DD283918A5 - Herbizide und pflanzenwachsumsregulierende mittel und verfahren zur herstellung der wirkstoffe - Google Patents

Herbizide und pflanzenwachsumsregulierende mittel und verfahren zur herstellung der wirkstoffe Download PDF

Info

Publication number: DD283918A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; alkoxy; halogen; phenyl; formula
Prior art date: 1988-08-05

Application number

DD89331465A

Other languages

German (de)

English (en)

Inventor

Heinz-Josef Loeher

Lothar Willms

Michael Frey

Klaus Bauer

Hermann Bieringer

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.)

1988-08-05

Filing date

1989-08-03

Publication date

1990-10-31

1989-08-03 Application filed by ��@��k�� filed Critical ��@��k��

1990-10-31 Publication of DD283918A5 publication Critical patent/DD283918A5/de

Links

238000000034 method Methods 0.000 title claims description 14
239000003795 chemical substances by application Substances 0.000 title claims description 7
239000004009 herbicide Substances 0.000 title claims description 3
238000004519 manufacturing process Methods 0.000 title claims description 3
239000013543 active substance Substances 0.000 title description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 51
150000002367 halogens Chemical group 0.000 claims abstract description 50
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 42
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
-1 tetrahydrofurfuryl Chemical group 0.000 claims abstract description 28
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 20
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
230000002363 herbicidal effect Effects 0.000 claims abstract description 14
239000001257 hydrogen Substances 0.000 claims abstract description 12
229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims abstract description 7
150000002431 hydrogen Chemical class 0.000 claims abstract description 6
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
125000006678 phenoxycarbonyl group Chemical group 0.000 claims abstract description 5
230000008635 plant growth Effects 0.000 claims abstract description 5
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 3
125000002541 furyl group Chemical group 0.000 claims abstract description 3
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
125000004414 alkyl thio group Chemical group 0.000 claims abstract 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 3
230000001105 regulatory effect Effects 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 60
241000196324 Embryophyta Species 0.000 claims description 42
229910005965 SO 2 Inorganic materials 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 23
229910052799 carbon Inorganic materials 0.000 claims description 20
239000004480 active ingredient Substances 0.000 claims description 14
230000000694 effects Effects 0.000 claims description 14
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims description 4
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 3
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 3
229940100389 Sulfonylurea Drugs 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 3
235000013339 cereals Nutrition 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims description 3
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
125000005336 allyloxy group Chemical group 0.000 claims description 2
230000002688 persistence Effects 0.000 claims 3
125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims 2
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 1
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims 1
125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
230000001276 controlling effect Effects 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 claims 1
150000003254 radicals Chemical group 0.000 abstract description 27
125000000392 cycloalkenyl group Chemical group 0.000 abstract description 2
125000003545 alkoxy group Chemical group 0.000 abstract 10
125000004417 unsaturated alkyl group Chemical group 0.000 abstract 5
125000000753 cycloalkyl group Chemical group 0.000 abstract 3
125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 abstract 1
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 abstract 1
108010081348 HRT1 protein Hairy Proteins 0.000 abstract 1
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 abstract 1
241000209510 Liliopsida Species 0.000 abstract 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
235000013877 carbamide Nutrition 0.000 abstract 1
241001233957 eudicotyledons Species 0.000 abstract 1
125000005359 phenoxyalkyl group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000000126 substance Substances 0.000 description 11
238000009472 formulation Methods 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
230000012010 growth Effects 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000002689 soil Substances 0.000 description 6
239000002904 solvent Substances 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
238000009835 boiling Methods 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000008187 granular material Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
240000005979 Hordeum vulgare Species 0.000 description 3
235000007340 Hordeum vulgare Nutrition 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
240000007594 Oryza sativa Species 0.000 description 3
241000209056 Secale Species 0.000 description 3
235000007238 Secale cereale Nutrition 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
241000209140 Triticum Species 0.000 description 3
150000004657 carbamic acid derivatives Chemical class 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
239000000839 emulsion 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
