CA1109787A - Emploi comme pesticides de derives d'imidazoline - Google Patents

Emploi comme pesticides de derives d'imidazoline

Info

Publication number: CA1109787A
Authority: CA; Canada
Prior art keywords: hcl; parts; methyl; imidazoline; acid
Prior art date: 1976-11-16
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

CA356,272A

Other languages

English (en)

Inventor

Walter Traber

Haukur Kristinsson

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.)

Novartis AG

Original Assignee

Ciba Geigy Investments 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.)

1976-11-16

Filing date

1980-07-15

Publication date

1981-09-29

1977-10-11 Priority claimed from CH1239077A external-priority patent/CH630507A5/de

1977-11-14 Priority claimed from CA290,708A external-priority patent/CA1104143A/fr

1980-07-15 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1980-07-15 Priority to CA356,272A priority Critical patent/CA1109787A/fr

1981-09-29 Application granted granted Critical

1981-09-29 Publication of CA1109787A publication Critical patent/CA1109787A/fr

Status Expired legal-status Critical Current

Links

150000002462 imidazolines Chemical class 0.000 title 1
229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 title 1
230000000361 pesticidal effect Effects 0.000 title 1
239000000203 mixture Substances 0.000 claims abstract description 29
241000238876 Acari Species 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims abstract description 9
FOGAWQOYUUDCBT-UHFFFAOYSA-N 3-chloro-n-(4,5-dihydro-1h-imidazol-2-ylmethyl)-2-methylaniline Chemical compound CC1=C(Cl)C=CC=C1NCC1=NCCN1 FOGAWQOYUUDCBT-UHFFFAOYSA-N 0.000 claims abstract description 5
239000004480 active ingredient Substances 0.000 claims abstract description 3
230000001984 ectoparasiticidal effect Effects 0.000 claims abstract 4
150000001875 compounds Chemical class 0.000 claims description 24
239000000126 substance Substances 0.000 claims description 15
238000000034 method Methods 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
239000000654 additive Substances 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
239000002270 dispersing agent Substances 0.000 claims description 4
ZBEYBITZGAVVSD-UHFFFAOYSA-N 3-chloro-n-(4,5-dihydro-1h-imidazol-2-ylmethyl)-2-methylaniline;hydrochloride Chemical compound Cl.CC1=C(Cl)C=CC=C1NCC1=NCCN1 ZBEYBITZGAVVSD-UHFFFAOYSA-N 0.000 claims description 3
239000000853 adhesive Substances 0.000 claims description 3
230000001070 adhesive effect Effects 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
239000003995 emulsifying agent Substances 0.000 claims description 3
239000002562 thickening agent Substances 0.000 claims description 3
239000000080 wetting agent Substances 0.000 claims description 3
230000000996 additive effect Effects 0.000 claims 2
150000007522 mineralic acids Chemical class 0.000 claims 1
150000007524 organic acids Chemical class 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 60
244000078703 ectoparasite Species 0.000 abstract description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 61
239000013543 active substance Substances 0.000 description 26
239000000839 emulsion Substances 0.000 description 15
239000000243 solution Substances 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
241000196324 Embryophyta Species 0.000 description 12
239000000460 chlorine Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
239000012141 concentrate Substances 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 8
239000008187 granular material Substances 0.000 description 8
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 8
239000005995 Aluminium silicate Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
235000012211 aluminium silicate Nutrition 0.000 description 7
230000000694 effects Effects 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
241000233866 Fungi Species 0.000 description 6
229920000151 polyglycol Polymers 0.000 description 6
239000010695 polyglycol Substances 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 5
-1 methyL group Chemical group 0.000 description 5
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 5
235000012239 silicon dioxide Nutrition 0.000 description 5
244000105624 Arachis hypogaea Species 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
240000002024 Gossypium herbaceum Species 0.000 description 3
235000004341 Gossypium herbaceum Nutrition 0.000 description 3
241000238631 Hexapoda Species 0.000 description 3
206010061217 Infestation Diseases 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
235000019445 benzyl alcohol Nutrition 0.000 description 3
239000000969 carrier Substances 0.000 description 3
235000019993 champagne Nutrition 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
235000013399 edible fruits Nutrition 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000002156 mixing Methods 0.000 description 3
230000017448 oviposition Effects 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
GHCCHMFFNHOXEU-UHFFFAOYSA-N 2-(chloromethyl)-4,5-dihydro-1H-imidazole hydrochloride Chemical compound Cl.ClCC1=NCCN1 GHCCHMFFNHOXEU-UHFFFAOYSA-N 0.000 description 2
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
235000019483 Peanut oil Nutrition 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241001481703 Rhipicephalus <genus> Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 2
239000000470 constituent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 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
