DE2144124C3 - N,N-Dimethyl-O-pyrazolyl-carbaminsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide - Google Patents
N,N-Dimethyl-O-pyrazolyl-carbaminsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als InsektizideInfo
- Publication number
- DE2144124C3 DE2144124C3 DE2144124A DE2144124A DE2144124C3 DE 2144124 C3 DE2144124 C3 DE 2144124C3 DE 2144124 A DE2144124 A DE 2144124A DE 2144124 A DE2144124 A DE 2144124A DE 2144124 C3 DE2144124 C3 DE 2144124C3
- Authority
- DE
- Germany
- Prior art keywords
- dimethyl
- pyrazolyl
- acid esters
- active ingredient
- preparation
- 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
Links
- 238000000034 method Methods 0.000 title description 10
- 238000002360 preparation method Methods 0.000 title description 7
- RFENIVGIBCPTFQ-UHFFFAOYSA-N 1H-pyrazol-5-yl N,N-dimethoxycarbamate Chemical class CON(OC)C(=O)OC1=NNC=C1 RFENIVGIBCPTFQ-UHFFFAOYSA-N 0.000 title description 3
- 239000002917 insecticide Substances 0.000 title 1
- 239000004480 active ingredient Substances 0.000 description 25
- 239000002904 solvent Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 241001124076 Aphididae Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 240000007124 Brassica oleracea Species 0.000 description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- -1 chloroformic acid ester Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 150000003217 pyrazoles Chemical class 0.000 description 7
- 241000255925 Diptera Species 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 230000000749 insecticidal effect Effects 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000013312 flour Nutrition 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 4
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 4
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000721623 Myzus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 210000001550 testis Anatomy 0.000 description 3
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- 235000011303 Brassica alboglabra Nutrition 0.000 description 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001465977 Coccoidea Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 239000004606 Fillers/Extenders Substances 0.000 description 2
- 241000721703 Lymantria dispar Species 0.000 description 2
- 241000721621 Myzus persicae Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 2
- 235000001535 Ribes X utile Nutrition 0.000 description 2
- 235000016919 Ribes petraeum Nutrition 0.000 description 2
- 244000281247 Ribes rubrum Species 0.000 description 2
- 235000002355 Ribes spicatum Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 239000002270 dispersing agent Substances 0.000 description 2
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- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000002560 nitrile group Chemical group 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 241001143308 Acanthoscelides Species 0.000 description 1
- 241000238818 Acheta domesticus Species 0.000 description 1
- 241000426834 Aegina Species 0.000 description 1
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- 241000218473 Agrotis Species 0.000 description 1
- 241000449794 Alabama argillacea Species 0.000 description 1
- 241001414900 Anopheles stephensi Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 240000003291 Armoracia rusticana Species 0.000 description 1
- 235000011330 Armoracia rusticana Nutrition 0.000 description 1
- 241000387321 Aspidiotus nerii Species 0.000 description 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000238788 Blaberus craniifer Species 0.000 description 1
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- 241001674044 Blattodea Species 0.000 description 1
- 241000256593 Brachycaudus schwartzi Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 241000907225 Bruchidius Species 0.000 description 1
- 241001664260 Byturus tomentosus Species 0.000 description 1
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- 241001249699 Capitata Species 0.000 description 1
- 241001107116 Castanospermum australe Species 0.000 description 1
- 241001221118 Cecidophyopsis ribis Species 0.000 description 1
- 241000254137 Cicadidae Species 0.000 description 1
- 241001414836 Cimex Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000456565 Cryptolestes pusillus Species 0.000 description 1
- 241000256059 Culex pipiens Species 0.000 description 1
- 241000328422 Culiseta annulata Species 0.000 description 1
- 241000255601 Drosophila melanogaster Species 0.000 description 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000416536 Euproctis pseudoconspersa Species 0.000 description 1
- 241000239245 Euscelis Species 0.000 description 1
