DD147195A5 - Schaedlingsbekaempfungsmittel - Google Patents
Schaedlingsbekaempfungsmittel Download PDFInfo
- Publication number
- DD147195A5 DD147195A5 DD79216772A DD21677279A DD147195A5 DD 147195 A5 DD147195 A5 DD 147195A5 DD 79216772 A DD79216772 A DD 79216772A DD 21677279 A DD21677279 A DD 21677279A DD 147195 A5 DD147195 A5 DD 147195A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- oxime
- thiazoline
- methylcarbamoyl
- dimethyl
- oxo
- Prior art date
Links
- -1 carbamoyl halide Chemical class 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 150000002923 oximes Chemical class 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 230000000361 pesticidal effect Effects 0.000 claims abstract description 4
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 3
- 239000000575 pesticide Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 241000607479 Yersinia pestis Species 0.000 claims description 6
- 229960001330 hydroxycarbamide Drugs 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- MVNNZYFBJNHMRC-UHFFFAOYSA-N [(5,5-dimethyl-4-propan-2-yl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CNC(=O)ON=C1SC(C)(C)C(C(C)C)=N1 MVNNZYFBJNHMRC-UHFFFAOYSA-N 0.000 claims 1
- FINQJZYVXUUCIX-UHFFFAOYSA-N [(5,5-dimethyl-4-propyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CCCC1=NC(=NOC(=O)NC)SC1(C)C FINQJZYVXUUCIX-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract description 11
- 241000238631 Hexapoda Species 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 7
- 239000012948 isocyanate Substances 0.000 abstract description 6
- 150000002513 isocyanates Chemical class 0.000 abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 3
- 101100439974 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) clpE gene Proteins 0.000 abstract 3
- 101100354192 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) exp5 gene Proteins 0.000 abstract 2
- 101100242909 Streptococcus pneumoniae (strain ATCC BAA-255 / R6) pbpA gene Proteins 0.000 abstract 1
- 101100269618 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) aliA gene Proteins 0.000 abstract 1
- 101150109310 msrAB1 gene Proteins 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 239000007858 starting material Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 17
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 241000238876 Acari Species 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000011533 pre-incubation Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- WXDSOCYXOXOMDK-UHFFFAOYSA-N n-(4,5,5-trimethyl-1,3-thiazol-2-ylidene)hydroxylamine Chemical compound CC1=NC(=NO)SC1(C)C WXDSOCYXOXOMDK-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 241001558864 Aceria Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
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- 241000254137 Cicadidae Species 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
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- 150000001412 amines Chemical class 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
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- 241000497192 Phyllocoptruta oleivora Species 0.000 description 1
- 241001517955 Phyllonorycter blancardella Species 0.000 description 1
- 241000275067 Phyllotreta Species 0.000 description 1
- 241000255969 Pieris brassicae Species 0.000 description 1
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- 241000193943 Pratylenchus Species 0.000 description 1
- 241000193940 Pratylenchus penetrans Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 241001180370 Psylliodes chrysocephalus Species 0.000 description 1
- 241001136852 Rhagoletis Species 0.000 description 1
- 241001450655 Saissetia Species 0.000 description 1
