Pyrimidine derivatives and use thereof as agricultural and horticultural fungicides

A method of protecting plants or materials from undesired microorganisms in agriculture and horticulture comprising applying to the microorganisms and/or their habitat a benzylpyrimidine derivative represented by formula (I)

• wherein
• R1 and R2, together with the nitrogen atom to which they are bonded, form a 3- to 10-membered heterocyclic group that is optionally substituted and optionally contains one to three further hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and S(O)n in addition to the nitrogen atom to which R1 and R2 are bonded,
• n represents 0, 1, or 2,
• R3 represents hydrogen, halogen, cyano, hydroxy, amino, azido, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkylthio, alkenylthio, haloalkenylthio, alkylsulfinyl, alkylsulfonyl, phenoxy that is optionally substituted, benzyloxy that is optionally substituted, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted with a group selected from the group consisting of halogen, alkyl, and haloalkyl;
• or represents a moiety selected from the group consisting of formulas A to H and J to M
• in which
• R7 represents hydrogen atom, alkyl, or haloalkyl, and
• R8 represents alkyl, phenyl, alkoxy or cyano, or
• R7 and R8, together with the carbon atom to which they are bonded, form a cycloalkylidene,
• R9 represents alkyl, haloalkenyl, or benzyl,
• R10 represents hydrogen atom or alkyl,
• R11 represents alkyl, alkoxyalkyl, dialkylaminoalkyl, phenyl, benzyl, or cyano,
• R12 represents alkyl or phenyl,
• R13 represents alkyl or benzyl,
• R14 represents hydrogen atom or alkyl,
• R15 represents hydrogen atom, haloalkyl, or phenyl,
• R16 represents hydrogen atom or alkyl,
• R17 represents hydrogen atom, alkyl, or haloalkyl,
• R18 represents alkyl or phenyl,
• R19 represents hydrogen atom or alkyl,
• R20 represents alkyl,
• R21 represents alkyl,
• R22 represents alkyl, alkenyl, haloalkenyl, alkoxyalkyl, phenoxyalkyl, or alkoxycarbonylalkyl,
• R23 represents alkyl, and
• R24 represents hydrogen atom or alkyl, and
• R25 represents alkyl or phenyl, or
• R24 and R25, together with the nitrogen atom to which they are bonded, form a 5- to 8-membered saturated monoheterocyclic group that is optionally substituted and optionally contains one or two further hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and S(O)n in addition to the nitrogen atom to which R24 and R25 are bonded,
• R4 represents hydrogen atom, halogen, cyano, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, or a group
• where R1 and R2 are as defined above,
• R5 and R6 each independently represents hydrogen atom, halogen, alkyl, haloalkyl, or phenyl that is optionally substituted, and
• Q represents aryl that is optionally substituted or a 5- or 6-membered heterocyclic group that contains one hetero atom selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted.

A benzylpyrimidine derivative represented by formula (IA)

• wherein
• R1A and R2A, together with the nitrogen atom to which they are bonded, form a 3- to 10-membered heterocyclic group that is optionally substituted and optionally contains one to three further hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and S(O)m in addition to the nitrogen atom to which R1A and R2A are bonded,
• m represents 0, 1, or 2,
• R3A represents hydrogen, halogen, cyano, hydroxy, amino, azido, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkylthio, alkenylthio, haloalkenylthio, alkylsulfinyl, alkylsulfonyl, phenoxy that is optionally substituted, benzyloxy that is optionally substituted, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted with a group selected from the group consisting of halogen, alkyl, and haloalkyl;
• or represents a moiety selected from the group consisting of A to H and J to M
• in which
• R7A represents hydrogen atom, alkyl, or haloalkyl, and
• R8A represents alkyl, phenyl, alkoxy, or cyano, or
