WO2014086738A1 - 4-amino-6-acyloxyméthylpyrimidines et 4-amino-2-acyloxyméthyl­pyridines à action herbicide - Google Patents

4-amino-6-acyloxyméthylpyrimidines et 4-amino-2-acyloxyméthyl­pyridines à action herbicide Download PDF

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WO2014086738A1
WO2014086738A1 PCT/EP2013/075307 EP2013075307W WO2014086738A1 WO 2014086738 A1 WO2014086738 A1 WO 2014086738A1 EP 2013075307 W EP2013075307 W EP 2013075307W WO 2014086738 A1 WO2014086738 A1 WO 2014086738A1
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alkyl
cycloalkyl
halo
halogen
heterocyclyl
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PCT/EP2013/075307
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German (de)
English (en)
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Michael Gerhard Hoffmann
Uwe Döller
Marco BRÜNJES
Hansjörg Dietrich
Elmar Gatzweiler
Dirk Schmutzler
Christopher Hugh Rosinger
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Bayer Cropscience Ag
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Publication of WO2014086738A1 publication Critical patent/WO2014086738A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom

Definitions

  • the invention relates to the technical field of herbicides, in particular that of herbicides for the selective control of weeds and weeds in
  • WO 95/19358 A1 and EP 0 222 254 A2 disclose herbicidally active aryl- and heteroarylpyrimidines which carry a nicotinic acid radical.
  • the compounds known from this document often show inadequate herbicidal activity and / or compatibility with crop plants.
  • the object of the present invention is therefore the provision of further herbicidally active compounds. It has now been found that certain 4-amino-6-acyloxymethyl-pyrimidines and 4-amino-2-acyloxymethylpyridine are particularly well suited as herbicides.
  • An object of the present invention are 4-amino-6-acyloxymethyl-pyrimidines and 4-amino-2-acyloxymethylpyridine of the formula (I) or their N-oxides
  • A denotes in each case by s radicals from the group consisting of nitro, halogen, cyano, rhodano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl.
  • Heterocyclyl (Ci-C6) alkyl in each case by s radicals selected from the group consisting of halogen, nitro, cyano, (CrC 6) alkyl, halo (Ci-C 6) alkyl, S (0) n - (C -C 6 ) alkyl, (d-Ce) alkoxy and halo (Ci-C6) alkoxy are substituted, and wherein Heterocyclyi n carries oxo groups, or
  • radicals from the group consisting of (Ci-Ce) -alkyl and halogen-substituted
  • R 1 represents LR 1 ', is hydrogen, (Ci-Ce) alkyl, halo (Ci-C 6) 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, (C 3 -C 6 ) -Cycloalkyl- (C 1 -C 6 ) -alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , N (R 6 ) 2 , NR 6 COOR 5 , C (O) N (R 6 ) 2 ,
  • R 2 is hydrogen. (CrC 6) alkyl, halo (CrC 6) alkyl, (C 3 -C 6) cycloalkyl, halo (C3-C6) cycloalkyl or halogen,
  • R 3 and R 4 are each independently hydrogen, (Ci-Ce) - alkyl, halo (Ci-C 6) 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, (C 3 - C6) - cycloalkyl- (Ci-C6) alkyl, halo (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, COR 8 or S (0) n R 6,
  • R 5 represents (Ci-COE) alkyl, halo (Ci-C 6) -alkyl, (C2 -Ce) 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, (C 4 -C 8 ) cycloalkenyl, halogeno ( C 3 -C 6) cycloalkenyl, (C 3 -C 6) -cycloalkyl- (Ci-C (6) alkyl or halo C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl,
  • R 6 represents hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) -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, (C4-C8) cycloalkenyl, halogen (C 3 -C 6) -cycloalkenyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl or halogeno (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl,
  • alkyl radicals having more than two carbon atoms may be straight-chain or branched.
  • 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.
  • alkenyl is for example allyl, 1-methylprop-2-en-1-yl,
  • Alkynyl means e.g. Propargyl, but-2-yn-1-yl, but-3-yn-yl, 1-methyl-but-3-yn-1-yl.
  • the multiple bond can each be in any position of the unsaturated radical.
  • Cycloalkyl means a carbocyclic saturated ring system having three to six carbon atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • cycloalkenyl is a monocyclic alkenyl group having three to six carbon ring members, e.g. Cyclopropenyl, cyclobutenyl,
  • Cyclopentenyl and cyclohexenyl, wherein the double bond may be in any position.
  • 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 oxygen, nitrogen and sulfur, and additionally by a
  • heterocyclyl is piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl.
  • Heteroaryl means an aromatic 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.
  • heteroaryl is benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1, 2.3-oxadiazolyl, 1, 2,4- Oxadiazolyl, 1, 2,5-oxadiazolyl, 1, 3, 4-oxadiazolyl, 1, 2,4-triazolyl, 1, 2,3-triazolyl, 1, 2,5-triazolyl, 1, 3, 4-triazolyl, 1, 2, 4-triazolyl, 1, 2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2,3-thiadiazolyl, 1, 2, 5-thiadiazolyl, 2H-1, 2.3.4-tetrazolyl, 1H-1,
  • the compounds of the general formula (I) can exist as stereoisomers. For example, if one or more asymmetric carbon atoms are present, then enantiomers and
  • stereoisomers 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. Likewise, stereoisomers can be prepared by using stereoselective reactions using optically active starting materials and / or
  • the invention also relates to all stereoisomers and mixtures thereof which are of the general formula (I), but not specifically defined.
  • A is in each case substituted by s radicals selected from the group consisting of nitro, halogen, cyano, (Ci-Ce) alkyl, halo (CrC 6) alkyl, (C 2 -C 6) alkenyl, halo (C 2 - C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, halogeno (C 3 -C 6 ) alkynyl, (C 3 -C 6 ) -cycloalkyl, halogeno (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 6 , COOR 6 , N (R 6 ) 2 , C (O) N (R 6 ) 2
  • R 1 represents LR 1 ', is hydrogen, (CrC 6) alkyl, halo (Ci-C 6) 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, (C -C 6 ) - Cycloalkyl- (C 1 -C 6 ) -alkyl, halo (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , N (R 6 ) 2 , NR 6 COOR 5 , C (0) N (R 6 ) 2 ,
