GB1579112A - Carbamoyloxy-substituted pyrimidinyl (thiono) (thiol)-phosphoric (phosphonic) acid esters and ester-amides and their use as insecticides and acaricides - Google Patents
Carbamoyloxy-substituted pyrimidinyl (thiono) (thiol)-phosphoric (phosphonic) acid esters and ester-amides and their use as insecticides and acaricides Download PDFInfo
- Publication number
- GB1579112A GB1579112A GB8323/78A GB832378A GB1579112A GB 1579112 A GB1579112 A GB 1579112A GB 8323/78 A GB8323/78 A GB 8323/78A GB 832378 A GB832378 A GB 832378A GB 1579112 A GB1579112 A GB 1579112A
- Authority
- GB
- United Kingdom
- Prior art keywords
- yll
- pyrimidin
- hydroxy
- iso
- methyl
- 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
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- -1 Carbamoyloxy-substituted pyrimidinyl (thiono) Chemical class 0.000 title claims description 179
- 239000002253 acid Substances 0.000 title claims description 44
- 150000002148 esters Chemical class 0.000 title claims description 24
- 150000003573 thiols Chemical class 0.000 title claims description 15
- 230000000895 acaricidal effect Effects 0.000 title description 7
- 239000000642 acaricide Substances 0.000 title description 3
- 239000002917 insecticide Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 19
- 239000003085 diluting agent Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 241000238421 Arthropoda Species 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 230000006378 damage Effects 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical class 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 241000238631 Hexapoda Species 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000005864 Sulphur Chemical group 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229940125846 compound 25 Drugs 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 27
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 14
- 229910052717 sulfur Inorganic materials 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- QWIDYOLZFAQBOB-UHFFFAOYSA-N 2-methyl-1h-pyrimidin-6-one Chemical compound CC1=NC=CC(=O)N1 QWIDYOLZFAQBOB-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 7
- 241000607479 Yersinia pestis Species 0.000 description 7
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 125000005920 sec-butoxy group Chemical group 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 239000001273 butane Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- PCXCYBRMVAQGAJ-UHFFFAOYSA-N 2-bromo-1h-pyrimidin-6-one Chemical compound BrC1=NC=CC(=O)N1 PCXCYBRMVAQGAJ-UHFFFAOYSA-N 0.000 description 3
- BVAGDAFSWAHBDZ-UHFFFAOYSA-N 2-butyl-1h-pyrimidin-6-one Chemical compound CCCCC1=NC=CC(=O)N1 BVAGDAFSWAHBDZ-UHFFFAOYSA-N 0.000 description 3
- JJFMDOVUGJNEAD-UHFFFAOYSA-N 2-propan-2-yl-1h-pyrimidin-6-one Chemical compound CC(C)C1=NC=CC(O)=N1 JJFMDOVUGJNEAD-UHFFFAOYSA-N 0.000 description 3
- DOZKGELCYBIBBZ-UHFFFAOYSA-N 4-hydroxy-2-propan-2-yl-1h-pyrimidin-6-one Chemical compound CC(C)C1=NC(O)=CC(=O)N1 DOZKGELCYBIBBZ-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000500437 Plutella xylostella Species 0.000 description 3
- 241001454294 Tetranychus Species 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 2
- MIEQNBVNRFGOQC-UHFFFAOYSA-N 2-(dimethylamino)-1h-pyrimidin-6-one Chemical compound CN(C)C1=NC=CC(=O)N1 MIEQNBVNRFGOQC-UHFFFAOYSA-N 0.000 description 2
