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WO2004011467A1 - Derives de triazolopyrimidine et fongicides utilises dans l'agriculture et l'horticulture - Google Patents

Derives de triazolopyrimidine et fongicides utilises dans l'agriculture et l'horticulture Download PDF

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Publication number
WO2004011467A1
WO2004011467A1 PCT/JP2003/009615 JP0309615W WO2004011467A1 WO 2004011467 A1 WO2004011467 A1 WO 2004011467A1 JP 0309615 W JP0309615 W JP 0309615W WO 2004011467 A1 WO2004011467 A1 WO 2004011467A1
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group
compound
halogen atom
general formula
alkyl
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PCT/JP2003/009615
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Japanese (ja)
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Tatsuya Masumizu
Hidehiro Tajino
Hideyuki Murakami
Masaru Watanabe
Hitoshi Wakabayashi
Motohiro Hiramatsu
Tomomi Tahara
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Hokko Chemical Industry Co., Ltd.
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Priority to JP2005505578A priority Critical patent/JPWO2004011467A1/ja
Publication of WO2004011467A1 publication Critical patent/WO2004011467A1/fr

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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

  • Triazolopyrimidine derivative and fungicide for agricultural and horticultural use
  • the present invention relates to a novel triazolopyrimidine derivative and a fungicide for agricultural and horticultural use comprising the derivative as an active ingredient.
  • Japanese Patent Application Laid-Open No. 05-262773 describes that a triazo-opened pyrimidine represented by the following general formula has herbicidal activity.
  • R i a represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, a haloalkyl group, a haloalkoxy group, haloalkylthio group, a Shiano group
  • R 2 a represents an alkyl group, an alkoxy group, an alkylthio group
  • R 3 a represents an alkyl group, an alkoxy group, an alkylthio group, a haloalkyl group, c port alkoxy groups, haloalkylthio groups.
  • R b is an optionally substituted alkyl group, an alkenyl group, Arukini group, alkadienyl group, ⁇ Li Ichiru group, a cycloalkyl group or a consequent Roaruke two group
  • R 2 b is a hydrogen atom, halogen atom, hydroxy group, an an alkoxy group
  • R 3 b, R 4 bN R 5 b, R 6 b , and: 7 b is, its is it independently hydrogen atom, a halogen atom, an alkyl group, an alkoxy group , Represents a nitro group or a cyano group.
  • EP 2 153 382 discloses that triazolopyrimidine derivatives represented by the following general formula have bactericidal activity.
  • R 2 C and R 3 c represent a hydrogen atom, an alkyl group, an aryl group
  • A represents a nitrogen atom
  • CR 4c represents a hydrogen atom, a halogen atom, or an alkyl group.
  • R ld is a hydrogen atom, an alkyl group, an alkenyl group
  • R 2 d and R 3 d represents a hydrogen atom, a halogen atom, an alkyl group, a etc. alkenyl group
  • R 4 d is a hydrogen atom
  • R 5 d represents an alkyl group, an alkenyl group, etc.
  • A represents a nitrogen atom, CH, etc.
  • R ie represents alkyl group, alkenyl group, cycloalkyl group, and heterocyclic Shikimoto a
  • R 2e represents a hydrogen atom, an alkyl group, or, together with e and R 2 e is adjacent nitrogen atom
  • R 3e represents an aryl group
  • R 4e represents a hydrogen atom, a halogen atom, or an alkylamino group.
  • WO 01/96341 describes a method for producing a triazolopyrimidine-1 7-ylidene derivative using a triazolopyrimidine derivative represented by the following general formula as a raw material. Have been. Nevertheless, among the bets Riazoropiri thymidine derivative represented by the following general formula, derivative R 2 f is a complex ⁇ is a specific example is not disclosed.
  • R lf is a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a cycloalkyl group, phenyl group, naphthyl group, and heterocyclic Shikimoto a
  • R 3 f represents a halogen atom, an amino group, an alkoxy group, a haloalkoxy group, and alkylamino group.
  • An object of the present invention is to provide a novel compound meeting the above-mentioned demands and a fungicide for agricultural and horticultural use using the same.
  • a novel triazolopyrimidine derivative with a specific structure has a broad control spectrum and a high control effect as an agricultural and horticultural fungicide, and depending on the type of disease, has both preventive and therapeutic effects It has been found to have high disease control activity.
  • the present invention is as follows.
  • H et A denotes a 5- or 6-membered ring containing a hetero element, wherein these rings are a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, May be substituted with a C1-C6 haloalkyl group or a C2-C6 alkoxyalkyl group,
  • X A is a halogen atom, Shiano group, C 1 through C 6 alkoxy group, C l to C 6 alkylthio group, C. 1 to C 6 alkylsulfinyl group, C 1 through C 6 alkylsulfonyl group, C 1 through C 6 alkyl Represents an amino group or a C 1 -C 6 alkoxycarbonyl group, and
  • ⁇ represents the same or different, C 1 -C 10 alkyl group, C 2 -C 10 alkenyl group, C 2 -C 10 alkynyl group or phenyl group (the alkyl group, alkenyl group, alkynyl group And a phenyl group are a halogen atom, a C1-C6 alkyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkoxycarbonyl group. And may be substituted with one or more groups selected from the group consisting of carboxyl groups).
  • Het A is represented by the following general formula Hetet 5.
  • R 2 and R 3 are the same or different and represent a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkyl group, or a halogen atom
  • R 2 and R 3 are the same or different and represent a hydrogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkyl group, or a halogen atom
  • X A represents a halogen atom
  • R A and R A are the same or different from each other, are a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group or a C 2 -C 10 alkynyl group (the alkyl group, the alkenyl group and The alkynyl group may be substituted with a halogen atom, a C1-C6 alkyl group or a C1-C6 haloalkyl group)
  • the the He t A is characterized in that it is a group table in the the He t have H et 6 or H eti 2, preparative Riazoropiri midges down derivative according to (2). '
  • Het B represents a 5- or 6-membered ring containing a hetero element, which is a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkyl group or a C2.
  • a hetero element which is a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkyl group or a C2.
  • ⁇ C 6 alkoxyalkyl group may be substituted
  • X B is halogen atom, Shiano group, C 1 through C 6 alkoxy group, C l ⁇ C 6 alkylthio group, C. 1 to C 6 alkylsulfinyl group, C. 1 to C 6 alkylsulfonyl group, C 1 ⁇ C 6 Arukiruamino A C 1 -C 6 alkoxycarbonyl group; and R B is attached at the nitrogen atom, a nitrogen-containing heterocyclic ring which may be substituted.
