WO2011134867A1 - Azolopyrimidines herbicides - Google Patents

Azolopyrimidines herbicides Download PDF

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Publication number
WO2011134867A1
WO2011134867A1 PCT/EP2011/056339 EP2011056339W WO2011134867A1 WO 2011134867 A1 WO2011134867 A1 WO 2011134867A1 EP 2011056339 W EP2011056339 W EP 2011056339W WO 2011134867 A1 WO2011134867 A1 WO 2011134867A1
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formula
methyl
azolopyrimidines
plants
alkyl
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PCT/EP2011/056339
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English (en)
Inventor
Matthias Witschel
Ricarda Niggeweg
Liliana Parra Rapado
Hans Wolfgang Höffken
Thomas Mietzner
Robert Reinhard
Klaus Kreuz
Klaus Grossmann
Franz Röhl
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to azolopyrimidines of the general formula I defined below and to their use as herbicides. Moreover, the invention relates to compositions for crop protection and to a method for controlling unwanted vegetation.
  • azolopyrimidines which have high herbicidal activity, in particular even at low application rates, and which are sufficiently compatible with crop plants for commercial utilization.
  • the present invention provides azolopyrimidines of formula I
  • R 1 is CH 3 , F, CI or Br
  • R 2 is hydrogen or C1-C4 alkyl
  • R 3 is phenyl or thienyl
  • phenyl or thienyl ring is unsubstituted or substituted with halogen, cyano, nitro, Ci-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4- haloalkyl, Ci-C4-alkoxy or Ci-C4-alkylthio;
  • R 4 is hydrogen or Ci-C4-alkyl
  • X is nitrogen or CR 5 ,
  • R 5 is hydrogen, cyano, C1-C4 alkyl, hydroxycarbonyl, C1-C6- alkoxycarbonyl, C2-C6-alkenyloxycarbonyl, C2-C6- alkynyloxycarbonyl, benzyloxycarbonyl, halobenzyloxy- carbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl, di(Ci-C6)-alkylaminocarbonyl, C2-C6-alkenylamino- carbonyl, C2-C6-alkynylaminocarbonyl,
  • the present invention also provides the use of azolopyrimidines of the general formula I as herbicides, i.e. for controlling harmful plants.
  • the present invention also provides compositions comprising at least one
  • the present invention furthermore provides a method for controlling unwanted vegetation where a herbicidal effective amount of at least one azolopyrimidines of the formula I is allowed to act on plants, their seeds and/or their habitat.
  • Application can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
  • the azolopyrimidines of formula I as described herein are capable of forming geometrical isomers, for example E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention. If the azolopyrimidines of formula I as described herein have one or more centers of chirality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the compositions according to the invention. If the azolopyrimidines of formula I as described herein have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
  • Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4- alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammo- nium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2- hydroxyeth
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hy- drogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
  • the organic moieties mentioned in the definition of the variables R 1 to R 5 are - like the term halogen - collective terms for individual enumerations of the individual group members.
  • the term halogen denotes in each case fluorine, chlorine, bromine or iodine. All hydrocarbon chains, i.e. all alkyl, can be straight-chain or branched, the prefix C n -C m denoting in each case the possible number of carbon atoms in the group.
  • Ci-C 4 -alkyl for example CH 3 , C 2 H 5 , n-propyl, and CH(CH 3 ) 2 n-butyl, CH(CH 3 )- C 2 H 5 , CH 2 -CH(CH 3 ) 2 and C(CH 3 ) 3 ;
  • Ci-C6-alkyl Ci-C 4 -alkyl as mentioned above, and also, for example, n-pentyl, 1 - methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2- dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2- trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1
  • Ci-C 4 -haloalkyl a Ci-C 4 -alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloro- fluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2- fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoro- ethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2- trichloroethyl, pentafluorine,
  • C2-C 4 -alkynyl for example ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl,
  • Ci-C 4 -alkoxy for example methoxy, ethoxy, propoxy, 1-methylethoxy butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;
  • Ci-C4-alkylthio for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1 ,1— dimethylethylthio;
  • Ci-C6-alkylamino and the Ci-C6-alkylamino moieties of Ci-C6-alkylamino- carbonyl for example methylamino, ethylamino, propylamino, 1 -methylethylamino, bu- tylamino, 1 -methylpropylamino, 2-methylpropylamino, 1 ,1 -dimethylethylamino, pen- tylamino, 1 -methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethyl- propylamino, 1 -ethylpropylamino, hexylamino, 1 ,1-dimethylpropylamino, 1 ,2-dimethyl- propylamino, 1 -methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-me- thylpentylamino
  • di(Ci-C4-alkyl)amino and the di(Ci-C4-alky)lamino moieties of di(Ci-C4-alkyl)- aminocarbonyl: for example N,N-dimethylamino, ⁇ , ⁇ -diethylamino, N,N-dipropylamino, N,N-di(1 -methylethyl)amino, ⁇ , ⁇ -dibutylamino, N,N-di(1 -methylpropyl)amino, N,N-di(2- methylpropyl)amino, N,N-di(1 ,1 -dimethylethyl)amino, N-ethyl-N-methylamino, N-me- thyl-N-propylamino, N-methyl-N-(1 -methylethyl)amino, N-butyl-N-methylamino, N-me-
  • R 1 is CHs or CI
  • R 3 is phenyl, which is unsubstituted or substituted with halogen
  • phenyl which is unsubstituted or substituted with one to three halogen atoms
  • R 4 is hydrogen
  • R 5 is cyano
  • X is preferably nitrogen
  • CR 5 is also preferably CR 5 .
