US3201444A - Omicron-alkyl-omicron-cycloalkyl thiophosphoric acid s-phenylesters - Google Patents
Omicron-alkyl-omicron-cycloalkyl thiophosphoric acid s-phenylesters Download PDFInfo
- Publication number
- US3201444A US3201444A US271878A US27187863A US3201444A US 3201444 A US3201444 A US 3201444A US 271878 A US271878 A US 271878A US 27187863 A US27187863 A US 27187863A US 3201444 A US3201444 A US 3201444A
- Authority
- US
- United States
- Prior art keywords
- omicron
- acid
- alkyl
- ester
- cyclohexyl
- 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 description 21
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- 241000238876 Acari Species 0.000 description 6
- 244000078703 ectoparasite Species 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229950005499 carbon tetrachloride Drugs 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- -1 methyLethyl Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WVTOJNFZIVWNIY-UHFFFAOYSA-N (4-chlorophenyl) thiohypochlorite Chemical compound ClSC1=CC=C(Cl)C=C1 WVTOJNFZIVWNIY-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010008583 Chloroma Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000238680 Rhipicephalus microplus Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical class ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
-
- 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
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/177—Esters of thiophosphoric acids with cycloaliphatic alcohols
Definitions
- R preferably stands for methyLethyl and propyl.
- R preferably stands for cyclohexyl and cyclopentyl.
- R preferably stands for halogen, such as chlorine, bromine and fluorine, methyl, ethyl, methoxy and ethoxy.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
UnitedStates Patent O 7 The present invention relates to'and has, as its objects new and useful Oralkyl-O-cycloalkyl thiophosphoric acid S-phenylesters which show a remarkable activity against ectoparasites.
QO-dialkyl-phosphoric' acid-S-phenylester's are already known (cf. US. patent specification 2,861,876). These phosphorus containing compounds have only a very low activity. against ectoparasites. The most active compound of this group is the 0,0-diethyl-phosphoric acid- S(p-' chlorophenyl)ester .of the formula onrfio o J It has been foundthat the O-alkyl-O-cycloalkylthiophosphoric acid-S-phenylesters of the formula wherein 1 R stands for lower alkyl with 1 'to 4 carbon atoms or loweralkenyl with 1 to 4 carbon atoms,
R stands for cycloalkyl with 5 to 6 carbon atoms,.
R stands for'halogen, lower alkyl with 1 to 4 carbon atoms or lower alkoxy with l to 4 carbon atoms, and
It stands for 1 or 2,
possess a hi h activityagainst ectoparasites.
It is very surprising that the compounds according to the invention have a considerably higher activity against ectoparasites thanthe known compounds which are similar to the compoundsof the invention. It is completely surprising that the substitution of aicycloalkyl radical for alower alkyl radical increases the pesticidal activity of about 10 to 250 times (of. the table below).
In the above formula ofthe compounds according to the invention -R .preferably :stands for methyLethyl and propyl. R preferably stands for cyclohexyl and cyclopentyl. R preferably stands for halogen, such as chlorine, bromine and fluorine, methyl, ethyl, methoxy and ethoxy.
The following individually mentioned compounds represent a selection of especially suitable compounds which can be used in accordance with the invention:'
O-ethyl-O-cyclohexyl-thiolphosphoric-acid-S m-chloro- V phenyl)-ester,
V 0methyl-O-cyclopentyl-thiolphosphoric-acid-S(pchlorophenyl) ester, O-ethyl-O-cyclopentyl-thiolphosphoric-acid-S (p-chlorophenyl -ester,
r 3,201,444 Patented Aug. 17, 1965 O-ethyl-O-cyclohexyl-thiolphosphoric-acid-S (p-chlorom-methylphenyl) -ester,
O-ethyl-O-cyclohexyl-thiolphosphoric-acid-S (p-chlorom-rnethoxyphenyl -ester.
The compounds of the invention can be produced in accordance with known processes, for instance O-alkyl-O- cyclohlkyl phosphites can be reacted with phenylsulphenic acid chlorides preferably in the presence of inert solvent such as carbontetrachloride at temperatures between 0 and about 60. Representative examples for the preparation of compounds accordingto the invention are given below. V
The phosphorus containing compounds of the invention can be usedto combat ectoparasites such as the several typesof ticks which'belong' to the group of mites.
For cornbatting ectoparasites of domestic animals the spray or dippro cess is preferably used.
In the following the effectiveness of the compounds according to the invention and their superiority over the known chemically similar compounds is established.
The following compounds are prepared and compared:
(I, known) Aqueous dilutions of these compounds are prepared by admixing :themwith the same amount of dime-thyl formamide as an auxiliary solvent adding thereto 20% by weight referred :to the active ingredient of a commercial emulsifierconsisting of a ibenzyl hydroxy polyglyeol ether containing about 10 to.15 glycol residues, and diluting at least this premixture with water to the desired concentration indicated in the table below.
