US20150183750A1 - 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation - Google Patents

5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation Download PDF

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Publication number
US20150183750A1
US20150183750A1 US14/584,368 US201414584368A US2015183750A1 US 20150183750 A1 US20150183750 A1 US 20150183750A1 US 201414584368 A US201414584368 A US 201414584368A US 2015183750 A1 US2015183750 A1 US 2015183750A1
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compound
formula
group
dmf
molar ratio
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Inventor
Nakyen Choy
Ronald Ross, Jr.
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Adama Makhteshim Ltd
Corteva Agriscience LLC
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Dow AgroSciences LLC
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Priority to US14/584,368 priority Critical patent/US20150183750A1/en
Publication of US20150183750A1 publication Critical patent/US20150183750A1/en
Assigned to DOW AGROSCIENCES LLC reassignment DOW AGROSCIENCES LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHOY, NAKYEN, ROSS, RONALD, JR
Priority to US15/173,529 priority patent/US9840476B2/en
Assigned to ADAMA MAKHTESHIM LTD. reassignment ADAMA MAKHTESHIM LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DOW AGROSCIENCES LLC
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
    • C07D333/10—Thiophene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • N3-substituted-N1-sulfonyl-5-fluoropyrimidinone fungicides and related compounds e.g., by the use of reagents and/or chemical intermediates and isolation and purification techniques which provide improved time and cost efficiency.
  • R 1 is selected from:
  • R 2 is selected from:
  • a base such as an alkali carbonate, e.g., sodium-, potassium-, cesium-, and lithium carbonate (Na 2 CO 3 , K 2 CO 3 , Cs 2 CO 3 , and Li 2 CO 3 , respectively) or an alkali alkoxide, for example, potassium tert-butoxide (KO t Bu) and an alkylating agent, such as an alkyl halide of Formula R 2 —X, wherein R 2 is as previously defined and X is a halogen, e.g., iodine, bromine, and chlorine, in a polar solvent, such as N,N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), dimethylacetamide (DMA), N-methylpyrrolidone (NMP), acetonitrile (CH 3 CN), and the like, at concentrations from about 0.1 molar (M) to about 3 M.
  • a base such as an alkali carbonate, e.
  • a molar ratio of compounds of Formula II to the base is from about 3:1 to about 1:1 and a molar ratio of compounds of Formula II to alkylating agent is from about 1:1 to about 3:1.
  • molar ratios of compounds of Formula II to the base and compounds of Formula II to the alkylating agent of about 2:1 and about 1:3, respectively, are used.
  • the reactions are conducted at temperatures between ⁇ 78° C. and 90° C., and in other embodiments, the reactions are conducted between 22° C. and 60° C.
  • compositions comprising mixtures of compounds of Formulas II and III are preferred, as isolation and purification can be achieved through precipitation and recrystallization, and the intermediate compounds of Formula II can be recovered and recycled.
  • compositions comprising mixtures of compounds of Formulas III and IV require chromatographic separation to give III along with the undesired dialkylated by-product of Formula IV.
  • the desired crude composition i.e., mixtures of compounds of Formula II and compounds of Formula III, wherein R 1 is methoxy (OCH 3 ) and R 2 is methyl (CH 3 )
  • R 1 is methoxy
  • R 2 is methyl
  • the desired crude composition is obtained through contacting a compound of Formula II with Li 2 CO 3 and methyl iodide (CH 3 I) in DMF (1.0 M) in a molar ratio of about 1:0.6:3 at 45° C.
  • the ratio of CH 3 CN:DMF is about 1:2 and the ratio of 2.5% aqueous Na 2 S 2 O 3 :DMF is about 1:1
  • the resultant solid is further purified by crystallization/precipitation from a warmed solution, about 30° C.-40° C., of the solid in a solution of a polar, aprotic solvent, such as CH 3 CN, by the addition of water (H 2 O), wherein the ratio of H 2 O:CH 3 CN is from about 1:2 to about 3:1, to give the purified compound of Formula III, and in another embodiment the ratio of H 2 O:CH 3 CN to affect precipitation of pure III is about 2:1.
