WO1998001431A1 - Carbamoyltetrazolinones et herbicides - Google Patents

Carbamoyltetrazolinones et herbicides Download PDF

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Publication number
WO1998001431A1
WO1998001431A1 PCT/JP1997/002315 JP9702315W WO9801431A1 WO 1998001431 A1 WO1998001431 A1 WO 1998001431A1 JP 9702315 W JP9702315 W JP 9702315W WO 9801431 A1 WO9801431 A1 WO 9801431A1
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Prior art keywords
group
substituted
alkyl
phch
alkyl group
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PCT/JP1997/002315
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English (en)
Japanese (ja)
Inventor
Katsushi Morimoto
Masatoshi Onari
Hiroyuki Furusawa
Takumi Terachi
Koichi Nishio
Tsutomu Nawamaki
Kunimitsu Nakahira
Tooru Ohki
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Nissan Chemical Industries, Ltd.
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Application filed by Nissan Chemical Industries, Ltd. filed Critical Nissan Chemical Industries, Ltd.
Priority to AU33585/97A priority Critical patent/AU3358597A/en
Publication of WO1998001431A1 publication Critical patent/WO1998001431A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms

Definitions

  • the present invention relates to novel potato rubamoyl tetrazolinones and pesticides containing the same as an active ingredient, particularly herbicides.
  • R 1 and R 4 which it independently represent a hydrogen atom, C '-e alkyl group, C 3 - 7 shea click lower alkyl group, C shea click b alkyl S conversion has been C alkyl group I by the group, C- 7 !
  • C alkyl Cal Poni Le groups C ⁇ - 8 sheets click b alkyl local Poni Le groups, C substituted me by the C shea click lower alkyl group - 6 alkyl Cal Poni Le groups, C 3 - a Arukenirukaru Boniru groups, C 3 - 8 alkynyl Cal Poni group, phenylpropyl group (and however, full et two Le group C 'alkyl groups, C A C Roarukiru group, C, alkoxy groups, C 2 - t Al co Kishikaruponiru May be substituted with one or more substituents selected from a group, a cyano group, a nitro group and a halogen atom.), A C, - ⁇ - alkylsulfonyl group, a C- ⁇ alkenylsulfonyl group, C- ⁇ alkynylsulfonyl group, benzylsulfonyl group, phen
  • pin re di down ring (provided, however, alkyl groups, C i C port alkyl groups, C alkoxy group, C 2 alkoxy Karuponiru group, Shiano group, 1 or selected et or two collected by filtration group and a halogen atom Or it may be substituted by two or more substituents.
  • C) alkyl group, pyridine ring (provided by C alkyl group, C- * haloalkyl group, C alkoxy group, C 2 alkoxycarbonyl group, cyano group, nitro group) May be substituted with one or more substituents selected from a group and a halogen atom.)
  • a fuel group (however, a C,-* alkyl group, a C ' mouth alkyl group, C 'alkoxy group, C 2 - 4 alkoxy Cal Poni group, Shiano group, two collected by filtration group and halo gen atom or al chosen Ru was 1 or is substituted by Tsu by the two or more substituents ), Depending on the epoxy group.
  • a quinoxaline ring (provided that a C 1 -alkyl group, a C 1-, a -alkyl group, an alkoxy group, a C 2- ⁇ alkoxycarbonyl group, It may be substituted by one or more substituents selected from a cyano group, a nitro group and a halogen atom.),
  • a pyrimidine ring (however, C!-* 1 or 2 or more substitutions selected from alkyl, C, haloalkyl, alkoxy, C «alkoxyl, ponyl, cyano, nitro, and halogen atoms may be substituted me by the group.)
  • R 1 and R 4 may form 6 to 9 together with the nitrogen atom to which they are bonded, in which case an oxygen atom, a sulfur atom, a C, alkyl group It may contain a nitrogen atom, a carbonyl group, a sulfonyl group or an unsaturated bond which may be substituted with a ring, and the ring may be substituted with an alkyl group.
  • the ring may be bridged by alkylene, or the ring may be fused by benzene.
  • R 2 and R 3 represent independently hydrogen, C i-e alkyl group, C 3 - e consequent lower alkyl group, C 2 - alkenyl group, C 2 alkynyl group, C, -, mouth alkyl group, C 3 -a Ci- 2 alkyl group substituted with a ⁇ - cycloalkyl group, a C,- ⁇ > alkoxy group (however, R 2 and R 3 do not simultaneously represent an alkoxy group), C ⁇ Alkoxy C'-alkyl group, C>- ⁇ alkylthio C,- ⁇ ⁇ alkyl group, phenyl group (however, C!-, Alkyl Group, C, haloalkyl group, C!
  • R 2 and R 3 may form a 3- to 9-membered ring together with the nitrogen atom to which they are bonded, in which case an oxygen atom is contained in the ring.
  • ⁇ may be bridged by alkylene, and the ring may be fused by benzene.
  • R 5 is a hydrogen atom, C, - 8 alkyl group, C 3 - 7 shea click Roarukiru group, C 3 - 7 sheet C replaced I by the click Roaru kill group, - an alkyl group, C ⁇ - consequent Roarukeniru group A C-alkyl group, a C- ⁇ alkenyl group, a C- ⁇ alkenyl group,
  • R ′ and R 5 form a 3- to 9-membered ring together with the carbon atom to which they are attached.
  • a nitrogen atom which may be substituted with an oxygen atom, a sulfur atom, or a C alkyl group in the ring
  • a carbonyl group, a sulfonyl group or an unsaturated bond the ring may be substituted by a C ′ alkyl group, and the ring may be bridged by an alkylene.
