IP Library › Granted Patent US 11,117,863
Granted Patent B2
US 11,117,863 · App. 16/615,445 · Granted Sep 14, 2021

Pyridone compounds and agricultural and horticultural fungicides containing the same as active ingredients

Inventors: Hideki Umetani (Ritto, JP); Hideaki Ikishima (Chiba, JP); Kouji Takagi (Mobara, JP); Takeshi Fukumoto (Chiba, JP); Ryohei Naito (Kusatsu, JP); Tomomi Shirakawa (Ritto, JP); Hikaru Koishihara (Chiba, JP); Hisaki Yamanaka (Yasu, JP); Miyuki Kawashima (Chiba, JP); Akane Sakurada (Mobara, JP)
Assignee: MITSUI CHEMICALS AGRO, INC.
C07D213/80A01N43/40C07D213/74C07D213/75C07D401/10C07D409/10C07D417/10
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Quick Facts
Patent No.
US 11,117,863
App. No.
16/615,445
Granted
Sep 14, 2021
Kind
B2
Abstract

Provided are a pyridone compound represented by Formula (1): wherein R1 represents a C1-C6 alkyl group which may be substituted, etc., R2 represents a halogen atom, a cyano group, etc., R3 and R4 are independent to each other, and each represents a hydrogen atom, a C1-C6 alkyl group which may be substituted, etc., or in combination with the nitrogen atom to which they are bonded form a pyrrolidinyl group, a piperidinyl group, etc., which may be substituted, Y represents a phenyl group which may be substituted, etc., X represents an oxygen atom or a sulfur atom, and an agricultural and horticultural fungicide containing the same as an active ingredient.

Claims (294)

1. A compound represented by Formula (1)

wherein R1 represents

a hydroxyl group,

a cyano group,

a C1-C6 alkyl group optionally substituted with substituent A,

a C1-C6 haloalkyl group,

a C3-C8 cycloalkyl group optionally substituted with substituent A,

a C2-C6 alkenyl group optionally substituted with substituent A,

a C2-C6 haloalkenyl group,

a C2-C6 alkynyl group optionally substituted with substituent A,

a C2-C6 haloalkynyl group,

a C1-C6 alkoxy group optionally substituted with substituent A,

a C1-C6 haloalkoxy group,

a C3-C8 cycloalkoxy group optionally substituted with substituent A,

a C2-C6 alkenyloxy group optionally substituted with substituent A,

a C2-C6 haloalkenyloxy group,

a C3-C6 alkynyloxy group optionally substituted with substituent A,

a C3-C6 haloalkynyloxy group, or

an RaRbN— wherein Ra and Rb are independent to each other, and each represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb in combination 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 cyano group,

a nitro group,

a halogen atom,

a C1-C6 alkyl group optionally substituted with substituent A,

a C1-C6 haloalkyl group,

a C3-C8 cycloalkyl group optionally substituted with substituent A,

a C2-C6 alkenyl group optionally substituted with substituent A,

a C2-C6 haloalkenyl group,

a C2-C6 alkynyl group optionally substituted with substituent A,

a C2-C6 haloalkynyl group,

a C1-C6 alkoxy group optionally substituted with substituent A,

a C1-C6 haloalkoxy group,

a C3-C8 cycloalkoxy group optionally substituted with substituent A,

a C2-C6 alkenyloxy group optionally substituted with substituent A,

a C2-C6 haloalkenyloxy group,

a C3-C6 alkynyloxy group optionally substituted with substituent A,

a C3-C6 haloalkynyloxy group,

an Rc-L- wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO or SO 2 ,

an RaRbN— wherein Ra and Rb are the same as defined above, or

an RdC(═O)— wherein Rd represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent 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 an RaRbN— wherein Ra and Rb are the same as defined above;

