JPS623836B2 - - Google Patents

Info

Publication number: JPS623836B2
Authority: JP; Japan
Prior art keywords: formula; compound; carbon atoms; acid addition; imidazoline
Prior art date: 1978-06-19
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP54077463A

Other languages

English (en)

Japanese (ja)

Other versions

JPS554389A (en

Inventor

Koraado Debitsudo

Chaaruzu Kotsupu Furederitsuku

Debitsudo Furenkeru Arekusandaa

Terensu Robaatsu Piitaa

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wellcome Foundation Ltd

Original Assignee

Wellcome Foundation Ltd

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

1987-01-27

1979-06-19 Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd

1980-01-12 Publication of JPS554389A publication Critical patent/JPS554389A/ja

1987-01-27 Publication of JPS623836B2 publication Critical patent/JPS623836B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 75
239000000203 mixture Substances 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 30
125000004432 carbon atom Chemical group C* 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 17
238000000034 method Methods 0.000 claims description 10
239000007788 liquid Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000000843 powder Substances 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
239000012458 free base Substances 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 4
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 claims description 4
239000004563 wettable powder Substances 0.000 claims description 4
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 claims description 3
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 claims description 3
NCWQZRJXZSACLY-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-n-(4-nitrophenyl)-4,5-dihydroimidazole-1-carboxamide Chemical compound CC1=CC=CC(OCC=2N(CCN=2)C(=O)NC=2C=CC(=CC=2)[N+]([O-])=O)=C1C NCWQZRJXZSACLY-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
239000007900 aqueous suspension Substances 0.000 claims description 3
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
229910052717 sulfur Chemical group 0.000 claims description 3
239000004094 surface-active agent Substances 0.000 claims description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000008187 granular material Substances 0.000 claims description 2
239000004519 grease Substances 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims 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 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims 1
239000013056 hazardous product Substances 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
239000000375 suspending agent Substances 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
238000009472 formulation Methods 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
239000000543 intermediate Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
-1 N-substituted carbamoyl compound Chemical class 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
239000002585 base Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
241000607479 Yersinia pestis Species 0.000 description 8
239000002609 medium Substances 0.000 description 8
241000238876 Acari Species 0.000 description 7
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
150000002462 imidazolines Chemical class 0.000 description 6
150000002825 nitriles Chemical class 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000000243 solution Substances 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
241000238421 Arthropoda Species 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
150000007513 acids Chemical class 0.000 description 3
150000001409 amidines Chemical class 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
238000007598 dipping method Methods 0.000 description 3
235000013601 eggs Nutrition 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
230000000749 insecticidal effect Effects 0.000 description 3
150000004682 monohydrates Chemical class 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000000376 reactant Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
238000005507 spraying Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
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 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241001481703 Rhipicephalus <genus> 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
241001454294 Tetranychus Species 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
235000019329 dioctyl sodium sulphosuccinate Nutrition 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
230000000694 effects Effects 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012433 hydrogen halide Substances 0.000 description 2
229910000039 hydrogen halide Inorganic materials 0.000 description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
239000004540 pour-on Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000007787 solid 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
XMWOQBUECCSBEN-UHFFFAOYSA-N 2-(2,3-dimethylphenoxy)-4,5-dihydro-1h-imidazole Chemical compound CC1=CC=CC(OC=2NCCN=2)=C1C XMWOQBUECCSBEN-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
WAAAGQHQBWTGTM-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydro-1h-imidazole Chemical compound CC1=CC=CC(OCC=2NCCN=2)=C1C WAAAGQHQBWTGTM-UHFFFAOYSA-N 0.000 description 1
HOJMLTAFTQLGBS-UHFFFAOYSA-N 2-[(2,3-dimethylphenoxy)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical compound C(N)(=O)N1C(=NCC1)COC1=C(C(=CC=C1)C)C HOJMLTAFTQLGBS-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
HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241001480736 Amblyomma hebraeum Species 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
229910021580 Cobalt(II) chloride Inorganic materials 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
241000403354 Microplus Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
UKOOUFDVPQZLBF-UHFFFAOYSA-N N-(4-cyanophenyl)-2-[(2,3-dimethylanilino)methyl]-4,5-dihydroimidazole-1-carboxamide Chemical compound C(#N)C1=CC=C(C=C1)NC(=O)N1C(=NCC1)CNC1=C(C(=CC=C1)C)C UKOOUFDVPQZLBF-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
229910019142 PO4 Inorganic materials 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
241001649230 Psoroptes ovis Species 0.000 description 1
241000864202 Rhipicephalus evertsi Species 0.000 description 1
241000238680 Rhipicephalus microplus Species 0.000 description 1
101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
239000000654 additive Substances 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
125000003545 alkoxy group Chemical group 0.000 description 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
230000003197 catalytic effect Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
244000078703 ectoparasite Species 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 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
239000007789 gas 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
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 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
238000002156 mixing Methods 0.000 description 1
125000005609 naphthenate group Chemical group 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003053 piperidines Chemical class 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
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
101150035983 str1 gene Proteins 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 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
239000002562 thickening agent Substances 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 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)

