Hydramethylnon: Difference between revisions

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	{{Mergefrom\|Amdro\|date=October 2007}}
	{{chembox		{{chembox
			\| Watchedfields = changed
⚫	\| Name = ~~'''~~Hydramethylnon~~'''~~
			\| verifiedrevid = 461771725
⚫	\| ImageFile = Hydramethylnon.~~png~~
		⚫	\| Name = Hydramethylnon
	\| IUPACName = 2(1H)-pyrimidinone, tetrahydro-5,5-dimethyl-,
		⚫	\| ImageFile = Hydramethylnon.svg
			\| IUPACName=2(1H-4,4-dimethyl tetrahydro pyrimidinylidene )
	(3-(4-(trifluoromethyl)phenyl)		(3-(4-(trifluoromethyl)phenyl)
	-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)		-1-(2-(4-(trifluoromethyl)phenyl)ethenyl)
	-2-propenylidene)hydrazone		-2-propenylidene)hydrazone
	\| Section1 = {{Chembox Identifiers		\|Section1={{Chembox Identifiers
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
⚫	\| CASNo = 67485-29-4
			\| ChemSpiderID = 4445168
	\| SMILES = N1CC(C)(C)CNC1=NN=C(C=Cc1ccc(C(F)(F)F)cc1) C=Cc1ccc(C(F)(F)F)cc1<!--N1CC(C)(C)CNC1=NN=C(C=Cc1ccc(C(F)(F)F)cc1) C=Cc1ccc(C(F)(F)F)cc1-->
			\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| InChI = }}
			\| ChEMBL = 464812
⚫	\| Section2 = {{Chembox Properties
			\| PubChem = 5281875
	\| Formula = C<sub>25</sub>H<sub>24</sub>F<sub>6</sub>N<sub>4</sub>
			\| InChIKey = IQVNEKKDSLOHHK-FNCQTZNRBM
⚫	\| Appearance = ~~yellow~~ to orange crystalline solid
			\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| MolarMass = 494.50 g/mol
			\| StdInChI = 1S/C25H24F6N4/c1-23(2)15-32-22(33-16-23)35-34-21(13-7-17-3-9-19(10-4-17)24(26,27)28)14-8-18-5-11-20(12-6-18)25(29,30)31/h3-14H,15-16H2,1-2H3,(H2,32,33,35)/b13-7+,14-8+
⚫	\| Density =
			\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| MeltingPt = 185-190 °C
			\| StdInChIKey = IQVNEKKDSLOHHK-FNCQTZNRSA-N
⚫	\| BoilingPt =
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
		⚫	\| CASNo = 67485-29-4
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = J265GZ7MFJ
			\| KEGG_Ref = {{keggcite\|correct\|kegg}}
			\| KEGG = C10994
			\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
			\| ChEBI = 38531
			\| SMILES = FC(F)(F)c1ccc(cc1)C=CC(=NNC2=NCC(C)(C)CN2)C=Cc3ccc(cc3)C(F)(F)F
			\| InChI = 1/C25H24F6N4/c1-23(2)15-32-22(33-16-23)35-34-21(13-7-17-3-9-19(10-4-17)24(26,27)28)14-8-18-5-11-20(12-6-18)25(29,30)31/h3-14H,15-16H2,1-2H3,(H2,32,33,35)/b13-7+,14-8+
			}}
		⚫	\|Section2={{Chembox Properties
			\| C=25
			\| H=24
			\| F=6
			\| N=4
		⚫	\| Appearance = Yellow to orange crystalline solid
		⚫	\| Density =
			\| MeltingPtC = 185 to 190
			\| MeltingPt_notes =
		⚫	\| BoilingPt =
	}}		}}
	\| Section7 = {{Chembox Hazards		\|Section7={{Chembox Hazards
	\| NFPA-H = 1		\| NFPA-H = 1
	\| NFPA-F = 1		\| NFPA-F = 1
	\| NFPA-R = 0		\| NFPA-R = 0
	}}		}}
	}}		}}
			'''Hydramethylnon''' (AC 217,300) is an ] used primarily in the form of ] for ]es and ]s.<ref name=":02">{{Cite book \|last=Jeschke \|first=Peter \|url=https://onlinelibrary.wiley.com/doi/book/10.1002/9783527699261 \|title=Modern Crop Protection Compounds \|last2=Witschel \|first2=Matthias \|last3=Krämer \|first3=Wolfgang \|last4=Schirmer \|first4=Ulrich \|date=25 January 2019 \|publisher=Wiley‐VCH \|year=2019 \|isbn=9783527699261 \|edition=3rd \|pages=1156-1201 \|chapter=32.3 Inhibitors of Mitochondrial Electron Transport: Acaricides and Insecticides}}</ref><ref name="vspn"></ref><ref>{{cite web \| url = https://pubchem.ncbi.nlm.nih.gov/compound/hydramethylnon#section=Pharmacology-and-Biochemistry \| title = Hydramethylnon \| publisher = ]}}</ref> It works by inhibiting ] in the mitochondrial inner membrane and leads to a halting of ] (] class 20A). Some brands of hydramethylnon are ], Blatex, Combat, Cyaforce, Cyclon, Faslane, Grant's, Impact, Matox, Maxforce, Pyramdron, Siege, Scuttle and Wipeout. Hydramethylnon is a slow-acting poison with delayed toxicity that needs to be eaten to be effective.<ref name=npic/>
	'''Hydramethylnon''' is an ]. It is also known as AC 217,300. It is in a chemical class called trifluoromethyl aminohydrazone, which is a metabolic inhibitor. It is used primarily as an insecticide in the form of baits for ]es and ]s. Some brands of insecticides that include hydramethylnon are ], Combat, Blatex, Cyaforce, Cyclon, Faslane, Impact, Matox, Maxforce, Pyramdron, Siege, and Wipeout.

