Novel-alkynyl-substituted 3-phenylpyrrolidine-2,4-diones and use thereof as herbicides

Patent metadata

Field	Value
Publication number	US-10899709-B2
Application number	US-201615738292-A
Country	US
Kind code	B2
Filing date	Jun 20, 2016
Priority date	Jun 22, 2015
Publication date	Jan 26, 2021
Grant date	Jan 26, 2021

Abstract

Novel alkynyl-substituted 3-phenylpyrrolidine-2,4-diones and use thereof as herbicides
The present invention relates to novel effective alkynyl-substituted 3-phenylpyrrolidine-2,4-diones according to the general formula (I) or agrochemically acceptable salts thereof,

where

X═C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 3 -C 6 -cycloalkyl; Y═C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl; n=1, 2 or 3; m=1 or 2; R 1 =C 1 -C 6 -alkyl, or C 3 -C 6 -cycloalkyl; R 2 =hydrogen or methyl; R 3 ═C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, or a saturated five- or six-membered heterocycle with an oxygen or sulphur atom; G=hydrogen, a cleavable group L or a cation E.
The invention also relates to the use of the compounds according to the invention for controlling weeds and weed grasses in crops of useful plants.

First claim

The invention claimed is:

1. An alkynyl-substituted N-phenylpyrrolidine-2,4-dione of formula (I),

or an agrochemically acceptable salt thereof, wherein
X is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 3 -C 6 -cycloalkyl,
Y is C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl,
n is 1, 2 or 3,
m is 1 or 2,
R 1 is C 1 -C 6 -alkyl or C 3 -C 6 -cycloalkyl,
R 2 is hydrogen or methyl,
R 3 is C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl,
G is hydrogen, a cleavable group L or a cation E; wherein
L is one of the following radicals

wherein
R 4 is C 1 -C 4 -alkyl or C 1 -C 3 -alkoxy-C 1 -C 4 -alkyl;
R 5 is C 1 -C 4 -alkyl,
R 6 is C 1 -C 4 -alkyl or an unsubstituted phenyl or a phenyl substituted one or more times with halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, nitro or cyano,
R 7 , R 7′ is in each case independently of one another methoxy or ethoxy,
R 8 and R 9 is in each case independently of one another methyl, ethyl, phenyl or together form a saturated 5-, 6- or 7-membered ring, or together form a saturated 5-, 6- or 7-membered heterocycle with an oxygen or sulphur atom,
E is an alkali metal ion, an ion equivalent of an alkaline earth metal, an ion equivalent of aluminium or an ion equivalent of a transition metal, a magnesium halogen cation, or
an ammonium ion, in which optionally one, two, three or all four hydrogen atoms by identical or different radicals from the groups hydrogen, C 1 -C 5 -alkyl, C 1 -C 5 -alkoxy or C 3 -C 7 -cycloalkyl, which can in each case be substituted one or more times with fluorine, chlorine, bromine, cyano, hydroxy or be interrupted by one or more oxygen or sulphur atoms, or
a cyclic secondary or tertiary aliphatic or heteroaliphatic amino ion, morpholinium, thiomorpholinium, piperidinium, pyrrolidinium, or in each case protonated 1,4-diazabicyclo[2.2.2]octane (DABCO) or 1,5-diazabicyclo[4.3.0]undec-7-ene (DBU), or
a heterocyclic ammonium cation, in each case protonated pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, 2,4-dimethylpyridine, 2,5-di-methylpyridine, 2,6-dimethylpyridine, 5-ethyl-2-methylpyridine, pyrrole, imidazole, quinoline, quinoxaline, 1,2-dimethylimidazole, 1,3-dimethylimidazolium methyl sulphate, or
a sulphonium ion.

2. The compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, wherein X and Y, independently of one another, are in each case C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl.

3. The compound of formula (I) according to claim 2 or an agrochemically acceptable salt thereof, wherein X and Y, independently of one another, are in each case methyl, ethyl or cyclopropyl.

4. The compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, wherein R 1 is methyl, ethyl, isopropyl or cyclopropyl.

5. The compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, wherein n and m are in each case independently of one another 1 or 2.

