US3889600A - 1-(2-(Phenyl-lower-alkyl)-aziridines munition payload - Google Patents
1-(2-(Phenyl-lower-alkyl)-aziridines munition payload Download PDFInfo
- Publication number
- US3889600A US3889600A US172597A US17259771A US3889600A US 3889600 A US3889600 A US 3889600A US 172597 A US172597 A US 172597A US 17259771 A US17259771 A US 17259771A US 3889600 A US3889600 A US 3889600A
- Authority
- US
- United States
- Prior art keywords
- payload
- munition
- aziridines
- aziridine
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 abstract description 14
- -1 vinylsubstituted benzene Chemical class 0.000 abstract description 4
- ZSVSXKYSXIIVQN-UHFFFAOYSA-N 1-[1-(3,4,5-trimethoxyphenyl)propan-2-yl]aziridine Chemical compound COC1=C(OC)C(OC)=CC(CC(C)N2CC2)=C1 ZSVSXKYSXIIVQN-UHFFFAOYSA-N 0.000 abstract 1
- ZREMZAFUSXQXHN-UHFFFAOYSA-N 1-[1-(6-methoxy-1,3-benzodioxol-5-yl)propan-2-yl]aziridine Chemical compound COC1=CC=2OCOC=2C=C1CC(C)N1CC1 ZREMZAFUSXQXHN-UHFFFAOYSA-N 0.000 abstract 1
- MVMONJCRJMHFNE-UHFFFAOYSA-N 1-[2-(3,4,5-trimethoxyphenyl)ethyl]aziridine Chemical compound COC1=C(OC)C(OC)=CC(CCN2CC2)=C1 MVMONJCRJMHFNE-UHFFFAOYSA-N 0.000 abstract 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 150000001541 aziridines Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IONRJSKJWDOGAY-UHFFFAOYSA-N 1-(3,4,5-trimethoxyphenyl)ethanol Chemical compound COC1=CC(C(C)O)=CC(OC)=C1OC IONRJSKJWDOGAY-UHFFFAOYSA-N 0.000 description 2
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 2
- DBEJPQQGEMWGRE-UHFFFAOYSA-N 5-ethenyl-1,2,3-trimethoxybenzene Chemical compound COC1=CC(C=C)=CC(OC)=C1OC DBEJPQQGEMWGRE-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000008560 physiological behavior Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000009295 sperm incapacitation Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 1
- 235000015842 Hesperis Nutrition 0.000 description 1
- 235000012633 Iberis amara Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000036540 impulse transmission Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000002232 neuromuscular Effects 0.000 description 1
- 210000000715 neuromuscular junction Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B49/00—Use of single substances as explosives
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F42—AMMUNITION; BLASTING
- F42B—EXPLOSIVE CHARGES, e.g. FOR BLASTING, FIREWORKS, AMMUNITION
- F42B12/00—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material
- F42B12/02—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect
- F42B12/36—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect for dispensing materials; for producing chemical or physical reaction; for signalling ; for transmitting information
- F42B12/46—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect for dispensing materials; for producing chemical or physical reaction; for signalling ; for transmitting information for dispensing gases, vapours, powders or chemically-reactive substances
- F42B12/54—Projectiles, missiles or mines characterised by the warhead, the intended effect, or the material characterised by the warhead or the intended effect for dispensing materials; for producing chemical or physical reaction; for signalling ; for transmitting information for dispensing gases, vapours, powders or chemically-reactive substances by implantation, e.g. hypodermic projectiles
Definitions
- trimethoxyphenyl)-2-propy1]aziridine and l-[ 1(2- [52] US. Cl 102/90; 102/66 methoxy-4,S-mthylenedioxyphenyl)-2- [51] Int. Cl. F42b 11/24 propy1]aziridine are prepared from the appropriate vi- [58] Field of Search 102/24, 39, 90, 66; nyl-substituted benzene and ethylenimine.
- the aziridines of the invention have in the free base form the structural formulas and wherein R is hydrogen or methyl.
