WO2017144402A1 - Amides d'acide n-(5-halogèn-1,3,4-oxadiazol-2-yl)arylcarboxylique et leur utilisation comme herbicides - Google Patents

Amides d'acide n-(5-halogèn-1,3,4-oxadiazol-2-yl)arylcarboxylique et leur utilisation comme herbicides Download PDF

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Publication number
WO2017144402A1
WO2017144402A1 PCT/EP2017/053763 EP2017053763W WO2017144402A1 WO 2017144402 A1 WO2017144402 A1 WO 2017144402A1 EP 2017053763 W EP2017053763 W EP 2017053763W WO 2017144402 A1 WO2017144402 A1 WO 2017144402A1
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Prior art keywords
alkyl
cycloalkyl
heterocyclyl
halogen
halo
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PCT/EP2017/053763
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German (de)
English (en)
Inventor
Arnim Köhn
Christian Waldraff
Hartmut Ahrens
Hansjörg Dietrich
Elmar Gatzweiler
Christopher Rosinger
Jörg Tiebes
Armin SAUSEN
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Bayer Cropscience Aktiengesellschaft
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Publication of WO2017144402A1 publication Critical patent/WO2017144402A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and grass weeds in crops.
  • WO 2012/126932 A1 discloses herbicidally active N- (l, 3,4-oxadiazol-3-yl) arylcarboxamides which carry a hydrogen atom or a radical bonded via a carbon atom in the 5-position of the oxadiazole ring.
  • WO 2001/002354 A1 discloses N-heterocyclylphthalamides as insecticides. There is also the under the CAS no. No. 1,323,324-77-1 discloses a known compound N 1 - (5-chloro-1, 3,4-oxadiazol-2-yl) -N 2 , N 2 -diethyl-3-iodo-phthalamide.
  • Object of the present invention was the provision of other herbicidally active compounds. This object has been achieved by providing N- (l, 3,4-oxadiazol-2-yl) arylcarbonklareamiden which carry a halogen atom in the 5-position of the Oxadiazolrings.
  • An object of the present invention are thus N- (5-halo-l, 3,4-oxadiazol-2-yl) arylcarbonklareamide of formula I) and their salts
  • X is nitro, halogen, cyano, formyl, thiocyanato, (Ci-C6) alkyl, halo (Ci-C6) alkyl, (C 2 - C 6) alkenyl, halo (C 2 -C 6) - alkenyl, (C 2 -C 6) alkynyl, halo (C 3 -C 6) -alkynyl, (C 3 -C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (C3-C 6) -cycloalkyl- (Ci-C 6) alkyl, halo (C3-C6) cycloalkyl- (Ci-C 6) - alkyl, COR 1, COOR 1, OCOOR ' ⁇ R'COOR 1, C ( 0) N (R 1 ) 2 , NR 1 C (O) N (R 1 ) 2 , OC (O) N (
  • Y is hydrogen, nitro, halogen, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, halogen (C 2 -C 6 ) - alkenyl, (C 2 -C 6 ) alkynyl, halo (C 2 -C 6 ) alkynyl, (C 3 -C 6 ) cycloalkyl, (C 3 -C 6 ) cycloalkenyl, halogen (C 3 -) C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 1 , COOR
  • Z is hydrogen, halogen, cyano, thiocyanato, (Ci-C6) alkyl, (Ci-C6) alkoxy, halo (Ci- C6) alkyl, (C 2 -C 6) alkenyl, halo ( C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, halo (C 2 -C 6) -alkynyl, (C 3 - C 6) cycloalkyl, halo (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, halo (C 3 -C 6) - cycloalkyl- (Ci-C 6) alkyl, COR 1, COOR 1, OCOOR 1 , NR 1 COOR 1 , C (O) N (R 1 ) 2 , NR 1 C (O) N (R 1 ) 2 , OC (O
  • W is hydrogen, halogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, OR 1, S (0) n R 2, R 1 represents hydrogen, (Ci-C 6) alkyl, ( Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -
  • R 2 is (Ci-C 6) -alkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -haloalkenyl, (C 2 -C 6) - alkynyl , (C 2 -C 6) -haloalkynyl, (C3-C6) -cycloalkyl, (C3-C6) cycloalkenyl, (C3-C6) halocycloalkyl, (Ci-C6) alkyl-0- (Ci-C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, phenyl, phenyl (C 1 -C 6 ) -alkyl, heteroaryl, (C 1 -C 6 ) -alkyl-heteroaryl, heterocyclyl, ( C 1
  • R 3 is hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl or (C 3 -C 6 ) Cycloalkyl- (C 1 -C 6 ) -alkyl,
  • R 4 is (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl or (C 2 -C 6 ) -alkynyl, R 5 is methyl or ethyl, n is 0, 1 or 2, s is 0 , 1, 2 or 3,
  • Alkyl radicals are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Heterocyclyl means a saturated, partially saturated or fully unsaturated cyclic radical containing from 3 to 6 ring atoms, of which from 1 to 4 are from the group consisting of oxygen, nitrogen and sulfur, and may additionally be fused by a benzo ring. For example, stands
  • Heteroaryl means an aromatic cyclic radical containing 3 to 6 ring atoms, of which 1 to 4 are from the group oxygen, nitrogen and sulfur, and additionally by a
  • Benzoring can be annealed.
  • heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl,
  • the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers may occur. Similarly, stereoisomers occur when n is 1 (sulfoxides). Stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention also relates to all stereoisomers and mixtures thereof which are of the general formula (I), but not specifically defined.
  • A is N or CY
  • Hal is chlorine
  • X is nitro, halo, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl, OR 1, S (0) n R 2 , (C 1 -C 6 ) -alkyl-S (0) n R 2 , (C 1 -C 6 ) -alkyl-OR 1 , (C 1 -C 6 ) -alkyl-CON (R 1 ) 2 , (Ci -C 6) alkyl S0 2 N (R 1) 2, (Ci-C 6) alkyl-NR 1 COR 1, (Ci-C 6) alkyl-NR 1 S0 2 R 2, (Ci-C 6 ) -Alkyl heteroaryl, (Ci-C 6 ) - Alkyl heterocyclyl, where the latter two radicals in each case by s radicals from the group consisting of halogen, (Ci
  • Heterocyclyl where the 6 last-mentioned radicals in each case by s radicals selected from the group consisting of halogen, nitro, cyano, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 3 -C 6) - Cycloalkyl, S (0) n - (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy, halogeno (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkoxy- (C 1 -C 4) -alkyl and cyanomethyl are substituted, and wherein heterocyclyl carries n oxo groups,
  • Z is hydrogen, halogen, methyl, ethyl, isopropyl, halogeno (Ci-C6) -alkyl, (C 3 -Ce) -cycloalkyl, S (0) n R 2 or
  • V is hydrogen
  • W means hydrogen
  • R 1 represents hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (C 3 -C 6) -cycloalkyl, (C 3 - C 6 ) -Cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkyl-O- (C 1 -C 6 ) -alkyl, phenyl, phenyl- (C 1 -C 6 ) -alkyl, heteroaryl, (Ci -C 6 ) -alkyl heteroaryl, heterocyclyl, (C 1 -C 6 ) -alkyl heterocyclyl, (C 1 -C 6 ) -alkyl-0-heteroaryl, (C 1 -C 6 ) -alkyl-O-heterocyclyl, (Ci C 6 ) -
  • R 2 is (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl or (C 3 -C 6) -cycloalkyl- (Ci-C 6) -alkyl, where the three abovementioned radicals are each substituted by s radicals from the group consisting of halogen and OR 3 are substituted,
  • R 3 is hydrogen or (C 1 -C 6 ) -alkyl, is (C 1 -C 6 ) -alkyl, n is 0, 1 or 2, s is 0, 1, 2 or 3.
  • benzoic acid chlorides of the formula (II) or the benzoic acids on which they are based are known in principle and can be synthesized, for example, according to the methods described in WO 2012/126932 A1, US Pat
  • Amidation reactions such as. B. ⁇ , ⁇ -carbonyldiimidazole (CDI), dicyclohexyl-carbodiimide (DCC), 2,4,6-tripropyl-l, 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxides (T3P) etc . are used.
  • CDI ⁇ -carbonyldiimidazole
  • DCC dicyclohexyl-carbodiimide
  • T3P 3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxides
  • the 2-amino-5-halo-l, 3,4-oxadiazoles (III) are known and can be prepared according to methods known to those skilled in the art.
  • Collections of compounds of formula (I) and / or their salts, which may be synthesized following the above reactions, may also be prepared in a parallelized manner, which may be done in a manual, partially automated or fully automated manner. It is possible, for example, to automate the reaction procedure, the work-up or the purification of the products or intermediates. Overall, this is one
  • Calypso reaction blocks (Caylpso reaction blocks) from Barnstead International, Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Waiden, Essex, CB 11 3AZ, England or
  • Chromatographieapparaturen available, for example, the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
  • the listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed.
