IL25604A - Phosphorus-containing esters and process for the preparation thereof - Google Patents

Phosphorus-containing esters and process for the preparation thereof

Info

Publication number: IL25604A
Authority: IL; Israel
Prior art keywords: dimethyl; compound; mol; thioether; preparation
Prior art date: 1965-07-24

Application number

IL2560466A

Other languages

English (en)

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1965-07-24

Filing date

1966-04-19

Publication date

1969-11-30

1966-04-19 Application filed by Bayer Ag filed Critical Bayer Ag

1969-11-30 Publication of IL25604A publication Critical patent/IL25604A/en

Links

238000002360 preparation method Methods 0.000 title claims description 14
238000000034 method Methods 0.000 title claims description 13
150000002148 esters Chemical class 0.000 title claims description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title description 2
239000011574 phosphorus Substances 0.000 title description 2
229910052698 phosphorus Inorganic materials 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 41
238000006243 chemical reaction Methods 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 3
150000003568 thioethers Chemical class 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims 1
150000003863 ammonium salts Chemical class 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
239000002904 solvent Substances 0.000 description 20
238000003756 stirring Methods 0.000 description 17
239000000243 solution Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
-1 alkyl radical Chemical class 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
239000003995 emulsifying agent Substances 0.000 description 9
241000196324 Embryophyta Species 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
229910019142 PO4 Inorganic materials 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000005457 ice water Substances 0.000 description 7
239000010452 phosphate Substances 0.000 description 7
241000238876 Acari Species 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
241000238631 Hexapoda Species 0.000 description 6
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 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
244000075850 Avena orientalis Species 0.000 description 5
235000007319 Avena orientalis Nutrition 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
241000255925 Diptera Species 0.000 description 4
125000002877 alkyl aryl group Chemical group 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
230000006378 damage Effects 0.000 description 4
229960001760 dimethyl sulfoxide Drugs 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
241001124076 Aphididae Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
241001454295 Tetranychidae Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
241001425390 Aphis fabae Species 0.000 description 2
241000238657 Blattella germanica Species 0.000 description 2
241000255579 Ceratitis capitata Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241001327638 Cimex lectularius Species 0.000 description 2
241000255601 Drosophila melanogaster Species 0.000 description 2
241000254099 Melolontha melolontha Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000238814 Orthoptera Species 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000254179 Sitophilus granarius Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
241000255588 Tephritidae Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241001454293 Tetranychus urticae Species 0.000 description 2
230000000895 acaricidal effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
241000256118 Aedes aegypti Species 0.000 description 1
241001136265 Agriotes Species 0.000 description 1
241001136249 Agriotes lineatus Species 0.000 description 1
241000489242 Amphitetranychus viennensis Species 0.000 description 1
241000256186 Anopheles <genus> Species 0.000 description 1
241000239290 Araneae Species 0.000 description 1
241000387321 Aspidiotus nerii Species 0.000 description 1
241000256593 Brachycaudus schwartzi Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000257161 Calliphoridae Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241001221118 Cecidophyopsis ribis Species 0.000 description 1
241001221116 Cecidophyopsis selachodon Species 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
241001262789 Chrysomya chloropyga Species 0.000 description 1
241001465977 Coccoidea Species 0.000 description 1
241001479447 Coccus hesperidum Species 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
241001221110 Eriophyidae Species 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
241000238821 Gryllus Species 0.000 description 1
241000258937 Hemiptera Species 0.000 description 1
241001659688 Hercinothrips femoralis Species 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
241000256602 Isoptera Species 0.000 description 1
241000258915 Leptinotarsa Species 0.000 description 1
241000258916 Leptinotarsa decemlineata Species 0.000 description 1
241000283986 Lepus Species 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
241000736227 Lucilia sericata Species 0.000 description 1
241000721703 Lymantria dispar Species 0.000 description 1
241000403354 Microplus Species 0.000 description 1
241000257229 Musca <genus> Species 0.000 description 1
241000257159 Musca domestica Species 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000238890 Ornithodoros moubata Species 0.000 description 1
241000488583 Panonychus ulmi Species 0.000 description 1
241001548358 Parapiesma quadratum Species 0.000 description 1
241000219833 Phaseolus Species 0.000 description 1
241001396980 Phytonemus pallidus Species 0.000 description 1
241000690748 Piesma Species 0.000 description 1
241000500437 Plutella xylostella Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
235000005805 Prunus cerasus Nutrition 0.000 description 1
241000722238 Pseudococcus maritimus Species 0.000 description 1
241000125162 Rhopalosiphum Species 0.000 description 1
241000125167 Rhopalosiphum padi Species 0.000 description 1
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
241001454294 Tetranychus Species 0.000 description 1
241001414989 Thysanoptera Species 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
JWMLCCRPDOIBAV-UHFFFAOYSA-N chloro(methylsulfanyl)methane Chemical compound CSCCl JWMLCCRPDOIBAV-UHFFFAOYSA-N 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
241000894007 species Species 0.000 description 1
238000005507 spraying Methods 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
150000003738 xylenes Chemical class 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
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
- 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
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- 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)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds

