Beta-lactams and their use as herbicides

Patent metadata

Field	Value
Publication number	US-12389910-B2
Application number	US-202117917352-A
Country	US
Kind code	B2
Filing date	Apr 1, 2021
Priority date	Apr 14, 2020
Publication date	Aug 19, 2025
Grant date	Aug 19, 2025

Abstract

The invention relates to compounds of formula (I), and their use as herbicides. In said formula, R 1 to R 9 represent groups such as hydrogen, halo-gen or organic groups such as alkyl, alkenyl, alkynyl, or alkoxy; X is a bond or a divalent unit; Y is hydrogen, cyano, hydroxyl or a linear or cyclic organic group. The invention further refers to a composition comprising such compound and to the use thereof for controlling unwanted vegetation.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein the substituents have the following meanings:
R 1 hydrogen, (C 1 -C 3 )-alkyl, (C 3 -C 4 )-cycloalkyl, (C 1 -C 3 )-haloalkyl, (C 2 -C 3 )-alkenyl, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy;
R 2 hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy;
R 3 hydrogen, halogen, nitro, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, hydroxy-(C 1 -C 3 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 3 -C 5 )-halocycloalkyl, hydroxy-(C 3 -C 5 )-cycloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, (C 1 -C 3 )-alkoxycarbonyl, (C 2 -C 3 ) alkenyl, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 ) alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, (C 1 -C 3 )-alkylsulfonyl;
R 4 hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 3 -C 4 )-halocycloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 3 )-alkylthio;
R 5 hydrogen, halogen, nitro, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, hydroxy-(C 1 -C 3 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 3 -C 5 )-halocycloalkyl, hydroxy-(C 3 -C 5 )-cycloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy, (C 1 -C 3 )-alkoxycarbonyl, (C 2 -C 3 ) alkenyl, (C 2 -C 3 )-haloalkenyl, (C 2 -C 3 ) alkynyl, (C 2 -C 3 )-haloalkynyl, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, (C 1 -C 3 )-alkylsulfonyl;
R 6 hydrogen, halogen, hydroxyl, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy;
R 7 hydrogen, fluorine, cyano, or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 6 )-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano and (C 1 -C 6 )-alkoxy;
R 8 , R 9 each independently hydrogen, halogen, cyano, or (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, and cyano; or
R 8 and R 9 form, together with the carbon atom to which they are bound, a saturated, partially or fully unsaturated three to five-membered ring containing, in addition to this carbon atom, q carbon atoms and n oxygen atoms;
X a bond (X 0 ) or a divalent unit from the group consisting of (X 1 ), (X 2 ), (X 3 ), (X 4 ), (X 5 ), and (X 6 ):

R 10 -R 15 each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO 2 R e , CONR b R d , NR b CO 2 R e , R a , or (C 1 -C 6 )-alkyl, (C 3 -C 5 )-cycloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano, or (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkoxy, (C 3 -C 6 )-alkenyloxy, (C 3 -C 6 )-alkynyloxy, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, (C 1 -C 3 )-alkylsulfonyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C 1 -C 2 )-alkoxy;
Y hydrogen, cyano, hydroxyl, Z,
or
(C 1 -C 12 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C 12 )-alkenyl or (C 2 -C 12 )-alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR d , Z, OZ, NHZ, S(O) n R a , SO 2 NR b R d , SO 2 NR b COR e , CO 2 R e , CONR b R h , COR b , CONR e SO 2 R a , NR b R e , NR b COR e , NR b CONR e R e , NR b CO 2 R e , NR b SO 2 R e NR b SO 2 NR b R e , OCONR b R e , OCSNR b R e , POR f R f and C(R b )═NOR e ;