- 241000953886 Fannia canicularis Species 0.000 description 1
- 241000255896 Galleria mellonella Species 0.000 description 1
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- 241000257303 Hymenoptera Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 241000255676 Malacosoma Species 0.000 description 1
- 241000254099 Melolontha melolontha Species 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N Methyl ethyl ketone Natural products CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- 241000332345 Myzus cerasi Species 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000131101 Oryzaephilus surinamensis Species 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 241001608567 Phaedon cochleariae Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 235000014441 Prunus serotina Nutrition 0.000 description 1
- 241000722238 Pseudococcus maritimus Species 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 241001509967 Reticulitermes flavipes Species 0.000 description 1
- 241000125167 Rhopalosiphum padi Species 0.000 description 1
- 241001510241 Rhyparobia Species 0.000 description 1
- 241001510236 Rhyparobia maderae Species 0.000 description 1
- 241001412173 Rubus canescens Species 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 244000235659 Rubus idaeus Species 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- 241000254179 Sitophilus granarius Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241001494115 Stomoxys calcitrans Species 0.000 description 1
- 241001454294 Tetranychus Species 0.000 description 1
- 241001414831 Triatoma infestans Species 0.000 description 1
- 241000254113 Tribolium castaneum Species 0.000 description 1
- 241000267822 Trogoderma granarium Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 241001466337 Yponomeuta Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000008055 alkyl aryl sulfonates 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
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
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- 235000015241 bacon Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000021279 black bean Nutrition 0.000 description 1
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- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000020044 madeira Nutrition 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
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- 239000012074 organic phase Substances 0.000 description 1
- NAHBVNMACPIHAH-HLICZWCASA-N p-ii Chemical compound C([C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H]2CSSC[C@H](NC(=O)[C@H](CC=3C=CC=CC=3)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC2=O)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O)=O)C(C)C)C1=CC=CC=C1 NAHBVNMACPIHAH-HLICZWCASA-N 0.000 description 1
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- 239000002798 polar solvent Substances 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
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- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE788241D BE788241A (fr) | 1971-09-03 | Nouveaux esters de o-pyrazolyle d'acide n, n-dimethyl-carbamique, leur procede de preparation et leur application comme insecticides | |
| DE2144124A DE2144124C3 (de) | 1971-09-03 | 1971-09-03 | N,N-Dimethyl-O-pyrazolyl-carbaminsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
| EG342/72A EG10773A (en) | 1971-09-03 | 1972-08-21 | N,n-dimethyl-c-pyrazolylcarbamatic acide esters,process for their use as insecticides |
| US00284325A US3786065A (en) | 1971-09-03 | 1972-08-28 | N,n-dimethyl-o-(-substituted-3,4-polymethylene-pyrazolyl-(5))-carbamic acid esters |
| AU46043/72A AU463245B2 (en) | 1971-09-03 | 1972-08-28 | N, N-dimethyl-O-pyrazolylcarbamic acid esters, process for their preparation and their use as insecticides |
| NL7211883A NL7211883A (enExample) | 1971-09-03 | 1972-08-31 | |
| IL40268A IL40268A (en) | 1971-09-03 | 1972-08-31 | N,n-dimethyl-o-pyrazolylcarbamates,their preparation and their use as insecticides |
| DD165385A DD102152A5 (enExample) | 1971-09-03 | 1972-09-01 | |
| CH1293072A CH573705A5 (enExample) | 1971-09-03 | 1972-09-01 | |
| TR17265A TR17265A (tr) | 1971-09-03 | 1972-09-01 | N,n-dimetil-o-pirazolilkarbamik asid esterleri,bunlarin elde edilme usulue ve ensektisid olarak kullanimalari |
| FR7231093A FR2152045A5 (enExample) | 1971-09-03 | 1972-09-01 | |
| CA150,763A CA1020565A (en) | 1971-09-03 | 1972-09-01 | N,n-dimethyl-o-pyrazolylcarbamic acid esters, process for their preparation and their use as insecticides |
| ZA726015A ZA726015B (en) | 1971-09-03 | 1972-09-01 | N,n-dimethyl-o-pyrazolylcarbamic acid esters,process for their preparation and their use as insecticides |
