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EP1633728A1 - Pyrimidines substituees en position 2 - Google Patents

Pyrimidines substituees en position 2

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Publication number
EP1633728A1
EP1633728A1 EP04731893A EP04731893A EP1633728A1 EP 1633728 A1 EP1633728 A1 EP 1633728A1 EP 04731893 A EP04731893 A EP 04731893A EP 04731893 A EP04731893 A EP 04731893A EP 1633728 A1 EP1633728 A1 EP 1633728A1
Authority
EP
European Patent Office
Prior art keywords
formula
compound
compounds
corresponds
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04731893A
Other languages
German (de)
English (en)
Inventor
Jordi Tormo I Blasco
Carsten Blettner
Bernd Müller
Markus Gewehr
Wassilios Grammenos
Thomas Grote
Andreas Gypser
Joachim Rheinheimer
Peter Schäfer
Frank Schieweck
Anja Schwögler
Oliver Wagner
Siegfried Strathmann
Ulrich Schöfl
Maria Scherer
Reinhard Stierl
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1633728A1 publication Critical patent/EP1633728A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the invention relates to 2-substituted pyrimidines of the formula I,
  • n is an integer from 1 to 5, where at least one substituent L is located in the ortho position on the phenyl ring;
  • A, A ⁇ A "independently of one another hydrogen, dC 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkenyl, phenyl, where the organic radicals can be partially or completely halogenated or can be substituted by cyano or dC 4 -alkoxy; or A and A 'together with the atoms to which they are bonded for a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one to four heteroatoms from the group O, N or S;
  • R, R 2 independently of one another dC 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, CpCe haloalkyl, C 3 -C 6 halocycloalkyl, C 2 - C 6 -
  • R 2 can additionally signify hydrogen
  • R s halogen, cyano, CC 4 alkyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, dC 4 alkoxy, C 3 -C 4 alkenyloxy or C 3 -C alkynyloxy, where the alkyl , Alkenyl and alkynyl radicals of R 3 can be substituted by halogen, cyano, nitro, dC 2 alkoxy or dC 4 alkoxycarbonyl;
  • x represents 0 or 1
  • R a , R and R c independently of one another are hydrogen, d-Ce-alkyl, C 2 -C 3 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl, C 4 -C 6 -cycloalkenyl;
  • Z represents oxygen or NR c ;
  • YC represents (H) -R e , CR e , NN (H) -R C or NR c ;
  • iiii can mean a double or single bond
  • R d , R e have the same meanings as R c and can additionally mean halogen or cyano;
  • R d together with the carbon to which it is attached can represent a carbonyl group
  • R is halogen, cyano, d-Cs-alkyl, C 2 -C ⁇ 0 alkenyl, C 2 -C 10 alkynyl, dC 6 - alkoxy, C ⁇ -do-alkenyloxy, C 2 -C 10 alkynyloxy, C 3 - C 6 -Cycloalkyl, C 3 -C 6 cycloalkenyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 cycloalkenyloxy, and wherein two of the radicals R a , R b or R c together with the atoms to which they are attached are a five- or six-membered saturated, partially unsaturated or aromatic heterocycle containing one to four heteroatoms from the group O, N or S, can form.
  • the invention also relates to a process for the preparation of these compounds, compositions containing them and their use in combating phytopathogenic harmful fungi.
  • WO-A 01/96314 discloses fungicidal pyrimidines which carry a cyanamino substituent in the 2-position. Furthermore, WO 02/74753 discloses fungicidal pyrimidines which generally carry a hetrocyclyl radical in the 2-position. However, only heteroaryl-substituted pyrimidines are specifically disclosed.
  • the compounds 1 can be obtained in various ways. i
  • the hydrazine compound II is condensed with a dicarbonyl compound III, where the substituents R 1 , R 2 , R 3 , L n , R d and R e have the meaning given above and R 'is an alkyl, aryl or benzyl group (see Scheme 1) and thus the compounds of formula VI.
  • the dicarbonyl compounds of formula III are from Angew. Chem. Int. Ed. Concentrated. 1989 28, p. 500 known.
  • the condensation takes place as detailed in DE 19627002.
  • the ring closure to the compounds IA according to the invention takes place, for example, in the presence of bases such as, in particular, alkali metal alkoxylates.
  • the starting point for the synthesis of the compounds IC and IC is preferably the hydrazine compound II, the preparation of which has already been described in detail above.
  • the reaction with chloroformic acid ester (R "stands for an alkyl radical) to the acylated compounds V generally takes place in the presence of a base.
  • the further reaction of V with phosgene or a phosgene equivalent to VI and the subsequent ring closure in the presence of an amine / hydrazine and one Base can be carried out analogously to the method described in Chem. Ber. 1898, 31, page 2320 ff.
