WO1994007868A1 - Derives de naphtol, leur procede de production et leur utilisation comme herbicides - Google Patents

Derives de naphtol, leur procede de production et leur utilisation comme herbicides Download PDF

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Publication number
WO1994007868A1
WO1994007868A1 PCT/JP1993/001275 JP9301275W WO9407868A1 WO 1994007868 A1 WO1994007868 A1 WO 1994007868A1 JP 9301275 W JP9301275 W JP 9301275W WO 9407868 A1 WO9407868 A1 WO 9407868A1
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group
groups
naphthol derivative
alkyl
atom
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Mitsunori Hiratsuka
Toru Uekawa
Naonori Hirata
Kazuo Saito
Hiroyuki Yogai
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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Priority to EP93919629A priority Critical patent/EP0662963A1/fr
Priority to AU49833/93A priority patent/AU4983393A/en
Priority to BR9307115A priority patent/BR9307115A/pt
Publication of WO1994007868A1 publication Critical patent/WO1994007868A1/fr
Anticipated expiration legal-status Critical
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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
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
    • C07C239/08—Hydroxylamino compounds or their ethers or esters
    • C07C239/22—Hydroxylamino compounds or their ethers or esters having oxygen atoms of hydroxylamino groups esterified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
    • C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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 with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to novel naphthol derivatives, a method for producing the same and their use as herbicides.
  • naphthol derivatives represented by the following formula (I) are excellent compounds as herbicides which can control weeds widely generated in crop lands or non-crop lands at low dosage rate, have a broad herbicidal spectrum and also can safely be used for no-till cultivation.
  • the present invention is based on this finding.
  • the present invention provides naphthol derivatives represented by the formula (I) [hereinafter referred to as the present compound(s)], a method for producing the same and their use as herbicides:
  • each of R 1 and R 2 which may be the same or different, represents a hydrogen atom, a C 1 -C 6 alkyl group, a C 3 -C 6 cycloalkyl group, or a phenyl group optionally substituted with at least one member selected from the group consisting of C 1 -C 6 alkyl groups, halogen atoms, C 1 -C 6 alkoxy groups, halo-C 1 -C 6 alkyl groups, nitro groups, cyano groups and C 1 -C 6 alkoxycarbonyl groups or a benzyl group optionally substituted with at least one member selected from the group consisting of C 1 -C 6 alkyl groups, halogen atoms, C 1 -C 6 alkoxy groups, halo-C 1 -C 6 alkyl groups, nitro groups, cyano groups and C 1 -C 6 alkoxycarbonyl groups, or R 1 and R 2 are bonded together at their ends to form a C 4
  • each of R 3 and R 4 which may be the same or different, represents a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group or a halogen atom;
  • X represents CH or a nitrogen atom
  • Z represents CH or a nitrogen atom
  • W represents an oxygen atom or a sulfur atom; each of Y 1 , Y 2 and Y 3 which may be the same or different, represents a hydrogen atom, a C 1 -C 6 alkyl group, a halogen atom or a C 1 -C 6 alkoxy group.
  • each of R 3 and R 4 which may be the same or different, is preferably a C 1 -C 6 alkoxy, and more preferably both of R 3 and R 4 are methoxy groups.
  • W is preferably an oxygen atom.
  • examples of the C 1 -C 6 alkyl groups and alkyl moiety of the haloalkyl groups include methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl groups and the like;
  • examples of the C 1 -C 6 alkoxy groups and alkoxy moiety of the C 1 -C 6 alkoxycarbonyl groups include methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, n-hexyloxy groups and the like;
  • C 3 -C 6 cycloalkyl groups examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl groups and the like;
  • halogen atom and halogen moiety of the halo-C 1 -C 6 alkyl groups include fluorine, chlorine and bromine;
  • halo-C 1 -C 6 alkyl groups examples include 2-chloroethyl, 2-bromoethyl, 3-fluoropropyl, 2- chloropropyl, 4-chlorobutyl, 6-chlorohexyl groups and the like;
