WO2002040473A1 - Composes de pyrimidine ou leurs sels, herbicides contenant ces composes ou ces sels, leur procede d'utilisation dans l'elimination des mauvaises herbes - Google Patents

Composes de pyrimidine ou leurs sels, herbicides contenant ces composes ou ces sels, leur procede d'utilisation dans l'elimination des mauvaises herbes Download PDF

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WO2002040473A1
WO2002040473A1 PCT/JP2001/010060 JP0110060W WO0240473A1 WO 2002040473 A1 WO2002040473 A1 WO 2002040473A1 JP 0110060 W JP0110060 W JP 0110060W WO 0240473 A1 WO0240473 A1 WO 0240473A1
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Prior art keywords
optionally substituted
substituted
alkyl
phenyl
ring
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PCT/JP2001/010060
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English (en)
Japanese (ja)
Inventor
Toru Koyanagi
Hiroshi Kikugawa
Hitoshi Nakayama
Seiko Miyashita
Souichiro Nagayama
Makiko Sano
Ken Ohno
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Ishihara Sangyo Kaisha, Ltd.
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Priority to AU2002215222A priority Critical patent/AU2002215222A1/en
Publication of WO2002040473A1 publication Critical patent/WO2002040473A1/fr

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    • 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
    • C07D239/30—Halogen atoms or nitro radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/38—One sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D403/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to a novel pyrimidine compound useful as an active ingredient of a herbicide.
  • W098111 074 discloses a compound similar to the pyrimidine compound represented by the formula (I) below, but the substituent represented by Ar in the formula (I) described below Are distinguished by Disclosure of the invention
  • the present invention provides a compound represented by the formula (I):
  • R 1 is a hydrogen atom, a halogen, an optionally substituted alkyl, an optionally substituted alkoxy, an optionally substituted alkenyl, or an optionally substituted Alkynyl, optionally substituted cycloalkyl, — SR 6 , one N (R 6 ) 2 (where R 6 may be the same or different and two R 6 are joined together
  • a ring may be formed, and further, an oxygen atom may be contained in the ring when forming the ring) or a phenyl which may
  • R 6 may be the same or different, and two R 6 may be taken together to form a ring. May contain an oxygen atom in the ring), C (X 3 R 10 ) (XR n ) or a phenyl which may be substituted by R 8
  • R 6 is a hydrogen atom, which may be alkyl, alkenyl which may be substituted, alkynyl which may be substituted, optionally substituted consequent opening alkyl optionally, yo I pyrid Le be substituted by phenyl which may be substituted or R 8 in R 8
  • R 7 is an optionally substituted alkyl, an optionally substituted alkenyl, an optionally substituted alkynyl, an optionally substituted cycloalkyl, — SR 6 , 10 R 6 , 1 N (R 6 ) 2 (R 6 here it is may also be the same or different and to form a ring two R 6 gar ⁇ It is also possible, furthermore,
  • R 1 is a hydrogen atom or methyl
  • R 2 and R 3 are each a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a methyl or a methoxy
  • R 4 is a phenyl which may be substituted
  • Ar may be substituted with pyrazole-5-yl (substitution here)
  • the group is phenyl which may be substituted, phenylthio which may be substituted, phenylsulfinyl which may be substituted or phenylsulfonyl which may be substituted, wherein X 1 is an acid
  • R 4 is a hydrogen atom , Alkyl, haloalkyl, alkoxyalkyl, phenylalanine alkyl (phenyl moiety may be substituted
  • substituents of the optionally substituted alkyl, the optionally substituted alkoxy, the optionally substituted alkenyl, and the optionally substituted alkynyl included in RR 4 , R 5 , R 6 and R 7 include, for example, halogen , C -! 6 alkoxy, ( ⁇ -. 6 alkylthio, Bok 6 dialkyl ⁇ amino, trimethylsilyl, etc. also a good phenyl substituted with R 8 and the like substitution number of these substituents, there in one or more And in the case of two or more, those substituents may be the same or different.
