IL28866A - Alkyl ammonium phosphonoamidates and their preparation - Google Patents
Alkyl ammonium phosphonoamidates and their preparationInfo
- Publication number
- IL28866A IL28866A IL2886667A IL2886667A IL28866A IL 28866 A IL28866 A IL 28866A IL 2886667 A IL2886667 A IL 2886667A IL 2886667 A IL2886667 A IL 2886667A IL 28866 A IL28866 A IL 28866A
- Authority
- IL
- Israel
- Prior art keywords
- amine
- anhydride
- phenyl
- lauryl
- process according
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 6
- 125000005210 alkyl ammonium group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 10
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical group CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical group CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- MWGSSMAHEZDRQP-UHFFFAOYSA-N [hydroxy(phenyl)phosphoryl]oxy-phenylphosphinic acid Chemical group C=1C=CC=CC=1P(=O)(O)OP(O)(=O)C1=CC=CC=C1 MWGSSMAHEZDRQP-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 4
- -1 ammonium N-lauryl phenylphosphonamidate Chemical compound 0.000 description 4
- XNQULTQRGBXLIA-UHFFFAOYSA-O phosphonic anhydride Chemical compound O[P+](O)=O XNQULTQRGBXLIA-UHFFFAOYSA-O 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PNXWPUCNFMVBBK-UHFFFAOYSA-M 1-dodecylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCCCCCCCC[N+]1=CC=CC=C1 PNXWPUCNFMVBBK-UHFFFAOYSA-M 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- WTFUTSCZYYCBAY-SXBRIOAWSA-N 6-[(E)-C-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-N-hydroxycarbonimidoyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C/C(=N/O)/C1=CC2=C(NC(O2)=O)C=C1 WTFUTSCZYYCBAY-SXBRIOAWSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 231100001225 mammalian toxicity Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4403—Amides thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4419—Amides of aromatic acids (P-C aromatic linkage)
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3834—Aromatic acids (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4403—Amides thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4407—Amides of acyclic saturated acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
Description
Alkyl ammonium phosp onoaa&da ea and their preparation STAUFPER CHEMICAL COMPANY Ci 27390 28866 3 - la - of n name in which R is a halo substituted alkyl of from 1 to 8 carbon atoms inclusive, or a phenyl radical which may be substituted with one or more halogen, preferably chlorine atoms, hydroxy, cyano and/or nitro groups; and R* is an alkyl group containing from 12 to 18 carbon atoms inclusive.
According to the invention, the compounds of formula I above are prepared by reacting a phosphonic acid anhydride with a long chain alkyl amine in accordance with the following reaction diagram, wherein S and R' are as previously defined and n is an integer greater than 2.
The phosphonic acid anhydride and the amine are reacted at a temperature between about 0° and 150°C, and preferably between about 50°C. and 120°0, The reaction is exothermic until the mH bond is formed but the reaction may be easily controlled by external cooling and vigorous agitation* fhe phosphonic anhydride, which is a solid at room temperature, is preferably added in the liquid state to the amine in order to permit lower reaction temperatures. This can be accomplished by heating the anhydride to a temperature between abou 50°C. and 150°C. After the P-N bond is formed, the remainder of the reactants can be rapidly combined without the need for external cooling.
After the reactants have been combined, it is preferred to maintain the temperature of the reaction mixture between about 80°C. and 150°C« for 1- 2 hours, while agitating the mixture to insure completion of the reaction.
In order to inhibit reaction of the halogen-substituted alkyl group of the phosphonic anhydride with the alkyl amine reactant, it is preferred to conduct the reaction stepwise.
This can be accomplished by reacting n moles of amine per mole of phosphonic anhydride at a temperature between about 50°C. and 150°C» and thereafter reacting the resultant compound with n more moles of emine at a temperature between about 0 and 100°C. in the presence of an inert organic solvent. 28866 3 3 - Although the product is principally the slkylammonium alkylphosphonamidate depicted in the reaction diagram, minor amounts of the follovring by-products are also produced: wherein radical or an R'HNiCH^Jg- radical wherein n is an integer of from 1 to 8 inclusive; and R* is as previously defined. The compounds are not easil separated by conventional means such as crystallization or fractionation. The impure product mixture, however, has excellent pesticidal properties and consequently separation of the reaction components is not required or, in fact, for most uses ordinarily desirable.
If desired , the alkyl groups in the salt and amide portion of the molecule can be the same or different.
When dif erent, the compounds are prepared by reacting oae mole of the appropriate phosphonic anhydride with n moles of amine, and thereafter reacting the reaction product with n moles of a different amine.
Representative compounds within the ambit of this invention include the following: COMPOUND 1 COMPOUND 2 + im5(cH2)15-cB EXAMPLE 2 Preparation of 1auryl ammonium N-lauryl phenylphosphonamidate .
To a 500 cubic centimeter three-necked reaction flask fitted with a stirrer, thermometer and separatory funnel is added 37 grams (0.2 mole) of distilled lauryl amine. By way of the separatory funnel is added 14 grams (0·1 mole) of phenylphosphonic acid anhydride while maintaining the temperature of the reaction mixture below 6° C. The mixture is then maintained within a temperature range of 90° - 100° C for approximately 1-1/2 hours, during which time agitation of the mixture is continued. The mixture is then allowed to cool to room temperature, whereupon the mixture solidifies into a semi-solid and the product is recovered directly.
EXAMPLE J Preparation of stearylammonium N-stearyl phenylphosphonamidate To a 500 cubic centimeter three-necked reaction flask fitted with a stirrer, thermometer and separatory funnel is added 113 grams (0.42 mole) of stearyl amine.
