57369-32-1 Usage
Uses
Pyroquilon is used for the control of blast (Pyricularia oryzae) in
rice.
Definition
ChEBI: A pyrroloquinoline that is 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline in which the hydrogens at position 4 are replaced by an oxo group. A fungicide used to control rice blast, it is not approved wof use within the Eur
pean Union.
Metabolic pathway
The fate of pyroquilon in rice and rats has been reported. Given the metabolic
stability of cyclic amides, there are few options, other than hydroxylation,
open for the metabolism of the compound. Its biotransformation
involves initial hydroxylation at three sites in the molecule, followed by
ring-opening, dehydration and further oxidation affording a somewhat
complex picture. A study in rats revealed most of these metabolites
but with some further metabolic degradation. The usual differences in
conjugation were seen with mainly glucoside formation in plants and
glucuronide and sulfate formation in animals.
Metabolism
Animals: Rapidly metabolized and eliminated
via urine and feces. Residues in tissues were
generally low, and there was no evidence for accumulation
or retention of pyroquilon or its metabolites. Plants: Major
metabolites in rice grain were 3,4-dihydro-4-hydroxy-2-
oxoquinoline-8-acetic acid and two other acetic acid derivatives.
Soil/Environment: DT50 (silty soil) 2, (sandy loam)
18 w. Kd 1.3–42 μg/g soil, little to moderately mobile.
Photolysis in water, DT50 10 d.
Toxicity evaluation
Mammalian toxicology. Oral: Acute oral
LD50 for rats 321, mice 581 mg/kg. Skin and eye:
Acute percutaneous LD50 for rats >3100 mg/kg. Not
a skin irritant, minimal eye irritant (rabbits). Not a
skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for
rats >5.1 mg/l air. NOEL: (2 yr) for rats 22.5, mice
1.5 mg/kg b.w. daily; (1 yr) for dogs 60.5 mg/kg b.w.
daily. ADI: 0.015mg/kg b.w. Other: Not teratogenic, not
mutagenic, not oncogenic. Toxicity class: WHO (a.i.) II;
EPA (formulation) II RC risk R22. Ecotoxicology. Birds:
LC50 (8 d) for Japanese quail 794, chickens 431 mg/kg.
LC50 (8 d) for Japanese quail >10000 mg/kg. Fish LC50
(96 h) for catfish 21, rainbow trout 13, perch 20, guppy
30 mg/l. Bees: Practically nontoxic to honeybees; LD50
(oral) > 20, (contact) > 1000 mg/bee. Daphnia LC50 (48 h)
> 60 mg/L. Algae: No effect on Scenedemus acutus.
Degradation
Pyroquilon is stable to hydrolysis over a very wide pH range. It is
degraded under conditions of aqueous photolysis with a DT50 of 10 days
(PM). Details are not available.
Check Digit Verification of cas no
The CAS Registry Mumber 57369-32-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,7,3,6 and 9 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 57369-32:
(7*5)+(6*7)+(5*3)+(4*6)+(3*9)+(2*3)+(1*2)=151
151 % 10 = 1
So 57369-32-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H11NO/c13-10-5-4-8-2-1-3-9-6-7-12(10)11(8)9/h1-3H,4-7H2
57369-32-1Relevant articles and documents
Cobalt-Catalyzed One-Step Access to Pyroquilon and C-7 Alkenylation of Indoline with Activated Alkenes Using Weakly Coordinating Functional Groups
Banjare, Shyam Kumar,Biswal, Pragati,Ravikumar, Ponneri Chandrababu
, p. 5330 - 5341 (2020)
A new strategy for the C(7)-H functionalization of indoline derivatives using first-row transition-metal cobalt has been demonstrated wherein the pivaloyl group acts as a weakly coordinating directing group. Biologically important pyroquilon (tetrahydropyroquinolinone) derivatives have been synthesized in a one-pot manner through selective C(7)-H functionalization and concomitant cyclization. In this process, aromatic C-H and amidic C-N bonds are cleaved, and new C-C and C-N bonds are formed in a step-economical fashion. Further, selective C(7)-H alkenylation of indoline derivatives has also been accomplished using activated alkenes by varying the reaction conditions.
Bismuth(iii)-catalyzed regioselective alkylation of tetrahydroquinolines and indolines towards the synthesis of bioactive core-biaryl oxindoles and CYP19 inhibitors
Prusty, Namrata,Kinthada, Lakshmana K.,Meena, Rohit,Chebolu, Rajesh,Ravikumar, Ponneri Chandrababu
, p. 891 - 905 (2021/02/09)
Bismuth(iii)-catalyzed regioselective functionalization at the C-6 position of tetrahydroquinolines and the C-5 position of indolines has been demonstrated. For the first time, one pot symmetrical and unsymmetrical arylation of isatins with tetrahydroquinolines was accomplished giving a completely new product skeleton in good to excellent yields. Most importantly, this protocol leads to the formation of a highly strained quaternary carbon stereogenic center, which is a challenging task. Benzhydryl and 1-phenylethyl trichloroacetimidates have been used as the alkylating partners to functionalize the C-6 and C-5 positions of tetrahydroquinolines and indolines, respectively. The scope of the developed methodology has been extended for the synthesis of the bioactive CYP19-inhibitor and its analogue.
Rhodium-Catalyzed Regioselective C7-Functionalization of Indole Derivatives with Acrylates by Using an N-Imino Directing Group
Xu, Lanting,Tan, Lushi,Ma, Dawei
, p. 2839 - 2844 (2017/10/06)
An efficient rhodium-catalyzed method for C-H olefination at the C7 position of indoles has been developed. The N-imino directing group was shown to be crucial for high regioselectivity and reactivity of the metal catalyst. The utility of this protocol was further demonstrated through a concise, four-step synthesis of pyroquilon from indole.
