US 12,082,581 B2
Acrylate derivative, use and production intermediate compound of the same
Hiroto Tamashima, Takarazuka (JP)
Assigned to SUMITOMO CHEMICAL COMPANY, LIMITED, Chuo-ku (JP)
Appl. No. 17/623,129
Filed by SUMITOMO CHEMICAL COMPANY, LIMITED, Chuo-ku (JP)
PCT Filed Jun. 26, 2020, PCT No. PCT/JP2020/025341
§ 371(c)(1), (2) Date Dec. 27, 2021,
PCT Pub. No. WO2020/262648, PCT Pub. Date Dec. 30, 2020.
Claims priority of application No. 2019-120901 (JP), filed on Jun. 28, 2019; and application No. 2020-015184 (JP), filed on Jan. 31, 2020.
Prior Publication US 2022/0256844 A1, Aug. 18, 2022
Int. Cl. A01N 37/38 (2006.01); A01N 37/36 (2006.01); A01N 37/50 (2006.01); A01N 43/08 (2006.01); A01N 43/10 (2006.01); A01N 43/20 (2006.01); A01N 43/40 (2006.01); A01N 43/60 (2006.01); A01N 43/78 (2006.01); A01N 43/80 (2006.01); A01N 47/10 (2006.01); A01N 47/16 (2006.01); A01N 47/22 (2006.01); A01N 55/00 (2006.01); A01N 55/08 (2006.01); A61P 1/00 (2006.01); A61P 3/00 (2006.01); A61P 7/00 (2006.01); C07C 69/712 (2006.01); C07C 69/734 (2006.01); C07C 69/736 (2006.01); C07C 251/40 (2006.01); C07C 255/54 (2006.01); C07C 271/40 (2006.01); C07C 271/44 (2006.01); C07C 271/56 (2006.01); C07C 271/58 (2006.01); C07C 307/02 (2006.01); C07C 309/65 (2006.01); C07C 309/66 (2006.01); C07C 309/73 (2006.01); C07C 333/04 (2006.01); C07D 207/08 (2006.01); C07D 213/30 (2006.01); C07D 213/61 (2006.01); C07D 241/16 (2006.01); C07D 261/18 (2006.01); C07D 277/24 (2006.01); C07D 295/088 (2006.01); C07D 295/205 (2006.01); C07D 303/23 (2006.01); C07D 307/12 (2006.01); C07D 307/42 (2006.01); C07D 333/16 (2006.01); C07F 7/08 (2006.01)
CPC A01N 37/38 (2013.01) [A01N 37/50 (2013.01); A01N 43/08 (2013.01); A01N 43/10 (2013.01); A01N 43/20 (2013.01); A01N 43/40 (2013.01); A01N 43/60 (2013.01); A01N 43/78 (2013.01); A01N 43/80 (2013.01); A01N 55/00 (2013.01); C07C 69/736 (2013.01); C07C 251/40 (2013.01); C07D 213/61 (2013.01); C07D 241/16 (2013.01); C07D 261/18 (2013.01); C07D 277/24 (2013.01); C07D 295/088 (2013.01); C07D 303/23 (2013.01); C07D 307/12 (2013.01); C07D 333/16 (2013.01); C07F 7/081 (2013.01)] 11 Claims
 
1. A compound of the formula (I), an N-oxide thereof, an agriculturally acceptable salt of the compound, or an agriculturally acceptable salt of the N-oxide:

OG Complex Work Unit Chemistry
wherein L represents an oxygen atom or CH2,
E represents a methyl group which is substituted with one or more substituents selected from Group A, a C2-C10 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, R6C(O)—, R4OC(O)—, R3R5NC(O)—, R3R5NC(S)—, R4S(O)2—, or R3R5NS(O)2—,
R1 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom,
n is 0, 1, 2 or 3,
when n is 2 or 3, a plurality of R2 are identical to or different from each other,
R2 represents a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a cyclopropyl group, or a halogen atom,
R3 represents a hydrogen atom, a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, or a five- to ten-membered aromatic heterocyclic group, wherein the C6-C10 aryl group, and the five- to ten-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C,
R4 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, or a five- to ten-membered aromatic heterocyclic group, wherein the C6-C10 aryl group, and the five- to ten-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C,
R5 represents a hydrogen atom, a C1-C3 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, or a C1-C3 alkoxy group which may be optionally substituted with one or more halogen atoms,
R6 represents a hydrogen atom, a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C6-C10 aryl group, or a five- to ten-membered aromatic heterocyclic group, wherein the C6-C10 aryl group, and the five- to ten-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C,
R3 and R5 may be combined together with the nitrogen atom to which they are attached to form a four- to seven-membered non-aromatic heterocyclic group, wherein the four- to seven-membered non-aromatic heterocyclic group may have optionally one or more substituents selected from Group B,
Group A: a group consisting of OR11, S(O)mR13, OS(O)2R13, C(O)R11, C(O)OR11, OC(O)R11, OC(O)OR11, OC(O)NR11R12, NR11C(O)NR12R13, NR11R12, C(O)NR11R12, S(O)2NR11R12, NR12C(O)R11, NR12C(O)OR13, NR12S(O)2R13, C(R12)═N—OR11, O—N═CR11R13, SiR14R15R16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group, wherein the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group E, a halogen atom, a cyano group, and a nitro group,
