DD203678A5 - Schaedlingsbekaempfungsmittel - Google Patents
Schaedlingsbekaempfungsmittel Download PDFInfo
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- DD203678A5 DD203678A5 DD82243877A DD24387782A DD203678A5 DD 203678 A5 DD203678 A5 DD 203678A5 DD 82243877 A DD82243877 A DD 82243877A DD 24387782 A DD24387782 A DD 24387782A DD 203678 A5 DD203678 A5 DD 203678A5
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- DD
- German Democratic Republic
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- formula
- spp
- substituted
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- Prior art date
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- KGRJVKVOAVFJJS-UHFFFAOYSA-N 2-hydroxypropanediamide Chemical class NC(=O)C(O)C(N)=O KGRJVKVOAVFJJS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000005017 substituted alkenyl group Chemical group 0.000 claims abstract description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 42
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 40
- 238000002360 preparation method Methods 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 10
- 229910014033 C-OH Inorganic materials 0.000 claims description 8
- 229910014570 C—OH Inorganic materials 0.000 claims description 8
- 241000607479 Yersinia pestis Species 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 abstract description 18
- 229910052801 chlorine Chemical group 0.000 abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 70
- 150000001875 compounds Chemical class 0.000 description 65
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 41
- -1 1-ethylhexylamino-4-pyrimidinyl Chemical group 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- 229910052736 halogen Inorganic materials 0.000 description 13
- 150000002367 halogens Chemical class 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 229910021529 ammonia Inorganic materials 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- 238000007127 saponification reaction Methods 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 239000005457 ice water Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 150000007522 mineralic acids Chemical class 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- QMBLEDRWCLPDBX-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-2-trimethylsilyloxypropanedinitrile Chemical compound C[Si](C)(C)OC(C#N)(C#N)C1=CC=C(Cl)C(Cl)=C1 QMBLEDRWCLPDBX-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000239290 Araneae Species 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241001608567 Phaedon cochleariae Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
- 230000009435 amidation Effects 0.000 description 3
- 238000007112 amidation reaction Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical class OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- RDWBDFPCCJCIGV-UHFFFAOYSA-N 2-trimethylsilyloxypropanedioic acid Chemical class C[Si](C)(C)OC(C(O)=O)C(O)=O RDWBDFPCCJCIGV-UHFFFAOYSA-N 0.000 description 2
- 241001143309 Acanthoscelides obtectus Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241001481703 Rhipicephalus <genus> Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 241001454294 Tetranychus Species 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
