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US 2020/0045968 A1Published application
Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients
AssigneeMitsui Chemicals Agro, Inc.
InventorsHideki UMETANI, Shun OKAYA, Hideaki IKISHIMA, Takeshi FUKUMOTO, Akihiro NISHIDA, Masanori YANAGI, Ryohei NAITO, Koji MASUTOMI, Tomomi SHIRAKAWA, Akane SAKURADA, Satoshi YUTANI
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Abstract
Pyridine compounds of Formula (1) are provided: wherein R1, R2, X, Y and Het are defined. The pyridine compounds can be used to treat or prevent plant diseases.
Claims9
A compound represented by Formula (1)
- or a salt thereof
- [wherein R1 represents
- a hydroxyl group,
- a cyano group,
- a C1-C6 alkyl group optionally substituted with substituent(s) A,
- a C1-C6 haloalkyl group,
- a C3-C8 cycloalkyl group optionally substituted with substituent(s) A,
- a C2-C6 alkenyl group optionally substituted with substituent(s) A,
- a C2-C6 haloalkenyl group,
- a C2-C6 alkynyl group optionally substituted with substituent(s) A,
- a C2-C6 haloalkynyl group,
- a C1-C6 alkoxy group optionally substituted with substituent(s) A,
- a C1-C6 haloalkoxy group,
- a C3-C8 cycloalkoxy group optionally substituted with substituent(s) A,
- a C2-C6 alkenyloxy group optionally substituted with substituent(s) A,
- a C2-C6 haloalkenyloxy group,
- a C3-C6 alkynyloxy group optionally substituted with substituent(s) A,
- a C3-C6 haloalkynyloxy group,
- or RaRbN— (wherein Ra and Rb each independently represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group);
- R2 represents
- a hydrogen atom,
- a nitro group,
- a halogen atom,
- a C1-C6 alkyl group optionally substituted with substituent(s) A,
- a C1-C6 haloalkyl group,
- a C3-C8 cycloalkyl group optionally substituted with substituent(s) A,
- a C2-C6 alkenyl group optionally substituted with substituent(s) A,
- a C2-C6 haloalkenyl group,
- a C2-C6 alkynyl group optionally substituted with substituent(s) A,
- a C2-C6 haloalkynyl group,
- a C1-C6 alkoxy group optionally substituted with substituent(s) A,
- a C1-C6 haloalkoxy group,
- a C3-C8 cycloalkoxy group optionally substituted with substituent(s) A,
- a C2-C6 alkenyloxy group optionally substituted with substituent(s) A,
- a C2-C6 haloalkenyloxy group,
- a C3-C6 alkynyloxy group optionally substituted with substituent(s) A,
- a C3-C6 haloalkynyloxy group,
- Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group and L represents S, SO or SO2),
- or Rx1C(═O)— (wherein Rx1 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove));
- Het represents
- a 5 to 6-membered heterocyclic group or a 8 to 10-membered heterocyclic group, and the 5 to 6-membered heterocyclic group or the 8 to 10-membered heterocyclic group is optionally substituted with 0 to 6 substituents R3 (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent),
- R3 represents
- a hydroxyl group,
- a cyano group,
- a nitro group,
- a halogen atom,
- a C1-C6 alkyl group optionally substituted with substituent(s) C,
- a C1-C6 haloalkyl group,
- a C3-C8 cycloalkyl group optionally substituted with substituent(s) C,
- a C2-C6 alkenyl group optionally substituted with substituent(s) C,
- a C2-C6 haloalkenyl group,
- a C2-C6 alkynyl group optionally substituted with substituent(s) C,
- a C2-C6 haloalkynyl group,
- a C1-C6 alkoxy group optionally substituted with substituent(s) C,
- a C1-C6 haloalkoxy group,
- a C3-C8 cycloalkoxy group optionally substituted with substituent(s) C,
- a C2-C6 alkenyloxy group optionally substituted with substituent(s) C,
- a C2-C6 haloalkenyloxy group,
- a C3-C6 alkynyloxy group optionally substituted with substituent(s) C,
- a C3-C6 haloalkynyloxy group,
- an aryl group optionally substituted with substituent(s) D,
- a heteroaryl group optionally substituted with substituent(s) D,
- an aryloxy group optionally substituted with substituent(s) D,
- a heteroaryloxy group optionally substituted with substituent(s) D,
- an aralkyloxy group optionally substituted with substituent(s) D,
- RaRbN— (wherein Ra and Rb are the same as defined hereinabove),
- Rc-L- (wherein Rc and L are the same as defined hereinabove),
- Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove),
- Rx1C(═O)O— (wherein Rx1 is the same as defined hereinabove),
- Rx2C(═O)N(Rx3)- (wherein Rx2 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rx3 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group),
- Rx4Rx5C═N—O— (wherein Rx4 and Rx5 each independently represent a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove),
- or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms;
- Y represents
- a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group or a thiadiazolyl group,
- the phenyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 4 substituents R5 (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent),
- the pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group or the tetrazinyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 3 substituents R5 (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent),
- the thienyl group, the thiazolyl group, the isothiazolyl group or the thiadiazolyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 2 substituents R5 (with the proviso that when two substituents R5 are present, each R5 represents an independent substituent),