  • Het B represents any of the groups represented by the above general formula Hetet 15 .
  • X B represents a halogen atom
  • the the He t B is characterized in that it is a group table in ⁇ the He t have H et 6 or H et 2, preparative Riazoropiri midges down derivative according to ⁇ (5).
  • H et c represents a 5- or 6-membered ring containing a hetero element, and these 5- or 6-membered rings are a halogen atom, a C1-C6 alkyl group, a C1-C.6 alkoxy group, May be substituted by a group selected from the group consisting of C1 to G6 haloalkyl groups and C2 to C6 alkoxyalkyl groups,
  • Xc represents a halogen atom, a cyano group, a C1-C6 alkoxy group or a C1-C6 alkylthio group, and.
  • R c is, C 1 through C 10 alkyl group, C 2 ⁇ C 10 alkenyl group, C 2 ⁇ C 1 0 alkynyl group, C 3 ⁇ C 8 cycloalkyl group, C4 ⁇ C 10 shea click port alkyl group or Ararukiru
  • a benzene ring of the aralkyl group may be substituted with a halogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group or a C1-C6 alkylthio group. No. ]
  • H e t. C is characterized by a group represented by the general formula H et, preparative Ria triazolopyrimidine derivative according to (7).
  • a fungicide for agricultural and horticultural use comprising the triazolopyrimidine derivative according to any one of (1) to (8) as an active ingredient.
  • Formula (A;), Formula (B), Formula (C) or the general formula H etj ⁇ H eti 5 on the base is an alkyl group or a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group
  • the alkyl moiety of the alkoxycarbonyl group or the alkylamino group may be linear or branched.
  • H et A or in the general formula (B), H et B is an arbitrary 5-membered or 6-membered ring containing a hetero element within ⁇ , preferably, the general formula H a ring represented by any one of Eteti 5, more preferably the ring represented by the He t physician 116 seven 6 or 3 ⁇ 4 [6 "1 1 2.
  • H et c is an arbitrary 5- or 6-membered ring containing a hetero element in the ring, and is preferably any ring represented by the following general formula. Yes, and more preferably, Het! Is a ring represented by
  • Halogen atoms as R 2 or R 3 on Het A , Het B or Het c , or on Het to Het 5 include chlorine, bromine, iodine and fluorine atoms.
  • C 1 -C 6 alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, isobutyl, sec-butyl, n- Examples include a pentyl group, an isoamyl group, and an n-hexyl group.
  • Examples of the C 1 -C 6 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, and a sec-butoxy group. Group, t-butoxy group, isobutoxy group and isohexyloxy group.
  • Examples of the C 1 -C 6 haloalkyl group include trifluoromethyl group, difluoromethyl group, trichloromethyl group, dichloromethyl group, and fluoromethylyl.
  • the C2-C6 alkoxyalkyl group includes methoxymethyl group.
  • the C 1 -C 10 alkyl group represented by R A or R A is a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec group.
  • the -C 10 alkenyl group include a vinyl group, an aryl group, a 1-butenyl group, a 2-butenyl group, a 1-isobutenyl group, a 3-methyl-2-butenyl group, a 1-pentenyl group, a 1-hexenyl group, and a 1-hexenyl group.
  • a C 2 -C 10 alkynyl group such as ethynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 5-pentynyl group, 3,3-dimethyl-1-butynyl Group, 4-methyl-1-pen
  • alkenyl groups and 7 Okuchiniru group examples include a chlorine atom, a bromine atom, an iodine atom and a fluorine atom.
  • C1-C6 alkyl group A methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an isobutyl group, a sec-butyl group, an n-pentyl group, an isoamyl group, and an n-hexyl group.
  • C1-C6 haloalkyl groups include trifluoromethyl, difluoromethyl, trichloromethyl, dichloromethyl, fluoromethyl, chloromethyl, odomethyl, promomethyl, penfluorofluorethyl and penchlorochloroethyl.
  • Examples of the C 1 -C 6 alkoxy group include a methoxy group, an ethoxy group, an I-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a t-butoxy group, an isobutoxy group and a And an isohexyloxy group.
  • Examples of the C1-C6 alkylthio group include a methylthio group, Ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, sec-butylthio group, t-butylthio group, isoptylthio group, and isohexylthio group, and the like.
  • R B is an optionally substituted nitrogen-containing heterocyclic ring which is bonded to triazolopyrimidine and a nitrogen atom, and is preferably the following nitrogen-containing heterocycle. Rings. — Me
  • the C 1 to C 10 alkyl group as R c includes a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, Isobutyl, sec-butyl, t-butyl, n-pentyl, isoamyl, n-hexyl, n-heptyl, 'n-octyl, n-nonyl and n-decyl No.
  • Examples of the C 2 -C 10 alkenyl group include a vinyl group, an aryl group, a 1-butenyl group, a 2-butenyl group, a 1-isobutenyl group, a 3-methyl-2-butenyl group, a 1-pentenyl group, and a 1-hexenyl And a 1-octenyl group.
  • Examples of the C 2 -C 10 alkynyl group include ethynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 5-pentynyl group, 3,3-dimethyl-1-butynyl group, 4 -Methyl-1-pentynyl group and 7-octynyl group.
  • Examples of the C3-C8 cycloalkyl group include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like.
  • Examples of the C4-C10 cycloalkylalkyl group include a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a cyclohexylethyl group, and the like.
  • Examples of the aralkyl group include a pendyl group, a monophenyl group, a -phenyl group, a 3-phenylpropyl group and a 4-phenylbutyl group.
  • Examples of the aralkyl group having a halogen atom substituted on the benzene ring represented by R c in the general formula (C) include a 2-chloropentyl group, a 3-chlorobenzene group, a 4-chlorobenzyl group, and a 2-chlorobenzene group.
  • 6-Fluoropendyl group 2,6-dichlorobenzyl group, 2,3-dichlorobenzyl group, 2,4-dichlorobenzyl group, 3,4-dichlorobenzyl group, 3-bromobenzyl group, 2-Fluoro benzyl group, 3-Fluoro benzyl group, 4-Fluoro benzyl group, 2,6-Difluoro benzyl group, 2,5-Difluoro benzyl group, 3,4-Difluoro benzyl group Examples include a benzyl group, a 3,5-difluorobenzyl group, a 4-chloro-phenylene group and a 4-chloro-phenylene group.