The amine is maintained within a temperature range of 70° - 80° C. and 163 grams (0.78 mole) of phenyl phosphoric anhydride is added. After the addition is complete, the mixture is heated to a temperature of 100° C. at which point a red transparent liquid is observed. The mixture is then allowed to cool to room temperature, whereupon the mixture solidifies into a semi-solid material and the product is recovered directly.
EXAMPLE 5 4 Preparation of laurylammonium N-lauryl chloromethyl phosphonamidate To a three-necked 500 cubic centimeter flask fitted with a separatory funnel, stirrer and thermometer is added 119.4 grams (1·θ6 moles) of chloromethylphos-phonic anhydride. The solid is heated until in the molten state at a temperature of about 150° C. , and 182.5 grams (·1·θ6 moles) of freshly distilled lauryl amine is added to this melt. The reaction mixture is vigorously stirred and external cooling is applied during the addition, so that the temperature of the reaction mixture is maintained between about 110° C and 120° C. After the amine addition and the subsidence of the subsequent exothermic reaction is complete, an additional equivalent of amine, dissolved in 100 milliliters of toluene, is added. The reaction is conducted at room temperature and the resultant viscous material is recovered directly.
The compounds of the invention are useful as pesticides and exhibit, for example, fungicidal and bactericidal activity.
To test for protectant action of one of the invention compounds against fungi attacking plant foliage, 8 pinto bean plants are thoroughly sprayed with a concen-tration of dissolved or suspended compound in water. The plants are allowed to dry and are then inoculated with rust spores. Three to four weeks after treatment, the plants are observed and compared with untreated plants which have been infested with rust spores. The product of Exam le 1 is found to ive com lete control a ainst rust in an organic solvent may .be applied directly to the soil in the form of a spray. Alternatively dispersions of the compounds in a water media may be advantageously employed. In the latter case, the use of various surface-active agents or soaps may be desirable. . The surface-active agents may be of the anionic, cationic or non-ionic types to include the sulfonated animal and vegetable oils, sulfonated petroleum oils, sodium lauryl sulfonate, ethylene oxide condensation products of the type produced by reacting octyl phenol with ethylene oxide and higher alkyl pyridinium halides as exemplified by lauryl pyridinium bromide. In general, highly satisfactory results are obtained when the surface-active agent constitutes between about 1 - ±5% of the composition.
It is noteworthy that the compounds are non-toxic to mammals, a property which permits highly diversified use without danger of damage to livestock. Mammalian toxicity is determined by using albino mice, and the results are reported in milligrams of toxicant per kilogram of body weight required to produce 50% mortality, when administered by intraperitoneal injection. The product of Example 1 is found to have a MT-50 of 390 mg/kg.
Claims (9)
1. A process for the preparation of compounds of the general formula: in which R is a halo substituted alkyl of from 1 to 8 carbon atoms inclusive, or a phenyl radical which may be substituted with one or more halogen, preferably chlorine, atoms, hydroxy, cyano and/or nitro groups; and R« is an alkyl group containing from 12 to 18 carbon atoms Inclusive, wherein a phosphonic acid / anhydride of the general formula: 0 II H -0-P- OH I R n in which n is an integer greater than 2 and R has the same meaning as above, is reacted with 2n moles of a long chain alkyl amine of the general formula: R»NH2 in which R' has the same meaning as above.
2. A process according to Claim 1, wherein the phosphonic acid anhydride is chloromethylphosphonic anhydride. > -
3. A process according to Claim 1, wherein the phosphonic acid anhydride is phenylphosphonic anhydride.
4. ; A process according to any of Claims 1 to 3, wherein the amine is lauryl amine.
5. A process according to any of Claims 1 to-3, wherein the amine is stearyl amine.
6. Compounds of the general formula I in Claim 1, in which R is a halo substituted alkyl radical of 1 to 8 carbon atoms or a phenyl raetLcal, and R* has the same meaning as in Claim 1.
7. The compound of formul I in Claim 1 wherein R is chloromethyl and R1 is lauryl.
8. The compound of formula I ih Claim 1 wherein R is phenyl and R' is lauryl.
9. The compound of formula I in Claim 1 wherein R is phenyl and R' is a stearyl. MD:BH
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59232866A | 1966-11-07 | 1966-11-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL28866A true IL28866A (en) | 1971-12-29 |
Family
ID=24370222
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2886667A IL28866A (en) | 1966-11-07 | 1967-10-31 | Alkyl ammonium phosphonoamidates and their preparation |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE706152A (en) |
| CH (1) | CH491966A (en) |
| DE (1) | DE1668704A1 (en) |
| GB (1) | GB1205402A (en) |
| IL (1) | IL28866A (en) |
| NL (1) | NL6715107A (en) |
-
1967
- 1967-10-31 IL IL2886667A patent/IL28866A/en unknown
- 1967-11-03 CH CH1540367A patent/CH491966A/en not_active IP Right Cessation
- 1967-11-04 DE DE19671668704 patent/DE1668704A1/en active Pending
- 1967-11-07 NL NL6715107A patent/NL6715107A/xx unknown
- 1967-11-07 BE BE706152D patent/BE706152A/xx unknown
- 1967-11-07 GB GB5048767A patent/GB1205402A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6715107A (en) | 1968-05-08 |
| BE706152A (en) | 1968-05-07 |
| GB1205402A (en) | 1970-09-16 |
| DE1668704A1 (en) | 1971-09-16 |
| CH491966A (en) | 1970-06-15 |
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