HU184221B - Insecticide compositions containing 1-/phenyl-carbamoyl/-imida zoline derivatives as active substances and process for preparing the 1-/phenyl-carbamoyl/-imidazoline derivatives - Google Patents

Insecticide compositions containing 1-/phenyl-carbamoyl/-imida zoline derivatives as active substances and process for preparing the 1-/phenyl-carbamoyl/-imidazoline derivatives Download PDF

Info

Publication number: HU184221B
Authority: HU; Hungary
Prior art keywords: formula; imidazoline; oxygen; carbamoyl; iii
Prior art date: 1978-06-19

Application number

HU79WE601A

Other languages

English (en)

Hungarian (hu)

Inventor

David Collard

Frederick Ch Copp

Alexander D Frenkel

Peter T Roberts

Original Assignee

Wellcome Found

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.)

1978-06-19

Filing date

1979-06-19

Publication date

1984-07-30

1979-06-19 Application filed by Wellcome Found filed Critical Wellcome Found

1984-07-30 Publication of HU184221B publication Critical patent/HU184221B/hu

Links

239000000203 mixture Substances 0.000 title claims abstract description 37
239000013543 active substance Substances 0.000 title claims description 5
229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 title description 4
239000002917 insecticide Substances 0.000 title 1
238000004519 manufacturing process Methods 0.000 title 1
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
238000002360 preparation method Methods 0.000 claims abstract description 12
150000002462 imidazolines Chemical class 0.000 claims abstract description 9
229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims abstract description 7
229910052794 bromium Inorganic materials 0.000 claims abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
229910052740 iodine Inorganic materials 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 26
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
RUEDHJBESDYILP-UHFFFAOYSA-N n-phenyl-4,5-dihydroimidazole-1-carboxamide Chemical class C1CN=CN1C(=O)NC1=CC=CC=C1 RUEDHJBESDYILP-UHFFFAOYSA-N 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
239000012948 isocyanate Substances 0.000 claims description 7
150000002513 isocyanates Chemical class 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
125000000129 anionic group Chemical group 0.000 claims description 2
239000003945 anionic surfactant Substances 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
239000002736 nonionic surfactant Substances 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
125000001246 bromo group Chemical group Br* 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
238000009472 formulation Methods 0.000 abstract description 21
241000238876 Acari Species 0.000 abstract description 6
241000238421 Arthropoda Species 0.000 abstract description 5
125000004432 carbon atom Chemical group C* 0.000 abstract description 4
238000007792 addition Methods 0.000 abstract description 3
150000003839 salts Chemical class 0.000 abstract description 3
239000002253 acid Substances 0.000 abstract description 2
230000000361 pesticidal effect Effects 0.000 abstract 3
239000000575 pesticide Substances 0.000 abstract 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
229910052739 hydrogen Inorganic materials 0.000 abstract 1
239000001257 hydrogen Substances 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
WAAAGQHQBWTGTM-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydro-1h-imidazole Chemical class CC1=CC=CC(OCC=2NCCN=2)=C1C WAAAGQHQBWTGTM-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000010790 dilution Methods 0.000 description 6
239000012895 dilution Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 5
239000002585 base Substances 0.000 description 5
-1 bromo, fluoroiodo Chemical group 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
241000238631 Hexapoda Species 0.000 description 4
238000005507 spraying Methods 0.000 description 4
OBTMPVYDTRKARD-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-n-(4-methoxyphenyl)-4,5-dihydroimidazole-1-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)N1C(COC=2C(=C(C)C=CC=2)C)=NCC1 OBTMPVYDTRKARD-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
241000607479 Yersinia pestis Species 0.000 description 3
238000007654 immersion Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000003960 organic solvent 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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000238680 Rhipicephalus microplus 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
239000007900 aqueous suspension Substances 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000003925 fat Substances 0.000 description 2