  • Examples of the optionally substituted cycloalkyl substituent included in RR 4 , R 5 , R 6 and R 7 include, for example, halogen and Bok 6 alkyl, C, _ 6 haloalkyl, ⁇ alkoxy, ( ⁇ _ 6 alkylthio, etc. may phenyl substituted by R 8 is Ru mentioned. Substitution number of these substituents may be 1 or more In the case of two or more, those substituents may be the same or different.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 1 ° and alkyl or the alkyl moiety in R 11 each have 1 to 6 carbon atoms.
  • Linear or branched ones for example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl and the like.
  • the alkenyl or alkenyl moiety in RR 4 , R 5 , R 6 and R 7 is a straight-chain or branched-chain having 2 to 6 carbon atoms, respectively, for example, vinyl, probenyl, isopropenyl, butenyl, Pentenyl, hexenyl and the like.
  • the alkynyl or alkynyl moiety in R 1 , R 4 , R 5 , R 6, and R 7 is a straight-chain or branched-chain having 2 to 6 carbon atoms, respectively, such as ethynyl, propiel, butyral, and isoptynyl. Pentynyl, hexynyl and the like.
  • Examples of cycloalkyl in R 1 , R 4 , R 5 , R 6 and R 7 include those having 3 to 6 carbon atoms, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
  • Examples of the halogen or the halogen as a substituent in RR 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 include each atom of fluorine, chlorine, bromine or iodine .
  • the number of halogens as substituents may be 1 or 2 or more, and in the case of 2 or more, each halogen may be the same or different.
  • the halogen may be substituted at any position.
  • N (R 6) 2 the two R 6 form a connexion ring such together, for example, is formed pyrrolidinyl, imidazolidinyl, Birazorijiniru, piperidyl, Pipera Jiniru, morpholinyl and the like.
  • R 1 D and R 11 When the alkyls in R 1 D and R 11 are taken together to form a ring, for example, 1,3-dithian-2-yl, 1,3-dioxan-2-yl, 1,3-dioxolane -Forms 2-yl, 1,3-dithiolan-2-yl, 1,3-oxathiolan-2-yl, etc.
  • the pyrimidine-based compound represented by the formula (I) can form a salt.
  • the salts include all salts that are agriculturally acceptable, for example, alkali metal salts such as sodium salt and potassium salt; alkaline earth metal salts such as magnesium salt and calcium salt; dimethylamine salt And ammonium salts such as triethylamine salt.
  • the pyrimidine compound represented by the formula (I) includes an optical isomer or a geometric isomer, and the present invention includes both isomers and isomer mixtures.
  • the pyrimidine-based compound represented by the above formula (I) or a salt thereof (hereinafter, abbreviated as the compound of the present invention) can be produced according to the following reaction [A] to [D] or a usual salt production method.
  • Reaction [A] is usually performed in the presence of a base and a solvent.
  • Bases include, for example, alkali metal hydrides such as sodium hydride and potassium hydride; alkyllithiums such as n-butyllithium and t-butyllithium; triethylamine, pyridine, 1,8-diazabicyclo [5.4. [0] tertiary amines such as 7-indene; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkaline metal carbonates such as sodium carbonate and lithium carbonate; sodium methoxide, potassium One or more kinds are appropriately selected from alcohol salts such as butoxide.
  • the solvent may be any solvent as long as it is inert to the reaction.
  • polar aprotic solvents such as N, N-dimethylformamide and dimethylsulfoxide; ethers such as getyl ether and tetrahydrofuran; One or more types are appropriately selected.
  • Reaction [A] is performed in the presence of an inert gas, if necessary.
  • the inert gas is appropriately selected from, for example, nitrogen, helium, and argon.
  • the reaction temperature and reaction time of the reaction (A) differ depending on the type of the compound, the reaction conditions, and the like, and cannot be specified unconditionally. However, the reaction temperature is usually ⁇ 80 to + 120 ° C., preferably 0 to 100 ° C. ° C, and the reaction time is usually 1 to 24 hours, preferably 2 to 6 hours. However, the optimum reaction temperature and reaction time can be individually determined by appropriately conducting preliminary tests in consideration of various reaction conditions. Second step
  • the first step of the reaction [B] is usually performed in the presence of a solvent and an inert gas.
