EP0000351A1 - Phenoxy-phenylthio-alkancarbonsäurederivate, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und als Pflanzenwachstumsregulierungsmittel - Google Patents

Phenoxy-phenylthio-alkancarbonsäurederivate, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und als Pflanzenwachstumsregulierungsmittel Download PDF

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Publication number
EP0000351A1
EP0000351A1 EP78100270A EP78100270A EP0000351A1 EP 0000351 A1 EP0000351 A1 EP 0000351A1 EP 78100270 A EP78100270 A EP 78100270A EP 78100270 A EP78100270 A EP 78100270A EP 0000351 A1 EP0000351 A1 EP 0000351A1
Authority
EP
European Patent Office
Prior art keywords
halogen
formula
alkoxy
alkyl
hydrogen
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
EP78100270A
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German (de)
English (en)
French (fr)
Inventor
Dieter Dr. Dürr
Otto Dr. Rohr
Georg Dr. Pissiotas
Beat Dr. Böhner
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
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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of EP0000351A1 publication Critical patent/EP0000351A1/de
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • 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
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids

Definitions

  • the present invention relates to new phenoxy-phenylthio-alkanecarboxylic acid derivatives which show herbicidal and plant growth-regulating activity, processes for the preparation of these derivatives, herbicidal and plant-growth-regulating agent which contain these derivatives as active compounds and the use of the new phenoxy-phenyl-thio-alkanecarboxylic acid derivatives or the compositions containing them as herbicides and / or for regulating plant growth.
  • alkyl radicals in this formula can be branched or unbranched and contain the stated number of carbon atoms.
  • the alkylene bridge can be the methylene bridge, the 1- or 2-ethylene bridge can be a straight or 1- or 2-methylethyl or 1,1-dimethyl-methylene branched propylene bridge, as well as a straight or correspondingly branched butylene bridge.
  • the compounds of the present invention are not very toxic to warm-blooded animals and their application poses no problems. They are stable compounds which are soluble in the usual organic solvents, such as alcohols, ethers, ketones, dimethylformamide, dimethyl sulfoxide. Application rates between 0.1 and 5 kg per hectare are normally required.
  • the new active compounds of the formula I according to the present invention have herbicidal activity in the case of pre- and post-emergence use and can be used as weed compositions in monocotyledonous and dicotyledonous crops.
  • This diazo solution is added dropwise at 55-60 ° to a solution of 300 ml of water, 800 ml of toluene, 225 g of potassium methyl xanthate, 85 g of sodium carbonate and 75 ml of 30% sodium hydroxide solution.
  • the toluene phase is separated off. This is washed with water and, after drying over sodium sulfate in 100 ml of triethylamine, added dropwise at 70 °. 2 hours reflux, then cool and add 200 ml of 30% sodium hydroxide solution. The organic phase is separated off and distilled. 160 g of 4-chloro-3-methylmercaptoanisole are obtained.
  • the new active compounds of the formula I are stable compounds which are soluble in customary organic solvents, such as alcohols, ethers, ketones, dimethylformamide, dimethyl sulfoxide, etc.
  • the active substance concentrations in the agents according to the invention are 1 to 80 percent by weight and, if appropriate, can also be present in low concentrations, such as 0.05 to 1%, when used.
  • biocidal active substances or agents can be added to the agents according to the invention described.
  • the active substance is mixed with epichlorohydrin and dissolved in 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether are added. The solution thus obtained is sprayed onto kaolin and then evaporated in vacuo.
  • the specified active ingredient is applied to the appropriate carrier substances (kaolin and chalk) and then mixed and ground with the other ingredients. Spray powder of excellent wettability and suspension is obtained. From such wettable powders, suspensions of 0.1-80% active ingredient can be obtained by dilution with water, which are suitable for weed control in plant crops.
  • 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 new 3-phenoxy-a-phenylthioalkanecarboxylic acid derivatives of the formula I and the compositions comprising them have an excellent selective herbicidal action against weeds in various, preferably monocotyledonous crops, and they also have a plant growth-regulating action.
  • a particularly preferred area of application is the selective control of, above all, dicotyledon weeds in cereal crops, especially in rice.
  • the new active ingredients are preferred as e.g. 25% wettable powder or e.g. 20% emulsifiable concentrates formulated and diluted with water, applied to the plant stands post-emergent.
  • Various crops and weeds are grown from the seeds in pots in the greenhouse until they reach the 4 to 6 leaf stage. Then the plants are sprayed with aqueous active ingredient emulsions (obtained from a 20% emulsifiable concentrate) in various doses. The treated plants are then under optimal conditions of light, watering, temperature (22-25 ° C) and air humidity (50-70% relative) kept. The tests were evaluated 15 days after treatment.
  • Rice plants that are 25 days old are transplanted into large rectangular eternit bowls in the greenhouse. Seeds of the weeds Echinochloa crus galli, Cyperus difformis, Ammania and Rotala which are found in rice crops are then sown between the rows of rice plants.
  • the bowls are well watered and kept at a temperature of approx. 25 ° and high humidity. After 12 days, when the weeds have emerged and reached the 2-3 leaf stage, the earth in the bowl is covered with a 2.5 cm high layer of water.
  • the active ingredient is then applied as an emulsion concentrate by means of a pipette between the rows of plants, the emulsion concentrate being diluted and applied in such a way that it corresponds to an application amount in the field of 2 and 1 kg of active ingredient per hectare.
  • the experiment is evaluated after 4 weeks.
  • the tested compounds according to the present 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 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 I 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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP78100270A 1977-07-07 1978-06-29 Phenoxy-phenylthio-alkancarbonsäurederivate, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und als Pflanzenwachstumsregulierungsmittel Ceased EP0000351A1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH842677 1977-07-07
CH8426/77 1977-07-07
CH92978 1978-01-27
CH929/78 1978-01-27