  • Heterocyclyl (C 1 -C 6) -alkyl where the six last-mentioned radicals are in each case represented by s radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkyl, S (0) n - (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxy and halogeno (C 1 -C 6) -alkoxy, and where heterocyclyl carries n oxo groups,
  • L is in each case substituted by s radicals from the group consisting of (C 1 -C 12 -alkyl, nitro, cyano, halogen and OR 6 and in each case interrupted by s units from the group consisting of O, S (O) n and NR 6 ( Ci-Ce) alkylene, (C2 -Ce) - alkenylene or (C 2 -C 6) alkynylene chain,
  • R 1 ' is (C 3 -C 6 ) -cycloalkyl, halogeno (C 3 -C 6 ) -cycloalkyl, COR 6 , COOR 6 , N (R 6 ) 2 , NR 6 COOR 5 , C (O) N ( R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 . OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OCOR 6 , S (O) n R 5 , SO 2 N (R 6 ) 2 , NR 6 SO 2 R 5 , P (0 ) (OR 6 ) 2 , or
  • radicals from the group consisting of halogen, nitro, cyano,
  • R 3 and R 4 are each independently hydrogen, (C 1 -C 6 ) -alkyl, halogeno (C 1 -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, COR 8 or S (O) "R 6 , R 5 represents (Ci-C 6) alkyl, halo (Ci-C 6) -alkyl, (C2-C6) alkenyl, (C2-C6) -alkynyl, (C 3 -C 6) -cycloalkyl , (C 4 -C 8) cycloalkenyl, or (C3-C6) cycloalkyl (Ci-C 6) alkyl, R 6 is hydrogen,
  • X is CH or N, n is 0, 1 or 2, s is 0, 1, 2 or 3.
  • A is substituted by s radicals selected from the group consisting of nitro, halogen, cyano, (Ci-C 3) alkyl, halo (Ci-C 3) alkyl, (C 2 -C 3) alkenyl, (C 2 - C 3) -alkynyl, (C 3 -C 6) - cycloalkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 3) alkyl, COR 6, COOR 6, N (R 6) 2, C ( 0) N (R 6 ) 2 , OR 6 , S (O) n R 5 , S0 2 N (R 6 ) 2 and NR 6 S0 2 R 5 substituted phenyl, or
  • R 1 represents LR 1 ', is hydrogen, (Ci-C 6) alkyl, halo (Ci-C 6) alkyl, (C 2 -C 6) - alkenyl, (C2 -Ce) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, COR 6 , COOR 6 , N (R 6 ) 2 , NR 6 COOR 5 , C (O) N ( R 6 ) 2 , OR 6 , NR 6 S0 2 R 5 , (C 1 -C 6 ) -alkyl-S (0) n R 5 , (C 1 -C 6 ) -alkyl-OR 6 , (C 1 -C 6 ) alkyl-OS0 2 R 5, (Ci-C 6) alkyl-C0 2 R 6, (Ci-C
  • radicals in each case by s radicals selected from the group consisting of halogen, nitro, cyano, (CrC 6) alkyl, halo (Ci-C 6) alkyl, S (0) n - (Ci-C 6) alkyl, (C 1 -C 6) -alkoxy and halogeno (C 1 -C 6) -alkoxy, and wherein heterocyclyl carries n oxo groups.
  • L is a substituted by s radicals from the group consisting of (d-Ce) - alkyl, nitro, cyano, halogen and OR 6 and each interrupted by s units from the group consisting of O, S (0) n and NR 6 interrupted (C 1 -C 6) -alkylene, (C 2 -C 6) -alkenylene or (C 2 -C 6) -alkynylene chain,
  • R 1 ' is (C 3 -C 6 ) -cycloalkyl, COR 6 , COOR 6 , N (R 6 ) 2 , NR 6 COOR 5 , C (O) N (R 6 ) 2 , NR 6 C (O) N (R 6 ) 2 , OC (O) N (R 6 ) 2 , C (O) NR 6 OR 6 , OCOR 6 , S (O) n R 5 , SO 2 N (R 6 ) 2 ,
  • radicals from the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) -alkyl, halogeno (C 1 -C 6 ) -alkyl, S (O) n - (C 1 -C 6 ) -alkyl, ( -C 6) alkoxy and halo (CrC 6) - alkoxy substituted phenyl, heteroaryl or heterocyclyl, wherein heterocyclyl carries n oxo groups,
  • R 2 is hydrogen or halogen
  • R 3 and R 4 are each independently hydrogen, (C1-C3) - alkyl, halo (Ci-C 3) alkyl, (C 2 -C 3) alkenyl, (C 2 -C 3) alkynyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) - cycloalkyl (CrC 3) alkyl, COR 8 or S (0) "R 6, R 5 represents (Ci-C 3) -alkyl, (C 2 -C 3 ) -alkenyl, (C 2 -C 3 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 8 ) -cycloalkenyl or (C 3 -C 6 ) -cycloalkyl- (C 1 -C 3 ) -alkyl.
  • R 6 is hydrogen, (C 1 -C 3 ) -alkyl, (C 2 -C 3 ) -alkenyl, (C 2 -C 3 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 8 ) -Cycloalkenyl or (C 3 -C 6 ) -cycloalkyl- (C 1 -C 3 ) -alkyl,
  • X is CH or N, n is 0, 1 or 2, s is 0, 1. 2 or 3.
  • Hydroxymethyl compound (II) can be prepared with a carboxylic acid chloride (III).
  • the hydroxymethyl compounds (I I) can be prepared by methods known per se to those skilled in the art, for example by reduction of the corresponding carboxylic acid esters.
  • Such carboxylic acid esters are, for example, from WO
  • 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.
  • Synthesis methods allow a number of protocols known from the literature, which in turn can be carried out manually or automatically.
  • the reactions can be carried out, for example, by means of IRORI technology in microreactors. Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
  • the present invention therefore also provides a method for controlling undesirable plants or regulating the growth of plants, preferably in crops, wherein one or more compounds of the invention are applied to the plants (e.g., weeds, such as mono- or dicotyledons
  • the seeds eg grains, seeds or vegetative propagules such as tubers or sprout parts with buds
  • the area on which 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.
  • some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
  • the compounds according to the invention are applied to the surface of the earth prior to germination, either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then stop their growth and finally die after three to four weeks
  • Activity against monocotyledonous and dicotyledonous weeds are crops of economically important cultures such as dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum , Solanum, Vicia, or monocotyledonous crops of the genera Allium, Pineapple, Asparagus, Avena,
  • Crops such as agricultural crops or ornamental plantings.
  • Influence of phytonutrients and harvest relief e.g. 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 special traits 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.
  • transgenic cultures is the use of the invention Compounds in economically important transgenic crops of useful and ornamental plants, eg. As 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 according to the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or
  • 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 according to the invention can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • Glufosinate see, for example, EP-A-0242236, EP-A-242246) or glyphosate
  • transgenic crops for example cotton, with the ability