  • compounds of Formula II may be prepared by contacting compounds of Formula I with bis-N,O-trimethylsilylacetamide (BSA) at an elevated temperature, such as 70° C., for a period of about 1 hour (h), followed by cooling and contacting the solution containing the protected pyrimidinol with a substituted benzene sulfonyl chloride, generalized by R 1 —PhSO 2 Cl, wherein R 1 is as previously defined, at 20-25° C.
  • the molar ratio of the compound of Formula Ito BSA and the sulfonyl chloride is about 1:3:1.1, respectively, and in another embodiment reducing the molar ratio of the reactants to about 1:1.1:1.1 affords improved yields.
  • alkyl refers to a branched, unbranched, or saturated cyclic carbon chain, including, but not limited to, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tertiary butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
  • alkenyl refers to a branched, unbranched or cyclic carbon chain containing one or more double bonds including, but not limited to, ethenyl, propenyl, butenyl, isopropenyl, isobutenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and the like.
  • aryl refers to any aromatic, mono- or bi-cyclic, containing 0 heteroatoms.
  • heterocycle refers to any aromatic or non-aromatic ring, mono- or bi-cyclic, containing one or more heteroatoms.
  • alkoxy refers to an —OR substituent.
  • halogen refers to one or more halogen atoms, defined as F, Cl, Br, and I.
  • haloalkyl refers to an alkyl, which is substituted with Cl, F, I, or Br or any combination thereof.
  • references to the compounds of Formulas I, II, III, and IV are read as also including optical isomers and salts.
  • Exemplary salts may include: hydrochloride, hydrobromide, hydroiodide, and the like.
  • the compounds of Formulas I, II, III, and IV may include tautomeric forms.
  • a method of making compounds of Formula III includes contacting a compound of Formula II with an alkali alkoxide and an alkylating agent, and forming a compound of Formula III:
  • R 1 is selected from the group consisting of:
  • R 2 is selected from the group consisting of:
  • the contacting step is carried out between 22° C. and 60° C.
  • the contacting step further includes a solvent selected from the group consisting of DMF, DMSO, DMA, NMP, and CH 3 CN.
  • the alkali alkoxide is selected from the group consisting of: KO t Bu, CH 3 ONa, CH 3 CH 2 ONa, CH 3 CH 2 OLi, CH 3 OLi, CH 3 CH 2 OK, and CH3CH 2 ONa.
  • the alkylating agent is selected from the group consisting of: alkyl halides and benzyl halides.
  • the alkyl halide and benzyl halide are selected from methyl iodide (CH 3 I), ethyl iodide (C 2 H 5 1), and benzyl bromide (BnBr).
  • the alkali alkoxide is KO′Bu
  • the solvent is DMF
  • a molar ratio of Compound II to alkali alkoxide is from about 3:1 to about 1:1 and a molar ratio of Compound II to alkylating agent is from about 1:1 to about 3:1.
  • a molar ratio of Compound II to alkali alkoxide base is about 2:1
  • a molar ratio of Compound II to alkylating agent is 1:3.
  • the method includes diluting a completed reaction mixture with CH 3 CN and 2.5% aqueous Na 2 S 2 O 3 .
  • a ratio of DMF to CH 3 CN is from about 1:1 to about 3:1 and a ratio of DMF to 2.5% aqueous Na 2 S 2 O 3 is from about 1:2 to about 2:1.
  • a ratio of DMF to CH 3 CN is about 2:1 and a ratio of DMF to 2.5% aqueous Na 2 S 2 O 3 is about 1:1.
  • a method of preparing a compound of Formula II includes contacting a compound of Formula I with bis-N,O-trimethylsilylacetamide; and forming a compound of Formula II
  • R 1 is selected from the group consisting of:
  • R 2 is selected from the group consisting of:
  • a molar ratio of compound Ito bis-N,O-trimethylsilylacetamide (BSA) is 1:1.1 and the contacting step is carried out at about 22° C. to about 70° C.
  • the contacting step further includes contacting compound I with CH 3 CN.
  • the method includes contacting a BSA treated reaction mixture with an arylsulfonyl chloride.
  • a molar ratio of Compound Ito arylsulfonyl chloride is from about 1:2 to about 2:1.
  • a molar ratio of Compound I to arylsulfonyl chloride is 1:1.1.
  • the filter cake was washed with aqueous CH 3 CN (10% CH 3 CN in H 2 O) and air dried for 2 h.
  • the cake was dissolved in CH 3 CN (15 mL) at 40 ° C. and the solution was treated with H 2 O (30 mL).
  • the resulting suspension was cooled to room temperature, stirred for 2.5 h, and filtered.
  • the filter cake was again washed with 10% aqueous CH 3 CN and then dried under vacuum at 50 ° C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
US14/584,368 2013-12-31 2014-12-29 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation Abandoned US20150183750A1 (en)