- 241000722272 Schizaphis Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000176085 Sogatella Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 241001238451 Tortrix viridana Species 0.000 description 1
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- BGDCVXREYPNFKP-UHFFFAOYSA-N [(4,5-diethyl-5-methyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CCC1=NC(=NOC(=O)NC)SC1(C)CC BGDCVXREYPNFKP-UHFFFAOYSA-N 0.000 description 1
- KPBPGMGANQUCTE-UHFFFAOYSA-N [(4-butyl-5,5-dimethyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CCCCC1=NC(=NOC(=O)NC)SC1(C)C KPBPGMGANQUCTE-UHFFFAOYSA-N 0.000 description 1
- ORMVGNHPPUGQIL-UHFFFAOYSA-N [(4-ethyl-5,5-dimethyl-1,3-thiazol-2-ylidene)amino] n-methylcarbamate Chemical compound CCC1=NC(=NOC(=O)NC)SC1(C)C ORMVGNHPPUGQIL-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- RYCKULLUQHRYKP-UHFFFAOYSA-N [[4,5-dimethyl-5-(3-methylpent-2-enyl)-1,3-thiazol-2-ylidene]amino] n-methylcarbamate Chemical compound CCC(C)=CCC1(C)SC(=NOC(=O)NC)N=C1C RYCKULLUQHRYKP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000003975 aryl alkyl amines Chemical class 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- FLKYBGKDCCEQQM-WYUVZMMLSA-M cefazolin sodium Chemical compound [Na+].S1C(C)=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 FLKYBGKDCCEQQM-WYUVZMMLSA-M 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- FXPVUWKFNGVHIZ-UHFFFAOYSA-L disodium;dodecyl sulfate Chemical compound [Na+].[Na+].CCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCOS([O-])(=O)=O FXPVUWKFNGVHIZ-UHFFFAOYSA-L 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- JDUJUPAGCBYIRR-UHFFFAOYSA-N isocyanatocyclobutane Chemical compound O=C=NC1CCC1 JDUJUPAGCBYIRR-UHFFFAOYSA-N 0.000 description 1
- DBBRJAWSDTYYBM-UHFFFAOYSA-N isocyanatocyclopropane Chemical compound O=C=NC1CC1 DBBRJAWSDTYYBM-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 230000000974 larvacidal effect Effects 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- YHFHRXCSVIBEHA-UHFFFAOYSA-N n-(4,5-diethyl-5-methyl-1,3-thiazol-2-ylidene)hydroxylamine Chemical compound CCC1=NC(=NO)SC1(C)CC YHFHRXCSVIBEHA-UHFFFAOYSA-N 0.000 description 1
- CXSADFMXNCEZRB-UHFFFAOYSA-N n-(4,5-dimethyl-5-propyl-1,3-thiazol-2-ylidene)hydroxylamine Chemical compound CCCC1(C)SC(=NO)N=C1C CXSADFMXNCEZRB-UHFFFAOYSA-N 0.000 description 1
- ODNDQBPBNOIECI-UHFFFAOYSA-N n-(4-ethyl-5,5-dimethyl-1,3-thiazol-2-ylidene)hydroxylamine Chemical compound CCC1=NC(=NO)SC1(C)C ODNDQBPBNOIECI-UHFFFAOYSA-N 0.000 description 1
- RHTPHXUHXPNQFV-UHFFFAOYSA-N n-(5,5-dimethyl-4-propan-2-yl-1,3-thiazol-2-ylidene)hydroxylamine Chemical compound CC(C)C1=NC(=NO)SC1(C)C RHTPHXUHXPNQFV-UHFFFAOYSA-N 0.000 description 1
- BKXBEKRPFOBZJA-UHFFFAOYSA-N n-(5,5-dimethyl-4-propyl-1,3-thiazol-2-ylidene)hydroxylamine Chemical compound CCCC1=NC(=NO)SC1(C)C BKXBEKRPFOBZJA-UHFFFAOYSA-N 0.000 description 1
- RLXRUACBAYMYNS-UHFFFAOYSA-N n-(5-ethyl-4,5-dimethyl-1,3-thiazol-2-ylidene)hydroxylamine Chemical compound CCC1(C)SC(=NO)N=C1C RLXRUACBAYMYNS-UHFFFAOYSA-N 0.000 description 1
- NPLURDIHAHOVOX-UHFFFAOYSA-N n-(5-ethyl-5-methyl-4-propyl-1,3-thiazol-2-ylidene)hydroxylamine Chemical compound CCCC1=NC(=NO)SC1(C)CC NPLURDIHAHOVOX-UHFFFAOYSA-N 0.000 description 1
- PGZUJUTYIZKSJC-UHFFFAOYSA-N n-benzyl-4,4-dimethylcyclohexan-1-amine Chemical compound C1CC(C)(C)CCC1NCC1=CC=CC=C1 PGZUJUTYIZKSJC-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 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
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 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
- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
-
- 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
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1153178 | 1978-11-09 | ||
