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US 5,399,716 AGranted
N-oxygenated arylpyrrole insecticidal, acaricidal and nematicidal agents
AssigneeAmerican Cyanamid Company
InventorVenkataraman Kameswaran
Life of this patent
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Abstract
Novel N-oxygenated arylpyrrole compounds which are effective for the control of insects, acarids and nematodes are described. A method for the insecticidal, acaricidal and nematicidal use of said compounds and a method for the preparation of said compounds are presented.
Claims3
A method for the preparation of a compound having the structure:
- ##STR51## wherein X is H, F, Cl, Br or I;
- Y is H, F, Cl, Br or I;
- L is HA F, Cl or Br;
- and
- M and R are each independently H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, cyano, F, Cl, Br, I, nitro, CF.sub.3, R.sub.1 CF.sub.2 A, R.sub.2 CO or NR.sub.3 R.sub.4 ;
- and when M and R are on adjacent positions and taken with the carbon atoms to which they are attached they may form a ring in which MR represents the structure:
- ##STR52## Z is S(O).sub.n or O;
- R.sub.1 is H, F, CHF.sub.2, CHFCl or CF.sub.3 ;
- R.sub.2 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy or NR.sub.3 R.sub.4 ;
- R.sub.3 is H or C.sub.1 -C.sub.3 alkyl;
- R.sub.4 is H, C.sub.1 -C.sub.3 alkyl or R.sub.5 CO;
- R.sub.5 is H or C.sub.1 -C.sub.3 alkyl;
- and
- n is an integer of 0, 1 or 2;
- which comprises reacting a methyl benzoate having the structure:
- ##STR53## wherein L, M and R are as described above with cyanopropionaldehyde dimethyl acetal in the presence of sodium hydride, at a temperature of about 70.degree.-100.degree. C., to yield a 3-benzoyl-3-cyano-1-propionaldehyde, dimethyl acetal having the structure:
- ##STR54## wherein L, M and R are described above and reacting the thus formed 3-benzoyl-3-cyano-1-propionaldehyde, dimethyl acetal with hydroxylamine hydrochloride to yield a 1-hydroxy-2-substituted arylpyrrole-3-carbonitrile intermediate compound having the structure:
- ##STR55## wherein L, M and R are as described above and optionally reacting said intermediate compound with a halogenating agent selected from the group consisting of bromine, a sulfuryl halide, sodium hypochlorite, t-butylhypochlorite, N-bromosuccinimide, and N-iodosuccinimide.
15 more elements
A method for the preparation of a compound having the structure:
- ##STR56## wherein Y is H, F, Cl, Br or I;
- L is H or F, Cl or Br;
- and
- M and R are each independently H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, cyano, F, Cl, Br, I, nitro, CF.sub.3, R.sub.1 CF.sub.2 Z, R.sub.2 CO or NR.sub.3 R.sub.4 ;
- and when M and R are on adjacent positions and taken with the carbon atoms to which they are attached they may form a ring in which MR represents the structure:
- ##STR57## Z is S(O).sub.n or O:
- R.sub.1 is H, F, CHF.sub.2, CHFCl or CF.sub.3 ;
- R.sub.2 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy or NR.sub.3 R.sub.4 ;
- R.sub.3 is H or C.sub.1 -C.sub.3 alkyl;
- R.sub.4 is H, C.sub.1 -C.sub.3 alkyl or R.sub.5 CO;
- R.sub.5 is H or C.sub.1 -C.sub.3 alkyl;
- and
- n is an integer of 0, 1 or 2;
- which comprises reacting an acetophenone oxime having the structure:
- ##STR58## wherein, L, M and R are as described above with sodium diethyl oxalacetate to yield an intermediate compound having the structure:
- ##STR59## wherein L, M and R are as described above, reacting said intermediate with a mineral acid in the presence of an alcohol to give a 5-aryl-1-hydroxypyrrole-3carboxylate having the structural formula:
- ##STR60## wherein L, M and R are as described above, reacting the thus-obtained 1-hydroxypyrrole-3-carboxylate with methyl iodide in the presence of potassium t-butoxide to yield the corresponding 1-methoxypyrrole-3-carboxylate, saponifying the 1-methoxypyrrole-3-carboxylate to give the corresponding carboxylic acid, reacting said carboxylic acid with chlorosulfonyl isocyanate and dimethylformamide to yield a 1-methoxy-5-arylpyrrole-3-carbonitrile intermediate and optionally reacting said 1-methoxy-5-arylpyrrate-3-carbonitrile intermediate with a halogenating agent.
14 more elements
Dependencies are inferred from the claim text.