R3 and R4 are independent to each other, and each represents

a hydrogen atom,

a C1-C6 alkyl group optionally substituted with substituent C,

a C1-C6 haloalkyl group,

a C3-C8 cycloalkyl group optionally substituted with substituent C,

a C2-C6 alkenyl group optionally substituted with substituent C,

a C2-C6 haloalkenyl group,

a C2-C6 alkynyl group optionally substituted with substituent C,

a C2-C6 haloalkynyl group,

a C1-C6 alkoxy group optionally substituted with substituent C,

a C1-C6 haloalkoxy group,

a C3-C8 cycloalkoxy group optionally substituted with substituent C,

a C2-C6 alkenyloxy group optionally substituted with substituent C,

a C2-C6 haloalkenyloxy group,

a C3-C6 alkynyloxy group optionally substituted with substituent C,

a C3-C6 haloalkynyloxy group,

a phenyl group optionally substituted with 0 to 5 substituent D with the proviso that when there are two or more substituents D, they are independent to each other,

a C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 substituent D with the proviso that when there are two or more substituents D, they are independent to each other,

a C1-C6 haloalkyl group having a phenyl group optionally substituted with 0 to 5 substituent D with the proviso that when there are two or more substituents D, they are independent to each other,

an Rc-L- wherein Rc and L are the same as defined above, or

an ReC(═O)— wherein Re represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkenyloxy group, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group or an RaRbN— wherein Ra and Rb are the same as defined above,

or

R3 and R4 in combination with the nitrogen atom to which they are bonded form

an aziridinyl group optionally substituted with substituent E,

an azetidinyl group optionally substituted with substituent E,

a pyrrolidinyl group optionally substituted with substituent E,

a piperidinyl group optionally substituted with substituent E,

a homopiperidinyl group optionally substituted with substituent E,

an azocanyl group optionally substituted with substituent E,

a morpholinyl group optionally substituted with substituent E or

a C1-C6 alkylidene group optionally substituted with substituent F;

X represents an oxygen atom or a sulfur atom;

Y represents

a phenyl group optionally substituted with 0 to 5 R5 with the proviso that when there are two or more R5, they are independent to each other,

a pyridyl group optionally substituted with 0 to 4 R5 with the proviso that when there are two or more R5, they are independent to each other,

a pyridazinyl group optionally substituted with 0 to 3 R5 with the proviso that when there are two or more R5, they are independent to each other,

a pyrimidinyl group optionally substituted with 0 to 3 R5 with the proviso that when there are two or more R5, they are independent to each other,

a pyradinyl group optionally substituted with 0 to 3 R5 with the proviso that when there are two or more R5, they are independent to each other,

a triazinyl group optionally substituted with 0 to 2 R5 with the proviso that when there are two R5, they are independent to each other,

a tetrazinyl group optionally substituted with R5,

a thienyl group optionally substituted with 0 to 3 R5 with the proviso that when there are two or more R5, they are independent to each other,

a thiazolyl group optionally substituted with 0 to 2 R5 with the proviso that when there are two R5, they are independent to each other,

an isothiazolyl group optionally substituted with 0 to 2 R5 with the proviso that when there are two R5, they are independent to each other,

or a thiadiazolyl group optionally substituted with R5,

R5 represents

a hydroxyl group,

a cyano group,

a nitro group,

a halogen atom,

a C1-C6 alkyl group optionally substituted with substituent G,

a C1-C6 haloalkyl group,

a C3-C8 cycloalkyl group optionally substituted with substituent G,

a C2-C6 alkenyl group optionally substituted with substituent G,

a C2-C6 haloalkenyl group,

a C2-C6 alkynyl group optionally substituted with substituent G,

a C2-C6 haloalkynyl group,

a C1-C6 alkoxy group optionally substituted with substituent G,

a C1-C6 haloalkoxy group,

a C3-C8 cycloalkoxy group optionally substituted with substituent G,

a C2-C6 alkenyloxy group optionally substituted with substituent G,

a C2-C6 haloalkenyloxy group,

a C3-C6 alkynyloxy group optionally substituted with substituent G,

a C3-C6 haloalkynyloxy group,

an RdC(═O)— wherein Rd is the same as defined above,

an RdC(═O)O— wherein Rd is the same as defined above,

an Rc-L- wherein Rc and L are the same as defined above, or

an RaRbN— wherein Ra and Rb are the same as defined above; and

the substituent A is at least one member 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, an RaRbN— wherein Ra and Rb are the same as defined above, and an Rc-L- wherein Rc and L are the same as defined above;

the substituent B is at least one member 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 C is at least one member 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 alkenyloxy group, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group and an Rc-L- wherein Rc and L are the same as defined above;

the substituent D is at least one member selected from the group consisting of a hydroxyl group, a cyano group, a nitro group, a halogen atom, a C1-C6 alkyl group optionally substituted with substituent 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;