  • the ring may be condensed with a benzene ring.
  • R e and R 7 are each independently hydrogen atom, C -!, Alkyl group, C 3 - 7 alkenyl le group, C - 7 alkynyl or phenylalanine groups (and however, full et two Le group C, - * Substituted by one or more substituents selected from an alkyl group, a C, haloalkyl group, an alkoxy group, a C alkoxycarbonyl group, a cyano group, a nitro group, and a halogen atom.
  • R e and R ′ may form a 5- to 9-membered ring together with the nitrogen atom to which they are bonded, in which case the oxygen atom is included in the Hunch.
  • Sulfur An alkyl group, a nitrogen atom which may be substituted by a C! Alkyl group, a carbonyl group, a sulfonyl group or an unsaturated bond, and a ring which may be substituted by an alkyl group.
  • the ring may be bridged by C> --alkylene, or the ring may be fused by a benzene ring.
  • W 1 represents an oxygen atom or a sulfur atom.
  • n 0, 1 or 2.
  • R ′ represents a hydrogen atom.
  • carpamoyltetrazolinones represented by the following formula (hereinafter, referred to as the compound of the present invention) have strong herbicidal activity and high selectivity to crops, and It was completed.
  • the present invention relates to a pesticide, particularly a herbicide, containing the compound of the present invention as an active ingredient.
  • R 1 has the same meaning as described above. ]
  • M e methylation group
  • E t E Chinore group
  • P r - n Bruno luma Le profile propyl group
  • P r - iso Lee Seo profile Pi Le group
  • B u - n Bruno luma Le butyl Le Group
  • Bu—sec secondary butyl group
  • Bu—tert tert-butyl group
  • Pen-n normal pentynole group
  • H ex — n normal hexyl group
  • Hep—n normal heptyl group
  • Oct—n normal octyl group
  • Bu—eye cyclo Butyl group
  • Pen-cyc cyclopentyl group
  • Hex-eye cyclohexyl group
  • Ph phenyl group
  • Py pyridyl group
  • CH 2 C (N0 2) CHMe, CH 2 CH (NO 2) C ® CH, CH 2 CH (NO 2 ) C ® CMe, CH (NO 2) C ® CH, CH 2 CO 2 M e , CHzCOzEt, CH 2 C0 2 Pr-n, CH 2 CO 2 Pr - i so, CH 2 C (Bu - n, CHMeC0 2 Me, CHHeC0 2 Et,
  • CSNHCH 2 C ⁇ CMe CSNHCH 2 C ⁇ CEt
  • CSNHCH 2 CH 2 C ⁇ CH C SNHCH 2 CH 2 C ⁇ CMe, CSNHCH HeC ⁇ CH, CSNHCHMeC ⁇ CHe, CSNMe 2 , CSNEt 2 , CSN (Pr-n) 2 , CSN (Pri-iso) 2 , CSN (Bun), CSN (Bu-iso), CSN (Bu-sec), CSNEtMe, CSNMePr-n, CSNMePr-iso, CSNM eBu-n, CSNMeBu-iso , CSNMeBu-sec, CSNMeBu-tert, CSNMePen-n, CSNMeHex-n, C SNHeHep-n, CSNMeOct-n, CSNEt (Hex-cyc), PhNHCS, 2-C-PhNHCS, 3-C PhNHCS,
  • R 1 , R 2 , R 3 , X ′, X 2 and W ′ have the same meanings as described above, and Z ′ represents a halogen atom.
  • the reaction scheme 1 shows that the compound of the present invention (1) is obtained by reacting tetrazolinones (2) with a norporogenated (thio) -functional rubamoyl (3) in the presence or absence of a base. ) Is shown.
  • (3) is used in an amount of 1 to 10 times, preferably 1 to 2 times the mole of (2).
  • the base examples include inorganic bases such as sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate or sodium hydride, and pyridine.
  • Organic bases such as dimethylaminopyridine, triethylamine, N, N-dimethylaniline, DBU, and organic bases such as n-butyllithium or sec-butyllithium
  • Organic lithium amides such as lithium, lithium diisopropyl amide, and lithium bistrimethylsilyl amide.
  • the base is usually used in an amount of 0 to 10 times, preferably 1 to 2 times the mole of (2).
  • Power 5 solvent is not particularly limited as long as it is inert to the reaction, for example, to hexa emissions, hydrocarbons such as shea hexane click b, TMG Rue emissions was benzene or carbon tetrachloride, click b Mouth form or 1,2—Norogenous hydrocarbons such as dichloroethane, diethyl ether, diisopropyl ether, dioxane or tetrahydrofuran Ethers, acetate, etc.
  • hydrocarbons such as shea hexane click b, TMG Rue emissions was benzene or carbon tetrachloride, click b Mouth form or 1,2—Norogenous hydrocarbons such as dichloroethane, diethyl ether, diisopropyl ether, dioxane or tetrahydrofuran Ethers, acetate, etc.
  • Ketones such as methylethyl ketone or methyl isobutyl ketone; nitriles such as acetonitrile or propionitol; N, N-dimethylformamide or Acid amides such as N, N-dimethylacetamide, sulfur-containing polar solvents such as dimethylsulfoxide or sulfolane, hexamethylphosphoramide or hexamylphosphorus triamide
  • organic bases such as pyridine and quinoline.
  • the reaction temperature is usually from 190 to 200 ° C, preferably from 0 to 120 ° C.
  • the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 10 hours.
  • R 1 , R 2 and R 3 represent the same meaning as described above, and Z 2 represents a halogen atom. ]
  • Reaction formula 2 shows that 1-hydroxy 41- (N, N-di-g-substituted carpamoyl) -15 (4H) -tetrazolinones (la) ) Is reacted with an active halogen compound (4) in the presence or absence of a base to produce (lb) a part of the compound of the present invention.