  • examples of the phenyl group optionally substituted with at least one member selected from the group consisting of C 1 -C 6 alkyl groups, halogen atoms, C 1 -C 6 alkoxy groups, halo-C 1 -C 6 alkyl groups, nitro groups, cyano groups and C 1 -C 6 alkoxycarbonyl groups include phenyl, 2-methylphenyl, 3-ethylphenyl, 4-hexylphenyl, 2,6-dimethylphenyl, 2-fluorophenyl, 2-chlorophenyl, 3-bromophenyl, 2,4-dichlorophenyl, 2-chloro-4-methylphenyl, 3-methoxyphenyl, 3-ethoxyphenyl, 4-i-propoxyphenyl, 3-hexyloxyphenyl, 3-methoxycarbonylphenyl, 3-ethoxycarbonylphenyl, 4-i-propoxycarbonylphenyl, 3-hexyloxyphenyl
  • examples of the benzyl group optionally substituted with at least one member selected from the group consisting of C 1 -C 6 alkyl groups, halogen atoms, C 1 -C 6 alkoxy groups, halo-C 1 -C 6 alkyl groups, nitro groups, cyano groups and C 1 -C 6 alkoxycarbonyl groups include benzyl, 2-methylbenzyl, 3-ethylbenzyl, 4-hexylbenzyl, 2,6-dimethylbenzyl, 2-fluorobenzyl, 2-chlorobenzyl, 3-bromobenzyl, 2,4-dichlorobenzyl, 2-chloro-4-methylbenzyl, 3-methoxybenzyl, 3-ethoxybenzyl, 4-i-propoxybenzyl, 3-hexyloxybenzyl, 3-methoxycarbonyl- benzyl, 3-ethoxycarbonylbenzyl, 4-i-propoxycarbonylbenzyl, 3-hexyloxybenz
  • examples of the C 4 -C 6 alkylene group include tetramethylene, pentamethylene and hexamethylene groups;
  • examples of the C 4 -C 6 alkylene group having an oxygen atom include -CH 2 CH 2 OCH 2 CH 2 -, -CH 2 CH 2 CH 2 OCH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 OCH 2 CH 2 - and the like.
  • a method for producing the present compound is as follows:
  • the present compound (I) can be produced by reacting a naphthol derivative represented by the formula (II),
  • This reaction is usually carried out with or without a solvent in the presence of a base.
  • the reaction temperature usually ranges from room
  • the solvent includes aliphatic hydrocarbons (e.g. hexane, heptane, ligroin, petroleum ether), aromatic hydrocarbons (e.g. benzene, toluene, xylene),
  • halogenated hydrocabons e.g. chloroform, carbon
  • diisopropyl ether dioxane, tetrahydrofuran, diethylene glycol dimethyl ether
  • ketones e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone
  • esters e.g. ethyl formate, ethyl acetate, butyl acetate, diethyl carbonate
  • nitro compounds e.g. nitroethane, nitrobenzene
  • nitriles e.g. acetonitrile, isobutyronitrile
  • tertiary amines e.g.
  • pyridine triethylamine, N,N-diethylaniline, tributylamine, N-methylmorpholine
  • acid amides e.g. formamide, N,N-dimethylformamide, acetamine
  • sulfur compounds e.g. dimethyl sulfoxide, sulfolane
  • the base includes inorganic bases (e.g. sodium carbonate, potassium carbonate, sodium hydride), etc.
  • inorganic bases e.g. sodium carbonate, potassium carbonate, sodium hydride
  • reaction solution After completion of the reaction, the reaction solution is after-treated as usual. That is, water is added to the solution which is then extracted with an organic solvent and concentrated, and if necessary, the product obtained is subjected to chromatography, distillation, recrystallization, etc. Thus, the desired present compound can be obtained.
  • the present compound (I) can also be produced by reacting [reaction (i)] the compound (IV)
  • the acid-halogenating agent includes thionyl chloride, thionyl bromide, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, phosphorus oxychloride, phosgene, oxalyl chloride, etc.
  • the active esterifying agent includes N,N'-disubstituted carbodiimides such as N,N'-dicyclohexylcarbodiimide, N,N'-diisopropylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, etc.; arylsulfonyl chlorides such as 2,4,6-trimethylbenzenesulfonyl chloride, 2,4,6-triisopropylbenzenesulfonyl chloride, etc.; N,N'-carbonyldiimidazole; diphenylphosphorylazide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; N-ethyl-2'-hydroxybenzisoxazolium tetrafluoroborate; N-ethyl-5-phenylisoxazolium-3'-sulfonate; etc.
  • R 3 , R 4 , X, Y 1 , Y 2 , Y 3 , Z and W are as defined above, is produced in the reaction system.
  • the substituent W2 represents a halogen atom when the acid-halogenating agent was used;
  • W 2 represents an N,N'-disubstituted-2-isoureide group when N,N'-disubstituted carbodiimide was used as the active esterifying agent;
  • W2 represents an arylsulfonyloxy group when arylsulfonyl chloride was used as said agent;
  • W 2 represents an imidazolyl group when N,N'-carbonyldiimidazole was used as said agent;
  • W 2 represents an azide group when diphenylphosphorylazide was used as said agent;