  • Aralkyl groups having a benzene ring substituted with a C 1 -C 6 alkyl group include 2-methylbenzyl group, 3-methylbenzyl group, 4 monomethylbenzyl group, 2,4-dimethylbenzyl group, 3,4-dimethylbenzyl group, 2,4,6—trimethylbenzyl group, 4-ethylbenzyl group, 4-isopropylbenzyl group, 2,4,6 —Triisopropylbenzyl group, p-t-butylbenzyl group, and 3,5-di-t-butylbenzyl group.
  • Examples of the aralkyl group in which the benzene ring is substituted with a C1-C6 alkoxy group include a 2-methoxybenzyl group, a 3-methoxybenzyl group, a 3,4-dimethoxybenzyl group, and a 3,5-dimethoxybenzyl group. , 3-Methoxy- 4-ethoxybenzyl, 4-ethoxybenzyl, 4-n-propoxybenzyl, 4-isopropoxybenzyl, 4-n-butoxybenzyl, 4-sec-butoxybenzyl, Examples include 4-isobutoxypentyl group, 4-t-butoxybenzyl group and 4-isohexyloxybenzyl group.
  • Aralkyl groups in which the benzene ring has been substituted with a C1-C6 alkylthio group include 2-methylthiobenzyl, 3-methylthiobenzyl, 4-methylthiobenzyl, 4-ethylthiobenzyl, and 4-n —Propylthiobenzyl, 4-isopropylthiobenzyl, 4- ⁇ -butylthiobenzyl, 4-sec—Butylthiopendyl, 4-isobutylthiobenzyl, 4-t-butylthiobenzyl, and 4-t-butylthiobenzyl Cishexylthiobenzyl group and the like.
  • halogen atom is a X c in X B or the general formula X A, general formula in the formula (A) (B) (C ), a chlorine atom, a bromine atom, and an iodine atom and fluorine atom.
  • C 1 -C 6 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a t-butoxy group, an isobutoxy group, an n-pentyloxy group, and a And a so-hexyloxy group.
  • C1-C6 alkylthio groups include methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, t-butylthio, isobutylthio and isohexyl. And a silthio group.
  • the C 1 ⁇ C 6 alkylsulfinyl group is X B in X A or formula In Formula (A) (B), methylsulfinyl group, E Ji Rusurufieru group, n- propyl sulfinyl group, isopropyl sulphates Iniru group , N-butylsulfinyl, sec-butylsulfinyl, t-butylsulfinyl, isobutylsulfinyl, and isohexylsulfinyl.
  • C1-C6 alkylsulfonyl groups include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, sec-butylsulfonyl, t-butylsulfonyl, isobutyls And a ruphonyl group and an isohexylsulfonyl group.
  • the C 1 -C 6 alkylamino group may be a monoalkylamino group or a dialkylamino group.
  • alkyl moiety examples include methyl, ethyl, n-propyl, isopropyl, and n-alkyl. Butyl, isobutyl, isohexyl and the like.
  • alkoxy moiety of the C 1 -C 6 alkoxycarbonyl group examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, t-butoxy, isobutoxy, n-pentyloxy and isohexyloxy. Is mentioned.
  • Tables 1 to 10 show specific examples of the triazolopyrimidine derivative of the present invention represented by the general formula (A), and specific examples of the triazolopyrimidine derivative of the present invention represented by the general formula (B).
  • Tables 11 to 22 show specific examples of the triazolopyrimidine derivative represented by the general formula (C) according to the present invention in Tables 23 to 25.
  • Table 26 shows specific examples of compounds that can be intermediates of these derivatives (compounds represented by the general formula (1) in Scheme 1 described below).
  • Het represents any of Het A , Het B or Hetc
  • W represents Y represents a hydrogen atom or an alkali metal atom such as sodium or potassium
  • Y represents a cyano group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 group.
  • the step (Step 3) preferably comprises adding 1 equivalent of the compound of the general formula (2) or the compound of the general formula (4) to the compound of the general formula (1), and adding 1.0 to 2.5 equivalents of a base.
  • a suitable organic solvent In the presence of a suitable organic solvent.
  • the reaction temperature is 20 to 150 ° C, and the reaction time is 1 to 8 hours.
  • the base include organic bases such as triethylamine and N, N-getyl di'phosphorus; and inorganic bases such as sodium carbonate, sodium hydrogencarbonate, carbonated lime, and oily hydrogenated sodium.
  • organic solvent examples include hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chloroform and benzene; ethers such as dioxane and tetrahydrofuran; nitriles such as acetonitrile; Amides such as dimethylformamide and dimethylacetamide and dimethylsulfoxide can be used.
  • water and an organic solvent such as benzene, toluene, and chloroform are added to the reaction mixture for extraction.
  • the organic solvent layer is dehydrated with anhydrous sodium sulfate, magnesium sulfate anhydrous, etc., and the solvent is distilled off. Perform normal processing such as If necessary, purify by operations such as chromatography.
  • the compound of the general formula (2) and the compound of the general formula (4), which are the starting compounds for this reaction are commercially available products or are known compounds that can be easily produced by known methods.
  • the 5-halogen triazolopyrimidine derivative (A 5 ) or ( ⁇ ′) thus obtained is converted into an alcohol, alkylamine or a compound represented by the general formula (3) in the presence of a base.
  • the compound represented by the general formula (3), which is a starting compound for this reaction is a known compound that is commercially available or can be easily produced by a known method.
  • Examples of the compound represented by the general formula (3) include, for example, methyl alcohol, ethyl alcohol, isopropyl alcohol, methylamine, and ethylamine. , Methyl mercaptonate sodium, sodium cyanide, potassium cyanide and the like.
  • Step 5 of reacting the compound represented by the general formula (1) with the compound represented by the general formula (5), preferably, one equivalent of the compound (5) is added to the compound (1).
  • the reaction is carried out in a suitable organic solvent in the presence of 0.01 to 1.0 equivalent of a transition metal such as palladium or nickel.
  • a 5-halogentriazolopyrimidine derivative (compound (C ′)) in which X is a halogen atom is obtained.