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US14/584,368 US20150183750A1 (en) 2013-12-31 2014-12-29 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation
US15/173,529 US9840476B2 (en) 2013-12-31 2016-06-03 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation

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US201361922582P 2013-12-31 2013-12-31
US201361922572P 2013-12-31 2013-12-31
US14/584,368 US20150183750A1 (en) 2013-12-31 2014-12-29 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation

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US14/584,368 Abandoned US20150183750A1 (en) 2013-12-31 2014-12-29 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation
US14/584,347 Abandoned US20150183749A1 (en) 2013-12-31 2014-12-29 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation
US15/173,493 Active US9850215B2 (en) 2013-12-31 2016-06-03 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1 H)-one and processes for their preparation
US15/173,529 Active US9840476B2 (en) 2013-12-31 2016-06-03 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation
US15/813,562 Abandoned US20180072686A1 (en) 2013-12-31 2017-11-15 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation
US16/448,633 Abandoned US20190308941A1 (en) 2013-12-31 2019-06-21 5-fluoro-4-imino-3(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation
US16/585,239 Abandoned US20200024238A1 (en) 2013-12-31 2019-09-27 5-fluoro-4-imino-3(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation
US16/741,026 Active US10919864B2 (en) 2013-12-31 2020-01-13 5-fluoro-4-imino-3(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation

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US14/584,347 Abandoned US20150183749A1 (en) 2013-12-31 2014-12-29 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation
US15/173,493 Active US9850215B2 (en) 2013-12-31 2016-06-03 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1 H)-one and processes for their preparation
US15/173,529 Active US9840476B2 (en) 2013-12-31 2016-06-03 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation
US15/813,562 Abandoned US20180072686A1 (en) 2013-12-31 2017-11-15 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation
US16/448,633 Abandoned US20190308941A1 (en) 2013-12-31 2019-06-21 5-fluoro-4-imino-3(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation
US16/585,239 Abandoned US20200024238A1 (en) 2013-12-31 2019-09-27 5-fluoro-4-imino-3(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1h)-one and processes for their preparation
US16/741,026 Active US10919864B2 (en) 2013-12-31 2020-01-13 5-fluoro-4-imino-3(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation

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US (8) US20150183750A1 (enrdf_load_stackoverflow)
EP (4) EP3097096A4 (enrdf_load_stackoverflow)
JP (3) JP6804297B2 (enrdf_load_stackoverflow)
CN (4) CN106068268A (enrdf_load_stackoverflow)
AP (1) AP2016009342A0 (enrdf_load_stackoverflow)
AU (2) AU2014373959B2 (enrdf_load_stackoverflow)
BR (2) BR102014033037B1 (enrdf_load_stackoverflow)
CA (2) CA2935601C (enrdf_load_stackoverflow)
CL (1) CL2016001677A1 (enrdf_load_stackoverflow)
CR (2) CR20210172A (enrdf_load_stackoverflow)
DO (1) DOP2016000163A (enrdf_load_stackoverflow)
EA (2) EA201691353A1 (enrdf_load_stackoverflow)
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US9840475B2 (en) 2012-12-28 2017-12-12 Adama Makhteshim Ltd. N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxamide derivatives
US9840476B2 (en) 2013-12-31 2017-12-12 Adama Makteshim Ltd. 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one and processes for their preparation
US9908855B2 (en) 2012-12-28 2018-03-06 Adama Makhteshim Ltd. N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxylate derivatives
US10045533B2 (en) 2013-12-31 2018-08-14 Adama Makhteshim Ltd. Synergistic fungicidal mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one for fungal control
US10059703B2 (en) 2012-12-31 2018-08-28 Adama Makhteshim Ltd. 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides
US11632954B2 (en) 2017-07-17 2023-04-25 Adama Makhteshim Ltd. Polymorphs of 5-fluoro-4-imino-3-methyl-1 -tosyl-3,4-dihydropyrimidin-2-one

