US 12,010,995 B2
Oxadiazoline compounds or salts thereof, agrohorticultural fungicides containing the compounds, and methods of using the same
Naoya Fujita, Osaka (JP); Masao Yamashita, Osaka (JP); Ryusuke Kishigami, Osaka (JP); and Hiroko Satoh, Osaka (JP)
Assigned to NIHON NOHYAKU CO., LTD., Tokyo (JP)
Appl. No. 17/252,455
Filed by NIHON NOHYAKU CO., LTD., Tokyo (JP)
PCT Filed Aug. 6, 2019, PCT No. PCT/JP2019/030999
§ 371(c)(1), (2) Date Dec. 15, 2020,
PCT Pub. No. WO2020/032071, PCT Pub. Date Feb. 13, 2020.
Claims priority of application No. 2018-149473 (JP), filed on Aug. 8, 2018; and application No. 2019-083568 (JP), filed on Apr. 25, 2019.
Prior Publication US 2023/0121730 A1, Apr. 20, 2023
Int. Cl. C07D 271/06 (2006.01); A01N 25/04 (2006.01); A01N 25/14 (2006.01); A01N 43/82 (2006.01); A01N 43/90 (2006.01); A01P 3/00 (2006.01); C07D 413/10 (2006.01); C07D 413/12 (2006.01); C07D 417/10 (2006.01); C07D 417/12 (2006.01); C07D 471/04 (2006.01); C07D 487/04 (2006.01); C07D 495/04 (2006.01)
CPC A01N 43/82 (2013.01) [A01N 25/04 (2013.01); A01N 25/14 (2013.01); A01N 43/90 (2013.01); A01P 3/00 (2021.08); C07D 271/06 (2013.01); C07D 413/10 (2013.01); C07D 413/12 (2013.01); C07D 417/10 (2013.01); C07D 417/12 (2013.01); C07D 471/04 (2013.01); C07D 487/04 (2013.01); C07D 495/04 (2013.01)] 4 Claims
 
1. A compound represented by the general formula (I) or salts thereof:

OG Complex Work Unit Chemistry
wherein:
A is a single bond or the following structure A1, A2, A3, A4, A5, A6, or A7:

