NL8105127A - Acylureumverbindingen, deze verbindingen bevattende insecticiden, alsmede werkwijze voor het bereiden van deze verbindingen. - Google Patents

Acylureumverbindingen, deze verbindingen bevattende insecticiden, alsmede werkwijze voor het bereiden van deze verbindingen. Download PDF

Info

Publication number: NL8105127A
Authority: NL; Netherlands
Prior art keywords: urea; phenyl; compounds; methyl; dichloro
Prior art date: 1980-12-08

Application number

NL8105127A

Other languages

English (en)

Dutch (nl)

Original Assignee

Schering 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.)

1980-12-08

Filing date

1981-11-12

Publication date

1982-07-01

1981-11-12 Application filed by Schering Ag filed Critical Schering Ag

1982-07-01 Publication of NL8105127A publication Critical patent/NL8105127A/nl

Links

150000001875 compounds Chemical class 0.000 title claims description 44
238000000034 method Methods 0.000 title claims description 18
-1 Acylurea compounds Chemical class 0.000 claims description 47
239000004202 carbamide Substances 0.000 claims description 27
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
239000002917 insecticide Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
230000000749 insecticidal effect Effects 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
229940054066 benzamide antipsychotics Drugs 0.000 claims description 3
150000003936 benzamides Chemical class 0.000 claims description 3
239000012948 isocyanate Substances 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
XIWRCSVXKPGGAJ-UHFFFAOYSA-N 1-(5-tert-butyl-2-phenylpyrazol-3-yl)-3-(4-chlorophenyl)urea Chemical compound C=1C=CC=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC=C(Cl)C=C1 XIWRCSVXKPGGAJ-UHFFFAOYSA-N 0.000 claims 1
AJXYSUNGXJFJTE-UHFFFAOYSA-N 2-chloro-n-[[4-(2,2-dichlorocyclopropyl)oxyphenyl]carbamoyl]benzamide Chemical compound ClC1=CC=CC=C1C(=O)NC(=O)NC(C=C1)=CC=C1OC1C(Cl)(Cl)C1 AJXYSUNGXJFJTE-UHFFFAOYSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000011521 glass Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
230000000694 effects Effects 0.000 description 5
230000008569 process Effects 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 4
239000000969 carrier Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
241000462639 Epilachna varivestis Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
159000000007 calcium salts Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
229920005610 lignin Polymers 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000002828 nitro derivatives Chemical class 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000254173 Coleoptera Species 0.000 description 2
241000238631 Hexapoda Species 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
241000500437 Plutella xylostella Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
241000607479 Yersinia pestis Species 0.000 description 2
WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical class O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
210000000988 bone and bone Anatomy 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000002734 clay mineral Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical class Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
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 2
230000001418 larval effect Effects 0.000 description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
HYRFBZQNFPRBBS-UHFFFAOYSA-N n-carbamoyl-2,6-dichlorobenzamide Chemical compound NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl HYRFBZQNFPRBBS-UHFFFAOYSA-N 0.000 description 2
210000002741 palatine tonsil Anatomy 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
229920000151 polyglycol Polymers 0.000 description 2
239000010695 polyglycol Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
FOZVXADQAHVUSV-UHFFFAOYSA-N 1-bromo-2-(2-bromoethoxy)ethane Chemical compound BrCCOCCBr FOZVXADQAHVUSV-UHFFFAOYSA-N 0.000 description 1
DIVIIFDAYPYCMH-UHFFFAOYSA-N 1-cyclopropyloxy-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1CC1 DIVIIFDAYPYCMH-UHFFFAOYSA-N 0.000 description 1
125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 0.000 description 1
JACPTQMMZGZAOL-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCN(C)CCS(O)(=O)=O JACPTQMMZGZAOL-KHPPLWFESA-N 0.000 description 1
RZMVHCYCUAKRMM-UHFFFAOYSA-N 2-methylbenzoyl isocyanate Chemical compound CC1=CC=CC=C1C(=O)N=C=O RZMVHCYCUAKRMM-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 1
240000003259 Brassica oleracea var. botrytis Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
241000255925 Diptera Species 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
235000019738 Limestone Nutrition 0.000 description 1
150000007945 N-acyl ureas Chemical class 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
125000005036 alkoxyphenyl group Chemical group 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
230000012447 hatching Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000006028 limestone Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PPOSFCNLNROPTA-UHFFFAOYSA-N n-carbamoyl-2,6-difluorobenzamide Chemical compound NC(=O)NC(=O)C1=C(F)C=CC=C1F PPOSFCNLNROPTA-UHFFFAOYSA-N 0.000 description 1
VVFYDOYJKGPHFW-UHFFFAOYSA-N n-carbamoyl-2-fluorobenzamide Chemical compound NC(=O)NC(=O)C1=CC=CC=C1F VVFYDOYJKGPHFW-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
238000010926 purge Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

