US 2019/0047968 A1 · 6-ACYL-1,2,4-TRIAZINE-3,5-DIONE DERIVATIVE AND HERBICIDES

Abstract

Disclosed are triazine derivative compounds exhibiting sufficient herbicidal activity at low application dosage when they are applied to soils and foliage, and an agrochemical composition using the same, in particular herbicides.

Claims19

Dependent claims

1-12. (canceled)

A triazine derivative or a salt thereof represented by following Formula 2:

wherein B represents a hydroxyl group or a C1-C6 alkoxy group;
R1 represents a C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a C3-C6 cycloalkyl group;
a C3-C6 cycloalkenyl group;
a C3-C6 cycloalkyl C1-C6 alkyl group;
a C1-C6 haloalkyl group;
a C2-C6 haloalkenyl group;
a C2-C6 haloalkynyl group;
a C3-C6 halocycloalkyl group;
a C3-C6 halocycloalkyl C1-C6 alkyl group;
an amino C1-C6 alkyl group;
a nitro C1-C6 alkyl group;
a C1-C6 alkylamino C1-C6 alkyl group;
a di(C1-C6 alkyl)amino C1-C6 alkyl group;
a C1-C6 alkylthio C1-C6 alkyl group;
a C1-C6 alkylsulfinyl C1-C6 alkyl group;
a C1-C6 alkylsulfonyl C1-C6 alkyl group;
a C1-C6 haloalkylthio C1-C6 alkyl group;
a C1-C6 haloalkylsulfinyl C1-C6 alkyl group;
a C1-C6 haloalkylsulfonyl C1-C6 alkyl group;
a C1-C6 alkoxy C1-C6 alkyl group;
a hydroxy C1-C6 alkyl group;
a phenyl C1-C6 alkoxy C1-C6 alkyl group, wherein the phenyl in the group may be substituted with one substituent group selected from substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from substituent group α;
a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl group;
a C3-C6 cycloalkyloxy C1-C6 alkyl group;
a C3-C6 cycloalkyl C1-C6 alkyloxy C1-C6 alkyl group;
a phenyloxy C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylthio C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylsulfinyl C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylsulfonyl C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a C1-C6 haloalkoxy C1-C6 alkyl group;
a phenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C1-C6 alkyl group;
a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from the substituent group α;
a C1-C6 alkoxyimino C1-C6 alkyl group;
a phenoxyimino C1-C6 alkyl group which may be substituted with one or more substituents selected from the substituent group α;
a di(C1-C6 alkoxy) C1-C6 alkyl group;
a (R31R32N—C═O) C1-C6 alkyl group;
a C1-C6 alkoxycarbonyl C1-C6 alkyl group;
a C1-C6 alkylcarbonyl C1-C6 alkyl group;
a C1-C6 alkylcarbonyloxy C1-C6 alkyl group;
a C1-C6 alkylidene aminooxy C1-C6 alkyl group;
a formyl C1-C6 alkyl group;
a C1-C6 alkylthio C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylsulfinyl C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylsulfonyl C1-C6 alkoxy C1-C6 alkyl group;
a cyano C1-C6 alkoxy C1-C6 alkyl group;
a cyano C1-C6 alkyl group;
a C2-C6 alkylidene amino group;
a di(C1-C10 alkyl)amino C1-C6 alkylidene amino group;
a NR31R32 group;
a C1-C6 alkoxy group;
a C2-C6 alkenyloxy group;
a C2-C6 alkynyloxy group;
a C3-C6 cycloalkyloxy group;
a C3-C6 cycloalkyl C1-C6 alkyloxy group;
a C1-C6 haloalkoxy group;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone;
a C1-C6 alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a C1-C6 alkoxy C1-C6 alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
or a C1-C6 alkoxy C1-C6 alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
R2 represents a hydrogen atom;
a C1-C6 alkyl group;
a C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a C3-C6 cycloalkyl group;