  • (4) is usually used in a molar amount of 1 to 10 times, preferably 1 to 2 times the molar amount of (la).
  • inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium carbonate or sodium hydride, pyridine, 4 — Organic bases such as dimethylaminopyridine, triethylamine, N, N-dimethylaniline or DBU, n-butyllithium or sec-butyllithium Organic lithium such as um Organic lithium amides such as lithium diisoproviramide or lithium bistrimethinolesilyl amide.
  • the base is usually used in a molar amount of 0 to 10-fold, preferably 1 to 2-fold over (1a).
  • the solvent is not particularly limited as long as it is inert to the reaction.
  • hydrocarbons such as hexane, cyclohexanebenzene or toluene, carbon tetrachloride, cross-hole form or 1,2-Dichloroethane and other halogenated hydrocarbons, acetyl ether, diisopropyl ether, dioxane and ethers such as tetrahydrofuran, and acetate , Ketones such as methylethylketone or methylisobutylketone, nitriles such as acetonitrile or propionitol, N, N dimethylhonolemaure Acid or amides such as amide or N, N dimethyl acetate amide; sulfur-containing polar solvents such as dimethyl sulfoxide or sulfolane; hexamyl phosphoroamide or
  • the reaction temperature is usually from 90 to 200, preferably from 0 to 120 ° C.
  • the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to about 10 hours.
  • R 2 and R 3 have the same meaning as described above, and R ⁇ is C! - 5 alkyl group, C beta alkenyl, C 2 - «alkynyl group, phenylpropyl group (C, - * alkyl group, C b alkyl, C, alkoxy group, C - - alkoxycarbonyl group, Xia cyano group , Substituted by one or more substituents selected from nitro groups and halogen atoms You may be.
  • Reaction formula 3 shows that 1-hydroxy 41- (N, N-disubstituted carbamoyl) -5 (4H) -tetrazolinones (la ) Is reacted with a (thio) isocyanate (5) in the presence or absence of a base to produce (lc) which is a part of the compound of the present invention.
  • (5) is usually used in a molar amount of 1 to 10 times, preferably 1 to 2 times the molar amount of (la).
  • the base examples include inorganic bases such as sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate or sodium hydride; N, N-N-N-N-butyllithium or sec-butylyllithium, organic bases such as N, N-dimethylylaniline or DBU
  • Organic lithium such as organic lithium, lithium organic lithium amide such as lithium isopropylamide or lithium pistium methylsilyl amide.
  • the base is generally used in a molar amount of 0 to 10-fold, preferably 1 to 2-fold, relative to (la).
  • the solvent is not particularly limited as long as it is inert to the reaction.
  • hydrocarbons such as hexane, cyclohexane, benzene or toluene, carbon tetrachloride, and cross-linked form Or 1,2 — halogenated hydrocarbons such as dichloroethane, ethers such as getyl ether, diisopropyl ether, dioxane or tetrahydrofuran, acetone, Ketones such as methylethylketone or methylisobutylketone; nitriles such as acetonitrile or propionitol; N, N-dimensions Acid amides such as tilformamide or N, N-dimethylacetamide, sulfur-containing polar solvents such as dimethylsulfoxide or sulfolane, hexamylphosphoramide Is hexamet
  • the reaction temperature is usually from 190 to 200 ° C, preferably from 0 to 120 ° C.
  • the reaction time is usually from 0. 05 to 100 hours, preferably from 0.5 to 10 hours.
  • R 1 , R 2 , R 3 and R 4 have the same meaning as described above, and Z 2 and Z 3 each represent a halogen atom. ]
  • [1] is -amino 1- (N, N-disubstituted carpamoyl) -15 (4H) -tetrazolinones (Id) which are -parts of the compound of the present invention. Shows the step of reacting the compound with an active halogen compound (6) in the presence or absence of a base to produce (1e) which is a part of the compound of the present invention.
  • (6) is usually used at 1 to 10 moles, preferably 1 to 2 moles, compared to (Id).
  • the base examples include inorganic bases such as sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate or sodium hydride; Organic bases such as dimethylaminopyridine, triethylamine, N, N-dimethylaniline or DBU, n-butyllithium or sec-butyllithium, etc. Organic lithium compounds such as lithium bistrimethylsilyl amide and lithium bistrimethylsilyl amide.
  • the base is used usually in a molar amount of 0 to 10-fold, preferably 1 to 2-fold, relative to (Id).
  • the solvent is not particularly limited as long as it is inert to the reaction.
  • hydrocarbons such as hexane, cyclohexanebenzene or toluene, carbon tetrachloride, chloroform, or 1,1,2 2 ⁇ -Norogen hydrocarbons such as dichloroethane, ethers such as diethyl ether, diisopropyl ether, dioxane or tetrahydrofuran, acetone and methylethyl ketone Or ketones such as methylisobutylketone, etc., nitriles such as acetonitrile or propionitol, N, N-dimethylformamide or N, N — Acid amides such as dimethyl acetate, sulfur-containing polar solvents such as dimethyl sulfoxide or sulfolane, hexamethyl phosphoro 'amide or
  • the reaction temperature is usually from 190 to 200 ° C, preferably from 0 to 120 ° C.
  • the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 10 hours.