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins (Bt toxins) to produce, which the
  • transgenic crops characterized by a combination z. B. the o. G.
  • Numerous molecular biological techniques with which new transgenic plants with altered properties can be produced are known in principle, see, for example, BI Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, "Trends in Plant Science” 1 (1996) 423-431).
  • nucleic acid molecules can be used in any genetic manipulations.
  • nucleic acid molecules can be used in any genetic manipulations.
  • Plasmids are introduced which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, 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.
  • 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
  • Cosuppressions canes or the expression of at least one corresponding 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.
  • DNA sequences are known in the art (see, for example, Braun et al., EMBO J. 1 1 (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).
  • Expression of the nucleic acid molecules can also be found in the
  • transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants. Thus, transgenic plants are available, the altered properties by
  • the compounds of the invention can be used in transgenic cultures which are resistant to growth factors, such as. B. Dicamba or against
  • Herbicides containing essential plant enzymes e.g. Acetylactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD) inhibit, respectively against herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazole and analogous agents.
  • ALS Acetylactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydroxyphenylpyruvate dioxygenases
  • Harmful plants often have effects that are specific for application in the particular transgenic culture, such as altered or specially extended weed spectrum that can be controlled
  • 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 of the invention may be in the form of wettable powders
  • 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. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates,
  • EC emulsifiable concentrates
  • EW emulsions
  • 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),
  • the necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are, for example
  • Injectable powders are preparations which are uniformly dispersible in water and contain surfactants of the ionic and / or nonionic type (wetting agent, dispersing agent) in addition to the active ingredient, apart from a diluent or inert substance.
  • surfactants of the ionic and / or nonionic type (wetting agent, dispersing agent) in addition to the active ingredient, apart from a diluent or inert substance.
  • the herbicidal active compounds for example, in conventional apparatus such as hammer mills, blower mills and Air-jet mills finely ground and at the same time or subsequently with the
  • Formulation aids mixed.
  • Emulsifiable concentrates are made by dissolving the active ingredient in one
  • organic solvents 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).
  • emulsifiers which may be used are: 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.
  • 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 using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. upstairs with the others
  • Emulsions e.g. Oil-in-water emulsions (EW) can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as described e.g. listed above for the other formulation types.
  • Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • 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 .-%.
  • Dust-like formulations contain 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. In the water
  • the content of active ingredient is for example between 1 and 95 wt .-%, preferably between 10 and 80 wt .-%.
  • the active substance formulations mentioned optionally contain the customary adhesive, wetting, dispersing, emulsifying, penetrating, preserving, Antifreeze and solvents, fillers, carriers and dyes, defoamers,
  • Mixture formulations or in the tank mix are, for example, known active substances 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, e.g. from 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.
  • 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. Dusty preparations, ground or spreading granules and sprayable
  • 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.
  • 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 comminuted in a hammer mill.
  • a readily dispersible, water-wettable powder is obtained by: 25 parts by weight of a compound of the formula (I) and / or salts thereof, 64
  • a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3 parts by weight
  • Isotridecanol polyglycol ether (8 EO) and 71 parts by weight paraffinic Mineral oil (boiling range, for example, about 255 to about 277 C) mixed and ground in a ball mill to a fineness of less than 5 microns.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a
  • a water-dispersible granules are obtained by
  • a water-dispersible granule is also obtained by
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
  • test plants Greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
  • the compounds Nos. 1, 2, 5, 6, 22 and 24 at an application rate of 320 g / ha each have an at least 80% action against Amaranthus retroflexus.
  • Compounds Nos. 27, 49 and 58 each show an at least 80% Veronica persica at an application rate of 320 g / ha.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
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  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des 4-amino-6-acyloxyméthylpyrimidines et des 4-amino-2-acyloxyméthylpyridines de formule générale (I) utilisées comme herbicides. Dans la formule (I), R1 à R4 représentent des restes tels que l'hydrogène, des restes organiques tels que des alkyles, ainsi que d'autre restes tels que des restes halogène, nitro, cyano et formyle, et A représente un reste aryle substitué.
PCT/EP2013/075307 2012-12-06 2013-12-03 4-amino-6-acyloxyméthylpyrimidines et 4-amino-2-acyloxyméthyl­pyridines à action herbicide WO2014086738A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12195935 2012-12-06
EP12195935.7 2012-12-06