- QRHZRFZBNWIHRC-UHFFFAOYSA-N 2-butoxy-1H-pyrimidin-6-one Chemical compound C(CCC)OC1=NC=CC(=N1)O QRHZRFZBNWIHRC-UHFFFAOYSA-N 0.000 description 2
- FETSYNXZMUAONO-UHFFFAOYSA-N 2-chloro-1h-pyrimidin-6-one Chemical compound ClC1=NC=CC(=O)N1 FETSYNXZMUAONO-UHFFFAOYSA-N 0.000 description 2
- CAMDHKGJRSRSJR-UHFFFAOYSA-N 2-ethoxy-1h-pyrimidin-6-one Chemical compound CCOC1=NC=CC(=O)N1 CAMDHKGJRSRSJR-UHFFFAOYSA-N 0.000 description 2
- OHQPGIMLIAEFMM-UHFFFAOYSA-N 2-ethoxy-5-methyl-1h-pyrimidin-6-one Chemical compound CCOC1=NC=C(C)C(=O)N1 OHQPGIMLIAEFMM-UHFFFAOYSA-N 0.000 description 2
- OFPWIXYGAJDWPC-UHFFFAOYSA-N 2-ethyl-1h-pyrimidin-6-one Chemical compound CCC1=NC=CC(=O)N1 OFPWIXYGAJDWPC-UHFFFAOYSA-N 0.000 description 2
- VPLWQGMFSSWEIA-UHFFFAOYSA-N 2-ethyl-5-methyl-1h-pyrimidin-6-one Chemical compound CCC1=NC=C(C)C(O)=N1 VPLWQGMFSSWEIA-UHFFFAOYSA-N 0.000 description 2
- OEHRELACOJFJQI-UHFFFAOYSA-N 2-ethylsulfanyl-1h-pyrimidin-6-one Chemical compound CCSC1=NC=CC(=O)N1 OEHRELACOJFJQI-UHFFFAOYSA-N 0.000 description 2
- PDJZKZLISQIEOC-UHFFFAOYSA-N 2-methoxy-1h-pyrimidin-6-one Chemical compound COC1=NC=CC(=O)N1 PDJZKZLISQIEOC-UHFFFAOYSA-N 0.000 description 2
- FLEYOQDGUUJNHI-UHFFFAOYSA-N 2-methoxy-5-methyl-1h-pyrimidin-6-one Chemical compound COC1=NC=C(C)C(=O)N1 FLEYOQDGUUJNHI-UHFFFAOYSA-N 0.000 description 2
- LNJMHEJAYSYZKK-UHFFFAOYSA-N 2-methylpyrimidine Chemical compound CC1=NC=CC=N1 LNJMHEJAYSYZKK-UHFFFAOYSA-N 0.000 description 2
- UYHSQVMHSFXUOA-UHFFFAOYSA-N 2-methylthiouracil Chemical compound CSC1=NC=CC(O)=N1 UYHSQVMHSFXUOA-UHFFFAOYSA-N 0.000 description 2
- UTFIHZWGAPIHFU-UHFFFAOYSA-N 2-propoxy-1H-pyrimidin-6-one Chemical compound CCCOc1nccc(O)n1 UTFIHZWGAPIHFU-UHFFFAOYSA-N 0.000 description 2
- BZNZMDBBTRVRQI-UHFFFAOYSA-N 2-propylsulfanyl-1h-pyrimidin-6-one Chemical compound CCCSC1=NC=CC(=O)N1 BZNZMDBBTRVRQI-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- DUFGYCAXVIUXIP-UHFFFAOYSA-N 4,6-dihydroxypyrimidine Chemical class OC1=CC(O)=NC=N1 DUFGYCAXVIUXIP-UHFFFAOYSA-N 0.000 description 2
- NOKBGOCOBGTITR-UHFFFAOYSA-N 5-bromo-2-ethoxy-1H-pyrimidin-6-one Chemical compound C(C)OC1=NC(=C(C=N1)Br)O NOKBGOCOBGTITR-UHFFFAOYSA-N 0.000 description 2
- MWZGHIGOSHTXGY-UHFFFAOYSA-N 5-bromo-2-phenyl-1h-pyrimidin-6-one Chemical compound N1C(=O)C(Br)=CN=C1C1=CC=CC=C1 MWZGHIGOSHTXGY-UHFFFAOYSA-N 0.000 description 2
- YAUGBUJBSKRRAA-UHFFFAOYSA-N 5-bromo-2-propan-2-yl-1h-pyrimidin-6-one Chemical compound CC(C)C1=NC=C(Br)C(=O)N1 YAUGBUJBSKRRAA-UHFFFAOYSA-N 0.000 description 2
- DAEZJMUBVLKPBR-UHFFFAOYSA-N 5-chloro-2-ethylsulfanyl-1h-pyrimidin-6-one Chemical compound CCSC1=NC=C(Cl)C(=O)N1 DAEZJMUBVLKPBR-UHFFFAOYSA-N 0.000 description 2
- PRVJJVJTVJZKSV-UHFFFAOYSA-N 5-chloro-2-methoxy-1H-pyrimidin-6-one Chemical compound COC1=NC(=C(C=N1)Cl)O PRVJJVJTVJZKSV-UHFFFAOYSA-N 0.000 description 2
- GHJOKLMPIJLWBU-UHFFFAOYSA-N 5-chloro-2-methyl-1h-pyrimidin-6-one Chemical compound CC1=NC=C(Cl)C(=O)N1 GHJOKLMPIJLWBU-UHFFFAOYSA-N 0.000 description 2
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- MAEIXNMVPKKWPQ-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-pyrimidin-6-one Chemical compound N1C(=O)C(C)=CN=C1C1=CC=CC=C1 MAEIXNMVPKKWPQ-UHFFFAOYSA-N 0.000 description 2
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- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 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