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- 150000002430 hydrocarbons Chemical class 0.000 description 2
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- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- NNICRUQPODTGRU-UHFFFAOYSA-N mandelonitrile Chemical compound N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MJJBGAMKPIIFRR-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-hydroxypropanediamide Chemical compound NC(=O)C(O)(C(N)=O)C1=CC=C(Cl)C=C1Cl MJJBGAMKPIIFRR-UHFFFAOYSA-N 0.000 description 1
- AFQWUIHDLHMVEQ-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-2-hydroxypropanedioic acid Chemical compound OC(=O)C(O)(C(O)=O)C1=CC=C(Cl)C=C1Cl AFQWUIHDLHMVEQ-UHFFFAOYSA-N 0.000 description 1
- SZCHVGKAFJEVLR-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)-2-hydroxypropanediamide Chemical compound NC(=O)C(O)(C(N)=O)C1=CC(Cl)=CC=C1Cl SZCHVGKAFJEVLR-UHFFFAOYSA-N 0.000 description 1
- MWMVTKHRFQGQQC-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-2-hydroxypropanedioic acid Chemical compound OC(=O)C(O)(C(O)=O)C1=C(Cl)C=CC=C1Cl MWMVTKHRFQGQQC-UHFFFAOYSA-N 0.000 description 1
- MCFIUMFSHFOETG-UHFFFAOYSA-N 2-(2,6-dimethoxyphenyl)-2-hydroxypropanediamide Chemical compound COC1=CC=CC(OC)=C1C(O)(C(N)=O)C(N)=O MCFIUMFSHFOETG-UHFFFAOYSA-N 0.000 description 1
- NJYGAJVTOWHDRL-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-2-hydroxypropanediamide Chemical compound NC(=O)C(O)(C(N)=O)C1=CC=C(Cl)C(Cl)=C1 NJYGAJVTOWHDRL-UHFFFAOYSA-N 0.000 description 1
- RQJXLNQLXUWIIW-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-2-hydroxypropanedioic acid Chemical compound OC(=O)C(O)(C(O)=O)C1=CC=C(Cl)C(Cl)=C1 RQJXLNQLXUWIIW-UHFFFAOYSA-N 0.000 description 1
- GOWPTFJKMGIMBI-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)-2-hydroxypropanedioic acid Chemical compound OC(=O)C(O)(C(O)=O)C1=CC(Cl)=CC(Cl)=C1 GOWPTFJKMGIMBI-UHFFFAOYSA-N 0.000 description 1
- MXKXMSPRANCOBW-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-hydroxypropanediamide Chemical class NC(=O)C(O)(C(N)=O)C1=CC=C(F)C=C1 MXKXMSPRANCOBW-UHFFFAOYSA-N 0.000 description 1
- GAOCWUUUVPLJQC-UHFFFAOYSA-N 2-hydroxy-2-(4-methoxyphenyl)propanediamide Chemical compound COC1=CC=C(C(O)(C(N)=O)C(N)=O)C=C1 GAOCWUUUVPLJQC-UHFFFAOYSA-N 0.000 description 1
- PGFNTWBLZNWBNV-UHFFFAOYSA-N 2-hydroxy-2-(4-methylphenyl)propanediamide Chemical compound CC1=CC=C(C(O)(C(N)=O)C(N)=O)C=C1 PGFNTWBLZNWBNV-UHFFFAOYSA-N 0.000 description 1
- JBXNPBMXOOCVDY-UHFFFAOYSA-N 2-hydroxy-2-(4-nitrophenyl)propanedioic acid Chemical compound OC(=O)C(O)(C(O)=O)C1=CC=C([N+]([O-])=O)C=C1 JBXNPBMXOOCVDY-UHFFFAOYSA-N 0.000 description 1
- MXHAVCQPEZZERW-UHFFFAOYSA-N 2-hydroxy-2-[4-(trifluoromethoxy)phenyl]propanediamide Chemical class NC(=O)C(O)(C(N)=O)C1=CC=C(OC(F)(F)F)C=C1 MXHAVCQPEZZERW-UHFFFAOYSA-N 0.000 description 1
- IJUPGWBPDQPMQC-UHFFFAOYSA-N 2-hydroxy-2-[4-(trifluoromethyl)phenyl]propanedioic acid Chemical compound OC(=O)C(O)(C(O)=O)C1=CC=C(C(F)(F)F)C=C1 IJUPGWBPDQPMQC-UHFFFAOYSA-N 0.000 description 1
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- FRWLWDNANOVSOK-UHFFFAOYSA-N 2-hydroxy-2-phenylpropanedioic acid Chemical compound OC(=O)C(O)(C(O)=O)C1=CC=CC=C1 FRWLWDNANOVSOK-UHFFFAOYSA-N 0.000 description 1
