ES355037A1 - Method of obtaining organo-phosphate compositions of substituted oxymes, phosphonates, phosphinates and phosphoroamidates, used as insecticides, herbicides and fungicides. (Machine-translation by Google Translate, not legally binding) - Google Patents
Method of obtaining organo-phosphate compositions of substituted oxymes, phosphonates, phosphinates and phosphoroamidates, used as insecticides, herbicides and fungicides. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES355037A1 ES355037A1 ES355037A ES355037A ES355037A1 ES 355037 A1 ES355037 A1 ES 355037A1 ES 355037 A ES355037 A ES 355037A ES 355037 A ES355037 A ES 355037A ES 355037 A1 ES355037 A1 ES 355037A1
- Authority
- ES
- Spain
- Prior art keywords
- atoms
- substituted
- alkyl
- lower alkyl
- 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
Links
- 229910019142 PO4 Inorganic materials 0.000 title abstract 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title abstract 2
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 title abstract 2
- 239000000417 fungicide Substances 0.000 title 1
- 239000004009 herbicide Substances 0.000 title 1
- 239000002917 insecticide Substances 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 239000010452 phosphate Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 19
- 125000000217 alkyl group Chemical group 0.000 abstract 14
- -1 2-thiazolyl Chemical group 0.000 abstract 8
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 7
- 125000003545 alkoxy group Chemical group 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 abstract 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 150000002923 oximes Chemical class 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 abstract 2
- BXEAAHIHFFIMIE-UHFFFAOYSA-N 3-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC=CC=1Cl BXEAAHIHFFIMIE-UHFFFAOYSA-N 0.000 abstract 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Chemical class 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 abstract 1
- KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 125000005499 phosphonyl group Chemical group 0.000 abstract 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 abstract 1
- ACOOSTZBTYEGER-UHFFFAOYSA-N thiobenzaldehyde Chemical compound S=CC1=CC=CC=C1 ACOOSTZBTYEGER-UHFFFAOYSA-N 0.000 abstract 1
- 229940029273 trichloroacetaldehyde Drugs 0.000 abstract 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/242—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of hydroxyaryl compounds
-
- 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
-
- 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- 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
-
- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3282—Esters with hydroxyaryl compounds
-
- 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
- C07F9/4084—Esters with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Novel oxime-containing phosphates, phosphonates, phosphinates and phosphoroamidates of the general formula in which X and Y are independently oxygen or sulphur, R is lower alkyl or lower alkoxy (up to 6 C atoms), R 1 is lower alkyl or lower alkoxy (up to 6 C atoms), amino, lower alkyl-substituted amino or phenyl, Q is hydrogen, divalent tetramethylenediene - 1,3, lower alkoxy or lower alkyl (up to 4 carbon atoms), nitro, halogen or combinations thereof, or lower dialkyl substituted thionophosphoryloxy, R 2 is hydrogen, lower alkyl (up to 4 C atoms) or phenyl, and R 3 is one of the following: (a) hydrogen, (b) substituted carbonate and thiocarbonate-forming groups of the type in which Z is oxygen or sulphur and R 4 is lower alkyl (1 to 4 carbon atoms) or #-chloro lower alkyl (2 to 4 C atoms), (c) carbamate-forming groups of the type in which R 5 and R 6 are independently hydrogen, alkyl having 1 to 10 C atoms, substituted alkyl having 1 to 6 C atoms (substituent is hydroxy, halogen, amino, dialkylamino, lower