  • the solvent may be any solvent as long as it is inert to the reaction.
  • one or more solvents are appropriately selected from ethers such as tetrahydrofuran and dimethyl ether.
  • the inert gas is appropriately selected from, for example, nitrogen, helium, and argon.
  • the reaction temperature and the reaction time of the first step of the reaction [B] vary depending on the type of the compound, the difference in the reaction conditions, and the like, and cannot be specified unconditionally.
  • the reaction temperature is usually 1120 to 150 ° C, preferably -100
  • the reaction time is usually 0.05 to 6 hours, preferably 0.1 to 3 hours.
  • the optimum reaction temperature and reaction time can be individually determined by appropriately conducting preliminary tests in consideration of various reaction conditions.
  • the second step of the reaction (B) is usually performed subsequent to the first step, and the solvent or inert gas used in the first step can be used as it is, but in some cases, in the first step, The solvents or inert gases mentioned may additionally be used.
  • the reaction temperature and the reaction time in the second step of the reaction [B] vary depending on the type of the compound, the difference in the reaction conditions, and the like, and cannot be specified unconditionally, but the reaction temperature is usually from 120 to 50.
  • the reaction time is usually from 1 to 80 to 30 ° C, and the reaction time is usually from 2 to 24 hours, preferably from 3 to 16 hours. However, the optimum reaction temperature and reaction time can be individually determined by appropriately conducting preliminary tests in consideration of various reaction conditions.
  • the first step of the reaction [C] is usually performed in the presence of a solvent and a condensing agent.
  • the solvent may be any solvent as long as it is inert to the reaction.
  • one or more solvents are appropriately selected from acetic acid and organic acids such as acetic acid.
  • the condensing agent is appropriately selected from, for example, organic acid anhydrides such as acetic anhydride and propionic anhydride.
  • reaction temperature and reaction time of the first step of the reaction (C) vary depending on the type of the compound, the difference in the reaction conditions, and the like, and cannot be specified unconditionally, but the reaction temperature is usually 40 to 150 ° C, preferably 80 to 120 °. C, and the reaction time is usually 1 to 24 hours, preferably 6 to 12 hours. However, the optimum reaction temperature and reaction time can be individually determined by appropriately conducting preliminary tests in consideration of various reaction conditions.
  • the second step of the reaction [C] is usually performed in the presence of a solvent.
  • the solvent may be any solvent as long as it is inert to the reaction.
  • polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone, and pyridine; acetonitrile One or two or more of nitriles such as propionitrile and acrylonitrile; alcohols such as methanol, ethanol, propanol and tertiary alcohol are appropriately selected.
  • reaction temperature and reaction time of the second step of the reaction (C) vary depending on the type of the compound, the reaction conditions, and the like, and cannot be specified unconditionally, but the reaction temperature is usually 0 to 100 ° C, preferably 20 to 100 ° C.
  • the reaction time is usually 0.5 to 12 hours, preferably 3 to 6 hours.
  • the optimum reaction temperature and reaction time can be individually determined by appropriately conducting preliminary tests in consideration of various reaction conditions.
  • the third step of the reaction [C] is performed according to a usual reduction reaction for producing an alcohol from a ketone.
  • reducing reagent for example, sodium borohydride, lithium aluminum hydride, and the like can be appropriately selected from those described in New Experimental Chemistry Lecture 15, Oxidation and Reduction [ ⁇ ⁇ ], pp. 12-13.
  • the third step of the reaction [C] is usually performed in the presence of a solvent.
  • the solvent may be any solvent as long as it is inert to the reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and benzene; ethers such as dioxane, tetrahydrofuran, and methyl ether; One or more kinds of alcohols such as methanol, ethanol, propanol, and tertiary alcohol are appropriately selected depending on the type of the reducing reagent from water and the like.