6. The compound of formula (I) according to claim 1 , or an agrochemically acceptable salt thereof,
wherein G is hydrogen, or
a cleavable group L selected from

wherein
R 4 is C 1 -C 4 -alkyl, and R 5 is C 1 -C 4 -alkyl, or an alkali metal ion or ion equivalent of an alkaline earth metal ion selected from Na, K, Ca or Mg.

7. The compound of formula (I) according to claim 6 , or an agrochemically acceptable salt thereof,
wherein G is hydrogen, or a cleavable group L selected from

wherein R 4 is methyl, ethyl, or isopropyl, and R 5 is methyl or ethyl, or a sodium, potassium, trimethylammonium, pyridinium, quinolinium or trimethylsulphonium cation or an ion equivalent of calcium or magnesium.

8. The compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, wherein
X is methyl, ethyl or cyclopropyl,
Y is methyl or ethyl,
R 1 is methyl, ethyl, isopropyl or cyclopropyl, and
R 3 is CH 3 CH 2 OCH 2 — or CH 3 OCH 2 .

9. The compound of formula (I) according to claim 8 or an agrochemically acceptable salt thereof, wherein
G is hydrogen,
X is methyl or ethyl, and
R 1 is methyl or cyclopropyl.

10. The compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, wherein X is methyl and Y is ethyl.

11. The compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, wherein
X is methyl, ethyl or cyclopropyl,
Y is methyl or ethyl,
R 1 is methyl, ethyl, isopropyl or cyclopropyl, and
R 2 is hydrogen,
R 3 is CH 3 CH 2 OCH 2 — or CH 3 OCH 2
n and m are in each case independently of one another 1 or 2,
G=hydrogen, or
a cleavable group L selected from

wherein R 4 is methyl, ethyl, or isopropyl, and R 5 is methyl or ethyl, or
a cation E selected from sodium, potassium or an ion equivalent of calcium or magnesium.

12. The compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, wherein
R 2 is hydrogen, and
G is a cleavable group L.

13. The compound of formula (I) and/or an agrochemically acceptable thereof according to claim 1 for controlling harmful plants.

14. The compound and/or salt according to claim 13 , wherein the compound of formula (I) or an agrochemically acceptable salt thereof is used for controlling harmful plants in crops of useful plants.

15. The compound and/or salt according to claim 14 , wherein the useful plants are transgenic useful plants.

16. An herbicidal composition comprising the compound of formula (I) according to claim 1 or an agrochemically acceptable salt thereof, and optionally an agrochemically acceptable carrier, diluent and/or solvent.

17. The herbicidal composition according to claim 16 , further comprising at least one further pesticidally active substance selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.

18. The herbicidal composition according to claim 17 , wherein the at least one further pesticidally active substance comprises a safener.

19. The herbicidal composition according to claim 16 , comprising a further herbicide.

20. A method of controlling undesired plant growth, comprising applying the compound according to claim 1 or an agrochemically acceptable salt thereof, to a plant, a part of a plant, plant seed and/or an area on which undesired plant growth takes place.

21. The method according to claim 20 , wherein the undesired plant growth is monocotyledonous weeds.

22. The method according to claim 20 , wherein plant growth of resistant grasses in useful plants is controlled, and wherein an herbicidal composition comprising said compound and/or salt is applied to the weed to be controlled.

23. The method according to claim 22 , wherein the useful plant is selected from the group consisting of wheat, barley, rye, oats, rice, sugar

Assignees

• Bayer Cropscience Ag

Inventors

• Angermann Alfred
• Lehr Stefan
• Helmke Hendrik
• Fischer Reiner
• Bojack Guido
• Rosinger Christopher Hugh
• Gatzweiler Elmar
• Dietrich Hansjörg

Classifications

• C07D209/54 Primary

  Spiro-condensed · CPC title

• C07C2601/02

  with a three-membered ring · CPC title

• C07C57/48 Primary

  having unsaturation outside the aromatic rings · CPC title

• C07C57/42

  having unsaturation outside the rings · CPC title

• A01N43/38 Primary

  condensed with carbocyclic rings · CPC title