  • the organic solvent hydrocarbons such as toluene and xylene or ethers such as dioxane and tetrahydrofuran can be used.
  • the reaction temperature is 20 to 150 ° C., preferably used. The temperature is close to the boiling point of the organic solvent used, and the reaction time is 1 to 8 hours.
  • the triazolopyrimidine derivative represented by the general formula (C) of the present invention can be produced.
  • the base used in the present reaction include, for example, organic bases such as triethylamine, N, N-getylalanine and the like.
  • inorganic bases such as sodium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate or sodium hydride.
  • metal cyanides include, for example, sodium cyanide, potassium cyanide, etc. Is mentioned.
  • Compound (5) which is one of the starting compounds in the above-mentioned reaction, is a known compound, and is obtained by using a commercially available product or by producing it by a known method. Can be used ...
  • the dihalogentriazolo pyrimidine derivative represented by the general formula (1) in the above scheme 1 can be produced according to the following scheme 2.
  • the compound represented by the general formula (1) is composed of a malonic ester derivative represented by the general formula (7) and a 3-amino-1,2,4 represented by the general formula (6).
  • the compound can be produced by condensing triazole to obtain a compound represented by the general formula (8) and halogenating the compound. This reaction will be described separately in the following condensation step and halogenation step.
  • reaction step In the step of reacting compound (7) with compound (6), one equivalent of compound (7) is preferably added to compound (6), and the reaction is performed in the presence of 1 to 5 equivalents of a base.
  • the reaction is performed in an appropriate organic solvent according to Bases used in this reaction step include alkali metal alkoxides such as sodium methoxide, triethylamine, tri-n-propylamine, tri-n-butylamine, pyridine, dimethylaminoviridine, and N, N-ethylethylaniline.
  • Organic bases inorganic bases such as sodium carbonate, sodium hydrogen carbonate, and potassium carbonate.
  • Organic solvents include hydrocarbons such as toluene and xylene, and halogenated compounds such as benzene Hydrocarbons, ethers such as dioxane and tetrahydrofuran, alcohols such as methanol, ethanol, n-butanol, amides such as dimethylformamide and dimethylacetamide, and dimethylsulfoxide. Can be used.
  • a preferable reaction temperature for facilitating the above reaction is 20 to 150 ° C., preferably a temperature close to the boiling point of the organic solvent used, and a reaction time for the starting compound used. Although it varies depending on the catalyst, reaction temperature, etc., it is generally 1 to 8 hours. When the reaction is performed in this manner, compound (8) is obtained. This compound may be fractionated and used in the next reaction, but is preferably used as it is in the next reaction step.
  • the reaction solution containing the compound (8) generated in the above step is added to the deoxidizing agent if necessary.
  • the compound (8) may be reacted by adding 1 to 10 equivalents of a halogenating agent in the presence of the compound (8).
  • the reaction solution is subjected to a normal treatment such as distilling off the used solvent and excess halogenating agent, or, if necessary, purification by an operation such as chromatography and recrystallization.
  • the desired compound (1) can be obtained.
  • Examples of the deoxidizing agent that can be used in the nitrogenation step include organic bases such as triethylamine, tri-n-propylamine, tri-n-butylamine, pyridine, dimethylaminopyridine, N, N-jetylaniline, sodium carbonate, hydrogencarbonate and the like. Examples include inorganic bases such as sodium and potassium carbonate. Examples of the halogenating agent that can be used in the halogenation step include phosphorus oxychloride and phosphorus oxybromide.
  • the reaction does not require a reaction solvent.
  • an organic solvent for example, hydrocarbons such as benzene and toluene, chlorobenzene, and chloroform are used.
  • Halogenated hydrocarbons can be used.
  • the reaction temperature of the halogenation is 50 to 150 ° C., and the reaction time is 1 to 10 hours.
  • halogen triazolopyrimidine represented by the general formula (1)
  • the compound is reacted in a suitable organic solvent by adding 1 to 10 equivalents of a halogenating agent to compound (1) in the presence of 0.05 to 2.5 equivalents of a base, if necessary.
  • a hydrogen atom on Het can be replaced with a halogen atom.
  • the halogenating agent that can be used in the reaction include chlorine, sulfuryl chloride, N-chlorosuccinimide, bromine, and N-promosuccinimide.
  • bases examples include organic bases such as triethylamine, tri-n-propylamine, tri-n-butylamine, pyridine, dimethylaminoviridine, N, N-ethylethylphosphorus, sodium carbonate, hydrogen carbonate and the like.
  • Organic bases such as sodium and potassium carbonate can be used.
  • the reaction temperature of the halogenation is 50 to 150 ° C, and the reaction time is 1 to 10 hours.
  • the organic solvent hydrocarbons such as benzene and toluene, and halogenated hydrocarbons such as benzene and chloroform can be used .
  • the malonic ester derivative represented by the general formula (7) can be produced by the following method 3 (Method 1 to Method 3).
  • H et and R represent the same meaning as described above, and Z represents a halogen atom or a C 1 -C 10 alkoxy group.
  • Method 1 The reaction between the compound represented by the general formula (9) and the compound represented by the general formula (10) is performed by adding 1 to 2 equivalents of the compound (10) to the compound (9). The reaction is carried out in a suitable organic solvent in the presence of 1 to 2 equivalents of a base as necessary.
  • the reaction temperature is —70 to 150. C, and the reaction time is 1 to 8 hours.
  • the base include alkali metal alkoxides such as sodium methoxide, organic bases such as triethylamine, N, N-getylaniline, and inorganic bases such as sodium carbonate, sodium hydrogencarbonate, sodium carbonate, and oily sodium hydride. And lithium diisopropylamine.
  • organic solvent examples include hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chloroform and benzene, ethers such as dioxane and tetrahydrofuran, and amines such as dimethylformamide and dimethylacetamide. And dimethylsulfoxide.
  • water and an organic solvent such as benzene, toluene, or chloroform are added to the reaction mixture for extraction.
  • the organic solvent layer is dehydrated with anhydrous sodium sulfate, anhydrous magnesium sulfate, etc., and the solvent is distilled off. Perform normal processing such as If necessary, purify by chromatography, recrystallization, etc.
  • the compounds represented by the general formulas (9) and (10), which are the starting compounds for this reaction are known compounds, and may be obtained from commercial products or used, or produced by known methods. Can be used.