  • aromatic hydrocarbons such as benzene, toluene, xylene, and benzene
  • ethers such as dioxane, tetrahydrofuran, and methyl ether
  • One or more kinds of alcohols such as methanol, ethanol, propanol, and tertiary alcohol are appropriately selected depending on the type of the reducing reagent from water and the like.
  • the reaction temperature and the reaction time of the third step of the reaction (C) vary depending on the type of the compound, the difference in the reaction conditions, and the like, and cannot be specified unconditionally.
  • the reaction time is generally 0.5 to 12 hours, preferably 1 to 6 hours.
  • the optimal reaction temperature and reaction time can be individually determined by appropriately conducting preliminary tests, taking into account various reaction conditions.
  • Reaction [D] is usually performed in the presence of a base and a solvent.
  • a base and a solvent one or more kinds are appropriately selected from those exemplified in the aforementioned reaction [A].
  • Reaction [D] is performed in the presence of an inert gas, if necessary.
  • the inert gas is appropriately selected from, for example, nitrogen, helium, and argon.
  • Reaction (D) The reaction temperature and reaction time vary depending on the type of compound, reaction conditions, etc., and cannot be specified unconditionally, but the reaction temperature is usually 180 to + 100 ° C, preferably 0 to 50 ° C. The reaction time is usually 1 to 24 hours, preferably 2 to 6 hours. However, the optimum reaction temperature and reaction time can be individually determined by appropriately conducting preliminary tests in consideration of various reaction conditions.
  • the compound represented by the formula (III) used in the reaction [A] includes a novel compound. This compound can be produced according to the following reaction [E].
  • Reaction [E] is performed in the presence of a halogenating reagent.
  • halogenating reagent for example, thionyl chloride, phosphorus oxychloride, phosphorus pentachloride, thionyl bromide, phosphorus oxybromide, phosphorus pentabromide and the like can be used.
  • the reaction [E] is performed in the presence of a solvent, if necessary, but it is generally preferable to use a solvent.
  • the solvent may be any solvent as long as it is inert to the reaction.
  • the solvent include aromatic hydrocarbons such as benzene and toluene; alkyl halides such as methylene chloride and chloroform. The species or two or more species are appropriately selected.
  • reaction temperature and reaction time of reaction (E) vary depending on the type of compound, reaction conditions, and the like, and cannot be specified unconditionally, but the reaction temperature is usually 140 to 150 ° C, preferably 0 to 60 ° C. ° C, and the reaction time is usually 1 to 24 hours, preferably 2 to 6 hours. However, the optimum reaction temperature and reaction time can be individually determined by appropriately conducting preliminary tests in consideration of various reaction conditions.
  • particularly desirable compounds are as follows.
  • R 5 may be the same or different, or a pyrimidine compound of the formula (I) or a salt thereof
  • the pyrimidine compound of the formula (I) or a salt thereof is a pyrimidine compound of the formula (I) or a salt thereof.
  • the compound of the present invention shows an excellent herbicidal effect when used as an active ingredient of a herbicide.
  • the application range covers a wide range of fields, such as paddy fields, upland, orchards, mulberry fields, and other non-agricultural lands such as forests, agricultural roads, grounds, and plant premises. Can be appropriately selected.
  • the compound of the present invention may be used, for example, as described in the following species: Weeds such as yellowtail, hoyurui, mizugayari, tamagayari, matsubayari, krogwai, etc., weeds such as perica, omodaka, heromodaka, etc .; In addition to weedwort family weeds such as Kikasidasa and Himemisohagi, Ichibi, Malva Asagao, Shiroza, American Kingfisher, Suberihu, Aobu, Agaitou, Ebisda Weeds that can control harmful weeds that can control broadleaf weeds that can control phytosanitary grasses such as, swordfish, sasaetada, hakobe, fir tree fir, fir tree, red crocodile, red croaker, red croaker, yaemdara, sycamore, garland, asparagus japonicus, and e
  • the compound of the present invention is preferably used for corn, soybean, cotton, wheat, rice, rape, castor bean, sugar beet, It is effectively used in the cultivation of sugarcane, turf, peanuts, flax, tobacco, coffee, etc., and especially in the cultivation of corn, soybean, wheat, rice, etc., when selectively controlling harmful weeds.
