IP Library Granted Patent US 12,516,062
Granted Patent B2
US 12,516,062 · App. 17/641,249 · Granted Jan 6, 2026

Agricultural or horticultural insecticide or animal ectoparasite or endoparasite control agent each comprising an imidazopyridazine compound having a substituted cyclopropane-oxadiazole group or a salt thereof as active ingredient, and method for using the insecticide or the control agent

Inventors: Chiaki Yamauchi (Osaka, JP); Ikki Yonemura (Osaka, JP)
Assignee: NIHON NOHYAKU CO., LTD.
C07D487/04A01N43/90A01P7/00A61P33/10A61K9/0053
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Quick Facts
Patent No.
US 12,516,062
App. No.
17/641,249
Granted
Jan 6, 2026
Kind
B2
Abstract

In crop production in the fields of agriculture, horticulture and the like, the damage caused by insect pests etc. is still immense, and insect pests resistant to existing insecticides have emerged. The present invention has been made in view of such circumstances, and an object of the present invention is to develop and provide a novel agricultural or horticultural insecticide. Another object of the present invention is to provide an agent capable of eliminating ectoparasites or endoparasites of animals. These objects are achieved by an imidazopyridazine compound having a substituted cyclopropane-oxadiazole group represented by the general formula (1): [Chem. 1] (wherein R 1 preferably represents an alkyl group, R 2a and R 2b each represent a hydrogen atom, and R 3 represents a haloalkyl group) or a salt thereof, an agricultural or horticultural insecticide or an animal ectoparasite or endoparasite control agent each comprising the compound or the salt thereof as an active ingredient, and a method for using the compound or the salt thereof, the insecticide, or the control agent.

Claims (8)

1 . An imidazopyridazine compound having a substituted cyclopropane-oxadiazole group represented by formula (1):

wherein R 1 , R 2a , and R 2b may be the same or different and each represent (a1) a hydrogen atom; (a2) a cyano group; (a3) a (C 1 -C 6 ) alkyl group; (a4) a halo (C 1 -C 6 ) alkyl group; or (a5) a phenyl group, except for a case where R 1 , R 2a , and R 2b are all hydrogen atoms, and R 3 represents (b1) a halo (C 1 -C 6 ) alkyl group; (b2) a halo (C 1 -C 6 ) alkoxy group; (b3) a halo (C 1 -C 6 ) alkylthio group; (b4) a halo (C 1 -C 6 ) alkylsulfinyl group; or (b5) a halo (C 1 -C 6 ) alkylsulfonyl group, or a salt thereof.

2 . The imidazopyridazine compound having a substituted cyclopropane-oxadiazole group or the salt thereof according to claim 1 , wherein R 1 is (a3) a (C 1 -C 6 ) alkyl group; (a4) a halo (C 1 -C 6 ) alkyl group; or (a5) a phenyl group, R 2a and R 2b are (a1) hydrogen atoms, and R 3 is (b1) a halo (C 1 -C 6 ) alkyl group.

3 . The imidazopyridazine compound having a substituted cyclopropane-oxadiazole group or the salt thereof according to claim 1 , wherein R 1 and R 2a are (a1) hydrogen atoms, R 2b is (a3) a (C 1 -C 6 ) alkyl group, and R 3 is (b1) a halo (C 1 -C 6 ) alkyl group.

4 . An agricultural or horticultural insecticide comprising the imidazopyridazine compound having a substituted cyclopropane-oxadiazole group or the salt thereof according to claim 1 as an active ingredient, and optionally one or more additives.

5 . A method for using an agricultural or horticultural insecticide, comprising treating plants or soil with an effective amount of the imidazopyridazine compound having a substituted cyclopropane-oxadiazole group or the salt thereof according to claim 1 .

6 . An animal ectoparasite or endoparasite control agent comprising the imidazopyridazine compound having a substituted cyclopropane-oxadiazole group or the salt thereof according to claim 1 as an active ingredient, and optionally one or more additives.