  • This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots.
  • Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
  • Solid-phase assisted synthesis methods allow a number of protocols known from the literature, which in turn can be performed manually or automatically.
  • the reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
  • Both solid and liquid phases may require the performance of one or more
  • the preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries.
  • the present invention also provides libraries containing at least two compounds of formula (I) and their salts.
  • the compounds of the formula (I) according to the invention (and / or their salts), together referred to as “compounds according to the invention", have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants which are expelled from rhizomes, rhizomes or other long-term organs, are well detected by the active ingredients.
  • the present invention therefore also provides a method for combating
  • Plant cultures in which one or more compounds of the invention (s) on the plants eg harmful plants such as mono- or dicotyledonous weeds or undesirable crops
  • the seed eg grains, seeds or vegetative propagules such as tubers or sprouts with buds
  • the area on the plants grow eg the acreage
  • the compounds according to the invention can be applied, for example, in pre-sowing (optionally also by incorporation into the soil), pre-emergence or postemergence process.
  • the compounds according to the invention are applied to the surface of the earth before germination, then either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die off completely after a lapse of three to four weeks.
  • the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops, eg dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeal, Sorghum, Triticale, Triticum, Zea, especially Zea and Triticum, depending on the structure of the respective compound of the invention and its application rate only insignificantly damaged or not at all.
  • the present compounds are suitable for these Reason very well for the selective control of undesirable plant growth in crops such as agricultural crops or ornamental plantings.
  • the compounds according to the invention (depending on their respective structure and the applied application rate) have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, since, for example, storage formation can thereby be reduced or completely prevented.
  • the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. So are transgenic plants with increased starch content or altered quality of starch or those with others
  • transgenic crops Fatty acid composition of the crop known.
  • transgenic crops is the use of the compounds of the invention in economically important transgenic crops of useful and ornamental plants, eg.
  • cereals such as wheat, barley, rye, oats, millet, rice and corn or even crops of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • the compounds of the invention in economically important transgenic crops of useful and ornamental plants, eg.
  • cereals such as wheat, barley, rye, oats, millet, rice and corn or even crops of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • Compounds of the invention are used as herbicides in crops that are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.
  • the application of the compounds of the invention or their salts in economically important transgenic crops of useful and ornamental plants eg.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • the compounds of the invention or their salts in economically important transgenic crops of useful and ornamental plants, eg.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • the compounds of the invention or their salts in economically important transgenic crops of useful and ornamental plants, eg.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea
  • Compounds of the invention are used as herbicides in crops, which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • transgenic crops which are resistant to certain glufosinate-type herbicides (cf., for example, EP-A-0242236, EP-A-242246) or glyphosates
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) to produce, which the
  • transgenic crops which are characterized by higher yields or better quality transgenic crops characterized by a combination of z.
  • Numerous molecular biological techniques by which new transgenic plants with altered properties can be produced are known in principle, see, for example, I. Potrykus and G.
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With the help of standard methods z. B. base exchanges, Partial sequences are removed or natural or synthetic sequences are added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY, or Winnacker "Gene and Clones", VCH Weinheim 2nd edition, 1996
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect, or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227, Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850, Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants can in principle be plants of any one
  • Plant species that is, both monocotyledonous and dicotyledonous plants.
  • the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against herbicides, the essential plant enzymes, eg. Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate Dioxygenases (HPPD) inhibit or are resistant to herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues.
  • the essential plant enzymes eg. Acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate Dioxygenases (HPPD) inhibit or are resistant to herbicides from the group of sul
  • the invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the compounds according to the invention can be used in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules in the customary formulations.
  • the invention therefore also relates to herbicidal and plant growth-regulating agents which contain the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined.
  • Formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, Suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW emulsions
  • SC Suspension concentrates
  • SC oil- or water-based dispersions
  • Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain surfactants of an ionic and / or nonionic type (wetting agent,
  • Dispersant e.g. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalene-sulfonate, or sodium oleoylmethyltaurine.
  • the herbicidal active ingredients are finely ground, for example, in conventional apparatus such as hammer mills, blower mills and air jet mills and simultaneously or subsequently with the
  • Formulation aids mixed.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents
  • surfactants of ionic and / or nonionic type emulsifiers
  • alkylarylsulfonic acid calcium salts such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters
  • Alkylaryl polyglycol ethers fatty alcohol polyglycol ethers,
  • Propylene oxide-ethylene oxide condensation products alkyl polyethers, sorbitan esters, e.g.
  • Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g. Polyoxyethylene.
  • Dusts are obtained by milling the active ingredient with finely divided solids, e.g.
  • Talc natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding by means of commercially available bead mills and, if appropriate, addition of surfactants, as already listed above, for example, in the other formulation types.
  • Emulsions for example oil-in-water emulsions (EW)
  • EW oil-in-water emulsions
  • Granules can either be prepared by spraying the active ingredient onto adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, for example polyvinyl alcohol, polyacrylic acid sodium or else mineral oils to the
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
  • the drug concentration is e.g. about 10 to 90 wt .-%, the balance to 100 wt .-% consists of conventional formulation ingredients.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% active ingredient.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreezing and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.
  • other pesticidally active substances such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and / or growth regulators, for example in the form of a ready-to-use formulation or as a tank mix.
  • combination partners for the compounds according to the invention in mixture formulations or in the tank mix are known active compounds which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine Synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, can be used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 15th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2009 and cited therein.
  • herbicides or plant growth regulators with the inventive
  • Compounds can be combined, e.g. the following active ingredients (the compounds are denoted either by the "common name” according to the International Organization for Standardization (ISO) or the chemical name or with the code number) and always include all forms of use such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
  • ISO International Organization for Standardization
  • the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-like preparations, soil or
  • Spreading granulates and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the type of herbicide used u.a. varies the required application rate of the compounds of formula (I). It can vary within wide limits, e.g. between 0.001 and 1.0 kg / ha or more of active substance, but is preferably between 0.005 and 750 g / ha.
  • W stands for hydrogen and shark stands for chlorine
  • ⁇ 8.225 (2.4); 8.205 (2.5); 7,519 (0.9); 7.2733 (0.5); 7.2726 (0.6); 7.272 (0.7); 7.271 (0.7); 7.270 (0.9); 7.2693 (1.1); 7.2686 (1.2); 7.268 (1.5); 7.267 (1.7); 7.266 (1.9); 7.2653 (2.3); 7.2645 (3.0); 7,264 (4,1); 7.260 (167.9); 7.2563 (1.3); 7.2555 (1.0); 7.255 (0.8); 7.254 (0.6); 7.211 (1.1); 6.996 (1.0); 3,477 (16.0); 3.286 (0.5); 3,006 (0.5); 2,544 (10.9); 1,539 (14.4); 0.008 (2.1); 0.006 (0.6); 0.005 (0.7); 0,000 (73.2); -0.009 (2.0)
  • ⁇ 7.750 (0.7); 7.729 (0.7); 7.265 (0.5); 7.264 (0.7); 7,261 (29.5); 6,886 (1.6); 6.865 (1.5); 2,841 (0.6); 2,417 (16,0); 1,543 (6.5); 1.193 (1.1); 1,189 (1,1); 1.184 (0.6); 1.177 (0.6); 1,172 (1,1); 1.168 (1.1); 1.156 (0.5); 0.809 (0.5); 0.797 (1.1); 0.793 (1.1); 0.784 (1.0); 0.780 (1.2); 0,000 (12,8)
  • ⁇ 7.587 (0.7); 7,583 (0.7); 7,568 (0.9); 7,564 (0.9); 7.438 (1.7); 7,419 (3.0); 7,399 (2.3); 7.358 (1.5); 7,354 (1.5); 7,338 (0.9); 7.334 (0.8); 7.265 (0.6); 7.264 (0.8); 7,261 (33,9); 2,535 (16.0); 1.547 (2.4); 0.002 (0.6); 0.000 (13.9); -0.003 (0.5)
  • ⁇ 8.280 (0.5); 7,573 (1.9); 7,553 (2.0); 7.289 (2.0); 7.268 (2.4); 7,261 (34.4); 7.210 (0.8); 3,092 (16.0); 3.041 (0.5); 2,772 (11,4); 2,694 (10.1); 0.008 (0.6); 0.000 (13.7); -0.008 (0.7)
  • ⁇ 8.356 (1.0); 8.335 (1.1); 7.695 (1.2); 7.674 (1.1); 7,392 (0.7); 7,262 (14.4); 7.254 (1.5); 7.117 (0.7); 4,171 (16,0); 2,986 (0.9); 2,967 (2.7); 2,949 (2.8); 2,930 (0.9); 1,549 (0.5); 1,249 (3,4); 1,231 (7.0); 1,212 (3,2); 0,000 (6.0)
  • Table 5 Compounds of the general formula (I) according to the invention, in which A is N and V and W is hydrogen.