| IT28758/72A IT967101B (it) | 1971-09-03 | 1972-09-01 | Esteri dell acido n n dimetil o pirazolil carbammico procedimento per la loro preparazione e loro impiego come insetticidi |
| BR006063/72A BR7206063D0 (pt) | 1971-09-03 | 1972-09-01 | Processo para preparacao de novos esteres de acido n,n-dimetil-o-pirazolilcarbamico e composicoes inseticidas a base dos mesmos |
| HUBA2797A HU165296B (enExample) | 1971-09-03 | 1972-09-01 | |
| GB4070972A GB1354998A (en) | 1971-09-03 | 1972-09-01 | N,n-dimethyl-o-pyrazolylcarbamic acid esters process for their preparation and their use as insecticides |
| ES406334A ES406334A1 (es) | 1971-09-03 | 1972-09-02 | Procedimiento para la obtencion de un medio insecticida. |
| JP47088004A JPS4833029A (enExample) | 1971-09-03 | 1972-09-04 | |
| JP47088003A JPS4834159A (enExample) | 1971-09-03 | 1972-09-04 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2144124A DE2144124C3 (de) | 1971-09-03 | 1971-09-03 | N,N-Dimethyl-O-pyrazolyl-carbaminsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2144124A1 DE2144124A1 (de) | 1973-03-15 |
| DE2144124B2 DE2144124B2 (de) | 1979-05-17 |
| DE2144124C3 true DE2144124C3 (de) | 1980-01-17 |
Family
ID=5818551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2144124A Expired DE2144124C3 (de) | 1971-09-03 | 1971-09-03 | N,N-Dimethyl-O-pyrazolyl-carbaminsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US3786065A (enExample) |
| JP (2) | JPS4834159A (enExample) |
| AU (1) | AU463245B2 (enExample) |
| BE (1) | BE788241A (enExample) |
| BR (1) | BR7206063D0 (enExample) |
| CA (1) | CA1020565A (enExample) |
| CH (1) | CH573705A5 (enExample) |
| DD (1) | DD102152A5 (enExample) |
| DE (1) | DE2144124C3 (enExample) |
| EG (1) | EG10773A (enExample) |
| ES (1) | ES406334A1 (enExample) |
| FR (1) | FR2152045A5 (enExample) |
| GB (1) | GB1354998A (enExample) |
| HU (1) | HU165296B (enExample) |
| IL (1) | IL40268A (enExample) |
| IT (1) | IT967101B (enExample) |
| NL (1) | NL7211883A (enExample) |
| TR (1) | TR17265A (enExample) |
| ZA (1) | ZA726015B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2607658A1 (de) * | 1976-02-25 | 1977-09-01 | Bayer Ag | 0,s-dialkyl-0-pyrazolothionothiolphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| DE2931033A1 (de) * | 1979-07-31 | 1981-02-19 | Bayer Ag | N-methyl-o-pyrazol(4)yl-carbaminsaeureester, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| JPH04135402U (ja) * | 1991-05-31 | 1992-12-16 | 雅保 高見 | 荷造テープ締付機におけるテープ溶融時間調節装置 |
-
0
- BE BE788241D patent/BE788241A/xx unknown
-
1971
- 1971-09-03 DE DE2144124A patent/DE2144124C3/de not_active Expired
-
1972
- 1972-08-21 EG EG342/72A patent/EG10773A/xx active
- 1972-08-28 US US00284325A patent/US3786065A/en not_active Expired - Lifetime
- 1972-08-28 AU AU46043/72A patent/AU463245B2/en not_active Expired
- 1972-08-31 NL NL7211883A patent/NL7211883A/xx not_active Application Discontinuation
- 1972-08-31 IL IL40268A patent/IL40268A/xx unknown
- 1972-09-01 TR TR17265A patent/TR17265A/xx unknown
- 1972-09-01 DD DD165385A patent/DD102152A5/xx unknown
- 1972-09-01 IT IT28758/72A patent/IT967101B/it active
- 1972-09-01 HU HUBA2797A patent/HU165296B/hu unknown
- 1972-09-01 CH CH1293072A patent/CH573705A5/xx not_active IP Right Cessation
- 1972-09-01 ZA ZA726015A patent/ZA726015B/xx unknown
- 1972-09-01 FR FR7231093A patent/FR2152045A5/fr not_active Expired
- 1972-09-01 CA CA150,763A patent/CA1020565A/en not_active Expired
- 1972-09-01 BR BR006063/72A patent/BR7206063D0/pt unknown
- 1972-09-01 GB GB4070972A patent/GB1354998A/en not_active Expired
- 1972-09-02 ES ES406334A patent/ES406334A1/es not_active Expired
- 1972-09-04 JP JP47088003A patent/JPS4834159A/ja active Pending
- 1972-09-04 JP JP47088004A patent/JPS4833029A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA1020565A (en) | 1977-11-08 |
| DE2144124A1 (de) | 1973-03-15 |
| TR17265A (tr) | 1975-03-24 |
| JPS4833029A (enExample) | 1973-05-07 |
| JPS4834159A (enExample) | 1973-05-16 |
| US3786065A (en) | 1974-01-15 |
| IL40268A (en) | 1975-06-25 |
| ZA726015B (en) | 1973-05-30 |
| GB1354998A (en) | 1974-06-05 |
| FR2152045A5 (enExample) | 1973-04-20 |
| EG10773A (en) | 1976-09-30 |
| BR7206063D0 (pt) | 1973-07-17 |
| IL40268A0 (en) | 1972-10-29 |
| ES406334A1 (es) | 1975-07-01 |
| AU463245B2 (en) | 1975-07-17 |
| HU165296B (enExample) | 1974-08-28 |
| NL7211883A (enExample) | 1973-03-06 |
| AU4604372A (en) | 1974-03-07 |
| DE2144124B2 (de) | 1979-05-17 |
| BE788241A (fr) | 1973-02-28 |
| DD102152A5 (enExample) | 1973-12-05 |
| CH573705A5 (enExample) | 1976-03-31 |
| IT967101B (it) | 1974-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| EHV | Ceased/renunciation |