- the compounds of this invention are mildly toxic, and, due to the toxicity, the compounds of this invention interfere with the normal process of neuromuscular impulse transmission and disrupt the propagation of impulses from animal nerves to muscles and mildly incapacitate the animal. Accordingly, the compounds of my invention were conceived and reduced to practice to supply a long sought composition which, due to abnormal physiological behavior produced in animals as a result of the effect on the central nervous system caused by the toxicity of the compound, can be used as an agent to induce mild incapacitation in an animal.
- the abnormal physiological behavior can result from mere contact of the compounds of this invention with the skin of the animal, and such contact can be brought about by means of dissemination of the compound by any conventional chemical munition having the compounds of this invention as a payload such as bombs, shells, spray tanks, rockets, missiles, aerosol generatirs, etc.
- the principal object of this invention is to utilized as the payload in a chemical munition a new composition of matter useful to induce incapacitation in an animal.
- Example I end product herein Example ll end product herein LD dosage necessary to kill MEDSO dosage necessary to incapacitate
- the preparation of the new 2-(trisubstitutedphenyl)-ethylaziridines is carried out by treating the appropriately substituted vinylbenzene with ethylenimine in the presence of sodium metal. Conveniently the substituted phenyl alkene is interacted with an excess of ethylenimine as a solvent to produce the aziridines.
- the free base can be isolated as such or converted to any desired acid addition salt by treatment with one equivalent of the appropriate organic or inorganic acid.
- the acid addition salts of the base are the form in which the base is more conveniently prepared for use and are the full equivalents of the subject matter specifically claimed.
- the intermediate vinylbenzenes are a known class of compounds generally prepared by dehydration of the EXAMPLE 1 l-[2-( 3 ,4,5-Trimethoxyphenyl )ethyl]aziridine ether layer was washed with water, dried and the ether removed by evaporation. Fractional distillation gave 1.72 g. of l-[2(3,4,5-trimethoxy)-ethyl]aziridine, b.p.
- EXAMPLE 3 l-[ l-(2-Methoxy-4,5-methylenedioxyphenyl)-2- propyl)-aziridine was prepared was prepared from 7 g. of l-( 2-methoxy-4,5-methylene-dioxyphenyl l propene, 0.9 g. of atomized sodium in 9 ml. of ethylenimine using the procedure described in Example 1.
- a munition comprising: a means for delivery, and a payload, said payload comprising a compound of the formula R l CHN C H wherein R is hydrogen or methyl.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- General Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
A munition having a payload of 1-(2-(3,4,5trimethoxyphenyl)ethyl)aziridine, 1-(1-(3,4,5-trimethoxyphenyl)2-propyl)aziridine and 1-(1(2-methoxy-4,5-methylenedioxyphenyl)2-propyl)aziridine are prepared from the appropriate vinylsubstituted benzene and ethylenimine.
Description
States tent [1 1 Razdan 1 June 17, 1975 1 l-(2-(PHENYL-LOWER-ALKYL)- [56] References Cited AZIRIDINES MUNITION PAYLOAD UNITED STATES PATENTS Inventor: j Razdan, m nt, Mass. 2,654,737 10/1953 Bestian 260/239 Assigneez The United States of America as 3,352,238 1l/1967 Spragg et a1. 102/39 represented by the Secretary of the Army, Washington, DC Przmary Exammer-Ben am1n A. Borchelt Assistant Examiner-Harold Tudor Flledi g- 7, 1971 Attorney, Agent, or Firm-Robert P. Gibson; Nathan [21 Appl. No.1 172,597 Edelberg I t d A l' D t 'HReae US pplcatlon aa ABSTRACT [60] Dwrsron of Ser. No. 22,668, March 25, 1970, Pat.
NO. 3,637,662, which is a continuation-in-part ofSer. A munmon havmg a p y of I No. 640,815, May 24, 1967. trimethoxypher'xyUethyl]aziridine, l-[ -(3,4,5-
trimethoxyphenyl)-2-propy1]aziridine and l-[ 1(2- [52] US. Cl 102/90; 102/66 methoxy-4,S-mthylenedioxyphenyl)-2- [51] Int. Cl. F42b 11/24 propy1]aziridine are prepared from the appropriate vi- [58] Field of Search 102/24, 39, 90, 66; nyl-substituted benzene and ethylenimine. 260/239 4 Claims, No Drawings l-(Z-PHENYL-LOWER-ALKYL)-AZIRIDINES MUNITION PAYLOAD DEDICATORY CLAUSE The invention described herein may be manufacture, used, and licensed by or for the government purposes with the payment to me of any royalty thereon.
