WO1998025912A1 - Amides heterocycliques herbicides - Google Patents

Amides heterocycliques herbicides Download PDF

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WO1998025912A1
WO1998025912A1 PCT/US1997/022461 US9722461W WO9825912A1 WO 1998025912 A1 WO1998025912 A1 WO 1998025912A1 US 9722461 W US9722461 W US 9722461W WO 9825912 A1 WO9825912 A1 WO 9825912A1
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alkyl
haloalkyl
phenyl
compound
formula
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PCT/US1997/022461
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Morris Padgett Rorer
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E.I. Du Pont De Nemours And Company
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Priority to AU55190/98A priority Critical patent/AU5519098A/en
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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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings

Definitions

  • This invention relates to certain tetrazolinones, their N-oxides, agriculturally suitable salts, compositions thereof, and methods of their use for controlling undesirable vegetation.
  • the control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas is also important. Many products are commercially available for these purposes, but the need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
  • Patent application EP 692,482 discloses compounds of Formula i as herbicides:
  • R 1 and R 2 are independently alkyl, haloalkyl, cycloalkyl, alkenyl, alkynyl or phenyl; R 3 is nitro halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or phenoxy; and n is O, 1, 2 or 3.
  • the tetrazolinones of the present invention are not disclosed in this publication.
  • This invention is directed to compounds of Formula I including all geometric and stereoisomers, JV-oxides, and agriculturally suitable salts thereof, as well as agricultural compositions containing them and a method of their use for controlling undesirable vegetation:
  • A is phenyl or a 5- or 6-membered aromatic heterocyclic ring system containing 1 to 4 heteroatoms independently selected from the group nitrogen, oxygen, and sulfur, and each heterocyclic ring system is optionally substituted by one or more groups selected from halogen, nitro, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C r C 4 alkoxy, C r C 4 haloalkoxy, S(O) n R 4 , S(O) 2 OR 4 , SO2NR 5 R 6 , and phenyl optionally substituted on the phenyl ring with
  • W is CH orN
  • R 1 is C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 7 cycloalkyl, C 3 -C 7 cycloalkenyl, C 3 -C 6 alkenyl, C3-C6 haloalkenyl, C 3 -C 6 alkynyl, C3-C6 haloalkynyl or Ci-Cg alkoxy; or R 1 is phenyl optionally substituted on the phenyl ring with C1-C3 alkyl, halogen, cyano or nitro;
  • R 2 is C r C 6 alkyl, C r C 6 haloalkyl, C3-C7 cycloalkyl, C3-C7 cycloalkenyl, C 3 -C 6 alkenyl, C3- haloalkenyl, C3-C6 alkynyl, or C 3 -C 6 haloalkynyl; or R 2 is phenyl optionally substituted on the phenyl ring with C1-C3 alkyl, halogen, cyano or nitro; or R 1 and R 2 can be taken together as -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -,
  • each R 3 is independently H, halogen, C1-C4 alkoxy, C r C haloalkoxy, C1-C4 alkyl, C1-C4 haloalkyl, C -C 4 alkoxyalkyl, C 2 -C 4 alkylthioalkyl, cyano, nitro, NH(C r C 4 alkyl), N(C r C 4 alkyl) 2 , S(O) n R 4 , S(O) 2 OR 4 or SO 2 NR 5 R 6 ;
  • R 4 is C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl or C3-C6 haloalkynyl;
  • R 5 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl;
  • R 6 is H, C r C 6 alkyl, C r C 6 haloalkyl, C 3 -C 6 alkenyl.
  • C 3 -C 6 alkynyl or C r C 6 alkoxy; or R 5 and R 6 can be taken together as -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -,
  • n 0, 1 or 2.
  • alkyl used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, z ' -propyl, or the different butyl, pentyl or hexyl isomers.
  • 1-2 alkyl indicates that one or two of the available positions for that substituent may be alkyl which are independently selected.
  • Alkenyl includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2- ⁇ ropenyl, and the different butenyl, pentenyl and hexenyl isomers. "Alkenyl” also includes polyenes such as 1 ,2-propadienyl and 2,4-hexadienyl. "Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers.
  • Alkynyl can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.
  • Alkoxy includes, for example, methoxy, ethoxy, «-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers.
  • Alkoxyalkyl denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH 2 OCH 2 and
  • Alkylthio includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers.
  • Alkylthioalkyl denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” include CH 3 SCH 2 , CH 3 SCH 2 CH 2 , CH 3 CH 2 SCH 2 , CH 3 CH 2 CH 2 CH 2 SCH 2 and CH 3 CH 2 SCH 2 CH 2 .
  • Cycloalkyl includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • Cycloalkenyl includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1 ,4-cyclohexadienyl.
