13959-02-9

Basic information

• Product Name: 3-Bromoisonicotinic acid
• Synonyms: 3-Bromopyridine-4-carboxylic acid, 3-Bromo-4-carboxypyridine;3-Bromopyridine-4-carboxylicacid,97%;3-BROMOPYRIDINE-4-CARBOXYLIC ACID;3-BROMOISONICOTINIC ACID;3-BROMO-4-PYRIDINECARBOXYLIC ACID;IFLAB-BB F1957-0038;4-Pyridinecarboxylic acid, 3-bromo-;Vitamin E
• CAS NO: 13959-02-9
• Molecular Formula: C₆H₄BrNO₂
• Molecular Weight: 202.01
• EINECS: -0
• Product Categories: blocks;Bromides;Carboxes;Pyridines;Pyridines, Pyrimidines, Purines and Pteredines;Picolinic acid series;Building Blocks;C5 to C6;C6 to C7;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 13959-02-9.mol
• Article Data: 14

Chemical Properties

• Melting Point: 237-238
• Boiling Point: 403.1 at 760 mmHg
• Flash Point: 197.
• Appearance: /
• Density: 1.813 g/cm³
• Vapor Pressure: 3.19E-07mmHg at 25°C
• Refractive Index: 1.616
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 0.60±0.10(Predicted)
• CAS DataBase Reference: 3-Bromoisonicotinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromoisonicotinic acid(13959-02-9)
• EPA Substance Registry System: 3-Bromoisonicotinic acid(13959-02-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39-22
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 13959-02-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromoisonicotinic acid is used as an intermediate in the synthesis of various pharmaceuticals for its potential anti-inflammatory and antitumor activities. It contributes to the development of new drugs by providing a structural foundation that can be further modified to enhance therapeutic effects.
Used in Agrochemical Industry:
3-Bromoisonicotinic acid is used as a precursor in the production of agrochemicals, specifically in the synthesis of pesticides and other crop protection agents. Its incorporation into these products helps improve their efficacy in controlling pests and diseases, thereby supporting agricultural productivity.
Used in Organic Synthesis:
3-Bromoisonicotinic acid is used as a building block in organic synthesis to create more complex chemical structures. Its unique properties allow it to be a versatile component in the formation of various organic compounds, expanding the scope of chemical research and development.
It is important to handle 3-Bromoisonicotinic acid with care and use proper protective equipment when working with it in a laboratory setting to ensure safety.

InChI:InChI=1/C6H4BrNO2/c7-5-3-8-2-1-4(5)6(9)10/h1-3H,(H,9,10)

Synthetic route

pyridine-4-carboxylic acid (55-22-1) → 3-bromoisonicotinic acid (13959-02-9)

Conditions	Yield
With bromine In methanol at 30 - 45℃; for 5h; Temperature;	96.3%

3-Bromo-4-methylpyridin (3430-22-6) → 3-bromoisonicotinic acid (13959-02-9)

Conditions	Yield
Stage #1: 3-Bromo-4-methylpyridin With Co0.27CuO3; water Stage #2: With oxygen at 90℃;	90%
With potassium permanganate In water Heating / reflux;	32%
With hydrogenchloride; potassium permanganate In water

3-Bromopyridine (626-55-1) + carbon dioxide (124-38-9) → 3-bromoisonicotinic acid (13959-02-9)

Conditions	Yield
Stage #1: 3-Bromopyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran at 20℃; Inert atmosphere;	10%
Stage #1: 3-Bromopyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -60℃; for 0.5h; Cooling with acetone-dry ice; Stage #2: carbon dioxide In tetrahydrofuran; hexane
Stage #1: 3-Bromopyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -60℃; for 0.5h; Stage #2: carbon dioxide In tetrahydrofuran; hexane at 20℃; Stage #3: With hydrogenchloride In tert-butyl methyl ether; water pH=3;

3-bromo-N-phenylpyridine-4-carboxamide (71541-34-9) → 3-bromoisonicotinic acid (13959-02-9)