This application is a divisional application of my pending US. Pat. Application Ser. No. 22,668 filed Mar. 25, 1970, now US. Pat. No. 3,637,662 continuation-in-part of US. Pat. Application Ser. No. 640,815 filed May 24, 1967, and relates to novel aziridines as a chemical munition payload. More particularly, the invention here is to certain 2-(tri-substituted phenyl)ethylaziridines as ther munition payload.
The aziridines of the invention, have in the free base form the structural formulas and wherein R is hydrogen or methyl.
compounds as therapeutic agents and other prior art compounds as lethal or incapacitating agents. The nature of the functional groups of the compounds, the length and branching of aliphatic chains, and the number and configuration of aromatic and alicyclic rings affect the case or difficulty of approach of the compound to the specific neuromuscular junctions and other acetylcholine receptive sites. Substitution of different functional groups influence association and hydration and can considerably change the solubilities in animal physiological media, either in vivo or in vitro.
As demonstrated by the test data set forth in Table l, the compounds of this invention are mildly toxic, and, due to the toxicity, the compounds of this invention interfere with the normal process of neuromuscular impulse transmission and disrupt the propagation of impulses from animal nerves to muscles and mildly incapacitate the animal. Accordingly, the compounds of my invention were conceived and reduced to practice to supply a long sought composition which, due to abnormal physiological behavior produced in animals as a result of the effect on the central nervous system caused by the toxicity of the compound, can be used as an agent to induce mild incapacitation in an animal. The abnormal physiological behavior can result from mere contact of the compounds of this invention with the skin of the animal, and such contact can be brought about by means of dissemination of the compound by any conventional chemical munition having the compounds of this invention as a payload such as bombs, shells, spray tanks, rockets, missiles, aerosol generatirs, etc.
The principal object of this invention is to utilized as the payload in a chemical munition a new composition of matter useful to induce incapacitation in an animal.
Other objects of and uses for my invention will be obvious from and will appear hereinafter in the following detailed description of the invention.
TABLE I Dose/Animal Screen Animal Compound Tested Weight In mg/kg Symptoms Example I end product herein Example ll end product herein LD dosage necessary to kill MEDSO dosage necessary to incapacitate The preparation of the new 2-(trisubstitutedphenyl)-ethylaziridines is carried out by treating the appropriately substituted vinylbenzene with ethylenimine in the presence of sodium metal. Conveniently the substituted phenyl alkene is interacted with an excess of ethylenimine as a solvent to produce the aziridines. The free base can be isolated as such or converted to any desired acid addition salt by treatment with one equivalent of the appropriate organic or inorganic acid. The acid addition salts of the base are the form in which the base is more conveniently prepared for use and are the full equivalents of the subject matter specifically claimed.
The intermediate vinylbenzenes are a known class of compounds generally prepared by dehydration of the EXAMPLE 1 l-[2-( 3 ,4,5-Trimethoxyphenyl )ethyl]aziridine ether layer was washed with water, dried and the ether removed by evaporation. Fractional distillation gave 1.72 g. of l-[2(3,4,5-trimethoxy)-ethyl]aziridine, b.p.
EXAMPLE 2 l l-( 3 ,4,5-Trimethoxyphenyl)-2-propyl]aziridine was prepared from 6 g. of l-(3,4,5-trimethoxyphenyl)- l-propene and 0.13 g. of sodium-metal in 3 ml. of
ethylenimine using the procedure described in Example 1. There was thus obtained 2.1 g. of l-[1-(3,4,5- trimethoxyphenyl)-2-propyl]aziridine, b.p. lOO10l/0.4 mm.
