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US 2020/0267984 A1Published application
Herbicidally Active Pyridyl-/Pyrimidyl-Pyrazine Derivatives
AssigneeSyngenta Participations AG
InventorsJeffrey Steven WAILES, Neil Brian CARTER, John Martin CLOUGH, John WILLIAMS
Life of this patent
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Abstract
The present invention relates to herbicidally active pyridyl-/pyrimidyl-pyrazine derivatives, as well as to processes and intermediates used for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, as well as to the use of such compounds and compositions in controlling undesirable plant growth: in particular the use in controlling weeds, in crops of useful plants.
Claims15
A method, comprising:
- applying as an herbicide a compound of formula (I)
- or a salt thereof, wherein:
- X1 is N or CR1;
- R1 is selected from the group consisting of hydrogen, halogen, cyano, C1-C6alkyl, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxy, —C(O)OC1-C6alkyl, —S(O)pC1-C6alkyl, NR6R7, C1-C6haloalkoxy and C1-C6haloalkyl;
- R2 is selected from the group consisting of halogen, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, trimethylsilylC2-C6alkynyl-, C3-C6cycloalkyl, C5-C6cycloalkenyl, —C(O)OC1-C6alkyl, —S(O)p(C1-C6alkyl), C1-C6alkoxy, C1-C6haloalkoxy, —O—(CRaRb)qR9, or phenyl;
- R3 is selected from the group consisting of hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkenyl, C1-C6alkoxyC1-C3alkyl-, C1-C6haloalkyl- and —(CRaRb)qR5;
- Ra is hydrogen or C1-C2 alkyl;
- Rb is hydrogen or C1-C2 alkyl;
- R4 is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkenyl, C1-C6alkoxyC1-C3alkyl-, C1-C6haloalkyl- and —(CRaRb)qR5;
- R5 is hydroxy, —C(O)OC1-C6alkyl, —C3-C10cycloalkyl, -aryl, or -heteroaryl wherein said aryl and heteroaryl are optionally substituted by 1 to 3 independent R8;
- or R3 and R4 together with the nitrogen to which they are attached, form a saturated or partially unsaturated 4-6 membered ring system optionally containing 1 or 2 further heteroatoms independently selected from S, O and N, wherein said ring is optionally substituted by 1 to 3 R8;
- R6 and R7 are independently selected from the group consisting of hydrogen, C1-C6alkyl and —C(O)OC1-C6alkyl;
- each R8 is independently selected from the group consisting of halogen, C1-C6 alkyl and C1-C6alkoxy-, C1-C6 haloalkyl, C1-C6 haloalkoxy-, cyano and S(O)p(C1-C6alkyl);
- R9 is —C(O)ORc, —OC(O)Rc, —C3-C6cycloalkyl, or an -aryl, -aryloxy, -heteroaryl, -heteroaryloxy or -heterocyclyl ring, wherein said ring is optionally substituted by 1 to 3 independent R8;
- Rc is hydrogen or C1-C4alkyl;
- n is 0 or 1;
- p is 0, 1, or 2;
- and
- q is 0, 1, or 2.
16 more elements
A compound of Formula (I)
- or a salt thereof,
- wherein:
- X1 is N or CR1;
- R1 is selected from the group consisting of halogen, cyano, C1-C6alkyl, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxy, —C(O)OC1-C6alkyl, —S(O)pC1-C6alkyl, NR6R7, C1-C6haloalkoxy and C1-C6haloalkyl;
- R2 is selected from the group consisting of halogen, cyano, nitro, C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6alkynyl, trimethylsilylC2-C6alkynyl-, C3-C6cycloalkyl, C5-C6cycloalkenyl, —C(O)OC1-C6alkyl, —S(O)p(C1-C6alkyl), C1-C6alkoxy, C1-C6haloalkoxy, —O—(CRaRb)qR9, or phenyl;
- R3 is selected from the group consisting of hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkenyl, C1-C6alkoxyC1-C3alkyl-, C1-C6haloalkyl- and —(CRaRb)qR5;
- Ra is hydrogen or C1-C2 alkyl;
- Rb is hydrogen or C1-C2 alkyl;
- Rc is hydrogen or C1-C4alkyl;
- R4 is selected from the group consisting of hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkenyl, C1-C6alkoxyC1-C3alkyl-, C1-C6haloalkyl- and —(CRaRb)qR5;
- R5 is hydroxy, —C(O)OC1-C6alkyl, —C3-C10cycloalkyl, -aryl and -heteroaryl wherein said aryl and heteroaryl are optionally substituted by 1 to 3 independent R8;
- or R3 and R4 together with the nitrogen to which they are attached, form a saturated or partially unsaturated 4-6 membered ring system optionally containing 1 or 2 further heteroatoms independently selected from S, O and N, wherein said ring is optionally substituted by 1 to 3 R8;
- R6 and R7 are independently selected from the group consisting of hydrogen, C1-C6alkyl and —C(O)OC1-C6alkyl;
- each R8 is independently selected from the group consisting of halogen, C1-C6 alkyl and C1-C6alkoxy-, C1-C6 haloalkyl, C1-C6 haloalkoxy-, cyano and S(O)p(C1-C6alkyl);
- R9 is —C(O)ORc, —OC(O)Rc, —C3-C6cycloalkyl, or an -aryl, -aryloxy, -heteroaryl, -heteroaryloxy or -heterocyclyl ring, wherein said ring is optionally substituted by 1 to 3 independent R8;
- n is 0 or 1;
- p is 0, 1, or 2;
- and
- q is 0, 1, or 2;
- with the proviso that the compound of formula (I) is not:
- (i) methyl 6-(5-methyl-3-pyridyl)-3-morpholino-pyrazine-2-carboxylate, or
- (ii) methyl 3-amino-6-(3-pyridyl)pyrazine-2-carboxylate.
19 more elements
Dependencies are inferred from the claim text.