IL46172A - Pyrimidine Acid Esters - Olephosphoric Theones, Their Preparation and Use as Insecticides and Mites - Google Patents
Pyrimidine Acid Esters - Olephosphoric Theones, Their Preparation and Use as Insecticides and MitesInfo
- Publication number
- IL46172A IL46172A IL46172A IL4617274A IL46172A IL 46172 A IL46172 A IL 46172A IL 46172 A IL46172 A IL 46172A IL 4617274 A IL4617274 A IL 4617274A IL 46172 A IL46172 A IL 46172A
- Authority
- IL
- Israel
- Prior art keywords
- carbon atoms
- pyrimidine
- compound
- process according
- methyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 21
- 150000002148 esters Chemical class 0.000 title claims abstract description 14
- 230000000895 acaricidal effect Effects 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title description 11
- 239000002917 insecticide Substances 0.000 title description 3
- 239000000642 acaricide Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 5
- 150000001875 compounds Chemical class 0.000 claims description 46
- -1 methylthio, ethylthio, n-propylthio , iso-propylthio, methylthiomethyl- thio, ethylthioethylthio, methylthioethylthio Chemical group 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 11
- 241000607479 Yersinia pestis Species 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 241000238631 Hexapoda Species 0.000 claims description 8
- 230000006378 damage Effects 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 150000008081 1H-pyrimidin-4-ones Chemical class 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 230000001069 nematicidal effect Effects 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 241000255925 Diptera Species 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 241000254173 Coleoptera Species 0.000 description 4
- 241001454295 Tetranychidae Species 0.000 description 4
- 239000000969 carrier 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
- 239000011541 reaction mixture Substances 0.000 description 4
- 241001510109 Blaberus giganteus Species 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000721621 Myzus persicae Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 241000500437 Plutella xylostella Species 0.000 description 3
- 241000254154 Sitophilus zeamais Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241001454294 Tetranychus Species 0.000 description 3
- 241001454293 Tetranychus urticae Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- OCOHPSHRDKBGOZ-UHFFFAOYSA-N 6-methyl-2-methylsulfanyl-1h-pyrimidin-4-one Chemical compound CSC1=NC(=O)C=C(C)N1 OCOHPSHRDKBGOZ-UHFFFAOYSA-N 0.000 description 2
- 241001143309 Acanthoscelides obtectus Species 0.000 description 2
- 241000238818 Acheta domesticus Species 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000387321 Aspidiotus nerii Species 0.000 description 2
- 241000238662 Blatta orientalis Species 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 241001444260 Brassicogethes aeneus Species 0.000 description 2
- 241001221118 Cecidophyopsis ribis Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001327638 Cimex lectularius Species 0.000 description 2
- 241001581006 Dysaphis plantaginea Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 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 2
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 2
- 241000254099 Melolontha melolontha Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 241000810465 Myzus cerasi cerasi Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241001491877 Operophtera brumata Species 0.000 description 2
- 241000131101 Oryzaephilus surinamensis Species 0.000 description 2
- 241000488583 Panonychus ulmi Species 0.000 description 2
- 241000238675 Periplaneta americana Species 0.000 description 2
- 241001608567 Phaedon cochleariae Species 0.000 description 2
- 241000257186 Phormia regina Species 0.000 description 2
- 241001396980 Phytonemus pallidus Species 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- 241000500439 Plutella Species 0.000 description 2
