96489-71-3

Usage

Uses

Used in Agriculture:
Pyridaben is used as an acaricide for controlling mites and ticks that infest crops and as an insecticide to combat sucking insects that damage plants.
Used in Pest Control:
Pyridaben is used as a long-lasting solution for managing pest populations, particularly those that feed on plant sap, in various agricultural and horticultural settings.
Trade Names:
Some of the trade names under which Pyridaben is marketed include Nexter, Oracle, Poseidon, Pyramite, Sanmite, and Starling.

Acute Toxicity

Pyridaben shows moderate to low acute toxicity to mammals. The intraperitoneal LDso was 68 mg/kg in male rats (Igarashi and Sakamoto, 1994). The dermal toxicity is low but toxicity by the inhalation route is quite high. With sublethal doses in mice and rats, clinical signs included decreased food consumption, diarrhea, hypothermia, bradycardia, bradypnea, decreased spontaneous motor activity, abnormal gait, prostration, eye closing, amd piloerection. At near lethal or lethal doses (300 mg/kg or more) depression of the central nervous and cardiovascular systems were stronger, but no change occurred in motor functions, including coordination, muscle strength, and neuromuscular transmission, or in sensory functions. Early gastric lavage was effective in presenting poisoning in rats and loperamide was efficacious in reducing the diarrhea that occurred at low doses.

Carcinogenicity

Pyridaben was not oncogenic in typical lifetime feeding studies in the rat and mouse. It is classified by the U.S. Environmental Protection Agency as a Group E compound (no evidence for carcinogenicity to humans).

Neurotoxicity

Pyridaben caused only a low degree of acute neurotoxicity in a standard battery of neurobehavioral tests when given at a single oral dose of 200 mg/kg in males. Effects included piloerection, hypoactiviy, tremors, and lowered body temperature, but these were sporadic and transient. In a longer term (90 day) study in rats, no neurotoxicity or neuropathology was seen at oral doses up to 27 mg/kg/day, but plasma cholinesterase activity was reduced in females.

Environmental Fate and Toxicity

Pyridaben has a low acute toxicity to birds, but it is extremely toxic to aquatic species. Its persistence in soil is relatively brief due to rapid microbial degradation (e.g., the half-life under aerobic conditions is reported to be less than 3 weeks). In natural water in the dark, the half-life is about 10 days, due mainly to microbial action since pyridaben is stable to hydrolysis over the pH range 5-9. The half-life including aqueous photolysis is about 30 min at pH 7 (Tomlin, 2000).

Trade name

BAS?-300; NCI?-129; NESTER?; PYRAMITE?; SANMITE?

Potential Exposure

Pyridaben is a pyridazinone insecti- cide/acaricide/miticide used to control mites, whiteflies, leafhoppers and psyllids on fruit trees, vegetables, orna- mentals and other field crops. It is also used to control pests in apple, grapes, pear, pistachio, stone fruits, and the tree nuts group .

Shipping

UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN2902 Pesticides, liquid, toxic. UN2902 Pesticides, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Incompatibilities

Dust may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, perox- ides, permanganates, perchlorates, chlorine, bromine, fluo- rine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

It is the responsibility of chemical waste generators to determine the toxicity and physical properties and of a discarded chemical and to properly identify its classification and certification as a haz- ardous waste and to determine the disposal method. United States Environmental Protection Agency guidelines for the classification determination are listed in 40 CFR Parts 261.3. Additionally, waste generators must consult and follow all regional, national, state and local hazardous waste laws to ensure complete and accurate classification and disposal methods. Follow recommendations for the disposal of pesticides and pesticide containers. Containers must be disposed of properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.

InChI:InChI=1/C19H25ClN2OS/c1-18(2,3)14-9-7-13(8-10-14)12-24-15-11-21-22(19(4,5)6)17(23)16(15)20/h7-11H,12H2,1-6H3

Synthetic route

4-tert-butylbenzyl chloride (19692-45-6) + 2-tert-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone (96490-18-5) → pyridaben (96489-71-3)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide	87.9%
With sodium carbonate In water; N,N-dimethyl-formamide
With potassium carbonate In benzene

4-tert-butyltoluene (98-51-1) + 2-tert-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone (96490-18-5) → pyridaben (96489-71-3)

Conditions	Yield
With N-Bromosuccinimide; di-tert-butyl peroxide; Bathocuproine; nickel(II) acetate tetrahydrate In benzene at 140℃; for 24h; Inert atmosphere;	80%
With di-tert-butyl peroxide; Bathocuproine; nickel(II) acetate tetrahydrate at 140℃; for 24h; Inert atmosphere; Schlenk technique;	28%

1-(bromomethyl)-4-(1,1-dimethylethyl)benzene (18880-00-7) + 2-tert-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone (96490-18-5) → pyridaben (96489-71-3)

Conditions	Yield
With sodium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;

2-tert-butyl-4,5-dichloro-2H-pyridazin-3-one (84956-71-8) → pyridaben (96489-71-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogensulfide / ethanol / 1 h / 0 °C 2: nickel(II) acetate tetrahydrate; Bathocuproine; di-tert-butyl peroxide / 24 h / 140 °C / Inert atmosphere; Schlenk technique View Scheme

pyridaben (96489-71-3) → 2-tert-butyl-4-fluoro-5-(4-tert-butylbenzyl)mercapto-3-(2H)-pyridazinone

Conditions	Yield
With potassium fluoride; [2.2.2]cryptande In dimethyl sulfoxide at 120℃; for 2.5h;	25%
With potassium fluoride In dimethyl sulfoxide at 120℃; for 6h;

pyridaben (96489-71-3) → 2-tert-butyl-4-[18F]-fluoro-5-(4-tert-butylbenzyl)-thio-3(2H)-pyridazinone (1059611-74-3)