• R7A and R8A, together with the carbon atom to which they are bonded, form a cycloalkylidene,
• R9A represents alkyl, haloalkenyl, or benzyl,
• R10A represents hydrogen atom or alkyl,
• R11A represents alkyl, alkoxyalkyl, dialkylaminoalkyl, phenyl, benzyl, or cyano,
• R12A represents alkyl or phenyl,
• R13A represents alkyl or benzyl,
• R14A represents hydrogen atom or alkyl,
• R15A represents hydrogen atom, haloalkyl, or phenyl,
• R16A represents hydrogen atom or alkyl,
• R17A represents hydrogen atom, alkyl, or haloalkyl,
• R18A represents alkyl or phenyl,
• R19A represents hydrogen atom or alkyl,
• R20A represents alkyl,
• R21A represents alkyl,
• R22A represents alkyl, alkenyl, haloalkenyl, alkoxyalkyl, phenoxyalkyl, or alkoxycarbonylalkyl,
• R23A represents alkyl, and
• R24A represents hydrogen atom or alkyl, and
• R25A represents alkyl or phenyl, or
• R24A and R25A, together with the nitrogen atom to which they are bonded, form a 5- to 8-membered saturated monoheterocyclic group that is optionally substituted and optionally contains one or two further hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and S(O)n in addition to the nitrogen atom to which R24A and R25A are bonded,
• R4A represents hydrogen atom, halogen, cyano, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, or a group
• where R1A and R2A are as defined above,
• R5A and R6A each independently represents hydrogen atom, halogen, alkyl, haloalkyl, or phenyl that is optionally substituted, and
• QA represents aryl that is optionally substituted, a 5 or 6-membered heterocyclic group that contains one hetero atom selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted,
• with the proviso that the following cases (T-1) to (T-6) are excluded:
• (T-1) benzylpyrimidine derivatives in which
• the group
• represents 1-pyrrolyl, 1-imidazolyl, 3-oxopiperidino, or 4-oxopiperidino,
• R3A represents hydrogen atom,
• R4A represents hydrogen atom, and
• QA represents 1-naphthyl or phenyl group that is optionally substituted by one or two groups selected from the group consisting of chloro, methyl, ethyl, and trifluoromethyl,
• (T-2) benzylpyrimidine derivatives in which
• the group
• represents 3-oxopiperidino, 4-oxopiperidino, 4-hydroxypiperidino, 4-carbamoylpiperidino, 4-methylpiperazino, 4-ethylpiperazino, 4-(2-hydroxyethyl)piperazino, or morpholino,
• R3A represents amino,
• R4A represents hydrogen atom, and
• QA represents 3-pyridyl or phenyl group that is optionally substituted by one to three groups selected from the group consisting of fluoro, chloro, bromo, methyl, ethyl, isopropyl, trifluoromethyl, hydroxy, methoxy, and 4-chlorobenzyloxy,
• (T-3) benzylpyrimidine derivatives in which
• the group
• represents piperidino, 4-hydroxypiperidino, 4-methylpiperazino, morpholino, 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl or 6,7-dimethoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-2-yl,
• R3A represents chloro, dimethylamino, anilino, 2-(2-hydroxyethoxy)ethylamino, piperidino, 4-hydroxypiperidino, 4-carbamoylpiperidino, 4-methylpiperazino, or morpholino,
• R4A represents hydrogen atom, and
• QA represents phenyl group that is optionally substituted by one or two groups selected from the group consisting of methyl and methoxy,
• (T-4) benzylpyrimidine derivatives in which
• the group
• represents 1-pyrrolidinyl, piperidino, morpholino, or 1-pyrrolyl,
• R3A represents methyl or methoxymethyl,
• R4A represents chloro, and
• QA represents phenyl or 1-naphthyl,
• (T-5) benzylpyrimidine derivatives in which
• the group
• represents 1-azilidinyl, piperidino, or morpholino,
• R3A represents methylthio,
• R4A represents chloro, and
• QA represents phenyl group substituted by methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, or allyloxy, and
• (T-6) benzylpyrimidine derivatives in which
• the group
• represents 1-azilidinyl,
• R3A represents hydrogen atom or amino,
• R4A represents chloro, and
• QA represents phenyl group substituted by methoxy, ethoxy, or allyloxy.

