Molecules haveing pesticidal utiliy and intermediates, compositions and processes related thereto

a technology of pesticidal utiliy and molecules, applied in the field of molecules having pesticidal utiliy and intermediates, compositions and processes related thereto, can solve the problems of destroying more than 40% of all food production, prone to loss, and often one of the most insidious and costly problems

Inactive Publication Date: 2019-05-23
DOW AGROSCIENCES LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Each year insects, plant pathogens, and weeds, destroy more than 40% of all 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 other arthropods or nematodes, but in certain places, they 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 types of private and public structures, as well as to agricultural and forestry resources.
Consequently, for many reasons, including those mentioned above, there is an on-going need for the costly (estimated to be about US$256 million per pesticide in 2010), time-consuming (on average about 10 years per pesticide), and difficult, development of new pesticides (CropLife America).

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of trans-2-Chloro-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-carboxamido)-N-(2-methyl-4-(2,2,2-trifluoroacetamido)phenyl)benzamide (F1061)

[0235]

[0236]To a solution of trans-N-(4-amino-2-methylphenyl)-2-chloro-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-carboxamido)benzamide (DP1) (0.100 g, 0.179 mmol) and triethylamine (0.037 mL, 0.269 mmol) in dichloromethane (2.0 mL) was added trifluoroacetic anhydride (0.030 mL, 0.215 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was directly loaded onto a Celite® cartridge. Purification by flash column chromatography using 0-40% ethyl acetate / hexanes as eluent afforded the title compound as a white solid (0.080 g, 68%).

[0237]The following compounds were prepared in like manner to the procedure outlined in Example 1:

trans-2-Chloro-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-(2,2-difluoroacetamido)-2-methylphenyl)benzamide (F1062)

[0238]

[0239]...

example 2

Preparation of N-(3-acetamido-2,4-difluorophenyl)-2-chloro-5-((1R,3R)-2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-carboxamido)benzamide (F1083)

[0276]

[0277]To a solution of N-(3-amino-2,4-difluorophenyl)-2-chloro-5-((1R,3R)-2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-carboxamido)benzamide (DP2) (0.06 g, 0.104 mmol) in pyridine (0.30 mL, 3.71 mmol) stirred at room temperature was added acetic anhydride (9.77 μl, 0.104 mmol). The reaction mixture was stirred at room temperature for 18 hours, was quenched with water (3 mL), and was extracted with ethyl acetate (10 mL). The organic layer was washed with hydrochloric acid (1 N) and brine before being poured through a phase separator. The organic layer was concentrated under reduced pressure to give a residue. Purification by column chromatography using 0-30% ethyl acetate / hexanes as eluent afforded the title compound as a white solid (0.043 g, 67%).

[0278]The following compounds were prepared in like manner to the procedure out...

example 3

Preparation of 2-chloro-5-((1R,3R)-2,2-dichloro-3-(4-fluoro-3-(trifluoromethyl)phenyl)cyclopropane-1-carboxamido)-N-(2,4-difluoro-3-(2,2,2-trifluoroacetamido)phenyl)benzamide (F1169)

[0313]

[0314]Trifluoroacetic anhydride (0.035 g, 0.251 mmol) was added dropwise to a stirred solution of N-(3-amino-2,4-difluorophenyl)-2-chloro-5-((1R,3R)-2,2-dichloro-3-(4-fluoro-3-(trifluoromethyl)phenyl)cyclopropane-1-carboxamido)benzamide (DP9) (0.100 g, 168 mmol), and triethylamine (0.051 g, 0.503 mmol) in anhydrous dichloromethane (3 mL). The solution was stirred for 12 hours at 23° C. and concentrated. Purification by silica gel flash chromatography gave the title compound as a white foam (0.084 g, 69%).

[0315]The following compounds were prepared in like manner to the procedure outlined in Example 3:

2-Chloro-N-(3-(2-chloro-2,2-difluoroacetamido)-2,4-difluorophenyl)-5-((1R,3R)-2,2-dichloro-3-(4-fluoro-3-(trifluoromethyl)phenyl)cyclopropane-1-carboxamido)benzamide (F1170)

[0316]

[0317]Isolated as a wh...

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PUM

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Abstract

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

Description

CROSS-REFERENCES TO RELATED APPLICATIONS[0001]This Application is a continuation of, and claims the benefit of, U.S. nonprovisional application Ser. No. 15 / 727,878, which was filed Oct. 9, 2017, and is now allowed, and which claims the benefit of, and priority from, U.S. provisional applications Ser. Nos. 62 / 407,092 and 62 / 407,118; all of which were filed on Oct. 12, 2016. The entire contents of all of the above-identified applications are hereby incorporated by reference into this Application.FIELD OF THIS DISCLOSURE[0002]This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca, and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests. These pesticidal compositions may be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides.BACKGROU...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A01N53/00C07D239/42C07D237/20C07D333/38C07D213/81C07C381/00C07C255/19C07C237/42C07C337/06C07C311/10C07C311/09C07C281/06C07C281/02C07C271/28C07C271/22C07D213/77C07C255/60C07D307/68C07C237/52C07C243/38C07C255/46C07C255/58C07C271/18C07C271/66C07C311/21C07C311/48C07C317/24
CPCA01N53/00C07C2601/02C07D237/20C07D333/38C07D213/81C07C381/00C07C255/19C07C237/42C07C337/06C07C311/10C07C311/09C07C281/06C07C281/02C07C271/28C07C271/22C07D213/77C07C255/60C07D307/68C07C237/52C07C243/38C07C255/46C07C255/58C07C271/18C07C271/66C07C311/21C07C311/48C07C317/24C07C2601/04C07C2601/16C07C2601/08C07D239/42Y02A50/30C07C233/59C07C233/66C07C237/24C07C237/40
Inventor HEEMSTRA, RONALD J.ROSS, JR., RONALDMARTIN, TIMOTHY P.VERMEULEN, NICOLAASDAEUBLE, SR., JOHN F.ECKELBARGER, JOSEPH D.NOLAN, ALEXGRAY, KAITLYNDEMETER, DAVID A.HUNTER, RICKYTRULLINGER, TONY K.
Owner DOW AGROSCIENCES LLC
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