  • [2] is a part of the compound of the present invention by reacting (le), which is a part of the compound of the present invention, with an active halogen compound (7) in the presence or absence of a base (If)
  • the process for manufacturing is a part of the compound of the present invention by reacting (le), which is a part of the compound of the present invention, with an active halogen compound (7) in the presence or absence of a base (If)
  • the process for manufacturing is a part of the compound of the present invention by reacting (le), which is a part of the compound of the present invention, with an active halogen compound (7) in the presence or absence of a base (If)
  • (7) is generally used in a molar amount of 1 to 10 times, preferably 1 to 2 times the molar amount of (1e).
  • sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate Inorganic bases such as lithium or sodium hydride, pyridin, 4-dimethylaminoviridine, triethylamine, N, N-dimethylaniline
  • an organic base such as DBU
  • an organic lithium such as n-butyllithium or sec-butyllithium
  • lithium diisopropylamide or lithium bistrimethylsilyl
  • Organic lithium amides such as lithium amide.
  • the base is usually used in a molar amount of 0 to 10-fold, preferably 1 to 2-fold over (le).
  • hydrocarbons such as hexane, cyclohexanebenzene or toluene, carbon tetrachloride, and cross-linked form
  • halogenated hydrocarbons such as 1,2-dichloroethane, ethers such as getyl ether, diisopropyl alcohol, dioxane or tetrahydrofuran, Ketones such as acetate, methylethylketone or methylisobutylketone, nitriles such as acetonitrile or propionitol, N, N — Acid amides such as dimethylformamide or N, N-dimethylacetamide; sulfur-containing polar solvents such as dimethylsulfoxide or sulfolane; hexamethylphosphoramide. Or hexametylphos Phosphorus
  • the reaction temperature is usually from _90 to 200 ° C, preferably from 0 to 120 ° C.
  • the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 10 hours.
  • reaction formula 5 shows that one amino-4— (N, N—disubstitution force rubamoyl) _5 (4H) -tetrazolinones (I Method for producing (lg) which is a part of the compound of the present invention by reacting d) or (le) with (thio) isocyanoates (5) in the presence or absence of a base Is shown.
  • (5) is usually used in a molar amount of 1 to 10 times, preferably 1 to 2 times the molar amount of (Id) or (1e).
  • the base examples include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium carbonate, and sodium hydride; Organic bases such as N-, 4-dimethylaminopropylin, triethylamine, N, N-dimethylaniline or DBU, n-butyllithium or sec-butyllithium And organic lithium amides such as lithium and organic lithium amides such as lithium bisisopropyl amide and lithium bistrimethylsilyl amide.
  • the base is usually used in a molar amount of 0 to 10-fold, preferably 1 to 2-fold, relative to (Id) or (le).
  • the solvent is not particularly limited as long as it is inert to the reaction. Examples thereof include hexane, cyclohexane; hydrocarbons such as benzene and toluene; carbon tetrachloride; Or halogenated hydrocarbons such as 1,2-dichloroethane, ethers such as getyl ether, diisopropyl ether, dioxane or tetrahydrofuran, acetone, Ketones such as thiethylketone or methylisobutylketone; nitriles such as acetonitrile or propionitol; N, N-dimethylforma Acid or amides such as amide or N, N-dimethylacetamide; polar solvents such as dimethylsulfoxide or sulfolane; and hexamethylphosphoamide or Kisametyl Phosphorus Phosphorus-
  • the reaction temperature is usually from 190 to 200 ° C, preferably from 0 to 120 ° C.
  • reaction time is generally from 0.05 to 100 hours, preferably from 0.5 to 10 hours. (Reaction formula 6)
  • reaction formula 6 shows that a part of the compound of the present invention is composed of 11-amino 41- (N, N-disubstituted rubamoyl) -15 (4H) -tetrazolinones (I).
  • (lh) which is a part of the compound of the present invention, by reacting d) with (thio) ketones (8) in the presence or absence of an acid will be described.
  • (8) is generally used in an amount of 1 to 10 moles, preferably 1 to 2 moles, based on (Id).
  • the acid examples include inorganic mineral acids such as hydrochloric acid, sulfuric acid, and phosphoric acid, organic sulfuric acids such as methanesulfonic acid and p-toluenesulfonic acid, and formic acid and diacid.
  • Organic sulfonic acids The acid is usually used in a molar amount of 0 to 10-fold, preferably 0.01 to 1-fold with respect to (Id).
  • the reaction proceeds even without solvent, but a solvent can be used if necessary.
  • the solvent is not particularly limited as long as it is inert to the reaction.
  • examples include hydrocarbons such as hexane, cyclohexane, benzene, and toluene, W carbon chloride, and cross-linked form.
  • 1, 2—Norogen hydrocarbons such as dichloroethane, ethers such as getyl ether, diisopropyl ether, dioxane or tetrahydrofuran, Ketones such as acetone, methylethylketone or methylisobutylketone, nitriles such as acetonitrile or provonitrile, N, N—dimethylmethylforma Acid or amides such as amide or N, N-dimethylacetamide, polar sulfur-containing solvents such as dimethylsulfoxide or sulfolane, hexamylphosphoroamide or Hexame Phosphorus-containing polar solvents such as tyl phosphorous amide.
  • polar sulfur-containing solvents such as dimethylsulfoxide or sulfolane, hexamylphosphoroamide or Hexame Phosphorus-containing polar solvents such as tyl phosphorous amide.
  • the reaction temperature is usually from 190 to 200 ° C, preferably from 0 to 120 ° C.
  • the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 10 hours.
  • R ′ RR 3 and R 5 represent the same meaning as described above.