Publications (1)

Publication Number Publication Date
EP0000351A1 true EP0000351A1 (de) 1979-01-24

Family

ID=25686139

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100270A Ceased EP0000351A1 (de) 1977-07-07 1978-06-29 Phenoxy-phenylthio-alkancarbonsäurederivate, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und als Pflanzenwachstumsregulierungsmittel

Country Status (15)

Country Link
US (1) US4349377A (pt)
EP (1) EP0000351A1 (pt)
JP (1) JPS5416438A (pt)
AR (1) AR221487A1 (pt)
AT (1) AT358557B (pt)
AU (1) AU522170B2 (pt)
BR (1) BR7804382A (pt)
CA (1) CA1108172A (pt)
CS (1) CS222267B2 (pt)
DD (1) DD138142A5 (pt)
ES (1) ES471526A1 (pt)
HU (1) HU182473B (pt)
IL (1) IL55085A (pt)
IT (1) IT1096916B (pt)
TR (1) TR20047A (pt)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025773A1 (de) * 1979-09-13 1981-03-25 Ciba-Geigy Ag Schwefelhaltige Alkancarbonsäurederivate mit herbizider und den Pflanzenwuchs regulierender Wirkung, deren Herstellung und Verwendung
EP0089573A1 (de) * 1982-03-20 1983-09-28 BASF Aktiengesellschaft Thioalkansäure-silylalkylester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
EP0033885B1 (de) * 1980-02-08 1984-03-21 Bayer Ag Verfahren zur Herstellung von (2-Chlor-4-trifluormethyl-phenyl)-(3-methoxy-phenyl)-ether

Families Citing this family (42)