	==Toxicology==		==Toxicology==
			Hydramethylnon has low toxicity in mammals.<ref name=vspn/><ref name=npic>{{cite web \| url = http://npic.orst.edu/factsheets/hydragen.pdf \| title = Hydramethylnon \| publisher = National Pesticide Information Center}}</ref> The oral {{LD50}} is 1100–1300 mg/kg in rats and above 28,000 mg/kg in dogs.<ref name=npic/> Hydramethylnon is ]; the 96-hour LC<sub>50</sub> in rainbow trout is 0.16 mg/L, 0.10 mg/L in ], and 1.70 mg/L in ].
	Oral, rat: ] is 1100–1300 mg/kg.

			Hydramethylnon, when fed to rats for two years, led to an increase in ] and ]s at the highest dose; therefore, the ] classifies hydramethylnon as a possible human carcinogen.<ref name=npic/>
	Oral, dog: ] is above 28000 mg/kg.

	'''Hydramethylnon is especially toxic to fish'''
	*96-hour ] in rainbow trout is 0.16 mg/l, 0.10 mg/l in channel catfish, and 1.70 mg/l in bluegill sunfish.

	==See also==		==See also==
	* ], another insecticide used for similar purposes.		* ], another insecticide used for similar purposes

	==References==		==References==
			{{Reflist}}
	*
	*], 2000
⚫	* ].

	==External links==		==External links==
			* {{PPDB\|386}}
	*		*
	*		*
	*		*
		⚫	* ].
			* ]

			{{Insecticides}}
⚫	]

⚫	]
			]
		⚫	]
		⚫	]
	]		]
	]		]


	{{organic-compound-stub}}

Latest revision as of 21:14, 15 December 2024

Hydramethylnon
Names

IUPAC name 2(1H-4,4-dimethyl tetrahydro pyrimidinylidene ) (3-(4-(trifluoromethyl)phenyl) -1-(2-(4-(trifluoromethyl)phenyl)ethenyl) -2-propenylidene)hydrazone
Identifiers
CAS Number	67485-29-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:38531
ChEMBL	ChEMBL464812
ChemSpider	4445168
ECHA InfoCard	100.100.669
KEGG	C10994
PubChem CID	5281875
UNII	J265GZ7MFJ
CompTox Dashboard (EPA)	DTXSID6023868
InChI InChI=1S/C25H24F6N4/c1-23(2)15-32-22(33-16-23)35-34-21(13-7-17-3-9-19(10-4-17)24(26,27)28)14-8-18-5-11-20(12-6-18)25(29,30)31/h3-14H,15-16H2,1-2H3,(H2,32,33,35)/b13-7+,14-8+Key: IQVNEKKDSLOHHK-FNCQTZNRSA-N InChI=1/C25H24F6N4/c1-23(2)15-32-22(33-16-23)35-34-21(13-7-17-3-9-19(10-4-17)24(26,27)28)14-8-18-5-11-20(12-6-18)25(29,30)31/h3-14H,15-16H2,1-2H3,(H2,32,33,35)/b13-7+,14-8+Key: IQVNEKKDSLOHHK-FNCQTZNRBM
SMILES FC(F)(F)c1ccc(cc1)C=CC(=NNC2=NCC(C)(C)CN2)C=Cc3ccc(cc3)C(F)(F)F
Properties
Chemical formula	C₂₅H₂₄F₆N₄
Molar mass	494.485 g·mol
Appearance	Yellow to orange crystalline solid
Melting point	185 to 190 °C (365 to 374 °F; 458 to 463 K)
Hazards
NFPA 704 (fire diamond)	1 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

Hydramethylnon (AC 217,300) is an insecticide used primarily in the form of baits for cockroaches and ants. It works by inhibiting complex III in the mitochondrial inner membrane and leads to a halting of oxidative phosphorylation (IRAC class 20A). Some brands of hydramethylnon are Amdro, Blatex, Combat, Cyaforce, Cyclon, Faslane, Grant's, Impact, Matox, Maxforce, Pyramdron, Siege, Scuttle and Wipeout. Hydramethylnon is a slow-acting poison with delayed toxicity that needs to be eaten to be effective.