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
WLUCWSITOBZYRR-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-ylmethyl)-2,3-dimethylaniline Chemical class CC1=CC=CC(NCC=2NCCN=2)=C1C WLUCWSITOBZYRR-UHFFFAOYSA-N 0.000 description 2
GIBUUMBLBQUETG-UHFFFAOYSA-N n-(4-bromophenyl)-2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical compound CC1=CC=CC(OCC=2N(CCN=2)C(=O)NC=2C=CC(Br)=CC=2)=C1C GIBUUMBLBQUETG-UHFFFAOYSA-N 0.000 description 2
JGEBJBFRPSPWHR-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[(2,3-dimethylanilino)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical compound CC1=CC=CC(NCC=2N(CCN=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1C JGEBJBFRPSPWHR-UHFFFAOYSA-N 0.000 description 2
230000017448 oviposition Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
VYKNVAHOUNIVTQ-UHFFFAOYSA-N 1,2,2,3,3-pentamethylpiperidine Chemical compound CN1CCCC(C)(C)C1(C)C VYKNVAHOUNIVTQ-UHFFFAOYSA-N 0.000 description 1
YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 1
CZQIJQFTRGDODI-UHFFFAOYSA-N 1-bromo-4-isocyanatobenzene Chemical compound BrC1=CC=C(N=C=O)C=C1 CZQIJQFTRGDODI-UHFFFAOYSA-N 0.000 description 1
ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 description 1
PWEFJXHAOIJFNO-UHFFFAOYSA-N 2-[(2,3-dimethylanilino)methyl]-N-(4-methylphenyl)-4,5-dihydroimidazole-1-carboxamide Chemical compound CC1=CC=C(C=C1)NC(=O)N1C(=NCC1)CNC1=C(C(=CC=C1)C)C PWEFJXHAOIJFNO-UHFFFAOYSA-N 0.000 description 1
KLLAGQLUIGVWEB-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydro-1H-imidazole hydrate Chemical compound O.CC1=CC=CC(OCC=2NCCN=2)=C1C KLLAGQLUIGVWEB-UHFFFAOYSA-N 0.000 description 1
UNGNCSGRWHERGP-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-n-(4-fluorophenyl)-4,5-dihydroimidazole-1-carboxamide Chemical compound CC1=CC=CC(OCC=2N(CCN=2)C(=O)NC=2C=CC(F)=CC=2)=C1C UNGNCSGRWHERGP-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241001480736 Amblyomma hebraeum Species 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
NZCCHKPAMIQOJJ-UHFFFAOYSA-N N-(4-bromophenyl)-2-[(2,3-dimethylanilino)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical compound BrC1=CC=C(C=C1)NC(=O)N1C(=NCC1)CNC1=C(C(=CC=C1)C)C NZCCHKPAMIQOJJ-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
241001649230 Psoroptes ovis Species 0.000 description 1
241001481704 Rhipicephalus appendiculatus Species 0.000 description 1
241000864246 Rhipicephalus decoloratus Species 0.000 description 1
241000864202 Rhipicephalus evertsi Species 0.000 description 1
241001454294 Tetranychus Species 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
239000002390 adhesive tape 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
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000010410 dusting Methods 0.000 description 1
244000078703 ectoparasite Species 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
NNHREFKAXJZADC-UHFFFAOYSA-N ethyl 4-[[2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazole-1-carbonyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC(=O)N1C(COC=2C(=C(C)C=CC=2)C)=NCC1 NNHREFKAXJZADC-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
YENCJCFCSPYZRS-UHFFFAOYSA-N n-(4-bromophenyl)-2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazole-1-carboxamide;hydrate Chemical compound O.CC1=CC=CC(OCC=2N(CCN=2)C(=O)NC=2C=CC(Br)=CC=2)=C1C YENCJCFCSPYZRS-UHFFFAOYSA-N 0.000 description 1
NRIWPNBCXDJQET-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical group CC1=CC=CC(OCC=2N(CCN=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1C NRIWPNBCXDJQET-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
239000004540 pour-on Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000005199 trimethylbenzenes Chemical class 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- 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<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

HU79WE601A 1978-06-19 1979-06-19 Insecticide compositions containing 1-/phenyl-carbamoyl/-imida zoline derivatives as active substances and process for preparing the 1-/phenyl-carbamoyl/-imidazoline derivatives HU184221B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB7827295		1978-06-19

Publications (1)

Publication Number	Publication Date
HU184221B true HU184221B (en)	1984-07-30

Family

ID=10498035

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU79WE601A HU184221B (en)	1978-06-19	1979-06-19	Insecticide compositions containing 1-/phenyl-carbamoyl/-imida zoline derivatives as active substances and process for preparing the 1-/phenyl-carbamoyl/-imidazoline derivatives