- LDAWVYSUILLXOV-UHFFFAOYSA-N 2-tert-butyl-2-trimethylsilyloxypropanedioic acid Chemical compound CC(C)(C)C(C(O)=O)(C(O)=O)O[Si](C)(C)C LDAWVYSUILLXOV-UHFFFAOYSA-N 0.000 description 1
- TZDLVQKQBDXGEJ-UHFFFAOYSA-N 2-trimethylsilyloxypropanedinitrile Chemical class C[Si](C)(C)OC(C#N)C#N TZDLVQKQBDXGEJ-UHFFFAOYSA-N 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Measurement And Recording Of Electrical Phenomena And Electrical Characteristics Of The Living Body (AREA)
- Radar Systems Or Details Thereof (AREA)
- Farming Of Fish And Shellfish (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813140275 DE3140275A1 (de) | 1981-10-10 | 1981-10-10 | Substituierte hydroxy-malonsaeurediamide, verfahren zu ihrer herstellung sowie ihre verwendung als schaedlingsbekaempfungsmittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD203678A5 true DD203678A5 (de) | 1983-11-02 |
Family
ID=6143811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD82243877A DD203678A5 (de) | 1981-10-10 | 1982-10-08 | Schaedlingsbekaempfungsmittel |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP0076957B1 (en, 2012) |
| JP (1) | JPS5872547A (en, 2012) |
| KR (1) | KR840001948A (en, 2012) |
| AT (1) | ATE19058T1 (en, 2012) |
| AU (1) | AU551841B2 (en, 2012) |
| BR (1) | BR8205906A (en, 2012) |
| CS (1) | CS241124B2 (en, 2012) |
| DD (1) | DD203678A5 (en, 2012) |
| DE (2) | DE3140275A1 (en, 2012) |
| DK (1) | DK444982A (en, 2012) |
| EG (1) | EG15762A (en, 2012) |
| ES (1) | ES8306994A1 (en, 2012) |
| GR (1) | GR77719B (en, 2012) |
| HU (1) | HU188209B (en, 2012) |
| IL (1) | IL66943A (en, 2012) |
| MA (1) | MA19618A1 (en, 2012) |
| NZ (1) | NZ202106A (en, 2012) |
| OA (1) | OA07225A (en, 2012) |
| PH (1) | PH18860A (en, 2012) |
| PL (1) | PL134945B1 (en, 2012) |
| PT (1) | PT75637B (en, 2012) |
| ZA (1) | ZA827369B (en, 2012) |
| ZW (1) | ZW20082A1 (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0108351B1 (de) * | 1982-11-10 | 1987-07-22 | Bayer Ag | Verwendung substituierter Malonsäurederivate als Schädlingsbekämpfungsmittel |
| DE3241512A1 (de) * | 1982-11-10 | 1984-05-10 | Bayer Ag, 5090 Leverkusen | Substituierte malonsaeurediamide, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| DE3308464A1 (de) * | 1983-03-10 | 1984-09-13 | Bayer Ag, 5090 Leverkusen | Substituierte hydroxy-malonsaeureamidthioamide, verfahren zu ihrer herstellung sowie ihre verwendung als schaedlingsbekaempfungsmittel |
| DE3308463A1 (de) * | 1983-03-10 | 1984-09-20 | Bayer Ag, 5090 Leverkusen | Substituierte phenylhydroxy-thio-malonsaeurediamide, verfahren zu ihrer herstellung sowie ihre verwendung als schaedlingsbekaempfungsmittel |
| DE3310954A1 (de) * | 1983-03-25 | 1984-10-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von substituierten trialkylsilyloxymalonsaeuredinitrilen |
| DE3400401A1 (de) * | 1984-01-07 | 1985-08-22 | Bayer Ag, 5090 Leverkusen | Substituierte malonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| DE3626411A1 (de) * | 1986-08-05 | 1988-02-11 | Bayer Ag | Verfahren zur herstellung von dimeren aromatischen acylcyaniden |
| CN100358863C (zh) | 1999-09-24 | 2008-01-02 | 日本农药株式会社 | 芳族二酰胺衍生物或其盐、农艺组合物及其使用方法 |