the substituent E is at least one member selected from the group consisting of an oxo group, a halogen atom, a C1-C6 alkyl group, 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;

the substituent F is at least one member selected from the group consisting of, a C1-C6 alkoxy group, an RaRbN— wherein Ra and Rb are the same as defined above and RdC(═O)— wherein Rd is the same as defined above;

the substituent G is at least one member 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, an RaRbN— wherein Ra and Rb are the same as defined above, an Rc-L- wherein Rc and L are the same as defined above, an RdC(═O)— wherein Rd is the same as defined above, an RdC(═O)O— wherein Rd is the same as defined above, and a group of a 3-6 membered ring containing 1-2 oxygen atoms,

or a salt thereof.

2. The compound according to claim 1 , wherein

R1 represents

a C1-C6 alkyl group optionally substituted with substituent A,

a C1-C6 haloalkyl group,

a C2-C6 alkenyl group optionally substituted with substituent A,

a C2-C6 haloalkenyl group,

a C2-C6 alkynyl group optionally substituted with substituent A, or

a C2-C6 haloalkynyl group;

R2 represents

a hydrogen atom,

a cyano group,

a halogen atom,

a C1-C6 alkyl group optionally substituted with substituent A,

a C1-C6 haloalkyl group,

a C2-C6 alkynyl group optionally substituted with substituent A,

a C2-C6 haloalkynyl group,

a C1-C6 alkoxy group optionally substituted with substituent A,

a C1-C6 haloalkoxy group,

an Rc-L- wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO or SO 2 , or

an RdC(═O)— wherein Rd represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent 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 an RaRbN— wherein Ra and Rb are independent to each other, and each represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb in combination 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;

R3 and R4 are independent to each other, and each represents

a hydrogen atom,

a C1-C6 alkyl group optionally substituted with substituent C,

a C1-C6 haloalkyl group,

a C3-C8 cycloalkyl group optionally substituted with substituent C,

a C2-C6 alkenyl group optionally substituted with substituent C,

a C2-C6 haloalkenyl group,

a C2-C6 alkynyl group optionally substituted with substituent C,

a C2-C6 haloalkynyl group,

a phenyl group optionally substituted with 0 to 5 substituent D with the proviso that when there are two or more substituents D, they are independent to each other,

a C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 substituent D with the proviso that when there are two or more substituents D, they are independent to each other,

an Rc-L- wherein Rc and L are the same as defined above, or

an ReC(═O)— wherein Re represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkenyloxy group, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group or an RaRbN— wherein Ra and Rb are the same as defined above,

or

R3 and R4 in combination with the nitrogen atom to which they are bonded form

a pyrrolidinyl group optionally substituted with substituent E,

a piperidinyl group optionally substituted with substituent E,

a morpholinyl group optionally substituted with substituent E, or

a C1-C6 alkylidene group optionally substituted with substituent F;

Y represents

a phenyl group optionally substituted with 0 to 5 R5 with the proviso that when there are two or more R5, they are independent to each other, or

a pyridyl group optionally substituted with 0 to 4 R5 with the proviso that when there are two or more R5, they are independent to each other,

R5 represents

a hydroxyl group,

a cyano group,

a halogen atom,

a C1-C6 alkyl group optionally substituted with substituent G,

a C1-C6 alkoxy group optionally substituted with substituent G,

a C1-C6 haloalkoxy group,

a C2-C6 alkenyloxy group optionally substituted with substituent G,

a C2-C6 haloalkenyloxy group,

a C3-C6 alkynyloxy group optionally substituted with substituent G,

a C3-C6 haloalkynyloxy group, or

an RdC(═O)O— wherein Rd is the same as defined above,

or a salt thereof.

