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WO1992000976A1 - Derive de pyridine et herbicide selectif - Google Patents

Derive de pyridine et herbicide selectif Download PDF

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Publication number
WO1992000976A1
WO1992000976A1 PCT/JP1991/000918 JP9100918W WO9200976A1 WO 1992000976 A1 WO1992000976 A1 WO 1992000976A1 JP 9100918 W JP9100918 W JP 9100918W WO 9200976 A1 WO9200976 A1 WO 9200976A1
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Prior art keywords
group
carbon atoms
represent
general formula
formula
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English (en)
Japanese (ja)
Inventor
Hiromi Sano
Soji Sugai
Takeshi Endo
Masahiro Shindo
Toyokuni Honma
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Sankyo Co Ltd
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Sankyo Co Ltd
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    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to a novel pyridine derivative having excellent herbicidal activity and a selective herbicide containing the same as an active ingredient.
  • US Patent No. 4,406,690 describes herbicidal activity, but the dosage is described as being high, and its potency> is not mentioned about its selectivity for various crops.
  • German Offenlegungsschrift 3917169 states that the claims are not fully supported by the illustrations and examples of the concrete ligatures, and that the claims do not mention crop selectivity or herbicidal spectrum. It has not been.
  • the present inventors have conducted intensive studies and found that the compound of the present invention and the herbicidal composition can be sufficiently treated at a low dose in both the pretreatment for weed development and the treatment during the weed growing period. They have found that they have an extremely strong herbicidal activity and high selectivity for many crops, and have completed the present invention. (Structure of the invention)
  • the herbicidally active pyridine derivative of the present invention has the general formula (I-:
  • Q represents the following ( ⁇ -1) or (Q-2)!
  • R s and R s are the same or different and represent an alkyl group having 1 to 6 carbon atoms, or R 5 and a force s —
  • alkyl group having 1 to 6 carbon atoms which may have a substituent selected from the following group C
  • an alkenyl group having 2 to 6 carbon atoms which may have a substituent selected from the following group C and It may have a substituent selected from the following group C.
  • the “alkyl group having 1 to 6 carbon atoms” in R 5 , R 6 , group A and group B includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, S-butyl, t-butyl -Butyl, n-pentyl, isopentyl, 2-methylbutyl, neopentyl, n-hexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, A linear or branched alkyl group having 1 to 6 carbon atoms such as 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, etc.
  • R 5 and R 6 connexion alkylene group having 3 or 4 carbon such together
  • propylene a straight-chain or branched al Killen group having 3 or 4 carbon atoms, butylene
  • It is preferably a straight-chain alkylene group having 3 or 4 carbon atoms, and more preferably a straight-chain alkylene group having 4 carbon atoms.
  • halogen atom in R 1 , R 2 and R 3 described above is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom or a chlorine atom, and more preferably a fluorine atom. It is.
  • alkenyl group having 2 to 6 carbon atoms in the groups A and B described above includes, for example, butyl, aryl, 1-methyl-2-bromonyl, 2-methyl-2-bromonyl, Ethyl-2-propenyl, 2-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-ethyl-2-butul, 3-butenyl, 1-methyl 3-butenyl, 2-methyl-3-buteni, 1-ethyl-3-buteni, 2-penten, 1-methyl-2-pentene, 2-meth-2-penten, 3- Penteni, 1-Methyl-3-Penchi, 2-Meth--3 -Pente, 4-Pente, i-Methyl-4-Pente, 2-Men A straight-chain or branched alkenyl group having 2 to 6 carbon atoms such as 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and the like; preferably having 2 to
  • alkynyl group having 2 to 6 carbon atoms in Groups A and B described above is, for example, ethynyl, 2-propynyl, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 2-ethyl 2-propynyl, 2-butul, 1-methyl-2-butynyl, 2_methyl-2-butynyl, 1-ethyl-2-butynyl, 3-butynyl, 1-methyl-3-butynyl, 2-methyl- 3-butul, 1-ethyl-3-butul, 2-pentynyl, 1-methyl-2-pentynyl, 2-methyl-2-pentynyl, 3-pentynyl, 1-methyl- 3-pentynyl, 2-methyl- 3-pentynyl, 2-methyl- 3-pentynyl, 4-penturyl, 1-methyl-4-pentynyl, 2-methyl-4-II.
  • Carbon number 2 such as intinyl, 2-hexyl, 3-hexynyl, 4-hexynyl, 5-hexyl
  • a straight-chain or branched alkynyl group having 3 to 6 carbon atoms preferably a straight-chain or branched alkynyl group having 3 to 6 carbon atoms. More preferably a straight-chain or branched alkynyl group having 3 to 4 carbon atoms, more preferably a straight-chain alkynyl group having 3 to 4 carbon atoms, most preferably It is a straight-chain alkynyl group having 3 carbon atoms.
  • the “C1 to C6 alkyloxycarbonyl group” in Group C described above refers to the “C1 to C6 alkyloxycarbonyl group” in which the above “C1 to C6 alkyl group” is bonded to an oxygen atom.
  • a group is a group bonded to an s' carbonyl group.
  • the “alkyl group having 1 to 6 carbon atoms” in this case is preferably an alkylyl group having 1 to 4 carbon atoms, and more preferably an alkyl group having 1 to 2 carbon atoms.
  • alkenyloxycarbonyl group having 2 to 6 carbon atoms in the aforementioned group C refers to “alkenyl group having 2 to 6 carbon atoms” in which the above “alkenyl group having 2 to 6 carbon atoms” is bonded to an oxygen atom.