| US6306463B1 (en) * | 2000-07-20 | 2001-10-23 | Air Products And Chemicals, Inc. | Citric acid tri-alkylamide surfactants |
| US7439383B2 (en) | 2002-04-18 | 2008-10-21 | University Of Virginia Patent Foundation | Sodium channel blockers |
| CN110563582A (zh) * | 2019-10-09 | 2019-12-13 | 合肥诚志生物制药有限公司 | 2-羟基-2-苯基-丙二酰胺的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3946074A (en) * | 1970-10-05 | 1976-03-23 | Akzona Incorporated | Plant growth regulatory agents and process |
| US4208204A (en) * | 1977-10-07 | 1980-06-17 | Calbiochem-Behring Corp. | 3-Hydroxy-3-methylglutaric acid monoamide and derivatives thereof |
-
1981
- 1981-10-10 DE DE19813140275 patent/DE3140275A1/de not_active Withdrawn
-
1982
- 1982-09-20 ZW ZW200/82A patent/ZW20082A1/xx unknown
- 1982-09-25 EP EP82108882A patent/EP0076957B1/de not_active Expired
- 1982-09-25 DE DE8282108882T patent/DE3270446D1/de not_active Expired
- 1982-09-25 AT AT82108882T patent/ATE19058T1/de not_active IP Right Cessation
- 1982-10-01 PT PT75637A patent/PT75637B/pt unknown
- 1982-10-07 NZ NZ202106A patent/NZ202106A/en unknown
- 1982-10-07 CS CS827176A patent/CS241124B2/cs unknown
- 1982-10-07 DK DK444982A patent/DK444982A/da not_active Application Discontinuation
- 1982-10-07 IL IL66943A patent/IL66943A/xx unknown
- 1982-10-07 PH PH27956A patent/PH18860A/en unknown
- 1982-10-07 JP JP57175431A patent/JPS5872547A/ja active Pending
- 1982-10-08 PL PL1982238572A patent/PL134945B1/pl unknown
- 1982-10-08 HU HU823227A patent/HU188209B/hu unknown
- 1982-10-08 ES ES516369A patent/ES8306994A1/es not_active Expired
- 1982-10-08 DD DD82243877A patent/DD203678A5/de unknown
- 1982-10-08 MA MA19829A patent/MA19618A1/fr unknown
- 1982-10-08 OA OA57817A patent/OA07225A/xx unknown
- 1982-10-08 GR GR69480A patent/GR77719B/el unknown
- 1982-10-08 BR BR8205906A patent/BR8205906A/pt unknown
- 1982-10-08 KR KR1019820004552A patent/KR840001948A/ko not_active Withdrawn
- 1982-10-08 ZA ZA827369A patent/ZA827369B/xx unknown
- 1982-10-09 EG EG596/82A patent/EG15762A/xx active
- 1982-10-11 AU AU89257/82A patent/AU551841B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5872547A (ja) | 1983-04-30 |
| PL134945B1 (en) | 1985-09-30 |
| KR840001948A (ko) | 1984-06-07 |
| EP0076957B1 (de) | 1986-04-09 |
| PH18860A (en) | 1985-10-21 |
| EP0076957A1 (de) | 1983-04-20 |
| HU188209B (en) | 1986-03-28 |
| ES516369A0 (es) | 1983-06-16 |
| AU8925782A (en) | 1983-04-21 |
| PL238572A1 (en) | 1984-03-26 |
| ZA827369B (en) | 1983-08-31 |
| PT75637B (en) | 1985-01-11 |
| DE3270446D1 (en) | 1986-05-15 |
| IL66943A (en) | 1987-03-31 |
| PT75637A (en) | 1982-11-01 |
| OA07225A (fr) | 1984-04-30 |
| AU551841B2 (en) | 1986-05-15 |
| DK444982A (da) | 1983-04-11 |
| CS241124B2 (en) | 1986-03-13 |
| CS717682A2 (en) | 1985-06-13 |
| ATE19058T1 (de) | 1986-04-15 |
| EG15762A (en) | 1986-12-30 |
| ZW20082A1 (en) | 1982-12-15 |
| DE3140275A1 (de) | 1983-04-28 |
| ES8306994A1 (es) | 1983-06-16 |
| MA19618A1 (fr) | 1983-07-01 |
| GR77719B (en, 2012) | 1984-09-25 |
| IL66943A0 (en) | 1983-02-23 |
| NZ202106A (en) | 1985-08-30 |
| BR8205906A (pt) | 1983-09-06 |
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