A process for the preparation of compounds of formula (IA)

• wherein
• R1A and R2A, together with the nitrogen atom to which they are bonded, form a 3- to 10-membered heterocyclic group that is optionally substituted and optionally contains further one to three hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and S(O)m in addition to the nitrogen atom to which R1A and R2A are bonded,
• m represents 0, 1, or 2,
• R3A represents hydrogen, halogen, cyano, hydroxy, amino, azido, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkylthio, alkenylthio, haloalkenylthio, alkylsulfinyl, alkylsulfonyl, phenoxy that is optionally substituted, benzyloxy that is optionally substituted, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted with a group selected from the group consisting of halogen, alkyl, and haloalkyl;
• or represents a moiety selected from the group consisting of formulas A to H and J to M
• in which
• R7A represents hydrogen atom, alkyl, or haloalkyl, and
• R8A represents alkyl, phenyl, alkoxy or cyano, or
• R7A and R8A, together with the carbon atom to which they are bonded, form a cycloalkylidene or cyclohexylidene,
• R9A represents alkyl, haloalkenyl, or benzyl,
• R10A represents hydrogen atom or alkyl,
• R11A represents alkyl, alkoxyalkyl, dialkylaminoalkyl, phenyl, benzyl, or cyano,
• R12A represents alkyl or phenyl,
• R13A represents alkyl or benzyl,
• R14A represents hydrogen atom or alkyl,
• R15A represents hydrogen atom, haloalkyl, or phenyl,
• R16A represents hydrogen atom or alkyl,
• R17A represents hydrogen atom, alkyl, or haloalkyl,
• R18A represents alkyl or phenyl,
• R19A represents hydrogen atom or alkyl,
• R20A represents alkyl,
• R21A represents alkyl,
• R22A represents alkyl, alkenyl, haloalkenyl, alkoxyalkyl, phenoxyalkyl, or alkoxycarbonylalkyl,
• R23A represents alkyl, and
• R24A represents hydrogen atom or alkyl, and
• R25A represents alkyl or phenyl, or
• R24A and R25A, together with the nitrogen atom to which they are bonded, form a 5- to 8-membered saturated-monoheterocyclic group that is optionally substituted and optionally contains further one or two hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and S(O)n in addition to the nitrogen atom to which R24A and R25A are bonded,
• R4A represents hydrogen atom, halogen, cyano, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, or a group
• where R1A and R2A are as defined above,
• R5A and R6A each independently represents hydrogen atom, halogen, alkyl, haloalkyl, or phenyl that is optionally substituted, and
• QA represents aryl that is optionally substituted or a 5- or 6-membered heterocyclic group that contains one hetero atom selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted,
• with the proviso that the following cases (T-1) to (T-6) are excluded:
• (T-1) benzylpyrimidine derivatives in which
• the group
• represents 1-indolyl, 1-pyrrolyl, 1-imidazolyl, 3-oxopiperidino, or 4-oxopiperidino,
• R3A represents hydrogen atom,
• R4A represents hydrogen atom, and
• QA represents 1-naphthyl or phenyl group that is optionally substituted by one or two groups selected from the group consisting of chloro, bromo, methyl, ethyl, and trifluoromethyl,
• (T-2) benzylpyrimidine derivatives in which
• the group
• represents 3-oxopiperidino, 4-oxopiperidino, 4-hydroxypiperidino, 4-carbamoylpiperidino, 4-methylpiperazino, 4-ethylpiperazino, 4-(2-hydroxyethyl)piperazino, or morpholino,
• R3A represents amino,
• R4A represents hydrogen atom, and
• QA represents 3-pyridyl or phenyl group that is optionally substituted by one to three groups selected from the group consisting of fluoro, chloro, bromo, methyl, ethyl, isopropyl, trifluoromethyl, hydroxy, methoxy, and 4-chlorobenzyloxy,
• (T-3) benzylpyrimidine derivatives in which
• the group
• represents piperidino, 4-hydroxypiperidino, 4-methylpiperazino, morpholino, 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl, or 6,7-dimethoxy-1-(3,4-dimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-2-yl,
• R3A represents chloro, dimethylamino, anilino, 2-(2-hydroxyethoxy)ethylamino, piperidino, 4-hydroxypiperidino, 4-carbamoylpiperidino, 4-methylpiperazino, or morpholino,
• R4A represents hydrogen atom, and
• QA represents phenyl group that is optionally substituted by one or two groups selected from the group consisting of methyl and methoxy,
• (T-4) benzylpyrimidine derivatives in which
• the group
• represents 1-pyrrolidinyl, piperidino, morpholino, or 1-pyrrolyl,
• R3A represents methyl or methoxymethyl,
• R4A represents chloro, and
• QA represents phenyl or 1-naphthyl,
• (T-5) benzylpyrimidine derivatives in which
• the group
• represents 1-azilidinyl, piperidino, or morpholino,
• R3A represents methylthio,
• R4A represents chloro, and
• QA represents phenyl group substituted by methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, or allyloxy, and
• (T-6) benzylpyrimidine derivatives in which
• the group
• represents 1-azilidinyl,
• R3A represents hydrogen atom or amino,
• R4A represents chloro, and
• QA represents phenyl group substituted by methoxy, ethoxy, or allyloxy, comprising
• (a) for compounds of formula (IA) in which
• R3A represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkylthio, alkenylthio, haloalkenylthio, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted by a group selected from the group consisting of halogen, alkyl, and haloalkyl, and
• R4A represents hydrogen atom, halogen, alkyl, haloalkyl, or alkenyl,
• reacting a compound of formula (II)
• wherein
• Xa represents halogen,