3. The compound according to claim 2 , wherein

R1 represents

a C1-C6 alkyl group optionally substituted with substituent A, or

a C1-C6 haloalkyl group;

R2 represents

a hydrogen atom,

a cyano group,

a halogen atom,

a C1-C6 alkyl group optionally substituted with substituent A,

a C2-C6 alkynyl group optionally substituted with substituent A, or

a C1-C6 alkoxy group optionally substituted with substituent A;

R3 and R4 are independent to each other, and each represents

a hydrogen atom,

a C1-C6 alkyl group optionally substituted with substituent C,

a C1-C6 haloalkyl group,

a C3-C8 cycloalkyl group optionally substituted with substituent C,

a C2-C6 alkenyl group optionally substituted with substituent C,

a C2-C6 alkynyl group optionally substituted with substituent C,

a phenyl group optionally substituted with 0 to 5 substituent D with the proviso that when there are two or more substituents D, they are independent to each other,

a C1-C6 alkyl group having a phenyl group optionally substituted with 0 to 5 substituent D with the proviso that when there are two or more substituents D, they are independent to each other,

an Rc-L- wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO or SO 2 , or

an ReC(═O)— wherein Re represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group, a C3-C8 cycloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C1-C6 alkoxy group, a C1-C6 haloalkoxy group, a C3-C8 cycloalkoxy group, a C2-C6 alkenyloxy group, a C2-C6 haloalkenyloxy group, a C3-C6 alkynyloxy group, a C3-C6 haloalkynyloxy group or an RaRbN— wherein Ra and Rb are independent to each other, and each represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb in combination 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, or R3 and R4 in combination with the nitrogen atom to which they are bonded form

a pyrrolidinyl group optionally substituted with substituent E,

a piperidinyl group optionally substituted with substituent E,

a morpholinyl group optionally substituted with substituent E, or

a C1-C6 alkylidene group optionally substituted with substituent F;

Y represents

a phenyl group optionally substituted with 0 to 5 R5 with the proviso that when there are two or more R5, they are independent to each other,

R5 represents

a hydroxyl group,

a cyano group,

a halogen atom,

a C1-C6 alkyl group optionally substituted with substituent G,

a C1-C6 alkoxy group optionally substituted with substituent G,

a C2-C6 alkenyloxy group optionally substituted with substituent G, or

a C3-C6 alkynyloxy group optionally substituted with substituent G,

or a salt thereof.

4. An agricultural and horticultural pest control agent comprising the compound of claim 1 or a salt thereof as an active ingredient.

5. An agricultural and horticultural fungicide comprising the compound of claim 1 or a salt thereof as an active ingredient.

6. A method for controlling plants diseases, which comprises applying the agricultural and horticultural pest control agent of claim 4 to a plant, a plant seed or a soil for growing a plant.

7. A method for controlling plants diseases, which comprises applying the agricultural and horticultural fungicides of claim 5 to a plant, a seed of a plant or a soil for growing a plant.

8. A compound represented by Formula (2)

wherein

R1 represents

a hydroxyl group,

a cyano group,

a C1-C6 alkyl group optionally substituted with substituent A,

a C1-C6 haloalkyl group,

a C3-C8 cycloalkyl group optionally substituted with substituent A,

a C2-C6 alkenyl group optionally substituted with substituent A,

a C2-C6 haloalkenyl group,

a C2-C6 alkynyl group optionally substituted with substituent A,

a C2-C6 haloalkynyl group,

a C1-C6 alkoxy group optionally substituted with substituent A,

a C1-C6 haloalkoxy group,

a C3-C8 cycloalkoxy group optionally substituted with substituent A,

a C2-C6 alkenyloxy group optionally substituted with substituent A,

a C2-C6 haloalkenyloxy group,

a C3-C6 alkynyloxy group optionally substituted with substituent A,

a C3-C6 haloalkynyloxy group, or

an RaRbN— wherein Ra and Rb are independent to each other, and each represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent B, a C1-C6 haloalkyl group or a C3-C8 cycloalkyl group, or Ra and Rb in combination 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 cyano group,

a nitro group,

a halogen atom,

a C1-C6 alkyl group optionally substituted with substituent A,

a C1-C6 haloalkyl group,

a C3-C8 cycloalkyl group optionally substituted with substituent A,

a C2-C6 alkenyl group optionally substituted with substituent A,

a C2-C6 haloalkenyl group,

a C2-C6 alkynyl group optionally substituted with substituent A,

a C2-C6 haloalkynyl group,

a C1-C6 alkoxy group optionally substituted with substituent A,

a C1-C6 haloalkoxy group,

a C3-C8 cycloalkoxy group optionally substituted with substituent A,

a C2-C6 alkenyloxy group optionally substituted with substituent A,

a C2-C6 haloalkenyloxy group,

a C3-C6 alkynyloxy group optionally substituted with substituent A,

a C3-C6 haloalkynyloxy group,

an Rc-L- wherein Rc represents a C1-C6 alkyl group or a C1-C6 haloalkyl group, and L represents S, SO or SO 2 ,

an RaRbN— wherein Ra and Rb are the same as defined above, or

an RdC(═O)— wherein Rd represents a hydrogen atom, a C1-C6 alkyl group optionally substituted with substituent 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 an RaRbN— wherein Ra and Rb are the same as defined above;