a C1-C6 haloalkyl group;
a C2-C6 haloalkenyl group;
a C2-C6 haloalkynyl group;
a C1-C6 alkoxy C1-C6 alkyl group;
a C3-C6 cycloalkyloxy C1-C6 alkyl group;
a di(C1-C6 alkoxy) C1-C6 alkyl group;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C1-C6 alkyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from the substituent group α;
or a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from the substituent group α;
Y and Z represent an oxygen atom or a sulfur atom;
R31 and R32 each independently represent a C1-C6 alkyl group;
a phenyl group which may be substituted with one or more substituents selected from the substituent group α;
a benzyl group which may be substituted with one or more substituents selected from the substituent group α;
a C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylcarbonyl group;
a C1-C10 alkylthio carbonyl group;
a C1-C6 alkoxycarbonyl group;
a C1-C6 haloalkyl group;
a C3-C6 cycloalkyl group;
a C3-C6 cycloalkyl C1-C6 alkyl group;
a C1-C6 alkylsulfonyl group;
a phenylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α;
a benzylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
or a C1-C6 alkyl group substituted with a heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, wherein, R31 and R32 may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and the one or more carbon atoms in the ring may be substituted with a sulfur atom and/or an oxygen atom;
wherein, “substituent group α” represents a group selected from a group consisting of a halogen atom;
a hydroxyl group;
a C1-C6 alkyl group;
a C3-C6 cycloalkyl group;
a C3-C6 cycloalkyl C1-C6 alkyl group;
a C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a C1-C6 haloalkyl group;
a C2-C6 haloalkenyl group;
a C2-C6 haloalkynyl group;
a C3-C6 halocycloalkyl group;
a C3-C6 halocycloalkyl C1-C6 alkyl group;
a C1-C6 alkoxy group;
a C3-C6 cycloalkyloxy group;
a C2-C6 alkenyloxy group;
a C2-C6 alkynyloxy group;
a C1-C6 alkylcarbonyloxy group;
a C1-C6 haloalkoxy group;
a C1-C6 alkylthio group;
a C1-C6 alkylsulfinyl group;
a C1-C6 alkylsulfonyl group;
a C1-C6 haloalkylthio group;
a C1-C6 haloalkylsulfinyl group;
a C1-C6 haloalkylsulfonyl group;
an amino group;
a C1-C6 alkylcarbonylamino group;
a mono(C1-C6 alkyl)amino group;
a di(C1-C6 alkyl)amino group;
a hydroxy C1-C6 alkyl group;
a C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylthio C1-C6 alkyl group;
a C1-C6 alkylsulfinyl C1-C6 alkyl group;
a C1-C6 alkylsulfonyl C1-C6 alkyl group;
a C1-C6 haloalkylthio C1-C6 alkyl group;
a C1-C6 haloalkylsulfinyl C1-C6 alkyl group;
a C1-C6 haloalkylsulfonyl C1-C6 alkyl group;
a cyano C1-C6 alkyl group;
a C1-C6 alkoxy C1-C6 alkoxy group;
a C3-C6 cycloalkyl C1-C6 alkyloxy group;
a C1-C6 haloalkoxy C1-C6 alkoxy group;
a cyano C1-C6 alkoxy group;
a C1-C6 acyl group;
a C1-C6 alkoxyimino C1-C6 alkyl group;
a carboxyl group;
a C1-C6 alkoxycarbonyl group;
a carbamoyl group;
a mono(C1-C6 alkyl)aminocarbonyl group;
a di(C1-C6 alkyl)aminocarbonyl group;
a nitro group;
a cyano group;
a phenyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β;
a heterocyclic group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β;
a heterocyclic oxy group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β;
and a C3-C6 alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group;
and
“substituent group β” represents a group selected from a group consisting of a halogen atom, a nitro group, a cyano group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group.