Conditions	Yield
Stage #1: With [18F]-potassium fluoride; potassium carbonate; [2.2.2]cryptande In (18O)water; water; acetonitrile Stage #2: pyridaben In acetonitrile at 100℃; for 0.5h;

pyridaben (96489-71-3) → 2-t-butyl-4-butyl-5-(p-t-butylbenzylthio)-3(2H)-pyridazinone

Conditions	Yield
With n-butyllithium In tetrahydrofuran; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; hexane

Upstream product

• 84956-71-8 2-tert-butyl-4,5-dichloro-2H-pyridazin-3-one 
• 98-51-1 4-tert-butyltoluene 
• 96490-18-5 2-tert-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone 
• 18880-00-7 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene 
• 19692-45-6 4-tert-butylbenzyl chloride 

Downstream Products

• 1059611-74-3 2-tert-butyl-4-[18F]-fluoro-5-(4-tert-butylbenzyl)-thio-3(2H)-pyridazinone 

Relevant academic research and scientific papers

Nickel-catalyzed oxidative dehydrogenative coupling of alkane with thiol for C(sp3)-S bond formation

A nickel-catalyzed oxidative dehydrogenative coupling reaction of alkane with thiol for the construction of C(sp3)-S bond has been established, affording more than 50 alkyl thioethers. Notably, pharmaceutical and agrochemicals, such as Provigil, Chlorbenside and Pyridaben, were readily synthesized by this approach. The sterically hindered ligand BC and disulfide which was formed in situ oxidation of thiol, efficiently avoiding nickel-catalyst poisoning. A set of mechanistic experiments disclose both Ni-catalyzed and Ni-free HAA processes.

Preparation method of alkyl sulfide

The invention relates to a preparation method of alkyl sulfide. The method comprises the following steps: under the protection of nitrogen, sequentially adding transition metal, a nitrogen ligand, a cocatalyst, an oxidant, a solvent, alkane and thiophenol or mercaptan into a reaction tube, carrying out oxidative dehydrogenation coupling reaction at 80-150 DEG C, ending the reaction after 6-48 hours, evaporating the solvent to dryness, and carrying out column chromatography separation to obtain the alkyl sulfide compound. The method is simple in synthesis process, mild in reaction condition, high in yield and easy to industrialize.

ACTIVE COMPOUND COMBINATIONS HAVING INSECTICIDAL AND ACARICIDAL PROPERTIES

The novel active compound combinations comprising a compound of the formula (I-1) or (I-2) and the active compounds (1) to (26) listed in the description have very good insecticidal and acaricidal properties.

Contrast agents for myocardial perfusion imaging

The present disclosure is directed, in part, to compounds and methods for imaging myocardial perfusion, comprising administering to a patient a contrast agent which comprises a compound that binds MC-1, and an imaging moiety, and scanning the patient using diagnostic imaging.

Antitumor agent, novel 3(2H)-pyridazinone derivatives and their preparation

Anti-tomor agents comprising novel 3(2H)-pyridazinone derivatives or salts thereof and methods of producing the same are disclosed. Also disclosed is a method for treating or preventing tumors by administering to a mammal a therapeutically effective amount of 4,5-di substituted 3(2H)-pyridazinones and salts thereof.

Benzylthio pyridazinone derivatives, preparation thereof, and insecticidal acaricidal, fungicidal compositions

Novel 3(2H)-pyridazinone derivatives having the formula I: STR1 wherein, R is a straight or branched C2 to C6 alkyl, R1 and R2 are each independently hydrogen or a lower alkyl, R4 is a halogen, R3 is a halogen, an alkyl, a cycloalkyl, an alkoxy, a haloalkyl, a haloalkoxy, --CN, --NO2, a phenyl, a benzyloxy, a benzyl, a phenoxy, a phenylthio, a pyridyloxy, a quinoxalyloxy, a lower alkenyloxy, a lower alkylthio, a lower haloalkylthio, --Si(CH3)3, --OH, --N(CH3)2, --SCN, --COOCH3 or --OCH(CH3)COOC2 H5, and n is an integer of 1 to 5, said R3 being the same or different when n is an integer of 2 to 5. A process for preparation of said derivatives is also provided. These derivatives are useful as an active ingredient of insecticidal, acaricidal, nematicidal and/or fungicidal compositions for agricultural and horticultural uses as well as of expellent compositions for ticks parasitic on animals.

Pyridazinone derivatives, preparation thereof, and insecticidal, acaricidal, nematicidal, fungicidal compositions

Novel 3(2H)-pyridazinone derivatives having the general formula (I): STR1 wherein, R denotes a straight or branched C1 to C6 alkyl; A denotes a straight or branched C1 to C6 alkyl or a halogen; X denotes oxygen or sulfur atom; Q denotes a group; STR2 when A is a straight or branched C1 to C6 alkyl, and Q denotes a group: STR3 when A is a halogen atom; R1 and R2 denote each independently hydrogen, a lower alkyl, a lower haloalkyl, or 4-tert-butylphenyl; B denotes --CR6 =CR7 --, --CR6 R7 O--, or STR4 (wherein, R6 and R7 denote various specific organic radicals. A process for preparation of said derivatives is also provided. These derivatives are useful as an active ingredient of insecticidal, acaricidal, nematicidal and/or fungicidal compositions for agricultural and horticultural uses as well as of expellent compositions for ticks parasitic on animals.