239000003337 fertilizer Substances 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
HASWNCHYBAFUSB-PMACEKPBSA-N (3s,6s)-3,6-bis[(5-hydroxy-1h-indol-3-yl)methyl]piperazine-2,5-dione Chemical compound C1=C(O)C=C2C(C[C@H]3C(=O)N[C@H](C(N3)=O)CC3=CNC4=CC=C(C=C43)O)=CNC2=C1 HASWNCHYBAFUSB-PMACEKPBSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
SSZGZNMFUXOAFG-UHFFFAOYSA-N 1-chloro-2-ethylsulfonylethane Chemical compound CCS(=O)(=O)CCCl SSZGZNMFUXOAFG-UHFFFAOYSA-N 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
241000234653 Cyperus Species 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
241000219146 Gossypium Species 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
240000006694 Stellaria media Species 0.000 description 2
235000021536 Sugar beet Nutrition 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000002585 base Substances 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
244000038559 crop plants Species 0.000 description 2
108010087681 cyclo(5-hydroxytryptophyl-5-hydroxytryptophyl) Proteins 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
238000000227 grinding Methods 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
239000002480 mineral oil Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
238000009331 sowing Methods 0.000 description 2
241000894007 species Species 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
230000009105 vegetative growth Effects 0.000 description 2
238000009736 wetting Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
IDQNBVFPZMCDDN-UHFFFAOYSA-N 2-Amino-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(N)=N1 IDQNBVFPZMCDDN-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
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
FNCVECQZXCCHJM-UHFFFAOYSA-N 4,5-dimethoxypyrimidin-2-amine Chemical compound COC1=CN=C(N)N=C1OC FNCVECQZXCCHJM-UHFFFAOYSA-N 0.000 description 1
241000219144 Abutilon Species 0.000 description 1
241000209136 Agropyron Species 0.000 description 1
241000748223 Alisma Species 0.000 description 1
241000743985 Alopecurus Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241000219318 Amaranthus Species 0.000 description 1
235000005781 Avena Nutrition 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
RPKSXPXPCDSBCZ-UHFFFAOYSA-N B([O-])([O-])C#N.[K+].[K+] Chemical compound B([O-])([O-])C#N.[K+].[K+] RPKSXPXPCDSBCZ-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
241000339490 Brachyachne Species 0.000 description 1
235000006463 Brassica alba Nutrition 0.000 description 1
244000140786 Brassica hirta Species 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000006008 Brassica napus var napus Nutrition 0.000 description 1
244000192528 Chrysanthemum parthenium Species 0.000 description 1
244000144786 Chrysanthemum segetum Species 0.000 description 1
235000005470 Chrysanthemum segetum Nutrition 0.000 description 1
241000132536 Cirsium Species 0.000 description 1
241000207892 Convolvulus Species 0.000 description 1
201000003075 Crimean-Congo hemorrhagic fever Diseases 0.000 description 1
235000004035 Cryptotaenia japonica Nutrition 0.000 description 1
235000017896 Digitaria Nutrition 0.000 description 1
241001303487 Digitaria <clam> Species 0.000 description 1
241000192043 Echinochloa Species 0.000 description 1
241000202829 Eleocharis Species 0.000 description 1
241001101998 Galium Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
240000007171 Imperata cylindrica Species 0.000 description 1
235000021506 Ipomoea Nutrition 0.000 description 1
241000207783 Ipomoea Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000520028 Lamium Species 0.000 description 1
241000209082 Lolium Species 0.000 description 1
244000100545 Lolium multiflorum Species 0.000 description 1
235000017945 Matricaria Nutrition 0.000 description 1
235000007232 Matricaria chamomilla Nutrition 0.000 description 1
241000209504 Poaceae Species 0.000 description 1
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 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
241000219053 Rumex Species 0.000 description 1
240000009132 Sagittaria sagittifolia Species 0.000 description 1
241000202758 Scirpus Species 0.000 description 1
235000005775 Setaria Nutrition 0.000 description 1
241000232088 Setaria <nematode> Species 0.000 description 1
241000220261 Sinapis Species 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
235000011684 Sorghum saccharatum Nutrition 0.000 description 1
102000007641 Trefoil Factors Human genes 0.000 description 1
235000015724 Trifolium pratense Nutrition 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
241001464837 Viridiplantae Species 0.000 description 1
241001148683 Zostera marina Species 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000000274 adsorptive effect Effects 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007900 aqueous suspension Substances 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
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 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
239000004202 carbamide Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000035784 germination Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
VREBDQMPDDUVOI-UHFFFAOYSA-N methyl(methylsulfanylmethyl)azanium;chloride Chemical compound Cl.CNCSC VREBDQMPDDUVOI-UHFFFAOYSA-N 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
239000003921 oil Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000002970 ototoxic effect Effects 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001522 polyglycol ester Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
239000010453 quartz Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000013589 supplement Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