The tests are carried out as follows: a) 10 femaletioks each of the type Boophilus microplus are placed into mull bags which are brought into a solution prepared :as described above 'while moving them continuously. After 1 minute the mull bagsare taken off the active solutions and put into glass dishes in which filter paper is placed. .The ticks are taken off the mull bags and placed upon dry filter paper. Evaluation occurred after 72 hours. The following results are obtained:
Concentration Compound (in percent Killing rate active ingredi- (in percent) ent/water) The following example relates to the use of the cornpound of the invention for com'batting ticks in the skin of cattle: t n
(b) "8 young head of cattle infested by .ticks are sprayed with aqueous suspensions prepared as indicated above containing 0.0030% of compounds III and IV re- 7 spectively. The living status of the ticks is evaluated To a solution of 45 g. (0.25 mol) of O-methyl-O-cyclohexylphosphite (boiling point 124 C./7 mm.) in 150 com. of carbon tetrachloride are added at 20 C. with stirring 45 g. of 4-chlorophenylsulphenic acid chloride. Subsequently the reaction mixture is stirred for an hour at 20 C, Subsequently the reaction mixture is washed with a solution containing 3% by weight of sodium hydrogen carbonate until it reacts neutral. The organic layer is separated and dried over anhydrous sodium sulphate and finally distilled. There are obtained 71 g. (89% of the theory) of O-methyl-O-cyclohexyl-S-(4- c'hlorophenyl)-thiolphosphate in the form of a water insoluble colourless oil.
Analysis.-Oaloulated for a molecular weight of 321: P, 9. 6%; S, 10.0%. Found: P, 8.1%; S, 11.0%.
Example 2 96 g. (0.5 mol) of cyclohexyl-ethyl phosphite (boiling point 64 C./0.01 mm. Hg) are added with stirring to a solution of 90 g. of p-ohlorophenyl sulphenic acid chloride in 400 com, carbon tetrachloride. Subsequently the reaction mixture is stirred for an hour at '20 C. The reaction product is poured into 500 cc. iced water. The organic phase is separated and dried over anhydrous sodium sulphate. The carbon tetrachloride is evaponated and 142 g. of the above shown compound are obtained in a yield of 85% of the theoretical. The new ester is insoluble in water and constitutes a colourless oil, n 1,5332.
Analysis.Calcula-ted for a molecular weight of 335: C1, 10.6%; S, 9.6%; -P, 9.3%. Found: CI, 10.2%; S, 9.8%; P, 9.3%.
The toxicity of the compound is 25 mg. per kg. rat (DL per os). In the same way the following compounds can be obtained:
O-isopropyl-O-cyclohexyl-thiolphosphoric-acid-S (p-chlorophenyl) ester,
O-methyl-O-cyclohexyl-thiolphosphoric-acid-S(m-chlorophenyD-ester,
. a O-ethyl-O-cyclohexyl-thiolphosphoric-acid-S(tn-chloropheny1)-ester.
I claim: 11. A O-alkyl-O-cycloalkyl thiophosphoric acid-S-phenylester of the formula R11 R10 0 l in which R stands for a member selected from the group consisting of lower alkyl with 1 to 4 carbon atoms and .lower ialkenyl with 1 to 4 canbon atoms,
R stands -for cyclo'alkyl with 5 to 6 canbon atoms,
R stands for a member selected from the group consisting of halogen, lower alkyl with 1 to 4 carbon atoms and lower alkoxy with 1 to 4 carbon atoms, and
It stands for a member selected from the group consisting of -1 and 2.
'2. A compound according to claim 1 wherein R is lower alkyl, R is cyclohexyl, R is halogen and n is 1. 3. A compound according to claim '1 wherein R is lower alkyl, R is cyclopentyl, R is halogen and n is 1.
4. O methyl 0 cyclohexyl thiolphosphoric acid- S( p-chlorophenyl -ester.
5. O ethyl O cyclohexyl thiolphosphorie acid- S (pchl orophenyl) -ester.
6. O isopropyl O cyclohexyl thiolphosphoricacid-S(p-chlorophenyl -ester.
7. O methyl O cyclohexyl thiolphosphor-ic acid- S(m-ch1orophenyl)-cster.
8. O ethyl O cyclohexyl thiolphosphoric acid- S'(m-chlorophenyl)-ester.
9. 0 methyl O cyclopentyl thiolphosphoricacid-S(p-chlorop,henyl)-ester.