  • W 2 represents an ethoxycarbonyloxy group when N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline was used as said agent;
  • W 2 represents 3-(N-ethylaminocarbonyl)-2-hydroxyphenoxy group when N-ethyl-2'-hydroxybenzisox
  • W 2 can also take a form of an acid anhydride represented by the formula,
  • the amount of the foregoing acid-halogenating agent or active esterifying agent used is usually 1 to 10 equivalents based on 1 equivalent of the compound (IV).
  • the amount of the compound of the formula (V) used is usually 1 to 5 equivalents based on 1 equivalent of the compound (IV).
  • the reactions (i) and (ii) can also be carried out, if necessary, in the presence of a base.
  • a base includes organic bases (e.g. 1-methylimidazole, 3-nitro-1H-1,2,4-triazole, 1H-tetrazole, 1H-1,2,4-triazole, imidazole, pyridine, triethylamine) and inorganic bases (e.g. potassium carbonate).
  • organic bases e.g. 1-methylimidazole, 3-nitro-1H-1,2,4-triazole, 1H-tetrazole, 1H-1,2,4-triazole, imidazole, pyridine, triethylamine
  • inorganic bases e.g. potassium carbonate
  • the amount of the base used is 1 to 20 equivalents based on 1 equivalent of the compound (IV).
  • the reactions (i) and (ii) are usually carried out in the presence of an inert solvent.
  • a solvent includes aliphatic hydrocarbons (e.g. hexane, heptane, ligroin, petroleum ether), aromatic hydrocarbons (e.g. benzene, toluene, xylene), halogenated hydrocarbons
  • ethers e.g. diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether
  • ketones e.g.
  • esters e.g. ethyl formate, ethyl acetate, butyl acetate
  • nitro compounds e.g. nitroethane, nitrobenzene
  • nitriles e.g. acetonitrile, isobutyronitrile
  • tertiary amines e.g. pyridine, triethylamine, N,N-diethylaniline, tributylamine, N-methylmorpholine
  • acid amides e.g. N,N-dirnethylformamide
  • sulfur compounds e.g. dimethyl sulfoxide, sulfolane
  • mixtures thereof e.g. dimethyl sulfoxide, sulfolane
  • reaction temperature ranges from 0°C to the boiling point of the solvent in any of the reactions (i) and (ii).
  • the reaction time ranges from 1 to 24 hours for each reaction, and from about 1 to about 48 hours for the reactions (i) through (ii).
  • reaction solution After completion of the reaction, the reaction solution is after-treated as usual. That is, water is added to the solution which is then extracted with an organic solvent and concentrated, and if necessary, the product obtained is subjected to chromatography,
  • the present compounds (I) include their stereoisomers having a herbicidal activity.
  • the compound represented by the formula (II) can be produced by reacting a compound represented by the formula (VII),
  • reaction (iii) an acid-halogenating agent or an active esterifying agent
  • reaction (iv) reacting the resulting reaction product with the compound represented by the formula (V) (hereinafter reaction (iv)).
  • the above reactions (iii) and (iv) can be carried out according to the foregoing reactions (i) and (ii), respectively.
  • the compound (VII) can be produced according to
  • the compound represented by the formula (IV) can be produced by reacting the compound (VII) with the
  • the present compounds (I) have an excellent herbicidal activity and some of them have excellent selectivity between crops and weeds.
  • the present compounds when used for foliar treatment and soil treatment in upland fields, ridge or no-cultivating area, exhibit a herbicidal activity against various weeds, such as,
  • redroot pigweed (Amaranthus retroflexus), smooth pigweed (Amaranthus hybridus)
  • hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia), Florida beggarweed (Desmodium tortuosum), white clover (Trifolium repens)
  • some of the present compounds give such no phytotoxicity as becoming a problem to main crops such as corn (Zea mays), wheat (Triticum
  • the present compound (I) also can safely be used for no-till cultivation in soybean fields, peanut fields, corn fields, etc., and some of them give such no phytotoxicity as becoming a problem to crops.
  • the present compounds exhibit a herbicidal activity against weeds such as Gramineae
  • Some of the present compounds give such no phytotoxicity as becoming a problem to a transplanted rice plant or a direct seeded rice plant in paddy field.
  • the present compound (I) can be used as an active ingredient for herbicides used in orchards, pastures, turfs, forests, afforestation area and non- agricultural fields (e.g. water way, canal), etc.
