IL45926A - Thiadiazole phosphates and thiophosphates process for preparing them and pesticidal compositions - Google Patents

Thiadiazole phosphates and thiophosphates process for preparing them and pesticidal compositions

Info

Publication number: IL45926A
Authority: IL; Israel
Prior art keywords: thiadiazole; diethoxythiophosphoryloxy; formula; potassium; methyl
Prior art date: 1973-10-26

Application number

IL45926A

Other languages

English (en)

Other versions

IL45926A0 (en

Original Assignee

Roussel Uclaf

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.)

1973-10-26

Filing date

1974-10-24

Publication date

1977-08-31

1974-10-24 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1974-12-31 Publication of IL45926A0 publication Critical patent/IL45926A0/xx

1977-08-31 Publication of IL45926A publication Critical patent/IL45926A/en

Links

239000000203 mixture Substances 0.000 title claims abstract description 20
238000004519 manufacturing process Methods 0.000 title claims description 4
230000000361 pesticidal effect Effects 0.000 title abstract description 4
RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 title 1
OIQGUOUSNYMTMR-UHFFFAOYSA-N phosphoric acid;thiadiazole Chemical class C1=CSN=N1.OP(O)(O)=O OIQGUOUSNYMTMR-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 29
230000000749 insecticidal effect Effects 0.000 claims abstract description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 8
125000005843 halogen group Chemical group 0.000 claims abstract description 8
229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
230000001069 nematicidal effect Effects 0.000 claims abstract description 5
229910021529 ammonia Inorganic materials 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims abstract description 3
125000003545 alkoxy group Chemical group 0.000 claims abstract 2
-1 oxy radical Chemical class 0.000 claims description 49
YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
239000011149 active material Substances 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
YDJKOALREUJGEA-UHFFFAOYSA-N C(C)SC1=NC=NS1 Chemical compound C(C)SC1=NC=NS1 YDJKOALREUJGEA-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
XUEANMVGQZVXKZ-UHFFFAOYSA-N 5-ethoxy-1,2,4-thiadiazole Chemical compound CCOC1=NC=NS1 XUEANMVGQZVXKZ-UHFFFAOYSA-N 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
PDEWZQSQJDXSOG-UHFFFAOYSA-N n,n-dimethyl-1,2,4-thiadiazol-5-amine Chemical compound CN(C)C1=NC=NS1 PDEWZQSQJDXSOG-UHFFFAOYSA-N 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
QXQMHXFOKBUMBR-UHFFFAOYSA-N (5-butoxy-1,2,4-thiadiazol-3-yl)oxy-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCCCOC1=NC(OP(=S)(OCC)OCC)=NS1 QXQMHXFOKBUMBR-UHFFFAOYSA-N 0.000 claims 1
RBWBFQDYKPBURG-UHFFFAOYSA-N (5-ethylsulfanyl-1,2,4-thiadiazol-3-yl)oxy-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCSC1=NC(OP(=S)(OC)OC)=NS1 RBWBFQDYKPBURG-UHFFFAOYSA-N 0.000 claims 1
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
BQWONGJGXUBPCW-UHFFFAOYSA-N [5-[(4-chlorophenyl)methoxy]-1,2,4-thiadiazol-3-yl]oxy-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=NSC(OCC=2C=CC(Cl)=CC=2)=N1 BQWONGJGXUBPCW-UHFFFAOYSA-N 0.000 claims 1
239000003513 alkali Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
HGBLRZZIPGLOER-UHFFFAOYSA-N diethoxy-[(5-methylsulfanyl-1,2,4-thiadiazol-3-yl)oxy]-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=NSC(SC)=N1 HGBLRZZIPGLOER-UHFFFAOYSA-N 0.000 claims 1
PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 claims 1
239000002184 metal Chemical group 0.000 claims 1
MFVWSFXQWMYYSF-UHFFFAOYSA-L dipotassium;cyanoiminomethanedithiolate Chemical compound [K+].[K+].[S-]C([S-])=NC#N MFVWSFXQWMYYSF-UHFFFAOYSA-L 0.000 abstract description 10
229910052700 potassium Inorganic materials 0.000 abstract description 7
239000011591 potassium Substances 0.000 abstract description 7
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract description 6
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract description 5
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract description 5
229910052708 sodium Inorganic materials 0.000 abstract description 4
