NO742928L - - Google Patents

Info

Publication number: NO742928L
Authority: NO; Norway
Prior art keywords: active substance; alkyl; pyrimidine; hydrogen; methyl
Prior art date: 1973-08-31

Application number

NO74742928A

Other languages

English (en)

Norwegian (no)

Inventor

W Hofer

F Maurer

H-J Riebel

L Rohe

W Behrenz

I Hammann

W Stendel

B Homeyer

Original Assignee

Bayer Ag

Priority date (The priority date 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 date listed.)

1973-08-31

Filing date

1974-08-14

Publication date

1975-03-24

1974-08-14 Application filed by Bayer Ag filed Critical Bayer Ag

1975-03-24 Publication of NO742928L publication Critical patent/NO742928L/no

Links

239000002904 solvent Substances 0.000 claims description 40
-1 ester amide Chemical class 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 19
241000238631 Hexapoda Species 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
229910052698 phosphorus Inorganic materials 0.000 claims description 9
239000011574 phosphorus Substances 0.000 claims description 9
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
230000000895 acaricidal effect Effects 0.000 claims description 8
241000238876 Acari Species 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
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 claims description 5
241000607479 Yersinia pestis Species 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
230000000749 insecticidal effect Effects 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
239000000370 acceptor Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
150000008081 1H-pyrimidin-4-ones Chemical class 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
239000000642 acaricide Substances 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000002917 insecticide Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 claims description 2
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 2
229910001414 potassium ion Inorganic materials 0.000 claims description 2
159000000001 potassium salts Chemical class 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
229910001415 sodium ion Inorganic materials 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
239000005864 Sulphur Chemical group 0.000 claims 1
150000003573 thiols Chemical class 0.000 claims 1
239000000080 wetting agent Substances 0.000 claims 1
239000013543 active substance Substances 0.000 description 70
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
238000002360 preparation method Methods 0.000 description 26
241001465754 Metazoa Species 0.000 description 19
239000003995 emulsifying agent Substances 0.000 description 19
239000002689 soil Substances 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
229920000151 polyglycol Polymers 0.000 description 11
239000010695 polyglycol Substances 0.000 description 11
239000000203 mixture Substances 0.000 description 9
241000255925 Diptera Species 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
125000002877 alkyl aryl group Chemical group 0.000 description 8
239000012141 concentrate Substances 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000011521 glass Substances 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000000843 powder Substances 0.000 description 5
CRYUGFDHGVCIJW-UHFFFAOYSA-N 2-methoxy-6-methyl-1h-pyrimidin-4-one Chemical compound COC1=NC(C)=CC(O)=N1 CRYUGFDHGVCIJW-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
241000244206 Nematoda Species 0.000 description 4
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239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 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
241000196324 Embryophyta Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
244000046052 Phaseolus vulgaris Species 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000969 carrier Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
240000007124 Brassica oleracea Species 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000254173 Coleoptera Species 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000255601 Drosophila melanogaster Species 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
240000008415 Lactuca sativa Species 0.000 description 2
235000003228 Lactuca sativa Nutrition 0.000 description 2
241000257166 Lucilia cuprina 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
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000238675 Periplaneta americana Species 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000254179 Sitophilus granarius Species 0.000 description 2
241000254154 Sitophilus zeamais Species 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
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
241000254109 Tenebrio molitor Species 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000004927 clay Substances 0.000 description 2
238000001816 cooling Methods 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
239000000839 emulsion Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000006072 paste Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003892 spreading Methods 0.000 description 2
230000007480 spreading Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
229910052717 sulfur Chemical group 0.000 description 2
239000011593 sulfur Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
MUDVUWOLBJRUGF-UHFFFAOYSA-N (c-methoxycarbonimidoyl)azanium;chloride Chemical compound Cl.COC(N)=N MUDVUWOLBJRUGF-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
VUTMMWSZWICTSW-UHFFFAOYSA-N 2-dodecoxy-6-methyl-1h-pyrimidin-4-one Chemical compound CCCCCCCCCCCCOC1=NC(C)=CC(O)=N1 VUTMMWSZWICTSW-UHFFFAOYSA-N 0.000 description 1
CIJKVRCNKUAYKK-UHFFFAOYSA-N 2-ethoxy-6-methyl-1h-pyrimidin-4-one Chemical compound CCOC1=NC(C)=CC(O)=N1 CIJKVRCNKUAYKK-UHFFFAOYSA-N 0.000 description 1
QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 1
LHRIUKSRPHFASO-UHFFFAOYSA-N 6-methyl-1h-pyrimidin-4-one Chemical compound CC1=CC(=O)N=CN1 LHRIUKSRPHFASO-UHFFFAOYSA-N 0.000 description 1
CQNGWWLYGIOTAD-UHFFFAOYSA-N 6-methyl-2-prop-2-ynoxy-1h-pyrimidin-4-one Chemical compound CC1=CC(O)=NC(OCC#C)=N1 CQNGWWLYGIOTAD-UHFFFAOYSA-N 0.000 description 1
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LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
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125000004093 cyano group Chemical group *C#N 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
208000031513 cyst Diseases 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
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
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
244000078703 ectoparasite Species 0.000 description 1
235000014103 egg white Nutrition 0.000 description 1
210000000969 egg white Anatomy 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002084 enol ethers Chemical class 0.000 description 1
206010014881 enterobiasis Diseases 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000002191 fatty alcohols Chemical class 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
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000004088 foaming agent Substances 0.000 description 1
150000004820 halides 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
150000003840 hydrochlorides Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
229910017053 inorganic salt Inorganic materials 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
229920005610 lignin Polymers 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
229910052901 montmorillonite Inorganic materials 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
238000005554 pickling Methods 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 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
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011435 rock Substances 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
UJXHQRXBCSZHFA-UHFFFAOYSA-M sodium;5-chloro-2-methoxy-6-methylpyrimidin-4-olate Chemical compound COC1=NC(C)=C(Cl)C(O[Na])=N1 UJXHQRXBCSZHFA-UHFFFAOYSA-M 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
238000003860 storage 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
239000000375 suspending agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- 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)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO74742928A 1973-08-31 1974-08-14 NO742928L (ro)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19732343931 DE2343931A1 (de)	1973-08-31	1973-08-31	Pyrimidin(4)-yl-(thiono)-(thiol)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung sowie ihre verwendung als insetktizide und akarizide