  • aromatic ring system denotes fully unsaturated carbocycles and heterocycles in which the polycyclic ring system is aromatic (where aromatic indicates that the Hlickel rule is satisfied for the ring system).
  • aromatic heterocyclic ring system includes fully aromatic heterocycles and heterocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the H ⁇ ckel rule is satisfied).
  • the heterocyclic ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.
  • nitrogen containing heterocycles can form JV-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form JV-oxides.
  • tertiary amines can form N-oxides.
  • Synthetic methods for the preparation of .V-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and w-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as r-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.
  • MCPBA peroxy acids
  • alkyl hydroperoxides such as r-butyl hydroperoxide
  • sodium perborate sodium perborate
  • dioxiranes such as dimethyldioxirane
  • halogen either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine.
  • 1-2 halogen indicates that one or two of the available positions for that substituent may be halogen which are independently selected. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F 3 C, C1CH , CF 3 CH 2 and CF 3 CC1 2 .
  • haloalkynyl examples include HC ⁇ CCHCl, CF 3 C ⁇ C, CC1 3 C ⁇ C and FCH 2 C ⁇ CCH 2 .
  • haloalkoxy examples include CF 3 O, CCl 3 CH 2 O, HCF 2 CH 2 CH 2 O and CF 3 CH 2 O.
  • C1-C3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl
  • C 2 alkoxyalkyl designates CH 3 OCH 2
  • C 3 alkoxyalkyl designates, for example, CH 3 CH(OCH 3 ), CH 3 OCH 2 CH 2 or CH 3 CH 2 OCH 2
  • C4 alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 and CH 3 CH 2 OCH 2 CH 2 .
  • alkylcarbonyl examples include C(O)CH 3 , C(O)CH 2 CH 2 CH 3 and C(O)CH(CH 3 ) 2 .
  • the compounds of this invention thus include compounds of Formula I, geometric and stereoisomers thereof, N-oxides thereof and agriculturally suitable salts thereof.
  • the compound of the invention can exist as one or more stereoisomers.
  • the various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers.
  • one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers.
  • the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.
  • the salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.
  • the salts of the compounds of the invention also include those formed with organic bases (e.g., pyridine, ammonia, or triethylamine) or inorganic bases (e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium) when the compound contains an acidic group such as a carboxylic acid or phenol.
  • organic bases e.g., pyridine, ammonia, or triethylamine
  • inorganic bases e.g., hydrides, hydroxides, or carbonates of sodium, potassium, lithium, calcium, magnesium or barium
  • A is phenyl, pyridinyl or lH-pyrazolyl, each optionally substituted by one or more groups selected from halogen, C ⁇ -C alkyl, Cj-C 4 haloalkyl, C j -C 4 alkoxy, and C1-C4 haloalkoxy; and when A is 1H- pyrazolyl, then A can be bonded through any available carbon or nitrogen atom of said pyrazole ring to the phenyl or pyridyl ring;
  • R 1 is C r C 6 alkyl, C r C 6 haloalkyl or C 3 -C 7 cycloalkyl
  • R 2 is C r C 6 alkyl, C r C 6 haloalkyl or C 3 -C 7 cycloalkyl
  • R 1 and R 2 can be taken together as -CH 2 CH 2 -, -CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH 2 CH 2 CH 2 CH 2 - or -CH 2 CH 2 OCH 2 CH 2 -
  • each R 3 is independently halogen, C1-C 4 alkoxy, C1-C 4 haloalkoxy, C 1 -C 4 alkyl or C ⁇ -C 4 haloalkyl.
  • the substituent A and the tetrazolinone ring are attached to adjacent carbon atoms of the phenyl or pyridine ring.
  • Most preferred is the compound of Preferred 2 which is NJV-diethyl-4,5-dihydro-5-oxo-4-[2-[3-(trifluoromethyl)-lH-pyrazol-l- y l]phenyl] - 1 H-tetrazol- 1 -carboxamide .
  • This invention also relates to herbicidal compositions comprising herbicidally effective amounts of the compounds of the invention and at least one of a surfactant, a solid diluent or a liquid diluent.
  • the preferred compositions of the present invention are those which comprise the above preferred compounds.
  • This invention also relates to a method for controlling undesired vegetation comprising applying to the locus of the vegetation herbicidally effective amounts of the compounds of the invention (e.g., as a composition described herein).
  • the preferred methods of use are those involving the above preferred compounds.
  • the compounds of Formula I can be prepared by one or more of the following methods and variations as described in Schemes 1-17.
  • the definitions of A, W, R'-R 6 , m, and n in the compounds of Formulae 1-17 below are as defined above in the Summary of the Invention.
