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)

Applications Claiming Priority (4)

Publications (1)

Family

ID=25686139

Family Applications (1)

Country Status (15)

Cited By (3)

Families Citing this family (48)

Citations (6)

Family Cites Families (1)

• 1978
  • 1978-06-29 EP EP78100270A patent/EP0000351A1/de not_active Ceased
  • 1978-07-05 IL IL55085A patent/IL55085A/xx unknown
  • 1978-07-05 AR AR272847A patent/AR221487A1/es active
  • 1978-07-05 DD DD78206536A patent/DD138142A5/xx unknown
  • 1978-07-06 HU HU78CI1838A patent/HU182473B/hu unknown
  • 1978-07-06 ES ES471526A patent/ES471526A1/es not_active Expired
  • 1978-07-06 AT AT491978A patent/AT358557B/de not_active IP Right Cessation
  • 1978-07-06 CA CA306,928A patent/CA1108172A/en not_active Expired
  • 1978-07-06 AU AU37824/78A patent/AU522170B2/en not_active Expired
  • 1978-07-06 TR TR20047A patent/TR20047A/tr unknown
  • 1978-07-06 IT IT25415/78A patent/IT1096916B/it active
  • 1978-07-07 CS CS784551A patent/CS222267B2/cs unknown
  • 1978-07-07 BR BR7804382A patent/BR7804382A/pt unknown
  • 1978-07-07 JP JP8281778A patent/JPS5416438A/ja active Granted
• 1980
  • 1980-09-05 US US06/184,608 patent/US4349377A/en not_active Expired - Lifetime

Patent Citations (6)

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