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US4419123A (en) * 1981-10-19 1983-12-06 Rohm And Haas Company Herbicidal 4-trifluoromethyl-3'-carbon-substituted-4'-substituted diphenyl ethers
AU557324B2 (en) * 1981-12-25 1986-12-18 Sumitomo Chemical Company, Limited Tetrahydro phthalimide compounds
JPS59212472A (ja) * 1983-05-16 1984-12-01 Sumitomo Chem Co Ltd ４，５，６，７−テトラヒドロ−２ｈ−イソインド−ル−１，３−ジオン誘導体、その製造法およびそれを有効成分とする除草剤
JPS6054362A (ja) * 1983-08-31 1985-03-28 Sumitomo Chem Co Ltd テトラヒドロフタルイミド誘導体，その製造法およびそれを有効成分とする除草剤
US4902832A (en) * 1983-08-31 1990-02-20 Sumitomo Chemical Company, Limited 2-Substituted phenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-diones, and their production and use
US4600432A (en) * 1984-07-25 1986-07-15 Agro-Kanesho Co., Ltd. Propionic acid derivatives and herbicides employing them
EP0302203B1 (en) * 1987-08-05 1992-10-28 Dowelanco Herbicidal fluorophenoxyphenoxyalkanoic acids and derivatives thereof
DE3928988A1 (de) * 1989-09-01 1991-03-07 Bayer Ag Aryloxynaphthalinderivate
US9185915B2 (en) 2010-12-21 2015-11-17 Bayer Cropscience Lp Sandpaper mutants of bacillus and methods of their use to enhance plant growth, promote plant health and control diseases and pests
BR112014005654A2 (pt) 2011-09-12 2017-03-28 Bayer Cropscience Lp métodos para melhorar a saúde e promover o crescimento de uma planta e/ou de melhorar o amadurecimento da fruta
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH424761A (de) * 1963-06-28 1966-11-30 Sandoz Ag Verfahren zur Herstellung neuer Thiolcarbonsäureester
DE2130919A1 (de) * 1970-06-22 1971-12-30 Nippon Kayaku Kk Substituierte Diphenylaether,Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
DE2223894A1 (de) * 1972-05-17 1973-12-13 Hoechst Ag Herbizide mittel
DE2333848A1 (de) * 1973-07-03 1975-01-16 Bayer Ag Halogenierte 4-trifluormethyl-diphenyl (thio)aether, verfahren zu ihrer herstellung und ihre verwendung als herbizide
FR2285861A1 (fr) * 1974-09-30 1976-04-23 Lafon Labor Composes diaryle soufres et diaryle oxygenes
FR2325638A1 (fr) * 1975-09-27 1977-04-22 Ishihara Mining & Chemical Co Herbicides a base d'acide phenoxy phenoxy alcane carboxylique

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
US3784635A (en) * 1969-04-25 1974-01-08 Mobil Oil Corp Substituted phenoxybenzoic acids and esters thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH424761A (de) * 1963-06-28 1966-11-30 Sandoz Ag Verfahren zur Herstellung neuer Thiolcarbonsäureester
DE2130919A1 (de) * 1970-06-22 1971-12-30 Nippon Kayaku Kk Substituierte Diphenylaether,Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide
DE2223894A1 (de) * 1972-05-17 1973-12-13 Hoechst Ag Herbizide mittel
DE2333848A1 (de) * 1973-07-03 1975-01-16 Bayer Ag Halogenierte 4-trifluormethyl-diphenyl (thio)aether, verfahren zu ihrer herstellung und ihre verwendung als herbizide
FR2285861A1 (fr) * 1974-09-30 1976-04-23 Lafon Labor Composes diaryle soufres et diaryle oxygenes
FR2325638A1 (fr) * 1975-09-27 1977-04-22 Ishihara Mining & Chemical Co Herbicides a base d'acide phenoxy phenoxy alcane carboxylique

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025773A1 (de) * 1979-09-13 1981-03-25 Ciba-Geigy Ag Schwefelhaltige Alkancarbonsäurederivate mit herbizider und den Pflanzenwuchs regulierender Wirkung, deren Herstellung und Verwendung
EP0033885B1 (de) * 1980-02-08 1984-03-21 Bayer Ag Verfahren zur Herstellung von (2-Chlor-4-trifluormethyl-phenyl)-(3-methoxy-phenyl)-ether
US4450308A (en) * 1980-02-08 1984-05-22 Bayer Aktiengesellschaft Process for the preparation of trifluoromethylphenyl oxyphenyl ether compounds
EP0089573A1 (de) * 1982-03-20 1983-09-28 BASF Aktiengesellschaft Thioalkansäure-silylalkylester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses

Also Published As

Publication number Publication date
IL55085A0 (en) 1978-09-29
ATA491978A (de) 1980-02-15
HU182473B (en) 1984-01-30
BR7804382A (pt) 1979-03-06
IT7825415A0 (it) 1978-07-06
AR221487A1 (es) 1981-02-13
CA1108172A (en) 1981-09-01
IT1096916B (it) 1985-08-26
AT358557B (de) 1980-09-25
CS222267B2 (en) 1983-06-24
DD138142A5 (de) 1979-10-17
ES471526A1 (es) 1979-01-16
AU522170B2 (en) 1982-05-20
AU3782478A (en) 1980-01-10
JPS6230184B2 (pt) 1987-07-01
TR20047A (tr) 1980-07-02
JPS5416438A (en) 1979-02-07
US4349377A (en) 1982-09-14
IL55085A (en) 1983-02-23

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