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
  • C07C317/00—Sulfones; Sulfoxides

Definitions

• the present invention relates to novel phenoxy-phenyl-sulfinyl and -sulfonyl-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 the new phenoxy-phenyl-sulfinyl- and -sulfonyl-alkane carboxylic acid derivatives or compositions containing them as herbicides and / or for regulating plant growth.
• alkyl and alkenyl radicals in this definition can be branched or unbranched.
• the present phenoxy-phenylsulfinyl and sulfonyl alkane carboxylic acid derivatives are new compounds. Phenoxyphenylthio-alkane carboxylic acid derivatives with a similar structure, which can be used as starting materials for the preparation of the present compounds, are known.
• the FR-PS 285 861 describes compounds which show pharmacological activity, the DOS 2 223 894 those with herbicidal activity.
• herbicidal diphenyl ethers with alkyl and alkenylsulfinyl or sulfonyl radicals have been described in DT-OS 2 130 919 and 2 333 848.
• the compounds of the formula I have a herbicidal action which does not act equally strongly against all types of plants. This creates valuable selectivities that make it possible to specifically combat weeds in crops without noticeably damaging the crops. The best effect is achieved in the post-emergence process in cereal and rice crops against broad-leaved weeds.
• the compounds of the present invention are not very toxic to warm-blooded animals and their application poses no problems.
• the application rate is between 0.1 and 5 kg per hectare.
• Hal means a halogen atom, preferably chlorine or bromine.
• the preparation of such phenoxy-phenylthioalkanecarboxylic acid derivatives is also described, inter alia, in DOS 2 223 894.
• Another way to get to these phenoxy-phenylthio-alkane carboxylic acid derivatives of the formula II also starts from the optionally substituted halogenobenzenes of the formula III, which are e.g. condensed with an optionally further substituted hydroxyphenylthio-alkane carboxylic acid of formula VII in the presence of an acid-binding agent such as e.g. an inorganic base, in an aprotic solvent at elevated temperature.
• an acid-binding agent such as e.g. an inorganic base
• the process according to the invention for the preparation of the new phenoxyphenylsulfinyl and sulfonyl alkane carboxylic acid derivatives is characterized in that a phenoxy phenylthio alkane carboxylic acid derivative of the formula II (see formula scheme), in which B, C, D, E and Q have the meaning given under formula, treated with an oxidizing agent until the sulfide bridge to the sulfinyl - (- SO) or sulfonyl bridge (-S0 2 ) is oxidized.
• Suitable oxidizing agents for this reaction are, for example, hydrogen peroxide, oxygen or optionally also air which is blown through the reaction mixture.
• the phenoxy-phenylthio-alkane carboxylic acid derivative can be added to dilute sodium hydroxide solution and then slowly chlorine can be blown through the reaction mixture.
• the compounds of the formula I can also be prepared by reducing an appropriately substituted diphenyl ether sulfochloride with sodium sulfite to give the sulfinic acid and then, or a salt thereof, with a radical Hal-Q-COB, in which B, Q and Hal have the meaning given under formula I.
• phenoxy-phenylsulfinyl and - phenylsulfonylalkane-carboxylic acid derivatives of the formula are stable compounds which are soluble in common organic solvents, such as alcohols, ethers, ketones, dimethylformamide, dimethyl sulfoxide, etc.
• the invention also relates to herbicidal and plant growth-regulating agents which receive a new active ingredient of the formula I, and to processes for pre- and post-emergent weed control and for inhibiting the growth of monocotyledonous and dicotyledonous plants, in particular grasses, cereals, soybeans and tobacco stems.
• the agents according to the invention can be present in the usual formulations.
• Agents according to the invention are prepared in a manner known per se by intimately mixing and grinding active ingredients of the formula I with suitable carriers, optionally with the addition of dispersing agents or solvents which are inert to the active ingredients.
• suitable carriers optionally with the addition of dispersing agents or solvents which are inert to the active ingredients.
• the active ingredients can be present and used in the following forms:
• the active ingredients are mixed with solid carriers to produce solid processing forms (dusts, scattering agents, granules).
• Carriers include, for example, kaolin, talc, bolus, loess, chalk, limestone, lime grits, ataclay, dolomite, diatomaceous earth, precipitated silica, alkaline earth metal silicates, sodium and potassium aluminum silicates (feldspar and mica), calcium and magnesium sulfates, magnesium oxide, ground Plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ground vegetable products, such as grain flour, tree bark flour, wood flour, nutshell flour, cellulose powder, residues from plant extracts, activated carbon, etc., each individually or as a mixture with one another in question.
• 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.
• 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 as well as growth inhibition.
• Agents according to the invention which contain at least one compound of the formula I as active component are particularly suitable for inhibiting and controlling the plant growth of monocotyledonous and dicotyledonous plants, such as grasses, shrubs, trees, crops of cereals and legumes, sugar cane, tobacco, soybeans, Bulbs of onions and potatoes, ornamental plants, fruit trees and vines.
• monocotyledonous and dicotyledonous plants such as grasses, shrubs, trees, crops of cereals and legumes, sugar cane, tobacco, soybeans, Bulbs of onions and potatoes, ornamental plants, fruit trees and vines.
• Rice plants that are 25 days old were transplanted into large rectangular eternit bowls in the greenhouse. Seeds of the weeds Echinochloa crus galli found in rice crops were then placed between the rows of rice plants. Cyperus difformis, Ammania and Rotala sown. The dishes were well watered and kept at a temperature of approx. 25 ° C and high humidity. After 12 days, when the weeds had emerged and reached the 2-3 leaf stage, the earth in the bowl was covered with a 2.5 cm high layer of water.
• the active substance was then applied as an emulsion concentrate by means of a pipette between the rows of plants, the emulsion concentrate being diluted and applied so that it corresponded to an application amount in the field of 4, 2, 1 and 1/2 kg of active ingredient per hectare.
• the experiment was evaluated after 4 weeks. The results are summarized in Table 3.
• the compounds according to the invention generally show good herbicidal activity against dicotyledonous plants and some monocotyledon weeds.
• they could be used for selective control, especially dicotyledonous weeds in rice and certain cereals.
• the known compounds A, B and C showed no pronounced herbicidal action here, while the compound D acts differently and, above all, damages weeds which are monocotyledonous.

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• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Dentistry (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Plant Pathology (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

Applications Claiming Priority (2)

Publications (2)

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ID=4340163

Family Applications (1)

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• 1978
  • 1978-06-30 EP EP78100281A patent/EP0000359B1/de not_active Expired
  • 1978-06-30 DE DE7878100281T patent/DE2861187D1/de not_active Expired
  • 1978-07-05 CA CA306,855A patent/CA1102818A/en not_active Expired
  • 1978-07-05 IL IL55083A patent/IL55083A/xx unknown
  • 1978-07-06 ZA ZA00783883A patent/ZA783883B/xx unknown
  • 1978-07-06 ES ES471531A patent/ES471531A1/es not_active Expired
  • 1978-07-07 JP JP8281378A patent/JPS5416447A/ja active Pending

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