239000000428 dust Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000000605 extraction Methods 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000012467 final product Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
229920005610 lignin Polymers 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
244000005700 microbiome Species 0.000 description 2
WLUCWSITOBZYRR-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-ylmethyl)-2,3-dimethylaniline Chemical compound CC1=CC=CC(NCC=2NCCN=2)=C1C WLUCWSITOBZYRR-UHFFFAOYSA-N 0.000 description 2
JLRGGNFHZLXKOR-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-ylmethyl)-2,3-dimethylaniline;hydrochloride Chemical compound Cl.CC1=CC=CC(NCC=2NCCN=2)=C1C JLRGGNFHZLXKOR-UHFFFAOYSA-N 0.000 description 2
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 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000006072 paste Substances 0.000 description 2
239000000312 peanut oil Substances 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
230000003032 phytopathogenic effect Effects 0.000 description 2
239000004540 pour-on Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 2
239000002689 soil Substances 0.000 description 2
241000894007 species Species 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
MKSYSNRVVYYBIZ-UHFFFAOYSA-N 1-butyl-n-(3,4-dichlorophenyl)pyrrolidin-2-imine Chemical compound CCCCN1CCCC1=NC1=CC=C(Cl)C(Cl)=C1 MKSYSNRVVYYBIZ-UHFFFAOYSA-N 0.000 description 1
PTAKDFCWXDUSFL-UHFFFAOYSA-N 2,3-dichloro-n-(4,5-dihydro-1h-imidazol-2-ylmethyl)aniline Chemical compound ClC1=CC=CC(NCC=2NCCN=2)=C1Cl PTAKDFCWXDUSFL-UHFFFAOYSA-N 0.000 description 1
YZNYRQMEBVFFHW-UHFFFAOYSA-N 2,3-dichloro-n-(4,5-dihydro-1h-imidazol-2-ylmethyl)aniline;hydrochloride Chemical compound Cl.ClC1=CC=CC(NCC=2NCCN=2)=C1Cl YZNYRQMEBVFFHW-UHFFFAOYSA-N 0.000 description 1
VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
AIPXOOFOMCMUJZ-UHFFFAOYSA-N 2-amino-2-(2,3-dimethylphenyl)acetonitrile Chemical compound CC1=CC=CC(C(N)C#N)=C1C AIPXOOFOMCMUJZ-UHFFFAOYSA-N 0.000 description 1
TZVFFXNGZDPRSN-UHFFFAOYSA-N 2-chloro-n-(4,5-dihydro-1h-imidazol-2-ylmethyl)aniline;hydrochloride Chemical compound Cl.ClC1=CC=CC=C1NCC1=NCCN1 TZVFFXNGZDPRSN-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241000238679 Amblyomma Species 0.000 description 1
241001480736 Amblyomma hebraeum Species 0.000 description 1
235000010777 Arachis hypogaea Nutrition 0.000 description 1
241000235349 Ascomycota Species 0.000 description 1
241000221198 Basidiomycota Species 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241001260012 Bursa Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241001157813 Cercospora Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
240000008067 Cucumis sativus Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
101100456896 Drosophila melanogaster metl gene Proteins 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000223218 Fusarium Species 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
244000299507 Gossypium hirsutum Species 0.000 description 1
235000009432 Gossypium hirsutum Nutrition 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
241000238889 Ixodidae Species 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
241000315044 Passalora arachidicola Species 0.000 description 1
241001674048 Phthiraptera Species 0.000 description 1
241000233626 Plasmopara Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
241000221300 Puccinia Species 0.000 description 1
241000949016 Rhipicephalus bursa Species 0.000 description 1
241000238680 Rhipicephalus microplus Species 0.000 description 1
241001274197 Scatophagus argus Species 0.000 description 1
241000208292 Solanaceae Species 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
241001123669 Verticillium albo-atrum Species 0.000 description 1
240000006365 Vitis vinifera Species 0.000 description 1
235000014787 Vitis vinifera Nutrition 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000002390 adhesive tape Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229940115440 aluminum sodium silicate Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
230000002508 compound effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229960002380 dibutyl phthalate Drugs 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000004491 dispersible concentrate Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000284 extract Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
230000000855 fungicidal effect Effects 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
238000000227 grinding Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
230000003641 microbiacidal effect Effects 0.000 description 1
GGARFKXRBDJCPO-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-3-methyl-1,3-thiazol-2-imine Chemical compound CN1C=CSC1=NC1=CC=C(Cl)C(Cl)=C1 GGARFKXRBDJCPO-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000006408 oxalic acid Nutrition 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
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003209 petroleum derivative 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
150000003014 phosphoric acid esters Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000429 sodium aluminium silicate Substances 0.000 description 1
235000012217 sodium aluminium silicate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA356,272A 1976-11-16 1980-07-15 Emploi comme pesticides de derives d'imidazoline Expired CA1109787A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA356,272A CA1109787A (fr)	1976-11-16	1980-07-15	Emploi comme pesticides de derives d'imidazoline

