Herbicidal pyridino-/pyrimidino-thiazoles

Patent metadata

Field	Value
Publication number	US-11470846-B2
Application number	US-202016814320-A
Country	US
Kind code	B2
Filing date	Mar 10, 2020
Priority date	Sep 24, 2014
Publication date	Oct 18, 2022
Grant date	Oct 18, 2022

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.

First claim

The invention claimed is:

1. A compound of formula (I)

or a salt or N-oxide thereof, wherein,
X 1 is N or CR 1 ;
R 1 is hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, —C(O)OR 6 or S(O) n (C 1 -C 6 alkyl), formyl, hydroxyl, —C(O)NR 6 R 7 , NR 6 R 7 , benzyloxy, C 1 -C 6 haloalkoxy, or C 1 -C 6 haloalkyl;
R 2 is hydrogen, halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, —C(O)OR 6 , S(O) n (C 1 -C 6 alkyl), C 1 -C 6 alkoxy, or C 1 -C 6 haloalkoxy;
n is 0, 1, or 2;
R 3 is hydrogen, cyano, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 3 -C 10 cycloalkyl, NR 6 R 7 ,
R 4 is O, S, or N(C 1 -C 6 alkyl);
X 2 is O, S, or NR 8 ;
R 5 is C 2 -C 6 alkynyl
or R 3 and R 8 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 C 1 -C 6 alkyl;
R 6 and R 7 are each independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, or C 2 -C 6 alkynyl,
or R 6 and R 7 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 C 1 -C 6 alkyl;
R 8 is hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, or C 2 -C 6 alkynyl; C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 10 cycloalkyloxy, C 3 -C 10 cycloalkenyloxy, C 2 -C 6 haloalkenyloxy;
or R 7 and R 8 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 C 1 -C 6 alkyl.

2. The compound of claim 1 , wherein R 1 is hydrogen, halogen, formyl, cyano, C 1 -C 6 alkoxy, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylthio, C 1 -C 6 haloalkoxy, —C(O)NR 6 R 7 , NR 6 R 7 , or C 1 -C 6 haloalkyl.

3. The compound of claim 1 , wherein R 2 is halogen, cyano, nitro, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylthio, —C(O)OR 6 , C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 cycloalkyl, or C 2 -C 6 alkynyl.

4. The compound of claim 1 , wherein R 3 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 2 -C 6 alkenyloxy, C 3 -C 10 cycloalkyl, or NR 6 R 7 .

5. The compound of claim 1 , wherein R 4 is O.

6. The compound of claim 1 , wherein X 2 is O, or NR 8 .

7. A compound selected from:

8. The compound of claim 7 , wherein the compound is selected from:

9. An herbicidal composition comprising from 0.1 to 99% by weight, of a compound of Formula (I) as defined in claim 1 , and from 1 to 99.9% by weight of a formulation adjuvant, wherein the formulation adjuvant comprises from 0 to 25% by weight of a surface-active substance.

10. The herbicidal composition of claim 9 , further comprising at least one additional herbicide or herbicide safener.

11. 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 at a rate of from 50 to 1000 g/Ha of (i) a compound of formula (I) of claim 1 .

12. A method of controlling unwanted plant growth, comprising applying a weed-controlling amount of a compound of formula (I) of claim 1 to the unwanted plants or to a locus thereof, such that the unwanted plants are controlled by killing, reducing or retarding growth, or by preventing or reducing germination thereof.

Assignees

• Syngenta Participations Ag

Inventors

• Carter Neil Brian
• Elliott Alison Clare
• Mccormack Derek
• Mclachlan Matthew Murdoch Woodhead
• Seville Anne Mary
• Webber Matthew John

Classifications

• C07D417/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D213/76

  to which a second hetero atom is attached (nitro radicals C07D213/61) · CPC title

• A01N43/78 Primary

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title

• A01N47/18

  containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring · CPC title

• C07D277/44

  Acylated amino or imino radicals · CPC title