  • the compound of the present invention is usually mixed with various agricultural auxiliaries to prepare powders, granules, wettable granules, wettable powders, aqueous suspensions, oily suspensions, aqueous solvents, emulsions, tablets, capsules, etc. It is formulated into a form and used as a herbicide, but it can be made into any usual form used in the art as long as it meets the purpose of the present invention.
  • Auxiliaries used in the formulation include diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, mixtures of kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium bicarbonate, sodium sulfate, zeolite, starch, etc.
  • Solvents such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, benzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, N-methyl_2-pyrrolidone, alcohol, etc .; Fatty acid salt, benzoate, alkyl sulfosuccinate, dialkyl sulfosuccinate, polycarboxylate, alkyl sulfate, alkyl sulfate, alkyl aryl sulfate, alkyl diglycol ether sulfate, alcohol Chole sulfate, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonic acid salt, polystyrene sul
  • adjuvants can be selected from those known in the art without departing from the purpose of the present invention.
  • various commonly used auxiliaries such as a bulking agent, a thickener, an anti-settling agent, an anti-freezing agent, a dispersion stabilizer, a safener, and a fungicide can be used.
  • the compounding ratio of the compound of the present invention and various adjuvants is 0.1: 99.9 to 95: 5, preferably 0.2: 99.8 to 85:15.
  • the application rate of the herbicide containing the compound of the present invention cannot be unconditionally specified due to differences in weather conditions, soil conditions, formulation, types of target weeds, application time, and the like. It is applied so as to have a weight of 5 to 5000 g, preferably 1 to 1000 g, and more preferably 10 to 500 g.
  • the present invention also includes a method for controlling harmful weeds by applying such a herbicide.
  • the herbicide containing the compound of the present invention can be mixed or used in combination with other pesticides, fertilizers, safeners, and the like. In this case, more excellent effects and effects may be exhibited.
  • Other pesticides include herbicides, fungicides, antibiotics, plant hormones, and pesticides.
  • a mixed herbicidal composition in which the compound of the present invention and one or more active ingredient compounds of other herbicides are mixed or used in combination, the range of applicable herb species, the time of chemical treatment, the herbicidal activity, etc. It is possible to improve in a favorable direction.
  • the compound of the present invention and the active ingredient compound of the other herbicide may be prepared separately and mixed at the time of spraying, or both may be prepared together and used.
  • the present invention also includes the above-mentioned mixed herbicidal composition.
  • the mixing ratio of the compound of the present invention to the active ingredient compound of other herbicides cannot be unconditionally specified due to differences in weather conditions, soil conditions, drug formulation, application time, application method, and the like.
  • other herbicides contain the active ingredient compound in an amount of 0.01 to 10,000 parts by weight, preferably 0.01 to 1000 parts by weight, per compound.
  • the appropriate amount of application is 0.1 to 10,000 g, preferably 0.2 to 5000 g, more preferably 10 to 3000 g, as the total amount of the active ingredient compound per 1 hectare.
  • the present invention also includes a method for controlling harmful weeds by applying such a mixed herbicidal composition.
  • Examples of the active ingredient compounds of other herbicides include the following (generic names; some of which are under ISO application). Salts, alkyl esters, etc. exist in these compounds even if not specified. If so, they are of course included.
  • aromatic carponic acid such as cloviralide (c 1 opyra 1 id), other benazoline (bena zolin), kink mouth lac (quinc 1 orac), quin merac (qu i nme rac) ), Diflufenzopyr (thiflupyren), and thiazopyr (thiaz opyr), which are said to exhibit herbicidal efficacy by disrupting the hormonal action of plants.