Z a three-, four-, five- or six-membered saturated, partly unsaturated, fully unsaturated or aromatic ring, except phenyl, which is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and which is substituted by m radicals from the group consisting of CO 2 R e , CONR b R h , S(O) n R a , SO 2 NR b R d , SO 2 NR b COR e , COR b , CONR e SO 2 R a , NR b R e , NR b COR e , NR b CONR e R e , NR b CO 2 R e , NR b SO 2 R e NR b SO 2 NR b R e , OCONR b R e , OCSNR b R e , POR f R f , C(R b )═NOR e , R b , R c , R e and R f , and where the sulfur atoms and carbon atoms bear n oxo groups;
R a (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C 1 -C 3 )-alkoxy;
R b hydrogen, (C 1 -C 3 )-alkoxy or R a ;
R c fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O) n R a or (C 1 -C 6 )-alkoxy, (C 3 -C 6 )-alkenyloxy or (C 3 -C 6 )-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (C 1 -C 2 )-alkoxy;
R d hydrogen or (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 3 )-alkyl, phenyl-(C 1 -C 3 )-alkyl, furanyl-(C 1 -C 3 )-alkyl or (C 2 -C 4 )-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO 2 R a , CONR b R h , (C 1 -C 2 )-alkoxy, (C 1 -C 3 )-alkylthio, (C 1 -C 3 )-alkylsulfinyl, (C 1 -C 3 )-alkylsulfonyl, phenylthio, phenylsulfinyl, and phenylsulfonyl;
R e R d ;
R f (C 1 -C 3 )-alkyl or (C 1 -C 3 )-alkoxy;
R h hydrogen or (C 1 -C 6 )-alkyl, (C 1 -C 2 )-alkoxy, (C 3 -C 6 )-cycloalkyl, (C 2 -C 4 )-alkenyl, (C 1 -C 6 )-alkoxycarbonyl-(C 1 -C 6 )-alkyl, or (C 2 -C 4 )-alkynyl each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO 2 R a and (C 1 -C 2 )-alkoxy;
m 0, 1, 2, 3, 4 or 5;
n 0, 1 or 2;
q 1, 2, 3, or 4;
r 1, 2, 3, 4, 5 or 6;
including their agriculturally acceptable salts, amides, esters or thioesters, provided the compounds of formula (I) have a carboxyl group.

2. The compound as claimed in claim 1 , wherein wherein the substituents have the following meaning:
R 1 hydrogen.

3. The compound as claimed in claim 1 , wherein wherein the substituents have the following meaning:
R 2 hydrogen, halogen, (C 1 -C 3 )-alkyl;
R 6 hydrogen, halogen, (C 1 -C 3 )-alkyl.

4. The compound as claimed in claim 1 , wherein wherein the substituents have the following meaning:
R 3 hydrogen, halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkoxy;
R 5 hydrogen, halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkoxy.

5. The compound as claimed in claim 1 , wherein wherein the substituents have the following meaning:
R 4 hydrogen, halogen.

6. The compound as claimed in claim 1 , wherein wherein the substituents have the following meaning:
R 7 (C 1 -C 2 )-alkyl, cyclopropyl, (C 1 -C 2 )-haloalkyl, (C 2 -C 3 )-alkenyl, (C 1 -C 2 )-alkoxy.

7. The compound as claimed in claim 1 , wherein wherein the substituents have the following meaning:
R 8 hydrogen, halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl;
R 9 hydrogen, halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl.

8. The compound as claimed in claim 1 , wherein wherein the substituents have the following meaning:
X a bond.

9. The compound as claimed in claim 1 , wherein wherein the substituents have the following meaning:
X a bond;
Y (C 1 -C 8 )-alkyl, (C 3 -C 8 )-cycloalkyl, (C 2 -C

Assignees

• Basf Se

Inventors

• Zimmermann Gunther
• Kordes Markus
• Seiser Tobias
• Kraemer Gerd
• Newton Trevor William
• Campe Ruth
• Seitz Thomas
• Johnen Philipp Rudi

Classifications

• C07D205/08 Primary

  with one oxygen atom directly attached in position 2, e.g. beta-lactams · CPC title

• A01P13/00

  Herbicides; Algicides · CPC title

• A01N43/44 Primary

  three- or four-membered rings · CPC title