogenation, e.g. with a palladium-on-carbon catalyst, the benzyl residue leaving as toluene.
  • the starting products of the formula IV can be obtained by reacting hydroquinone, resorcinol or pyrocatechol with halopyridines in equimolar amounts and in the presence of a base.
  • Carboxylic acid derivatives of the formula V are also known.
  • the simplest representatives are, for example, chloroacetic acid, its esters, thioesters, amides and hydrazides.
  • other a-halocarboxylic acid derivatives substituted according to R 1 and R z can also be used.
  • pyridyloxy-phenoxy-alkane carboxylic acid derivatives of the formula I are stable compounds which are soluble in customary organic solvents, such as alcohols, ethers, ketones, dimethylformamide or dimethyl sulfoxide.
  • the content of active ingredient in the agents described above is between 0.1 to 95%, preferably between 1 to 80%.
  • Application forms can be diluted down to 0.001%.
  • the application rates are generally 0.1 to 10 kg ai / ha, preferably 0.25 to 5 kg ai / ha.
  • Other biocidal active substances or agents can also be added to the agents according to the invention described.
  • the active ingredients of Formula 1 can be formulated, for example, as follows (parts mean parts by weight):
  • the active ingredients are mixed and ground with the carriers.
  • the active substance is mixed with epichlorohydrin and dissolved in 6 parts of acetone, whereupon polyethylene glycol and cetylpolyethylene glycol ether are added.
  • the solution thus obtained is sprayed onto kaolin and then evaporated in vacuo.
  • the specified active ingredient is drawn onto the corresponding carrier substances (kaolin and chalk) and then mixed and ground. Spray powder of excellent wettability and suspension is obtained. Suspensions of any desired active ingredient concentration can be obtained from such wettable powders by dilution with water. Such suspensions are used to control weeds and weeds in crops in pre-emergence and for the treatment of lawns.
  • the active ingredient is intimately mixed and ground with the additives in suitable devices.
  • a paste is obtained, from which suspensions of any desired concentration can be prepared by dilution with water.
  • the suspensions are suitable for the treatment of lawns.
  • This concentrate can be diluted with water to emulsions to suitable concentrations.
  • the active substances contained in the agents according to the invention influence plant growth in various ways. In the first place, they inhibit, delay or prevent growth and germination. It is therefore both a pre- and post-emergent herbicide effect and an inhibition of growth.
  • Agents according to the invention which contain at least one compound of the formula I as the active component are particularly suitable for inhibiting the control of the plant growth of monocotyledon and dicotyledonous plants, such as grasses, shrubs, trees, crops of cereals and legumes, sugar cane, tobacco, soybeans, onions and Potato tubers, ornamental plants, fruit trees and vines.
  • monocotyledon and dicotyledonous plants such as grasses, shrubs, trees, crops of cereals and legumes, sugar cane, tobacco, soybeans, onions and Potato tubers, ornamental plants, fruit trees and vines.
  • the effect achieved primarily by the active compounds of the formula I consists in the desired reduction in the plant size, in particular the stature height. In general, this involves a certain change in the shape of the plant. In direct connection with the reduction in growth height, the plant is strengthened. Leaves and stems are stronger. The kink resistance is increased by shortening the internode spacing on monocotyledonous plants. In this way, crop failures due to thunderstorms, continuous rain, etc., which normally lead to the storage of crops of cereals and legumes, can be largely prevented and harvesting work can thus be made easier. As a side effect, the reduced height of crops leads to savings in fertilizers. This also applies to ornamental plants, ornamental turf, sports turf or other green plants.
  • active compounds of the formula 1 according to the invention can also advantageously influence the growth of shoots and / or the fertility of fruit trees and vines.
  • Ornamental plants with strong growth in length can be grown as compact potted plants by treatment with active substances according to the invention.
  • the active compounds of the formula I are also used to inhibit the growth of undesired poultry drives, e.g. in tobacco and ornamental plants, which avoids the labor-intensive breakout of these shoots by hand, also to prevent shoots in stored bulbs, for example in ornamental plant bulbs, in onions and potatoes, and finally to increase the yield in crops which grow strongly vegetatively, such as soybeans and sugar cane, by application active ingredients according to the invention the transition from the vegetative to the generative growth phase is accelerated.
  • the active compounds of the formula according to the invention are preferably used to inhibit the growth of grasses, cereal crops, tobacco, soybeans and ornamental plants.
  • the application rates are different and depend on the time of application. They are generally between 0.1 and 5 kg of active ingredient per hectare, preferably up to 4 kg per hectare when applied before emergence of the plants and for the treatment of existing crops.
  • This inhibition of growth occurs in some plant species at a dosage of 0.5 kg / ha and below.
  • the active compounds according to the invention are also interesting combination partners for a number of herbicides of the phenylurea and triazine series in cereal crops, maize, sugar cane and. in fruit and wine growing.
  • the active compounds according to the invention can be used as growth inhibitors in a wide variety of crops.
  • the weed cover is not removed, but only so strongly inhibited that the crop plants no longer compete.
  • the active ingredients of the formula are also characterized by a very strong pre-emergent herbicide effect, so they are also pronounced germination inhibitors.
  • the tested compounds according to the invention showed pronounced contact herbicidal activity on some plants and growth arrest on many plants as a symptom of the growth-inhibiting properties.
  • Seeds of the grasses Lolium perenne, Poa pratensis, Festuca ovina and Dactylis glomerata were sown in plastic trays with a soil-peat-sand mixture (6: 3: 1) and watered normally.
  • the accumulated grasses were cut back to a height of 4 cm weekly and sprayed with aqueous spray liquors of an active ingredient of the formula 40 days after sowing and 1 day after the last cut.
  • the amount of active ingredient was the equivalent of 5 kg of active ingredient per hectare.
  • the growth of the grasses was assessed 10 and 21 days after application.
  • the active substances according to the invention cause a noticeable growth inhibition both in the grasses and in the cereals.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP78100209A 1977-06-29 1978-06-21 Pyridyloxy-phenoxy-alkancarbonsäurederivate, Verfahren zu deren Herstellung, und deren Verwendung als Herbizide oder als pflanzenwachstumsregulierende Mittel Expired EP0000176B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH802377 1977-06-29
CH8023/77 1977-06-29