  • the content of the compound (I) as an active ingredient in these preparations is normally within a range of about 0.003 to 90% by weight, preferably of about 0.01 to 80% by weight.
  • solid carriers examples include fine powders or granules of kaolin clay, attapulgite clay, bentonite, terra alba, pyrophyllite, talc, diatomaceous earth, calcite, walnut shell powders, urea, ammonium sulfate, synthetic hydrated silicon dioxide, etc.
  • liquid carriers examples include aromatic hydrocarbons (e.g. xylene, alkylbenzene, methylnaphthalene, phenylquinolylethane), alcohols (e.g.
  • esters e.g. dialkyl phthalate
  • ketones e.g. acetone, cyclohexanone, isophorone
  • mineral oils e.g. machine oil
  • vegetable oils e.g. soybean oil, cotton seed oil
  • dimethyl sulfoxide N,N-dimethylformamide, acetonitrile, N-methylpyrrolidone, water, etc.
  • Examples of the surface active agents used for emulsification, dispersion, spreading, etc. are anionic surface active agents such as salts of alkyl sulfates, alkylsulfonates, alkylarylsulfonates, dialkyl sulfosuccinates, salts of polyoxyethylene alkylaryl ether phosphoric acid esters, etc., and nonionic surface active agents such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, etc.
  • anionic surface active agents such as salts of alkyl sulfates, alkylsulfonates, alkylarylsulfonates, dialkyl sulfosuccinates, salts of polyoxyethylene alkylaryl ether phosphoric acid esters, etc.
  • nonionic surface active agents such as polyoxyethylene alky
  • lignosulfonates alginates, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate), etc.
  • the present compound (I) is usually formulated and used in soil treatment, foliar treatment or flooding treatment before or after emergence of weeds.
  • the soil treatment includes soil surface treatment, soil incorporation treatment, etc.
  • the foliar treatment includes, in addition to treatment of plants from above, directed treatment in which treatment is limited to weeds only so as not to adhere to crops.
  • the present compound (I) when used as an active ingredient for herbicides, their dosage rate varies with weather conditions, preparation forms, when, how and where the treatment is carried out, weeds species to be controlled, crops species to be protected, etc. Usually, however, the dosage rate is from 1 gram to 10000 grams of the active ingredient per hectare, preferably from 3 grams to 5000 grams of the active ingredient per hectare.
  • the herbicidal composition of the present invention formulated into the form of an emulsifiable concentrate, a wettable powder, a suspension formulation or water dispersible granules may ordinarily be employed by diluting it with water at a volume of about 10 to 1000 liters per hectare (if necessary, adjuvants such as a spreading agent are added to the water).
  • adjuvants such as a spreading agent are added to the water.
  • the granules and some suspension formulations are usually applied without being diluted.
  • the adjuvants include, in addition to the foregoing surface active agents, substances such as polyoxyethylene resin acids (esters), lignosulfonates, abietates, dinaphthylmethanedisulfonates and vegetable oils (e.g. crop oil concentrate, soybean oil, corn oil, cotton seed oil, sunflower oil).
  • substances such as polyoxyethylene resin acids (esters), lignosulfonates, abietates, dinaphthylmethanedisulfonates and vegetable oils (e.g. crop oil concentrate, soybean oil, corn oil, cotton seed oil, sunflower oil).
  • N,N-dimethylformamide solution (0.47 g of N,N-dimethylhydroxylamine hydrochloride and 0.58 g of triethylamine dissolved in 5 ml of N,N-dimethylformamide) was added thereto and stirred for 1 hour at room temperature.
  • reaction solution was poured into water and extracted with ethyl acetate.
  • organic layer was washed five times saturated sodium chloride solution and dried over anhydrous magnesium sulfate.
  • the solvent was removed under reduced pressure and the residue obtained was subjected to thin-layer chromatography (silica gel, hexane/ethyl acetate 2:1 (v/v)) to obtain 1.20 g of 2- ⁇ (4,6-dimethoxypyrimidine-2-yl)oxy ⁇ -1-(N,N-dimethylaminooxycarbonyl)naphthalene (the present compound (1)).
  • 7-hydroxy-8-(N,N-dimethylaminooxycarbonyl)quinoline can be used instead of 2-hydroxy-1-(N,N-dimethylaminooxycarbonyl)naphthalene to obtain 7- ⁇ (4,6-dimethoxy-1,3,5-triazine-2-yl)oxy ⁇ -8-(N,N-dimethylaminooxycarbonyl)quinoline.