239000011734 sodium Substances 0.000 abstract description 4
229910052783 alkali metal Inorganic materials 0.000 abstract description 3
150000001340 alkali metals Chemical class 0.000 abstract description 3
238000006243 chemical reaction Methods 0.000 abstract description 3
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 abstract description 3
PTHGDVCPCZKZKR-UHFFFAOYSA-N (4-chlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C=C1 PTHGDVCPCZKZKR-UHFFFAOYSA-N 0.000 abstract description 2
JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 abstract description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract description 2
BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 abstract description 2
239000012312 sodium hydride Substances 0.000 abstract description 2
229910000104 sodium hydride Inorganic materials 0.000 abstract description 2
150000004867 thiadiazoles Chemical class 0.000 abstract description 2
238000006798 ring closing metathesis reaction Methods 0.000 abstract 2
YQTQAMSXVLIMPO-UHFFFAOYSA-N CCCC[SH](C(O)=S)OC Chemical compound CCCC[SH](C(O)=S)OC YQTQAMSXVLIMPO-UHFFFAOYSA-N 0.000 abstract 1
SMBDXOGWUSECEL-UHFFFAOYSA-N CCC[SH](C(O)=S)OC Chemical compound CCC[SH](C(O)=S)OC SMBDXOGWUSECEL-UHFFFAOYSA-N 0.000 abstract 1
MHNQYHXQUDQPOS-UHFFFAOYSA-N CO[SH](CC(C=C1)=CC=C1Cl)C(O)=S Chemical compound CO[SH](CC(C=C1)=CC=C1Cl)C(O)=S MHNQYHXQUDQPOS-UHFFFAOYSA-N 0.000 abstract 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
239000004480 active ingredient Substances 0.000 abstract 1
125000003342 alkenyl group Chemical group 0.000 abstract 1
BJIKOZOULYUROB-UHFFFAOYSA-N dimethoxymethanethione Chemical compound COC(=S)OC BJIKOZOULYUROB-UHFFFAOYSA-N 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
230000001035 methylating effect Effects 0.000 abstract 1
230000003647 oxidation Effects 0.000 abstract 1
238000007254 oxidation reaction Methods 0.000 abstract 1
229910052698 phosphorus Inorganic materials 0.000 abstract 1
239000011574 phosphorus Substances 0.000 abstract 1
239000007858 starting material Substances 0.000 abstract 1
229910052717 sulfur Inorganic materials 0.000 abstract 1
239000000047 product Substances 0.000 description 55
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
229940093499 ethyl acetate Drugs 0.000 description 12
235000019439 ethyl acetate Nutrition 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
238000013019 agitation Methods 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
241000238631 Hexapoda Species 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 5
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
241000254179 Sitophilus granarius Species 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
LOCFEBZCHQFGKQ-UHFFFAOYSA-N 5-methylsulfanyl-1,2,4-thiadiazole Chemical compound CSC1=NC=NS1 LOCFEBZCHQFGKQ-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
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 3
241000257159 Musca domestica Species 0.000 description 3
241000244198 Panagrellus silusiae Species 0.000 description 3
244000046052 Phaseolus vulgaris Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
XFBJRFNXPUCPKU-UHFFFAOYSA-N chloro-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(Cl)(=S)OC XFBJRFNXPUCPKU-UHFFFAOYSA-N 0.000 description 3
238000000034 method Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
229940072033 potash Drugs 0.000 description 3
235000015320 potassium carbonate Nutrition 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
UITSDXCBKVVYDW-UHFFFAOYSA-N 5-(dimethylamino)-1,2,4-thiadiazol-3-one Chemical compound CN(C)C1=NC(O)=NS1 UITSDXCBKVVYDW-UHFFFAOYSA-N 0.000 description 2
241000238657 Blattella germanica Species 0.000 description 2
241001674044 Blattodea Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000244206 Nematoda Species 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
241000985245 Spodoptera litura Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000005507 spraying Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
SONBBXPHMJJBIC-UHFFFAOYSA-N 3-diethoxyphosphinothioyloxy-n,n-dimethyl-1,2,4-thiadiazol-5-amine Chemical compound CCOP(=S)(OCC)OC1=NSC(N(C)C)=N1 SONBBXPHMJJBIC-UHFFFAOYSA-N 0.000 description 1