148 more elements

A method of preparing a compound of Formula 13b, comprising treating a compound of Formula 13a with a sulfurizing agent,

wherein
R1 represents a C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a C3-C6 cycloalkyl group;
a C3-C6 cycloalkenyl group;
a C3-C6 cycloalkyl C1-C6 alkyl group;
a C1-C6 haloalkyl group;
a C2-C6 haloalkenyl group;
a C2-C6 haloalkynyl group;
a C3-C6 halocycloalkyl group;
a C3-C6 halocycloalkyl C1-C6 alkyl group;
an amino C1-C6 alkyl group;
a nitro C1-C6 alkyl group;
a C1-C6 alkylamino C1-C6 alkyl group;
a di(C1-C6 alkyl)amino C1-C6 alkyl group;
a C1-C6 alkylthio C1-C6 alkyl group;
a C1-C6 alkylsulfinyl C1-C6 alkyl group;
a C1-C6 alkylsulfonyl C1-C6 alkyl group;
a C1-C6 haloalkylthio C1-C6 alkyl group;
a C1-C6 haloalkylsulfinyl C1-C6 alkyl group;
a C1-C6 haloalkylsulfonyl C1-C6 alkyl group;
a C1-C6 alkoxy C1-C6 alkyl group;
a hydroxy C1-C6 alkyl group;
a phenyl C1-C6 alkoxy C1-C6 alkyl group, wherein the phenyl in the group may be substituted with one substituent group selected from substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from substituent group α;
a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl group;
a C3-C6 cycloalkyloxy c1-c6 alkyl group;
a C3-C6 cycloalkyl C1-C6 alkyloxy C1-C6 alkyl group;
a phenyloxy C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylthio C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylsulfinyl C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylsulfonyl C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a C1-C6 haloalkoxy C1-C6 alkyl group;
a phenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C1-C6 alkyl group;
a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from the substituent group α;
a C1-C6 alkoxyimino C1-C6 alkyl group;
a phenoxyimino C1-C6 alkyl group which may be substituted with one or more substituents selected from the substituent group α;
a di(C1-C6 alkoxy) C1-C6 alkyl group;
a (R31R32N—C═O) C1-C6 alkyl group;
a C1-C6 alkoxycarbonyl C1-C6 alkyl group;
a C1-C6 alkylcarbonyl C1-C6 alkyl group;
a C1-C6 alkylcarbonyloxy C1-C6 alkyl group;
a C1-C6 alkylidene aminooxy C1-C6 alkyl group;
a formyl C1-C6 alkyl group;
a C1-C6 alkylthio C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylsulfinyl C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylsulfonyl C1-C6 alkoxy C1-C6 alkyl group;
a cyano C1-C6 alkoxy C1-C6 alkyl group;
a cyano C1-C6 alkyl group;
a C2-C6 alkylidene amino group;
a di(C1-C10 alkyl)amino C1-C6 alkylidene amino group;
a NR31R32 group;
a C1-C6 alkoxy group;
a C2-C6 alkenyloxy group;
a C2-C6 alkynyloxy group;
a C3-C6 cycloalkyloxy group;
a C3-C6 cycloalkyl C1-C6 alkyloxy group;
a C1-C6 haloalkoxy group;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone;
a C1-C6 alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a C1-C6 alkoxy C1-C6 alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
or a C1-C6 alkoxy C1-C6 alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
R2 represents a hydrogen atom;
a C1-C6 alkyl group;
a C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a C3-C6 cycloalkyl group;
a C1-C6 haloalkyl group;
a C2-C6 haloalkenyl group;
a C2-C6 haloalkynyl group;
a C1-C6 alkoxy C1-C6 alkyl group;
a C3-C6 cycloalkyloxy C1-C6 alkyl group;
a di(C1-C6 alkoxy) C1-C6 alkyl group;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C1-C6 alkyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from the substituent group α;
or a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from the substituent group α;