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WO2014086738A1 true WO2014086738A1 (fr) 2014-06-12

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0222254A2 (fr) * 1985-11-09 1987-05-20 Bayer Ag Dérivés d'acide nicotinique
WO1995019358A1 (fr) * 1994-01-12 1995-07-20 Sandoz Ltd. Pyrimidines herbicides d'aryle et d'heteroaryle
WO2005063721A1 (fr) * 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Pyrimidines herbicides
WO2009081112A2 (fr) * 2007-12-24 2009-07-02 Syngenta Limited Composés chimiques

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0222254A2 (fr) * 1985-11-09 1987-05-20 Bayer Ag Dérivés d'acide nicotinique
WO1995019358A1 (fr) * 1994-01-12 1995-07-20 Sandoz Ltd. Pyrimidines herbicides d'aryle et d'heteroaryle
WO2005063721A1 (fr) * 2003-12-19 2005-07-14 E.I. Dupont De Nemours And Company Pyrimidines herbicides
WO2009081112A2 (fr) * 2007-12-24 2009-07-02 Syngenta Limited Composés chimiques

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
TERAUCHI H ET AL: "NICOTINAMIDE DERIVATIVES AS A NEW CLASS OF GASTRIC (H+/K+)-ATPASE INHIBITORS. II. SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONSHIPS OF 2-Ä(2,4-DIMETHOXYBENZYL)SULFINYLÜ-N-(4-PYRIDINYL)PYRIDINE-3-CARBOXAMIDES", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, JP, vol. 45, no. 6, 1 June 1997 (1997-06-01), pages 1027 - 1038, XP001246819, ISSN: 0009-2363 *

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