CA1108621A - Pesticidal imidazolines - Google Patents

Pesticidal imidazolines

Info

Publication number: CA1108621A
Authority: CA; Canada
Prior art keywords: compound; formula; imidazoline; carbamoyl; acid addition
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

CA330,075A

Other languages

English (en)

French (fr)

Inventor

Frederick C. Copp

David Collard

Alexander D. Frenkel

Peter T. Roberts

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.)

Sanofi Aventis France

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

1981-09-08

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

1981-09-08 Application granted granted Critical

1981-09-08 Publication of CA1108621A publication Critical patent/CA1108621A/en

Status Expired legal-status Critical Current

Links

230000000361 pesticidal effect Effects 0.000 title abstract description 8
150000002462 imidazolines Chemical class 0.000 title abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 34
239000002253 acid Substances 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 20
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
241000238876 Acari Species 0.000 claims abstract description 9
241000238421 Arthropoda Species 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 76
238000006243 chemical reaction Methods 0.000 claims description 19
-1 ester amidine Chemical class 0.000 claims description 14
241000607479 Yersinia pestis Species 0.000 claims description 13
150000002825 nitriles Chemical class 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 4
238000007598 dipping method Methods 0.000 claims description 4
239000012458 free base Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
238000005507 spraying Methods 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 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 claims description 3
241000124008 Mammalia Species 0.000 claims description 2
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
239000005864 Sulphur Chemical group 0.000 claims description 2
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000005279 aryl sulfonyloxy group Chemical group 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
238000010410 dusting Methods 0.000 claims description 2
244000078703 ectoparasite Species 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
150000002905 orthoesters Chemical class 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
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 2
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 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 claims 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 claims 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 2
125000004423 acyloxy group Chemical group 0.000 claims 1
150000007970 thio esters Chemical class 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 20
238000007792 addition Methods 0.000 abstract description 18
238000009472 formulation Methods 0.000 abstract description 16
239000000543 intermediate Substances 0.000 abstract description 12
239000000575 pesticide Substances 0.000 abstract description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
239000002609 medium Substances 0.000 description 9
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 8
239000007788 liquid Substances 0.000 description 8
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
239000000843 powder Substances 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
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 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
150000001409 amidines Chemical class 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000003960 organic solvent Substances 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
238000003756 stirring Methods 0.000 description 3
239000004563 wettable powder Substances 0.000 description 3
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 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
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
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
239000004519 grease Substances 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
230000005764 inhibitory process Effects 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003921 oil Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
239000004540 pour-on Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000004094 surface-active agent 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
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
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 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
241000972142 Boophis <genus> Species 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
241000403354 Microplus Species 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-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
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
AEKNYBWUEYNWMJ-QWOOXDRHSA-N Pramiconazole Chemical compound O=C1N(C(C)C)CCN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(CO3)C=3C(=CC(F)=CC=3)F)=CC=2)C=C1 AEKNYBWUEYNWMJ-QWOOXDRHSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 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
150000001408 amides Chemical class 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 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
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
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
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*: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
239000000470 constituent Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
238000007865 diluting Methods 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
229940113088 dimethylacetamide Drugs 0.000 description 1
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
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CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007789 gas 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
150000004820 halides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 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
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239000011261 inert gas Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
125000002346 iodo group Chemical group I* 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
150000007522 mineralic acids Chemical class 0.000 description 1
125000005609 naphthenate group Chemical group 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
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
239000006072 paste Substances 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
235000019271 petrolatum Nutrition 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
239000002798 polar solvent 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
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
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000003892 spreading Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
229910021653 sulphate ion Inorganic materials 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
230000008719 thickening Effects 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
238000009736 wetting Methods 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)

CA330,075A 1978-06-19 1979-06-19 Pesticidal imidazolines Expired CA1108621A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7827295		1978-06-19
GB27295/78		1978-06-19

Publications (1)

Publication Number	Publication Date
CA1108621A true CA1108621A (en)	1981-09-08

Family

ID=10498035

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA330,075A Expired CA1108621A (en)	1978-06-19	1979-06-19	Pesticidal imidazolines

Country Status (21)

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

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 (de)	1983-06-03
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 (de)	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
1998-09-08	MKEX	Expiry

Publication	Publication Date	Title
US4238497A (en)	1980-12-09	Imidazoline derivatives, salts thereof and their use as pesticides
JPH01121287A (ja)	1989-05-12	イミダゾリン類及び殺虫剤
EP4050000A1 (de)	2022-08-31	Arylsulfidhaltige benzylaminstruktur, verfahren zur synthese und anwendung davon
US5134145A (en)	1992-07-28	Pesticidal pyrimidinyl benzoic acids and esters
US4226876A (en)	1980-10-07	Arthropodicidal imidazoline derivatives
US4414223A (en)	1983-11-08	Pesticidal anilinomethylimidazolines
DE69221234T2 (de)	1998-03-12	Oxa(thia)diazole- und Thiazolone als Wirkstoff gegen Milben und Insekten
CS214681B2 (en)	1982-05-28	Fungicide means
US4320125A (en)	1982-03-16	Thiazolylidene-oxo-propionitrile salts and insecticidal compositions containing these salts
US2902356A (en)	1959-09-01	Certain 2-phenylimino, 3-alkyl oxazolidines, compositions and methods of use as herbicides
EP1129083A1 (de)	2001-09-05	Isothiazolecarbonsäure derivate
US4297361A (en)	1981-10-27	Thiazolylidene-oxo-propionitriles, insecticidal composition containing these compounds
CA1108620A (en)	1981-09-08	Imidazolines
US4479953A (en)	1984-10-30	Pyrazine aldimine compounds as antimicrobial agents
CA1108621A (en)	1981-09-08	Pesticidal imidazolines
US3879190A (en)	1975-04-22	Herbicidal allophanimidates
GB2023603A (en)	1980-01-03	Pesticidal imidazolines, and their preparation and use
GB1592649A (en)	1981-07-08	Imidazoline derivatives and their use as pesticides
IL39395A (en)	1977-04-29	Oxazolidine and thiazolidine 2-(or4)-carbamoyloxime derivatives preparation thereof and compositions containing the
CA1060464A (en)	1979-08-14	Pesticidal triazapentadienes
US4874786A (en)	1989-10-17	Cyanoacetamido-derivatives having a fungicidal activity
US4038403A (en)	1977-07-26	Benzotriazole ovicides and larvicides
US3721679A (en)	1973-03-20	1,3-disubstituted-2-trichloromethyl-5-imino-4-imidazolidinones
US4156017A (en)	1979-05-22	Pesticides
GB1593276A (en)	1981-07-15	Imidazoline derivatives and their use as pesticides