  • Scheme 1 illustrates the preparation of compounds of Formula I whereby a tetrazolinone of Formula 1 is reacted with a carbamyl chloride of Formula 2 in the presence of a suitable acid acceptor agent.
  • Suitable acid acceptor agents include alkali carbonates, alkali bicarbonates, alkyl tertiary amines such as triethylamine, pyridine, and, preferably, 4-dimethylaminopyridine (DMAP).
  • DMAP can be used as a catalyst in the presence of another suitable acid acceptor agent in order to selectively synthesize a compound of Formula I.
  • the reaction is carried out in an inert solvent such as tetrahydrofuran, acetone, chloroform, chlorobenzene or preferably acetonitrile or toluene, and at a temperature range between 0 °C and 110 °C by methods known in the art (or slight modification of these methods); for example, see Yanagi, A. et al. EP 646,577; Goto, T. et al. EP 708,097; Covey, R. A. et al. U.S. Patent 4,618,365.
  • compounds of Formula I can be prepared whereby a tetrazolinone of Formula 1 in an inert solvent such as toluene or ethyl acetate is reacted with phosgene and a suitable tertiary amine base such as triethylamine, and the product of such reaction is reacted with a secondary amine of Formula 3, optionally in the presence of a suitable base such as pyridine (Scheme 2).
  • This type of reaction can be carried out by methods known in the art (or slight modification of these methods); see, for example, Covey, R. A. et al. U.S. Patent 5,019,152.
  • base e.g., pyridine
  • Carbamyl chlorides of Formula 2 are well known in the art; see, for example, Goto, T. et al. EP 711,761, EP 692,482, and EP 695,748.
  • Scheme 3 illustrates a preferred method for preparing tetrazolinones of Formula 1 whereby an isocyanate of Formula 4 is reacted with refluxing trimethylsilylazide (also known as azidotrimethylsilane), followed by treatment of the product of such reaction with a protic solvent such as water or preferably with methanol.
  • a protic solvent such as water or preferably with methanol.
  • isocyanates of Formula 4 can be prepared by Curtius rearrangement of appropriate acid chlorides of Formula 5 using methods generally known in the art (Scheme 4); see, for example, March, J. Advanced Organic Chemistry, 3rd edition; John Wiley & Sons, 1985; pp 984-985 and 380.
  • Acid chlorides of Formula 5 can be prepared by reacting an acid of Formula 6 with oxalyl chloride (or thionyl chloride) and optionally a catalytic amount of dimethylformamide (Scheme 5).
  • This chlorination is well known in the art; see, for example, Michaely, W. J. EP 369,803; Goto, T. et al. EP 695,748.
  • Other methods are also well known in the art for converting carboxylic acids to acid chlorides; see, for example, Ogliaruso, M. A. et al. Synthesis of Carboxylic Acids, Esters and Their Derivatives; John Wiley & Sons, 1991, pp 172-174.
  • Carboxylic acids of Formula 6 can be prepared as illustrated in Scheme 6, whereby an ester of Formula 7 is saponified (e.g., potassium hydroxide in methanol, then acidified with an acid such as hydrochloric acid) or, alternatively, is acid hydrolyzed (e.g., 5NHC1 in acetic acid) by methods known in the art (or slight modification of these methods); see for example, Ogliaruso, M. A. et al. Synthesis of Carboxylic Acids, Esters and Their Derivatives; John Wiley & Sons, 1991, pp 5-7.
  • R ⁇ is C j -C 2 alkyl
  • Isocyanates of Formula 4 can also be prepared by treatment of corresponding amines of Formula 8 with phosgene or known phosgene equivalents (e.g., diphosgene or triphosgene) by methods generally known in the art (Scheme 7); see for example, March, J. Advanced Organic Chemistry, 3rd edition; John Wiley & Sons, 1985, p 370; Chem. Rev. (1972), 72, pp 457-496; Sandier, R. S. et al. Organic Functional Group Preparations, 2nd edition; Academic Press; Vol. II, pp 152 and 260; Lehman, G. et al. Preparative Organic Chemistry; John Wiley & Sons, 1972; p 472.
  • phosgene or known phosgene equivalents e.g., diphosgene or triphosgene
  • Amines of Formula 8 can be prepared by reduction of corresponding nitro compounds of Formula 9 (Scheme 8).
  • Scheme 8 A wide variety of methods are documented in the chemical literature for carrying out such transformations; see for example, Rorer, M. P. U.S. Patent 4,511,392; Ohme, R. et al. Preparative Organic Chemistry; John Wiley & Sons, 1972; p 557; Groggins Unit Processes in Organic Chemistry; McGraw-Hill Book Co.: New York, 1947; pp 73-128; March, J. Advanced Organic Chemistry, 3rd edition; John Wiley & Sons, 1985; pp 1103-1104.