NL8105127A 1980-12-08 1981-11-12 Acylureumverbindingen, deze verbindingen bevattende insecticiden, alsmede werkwijze voor het bereiden van deze verbindingen. NL8105127A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19803046672 DE3046672A1 (de)	1980-12-08	1980-12-08	Acylharnstoffe, insektizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung
DE3046672		1980-12-08

Publications (1)

Publication Number	Publication Date
NL8105127A true NL8105127A (nl)	1982-07-01

Family

ID=6118899

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8105127A NL8105127A (nl)	1980-12-08	1981-11-12	Acylureumverbindingen, deze verbindingen bevattende insecticiden, alsmede werkwijze voor het bereiden van deze verbindingen.

Country Status (38)

Country	Link
US (1)	US4472434A (fr)
JP (1)	JPS599545B2 (fr)
AR (1)	AR229036A1 (fr)
AT (1)	AT376357B (fr)
AU (1)	AU546227B2 (fr)
BE (1)	BE891381A (fr)
BR (1)	BR8107927A (fr)
CA (1)	CA1176658A (fr)
CH (1)	CH647754A5 (fr)
CS (1)	CS221997B2 (fr)
DD (1)	DD201843A5 (fr)
DE (1)	DE3046672A1 (fr)
DK (1)	DK508481A (fr)
EG (1)	EG15299A (fr)
ES (1)	ES507468A0 (fr)
FI (1)	FI71730C (fr)
FR (1)	FR2495609A1 (fr)
GB (1)	GB2091245B (fr)
GR (1)	GR76376B (fr)
HU (1)	HU188306B (fr)
IE (1)	IE51860B1 (fr)
IL (1)	IL64416A (fr)
IN (1)	IN157780B (fr)
IT (1)	IT1169284B (fr)
LU (1)	LU83815A1 (fr)
MA (1)	MA19354A1 (fr)
MX (1)	MX6699E (fr)
NL (1)	NL8105127A (fr)
NZ (1)	NZ198997A (fr)
PH (1)	PH18250A (fr)
PL (1)	PL129600B1 (fr)
PT (1)	PT74096B (fr)
RO (1)	RO84236B (fr)
SE (1)	SE8107235L (fr)
SU (2)	SU1097193A3 (fr)
TR (1)	TR20873A (fr)
YU (1)	YU277781A (fr)
ZA (1)	ZA818522B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5245071A (en) *	1970-05-15	1993-09-14	Duphar International Research B.V.	Organic compounds derived from urea or thiourea
NL160809C (nl) *	1970-05-15	1979-12-17	Duphar Int Res	Werkwijze ter bereiding van benzoylureumverbindingen, alsmede werkwijze ter bereiding van insekticide prepara- ten op basis van benzoylureumverbindingen.
US5342958A (en) *	1970-05-15	1994-08-30	Solvay Duphar International Research B.V.	Organic compounds derived from urea or thiourea
EP0131071B1 (fr) *	1983-01-24	1987-05-13	Duphar International Research B.V	Dérivés de benzoylurées et les compositions pesticides et pharmaceutiques renfermant ces composés
US4783485A (en) *	1983-01-24	1988-11-08	Duphar International Research B.V.	Benzoylurea compounds, and insecticidal and acaricidal compositions comprising same
ATE40111T1 (de) *	1984-07-05	1989-02-15	Duphar Int Res	Benzoylharnstoffverbindungen sowie solche enthaltende insektizide und akarizide zusammensetzungen.
DE3504749A1 (de) *	1985-02-08	1986-08-14	Schering AG, 1000 Berlin und 4709 Bergkamen	Acylharnstoffe, insektizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung
EP0190611A3 (fr) *	1985-02-08	1987-02-04	Schering Aktiengesellschaft	Acylurées, leurs compositions insecticides et leurs procédés de préparation

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL160809C (nl)	1970-05-15	1979-12-17	Duphar Int Res	Werkwijze ter bereiding van benzoylureumverbindingen, alsmede werkwijze ter bereiding van insekticide prepara- ten op basis van benzoylureumverbindingen.
US4170657A (en) *	1977-05-13	1979-10-09	The Dow Chemical Company	Substituted(((phenyl)amino)carbonyl)-benzamides
DE2804739A1 (de) *	1978-02-02	1979-08-09	Schering Ag	Phenylharnstoff-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes selektives herbizides mittel
DE2928410A1 (de) *	1979-07-11	1981-01-29	Schering Ag	Acylharnstoffe, insektizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung
JPS56135456A (en) *	1980-03-27	1981-10-22	Sumitomo Chem Co Ltd	Substituted phenylurea derivative, its preparation and herbicide containing the same as active constituent