  • Reaction Scheme 7 shows that 1-alkylideneamino or 1-aralkylideneamino41- (N, N-disubstituted carboxyl) which is a part of the compound of the present invention that can be produced by Reaction Scheme 1 Molyl) 15 (4H) -tetrazolinones (lh) are hydrolyzed in the presence of acid to give 1-amino-4- (N, N-disubstituted rubamoinole) One 5 (4H) one tetrazolinone
  • the acids include inorganic mineral acids such as hydrochloric acid, sulfuric acid or phosphoric acid, organic sulfuric acids such as methanesulfonic acid or p-toluenesulfonic acid, and right-handed powers such as formic acid or acetic acid. Ruponic acids are mentioned.
  • the acid is usually used in a molar amount of 0 to 10-fold, preferably 0.01 to 1-fold with respect to (1 h).
  • This reaction is carried out in water, but in some cases, an appropriate solvent can be used.
  • the solvent is not particularly limited as long as it is inert to the reaction.
  • hydrocarbons such as hexane, cyclohexane, benzene or toluene, carbon tetrachloride, and cross-linked form Or 1,2—logenogenic hydrocarbons such as dichloroethane, tereyl such as getyl ether, diisopropyl ether, dioxane or tetrahydrofuran; Ketones such as acetone, methylethylketone or methylisobutylketone, nitriles such as acetonitrile or propionitol, N, N—Dimethyl Acid amides such as ruformamide or N, ⁇ -dimethylacetamide, sulfur-containing polar solvents such as dimethyl sulfoxide or sulfolane, hexamyl phosphor
  • Reaction formula 8 shows that 1-benzyloxy 41- (N, N-disubstituted carnodi-moyl) 1-5 (4H) which is a part of the compound of the present invention which can be produced by reaction formula 1 ) —Tetrazolinones (1i) are hydrogenated in the presence of one carbon atom of palladium to give 1-hydroxy 41- (N, N— Disubstitution power (Lubamoyl) -1 5 (4H) —Shows the method for producing tetrazolinones (la).
  • the solvent used in this reaction is not particularly limited as long as it is inert to the anti-I core.
  • aliphatic hydrocarbons such as hexane or cyclohexane, and getyl ether disopro Ethers such as pill ether, dioxane, or tetrahydrofuran; alcohols such as methanol or ethanol; or water.
  • the reaction can be carried out under normal to elevated pressure.
  • the reaction temperature is usually from 190 to 200 "C, preferably from 0 to 120 ° C.
  • the reaction time is usually from 0.05 to 100 hours, preferably. Is 0.5 to 24 hours You.
  • [3] is a method for reacting tetrazolinones (2) with (thio) phosphogen (9) in the presence or absence of a base to form (thio) carbamoyl liposomes (9). 10) Indicates the manufacturing process.
  • (9) is usually used in an amount of 1 to 100 times, preferably 1 to 10 times, that of (10).
  • the solvent used in this reaction is not particularly limited as long as it is inert to the reaction.
  • examples thereof include hydrocarbons such as hexane, cyclohexane, benzene or toluene, and tetrachloride.
  • Carbon, halogen form, or halogenated hydrocarbons such as 1,2-dichloroethane, getyl ether, diisopropyl ether, dioxane or tetrahydrofuran.
  • Ethers such as lan;
  • the reaction temperature is usually from 190 to 200 ° C, preferably from ⁇ 20 to 120 ° C.
  • the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 10 hours.
  • [4] shows a process for producing the compound (1) of the present invention by reacting the (chi) carno-moyl-mouth lids (10) with the amines (11).
  • (11) is usually 1 to 100 moles, preferably 1 to 2 moles, relative to (10). use.
  • the base includes inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium carbonate, and sodium hydride; Organic bases such as dimethylaminopropyl, triethylamine, N, N-dimethylaniline or DBU.
  • the base is generally used in a molar amount of 0 to 100-fold, preferably 0 to 2-fold, relative to (2).
  • the solvent is not particularly limited as long as it is inert to the reaction.
  • hydrocarbons such as hexane, cyclohexane benzene or toluene, carbon tetrachloride, chloroform, or chloroform
  • Halogen hydrocarbons such as 1,2-dichloromethane ethane, ethers such as getyl ether, diisopropyl ether, dioxane or tetrahydrofuran, acetone, methylethylke Ketones such as tones or methylisobutyl ketone; nitriles such as acetonitrile or propionitol; N, N—dimethylformamide or Acid amides such as N, N-dimethylacetamide, sulfur-containing polar solvents such as dimethylsulfoxide or sulfolane, hexamethylphosphoramide or hexamethylphosphoric acid
  • the reaction temperature is usually from 190 to 200 ° C (: preferably from 0 to 120 ° C.
  • the reaction time is usually from 0.05 to 100 hours, preferably. Is from 0.5 to 10 hours.
  • Reaction formula 10 is obtained by hydrogenating 1-benzyl-41- (N, N-disubstituted rubamoyl) -15 (4H) -tetrazolinones (12) in the presence of a catalyst.
  • a method for producing 11 (N, N-disubstituted rubamoyl) -15 (4H) -tetrazolinones (1j) which is a part of the compound of the present invention will be described.
  • Examples of the catalyst used in this reaction include palladium monocarbon, platinum monocarbon, palladium hydroxide-carbon, palladium oxide or gold oxide.
  • the catalyst is usually used in an amount of 0.1 to 200% by weight, preferably 1 to 10% by weight, based on (12).
  • the solvent used in this reaction is not particularly limited as long as it is inert to the reaction.
  • examples thereof include aliphatic hydrocarbons such as hexane and cyclohexane, and gethyrudel delisoisopropyl ether.
  • ethers such as dioxane or tetrahydrofuran, alcohols such as methanol or ethanol, and water.
  • the reaction can be carried out under normal to elevated pressure.
  • the reaction temperature is usually from 190 to 200 ° C (: preferably from 0 to 120 ° C.