Z represent an oxygen atom or a sulfur atom;
R31 and R32 each independently represent a C1-C6 alkyl group;
a phenyl group which may be substituted with one or more substituents selected from the substituent group α;
a benzyl group which may be substituted with one or more substituents selected from the substituent group α;
a C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylcarbonyl group;
a C1-C10 alkylthio carbonyl group;
a C1-C6 alkoxycarbonyl group;
a C1-C6 haloalkyl group;
a C3-C6 cycloalkyl group;
a C3-C6 cycloalkyl C1-C6 alkyl group;
a C1-C6 alkylsulfonyl group;
a phenylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α;
a benzylsulfonyl group which may be substituted with one or more substituents selected from the substituent group α;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
or a C1-C6 alkyl group substituted with a heterocyclic group in which the heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, wherein, R31 and R32 may be joined together to form a 5- to 6-membered ring with adjacent nitrogen atom, and the one or more carbon atoms in the ring may be substituted with a sulfur atom and/or an oxygen atom;
wherein, “substituent group α” represents a group selected from a group consisting of a halogen atom;
a hydroxyl group;
a C1-C6 alkyl group;
a C3-C6 cycloalkyl group;
a C3-C6 cycloalkyl C1-C6 alkyl group;
a C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a C1-C6 haloalkyl group;
a C2-C6 haloalkenyl group;
a C2-C6 haloalkynyl group;
a C3-C6 halocycloalkyl group;
a C3-C6 halocycloalkyl C1-C6 alkyl group;
a C1-C6 alkoxy group;
a C3-C6 cycloalkyloxy group;
a C2-C6 alkenyloxy group;
a C2-C6 alkynyloxy group;
a C1-C6 alkylcarbonyloxy group;
a C1-C6 haloalkoxy group;
a C1-C6 alkylthio group;
a C1-C6 alkylsulfinyl group;
a C1-C6 alkylsulfonyl group;
a C1-C6 haloalkylthio group;
a C1-C6 haloalkylsulfinyl group;
a C1-C6 haloalkylsulfonyl group;
an amino group;
a C1-C6 alkylcarbonylamino group;
a mono(C1-C6 alkyl)amino group;
a di(C1-C6 alkyl)amino group;
a hydroxy C1-C6 alkyl group;
a C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylthio C1-C6 alkyl group;
a C1-C6 alkylsulfinyl C1-C6 alkyl group;
a C1-C6 alkylsulfonyl C1-C6 alkyl group;
a C1-C6 haloalkylthio C1-C6 alkyl group;
a C1-C6 haloalkylsulfinyl C1-C6 alkyl group;
a C1-C6 haloalkylsulfonyl C1-C6 alkyl group;
a cyano C1-C6 alkyl group;
a C1-C6 alkoxy C1-C6 alkoxy group;
a C3-C6 cycloalkyl C1-C6 alkyloxy group;
a C1-C6 haloalkoxy C1-C6 alkoxy group;
a cyano C1-C6 alkoxy group;
a C1-C6 acyl group;
a C1-C6 alkoxyimino C1-C6 alkyl group;
a carboxyl group;
a C1-C6 alkoxycarbonyl group;
a carbamoyl group;
a mono(C1-C6 alkyl)aminocarbonyl group;
a di(C1-C6 alkyl)aminocarbonyl group;
a nitro group;
a cyano group;
a phenyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β;
a heterocyclic group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β;
a heterocyclic oxy group comprising 2 to 10 carbon atoms and 1 to 5 identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group β;
and a C3-C6 alkylene group formed with two adjacent substituent groups, wherein 1 to 3 carbon atoms in the alkylene group may be substituted with an atom selected from a group consisting of an oxygen atom, a sulfur atom, a nitrogen atom, and a carbon atom constituting an carbonyl group;
and
“substituent group β” represents a group selected from a group consisting of a halogen atom, a nitro group, a cyano group, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 alkoxy group, and a C1-C6 haloalkoxy group.