  • the “alkenyl group having 2 to 6 carbon atoms” in this case is preferably a straight-chain or branched alkenyl group having 2 to 4 carbon atoms, more preferably a straight-chain or branched alkenyl group having 3 to 4 carbon atoms. It is a straight-chain alkenyl group, most preferably a straight-chain alkenyl group having 3 carbon atoms.
  • alkynyloxycarbonyl group having 2 to 6 carbon atoms in the aforementioned group C refers to “alkynyl group having 2 to 6 carbon atoms” in which the above “alkynyl group having 2 to 6 carbon atoms” is bonded to an oxygen atom.
  • Oxy group is a group bonded to a carbonyl group.
  • the “alkynyl group having 2 to 6 carbon atoms” in this case is preferably a straight-chain or branched alkynyl group having 3 to 6 carbon atoms, more preferably a straight-chain or branched alkynyl group having 3 to 6 carbon atoms.
  • a straight-chain or branched-chain alkynyl group more preferably a straight-chain alkynyl group having 3 to 4 carbon atoms, still more preferably a straight-chain alkynyl group having 3 to 4 carbon atoms, most preferably Is a straight-chain alkynyl group having 3 carbon atoms.
  • amino group optionally having one or two substituents selected from group A” in R 4 is an unsubstituted amino group such as ethylamino, isopropylamino, n-butylamino, t-butylamino.
  • amino groups such as dimethylamino, getylamino, diisopropylamino, di ( ⁇ -butyl) amino, di (: t-butylamino, di (3-methylbutyl) ) Amino, di (3,3-dimethylbutyl; 'amino, diarylamino, di (1-methyl-2-propenyl) amino, di (2-methyl-2-probenyl) amino, di (2- Butenyl) amino, di (3-butenyl) amino, di (3-methyl ⁇ -butenyl) amino, di (2-pentenyl) amino, di (2-propynyl) amino, di (1-methyl-2-propyl)
  • An amino group having two identical substituents selected from group ⁇ such as amino, di (2-butynyl) amino, di (3-butulyl) amino, di (2-pentynyl) amino, or N-methyl- N-ethylamino, N-ethylisopropy
  • the substituent in Group A is preferably an alkenyl group having 2 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms, and more preferably an alkynyl group having 2 to 6 carbon atoms. is there.
  • the “substituted oxy group having a substituent selected from Group B” in R 4 described above includes, for example, methoxy, ethoxy, ⁇ -propoxy, isopropoxy, n-butoxy, 1-methylpropoxy, Methylpropoxy, t-butoxy, 3-methylbutoxy, ⁇ -pentyloxy, 3,3-dimethylbutoxy, vinyloxy, aryloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy 2-butenyloxy, 3-butenyloxy, 3-methyl-2-butenyloxy, 3-pentenyloxy, 2-propynyloxy, 1-methyl-2-propynyloxy, 2-butynyloxy, 1-methyl-2-butynyloxy, 3- Butynyloxy, 4-pentynyloxy, methoxycarbonylmethyloxy, ethoxycarbonylmethyloxy, isopropoxycarbonylmethyloxy n-butoxycarbonylmethyloxy, t-butoxy
  • the substituent in Group B is preferably an alkenyl group having 2 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms, and more preferably an alkynyl group having 2 to 6 carbon atoms.
  • the “substituted thio group having a substituent selected from Group B” in R 4 described above includes, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, 1-methylpropylthio, 2-methylpropyl Thio, t-butylthio, 3-methylbutylthio, ri-pentylthio, 3,3-dimethylbutylthio, vinylthio, arylthio, 1-methyl-2-bromothiol, 2-methyl-2-propenylthio, 2 -Butenylthio, 3-butenylthio, 3-methyl-2-butenylthio, 3-pentenylthio, 2-propynylthio, 1-methyl-2-propynylthio, 2-butynylthio, 1-methyl-2-butynylthio, 3-butynylthio, 4-pentynylthi
  • the aforementioned Q is preferably (Q-1).
  • X mentioned above is preferably an oxygen atom.
  • R 5 and R 6 described above are preferably a methyl group or an alkylene group having 3 or 4 carbon atoms together, more preferably an alkylene group having 3 or 4 carbon atoms together. And most preferably a butylene group.
  • R 1 and R 3 described above are preferably a halogen atom, more preferably a fluorine atom or a chlorine atom, and most preferably a fluorine atom.
  • R 2 described above is preferably a hydrogen atom or a hydrogen atom, and more preferably a hydrogen atom. I am a child.
  • R 4 described above is preferably an alkenylamino group having 2 to 6 carbon atoms, an alkynylamino group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, and an alkyloxy group having 2 to 6 carbon atoms.
  • an alkynylthio group having 2 to 6 carbon atoms or an alkynylthio group having 2 to 6 carbon atoms more preferably an alkynyloxy group having 2 to 6 carbon atoms or an alkynyloxy group having 2 to 6 carbon atoms.
  • From 6 to 6 alkynylthio groups most preferably 2 to 6 carbon atoms Which is the Arukiniruokishi group.
  • Q is - a (Q 1) or (Q-2), X is an oxygen atom, a halogen atom R 1 and R 3 are identical or different and, R 2 force s hydrogen atom,
  • R 4 may have one or two substituents selected from group A, a substituted oxy group having a substituent selected from group B, or a substituted thio group having a substituent selected from group B;
  • An alkenyl group having 2 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms is an alkenyl group having 2 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms.
  • Q is (Q-1) or (Q-2), X is an oxygen atom, R 1 , R 2 and R 3 are the same or different and are a hydrogen atom or a halogen atom, and R 4 is serial B is a substituted Chio group having location ⁇ selected from "substituent Okishi group or the following B having a substituent selected from group" group, R 5 and R e is C 1 to carbon atoms the same or different 6 Compounds which are an alkyl group of 3 or 4 or an alkylene group having 3 or 4 carbon atoms in connection with R 5 and R 6 ;
  • An alkenyl group having 2 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms is an alkenyl group having 2 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms.
  • Q is (Q-1) or (Q-2), X is an oxygen atom, R 1 and R 3 are the same or different and are halogen atoms, R 2 is a hydrogen atom, R 4 is a substituted Chio group having substituents that will be selected from the "substituent Okishi or a group B having a substituent selected from group” group wherein B, R 5 and R s force s the same or different carbon atoms by 1 or a 6 alkyl groups or R 5 and R 6 force s' - compounds connection is the number 3 or 4 alkylene group having a carbon to cord;
  • (6) is (Q-1) or (Q-2), X is an oxygen atom, R 1 and R 3 are independently or differently a fluorine atom or a chlorine atom, and R 2 is a hydrogen atom R 4 is a substituted oxy group having a substituent selected from the group B "or a substituted thio group having a substituent selected from the group B", and R 5 and R 6 are the same or different methyl
  • (7) is (Q-1), R 1 and R 3 are a fluorine atom, R 2 is a hydrogen atom, and R 4 is a substituted oxy group having a substituent selected from the group B "or A compound which is a substituted thio group having a substituent selected from the group B "and is a butylene group together with R 5 and R s ; (8) Q is -1) or (Cl-2), X is an oxygen atom, FT, R 2 and R 3 are the same or different and are a hydrogen atom or a halogen atom, and R 4 has 2 carbon atoms.
  • R 5 and R 6 From 6 to 6 alkynyloxy groups; R 5 and R 6, or different alkyl groups having 1 to 6 carbon atoms; or R s and R 6 are linked together to reduce the number of carbon atoms to 3 Or a compound which is four alkylene groups;
  • Q is - a (Q 1) or (Q-2)
  • X is an oxygen atom
  • R 1 and R 3 force s identical or different halogen atoms
  • R 2 forces a hydrogen atom
  • R 4 is a alkynyloxy group having 2 to 6 carbon atoms
  • RS or RS is a single or different alkyl group having 1 to 6 carbon atoms or R s and R 6 are taken together.
  • Q is (Q-1), X is an oxygen atom, R 1 and R 3 are the same or different and are a fluorine atom or a chlorine atom, R 2 is a hydrogen atom, and R 4 is a carbon atom. R 5 and R s are the same or different and are methyl groups, or R s and R 6 are together and are an alkylene group having 3 or 4 carbon atoms.
  • Q is (Q-1), R 1 and R s are fluorine atoms, R 2 is a hydrogen atom, R 4 is an alkynyloxy group having 2 to 6 carbon atoms. , R 5 and a force; and a compound which is a butylene group together.
  • R 1 and R s are fluorine atoms
  • R 2 is a hydrogen atom
  • R 4 is an alkynyloxy group having 2 to 6 carbon atoms.
  • R 5 and a force and a compound which is a butylene group together.
  • Examples of the compound of the present invention include the compounds described in Table 11, but the present invention is not limited to these compounds.
  • (Q-la) and (Q-lb) represent a structure represented by the following formula, (Q-2) has the same meaning as described above, "" represents a methyl group, “EtJ represents a dityl group,“ nPr J represents a maltopropyl group, “iPr” represents an isopropyl group, “11” represents an aryl group, and “Prg” represents a 2-propyl group.
  • preferred compounds include
  • more preferred compounds include
  • more preferred compounds include
  • more preferred compounds include:
  • R 1 , R 2 and R 3 have the same meanings as above, and Y 1 and Y 2 are the same or different and represent a halogen atom. Y 1 and Y 2 are preferably the same or different and are fluorine Atom or chlorine atom.
  • This step is a step for producing a compound represented by the general formula (IV) (intermediate of the compound of the present invention) by reacting the compound represented by the general formula (III) with ammonia.
  • the compound of formula (III), which is a raw material of this step, can be easily obtained as a reagent such as 2,6-dichloropyridine, 2,6-dibromopyridine, or 2,6-difluoropyridine.
  • a reagent such as 2,6-dichloropyridine, 2,6-dibromopyridine, or 2,6-difluoropyridine.
  • the alcohol to be used is a lower alcohol such as methanol, ethanol, or isoblovanol.
  • the reaction temperature is 50 to 300 ° C., preferably 90 to 200 ° C.
  • the reaction time depends mainly on the reaction temperature, the starting compound and the type of solvent used. However, it is usually 3 to 70 hours, preferably 10 to 30 hours ⁇ (second step)
  • R 9 is an amino group optionally having one or two substituents selected from the following group A, A substituted oxy group having a substituent selected from the group or a substituted thio group having a substituent selected from the following group B.
  • alkyl group having 1 to 6 carbon atoms which may have a substituent selected from the following group C an alkenyl group having 2 to 6 carbon atoms which may have a substituent selected from the following group C and An alkynyl group having 2 to 6 carbon atoms which may have a substituent selected from the following group C.
  • a compound represented by the general formula ' ⁇ ' is subjected to a nucleophilic substitution reaction in the presence of a base using the compound of the formula (IV) produced in the first step as a raw material;
  • This is a step of producing a compound represented by I a! (An intermediate of the compound of the present invention).
  • This step is performed in Hetrocycles, (1986) 24, 3213 Yakugaku Zasshi (1968) 88, 1610 Chem. Soc, (1964) 3736 Advances in Heterocyclic Chemistry; AR Katritzk, FRS Ed .; Academic press, Inc .: California, 1988; vol. 43 p301 Comprehensive Heterocyclic Chemistry; AR Katritzky Ed .; Pergamon: Oxford, 1984; vol. 2 pl65-315 and the like.
  • aqueous ammonia for example, alkali metals such as sodium hydroxide and potassium hydroxide, for example, alkali metal carbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, and potassium carbonate, for example, hydrogen Alkali metal hydrides such as sodium and potassium hydrides; organic metal salts such as lithium diisopropylamide, lithium hexamethyldisilazane and potassium hexamethyldisilazane; Salts such as 1,4-diazabicyclo [2,2,2] octane, 1,8-diazabicyclo [5,4,0] cycloaliphatic tertiary amines such as pendene, such as pyridine, 4-dimethylaminopyridine Aromatic tertiary amines, etc .; Salts, alkali metal hydrides, organometallic salts, Ru cycloaliphatic tertiary Amin class der.
  • alkali metals such as sodium hydrox
  • the solvent used is not limited as long as it does not participate in anti-s, but aromatic hydrocarbons such as benzene, toluene and xylene, for example, acetyl ether, tetrahydrofuran, dimethoxyethane Ethers, for example, alcohols such as methanol and ethanol, for example, nitriles such as acetate and propionyl nitrile, for example, amides such as dimethylformamide and dimethylacetamide, for example, dimethyl sulfoxide Sulfoxides, water, etc., preferably aromatic hydrocarbons, ethers, amides, and sulfoxides.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • acetyl ether tetrahydrofuran
  • dimethoxyethane Ethers for example, alcohols such as methanol and ethanol
  • nitriles such as acetate and propionyl n
  • the reaction temperature is from 120 to 15 ° C, preferably from 20 to 10 CTC.
  • the reaction time depends mainly on the reaction temperature, the starting compound and the type of the solvent used; it varies depending on the type of the solvent, but is usually 30 minutes to 70 hours, preferably 3 hours to 30 hours.
  • Some of the compounds represented by the formula ( ⁇ 'I a) are 2-aminoquinoline. Some are easily available as reagents,
  • the compound represented by the general formula (VIb) is heated by heating an ammonia solution or an alcohol solution obtained by dissolving ammonia in the compound represented by the general formula (III) in a sealed tube.
  • This is a process for producing an intermediate of the compound of the formula (1), which is carried out according to the first step.
  • the alcohol used is a lower alkyl alcohol such as methanol, ethanol, or isopropanol.
  • the reaction temperature is from 90 to 350 ° C, preferably from 120 to 250 ° C.
  • the reaction time varies depending on the reaction temperature, the starting compound or the type of the solvent used.
  • the reaction time is generally 10 to 100 hours, preferably 15 to 50 hours.
  • This step is performed using the force produced in the second and third steps or a commercially available lig compound represented by the general formula (VI), Med. Chem., (1979) 22, 31; Reaction of thiophosgene in the presence of solvent O according to the method described in Cheni. Acta., (198 3) 6148.
  • the reaction in this step can be completed in a short time by being carried out in the presence of an acid or a base.
  • the acid used include mineral acids such as hydrochloric acid, sulfuric acid, and phosphoric acid.
  • Examples of the base to be used include alkali metals such as sodium hydroxide and hydroxylated lime; alkali metal carbonates such as sodium hydrogen carbonate, sodium carbonate and carbonated lime; Aliphatic tertiary amines such as diazabicyclo [2,2,2] octane, 1, diazabicyclo [5,4,0] indene, for example, aliphatic tertiary amines such as trimethylamine, triethylamine, etc. For example, aromatic tertiary amines such as pyridine, and preferred are alkali metals and alkali metal carbonates.
  • alkali metals such as sodium hydroxide and hydroxylated lime
  • alkali metal carbonates such as sodium hydrogen carbonate, sodium carbonate and carbonated lime
  • Aliphatic tertiary amines such as diazabicyclo [2,2,2] octane, 1, diazabicyclo [5,4,0] indene
  • the solvents used are not limited, as long as they do not participate in the reaction, but include, for example, aromatic hydrocarbons such as benzene, toluene and xylene, for example esters such as ethyl acetate and propyl acetate, for example Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, and water, and a mixed solvent such as chloroform-water and toluene-water may be used.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • esters such as ethyl acetate and propyl acetate
  • Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane
  • water and a mixed solvent such as chloroform-water and toluene-water may be used.
  • the reaction temperature is from 120 to 150 ° C, preferably from 0 to 100 ° C.
  • the reaction time is usually 30 minutes to 30 hours, preferably 2 hours to 20 hours, depending on the reaction temperature, the starting compound or the type of solvent used.
  • the azothiocyanate of the formula (VII) produced in the fourth step is used as a raw material.
  • a compound represented by the general formula (IX) (intermediate of the compound of the present invention) is produced.
  • This is the step of performing The reaction can be completed in a short time by adding a base as a catalyst.
  • Examples of the base used include alkali metal hydrides such as sodium hydrogen hydride and potassium hydrogen hydride, and organic metal salts such as lithium diisopropylamide, lithium hexamethyldisilazane, and potassium hexamethyldisilazane.