  • a dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuting in a hammer mill.
  • a wettable powder readily dispersible in water is obtained by adding 25
  • a dispersion concentrate readily dispersible in water is obtained by adding 20 parts by weight of a compound of the formula (I) and / or its salts with 6 parts by weight
  • Alkylphenolpolyglyko lether (®Triton X 207), 3 parts by weight Isotridecanolpolyglykolether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to about 277 C) mixed and in a ball mill to a fineness of less than 5 microns married.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • a water-dispersible granules are obtained by
  • a water-dispersible granule is also obtained by
  • Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in sandy loam in wood fiber pots and covered with soil.
  • the compounds of the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion having a water application rate of 600 to 800 l / ha with the addition of 0.2% wetting agent applied.
  • WP wettable powders
  • EC emulsion concentrates
  • Seeds of monocotyledonous or dicotyledonous crops are laid out in sandy loam soil in wood fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage.
  • compounds Nos. 1-143, 1-145, 1-153, 1-161, 1-185, 1-250, 1-290, 1-384, 1-385, 1-448, 1-451 show , 1-454, 1-455, 1-461, 1-469 and 1-472 at an application rate of 80 g / ha each have at least 80% activity against Amaranthus retroflexus, Setaria viridis and

Abstract

L'invention concerne des amides d'acide N-(5-Halogèn-1,3,4-oxadiazol-2-yl)arylcarboxylique de la formule générale (I) et leur utilisation comme herbicides. Dans la formule (I), A représente azote ou CY. R, V, X, Y et Z représentent des groupes comme hydrogène, des groupes organiques comme alkyle, et d'autres groupes comme halogène.
PCT/EP2017/053763 2016-02-24 2017-02-20 Amides d'acide n-(5-halogèn-1,3,4-oxadiazol-2-yl)arylcarboxylique et leur utilisation comme herbicides WO2017144402A1 (fr)

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CN110016019A (zh) * 2019-04-30 2019-07-16 河北大学 一种基于呋喃酚的噁二唑类衍生物及其制备方法与应用
WO2020108518A1 (fr) * 2018-11-30 2020-06-04 青岛清原化合物有限公司 Formamides de n-(1,3,4-oxadiazole-2-yl)aryle ou leur sel, procédé de préparation correspondant, composition herbicide et utilisation associée
CN111484487A (zh) * 2019-01-29 2020-08-04 青岛清原化合物有限公司 杂环基芳基甲酰胺类或其盐、制备方法、除草组合物和应用
WO2021078174A1 (fr) 2019-10-23 2021-04-29 青岛清原化合物有限公司 Composé de formamide aryl contenant de l'oxyde de soufre chiral et sel de celui-ci, son procédé de préparation, composition herbicide et utilisation
WO2021083245A1 (fr) * 2019-10-30 2021-05-06 江苏清原农冠杂草防治有限公司 Composition herbicide comprenant un composé de n-(1,3,4-oxadiazole-2-yl)arylformamide et son utilisation
DE112019005943T5 (de) 2018-11-30 2021-08-26 Qingdao Kingagroot Chemical Compound Co., Ltd. N-(1, 3, 4-Oxadiazol-2-yl)arylcarboxamide oder deren Salze, Herstellungsverfahren, Herbizidzusammensetzungen und Verwendungen dieser
WO2021204666A1 (fr) 2020-04-07 2021-10-14 Bayer Aktiengesellschaft Diamides d'acide isophtalique substitués et leur utilisation en tant qu'herbicides
WO2021204665A1 (fr) 2020-04-07 2021-10-14 Bayer Aktiengesellschaft Diamides d'acide isophtalique substitués
WO2021204667A1 (fr) 2020-04-07 2021-10-14 Bayer Aktiengesellschaft Diamides d'acide isophtalique substitués
WO2021204669A1 (fr) 2020-04-07 2021-10-14 Bayer Aktiengesellschaft Diamides d'acide isophtalique substitués
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RU2789195C2 (ru) * 2018-11-30 2023-01-31 Циндао Кингагрут Кемикал Компаунд Ко., Лтд. N-(1,3,4-оксадиазол-2-ил)арилкарбоксамиды или их соли, способы получения, гербицидные композиции и их применения
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