  • nitro compounds of Formula 9a can be prepared as illustrated in Scheme 9 whereby an appropriate nitro compound of Formula 10 in an inert solvent is reacted with a nucleophilic heterocycle of Formula 11 in the presence of a suitable base.
  • Suitable bases include alkali carbonates such as potassium carbonate, potassium tert- butoxide, and sodium hydride.
  • Suitable solvents include dimethylformamide, 2- butanone, and tetrahydrofuran. The reaction is carried out at a temperature range of about 0 °C to 150 °C, preferably about 80 °C to 120 °C, with dimethylformamide as the solvent and potassium carbonate as the base.
  • the compound of Formula 9a can be purified by recrystallization or flash column chromatography on silica gel by those skilled in the art. Protecting and deprotecting functional groups not compatible with reaction conditions may be necessary for compounds with such functional groups.
  • X is F, Cl, Br, CH3S0 2 0 or CF3SO2O and X is ortho o para to the N0 2 group;
  • Nu is an optionally-substituted imidazole, pyrazole, triazole or tetrazole; and
  • a 1 is an optionally-substituted 1 / -imidazole, 1 //-pyrazole, l//-l,2,4-triazole, 4//-l,2,4-triazole or tetrazole and A* is ortho o ⁇ para to the N0 2 group.
  • Scheme 10 illustrates the preparation of many esters of Formula 7a whereby an appropriate ester of Formula 12 in an inert solvent is reacted with a nucleophilic heterocycle of Formula 13 in the presence of a suitable base. Reaction conditions are as described for Scheme 9.
  • X is F, Cl, Br, CH3S0 2 0 or CF3S0 2 0 and X is ortho or para to the C0 2 R 7 group;
  • Nu is an optionally-substituted imidazole, pyrazole, triazole or tetrazole; and
  • Al is an optionally-substituted 1 -imidazole, l /-pyrazole, l /-l,2,4-triazole, 4 /-l,2,4-triazole or tetrazole and Al is ortho or para to the C0 2 R7 group.
  • Scheme 11 illustrates the preparation of many carboxylic acids of Formula 6 whereby a bromide compound of Formula 13 is treated with «-butyllithium (or magnesium) and the lithium salt (or the Grignard reagent) generated in situ is then reacted with carbon dioxide followed by acidification with an acid such as hydrochloric acid.
  • This conversion is carried out by using methods known in the art (or by slights modification of these methods); see for example, Ogliaruso, M. A. et al. Synthesis of Carboxylic Acids, Esters and Their Derivatives; John Wiley & Sons; pp 27-28; Bridges, A. J. et al. J. Org. Chem. (1990), 55, 773; Franke, C. et al. Angew. Chem. Int. Ed. (1969), 8, 68. Protecting and deprotecting functional groups not compatible with the reaction conditions may be necessary for compounds with such functional groups.
  • Some bromo compounds of Formula 13 can be prepared by bromination of the corresponding substituted benzene or pyridine of Formula 14 with bromine or other equivalent reagent in an inert solvent as shown in Scheme 12. This bromination is carried out by general methods known in the art; see for example, Campaigne, E. et al. J. Heterocycl. Chem. (1969), 6, 517; Gilman, H. J. Am. Chem. Soc. (1955), 77, 6059. Scheme 12
  • nitro compounds of Formula 9, benzene and pyridine compounds of Formula 14, bromo compounds of Formula 13, and ester compounds of Formula 7 can be prepared by those skilled in the art using methods known in the art (or by obvious modification of these methods); see for example, Rorer, M. P. U.S. Patent 4,511,392; Wolf, A. D. U.S. Patent 4,465,505; Sauers, R. F. U.S. Patent 4,460,401 ; Denes, R. WO 93/11097; Petersen, C. et al. WO 96/31517; Denes, R. WO 95/09846; Katritzky, A. R. et al. Comprehensive Heterocyclic Chemistry; Pergamon Press; Volumes 2-6. Protecting and deprotecting functional groups not compatible with the reaction conditions may be necessary for compounds with such functional groups.
  • Scheme 13 illustrates another preferred method for preparing tetrazolinones of
  • tetrazolinones of Formula 1 can be prepared by a multi-step reaction sequence starting from an amino compound of Formula 8. These types of reactions can be carried out by methods known in the art (or slight modification of these methods).
  • an amino compound of Formula 8 is reacted with carbon disulfide and a tertiary amine base such as triethylamine either neat or preferably in a solvent such as ethanol;
  • the product of such reaction is reacted with an alkylating agent such as methyl iodide to form the corresponding methyl dithiocarbamate (see, for example, Fairfull, A. E. S. J. Chem. Soc. (1955), 796; Knott, E. B. J.