  • the reaction time is usually from 0.05 to 100 ° C. Preferably 0.5 to 24 hours.
  • the reaction formula 11 shows that 11 (N, N-disubstituted carbamoyl) -15 (4H) -tetrazolinones (lj), which are a part of the compound of the present invention, can be obtained in the presence of base or In the absence of a compound of the present invention, the compound is reacted with a sulfenyl sulfide, a sulfinyl sulfide or a sulfonyl hydride (13) to form one of the compounds of the present invention. (13) showing the method for producing (lk) is usually 1 to 10 times, preferably 1 to 2 times the mole of (1j).
  • the base examples include inorganic bases such as sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate or sodium hydride; pyridin; Organic bases such as dimethylaminopyridine, triethylamine, N, N—dimethylaniline or DBU, n—organic lithium such as butyllithium or sec-butyllithium. And organic lithium amides such as lithium lithoisopropyl amide or lithium pistium methylsilyl amide.
  • the base is usually used in a molar amount of 0 to 10-fold, preferably 1 to 2-fold, relative to (l j).
  • the solvent is not particularly limited as long as it is inert to the reaction. Examples thereof include hexane, cyclohexane; hydrocarbons such as benzene and toluene; carbon tetrachloride; Or 1,2—halogen hydrocarbons such as dichloroethane, methyl ether, diisopropyl ether, dioxane or tetrahydrofuran, etc.
  • Ethers ketones such as acetate, methylethylketone or methylisobutylketone, nitriles such as acetonitrile or propionitol, N , N — dimethylformamide or N, N — acid amides such as dimethylacetamide, polar sulfur-containing solvents such as dimethylsulfoxide or sulfolane, hexamethylphosphoroamide Or hexamethylphospho It is sampled Li A mi de phosphorus-containing polar solvents such as, pin re di emissions or the organic bases such as onboard Li emissions and the like.
  • the reaction temperature is usually from 190 to 200 ° C, preferably from 0 to 120 ° C.
  • the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 10 hours.
  • One amino-5 (H) -tetrazolinonone (2d) and 5 (4H), which are part of the tetrazolinones (2) used in Reaction Scheme 1, ) -Tetrazolinon (2j) is the journal 'ob', 'American', 'chemical' society (J. Am. Chem. Soc.), 105 (4 ), 902 (1983), and the journal 'Ob' Organic 'Chemistry (J. Org. Chem.), 47, 474 (1982).
  • the other (2) can be produced by the method of Reaction Formula II to D.
  • RX 3 and X * have the same meanings as described above, R ′ represents C, an alkyl group or a phenyl group, and Z 5 represents a halogen atom. ]
  • carbamates (16) are produced by reacting an amine (14) with a halogenocarbonate ester (15) in the presence or absence of a base. The following steps are shown.
  • (15) is generally used in 1 to 10 times, preferably 1 to 2 times, the amount of (14).
  • the salt examples include inorganic bases such as sodium hydroxide, sodium hydroxide, sodium carbonate, sodium carbonate or hydrogenated sodium; Pyridines, 4-methylethylaminopyridine, triethylamine, N, N — organic bases such as dimethylylaniline or DBU, n — butyllithium Or lithium organic lithium such as monobutyllithium, and organic lithium such as lithium bisisopropylamide or lithium bistrimethylsilylamide Muamides.
  • the base is usually from 0 for (14); 0 times Molar, preferably 1 to 2 times.
  • the solvent is not particularly limited as long as it is inert to the reaction, and examples thereof include hydrocarbons such as hexane, cyclohexanebenzene or toluene, carbon tetrachloride, and chloroform.
  • hydrocarbons such as hexane, cyclohexanebenzene or toluene, carbon tetrachloride, and chloroform.
  • 1,2-dichloroethane and other hydrocarbons such as ethers such as diethyl ether, diisopropyl ether, dioxane or tetrahydrofuran, acetate, and methyl ether.
  • Ketones such as tilethyl ketone or methinoleisobutyl ketone; nitriles such as acetonitrile or propionitol; N, N-dimethylformol Acid amides such as amide or N, N-dimethylacetamide, sulfur-containing polar solvents such as dimethyl sulfoxide or sulfolane, hexamethyl phosphoroamide Is Hexame Phosphorus-containing polar solvents such as Hora be sampled Li A Mi de, pin Li di down or is your machine bases such as on-board Li down, and the like.
  • the reaction temperature is usually from 190 to 200 ° C (: preferably from 0 to 120 ° C.
  • the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 10 hours.
  • [6] shows a step of producing an intermediate (2a) of the compound of the present invention by azide conversion of (16) in the presence or absence of Lewis acid.
  • the azide agent examples include inorganic azides such as sodium azide, barium azide and lithium azide, azide trimethylsilyl or Organic azides such as diphenylphosphoryl azide are exemplified.
  • the azide agent is used in an amount usually 10 to 10 times, preferably 1 to 2 times the mol of (16).
  • Examples of the Louis acid include metal chlorides such as aluminum chloride and zinc chloride.
  • Lewis acid is generally used in a molar amount of 0 to 10-fold, preferably 1 to 2-fold over (16).
  • the solvent is not particularly limited as long as it is inert to the reaction.
  • the solvent include hydrocarbons such as hexane, cyclohexane, benzene, and toluene, carbon tetrachloride, and cross-linked form.