R11 and R12 are identical to or different from each other, and each represents a hydrogen atom, a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group E, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, or a three- to eight-membered non-aromatic heterocyclic group, wherein the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F,
R13 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group E, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, or a three- to eight-membered non-aromatic heterocyclic group, wherein the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F,
R14, R15 and R16 are identical to or different from each other, and each represents a C1-C6 chain hydrocarbon group or a phenyl group,
m is 0, 1 or 2,
Group B: a group consisting of a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, OR11, S(O)mR13, OS(O)2R13,C(O)R11, C(O)OR11, OC(O)R11, OC(O)OR11, OC(O)NR11R12, NR11C(O)NR12R13, NR11R12, C(O)NR11R12, S(O)2NR11R12, NR12C(O)R11, NR12C(O)OR13, NR12S(O)2R13, C(R12)═N—OR11, O—N═CR11R13, SiR14R15R16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group, wherein the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group E, an oxo group, a thioxo group, a halogen atom, a cyano group, and a nitro group,
Group C: a group consisting of a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group D, OR11, S(O)mR13, OS(O)2R13, C(O)R11, C(O)OR11, OC(O)R11, OC(O)OR11, OC(O)NR11R12, NR11C(O)NR12R13, NR11R12, C(O)NR11R12, S(O)2NR11R12, NR12C(O)R11, NR12C(O)OR13, NR12S(O)2R13, C(R12)═N—OR11, O—N═CR11R13, SiR14R15R16, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, a three- to eight-membered non-aromatic heterocyclic group, wherein the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group E, a halogen atom, a cyano group, and a nitro group,
Group D: a group consisting of a C3-C6 cycloalkyl group, wherein the C3-C6 cycloalkyl group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group, OR17, S(O)mR19, OS(O)2R19, C(O)R17, C(O)OR17, OC(O)R17, OC(O)OR17, OC(O)NR17R18, NR17C(O)NR18R19, NR17R18, C(O)NR17R18, S(O)2NR17R18, NR18C(O)R17, NR18C(O)OR19, NR18S(O)2R19, C(R18)═N—OR17, O—N═CR17R19, SiR14R15R16, a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group and a three- to eight-membered non-aromatic heterocyclic group, wherein the phenoxy group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F,
R17 and R18 are identical to or different from each other, and each represents a hydrogen atom, a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, or a three- to eight-membered non-aromatic heterocyclic group, wherein the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group,
R19 represents a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, or a three- to eight-membered non-aromatic heterocyclic group, wherein the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group, and a C1-C3 alkoxy group,
Group E: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, wherein the C1-C6 chain hydrocarbon group, and the C3-C6 cycloalkyl group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom, a cyano group and a C1-C3 alkoxy group, OR17, S(O)mR19, OS(O)2R19, C(O)R17, C(O)OR17, OC(O)R17, OC(O)OR17, OC(O)NR17R18, NR17C(O)NR18R19, NR17R18, C(O)NR17R18, S(O)2NR17R18, NR18C(O)R17, NR18C(O)OR19, NR18S(O)2R19, C(R18)═N—OR17, O—N═CR17R19, SiR14R15R16, a halogen atom, a cyano group, a nitro group, a hydroxy group, a phenoxy group, a phenyl group, a naphthyl group, a five- to six-membered aromatic heterocyclic group, and a three- to eight-membered non-aromatic heterocyclic group, wherein the phenoxy group, the phenyl group, the naphthyl group, the five- to six-membered aromatic heterocyclic group, and the three- to eight-membered non-aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F,
Group F: a group consisting of a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C6 alkoxy group, and a C1-C6 alkylthio group, wherein the C1-C6 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C6 alkoxy group, and the C1-C6 alkylthio group may be optionally substituted with one or more substituents selected from a group consisting of a halogen atom and a cyano group, a halogen atom, a cyano group, a nitro group, and a hydroxy group.