  • Scheme 15 illustrates another multi-step reaction sequence for preparing tetrazolinones of Formula 1 from corresponding amines of Formula 8.
  • These types of reactions can also be carried out by methods known in the art (or slight variations of these methods).
  • an amino compound of Formula 8 is converted to the corresponding methyl dithiocarbamate (see steps 1 and 2 of Scheme 14);
  • subsequent reaction of this product with hydrazine monohydrate in a solvent such as ethanol provides the corresponding 3-thiosemicarbazide;
  • alkylation of this product with, e.g., dimethyl sulfate followed by treatment of the product of such reaction with sodium nitrite in hydrochloric acid provides the corresponding 5-methylthiotetrazole;
  • oxidation of this reagent with a suitable oxidizing agent such as Oxone® or peracetic acid provides a sulfone of Formula 16;
  • reaction of this reagent with an inorganic base such as sodium hydroxide in a solvent such as te
  • tetrazolinones of Formula 1 can also be prepared as illustrated in Scheme 16 whereby a phenyl carbamate of Formula 17 is reacted in an inert solvent such as dimethylformamide with sodium azide in the presence of aluminum chloride.
  • This type of reaction can be carried out by methods known in the art (or slight modification of these methods); see for example, Goto, T. et al. EP 692,482 and EP 695,748.
  • Phenyl carbamates of Formula 17 can be prepared by reaction of an amine of
  • tetrazolinones of Formula 1 can be prepared as illustrated in Scheme 17, whereby an appropriate acid chloride of Formula 5 is refluxed with excess trimethylsilylazide, and the product of such reaction is treated with a protic solvent such as water or, preferably with methanol.
  • a protic solvent such as water or, preferably with methanol.
  • This type of reaction can be carried out by methods known in the art (or by slight modification of these methods); see, for example, Toselli, M. et al. J. Chem. Soc. Perkin Trans 1, (1992), 1 101 ; Goto, T. et al. EP 695,748 and EP 692,482; Horwitz, J. P. et al. J. Am. Chem. Soc. (1959), 81, 3076.
  • Step C Preparation of L4-dihvdro-4-[2-[3-(trifluoromethyl>lH-pyrazol-l- yllphenyll-5H-tetrazol-5-one 3.0 g (0.0132 mol) of the title compound of Step B was added portionwise to a solution under a nitrogen atmosphere containing 4.9 g (0.0264 mol) of trichloromethyl chloroformate dissolved in 50 mL of ethyl acetate, while maintaining the reaction temperature at about 5 °C with external cooling. After addition was complete, the suspension was refluxed under nitrogen for 7 h, then evaporated to dryness under reduced pressure.
  • Step D Preparation of N V-diethyl-4,5-dihydro-5-oxo-4-r2-r3-( ' trifluoromethyl)- lH-pyrazol- 1 -yllphenyl]- lH-tetrazol- 1 -carboxamide To a suspension containing 1.35 g (0.0046 mol) of the title compound of Step C in
  • the suspension was refluxed under nitrogen for 24 h and then concentrated under reduced pressure at about 90 °C to remove excess azidotrimethylsilane. After cooling the residue to 25 °C, about 20 mL of methanol was added. The suspension was stirred about 0.25 h and then concentrated under reduced pressure at 90 °C. An additional 20 mL of methanol was added to the residue and the suspension again concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel with hexane:ethyl acetate (8:2, then 1 : 1, then 100% ethyl acetate) to yield a gum.
  • Step D Preparation of N V-diethyl-4,5-dihvdro-5-oxo-4-r2-r3-(trifluoromethyl - lH-pyrazol- 1 -yll-3-pyridinyl]- lH-tetrazol- 1 -carboxamide
  • a suspension containing 1.0 g (0.0034 mol) of the title compound of Step C in 17 mL of toluene was added 0.5 g (0.0041 mol) of 4-dimethylaminopyridine. After stirring for several minutes, 0.55 g (0.0041 mol) of diethylcarbamyl chloride (Aldrich) was added.