  • 1,2 — halogenated hydrocarbons such as dichloroethane, ethers such as getylether, diisopropylether, dioxane or tetrahydrofuran , Aston, Ketones such as methylethyl ketone or methyl isobutyl ketone; nitriles such as acetonitrile or propionitol; N, N—dimethylformamide Or acid amides such as N, N-dimethylacetamide, sulfur-containing polar solvents such as dimethylsulfoxide or sulfolane, hexamethylphosphoramide or hexame Phosphorus-containing polar solvents such as tyl phosphorous triamide; and organic bases such as pyridin or quinoline.
  • ethers such as getylether, diisopropylether, dioxane or tetrahydrofuran , Aston, Ketones such as methylethyl
  • the reaction temperature is usually from -90 to 200 ° C, preferably from 0 to 120 ° C.
  • the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 10 hours.
  • [7] shows the step of reacting (14) with carbon disulfide in the presence of a base, and then reacting it with a methylating agent to produce dithiocanomates (17).
  • sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate Inorganic bases such as lithium or sodium hydride, pyridine, 4-dimethylamino pyridine, triethylamine, N, N-dimethylaniline
  • organic bases such as DBU, n-butyllithium or sec-organic lithium such as butyllithium lithium lithium diisopropylamide or lithium pyridine
  • Organic lithium amides such as tilsilyl amide and the like can be mentioned.
  • methylating agent examples include methyl iodide, methyl bromide, methyl chloride or dimethyl sulfuric acid.
  • [8] shows the step of reacting (17) with hydrazine hydrate to produce thiosemicarbazides (18).
  • [9] shows a step of producing (18) by methylating (18) and diazotizing it to produce 5-methylthiotetrazole (19).
  • methylating agent examples include methyl iodide, methyl bromide, methyl chloride and dimethyl sulfuric acid.
  • oxidizing agent examples include organic peroxides such as m-chloroperbenzoic acid or peracetic acid, aqueous hydrogen peroxide, potassium permanganate or persulfate (for example, 2KHS0 5 ⁇ KHS04 -. K 2 S 0 inorganic oxidizing agent, and the like.
  • reaction formula C is obtained by converting 11 amino 5 (4H) 1 tetrazolinone (2d) to (thio) ketones (8) in the presence or absence of an acid.
  • Reaction of the intermediate of the compound of the present invention is a method to manufacture part (2h).
  • (8) is usually used in an amount of 1 to 10 times, preferably 1 to 2 times, the mole of (2d).
  • the acid examples include inorganic mineral acids such as hydrochloric acid, sulfuric acid, and phosphoric acid, organic sulfonates such as methansulfonate and P-toluenesulfonate, and organic powers such as formic acid and acetic acid. Ruponic acids.
  • the acid is usually used in a molar amount of 0 to 10-fold, preferably 0.01 to 1-fold, relative to (2d).
  • the solvent is not particularly limited as long as it is inert to the reaction.
  • the solvent include hydrocarbons such as hexane, cyclohexanebenzene or toluene, carbon tetrachloride, chloroform, and 1 , 2-dichloroethane, etc., halogenated hydrocarbons, acetyl ether, diisopropyl ether, dioxane or ether such as tetrahydrofuran, acetate , Ketones such as methylethylketone or methyltinolesobutylketone, nitriles such as acetonitril or propionitol, N, N — Acid amides such as dimethylformamide or N, N-dimethylacetamide; polar sulfur-containing solvents such as dimethylsulfoxide or sulfolane; hexamylphosphoramide.
  • the reaction temperature is usually from 90 to 200 ° C, preferably from 0 to 120 ° C. Reaction when the question is usually 0. 0 5 force 3 et al 1 0 0 hour, rather than the preferred Ru 0. 5 or et al. 1 0 hours der.
  • reaction formula D is obtained by reacting 1-benzyloxy-5 (4H) -tetrazolinones (21) which are a part of the intermediate of the compound of the present invention which can be produced by the reaction formula A. Hydrogenation in the presence of palladium-single carbon to give 1-hydroxyl 5 (4H) -tetrazolinones (2 m) which is a part of the intermediate of the compound of the present invention. The method of manufacturing is shown.
  • Palladium-carbon is usually used in an amount of 0.1 to 200% by weight, preferably 1 to 10% by weight, based on (21).
  • the solvent used in this reaction is not particularly limited as long as it is inert to the reaction; for example, aliphatic hydrocarbons such as hexane or cyclohexane, getyl ether, Examples include ethers such as diisopropyl ether, dioxane or tetrahydrofuran, alcohols such as methanol or ethanol, or water.
  • the reaction can be carried out under normal to elevated pressure.
  • the reaction temperature is usually from 190 to 200 ° C, preferably from 0 to 120 ° C.
  • the reaction time is usually from 0.05 to 100 hours, preferably from 0.5 to 24 hours.
  • N, N—dimethylformamide 50 ml was added to aluminum chloride (13 g, 98 mmo1) and sodium azide (4.3 g, 66 mmo). 1) was added, and the mixture was stirred for 15 minutes. Then, phenyl N-benzyloxycarbamate (8.0 g, 33 mmo 1) was added, and the mixture was stirred at 80 ° C. for 3 hours. After cooling the reaction mixture to room temperature, The mixture was slowly poured into ice water (600 ml) containing sodium nitrate (4.0 g, 58 mmol) and stirred for 15 minutes.
  • N, N-dimethylformamide (10 ml) is added to 1-hydroxyl 4- (N, N-Jetylcarbamoyl) -15 (4H) -tetrazolinone ( 0.15 g, 0.74 mmol), potassium carbonate (0.10 g, 0.75 mmo1) and 2,4-dichloropyrimidine (0.1 llg, 0. .75 mmo1) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water (30 ml), and the product was extracted with ethyl acetate.