  • Method 2 The step of reacting the compound represented by the general formula (11) with the compound represented by the general formula (12) is performed in an amount of 1 to 2.5 equivalents of the compound represented by the formula (11). (12) is added, and the reaction is carried out in an appropriate organic solvent in the presence of 1.0 to 2. equivalents of a base, if necessary.
  • the reaction temperature is 20 to 150 ° C, and the reaction time is 1 to 8 hours.
  • the base include organic bases such as alkali metal alkoxides such as sodium methoxide, triethylamine, N, N-methylethylaniline, and inorganic bases such as sodium carbonate, sodium hydrogencarbonate, potassium carbonate, and oily sodium hydride. Can be used.
  • organic solvent examples include hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chloroform and benzene, ethers such as dioxane and tetrahydrofuran, and nitriles such as acetonitrile. Amides such as dimethylformamide and dimethylacetamide, and dimethylsulfoxide can be used.
  • water and an organic solvent such as benzene, toluene, and chloroform are added to the reaction solution for extraction.
  • the organic solvent layer is dehydrated with anhydrous sodium sulfate, anhydrous magnesium sulfate, etc., and the solvent is distilled off. Normal processing such as is performed. If necessary, purify by chromatography or other procedures.
  • the compounds represented by the general formulas (11) and (12), which are the starting compounds for this reaction, are known compounds, and may be obtained by using commercially available products or produced by known methods. Can be used.
  • Method 3 The step of reacting the compound represented by the general formula (13) with the compound represented by the general formula (14) is performed in an amount of 1 to 2.5 equivalents of the compound (14) with respect to the compound (13).
  • the reaction is carried out in a suitable organic solvent in the presence of 1.0 to 2.5 equivalents of a base, if necessary.
  • the reaction temperature is 20 to 150 ° C, preferably, a temperature close to the boiling point of the organic solvent used, and the reaction time.
  • Examples of the base include alkali metal alkoxides such as sodium-toxide, organic bases such as triethylamine, N, N-ethylylaniline, sodium carbonate, sodium hydrogencarbonate, sodium carbonate, and sodium oil hydride. Inorganic bases can be used.
  • Examples of the organic solvent include hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chloroform and benzene, ethers such as dioxane and tetrahydrofuran, nitriles such as acetonitrile, and the like. Amides such as dimethylformamide and dimethylacetamide and dimethylsulfoxide can be used.
  • the compounds of the general formulas (13) and (14), which are the starting compounds for this reaction, are known compounds, and are obtained by using commercially available products or manufactured and used by known methods. be able to.
  • the derivatives represented by the general formula (A), (B) or (C) include salts thereof.
  • the salt include an inorganic acid salt such as hydrochloride and sulfate, and an organic acid salt such as acetate, oxalate and methyl sulfonate.
  • compositions containing one or more of the compounds according to the present invention can be used as fungicides.
  • compositions containing one or more of the compounds according to the present invention can be used as agricultural and horticultural fungicides.
  • preferred compounds as components of agricultural and horticultural fungicides are triazolopyrimidine derivatives shown in Tables 1 to 25, and more preferably, 31 is a triazolic pyrimidine derivative shown in FIG. Table 27 Compounds in Kakko in 7 to 31 The product numbers correspond to the compound numbers in Tables 1-25. '
  • composition containing the compound according to the present invention as an active ingredient can be used for various diseases of agricultural and horticultural crops including petals, turf, etc. by foliage application, water application, soil application, seed treatment, or the like. Can be done.
  • the compounds according to the present invention have a particularly high controlling effect in controlling the diseases shown in Tables 32 to 34 described below.
  • Vine blight Mycospaerella melonis
  • Nettle spot (Pyrenophora teres) Black smut (Tille tia con tro versa) Wheat powdery mildew (Erysiphe graminis f. Sp.tritici) Red mold (Gibberella zeae) Red rust (Puccinia recondita)
  • Leaf blight (Septoria tritici)
  • Rust (Physopella ampelopsidis) ⁇ Rot (Glomerella cingulata)
  • Black spot (Alternaria kikuchiana) Scab (Gymn osp orangium a si a ticu) Ring spot (Bo tryosph a eria berengeriana) Oyster powdery mildew (Phyllactinia kakicola)
  • Idiot disease (Gibberella fujik uroi) sesame leaf blight (Cochliobolus miyabean us) octopus powdery mildew (Erysiphe cichoracearum) sclerotium disease (Sclerotinia sclerotioruni) plague (Phytoph th ora nico tian ae) red scab (Alternaria longipes)
  • Charcoal purse (CoUectotrich um tabacum) Tulip gray rot (Bo trytis cin ere a) Rose powdery mildew (Sphaerotheca pannosa)
  • Soybean purpura (Cercospora kikuchii) Potato blight (Phytophthora infestans)
  • the compound according to the present invention can be formulated into a conventional formulation and used. That is, the compound according to the present invention and a suitable carrier and auxiliary agent, for example, a surfactant, a binder, a stabilizer and the like can be blended to prepare a formulation generally used as a formulation of an agricultural chemical. That is, the compound of the general formula (1) according to the present invention includes, for example, powder, coarse powder, DL (driftless type) powder, flodstat, fine granule, fine granule, granule, tablet, and wettable powder. It can be formulated into hydrated granules, sols (flowables), emulsions and oils. The dosage forms that can be prepared are not limited to those listed here.
  • any carrier that is commonly used for agricultural and horticultural fungicides can be used, and it is not limited to a specific carrier.
  • Such solid carriers include, for example, animal and plant powders such as starch, activated carbon, soy flour, flour, wood flour, fish meal, milk powder, talc, kaolin, bentonite, zeolite diatomaceous earth, white carbon, clay, alumina And mineral powders such as calcium carbonate, potassium chloride and ammonium sulfate. .
  • animal and plant powders such as starch, activated carbon, soy flour, flour, wood flour, fish meal, milk powder, talc, kaolin, bentonite, zeolite diatomaceous earth, white carbon, clay, alumina And mineral powders such as calcium carbonate, potassium chloride and ammonium sulfate. .
  • liquid carrier examples include water; alcohols such as isopropyl alcohol and ethylene glycol; ketones such as hexahexanone and methylethyl ketone; propylene glycol monomethyl ether, and ethylene glycol mono-n-butyl ether.