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UY36964A (es) 2015-10-27 2017-05-31 Bayer Cropscience Ag Combinaciones de principios activos que comprenden un derivado de (tio) carboxamida y un compuesto funguicida
JP6922271B2 (ja) * 2016-03-11 2021-08-18 住友化学株式会社 植物病害防除組成物及び植物病害防除方法
IL282939B2 (en) 2018-11-05 2024-10-01 Adama Makhteshim Ltd Mixtures and compositions comprising 5-fluoro-4-imino-3- methyl-1-tosyl-3,4- dihydropyrimidin-2-one, and methods of use thereof
EP4003017A1 (en) 2019-07-22 2022-06-01 Adama Makhteshim Ltd. Fungicidal combinations, mixtures and compositions and uses thereof
WO2021059160A1 (en) 2019-09-23 2021-04-01 Adama Makhteshim Ltd. Process for preparing 5-(fluoro-4-imino-3-methyl)-1-tosyl-3,4 dihydropyrimidine -(1h)-one
CN115776980A (zh) * 2020-03-09 2023-03-10 阿达玛马克西姆有限公司 用于制备5-氟-4-亚氨基-3-甲基-1-(甲苯-4-磺酰基)-3,4-二氢-1h-嘧啶-2-酮的方法
KR20230069875A (ko) * 2020-05-04 2023-05-19 아다마 마켓심 리미티드 5-플루오로-4-이미노-3-메틸-1-토실-3,4-디하이드로피리미딘-2-온을 포함하는 혼합물 및 조성물, 및 이의 사용 방법
JP2023533554A (ja) 2020-07-08 2023-08-03 アダマ・マクテシム・リミテッド 殺菌・殺カビ性混合物
WO2022162591A1 (en) 2021-01-27 2022-08-04 Adama Makhteshim Ltd. 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1 h)-one for controlling plant diseases
AU2022268726A1 (en) 2021-05-04 2023-11-23 Adama Makhteshim Ltd. Crystalline forms of 5-fluoro-4-imino-3-methyl-1-tosyl-3,4- dihydropyrimidin-2-one, and mixtures, compositions and methods of use thereof
IL311455A (en) 2021-09-15 2024-05-01 Adama Makhteshim Ltd Method for preparing 5-fluoro-4-imino-3-methyl-1-(toluene-4-sulfonyl)-3,4-dihydro-H1-pyrimidin-2-one
KR20240159928A (ko) 2022-03-03 2024-11-07 아다마 마켓심 리미티드 살진균성 조합물, 혼합물 및 조성물 및 이의 용도
EP4531570A1 (en) 2022-05-26 2025-04-09 Adama Makhteshim Ltd. Fungicidal combinations, mixtures and compositions and uses thereof
AU2023318916A1 (en) 2022-08-03 2025-02-20 Adama Makhteshim Ltd. 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1h)-one for fungicide-resistant fungus
AR132077A1 (es) 2023-03-09 2025-05-21 Adama Makhteshim Ltd Combinaciones, mezclas y composiciones fungicidas y usos de las mismas
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TW202444696A (zh) 2023-03-23 2024-11-16 以色列商安道麥馬克西姆有限公司 用於製備5-氟-4-亞胺基-3-甲基-1-(甲苯-4-磺醯基)-3,4-二氫-1h-嘧啶-2-酮的方法
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