DD89331465A 1988-08-05 1989-08-03 Herbizide und pflanzenwachsumsregulierende mittel und verfahren zur herstellung der wirkstoffe DD283918A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3826609A DE3826609A1 (de)	1988-08-05	1988-08-05	Heterocyclisch substituierte sulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide oder pflanzenwachstumsregulatoren

Publications (1)

Publication Number	Publication Date
DD283918A5 true DD283918A5 (de)	1990-10-31

Family

ID=6360287

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD89331465A DD283918A5 (de)	1988-08-05	1989-08-03	Herbizide und pflanzenwachsumsregulierende mittel und verfahren zur herstellung der wirkstoffe

Country Status (17)

Country	Link
US (1)	US5030270A (pt)
EP (1)	EP0353641B1 (pt)
JP (1)	JP2818799B2 (pt)
KR (1)	KR900003137A (pt)
AT (1)	ATE115138T1 (pt)
AU (1)	AU617205B2 (pt)
BR (1)	BR8903945A (pt)
CA (1)	CA1339993C (pt)
DD (1)	DD283918A5 (pt)
DE (2)	DE3826609A1 (pt)
DK (1)	DK384389A (pt)
ES (1)	ES2067504T3 (pt)
GR (1)	GR3015098T3 (pt)
HU (1)	HUT52761A (pt)
IL (1)	IL91198A (pt)
SU (1)	SU1741598A3 (pt)
ZA (1)	ZA895960B (pt)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3811777A1 (de) *	1988-04-08	1989-10-19	Hoechst Ag	Heterocyclisch substituierte alkyl- und alkenylsulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide oder pflanzenwachstumsregulatoren
DE3822841A1 (de) *	1988-06-18	1989-12-21	Hoechst Ag	Substituierte sulfonyldiamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren
DE59007677D1 (de) *	1989-07-19	1994-12-15	Hoechst Schering Agrevo Gmbh	Heterocyclisch substituierte Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide oder Pflanzenwachstumsregulatoren.
US5009699A (en) *	1990-06-22	1991-04-23	American Cyanamid Company	1-{[O-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea herbicidal composition and use
DE4021489A1 (de) *	1990-07-06	1992-01-09	Hoechst Ag	Substituierte sulfonalkylsulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren
DE4022983A1 (de) *	1990-07-19	1992-01-23	Hoechst Ag	Verfahren zur herstellung von n-alkylsulfonylaminosulfonylharnstoffen
DE4022982A1 (de) *	1990-07-19	1992-01-23	Hoechst Ag	Verfahren zur herstellung von n-alkylsulfonylaminosulfonylharnstoffen
ATE139529T1 (de) *	1991-03-07	1996-07-15	Hoechst Schering Agrevo Gmbh	Verfahren zur herstellung von sulfonylharnstoffen
ATE171699T1 (de) *	1991-06-28	1998-10-15	Nissan Chemical Ind Ltd	Iminosulfonylharnstoffderivate und herbizide
DE4217719A1 (de) *	1992-05-29	1993-12-02	Bayer Ag	Zweifach heterocyclisch substituierte Sulfonylamino(thio)carbonylverbindungen
JPH0841019A (ja) *	1994-05-27	1996-02-13	Nippon Bayeragrochem Kk	スルファミド誘導体、及び殺虫剤
PE20141468A1 (es)	2010-12-21	2014-11-05	Bayer Cropscience Lp	Mutantes tipo papel de lija de bacillus y metodos de uso de los mismo para mejorar el crecimiento vegetal, promover la salud de plantas y controlar enfermedades y plagas
BR112014005654A2 (pt)	2011-09-12	2017-03-28	Bayer Cropscience Lp	métodos para melhorar a saúde e promover o crescimento de uma planta e/ou de melhorar o amadurecimento da fruta