  • alkali metal hydrides such as sodium hydrogen hydride and potassium hydrogen hydride
  • organic metal salts such as lithium diisopropylamide, lithium hexamethyldisilazane, and potassium hexamethyldisilazane.
  • Trialkylamines such as ethylamine and ethyldiisopropylamine, for example, cyclic fats such as 1,4-diazabicyclo [2,2,2] octane and 1,8-diazabicyclo [5,4,0] ndene
  • Aromatic tertiary amines for example, aromatic tertiary amines such as pyridine and 4-dimethylaminopyridine, and preferably trialkylamines and cycloaliphatic amines.
  • the solvent used is not limited as long as it does not participate in the reaction.
  • aromatic hydrocarbons such as benzene, toluene, and xylene, for example, dichloromethane, tetrachloroethane, and 1,2-dichloroethane
  • halogenated hydrocarbons for example, ethers such as diethyl ether, tetrahydrofuran, and dimethyloxetane; and nitriles such as acetonitrile and propionylnitrile; preferably, aromatic hydrocarbons, Ethers.
  • the reaction temperature is from 0 to 150 ° C, preferably from 20 to 100 ° C.
  • the reaction time varies depending on the reaction temperature, the starting compound and the type of the solvent used, but is usually 30 minutes to 70 hours, preferably 3 hours to 30 hours. (Step 6)
  • the reaction is achieved by heating the compound of formula (X) and the compound of formula ( ⁇ '1) in the presence or absence of a solvent.
  • the reaction can be completed in a short time by adding a catalyst.
  • the catalyst used is, for example, a mineral acid such as sulfuric acid or phosphoric acid, a fatty acid such as acetic acid, or a sulfonic acid such as paratonin sulfonic acid.
  • the solvent to be used is not limited as long as it does not participate in the reaction.
  • Examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene, for example, dichloromethane, tetrachloroethane, trichloroethane, 1 Halogenated hydrocarbons such as 1,2-dichlorobenzene, for example ketones such as methylethyl ketone, getyl ketone and methyl isobutyl ketone, for example esters such as diacetyl acetate and ethyl propionate, for example acetic acid And carboxylic acids such as brobionic acid.
  • the reaction temperature is usually 70-250 ° C, preferably 90-20 CTC.
  • the reaction time varies depending mainly on the reaction temperature, the starting compound and the type of the solvent used, but is usually 2 to 72 hours, preferably 3 hours to 50 hours.
  • R 1 , R 2 , R s , R 4 and X are as defined above.
  • the compound represented by the general formula produced in the fifth step ⁇ ⁇ 'and phosgene
  • the compound represented by the general formula (lb) by reacting thiophosgene with a base in the presence or absence of a solvent in the presence of a base, the compound represented by the general formula (lb) (in the general formula (I) of the present invention, 0 ⁇ )).
  • the solvent used is not limited as long as it does not participate in the reaction.
  • examples include halogenated hydrocarbons such as dichloromethane, chloroform, and tetrachloromethane, for example, dimethyl ether, tetrahydrofuran, and dioxane.
  • Ethers for example, aromatic hydrocarbons such as benzene and toluene; sulfoxides, for example, dimethyl sulfoxide; and amides, for example, N, N-dimethylformamide.
  • Examples of the base used include aliphatic tertiary amines such as small methylamine and triethylamine; aromatics such as pyridine and quinoline; tertiary amines such as sodium hydroxide and carbonic acid.
  • Organic bases such as lime and sodium carbonate, for example, alkali metal hydrides such as sodium hydride, potassium hydride and lithium hydride.
  • the reaction is carried out usually at a temperature of from 20 to 40 ° C, preferably from 0 to 25 ° C.
  • the reaction time is mainly 15 minutes to 5 hours, and preferably 30 minutes to 3 hours, depending on the reaction temperature, the starting compound or the type of the solvent used.
  • R 7 is an amino group having one or two substituents selected from Group A, a substituent selected from Group B Or a substituted thio group having a substituent selected from the group B, Z 1 represents a halogen atom, .Z 1 preferably represents a fluorine atom or a chlorine atom.
  • the compound represented by the general formula (XIIa) and the compound represented by the general formula (XIII ′) The compound in the presence or absence of a solvent selected, by the presence of a base reaction, the compound represented by the general formula (I c) (compounds of general formula (I), wherein the R 4 forces group A substituted or unsubstituted amino group having one or two substituents selected from the group B, or a substituted thio group having a substituted moiety selected from the group B).
  • the compound represented by the general formula (XIla), which is a starting compound in this step, can be produced by a method according to the sixth step or the seventh step.
  • the solvent used in this step is not limited as long as it does not take part in the reaction.
  • aromatic hydrocarbons such as benzene, toluene, and xylene
  • dimethyl ether, tetrahydrofuran, dimethoxyethane Ethers such as methanol, alcohols such as ethanol, acetonitrile, nitriles such as propionylnitrile, amides such as dimethylformamide, dimethylacetamide, and dimethyl sulfoxide Sulfoxides and the like
  • aromatic hydrocarbons such as benzene, toluene, and xylene
  • dimethyl ether, tetrahydrofuran, dimethoxyethane Ethers such as methanol
  • alcohols such as ethanol
  • acetonitrile such as propionylnitrile
  • amides such as dimethylformamide, dimethylacetamide, and dimethyl sulfoxide Sulfoxides and the like
  • the base used is, for example, aqueous ammonia.
