IP Library › Granted Patent US 12,258,326
Granted Patent B2
US 12,258,326 · App. 18/608,090 · Granted Mar 25, 2025

Pyrazole derivative and harmful organism-controlling agent

Inventors: Ryo Ishikawa (Tokyo, JP); Akira Kinpara (Tokyo, JP); Keiji Toriyabe (Tokyo, JP); Akira Watanabe (Tokyo, JP); Masao Nakatani (Tokyo, JP); Akira Takanezawa (Tokyo, JP); Takeshi Matsuda (Tokyo, JP)
Assignee: KUMIAI CHEMICAL INDUSTRY CO., LTD.
C07D401/04A01N25/04A01N25/14A01N25/30A01N43/56
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,258,326
App. No.
18/608,090
Granted
Mar 25, 2025
Kind
B2
Abstract

Embodiments provide a pest control agent that is excellent in safety, controlling effect, residual activity, and so on. According to an embodiment, there is provided a pyrazole derivative represented by general formula [II] or an agriculturally acceptable salt thereof:

Claims (11)

1. A pyrazole derivative represented by general formula [II] or an agriculturally acceptable salt thereof

wherein,

p represents an integer of 0 or 1,

R 1 , R 2 , R 3 , R 4 , and R 5 each independently represent a hydrogen atom, halogen atom, C 1 -C 6 alkyl group, hydroxy group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 3 -C 6 cycloalkyl group, C 1 -C 6 alkylthio group, C 1 -C 6 alkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, amino group, mono(C 1 -C 6 alkyl)amino group, di(C 1 -C 6 alkyl)amino group, cyano group, or nitro group,

R 16 represents a hydrogen atom or C 1 -C 6 alkyl group,

Q′ represents a halogen atom, C 1 -C 6 alkylsulfonyloxy group, C 1 -C 6 haloalkylsulfonyloxy group, di(C 1 -C 6 alkyl)sulfamoyloxy group, phenylsulfonyloxy group that is unsubstituted or substituted with (R 9 ) n , C 6 -C 10 aryl group that is unsubstituted or substituted with (R 8 ) m , or heteroaryl group that is unsubstituted or substituted with (R 8 ) m ,

R 8 represents a hydrogen atom, halogen atom, hydroxy group, thiol group, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 3 -C 6 cycloalkyl group, C 3 -C 6 cycloalkyl C 1 -C 6 alkyl group, C 3 -C 6 cycloalkyl C 2 -C 6 alkynyl group, C 3 -C 6 halocycloalkyl group, C 3 -C 6 halocycloalkyl C 1 -C 6 alkyl group, C 2 -C 6 alkenyl group, C 2 -C 6 haloalkenyl group, C 2 -C 7 alkynyl group, C 2 -C 6 haloalkynyl group, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 3 -C 6 cycloalkoxy group, oxirane-2-yl group, mono(oxirane-2-yl)C 1 -C 3 alkyl group, C 3 -C 6 halocycloalkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 alkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, C 3 -C 6 cycloalkylthio group, C 3 -C 6 cycloalkylsulfinyl group, C 3 -C 6 cycloalkylsulfonyl group, C 1 -C 6 haloalkylthio group, C 1 -C 6 haloalkylsulfinyl group, C 1 -C 6 haloalkylsulfonyl group, formyl group, C 1 -C 6 alkylcarbonyl group, C 1 -C 6 haloalkylcarbonyl group, C 1 -C 6 alkoxycarbonyl group, aminocarbonyl group, mono(C 1 -C 6 alkyl)aminocarbonyl group, di(C 1 -C 6 alkyl)aminocarbonyl group, amino C 1 -C 6 alkyl group, mono(C 1 -C 6 alkyl)amino C 1 -C 6 alkyl group, di(C 1 -C 6 alkyl)amino C 1 -C 6 alkyl group, tri(C 1 -C 6 alkyl)silyloxy C 1 -C 6 alkyl group, C 1 -C 6 alkylcarbonyl C 1 -C 6 alkyl group, C 1 -C 6 alkylcarbonyloxy C 1 -C 6 alkyl group, C 1 -C 6 haloalkylcarbonyl C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl group, hydroxy C 1 -C 6 alkyl group, C 1 -C 6 alkoxy C 1 -C 6 alkyl group, C 1 -C 6 haloalkoxy C 1 -C 6 alkyl group, C 1 -C 6 alkoxy C 1 -C 6 haloalkyl group, C 1 -C 6 haloalkoxy C 1 -C 6 haloalkyl group, formyloxy group, C 1 -C 6 alkylcarbonyloxy group, C 1 -C 6 haloalkylcarbonyloxy group, aminocarbonyloxy group, mono(C 1 -C 6 alkyl)aminocarbonyloxy group, di(C 1 -C 6 alkyl)aminocarbonyloxy group, aminocarbonyloxy C 1 -C 6 alkyl group, mono(C 1 -C 6 alkyl)aminocarbonyloxy C 1 -C 6 alkyl group, di(C 1 -C 6 alkyl)aminocarbonyloxy C 1 -C 6 alkyl group, C 1 -C 6 alkoxycarbonyloxy group, C 1 -C 6 alkoxycarbonyloxy C 1 -C 6 alkyl group, C 1 -C 6 alkylsulfonyloxy group, C 1 -C 6 haloalkylsulfonyloxy group, C 1 -C 6 alkylthio C 1 -C 6 alkyl group, C 1 -C 6 alkylsulfinyl C 1 -C 6 alkyl group, C 1 -C 6 alkylsulfonyl C 1 -C 6 alkyl group, C 1 -C 6 haloalkylthio C 1 -C 6 alkyl group, C 1 -C 6 haloalkylsulfinyl C 1 -C 6 alkyl group, C 1 -C 6 haloalkylsulfonyl C 1 -C 6 alkyl group, C 3 -C 6 cycloalkyl C 1 -C 6 alkoxy group, C 3 -C 6 halocycloalkyl C 1 -C 6 alkoxy group, C 3 -C 6 cycloalkyl C 1 -C 6 alkylthio group, C 3 -C 6 cycloalkyl C 1 -C 6 alkylsulfinyl group, C 3 -C 6 cycloalkyl C 1 -C 6 alkylsulfonyl group, C 3 -C 6 halocycloalkyl C 1 -C 6 alkylthio group, C 3 -C 6 halocycloalkyl C 1 -C 6 alkylsulfinyl group, C 3 -C 6 halocycloalkyl C 1 -C 6 alkylsulfonyl group, phenyl group that is unsubstituted or substituted with (R 9 ) n , phenoxy group that is unsubstituted or substituted with (R 9 ) n , benzyl group that is unsubstituted or substituted with (R 9 ) n , benzyloxy group that is unsubstituted or substituted with (R 9 ) n , amino group, mono(C 1 -C 6 alkyl)amino group, di(C 1 -C 6 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 R 8 s may form, together with a carbon atom bound to each R 8 , 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, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, or oxo group,

