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Fused Heterocyclic Compounds and Pest Control Agents

A technology of fused heterocycles and compounds, applied in the field of pest control agents, can solve the problems that fused heterocycles have no disclosure and usefulness is not known

Active Publication Date: 2020-06-05
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Condensed heterocyclic compounds are disclosed in, for example, Patent Document 1 to Patent Document 31, but there is nothing disclosed about the condensed heterocyclic compound of the present invention.
Moreover, its usefulness as a pest control agent, particularly as an insecticide-acaricide and an internal or external parasite control agent for mammals or birds is not known at all

Method used

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  • Fused Heterocyclic Compounds and Pest Control Agents
  • Fused Heterocyclic Compounds and Pest Control Agents
  • Fused Heterocyclic Compounds and Pest Control Agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[1485] The present invention will be further described in detail below by describing the synthesis examples and test examples of the compounds of the present invention as examples, but the present invention is not limited thereto.

[1486] The medium-pressure fractionation liquid chromatography described in the synthesis example and the reference example used the medium-pressure fractionation apparatus of Yamazen Co., Ltd.; YFLC-Wprep (flow rate 18 ml / min, silica gel 40 μm column).

[1487] In addition, the chemical shift value of the proton nuclear magnetic resonance (NMR) in the synthesis example and the reference example uses Me 4 Si (tetramethylsilane) was measured at 300 MHz (model; ECX300 or ECP300, manufactured by JEOL Corporation) as a reference substance.

[1488] The symbols in the proton nuclear magnetic resonance chemical shift values ​​have the following meanings.

[1489] s: singlet, brs: broad singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: ...

Synthetic example 1

[1491]Synthesis Example 1: 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazol[1,2-a]pyridin-2-yl]-7-(trifluoromethyl)imidazol[1 , 2-c] the synthesis of pyrimidine (compound No.1-3-001a of the present invention)

[1492] Dissolve 82 mg of 6-(trifluoromethyl)pyrimidin-4-amine in 5 ml of chlorobenzene, and add 2-bromo-1-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazole at room temperature [1,2-a]pyridin-2-yl]ethanone 200mg. After the addition was complete, the reaction mixture was stirred with heating at reflux for 9 hours. After completion of the reaction, 10 ml of a 1M aqueous sodium hydroxide solution was added to the reaction mixture, followed by extraction with ethyl acetate (10 ml×2). The obtained organic layer was dehydrated and dried in the order of saturated brine, then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium-pressure fractionation liquid chromatography eluted with n-hexane-ethyl aceta...

Synthetic example 2

[1495] Synthesis Example 2: 2-[3-(ethylthio)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl )-3H-imidazol[4,5-b]pyridine (compound No.1-1-002b of the present invention) and 2-[3-(ethylsulfonyl)-7-(trifluoromethyl)imidazol[1, Synthesis of 2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine (Compound No.1-1-002a of the present invention)

[1496] Step 1: 3-(ethylthio)-N-[2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl]-7-(trifluoromethyl)imidazol[1,2 -a] Synthesis of pyridine-2-carboxamide

[1497] Will N 2 -Methyl-5-(trifluoromethyl)pyridine-2,3-diamine 856mg was dissolved in 20ml of pyridine, and 3-(ethylthio)-7-(trifluoromethyl)imidazole[1, 2-a] 1.00 g of pyridine-2-carboxylic acid, 1.32 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 42 mg of 4-(dimethylamino)pyridine. After the addition was complete, the reaction mixture was stirred at room temperature for 6 hours. After completion of the reaction, t...

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Abstract

The present invention provides novel pest control agents, in particular insecticides or acaricides. A fused heterocyclic compound represented by formula (1) or its salt or their N-oxide [in the formula, substituted with -S(O) n R 1 D represents the ring represented by any one of D1, D2 or D3, Q represents the ring represented by any one of Q1, Q2, Q3 or Q4, and R 1 means C 1 ‑C 6 Alkyl, C 1 ‑C 6 Haloalkyl, optionally substituted with R 1a of(C 1 ‑C 6 )alkyl, C 2 ‑C 6 Alkenyl, C 2 ‑C 6 Haloalkenyl, C 2 ‑C 6 Alkynyl, C 2 ‑C 6 Halogenated alkynyl, C 3 ‑C 6 Cycloalkyl, C 3 ‑C 6 Halogenated cycloalkyl, C 3 ‑C 6 Cycloalkyl(C 1 ‑C 6 )alkyl, C 3 ‑C 6 Halogenated cycloalkyl (C 1 ‑C 6 )alkyl or hydroxyl (C 1 ‑C 6 )Alkyl, R 1a means C 1 ‑C 8 Alkoxycarbonyl group, n represents an integer of 0, 1 or 2. ].

Description

Technical field [0001] The present invention relates to novel condensed heterocyclic compounds and their salts, and pest control agents characterized by containing the compounds as active ingredients. Background technique [0002] For example, Patent Documents 1 to 31 disclose condensed heterocyclic compounds, but there is no disclosure regarding the condensed heterocyclic compound of the present invention. Furthermore, its usefulness as a pest control agent, particularly as an insecticide, acaricide, and a control agent for internal or external parasites of mammals or birds, is not known at all. [0003] existing technical documents [0004] patent documents [0005] Patent Document 1: International Publication No. 2016 / 005263 [0006] Patent Document 2: International Publication No. 2015 / 198859 [0007] Patent Document 3: International Publication No. 2015 / 133603 [0008] Patent Document 4: International Publication No. 2015 / 121136 [0009] Patent Document 5: Interna...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A01N43/90A01P7/02A01P7/04A61K31/437A61K31/5025A61K31/519A61P33/00A61P33/14C07D519/00
CPCA01N43/90A61K31/437A61K31/5025A61K31/519C07D471/04C07D513/04C07D519/00A61P33/00A61P33/14
Inventor 工藤隆生舞鹤幸裕田中绫乃能登健吉松井洋人小林正树
Owner NISSAN CHEM IND LTD
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