Country Status (21)

Country	Link
JP (1)	JPS554389A (da)
AR (1)	AR228841A1 (da)
AU (1)	AU525698B2 (da)
BE (1)	BE877094R (da)
BR (1)	BR7903857A (da)
CA (1)	CA1108621A (da)
CH (1)	CH643544A5 (da)
DE (1)	DE2924715A1 (da)
DK (1)	DK255879A (da)
ES (3)	ES481670A2 (da)
FR (1)	FR2429206A2 (da)
HU (1)	HU184221B (da)
IE (1)	IE48760B1 (da)
IT (1)	IT1162645B (da)
LU (1)	LU81394A1 (da)
MW (1)	MW1679A1 (da)
NL (1)	NL7904810A (da)
SE (1)	SE444936B (da)
ZA (1)	ZA787351B (da)
ZM (1)	ZM5379A1 (da)
ZW (1)	ZW12079A1 (da)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH529766A (de) *	1967-02-23	1972-10-31	Horst Prof Baganz	Verfahren zur Herstellung von Aryloxy-isoalkyl- 2-imidazolinen
GB1469772A (en) *	1973-06-21	1977-04-06	Boots Co Ltd	Fungicidal imidazole derivatives
GB1486192A (en) *	1973-11-19	1977-09-21	Boots Co Ltd	Imidazole derivatives
NL7712401A (nl) *	1976-11-16	1978-05-18	Ciba Geigy	Werkwijze voor het bereiden van preparaten voor het bestrijden van schadelijke organismen.
AU521328B2 (en) *	1976-12-20	1982-03-25	Wellcome Foundation Limited, The	Imidazolines
JPS5484575A (en) *	1977-10-26	1979-07-05	Wellcome Found	Imidazoline compound*its manufacture and insecticide composition

1978
- 1978-12-28 ZA ZA787351A patent/ZA787351B/xx unknown
1979
- 1979-06-16 ZM ZM53/79A patent/ZM5379A1/xx unknown
- 1979-06-18 LU LU81394A patent/LU81394A1/fr unknown
- 1979-06-19 JP JP7746379A patent/JPS554389A/ja active Granted
- 1979-06-19 AR AR276980A patent/AR228841A1/es active
- 1979-06-19 IT IT49462/79A patent/IT1162645B/it active
- 1979-06-19 HU HU79WE601A patent/HU184221B/hu not_active IP Right Cessation
- 1979-06-19 AU AU48201/79A patent/AU525698B2/en not_active Expired
- 1979-06-19 MW MW16/79A patent/MW1679A1/xx unknown
- 1979-06-19 CA CA330,075A patent/CA1108621A/en not_active Expired
- 1979-06-19 ZW ZW120/79A patent/ZW12079A1/xx unknown
- 1979-06-19 SE SE7905374A patent/SE444936B/sv not_active IP Right Cessation
- 1979-06-19 FR FR7915663A patent/FR2429206A2/fr active Granted
- 1979-06-19 BR BR7903857A patent/BR7903857A/pt unknown
- 1979-06-19 DE DE19792924715 patent/DE2924715A1/de not_active Ceased
- 1979-06-19 CH CH571779A patent/CH643544A5/de not_active IP Right Cessation
- 1979-06-19 ES ES481670A patent/ES481670A2/es not_active Expired
- 1979-06-19 NL NL7904810A patent/NL7904810A/xx not_active Application Discontinuation
- 1979-06-19 BE BE0/195834A patent/BE877094R/xx not_active IP Right Cessation
- 1979-06-19 DK DK255879A patent/DK255879A/da not_active Application Discontinuation
- 1979-08-08 IE IE1153/79A patent/IE48760B1/en unknown
1980
- 1980-03-17 ES ES489642A patent/ES8400413A2/es not_active Expired
- 1980-03-17 ES ES489641A patent/ES8104240A1/es not_active Expired