  • pyridazinones such as norflurazon (no rflurazon) and metflurasone (metf1 urazon), pyrazolate (py razolate), pyrazoxyfen (py raz oxyfen), benzophenap (ben zofena) Pyrazoles such as amitrol, fluridone (fluri done), flurmon (flurt amone), diflufenican (difluf en ic an), methoxyphenone (me th oxyphenone), clomazone (cl omaz) one), Su J Recotrion
  • bifluptamide (bef1ubutamid), which inhibits pigment biosynthesis in plants such as chinout, and is said to exhibit herbicidal activity characterized by whitening.
  • diclohop-methyl (dic 1 ofo ⁇ -methy 1), flamprop-M-iiietliyl, pyriphenop-sodium sodium salt (pyri phenop-sod i um) (f1 uazif op—butyl), haloxyfopmethyl (ha1oxyfop—mety1), quizalofopethyl (Quizalof op—et hyl), cyhalofopbutyl (cyh a1 ofo p-) aryloxyphenoxypropionic acid, such as buty 1), phenoxaprophetyl (fe nox apro-e-t hy 1), and alkoxydim sodium salt (a 11 oyd im-sodi) um), Klesoji (Clet hod im), setoxydim (set hoxyd im), tiger J reco xydim (tral koxyd im), flu
  • Chlorimronethyl (ch 1 or imuron-et thy1), sulfomelon-methyle (sulfome turon-methy1), primisulfuron-methyl (primisulfuron-methy1), bensulfuronmethy Le (b en sulfur on—met hy l), Kusu rusulfuron (ch 1 orsu 1 fur on), Methos J refuron methinolle (me tsulfur on—methy 1), sinosulfuron (ci no sulfur on), pyrazosulfuron Chile (py razosulfur on— et hy l), AZIMUS J refuron (azimsu 1 fur on), furasasunofuron (flazasulfur on), rimsulfuron (rims ulfur on), nicosulfuron (nicosu 1 fur on), imazosulfuron ( i ma zos
  • Dinitroaniline such as trifluralin (trif 1 ura 1 in), oryzalin (oryza 1 in), nitrolaline (nitra 1 in), pendimethalin (pendimeta 1 in), ethalfluralin (etha 1 f 1 ura 1 in), Organophosphorus compounds such as amiprofosmethyl (am i rofos-methhy1), bushi mifos (butamifos), anilofos (ani1ofos), piperophos (piper ophos), and chlor Chlorpropham, barban-like fermented bamates, daimuron, cumy luron (cumy lur on) ), Cumylamines such as bromo butide, other ashram (asu 1 am), dithiopyrile, thiazopyre
  • EPTC Butyrate (buty 1 ate), Molinate (mo1inate), Dimepirate (dimepipaterate), Fluazolate (f
  • the compounds of the present invention are safe for crops such as corn, soybean, wheat, and rice, and can be selected for good control of weeds.
  • the compound of the present invention may be mixed or used in combination with one or more of the following compounds in the active ingredient compounds of the other herbicides. A synergistic effect may be obtained.
  • MC PB diclobenyl, kimmerac, chlorotoluron, linuron, isoproturon, promethrin, bromoxynil, bromoxynil 'octanoate, pyridate, bifenox, kafentrazoneethyl, thidiadimine, pyraflumine Chill, furultamon, diflufenican, sulcotrione, diclohopmethyl, flamprophemetyl, tralkodymium, chlorsulfuron, metsulfuron-methyl, prosulfuron, halosulfuron-methyl, flumelam, metoslam, pendimethalin, pa Bread, imazametame benz, sinidoneethyl, ethoxyphenethyl, florasulam, fluazolate, flupoxam, eodosulfuron, metsulfam, pyribenzoxi
  • Synthesis Example 1 Synthesis of ⁇ - (4-promothiophene-2-yl) -14-methylthiopyrimidin-5-ylmethanol (Compound No.2-4)
  • reaction solution was cooled to 0 ° C., ethyl acetate and an aqueous solution of ammonium chloride were added, and the mixture was stirred for a while, followed by extraction.
  • the organic layer was washed with water and then with a saturated saline solution, and dried by adding anhydrous sodium sulfate.
  • the NMR spectrum data for this is as follows.
