DD231481A5 - Herbizide und wachstumsregulierende mittel - Google Patents

Herbizide und wachstumsregulierende mittel Download PDF

Info

Publication number: DD231481A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; phenyl; growth; substituted; halogen
Prior art date: 1983-11-10

Application number

DD84269265A

Other languages

German (de)

English (en)

Inventor

Roland Schmierer

Reinhard Handte

Rainer Liebl

Hilmar Mildenberger

Klaus Bauer

Hermann Bieringer

Helmut Buerstell

Original Assignee

��@��k��

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.)

1983-11-10

Filing date

1984-11-08

Publication date

1986-01-02

1984-11-08 Application filed by ��@��k�� filed Critical ��@��k��

1986-01-02 Publication of DD231481A5 publication Critical patent/DD231481A5/de

Links

239000003795 chemical substances by application Substances 0.000 title claims description 8
239000004009 herbicide Substances 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 21
-1 cyanomethyl Chemical group 0.000 claims abstract description 15
230000002363 herbicidal effect Effects 0.000 claims abstract description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
238000000034 method Methods 0.000 claims abstract description 7
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
239000003630 growth substance Substances 0.000 claims abstract description 3
125000004849 alkoxymethyl group Chemical group 0.000 claims abstract 2
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000000068 chlorophenyl group Chemical group 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
125000003944 tolyl group Chemical group 0.000 claims description 4
150000001204 N-oxides Chemical class 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
230000026267 regulation of growth Effects 0.000 claims description 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
239000012050 conventional carrier Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
241000196324 Embryophyta Species 0.000 abstract description 29
125000001188 haloalkyl group Chemical group 0.000 abstract description 5
238000004519 manufacturing process Methods 0.000 abstract description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 2
125000003342 alkenyl group Chemical group 0.000 abstract 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
239000004480 active ingredient Substances 0.000 description 17
230000006378 damage Effects 0.000 description 11
230000012010 growth Effects 0.000 description 10
239000000203 mixture Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 7
238000009472 formulation Methods 0.000 description 6
230000009036 growth inhibition Effects 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000004495 emulsifiable concentrate Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000013543 active substance Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
240000005979 Hordeum vulgare Species 0.000 description 3
235000007340 Hordeum vulgare Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
235000007238 Secale cereale Nutrition 0.000 description 3
244000082988 Secale cereale Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
241000209140 Triticum Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
239000003337 fertilizer Substances 0.000 description 3
238000000227 grinding Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
YZUAOVCUGSBIPP-UHFFFAOYSA-N tert-butyl N-[1-([1,2,4]triazolo[4,3-a]pyridin-3-yl)ethyl]carbamate Chemical compound C1=CC=CN2C(C(NC(=O)OC(C)(C)C)C)=NN=C21 YZUAOVCUGSBIPP-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
241001300479 Macroptilium Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
238000009835 boiling Methods 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
244000038559 crop plants Species 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
208000014674 injury Diseases 0.000 description 2