148 more elements

A method of preparing a compound of Formula 1a, comprising reacting at least one of a compound of Formula 5a and a compound of Formula 5b with a cyano compound in the presence of a base,

wherein R1 represents a hydrogen atom;
a C1-C12 alkyl group;
a C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a C3-C6 cycloalkyl group;
a C3-C6 cycloalkenyl group;
a C3-C6 cycloalkyl C1-C6 alkyl group;
a C1-C6 haloalkyl group;
a C2-C6 haloalkenyl group;
a C2-C6 haloalkynyl group;
a C3-C6 halocycloalkyl group;
a C3-C6 halocycloalkyl C1-C6 alkyl group;
an amino C1-C6 alkyl group;
a nitro C1-C6 alkyl group;
a C1-C6 alkylamino C1-C6 alkyl group;
a di(C1-C6 alkyl)amino C1-C6 alkyl group;
a C1-C6 alkylthio C1-C6 alkyl group;
a C1-C6 alkylsulfinyl C1-C6 alkyl group;
a C1-C6 alkylsulfonyl C1-C6 alkyl group;
a C1-C6 haloalkylthio C1-C6 alkyl group;
a C1-C6 haloalkylsulfinyl C1-C6 alkyl group;
a C1-C6 haloalkylsulfonyl C1-C6 alkyl group;
a C1-C6 alkoxy C1-C6 alkyl group;
a hydroxy C1-C6 alkyl group;
a phenyl C1-C6 alkoxy C1-C6 alkyl group, wherein the phenyl in the group may be substituted with one substituent group selected from substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from substituent group α;
a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl group;
a C3-C6 cycloalkyloxy C1-C6 alkyl group;
a C3-C6 cycloalkyl C1-C6 alkyloxy C1-C6 alkyl group;
a phenyloxy C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylthio C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylsulfinyl C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylsulfonyl C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a C1-C6 haloalkoxy C1-C6 alkyl group;
a phenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C1-C6 alkyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from the substituent group α;
a C1-C6 alkoxyimino C1-C6 alkyl group;
a phenoxyimino C1-C6 alkyl group which may be substituted with one or more substituents selected from the substituent group α;
a di(C1-C6 alkoxy)C1-C6 alkyl group;
a (R31R32N—C═O)C1-C6 alkyl group;
a C1-C6 alkoxycarbonyl C1-C6 alkyl group;
a C1-C6 alkylcarbonyl C1-C6 alkyl group;
a C1-C6 alkylcarbonyloxy C1-C6 alkyl group;
a C1-C6 alkylidene aminooxy C1-C6 alkyl group;
a formyl C1-C6 alkyl group;
a C1-C6 alkylthio C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylsulfinyl C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylsulfonyl C1-C6 alkoxy C1-C6 alkyl group;
a cyano C1-C6 alkoxy C1-C6 alkyl group;
a cyano C1-C6 alkyl group;
a C2-C6 alkylidene amino group;
a di(C1-C10 alkyl)amino C1-C6 alkylidene amino group;
a NR31R32 group;
a C1-C6 alkoxy group;
a C2-C6 alkenyloxy group;
a C2-C6 alkynyloxy group;
a C3-C6 cycloalkyloxy group;
a C3-C6 cycloalkyl C1-C6 alkyloxy group;
a C1-C6 haloalkoxy group;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone;
a C1-C6 alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a C1-C6 alkoxy C1-C6 alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
or a C1-C6 alkoxy C1-C6 alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
R2 represents a hydrogen atom;
a C1-C6 alkyl group;
a C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a C3-C6 cycloalkyl group;
a C1-C6 haloalkyl group;
a C2-C6 haloalkenyl group;
a C2-C6 haloalkynyl group;
a C1-C6 alkoxy C1-C6 alkyl group;
a C3-C6 cycloalkyloxy C1-C6 alkyl group;
a di(C1-C6 alkoxy) C1-C6 alkyl group;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C1-C6 alkyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from the substituent group α;
or a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from the substituent group α,
Y and Z represent an oxygen atom or a sulfur atom,
A1 represents a group represented by the following formula
A2 represents a group represented by the following formula
A3 represents a group represented by the following formula
n represents 0, 1, or 2,
R5, R6, R8, R9, R35 and R36 each independently represent a hydrogen atom or a C1-C6 alkyl group, wherein, R5 and R8 may be joined together to form a C2-C5 alkylene chain or a C2-C5 alkenylene chain, and may form a ring together with adjacent carbon atoms, and R5 and R35 may be joined together to form a C1-C5 alkylene chain to form a ring with adjacent carbon atoms,
and
R7, R33, and R34 each independently represent a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, or a C1-C6 alkoxy group.