Publications (1)

Publication Number	Publication Date
NO742928L true NO742928L (ro)	1975-03-24

Family

ID=5891238

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO74742928A NO742928L (ro)	1973-08-31	1974-08-14

Country Status (28)

Country	Link
US (1)	US3966730A (ro)
JP (2)	JPS5049431A (ro)
AR (1)	AR209594A1 (ro)
AT (1)	AT326147B (ro)
BE (1)	BE819278A (ro)
BR (1)	BR7407284D0 (ro)
CA (1)	CA1027565A (ro)
CH (1)	CH606042A5 (ro)
CS (1)	CS188925B2 (ro)
DD (1)	DD114818A5 (ro)
DE (1)	DE2343931A1 (ro)
DK (1)	DK136368C (ro)
EG (1)	EG11113A (ro)
ES (1)	ES429674A1 (ro)
FI (1)	FI253374A (ro)
FR (1)	FR2242396B1 (ro)
GB (1)	GB1483531A (ro)
HU (1)	HU169164B (ro)
IL (1)	IL45560A (ro)
LU (1)	LU70821A1 (ro)
NL (1)	NL7411460A (ro)
NO (1)	NO742928L (ro)
PL (2)	PL97978B1 (ro)
RO (1)	RO65813A (ro)
SE (1)	SE409208B (ro)
SU (1)	SU529802A3 (ro)
TR (1)	TR18078A (ro)
ZA (1)	ZA745545B (ro)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2545881C2 (de) *	1975-10-14	1985-08-29	Bayer Ag, 5090 Leverkusen	0-Pyrazolopyrimidinthionothiolphosphorsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Bekämpfung von Insekten, Milben und Nematoden
DE2620089A1 (de) *	1976-05-06	1977-11-24	Bayer Ag	Substituierte pyrimidin-bis- eckige klammer auf (thiono)(thiol)-phosphor(phosphon)-saeureester eckige klammer zu, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide
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
DE2642981C2 (de) *	1976-09-24	1984-11-08	Bayer Ag, 5090 Leverkusen	Alkoxysubstituierte Pyrimidinyl-thionophosphonsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide und Akarizide
NL7712098A (nl) *	1976-11-10	1978-05-12	Ciba Geigy	Werkwijze ter bereiding van fosforzuurderivaten, alsmede de toepassing ervan als gewasbescher- mingsmiddelen.
DE2747357A1 (de) *	1977-10-21	1979-04-26	Bayer Ag	Substituierte pyrimidinyl(thiono) (thiol)phosphor (phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2831165A1 (de) *	1978-07-15	1980-01-24	Bayer Ag	2-cyclopropyl-pyrimidin(4)yl-thionophosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
JPS5615296A (en) *	1979-07-17	1981-02-14	Otsuka Pharmaceut Co Ltd	Quinazoline derivative
US4489068A (en) *	1983-04-28	1984-12-18	The Dow Chemical Company	Method and composition for enhancing the insecticidal activity of certain organophosphorus compounds
US5034529A (en) *	1988-04-28	1991-07-23	Ciba-Geigy Corporation	Process for the production of thiophosphoric acid esters of hydroxypyrimidines
CA2199899C (en) *	1996-03-26	2004-05-11	Beat Schmidt	Process for the preparation of a 2-alkoxy-6-(trifluoro-methyl)pyrimidin-4-ol
CA2512034A1 (en) *	2003-01-31	2004-08-12	Lonza Ltd.	Process for preparation of 2-alkoxy-6-(trifluoromethyl)pyrimidin-4-ol