1980
- 1980-12-08 DE DE19803046672 patent/DE3046672A1/de not_active Withdrawn
1981
- 1981-11-12 NL NL8105127A patent/NL8105127A/nl not_active Application Discontinuation
- 1981-11-13 IN IN713/DEL/81A patent/IN157780B/en unknown
- 1981-11-17 FI FI813643A patent/FI71730C/fi not_active IP Right Cessation
- 1981-11-17 DK DK508481A patent/DK508481A/da not_active Application Discontinuation
- 1981-11-19 NZ NZ198997A patent/NZ198997A/en unknown
- 1981-11-25 CH CH7546/81A patent/CH647754A5/de not_active IP Right Cessation
- 1981-11-26 ES ES507468A patent/ES507468A0/es active Granted
- 1981-11-26 YU YU02777/81A patent/YU277781A/xx unknown
- 1981-11-27 AT AT0512181A patent/AT376357B/de not_active IP Right Cessation
- 1981-11-30 CS CS818860A patent/CS221997B2/cs unknown
- 1981-11-30 GB GB8136059A patent/GB2091245B/en not_active Expired
- 1981-11-30 US US06/325,842 patent/US4472434A/en not_active Expired - Fee Related
- 1981-12-01 IL IL64416A patent/IL64416A/xx unknown
- 1981-12-02 FR FR8122549A patent/FR2495609A1/fr active Granted
- 1981-12-02 CA CA000391383A patent/CA1176658A/fr not_active Expired
- 1981-12-02 DD DD81235334A patent/DD201843A5/de unknown
- 1981-12-02 IT IT25399/81A patent/IT1169284B/it active
- 1981-12-03 AR AR287684A patent/AR229036A1/es active
- 1981-12-03 SE SE8107235A patent/SE8107235L/ not_active Application Discontinuation
- 1981-12-03 SU SU813363104A patent/SU1097193A3/ru active
- 1981-12-03 SU SU813359633A patent/SU1210651A3/ru active
- 1981-12-04 TR TR20873A patent/TR20873A/xx unknown
- 1981-12-04 MX MX819800U patent/MX6699E/es unknown
- 1981-12-04 LU LU83815A patent/LU83815A1/de unknown
- 1981-12-04 PL PL1981234091A patent/PL129600B1/pl unknown
- 1981-12-07 PT PT74096A patent/PT74096B/pt unknown
- 1981-12-07 HU HU813683A patent/HU188306B/hu unknown
- 1981-12-07 BE BE0/206762A patent/BE891381A/fr not_active IP Right Cessation
- 1981-12-07 BR BR8107927A patent/BR8107927A/pt unknown
- 1981-12-07 EG EG716/81A patent/EG15299A/xx active
- 1981-12-07 GR GR66716A patent/GR76376B/el unknown
- 1981-12-07 JP JP56195752A patent/JPS599545B2/ja not_active Expired
- 1981-12-07 RO RO105936A patent/RO84236B/ro unknown
- 1981-12-07 MA MA19558A patent/MA19354A1/fr unknown
- 1981-12-07 AU AU78316/81A patent/AU546227B2/en not_active Ceased
- 1981-12-08 IE IE2878/81A patent/IE51860B1/en unknown
- 1981-12-08 ZA ZA818522A patent/ZA818522B/xx unknown
- 1981-12-08 PH PH26600A patent/PH18250A/en unknown