JRQBPKAKGKCDIW-UHFFFAOYSA-N 5-[(2,4-dichlorophenyl)methylsulfanyl]-1,2,4-thiadiazol-3-one Chemical compound OC1=NSC(SCC=2C(=CC(Cl)=CC=2)Cl)=N1 JRQBPKAKGKCDIW-UHFFFAOYSA-N 0.000 description 1
UOBUZGOMCUYWTB-UHFFFAOYSA-N 5-[(4-chlorophenyl)methylsulfanyl]-1,2,4-thiadiazol-3-one Chemical compound OC1=NSC(SCC=2C=CC(Cl)=CC=2)=N1 UOBUZGOMCUYWTB-UHFFFAOYSA-N 0.000 description 1
BBAGRZXUUFLZGT-UHFFFAOYSA-N 5-ethylsulfanyl-1,2,4-thiadiazol-3-one Chemical compound CCSC1=NC(=O)NS1 BBAGRZXUUFLZGT-UHFFFAOYSA-N 0.000 description 1
UOGIBRBPAGZREF-UHFFFAOYSA-N 5-methylsulfanyl-1,2,4-thiadiazol-3-one Chemical compound CSC1=NC(=O)NS1 UOGIBRBPAGZREF-UHFFFAOYSA-N 0.000 description 1
NOVZIYGNNWNQAT-UHFFFAOYSA-N 5-prop-2-enylsulfanyl-1,2,4-thiadiazol-3-one Chemical compound C=CCSC1=NC(=O)NS1 NOVZIYGNNWNQAT-UHFFFAOYSA-N 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
241001425390 Aphis fabae Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000399934 Ditylenchus Species 0.000 description 1
241000255601 Drosophila melanogaster Species 0.000 description 1
206010061217 Infestation Diseases 0.000 description 1
240000008415 Lactuca sativa Species 0.000 description 1
235000003228 Lactuca sativa Nutrition 0.000 description 1
241001599018 Melanogaster Species 0.000 description 1
241001585712 Noctua Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
240000001987 Pyrus communis Species 0.000 description 1
239000005708 Sodium hypochlorite Substances 0.000 description 1
241000255588 Tephritidae Species 0.000 description 1
241000254086 Tribolium <beetle> Species 0.000 description 1
241000254112 Tribolium confusum Species 0.000 description 1
240000006677 Vicia faba Species 0.000 description 1
235000010749 Vicia faba Nutrition 0.000 description 1
PNVZEKVQKPXPMN-UHFFFAOYSA-N [5-[(4-chlorophenyl)methylsulfanyl]-1,2,4-thiadiazol-3-yl]oxy-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=NSC(SCC=2C=CC(Cl)=CC=2)=N1 PNVZEKVQKPXPMN-UHFFFAOYSA-N 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
KMJJJTCKNZYTEY-UHFFFAOYSA-N chloro-diethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(Cl)(=S)OCC KMJJJTCKNZYTEY-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000000151 deposition Methods 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
ZJBWZXZZYGUIPG-UHFFFAOYSA-N dimethoxy-[(5-methylsulfanyl-1,2,4-thiadiazol-3-yl)oxy]-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)OC1=NSC(SC)=N1 ZJBWZXZZYGUIPG-UHFFFAOYSA-N 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
230000037406 food intake Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
XMZXGEVIICDLLD-UHFFFAOYSA-N o-[(4-chlorophenyl)methyl] methylsulfanylmethanethioate Chemical compound CSC(=S)OCC1=CC=C(Cl)C=C1 XMZXGEVIICDLLD-UHFFFAOYSA-N 0.000 description 1
GMKACRZKTZATLU-UHFFFAOYSA-N o-butyl methylsulfanylmethanethioate Chemical compound CCCCOC(=S)SC GMKACRZKTZATLU-UHFFFAOYSA-N 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-AKLPVKDBSA-N potassium-42 Chemical compound [42K] ZLMJMSJWJFRBEC-AKLPVKDBSA-N 0.000 description 1
OMKVZYFAGQKILB-UHFFFAOYSA-M potassium;butoxymethanedithioate Chemical compound [K+].CCCCOC([S-])=S OMKVZYFAGQKILB-UHFFFAOYSA-M 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
FSSNFWCACYQWBY-UHFFFAOYSA-M sodium;(4-chlorophenyl)methoxymethanedithioate Chemical compound [Na+].[S-]C(=S)OCC1=CC=C(Cl)C=C1 FSSNFWCACYQWBY-UHFFFAOYSA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000004094 surface-active agent Substances 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
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
- 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
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- C07F9/65392—Five-membered rings containing two nitrogen atoms
- C07F9/65397—Five-membered rings containing two nitrogen atoms having the two nitrogen atoms in positions 1 and 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Agronomy & Crop Science (AREA)
Engineering & Computer Science (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Dentistry (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