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL126404C (ro) *	1959-03-28	1900-01-01
DE1193055B (de) *	1962-07-28	1965-05-20	Bayer Ag	Verfahren zur Herstellung von Thionophosphon-saeureestern
DK130683B (da) *	1971-03-04	1975-03-24	Sandoz Ag	Pesticidt virksomme pyrimidinylphosphorsyreestere.
DE2144392A1 (de) *	1971-09-04	1973-03-08	Bayer Ag	0-pyrimidyl-(thiono)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide

1973
- 1973-08-31 DE DE19732343931 patent/DE2343931A1/de active Pending
1974
- 1974-08-14 NO NO74742928A patent/NO742928L/no unknown
- 1974-08-15 SU SU2051826A patent/SU529802A3/ru active
- 1974-08-22 US US05/499,808 patent/US3966730A/en not_active Expired - Lifetime
- 1974-08-26 EG EG354/74A patent/EG11113A/xx active
- 1974-08-27 AR AR255326A patent/AR209594A1/es active
- 1974-08-28 BE BE147972A patent/BE819278A/xx unknown
- 1974-08-28 NL NL7411460A patent/NL7411460A/xx not_active Application Discontinuation
- 1974-08-28 IL IL7445560A patent/IL45560A/xx unknown
- 1974-08-29 SE SE7410957A patent/SE409208B/xx unknown
- 1974-08-29 PL PL1974193013A patent/PL97978B1/pl unknown
- 1974-08-29 JP JP49098466A patent/JPS5049431A/ja active Pending
- 1974-08-29 JP JP49098465A patent/JPS5050382A/ja active Pending
- 1974-08-29 RO RO197479872A patent/RO65813A/ro unknown
- 1974-08-29 AT AT699474A patent/AT326147B/de not_active IP Right Cessation
- 1974-08-29 PL PL1974173764A patent/PL93399B1/pl unknown
- 1974-08-29 CH CH1178674A patent/CH606042A5/xx not_active IP Right Cessation
- 1974-08-29 TR TR18078A patent/TR18078A/xx unknown
- 1974-08-29 LU LU70821A patent/LU70821A1/xx unknown
- 1974-08-29 FI FI2533/74A patent/FI253374A/fi unknown
- 1974-08-30 DK DK461874A patent/DK136368C/da active
- 1974-08-30 ES ES429674A patent/ES429674A1/es not_active Expired
- 1974-08-30 CA CA208,171A patent/CA1027565A/en not_active Expired
- 1974-08-30 CS CS746012A patent/CS188925B2/cs unknown
- 1974-08-30 GB GB38004/74A patent/GB1483531A/en not_active Expired
- 1974-08-30 ZA ZA00745545A patent/ZA745545B/xx unknown
- 1974-08-30 DD DD180832A patent/DD114818A5/xx unknown
- 1974-08-30 FR FR7429764A patent/FR2242396B1/fr not_active Expired
- 1974-08-30 HU HUBA3136A patent/HU169164B/hu unknown
- 1974-08-30 BR BR7284/74A patent/BR7407284D0/pt unknown