  • Table 1 illustrates examples of the compound (I) which can be produced by the above procedure of Production Examples.
  • Table 2 illustrates specific examples of the compound (II), which can be produced by using the corresponding starting materials. Formulation examples are shown below. In the examples, the present compound (I) is shown by Compound No. in Table 1, and parts are by weight.
  • the herbicidal activity and phytotoxicity were evaluated in eleven stages, 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 and 10 by comparing germination and growth of test plants with those untreated.
  • Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with upland field soil, and the seeds of plants in Table 4 were sowed in the pots and cultivated for 10 days in a greenhouse.
  • test compounds were formulated into emulsifiable concentrates according to Formulation Example 2 and the prescribed amount of each emulsifiable concentrate was diluted with a spreading agent-containing water at a spray volume of 1000 liters/hectare and
  • test plants were cultivated for 19 days in a greenhouse, and the herbicidal activity was examined.
  • Cylindrical plastic pots of 10 cm in diameter and 10 cm in depth were filled with upland field soil, and seeds of plants in Table 5 were sowed in the respective pots and covered with soil.
  • the test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with water at a spray volume of 1000 liters/hectare and uniformly applied onto the whole soil surface by means of a sprayer. After application, the test plants were cultivated for 19 days in a greenhouse, and the herbicidal activity was examined. The results are shown in Table 5.
  • Test Example 3 Soil treatment test in upland field
  • Vats of 33 ⁇ 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and the seeds of the test plant shown in Table 6 were sowed in the respective vats and covered with soil in a thickness of 1 to 2 cm.
  • the test compounds were formulated into emulsifiable concentrates according to Formulation Example 2, and the prescribed amount of each emulsifiable concentrate was diluted with water at a spray volume of 1000 liters/hectare and uniformly applied onto the whole soil surface by means of a sprayer. After application, the test plants were cultivated for 18 days in a greenhouse, and the herbicidal activity and phytotoxicity were examined. The results are shown in Table 6.
  • Test Example 4 Foliar treatment test in upland field
  • Vats of 33 ⁇ 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of test plants shown in Table 7 were sowed in the respective vats and cultivated for 30 days. Thereafter, the test
  • test plants uniformly applied from above onto the whole foliar portion of the test plants by means of a sprayer.
  • the conditions of growth of the weed and crops at that time varied depending upon the kind of the test plants, but the test plants were in the 1- to 4-leaf stage and were 2 to 12 cm in height. Eighteen days after application, the
  • Vats of 33 ⁇ 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of test plants shown in Table 8 were sowed in the respective vats and cultivated for 16 days. Thereafter, the test
  • test plants uniformly applied from above onto the whole foliar portion of the test plants by means of a sprayer.
  • the conditions of growth of the weed and crops at that time varied depending upon the kind of the test plants, but the test plants were in the 1- to 4-leaf stage and were 2 to 15 cm in height. Eighteen days after application, the
  • Wager's pots of 1/5000 ares were filled with paddy field soil, and seeds of test plants shown in Table 9 were sowed and covered with soil in a thickness of 1 to 2 cm. After creating a state of paddy field by water flooding, rice (at the 3-leaf stage) was transplanted and they were cultivated in a greenhouse. After 5 days (at the germination stage of barnyardgrass), the test
  • Vats of 33 ⁇ 23 cm 2 in area and 11 cm in depth were filled with upland field soil, and seeds of test plants shown in Table 10 were sowed in the respective vats and cultivated for 30 days. Thereafter, the test
  • test plants uniformly applied from above onto the whole foliar portion of the test plants by means of a sprayer.
  • the conditions of growth of the weed and crops at that time varied depending upon the kind of the test plants, but the test plants were in the 1- to 4-leaf stage and were 2 to 12 cm in height. Eighteen days after application, the