IL45926A 1973-10-26 1974-10-24 Thiadiazole phosphates and thiophosphates process for preparing them and pesticidal compositions IL45926A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7338223A FR2249092B1 (fr)	1973-10-26	1973-10-26

Publications (2)

Publication Number	Publication Date
IL45926A0 IL45926A0 (en)	1974-12-31
IL45926A true IL45926A (en)	1977-08-31

Family

ID=9126960

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL45926A IL45926A (en)	1973-10-26	1974-10-24	Thiadiazole phosphates and thiophosphates process for preparing them and pesticidal compositions

Country Status (19)

Country	Link
JP (1)	JPS5071677A (fr)
AR (1)	AR210251A1 (fr)
BE (1)	BE821420A (fr)
BR (1)	BR7408951A (fr)
CA (1)	CA1024151A (fr)
CH (1)	CH594691A5 (fr)
DD (2)	DD118225A5 (fr)
DE (1)	DE2450815A1 (fr)
DK (1)	DK559474A (fr)
FR (1)	FR2249092B1 (fr)
GB (1)	GB1434699A (fr)
HU (1)	HU171036B (fr)
IE (1)	IE41208B1 (fr)
IL (1)	IL45926A (fr)
LU (1)	LU71167A1 (fr)
NL (1)	NL7413912A (fr)
PH (1)	PH12199A (fr)
SU (1)	SU607531A3 (fr)
ZA (1)	ZA746781B (fr)

1973
- 1973-10-26 FR FR7338223A patent/FR2249092B1/fr not_active Expired
1974
- 1974-10-22 CA CA211,904A patent/CA1024151A/fr not_active Expired
- 1974-10-24 BE BE149830A patent/BE821420A/fr unknown
- 1974-10-24 PH PH16447A patent/PH12199A/en unknown
- 1974-10-24 HU HU74RO00000807A patent/HU171036B/hu unknown
- 1974-10-24 NL NL7413912A patent/NL7413912A/xx not_active Application Discontinuation
- 1974-10-24 GB GB4685674A patent/GB1434699A/en not_active Expired
- 1974-10-24 DD DD181897A patent/DD118225A5/xx unknown
- 1974-10-24 IL IL45926A patent/IL45926A/en unknown
- 1974-10-24 JP JP49122004A patent/JPS5071677A/ja active Pending
- 1974-10-24 LU LU71167A patent/LU71167A1/xx unknown
- 1974-10-24 DD DD190828A patent/DD123475A5/xx unknown
- 1974-10-25 CH CH1434374A patent/CH594691A5/xx not_active IP Right Cessation
- 1974-10-25 ZA ZA00746781A patent/ZA746781B/xx unknown
- 1974-10-25 DE DE19742450815 patent/DE2450815A1/de not_active Withdrawn
- 1974-10-25 BR BR8951/74A patent/BR7408951A/pt unknown
- 1974-10-25 DK DK559474A patent/DK559474A/da unknown
- 1974-10-25 AR AR256266A patent/AR210251A1/es active
- 1974-10-25 IE IE2204/74A patent/IE41208B1/xx unknown
1975
- 1975-08-07 SU SU752162198A patent/SU607531A3/ru active