  • A- l A-25 ( 1 -methyl- 1 //-imidazol-4-yl)- A-2
  • A-26 (1 -methyl- l//-imidazol-5-yl)-
  • A-4 A-28 (2-methyl-5-oxazolyl)-
  • A-5 A-29 (2-methyl-4-oxazolyl)-
  • A-6 A-30 (4-methyl-2-thiazolyl)-
  • A-7 A-31 (5-methyl-2-thiazolyl)-
  • A-8 A-32 (2-thiazolyl)-
  • A-33 (2-methyl-5-thiazolyl)-
  • A-10 A-35 (3-methyl-4-isothiazolyl)-
  • A-l l A-36 (3-methyl-5-isothiazolyl)-
  • A-12 A-37 (5-methyl-3-isothiazolyl)-
  • A-13 A-38 (l//-l,2,4-triazol-l-yl)-
  • A-14 A-39 (1 -methyl- 1 /-1, 2,4-triazol-3-yl)-
  • A-15 A-40 (3-methyl-l/ ⁇ -l,2,4-triazol-l-yl)-
  • A-16 A-41 (3-trifluoromethyl- l /-l,2,4-triazol- 1-
  • A-18 A-42 (5-methyl-l/ -l,2,4-triazol-l-yl)-
  • A-19 A-43 (4//-l,2,4-triazol-4-yl)-
  • A-20 A-44 (3-methyl-l,2,4-oxadiazol-5-yl)-
  • A-21 A-45 (5-trifluoromethyl-l,3,4-oxadiazol-2-
  • A-23 A-46 (5-methyl-l,2,4-oxadiazol-3-yl)-
  • A-24 A-47 (4-methyl-3-furazanyl)- A-48 (3-methyl- l,2,4-tr ⁇ az ⁇ n-5-yl)-
  • Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant.
  • the formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.
  • Useful formulations include liquids such as solutions (including emulsif ⁇ able concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels.
  • Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible ("wettable") or water-soluble.
  • Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or "overcoated”). Encapsulation can control or delay release of the active ingredient.
  • Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon 's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses.
  • All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.
  • Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, ⁇ N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers.
  • Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate.
  • Liquid diluents include, for example, water, N ⁇ V-dimethylformamide, dimethyl sulfoxide, vV-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, rung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.
  • Solutions can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714.
  • Water-dispersible and water-soluble granules can be prepared as taught in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. 3,299,566.
  • Compound 1 98.5% silica aerogel 0.5% synthetic amorphous fine silica 1.0%.
  • Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%.
  • Compound 1 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%.
  • Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%.
  • Some of the compounds are useful for the control of selected grass and broadleaf weeds with tolerance to important agronomic crops which include but are not limited to alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine), and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass).
  • important agronomic crops which include but are not limited to alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize), sorghum, soybeans, rice, oats, peanuts, vegetables, tomato,
  • a herbicidally effective amount of the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of compounds of this invention is 0.001 to 20 kg/ha with a preferred range of 0.004 to 1.0 kg/ha. One skilled in the art can easily determine the herbicidally effective amount necessary for the desired level of weed control.
  • Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. Compounds of this invention can also be used in combination with commercial herbicide safeners such as benoxacor, dichlormid and furilazole to increase safety to certain crops.
  • commercial herbicide safeners such as benoxacor, dichlormid and furilazole to increase safety to certain crops.
  • a mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control: acetochlor, acifluorfen and its sodium salt, aclonifen, acrolein (2-propenal), alachlor, ametryn, amidosulfuron, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl, bensulide, bentazone, bifenox, bispyribac and its sodium salt, bromacil, bromoxynil, bromoxynil octanoate, butachlor, butralin, butroxydim (ICIA0500), butylate, caloxydim (BAS 620H), carfentrazone-ethyl,
  • Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments.
  • Plant species in the flood test consisted of rice (Oryza sativa), smallflower flatsedge (Cyperus difformis), duck salad (Heteranthera limosa) and bamyardgrass (Echinochloa crus-galli) grown to the 2-leaf stage for testing.
  • Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated.
  • Plant response ratings, summarized in Table A are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control.
  • a dash (-) response means no test result.
  • Rate 2000 g/ha 1 3 4 Rate 2000 g/ha 1 3 4
  • Rate 1000 g/ha 5 6 7 8 Rate 1000 g/ha 5 6 7 8
  • Redroot pigweed - - - 6 Redroot pigweed - - - 8
  • Plants ranged in height from 2 to 18 cm (1- to 4-leaf stage) for postemergence treatments.
  • Plant species in the flood test consisted of rice (Oryza sativa), smallflower flatsedge (Cyperus difformis), duck salad (Heteranthera limosa) and bamyardgrass (Echinochloa crus-galli) grown to the 2-leaf stage for testing.
  • Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated.
  • Plant response ratings, summarized in Table B are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (-) response means no test result.
  • Indica Rice (Oryza sativa) seed (designated rice, indica 1) and seedlings (designated rice, indica 3) at the 2 leaf stage, seeds, tubers or plant parts selected from bamyardgrass (Echinochloa crus-galli), ducksalad (Heteranthera limosa), early watergrass (Echinochloa oryzoides), junglerice (Echinochloa colonum), late watergrass (Echinochloa oryzicola), redstem (Ammania species), rice flatsedge (Cyperus iria), smallflower flatsedge (Cyperus difformis) and tighthead sprangletop (Leptochloa fasicularis), were planted into this soil.