Toxicology

Hydramethylnon has low toxicity in mammals. The oral LD₅₀ is 1100–1300 mg/kg in rats and above 28,000 mg/kg in dogs. Hydramethylnon is toxic to fish; the 96-hour LC₅₀ in rainbow trout is 0.16 mg/L, 0.10 mg/L in channel catfish, and 1.70 mg/L in bluegill sunfish.

Hydramethylnon, when fed to rats for two years, led to an increase in uterine and adrenal tumors at the highest dose; therefore, the Environmental Protection Agency classifies hydramethylnon as a possible human carcinogen.

References

Jeschke, Peter; Witschel, Matthias; Krämer, Wolfgang; Schirmer, Ulrich (25 January 2019). "32.3 Inhibitors of Mitochondrial Electron Transport: Acaricides and Insecticides". Modern Crop Protection Compounds (3rd ed.). Wiley‐VCH. pp. 1156–1201. ISBN 9783527699261.{{cite book}}: CS1 maint: date and year (link)
^ Veterinary Support Personnel Network
"Hydramethylnon". PubChem.
^ "Hydramethylnon" (PDF). National Pesticide Information Center.

External links

Hydramethylnon in the Pesticide Properties DataBase (PPDB)
Hydramethylnon Technical Fact Sheet - National Pesticide Information Center
Hydramethylnon General Fact Sheet - National Pesticide Information Center
Hydramethylnon Pesticide Information Profile - Extension Toxicology Network
Maxforce MSDS.
Amdro MSDS

v t e Pest control: Insecticides
Carbamates	Aldicarb Aminocarb Bendiocarb Butocarboxim Carbaryl Carbofuran Carbosulfan m-Cumenyl methylcarbamate Ethienocarb Fenobucarb Isoprocarb Methomyl Metolcarb Oxamyl Promecarb Propoxur
Inorganic compounds	Aluminium phosphide Boric acid Chromated copper arsenate Copper(II) arsenate Copper(I) cyanide Cryolite Diatomaceous earth Lead hydrogen arsenate Paris Green Scheele's Green
Insect growth regulators	Benzoylureas Diflubenzuron Flufenoxuron Hydroprene Lufenuron Methoprene Noviflumuron Pyriproxyfen
Neonicotinoids	Acetamiprid Clothianidin Dinotefuran Imidacloprid Imidaclothiz Nitenpyram Nithiazine Paichongding Thiacloprid Thiamethoxam
Organochlorides	Aldrin Beta-HCH Carbon tetrachloride Chlordane Cyclodiene 1,2-DCB 1,4-DCB 1,1-DCE 1,2-DCE DDD DDE DDT DFDT Dicofol Dieldrin Endosulfan Endrin Heptachlor Kepone Lindane Methoxychlor Mirex Tetradifon Toxaphene
Organophosphorus	Acephate Azamethiphos Azinphos-methyl Bensulide Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Demeton-S-methyl Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Dimefox Dimethoate Dioxathion Disulfoton Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate Isoxathion Malathion Methamidophos Methidathion Mevinphos Mipafox Monocrotophos Naled Omethoate Oxydemeton-methyl Parathion Parathion-methyl Phenthoate Phorate Phosalone Phosmet Phoxim Pirimiphos-methyl Quinalphos R-16661 Schradan Temefos Tebupirimfos Terbufos Tetrachlorvinphos Tribufos Trichlorfon
Pyrethroids	Acrinathrin Allethrins Bifenthrin Bioallethrin Cyfluthrin Cyhalothrin Cypermethrin Cyphenothrin Deltamethrin Empenthrin Esfenvalerate Etofenprox Fenpropathrin Fenvalerate Flumethrin Fluvalinate Imiprothrin Metofluthrin Permethrin Phenothrin Prallethrin Pyrethrin (I, II; chrysanthemic acid) Pyrethrum Resmethrin Silafluofen Tefluthrin Tetramethrin Tralomethrin Transfluthrin
Diamides	Chlorantraniliprole Cyantraniliprole Flubendiamide
Other chemicals	Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner (+milbemycin oxime) Pyridaben Pyriprole Sarolaner Adjuvants (Piperonyl butoxide, Sesamex) Spinosad Sulfluramid Tebufenozide Tebufenpyrad Veracevine Xanthone Metaflumizone Ryanodine Ryanodol
Metabolites	Oxon Malaoxon Paraoxon TCPy
Biopesticides	Bacillus thuringiensis Baculovirus Beauveria bassiana Beauveria brongniartii Isaria fumosorosea Metarhizium acridum Metarhizium anisopliae Nomuraea rileyi Lecanicillium lecanii Paenibacillus popilliae Purpureocillium lilacinum Spinosad

Categories:

Latest revision as of 21:14, 15 December 2024

Toxicology

See also

References

External links