Publications (2)

Publication Number Publication Date
EP0000176A1 EP0000176A1 (de) 1979-01-10
EP0000176B1 true EP0000176B1 (de) 1981-09-16

Family

ID=4333965

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100209A Expired EP0000176B1 (de) 1977-06-29 1978-06-21 Pyridyloxy-phenoxy-alkancarbonsäurederivate, Verfahren zu deren Herstellung, und deren Verwendung als Herbizide oder als pflanzenwachstumsregulierende Mittel

Country Status (17)

Country Link
US (5) US4329167A (cs)
EP (1) EP0000176B1 (cs)
JP (1) JPS5412379A (cs)
AT (1) AT362956B (cs)
AU (1) AU526393B2 (cs)
BR (1) BR7804115A (cs)
CA (1) CA1100964A (cs)
CS (1) CS222264B2 (cs)
DD (1) DD137879A5 (cs)
DE (1) DE2861073D1 (cs)
ES (1) ES471216A1 (cs)
HU (1) HU180704B (cs)
IL (1) IL55016A (cs)
IT (1) IT1097282B (cs)
PH (1) PH18510A (cs)
TR (1) TR20086A (cs)
ZA (1) ZA783719B (cs)

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US4558134A (en) * 1983-01-03 1985-12-10 The Dow Chemical Company Certain phenoxy-pyridine-carbonitriles having antiviral activity
US4486593A (en) * 1983-01-19 1984-12-04 The Upjohn Company 2-,3-, or 4-Pyridinylmethylamino arylic acids as thromboxane A2 synthetase and 5-lipoxygenase inhibitors
US4599105A (en) * 1983-06-20 1986-07-08 The Dow Chemical Company 2-[16-(3-fluoro-5-trifluoromethyl-pyridinyl-2-oxy)-3-nitro-phenoxy]-propionic acid derivatives, herbicidal compositions containing same and herbicidal method of use
US4539039A (en) * 1984-04-26 1985-09-03 The Dow Chemical Company Herbicidal (-3-fluoro-5-trifluoromethyl-pyridyl)oxy phenyloxime derivatives
US4775410A (en) * 1985-08-19 1988-10-04 Sandoz Ltd. 2-[4-(2-pyridinyloxy)phenoxy]propionyl-2-oxazolidinones
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Also Published As

Publication number Publication date
EP0000176A1 (de) 1979-01-10
IL55016A (en) 1982-02-28
CS222264B2 (en) 1983-06-24
CA1100964A (en) 1981-05-12
US4329167A (en) 1982-05-11
ATA470878A (de) 1980-11-15
PH18510A (en) 1985-08-02
US4384882A (en) 1983-05-24
ES471216A1 (es) 1979-09-01
DD137879A5 (de) 1979-10-03
US4433998A (en) 1984-02-28
AU526393B2 (en) 1983-01-06
IL55016A0 (en) 1978-08-31
IT1097282B (it) 1985-08-31
AT362956B (de) 1981-06-25
DE2861073D1 (en) 1981-12-03
JPS5412379A (en) 1979-01-30
BR7804115A (pt) 1979-02-20
IT7825083A0 (it) 1978-06-28
TR20086A (tr) 1980-07-07
US4425157A (en) 1984-01-10
US4443247A (en) 1984-04-17
AU3751778A (en) 1980-01-03
ZA783719B (en) 1979-06-27
HU180704B (en) 1983-04-29

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