US 12,454,507 B2
Compounds having a fungicidal activity, their agronomic compositions and use thereof for the control of phytopathogenic fungi
Marilena Gusmeroli, Monza (IT); Silvia Mormile, Novara (IT); Alexia Elmini, Cigliano (IT); Paolo Boggio, Turin (IT); Paolo Bellandi, Carcare (IT); Matteo Vazzola, Cogliate (IT); Giovanni Venturini, Cassano d'Adda (IT); Riccardo Liguori, Monza (IT); and Christian Badaracco, Vittuone (IT)
Appl. No. 17/767,752
Filed by ISAGRO S.p.A., Milan (IT)
PCT Filed Jul. 7, 2020, PCT No. PCT/IB2020/056385
§ 371(c)(1), (2) Date Apr. 8, 2022,
PCT Pub. No. WO2021/005512, PCT Pub. Date Jan. 14, 2021.
Claims priority of application No. 102019000011127 (IT), filed on Jul. 8, 2019.
Prior Publication US 2024/0116855 A1, Apr. 11, 2024
Int. Cl. C07C 233/81 (2006.01); A01N 37/20 (2006.01); A01P 3/00 (2006.01); C07C 237/44 (2006.01); C07C 237/46 (2006.01)
CPC C07C 233/81 (2013.01) [A01N 37/20 (2013.01); A01P 3/00 (2021.08); C07C 237/44 (2013.01); C07C 237/46 (2013.01)] 14 Claims
 
1. A compound Compounds having general formula (I):

OG Complex Work Unit Chemistry
wherein:
Rc represents a formylamine group;
M represents a W1—R6 group;
W and W1, the same or different, represent an oxygen atom or a sulfur atom;
Rd represents a hydrogen atom, a halogen atom selected from fluorine, chlorine, bromine or iodine, a nitro group, an amino group, a formylamine group, a cyano group, a C1-C18 alkyl group, a C3-C18 cycloalkyl group, a C3-C18 cycloalkyl-C1-C12-alkyl group, C1-C18 haloalkyl group, a C2-C18 alkenyl group, a C2-C18 haloalkenyl group, a C3-C18 cycloalkenyl group, a C1-C18 alkoxyl group, a C1-C18 haloalkoxyl group, a C1-C18 thioalkoxyl group, a C1-C18 alkylsulfonyl group, a C1-C18 alkylsulfinyl group, a C3-C18 cycloalkoxyl group, an aryl group, a phenoxyl group, a benzyloxy group, an aryl-C1-C18-alkyl group, a heterocyclic group, penta- or hexa-atomic, aromatic or non-aromatic, also benzocondensed or heterobicyclic, containing at least one heteroatom selected from oxygen, sulfur, optionally oxidized to sulfoxide or to sulfone, nitrogen, optionally oxidized to N-oxide or a heterocyclyl-C1-C18-alkyl group wherein the heterocyclic group is as defined above; a C (═W1) R8 group, a C (═O)OR8 group, a C (═O) NR8R9 group, a S (═O)2NR8R9 group;
n represents a number ranging from 0 to 2;
R6 represents a CH2OR7 group, a CH2SR7 group, a COR7 group, a CH2OCOR7 group;
R7 represents a C1-C18 alkyl group, a C3-C18 cycloalkyl group, a C1-C18 haloalkyl group, a C1-C18 alkoxyl group, an aryl group, a benzyl group, said groups being optionally substituted with one or more Rd groups the same as or different from each other;
R8 and R9, the same or different, represent a hydrogen atom, a C1-C18 alkyl group, a C1-C18 haloalkyl group, a C2-C18 alkenyl group, a C2-C18 haloalkenyl group, a C3-C18 cycloalkyl group, a C3-C18 halocycloalkyl group, an aryl group, an aryl-C1-C18-alkyl group, each of said groups R8 and R9 can be optionally substituted by 0, 1 or multiples of Rd;
Y represents one of the following Y1 or Y2 groups