- 241000952063 Polyphagotarsonemus latus Species 0.000 description 2
- 241000722238 Pseudococcus maritimus Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000125167 Rhopalosiphum padi Species 0.000 description 2
- 241000254179 Sitophilus granarius 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241001494115 Stomoxys calcitrans Species 0.000 description 2
- 241000254109 Tenebrio molitor Species 0.000 description 2
- 241001414989 Thysanoptera Species 0.000 description 2
- 241000267822 Trogoderma granarium Species 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 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
- 238000010410 dusting Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 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
- VWXLCWNPSOUPPE-UHFFFAOYSA-N (1-amino-2-methylpropylidene)azanium;chloride Chemical compound Cl.CC(C)C(N)=N VWXLCWNPSOUPPE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- YPQSUXWNLKGWTQ-UHFFFAOYSA-N 6-methyl-5-methylsulfanyl-2-propan-2-yl-1h-pyrimidin-4-one Chemical compound CSC1=C(C)N=C(C(C)C)N=C1O YPQSUXWNLKGWTQ-UHFFFAOYSA-N 0.000 description 1
- 241000253994 Acyrthosiphon pisum Species 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241001136249 Agriotes lineatus Species 0.000 description 1
- 241000218473 Agrotis Species 0.000 description 1
- 241000449794 Alabama argillacea Species 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 241001414900 Anopheles stephensi Species 0.000 description 1
- 241000238805 Blaberus Species 0.000 description 1
- 241000238658 Blattella Species 0.000 description 1
- 241000238657 Blattella germanica Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 235000011303 Brassica alboglabra Nutrition 0.000 description 1
- 235000011302 Brassica oleracea Nutrition 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 241000907225 Bruchidius Species 0.000 description 1
- 241001664277 Byturus Species 0.000 description 1
- 241000042459 Byturus aestivus Species 0.000 description 1
- 241000257160 Calliphora Species 0.000 description 1
- 241000257163 Calliphora vicina Species 0.000 description 1
- 241000254137 Cicadidae Species 0.000 description 1
- 241001415288 Coccidae Species 0.000 description 1
- 241001465977 Coccoidea Species 0.000 description 1
- 241001479447 Coccus hesperidum Species 0.000 description 1
- 241001094913 Cryptomyzus Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000256059 Culex pipiens Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- 241000289763 Dasygaster padockina Species 0.000 description 1
- 241001641895 Dermestes Species 0.000 description 1
- 241001513837 Dermestes maculatus Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
- 241001425477 Dysdercus Species 0.000 description 1
- 241001425472 Dysdercus cingulatus Species 0.000 description 1
- 241000122098 Ephestia kuehniella Species 0.000 description 1
- 241001221110 Eriophyidae Species 0.000 description 1
- 241001331999 Euproctis Species 0.000 description 1
- 241000483001 Euproctis chrysorrhoea Species 0.000 description 1
- 241000239245 Euscelis Species 0.000 description 1
- 241000953886 Fannia canicularis Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000255896 Galleria mellonella Species 0.000 description 1
- 241001675057 Gastrophysa viridula Species 0.000 description 1
- 241001232715 Granaria Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241000652697 Henschoutedenia flexivitta Species 0.000 description 1
- 241001659688 Hercinothrips femoralis Species 0.000 description 1
- 241001251909 Hyalopterus pruni Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000256686 Lasius <genus> Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000721703 Lymantria dispar Species 0.000 description 1
- 241000721715 Macrosiphum Species 0.000 description 1
- 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
- 241000255676 Malacosoma Species 0.000 description 1
- 241000255685 Malacosoma neustria Species 0.000 description 1
- 241000555303 Mamestra brassicae Species 0.000 description 1