Also Published As

Publication number	Publication date
IL45560A (en)	1979-09-30
TR18078A (tr)	1976-09-21
DK136368C (da)	1978-02-27
ATA699474A (de)	1975-02-15
AT326147B (de)	1975-11-25
GB1483531A (en)	1977-08-24
AU7262674A (en)	1976-02-26
RO65813A (fr)	1980-01-15
JPS5049431A (ro)	1975-05-02
PL97978B1 (pl)	1978-04-29
BE819278A (fr)	1975-02-28
CH606042A5 (ro)	1978-10-13
FR2242396A1 (ro)	1975-03-28
SU529802A3 (ru)	1976-09-25
DE2343931A1 (de)	1975-04-03
EG11113A (en)	1977-03-31
IL45560A0 (en)	1974-11-29
BR7407284D0 (pt)	1975-06-24
DD114818A5 (ro)	1975-08-20
PL93399B1 (ro)	1977-05-30
FI253374A (ro)	1975-03-01
LU70821A1 (ro)	1975-06-11
NL7411460A (nl)	1975-03-04
CS188925B2 (en)	1979-03-30
HU169164B (ro)	1976-10-28
JPS5050382A (ro)	1975-05-06
US3966730A (en)	1976-06-29
SE409208B (sv)	1979-08-06
DK461874A (ro)	1975-04-28
ZA745545B (en)	1975-08-27
ES429674A1 (es)	1976-10-01
DK136368B (da)	1977-10-03
SE7410957L (ro)	1975-03-03
AR209594A1 (es)	1977-05-13
CA1027565A (en)	1978-03-07
FR2242396B1 (ro)	1979-01-05

Publication	Publication Date	Title
US3591662A (en)	1971-07-06	Phosphorus containing alpha oximino acetic acid nitriles
NO742928L (ro)	1975-03-24
NO752789L (ro)	1976-02-25
DE2144392A1 (de)	1973-03-08	0-pyrimidyl-(thiono)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
US3914243A (en)	1975-10-21	O-alkyl-o-{8 7-substituted-benzisoxazol(3)yl{9 -(thiono)-phosphoric (phosphonic) acid esters
US3954755A (en)	1976-05-04	7-Bromoquinoxal-6-yl-(thiono)-(thiol)-phosphoric and (phosphonic) acid esters of ester-amides
US3761479A (en)	1973-09-25	O-pyrazolo-pyrimidine-(thiono)-phosphoric (phosphonic) acid esters
US3749720A (en)	1973-07-31	Pyridazinothionophosphoric (phosphonic) acid esters
US3894020A (en)	1975-07-08	3,4,-Dihydro-4-oxo-quinazolin (3)-yl-(thiono)-phosphoric (phosphonic) acid esters
DE2527676A1 (de)	1977-01-20	Triazolylmethylthiol(thiono)phosphor(phosphon)-saeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide, akarizide und nematizide
US3950337A (en)	1976-04-13	O-pyrazolopyrimidine-(thiono)-phosphoric(phosphonic) acid esters
US3981993A (en)	1976-09-21	O-Alkyl-O-n-propyl-O-pyrimidin(2)yl-thiono-phosphoric acid esters
NO744207L (ro)	1975-07-07
DE2304062A1 (de)	1974-08-01	0-aryl-thionoalkanphosphonsaeureesterimidderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide
US4233293A (en)	1980-11-11	Insecticidal and acaricidal O-alkyl-O-[1-(2-cyanoalkyl)-5-halo-1,2,4-triazol(3)yl]-(thiono)(thiol)-phosphoric(phosphonic) acid esters and ester-amides
US4000268A (en)	1976-12-28	N,N-dimethyl-N'-[O-phenyl-(thiono)-alkane-phosphonyl]-formamidines
US4127653A (en)	1978-11-28	O-alkyl-6-chloro-benzisoxazol-(3)-yl-thionophosphoric (phosphonic) acid esters
US3862271A (en)	1975-01-21	O-alkyl-(thiono) thiol-s-(s-alkylmercapto-s-benzylmercapto-methyl)-phosphoric (phosphonic) acid esters
US4112081A (en)	1978-09-05	O,O-Di-alkyl-O-(1-6-pyridazinon-3-yl)-(thiono)-phosphoric acid esters and their pesticidal use
PL93826B1 (ro)	1977-06-30
US3819753A (en)	1974-06-25	O-vinyl-thionophosphoric(-phosphonic)acid esters
DE2424571A1 (de)	1975-12-04	S-triazolopyridinmethyl-thiolo(thion)phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
IL46688A (en)	1977-04-29	Thionophosphoric acid esters their preparation and their use as insecticides and acaricides
US4035382A (en)	1977-07-12	O-alkyl-O-[5- methyl-7-halo-benzisoxazol (3)yl]-thiono-(thiol)-phosphoric (phosphonic) acid esters and ester amides
NO744196L (ro)	1975-06-30