  • the ring closure in the presence of amines R C NH 2 leads to triazolidinediones IC while the ring closure in the presence of hydrazines R C NH-NH 2 leads to the compounds IC "leads.
  • Triazolidinones of type ID can advantageously be constructed as shown in Scheme 3.
  • the condensed compound VII is obtained analogously to that in J.Am.Chem.Soc. 1995, 77, p.1148 described method. VII is continued with chloroformic acid ester to VIII analogous to that in Compt. Rend. Acad. Be. 1981, 293, N8, 573-76 method described.
  • R "in the ortho ester and chloroformic acid ester means dC 6 -alkyl.
  • the ring closure to the compounds ID according to the invention takes place in the presence of amines R ° NH 2. If hydrazines of the formula R C NH-NH 2 are used instead of amines, triazolidinones are used Formula ID "received.
  • the radical R 3 (in particular alkyl) in the 6-position on the pyrimidine ring can be introduced by reaction with transition metal catalysis, such as Ni or Pd catalysis. In some cases it can be puzzling to reverse the order and introduce the substituent R 3 before the substituent NR 1 R 2 .
  • w X w -M y M stands for a metal ion of valence Y, such as B, Zn, Mg, Cu or Sn, X stands for chlorine, bromine, iodine or hydroxy, R 3 preferably means C-rd-alkyl and w stands for a number from 0 to 3.
  • This reaction can be carried out, for example, analogously to the following methods: J. Chem. Soc. Perkin Trans. 1, 1187 (1994), ibid. 1, 2345 (1996); WO-A 99/41255; Aust. J. Chem., Vol. 43, 733 (1990); J Org. Chem., Vol. 43, 358 (1978); J. Chem. Soc. Chem. Commun. 866 (1979); Tetrahedron Lett., Vol. 34, 8267 (1993); ibid., vol. 33, 413 (1992).
  • R 3 represents an alkyl group. If R 3 is a cyano group or an alkoxy substituent, the radical R 3 can be introduced by reaction with alkali metal cyanides or alkali metal alcoholates.
  • R 3 is a cyano group or an alkoxy substituent
  • R 3 can be introduced by reaction with alkali metal cyanides or alkali metal alcoholates.
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyi saturated, straight-chain or branched hydrocarbon radicals with 1 to 4, 6, 8 or 10 carbon atoms, for example dC 6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2- Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-di ' methylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1- Ethyl butyl, 2-
  • Haloalkyl straight-chain or branched alkyl groups with 1 to 10 carbon atoms (as mentioned above), it being possible for part or all of the hydrogen atoms in these groups to be replaced by halogen atoms as mentioned above, for example CC 2 haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl , Difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl , 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethy
  • Alkenyl unsaturated, straight-chain or branched hydrocarbon residues with 2 to 4, 6, 8 or 10 carbon atoms and a double bond in any position, for example C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2- Pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-but
  • Alkadienyl unsaturated, straight-chain or branched hydrocarbon radicals with 4, 6, 8 or 10 carbon atoms and two double bonds in any position;
  • Haloalkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 10 carbon atoms and a double bond in any position (as mentioned above), the hydrogen atoms in these groups being partially or completely replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine can;
  • Alkynyl straight-chain or branched hydrocarbon groups with 2 to 4, 6, 8 or 10 carbon atoms and a triple bond in any position, for example C 2 -C 6 -alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2- Butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl 3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl,
  • Cycloalkyl mono- or bicyclic, saturated hydrocarbon groups with 3 to 6 or 8 carbon ring members, for example C 3 -C 8 cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
  • Triazolidin-2-yl 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3- Dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3- yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3- isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazoiin-5-yl, 4- isoxazoi
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom: 5-ring heteroaryl groups, which in addition to carbon atoms can contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, eg 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3- Pyrazolyl, 4-pyrazolyI, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyI, 1, 2,4-oxadiazole 3- yl, 1, 2,4-oxadia