85 more elements

A method of preparing a compound of Formula 1a, comprising reacting a compound of Formula 3 with a compound of Formula 4c,

wherein R1 represents a hydrogen atom;
a C1-C12 alkyl group;
a C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a C3-C6 cycloalkyl group;
a C3-C6 cycloalkenyl group;
a C3-C6 cycloalkyl C1-C6 alkyl group;
a C1-C6 haloalkyl group;
a C2-C6 haloalkenyl group;
a C2-C6 haloalkynyl group;
a C3-C6 halocycloalkyl group;
a C3-C6 halocycloalkyl C1-C6 alkyl group;
an amino C1-C6 alkyl group;
a nitro C1-C6 alkyl group;
a C1-C6 alkylamino C1-C6 alkyl group;
a di(C1-C6 alkyl)amino C1-C6 alkyl group;
a C1-C6 alkylthio C1-C6 alkyl group;
a C1-C6 alkylsulfinyl C1-C6 alkyl group;
a C1-C6 alkylsulfonyl C1-C6 alkyl group;
a C1-C6 haloalkylthio C1-C6 alkyl group;
a C1-C6 haloalkylsulfinyl C1-C6 alkyl group;
a C1-C6 haloalkylsulfonyl C1-C6 alkyl group;
a C1-C6 alkoxy C1-C6 alkyl group;
a hydroxy C1-C6 alkyl group;
a phenyl C1-C6 alkoxy C1-C6 alkyl group, wherein the phenyl in the group may be substituted with one substituent group selected from substituent group α or 2 to 5 substituent groups that are the same or different from each other and selected from substituent group α;
a C1-C6 alkoxy C1-C6 alkoxy C1-C6 alkyl group;
a C3-C6 cycloalkyloxy C1-C6 alkyl group;
a C3-C6 cycloalkyl C1-C6 alkyloxy C1-C6 alkyl group;
a phenyloxy C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylthio C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylsulfinyl C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenylsulfonyl C1-C6 alkyl group, wherein the phenyl in the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a C1-C6 haloalkoxy C1-C6 alkyl group;
a phenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C1-C6 alkyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from the substituent group α;
a C1-C6 alkoxyimino C1-C6 alkyl group;
a phenoxyimino C1-C6 alkyl group which may be substituted with one or more substituents selected from the substituent group α;
a di(C1-C6 alkoxy)C1-C6 alkyl group;
a (R31R32N—C═O)C1-C6 alkyl group;
a C1-C6 alkoxycarbonyl C1-C6 alkyl group;
a C1-C6 alkylcarbonyl C1-C6 alkyl group;
a C1-C6 alkylcarbonyloxy C1-C6 alkyl group;
a C1-C6 alkylidene aminooxy C1-C6 alkyl group;
a formyl C1-C6 alkyl group;
a C1-C6 alkylthio C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylsulfinyl C1-C6 alkoxy C1-C6 alkyl group;
a C1-C6 alkylsulfonyl C1-C6 alkoxy C1-C6 alkyl group;
a cyano C1-C6 alkoxy C1-C6 alkyl group;
a cyano C1-C6 alkyl group;
a C2-C6 alkylidene amino group;
a di(C1-C10 alkyl)amino C1-C6 alkylidene amino group;
a NR31R32 group;
a C1-C6 alkoxy group;
a C2-C6 alkenyloxy group;
a C2-C6 alkynyloxy group;
a C3-C6 cycloalkyloxy group;
a C3-C6 cycloalkyl C1-C6 alkyloxy group;
a C1-C6 haloalkoxy group;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α, and when the heteroatom in the heterocyclic group is a sulfur atom, the sulfur atom may be oxidized to sulfoxide or sulfone;
a C1-C6 alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a C1-C6 alkoxy C1-C6 alkyl group substituted with a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
or a C1-C6 alkoxy C1-C6 alkyl group substituted with a heterocyclic-oxy group in which the heterocyclic group in the heterocyclic-oxy group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
R2 represents a hydrogen atom;
a C1-C6 alkyl group;
a C2-C6 alkenyl group;
a C2-C6 alkynyl group;
a C3-C6 cycloalkyl group;
a C1-C6 haloalkyl group;
a C2-C6 haloalkenyl group;
a C2-C6 haloalkynyl group;
a C1-C6 alkoxy C1-C6 alkyl group;
a C3-C6 cycloalkyloxy C1-C6 alkyl group;
a di(C1-C6 alkoxy) C1-C6 alkyl group;
a heterocyclic group comprising 3 to 10 carbon atoms and one or more identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, wherein the group may be substituted with 1 to 5 identical or different substituents selected from the substituent group α;
a phenyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C1-C6 alkyl group which may be substituted with one or more substituents selected from the substituent group α;
a phenyl C2-C6 alkenyl group which may be substituted with one or more substituents selected from the substituent group α;
or a phenyl C2-C6 alkynyl group which may be substituted with one or more substituents selected from the substituent group α,
Y and Z represent an oxygen atom or a sulfur atom,
A1 represents a group represented by the following formula
A2 represents a group represented by the following formula
A3 represents a group represented by the following formula
n represents 0, 1, or 2,
R5, R6, R8, R9, R35 and R36 each independently represent a hydrogen atom or a C1-C6 alkyl group, wherein, R5 and R8 may be joined together to form a C2-C5 alkylene chain or a C2-C5 alkenylene chain, and may form a ring together with adjacent carbon atoms, and R5 and R35 may be joined together to form a C1-C5 alkylene chain to form a ring with adjacent carbon atoms,
and
R7, R33, and R34 each independently represent a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, or a C1-C6 alkoxy group.