Conditions	Yield
With hydrogenchloride for 15h; Heating;

N-phenylisonicotinamide (3034-31-9) → 3-bromoisonicotinic acid (13959-02-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) n-BuLi, 2.) 1,2-dibromoethane / 1.) THF, -78 deg C - 0.5 h, room temperature - 1 h, 2.) THF, -78 deg C - 1 h, room temperature - 2 h 2: aq. HCl / 15 h / Heating View Scheme

3-Bromopyridine (626-55-1) → 3-bromoisonicotinic acid (13959-02-9)

Conditions	Yield
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -40℃; for 0.5h; Cooling with acetone-dry ice; Stage #2: 3-Bromopyridine In tetrahydrofuran; hexane at -60℃; for 0.5h; Stage #3: With hydrogenchloride In water for 1h; pH=3; Cooling with ice;

2-aminopyridine-5-boronic acid pinacol ester (827614-64-2) + 3-bromoisonicotinic acid (13959-02-9) → 6'-amino-[3,3'-bipyridine]-4-carboxylic acid

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 120℃; for 16h; Inert atmosphere;	100%

3-bromoisonicotinic acid (13959-02-9) + pinacol vinylboronate (75927-49-0) → 3-vinyl-4-picolinic acid

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;	100%

3-bromoisonicotinic acid (13959-02-9) → 3-Aminopyridine-4-carboxylic acid (7579-20-6)

Conditions	Yield
With ammonium hydroxide; copper(l) iodide at 100 - 105℃; for 8h; Time; Autoclave;	95.2%

ethanol (64-17-5) + 3-bromoisonicotinic acid (13959-02-9) → ethyl 3-bromopyridine-4-carboxylate (13959-01-8)

Conditions	Yield
With sulfuric acid for 12h; Reflux;	95%
With sulfuric acid for 12h; Reflux;	88%
With sulfuric acid Reflux; Inert atmosphere;	78%

3-bromoisonicotinic acid (13959-02-9) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 3-bromoisonicotinate (59786-31-1)

Conditions	Yield
In methanol; diethyl ether; toluene for 2h; Inert atmosphere; Schlenk technique;	94%
In methanol; diethyl ether; toluene at 20℃; for 2h;

4-amino-5-(2,3,5-trichlorophenyl)-4H-[1,2,4]triazole-3-thiol (1029491-80-2) + 3-bromoisonicotinic acid (13959-02-9) → 6-(3-bromopyridin-4-yl)-3-(2,3,5-trichlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

Conditions	Yield
With trichlorophosphate Heating;	84%

2-isopropyliodobenzene (19099-54-8) + 3-bromoisonicotinic acid (13959-02-9) + diphenyl acetylene (501-65-5) → 7-isopropyl-5,6-diphenylbenzo[h]isoquinoline

Conditions	Yield
With norborn-2-ene; palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 130℃; for 20h; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction;	80%

3-bromoisonicotinic acid (13959-02-9) + aniline (62-53-3) → 3-bromo-N-phenylpyridine-4-carboxamide (71541-34-9)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	79%

chloroformic acid ethyl ester (541-41-3) + 3-bromoisonicotinic acid (13959-02-9) → ethyl 3-bromopyridine-4-carboxylate (13959-01-8) + 3-bromopyridine-4-carboxamide (13958-99-1)

Conditions	Yield
Stage #1: chloroformic acid ethyl ester; 3-bromoisonicotinic acid With triethylamine In tetrahydrofuran at 0℃; for 1h; Stage #2: With ammonia In tetrahydrofuran for 0.25h;	A 5% B 78%

6-amino-4-methylquinolin-2-ol (90914-95-7) + 3-bromoisonicotinic acid (13959-02-9) → 3-bromo-N-(2-hydroxy-4-methyl-6-quinolyl)pyridine-4-carboxamide

Conditions	Yield
With dmap; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 80℃; for 1h;	78%