- R4 represents
- a hydroxyl group,
- a cyano group,
- a nitro group,
- a halogen atom,
- a C1-C6 alkyl group optionally substituted with substituent(s) C,
- a C1-C6 haloalkyl group,
- a C3-C8 cycloalkyl group optionally substituted with substituent(s) C,
- a C2-C6 alkenyl group optionally substituted with substituent(s) C,
- a C2-C6 haloalkenyl group,
- a C2-C6 alkynyl group optionally substituted with substituent(s) C,
- a C2-C6 haloalkynyl group,
- a C1-C6 alkoxy group optionally substituted with substituent(s) C,
- a C1-C6 haloalkoxy group,
- a C3-C8 cycloalkoxy group optionally substituted with substituent(s) C,
- a C2-C6 alkenyloxy group optionally substituted with substituent(s) C,
- a C2-C6 haloalkenyloxy group,
- a C3-C6 alkynyloxy group optionally substituted with substituent(s) C,
- a C3-C6 haloalkynyloxy group,
- an aryl group optionally substituted with substituent(s) D,
- a heteroaryl group optionally substituted with substituent(s) D,
- an aryloxy group optionally substituted with substituent(s) D,
- a heteroaryloxy group optionally substituted with substituent(s) D,
- an aralkyloxy group optionally substituted with substituent(s) D,
- RaRbN— (wherein Ra and Rb are the same as defined hereinabove),
- Rc-L- (wherein Rc and L are the same as defined hereinabove),
- Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove),
- Rx1C(═O)O— (wherein Rx1 is the same as defined hereinabove),
- Rx2C(═O)N(Rx3)- (wherein Rx2 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rx3 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group),
- Rx4Rx5C═N—O— (wherein Rx4 and Rx5 each independently represent a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove)),
- or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms,
- R5 is defined the same as R4 described hereinabove;
- X represents an oxygen atom or a sulfur atom;
- a bond containing the broken line represents a double bond or a single bond;
- and the substituent(s) A is at least one kind selected from the group consisting of a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN— (wherein Ra and Rb are the same as defined hereinabove) and Rc-L- (wherein Rc and L are the same as defined hereinabove);
- the substituent(s) B is at least one kind selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;
- the substituent(s) C is at least one kind selected from the group consisting of a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rc-L- (wherein Rc and L are the same as defined hereinabove), Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove) and a 3 to 6-membered ring group containing 1 to 2 oxygen atoms;
- the substituent(s) D is at least one kind selected from the group consisting of a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group which may be substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group.
112 more elements
A compound represented by Formula (2)
- or a salt thereof
- [wherein R2 represents
- a hydrogen atom,
- a nitro group,
- a halogen atom,
- a C1-C6 alkyl group optionally substituted with substituent(s) A,
- a C1-C6 haloalkyl group,
- a C3-C8 cycloalkyl group optionally substituted with substituent(s) A,
- a C2-C6 alkenyl group optionally substituted with substituent(s) A,
- a C2-C6 haloalkenyl group,
- a C2-C6 alkynyl group optionally substituted with substituent(s) A,
- a C2-C6 haloalkynyl group,
- a C1-C6 alkoxy group optionally substituted with substituent(s) A,
- a C1-C6 haloalkoxy group,
- a C3-C8 cycloalkoxy group optionally substituted with substituent(s) A,
- a C2-C6 alkenyloxy group optionally substituted with substituent(s) A,
- a C2-C6 haloalkenyloxy group,
- a C3-C6 alkynyloxy group optionally substituted with substituent(s) A,
- a C3-C6 haloalkynyloxy group,
- Rc-L- (wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group and L represents S, SO or SO2),
- or Rx1C(═O)— (wherein Rx1 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb each independently represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group or Ra and Rb together with the nitrogen atom to which they are bonded form an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidinyl group, a homopiperidinyl group or an azocanyl group));
- Het represents
- a 5 to 6-membered heterocyclic group or a 8 to 10-membered heterocyclic group, and the 5 to 6-membered heterocyclic group or the 8 to 10-membered heterocyclic group may be optionally substituted with 0 to 6 substituents R3 (with the proviso that when two or more substituents R3 are present, each R3 represents an independent substituent),
- R3 represents
- a hydroxyl group,
- a cyano group,
- a nitro group,
- a halogen atom,
- a C1-C6 alkyl group optionally substituted with substituent(s) C,
- a C1-C6 haloalkyl group,
- a C3-C8 cycloalkyl group optionally substituted with substituent(s) C,
- a C2-C6 alkenyl group optionally substituted with substituent(s) C,
- a C2-C6 haloalkenyl group,
- a C2-C6 alkynyl group optionally substituted with substituent(s) C,
- a C2-C6 haloalkynyl group,
- a C1-C6 alkoxy group optionally substituted with substituent(s) C,
- a C1-C6 haloalkoxy group,
- a C3-C8 cycloalkoxy group optionally substituted with substituent(s) C,
