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Molecules having certain pesticidal utilities, and intermediates, compositions, and processes related thereto

a technology of pesticidal utilities and molecules, applied in the field of molecules, can solve the problems of destroying more than 40% of all potential food production by weeds, affecting the quality of food, and often one of the most insidious and costly problems

Inactive Publication Date: 2014-09-18
CORTEVA AGRISCIENCE LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patent relates to molecules that can be used as pesticides to protect against pests such as nematodes, arthropods, and molluscs. These molecules can be produced using a process called aromatization, which involves adding a carbon-oxygen double bond to an alkyl group. The patent also describes the various types of substituents that can be added to the molecule, such as alkenyl, alkenyloxy, and alkoxy. The technical effect of this patent is the development of new pesticides that can protect against a wide range of pests and reduce the economic damage caused by these pests.

Problems solved by technology

Each year insects, plant pathogens, and weeds destroy more than 40% of all potential food production.
This loss occurs despite the application of pesticides and the use of a wide array of non-chemical controls, such as crop rotations and biological controls.
Plant parasitic nematodes are among the most widespread pests, and are frequently one of the most insidious and costly.
It is noted that gastropods (slugs and snails) are pests of less economic importance than insects or nematodes, but in certain areas, gastropods may reduce yields substantially, severely affecting the quality of harvested products, as well as transmitting human, animal, and plant diseases.
Termites cause damage to all kinds of private and public structures, as well as to agricultural and forestry resources.

Method used

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  • Molecules having certain pesticidal utilities, and intermediates, compositions, and processes related thereto
  • Molecules having certain pesticidal utilities, and intermediates, compositions, and processes related thereto
  • Molecules having certain pesticidal utilities, and intermediates, compositions, and processes related thereto

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C1)

[0093]

[0094]To a 100 mL round bottomed flask, equipped with a stir bar, was added copper(I) iodide (0.397 g, 2.08 mmol), 3-bromo-1H-1,2,4-triazole (4.62 g, 31.2 mmol), and cesium carbonate (6.79 g, 20.83 mmol), as solids. These solids were diluted with anhydrous dimethyl sulfoxide (34.7 mL). Then 1-iodo-4-(trifluoromethoxy)benzene (1.65 mL, 10.4 mmol) was added as a liquid. The flask was placed under nitrogen atmosphere, and the suspension was heated to an internal temperature of 100° C. for 20 hours. The reaction mixture was allowed to cool to room temperature and filtered through a pad of Celite®, washing with excess ethyl acetate (200 mL). The filtrate was poured into a brine solution (200 mL), and the layers were partitioned. The aqueous phase was extracted with additional ethyl acetate (2×100 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated. The re...

example 2

Preparation of methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (C2)

[0100]

[0101]To a 200 mL round bottomed flask, equipped with a stir bar, was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.799 g, 1.09 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (6.65 g, 26.2 mmol), and potassium acetate (4.28 g, 43.7 mmol) as solids. These solids were diluted with dioxane (100 mL). The flask was sealed and pumped and purged with nitrogen atmosphere. Then methyl 2-(4-bromophenyl)acetate (5.00 g, 21.8 mmol) was added. The reaction mixture was then warmed to an internal temperature of 70° C. for 6 hours. The reaction mixture was allowed to cool to room temperature, and was poured into a brine solution and the layers were partitioned. The aqueous phase was extracted with ethyl acetate (3×125 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting residue was purified via ...

example 3

Preparation of methyl 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetate (C3)

[0102]

[0103]To a 200 mL round bottomed flask equipped with a magnetic stir bar was added 3-bromo-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole (C1) (3.45 g, 11.2 mmol), and methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (C2) (3.71 g, 13.4 mmol). These reagents were diluted with dioxane (45.0 mL) and water (11.3 mL) and the resulting solution was sparged with nitrogen gas for 10 minutes. Tri-tert-butylphosphonium tetrafluoroborate (0.325 g, 1.12 mmol), palladium(II) acetate (0.126 g, 0.560 mmol) and cesium fluoride (3.40 g, 22.4 mmol) were added as solids. The flask was sealed and placed under nitrogen atmosphere. The reaction mixture was heated to an internal temperature of 60° C. The reaction mixture was allowed to cool to room temperature, and was poured into a brine solution and the layers were partitioned. The aqueous phase was extracted with ethyl acet...

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Abstract

This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Nematoda, Arthropoda, and / or Mollusca, processes to produce such molecules and intermediates used in such processes, compositions containing such molecules, and processes of using such molecules against such pests. These molecules may be used, for example, as nematicides, acaricides, insecticides, miticides, and / or molluscicides. This document discloses molecules having the following formula (“Formula One”).

Description

FIELD OF THE DISCLOSURE[0001]This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Nematoda, Arthropoda, and Mollusca, processes to produce such molecules and intermediates used in such processes, compositions containing such molecules, and processes of using such molecules against such pests. These molecules may be used, for example, as nematicides, acaricides, insecticides, miticides, and molluscicides.BACKGROUND OF THE DISCLOSURE[0002]“Many of the most dangerous human diseases are transmitted by insect vectors” (Rivero, A. et al., Insect Control of Vector-Borne Diseases: When is Insect Resistance a Problem? Public Library of Science Pathogens, 6(8) (2010)). Historically, vector-borne diseases, such as, malaria, dengue, yellow fever, plague, and louse-borne typhus, among others, were responsible for more human disease and death from the 1600's through the early 1900's than all other causes combined (Gubler D., Resurgent Vector-Borne Dis...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A01N47/36A01N47/34A01N25/00A01N47/12A01N53/00A01N25/32A01N55/08A01N43/653
CPCA01N47/36A01N55/08A01N47/34A01N43/653A01N47/12A01N53/00A01N25/32A01N25/00C07C211/45C07D417/12A01N47/42C07C335/16C07C335/26C07D249/08C07D277/54C07D403/10C07D285/01C07D405/10Y02A50/30C07F5/04C07C335/02C07C267/00A01N47/40C07C335/12C07D249/10C07D285/04
Inventor FISCHER, LINDSEY G.BAUM, ERICH W.CROUSE, GARY D.DEAMICIS, CARLLORSBACH, BETHPETKUS, JEFFSPARKS, THOMAS C.WHITEKER, GREGORY T.
Owner CORTEVA AGRISCIENCE LLC
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