Herbicidal Pyridino-/Pyrimidino-Thiazoles
AssigneeSyngenta Participations AG
InventorsNeil Brian CARTER, Derek MCCORMACK, Anne Mary SEVILLE, Matthew John WEBBER, Matthew Murdoch MCLACHLAN, Alison Clare ELLIOTT
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Abstract
The present invention relates to herbicidally active pyridino-/pyrimidino-thiazole 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.
Claims21
A method of controlling unwanted plant growth, comprising applying a compound of formula (I)
- or a salt or N-oxide thereof, wherein,
- X1 is N or CR1;
- R1 is hydrogen, halogen, cyano, C1-C6alkyl, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxy, —C(O)OR6 or S(O)n(C1-C6alkyl), formyl, hydroxyl, —C(O)NR6R7, NR6R7, benzyloxy, C1-C6 haloalkoxy, or C1-C6 haloalkyl;
- R2 is hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6 alkynyl, C3-C6cycloalkyl, —C(O)OR6, S(O)n(C1-C6alkyl), C1-C6 alkoxy, or C1-C6 haloalkoxy;
- n is 0, 1, or 2;
- R3 is hydrogen, cyano, C1-C6alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6haloalkoxy, C2-C6alkenyloxy, C3-C10cycloalkyl, NR6R7,
- R4 is O, S, or N(C1-C6alkyl);
- X2 is O, S, or NR8;
- R5 is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C10cycloalkyl, C3-C10cycloalkenyl, C1-C6haloalkyl, C2-C6haloalkenyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyloxy, C2-C6alkynyloxy, C3-C10cycloalkyloxy, C3-C10cycloalkenyloxy, C2-C6haloalkenyloxy, C6-C10aryl or C6-C10aryl substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, and C1-C3 haloalkoxy;
- C3-C10heterocylcyl or C3-C10heterocyclycl substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, and C1-C3 haloalkoxy;
- or NR6R7;
- or R3 and R5 together with X2 and the atoms to which they are attached, form a saturated or partially unsaturated 5-9 membered ring system optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C1-C6 alkyl;
- or R3 and R8 together with the atoms to which they are attached form a saturated or partially unsaturated 5-9 membered ring system optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C1-C6 alkyl;
- R6 and R7 are each independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl,
- or R4 and R5 together with X2 and the atoms to which they are attached, form a saturated or partially unsaturated 5-9 membered ring system optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C1-C6 alkyl;
- or R6 and R7 together with the nitrogen atom to which they are attached form a saturated or partially unsaturated 3-6 membered ring optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C1-C6 alkyl;
- R8 is hydrogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl;
- C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyloxy, C2-C6alkynyloxy, C3-C10cycloalkyloxy, C3-C10cycloalkenyloxy, C2-C6haloalkenyloxy;
- or R7 and R8 together with the carbon atoms to which they are attached form a saturated or partially unsaturated 3-9 membered ring optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C1-C6 alkyl,
- to the unwanted plants or to the locus thereof.
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A method of selectively controlling weeds at a locus comprising crop plants and weeds, wherein the method comprises application to the locus, of a weed-controlling amount of (i) a compound of formula (I):
- or a salt or N-oxide thereof, wherein,
- X1 is N or CR1;
- R1 is hydrogen, halogen, cyano, C1-C6alkyl, C3-C6cycloalkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6alkoxy, —C(O)OR6 or S(O)n(C1-C6alkyl), formyl, hydroxyl, —C(O)NR6R7, NR6R7, benzyloxy, C1-C6 haloalkoxy, or C1-C6 haloalkyl;
- R2 is hydrogen, halogen, cyano, nitro, C1-C6 alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6 alkynyl, C3-C6cycloalkyl, —C(O)OR6, S(O)n(C1-C6alkyl), C1-C6 alkoxy, or C1-C6 haloalkoxy;
- n is 0, 1, or 2;
- R3 is hydrogen, cyano, C1-C6alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6haloalkenyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6haloalkoxy, C2-C6alkenyloxy, C3-C10cycloalkyl, NR6R7,
- R4 is O, S, or N(C1-C6alkyl);
- X2 is O, S, or NR8;
- R5 is hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C3-C10cycloalkyl, C3-C10cycloalkenyl, C1-C6haloalkyl, C2-C6haloalkenyl, C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyloxy, C2-C6alkynyloxy, C3-C10cycloalkyloxy, C3-C10cycloalkenyloxy, C2-C6haloalkenyloxy, C6-C10aryl or C6-C10aryl substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, and C1-C3 haloalkoxy;
- C3-C10heterocylcyl or C3-C10heterocyclycl substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl, and C1-C3 haloalkoxy;
- or NR6R7;
- or R3 and R5 together with X2 and the atoms to which they are attached, form a saturated or partially unsaturated 5-9 membered ring system optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C1-C6 alkyl;
- or R3 and R8 together with the atoms to which they are attached form a saturated or partially unsaturated 5-9 membered ring system optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C1-C6 alkyl;
- R6 and R7 are each independently hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl,
- or R4 and R5 together with X2 and the atoms to which they are attached, form a saturated or partially unsaturated 5-9 membered ring system optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C1-C6 alkyl;
- or R6 and R7 together with the nitrogen atom to which they are attached form a saturated or partially unsaturated 3-6 membered ring optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C1-C6 alkyl;
- R8 is hydrogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, or C2-C6 alkynyl;
- C1-C6alkoxy, C1-C6haloalkoxy, C2-C6alkenyloxy, C2-C6alkynyloxy, C3-C10cycloalkyloxy, C3-C10cycloalkenyloxy, C2-C6haloalkenyloxy;
- or R7 and R8 together with the carbon atoms to which they are attached form a saturated or partially unsaturated 3-9 membered ring optionally comprising 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with 1 to 3 groups independently selected from halogen or C1-C6 alkyl.
Dependencies are inferred from the claim text.