7 . A method for using an animal ectoparasite or endoparasite control agent, comprising transdermally applying or orally administering an effective amount of the imidazopyridazine compound having a substituted cyclopropane-oxadiazole group or the salt thereof according to claim 1 to an animal.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 8, 2022
From: YAMAUCHI, CHIAKI; YONEMURA, IKKI
To: NIHON NOHYAKU CO., LTD.
Reel/Frame 059197/0430 →
Priority Claims (1)
JP 2019-165793 · Sep 12, 2019 · national
Continuity (1)
Related Publication 20220340578A1 · Oct 27, 2022
References Cited (56)
US 5254799A · De Greve et al. · 1993 [cited by applicant]
US 5317096A · De Greve et al. · 1994 [cited by applicant]
US 5407454A · Cavalieri et al. · 1995 [cited by applicant]
US 5438066A · Matthews · 1995 [cited by examiner]
US 5530195A · Kramer et al. · 1996 [cited by applicant]
US 5545565A · De Greve et al. · 1996 [cited by applicant]
US 5625136A · Koziel et al. · 1997 [cited by applicant]
US 5760181A · De Greve et al. · 1998 [cited by applicant]
US 5767372A · De Greve et al. · 1998 [cited by applicant]
US 5843898A · De Greve et al. · 1998 [cited by applicant]
US 5859336A · Koziel et al. · 1999 [cited by applicant]
US 6018104A · Koziel et al. · 2000 [cited by applicant]
US 6051760A · Koziel et al. · 2000 [cited by applicant]
US 6075185A · Koziel et al. · 2000 [cited by applicant]
US 6107546A · De Greve et al. · 2000 [cited by applicant]
US 6121014A · Koziel et al. · 2000 [cited by applicant]
US 6320100B1 · Koziel et al. · 2001 [cited by applicant]
US 6403865B1 · Koziel et al. · 2002 [cited by applicant]
US 6689356B1 · Zlotkin et al. · 2004 [cited by applicant]
US 6720488B2 · Koziel et al. · 2004 [cited by applicant]
US 8273741B2 · Sakai et al. · 2012 [cited by applicant]
US 10544148B2 · Edmunds et al. · 2020 [cited by applicant]
US 11089783B2 · Mosrin et al. · 2021 [cited by applicant]
US 20030046726A1 · Koziel et al. · 2003 [cited by applicant]
US 20030237117A1 · Koziel et al. · 2003 [cited by applicant]
US 20060021095A1 · Koziel et al. · 2006 [cited by applicant]
US 20060117407A1 · Koziel et al. · 2006 [cited by applicant]
US 20160021886A1 · Yonemura et al. · 2016 [cited by applicant]
US 20170240554A1 · Edmunds et al. · 2017 [cited by applicant]
US 20200146293A1 · Mosrin et al. · 2020 [cited by applicant]
US 20200361940A1 · Yamauchi et al. · 2020 [cited by applicant]
US 20210371424A1 · Sano et al. · 2021 [cited by applicant]
US 20220361499A1 · Yamauchi et al. · 2022 [cited by applicant]
CN 106795167 · 2017 [cited by applicant]
EP 0374753 · 1990 [cited by applicant]
EP 0427529 · 1991 [cited by applicant]
EP 0451878 · 1991 [cited by applicant]
JP 201919116 · 2019 [cited by applicant]
WO 9307278 · 1993 [cited by applicant]
WO 9534656 · 1995 [cited by applicant]
WO 03052073 · 2003 [cited by applicant]
WO 2012086848 · 2012 [cited by applicant]
WO 2014142292 · 2014 [cited by applicant]
WO 2016104746 · 2016 [cited by applicant]
WO 2017065183 · 2017 [cited by applicant]
WO 2017146221 · 2017 [cited by applicant]
WO 2018202494 · 2018 [cited by applicant]
First Examination Report issued Aug. 22, 2022 in corresponding Indian Patent Application No. 202227012228, with English language translation. [cited by applicant]
International Preliminary Report on Patentability issued Mar. 15, 2022 in International (PCT) Application No. PCT/JP2020/034388. [cited by applicant]
Search Report issued Sep. 21, 2022 in Russian Patent Application No. 2022106134, with English-language translation. [cited by applicant]
Office Action issued Sep. 23, 2022 in Russian Patent Application No. 2022106134, with English-language translation. [cited by applicant]
Office Action issued Apr. 18, 2023 in corresponding Japanese Patent Application No. 2021-545605, with English language translation. [cited by applicant]
International Search Report (ISR) issued Nov. 10, 2020 in International (PCT) Application No. PCT/JP2020/034388. [cited by applicant]
William B. Parker et al., “Dominant mutations causing alterations in acetyl-coenzyme A carboxylase confer tolerance to cyclohexanedione and aryloxyphenoxypropionate herbicides in maize”, Proc. Natl. Acad. Sci., vol. 87,… [cited by applicant]
“Weed resistance to acetyl coenzyme A carboxylase inhibitors: an update”, Weed Science, vol. 53, Issue 5, pp. 728-746, Oct. 2005. [cited by applicant]
T. Gura, “Repairing the Genome's Spelling Mistakes”, Science, 285, pp. 316-318, 1999. [cited by applicant]