4-[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1,2,3-triazol-1-yl]piperidine + 3-bromoisonicotinic acid (13959-02-9) → (3-bromopyridin-4-yl)-{4-[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1H-1,2,3-triazol-1-yl]piperidin-1-yl}methanone

Conditions	Yield
Stage #1: 3-bromoisonicotinic acid With 1,1'-carbonyldiimidazole In 1,4-dioxane at 80℃; for 0.5h; Stage #2: 4-[4-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-1,2,3-triazol-1-yl]piperidine In 1,4-dioxane at 100℃; for 3h;	75%

2-isopropyliodobenzene (19099-54-8) + 3-bromoisonicotinic acid (13959-02-9) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → 7-isopropylbenzo[h]isoquinoline

Conditions	Yield
With palladium diacetate; caesium carbonate; tricyclohexylphosphine In 1,4-dioxane at 130℃; for 18h; Schlenk technique; Sealed tube; Inert atmosphere;	72%

3-bromoisonicotinic acid (13959-02-9) + N-[(diphenylphosphinoyl)methyl]-N-methylamine (122365-23-5) → 3-chloro-N-(diphenylphosphinoylmethyl)-N-methylisonicotinamide (380227-43-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 2h; Ambient temperature;	69%

pyrrolidine (123-75-1) + 3-bromoisonicotinic acid (13959-02-9) → (3-bromopyridin-4-yl)(pyrrolidin-1-yl)methanone (1357094-61-1)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 3h;	68.7%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + 3-bromoisonicotinic acid (13959-02-9) → 3-bromo-N-methyl-N-(methyloxy)-4-pyridinecarboxamide (909532-61-2)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane; water at 20℃; for 16h;	67%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 16h;	67%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; Schlenk technique;

3-bromoisonicotinic acid (13959-02-9) + diethyl malonate (105-53-3) → 3-[2-ethoxy-1-(ethoxycarbonyl)-2-oxoethyI]isonicotinic acid (929301-89-3)

Conditions	Yield
Stage #1: 3-bromoisonicotinic acid; diethyl malonate With sodium hydride; copper(I) bromide at 80℃; for 2h; Stage #2: With hydrogenchloride In water pH=4;	66%

diazomethane (186581-53-3, 908094-01-9) + 3-bromoisonicotinic acid (13959-02-9) → methyl 3-bromoisonicotinate (59786-31-1)

Conditions	Yield
In tetrahydrofuran; methanol at 0 - 20℃; for 1h; Inert atmosphere;	66%

4-methoxy-aniline (104-94-9) + 3-bromoisonicotinic acid (13959-02-9) → 3-bromo-N-(4-methoxyphenyl)pyridine-4-carboxamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	64%

methanol (67-56-1) + 3-bromoisonicotinic acid (13959-02-9) → methyl 3-bromoisonicotinate (59786-31-1)

Conditions	Yield
With sulfuric acid Heating / reflux;	62%
Stage #1: methanol; 3-bromoisonicotinic acid With sulfuric acid Reflux; Stage #2: With sodium hydrogencarbonate; sodium hydroxide In water at 0℃; pH=7 - 8;
With sulfuric acid for 14h; Reflux;
With sulfuric acid Cooling with ice; Reflux;	335.3 mg

5-iodoquinoline (1006-50-4) + 4,4'-dimethoxydiphenylacetylene (2132-62-9) + 3-bromoisonicotinic acid (13959-02-9) → 5,6-bis(4-methoxyphenyl)isoquinolino[7,8-f]quinoline

Conditions	Yield
With norborn-2-ene; palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 130℃; for 20h; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction;	55%

3,3-difluoroazetidine hydrochloride (288315-03-7) + 3-bromoisonicotinic acid (13959-02-9) → (3-bromopyridin-4-yl)(3,3-difluoroazetidin-1-yl)methanone

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 48h;	55%

3-bromoisonicotinic acid (13959-02-9) → 3-bromo-4-(hydroxymethyl)pyridine (146679-66-5)

Conditions	Yield
Stage #1: 3-bromoisonicotinic acid With triethylamine; methyl chloroformate In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: With sodium tetrahydroborate In water at 0℃; for 1h;	52%