85 more elements

Dependencies are inferred from the claim text.

Facts

Application

16/139,318Filed 24 Sep 2018

Priority

28 Dec 2012

Published

14 Feb 2019

Term ends

Not estimatedThe source records don’t support an estimate.

Classification43 codes

C07D 253/075
With hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
A01N 43/707
Having rings with three nitrogen atoms as the only ring hetero atoms: 1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
A01N 43/78
Five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
A01N 43/80
Having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms: five-membered rings with one nitrogen atom and either one oxygen…

Family

Application13/807,590Continuation · filed 28 Dec 2012

Application14/603,029Continuation · filed 22 Jan 2015

Application15/393,850Continuation · filed 29 Dec 2016

Application16/139,318Continuation

US 10,081,608 B2Related patent

US 2013/0102468 A1Published application

US 2015/0203457 A1Published application

US 2017/0129861 A1Published application

US 8,969,554 B2Related patent

US 9,573,909 B2Related patent

US 2019/0047968 A1This patent

From the US filing history. Foreign family members aren’t listed.

6-acyl-1,2,4-triazine-3,5-dione derivative and herbicides

Life of this patent

Abstract

Claims19

6-acyl-1,2,4-triazine-3,5-dione derivative and herbicides

Life of this patent

Abstract

Claims19