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, for example 2-pyridinyl, 3- Pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1, 2,4-triazine 3-yl;
  • the scope of the present invention includes the (R) and (S) isomers and the racemates ( ⁇ ) of compounds of the formula I which have chiral centers.
  • R 1 is dC 6 alkyl, CC 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl and R 2 is hydrogen ,
  • R 1 represents dC 6 -alkyl or d-Ce-haloalkyl which is branched in the ⁇ -position.
  • R 1 is dC 4 -haloalkyl and R 2 is hydrogen.
  • R 1 and R 2 together with the nitrogen to which they are attached form a five- or six-membered ring which can be interrupted by an oxygen atom and can carry one or two dC 6 -alkyl substituents.
  • Groups NR R 2 such as - in particular in the ⁇ -position - methylated pyrrolidines or piperidines are particularly preferred.
  • pyrimidines I are particularly preferred, the index n and the substituents L to L 5 having the following meaning:
  • A, A ⁇ A "independently of one another are hydrogen, dC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, where the organic radicals can be partially or completely halogenated or substituted by cyano or dC -alkoxy can, or A and A 'together with the atoms to which they are attached represent a five- or six-membered saturated heterocycle containing one to four heteroatoms from the group O, N, or S.
  • pyrimidines I are preferred, the substituents L 1 to L 5 having the following meaning:
  • R u is halogen, cyano, C -> - Ce alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, dC 6 alkoxy, C 2 -C 6 - Alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkyl, C 5 -C 6 cycloalkenyl.
  • L 5 is hydrogen, fluorine, chlorine or CH 3 .
  • R 3 represents halogen, cyano, dC 4 alkyl or dd-alkoxy.
  • R 3 is methyl, ethyl, cyano, bromine or in particular chlorine.
  • R a, R b and R c are preferably independently hydrogen, CC 6 - alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl.
  • R a , R b and R c are preferably independently of one another hydrogen, methyl or ethyl.
  • R a , R b and R c are preferably independently of one another hydrogen, methyl or ethyl.
  • the same preferences apply to the intermediates of the formulas IV, V, VI and VII as to the active ingredients mentioned above.
  • the preferred substituent meanings apply individually as well as in combination with other preferences.
  • Table 12 Compounds of the formulas Ia, Ib, Ic, Id, le, If, Ig and Ih, in which L n is 2,4-difluoro, R 3 is methyl and R 1 , R 2 for a compound in each case one row of Table A corresponds to Table 13
  • R 3 is methyl and R 1 , R 2 for each compound corresponds to one row of Table A.
  • R 3 is methyl and R 1 , R 2 for each compound corresponds to one row of Table A.
  • R 3 is methyl and R 1 , R 2 for each compound corresponds to one row of Table A.
  • R 3 is chlorine and R 1 , R 2 for each compound corresponds to one row of Table A.
  • R 3 is chlorine and R 1 , R 2 for each compound corresponds to one row of Table A.
  • Table 102 Compounds of the formulas Ia, Ib, Ic, Id, le, If, Ig and Ih, in which L n is 2,4-difluoro, R 3 is bromine and R 1 , R 2 for a compound in each case one row of Table A corresponds to
  • R 3 is bromine and R 1 , R 2 for each compound corresponds to one row of Table A.
  • R 3 is bromine and R 1 , R 2 for each compound corresponds to one row of Table A.
  • R 3 is bromine and R 1 , R 2 for each compound corresponds to one row of Table A.
  • R 3 is bromine and R 1 , R 2 for each compound corresponds to one row of Table A.
  • Table 138 Compounds of the formula la, Ib, Ic, Id, le, If, Ig and Ih, in which L n is 2-fluorine, 6-methyl, R 3 is cyano and R 1 , R 2 for each compound are one line of Table A corresponds
  • Table 139 Compounds of the formula la, Ib, Ic, Id, le, If, Ig and Ih, in which L n is 2,4,6-trifluoro, R 3 is cyano and R 1 , R 2 for each compound are one line of Table A corresponds Table 140
  • Table 146 Compounds of the formula la, Ib, Ic, Id, le, If, Ig and Ih, in which L n is 2-fluorine, R 3 is cyano and R 1 , R 2 for each compound corresponds to one row of Table A.
  • Table 152 Compounds of the formula Ia, Ib, Ic, Id, Le, If, Ig and Ih, in which L n is 2,3,4-trifluoro, R 3 is cyano and R 1 , R 2 for each compound are one line of Table A corresponds
  • Table 153 Compounds of the formula la, Ib, Ic, Id, le, If, Ig and Ih, in which L n is 2-methyl, R 3 is cyano and R 1 , R 2 for each compound corresponds to one row of Table A.