Also Published As

Publication number	Publication date
ZA746781B (en)	1975-11-26
NL7413912A (nl)	1975-04-29
SU607531A3 (ru)	1978-05-15
DK559474A (fr)	1975-07-07
GB1434699A (en)	1976-05-05
JPS5071677A (fr)	1975-06-13
FR2249092A1 (fr)	1975-05-23
DD123475A5 (fr)	1976-12-20
LU71167A1 (fr)	1975-06-24
CH594691A5 (fr)	1978-01-31
IE41208B1 (en)	1979-11-07
PH12199A (en)	1978-11-28
CA1024151A (fr)	1978-01-10
IE41208L (en)	1975-04-26
AR210251A1 (es)	1977-07-15
BR7408951A (pt)	1976-05-04
HU171036B (hu)	1977-10-28
BE821420A (fr)	1975-04-24
FR2249092B1 (fr)	1977-01-07
DD118225A5 (fr)	1976-02-20
IL45926A0 (en)	1974-12-31
DE2450815A1 (de)	1975-04-30

Publication	Publication Date	Title
US3867396A (en)	1975-02-18	Triazolyl phosphorus compounds
US3867397A (en)	1975-02-18	Triazolyl phosphorus compounds
SU795485A3 (ru)	1981-01-07	Способ получени триазолсодержа-щиХ эфиРОВ ТиОфОСфОРНыХ КиСлОТ
US3422190A (en)	1969-01-14	Aromatic isonitrile pest controlling agents
US3948935A (en)	1976-04-06	Pyrazoline derivatives
US4069319A (en)	1978-01-17	Novel thiadiazoles
US3661926A (en)	1972-05-09	Physiologically active oxadiazoline and thiadiazoline derivatives of phosphoric acid and thiophosphoric acid
US4020076A (en)	1977-04-26	Novel phosphoryloxy-thiazoles
US4560682A (en)	1985-12-24	Organophosphoric acid esters of benzofuranols and pesticidal compositions thereof
US4499098A (en)	1985-02-12	Insecticidal N-carbamoyl-oxadiazolidin-5-ones and thiones
US3524861A (en)	1970-08-18	Phosphorylated benzofurazans
US3886274A (en)	1975-05-27	Control of animal pests with 3H-oxazol-{8 4,5-6{9 pyridine-2-one esters of 3-(-o-)or (-s-)-0,0{40 di(lower alkyl) phosphates and thiophosphates
US4478832A (en)	1984-10-23	Pesticidal O-(N-alkoxy-substituted-benzimidoyl)-phosphorus esters and thioesters
US3220922A (en)	1965-11-30	Amino-triazol derivatives
US3766200A (en)	1973-10-16	Certain diazolylaliphatic esters of thiophosphoric and dithiophosphoric acids
US4599329A (en)	1986-07-08	O,S-dialkyl S-[carbamyloxyalkyl] dithiophosphates and their use as pesticides
US3931175A (en)	1976-01-06	Imidazo(1,2b)pyridazinyl esters, process and insecticidal compositions
EP0081945B1 (fr)	1986-09-03	Composés organophosphorés de pyrimidinyle substitués, compositions les contenant et procédés de contrôle des organismes nuisibles
US3929809A (en)	1975-12-30	Oxazolo-{8 4,5-b{9 -pyridine-2-ones and -2-thiones as intermediates
US3755571A (en)	1973-08-28	Use of substituted 1,2,4-thiadiazoles for killing insects
US3798230A (en)	1974-03-19	O,o-dialkyl-o-(1-oxa-2,4-diazolidinon-5-yl-3)-thionophosphates
US3718661A (en)	1973-02-27	Phosphoric esters
US3904639A (en)	1975-09-09	Thiazolotriazolyphosphonothioates
KR800001183B1 (ko)	1980-10-20	1,2,4-트리아졸 인산에스테르의 제조법
US4150124A (en)	1979-04-17	2,5-Dichloro-4-cyano-phenyl esters of thionophosphoric, thionothiolphosphoric and thionophosphonic acids