3-bromoisonicotinic acid (13959-02-9) + methyl chloroformate (79-22-1) → 3-bromo-4-(hydroxymethyl)pyridine (146679-66-5)

Conditions	Yield
Stage #1: 3-bromoisonicotinic acid; methyl chloroformate With triethylamine In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 1h;	52%

azetidine (503-29-7) + 3-bromoisonicotinic acid (13959-02-9) → Azetidin-1-yl(3-bromopyridin-4-yl)methanone

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 48h;	52%

3-bromoisonicotinic acid (13959-02-9) + beta-Naltrexamine dihydrochloride (63463-07-0) → C26H28BrN3O4*2ClH

Conditions

Yield

Stage #1: 3-bromoisonicotinic acid; beta-Naltrexamine dihydrochloride With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere; Molecular sieve; Stage #2: With potassium carbonate In methanol; N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #3: With hydrogenchloride In methanol at 20℃; for 0.5h;

51.4%

3-bromoisonicotinic acid (13959-02-9) + 3,4,5-trifluoro aniline (163733-96-8) → 2-bromo-N-(3,4,5-trifluorophenyl)isonicotinamide

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	50%

5-iodoquinoline (1006-50-4) + bis(4-chlorophenyl)acetylene (1820-42-4) + 3-bromoisonicotinic acid (13959-02-9) → 5,6-bis(4-chlorophenyl)isoquinolino[7,8-f]quinoline

Conditions	Yield
With norborn-2-ene; palladium diacetate; potassium carbonate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 130℃; for 20h; Schlenk technique; Inert atmosphere; Sealed tube; regioselective reaction;	42%

2-amino-4-methoxyacetophenone hydrochloride (335104-63-7) + 3-bromoisonicotinic acid (13959-02-9) → PC-033 (1202402-05-8)

Conditions	Yield
With 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In dichloromethane at 22℃; for 18h;	41.7%

Upstream product

• 71541-34-9 3-bromo-N-phenylpyridine-4-carboxamide 
• 55-22-1 pyridine-4-carboxylic acid 
• 626-55-1 3-Bromopyridine 
• 124-38-9 carbon dioxide 
• 3430-22-6 3-Bromo-4-methylpyridin 
• 3034-31-9 N-phenylisonicotinamide 

Downstream Products

• 59786-31-1 methyl 3-bromoisonicotinate 
• 909532-61-2 3-bromo-N-methyl-N-(methyloxy)-4-pyridinecarboxamide 
• 1192021-09-2 3-bromo-N-[2-hydroxy-5-(trifluoromethyl)phenyl]isonicotinamide 
• 1261743-67-2 3-phenyl ethyl isonicotinate 
• 1423014-73-6 ethyl 1-methyl-3-phenyl-1,2,5,6-tetrahydropyridine-4-carboxylate 
• 1423014-72-5 C₁₅H₁₆NO₂⁽¹⁺⁾*I^(1-) 
• 1423014-74-7 C₂₃H₂₇NO₄ 
• 1423014-75-8 C₂₃H₂₅NO₃ 
• 1613435-99-6 4-cyano-3-(4-methylphenylethynyl)pyridine 
• 118160-00-2 4-cyano-3-(phenylethynyl)pyridine 
• 118160-04-6 3-phenyl-1H-pyrano(4,3-c)pyridin-1-one 
• 35968-87-7 3-phenyl-2,6-naphthyridin-1(2H)-one 
• 13959-01-8 ethyl 3-bromopyridine-4-carboxylate 
• 13958-99-1 3-bromopyridine-4-carboxamide 

Relevant articles and documents

High-yield synthesis method of methyl 3-aminoisonicotinate

The invention belongs to the field of chemical pharmacy, and particularly discloses a high-yield synthesis method of methyl 3-aminoisonicotinate. According to the high-yield synthesis method, 4-picolinic acid is used as a raw material and subjected to brominating, ammonifying and esterifying to obtain methyl 3-aminoisonicotinate. The high-yield synthesis method of methyl 3-aminoisonicotinate has the advantages of mild reaction conditions, high total yield, realization of repeated use of a 3-bromo-4-picolinic acid reaction waste filtrate, improvement of the utilization rate of the raw material,reduction of resource waste, maximum reduction of the production cost of the whole process, and extremely high application value.