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000002689 soil Substances 0.000 description 2
238000005507 spraying Methods 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
230000009105 vegetative growth Effects 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
238000009736 wetting Methods 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
YCPQUHCGFDFLSI-LURJTMIESA-N (2s)-2-amino-2,3-dimethylbutanamide Chemical compound CC(C)[C@](C)(N)C(N)=O YCPQUHCGFDFLSI-LURJTMIESA-N 0.000 description 1
125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
NFNXIOZUYLDOQS-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4,5-dihydroimidazole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C=NCC1 NFNXIOZUYLDOQS-UHFFFAOYSA-N 0.000 description 1
XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
OSGMRWXDUYAHMO-UHFFFAOYSA-N 2-(aminomethyl)-3-methylbutanamide Chemical compound CC(C)C(CN)C(N)=O OSGMRWXDUYAHMO-UHFFFAOYSA-N 0.000 description 1
MXIUWSYTQJLIKE-UHFFFAOYSA-N 2-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)=O MXIUWSYTQJLIKE-UHFFFAOYSA-N 0.000 description 1
CMJUNAQINNWKAU-KTKRTIGZSA-N 2-[[(z)-2-oxononadec-10-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)CNCCS(O)(=O)=O CMJUNAQINNWKAU-KTKRTIGZSA-N 0.000 description 1
XUNMBHZKXIOKMO-UHFFFAOYSA-N 4,4-diethyl-1h-imidazol-5-one Chemical compound CCC1(CC)N=CNC1=O XUNMBHZKXIOKMO-UHFFFAOYSA-N 0.000 description 1
NOKZRORHBQSMJX-UHFFFAOYSA-N 4-methyl-4-propan-2-yl-2-[2-(trifluoromethyl)phenyl]-1h-imidazol-5-one Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC=CC=C1C(F)(F)F NOKZRORHBQSMJX-UHFFFAOYSA-N 0.000 description 1
241001621841 Alopecurus myosuroides Species 0.000 description 1
244000237956 Amaranthus retroflexus Species 0.000 description 1
235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
235000006463 Brassica alba Nutrition 0.000 description 1
244000140786 Brassica hirta Species 0.000 description 1
244000144786 Chrysanthemum segetum Species 0.000 description 1
235000005470 Chrysanthemum segetum Nutrition 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
244000100545 Lolium multiflorum Species 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
244000088461 Panicum crus-galli Species 0.000 description 1
235000011999 Panicum crusgalli Nutrition 0.000 description 1
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
240000006694 Stellaria media Species 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
GELXFVQAWNTGPQ-UHFFFAOYSA-N [N].C1=CNC=N1 Chemical compound [N].C1=CNC=N1 GELXFVQAWNTGPQ-UHFFFAOYSA-N 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000000274 adsorptive effect Effects 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
230000035784 germination Effects 0.000 description 1
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
208000037824 growth disorder Diseases 0.000 description 1
238000003306 harvesting Methods 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
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
150000002462 imidazolines Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
229920002113 octoxynol Polymers 0.000 description 1
XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920001522 polyglycol ester Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000004576 sand Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
230000036435 stunted growth Effects 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
238000012549 training Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- 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
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/70—One oxygen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DD84269265A 1983-11-10 1984-11-08 Herbizide und wachstumsregulierende mittel DD231481A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19833340595 DE3340595A1 (de)	1983-11-10	1983-11-10	Imidazolinone, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz

