Novel halogen-substituted compounds

A compound, a representative technology, applied in the field of new halogen-substituted compounds, which can solve problems such as resistance

Inactive Publication Date: 2017-05-31
BAYER CROPSCIENCE AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, resistance to

Method used

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  • Novel halogen-substituted compounds

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preparation example Construction

[2319] Preparation of starting materials

[2320] Synthesis of 3-(1-fluorocyclopropyl)-1-methyl-1H-pyrazole (10)

[2321]

[2322] (2E)-3-(Dimethylamino)-1-(1-fluorocyclopropyl)prop-2-en-1-one (16)

[2323] According to the description of (2E)-3-(dimethylamino)-1-(cyclopropyl)prop-2-en-1-one in J.Med.Chem.2011,54,7974, by (15) Initial synthesis of (2E)-3-(dimethylamino)-1-(1-fluorocyclopropyl)prop-2-en-1-one (16).

[2324] HPLC-MS ＊) : logP=1.16, mass (m / z)=158[M+H] + .

[2325] 1 H-NMR (400MHz, DMSO-d6): 7.63(d, 1H), 5.47-5.43(m, 1H), 3.12(s, 3H), 2.84(s, 3H), 1.28-1.10(m, 4H)

[2326] 3-(1-fluorocyclopropyl)-1-methyl-1H-pyrazole (10)

[2327] Dissolve 685 mg (4.35 mmol) of (2E)-3-(dimethylamino)-1-(1-fluorocyclopropyl)prop-2-en-1-one (16) in 10 mL of EtOH and add 0.35 mL Methylhydrazine (6.53 mmol). The mixture was stirred overnight at 60 °C. 1.16 mL methylhydrazine (2.18 mmol) was added and stirring was continued for a further 5 hours at 60°C. The mixtur...

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Abstract

The invention relates inter alia to halogen-substituted compounds of the general formula (I), in which the substituents A1, R1-R3 and Z1-Z3 have the meanings given in the description. Also described are processes for preparing the compounds of the formula (I) and possible intermediates for the preparation of these compounds. The compounds according to the invention are particularly suitable for controlling insects, arachnids and nematodes in agriculture and ectoparasites in veterinary medicine.

Description

[0001] technical background [0002] The present application relates to novel halogen-substituted compounds, processes for their preparation and their use for controlling animal pests, in particular arthropods, and especially insects, arachnids and nematodes. [0003] Certain halogen-substituted compounds are known to have herbicidal activity (see J. Org. Chem. 1997, 62(17), 5908-5919; J. Heterocycl. Chem. 1998, 35(6), 1493-1499; WO 2004 / 035545; WO 2004 / 106324; US2006 / 069132; WO 2008 / 029084). [0004] Furthermore, certain halogen-substituted compounds are known to be insecticidal (EP 1 911 751, WO2012 / 069366, WO2012 / 080376 & WO2012 / 107434). [0005] Additionally, certain halogen-substituted compounds are known to have cytokine inhibitory activity (WO 2000 / 07980). [0006] Modern crop protection compositions must meet many requirements, such as regarding efficacy, persistence and spectrum of action of their action as well as possible uses. Questions of toxicity, combinability...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D403/04C07D231/12A01N43/56A01N51/00A01P7/04A01P5/00A01P7/02
CPCC07D401/14A01N43/56C07D403/04A01N51/00C07D231/12C07D231/16A61P33/00A61P33/02A61P33/10A61P33/14
Inventor M·毛埃T·哈施内克R·菲舍尔T·布雷特施奈德J·J·哈恩A·迪克W·哈伦巴赫H-G·施瓦茨J·库伯灵W·胡布施
Owner BAYER CROPSCIENCE AG
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