Labelled organophosphorus pesticides. III. Synthesis of carbon-14 labelled o-(2,6-dichloro-4-methylphenyl) O,O-dlmethyl phosphorothioate

✍ Scribed by Akira Yoshitake; Hiroshi Kanamaru; Fumiaki Shono; Iwao Nakatsuka

• Publisher: John Wiley and Sons
• Year: 1979
• Tongue: French
• Weight: 260 KB
• Volume: 16
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580160314

✦ Synopsis

0-(2,6-Dichloro-4-me t h y l p h e n y l ) 0,O-dime t h y l p h o s p h o r o t h i o a t e (5-3349) (lJ, a f u n g i c i d e i n s o i l , was l a b e l l e d w i t h carbon-14 i n d i v i d u a l l y a t the a r y l m e t h y l and the phenyl r i n g for u s e i n m e t a b o l i c s t u d i e s . T h e synthetic p r o c e d u r e s are i l l u s t r a t e d i n

methyl-14C-pheraol (2) b y c a t a l y t i c h y d r o g e n a t i o n u s i n g 10% Pd-C a s a c a t a l y s t . Dichlorination of & w i t h chlorine g a v e 2,6-di-chl0ro-4-methyl-~~C-phenol (el. Condensation of w i t h 0,Od i m e t h y l p h o s p h o r o c h l o r i d o t h i o a te gave S-3349-( a r y l m e t h y1-14C)

(&) i n the overall y i e l d o f 22% from p o t a s s i u m ~y a n i d e -' ~C . By the s i m i l a r p r o c e d u r e s , I -m e t h y l p h e n ~l -~~C ~ (g) was c o n v e r t e d t o S-3349-(phenyl-14C6) (g) i n 70% y i e l d .