US 12,225,904 B2
Phenylpyrazole compound and method for controlling plant disease
Nao Maehata, Takarazuka (JP); Hiroshi Sakaguchi, Takarazuka (JP); Shuhei Azuma, Osaka (JP); and Yusuke Ota, Osaka (JP)
Assigned to SUMITOMO CHEMICAL COMPANY, LIMITED, Chuo-ku (JP)
Appl. No. 17/285,687
Filed by SUMITOMO CHEMICAL COMPANY, LIMITED, Chuo-ku (JP)
PCT Filed Oct. 18, 2019, PCT No. PCT/JP2019/041139
§ 371(c)(1), (2) Date Apr. 15, 2021,
PCT Pub. No. WO2020/080534, PCT Pub. Date Apr. 23, 2020.
Claims priority of application No. 2018-196428 (JP), filed on Oct. 18, 2019.
Prior Publication US 2021/0321614 A1, Oct. 21, 2021
Int. Cl. A01N 43/56 (2006.01); A01N 43/76 (2006.01); A01N 43/78 (2006.01); A01N 43/82 (2006.01); A01N 43/84 (2006.01)
CPC A01N 43/56 (2013.01) [A01N 43/76 (2013.01); A01N 43/78 (2013.01); A01N 43/82 (2013.01); A01N 43/84 (2013.01)] 8 Claims
 
1. A compound represented by formula (II):

OG Complex Work Unit Chemistry
wherein
ZA represents —NR8AR9A, a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group IA, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, or a three to seven membered non-aromatic heterocyclic group, wherein the three to seven membered non-aromatic heterocyclic group may optionally have one or more substituents selected from the group consisting of a C1-C3 alkyl group optionally having one or more halogen atoms and a halogen atom,
R8A and R9A are identical to or different from each other and represent a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group IA, a C3-C6 cycloalkyl group optionally having one or more halogen atoms or a hydrogen atom,
R1A, R2A, R3A and R7A represent a hydrogen atom,
a combination of R4A, R5A and R6A represents any combination of a or b,
a: a combination wherein R5A represents a hydrogen atom, R4A represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group IB, a halogen atom, a cyano group, —OR15B, —CR39BR40BOR41B, —CR43BR44BSR45B, —S(O)qR16B, —C(O)R17B, —CR18B═N—O—R19B, —O—N═CR20BR46B, —N═N—CR21BR47B, —C(O)NR22BR23B, —NR24BC(O)R25B, —C(O)N(OR26B)R27B, —N(OR28B)C(O)R29B, —NR30BC(O)NR31BR32B, —OC(O)NR33BR34B, —NR35BC(O)OR36B, —NR48BC(O)C(O)NR49BR50B, —CR51BR52BNR53BC(O)C(O)NR54BR55B, —NR56BC(O)C(O)N(OR57B)R58B, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a five to ten membered aromatic heterocyclic group, wherein each of the C3-C6 cycloalkyl group, the C6-C10 aryl group and the five to ten membered aromatic heterocyclic group may optionally have one or more substituents selected from Group KB, and R6A represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group IB, a hydrogen atom, a halogen atom, a cyano group, —OR15B, —CR39BR40BOR41B, —CR43BR44BSR45B, —S(O)qR16B, —C(O)R17B, —CR18B═N—O—R19B, —O—N═CR20BR46B, —N═N═CR21BR47B, —C(O)NR22BR23B, —NR24BC(O)R25B, —C(O)N(OR26B)R27B, —N(OR28B)C(O)R29B, —NR30BC(O)NR31BR32B, —OC(O)NR33BR34B, —NR35BC(O)OR36B, —NR48BC(O)C(O)NR49BR50B, —CR51BR52BNR53BC(O)C(O)NR54BR55B, —NR56BC(O)C(O)N(OR57B)R58B, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a five to ten membered aromatic heterocyclic group, wherein each of the C3-C6 cycloalkyl group, the C6-C10 aryl group and the five to ten membered aromatic heterocyclic group may optionally have one or more substituents selected from Group KB;
b: a combination wherein R5A represents a halogen atom, a nitro group, a C1-C6 chain hydrocarbon group, a C3-C6 cycloalkyl group, or —S(O)2R11A, wherein each of the C1-C6 chain hydrocarbon group and the C3-C6 cycloalkyl group may optionally have one or more halogen atoms, wherein R11A represents a C1-C4 chain hydrocarbon group optionally having one or more halogen atoms, and R4A and R6A are identical to or different from each other and represent a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a hydrogen atom, a halogen atom, or a nitro group,
R4A and R5A may be taken together with a carbon to which they are attached to form a C4-C7 carbocycle group, or a five to seven membered heterocyclic group, wherein each of the C4-C7 carbocycle group and the five to seven membered heterocyclic group may optionally have one or more substituents selected from the group consisting of a halogen atom and a C1-C3 chain hydrocarbon group,