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)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL2560466A 1965-07-24 1966-04-19 Phosphorus-containing esters and process for the preparation thereof IL25604A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE1965F0046711 DE1238904B (de)	1965-07-24	1965-07-24	Verfahren zur Herstellung von Thiol- bzw. Thionothiolphosphor-(-phosphon)-saeureestern

Publications (1)

Publication Number	Publication Date
IL25604A true IL25604A (en)	1969-11-30

Family

ID=7101190

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL2560466A IL25604A (en)	1965-07-24	1966-04-19	Phosphorus-containing esters and process for the preparation thereof

Country Status (7)

Country	Link
BE (1)	BE684453A (de)
CH (1)	CH469741A (de)
DE (1)	DE1238904B (de)
ES (1)	ES329429A1 (de)
GB (1)	GB1081277A (de)
IL (1)	IL25604A (de)
NL (1)	NL6607832A (de)

1965
- 1965-07-24 DE DE1965F0046711 patent/DE1238904B/de active Pending
1966
- 1966-04-15 CH CH546666A patent/CH469741A/de unknown
- 1966-04-19 IL IL2560466A patent/IL25604A/en unknown
- 1966-04-25 GB GB1791366A patent/GB1081277A/en not_active Expired
- 1966-06-06 NL NL6607832A patent/NL6607832A/xx unknown
- 1966-07-22 BE BE684453D patent/BE684453A/xx unknown
- 1966-07-23 ES ES0329429A patent/ES329429A1/es not_active Expired

Also Published As

Publication number	Publication date
CH469741A (de)	1969-03-15
NL6607832A (de)	1967-01-25
DE1238904B (de)	1967-04-20
BE684453A (de)	1967-01-23
GB1081277A (en)	1967-08-31
ES329429A1 (es)	1967-05-16

Publication	Publication Date	Title
DE1238902B (de)	1967-04-20	Verfahren zur Herstellung von Phosphor-, Phosphon- bzw. Thionophosphor-, -phosphon-saeureestern
IL44235A (en)	1977-06-30	N-sulphenylated n-methylcarbamidoximes of 2-oxoalkanenitriles their preparation and insecticidal acaricidal and fungicidal compositions containing them
US4564611A (en)	1986-01-14	(Di)thio-phosphoric and -phosphonic acid derivatives, and their use in plant protection
US3763160A (en)	1973-10-02	Phosphorus containing esters of 2-hydroxyquinoxaline
GB2047250A (en)	1980-11-26	Pyrazol-4-yl phosphates
US3371132A (en)	1968-02-27	O-alkyl o(s)-(n-alkoxy-n-alkyl-carbamyl methyl) phenyl (thiolo) (thiono)phosphonates
US3712915A (en)	1973-01-23	Indanyl-n-methyl-carbamic acid esters
US3911055A (en)	1975-10-07	O-alkyl-O-(1-cyano-1-tert.-butylketonoxime)-thionophosphoric (phosphonic) acid esters
US3644598A (en)	1972-02-22	1 - alkoxy(-alkenyloxy -phenoxy) - 1-thiono-3-chloro(3-alkyl)phospholines
US3420829A (en)	1969-01-07	3,4 - dihydro - 4 - oxo - 1,2,3 - benzotriazine-3-yl-ethyl phosphoric and phosphonic acid esters
JPS5838439B2 (ja)	1983-08-23	トリアゾロチアゾリル−（チオノ）−リン酸（ホスホン酸）エステルの製造方法
US3962316A (en)	1976-06-08	Carbamate
US4096268A (en)	1978-06-20	1-Methyl-1,2,5,6-tetrahydropyridine-3-carboxylic acid esters and a method of use for combating insects or acarids
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