Method for synthesizing 3-bromoisonicotinic acid intermediate

The invention relates to a method for synthesizing a 3-bromoisonicotinic acid intermediate, and belongs to the technical field of pharmaceutical intermediates. The process comprises the following steps: 4-methylpyridine is adopted as a raw material, and the 4-methylpyridine is reacted with bromine under the catalysis of an aluminum trichloride catalyst to form intermediate 3-bromo-4-methylpyridine; and a novel catalyst Co0.27CuO3 is added, oxygen is introduced for oxidization to form the target product 3-bromoisonicotinic acid. According to the method provided by the invention, in the oxidation reaction process, water is used as a solvent, the novel catalyst Co0.27CuO3 is introduced, the oxygen is used as an oxidant to replace a traditional KMnO4 oxidant, so that pollution of heavy metalsto the environment can be avoided; because the novel catalyst is not affected by the reaction environment, catalytic activity of the novel catalyst is not reduced, and after 25 cycles, activity of thecatalyst is not significantly reduced; and the method has the advantages of greatly improving the yield, reducing the costs, improving the safety, saving the energy, and the like, and conforms to modern chemical industry production requirements of a green reaction.

Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases

Abstract The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl)ate their target proteins using NAD+ as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with β-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused >1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2.

HARMFUL ARTHROPOD CONTROL COMPOSITION, AND FUSED HETEROCYCLIC COMPOUND

Disclosed is a harmful arthropod control composition comprising, as an active ingredient, a fused heterocyclic compound represented by formula (1) [wherein A1 and A2 independently represent a nitrogen atom or the like; R1 and R4 independently represent a halogen atom or the like; R2 and R3 independently represent a halogen atom or the like; R5 and R6 independently represent a linear C1-C6 hydrocarbon group which may be substituted, or the like (provided that both R5 and R6 cannot represent a hydrogen atom simultaneously); and n represents 0 or 1]. The harmful arthropod control composition has an excellent efficacy to control harmful arthropods.

HARMFUL ARTHROPOD CONTROL COMPOSITION, AND FUSED HETEROCYCLIC COMPOUND

Disclosed is a harmful arthropod control composition comprising, as an active ingredient, a fused heterocyclic compound represented by formula (1) [wherein A1 and A2 independently represent a nitrogen atom or the like; R1 and R4 independently represent a halogen atom or the like; R2 and R3 independently represent a halogen atom or the like; R5 and R6 independently represent a linear C1-C6 hydrocarbon group which may be substituted, or the like (provided that both R5 and R6 cannot represent a hydrogen atom simultaneously); and n represents 0 or 1]. The harmful arthropod control composition has an excellent efficacy to control harmful arthropods.

COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS

The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and a neonicotinoid compound; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and a neonicotinoid compound to the arthropod pests or a locus where the arthropod pests inhabit; and so on.

COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS

The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and pyriproxyfen; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and pyriproxyfen to the arthropod pests or a locus where the arthropod pests inhabit; and so on.

COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS

The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and pyridalyl; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and pyridalyl to the arthropod pests or a locus where the arthropod pests inhabit; and so on.

COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS

The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and a diamide compound; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and a diamide compound to the arthropod pests or a locus where the arthropod pests inhabit; and so on.

COMPOSITION AND METHOD FOR CONTROLLING ARTHROPOD PESTS

The present invention provides: an arthropod pests control composition comprising, as active ingredients, a condensed heterocyclic compound and a pyrethroid compound; a method for controlling arthropod pests which comprises applying effective amounts of a condensed heterocyclic compound and a pyrethroid compound to the arthropod pests or a locus where the arthropod pests inhabit; and so on.