R15B represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group LB, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a five to ten membered aromatic heterocyclic group, with the proviso that a pyridyl group is excluded, wherein each of the C3-C6 cycloalkyl group, the C6-C10 aryl group and the five to ten membered aromatic heterocyclic group, with the proviso that a pyridyl group is excluded, may optionally have one or more substituents selected from Group KB,
R17B, R18B, R19B, R20B, R21B, R22B, R23B, R24B, R25B, R26B, R27B, R28B, R29B, R30B, R31B, R32B, R33B, R34B, R35B, R39B, R40B, R41B, R43B, R44B, R45B, R46B, R47B, R48B, R49B, R50B, R51B, R52B, R53B, R54B, R55B, R56B, R57B, and R58B are identical to or different from each other and represent a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group LA, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a five to ten membered aromatic heterocyclic group, wherein each of the C3-C6 cycloalkyl group, the C6-C10 aryl group and the five to ten membered aromatic heterocyclic group may optionally have one or more substituents selected from Group KA,
R36B represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group LA, a C3-C6 cycloalkyl group, a C6-C10 aryl group, or a five to ten membered aromatic heterocyclic group, wherein each of the C3-C6 cycloalkyl group, the C6-C10 aryl group and the five to ten membered aromatic heterocyclic group may optionally have one or more substituents selected from Group KA,
R16B represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group LA, or a C3-C6 cycloalkyl group, wherein the C3-C6 cycloalkyl group may optionally have one or more substituents selected from the group consisting of a halogen atom and a cyano group,
q is 0, 1 or 2,
Group IA: a group consisting of a halogen atom, a cyano group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group and a C1-C3 alkylthio group, wherein each of the C3-C6 cycloalkyl group, the C1-C3 alkoxy group and the C1-C3 alkylthio group may optionally have one or more halogen atoms,
Group KA: a group consisting of a halogen atom, a cyano group, a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, and a C1-C3 alkylthio group, wherein each of the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C3 alkoxy group and the C1-C3 alkylthio group may optionally have one or more substituents selected from the group consisting of a halogen atom and a cyano group,
Group LA: a group consisting of a halogen atom, a cyano group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, and a five to ten membered aromatic heterocyclic group, wherein each of the C1-C3 alkoxy group and the C1-C3 alkylthio group may optionally have one or more halogen atoms, and each of the C3-C6 cycloalkyl group, the C6-C10 aryl group and the five to ten membered aromatic heterocyclic group may optionally have one or more substituents selected from Group KA,
Group IB: a group consisting of a halogen atom, a cyano group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group and a C1-C3 alkylthio group, wherein each of the C3-C6 cycloalkyl group, the C1-C3 alkoxy group and the C1-C3 alkylthio group may optionally have one or more halogen atoms,
Group KB: a group consisting of a halogen atom, a cyano group, a C1-C3 chain hydrocarbon group, a C3-C6 cycloalkyl group, a C1-C3 alkoxy group, and a C1-C3 alkylthio group, wherein each of the C1-C3 chain hydrocarbon group, the C3-C6 cycloalkyl group, the C1-C3 alkoxy group and the C1-C3 alkylthio group may optionally have one or more substituents selected from the group consisting of a halogen atom and a cyano group,
Group LB: a group consisting of a halogen atom, a cyano group, a C1-C3 alkoxy group, a C1-C3 alkylthio group, a C3-C6 cycloalkyl group, a C6-C10 aryl group, and a five to ten membered aromatic heterocyclic group, wherein each of the C1-C3 alkoxy group and the C1-C3 alkylthio group may optionally have one or more halogen atoms, and each of the C3-C6 cycloalkyl group, the C6-C10 aryl group and the five to ten membered aromatic heterocyclic group may optionally have one or more substituents selected from Group KA.