Also Published As

Publication number	Publication date
NL7904810A (nl)	1979-12-21
ZW12079A1 (en)	1981-01-21
IT1162645B (it)	1987-04-01
DE2924715A1 (de)	1980-01-03
ES481670A2 (es)	1980-06-16
FR2429206A2 (fr)	1980-01-18
AU525698B2 (en)	1982-11-25
ES489641A0 (es)	1981-04-01
ZM5379A1 (en)	1981-07-21
FR2429206B2 (da)	1983-06-03
CA1108621A (en)	1981-09-08
BR7903857A (pt)	1980-03-04
DK255879A (da)	1979-12-20
LU81394A1 (fr)	1980-01-22
ES489642A0 (es)	1983-10-16
ZA787351B (en)	1980-08-27
SE444936B (sv)	1986-05-20
SE7905374L (sv)	1979-12-20
IE48760B1 (en)	1985-05-15
IT7949462A0 (it)	1979-06-19
AR228841A1 (es)	1983-04-29
ES8400413A2 (es)	1983-10-16
IE791153L (en)	1979-12-19
MW1679A1 (en)	1981-04-08
JPS623836B2 (da)	1987-01-27
ES8104240A1 (es)	1981-04-01
JPS554389A (en)	1980-01-12
CH643544A5 (en)	1984-06-15
AU4820179A (en)	1980-03-20
BE877094R (fr)	1979-12-19

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628
1991-05-28	HMM4	Cancellation of final prot. due to non-payment of fee

Publication	Publication Date	Title
US4238497A (en)	1980-12-09	Imidazoline derivatives, salts thereof and their use as pesticides
US5134145A (en)	1992-07-28	Pesticidal pyrimidinyl benzoic acids and esters
DE1817879C3 (de)	1974-07-11	l-(N-Äthoxycarbonyl-N'-thioureido)-2-(N-methoxycarbonyl-N'-thioureido) benzol, seine Herstellung und seine Verwendung als Fungicid. Ausscheidung aus: 1806123
US3674874A (en)	1972-07-04	Insecticidal and acaricidal compositions
US4226876A (en)	1980-10-07	Arthropodicidal imidazoline derivatives
US4414223A (en)	1983-11-08	Pesticidal anilinomethylimidazolines
US4863966A (en)	1989-09-05	Pesticidal amines
CS246090B2 (en)	1986-10-16	Insecticide and method of its efficient component production
HU184221B (en)	1984-07-30	Insecticide compositions containing 1-/phenyl-carbamoyl/-imida zoline derivatives as active substances and process for preparing the 1-/phenyl-carbamoyl/-imidazoline derivatives
US4320142A (en)	1982-03-16	N-[(phenyl(oxy or amino))thioacetyl]-1,2-diamine anthropodicides
IE58812B1 (en)	1993-11-17	Imidazole derivatives, their preparation and their use as fungicides
US3772320A (en)	1973-11-13	N1-sulfonyl-2-phenylhydrazino-2-imidazolines
US4254133A (en)	1981-03-03	Combatting ectoparasites with phenylaminoalkyl-2-imidazoline compounds
US4011343A (en)	1977-03-08	Triazapentadienes as acaricides and insecticides
US3799921A (en)	1974-03-26	N1-acyl-2-phenylhydrazino-2-imidazolines and processes for their preparation and use
DE3311636A1 (de)	1984-10-04	Neue fuenfgliedrige stickstoffhaltige heterocyclen, verfahren zu ihrer herstellung sowie ihre verwendung als schaedlingsbekaempfungsmittel
EP0073960A1 (de)	1983-03-16	2-Arylhydrazino-2-imidazoline, deren Acylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Endo- und Ektoparasiten
IE46119B1 (en)	1983-02-23	Imidazoline derivatives and their use as pesticides
US3953447A (en)	1976-04-27	Esterified 2-amino pyrimidine derivatives
CS264299B2 (en)	1989-06-13	Insecticide and acaricide and process for preparing active component
US3962442A (en)	1976-06-08	Fungicidal compositions containing 2-amino pyrimidines and methods of using the same
GB2055092A (en)	1981-02-25	Novel thioamide pesticides, preparation and use
US4489083A (en)	1984-12-18	Phenyl imidazole derivatives
IL26979A (en)	1970-08-19	4-phosphinothioyl-1,3,4-thiadiazol-5(4h)-one derivatives and pesticidal compositions containing them
HU176496B (en)	1981-03-28	Insecticides and acaricides containing substituted 1-phenyl-3-penyl-2-trichloromethyl-imidazolidines and process for prenaring the active materials thereof