  • Ethers aliphatic hydrocarbons such as kerosene and gas oil; xylene, trimethylbenzene, tetramethylbenzene, methylnaphthine, sorbent and naphtha; aromatic hydrocarbons such as N-methyl-2-pyrrolidone Amides; esters such as glycerin esters of fatty acids; and vegetable oils such as soybean oil and rapeseed oil.
  • Surfactants that can be used in the formulation include nonionic surfactants, anionic surfactants, cationic surfactants, and amphoteric surfactants. Things can be used.
  • nonionic surfactants include, for example, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene alkyl ester, polyoxyethylene sorbin alkylate, polyoxyethylene Examples include ethylene phenyl ether polymer, polyoxyethylene alkylene aryl phenyl ether, polyoxyethylene alkylene glycol, and polyoxyethylene polyoxypropylene block polymer.
  • anionic surfactants include, for example, lignin sulfonate, alkylaryl sulfonate, dialkyl sulfosuccinate, polyoxyethylene alkylaryl ether sulfate, alkyl naphthylene sulfonate, polyoxyethylene Styrylphenyl ether sulfate and the like.
  • cationic surfactant examples include, for example, an alkylamine salt and the like.
  • amphoteric surfactant examples include, for example, quaternary ammonium salt alkylbenzene in, amine oxide and the like.
  • the surfactants that can be used in the formulation are not limited to these, and they may be used alone or in combination of two or more.
  • auxiliary agents include binders, thickeners, fixing agents, preservatives, fungicides, solvents, pesticide active ingredient stabilizers, antioxidants, UV inhibitors, crystal precipitation inhibitors, defoamers, Examples include, but are not limited to, physical property improvers, colorants, and the like, and these auxiliaries can be added as needed.
  • the binding agent, thickening agent and fixing agent are not particularly limited, For example, starch, dextrin, cellulose, methylcellulose, ethylcellulose, carboxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, carboxymethylstarch, pullulan, sodium alginate, ammonium alginate Propylene glycol alginate, guar gum, 'gum cast bean gum, gum arabic, xanthan gum, gelatin, casein, polyvinyl alcohol, polyethylene oxide, polyethylene glycol, ethylene.Propylene block polymer-sodium polyacrylate And polyvinyl alcohol.
  • the amount of the compound of the present invention to be added can be appropriately determined depending on the dosage form of the preparation and the method of use, and it is generally desirable to use the compound in the range of 0.1 to 90% by weight.
  • the compound according to the present invention is sufficiently effective when used alone, it is used in combination with one or more selected from various fungicides, insecticides and acaricides, and synergists. You can also. Representative examples of fungicides, insecticides, and acaricides that can be used by mixing with the compound of the present invention are shown below. .
  • Pyrethroid insecticides Pyrethroid insecticides; permethrin, cypermethrin, del yus metrine, fenvalerate, fenpronotrin, pyrethrin, arelesli , Tetramethrin, resmethrin, dimethrin, propasulin, phenothrin, protrin, fluparinate, cyfluthrin, cyhalothrin, flucitrinet, etofenprox, cycloprotrin, tralomethrin, silafluophan, brofenprox , Acrinasulin and the like.
  • Benzoylpereas and other insecticides difluvenzuron, chlorfluazuron, hexaflumuron, triflumuron, tetrabenzuron, flufenoxuron, flucycloxuron, puprofezin, pyriproxyfen, methoprene, benzepin, diafenthiuron, acetamimi Pride, imidacloprid, ditenviram, fipronil, cartap, thiocyclam, bensultap., Nicotine sulfate, rotenone, metaaldehyde, machine oil, microbial pesticides such as BT and insect viruses.
  • a fungicide for agricultural and horticultural use containing the compound represented by the general formula (A), the general formula (B) or the general formula (C) as an active ingredient (hereinafter, also referred to as “a fungicide for agricultural and horticultural use according to the present invention”)
  • the usage of is generally as follows. That is, in the case of wettable powders, solutions, emulsions, sols (flowables), granule wettable powders and oils, the active ingredient is generally diluted 50-1000 times with water. It is adjusted to a concentration of ⁇ 100 ppm. This diluted solution is applied to the foliage of the site where the disease of the plant occurs in the range of 10 to 2000 liters per 10 ares, usually in the range of 20 to 700 liters.
  • liquids In the case of liquids, emulsions and sols (floor pulls), they are not diluted with water, but are used as a concentrated solution, or diluted with water within 50 times, mainly for aerial spraying.
  • spraying agents LV spraying, ULV spraying, S spraying
  • 50-5000ml per 10 is sprayed using a helicopter.
  • powder coarse powder, DL powder, flodust, fine granules, fine granules and granules, 2 to 5 kg (about 5 to 500 g as active ingredient) per 10 ares It is applied to foliage at the site of disease, soil surface, in soil or on the water surface.
  • the toluene layer was washed three times with a saturated saline solution, and then dried with anhydrous sodium sulfate.
  • the toluene layer was washed three times with a saturated saline solution and then dried over anhydrous sodium sulfate.
  • Powders can be obtained in the same manner by using the compounds shown in Tables 1 to 10 in place of the compound No. A-11.
  • Powders can be obtained in the same manner by using the compounds shown in Tables 11 to 22 in place of the compound No. B-19.
  • Powders can be obtained in the same manner by using the compounds shown in Tables 23 to 25 in place of the compound N0.C-11.
  • a wettable powder can be obtained in the same manner by using the compounds shown in Tables 1 to 10 in place of the compound N0.A-64.
  • a wettable powder can be obtained in the same manner by using the compounds described in Tables 11 to 22 in place of the compound No. B-1_2_7.
  • a wettable powder can be obtained in the same manner by using the compounds shown in Tables 23 to 25 in place of the compound No. C-1.
  • a compound containing 30% of the active ingredient can be dissolved by mixing and dissolving 30 parts of compound No. A—11, 40 parts of methylethyl ketone and 30 parts of polyoxyethylene nonylphenyl ether. obtain.
  • Emulsions can be obtained in the same manner by using the compounds shown in Tables 1 to 10 in place of the compound No. A-11.
  • Example-2 1_ When 30 parts of compound No. B-68, 40 parts of methylethyl ketone and 30 parts of polyoxyethylene nonylphenyl ether are mixed and dissolved, an emulsion containing 30% of the active ingredient is obtained.