EXAMPLE 3 l-[ l-(2-Methoxy-4,5-methylenedioxyphenyl)-2- propyl)-aziridine was prepared was prepared from 7 g. of l-( 2-methoxy-4,5-methylene-dioxyphenyl l propene, 0.9 g. of atomized sodium in 9 ml. of ethylenimine using the procedure described in Example 1. The 1-[ l-(2-methoxy-4,S-methylenedioxyphenyl)-2- propyl]aziridine thus obtained had the b.p. lOl/O.3 55
CH 0 .CH2CHNQ OR CH 2 o Intermediates I l-(3,4,5 Trimethoxyphenyl)ethanol A solution of 25 g. of 3,4,5-trimethoxybenzaldehyde in 720 ml. of ether was added to a refluxing solution of methylmagnesium bromide made from 6.22 g. of magnesium turnings and 25.26 g. of methyl bromide in 400 ml. of ether. The mixture was refluxed for 12 hours then hydrolyzed with 300 ml. of 10% ammonium chloride. The ether layer was separated, the aqueous layer extracted with ether and the combined extracts washed with water and dried. The ether was removed by evaporation and the residue fractionally distilled to give 2l g. of 1(3,4,5-trimethoxyphenyl)ethanol, b.p.
l33l34/0.l mm.
3 ,4,5-Trimethoxystyrene The 1-(3,4,5-trimethoxyphenyl)ethanol prepared as above 14.6 g.) was added dropwise to 2.5 g. of freshly fused potassium hydrogen sulfate, containing a small crystal of p-t-butyl-catechol, at 220-230, while the pressure was kept at 18 mm. After the addition was complete the temperature and pressure were held constant for 10 minutes, then the pressure was slowly lowered and the product distilled at 0.2 mm. The distillate was dissolved in 50 ml. of ether, the ether solution washed with water and dried, and a small amount of tbutylcatichol added. After the ether was removed by distillation the residue was fractionated to give 5.8 g. of 3,4,5-trimethoxystyrene, b.p. 99-lOl/0.5 mm.
It is obvious that other modifications may be made of my invention, and I desire that my invention be limited only by thescope of the appended claims.
What is claimed is:
l. A munition comprising: a means for delivery, and a payload, said payload comprising a compound of the formula R l CHN C H wherein R is hydrogen or methyl.
2. A compound according to claim 1 of formula (A) wherein R is hydrogen.
3. A compound according to claim 1 of Formula (A) wherein R is methyl.
4. A compound according to claim 1 of Formula (B) wherein R is methyl.
Claims (4)
1. A MUNITION COMPRISING: A MEANS FOR DELIVERY, AND A PAYLOAD, SAID PAYLOAD COMPRISING A COMPOUND OF THE FORMULA
2. A compound according to claim 1 of formula (A) wherein R is hydrogen.
3. A compound according to claim 1 of Formula (A) wherein R is methyl.
4. A compound according to claim 1 of Formula (B) wherein R is methyl.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US172597A US3889600A (en) | 1970-03-25 | 1971-08-17 | 1-(2-(Phenyl-lower-alkyl)-aziridines munition payload |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2266870A | 1970-03-25 | 1970-03-25 | |
| US172597A US3889600A (en) | 1970-03-25 | 1971-08-17 | 1-(2-(Phenyl-lower-alkyl)-aziridines munition payload |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3889600A true US3889600A (en) | 1975-06-17 |
Family
ID=26696210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US172597A Expired - Lifetime US3889600A (en) | 1970-03-25 | 1971-08-17 | 1-(2-(Phenyl-lower-alkyl)-aziridines munition payload |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3889600A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6060100A (en) * | 1999-01-05 | 2000-05-09 | Koller; Thomas J. | Method of preparing pet chew products |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2654737A (en) * | 1949-09-26 | 1953-10-06 | Hoechst Ag | Process of preparing derivatives of ethyleneimine |
| US3352238A (en) * | 1965-10-12 | 1967-11-14 | Universal Match Corp | Atomizer and method for disseminating toxicants |
-
1971
- 1971-08-17 US US172597A patent/US3889600A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2654737A (en) * | 1949-09-26 | 1953-10-06 | Hoechst Ag | Process of preparing derivatives of ethyleneimine |
| US3352238A (en) * | 1965-10-12 | 1967-11-14 | Universal Match Corp | Atomizer and method for disseminating toxicants |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6060100A (en) * | 1999-01-05 | 2000-05-09 | Koller; Thomas J. | Method of preparing pet chew products |
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