103474-01-7

Upstream product

• 5781-53-3 monomethyl oxalyl chloride 
• 553-90-2 Dimethyl oxalate 
• 109-72-8 n-butyllithium 
• 865-47-4 potassium tert-butylate 
• 101-84-8 diphenylether 

Downstream Products

• 156489-61-1 2-(2-phenoxyphenyl)-2-methoxyiminoacetamide 
• 115199-04-7 methyl (Z)-O-methyloximino-2-(2-phenoxy)phenylacetate 

Relevant academic research and scientific papers

Synthetic method for (E)-2-methoximino-N-methyl-2-(2-phenoxyphenyl)acetamide

The invention discloses a synthetic method for (E)-2-methoximino-N-methyl-2-(2-phenoxyphenyl)acetamide. The synthetic method comprises the following steps: with diphenyl ether as a starting material,allowing the diphenyl ether to react with dimethyl oxalate so as to prepare an intermediate namely 2-(2-phenoxyphenyl)-2-methyl oxoacetate, then allowing the 2-(2-phenoxyphenyl)-2-methyl oxoacetate toreact with hydroxylamine so as to prepare an oxime compound, and subjecting the oxime compound to amination so as to prepare the (E)-2-methoximino-N-methyl-2-(2-phenoxyphenyl)acetamide. The preparation method provided by the invention has the advantages of cheap and easily-available raw materials, simple process, less three wastes, avoidance of using highly-toxic raw materials, applicability to industrial production, etc. The (E)-2-methoximino-N-methyl-2-(2-phenoxyphenyl)acetamide provided by the invention is a highly-efficient agricultural fungicide, and has strong prevention and treatment effects on diseases like rice blast, sheath blight, cucumber powdery mildew and downy mildew.

A novel method for the efficient synthesis of methyl 2-oxo-2- arylacetates and its application to the preparation of fungicidal methyl (E)- O-methyloximino-2-arylacetates and their (Z)-stereoisomers

Methyl 2-oxo-2-arylacetates 1, which include some fluorinated compounds, have been synthesized in moderate to excellent yields by reaction of methyl oxalyl chloride with arylzinc halides in the presence of Pd(PPh3)4. The highest yields have been obtained when these reactions involved arylzinc bromides which were prepared by conversion of the corresponding aryl bromides to organolithiums, followed by transmetallation with ZnBr2. Compounds 1 have been converted in high yields to the corresponding (E)- and (Z)-O- methyloximino-2-arylacetates (E)- and (Z)-5 by treatment with O- methylhydroxylamine hydrochloride in pyridine. Compounds (E)- and (Z)-5 have been easily separated by MPLC on silica gel and their structure and stereochemistry have been assigned by NMR techniques. So prepared compounds of general formula 5 included an agrochemically important fungicide, i.e. (E)-5c, its fluorinated structural analogues, as well as compounds which proved to be able to delay the growth of fungal species isolated from deteriorated papers. Interestingly, several compounds of general formula (Z)- 5 underwent partial stereomutation in the presence of daylight and catalytic amounts of iodine.

Alkoxyiminoacetamide derivatives and their use as fungicides

A fungicidal composition for agricultural use, which comprises a compound of the formula: STR1 wherein R1 and R2 are each hydrogen, lower alkyl or cyclo(lower)alkyl; R3 is lower alkyl or cyclo(lower)alkyl; R4 and R5 are each hydrogen, lower alkyl, lower alkoxy, halogen-substituted lower alkyl, lower alkyl-substituted silyl, halogen or nitro; A represents an unsaturated hydrocarbon group, a halogen-substituted unsaturated hydrocarbon group, a phenyl group or a heterocyclic group, among which the phenyl group and the heterocyclic group may be optionally substituted with not more than three substituents; and Z is --CH2 --, --CH(OH)--, --CO--, --O--, --S--, --NR-- (R being hydrogen or lower alkyl), --CH2 CH2 --, --CH=CH--, --CH2 O--, --CH2 S--, --CH2 SO--, --OCH2 --, --SCH2 -- or --SOCH2 --. STR2

Derivatives of alphaphenylacrylic acid and their use in agriculture

Compounds of formula: STR1 and stereoisomers thereof, wherein R1 and R2, which are the same or different, are optionally substituted alkyl; W, X, Y and Z, which are the same or different, are hydrogen, halogen, hydroxy, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted aryloxyalkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted alkynyl, optionally substituted amino, optionally substituted arylazo, optionally substituted heteroarylalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted acylamino, nitro, cyano, --OR3, --SR3, --CO2 R4, --CONR5 R6, --COR7, --CR8 =NR9, --N=CR10 R11, --SOR12 or --SO2 R13, or any two of W, X, Y, and Z, in adjacent positions on the phenyl ring, optionally join to form an optionally substituted fused ring, either aromatic or aliphatic, optionally containing one or more heteroatoms; R3 is optionally substituted alkyl, or cycloalkyl optionally containing a hetero atom in the cycloalkyl ring, optionally substituted alkenyl, optionally substituted aryl, optionally substituted aralkyl, optionally substituted acyl, or optionally substituted heteroaryl; R4, R5, R6, R7, R8, R10 and R11, which are the same or different, are hydrogen or optionally substituted alkyl, optionally substituted cycloalkyl, cycloalkylalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted aralkyl; and R9, R12 and R13 are optionally substituted aryl or optionally substituted heteroaryl. The compounds are useful in agriculture as fungicides, plant growth regulators and insecticides.

Phenyl oximino-acetate fungicides

Compounds of the fomrula (I): STR1 and sterioisomers thereof, wherein X is halogen, alkyl, cycloalkyl, aralkyl, aryloxyalkyl, alkenyl, alkynyl, aryl, amino, arylazo, heteroarylalkyl, heteroaryloxyalkyl, acylamino nitro, nitride, trifluoromethyl, -OR1