  • the compounds I are suitable as fungicides. They are characterized by excellent activity against a broad spectrum of phytopathogenic fungi, in particular from the class of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. Some of them are systemically effective and can be used in plant protection as leaf and soil fungicides. They are of particular importance for combating a large number of fungi on various crops such as wheat, rye, barley, oats, rice, corn, grass, bananas, cotton, soybeans, coffee, sugar cane, wine, fruit and ornamental plants and vegetable plants such as Cucumbers, beans, tomatoes, potatoes and squash, as well as on the seeds of these plants.
  • Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and vines
  • Rhizoctonia species on cotton, rice and lawn are Rhizoctonia species on cotton, rice and lawn.
  • the compounds I are also suitable for combating harmful fungi such as Pacilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
  • harmful fungi such as Pacilomyces variotii in the protection of materials (e.g. wood, paper, dispersions for painting, fibers or fabrics) and in the protection of stored products.
  • the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally active amount of the active compounds.
  • the application can take place both before and after the infection of the materials, plants or seeds by the fungi.
  • the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90% by weight of active ingredient.
  • the application rates in crop protection are between 0.01 and 2.0 kg of active ingredient per ha.
  • amounts of active compound of 0.001 to 0.1 g, preferably 0.01 to 0.05 g, are generally required per kilogram of seed.
  • the amount of active ingredient applied depends on the type of application and the desired effect. Usual application rates in material protection are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active ingredient per cubic meter of treated material.
  • the compounds I can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the form of application depends on the respective purpose; in any case, it should ensure a fine and uniform distribution of the connection according to the invention.
  • the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants.
  • solvents and auxiliaries The following are essentially considered as solvents / auxiliaries:
  • aromatic solvents e.g. Solvesso products, xylene
  • paraffins e.g. petroleum fractions
  • alcohols e.g. methanol, buta ⁇ ol, pentanol, benzyl alcohol
  • ketones e.g. cyclohexanone, gamma-butryolactone
  • pyrrolidones NMP, NOP
  • Acetates glycoie, dimethyl fatty acid amides, fatty acids and fatty acid esters.
  • solvent mixtures can also be used
  • - Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquors and methyl cellulose.
  • Alkali, alkaline earth, ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid come as surface-active substances,
  • Alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers are used, furthermore condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of
  • mineral oil fractions from medium to high boiling points such as kerosene or diesel oil, furthermore coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strongly polar solvents, e.g. Dimethyl sulfoxide, N-methylpyrroidone or water into consideration.
  • mineral oil fractions from medium to high boiling points such as kerosene or diesel oil
  • coal tar oils as well as oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated n
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
  • Mineral earths such as silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics
  • the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum). Examples of formulations are: 1. Products for dilution in water
  • a compound according to the invention 10 parts by weight of a compound according to the invention are dissolved in water or a water-soluble solvent. Alternatively, wetting agents or other aids are added. The active ingredient dissolves when diluted in water.
  • a compound according to the invention 20 parts by weight of a compound according to the invention are dissolved in cyclohexanone with the addition of a dispersant e.g. Polyvinyl pyrrolidone dissolved. When diluted in water, a dispersion results.
  • a dispersant e.g. Polyvinyl pyrrolidone
  • a compound according to the invention 40 parts by weight of a compound according to the invention are dissolved in xylene with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (5% each).
  • This mixture is introduced into water using an emulsifying machine (Ultraturax) and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
  • a compound according to the invention 20 parts by weight of a compound according to the invention are comminuted in a stirred ball mill to form a fine active ingredient suspension with the addition of dispersing and wetting agents and water or an organic solvent. Dilution in water results in a stable suspension of the active ingredient.