  • Alkali metals such as sodium hydroxide and potassium hydroxide, for example, alkali metal carbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, and potassium carbonate, for example, hydrogen
  • Alkali metal hydrides such as sodium hydride and potassium hydride, for example, organic metal salts such as lithium diisopropylamide, lithium hexamethyldisilazane, and potassium bexamethyldisilazane, lower metal salts such as butyllithium Cycloaliphatic tertiary amines such as 1,4-diazabicyclo [2,2,2] octane and 1,8-diazabicyclo [5,4,0] ndene, such as pyridine and 4-dimethylaminopyridine Aromatic tertiary amines and the like, preferably alkali metal carbonates , Alkali metal hydrides, organic metal salts, and
  • the reaction temperature is from 120 to 15 (TC, preferably from 0 to 100).
  • the reaction time depends mainly on the temperature, the starting compounds and the type of solvent used. Power is usually 30 minutes to 30 hours, preferably 2 to 15 hours.
  • Z 2 represents an OH group, an SH group, or an NH 2 group
  • R 8 is a substituent selected from Group C.
  • Y represents a halogen atom
  • Y preferably represents a fluorine atom or a chlorine atom.
  • the compound represented by the general formula (XI lb) is reacted with the compound represented by the general formula (XIV) in the presence or absence of a solvent in the presence of a base to obtain a compound represented by the general formula (XI A compound represented by Id) (in the general formula (I) of the present invention, an amino group having one or two substituents selected from the group R 4 , a substituent having a substituent selected from the group B) Or a substituted thio group having a substituent selected from Group B).
  • the compound represented by the general formula (XIlb) as a starting compound in this step can be produced by a method according to the sixth step or the seventh step.
  • the solvent used in this step is not limited as long as it does not take part in the reaction.
  • aromatic hydrocarbons such as benzene, toluene, and xylene, such as dimethyl ether, tetrahydrofuran, and dimethoxyethane Ethers such as alcohols such as methanol and ethanol, nitriles such as acetonitrile and propionylnitrile, amides such as dimethylformamide and dimethylacetamide, and sulfoxides such as dimethylsulfoxide And the like, preferably aromatic hydrocarbons, neethers, amides, sulfones, etc. It is a foxide.
  • alkali metals such as ammonia water, sodium hydroxide and potassium hydroxide, and alkali metal carbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, sodium carbonate and carbonated lime.
  • Alkali metal hydrides such as sodium hydride and potassium hydride; organic metal salts such as lithium diisopropylamide, lithium hexamethyldisilazane and potassium hexamethyldisilazane; lower alkyl salts such as butyllithium Metal salts, such as 1,4-diazabicyclo [2,2,2] octane and 1,8-diazabicyclo [5,4,0] cycloaliphatic tertiary amines such as pendene, for example, pyridine, 4-dimethylaminopyridine And aromatic tertiary amines such as S, alkali metal hydrides, organometallic salts, Ru cycloaliphatic tertiary Amin class der.
  • the reaction temperature is from 120 to 150 ° C, preferably from 0 to 100 ° C.
  • reaction time varies depending mainly on the reaction temperature, the starting compound and the type of the solvent used, but is usually 30 minutes to 30 hours, preferably 2 to 15 hours.
  • each target compound is isolated by filtration according to a conventional method, or by filtering out a precipitated crystal or diluting with water and extracting with a water-immiscible solvent. If necessary, it can be purified by recrystallization or column chromatography.
  • Example 3 25% of the compound obtained in Example 3, 2.5% of sodium dodecylbenzenesulfonate, 2.5% of calcium ligninsulfonate and 70% of diatomaceous earth were mixed and ground to obtain a wettable powder.
  • Example 2 15% of the compound obtained in Example 2, cyclohexanone 35%, calcium salt of dodecylbenzenesulfonate 2.61%, polyoxyethylene distyrenated methylphenol ether 3.96%, polyoxyethylene alkyl ether 1.87 %, 0.26% of polyoxyethylene nonylphenyl ether phosphate calcium salt, 1.3% of xylene and 40% of mesitylene were uniformly dissolved to obtain an emulsion.
  • Example 2 30% of the compound obtained in Example 1, 2.61% of calcium salt of dodecylbenzenesulfonic acid, 3.96% of polyoxyethylene distyrenated methylphenol ether, 1.87% of polyoxyethylene alkyl ether, 1.87% of polyoxyethylene Emulsion was obtained by mixing 0.26% of nonyl-funinyl ether calcium phosphate and 61.3% of xylene well.
  • Example 2 5% of the compound obtained in Example 2, 30% of bentonite, 62.5% of talc, 2% of sodium ligninsulfonate, 0.35% of sodium dioctyl sulfosuccinate, 0.35% of propylene glycol. 075% and water 0.075% were uniformly mixed and pulverized. 20 parts by weight of water was added to 100 parts by weight of this mixture, kneaded, processed into granules of 14 to 32 mesh using an extrusion granulator, and dried to obtain granules. (Formulation Example 10) (Granules)
  • Example 4 4% of the compound obtained in Example 4, 30% of bentonite, 63% of clay, 1% of polybutyl alcohol and 2% of sodium benzenesulfonic acid sodium salt were uniformly mixed and pulverized. 20 parts by weight of water was added to 100 parts by weight of this mixture and kneaded. The mixture was processed into granules of 14 to 32 mesh using two extruding granulators, and then dried to obtain granules.