OG Complex Work Unit Chemistry
B is a single bond, an oxygen atom, C(R1)(R2), or a carbonyl group;
Y is a single bond, an oxygen atom, C(R1)(R2), or N(R3);
R1 and R2 are each independently:
(a1) a hydrogen atom;
(a2) a halogen atom;
(a3) a (C1-C6)alkyl group;
(a4) a (C1-C6)alkoxy group; or
(a5) a halo(C1-C6)alkyl group; or
R1 and R2 form a cyclopropyl group with a carbon atom to which they bond;
R3 is:
(b1) a hydrogen atom;
(b2) a (C1-C6)alkyl group;
(b3) a (C1-C6)alkoxy group;
(b4) a (C3-C6)cycloalkyl group;
(b5) a (C1-C6)alkylcarbonyl group;
(b6) a (C1-C6)alkoxycarbonyl group;
(b7) a (C2-C6)alkenyl group;
(b8) a (C2-C6)alkynyl group; or
(b9) a (C3-C6)cycloalkyl(C1-C6) alkyl group;
Q is:
(c1) a hydrogen atom;
(c2) a (C1-C6)alkyl group;
(c3) a (C2-C6)alkenyl group;
(c4) a (C2-C6)alkynyl group;
(c5) a (C3-C6)cycloalkyl group;
(c6) a (C1-C6)alkoxy group;
(c7) a halo(C1-C6)alkyl group;
(c8) a halo(C2-C6)alkenyl group;
(c9) a halo(C2-C6)alkynyl group;
(c10) a halo(C3-C8)cycloalkyl group;
(c11) a halo(C1-C6)alkoxy group;
(c12) an Ra(Rb)N group, wherein Ra and Rb are each independently a hydrogen atom, a (C1-C6)alkyl group, a (C2-C6)alkenyl group, a (C2-C6)alkynyl group, a (C3-C6)cycloalkyl group, a (C1-C6)alkoxy group, a halo(C1-C6)alkyl group, a (C3-C6)cycloalkyl(C1-C6)alkyl group, a phenyl group, a (C1-C6)alkoxy(C1-C6)alkyl group, a di(C1-C6)alkoxy(C1-C6)alkyl group, a cyano(C1-C6)alkyl group, a (C1-C6)alkylthio(C1-C6)alkyl group, a di(C1-C6)alkylamino(C1-C6)alkyl group, a (C1-C6)alkylcarbonyl group, a (C1-C6)alkoxycarbonyl(C1-C6) alkyl group, a phenylcarbonyl group, or a benzyl group;
(c13) an aryl group;
(c14) an aryl group, independently having on the ring 1 to 8 substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a halo(C1-C6) alkyl group, a halo(C1-C6)alkoxy group, a halo(C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfonyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylthio group, a halo(C1-C6) alkylsulfinyl group, a halo(C1-C6)alkylsulfonyl group, an Ra(Rb)N group, wherein Ra and Rb are the same as above, a (C1-C6)alkoxycarbonyl group, and Ra(Rb)Ncarbonyl group (wherein Ra and Rb are the same as above);
(c15) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring;
(c16) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring, each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, (C1-C6)alkyl group, (C1-C6)alkoxy group, (C3-C6)cycloalkyl group, halo(C1-C6)alkyl group, halo(C1-C6)alkoxy group, halo(C3-C6)cycloalkyl group, (C1-C6)alkylthio group, (C1-C6)alkylsulfinyl group, (C1-C6)alkylsulfonyl group, halo(C1-C6)alkylthio group, halo(C1-C6)alkylsulfinyl group, halo(C1-C6)alkylsulfonyl group, Ra(Rb)N group (wherein Ra and Rb are the same as above), (C1-C6)alkylthio(C1-C6)alkyl group, phenyl group, halogen-substituted phenoxy group, (C1-C6)alkoxycarbonyl group and Ra(Rb)Ncarbonyl group (wherein Ra and Rb are the same as above);
(c17) an aryl (C1-C6)alkyl group;
(c18) an aryl (C1-C6)alkyl group, each independently having on the ring 1 to 8 substituents selected from the group consisting of a halogen atom, cyano group, nitro group, (C1-C6)alkyl group, (C1-C6)alkoxy group, (C3-C6)cycloalkyl group, halo(C1-C6)alkyl group, halo(C1-C6)alkoxy group, halo(C3-C6)cycloalkyl group, (C1-C6)alkylthio group, (C1-C6)alkylsulfonyl group, (C1-C6)alkylsulfonyl group, halo(C1-C6)alkylthio group, halo(C1-C6)alkylsulfinyl group, halo(C1-C6)alkylsulfonyl group, Ra(Rb)N group (wherein Ra and Rb are the same as above), (C1-C6)alkoxycarbonyl group, and Ra(Rb)Ncarbonyl group, wherein Ra and Rb are the same as above;
(c19) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring (C1-C6)alkyl group;
(c20) a 5- to 6-membered hetero ring or an 8- to 10-membered fused hetero ring (C1-C6)alkyl group, each independently having on the ring 1 to 3 substituents selected from the group consisting of a halogen atom, a cyano group, a nitro group, a (C1-C6)alkyl group, a (C1-C6)alkoxy group, a (C3-C6)cycloalkyl group, a halo(C1-C6)alkyl group, a halo(C1-C6)alkoxy group, a halo(C3-C6)cycloalkyl group, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfonyl group, a (C1-C6)alkylsulfonyl group, a halo(C1-C6)alkylthio group, a halo(C1-C6)alkylsulfinyl group, a halo(C1-C6)alkylsulfonyl group, an Ra(Rb)N group, wherein Ra and Rb are the same as above, a (C1-C6)alkylthio(C1-C6)alkyl group, a phenyl group, a halogen-substituted phenoxy group, a (C1-C6)alkoxycarbonyl group, and an Ra(Rb)Ncarbonyl group, wherein Ra and Rb are the same as above;
(c21) a (C1-C6)alkyl group, each independently having on the chain 1 to 3 substituents selected from the group consisting of a cyano group, a (C1-C6)alkoxy group, an Ra(Rb)N group, wherein Ra and Rb are the same as above, a (C1-C6)alkylthio group, a (C1-C6)alkylsulfinyl group, and a (C1-C6)alkylsulfonyl group;
(c22) an RcON═C(Rd)NH group, wherein Rc and Rd are each independently a hydrogen atom or a (C1-C6)alkyl group); or
(c23) a 3-ethoxyiminoazetidin-1-yl group;
R5 is:
(d1) a hydrogen atom;
(d2) a (C1-C6)alkyl group;
(d3) a (C1-C6)alkylcarbonyl group;
(d4) a (C1-C6)alkoxycarbonyl group; or
(d5) a benzyl group;
R6 is:
(e1) a hydrogen atom; and
X1, X2, X3, and X4 are each independently:
(f1) a hydrogen atom;
(f2) a halogen atom;
(f3) a cyano group;
(f4) a nitro group;
(f5) a (C1-C6)alkyl group;
(f6) a (C3-C6)cycloalkyl group;
(f7) a (C1-C6)alkoxy group;
(f8) a halo(C1-C6)alkyl group;
(f9) a halo(C1-C6)alkoxy group;
(f10) a halo(C3-C6)cycloalkyl group;
(f11) a (C1-C6)alkylthio group;
(f12) a (C1-C6)alkylsulfinyl group;
(f13) a (C1-C6)alkylsulfonyl group;
(f14) a halo(C1-C6)alkylthio group;
(f15) a halo(C1-C6)alkylsulfinyl group; or
(f16) a halo(C1-C6)alkylsulfonyl group.