  • a compound according to the invention 50 parts by weight of a compound according to the invention are finely ground with the addition of dispersing and wetting agents and by means of technical equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules manufactured. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • technical equipment for example extrusion, spray tower, fluidized bed
  • 75 parts by weight of a compound according to the invention are ground in a rotor-strator mill with the addition of dispersing and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • a compound according to the invention 0.5 part by weight is ground finely and combined with 95.5% carriers.
  • Common processes are extrusion, spray drying or fluidized bed. This gives granules for direct application.
  • the active ingredients as such in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprinkling agents, granules by spraying, atomizing, dusting, scattering or pouring.
  • the application forms depend entirely on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water the.
  • emulsions, pastes or oil dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates composed of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • the active ingredient concentrations in the ready-to-use preparations can be varied over a wide range. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
  • the active ingredients can also be used with great success in the ultra-low-volume process (ULV), it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
  • UUV ultra-low-volume process
  • Oils of various types, wetting agents, adjuvants, herbicides, fungicides, other pesticides, bactericides can be added to the active compounds, if appropriate also only immediately before use (tank mix). These agents can be added to the agents according to the invention in a weight ratio of 1:10 to 10: 1.
  • compositions according to the invention can also be present together with other active compounds which, e.g. with herbicides, insecticides, growth regulators, fungicides or also with fertilizers. Mixing the compounds I or the compositions containing them in the use form as fungicides with other fungicides results in an enlargement of the fungicidal spectrum of action in many cases.
  • Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl,
  • Amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine, tridemorph
  • Anionopyrimidines such as pyrimethanil, mepanipyrim or cyprodinyl,
  • Antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin, Azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochlorazol, trichlorozol, trichlorozol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, trichazol, tri
  • Dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propineb, Polycarbamat, Thiram, Ziram, Zineb,
  • Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadone, fenamidon, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolan, mepronil, nuar
  • copper fungicides such as Bordeaux broth, copper acetate, copper oxychloride, basic copper sulfate, • nitrophenyl derivatives, such as binapacryl, dinocap, dinobutone, nitrophthaloisopropyl
  • Phenylpyrroles such as fenpiclonil or fludioxonil
  • fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chlorothalhalil, cyflufenamide, cymoxanil, Dazomet, diclomezin, diclocymet, Diethofen-carb, edifenphos, ethaboxam, fenhexamide, fentin acetate, fenoxanil, ferim
  • strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin, • sulfenoic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid
  • Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.
  • the active ingredients were prepared separately or together as a stock solution with 0.25% by weight of active ingredient in acetone or DMSO. 1% by weight of emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) was added to this solution and diluted with water to the desired concentration.
  • emulsifier Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
  • Leaves of potted plants of the "Large Meat Tomato St. Pierre" type were sprayed with an aqueous suspension in the active ingredient concentration given below to the point of dripping wet. The following day, the leaves were infected with an aqueous spore suspension of Alternaria solani in 2% biomalt solution with a density of 0.17 x 10 6 spores / ml. The plants were then placed in a water vapor-saturated chamber at temperatures between 20 and 22 ° C. After 5 days The late blight on the untreated but infected control plants had developed so strongly that the infestation could be determined visually in%.
  • the plants treated with the active compounds according to the invention showed a significantly lower infection than the untreated plants.