  • Example 3 4% of the compound obtained in Example 3, 35% of bentonite, 58% of talc, 2% of sodium alkylnaphthalenesulfonate and 1% of sodium sodium dioctyl sulfosuccinate were uniformly mixed and pulverized. 100 parts by weight of this mixture was mixed with 20 parts by weight of water, kneaded, processed into granules of 14 to 32 mesh using an extrusion granulator, and dried to obtain granules.
  • Example 2 80% of the compound obtained in Example 2, sodium dodecyl pencene sulfonate 3%, sodium alkyl naphthalene sulfonate 2%, sodium lignin sulfonate 2%, synthetic amorphous silica 3%, strength 10% of the oligin was mixed, pulverized by an air-mill, mixed again, and packed.
  • the wettable powder of Formulation Example 13 (15%), kaolin clay (50%), talc (25%) and ligninsulfonic acid sodium salt (10%) were mixed in a rotary mixer or a fluidized-bed mixer, and were granulated by spraying water. When most became 1.0-0.15 mm, the condyles were removed, dried and sieved. The oversized material was crushed to give granules of 1.0-0.15 mm.
  • Example 3 80% of the compound obtained in Example 3, special holica hongjun polymer sodium salt 1.2 5%, 3.75% water, 3% sodium dodecylbenzenesulfonate, 7% dextrin and 5% titanium oxide, then pulverize with an air mill and add to a rotary mixer or fluid bed mixer, Water was sprayed to granulate. When most of them became 1.0-0.15 mm, the granules were taken out, dried and sieved. The oversized material was crushed to obtain granules of 1.0-0.15 mm.
  • the annual weeds Akinoenokorogusa, Inubie, Seibanmorokoshi, Ichibi, Onamimomi, Inuhozuki, Noharagarashi, and various crops of wheat, soybean and maize are sown. Seeds were then covered with the same soil.
  • the compound of the present invention was prepared in a wettable powder of a predetermined concentration, and 15 ml of the powder was uniformly treated per pot. The pots after the treatment were placed in a glass greenhouse, and after 3 weeks, the growth state of the plants was observed, and the herbicidal efficacy was determined according to the following criteria.
  • Table 13 shows the results of Test Example 2.
  • the compound of the present invention shows an excellent herbicidal effect against various weeds by both pre-emergence and post-emergence treatment methods, and also shows excellent selectivity between crops and weeds.
  • various weeds growing in the field for example, Soba kazula, Sanae yude, Suberihu, Hakobe, Shiroza, Agaei tou, Noharagarashi, Nazuna, Ichibi, American dragonfly Broadleaf weeds such as mosquitoes, field panjis, yaemgras, balsam pears, balsam pears, pygmy pygmy moss, pygmy moss, shirobana kosemasagao, yinhozuki, ooinu nofuguri, linu camouflage, corn marii gold, corn marigold, sylvanus Grass weeds, such as cedar
  • grass weeds such as porpoise
  • broadleaf weeds such as oak, azaena, kikasigusa, and mizohakobe
  • tamagayari firefly
  • matsubayashi matsubayashi
  • mizugayari It shows herbicidal activity against grasses and does not show problematic phytotoxicity against rice.
  • it can be used not only in fields and paddy fields, but also in orchards, mulberry fields, and non-agricultural lands. Can be.
  • the compound of the present invention also has an action of suppressing the growth of the plant without killing the plant. Therefore, for example, various methods such as prevention of lodging due to short rice paddy rice, reduction of the number of times of cutting by suppressing growth of the lawn, etc. Expected to be useful.
  • powders are prepared by diluting with a carrier such as a solid carrier or a liquid carrier and, if necessary, adding other preparations such as surfactants and auxiliary agents. , Coarse powders, granules, fine granules, emulsions, suspensions, wettable powders, flowables , Water solvents, liquid preparations and the like.
  • a carrier such as a solid carrier or a liquid carrier
  • Carriers are synthetic or natural, inorganic, which are mixed with herbicides and plant growth regulators to help the active ingredient reach the plant or to facilitate storage, transport or handling of the active ingredient. Or an organic substance.
  • Suitable solid carriers include, for example, clay, talc, dikryte, bamiki ureite, slaked lime, silica sand, diatomaceous earth, kaolin, attapulgite clay, bentonite, calcium carbonate, ammonium sulfate, acid clay, hydrous clay Inorganic substances such as amorphous silicon dioxide, calcite, dolomite, phosphorous lime, and zeolite; resins such as coumarone resin, alkyd resin, petroleum resin, polychlorinated vinyl, coal balgam, dammar gum, and stergel; carnapalow, Waxes such as paraffin wax; nut shells such as walnuts and nuts; tobacco flour, flour, wood flour, kinako flour, starch, soy flour; urea.
  • Suitable liquid carriers include, for example, water; aromatic hydrocarbons such as xylene and methylnaphthalene; alcohols such as methanol, ethanol, isopropanol, ethylene glycol and cerolylbu; acetone, cyclohexanone and isophorone. Ketones; vegetable oils such as soybean oil and cottonseed oil; polar solvents such as dimethyl sulfoxide, ⁇ , ⁇ -dimethylformamide, and acetonitrile.
  • Surfactants used for dispersion, emulsification, wetting, spreading, etc. may be ionic or non-ionic.
