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Synergistic pesticidal compositions and related methods

An insecticidal composition and composition technology, applied in synergistic insecticidal compositions and related fields, can solve problems such as not necessarily giving satisfactory insect control

Inactive Publication Date: 2016-08-10
DOW AGROSCIENCES LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] While alternating applications of insecticides with different modes of action can be used for good pest management practice, this approach does not necessarily give satisfactory insect control
Furthermore, even when combinations of insecticides have been studied, high synergy is not always obtained

Method used

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  • Synergistic pesticidal compositions and related methods
  • Synergistic pesticidal compositions and related methods
  • Synergistic pesticidal compositions and related methods

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Preparation of 3-((3,3,3-trifluoropropyl)thio)propionyl chloride

[0079]

[0080] A dry five-liter round-bottomed flask equipped with a magnetic stirrer, nitrogen inlet, reflux condenser and thermometer was charged in dichloromethane (CH 2 Cl 2 ) 3-((3,3,3-trifluoropropyl)thio)propionic acid in (3L) (prepared as described in PCT Publication No. WO 2013 / 062981 by Niyaz et al.) (188 g, 883 mmol). Thionyl chloride (525 g, 321 mL, 4.42 mol) was added dropwise over 50 minutes. The reaction mixture was heated to reflux (about 36°C) for two hours and then cooled to room temperature (about 22°C). The resulting mixture was concentrated on a rotary evaporator under vacuum, and then distilled (40 Torr, the product collected at a temperature of about 123°C to about 127°C) to provide the title compound (177.3g, 86%) as a clear colorless liquid ): 1 H NMR(400MHz, CDCl 3 )δ3.20(t,J=7.1Hz,2H), 2.86(t,J=7.1Hz,2H), 2.78–2.67(m,2H), 2.48–2.31(m,2H); 19 F NMR(376MHz, CDCl 3 )δ-66.42, -66.43...

Embodiment 2

[0082] Preparation of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)sulfanyl ) Propionamide (I)

[0083]

[0084] At a temperature of about 0℃ and at N 2 Next, add 3-chloro-N-ethyl-1-(pyridin-3-yl)-1H-pyrazol-4-amine (prepared as described in U.S. Publication No. 2012 / 0110702 of Yap et al.) (10.0g , 44.9mmol) in CH 2 Cl 2 (100mL), add pyridine (5.45mL, 67.4mmol), 4-dimethylaminopyridine (DMAP) (2.74g, 22.45mmol) and 3-((3,3,3-trifluoropropyl) sequentially Thio)propionyl chloride (9.91 g, 44.9 mmol). The reaction was warmed to room temperature and stirred for one hour. The reaction mixture was poured into water (100 mL), and the resulting mixture was stirred for five minutes. Transfer the mixture to a separatory funnel and separate the layers. Use CH for water phase 2 Cl 2 (3x 50mL) extraction, the combined organic extracts were subjected to sodium sulfate (Na 2 SO 4 ) Dry, filter, and concentrate in vacuo. The crude product was subjected to ...

Embodiment 3

[0086] Preparation of N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)sulfite Acyl) propionamide (II)

[0087]

[0088] Under stirring at room temperature, to N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoro A solution of propyl)thio)propionamide (I) (500 mg, 1.229 mmol) in hexafluoroisopropanol (5 mL) was added with 30% hydrogen peroxide (523 mg, 4.92 mmol). The solution was stirred for 15 minutes at room temperature. Quench it with saturated sodium sulfite solution and use CH 2 Cl 2 extraction. Silica gel chromatography (0%-10%MeOH / CH 2 Cl 2 ) Gives the title compound as a white semi-solid (495 mg, 95%): IR (film) 1660 cm -1 ; 1 H NMR(400MHz, CDCl 3 )δ8.96(d,J=2.4Hz,1H), 8.64(dd,J=4.7,1.4Hz,1H), 8.07–8.00(m,2H),7.46(ddd,J=8.3,4.8,0.7Hz ,1H),3.85-3.61(m,2H),3.23-3.08(m,1H),3.03-2.76(m,3H),2.74-2.52(m,4H),1.18(t,J=7.2Hz,3H ); ESIMS m / z 423([M+H] + ).

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Abstract

A pesticidal composition comprises a synergistically effective amount of a chloride channel activator compound and a pesticide selected from N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)thio) propanamide (I), N-(3-chloro-1-(pyridine-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl) sulfinyl)propanamide (II), or any agriculturally acceptable salt thereof. A method of controlling pests comprises applying the pesticidal composition near a population of pests. A method of protecting a plant from infestation and attack by pests comprises contacting the plant with the synergistic pesticidal composition.

Description

[0001] Priority statement [0002] This application claims the rights of the "Synergy Insecticidal Composition and Related Methods" application with the serial number 61 / 894,167 and the filing date of October 22, 2013 in the United States Provisional Patent Application. Technical field [0003] The present disclosure relates to compounds having insecticidal effects against pests in the Phyla Nematoda, Arthropoda and / or Mollusca, methods for preparing such compounds, and methods for use in such methods The field of intermediates. These compounds can be used, for example, as nematicides, acaricides, miticides, and / or molluscicides. Background technique [0004] Controlling pest populations is necessary for human health, modern agriculture, food storage and sanitation. More than 10,000 species of pests cause agricultural losses and global agricultural losses, with annual losses of billions of dollars. Therefore, there is an ongoing need for new insecticides and methods of preparing ...

Claims

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Application Information

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IPC IPC(8): A01N43/40A01N43/56A01N33/06
CPCA01N43/56A01N43/90A01N25/30A01N25/32A01N33/06C07D231/38C07D231/40C07D401/04C07D403/04Y10S424/10
Inventor L·E·戈麦斯R·亨特M·肖T·K·特鲁林格M·E·库比斯恰克J·赫伯特
Owner DOW AGROSCIENCES LLC
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