US 12,258,326 B2
Pyrazole derivative and harmful organism-controlling agent
Ryo Ishikawa, Tokyo (JP); Akira Kinpara, Tokyo (JP); Keiji Toriyabe, Tokyo (JP); Akira Watanabe, Tokyo (JP); Masao Nakatani, Tokyo (JP); Akira Takanezawa, Tokyo (JP); and Takeshi Matsuda, Tokyo (JP)
Assigned to KUMIAI CHEMICAL INDUSTRY CO., LTD., (JP)
Filed by KUMIAI CHEMICAL INDUSTRY CO., LTD., Tokyo (JP)
Filed on Mar. 18, 2024, as Appl. No. 18/608,090.
Application 18/608,090 is a division of application No. 17/250,107, granted, now 11,964,957, previously published as PCT/JP2019/020656, filed on May 24, 2019.
Claims priority of application No. 2018-102614 (JP), filed on May 29, 2018; and application No. 2019-045383 (JP), filed on Mar. 13, 2019.
Prior Publication US 2024/0254102 A1, Aug. 1, 2024
Int. Cl. C07D 401/04 (2006.01); A01N 25/04 (2006.01); A01N 25/14 (2006.01); A01N 25/30 (2006.01); A01N 43/56 (2006.01)
CPC C07D 401/04 (2013.01) [A01N 25/04 (2013.01); A01N 25/14 (2013.01); A01N 25/30 (2013.01); A01N 43/56 (2013.01)] 1 Claim
 
1. A pyrazole derivative represented by general formula [II] or an agriculturally acceptable salt thereof

OG Complex Work Unit Chemistry
wherein,
p represents an integer of 0 or 1,
R1, R2, R3, R4, and R5 each independently represent a hydrogen atom, halogen atom, C1-C6 alkyl group, hydroxy group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C6 cycloalkyl group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, amino group, mono(C1-C6 alkyl)amino group, di(C1-C6 alkyl)amino group, cyano group, or nitro group,
R16 represents a hydrogen atom or C1-C6 alkyl group,
Q′ represents a halogen atom, C1-C6 alkylsulfonyloxy group, C1-C6 haloalkylsulfonyloxy group, di(C1-C6 alkyl)sulfamoyloxy group, phenylsulfonyloxy group that is unsubstituted or substituted with (R9)n, C6-C10 aryl group that is unsubstituted or substituted with (R8)m, or heteroaryl group that is unsubstituted or substituted with (R8)m,
R8 represents a hydrogen atom, halogen atom, hydroxy group, thiol group, C1-C6 alkyl group, C1-C6 haloalkyl group, C3-C6 cycloalkyl group, C3-C6 cycloalkyl C1-C6 alkyl group, C3-C6 cycloalkyl C2-C6 alkynyl group, C3-C6 halocycloalkyl group, C3-C6 halocycloalkyl C1-C6 alkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2-C7 alkynyl group, C2-C6 haloalkynyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C3-C6 cycloalkoxy group, oxirane-2-yl group, mono(oxirane-2-yl)C1-C3 alkyl group, C3-C6 halocycloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C3-C6 cycloalkylthio group, C3-C6 cycloalkylsulfinyl group, C3-C6 cycloalkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, formyl group, C1-C6 alkylcarbonyl group, C1-C6 haloalkylcarbonyl group, C1-C6 alkoxycarbonyl group, aminocarbonyl group, mono(C1-C6 alkyl)aminocarbonyl group, di(C1-C6 alkyl)aminocarbonyl group, amino C1-C6 alkyl group, mono(C1-C6 alkyl)amino C1-C6 alkyl group, di(C1-C6 alkyl)amino C1-C6 alkyl group, tri(C1-C6 alkyl)silyloxy C1-C6 alkyl group, C1-C6 alkylcarbonyl C1-C6 alkyl group, C1-C6 alkylcarbonyloxy C1-C6 alkyl group, C1-C6 haloalkylcarbonyl C1-C6 alkyl group, C1-C6 alkoxycarbonyl C1-C6 alkyl group, hydroxy C1-C6 alkyl group, C1-C6 alkoxy C1-C6 alkyl group, C1-C6 haloalkoxy C1-C6 alkyl group, C1-C6 alkoxy C1-C6 haloalkyl group, C1-C6 haloalkoxy C1-C6 haloalkyl group, formyloxy group, C1-C6 alkylcarbonyloxy group, C1-C6 haloalkylcarbonyloxy group, aminocarbonyloxy group, mono(C1-C6 alkyl)aminocarbonyloxy group, di(C1-C6 alkyl)aminocarbonyloxy group, aminocarbonyloxy C1-C6 alkyl group, mono(C1-C6 alkyl)aminocarbonyloxy C1-C6 alkyl group, di(C1-C6 alkyl)aminocarbonyloxy C1-C6 alkyl group, C1-C6 alkoxycarbonyloxy group, C1-C6 alkoxycarbonyloxy C1-C6 alkyl group, C1-C6 alkylsulfonyloxy group, C1-C6 haloalkylsulfonyloxy group, C1-C6 alkylthio C1-C6 alkyl group, C1-C6 alkylsulfinyl C1-C6 alkyl group, C1-C6 alkylsulfonyl C1-C6 alkyl group, C1-C6 haloalkylthio C1-C6 alkyl group, C1-C6 haloalkylsulfinyl C1-C6 alkyl group, C1-C6 haloalkylsulfonyl C1-C6 alkyl group, C3-C6 cycloalkyl C1-C6 alkoxy group, C3-C6 halocycloalkyl C1-C6 alkoxy group, C3-C6 cycloalkyl C1-C6 alkylthio group, C3-C6 cycloalkyl C1-C6 alkylsulfinyl group, C3-C6 cycloalkyl C1-C6 alkylsulfonyl group, C3-C6 halocycloalkyl C1-C6 alkylthio group, C3-C6 halocycloalkyl C1-C6 alkylsulfinyl group, C3-C6 halocycloalkyl C1-C6 alkylsulfonyl group, phenyl group that is unsubstituted or substituted with (R9)n, phenoxy group that is unsubstituted or substituted with (R9)n, benzyl group that is unsubstituted or substituted with (R9)n, benzyloxy group that is unsubstituted or substituted with (R9)n, amino group, mono(C1-C6 alkyl)amino group, di(C1-C6 alkyl)amino group, carboxy group, 1,3-dioxolane-2-yl group, 1,3-dioxane-2-yl group, 1H-imidazole-2-yl group, thiazole-2-yl group, oxazole-2-yl group, (hydroxyimino)methyl group, (methyloxyimino)methyl group, isoxazole-3-yl, 4,5-dihydro-3-isoxazolyl group, cyano group, or nitro group, and further, neighboring two R8s may form, together with a carbon atom bound to each R8, a 4 to 8-membered carbon ring, or a 4 to 8-membered hetero ring having 1 to 4 hetero atoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom, the carbon ring or hetero ring formed at this time may be substituted with one or more chemically acceptable substituents selected from a halogen atom, cyano group, nitro group, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, or oxo group,
R9 represents a halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 alkylsulfinyl group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylthio group, C1-C6 haloalkylsulfinyl group, C1-C6 haloalkylsulfonyl group, amino group, mono(C1-C6 alkyl)amino group, di(C1-C6 alkyl)amino group, cyano group, or nitro group,
m represents a number of chemically acceptable R8s and is an integer of 0 to 7,
R8s may be the same or different from each other when m is 2 or more,
n represents a number of chemically acceptable R9s and is an integer of 0 to 5, and R9s may be the same or different from each other when n is 2 or more.