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des nouveaux dérivés de naphtol représentés par la formule (I) dans laquelle R1 et R2 qui peuvent être identiques ou différents, représentent hydrogène, alkyle, cycloalkyle ou phényle éventuellement substitués par au moins un élément sélectionné parmi alkyle, halogène, alcoxy, haloalkyle, nitro, cyano et alcoxycarbonyle ou benzyle éventuellement substitués par au moins un élément sélectionné parmi alkyle, halogène, alcoxy, haloalkyle, nitro, cyano et alcoxycarbonyle, ou R1 et R2 sont fixés ensemble à leurs extrémités afin de former alkylène, ou R1 et R2 sont fixés ensemble à leur extrémité afin de former de l'alkylène contenant de l'oxygène; R3 et R4, qui peuvent être identiques ou différents, représentent chacun alkyle, alcoxy ou halogène; X représente CH ou azote; Z représente CH ou azote; W représente oxygène ou soufre; Y?1, Y2 et Y3¿, qui peuvent être identiques ou différents, représentent chacun hydrogène, alkyle, halogène ou alcoxy. Ces dérivés présentent d'excellentes propriétés herbicides et de sélectivité dans les cultures et peuvent être utilisés comme ingrédient actif pour herbicides.
PCT/JP1993/001275 1992-09-29 1993-09-08 Derives de naphtol, leur procede de production et leur utilisation comme herbicides Ceased WO1994007868A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP93919629A EP0662963A1 (fr) 1992-09-29 1993-09-08 Derives de naphtol, leur procede de production et leur utilisation comme herbicides
AU49833/93A AU4983393A (en) 1992-09-29 1993-09-08 Naphthol derivatives, a method for producing the same and their use as herbicides
BR9307115A BR9307115A (pt) 1992-09-29 1993-09-08 Derivado de naftol processo para a preparação do derivado de naftol composição herbicida processo para controlar ervas daninhas indesejadas e uso do derivado de naftol como um herbicida

