67306-00-7

Usage

Metabolic pathway

Limited data are available in the open literature. Information presented in this summary is abstracted from the data evaluation published by the Pesticide Safety Directorate (PSD, 1993). Fenpropidin is stable to aqueous hydrolysis and photodegradation. Hydroxylation of the piperidine ring is the primary metabolic pathway in soil and wheat plants. Hydroxylation and oxidation of one of the methyl groups of the tert-butyl moiety are the major reactions in rats and lactating goats. The primary metabolic pathways of fenpropidin are presented in Scheme 1.

Degradation

Fenpropidin (1)i s stable to hydrolytic degradation (50 °C)in the pH range of 3-9 and when exposed to UV light in pH 5 buffer solution.

InChI:InChI=1/C19H31N/c1-16(15-20-12-6-5-7-13-20)14-17-8-10-18(11-9-17)19(2,3)4/h8-11,16H,5-7,12-15H2,1-4H3

Upstream product

• 74879-98-4 N-(2-methyl-3-phenylpropyl)piperidine 
• 115-11-7 isobutene 
• 17201-04-6 2-methyl-1-(piperidin-1-yl)propan-1-one 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 110-89-4 piperidine 
• 80-54-6 lilial 
• 67306-24-5 1-[3-(p-tert.butyl-phenyl)-2-methyl-2-propenyl]-piperidine 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 67306-64-3 1-[3-(p-tert-butyl-phenyl)-2-methyl-propyl]-piperidine-1-oxide 
• 81721-44-0 1-[3-(4-tert-butyl-cyclohexyl)-2-methyl-propyl]-piperidine 

Relevant academic research and scientific papers

Pd-catalysed β-selective C(sp3)-H arylation of simple amides

An efficient Pd-catalysed β-C(sp3)-H arylation of diverse native amides with aryl iodides was developed. This protocol overcomes the necessity of the Thorpe-Ingold effect and features broad substrate scope and good functional group tolerance. The potential application of this protocol is collectively demonstrated by gram-scale synthesis and the synthesis of several bioactive molecules.

Synthesis of β-Chiral Amines by Dynamic Kinetic Resolution of α-Branched Aldehydes Applying Imine Reductases

Imine reductases (IREDs) allow the one-step preparation of optically active secondary and tertiary amines by reductive amination of ketones. Until now, mainly α-chiral amines have been prepared by this route. In this study, we explored the possibility of synthesizing β-chiral amines, a class of compounds which is also frequently found as structural motif in pharmaceuticals but much more challenging to prepare due to the following reasons: (i) The aldehyde substrate already contains the chiral center and needs to be racemized to enable full conversion. (ii) Because the intermediate imine bears the stereo center two carbon atoms remote to the imine nitrogen, it is more challenging to achieve high enantioselectivity compared to α-chiral amine synthesis. For investigating the proof of concept, we first confirmed that different IREDs are able to convert a variety of α-branched aldehydes when combined with five different amine substrates. The IRED from Streptomyces ipomoeae was a suitable enzyme facilitating the dynamic kinetic resolution of 2-phenylpropanal and a substituted 2-methyl-3-phenylpropanal: the corresponding N-methylated β-chiral amines were obtained with '95 % conversion and 78 and 95 %ee. Other amines were formed with low to moderate enantiomeric excess. This exemplifies the potential of IREDs for the one-step synthesis of secondary β-chiral amines, but also the challenge to identify highly selective enzymes for a desired amine product.

P-hydroxyaniline derivatives, their preparation and their use

p-Hydroxyaniline derivatives of the formula I STR1 where the substituents have the following meanings: R1 is unsubstituted or substituted bicycloalkyl or bicycloalkenyl; R2 and R3 independently of one another are halogen, alkyl, haloalkyl, alkoxy or haloalkoxy; R4 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, OR5 or NR5 R6, where R5 is unsubstituted or substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl, and R6 is hydrogen or alkyl, and their salts, processes for their preparation, compositions containing them and their use for controlling harmful fungi or pests are described.

Process for the preparation of morpholine and piperidine derivatives

The invention relates to an improved process for the preparation of fungicidally active compounds of the formula STR1 wherein R1 and R2 individually are lower alkyl of from 1 to 4 carbons or halo-(lower alkyl) of from 1 to 4 carbons or R1 and R2 together with the carbon to which they are attached form a 3 to 7 membered cycloalkyl ring or lower alkyl-substituted cycloalkyl of from 4 to 9 carbons, R3, R4 and R5 individually are hydrogen or lower alkyl of from 1 to 4 carbons and X is methylene or oxygen, and salts of those compounds which are basic. The improved process comprises the reaction of a compound of the formula, STR2 wherein R3, R4, R5 and X have the significance given hereinabove, with a compound which forms a carbonium ion of the formula STR3 wherein R1 and R2 have the significance as given hereinabove.

Heterocyclics useful as fungicides and fungicidal compositions thereof

Heterocyclic compounds characterized by the formula STR1 wherein R1, R3, R4, R5, R6, X and z are as hereinafter set forth, prepared, inter alia, by reacting a compound characterized by the formula STR2 with an amine characterized by the formula STR3 wherein R1, R3, R4, R5, R6, X and Y are as hereinafter set forth, are described. The end products are useful as fungicidal agents.