X represents an oxygen atom or a sulfur atom;

Y represents

a phenyl group optionally substituted with 0 to 5 R5 with the proviso that when there are two or more R5, they are independent to each other,

a pyridyl group optionally substituted with 0 to 4 R5 with the proviso that when there are two or more R5, they are independent to each other,

a pyridazinyl group optionally substituted with 0 to 3 R5 with the proviso that when there are two or more R5, they are independent to each other,

a pyrimidinyl group optionally substituted with 0 to 3 R5 with the proviso that when there are two or more R5, they are independent to each other,

a pyradinyl group optionally substituted with 0 to 3 R5 with the proviso that when there are two or more R5, they are independent to each other,

a triazinyl group optionally substituted with 0 to 2 R5 with the proviso that when there are two R5, they are independent to each other,

a tetrazinyl group optionally substituted with R5,

a thienyl group optionally substituted with 0 to 3 R5 with the proviso that when there are two or more R5, they are independent to each other,

a thiazolyl group optionally substituted with 0 to 2 R5 with the proviso that when there are two R5, they are independent to each other,

an isothiazolyl group optionally substituted with 0 to 2 R5 with the proviso that when there are two R5, they are independent to each other, or

a thiadiazolyl group optionally substituted with R5,

R5 represents

a hydroxyl group,

a cyano group,

a nitro group,

a halogen atom,

a C1-C6 alkyl group optionally substituted with substituent G,

a C1-C6 haloalkyl group,

a C3-C8 cycloalkyl group optionally substituted with substituent G,

a C2-C6 alkenyl group optionally substituted with substituent G,

a C2-C6 haloalkenyl group,

a C2-C6 alkynyl group optionally substituted with substituent G,

a C2-C6 haloalkynyl group,

a C1-C6 alkoxy group optionally substituted with substituent G,

a C1-C6 haloalkoxy group,

a C3-C8 cycloalkoxy group optionally substituted with substituent G,

a C2-C6 alkenyloxy group optionally substituted with substituent G,

a C2-C6 haloalkenyloxy group,

a C3-C6 alkynyloxy group optionally substituted with substituent G,

a C3-C6 haloalkynyloxy group,

an RdC(═O)— wherein Rd is the same as defined above,

an RdC(═O)O— wherein Rd is the same as defined above,

an Rc-L- wherein Rc and L are the same as defined above, or

an RaRbN— wherein Ra and Rb are the same as defined above,

the substituent A is at least one member 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, an RaRbN— wherein Ra and Rb are the same as defined above, and an Rc-L- wherein Rc and L are the same as defined above;

the substituent B is at least one member 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; and

the substituent G is at least one member 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, an RaRbN— wherein Ra and Rb are the same as defined above, an Rc-L- wherein Rc and L are the same as defined above, an RdC(═O)— wherein Rd is the same as defined above, an RdC(═O)O— wherein Rd is the same as defined above, and a group of a 3-6 membered ring containing 1-2 oxygen atoms,

or a salt thereof.

Assignments (2)
CHANGE OF NAME Recorded Feb 7, 2024
From: MITSUI CHEMICALS AGRO, INC.
To: MITSUI CHEMICALS CROP & LIFE SOLUTIONS, INC.
Reel/Frame 066508/0493 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 21, 2019
From: UMETANI, HIDEKI; IKISHIMA, HIDEAKI; TAKAGI, KOUJI; FUKUMOTO, TAKESHI; NAITO, RYOHEI; SHIRAKAWA, TOMOMI; KOISHIHARA, HIKARU; YAMANAKA, HISAKI; KAWASHIMA, MIYUKI; SAKURADA, AKANE
To: MITSUI CHEMICALS AGRO, INC.
Reel/Frame 051073/0350 →