US Government As Represented by the Secretary of the Army

Harold Z Sommer

George E Wicks, Jr

Omer O Owens

Jacob I Miller

John Krenzer

Emory W Sarver

John J Martin

Benjamin Witten

Paul C Bossle

New chmeical compounds having the generic formula: ##STR1## wherein n is 5-16, R, R' are radicals selected from the group consisting methyl, ethyl, propyl, isopropyl, butyl, and X is one equivalent of an anion selected from the group consisting of monovalent or polyvalent anions, and having utility as toxic agents and in munitions.

Chemical agents

New toxic chemical compounds having the generic formula: ##STR1## and utility and method of preparation thereof wherein X is one equivalent f an anion selected from the group consisting of halide, hydrogen sulfate, nitrate, hydrogen oxalate and perchlorate and R and R.sub.1 are methyl while Z is a radical selected from 3-dimethylcarbamoxyphenyl, 2-dimethylcarbamoxybenzyl or 3-dimethyl carbamoxy-.alpha.-picolinyl.

New chemical compounds having the generic formula: ##STR1## wherein n is 5-16 methylene groups, R, R' are radicals selected from the oup consisting of methyl, ethyl, propyl, isopropyl, butyl, benzyl, and x is one equivalent of an anion selected from the group consisting of monovalent and polyvalent anions, and having utility as incapacitating agents and in munitions.

New chemical compounds having the generic formula: ##STR1## wherein X is one equivalent of an anion selected from the group consisting of monovalent or polyvalent anions, and having utility as incapacitating agents and in munitions.

Chemical agent

1. A chemical toxic agent selected from the group consisting of: ##STR1## where n is an integer from 3 to 11 and X represents one equivalent of an ion.

New chemical compounds, bis-quaternary carbamates, having the generic fora: ##STR1## wherein X is one equivalent of a monovalent or polyvalent anion, wherein R and R.sub.1 are aliphatic radicals selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, wherein Z is a radical selected from the group consisting of hydrogen, methyl, or ethyl, wherein n is 2-12, wherein the dimethylcarbamoxy group is in the ortho, meta, or para position in the benzyl moiety, and having utility as toxic agents.

Ketobenzylcarbamates

Novel toxic compounds being useful as chemical warfare agents in various itions. The compound having the following structure: ##STR1## where n is an integer from 6 to 16 and where X is halide, sulfate, nitrate, hydrogenoxalate or perchlorate forming a stable salt.

New chemical compounds having the generic formula: ##STR1## where n is 3 to 16 carbon atoms and where X is one equivalent of a monovnt or polyvalent anion, and having utility as toxic agents.

Isoquinilinium chemical agents

New chemical compounds having the generic formula: ##STR1## wherein X is one equivalent of a monovalent or polyvalent anion; R and R' re methyl or ethyl radicals; R.sub.1, R.sub.1 ', R.sub.2, R.sub.2 ' are hydrogen or a methyl radical; and Z is a radical selected from methyl, ethyl, propyl, butyl, or pentyl and having utility as incapacitating agents and in munitions.

New chemical compounds, bis quaternary carbamates, having the generic fora: ##STR1## wherein NRR.sub.1 R.sub.2 is a radical selected from the group consisting of N-methylpyrrolidinio, N-methylpiperidinio, N-methyl-3-hydroxypiperidinio, quinuclidinio, 3-hydroxyquinuclidinio, and 3-oxoquinuclidinio and wherein X is one equivalent of a monovalent or polyvalent anion.

New chemical compounds having the generic formula: ##STR1## wherein X is one-equivalent of an anion selected from the group consisting f monovalent and polyvalent anions, and having utility as incapacitating agents and in munitions.

New chemical compounds having the generic formula: ##STR1## wherein X is one equivalent of an anion selected from monovalent and pollent anions, and R,R' and Z are aliphatic radicals selected from the group consisting of ethyl, propyl, and butyl, with the provision that when Z is a radical selected from the group of octyl, dodecyl, and cyclohexyl, R,R' are selected from methyl and ethyl groups, and having utility as incapacitating agents and in munitions.

New chemical compounds, bis quaternary carbamates, having the generic fora: ##STR1## wherein X is one equivalent of an anion selected from monovalent or polyvalent anions, wherein n is 1 to 8, and wherein R, R' are aliphatic radicals selected from the group consisting of methyl, ethyl, propyl, and butyl, and having utility as toxic agents.

A method for the simultaneous detection, separation and analysis by reverse hase HPLC of sulfur mustard type compounds and their major hydrolysis and oxidation by-products utilizes a novel precolumn enhancement derivatization procedure. The method involves the reaction of these nonchromophoric sulfides with N-halogeno-N-metal arylsulfonamidates on a microscale to produce UV or visible absorbing or fluorescing arylsulfonylsulfilimine compounds. These arylsulfonylsulfilimine derivatives can then be readily separated on a low polarity C-18 column by reverse phase HPLC. The method permits quantitation of these sulfides by UV detector response in quantities as small as 20 nanograms.

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Havre de Grace, MD, United States of America

Harold Z Sommer