• R3Aa represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkylthio, alkenylthio, haloalkenylthio, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted by a group selected from the group consisting of halogen, alkyl, and haloalkyl,
• R4Aa represents hydrogen atom, halogen, alkyl, haloalkyl or alkenyl, and
• R5A, R6A, and QA have the same definitions as for formula (IA),
• with a compound of formula (III)
• wherein R1A and R2A have the same definitions as for formula (IA), in the presence of an inert solvent and optionally in the presence of an acid binder,
• or
• (b) for compounds of formula (IA) in which
• (i)
• R3A represents alkylsulfinyl or alkylsulfonyl, and
• R4A represents hydrogen atom, halogen, cyano, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy or a group
• where R1A and R2A are as defined above,
• reacting a compound of formula (IAb)
• wherein
• R3Ab represents alkylthio, and
• R4Ab represents hydrogen atom, halogen, cyano, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, or a group
• where R1A and R2A are as defined above, and
• R1A, R2A, R5A, R6A, and QA have the same definitions as for formula (IA),
• with an oxidizing agent in the presence of an inert solvent,
• or
• (ii)
• R3A represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkenyl, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted by a group selected from the group consisting of halogen, alkyl, and haloalkyl, and
• R4A represents alkylsulfinyl or alkylsulfonyl,
• reacting a compound of formula (IAb)
• wherein
• R3Ab represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkenyl, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted by a group selected from the group consisting of halogen, alkyl, and haloalkyl, and
• R4Ab represents alkylthio, and
• R1A, R2A, R5A, R6A, and QA have the same definitions as for formula (IA),
• with an oxidizing agent in the presence of an inert solvent,
• or
• (c) for compounds of formula (IA) in which
• R3A represents cyano, hydroxy, azido, alkynyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkylthio, alkenylthio, haloalkenylthio, phenoxy that is optionally substituted, benzyloxy that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted by a group selected from the group consisting of halogen, alkyl, and haloalkyl;
• or represents a group A, group B, group C, group F, group G, or group H as defined for formula (IA), and
• R4A represents hydrogen atom, halogen, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, cyano, or a group
• where R1A and R2A are as defined above,
• reacting a compound of formula (IAc)
• wherein
• Xc represents halogen or methylsulfonyl,
• R4Ac represents hydrogen atom, halogen, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, cyano or a group
• where R1A and R2A are as defined above, and
• R1A, R2A, R5A, R6A, and QA have the same definitions as for formula (IA),
• with a compound of formula (IV)
• Y—R3Ac (IV)
• wherein
• Y represents hydrogen, sodium, potassium, copper, trimethylsilyl, or tetraalkylammonium,
• R3Ac represents cyano, hydroxy, azido, alkynyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkylthio, alkenylthio, haloalkenylthio, phenoxy that is optionally substituted, benzyloxy that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted by a group selected from the group consisting of halogen, alkyl, and haloalkyl;
• or represents a group A, group B, group C, group F, group G, or group H as defined for R3A of formula (IA),
• in the presence of an inert solvent, optionally in the presence of an acid binder, and optionally in the presence of a catalyst,
• or
• (d) for compounds of formula (IA) in which
• R3A represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkylthio, alkenylthio, haloalkenylthio, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted by a group selected from the group consisting of halogen, alkyl, and haloalkyl, and
• R4A represents cyano, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio or a group
• where R1A and R2A are as defined above,
• reacting a compound of formula (IAd)
• wherein
• Xd represents halogen or methylsulfonyl,
• R3Ad represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkylthio, alkenylthio, haloalkenylthio, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted by a group selected from the group consisting of halogen, alkyl, and haloalkyl, and
• R1A, R2A, R5A, R6A, and QA have the same definitions as for formula (IA),
• with a compound of formula (V)
• Y—R4Ad (V)
• wherein
• Y represents hydrogen, sodium, potassium, copper, trimethylsilyl, or tetraalkylammonium, and
• R4Ad represents cyano, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, or a group
• where R1A and R2A are as defined above,
• in the presence of an inert solvent, optionally in the presence of an acid binder, and optionally in the presence of a catalyst,
• or
• (e) for compounds of formula (IA) in which
• R3A represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkylthio, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted by a group selected from the group consisting of halogen, alkyl, and haloalkyl, and
• R4A represents hydrogen,
• hydrogenating a compound of formula (IAe)
• wherein
• Xe represents halogen,
• R3Ae represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkylthio, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted by a group selected from the group consisting of halogen, alkyl, and haloalkyl, and
• R1A, R2A, R5A, R6A, and QA have the same definitions as for formula (IA),
• in the presence of an inert solvent, optionally in the presence of a catalyst, and optionally in the presence of an acid binder,
