IP Library Granted Patent US 10,813,354
Granted Patent B2
US 10,813,354 · App. 16/093,338 · Granted Oct 27, 2020

Herbicidal pyridazinone compounds

Inventors: Paul Matthew Burton (Bracknell, GB); Steven Gaulier (Bracknell, GB); Paula Rocha Rzepa (Bracknell, GB); Melanie Jayne Watkins (Bracknell, GB); Mary Bernadette Aspinall (Bracknell, GB); Edward John Emmett (Bracknell, GB)
Assignee: SYNGENTA PARTICIPATIONS AG
A01N43/58C07D237/14C07D403/06C07D405/06C07D407/06
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Quick Facts
Patent No.
US 10,813,354
App. No.
16/093,338
Granted
Oct 27, 2020
Kind
B2
Abstract

The present invention relates to compounds of Formula (I), or an agronomically acceptable salt of said compounds wherein A 1 , R 1 , R a , R b , R c and R d are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), to intermediate compounds used to produce compounds of Formula (I), to processes for producing compounds of Formula (I) and to the use of compounds of Formula (I) for controlling weeds, in particular in crops of useful plants.

Claims (34)

1. A compound of Formula (I):

or an agronomically acceptable salt thereof,

wherein

R 1 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C 1 -C 6 alkyl-, C 3 -C 6 cycloalkyl-, C 2 -C 6 -alkenyl-, C 2 -C 6 alkynyl-, C 1 -C 6 haloalkyl-, C 1 -C 6 alkoxy-, C 1 -C 3 haloalkoxy-, C 1 -C 6 alkoxy-C 1 -C 3 alkyl-, C 1 -C 6 alkyl-S(O)p- and C 1 -C 6 haloalkyl-S(O)p-;

A 1 is selected from the group consisting of O, C(O) and (CReR f );

R a , R b , R c , R d , R e and R f are each independently selected from the group consisting of hydrogen and C 1 -C 4 alkyl- wherein R a and R c may together form a C 1 -C 3 alkylene chain; and

p is 0, 1 or 2.

2. The compound according to claim 1 , wherein R 1 is C 1 -C 6 alkyl- or C 3 -C 6 cycloalkyl-.

3. The compound according to claim 1 , wherein R 1 is methyl or cyclopropyl-.

4. The compound according to claim 1 , wherein A 1 is CR e R f and R e and R f are hydrogen.

5. The compound according to claim 1 , wherein R a , R b , R c and R d are hydrogen.

6. The compound according to claim 1 , wherein R a and R c together form a —CH 2 —CH 2 — chain and R b and R d are hydrogen.

7. The compound according to claim 1 , wherein A 1 is O and R a , R b , R c and R d are methyl.

8. The compound according to claim 1 in the form of an agrochemically acceptable salt, wherein the agrochemically acceptable salt is selected from the group consisting of aluminium, calcium, cobalt, copper, iron, magnesium, potassium, sodium and zinc.

9. A herbicidal composition comprising a compound according to claim 1 and an agriculturally acceptable formulation adjuvant.

10. A herbicidal composition according to claim 9 , further comprising at least one additional pesticide.

11. A herbicidal composition according to claim 10 , wherein the additional pesticide is a herbicide or herbicide safener.

12. A method of controlling weeds at a locus comprising application to the locus of a weed controlling amount of a composition according to claim 9 .

13. A method of producing the compound of Formula (I) in claim 1 comprising:

(i) reacting, in an inert organic solvent and in the presence of a base, a compound of Formula (IIc):

where the definition of R 1 is as for Formula (I) in claim 1 and LG is a suitable leaving group, with a diketone of Formula (III)

wherein A 1 , R a , R b , R c , and R d are as for Formula (I) in claim 1 , and

(ii) rearrangement of the resulting product into the compound of Formula (I).

14. A compound of Formula (II)

wherein

R 1 is selected from the group consisting of hydrogen, halogen, cyano, nitro, C 1 -C 6 alkyl-, C 3 -C 6 cycloalkyl-, C 2 -C 6 -alkenyl-, C 2 -C 6 alkynyl-, C 1 -C 6 haloalkyl-, C 1 -C 6 alkoxy-, C 1 -C 3 haloalkoxy-, C 1 -C 6 alkoxy-C 1 -C 3 alkyl-, C 1 -C 6 alkyl-S(O)p- and C 1 -C 6 haloalkyl-S(O)p-;

p is 0, 1 or 2; and

R 2 is selected from the group consisting of halogen, OH, C 1 -C 6 alkoxy-, aryloxy and N-linked imdazolyl.

15. The compound according to claim 14 , wherein R 1 is C 3 -C 6 cycloalkyl-, C 2 -C 6 -alkenyl-, C 2 -C 6 alkynyl-, C 1 -C 6 alkoxy-C 1 -C 3 alkyl-, C 1 -C 6 alkyl-S(O)p- and C 1 -C 6 haloalkyl-S(O)p-, and wherein p is 1 or 2.

16. The compound according to claim 14 , wherein R 1 is methyl or cyclopropyl-.

17. The compound according to claim 16 , wherein R 2 is selected from the group consisting of halogen, aryloxy and N-linked imdazolyl.

18. The compound according to claim 14 , wherein R 2 is selected from the group consisting of halogen, aryloxy and N-linked imdazolyl.

19. The compound according to claim 14 , wherein R 1 is C 3 -C 6 cycloalkyl-.

20. The compound according to claim 14 , wherein R 1 is cyclopropyl.

Assignments (2)
CHANGE OF NAME Recorded Apr 28, 2025
From: SYNGENTA PARTICIPATIONS AG
To: SYNGENTA CROP PROTECTION AG
Reel/Frame 071085/0107 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 7, 2020
From: ASPINALL, MARY BERNADETTE; BURTON, PAUL MATTHEW; GAULIER, STEVEN; RZEPA, PAULA ROCHA; WATKINS, MELANIE JAYNE; EMMETT, EDWARD JOHN
To: SYNGENTA PARTICIPATIONS AG
Reel/Frame 051438/0697 →