DD234223A5 - Herbizide und wachstumsregulierende mittel - Google Patents

Herbizide und wachstumsregulierende mittel Download PDF

Info

Publication number: DD234223A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; phenyl; growth; substituted; alkoxy
Prior art date: 1983-11-10

Application number

DD84269267A

Other languages

German (de)

English (en)

Inventor

Roland Schmierer

Reinhard Handte

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

1986-03-26

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

1986-03-26 Publication of DD234223A5 publication Critical patent/DD234223A5/de

Links

239000003795 chemical substances by application Substances 0.000 title claims description 8
239000004009 herbicide Substances 0.000 title abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
-1 carbon ester Chemical class 0.000 claims abstract description 19
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 9
229910052799 carbon Inorganic materials 0.000 claims abstract description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 4
239000003630 growth substance Substances 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 33
239000004480 active ingredient Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 16
230000002363 herbicidal effect Effects 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
238000009472 formulation Methods 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000000068 chlorophenyl group Chemical group 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000003944 tolyl group Chemical group 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
230000008635 plant growth Effects 0.000 claims description 3
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
125000000466 oxiranyl group Chemical group 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
150000003254 radicals Chemical group 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims 3
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
230000026267 regulation of growth Effects 0.000 claims 1
125000001425 triazolyl group Chemical group 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 abstract description 8
125000003342 alkenyl group Chemical group 0.000 abstract description 3
125000002252 acyl group Chemical group 0.000 abstract 1
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
125000000304 alkynyl group Chemical group 0.000 abstract 1
125000005521 carbonamide 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
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
239000003921 oil Substances 0.000 description 24
241000196324 Embryophyta Species 0.000 description 23
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
230000000694 effects Effects 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
230000006378 damage Effects 0.000 description 7
230000012010 growth Effects 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
229920000151 polyglycol Polymers 0.000 description 5
239000010695 polyglycol Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
208000027418 Wounds and injury Diseases 0.000 description 4
150000001408 amides Chemical class 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
230000009036 growth inhibition Effects 0.000 description 4
208000014674 injury Diseases 0.000 description 4
238000002156 mixing Methods 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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
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
241000209048 Poa 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
230000015572 biosynthetic process Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 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
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
150000002191 fatty alcohols Chemical class 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
239000008096 xylene Substances 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
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 2
239000005995 Aluminium silicate Substances 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare 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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
235000007238 Secale cereale Nutrition 0.000 description 2
244000082988 Secale cereale Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
239000013543 active substance Substances 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000000969 carrier Substances 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
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
239000000945 filler Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
150000007529 inorganic bases Chemical class 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
238000006386 neutralization reaction Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
238000007127 saponification reaction Methods 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
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001424 substituent group Chemical group 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
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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
125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-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
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229920000742 Cotton Polymers 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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
244000292693 Poa annua Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
229920001214 Polysorbate 60 Polymers 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
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 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
230000006578 abscission Effects 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
125000003282 alkyl amino group Chemical group 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
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
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SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
125000004663 dialkyl amino group Chemical group 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
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
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230000001804 emulsifying effect Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
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SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
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ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
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SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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150000007524 organic acids Chemical class 0.000 description 1
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LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
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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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD84269267A 1983-11-10 1984-11-08 Herbizide und wachstumsregulierende mittel DD234223A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19833340594 DE3340594A1 (de)	1983-11-10	1983-11-10	2-arylsubstituierte imidazolinone, verfahren zu ihrer herstellung und ihre verwendung im pflanzenschutz

Publications (1)

Publication Number	Publication Date
DD234223A5 true DD234223A5 (de)	1986-03-26

Family

ID=6213908

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84269267A DD234223A5 (de)	1983-11-10	1984-11-08	Herbizide und wachstumsregulierende mittel

Country Status (12)

Country	Link
EP (1)	EP0144749A3 (fr)
JP (1)	JPS60123474A (fr)
KR (1)	KR850003721A (fr)
CN (1)	CN85101342A (fr)
AU (1)	AU3528784A (fr)
BR (1)	BR8405755A (fr)
DD (1)	DD234223A5 (fr)
DE (1)	DE3340594A1 (fr)
ES (1)	ES537504A0 (fr)
HU (1)	HUT36340A (fr)
IL (1)	IL73469A0 (fr)
ZA (1)	ZA848757B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2677984B1 (fr) *	1991-06-21	1994-02-25	Elf Sanofi	Derives d'imidazoline n-substitues, leur preparation, les compositions pharmaceutiques en contenant.