  • Emulsions can be obtained in the same manner by using the compounds shown in Tables 11 to 22 in place of the compound N0.B-68.
  • Emulsions can be obtained in the same manner by using the compounds shown in Tables 23 to 25 in place of the compound No. C-1.
  • a sol can be obtained in the same manner by using the compounds described in Tables 1 to 10 in place of the compound N 0 .A-99.
  • a sol can be obtained in the same manner by using the compounds described in Tables 11 to 22 in place of the compound No. B-127.
  • a sol can be obtained in the same manner by using the compounds shown in Tables 23 to 25 in place of the compound No. C-11.
  • Granules can be obtained in the same manner by using the compounds shown in Tables 1 to 10 in place of the compound No. A-64.
  • Granules can be obtained in the same manner by using the compounds shown in Tables 11 to 22 in place of the compound ⁇ . ⁇ -68.
  • Granules can be obtained in the same manner by using the compounds described in Tables 23 to 25 in place of the compound N0.C-1.
  • Test Examples Specific examples of the usefulness of the compound according to the present invention as an active ingredient of the agricultural and horticultural fungicide and the usefulness of the agricultural and horticultural fungicide according to the present invention are shown in Test Examples 1 to 17.
  • Rice Blast Prevention Effect Test (Test Examples 1-3)
  • a three-leaf stage seedling of rice (cultivar: Asahi) cultivated in a plastic pot having a diameter of 6 cm in a greenhouse was diluted with a predetermined concentration of a wettable powder prepared according to Example 17 in 1 step. 1 O ml was sprayed per pot.
  • conidia of Pyr iculariao ryz ae (Pyricularia ryz ae) formed on oatmeal agar medium were inoculated in advance, and the disease was controlled in a 24 ° C climate chamber. .
  • Five days after the inoculation of the fungus the number of rice blast spots on the three leaves was investigated, and the control value (%) was calculated by the following formula. The control value (%) was converted into an evaluation value according to the following criteria.
  • Comparative drug A is the following comparative drug A, which was prepared and used in place of the compound of the present invention. The same applies to the following table.
  • Comparative drug A is a compound represented by the following formula, and is a compound described in US Pat. No. 5,593,996. .
  • control value of the wettable powder prepared according to Example 18 was calculated in the same manner as in Test Example 1, and the control value was converted to an evaluation value according to the same standard.
  • phytotoxicity to paddy rice was investigated according to the same criteria as in Test Example 1. The results are shown in Table 36.
  • Comparative agent B 200 1 0 No spray area 0 (26)
  • Comparative drug ⁇ is the following comparative drug ⁇ and was prepared and used in the same manner instead of the compound of the present invention. The same applies to the following table.
  • Comparative drug ⁇ is a compound represented by the following formula, and is a compound described in US Pat. No. 5,593,996.
  • control value was calculated by the same method as in Test Example 1, and the control value was converted to an evaluation value according to the same standard.
  • phytotoxicity to paddy rice was investigated according to the same criteria as in Test Example 1. The results are shown in Table 37.
  • Comparative drug C is the following Comparative Fiber ijC, which was prepared and used in place of the compound of the present invention. The same applies to the following table. Comparative drug C is a compound represented by the following formula, and is a compound described in International Patent Publication No. WO99 / 41255.
  • control value was calculated by the same method as in Test Example 4, and the control value was converted to an evaluation value according to the same standard.
  • phytotoxicity to barley was investigated according to the same criteria as in Test Example 1. The results are shown in Table 39.
  • Test compound D C No. Spraying chemical concentration Control effect
  • control value was calculated in the same manner as in Test Example 4, and the control value was converted to an evaluation value according to the same standard.
  • phytotoxicity to barley was investigated according to the same criteria as in Test Example 1. Table 40 shows the results.
  • a diluent of a predetermined concentration of a hydrating agent prepared according to Example 1 in a two-leaf stage seedling of a cucumber (variety: Sagami Hanshiro) cultivated in a plastic pot having a diameter of 6 cm in a greenhouse was sprayed at a rate of 10 ml per pot.
  • the day after the treatment with the agent spores of Cucumber blight and a fungus (Pseudoperonos spora cuben s sis: Pseudomonas borax benbensis) previously formed on cucumber leaves were inoculated, and the disease was controlled in an artificial weather chamber at 20 ° C.
  • Pillars 1 The values in parentheses in the non-sprayed plot are the average lesion area percentage of cucumber and disease per leaf.
  • control value was calculated in the same manner as in Test Example 10, and the control value was converted to an evaluation value according to the same standard.
  • phytotoxicity to Kiyuri ' was investigated using the same criteria as in Test Example 1. The results are shown in Table 45.
  • control value was calculated by the same method as in Test Example 10, and the control value was converted to an evaluation value according to the same standard.
  • phytotoxicity to cucumbers was investigated according to the same criteria as in Test Example 1. The results are shown in Table 46.
  • control value was calculated by the same method as in Test Example 13, and the control value was converted to an evaluation value according to the same standard.
  • phytotoxicity to cucumbers was investigated according to the same criteria as in Test Example 1. The results are shown in Table 48.
  • control value was calculated in the same manner as in Test Example 13, and the control value was converted to an evaluation value according to the same standard.
  • phytotoxicity to cucumbers was investigated according to the same criteria as in Test Example 1. The results are shown in Table 49.
  • control value of the wettable powder prepared according to Example 18 was calculated in the same manner as in Test Example 16. The results are shown in Table 51.
  • composition containing the compound according to the present invention can be used for the above-mentioned important diseases of agricultural crops, especially rice blast, rye powdery mildew, wheat red rust, rye downy mildew and rye gray.
  • Various diseases such as mold can be effectively controlled. Therefore, the compound according to the present invention is useful as an aromatic component of an agricultural and horticultural fungicide.

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Abstract

L'invention concerne des fongicides utilisés dans l'agriculture et l'horticulture contenant de nouveaux dérivés de triazolopyrimidine représentés par la formule (A), (B), ou (C) et présentant une activité de contrôle des maladies élevée et n'entraîne pas de dommages chimiques. Dans la formule (A), (B), ou (C) HetA-C est un noyau à 5 ou 6 éléments contenant un hétéroatome ; XA-C est halogène, cyano, ou similaire ; RA et RA' peuvent être identiques ou différents et sont C1-10alkyl, C2-10alcényl, C2-10 alkynyl, ou phényle ; RB est un hétérocycle azoté fixé à l'atome d'azote ; et RC est C1-10alkyl, C2-10alcényl, C2-10alkynyl, C3-8cycloalkyl, C4-10cycloalkylalkyl, ou aralkyl.