  • bamyardgrass Echinochloa crus-galli
  • ducksalad Heteranthera limosa
  • early watergrass Echinochloa oryzoides
  • junglerice Echinoch
  • Plantings and waterings of these crops and weed species were adjusted to produce plants of appropriate size for the test. At the 2-leaf stage, water levels were raised to 3 cm above the soil surface and maintained at this level throughout the test. Chemical treatments were formulated in a non-phytotoxic solvent mixture which included a surfactant and applied directly to the paddy water by pipette, or to the plant foliage by an air pressure-assisted, calibrated belt-conveyer spray system.

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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)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des composés de la Formule (I), ainsi que leurs N-oxydes et leurs sels adaptés à l'agriculture, lesquels sont utiles pour lutter contre la végétation indésirable, formule dans laquelle A, W, R?1, R2, R3¿ et m sont définis dans la description de l'invention. L'invention concerne également des compositions contenant les composés de la formule (I), ainsi qu'un procédé de lutte contre la végétation indésirable consistant à mettre la végétation ou son environnement en contact avec une dose efficace d'un composé de la formule (I).
PCT/US1997/022461 1996-12-13 1997-12-09 Amides heterocycliques herbicides WO1998025912A1 (fr)

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999048890A1 (fr) * 1998-03-26 1999-09-30 E.I. Du Pont De Nemours And Company Tetrazolinones herbicides
WO2006067139A1 (fr) * 2004-12-21 2006-06-29 Janssen Pharmaceutica N.V. Derives de triazolone, tetrazolone et imidazolone utilises comme antagonistes des recepteurs alpha2c-adrenergiques
US20110274655A1 (en) * 2010-05-05 2011-11-10 Infinity Pharmaceuticals Tetrazolones as inhibitors of fatty acid synthase
WO2012052412A1 (fr) 2010-10-22 2012-04-26 Bayer Cropscience Ag Nouveaux composés hétérocycliques utilisés en tant qu'agents pour lutter contre des nuisibles
JP2012529512A (ja) * 2009-06-08 2012-11-22 アブラクシス バイオサイエンス リミテッド ライアビリティー カンパニー トリアジン誘導体類及びそれらの治療応用
WO2015056811A1 (fr) * 2013-10-17 2015-04-23 住友化学株式会社 Composé tétrazolinone et son application
WO2017110862A1 (fr) * 2015-12-25 2017-06-29 住友化学株式会社 Composé d'oxadiazole et son utilisation
US9822095B2 (en) 2014-03-28 2017-11-21 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
US9826741B2 (en) 2014-03-28 2017-11-28 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
CN107501270A (zh) * 2017-09-01 2017-12-22 南京宏腾建设工程有限公司 一种含有磺酰吖丙啶结构的化合物、药物组合物以及其应用
US10070646B2 (en) 2014-03-28 2018-09-11 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
EP3275968A4 (fr) * 2015-03-27 2019-05-08 cynora GmbH Matériau à fluorescence retardée thermo-activée ortho-substituée et dispositif électroluminescent organique le comprenant

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US4618365A (en) * 1983-12-09 1986-10-21 Uniroyal Chemical Company, Inc. Substituted tetrazolinones and their use as herbicides
US5019152A (en) * 1983-12-09 1991-05-28 Uniroyal Chemical Company, Inc. Substituted tetrazolinones and their use as herbicides
EP0646577A1 (fr) * 1993-09-30 1995-04-05 Nihon Bayer Agrochem K.K. Procédé pour la préparation de dérivés de la 5(4H)-tétrazoline substitués aux positions 1 et 4
EP0692482A2 (fr) * 1994-07-12 1996-01-17 Nihon Bayer Agrochem K.K. Dérivés de 1-pyridyltétrazolinone
EP0695748A1 (fr) * 1994-08-05 1996-02-07 Nihon Bayer Agrochem K.K. Herbicides tétrazolinones
EP0708097A1 (fr) * 1994-10-18 1996-04-24 Nihon Bayer Agrochem K.K. Tétrazolinones à activité herbicide
EP0711761A1 (fr) * 1994-11-11 1996-05-15 Nihon Bayer Agrochem K.K. Tétrazolinones
EP0726259A1 (fr) * 1995-02-08 1996-08-14 Bayer Ag Procédé de préparation de N-carbamoyl-tétrazolinones substituées