  • azolopyrimidines of formula I according to the invention can be prepared by standard processes of organic chemistry, for example by the following process:
  • the azolopyrimidines of formula I wherein R 1 is halogen can be prepared by substitution of the respective hydroxy groups in the hydroxyazolopyrimidine III by halogen and subsequent replacing in the resulting dihaloazolopyrimidine II one halogen with an hydrox rou :
  • L 1 R 1 is an halogenating agent like SOC , POCI 3 , PCI 5 , POBr 3 , PBr 5 , SOBr 2 .
  • MOH is an alkali metal and/or alkaline earth metal hydroxide such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide.
  • substitution of hydroxyazolopyrimidine III is usually carried out at from 0°C to the boiling point of the reaction mixture, preferably at from 10°C to 150°C, particularly preferably at from 50°C to 100°C, in an inert organic solvent.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons such as tolene, o-, m- and p- xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chlo- roform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.
  • -butyl methylether dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert- butyl methyl ketone, as well as dimethylsulfoxide, dimethylformamide and N,N- dimethylacetamide or N-methylpyrrolidone.
  • toluene It is also possible to use mixtures of the solvents mentioned. It is also possible to use a phase-transfer catalyst like triethylaminhydrochloride.
  • the substitution of the dihaloazolopyrimidine II is usually carried out at from 0°C to the boiling point of the reaction mixture, preferably at from 10°C to 150°C, particularly pref- erably at from 50°C to 100°C, in an inert organic solvent
  • Suitable solvents are dimethylsulfoxide, dimethylformamide and N,N-dimethylacet- amide or N.methylpyrrolidone, alcohols like methanol, ethanol, isopropanol and water. Particular preference is given to water. It is also possible to use mixtures of the sol- vents mentioned.
  • reaction mixtures are worked up in a customary manner, for example by mixing with water, separation of the phases and, if appropriate, chromatographic purification of the crude product.
  • Some of the intermediates and end products are obtained in the form of viscous oils, which can be purified or freed from volatile components under reduced pressure and at moderately elevated temperature.
  • purification can also be carried out by recrystallisation or digestion.
  • azolopyrimidines of formula I wherein R 1 is CH3 or alkyl can be prepared by cycli- sation of a acylacetate V with an aminoazol IV:
  • L 2 stands for Ci-C6-alkyl.
  • the reaction of the acylacetate V with the aminoazol IV is usually carried out at from 0°C to the boiling point of the reaction mixture, preferably at from 0°C to 150°C, particularly preferably at from 50°C to 100°C, in an inert organic solvent in the presence of a base (e.g. T. Russ, Synthesis, 1990, 8, 721 -723).
  • a base e.g. T. Russ, Synthesis, 1990, 8, 721 -723.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons such as tolene, o-, m- and p- xylene, halogenated hydrocarbons such asdichloromethane, 1 ,2-dichloroethane, chlo- roform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.
  • aromatic hydrocarbons such as tolene, o-, m- and p- xylene
  • halogenated hydrocarbons such asdichloromethane, 1 ,2-dichloroethane, chlo- roform and chlorobenzene
  • ethers such as diethyl ether, diisopropyl ether, tert.