alkoxy or tetrahydrofuryl), lower alkenyl (2 to 4 C atoms) carboalkoxy alkyl having a total of from 3 to 8 C atoms, cycloalkyl having from 3 to 6 C atoms, 2-thiazolyl, phenyl, naphthyl, or substituted phenyl (substituent is halogen, lower alkyl, lower alkoxy, lower alkylthio, lower dialkyl-amino, having 1 to 4 C atoms, nitro, cyano, trifluoromethyl or combinations thereof) or in which is an N-containing heterocyclic radical selected from morpholino, piperazino, N-methyl piperazino, pyrrolidono, piperidino, hexamethyleneimino, pyrryl, indolyl, imidazolyl, benzimidazolyl, pyrazolyl, 1,3 - oxazolidino, and 1,3- thiazolidino, (d) groups of the type in which R 7 is alkyl having 1 to 8 C atoms, trichloromethyl, lower alkenyl having from 2 to 4 C atoms or the radical -(CH 2 )m-SR in which m is 1 or 2, R is alkyl having 1 to 6 C atoms, alkenyl having 2 to 4 C atoms, phenyl or substituted phenyl (substituent being halogen, lower alkyl having 1 to 4 carbon atoms, or lower alkoxy having 1 to 4 carbon atoms), (e) lower alkyl sulphonyl having from 1 to 6 C atoms, (f) lower alkyl substituted thionophosphoryl or (g) 2,2,2 - trichloro - 1 - hydroxyethyl, 4 - cyanophenyl, 2,4,5 - trichlorophenyl, or 4 - methylthiophenyl, are prepared by reacting the appropriate substituted phosphoryl, phosphonyl or phosphinyl oxy or thio benzaldehyde (R 2 = H) or phenyl lower-alkyl ketone (R 2 = lower alkyl) with hydroxylamine hydrochloride to give the corresponding oxime, which is then further reacted (unless R 3 = H) with the appropriate substituted isocyanate, acid chlorides, chloroformate, chlorothiolformate, sulphonyl chloride, N - mono or N,N - disubstituted carbamyl chlorides, substituted thionophosphoryl chloride or anhydrous trichloroacetaldehyde. The compounds have pesticidal properties. 3 - O,O - diethylphosphorothioyloxy benzaldehyde is prepared by reacting O,O - diethylthionophosphoryl chloride with 3-hydroxybenzaldehyde in the presence of K 2 CO 3 .
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64646767A | 1967-06-16 | 1967-06-16 | |
| US73058868A | 1968-05-20 | 1968-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES355037A1 true ES355037A1 (en) | 1970-10-16 |
Family
ID=27094939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES355037A Expired ES355037A1 (en) | 1967-06-16 | 1968-06-15 | Method of obtaining organo-phosphate compositions of substituted oxymes, phosphonates, phosphinates and phosphoroamidates, used as insecticides, herbicides and fungicides. (Machine-translation by Google Translate, not legally binding) |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE716339A (en) |
| CH (1) | CH509761A (en) |
| DE (1) | DE1768676C3 (en) |
| ES (1) | ES355037A1 (en) |
| FR (1) | FR1583911A (en) |
| GB (1) | GB1229853A (en) |
| IL (1) | IL30131A (en) |
| NL (1) | NL6808399A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112391096A (en) * | 2019-08-13 | 2021-02-23 | 石鑫 | Flame-retardant waterproof exterior wall paint |
-
1968
- 1968-06-05 IL IL30131A patent/IL30131A/en unknown
- 1968-06-10 BE BE716339D patent/BE716339A/xx unknown
- 1968-06-13 GB GB1229853D patent/GB1229853A/en not_active Expired
- 1968-06-14 FR FR1583911D patent/FR1583911A/fr not_active Expired
- 1968-06-14 NL NL6808399A patent/NL6808399A/xx unknown
- 1968-06-15 DE DE1768676A patent/DE1768676C3/en not_active Expired
- 1968-06-15 ES ES355037A patent/ES355037A1/en not_active Expired
- 1968-06-17 CH CH893568A patent/CH509761A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL30131A0 (en) | 1968-09-26 |
| FR1583911A (en) | 1969-12-05 |
| DE1768676C3 (en) | 1978-11-16 |
| IL30131A (en) | 1972-08-30 |
| CH509761A (en) | 1971-07-15 |
| GB1229853A (en) | 1971-04-28 |
| DE1768676B2 (en) | 1978-03-16 |
| NL6808399A (en) | 1968-12-17 |
| BE716339A (en) | 1968-12-10 |
| DE1768676A1 (en) | 1971-11-18 |
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