Labile esters of agrochemicals for controlled release and reduction of off-site movement

Patent metadata

Field	Value
Publication number	US-11465960-B2
Application number	US-202017008880-A
Country	US
Kind code	B2
Filing date	Sep 1, 2020
Priority date	Oct 11, 2011
Publication date	Oct 11, 2022
Grant date	Oct 11, 2022

Abstract

The present invention relates to esters of carboxylic acid agrochemicals comprising a labile protecting group and having formula (I). Certain of the esters of carboxylic acid agrochemicals do not undergo hydrolysis to a significant degree in the dark, but are cleaved to regenerate the parent carboxylic acid agrochemical when exposed to light. Others of the esters of carboxylic acid agrochemicals undergo hydrolysis under both light and dark conditions. The present invention further relates to methods for the controlled release of a carboxylic acid agrochemicals, and to methods of controlling unwanted plants comprising applying to the unwanted plants an ester of a carboxylic acid agrochemical.

First claim

What is claimed is:

1. An ester of a carboxylic acid agrochemical comprising a labile protecting group and having the formula (XV):

wherein A represents the remainder of the carboxylic acid agrochemical bonded to the carboxylic acid moiety;
R 1 is an electron-withdrawing group;
and wherein R 2 and R 3 are independently H or alkyl.

2. The ester of a carboxylic acid agrochemical of claim 1 , wherein the carboxylic acid agrochemical is a herbicide, a fungicide, an insecticide, a plant health agent, or a plant growth regulator.

3. The ester of a carboxylic acid agrochemical of claim 1 , wherein the carboxylic acid agrochemical is a herbicide selected from the group consisting of dicamba, 2,4-dichlorophenoxyacetic acid (2,4-D), fenoxaprop, fenoxaprop-P, desmedipham, cyhalofop, carfentrazone, flufenpyr, fluthiacet, fluroglycofen, pyraflufen, flumiclorac, 4-(4-chloro-2-methylphenoxy) butanoic acid (MCPB), fluroxypyr, picloram, quinclorac, benazolin, clodinafop, 4-(2,4-dichlorophenoxy)butanoic acid (2,4-DB), 2,4,5-trichlorophenoxy acetic acid (2,4,5-T), dichlorprop, dichlorprop-P, diethatyl, endothall, fluazifop, flufenpyr, flumiclorac, fluoroglycofen, haloxyfop, indole-3-acetic acid, indole-3-butyric acid, mecoprop, mecoprop-P, pyrafluren, fenoprop, triclopyr, aminopyralid, bispyribac, chlorthal, imazamethabenz, pyrothiobac, quinmerac, quizalofop, quizalofop-P, diclofop, and lactofen.

4. The ester of a carboxylic acid agrochemical of claim 1 , wherein the carboxylic acid agrochemical is dicamba.

5. The ester of a carboxylic acid agrochemical of claim 1 wherein the carboxylic acid agrochemical is 2,4-dichlorophenoxyacetic acid (2,4-D).

6. The ester of a carboxylic acid agrochemical of claim 1 , wherein the carboxylic acid agrochemical is:
a fungicide selected from the group consisting of benalaxyl and picoxystrobin;
a plant health agent selected from the group consisting of salicylic acid and 3,6-dichlorosalicylic acid; or
a plant growth regulator selected from the group consisting of cloprop and 4-chlorophenoxyacetic acid (4-CPA).

7. The ester of a carboxylic acid agrochemical of claim 1 , wherein the electron-withdrawing group is selected from nitriles, ketones, aldehydes, esters, carboxylates, and nitro.

8. The ester of a carboxylic acid agrochemical of claim 1 , wherein:
R 2 and R 3 are both H; or
one or both of R 2 and R 3 is alkyl.

9. The ester of a carboxylic acid agrochemical of claim 8 , wherein one or both of R 2 and R 3 is C 1 -C 18 alkyl.

10. The ester of a carboxylic acid agrochemical of claim 1 , wherein R 1 is selected from the group consisting of —COCH 3 , —CHO, —CN, and, —COOCH 2 CH 3 .

11. The ester of a carboxylic acid agrochemical of claim 1 , wherein:
R 1 is —COCH 3 and R 2 and R 3 are both H;
R 1 is —CHO and R 2 and R 3 are both H;
R 1 is —CN and R 2 and R 3 are both H; or
R 1 is —COOCH 2 CH 3 and R 2 and R 3 are both H.

12. The ester of a carboxylic acid agrochemical of claim 1 , wherein the carboxylic acid agrochemical is dicamba or 2,4-dichlorophenoxyacetic acid (2,4-D) and the ester is selected from the group consisting of:

13. A composition comprising an ester of a carboxylic acid agrochemical of claim 1 .

14. The composition of claim 13 , which is in the form of an emulsifiable concentrate or suspension concentrate.

15. The composition of claim 13 , further comprising one or more adjuvants selected from the group consisting of solvents, surfactants, dispersants, antifreeze agents, antifoam agents, thickeners, bacteriostats, wetting agents, dyes, and combinations or mixtures thereof.

16. The composition of claim 13 , wherein:
the solvent comprises an aromatic hydrocarbon, monochlorobenzene, a naphthalenic organic solvent, isophorone, a carboxylic acid ester, a carboxylic acid diester, a pyrrolidone, or a combination or mixture thereof;
the surfactant comprises a mixture of a nonionic surfactant and an anionic surfactant;
the surfactant comprises an ethoxylated alkyl alcohol, an ethoxylated vegetable oil, a sulfonate, or a combination or mixture thereof;
the surfactant comprises ethoxylated castor oil, an alkylbenzene sulfonate calcium salt, or a combination or mixture thereof;
the dispersant comprises a lignosulfonate, a sulfonated naphthalene-formaldehyde condensate, a polymeric dispersant, or a combination or mixture thereof;
the antifreeze agent comprises propylene glycol, glycerin, or a combination or mixture thereof;
the antifoam agent comprises a silicone antifoam agent; and/or
the thickener comprises xanthan gum, a silica, a clay, or a combination or mixture thereof.

17. The composition of claim 13 , wherein the carboxylic acid agrochemical is dicamba or 2,4-dichlorophenoxyacetic acid (2,4-D).

18. The composition of claim 13 , further comprising a second agrochemical.

19. The composition of claim 18 , wherein the second agrochemical is an herbicide.

20. A method for the controlled release of a carboxylic acid agrochemical comprising exposing an ester of a carboxylic acid agrochemical of claim 1 to artificial or natural light.

21. A method of controlling unwanted plants comprising applying to the unwanted plants an ester of a carboxylic acid agrochemical of claim 1 .

Assignees

• Monsanto Technology Llc

Inventors

• Morgenstern David A

Classifications

• C07C65/21 Primary

  containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups · CPC title

• C07D237/26

  condensed with carbocyclic rings or ring systems · CPC title

• C07D213/64

  attached in position 2 or 6 · CPC title

• A01N43/58

  1,2-Diazines; Hydrogenated 1,2-diazines · CPC title

• C07D213/63

  One oxygen atom · CPC title