  • -butyl methylether dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert- butyl methyl ketone, alkoholes such as methanol, ethanol, n-propanol, isopropanol, n- butanol and tert.-butanol, as well as dimethylsulfoxide, dimethylformamide and N,N- dimethylacetamide or N-methylpyrrolidone. Particular preference is given to alcohols like methanol or ethanol. It is also possible to use mixtures of the solvents mentioned.
  • hydroxyazolopyrimidines II required for the preparation of the azolopyrimidines I are known from the literature (e.g. T. Russ, Synthesis, 1990, 8, 721 -723) and can be prepared by cyclisation of a malonate VI with an aminoazol IV:
  • L 2 stands for Ci-C6-alkyl.
  • the reaction of the malonate VI with the aminoazol IV is usually carried out at from 0°C to the boiling point of the reaction mixture, preferably at from 0°C to 150°C, particularly preferably at from 50°C to 100°C, in an inert organic solvent in the presence of a base (e.g. T. Russ, Synthesis, 1990, 8, 721 -723).
  • a base e.g. T. Russ, Synthesis, 1990, 8, 721 -723.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons such as tolene, o-, m- and p- xylene, halogenated hydrocarbons such asdichloromethane, 1 ,2-dichloroethane, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes
  • aromatic hydrocarbons such as tolene, o-, m- and p- xylene
  • halogenated hydrocarbons such asdichloromethane, 1 ,2-dichloroethane, chloroform and chlorobenzene
  • ethers such as diethyl
  • -butyl methylether dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert- butyl methyl ketone, alkoholes such as methanol, ethanol, n-propanol, isopropanol, n- butanol and tert.-butanol, as well as dimethylsulfoxide, dimethylformamide and N,N- dimethylacetamide or N-methylpyrrolidone. Particular preference is given to alkohols like methanol or ethanol. It is also possible to use mixtures of the solvents mentioned. Work up can be carried out in a known manner.
  • the malonates VI required for the preparation of the hydroxyazolopyrimidines III are known from the literature and can be prepared by the alkylation of an alkylmalonate VII with a bromide VIII:
  • the reaction of the alkylmalonate VII with the bromide VIII is usually carried out at from -80°C to the boiling point of the reaction mixture, preferably at from 0°C to 100°C, particularly preferably at from 0°C to 50°C, in an inert organic solvent in the presence of a base (e.g. T. Eisenaecher, Pharmazie, 1992, 47, 8, 580-581 ).
  • a base e.g. T. Eisenaecher, Pharmazie, 1992, 47, 8, 580-581 .
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons such as tolene, o-, m- and p- xylene, halogenated hydrocarbons such as dichloromethane, 1 ,2-dichloroethane, chlo- roform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.
  • -butyl methylether dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert- butyl methyl ketone, as well as dimethylsulfoxide, dimethylformamide and N,N- dimethylacetamide or N-methylpyrrolidone.
  • tetrahydro- furane It is also possible to use mixtures of the solvents mentioned.
  • Suitable bases are, in general Inorganic compounds such as alkali metal and alkaline earth metal oxide such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate, as well as alkali metal bicarbonates such as sodium bicarbonate, metal organic compounds, preferably alkali metal alkyls such as methyl lithium, butyl lithium and phenyl lithium, alkyl magnesium halides such as methyl magnesium chloride as well as and furthermore organic bases, such as tertiary amines such as trimethylamine, triethyl- amine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine, N-methylmorpholine and 4-dimethylaminopyridine and also bicyclic
  • the bases are generally employed in catalytic amounts, however they can also be em- ployed in equimolar amounts, in excess or, if appropriate, be used as solvent.
  • aminoazoles IV required for the preparation of the hydroxyazolopyrimidines III are known from the literature and can be prepared in accordance with the literature cited and/or are commercially available.
  • alkylmalonates VII and the broimdes VIII required for the preparation of the malo- nates VI are known from the literature and can be prepared in accordance with the literature cited and/or are commercially available.
  • the azolopyrimidines I are suitable as herbicides. They are suitable as such or as an appropriately formulated composition (herbicidal composition). As used in this application, the terms "formulated composition” and “herbicidal composition” are synonyms.
  • the herbicidal compositions comprising the azolopyrimidines of formula I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
  • the triazolopyrimodines of formula I or compositions comprising them can additionally be employed in a further number of crop plants for eliminating undesirable plants.
  • suitable crops are the following:
  • Preferred crops are the following: Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max,
  • Gossypium hirsutum (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
  • the azolopyrimidines of formula I according to the invention can also be used in genetically modified plants.
  • genetically modified plants is to be understood as plants, which genetic material has been modified by the use of recombinant DNA techniques in a way that under natural circumstances it cannot readily be obtained by cross breeding, mutations or natural recombination.
  • one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.
  • Such genetic modifications also include but are not limited to targeted post-transtional modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moie- ties or PEG moieties.
  • auxin herbicides such as dic
  • plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or AC- Case inhibitors.
  • herbicide resistance technologies are, for example, described in Pest Management Science 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of Agricultural Research 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein.
  • mutagenesis e. g. Clearfield ® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g.
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as a- endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp.
  • VIP vegetative insecticidal proteins
  • toxins produced by animals such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins
  • toxins produced by fungi such Streptomy- cetes toxins, plant lectins, such as pea or barley lectins; agglutinins
  • proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors
  • ribosome-inactivating proteins (RIP) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin
  • steroid metabolism enzymes such as 3-hydroxy-steroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase
  • ion channel blockers such as blockers of
  • these insecticidal proteins or toxins are to be under-stood ex- pressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ).
  • Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are dis-closed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073.
  • the methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.
  • These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of athropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda).
  • Genetically modified plants capable to synthesize one or more insecticidal proteins are, e.
  • WO 03/018810 MON 863 from Monsanto Europe S.A., Belgium (corn cultivars produ-cing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn culti- vars producing the Cry1 F toxin and PAT enzyme).
  • plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to in-crease the resistance or tolerance of those plants to bacterial, viral or fungal pathogens.
  • proteins are the so-called "pathogenesis-related proteins" (PR proteins, see, e.g. EP-A 392 225), plant disease resistance genes (e. g. potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solarium bulbocastanum) or T4-lyso-zym (e.g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora).
  • PR proteins pathogenesis-related proteins
  • plant disease resistance genes e. g. potato culti-vars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solarium bulbocastanum
  • T4-lyso-zym
  • plants are also covered that are by the use of recombinant DNA tech- niques capable to synthesize one or more proteins to increase the productivity (e.g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environ-mental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health- promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ® rape, DOW Agro Sciences, Canada).
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e.g. potatoes that produce increased amounts of amylopectin (e.g. Amflora ® potato, BASF SE, Germany).
  • a modified amount of substances of content or new substances of content specifically to improve raw material production, e.g. potatoes that produce increased amounts of amylopectin (e.g. Amflora ® potato, BASF SE, Germany).
  • the azolopyrimidines I or the herbicidal compositions comprising the azolopyrimidines I, can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, spreading, watering or treatment of the seed or mixing with the seed.
  • the use forms depend on the intended purpose; in any case, they should ensure the finest possible distribution of the active ingredients according to the invention.
  • the herbicidal compositions comprise an herbicidal effective amount of at least one azolopyrimidine of the formula I and auxiliaries which are customary for the formulation of crop protection agents.
  • auxiliaries customary for the formulation of crop protection agents are inert auxiliaries, solid carriers, surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, optionally colorants and, for seed formulations, adhesives.
  • surfactants such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers
  • organic and inorganic thickeners such as bactericides, antifreeze agents, antifoams, optionally colorants and, for seed formulations, adhesives.
  • thickeners i.e. compounds which impart to the formulation modified flow properties, i.e. high viscosity in the state of rest and low viscosity in motion
  • thickeners are polysaccharides, such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet minerals, such as Attaclay® (from Engelhardt).
  • antifoams examples include silicone emulsions (such as, for example, Silikon ® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
  • Bactericides can be added for stabilizing the aqueous herbicidal formulations.
  • bactericides are bactericides based on diclorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).
  • antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.
  • colorants are both sparingly water-soluble pigments and water-soluble dyes. Examples which may be mentioned are the dyes known under the names Rhodamin B, C.I. Pigment Red 1 12 and C.I. Solvent Red 1 , and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 1 12, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.
  • Suitable inert auxiliaries are, for example, the following: mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons for example paraffin, tetrahydronaphthalene, alkylated naphthal
  • Suitable carriers include liquid and solid carriers.
  • Liquid carriers include e.g. non- aqeuos solvents such as cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. amines such as N- methylpyrrolidone, and water as well as mixtures thereof.
  • Solid carriers include e.g.
  • mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.
  • mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and
  • Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids (e.g.
  • Powders, materials for broadcasting and dusts can be prepared by mixing or concomitant grinding the active ingredients together with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the ... of the formula I can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier.
  • a wetting agent tackifier, dispersant or emulsifier.