PCT/JP2003/009615 2002-07-29 2003-07-29 Derives de triazolopyrimidine et fongicides utilises dans l'agriculture et l'horticulture WO2004011467A1 (fr)

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WO2004108727A1 (fr) * 2003-06-04 2004-12-16 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines
WO2004113342A1 (fr) * 2003-06-25 2004-12-29 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines
WO2004112480A2 (fr) * 2003-06-24 2004-12-29 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines
WO2006066818A2 (fr) * 2004-12-17 2006-06-29 Basf Aktiengesellschaft 7-amino-6-hetaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles
WO2006066799A1 (fr) * 2004-12-17 2006-06-29 Basf Aktiengesellschaft 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre les champignons pathogenes
WO2006122740A2 (fr) * 2005-05-17 2006-11-23 Basf Aktiengesellschaft 7-amino-6-hetarylimidazolo[1,2-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles
WO2007006723A1 (fr) * 2005-07-13 2007-01-18 Basf Aktiengesellschaft Composes de 7-amino-6-tetrazolyl-1,2,4-triazolo[1,5-a]pyrimidine et utilisation de ceux-ci pour lutter contre des champignons nuisibles
WO2007006724A1 (fr) * 2005-07-13 2007-01-18 Basf Aktiengesellschaft Composes de 5-alkyl-7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine et utilisation de ceux-ci pour lutter contre des champignons nuisibles
WO2007006722A1 (fr) * 2005-07-13 2007-01-18 Basf Aktiengesellschaft Composes de 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine 2-substitues et utilisation de ceux-ci pour lutter contre des champignons nuisibles
WO2007023020A1 (fr) * 2005-07-13 2007-03-01 Basf Aktiengeseelschaft Composes 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine et utilisation dans la lutte contre des champignons parasites
JP2007506657A (ja) * 2003-06-24 2007-03-22 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 殺真菌性トリアゾロピリミジン類
WO2007101870A1 (fr) * 2006-03-08 2007-09-13 Basf Se Triazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant
US7598255B2 (en) 2005-08-04 2009-10-06 Janssen Pharmaceutica Nv Pyrimidine compounds as serotonin receptor modulators
US8618288B2 (en) 2003-09-17 2013-12-31 Janssen Pharmaceutica Nv Pyrimidine compounds as serotonin receptor modulators
US11814734B2 (en) 2019-05-13 2023-11-14 Ecolab Usa Inc. 1,2,4-triazolo[1,5-a] pyrimidine derivative as copper corrosion inhibitor

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JP2006526587A (ja) * 2003-06-04 2006-11-24 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト トリアゾロピリミジン類
WO2004108727A1 (fr) * 2003-06-04 2004-12-16 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines
WO2004112480A2 (fr) * 2003-06-24 2004-12-29 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines
WO2004112480A3 (fr) * 2003-06-24 2005-09-22 Bayer Cropscience Ag Triazolopyrimidines
JP2007506657A (ja) * 2003-06-24 2007-03-22 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 殺真菌性トリアゾロピリミジン類
JP2007506656A (ja) * 2003-06-24 2007-03-22 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト トリアゾロピリミジン類
WO2004113342A1 (fr) * 2003-06-25 2004-12-29 Bayer Cropscience Aktiengesellschaft Triazolopyrimidines
US8618288B2 (en) 2003-09-17 2013-12-31 Janssen Pharmaceutica Nv Pyrimidine compounds as serotonin receptor modulators
WO2006066799A1 (fr) * 2004-12-17 2006-06-29 Basf Aktiengesellschaft 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre les champignons pathogenes
WO2006066818A3 (fr) * 2004-12-17 2006-11-02 Basf Ag 7-amino-6-hetaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles
WO2006066818A2 (fr) * 2004-12-17 2006-06-29 Basf Aktiengesellschaft 7-amino-6-hetaryl-1,2,4-triazolo[1,5-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles
WO2006122740A3 (fr) * 2005-05-17 2007-02-22 Basf Ag 7-amino-6-hetarylimidazolo[1,2-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles
WO2006122740A2 (fr) * 2005-05-17 2006-11-23 Basf Aktiengesellschaft 7-amino-6-hetarylimidazolo[1,2-a]pyrimidines et leur utilisation pour lutter contre des champignons nuisibles
WO2007006723A1 (fr) * 2005-07-13 2007-01-18 Basf Aktiengesellschaft Composes de 7-amino-6-tetrazolyl-1,2,4-triazolo[1,5-a]pyrimidine et utilisation de ceux-ci pour lutter contre des champignons nuisibles
WO2007006724A1 (fr) * 2005-07-13 2007-01-18 Basf Aktiengesellschaft Composes de 5-alkyl-7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine et utilisation de ceux-ci pour lutter contre des champignons nuisibles
WO2007006722A1 (fr) * 2005-07-13 2007-01-18 Basf Aktiengesellschaft Composes de 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine 2-substitues et utilisation de ceux-ci pour lutter contre des champignons nuisibles
WO2007023020A1 (fr) * 2005-07-13 2007-03-01 Basf Aktiengeseelschaft Composes 7-amino-6-heteroaryl-1,2,4-triazolo[1,5-a]pyrimidine et utilisation dans la lutte contre des champignons parasites
US7598255B2 (en) 2005-08-04 2009-10-06 Janssen Pharmaceutica Nv Pyrimidine compounds as serotonin receptor modulators
US8883808B2 (en) 2005-08-04 2014-11-11 Janssen Pharmaceutica N.V. Combination of 5-HT7 receptor antagonist and serotonin reuptake inhibitor therapy
WO2007101870A1 (fr) * 2006-03-08 2007-09-13 Basf Se Triazolopyrimidines substituées, procédés de production associés et leur utilisation pour lutter contre des champignons nuisibles, et agents les contenant
US11814734B2 (en) 2019-05-13 2023-11-14 Ecolab Usa Inc. 1,2,4-triazolo[1,5-a] pyrimidine derivative as copper corrosion inhibitor

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