JP7746379A 1978-06-19 1979-06-19 Imidazoline derivative Granted JPS554389A (en)

Applications Claiming Priority (1)

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

Publications (2)

Publication Number	Publication Date
JPS554389A JPS554389A (en)	1980-01-12
JPS623836B2 true JPS623836B2 (da)	1987-01-27

Family

ID=10498035

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7746379A Granted JPS554389A (en)	1978-06-19	1979-06-19	Imidazoline derivative

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
HU184221B (en)	1984-07-30
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
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

Publication	Publication Date	Title
DE69304057T2 (de)	1997-02-06	Indole fungizide
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
US4226876A (en)	1980-10-07	Arthropodicidal imidazoline derivatives
EP0352581A2 (de)	1990-01-31	Aethylendiaminmonoamid-Derivate
US4414223A (en)	1983-11-08	Pesticidal anilinomethylimidazolines
JP3156268B2 (ja)	2001-04-16	イミノチアゾリン誘導体、その製造法、それを有効成分とする除草剤およびその製造中間体
DE2854598A1 (de)	1980-07-03	N-substituierte carbonsaeureanilide, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide
GB2023603A (en)	1980-01-03	Pesticidal imidazolines, and their preparation and use
EP0044497A2 (de)	1982-01-27	Verfahren zur Herstellung heterocyclisch substituierter 4-Oxiphenoxialkancarbonsäurederivate
US4233306A (en)	1980-11-11	1-Iminomethylene-substituted 2-(phenoxy-alkyl)-2-imidoazoline derivatives
JPS623836B2 (da)	1987-01-27
US4863966A (en)	1989-09-05	Pesticidal amines
GB1592649A (en)	1981-07-08	Imidazoline derivatives and their use as pesticides
MC1173A1 (fr)	1978-09-25	Imidazolines et leur emploi comme agents pesticides
US4874786A (en)	1989-10-17	Cyanoacetamido-derivatives having a fungicidal activity
US4011343A (en)	1977-03-08	Triazapentadienes as acaricides and insecticides
DE69131002T2 (de)	1999-09-30	Verfahren zur Herstellung von 2-Aryl-1-substituierten-5-(Trifluormethyl)-Pyrrolen als Insektizide, Akarizide und Nematizide Wirkstoffe sowie als Zwischenprodukte zur Herstellung dieser Wirkstoffe
JPH05279210A (ja)	1993-10-26	スルホンアミド除草剤
EP3486237B1 (en)	2019-12-11	Triazinone derivative containing sulfonyl structure and preparation method therefor, and insecticidal and bactericidal uses thereof
GB1593276A (en)	1981-07-15	Imidazoline derivatives and their use as pesticides
DE3630732A1 (de)	1988-03-17	2-cyano-2-alkoximino-acetamide
DE68919950T2 (de)	1995-06-22	S-(N-Alkoxycarbonyl, N-substituierte)aminomethylisothioharnstoff-Derivat.
EP0152129B1 (en)	1991-06-12	N-acyl amino acid derivatives, their preparation and their use as fungicides
CS208186B2 (en)	1981-08-31	Fungicide means and method of making active substances