| CH772879 | 1979-08-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD147195A5 true DD147195A5 (de) | 1981-03-25 |
Family
ID=25702045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79216772A DD147195A5 (de) | 1978-11-09 | 1979-11-08 | Schaedlingsbekaempfungsmittel |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4255436A (cs) |
| EP (1) | EP0011221B1 (cs) |
| AR (1) | AR224136A1 (cs) |
| AU (1) | AU529272B2 (cs) |
| BR (1) | BR7907182A (cs) |
| CA (1) | CA1126278A (cs) |
| CS (1) | CS208682B2 (cs) |
| DD (1) | DD147195A5 (cs) |
| DE (1) | DE2965046D1 (cs) |
| DK (1) | DK474179A (cs) |
| EG (1) | EG13808A (cs) |
| ES (1) | ES485806A1 (cs) |
| IL (1) | IL58619A (cs) |
| PL (1) | PL219513A1 (cs) |
| TR (1) | TR20531A (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3163048D1 (en) * | 1980-05-07 | 1984-05-17 | Hoffmann La Roche | Carbamoyl oximes, processes and intermediates for their preparation, pesticides containing them and use of these compounds as pesticides |
| US4514566A (en) * | 1981-04-24 | 1985-04-30 | Hoffmann-La Roche Inc. | 5-Oxo-3-thiazoline oxime and 2-oxo-5,6-dihydro-2H-1,4-thiazine oxime derivatives |
| US4427687A (en) | 1981-04-24 | 1984-01-24 | Hoffmann-La Roche Inc. | Thiazoline carbamoyl-oximes |
| US4640927A (en) * | 1984-03-30 | 1987-02-03 | Uniroyal Chemical Company, Inc. | Substituted oxime carbamates |
| DE3905714A1 (de) * | 1989-02-24 | 1990-09-06 | Bayer Ag | Sulfonylimino-azinylheteroazole, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3875232A (en) * | 1971-04-08 | 1975-04-01 | Diamond Shamrock Corp | AC Ketoxime carbamates |
| GB1357771A (en) * | 1971-05-07 | 1974-06-26 | Ici Ltd | Carbamoyloxime compounds and compositions and processes for pre paring them |
| US3966953A (en) * | 1972-12-29 | 1976-06-29 | Union Carbide Corporation | 2-(Carbamoyloximino)-4-thiazolidinone compounds as insecticidal, miticidal or nematocidal agents |
| US4315928A (en) * | 1975-06-26 | 1982-02-16 | Union Carbide Corporation | N-Aminosulfenyl carbamate compounds, compositions and use |
| US4181661A (en) * | 1976-05-03 | 1980-01-01 | Merck & Co., Inc. | Derivatives of 2-iminothiazolidines and thiazolines |
-
1979
- 1979-09-28 CA CA336,601A patent/CA1126278A/en not_active Expired
- 1979-10-31 US US06/089,793 patent/US4255436A/en not_active Expired - Lifetime
- 1979-11-02 IL IL58619A patent/IL58619A/xx unknown
- 1979-11-05 AU AU52483/79A patent/AU529272B2/en not_active Expired - Fee Related
- 1979-11-06 DE DE7979104345T patent/DE2965046D1/de not_active Expired
- 1979-11-06 BR BR7907182A patent/BR7907182A/pt unknown
- 1979-11-06 EP EP79104345A patent/EP0011221B1/de not_active Expired
- 1979-11-07 EG EG673/79A patent/EG13808A/xx active
- 1979-11-07 TR TR20531A patent/TR20531A/xx unknown
- 1979-11-07 AR AR278807A patent/AR224136A1/es active
- 1979-11-07 CS CS797593A patent/CS208682B2/cs unknown
- 1979-11-08 DK DK474179A patent/DK474179A/da not_active Application Discontinuation
- 1979-11-08 ES ES485806A patent/ES485806A1/es not_active Expired
- 1979-11-08 DD DD79216772A patent/DD147195A5/de unknown
- 1979-11-09 PL PL21951379A patent/PL219513A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU5248379A (en) | 1980-05-15 |
| US4255436A (en) | 1981-03-10 |
| IL58619A (en) | 1982-12-31 |
| CA1126278A (en) | 1982-06-22 |
| IL58619A0 (en) | 1980-02-29 |
| CS208682B2 (en) | 1981-09-15 |
| EG13808A (en) | 1982-06-30 |
| EP0011221A1 (de) | 1980-05-28 |
| TR20531A (tr) | 1981-10-21 |
| ES485806A1 (es) | 1980-10-01 |
| DE2965046D1 (en) | 1983-04-21 |
| AU529272B2 (en) | 1983-06-02 |
| AR224136A1 (es) | 1981-10-30 |
| BR7907182A (pt) | 1980-08-05 |
| DK474179A (da) | 1980-05-10 |
| PL219513A1 (cs) | 1980-12-15 |
| EP0011221B1 (de) | 1983-03-16 |
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