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

Abstract

Pyrimidines de formule (I) dans laquelle l'indice n et les substituants L et R1 à R3 possèdent la signification figurant dans le descriptif et R4 correspond à l'une des formules (II, III), procédés ainsi que produits intermédiaires pour la préparation de ces composés, et substances contenant ces composés ainsi qu'utilisation desdites substances pour lutter contre les champignons phytopathogènes.
EP04731893A 2003-05-20 2004-05-10 Pyrimidines substituees en position 2 Withdrawn EP1633728A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10323026 2003-05-20
PCT/EP2004/004957 WO2004103978A1 (fr) 2003-05-20 2004-05-10 Pyrimidines substituees en position 2

Publications (1)

Publication Number Publication Date
EP1633728A1 true EP1633728A1 (fr) 2006-03-15

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EP04731893A Withdrawn EP1633728A1 (fr) 2003-05-20 2004-05-10 Pyrimidines substituees en position 2

Country Status (13)

Country Link
US (1) US20070054929A1 (fr)
EP (1) EP1633728A1 (fr)
JP (1) JP2007502846A (fr)
KR (1) KR20060013665A (fr)
CN (1) CN100453535C (fr)
AU (1) AU2004240717A1 (fr)
BR (1) BRPI0410482A (fr)
CA (1) CA2525762A1 (fr)
CO (1) CO5630009A2 (fr)
CR (1) CR8078A (fr)
EA (1) EA200501736A1 (fr)
MX (1) MXPA05011549A (fr)
WO (1) WO2004103978A1 (fr)

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DE102004003428A1 (de) * 2004-01-23 2005-08-11 Boehringer Ingelheim Pharma Gmbh & Co. Kg Neue langwirksame Beta-2-Agonisten, und deren Verwendung als Arzneimittel
NZ550933A (en) * 2004-05-19 2009-05-31 Basf Ag 2-substituted pyrimidines and their use as pesticides
TW200637556A (en) 2005-01-31 2006-11-01 Basf Ag Substituted 5-phenyl pyrimidines I in therapy
DE102005046592A1 (de) * 2005-09-28 2007-03-29 Basf Ag 2-Substituierte Hydroxylaminopyrimidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Pestizid
EP1987011A1 (fr) * 2006-02-15 2008-11-05 Basf Se Pyrimidines substituées en position 2 et leur utilisation comme pesticides
US20110201496A1 (en) * 2006-03-27 2011-08-18 Joachim Rheinheimer Substituted 5-Hetaryl-4-Aminopyrimidines
CL2007002231A1 (es) * 2006-08-02 2008-04-11 Basf Ag Uso de compuestos derivados de 5-(het) arilpirimidina para combatir hongos daninos; compuestos derivados de 5-(het) arilpirimidina; agente fungicida; y agente farmaceutico.

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DE3419127A1 (de) * 1984-05-23 1985-11-28 Bayer Ag, 5090 Leverkusen 1-heteroaryl-4-aryl-pyrazolin-5-one
US4663327A (en) * 1984-05-23 1987-05-05 Bayer Aktiengesellschaft 1-heteroaryl-4-aryl-pyrazolin-5-ones
CN1178792A (zh) * 1996-10-07 1998-04-15 美国氰胺公司 五氟苯基唑类并嘧啶
AU778913B2 (en) * 2000-06-13 2004-12-23 Basf Aktiengesellschaft Fungicidal 5-phenyl substituted 2-(cyanoamino) pyrimidines
WO2002074753A2 (fr) * 2001-03-15 2002-09-26 Basf Aktiengesellschaft 5-phenylpyrimidines, procede et produits intermediaires utilises pour les produire et leur utilisation pour lutter contre des champignons nuisibles
CN1312134C (zh) * 2001-11-19 2007-04-25 巴斯福股份公司 5－苯基嘧啶化合物、包含它们的组合物、其制备方法及其用途

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See references of WO2004103978A1 *

Also Published As

Publication number Publication date
MXPA05011549A (es) 2005-12-15
AU2004240717A1 (en) 2004-12-02
EA200501736A1 (ru) 2006-04-28
CN1791583A (zh) 2006-06-21
US20070054929A1 (en) 2007-03-08
BRPI0410482A (pt) 2006-06-13
JP2007502846A (ja) 2007-02-15
CA2525762A1 (fr) 2004-12-02
KR20060013665A (ko) 2006-02-13
WO2004103978A1 (fr) 2004-12-02
CN100453535C (zh) 2009-01-21
CO5630009A2 (es) 2006-04-28
CR8078A (es) 2006-07-14

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