Plant growth regulating compounds

Patent metadata

Field	Value
Publication number	US-9751867-B2
Application number	US-201515121074-A
Country	US
Kind code	B2
Filing date	Feb 24, 2015
Priority date	Feb 26, 2014
Publication date	Sep 5, 2017
Grant date	Sep 5, 2017

Abstract

The present invention relates to novel heterocyclic derivatives of Formula (I), to processes and intermediates for preparing them, to plant growth regulator and seed germination promoting compositions comprising them and to methods of using them for controlling the growth of plants and/or promoting the germination of seeds.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
W 1 and W 2 are each independently O or S;
R 1 and R 2 are each independently hydrogen, halogen, nitro, hydroxyl, cyano, substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; or
R 1 and R 2 together with the carbon atoms to which they are joined form a saturated or unsaturated, aromatic or non-aromatic, substituted or unsubstituted 3-7-membered carbocycle; or,
R 1 and R 2 together with the carbon atoms to which they are joined form a saturated or unsaturated, aromatic or non-aromatic, substituted or unsubstituted 4-7-membered carbocycle fused to another saturated or unsaturated, aromatic or non-aromatic, substituted or unsubstituted 3-7-membered carbocycle or heterocycle;
X 1 and X 2 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, halogen, C 1 -C 6 alkoxy, cyano, nitro, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl or C 1 -C 6 alkylthio;
Y 2 is oxygen, or —(CR 4 R 7 ) p (CR 3 R 8 ) n N(R 6 )—, wherein n is 0 or 1, and p is 0 or 1;
R 3 and R 4 are each independently hydrogen, halogen, nitro, hydroxyl, cyano, substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 1 -C 6 alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; or,
R 3 and R 4 together with the carbon atoms to which they are joined form a saturated or unsaturated, non-aromatic, substituted or unsubstituted 3-7-membered carbocycle; or
R 3 and R 4 together with the carbon atoms to which they are joined form a saturated or unsaturated, aromatic or non-aromatic, substituted or unsubstituted 4-7-membered carbocycle fused to another saturated or unsaturated, aromatic or non-aromatic, substituted or unsubstituted 3-7-membered carbocycle; or
R 2 and R 3 together with the carbon atoms to which they are joined form (i) a saturated or unsaturated, non-aromatic, substituted or unsubstituted 3-7-membered carbocycle, or (ii) a saturated or unsaturated, aromatic or non-aromatic, substituted or unsubstituted 4-7-membered carbocycle fused to another saturated or unsaturated, aromatic or non-aromatic, substituted or unsubstituted 3-7-membered carbocycle;
R 7 and R 8 are each independently selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, halogen, C 1 -C 6 alkoxy, aryloxy, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylthio;
Y 1 is S or NR 5 ;
R 5 and R 6 are each independently hydrogen, C 1 -C 6 alkoxy, hydroxyl, amine, N—C 1 -C 6 alkylamine, N,N-di-C 1 -C 6 alkylamine, substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 3 -C 6 cycloalkyl, substituted or unsubstituted C 2 -C 6 alkenyl, substituted or unsubstituted C 2 -C 6 alkynyl, substituted or unsubstituted C 1 -C 8 alkylcarbonyl, substituted or unsubstituted C 1 -C 8 alkoxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclyl, substituted or unsubstituted benzyl; and
X 3 and X 4 are each independently selected from hydrogen, C 1 -C 6 alkyl, C 2 -C 3 alkynyl, C 1 -C 6 haloalkyl, halogen, C 1 -C 6 alkoxy, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylthio; or
X 3 and X 4 together with the carbon atoms to which they are attached form a C 5 - or C 6 -cycloalkyl;
or an agrochemically acceptable salt or N-oxide thereof.

2. The compound according to claim 1 , wherein W 1 is O and W 2 is O.

3. The compound according to claim 1 , wherein R 1 , R 2 and R 3 are each independently hydrogen, substituted or unsubstituted C 1 -C 6 alkyl, substituted or unsubstituted C 1 -C 6 haloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; or,
R 1 and R 2 , or R 2 and R 3 , together with the carbon atoms to which they are joined form a substituted or unsubstituted, saturated or unsaturated, 5-6-membered carbocycle; or
R 1 and R 2 , or R 2 and R 3 , together with the carbon atoms to which they are joined form a substituted or unsubstituted, saturated or unsaturated 5-6-membered carbocycle fused to a further unsaturated aromatic or non-aromatic, substituted or unsubstituted 5-6-membered carbocycle or heterocycle.

4. The compound according to claim 1 , which is Formula (IA)

5. The compound according to claim 1 , wherein Y 2 is —N(R 6 )—.

6. The compound according to claim 1 , wherein R 6 is hydrogen, substituted or unsubstituted C 1 -C 6 alkyl, C 1 -C 8 alkylcarbonyl, C 1 -C 8 alkoxycarbonyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl.

7. The compound according to claim 1 , wherein X 3 and X 4 are each independently selected from hydrogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, and halogen.

8. The compound according to claim 1 , wherein Y 1 is NR 5 .

9. The compound according to claim 1 , wherein R 5 is hydrogen, substituted or unsubstituted C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 alkoxy, substituted or unsubstituted phenyl, or substituted or unsubstituted benzyl.

10. A plant growth regulating or seed germination promoting composition, comprising a compound according to claim 1 , and an agriculturally acceptable formulation adjuvant.

11. A method for regulating the growth of plants at a locus, said method comprising applying to the locus a compound according to claim 1 .

12. A method for promoting the germination of seeds, comprising applying to the seeds, or a locus containing the seeds, a compound according to claim 1 .

13. A method for controlling weeds comprising applying to a locus containing weed seeds, a compound according to claim 1 , allowing the weed seeds to germinate, and then applying to the locus a post-emergence herbicide.

Assignees

• Syngenta Participations Ag

Inventors

• Lachia Mathilde Denise
• Screpanti Claudio
• De Mesmaeker Alain
• Lumbroso Alexandre Franco Jean Camille
• Rendine Stefano

Classifications

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title

• A01N43/36 Primary

  five-membered rings · CPC title

• A01N43/38

  condensed with carbocyclic rings · CPC title

• C07D207/36

  Oxygen or sulfur atoms · CPC title