• or
• (f) for compounds of formula (IA) in which
• R3A represents hydrogen, halogen, cyano, hydroxy, amino, azido, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, phenoxy that is optionally substituted, benzyloxy that is optionally substituted, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted by a group selected from the group consisting of halogen, alkyl, and haloalkyl;
• or represents a group A, group B, group C, group F, group G, or group H as defined for formula (IA),
• R4A represents hydrogen atom, halogen, cyano, alkyl, haloalkyl, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, or a group
• where R1A and R2A are as defined above,
• reacting a compound of formula (IAf)
• wherein
• R3Af represents hydrogen, halogen, cyano, hydroxy, amino, azido, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, phenoxy that is optionally substituted, benzyloxy that is optionally substituted, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted by a group selected from the group consisting of halogen, alkyl, and haloalkyl;
• or represents a group A, group B, group C, group F, group G, or group H as defined for R3A of formula (IA),
• R4Af represents hydrogen atom, halogen, cyano, alkyl, haloalkyl, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, or a group
• where R1A and R2A are as defined above,
• R5A, R6A, and QA have the same definitions as for formula (IA),
• R26A represents alkyl,
• p represents 1 or 2, and
• q represents 0, 1, or 2,
• with difluorocarbene derived from sodium chlorodifluoroacetate or with dichlorocarbene derived from chloroform, in the presence of an inert solvent and optionally in the presence of a phasetransfer catalyst,
• or
• (g) for compounds of formula (IA) in which R3A represents amino,
• hydrogenating or reacting with metal hydride a compound of formula (IAg)
• wherein R1A, R2A, R4A, R5A, R6A, and QA have the same definitions as for formula (IA),
• in the presence of an inert solvent and optionally in the presence of a catalyst,
• or
• (h) for compounds of formula (IA) in which R3A represents halogen,
• (1) in a first step, reacting a compound of formula (IAh)
• wherein R1A, R2A, R4A, R5A, R6A, and QA have the same definitions as for formula (IA),
• with a nitrite ester or nitrous acid in the presence of an inert solvent and optionally in the presence of acid catalyst to form a diazonium salt, and
• (2) in a second step, reacting the diazonium salt obtained in the first step according to Sandmeyer process or Gattermann process in the presence of copper halide, potassium halide, or copper powder, in the presence an inert solvent and optionally in the presence of acid catalyst,
• or
• (i) for compounds of formula (IA) in which R3A represents group E,
• (1) in a first step, reacting a compound of formula (IAh) with dimethylformamide dimethylacetal in the presence of an inert solvent, to form a compound of formula (VI)
• wherein R1A, R2A, R4A, R5A, R6A and QA have the same definitions as for formula (IA), and
• (2) in a second step, reacting the compound of formula (VI) obtained in the first step with a compound of formula (VII)
• wherein R13A has the same definition as for formula (IA),
• in the presence of an inert solvent, optionally in the presence of an acid binder, and optionally in the presence of an acid catalyst,
• or
• (j) for compounds of formula (IA) in which R3A represents the group D,
• reacting a compound of formula (IAh) with a compound of formula (VIII)
• wherein R26A represents chloro or a group
• wherein R12A has the same definition as for formula (IA),
• in the presence of an inert solvent and optionally in the presence of an acid binder,
• or
• (k) for compounds of formula (IA) in which
• R3A represents the group K, and
• R4A represents hydrogen atom, halogen, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, or a group
• where R1A and R2A are as defined above,
• reacting a compound of formula (IAk)
• wherein
• R4A represents hydrogen atom, halogen, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, or a group
• where R1A and R2A are as defined above, and
• R1A, R2A, R5A, R6A, and QA have the same definitions as for formula (IA),
• with a compound of formula (IX)
• R20A—Mg—Xk (IX)
• wherein
• Xk represents halogen, and
• R20A has the same definition as for formula (IA),
• in the presence of an inert solvent,
• or
• (l) for compounds of formula (IA) in which
• R3A represents group L or group M, and
• R4A represents hydrogen atom, halogen, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, or a group
• where R1A and R2A are as defined above,
• reacting a compound of formula (IAl)
• wherein
• R27A represents alkyl,
• R4Al represents hydrogen atom, halogen, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, or a group
• where R1A and R2A are as defined above, and
• R1A, R2A, R5A, R6A, and QA have the same definitions as for formula (IA),
• with a compound of formula (X)
• H2N—R28A (X)
• wherein R28A represents a group —O—R22A or a group
• wherein R22A, R24A, and R25A have the same definitions as for formula (IA),
• in the presence of an inert solvent, optionally in the presence of acid binder, and optionally in the presence of acid catalyst,
• or
• (m) for compounds of formula (IA) in which R3A represents group J,
• reacting a compound of formula (IAk) with a compound of formula (XI)
• H2NO—R19A (XI)
• wherein R19A has the same definition as for formula (IA),
• in the presence of AN inert solvent, optionally in the presence of acid binder, and optionally in the presence of acid catalyst.