  • concentrates comprising active compound, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.
  • concentrations of the azolopyrimidines of the formula I in the ready-to-use preparations (formulations) can be varied within wide ranges. In general, the concentrations of the azolopyrimidines of the formula I in the ready-to-use preparations (formulations) can be varied within wide ranges. In general, the concentrations of the azolopyrimidines of the formula I in the ready-to-use preparations (formulations) can be varied within wide ranges. In general, the concentrations of the azolopyrimidines of the formula I in the ready-to-use preparations (formulations) can be varied within wide ranges. In general, the concentrations of the azolopyrimidines of the formula I in the ready-to-use preparations (formulations) can be varied within wide ranges. In general, the concentrations of the azolopyrimidines of the formula I in the ready-to-use preparations (formulations) can be varied within wide ranges. In general, the concentrations of the azolopy
  • formulations comprise approximately from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active ingredient.
  • the active ingredients are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • the active ingredients e.g. the azolopyrimidines of formula I
  • the active ingredients are present in sus- pended, emulsified or dissolved form.
  • the formulation according to the invention can be in the form of aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, aqueous emulsions, aqueous mi- croemulsions, aqueous suspo-emulsions, oil dispersions, pastes, dusts, materials for spreading or granules.
  • the azolopyrimidines of formula I according to the present invention can, for example, be formulated as follows: 1 . Products for dilution with water
  • active compound 10 parts by weight of active compound are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other adjuvants are added. The active compound dissolves upon dilution with water. This gives a formulation with an active compound content of 10% by weight.
  • active compound 20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion.
  • a dispersant for example polyvinylpyrrolidone.
  • the active compound content is 20% by weight.
  • dodecylbenzenesulfonate and castor oil ethoxylate in each case 5 parts by weight. Dilution with water gives an emulsion.
  • the formulation has an active compound content of 15% by weight.
  • dodecylbenzenesulfonate and castor oil ethoxylate in each case 5 parts by weight.
  • This mixture is introduced into 30 parts by weight of water by means of an emulsifier (Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion.
  • the formulation has an active compound content of 25% by weight.
  • active compound 20 parts by weight of active compound are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound.
  • the active compound content in the formulation is 20% by weight.
  • active compound 50 parts by weight of active compound are ground finely with addition of 50 parts by weight of dispersants and wetters and made into water-dispersible or water- soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound.
  • the formulation has an active compound content of 50% by weight.
  • active compound 75 parts by weight of active compound are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound.
  • the active compound content of the formulation is 75% by weight.
  • Granules (GR, FG, GG, MG)
  • active compound 0.5 parts by weight are ground finely and associated with 99.5 parts by weight of carriers. Current methods here are extrusion, spray- drying or the fluidized bed. This gives granules to be applied undiluted with an active compound content of 0.5% by weight.
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the azolopyrimidines of the formula I or the herbicidal compositions comprising them can be applied pre-, post-emergence or pre-plant, or together with the seed of a crop plant. It is also possible to apply the herbicidal composition or active compounds by applying seed, pretreated with the herbicidal compositions or active compounds, of a crop plant. If the active ingredients are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active ingredients reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
  • the azolopyrimidines of the formula I or the herbicidal compositions can be applied by treating seed.
  • the treatment of seeds comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the azolopyrimidines of the formula I according to the invention or the compositions prepared therefrom.
  • the herbicidal compositions can be applied diluted or undiluted.
  • seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms.
  • seed describes corns and seeds.
  • the seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
  • the rates of application of the active azolopyrimidines of formula I according to the present invention are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.
  • the application rates of the azolopyrimidines of formula I are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha of active sub- stance (a.s.).
  • azolopyrimidines of formula I is 0.1 to 1000 g/ha, preferablyl to 750 g/ha, more preferably 5 to 500 g/ha, of active substance.
  • the azolopyrimidines of formula I are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
  • azolopyrimidines of the formula I may be mixed with a large number of representatives of other herbicidal or growth-regulating active ingredient groups and then applied concomitantly.
  • Suitable components for mixtures are, for example, 1 ,2,4-thiadiazoles, 1 ,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, (het)aryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1 ,3-cyclohexanediones, 2-hetaroyl-1 ,3-cyclo- hexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetani- lides, cyclohexenone oxime ether
  • azolopyrimidines of the formula I alone or in combination with other herbicides, or else in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or
  • phytopathogenic fungi or bacteria Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies.
  • mineral salt solutions which are employed for treating nutritional and trace element deficiencies.