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP25969192 1992-09-29
JP4/259691 1992-09-29

Publications (1)

Publication Number Publication Date
WO1994007868A1 true WO1994007868A1 (fr) 1994-04-14

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PCT/JP1993/001275 Ceased WO1994007868A1 (fr) 1992-09-29 1993-09-08 Derives de naphtol, leur procede de production et leur utilisation comme herbicides

Country Status (8)

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EP (1) EP0662963A1 (fr)
CN (1) CN1085215A (fr)
AU (1) AU4983393A (fr)
BR (1) BR9307115A (fr)
CA (1) CA2144074A1 (fr)
HU (1) HUT70686A (fr)
RU (1) RU95117104A (fr)
WO (1) WO1994007868A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015162169A1 (fr) 2014-04-23 2015-10-29 Basf Se Composés de diaminotriazine en tant qu'herbicides

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0223406A1 (fr) * 1985-10-15 1987-05-27 Kumiai Chemical Industry Co., Ltd. Dérivés de pyrimidine et leurs applications comme herbicide
EP0336494A2 (fr) * 1988-04-07 1989-10-11 Shell Internationale Researchmaatschappij B.V. Triazines pour utilisation comme herbicides
EP0346789A2 (fr) * 1988-06-16 1989-12-20 BASF Aktiengesellschaft Dérivés d'acide salicylique et leurs analogues soufrés
EP0360163A2 (fr) * 1988-09-22 1990-03-28 BASF Aktiengesellschaft Dérivés d'acides carboxyliques aromatiques et leur utilisation pour combattre la croissance des plantes indésirables
EP0402751A1 (fr) * 1989-06-14 1990-12-19 BASF Aktiengesellschaft Dérivés d'aldéhyde salicylique et d'acide salicylique et leurs analogues à base de soufre, procédés pour leur préparation et leur utilisation comme herbicides et biorégulateurs
EP0426476A1 (fr) * 1989-11-01 1991-05-08 Sumitomo Chemical Company, Limited Dérivés de la pyrimidine, leur préparation et utilisation
EP0435170A2 (fr) * 1989-12-28 1991-07-03 Kumiai Chemical Industry Co., Ltd. Dérivés de pyrimidine ou de triazine et composition herbicide les contenant
WO1991013065A1 (fr) * 1990-02-20 1991-09-05 Fmc Corporation Herbicides a base d'acide benzoique 6-aryl-2-substitue
DE4034045A1 (de) * 1990-10-26 1992-04-30 Basf Ag Salicylsaeurederivate

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0223406A1 (fr) * 1985-10-15 1987-05-27 Kumiai Chemical Industry Co., Ltd. Dérivés de pyrimidine et leurs applications comme herbicide
EP0336494A2 (fr) * 1988-04-07 1989-10-11 Shell Internationale Researchmaatschappij B.V. Triazines pour utilisation comme herbicides
EP0346789A2 (fr) * 1988-06-16 1989-12-20 BASF Aktiengesellschaft Dérivés d'acide salicylique et leurs analogues soufrés
EP0360163A2 (fr) * 1988-09-22 1990-03-28 BASF Aktiengesellschaft Dérivés d'acides carboxyliques aromatiques et leur utilisation pour combattre la croissance des plantes indésirables
EP0402751A1 (fr) * 1989-06-14 1990-12-19 BASF Aktiengesellschaft Dérivés d'aldéhyde salicylique et d'acide salicylique et leurs analogues à base de soufre, procédés pour leur préparation et leur utilisation comme herbicides et biorégulateurs
EP0426476A1 (fr) * 1989-11-01 1991-05-08 Sumitomo Chemical Company, Limited Dérivés de la pyrimidine, leur préparation et utilisation
EP0435170A2 (fr) * 1989-12-28 1991-07-03 Kumiai Chemical Industry Co., Ltd. Dérivés de pyrimidine ou de triazine et composition herbicide les contenant
WO1991013065A1 (fr) * 1990-02-20 1991-09-05 Fmc Corporation Herbicides a base d'acide benzoique 6-aryl-2-substitue
DE4034045A1 (de) * 1990-10-26 1992-04-30 Basf Ag Salicylsaeurederivate

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015162169A1 (fr) 2014-04-23 2015-10-29 Basf Se Composés de diaminotriazine en tant qu'herbicides
US9822105B2 (en) 2014-04-23 2017-11-21 Basf Se Diaminotriazine compounds as herbicides

Also Published As

Publication number Publication date
AU4983393A (en) 1994-04-26
CA2144074A1 (fr) 1994-04-14
CN1085215A (zh) 1994-04-13
BR9307115A (pt) 1999-03-30
RU95117104A (ru) 1997-01-10
EP0662963A1 (fr) 1995-07-19
HUT70686A (en) 1995-10-30
HU9500898D0 (en) 1995-05-29

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