Also Published As

Publication number	Publication date
JPS599545B2 (ja)	1984-03-03
PH18250A (en)	1985-05-03
FI813643L (fi)	1982-06-09
ES8206454A1 (es)	1982-09-01
RO84236A (fr)	1984-05-23
IN157780B (fr)	1986-06-14
PL234091A1 (en)	1983-01-31
IL64416A0 (en)	1982-03-31
FI71730B (fi)	1986-10-31
RO84236B (ro)	1984-07-30
SU1097193A3 (ru)	1984-06-07
GR76376B (fr)	1984-08-06
DK508481A (da)	1982-06-09
GB2091245B (en)	1984-08-22
IE51860B1 (en)	1987-04-15
US4472434A (en)	1984-09-18
MX6699E (es)	1985-10-21
AU546227B2 (en)	1985-08-22
BR8107927A (pt)	1982-09-14
SU1210651A3 (ru)	1986-02-07
IT8125399A0 (it)	1981-12-02
ATA512181A (de)	1984-04-15
SE8107235L (sv)	1982-06-09
CS221997B2 (en)	1983-04-29
DE3046672A1 (de)	1982-07-08
YU277781A (en)	1983-09-30
AT376357B (de)	1984-11-12
NZ198997A (en)	1984-03-16
IL64416A (en)	1984-12-31
BE891381A (fr)	1982-06-07
TR20873A (tr)	1982-11-18
PT74096A (de)	1982-01-01
LU83815A1 (de)	1982-05-07
AU7831681A (en)	1982-06-17
CA1176658A (fr)	1984-10-23
EG15299A (en)	1986-12-30
CH647754A5 (de)	1985-02-15
FR2495609B1 (fr)	1984-05-18
MA19354A1 (fr)	1982-07-01
PL129600B1 (en)	1984-05-31
ES507468A0 (es)	1982-09-01
IE812878L (en)	1982-06-08
AR229036A1 (es)	1983-05-31
GB2091245A (en)	1982-07-28
HU188306B (en)	1986-04-28
ZA818522B (en)	1982-10-27
JPS57122057A (en)	1982-07-29
FR2495609A1 (fr)	1982-06-11
FI71730C (fi)	1987-02-09
DD201843A5 (de)	1983-08-17
PT74096B (de)	1983-05-11
IT1169284B (it)	1987-05-27

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1988-07-01	BV	The patent application has lapsed

Publication	Publication Date	Title
CA1179688A (fr)	1984-12-18	Phenyluree
CA1136647A (fr)	1982-11-30	Phenylurees
EP0116729B1 (fr)	1988-10-12	Dérivés de benzoylurées et les compositions pesticides renfermant ces composés
EP0194688B1 (fr)	1990-07-18	Benzoylurées à activité insecticide
CA1293264C (fr)	1991-12-17	Les n-benzoyl-n'-2,5-dihalo-4-perfluoroalkoxy-phenylurees, leur preparation etleur utilisation pour la lutte contre les parasites
CA1340467C (fr)	1999-03-30	Benzoylphenylurees; methode de preparation et utilisation comme produits antiparasitaires
FI71730B (fi)	1986-10-31	Acylurinaemnen insekticidaemnen som innehaoller dessa foereningar samt foerfarande foer deras framstaellning
CA1247609A (fr)	1988-12-28	Composes de benzoyluree et composes pesticides les contenant
JPH0637455B2 (ja)	1994-05-18	フェノキシフェニルチオ尿素、フェノキシフェニルイソチオ尿素およびフェノキシフェニルカルボジイミド、それらの中間体および製法
IE50005B1 (en)	1986-01-22	Insecticidally active acyl-ureas and their manufacture and use
EP0167197B1 (fr)	1989-01-18	Benzoylurées et compositions insecticides et acaricides les contenant
BG61199B2 (bg)	1997-02-28	Инсектицидно-активни (2,3-дихидро-2,2-диметилбензофуран-7-илокси-n- метилкарбамоил)-(n'-алкоксикарбамоил)-сулфиди
US4540578A (en)	1985-09-10	Pesticidal phenoxypyridyl benzoyl ureas
JPH0115502B2 (fr)	1989-03-17
US4602109A (en)	1986-07-22	Novel pesticidal phenoxyphenyl and phenoxypyridyl benzoyl ureas and process for preparation
US4098900A (en)	1978-07-04	N,N'-Diphenyl-guanidine derivatives
US4578402A (en)	1986-03-25	Pesticidal alpha-cyanobenzyl phenyl benzoyl urea compounds
EP0115210A1 (fr)	1984-08-08	Benzoyl uréas à activité pesticide et procédé pour leur préparation
CA1241005A (fr)	1988-08-23	Benzoylphenilurees
CA1185266A (fr)	1985-04-09	Derives de phenyluree
US3995063A (en)	1976-11-30	Insecticidal 1,1-diphenyl-2-nitroalkanes
DE3133009A1 (de)	1982-04-08	N-pyridinyl-n'-benzoylharnstoffe
JPS5835163A (ja)	1983-03-01	Ｎ−ベンゾイル−ｎ′−フエノキシフエニルウレア系化合物及びそれらを含有する殺虫剤
IL89101A (en)	1994-11-11	Derivatives of 1-benzoyl-3-trifluorophenylurea, their preparation and insecticidal compounds containing them
JPH0369338B2 (fr)	1991-10-31