- HWGBHCRJGXAGEU-UHFFFAOYSA-N Methylthiouracil Chemical compound CC1=CC(=O)NC(=S)N1 HWGBHCRJGXAGEU-UHFFFAOYSA-N 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 241000961933 Nephotettix virescens Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000238887 Ornithodoros Species 0.000 description 1
- 241001481099 Ornithodoros turicata Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241001548358 Parapiesma quadratum Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 241001097374 Pselliopus cinctus Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241001509970 Reticulitermes <genus> Species 0.000 description 1
- 241001509967 Reticulitermes flavipes Species 0.000 description 1
- 241000722249 Rhodnius prolixus Species 0.000 description 1
- 241001510241 Rhyparobia Species 0.000 description 1
- 241001510236 Rhyparobia maderae Species 0.000 description 1
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 1
- 235000001535 Ribes X utile Nutrition 0.000 description 1
- 235000016919 Ribes petraeum Nutrition 0.000 description 1
- 244000281247 Ribes rubrum Species 0.000 description 1
- 235000002355 Ribes spicatum Nutrition 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 241001177161 Stegobium paniceum Species 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 241001414831 Triatoma infestans Species 0.000 description 1
- 241000254113 Tribolium castaneum Species 0.000 description 1
- 241001466337 Yponomeuta Species 0.000 description 1
- 241000064240 Yponomeuta padellus Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals 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
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000011230 binding agent Substances 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
- 239000000470 constituent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 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
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- OTSZNJPJMBPQTN-UHFFFAOYSA-N ethyl 2-methylsulfanyl-3-oxobutanoate Chemical compound CCOC(=O)C(SC)C(C)=O OTSZNJPJMBPQTN-UHFFFAOYSA-N 0.000 description 1
- MBSGUVQNCRQQHC-UHFFFAOYSA-N ethyl 6-methyl-5-methylsulfanyl-4-oxo-1h-pyrimidine-2-carboxylate Chemical compound CCOC(=O)C1=NC(=O)C(SC)=C(C)N1 MBSGUVQNCRQQHC-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 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
- 235000013312 flour Nutrition 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2360877A DE2360877A1 (de) | 1973-12-06 | 1973-12-06 | Pyrimidin-thionothiolphosphorsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL46172A0 IL46172A0 (en) | 1975-03-13 |
| IL46172A true IL46172A (en) | 1977-12-30 |
Family
ID=5900103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL46172A IL46172A (en) | 1973-12-06 | 1974-12-03 | Pyrimidine Acid Esters - Olephosphoric Theones, Their Preparation and Use as Insecticides and Mites |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US3951975A (da) |
| JP (2) | JPS5084581A (da) |
| AR (1) | AR204843A1 (da) |
| AT (1) | AT327953B (da) |
| BE (1) | BE822986A (da) |
| BG (1) | BG21856A3 (da) |
| BR (1) | BR7410175A (da) |
| CA (1) | CA1029728A (da) |
| DD (1) | DD116046A5 (da) |
| DE (1) | DE2360877A1 (da) |
| DK (1) | DK135046C (da) |
| ES (1) | ES432613A1 (da) |
| FI (1) | FI351974A (da) |
| FR (1) | FR2253757B1 (da) |
| GB (1) | GB1468270A (da) |
| HU (1) | HU169967B (da) |
| IL (1) | IL46172A (da) |
| KE (1) | KE2771A (da) |
| LU (1) | LU71424A1 (da) |
| MY (1) | MY7800145A (da) |
| NL (1) | NL7415815A (da) |
| NO (1) | NO744208L (da) |
| OA (1) | OA04805A (da) |
| PL (1) | PL93687B1 (da) |
| SE (1) | SE7415260L (da) |
| SU (1) | SU520872A3 (da) |
| TR (1) | TR18127A (da) |
| ZA (1) | ZA747748B (da) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2501769A1 (de) * | 1975-01-17 | 1976-07-22 | Bayer Ag | Substituierte pyrimidinyl(thiono)(thiol)-phosphor (phosphon)-saeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematozide |
| DE2639256A1 (de) * | 1976-09-01 | 1978-03-02 | Bayer Ag | Alkoxy- bzw. alkylthiosubstituierte pyrimidin(thiono)-(thiol)-phosphor(phosphon)-saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| DE2639433A1 (de) * | 1976-09-02 | 1978-03-09 | Bayer Ag | Pyrimidinyl(thiono)(thiol)-phosphor(phosphon)-saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| AU511744B2 (en) * | 1976-09-25 | 1980-09-04 | Bayer Aktiengesellschaft | Pyrimidin(5)yl-(thiono) (thiol) phosporic-(phosphonic) acid esters and ester-amides |
| US4654329A (en) * | 1978-07-28 | 1987-03-31 | The Dow Chemical Company | Insecticidal, miticidal or nematocidal phosphorus esters of 5-pyrimidinols |
| DE2835492A1 (de) * | 1978-08-12 | 1980-02-21 | Bayer Ag | 2-cycloalkyl-pyrimidin(5)yl-(thiono) (thiol)-phosphor-(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide |
| US4486422A (en) * | 1982-11-22 | 1984-12-04 | The Dow Chemical Company | Insecticidal phosphorus derivatives of 5-pyrimidinols |
| US4486421A (en) * | 1982-11-22 | 1984-12-04 | The Dow Chemical Company | Insecticidal phosphorus derivatives of 4-pyrimidinols |
| US4588711A (en) * | 1982-11-22 | 1986-05-13 | The Dow Chemical Company | Insecticidal phosphorus derivatives of 6-cycloalkyl-4-pyrimidinols |
| US4575499A (en) * | 1982-11-22 | 1986-03-11 | The Dow Chemical Company | Phosphorus derivatives of 4-pyrimidinols |
| DE3729264A1 (de) * | 1987-09-02 | 1989-03-23 | Bayer Ag | Pyrimidinyl(thiono)(thiol)-phosphorsaeureester |
| IL110096A (en) * | 1994-06-23 | 1998-07-15 | Makhteshim Chem Works Ltd | Process for preparing diazinon |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU31414A1 (da) * | 1951-04-20 | 1900-01-01 | ||
| US3328405A (en) * | 1964-05-22 | 1967-06-27 | Stauffer Chemical Co | Process for the production of substituted pyrimidines |
-
1973
- 1973-12-06 DE DE2360877A patent/DE2360877A1/de active Pending
-
1974
- 1974-01-01 AR AR256244A patent/AR204843A1/es active
- 1974-11-22 NO NO744208A patent/NO744208L/no unknown
- 1974-12-02 BG BG028328A patent/BG21856A3/xx unknown
- 1974-12-03 IL IL46172A patent/IL46172A/en unknown
- 1974-12-03 JP JP49137796A patent/JPS5084581A/ja active Pending
- 1974-12-03 JP JP49137797A patent/JPS5089538A/ja active Pending
- 1974-12-04 DD DD182773A patent/DD116046A5/xx unknown
- 1974-12-04 AT AT968574A patent/AT327953B/de not_active IP Right Cessation
- 1974-12-04 US US05/529,658 patent/US3951975A/en not_active Expired - Lifetime
- 1974-12-04 FI FI3519/74A patent/FI351974A/fi unknown
- 1974-12-04 SU SU2081672A patent/SU520872A3/ru active
- 1974-12-04 LU LU71424A patent/LU71424A1/xx unknown
- 1974-12-04 PL PL1974176174A patent/PL93687B1/pl unknown
- 1974-12-04 NL NL7415815A patent/NL7415815A/xx not_active Application Discontinuation
- 1974-12-04 CA CA215,194A patent/CA1029728A/en not_active Expired
- 1974-12-05 GB GB5263274A patent/GB1468270A/en not_active Expired
- 1974-12-05 DK DK633574A patent/DK135046C/da active
- 1974-12-05 BR BR10175/74A patent/BR7410175A/pt unknown
- 1974-12-05 TR TR18127A patent/TR18127A/xx unknown
- 1974-12-05 BE BE151184A patent/BE822986A/xx unknown
- 1974-12-05 SE SE7415260A patent/SE7415260L/xx unknown
- 1974-12-05 HU HUBA3176A patent/HU169967B/hu unknown
- 1974-12-05 ES ES432613A patent/ES432613A1/es not_active Expired
- 1974-12-05 ZA ZA00747748A patent/ZA747748B/xx unknown
- 1974-12-06 OA OA55357A patent/OA04805A/xx unknown
- 1974-12-06 FR FR7440058A patent/FR2253757B1/fr not_active Expired
-
1977
- 1977-09-08 KE KE2771A patent/KE2771A/xx unknown
-
1978
- 1978-12-30 MY MY145/78A patent/MY7800145A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TR18127A (tr) | 1977-03-01 |
| FR2253757A1 (da) | 1975-07-04 |
| DD116046A5 (da) | 1975-11-05 |
| DK135046B (da) | 1977-02-28 |
| BG21856A3 (bg) | 1976-09-20 |
| ATA968574A (de) | 1975-05-15 |
| ES432613A1 (es) | 1976-12-01 |
| OA04805A (fr) | 1980-08-31 |
| SE7415260L (da) | 1975-06-09 |
| ZA747748B (en) | 1975-12-31 |
| US3951975A (en) | 1976-04-20 |
| KE2771A (en) | 1977-10-21 |
| CA1029728A (en) | 1978-04-18 |
