Abstract: A tetrazolinone compound represented by formula (1): [in the formula, R1 represents an alkyl group having 1-6 carbon atoms or the like] can be produced by reacting a compound represented by formula (2): [in the formula, X1 represents a bromine atom or the like, and R1 represents an alkyl group having 1-6 carbon atoms or the like] with a compound represented by formula (A): R—Mg—X??(A) [in the formula, R represents an alkyl group having 1-6 carbon atoms or the like, and X1 represents a bromine atom or the like] to provide a compound represented by formula (3): [in the formula, X2 represents a chlorine atom or the like] and reacting the compound represented by formula (3) with formaldehyde or a compound represented by formula (4): [in the formula, R6 represents an alkyl group having 1-6 carbon atoms or the like, and X3 represents a chlorine atom, bromine atom or iodine atom].

Abstract: Position-1 halogen can be selectively reduced by reacting a compound represented by formula (3): [wherein X represents a chlorine atom, a bromine atom, or an iodine atom] with halogen in the presence of a heterogeneous transition metal catalyst to produce 2-(halogenomethyl)-1-methyl-3-nitrobenzene represented by formula (1): [wherein the symbol is as defined above].

Abstract: The present invention provides a method for manufacturing an optically active compound of formula (2), which contains bringing hydrogen into contact with a compound of formula (1) in the presence of a transition metal catalyst having an optically active ligand. In the formula, R1 represents a hydrogen atom or an acetyl group, R2, R3, R4, and R5 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxy group, a nitro group, an amino group, or an acyl group, R6 represents an alkyl group, R7 and R8 each independently represents a hydrogen atom or an alkyl group, and a carbon atom marked with an asterisk (*) represents an asymmetric carbon atom.

Abstract: A tetrazolinone compound represented by formula (1): [in the formula, R1 represents an alkyl group having 1-6 carbon atoms or the like] can be produced by reacting a compound represented by formula (2): [in the formula, X1 represents a bromine atom or the like, and R1 represents an alkyl group having 1-6 carbon atoms or the like] with a compound represented by formula (A): R—Mg—X??(A) [in the formula, R represents an alkyl group having 1-6 carbon atoms or the like, and X1 represents a bromine atom or the like] to provide a compound represented by formula (3): [in the formula, X2 represents a chlorine atom or the like] and reacting the compound represented by formula (3) with formaldehyde or a compound represented by formula (4): [in the formula, R6 represents an alkyl group having 1-6 carbon atoms or the like, and X3 represents a chlorine atom, bromine atom or iodine atom].

Abstract: The present invention provides a method for manufacturing an optically active compound of formula (2), which contains bringing hydrogen into contact with a compound of formula (1) in the presence of a transition metal catalyst having an optically active ligand. In the formula, R1 represents a hydrogen atom or an acetyl group, R2, R3, R4, and R5 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a hydroxy group, a nitro group, an amino group, or an acyl group, R6 represents an alkyl group, R7 and R8 each independently represents a hydrogen atom or an alkyl group, and a carbon atom marked with an asterisk (*) represents an asymmetric carbon atom.

Abstract: Position-1 halogen can be selectively reduced by reacting a compound represented by formula (3): [wherein X represents a chlorine atom, a bromine atom, or an iodine atom] with halogen in the presence of a heterogeneous transition metal catalyst to produce 2-(halogenomethyl)-1-methyl-3-nitrobenzene represented by formula (1): [wherein the symbol is as defined above].

Abstract: A method for producing a methanol solvate of D-tartrate of (R)-1,1,3-trimethyl-4-aminoindane, the method comprising steps (a), (b), and (c) below, and comprising adding water to a reaction system before step (c): step (a) of mixing 1,1,3-trimethyl-4-aminoindane, D-tartaric acid, and methanol to provide a mixture containing a methanol solvate of D-tartrate of (R)-1,1,3-trimethyl-4-aminoindane; step (b) of cooling the obtained mixture; and step (c) of retrieving the methanol solvate of D-tartrate of (R)-1,1,3-trimethyl-4-aminoindane.

Abstract: A method for producing a methanol solvate of D-tartrate of (R)-1,1,3-trimethyl-4-aminoindane, the method comprising steps (a), (b), and (c) below, and comprising adding water to a reaction system before step (c): step (a) of mixing 1,1,3-trimethyl-4-aminoindane, D-tartaric acid, and methanol to provide a mixture containing a methanol solvate of D-tartrate of (R)-1,1,3-trimethyl-4-aminoindane; step (b) of cooling the obtained mixture; and step (c) of retrieving the methanol solvate of D-tartrate of (R)-1,1,3-trimethyl-4-aminoindane.

Abstract: Provided is an agricultural composition comprising a compound represented by the formula (I) or a salt thereof or a hydrate thereof, for controlling a plant disease due to a plant pathogen: [wherein, G represents a di-valent aromatic hetero 5-membered ring optionally having a halogen atom or C1 to 3 alkyl group (with the proviso that a hetero atom of the aromatic hetero 5-membered ring is a nitrogen atom, oxygen atom or sulfur atom), R1 represents a hydrogen atom or amino group, R2, R3 and R4 represent each independently a hydrogen atom or the like, and E represents an optionally substituted 5 to 10-membered heterocyclic group or C6-10 aryl group.].