Molinate 4- hydroxy

Figure 11. MS of the metabolite 2-hydroxy molinate (GC Conditions OV 17, 10% on Gas Chrom Q (4 ) helium flow rate, 30 mL/min temperature, 150°C ...

The five major organosoluble metabolites in the water were molinate sulfoxide, 3- and 4-hydroxy molinate, 4-keto molinate, and keto hexamethyleneimine (keto HMI). The amount of each metabolite in tap water remained fairly constant (below 2%) throughout the 14 days. In water previously containing fish, molinate sulfoxide was 2.1% 4 days after treatment, while other metabolites remained below 2% for the first 7 days. By the 14th day, however, molinate sulfoxide totaled 12.8% and 4-hydroxy and 3-hydroxy molinate were 2.2 and 3.7%, respectively. 

In the presence of carp, molinate was rapidly transformed into more polar metabolites. Twenty-four hours after treatment, conversion of molinate to organosoluble metabolites was extensive (Table II). The proportion of molinate sulfoxide increased from 1.2% on day 1 to 10.2% by the 14th day. Molinate, hydroxylated at the 4 position, decreased from 10.8% to 4.6% in 14 days. However, 4-keto and 3-hydroxy molinate together gradually increased over the 14 days from 6.9% to 77.7%. Another metabolite, a keto HMI,... 

Molinate Metabolism in Carp Hepatic Mixed-function Oxidase System. Incubation of molinate with carp liver microsomes produced four major organosoluble metabolites (molinate sulfoxide, 3- and 4-hydroxy molinate, and keto HMI). Parameters affecting... 

In water containing fish, 4-keto molinate constituted 36.8% of all organosoluble metabolites 4 days after molinate addition. However, in the in vitro microsomal mixed-function oxidase system 4-hydroxy molinate was a principal metabolite (14.3%) and 4-keto molinate represented only 0.16% of the total metabolites. Keto-HMI (2.71%) also constituted a substantial proportion of the identified metabolites. 

Molinate has a low toxicity to rats, oral LDso=720 mg/kg, and is rapidly metabolized by plants to CO2 (1) (5) and naturally occurring plant constituents (1). Molinate is also readily metabolized by soil microorganisms (6). After incubation of molinate with Bacillus sp. 24, Nocardia sp. 119, and Micrococcus sp. 22r which were isolated from Russian garden soils and rice field drains (7,8), it was found that molinate was completely degraded into various hydroxy and oxidized products in the medium. Molinate can be metabolized to its corresponding sulfoxide in the mouse in vivo and by the microsome-NADPH system of mouse liver (9, 10). Hubbell et al. (11) and DeBaun et al. (12) also found molinate sulfoxide along with other polar and nonpolar metabolites in rat urine. 

Chemicals. [Ring-ll4C]molinate, S-ethyl hexahydro-[2-1 Clazepine-l-carbothioate (8.2 mCi/raM) 3-hydroxy, 4-hydroxy, 4-keto, and 2-keto molinate and -carboxymethyl hexahydro-azepine-1-earbothioate (carboxy molinate) were provided by Stauffer Chemical... 

Ethyl -2 -hydroxy-1 - (methylmethoxy) -1,2,3,4-tetrahydroquinone, see Alachlor Ethyl mercaptan, see Butvlate. EPTC. Ethylene dibromide, Molinate... 

Hydroxy-lV-acetyl-hexahydroazepine, see Molinate Hydroxyadipic acid, see Cyclohexene Hydroxyalachlor, see Alachlor Hydroxyametryne, see Ametrvn 2-Hydroxyamino-4,6-dinitrotoluene, see 2,4,6-Trinitrotoluene... 

Soil. Hydrolyzes in soil forming ethyl mercaptan, carbon dioxide, and dialkylamine (half-life approximately 2-5 wk) (Hartley and Kidd, 1987). At recommended rates of application, the half-life of molinate in moist loam soils at 21-27 °C was approximately 3 wk (Humburg et al., 1989). Rajagopal et al. (1984) reported that under flooded conditions, molinate was hydroxylated at the 3- and 4-position with subsequent oxidation forming many compounds including molinate sulfoxide, carboxymethyl molinate, hexahydroazepine-l-carbothioate, 4-hydroxymolinate, 4-hy-droxymolinate sulfoxide, hexahydroazepine, 5-methyl hexahydroazepine-l-carbothioate, 4-keto-molinate, 4-hydroxyhexahydroazepine, 4-hydroxy-Wacetyl-hexahydroazepine, carbon dioxide, and bound residues. 

Hydroxy-6-methoxy-2-methyl-i- 2-(3,4,5-tri-melhoxy-phenyl)-dthyl -I,2,3,4-tetrahydro-iso-ch molin ... 

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