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

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

US20190150452A1Inactive Publication Date: 2019-05-23DOW AGROSCIENCES LLC
1 Cites 3 Cited by

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 CeliteĀ® 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 Ī¼l, 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 23Ā° 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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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 (ā€œFormula Oneā€).

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
23 May 2019
Publication
US20190150452A1
IPC
A01N53/00; C07D239/42; C07D237/20; C07D333/38; C07D213/81; C07C381/00; C07C255/19; C07C237/42; C07C337/06; C07C311/10; C07C311/09; C07C281/06; C07C281/02; C07C271/28; C07C271/22; C07D213/77; C07C255/60; C07D307/68; C07C237/52; C07C243/38; C07C255/46; C07C255/58; C07C271/18; C07C271/66; C07C311/21; C07C311/48; C07C317/24
CPC
A01N53/00; C07C2601/02; C07D237/20; C07D333/38; C07D213/81; C07C381/00; C07C255/19; C07C237/42
Inventors
HEEMSTRA, RONALD J.; ROSS, JR., RONALD