An agrohorticultural fungicide comprising a benzylpyrimidine derivative of formula (I)

• wherein
• R1 and R2, together with the nitrogen atom to which they are bonded, form a 3- to 10-membered heterocyclic group that is optionally substituted and optionally contains one to three further hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and S(O)n in addition to the nitrogen atom to which R1 and R2 are bonded,
• n represents 0, 1, or 2,
• R3 represents hydrogen, halogen, cyano, hydroxy, amino, azido, alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkylthio, alkenylthio, haloalkenylthio, alkylsulfinyl, alkylsulfonyl, phenoxy that is optionally substituted, benzyloxy that is optionally substituted, phenyl that is optionally substituted, phenylalkyl that is optionally substituted, phenoxyalkyl that is optionally substituted, or 5- to 10-membered heterocyclic group that contains one to four hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted with a group selected from the group consisting of halogen, alkyl, and haloalkyl;
• or represents a moiety selected from the group consisting of formulas A to H and J to M
• in which
• R7 represents hydrogen atom, alkyl, or haloalkyl, and
• R8 represents alkyl, phenyl, alkoxy or cyano, or
• R7 and R8, together with the carbon atom to which they are bonded, form a cycloalkylidene,
• R9 represents alkyl, haloalkenyl, or benzyl,
• R10 represents hydrogen atom or alkyl,
• R11 represents alkyl, alkoxyalkyl, dialkylaminoalkyl, phenyl, benzyl, or cyano,
• R12 represents alkyl or phenyl,
• R13 represents alkyl or benzyl,
• R14 represents hydrogen atom or alkyl,
• R15 represents hydrogen atom, haloalkyl, or phenyl,
• R16 represents hydrogen atom or alkyl,
• R17 represents hydrogen atom, alkyl, or haloalkyl,
• R18 represents alkyl or phenyl,
• R19 represents hydrogen atom or alkyl,
• R20 represents alkyl,
• R21 represents alkyl,
• R22 represents alkyl, alkenyl, haloalkenyl, alkoxyalkyl, phenoxyalkyl, or alkoxycarbonylalkyl,
• R23 represents alkyl, and
• R24 represents hydrogen atom or alkyl, and
• R25 represents alkyl or phenyl, or
• R24 and R25, together with the nitrogen atom to which they are bonded, form a 5- to 8-membered saturated monoheterocyclic group that is optionally substituted and optionally contains one or two further hetero atoms selected from the group consisting of nitrogen atom, oxygen atom, and S(O)n in addition to the nitrogen atom to which R24 and R25 are bonded,
• R4 represents hydrogen atom, halogen, cyano, alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, or a group
• where R1 and R2 are as defined above,
• R5 and R6 each independently represents hydrogen atom, halogen, alkyl, haloalkyl, or phenyl that is optionally substituted, and
• Q represents aryl that is optionally substituted or a 5- or 6-membered heterocyclic group that contains one hetero atom selected from the group consisting of nitrogen atom, oxygen atom, and sulfur atom and is optionally substituted,
• and optionally one or more extenders and/or carriers and/or surfactants and/or further formulation auxiliaries.