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
CH14401/76		1976-11-16
CH14402/76		1976-11-16
CH1440176		1976-11-16
CH1440276		1976-11-16
CH12390/77		1977-10-11
CH1239077A CH630507A5 (en)	1977-10-11	1977-10-11	Pesticides
CA290,708A CA1104143A (fr)	1976-11-16	1977-11-14	Traduction non-disponible
CA356,272A CA1109787A (fr)	1976-11-16	1980-07-15	Emploi comme pesticides de derives d'imidazoline

Publications (1)

Publication Number	Publication Date
CA1109787A true CA1109787A (fr)	1981-09-29

Family

ID=27508105

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA356,272A Expired CA1109787A (fr)	1976-11-16	1980-07-15	Emploi comme pesticides de derives d'imidazoline

Country Status (1)

Country	Link
CA (1)	CA1109787A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2006119411A1 (fr) *	2005-05-03	2006-11-09	Bayer Cropscience Ag	Derives aminoalkyles heterocycliques et heteroaryles substitues insecticides

1980
- 1980-07-15 CA CA356,272A patent/CA1109787A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2006119411A1 (fr) *	2005-05-03	2006-11-09	Bayer Cropscience Ag	Derives aminoalkyles heterocycliques et heteroaryles substitues insecticides

Legal Events

Date	Code	Title	Description
1998-09-29	MKEX	Expiry

Publication	Publication Date	Title
EP0071568B1 (fr)	1987-01-21	Dérivés d'acide mandélique, procédé de préparation et leur application comme microbicide
EP0040350A1 (fr)	1981-11-25	Nouveaux composés azoliques, leur préparation, leur utilisation pour le traitement des plantes et compositions à cette fin
DE3413996A1 (de)	1985-10-24	Tetrahydrofuran-2-ylmethylamine
JPS61229876A (ja)	1986-10-14	新規なアニリノベンゾオキソール化合物、その製造方法、及び該化合物を含有する組成物、並びに前記化合物の使用方法
CS199732B2 (en)	1980-07-31	Fungicide
US4491595A (en)	1985-01-01	Combating fungi with trisubstituted cyanoguanidines
EP0028011A1 (fr)	1981-05-06	Dérivés d'homosérine, procédé pour leur préparation et leur utilisation comme microbicides
CA1109787A (fr)	1981-09-29	Emploi comme pesticides de derives d'imidazoline
CS212338B2 (en)	1982-03-26	Means for regulation of the plant growth and fungicide means and method of making the active substance
HU184822B (en)	1984-10-29	Insecticide and nematocide compositions containing asymmetric thiophosphonates
DE2643403A1 (de)	1977-04-07	Mikrobizide mittel
US4933328A (en)	1990-06-12	Phosphonium salts and fungicidal use
EP0044276A2 (fr)	1982-01-20	Dérivés de (1H-azolylméthyl)-4, dioxolan-1,3, one-5, leur préparation et leur emploi comme régulateurs de croissance des plantes et/ou pesticides
CS195340B2 (en)	1980-01-31	Fungicide and growth plant regulator and process for preparing effective compounds
US4417050A (en)	1983-11-22	Fungicidal, herbicidal and plant growth-regulating pyrimidyl-containing ethers
SU1243624A3 (ru)	1986-07-07	Способ получени производных 3-/1-триазолил/-фурана
US3812262A (en)	1974-05-21	Substituted propiolophenones used as plant fungicides
EP0096660B1 (fr)	1985-12-11	Microbicides, leur procédé de préparation et leur utilisation pour combattre des micro-organismes
US4416889A (en)	1983-11-22	Combating fungi with N-allenyl-acetanilides
US4407806A (en)	1983-10-04	Fungicidal, herbicidal and plant growth regulating pyridyl-containing ethers
CH627343A5 (en)	1982-01-15	Microbicide
US4532732A (en)	1985-08-06	Oxime derivatives for protecting plant crops
AU612162B2 (en)	1991-07-04	Phosphonium salts
EP0256789B1 (fr)	1993-05-05	Fongicide de benzimidazole substitué
DE2938575A1 (de)	1981-04-23	Acylierte imidazolyl-(gamma)-fluorpinakolyl-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide

CA1109787A - Emploi comme pesticides de derives d'imidazoline - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (8)

Publications (1)

Family

ID=27508105

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

Similar Documents

Legal Events