R 9 represents a halogen atom, C 1 -C 6 alkyl group, C 1 -C 6 haloalkyl group, C 1 -C 6 alkoxy group, C 1 -C 6 haloalkoxy group, C 1 -C 6 alkylthio group, C 1 -C 6 alkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, C 1 -C 6 haloalkylthio group, C 1 -C 6 haloalkylsulfinyl group, C 1 -C 6 haloalkylsulfonyl group, amino group, mono(C 1 -C 6 alkyl)amino group, di(C 1 -C 6 alkyl)amino group, cyano group, or nitro group,

m represents a number of chemically acceptable R 8 s and is an integer of 0 to 7,

R 8 s may be the same or different from each other when m is 2 or more,

n represents a number of chemically acceptable R 9 s and is an integer of 0 to 5, and R 9 s may be the same or different from each other when n is 2 or more.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 18, 2024
From: ISHIKAWA, RYO; KINPARA, AKIRA; TORIYABE, KEIJI; WATANABE, AKIRA; NAKATANI, MASAO; TAKANEZAWA, AKIRA; MATSUDA, TAKESHI
To: KUMIAI CHEMICAL INDUSTRY CO., LTD.
Reel/Frame 066815/0018 →
Priority Claims (2)
JP 2018-102614 · May 29, 2018 · national
JP 2019-045383 · Mar 13, 2019 · national
Continuity (2)
Division 17250107
Related Publication 20240254102A1 · Aug 1, 2024
References Cited (13)
JP 2010514710A · 2010 [cited by applicant]
JP 2013082699A · 2013 [cited by applicant]
JP 2014015447A · 2014 [cited by applicant]
JP 2014504267A · 2014 [cited by applicant]
RU 2343151C2 · 2009 [cited by applicant]
WO 2004067528A1 · 2004 [cited by applicant]
WO 2012102387A1 · 2012 [cited by applicant]
WO 2018207847A1 · 2018 [cited by applicant]
Database Registry, Chemical Abstracts Service, Columbus, Ohio, US, Oct. 23, 2016, “1H-Pyrazole-3-carboxylic acid compounds”, 5 pgs, XP055871183. [cited by applicant]
EP19811742.6 Extended European Search Report dated Dec. 20, 2021, 8 pgs. [cited by applicant]
Jaisankar, et al., Synthesis of Novel Heterocyclic Pyrazole-3-carboxamides using Nitrilimines, International Journal of ChemTech Research, vol. 5, Jan. 1, 2013, pp. 80-84, XP055662607. [cited by applicant]
PCT/JP2019/020656 International Search Report dated Aug. 13, 2019; 4 pgs. [cited by applicant]
RU2020142980 Office Action dated Sep. 2, 2022, 24 pgs. [cited by applicant]