  • 3-C-thiophen-2-yl represents a thiophen-2-yl group substituted with C1 (chlorine atom) at the 3-position
  • 4-SMe-thiophen-2-yl Le and located in the 4-position Chiofen SMe (methylthio) has been substituted with - represents 2 I le group
  • 2 - (4-CF 3 -SPh) - Chiofen - there with 3 I le is 2
  • Table 1 (continued)
  • a wettable powder or an emulsion prepared according to a usual preparation method was weighed so as to have a predetermined amount of the active ingredient, and diluted with 500 l of water per hectare. Further, 0.1% by volume of an agricultural spreading agent was added to the diluted solution, and foliage treatment was performed with a small spray.
  • Field soil was filled into 1 / 170,000 hectare pots, and seeds of various plants (Nobie, Mehishiba, Agoito, American stag, Malpaa sagao, Ponami, rice, wheat, corn and soybean) were sown.
  • a wettable powder or an emulsion prepared according to the usual formulation method of the compound of the present invention was weighed so as to have a predetermined amount of the active ingredient, diluted into 1500 liters of water per hectare, and soil-treated with a small spray.
  • Paddy soil was filled in 1 / 1,000,000 hectare pots, and seeds of nobie and hoyui were sown and lightly covered with soil. After that, it is left still in the greenhouse at a waterlogging depth of 0.5 to lcni. The next day or two days later, ⁇ rica ⁇ tubers were planted. After that, the waterlogging depth was kept at 3-4cm, and when the Nobie and Hoyurui reached the 0.5-leaf stage and the pericalea reached the primary-leaf stage, the compound of the present invention was prepared according to the usual formulation method. A water dilution of the preparation or emulsion was uniformly dropped with a pipette so as to have a predetermined amount of the active ingredient.
  • Paddy soil was packed in 1 / 1,000,000 hectare pots, paddy was padded, the flooding depth was set to 3 to 4 cm, and the next day the two-leaf rice (cultivar: Nipponbare) was transplanted to a transplanting depth of 3 cm.
  • the compound of the present invention was treated in the same manner as described above.
  • Each of the above components is placed in a high-speed mixing fine granulator, and 20% water is added thereto, followed by granulation and drying to obtain a wettable powder.
  • a wettable powder is obtained by mixing the mixture of the components (1) to (4) and the compound of the present invention at a weight ratio of 9: 1.
  • the wettable powder is obtained by mixing the above components (1) to (4).
  • New Cargen FS-7 (trade name; manufactured by Takemoto Yushi Co., Ltd.) 5 parts by weight
  • (1), (2) and (3) are mixed, passed through a pulverizer, (4) is added, kneaded, and extruded and granulated. Thereafter, drying and sizing are performed to obtain a wettable powder for granules.
  • Sopropol FL trade name; manufactured by Rh ⁇ ne Poulin
  • Solpol 355 trade name; manufactured by Toho Chemical Industry Co., Ltd.
  • IP Solvent 1620 (trade name; manufactured by Idemitsu Petrochemical Co., Ltd.) 32 parts by weight
  • the above components (1) to (6) are mixed and pulverized using a wet pulverizer (Dynomill) to obtain an aqueous suspension.
  • a wet pulverizer Dynomill
  • the pyrimidine compound or a salt thereof according to the present invention is useful as an active ingredient of a herbicide.

Abstract

L'invention concerne des composés de pyrimidine représentés par la formule générale (I) ou leurs sels, ainsi que des herbicides contenant ces composés ou ces sels : (I) où Ar est thiényl éventuellement substitué, furyle éventuellement substitué, ou similaire ; R1 est hydrogène, halogéno, alkyle éventuellement substitué, alcoxy éventuellement substitué, alcényle éventuellement substitué, alcynyle éventuellement substitué, cycloalkyle éventuellement substitué, ou similaire ; R2 et R3 sont chacun hydrogène, halogéno, alkyle, haloalkyle, alcoxy, ou alkylthio ; R4 est hydrogène, alkyle éventuellement substitué, -CH¿2?CN, alcényle éventuellement substitué, alcynyle éventuellement substitué, cycloalkyle éventuellement substitué, ou similaire ; et X?1¿ est oxygène ou soufre.