  • Toluene (10 ml) is added to 1-ethoxy-5 (4H) -tetrazolinone (0.20 g, 1.4 mmol) and 4-dimethylaminovinylidine (0 25 g, 2.1 mmo 1) and N, N-dimethylthiocarpamoylnorrechloride (0.57 g, 1.5 mmo 1) were added to give 100.
  • the mixture was stirred at C for 2 hours. After filtering off the impurities, the solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (eluent: chromatographic form) to obtain 0.1 lg of the desired product. Obtained. Oily substance.
  • Tables 1 and 2 show the structural formulas and physical properties of the compounds synthesized by using the same method as in the above examples. However, the symbols in the table have the following meanings. Qy--N
  • Oil g 1 0 2-Cl -PhCOO 0 Q
  • Oil g 1 Bilyzin-2-ylmethyl-0 0 Q
  • Oil g 1 3 4-CFi-PhCH, 0 Q
  • Oil S 17 C1CH CHCH.0 Q.
  • Oil S 20 Epoxy methyl -0 Q: Oil
  • Child 9 C'H, C ⁇ CH ⁇ ⁇ , CH 2 CH 2 a
  • CH 2 C (N0 2 ) CHMe, CH 2 CH (NO 2 ) C ⁇ CH, CH 2 CH (NO 2 ) C3 CMe, CH (NO 2 ) C ⁇ CH, CH 2 CO 2 Me, CH 2 C0 2 Et, CH 2 CO 2 Pr-n, CH 2 C0 2 Pr- i so, CH 2 C0 2 Bu - n, CHMeC0 2 Me, CHMeCOzEt,

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Abstract

Cette invention concerne de nouveaux produits chimiques agricoles contenant des herbicides. De manière spécifique, elle concerne les carbamoyltétrazolinones représentées par la formule générale (1) ainsi que des produits chimiques agricoles contenant de tels composés. Dans la formule (1), R1 est hydrogène, alkyle C¿1?-C8, cycloalkyle C3-C7 ou analogue; X?1 et X2¿ sont chacun oxygène, NR4, S(O)¿n? ou analogue, R?2 et R3¿ sont chacun indépendamment hydrogène, alkyle C¿1?-C6, cycloalkyle C3-C6 ou analogue et W?1¿ est oxygène ou soufre.
PCT/JP1997/002315 1996-07-03 1997-07-03 Carbamoyltetrazolinones et herbicides WO1998001431A1 (fr)

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JP17320796 1996-07-03
JP8/173207 1996-07-03
JP24017496 1996-09-11
JP8/240174 1996-09-11
JP8/292432 1996-11-05
JP29243296 1996-11-05
JP9/2085 1997-01-09
JP208597 1997-01-09
JP9/154849 1997-06-12
JP15484997 1997-06-12

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019002158A1 (fr) 2017-06-30 2019-01-03 Basf Se Trifluorométhyloxadiazoles substitués utilisés pour lutter contre des champignons phytopathogènes

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1985001939A1 (fr) * 1983-11-04 1985-05-09 Fmc Corporation 1-aryl-4-substitue-1,4-dihydro-5h-tetrazol-5-ones herbicides et leurs analogues a base de soufre
EP0146729A1 (fr) * 1983-11-07 1985-07-03 Hans-Heinrich Willberg Dispositif de transfert de composants, particulièrement des puces intégrées, d'un bac d'entrée à un bac de sortie
EP0202929A2 (fr) * 1985-05-23 1986-11-26 UNIROYAL CHEMICAL COMPANY, Inc. Tetrazolinones substitués
EP0571855A1 (fr) * 1992-05-28 1993-12-01 Nihon Bayer Agrochem K.K. Dérivés de 1-(3-halo-4-trifluorométhylphényle) tetrazolinone, leur préparation et leur utilisation comme herbicides
EP0571854A1 (fr) * 1992-05-28 1993-12-01 Nihon Bayer Agrochem K.K. Dérivés de 1-(3,4-disubstitué phényle) tetrazolinone, leur préparation et leur utilisation comme herbicides
EP0643049A1 (fr) * 1993-09-14 1995-03-15 Nihon Bayer Agrochem K.K. Procédé pour la préparation de dérivés de la 5(4H)-tétrazolinone substitués à la position-1

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1985001939A1 (fr) * 1983-11-04 1985-05-09 Fmc Corporation 1-aryl-4-substitue-1,4-dihydro-5h-tetrazol-5-ones herbicides et leurs analogues a base de soufre
EP0146729A1 (fr) * 1983-11-07 1985-07-03 Hans-Heinrich Willberg Dispositif de transfert de composants, particulièrement des puces intégrées, d'un bac d'entrée à un bac de sortie
EP0202929A2 (fr) * 1985-05-23 1986-11-26 UNIROYAL CHEMICAL COMPANY, Inc. Tetrazolinones substitués
EP0571855A1 (fr) * 1992-05-28 1993-12-01 Nihon Bayer Agrochem K.K. Dérivés de 1-(3-halo-4-trifluorométhylphényle) tetrazolinone, leur préparation et leur utilisation comme herbicides
EP0571854A1 (fr) * 1992-05-28 1993-12-01 Nihon Bayer Agrochem K.K. Dérivés de 1-(3,4-disubstitué phényle) tetrazolinone, leur préparation et leur utilisation comme herbicides
EP0643049A1 (fr) * 1993-09-14 1995-03-15 Nihon Bayer Agrochem K.K. Procédé pour la préparation de dérivés de la 5(4H)-tétrazolinone substitués à la position-1

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019002158A1 (fr) 2017-06-30 2019-01-03 Basf Se Trifluorométhyloxadiazoles substitués utilisés pour lutter contre des champignons phytopathogènes

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