- a C2-C6 alkenyloxy group optionally substituted with substituent(s) C,
- a C2-C6 haloalkenyloxy group,
- a C3-C6 alkynyloxy group optionally substituted with substituent(s) C,
- a C3-C6 haloalkynyloxy group,
- an aryl group optionally substituted with substituent(s) D,
- a heteroaryl group optionally substituted with substituent(s) D,
- an aryloxy group optionally substituted with substituent(s) D,
- a heteroaryloxy group optionally substituted with substituent(s) D,
- an aralkyloxy group optionally substituted with substituent(s) D,
- RaRbN— (wherein Ra and Rb are the same as defined hereinabove),
- Rc-L- (wherein Rc and L are the same as defined hereinabove),
- Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove),
- Rx1C(═O)O— (wherein Rx1 is the same as defined hereinabove),
- Rx2C(═O)N(Rx3)- (wherein Rx2 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rx3 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group),
- Rx4Rx5C═N—O— (wherein Rx4 and Rx5 each independently represent a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove)),
- or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms;
- Y represents
- a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, a tetrazinyl group, a thienyl group, a thiazolyl group, an isothiazolyl group or a thiadiazolyl group,
- the phenyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 4 substituents R5 (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent),
- the pyridyl group, the pyridazinyl group, the pyrimidinyl group, the pyrazinyl group, the triazinyl group or the tetrazinyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 3 substituents R5 (with the proviso that when two or more substituents R5 are present, each R5 represents an independent substituent),
- the thienyl group, the thiazolyl group, the isothiazolyl group or the thiadiazolyl group is substituted with R4 at the ortho position and further optionally substituted with 0 to 2 substituents R5 (with the proviso that when two substituents R5 are present, each R5 represents an independent substituent),
- R4 represents
- a hydroxyl group,
- a cyano group,
- a nitro group,
- a halogen atom,
- a C1-C6 alkyl group optionally substituted with substituent(s) C,
- a C1-C6 haloalkyl group,
- a C3-C8 cycloalkyl group optionally substituted with substituent(s) C,
- a C2-C6 alkenyl group optionally substituted with substituent(s) C,
- a C2-C6 haloalkenyl group,
- a C2-C6 alkynyl group optionally substituted with substituent(s) C,
- a C2-C6 haloalkynyl group,
- a C1-C6 alkoxy group optionally substituted with substituent(s) C,
- a C1-C6 haloalkoxy group,
- a C3-C8 cycloalkoxy group optionally substituted with substituent(s) C,
- a C2-C6 alkenyloxy group optionally substituted with substituent(s) C,
- a C2-C6 haloalkenyloxy group,
- a C3-C6 alkynyloxy group optionally substituted with substituent(s) C,
- a C3-C6 haloalkynyloxy group,
- an aryl group optionally substituted with substituent(s) D,
- a heteroaryl group optionally substituted with substituent(s) D,
- an aryloxy group optionally substituted with substituent(s) D,
- a heteroaryloxy group optionally substituted with substituent(s) D,
- an aralkyloxy group optionally substituted with substituent(s) D,
- RaRbN— (wherein Ra and Rb are the same as defined hereinabove),
- Rc-L- (wherein Rc and L are the same as defined hereinabove),
- Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove),
- Rx1C(═O)O— (wherein Rx1 is the same as defined hereinabove),
- Rx2C(═O)N(Rx3)- (wherein Rx2 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rx3 represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group),
- Rx4Rx5C═N—O— (wherein Rx4 and Rx5 each independently represent a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group or RaRbN— (wherein Ra and Rb are the same as defined hereinabove)),
- or a 3 to 6-membered ring group containing 1 to 2 oxygen atoms,
- R5 is defined the same as R4 described hereinabove;
- X represents an oxygen atom or a sulfur atom;
- and the substituent(s) A is at least one kind selected from the group consisting of a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, RaRbN— (wherein Ra and Rb are the same as defined hereinabove) and Rc-L- (wherein Rc and L are the same as defined hereinabove);
- the substituent(s) B is at least one kind selected from the group consisting of a cyano group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group;
- the substituent(s) C is at least one kind selected from the group consisting of a hydroxyl group, a cyano group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkoxyalkoxy group, RaRbN— (wherein Ra and Rb are the same as defined hereinabove), Rc-L- (wherein Rc and L are the same as defined hereinabove), Rx1C(═O)— (wherein Rx1 is the same as defined hereinabove) and a 3 to 6-membered ring group containing 1 to 2 oxygen atoms;
- and
- the substituent(s) D is at least one kind selected from the group consisting of a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group which may be substituted with substituent(s) B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C1-C6 alkoxy group,
- a C1-C6 haloalkoxy group and a C3-C8 cycloalkoxy group.
95 more elements
Dependencies are inferred from the claim text.