PCT/JP2001/010060 2000-11-17 2001-11-16 Composes de pyrimidine ou leurs sels, herbicides contenant ces composes ou ces sels, leur procede d'utilisation dans l'elimination des mauvaises herbes WO2002040473A1 (fr)

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7196089B2 (en) 2003-01-29 2007-03-27 Asterand Uk Limited EP4 receptor antagonists
US7417068B2 (en) 2003-10-16 2008-08-26 Asterand Uk Limited EP4 receptor antagonists
WO2013040117A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040021A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
AU2008274558B2 (en) * 2007-07-11 2013-07-18 Syngenta Participations Ag Isothiazole and pyrazole derivatives as fungicides
WO2014151255A1 (fr) 2013-03-15 2014-09-25 Monsanto Technology Llc Méthodes et compositions pour lutter contre les mauvaises herbes
EP3296402A2 (fr) 2011-09-13 2018-03-21 Monsanto Technology LLC Procédés et compositions pour lutter contre les mauvaises herbes
EP3382027A2 (fr) 2011-09-13 2018-10-03 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
EP3434780A1 (fr) 2011-09-13 2019-01-30 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
CN114644596A (zh) * 2022-03-31 2022-06-21 青岛科技大学 一种含氟嘧啶芳胺类化合物及其用途

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JPH0873441A (ja) * 1993-11-01 1996-03-19 Nissan Chem Ind Ltd 新規４，５−ジ置換ピリミジン誘導体及び除草剤

Patent Citations (1)

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JPH0873441A (ja) * 1993-11-01 1996-03-19 Nissan Chem Ind Ltd 新規４，５−ジ置換ピリミジン誘導体及び除草剤

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7196089B2 (en) 2003-01-29 2007-03-27 Asterand Uk Limited EP4 receptor antagonists
US7507754B2 (en) 2003-01-29 2009-03-24 Asterand Uk Limited EP4 receptor antagonists
US7528157B2 (en) 2003-01-29 2009-05-05 Asterand Uk Limited EP4 receptor antagonists
US7858644B2 (en) 2003-01-29 2010-12-28 Asterand Uk Limited EP4 receptor antagonists
US7417068B2 (en) 2003-10-16 2008-08-26 Asterand Uk Limited EP4 receptor antagonists
US7569602B2 (en) 2003-10-16 2009-08-04 Asterand Uk Limited Furan derivatives as EP4 receptor antagonists
AU2008274558B2 (en) * 2007-07-11 2013-07-18 Syngenta Participations Ag Isothiazole and pyrazole derivatives as fungicides
AU2008274558B8 (en) * 2007-07-11 2013-08-01 Syngenta Participations Ag Isothiazole and pyrazole derivatives as fungicides
WO2013040021A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
WO2013040117A1 (fr) 2011-09-13 2013-03-21 Monsanto Technology Llc Procédés et compositions de lutte contre les mauvaises herbes
EP3296402A2 (fr) 2011-09-13 2018-03-21 Monsanto Technology LLC Procédés et compositions pour lutter contre les mauvaises herbes
EP3382027A2 (fr) 2011-09-13 2018-10-03 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
EP3434780A1 (fr) 2011-09-13 2019-01-30 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
EP3434779A1 (fr) 2011-09-13 2019-01-30 Monsanto Technology LLC Procédés et compositions de lutte contre les mauvaises herbes
WO2014151255A1 (fr) 2013-03-15 2014-09-25 Monsanto Technology Llc Méthodes et compositions pour lutter contre les mauvaises herbes
CN114644596A (zh) * 2022-03-31 2022-06-21 青岛科技大学 一种含氟嘧啶芳胺类化合物及其用途
CN114644596B (zh) * 2022-03-31 2024-01-30 青岛科技大学 一种含氟嘧啶芳胺类化合物及其用途

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