10. O ethyl O cyclopentyl thiolphosphoric acid- S(p-ohlorophenyl)-ester.
11. O ethyl O cyclohexyl thiolphosphoric acid- S(p-chloro-m-methylphenyl -ester.
12. O ethyl O cyclohexyl thiolphosphoric acid- S(p-clrloro-m-methoxypheny1)-ester.
References Cited by the Examiner UNITED STATES PATENTS 2,690,450 9/54 Gilbert et a1 260--461 2,861,876 11/58 Birum 260-461 X 2,962,518 11/60 Lorenz ct a1. 26046'1 OTHER REFERENCES Bianchetti: Rend 1st Lombardo Sci, Pt. I, vol. 91, pp. 68-75 (1957).
CHARLES B. PARKER, Primary Examiner,
Claims (1)
1. A O-ALKYL-O-CYCLOALKYL THIOPHOSPHORIC ACID-S-PHENYLESTER OF THE FORMULA
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF34558A DE1212554B (en) | 1961-07-28 | 1961-07-28 | Process for the preparation of ring-substituted O, O-dialkyl-S-phenyl-thiolphosphoric acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3201444A true US3201444A (en) | 1965-08-17 |
Family
ID=7095608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US271878A Expired - Lifetime US3201444A (en) | 1961-07-28 | 1963-04-10 | Omicron-alkyl-omicron-cycloalkyl thiophosphoric acid s-phenylesters |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3201444A (en) |
| BE (2) | BE620621A (en) |
| BR (1) | BR6241516D0 (en) |
| CH (1) | CH421081A (en) |
| DE (1) | DE1212554B (en) |
| DK (1) | DK102941C (en) |
| GB (2) | GB966057A (en) |
| NL (3) | NL281500A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3444274A (en) * | 1964-10-29 | 1969-05-13 | Bayer Ag | Asymmetrical para-nitrophenyl phosphates |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4833371B1 (en) * | 1968-07-19 | 1973-10-13 | ||
| CH508347A (en) * | 1969-04-28 | 1971-06-15 | Ciba Geigy Ag | Pesticides |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2690450A (en) * | 1951-03-23 | 1954-09-28 | Allied Chem & Dye Corp | Method for preparation of sulfur-containing esters of phosphoric acid |
| US2861876A (en) * | 1955-12-01 | 1958-11-25 | Monsanto Chemicals | Method of destroying undesired plants |
| US2962518A (en) * | 1957-09-28 | 1960-11-29 | Bayer Ag | Phosphonic acid esters |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR994479A (en) * | 1949-07-10 | 1951-11-16 | S-nitrophenyl-0, 0-dialkylthiolphosphates and process for obtaining them | |
| DE817057C (en) * | 1949-10-11 | 1951-10-15 | Bayer Ag | Pest repellants |
| US2897227A (en) * | 1956-04-04 | 1959-07-28 | Dow Chemical Co | S-(chlorophenyl) o,o-dialkyl phosphorodithioates |
-
0
- NL NL281501D patent/NL281501A/xx unknown
- BE BE620758D patent/BE620758A/xx unknown
- BE BE620621D patent/BE620621A/xx unknown
- NL NL135595D patent/NL135595C/xx active
- NL NL281500D patent/NL281500A/xx unknown
-
1961
- 1961-07-28 DE DEF34558A patent/DE1212554B/en active Pending
-
1962
- 1962-07-06 CH CH814862A patent/CH421081A/en unknown
- 1962-07-26 DK DK332962AA patent/DK102941C/en active
- 1962-07-27 BR BR141516/62A patent/BR6241516D0/en unknown
- 1962-07-27 GB GB29057/62A patent/GB966057A/en not_active Expired
- 1962-07-30 GB GB29262/62A patent/GB983886A/en not_active Expired
-
1963
- 1963-04-10 US US271878A patent/US3201444A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2690450A (en) * | 1951-03-23 | 1954-09-28 | Allied Chem & Dye Corp | Method for preparation of sulfur-containing esters of phosphoric acid |
| US2861876A (en) * | 1955-12-01 | 1958-11-25 | Monsanto Chemicals | Method of destroying undesired plants |
| US2962518A (en) * | 1957-09-28 | 1960-11-29 | Bayer Ag | Phosphonic acid esters |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3444274A (en) * | 1964-10-29 | 1969-05-13 | Bayer Ag | Asymmetrical para-nitrophenyl phosphates |
Also Published As
| Publication number | Publication date |
|---|---|
| NL135595C (en) | |
| CH421081A (en) | 1966-09-30 |
| NL281500A (en) | |
| DE1212554B (en) | 1966-03-17 |
| BE620621A (en) | |
| BR6241516D0 (en) | 1973-05-24 |
| GB983886A (en) | 1965-02-17 |
| GB966057A (en) | 1964-08-06 |
| DK102941C (en) | 1965-10-25 |
| BE620758A (en) | |
| NL281501A (en) |
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