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4122275A (en) *	1977-08-08	1978-10-24	American Cyanamid Company	Imidazolinyl benzamides 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
US4221586A (en) *	1979-01-30	1980-09-09	American Cyanamid Company	Imidazolinyl benzamides as herbicidal agents

1983
- 1983-11-10 DE DE19833340594 patent/DE3340594A1/de not_active Withdrawn
1984
- 1984-11-02 HU HU844075A patent/HUT36340A/hu unknown
- 1984-11-03 EP EP84113260A patent/EP0144749A3/fr not_active Withdrawn
- 1984-11-08 DD DD84269267A patent/DD234223A5/de unknown
- 1984-11-08 ES ES537504A patent/ES537504A0/es active Granted
- 1984-11-09 ZA ZA848757A patent/ZA848757B/xx unknown
- 1984-11-09 IL IL73469A patent/IL73469A0/xx unknown
- 1984-11-09 BR BR8405755A patent/BR8405755A/pt unknown
- 1984-11-09 KR KR1019840007011A patent/KR850003721A/ko not_active Withdrawn
- 1984-11-09 JP JP59235342A patent/JPS60123474A/ja active Pending
- 1984-11-09 AU AU35287/84A patent/AU3528784A/en not_active Abandoned
1985
- 1985-04-01 CN CN198585101342A patent/CN85101342A/zh active Pending

Also Published As

Publication number	Publication date
KR850003721A (ko)	1985-06-26
EP0144749A3 (fr)	1985-07-03
HUT36340A (en)	1985-09-30
CN85101342A (zh)	1987-01-31
BR8405755A (pt)	1985-09-17
ES8600249A1 (es)	1985-10-16
AU3528784A (en)	1985-05-16
IL73469A0 (en)	1985-02-28
DE3340594A1 (de)	1985-05-23
ZA848757B (en)	1985-06-26
EP0144749A2 (fr)	1985-06-19
JPS60123474A (ja)	1985-07-02
ES537504A0 (es)	1985-10-16

Publication	Publication Date	Title
EP0084893B1 (fr)	1987-01-14	Dérivés de 4H-3,1-benzoxazine, procédés pour leur préparation et leur utilisation dans la lutte contre la végétation indésirable
EP0360163B1 (fr)	1994-01-12	Dérivés d'acides carboxyliques aromatiques et leur utilisation pour combattre la croissance des plantes indésirables
DD231481A5 (de)	1986-01-02	Herbizide und wachstumsregulierende mittel
EP0207894B1 (fr)	1991-11-21	Dérivés du N-phényl tétrahydro-3,4,5,6 phtalimide dotés d'activité herbicide
DE69334162T2 (de)	2008-04-24	Heteroaroyl-isoxazole und ihre Verwendung als Herbizide
EP0136647A2 (fr)	1985-04-10	Dérivés de cyclohexénone, leur procédé de préparation et leur utilisation pour lutter contre la croissance de plantes non désirées
EP0135838B1 (fr)	1990-04-18	3-Phényl-4-méthoxy carbonylepyrazoles, leur procédé de préparation et leur utilisation dans la lutte contre la croissance de plantes indésirables
DD261084A5 (de)	1988-10-19	1,2-disubstituierte piperidine, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz
EP0224823A2 (fr)	1987-06-10	Dérivés de la quinoléine et leur utilité pour contrôler la croissance non voulue des plantes
DE68910423T2 (de)	1994-03-03	5-Substituierte-2,4-Diphenylpyrimidin-Derivate, deren Herstellung und herbizide Verwendung.
DD273436A5 (de)	1989-11-15	Verfahren zur herstellung substituierter tetrahydrophtholimide und ihre verwendung der herbezide
DD249623A5 (de)	1987-09-16	Herbizide mittel
DD239515A5 (de)	1986-10-01	Pflanzenwachstumsregulierende mittel
EP0151744B1 (fr)	1989-04-26	1-Acylimidazolinones, procédé de leur préparation et leur application dans l'agriculture
EP0410265B1 (fr)	1994-12-14	Esters de l'acide cinnamique
EP0456089B1 (fr)	1996-04-03	Ethers de cyclohexénonoximes, leur procédé de production et leur application comme herbicides
EP0358108B1 (fr)	1992-04-15	Dérivés de l'acide 5-(N-3,4,5,6-tétrahydrophthalimido)-cinnamique
EP0419917B1 (fr)	1994-11-17	Amides l'acide pyrazole-3-carboxylique
EP0120448A1 (fr)	1984-10-03	Dérivés du cyclohexane-1,3-dion, leur méthode de préparation et leur utilisation dans la lutte contre des plantes non-désirées
DD234223A5 (de)	1986-03-26	Herbizide und wachstumsregulierende mittel
EP0090258A2 (fr)	1983-10-05	3-Chloro-8-cyanoquinoléines, procédé pour leur préparation et leur utilisation pour contrôler la croissance des plantes indésirables
EP0098440B1 (fr)	1986-12-30	Dérivés de la 3,7-dichloroquinoléine, procédé pour leur préparation et leur utilisation pour lutter contre la croissance non-désirable des plantes
EP0407888A1 (fr)	1991-01-16	Pyrimido[5,4-e]-as-triazine-5,7(6H,8H)-diones pour lutter contre une croissance indésirable des plants
EP0400427B1 (fr)	1995-04-05	Esters herbicides de l'acide (N-tétrahydro-3,4,5,6 phtalimido)-5 cinnamique, procédé pour leur préparation et leur application
DD234224A5 (de)	1986-03-26	Herbizide und wachstumsregulierende mittel