| AT327953B (de) | 1976-02-25 |
| NO744208L (da) | 1975-06-30 |
| AU7600074A (en) | 1976-06-03 |
| SU520872A3 (ru) | 1976-07-05 |
| MY7800145A (en) | 1978-12-31 |
| LU71424A1 (da) | 1975-08-20 |
| GB1468270A (en) | 1977-03-23 |
| JPS5089538A (da) | 1975-07-18 |
| PL93687B1 (da) | 1977-06-30 |
| BE822986A (fr) | 1975-06-05 |
| JPS5084581A (da) | 1975-07-08 |
| DE2360877A1 (de) | 1975-06-19 |
| DK633574A (da) | 1975-07-28 |
| DK135046C (da) | 1977-07-25 |
| HU169967B (en) | 1977-03-28 |
| AR204843A1 (es) | 1976-03-05 |
| FR2253757B1 (da) | 1978-06-23 |
| BR7410175A (pt) | 1976-06-08 |
| FI351974A (da) | 1975-06-07 |
| NL7415815A (nl) | 1975-06-10 |
| IL46172A0 (en) | 1975-03-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3932406A (en) | 2-Trifluoromethylimino-1,3-dithiolo [4,5-b]-quinoxalines | |
| US3951975A (en) | O-Alkyl-S-alkyl-O-[2-substituted-pyrimidin(4)yl]thionothiolphosphoric acid esters | |
| IL43411A (en) | N,n-dimethyl-o-(3-alkylthio-1,2,4-triazol-5-yl)-carbamic acid esters,their preparation and insecticidal and acaricidal compositions containing them | |
| IL47958A (en) | Pyrimidinylthionophosphonic acid esters process for their preparation and insecticidal acaricidal and nematicidal compositions containing them | |
| IL46687A (en) | N-sulphenylated oxime-carbamates their preparation and insecticidal acaricidal and nematicidal compositions containing them | |
| IL34985A (en) | Triazolothiazole esters of phosphoric, phosphonic and phosphonic acids and of the appropriate tionic acids, their preparation and use as insecticides and acaricides | |
| US3954755A (en) | 7-Bromoquinoxal-6-yl-(thiono)-(thiol)-phosphoric and (phosphonic) acid esters of ester-amides | |
| US3996367A (en) | N,N-dimethyl-O-[1-methyl-3-N-methylcarbaminyl-methyl-pyrazol(5)yl]-carbamic acid ester | |
| IL31318A (en) | Phosphoric,phosphonic or thionophosphoric(-phosphonic)acid esters of pyridazinediol,their preparation and pest control compositions containing them | |
| IL45403A (en) | O-phenyl-thionophosphoric and-phosphonic acid ester-amide and ester-imide derivatives their preparation and their use as insecticides and acaricides | |
| US4058603A (en) | Insecticidal and acaricidal O-ethyl-O-[1,6-dihydro-1-substituted-6-oxo-pyridazin(3)yl]-thionobenzenephosphonic acid esters | |
| US4006244A (en) | Benzo-1,3-dioxolan-4-yl N-methyl-N-phenylmercapto-carbamates | |
| IL31640A (en) | Thionophosphonic acid esters,their preparation and use for pest control | |
| US3974171A (en) | O-[3-methyl-1,3,4-triazole-(2,3,-b)-thiazol(6)yl]-(thiono)-phosphoric(phosphonic) acid esters | |
| IL46198A (en) | Triazolothiazolyl-(thiono)-phosphoric (phosphonic)- acid esters their preparation and insecticidal and acaricidal compositions containing them | |
| US3981993A (en) | O-Alkyl-O-n-propyl-O-pyrimidin(2)yl-thiono-phosphoric acid esters | |
| US3980783A (en) | O-Alkyl-S-[3-oxo-triazolo-(4,3-α-pyridin(2)yl-methyl]-(thiono)thiol-phosphoric(phosphonic) acid esters and ester-amides | |
| US3950337A (en) | O-pyrazolopyrimidine-(thiono)-phosphoric(phosphonic) acid esters | |
| IL37223A (en) | Esters of O-pyrazolo-pyrimidine- (thionic) - phosphorous and phosphonic acids, their preparation and use as insecticides and mites | |
| US3966920A (en) | O,S-Dialkyl-O-(2-cyanophenyl)-thionothiolphosphoric acid esters and insecticidal and acaricidal compositions and method | |
| US4013794A (en) | O-alkyl-s-alkyl-o-phenyl phosphates and insecticidal and acaricidal method of use | |
| IL38701A (en) | Substituted pyrazol(3)yl-carbamic acid esters,their preparation and their use as insecticides or acaricides | |
| US4000268A (en) | N,N-dimethyl-N'-[O-phenyl-(thiono)-alkane-phosphonyl]-formamidines | |
| IL47240A (en) | O-triazolyl-(thiono)-phosphoric(phosphonic phosphinic) acid esters and ester-amides their preparation and their use as insecticides acaricides or nematicides | |
| IE41829B1 (en) | N-sulphenylated n-methyl-carbamates, process for their preparation, and their use as insecticides or acaricides |