Publications (1)

Publication Number	Publication Date
DD231481A5 true DD231481A5 (de)	1986-01-02

Family

ID=6213909

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84269265A DD231481A5 (de)	1983-11-10	1984-11-08	Herbizide und wachstumsregulierende mittel

Country Status (14)

Country	Link
US (1)	US4614535A (fr)
EP (1)	EP0144748A3 (fr)
JP (1)	JPS60123475A (fr)
KR (1)	KR850003722A (fr)
CN (1)	CN85101424A (fr)
AU (1)	AU3528884A (fr)
BR (1)	BR8405750A (fr)
DD (1)	DD231481A5 (fr)
DE (1)	DE3340595A1 (fr)
ES (1)	ES8600248A1 (fr)
HU (1)	HUT36341A (fr)
IL (1)	IL73470A0 (fr)
PH (1)	PH20098A (fr)
ZA (1)	ZA848760B (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4798619A (en) *	1980-06-02	1989-01-17	American Cyanamid Co.	2-(2-imidazolin-2-yl)-pyridines and quinolines and use of said compounds as herbicidal agents
GR861747B (en) *	1985-07-25	1986-09-23	Nissan Chemical Ind Ltd	Pyridine derivatives process for their production and herbicidal compositions
CN86106435A (zh) *	1985-09-24	1987-05-27	舍林股份公司	咪唑啉基衍生物，其制备方法和含有这类化合物的具有除草作用的制剂
GB2174395A (en) *	1986-05-09	1986-11-05	American Cyanimid Co	Herbicidal 2-(2-imidazolin-2-yl)pyridine derivatives
EP0261705A1 (fr) *	1986-08-25	1988-03-30	Shell Internationale Researchmaatschappij B.V.	Acides imidazolinyl benzoiques herbicides et dérivés
DE3634887A1 (de) *	1986-10-14	1988-04-21	Bayer Ag	2-(5-oxo-2-imidazolin-2-yl)-pyridin-derivate
EP0303863A3 (fr) *	1987-08-17	1991-10-23	American Cyanamid Company	Composés de benzène sulfonyl carboxamide, composés intermédiaires et procédés pour leur préparation et l'utilisation de ces composés et intermédiaires comme herbicides
US5034532A (en) *	1988-01-27	1991-07-23	American Cyanamid Company	Method for the preparation of quinolyl and pyridyl substituted imidazolinones
US5062881A (en) *	1989-12-20	1991-11-05	American Cyanamid Company	2-(1-substituted-2-imidazolin-2-yl)benzoic and nicotinic acids and a method for their preparation
TW201738B (fr) *	1990-03-20	1993-03-11	Sanofi Co
US5270317A (en) *	1990-03-20	1993-12-14	Elf Sanofi	N-substituted heterocyclic derivatives, their preparation and the pharmaceutical compositions in which they are present
US5076832A (en) *	1990-07-20	1991-12-31	Ici Americas Inc.	Certain 3-(substituted phenyl)-5-(substituted phenyl)-1-ethylimidazolidine-4-ones as herbicides
US5108485A (en) *	1990-08-31	1992-04-28	American Cyanamid Company	Herbicidal 2-(2-imidazolin-2-yl)-benzazoles
FR2677984B1 (fr) *	1991-06-21	1994-02-25	Elf Sanofi	Derives d'imidazoline n-substitues, leur preparation, les compositions pharmaceutiques en contenant.
US6002016A (en) *	1991-12-20	1999-12-14	Rhone-Poulenc Agrochimie	Fungicidal 2-imidazolin-5-ones and 2-imidazoline-5-thiones
FR2706456B1 (fr)	1993-06-18	1996-06-28	Rhone Poulenc Agrochimie	Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides.
FR2685328B1 (fr) *	1991-12-20	1995-12-01	Rhone Poulenc Agrochimie	Derives de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides.
US6008370A (en) *	1992-11-25	1999-12-28	Rhone-Poulenc Agrochimie	Fungicidal-2-alkoxy/haloalkoxy-1-(mono- or disubstituted)amino-4,4-disubstituted-2-imidazolin-5-ones
TWI346108B (en) *	2004-08-23	2011-08-01	Bristol Myers Squibb Co	A method for preparing irbesartan and intermediates thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4125727A (en) *	1976-10-18	1978-11-14	American Cyanamid Company	Method of preparing imidazoisoindolediones
US4188487A (en) *	1977-08-08	1980-02-12	American Cyanamid Company	Imidazolinyl benzoic acids, esters and salts and their use as herbicidal agents
IL55064A (en) *	1977-08-08	1983-06-15	American Cyanamid Co	5,5-disubstituted-4-oxo-2-imidazolin-2-yl benzoic acid esters,their preparation and herbicidal compositions comprising them
IL55854A0 (en) *	1978-01-09	1979-01-31	American Cyanamid Co	Method for controlling the growth of plants by using imidazole derivatives

1983
- 1983-11-10 DE DE19833340595 patent/DE3340595A1/de not_active Withdrawn
1984
- 1984-11-02 HU HU844076A patent/HUT36341A/hu unknown
- 1984-11-03 EP EP84113259A patent/EP0144748A3/fr not_active Withdrawn
- 1984-11-08 ES ES537502A patent/ES8600248A1/es not_active Expired
- 1984-11-08 PH PH31423A patent/PH20098A/en unknown
- 1984-11-08 US US06/669,620 patent/US4614535A/en not_active Expired - Fee Related
- 1984-11-08 DD DD84269265A patent/DD231481A5/de unknown
- 1984-11-09 BR BR8405750A patent/BR8405750A/pt unknown
- 1984-11-09 AU AU35288/84A patent/AU3528884A/en not_active Abandoned
- 1984-11-09 ZA ZA848760A patent/ZA848760B/xx unknown
- 1984-11-09 JP JP59235343A patent/JPS60123475A/ja active Pending
- 1984-11-09 KR KR1019840007012A patent/KR850003722A/ko not_active Withdrawn
- 1984-11-09 IL IL73470A patent/IL73470A0/xx unknown
1985
- 1985-04-01 CN CN198585101424A patent/CN85101424A/zh active Pending

