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-alkane carboxylic 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 new phenoxy-phenyl-sulfinyl- and -sulfonyl-alkane carboxylic acid derivatives or agents containing them as herbicides and / or for regulating plant growth.
• the new phenoxy-phenyl-sulfinyl and -sulfonyl-alkane carboxylic acid derivatives correspond to the formula I.
• alkyl and alkylene radicals in this formula can be branched or unbranched and contain the specified number of carbon atoms.
• the radicals R 5 and R 6 can be hydrogen or aliphatic, cycloaliphatic, aromatic radicals or, together with the nitrogen atom to which they are attached, they can form a preferably 5-6-membered heterocycle which can also contain further heteroatoms.
• hydrogen and lower C 1 -C 4 alkyl radicals are preferred.
• the compounds of the present invention are not very toxic to warm-blooded animals and their application poses no problems.
• the amount of effort - is between 0.1 and 5 kg per hectare.
• A, C, D, E, Q, n and p have the meaning given under formula I and Hal represents a halogen atom, preferably chlorine or bromine.
• the preparation of such fhenoxy-phenylthio-alkane carboxylic 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 phenoxy-phenylsulfinyl- and sulfonyl-alkanecarboxylic acid derivatives is characterized in that a phenoxy-phenylthio-alkanecarboxylic acid derivative of the formula II (see formula scheme), in which A, C, D, E, Q , Hal and n have the meaning given under formula I, as long as treated with an oxidizing agent until the sulfide bridge to the sulfinyl - (- 50-) or sulfonyl bridge (-SO 2 ) is oxidized.
• Suitable oxidizing agents for this reaction are, for example, hydrogen peroxide, oxygen or, if appropriate, also air which passes through the reaction mixture. You can also add the phenoxy-phenylthio-alkane carboxylic acid derivative to dilute sodium hydroxide solution and then slowly blow chlorine 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 this, or a salt thereof, with a radical Hal-QA in which A, Q and Hal are those of formula I have given meaning.
• phenoxy-phenylsulfinyl- and -phenylsulfonylalkane-carboxylic acid derivatives of the formula I are stable compounds which are soluble in customary 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 stingers.
• the agents according to the invention can be present in the usual formulations.
• 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 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.
• 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-emergence 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, onions and potato tubers, ornamental plants, fruit trees and vines.
• monocotyledonous 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 new 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.
• the labor-intensive cutting work can be reduced by treating trees, shrubs and hedges, especially in residential and industrial areas, with compounds of the formula I according to the invention.
• active compounds of the formula I 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, further to inhibit the sprouting of stored tubers, for example in ornamental plant tubers, in onions and potatoes, and finally to increase the yield in crops which grow strongly vegetatively, such as soya and sugar cane, by application active substances according to the invention the transition from the vegetative to the generative growth phase is accelerated.
• the active compounds of the formula I 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.
• active compounds of the formula I and compositions containing them are also suitable for other influences on plant growth, such as, in particular, to facilitate the removal of fruit and leaves by forming separating tissues on the fruit and leaf stalks, which results in a considerable reduction in the tear-off force and thus a great deal Brings easier harvesting.
• flowers and fruit are also thinned out.
• 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 and sugar cane. 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 new active ingredients of Formula I are also characterized by a very strong pre-emergent herbicide effect, so they are also pronounced germination inhibitors.
• 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.

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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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Citations (6)

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• 1978
  • 1978-06-30 EP EP78100281A patent/EP0000359B1/fr not_active Expired
  • 1978-06-30 DE DE7878100281T patent/DE2861187D1/de not_active Expired
  • 1978-07-05 CA CA306,855A patent/CA1102818A/fr 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

Patent Citations (6)

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