  • Suitable anionic surfactants include, for example, alkyl sulfates such as sodium salt of lauryl sulfate; alkyl sulfonates such as sodium salt of paraffinsulfonic acid; sodium salt of dodecylbenzenesulfonic acid
  • Alkyl aryl sulfonates such as sodium salt of naphthalenesulfonic acid; dialkyl sulfosuccinates such as sodium salt of getylhexylsuccinic acid; phosphorus of polyoxynitylene nonylphenyl ether Esthetics and their salts, such as polyethylene ethylene; Monoteryl phosphates; poly (or alkylaryl) ether sulfates, such as sulfates and salts thereof, and lignin sulfonates, such as sodium or calcium salts of ligninsulfonic acid. Salts of higher fatty acids, such as sodium oleate, and the like. .
  • Suitable cationic surfactants include, for example, salts of higher fatty acid amines such as laurylamine acetate; higher fatty acid amine oxidized ethylene condensates such as polyoxetylene stearylamine.
  • Suitable nonionic surfactants include, for example, glycerides of fatty acids; sucrose esters of fatty acids; polyoxyethylene alkyl esters such as polyoxyethylene oleate; ethylene oxide condensates of higher fatty alcohols.
  • sorbitan fatty acid esters such as monoalkylates and their ethylenoxide adducts, and polyoxyxylene sorbin fatty acid esters.
  • CMC carboxymethylcellulose
  • PAP isopropyl propyl phosphate
  • the range of application is expanded by mixing with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers, soil conditioners, etc. And save labor.
  • the treatment method is usually to formulate a preparation and treat it with soil, foliage or flooding before or within about one month after germination of the weed.
  • Soil treatment includes soil surface treatment and soil admixture treatment.
  • Stalk and foliage treatment includes local treatment that treats only weeds so that they do not adhere to crops.
  • the compound of the present invention can be used as a herbicide for paddy fields, fields, orchards, pastures, turf lands, forests or non-agricultural lands.
  • the amount of treatment varies depending on the weather conditions, formulation, treatment time, treatment method, location, target weeds, target crops, etc.
  • the active ingredient is 1 g to 100 g per are, preferably 2 g.
  • Emulsions, wettable powders, suspending agents, etc. are usually prepared in a predetermined amount of 1 to 10 liters of water per are (surfactant, polyoxyethylene resin if desired).
  • Spreading agents such as acid, lignin sulfonate, abietic acid salt, dinaphthyl methane disulfonate, and paraffin can be added.) Dilute and treat, and granules are usually treated without any dilution I do.

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Abstract

Nouveau dérivé de pyridine représenté par la formule générale (I), ledit dérivé de pyridine ayant une activité herbicide très puissante et une sélectivité très élevée contre plusieurs cultures. Dans cette formule, Q représente Q-1 ou Q-2, où X représente oxygène ou soufre et R5 et 6 peuvent être identiques ou différents l'un de l'autre, chacun représentant alkyle C¿1? à C6, ou R?5 et R6¿ peuvent être combinés pour représenter alkylène C¿3? ou C4; R?1, R2 et R3¿ peuvent être identiques ou différents les uns des autres, chacun représentant hydrogène ou halogène; et R4 représente amino facultativement monosubstitué ou bisubstitué, hydroxy substitué ou thio substitué, ou bien encore R3 et R4 peuvent être combinés pour former -CH=CH-CH=CH-.
PCT/JP1991/000918 1990-07-12 1991-07-10 Derive de pyridine et herbicide selectif Ceased WO1992000976A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999055693A3 (fr) * 1998-04-28 1999-12-16 Novartis Ag Nouveaux herbicides
CN1326849C (zh) * 2005-09-23 2007-07-18 南开大学 六氢酞酰亚胺类化合物及其制备和用途
CN1331863C (zh) * 2005-08-17 2007-08-15 南开大学 一种酰亚胺类化合物及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4072499A (en) * 1976-12-22 1978-02-07 Monsanto Company Use of pyridyl phthalimides as plant growth regulants
JPS5323965A (en) * 1976-08-12 1978-03-06 Ciba Geigy Ag 3*44dimethyll22hydroxyy55oxoo2*55dihydropyrrole derivative* its preparation and combating agent against harmful animals or plants containing same as acitive ingredient
US4124375A (en) * 1977-10-12 1978-11-07 Monsanto Company Substituted phthalimides for regulating the growth of plants

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5323965A (en) * 1976-08-12 1978-03-06 Ciba Geigy Ag 3*44dimethyll22hydroxyy55oxoo2*55dihydropyrrole derivative* its preparation and combating agent against harmful animals or plants containing same as acitive ingredient
US4072499A (en) * 1976-12-22 1978-02-07 Monsanto Company Use of pyridyl phthalimides as plant growth regulants
US4124375A (en) * 1977-10-12 1978-11-07 Monsanto Company Substituted phthalimides for regulating the growth of plants

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Title
CHEMICAL ABSTRACTS, Vol. 114, No. 17, Abs. No. 164251f. *
CHEMICAL ABSTRACTS, Vol. 90, No. 25, Abs. No. 203719x. *
CHEMICAL ABSTRACTS, Vol. 98, No. 15, Abs. No. 121386n. *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999055693A3 (fr) * 1998-04-28 1999-12-16 Novartis Ag Nouveaux herbicides
US6369002B1 (en) 1998-04-28 2002-04-09 Syngenta Crop Properties, Inc. N-heteroaryl-substituted pyridine derivatives and their use as herbicides
CN1331863C (zh) * 2005-08-17 2007-08-15 南开大学 一种酰亚胺类化合物及其制备方法
CN1326849C (zh) * 2005-09-23 2007-07-18 南开大学 六氢酞酰亚胺类化合物及其制备和用途

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