Also Published As

Publication number	Publication date
AU3528884A (en)	1985-05-16
BR8405750A (pt)	1985-09-17
HUT36341A (en)	1985-09-30
ES537502A0 (es)	1985-10-16
EP0144748A2 (fr)	1985-06-19
CN85101424A (zh)	1987-01-17
KR850003722A (ko)	1985-06-26
JPS60123475A (ja)	1985-07-02
DE3340595A1 (de)	1985-05-23
EP0144748A3 (fr)	1985-07-03
US4614535A (en)	1986-09-30
ES8600248A1 (es)	1985-10-16
PH20098A (en)	1986-09-24
IL73470A0 (en)	1985-02-28
ZA848760B (en)	1985-06-26

Publication	Publication Date	Title
EP0131258B1 (fr)	1989-08-30	Urées N-alkoxy- et N-alkylsulfonylaminosulfonyliques et pyrimido- ou triazino-thiatriazine-oxides comme intermédiaires
EP0144748A2 (fr)	1985-06-19	Imidazolinones, procédé de leur préparation et leur application dans la protection des plantes
DE3217094C2 (fr)	1989-12-14
EP0207894B1 (fr)	1991-11-21	Dérivés du N-phényl tétrahydro-3,4,5,6 phtalimide dotés d'activité herbicide
DE69126836T2 (de)	1998-01-02	Herbizide
DD264844A5 (de)	1989-02-15	Herbizide mittel
EP0248968A1 (fr)	1987-12-16	Ester propynylique de l'acide (R)-2-[4-(5-chloro-3-fluoropyridine-2-yloxy)-phénoxy]-propionique à activité herbicide
EP0075840B1 (fr)	1987-11-11	Phényléthers hétérocycliques, procédé pour leur préparation et herbicides les contenant
DD283918A5 (de)	1990-10-31	Herbizide und pflanzenwachsumsregulierende mittel und verfahren zur herstellung der wirkstoffe
DD261084A5 (de)	1988-10-19	1,2-disubstituierte piperidine, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz
DD273436A5 (de)	1989-11-15	Verfahren zur herstellung substituierter tetrahydrophtholimide und ihre verwendung der herbezide
DD249623A5 (de)	1987-09-16	Herbizide mittel
EP0151744B1 (fr)	1989-04-26	1-Acylimidazolinones, procédé de leur préparation et leur application dans l'agriculture
EP0135838A2 (fr)	1985-04-03	3-Phényl-4-méthoxy carbonylepyrazoles, leur procédé de préparation et leur utilisation dans la lutte contre la croissance de plantes indésirables
DD148708A5 (de)	1981-06-10	Herbizide mittel
DE3545597A1 (de)	1987-07-02	Neue herbizid wirksame imidazolinone
EP0090258A2 (fr)	1983-10-05	3-Chloro-8-cyanoquinoléines, procédé pour leur préparation et leur utilisation pour contrôler la croissance des plantes indésirables
DD254317A5 (de)	1988-02-24	Herbizide und wachstumsregulierende mittel
EP0037526A1 (fr)	1981-10-14	Acétanilides substitués, procédé pour les préparer et leur utilisation comme herbicides
DE3408403A1 (de)	1985-09-12	Substituierte 2-arylimidazolinone, verfahren zu ihrer herstellung und ihre verwendung als pflanzenbehandlungsmittel
DE3403730A1 (de)	1985-08-08	Isoindole, verfahren zu ihrer herstellung und ihre verwendung in der landwirtschaft
DE4237920A1 (en)	1993-05-19	3-Aryl-uracil derivs. - are effective against weeds, act as dessicants, and facilitate harvesting of cotton, potato or rape
EP0144749A2 (fr)	1985-06-19	Imidazolinones-2-aryl substitués, procédé de leur préparation et leur application dans la protection des plantes
EP0133162A2 (fr)	1985-02-13	Dérivés d'oxydes de phosphine et leur utilisation comme agents herbicides et régulateurs de la croissance des plantes
EP0009555A1 (fr)	1980-04-16	Agents herbicides à base d'un thiolcarbamate contenant un haloacylamide comme antagoniste et leur utilisation dans un procédé de lutte sélective contre la croissance de plantes indésirables