  • Other additives such as non-phytotoxic oils and oil concentrates may also be added.
  • Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the
  • azolopyrimidines of the formula I towards unwanted plants. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or post-emergence application of the useful plant.
  • the safeners and the azolopyrimidines of the formula I can be applied simultaneously or in succession.
  • Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1 -phenyl-5-haloalkyl-1 H-1 ,2,4- triazol-3-carboxylic acids, 1 -phenyl-4,5-dihydro-5-alkyl-1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha- oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4- (aminocarbonyl)phenyl]sulfonyl]-2-benzoic amides, 1 ,8-naphthalic anhydride, 2-halo-4- (haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcar
  • R 3 is 3(5-chloro)thienyl Table 3
  • the culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate.
  • the seeds of the test plants were sown separately for each species.
  • the active ingredients which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles.
  • the containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this has been impaired by the active ingredients.
  • the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
  • the plants were kept at 10 - 25°C or 20 - 35°C.
  • the test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.
  • Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.
  • the compounds 1 .4, 1 .6, 1.7 and 1 .17 showed good herbicidal activity and compound 1 .5 showed very good herbicidal activity against Abutilon theophrasti.
  • the compounds 1 .4, 1 .5, 1.8 and 1 .16 applied by the post-emergence method showed good herbicidal activity against Alopercurus myosuroides.
  • the compound 1 .8 applied by the post-emergence method showed good herbicidal activity against Avena fatua.
  • the compounds 1 .4, 1 .5, 1 .6, 1.7, 1.8, 1.16 andl .17 applied by the post-emergence method showed good herbicidal activity against Se- taria faberi.

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Abstract

La présente invention concerne des azolopyrimidines de formule (I) où les variables sont telles que définies dans la description, les compositions les incluant et leur emploi comme herbicides, c'est-à-dire dans la maîtrise de végétaux nocifs, ainsi qu'une méthode de maîtrise d'une végétation non désirée qui comprend le fait de laisser une quantité herbicide active d'au moins une azolopyrimidine de formule (I) agir sur des végétaux, leurs graines et/ou leur habitat.
PCT/EP2011/056339 2010-04-26 2011-04-20 Azolopyrimidines herbicides WO2011134867A1 (fr)

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US20130252951A1 (en) * 2010-09-27 2013-09-26 Proximagen Limited 7-hydroxy-pyrazolo[1,5-a] pyrimidine compounds and their use as ccr2 receptor antagonists
WO2016018773A1 (fr) * 2014-08-01 2016-02-04 Merck Sharp & Dohme Corp. Composés antagonistes de ccr9
WO2018071282A1 (fr) * 2016-10-12 2018-04-19 Merck Sharp & Dohme Corp. Inhibiteurs de kdm5
WO2018071283A1 (fr) * 2016-10-12 2018-04-19 Merck Sharp & Dohme Corp. Inhibiteurs de kdm5
CN108586464A (zh) * 2018-04-12 2018-09-28 苏州康润医药有限公司 一种3-溴吡唑并[1,5-α]嘧啶-6-甲酸的合成方法

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KR20150130491A (ko) * 2013-03-13 2015-11-23 제넨테크, 인크. 피라졸로 화합물 및 그것의 용도

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130252951A1 (en) * 2010-09-27 2013-09-26 Proximagen Limited 7-hydroxy-pyrazolo[1,5-a] pyrimidine compounds and their use as ccr2 receptor antagonists
JP2013538838A (ja) * 2010-09-27 2013-10-17 プロクシマゲン リミテッド ７−ヒドロキシ−ピラゾロ［１，５−ａ］ピリミジン化合物およびｃｃｒ２レセプターアンタゴニストとしてのその使用
WO2016018773A1 (fr) * 2014-08-01 2016-02-04 Merck Sharp & Dohme Corp. Composés antagonistes de ccr9
WO2018071282A1 (fr) * 2016-10-12 2018-04-19 Merck Sharp & Dohme Corp. Inhibiteurs de kdm5
WO2018071283A1 (fr) * 2016-10-12 2018-04-19 Merck Sharp & Dohme Corp. Inhibiteurs de kdm5
US10975084B2 (en) 2016-10-12 2021-04-13 Merck Sharp & Dohme Corp. KDM5 inhibitors
CN108586464A (zh) * 2018-04-12 2018-09-28 苏州康润医药有限公司 一种3-溴吡唑并[1,5-α]嘧啶-6-甲酸的合成方法

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