OG Complex Work Unit Chemistry
wherein:
Ra and Rb, the same or different, represent a hydrogen atom, a C1-C18 alkyl group, a C1-C18 haloalkyl group, a C3-C18 cycloalkyl group, an aryl group, an aryl-C1-C18-alkyl group, a heterocyclic group, penta- or hexa-atomic, aromatic or non-aromatic, containing at least one heteroatom selected from oxygen, sulfur, possibly oxidized to sulfoxide or sulfone, nitrogen, possibly oxidized to N-oxide, a heterocyclyl-C1-C18-alkyl group wherein the heterocyclic group is as defined above; said groups being optionally substituted with one or more Rd groups, the same as or different from each other;
or Ra and Rb together with the carbon atom to which they are bound form a C3-C18 cycloalkyl ring;
Re and Rf, the same or different, represent a hydrogen atom, a C1-C18 alkyl group, a C1-C18 haloalkyl group, said groups being optionally substituted with one or more Rd groups the same as or different from each other;
R1 represents a hydrogen atom, a C1-C18 alkyl group, a C1-C18 haloalkyl group, a C2-C18 alkenyl group, a C2-C18 haloalkenyl group, a C2-C18 alkynyl group, a C3-C18 cycloalkyl group, a C3-C18 cycloalkenyl group, a C3-C18 cycloalkyl-C1-C18-alkyl group, an aryl group, an aryl-C1-C18-alkyl group, a heterocyclic group, penta- or hexa-atomatic, aromatic or non-aromatic, also benzocondensed or heterobicyclic, containing at least one heteroatom selected from oxygen, sulfur, possibly oxidized to sulfoxide or sulfone, nitrogen, possibly oxidized to N-oxide or a heterocyclyl-C1-C18-alkyl group wherein the heterocyclic group is as defined above; said groups being optionally substituted with one or more Rd groups, the same as or different from each other;
R2 represents a C1-C18 alkyl group, a C1-C18 haloalkyl group, a C2-C18 alkenyl group, a C2-C18 haloalkenyl group, a C3-C18 cycloalkyl group, a C3-C18 cycloalkenyl group, a C3-C18 cycloalkyl -C1-C18-alkyl group, an aryl group, an aryl-C1-C18-alkyl group, a heterocyclic group, penta- or hexa-atomatic, aromatic or non-aromatic, also benzocondensed or heterobicyclic, containing at least one heteroatom selected from oxygen, sulfur, possibly oxidized to sulfoxide or to sulfone, nitrogen, possibly oxidized to N-oxide or a heterocyclyl-C1-C18-alkyl group wherein the heterocyclic group is as defined above, a COOR2 group, a CONHR2 group, a CONR1 R2 group; said groups being optionally substituted with one or more Rd groups, the same as or different from each other, or R2 represents the following T group:
T=

OG Complex Work Unit Chemistry
wherein:
R3, R5, the same or different, represent a C1-C18 alkyl group, a C1-C18 haloalkyl group, a C1-C18 alkoxyl group, a C2-C18 alkenyl group, a C2-C18 haloalkenyl group, a C3-C18 cycloalkyl group, a C3-C18 cycloalkoxyl group, an NHR1 group, an NR12 group, an aryl group, a phenoxyl group, an aryl-C1-C18-alkyl group, an aryl-C1-C18-alkoxyl group, a heterocyclic group, penta- or hexa-atomic, aromatic or non-aromatic, also benzocondensed or heterobicyclic, containing at least one heteroatom selected from oxygen, sulfur, nitrogen, wherein the sulfur atom can be possibly oxidized to sulfoxide or sulfone and the nitrogen atom possibly oxidized to N-oxide or a heterocyclyl-C1-C18-alkyl group, said groups being optionally substituted with one or more Rd groups, the same as or different from each other;
R4 represents a hydrogen atom, a hydroxyl, a halogen atom selected from fluorine, chlorine, bromine or iodine, a C1-C18 alkyl group, a C1-C18 haloalkyl group, a C2-C18 alkenyl group, a C2-C18 haloalkenyl group, a C3-C18 cycloalkyl group, a C1-C18 alkoxyl group;
or R3 and R4 together with the carbon atom to which they are bound, form a C3-C18 cycloalkyl group or a heterocyclic group, penta- or hexa-atomic, containing at least one heteroatom selected from oxygen, sulfur, possibly oxidized to sulfoxide or sulfone, nitrogen, possibly oxidized to N-oxide, said groups being optionally substituted with one or more Rd groups the same as or different from each other;
or R1 and R2 together with the carbon atom to which they are bound, form a C3-C18 cycloalkyl ring;
with the proviso that:
when Rc represents a hydrogen atom, n is equal to 0, W and W1 are both oxygen, Y represents the group Y1 wherein Ra and Rb, different from each other, have the meaning of hydrogen and methyl, R1 represents a methyl group, R2 is a T group wherein R4 is a hydrogen atom, R3 and R5 both represent a 4-fluorophenyl group, then R6 is different from hydrogen or is different from a CH2OCOR7 group wherein R7 is a methyl.