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- A01N57/08—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 containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772709908 DE2709908A1 (de) | 1977-03-08 | 1977-03-08 | Carbamoyloxysubstituierte pyrimidinyl(thiono)-(thiol)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1579112A true GB1579112A (en) | 1980-11-12 |
Family
ID=6002991
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8323/78A Expired GB1579112A (en) | 1977-03-08 | 1978-03-02 | Carbamoyloxy-substituted pyrimidinyl (thiono) (thiol)-phosphoric (phosphonic) acid esters and ester-amides and their use as insecticides and acaricides |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4188383A (enExample) |
| JP (1) | JPS53112885A (enExample) |
| AT (1) | ATA156978A (enExample) |
| AU (1) | AU3391878A (enExample) |
| BE (1) | BE864628A (enExample) |
| BR (1) | BR7801401A (enExample) |
| CH (1) | CH633807A5 (enExample) |
| DE (1) | DE2709908A1 (enExample) |
| DK (1) | DK100578A (enExample) |
| FR (1) | FR2383195A1 (enExample) |
| GB (1) | GB1579112A (enExample) |
| IL (1) | IL54198A (enExample) |
| IT (1) | IT7820920A0 (enExample) |
| NL (1) | NL7802535A (enExample) |
| TR (1) | TR19774A (enExample) |
| ZA (1) | ZA781336B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3439363A1 (de) * | 1984-10-27 | 1986-04-30 | Bayer Ag, 5090 Leverkusen | Phosphorsaeureester |
| DE3704689A1 (de) * | 1987-02-14 | 1988-08-25 | Bayer Ag | Thionophosphonsaeureester |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE510817A (enExample) * | 1951-04-20 | 1900-01-01 | ||
| US3639616A (en) * | 1970-04-20 | 1972-02-01 | Shell Oil Co | Pesticidal formulations |
| DK130683B (da) * | 1971-03-04 | 1975-03-24 | Sandoz Ag | Pesticidt virksomme pyrimidinylphosphorsyreestere. |
| US4045561A (en) * | 1973-03-23 | 1977-08-30 | Sandoz Ltd. | Pesticidal pyrimidinyl phosphorus esters |
-
1977
- 1977-03-08 DE DE19772709908 patent/DE2709908A1/de not_active Withdrawn
-
1978
- 1978-02-21 US US05/879,423 patent/US4188383A/en not_active Expired - Lifetime
- 1978-03-02 GB GB8323/78A patent/GB1579112A/en not_active Expired
- 1978-03-06 CH CH240978A patent/CH633807A5/de not_active IP Right Cessation
- 1978-03-06 IT IT7820920A patent/IT7820920A0/it unknown
- 1978-03-06 JP JP2459178A patent/JPS53112885A/ja active Pending
- 1978-03-06 IL IL54198A patent/IL54198A/xx unknown
- 1978-03-06 AT AT156978A patent/ATA156978A/de not_active IP Right Cessation
- 1978-03-07 TR TR19774A patent/TR19774A/xx unknown
- 1978-03-07 AU AU33918/78A patent/AU3391878A/en active Pending
- 1978-03-07 BE BE185715A patent/BE864628A/xx not_active IP Right Cessation
- 1978-03-07 BR BR7801401A patent/BR7801401A/pt unknown
- 1978-03-07 FR FR7806488A patent/FR2383195A1/fr active Granted
- 1978-03-07 ZA ZA00781336A patent/ZA781336B/xx unknown
- 1978-03-07 DK DK100578A patent/DK100578A/da unknown
- 1978-03-08 NL NL7802535A patent/NL7802535A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ATA156978A (de) | 1979-11-15 |
| DK100578A (da) | 1978-09-09 |
| FR2383195A1 (fr) | 1978-10-06 |
| FR2383195B1 (enExample) | 1984-08-24 |
| TR19774A (tr) | 1979-11-30 |
| IL54198A (en) | 1982-02-28 |
| US4188383A (en) | 1980-02-12 |
| CH633807A5 (de) | 1982-12-31 |
| AU3391878A (en) | 1979-09-13 |
| IL54198A0 (en) | 1978-06-15 |
| NL7802535A (nl) | 1978-09-12 |
| IT7820920A0 (it) | 1978-03-06 |
| DE2709908A1 (de) | 1978-09-14 |
| ZA781336B (en) | 1979-02-28 |
| BE864628A (fr) | 1978-09-07 |
| BR7801401A (pt) | 1978-10-31 |
| JPS53112885A (en) | 1978-10-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |