IL45926A - Thiadiazole phosphates and thiophosphates process for preparing them and pesticidal compositions - Google Patents
Thiadiazole phosphates and thiophosphates process for preparing them and pesticidal compositionsInfo
- Publication number
- IL45926A IL45926A IL45926A IL4592674A IL45926A IL 45926 A IL45926 A IL 45926A IL 45926 A IL45926 A IL 45926A IL 4592674 A IL4592674 A IL 4592674A IL 45926 A IL45926 A IL 45926A
- Authority
- IL
- Israel
- Prior art keywords
- thiadiazole
- diethoxythiophosphoryloxy
- formula
- potassium
- methyl
- Prior art date
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7338223A FR2249092B1 (xx) | 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 (xx) |
| AR (1) | AR210251A1 (xx) |
| BE (1) | BE821420A (xx) |
| BR (1) | BR7408951A (xx) |
| CA (1) | CA1024151A (xx) |
| CH (1) | CH594691A5 (xx) |
| DD (2) | DD118225A5 (xx) |
| DE (1) | DE2450815A1 (xx) |
| DK (1) | DK559474A (xx) |
| FR (1) | FR2249092B1 (xx) |
| GB (1) | GB1434699A (xx) |
| HU (1) | HU171036B (xx) |
| IE (1) | IE41208B1 (xx) |
| IL (1) | IL45926A (xx) |
| LU (1) | LU71167A1 (xx) |
| NL (1) | NL7413912A (xx) |
| PH (1) | PH12199A (xx) |
| SU (1) | SU607531A3 (xx) |
| ZA (1) | ZA746781B (xx) |
-
1973
- 1973-10-26 FR FR7338223A patent/FR2249092B1/fr not_active Expired
-
1974
- 1974-10-22 CA CA211,904A patent/CA1024151A/en not_active Expired
- 1974-10-24 PH PH16447A patent/PH12199A/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 DD181897A patent/DD118225A5/xx unknown
- 1974-10-24 NL NL7413912A patent/NL7413912A/xx not_active Application Discontinuation
- 1974-10-24 IL IL45926A patent/IL45926A/en unknown
- 1974-10-24 DD DD190828A patent/DD123475A5/xx unknown
- 1974-10-24 GB GB4685674A patent/GB1434699A/en not_active Expired
- 1974-10-24 BE BE149830A patent/BE821420A/xx unknown
- 1974-10-24 HU HU74RO00000807A patent/HU171036B/hu unknown
- 1974-10-25 BR BR8951/74A patent/BR7408951A/pt unknown
- 1974-10-25 IE IE2204/74A patent/IE41208B1/xx unknown
- 1974-10-25 DE DE19742450815 patent/DE2450815A1/de not_active Withdrawn
- 1974-10-25 AR AR256266A patent/AR210251A1/es active
- 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 DK DK559474A patent/DK559474A/da unknown
-
1975
- 1975-08-07 SU SU752162198A patent/SU607531A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| HU171036B (hu) | 1977-10-28 |
| AR210251A1 (es) | 1977-07-15 |
| SU607531A3 (ru) | 1978-05-15 |
| BE821420A (fr) | 1975-04-24 |
| IE41208L (en) | 1975-04-26 |
| GB1434699A (en) | 1976-05-05 |
| ZA746781B (en) | 1975-11-26 |
| FR2249092B1 (xx) | 1977-01-07 |
| CA1024151A (en) | 1978-01-10 |
| IL45926A0 (en) | 1974-12-31 |
| DE2450815A1 (de) | 1975-04-30 |
| IE41208B1 (en) | 1979-11-07 |
| LU71167A1 (xx) | 1975-06-24 |
| BR7408951A (pt) | 1976-05-04 |
| PH12199A (en) | 1978-11-28 |
| DD118225A5 (xx) | 1976-02-20 |
| NL7413912A (nl) | 1975-04-29 |
| JPS5071677A (xx) | 1975-06-13 |
| DK559474A (xx) | 1975-07-07 |
| DD123475A5 (xx) | 1976-12-20 |
| FR2249092A1 (xx) | 1975-05-23 |
| CH594691A5 (xx) | 1978-01-31 |
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