EP0764642A2 (fr) * 1995-09-22 1997-03-26 Bayer Ag Procédé pour la préparation de 1-aryl-4-carbamoyl-tétrazolinones

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US4618365A (en) * 1983-12-09 1986-10-21 Uniroyal Chemical Company, Inc. Substituted tetrazolinones and their use as herbicides
US5019152A (en) * 1983-12-09 1991-05-28 Uniroyal Chemical Company, Inc. Substituted tetrazolinones and their use as herbicides
EP0646577A1 (fr) * 1993-09-30 1995-04-05 Nihon Bayer Agrochem K.K. Procédé pour la préparation de dérivés de la 5(4H)-tétrazoline substitués aux positions 1 et 4
EP0692482A2 (fr) * 1994-07-12 1996-01-17 Nihon Bayer Agrochem K.K. Dérivés de 1-pyridyltétrazolinone
EP0695748A1 (fr) * 1994-08-05 1996-02-07 Nihon Bayer Agrochem K.K. Herbicides tétrazolinones
EP0708097A1 (fr) * 1994-10-18 1996-04-24 Nihon Bayer Agrochem K.K. Tétrazolinones à activité herbicide
EP0711761A1 (fr) * 1994-11-11 1996-05-15 Nihon Bayer Agrochem K.K. Tétrazolinones
EP0726259A1 (fr) * 1995-02-08 1996-08-14 Bayer Ag Procédé de préparation de N-carbamoyl-tétrazolinones substituées
EP0764642A2 (fr) * 1995-09-22 1997-03-26 Bayer Ag Procédé pour la préparation de 1-aryl-4-carbamoyl-tétrazolinones

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999048890A1 (fr) * 1998-03-26 1999-09-30 E.I. Du Pont De Nemours And Company Tetrazolinones herbicides
WO2006067139A1 (fr) * 2004-12-21 2006-06-29 Janssen Pharmaceutica N.V. Derives de triazolone, tetrazolone et imidazolone utilises comme antagonistes des recepteurs alpha2c-adrenergiques
JP2008524312A (ja) * 2004-12-21 2008-07-10 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ アルファ−２ｃアドレノレセプターアンタゴニストとしての使用のためのトリアゾロン、テトラゾロン及びイミダゾロン誘導体
EA011514B1 (ru) * 2004-12-21 2009-04-28 Янссен Фармацевтика Н.В. Производные триазолона, тетразолона и имидазолона для применения в качестве антагонистов альфа-2с-адренорецептора
JP2012529512A (ja) * 2009-06-08 2012-11-22 アブラクシス バイオサイエンス リミテッド ライアビリティー カンパニー トリアジン誘導体類及びそれらの治療応用
US9346769B2 (en) 2010-05-05 2016-05-24 Infinity Pharmaceuticals, Inc. Tetrazolones as inhibitors of fatty acid synthase
US20110274655A1 (en) * 2010-05-05 2011-11-10 Infinity Pharmaceuticals Tetrazolones as inhibitors of fatty acid synthase
US8546432B2 (en) * 2010-05-05 2013-10-01 Infinity Pharmaceuticals, Inc. Tetrazolones as inhibitors of fatty acid synthase
WO2012052412A1 (fr) 2010-10-22 2012-04-26 Bayer Cropscience Ag Nouveaux composés hétérocycliques utilisés en tant qu'agents pour lutter contre des nuisibles
US9173396B2 (en) 2010-10-22 2015-11-03 Bayer Intellectual Property Gmbh Heterocyclic compounds as pesticides
WO2015056811A1 (fr) * 2013-10-17 2015-04-23 住友化学株式会社 Composé tétrazolinone et son application
JPWO2015056811A1 (ja) * 2013-10-17 2017-03-09 住友化学株式会社 テトラゾリノン化合物及びその用途
US10077254B2 (en) 2013-10-17 2018-09-18 Sumitomo Chemical Company, Limited Tetrazolinone compound and use thereof
US9822095B2 (en) 2014-03-28 2017-11-21 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
US9826741B2 (en) 2014-03-28 2017-11-28 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
US10070646B2 (en) 2014-03-28 2018-09-11 Sumitomo Chemical Company, Limited Tetrazolinone compound and application thereof
EP3275968A4 (fr) * 2015-03-27 2019-05-08 cynora GmbH Matériau à fluorescence retardée thermo-activée ortho-substituée et dispositif électroluminescent organique le comprenant
US11758808B2 (en) 2015-03-27 2023-09-12 Samsung Display Co., Ltd. Ortho-substituted thermally activated delayed fluorescence material and organic light-emitting device comprising same
WO2017110862A1 (fr) * 2015-12-25 2017-06-29 住友化学株式会社 Composé d'oxadiazole et son utilisation
CN107501270A (zh) * 2017-09-01 2017-12-22 南京宏腾建设工程有限公司 一种含有磺酰吖丙啶结构的化合物、药物组合物以及其应用

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