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3111451A1 (de) *	1981-03-24	1982-10-07	Hoechst Ag, 6000 Frankfurt	"heterocyclisch substituierte (halogen)alkyl- und alkoxysulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung in der landwirtschaft"
DE3131489A1 (de) *	1981-08-08	1983-02-24	Hoechst Ag, 6000 Frankfurt	Heterocyclisch substituierte sulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung in der landwirtschaft
GB2110689A (en) *	1981-12-03	1983-06-22	Sandoz Ltd	Herbicidal heterocyclic aminosulfonyl ureas and isoureas
AU9110982A (en) *	1981-12-07	1983-06-16	E.I. Du Pont De Nemours And Company	Sulfonamides
AU614485B2 (en) *	1982-02-27	1991-09-05	Nissan Chemical Industries Ltd.	Pyrazolesulfonylurea derivative, preparation thereof, herbicide containing said derivative as active ingredient and herbicidal method by use thereof
DE3324802A1 (de) *	1983-07-09	1985-01-17	Hoechst Ag, 6230 Frankfurt	Neue n-alkoxy- und n- alkylsulfonylaminosulfonylharnstoffe, und neue (pyrimido) triazino-thiadiazinoxide als vorprodukte
DE3330603A1 (de) *	1983-08-25	1985-03-21	Hoechst Ag, 6230 Frankfurt	Neue 2-amino-alkenylsulfonylharnstoffe
DE3822841A1 (de) *	1988-06-18	1989-12-21	Hoechst Ag	Substituierte sulfonyldiamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren

1988
- 1988-08-05 DE DE3826609A patent/DE3826609A1/de not_active Withdrawn
1989
- 1989-07-28 AT AT89113918T patent/ATE115138T1/de not_active IP Right Cessation
- 1989-07-28 EP EP89113918A patent/EP0353641B1/de not_active Expired - Lifetime
- 1989-07-28 DE DE58908721T patent/DE58908721D1/de not_active Expired - Fee Related
- 1989-07-28 ES ES89113918T patent/ES2067504T3/es not_active Expired - Lifetime
- 1989-08-03 DD DD89331465A patent/DD283918A5/de not_active IP Right Cessation
- 1989-08-03 US US07/389,070 patent/US5030270A/en not_active Expired - Fee Related
- 1989-08-03 IL IL9119889A patent/IL91198A/en not_active IP Right Cessation
- 1989-08-04 ZA ZA895960A patent/ZA895960B/xx unknown
- 1989-08-04 KR KR1019890011139A patent/KR900003137A/ko not_active Ceased
- 1989-08-04 SU SU894614736A patent/SU1741598A3/ru active
- 1989-08-04 DK DK384389A patent/DK384389A/da not_active Application Discontinuation
- 1989-08-04 CA CA000607540A patent/CA1339993C/en not_active Expired - Fee Related
- 1989-08-04 AU AU39296/89A patent/AU617205B2/en not_active Ceased
- 1989-08-04 HU HU893968A patent/HUT52761A/hu unknown
- 1989-08-04 BR BR898903945A patent/BR8903945A/pt unknown
- 1989-08-04 JP JP1201481A patent/JP2818799B2/ja not_active Expired - Lifetime
1995
- 1995-02-17 GR GR940404146T patent/GR3015098T3/el unknown

Also Published As

Publication number	Publication date
SU1741598A3 (ru)	1992-06-15
GR3015098T3 (en)	1995-05-31
JPH0291060A (ja)	1990-03-30
JP2818799B2 (ja)	1998-10-30
EP0353641A3 (de)	1991-10-30
AU3929689A (en)	1990-02-08
DK384389A (da)	1990-02-06
KR900003137A (ko)	1990-03-23
ZA895960B (en)	1990-08-29
US5030270A (en)	1991-07-09
IL91198A0 (en)	1990-03-19
AU617205B2 (en)	1991-11-21
CA1339993C (en)	1998-08-11
BR8903945A (pt)	1990-03-20
DK384389D0 (da)	1989-08-04
EP0353641A2 (de)	1990-02-07
ATE115138T1 (de)	1994-12-15
ES2067504T3 (es)	1995-04-01
HUT52761A (en)	1990-08-28
DE3826609A1 (de)	1990-02-08
EP0353641B1 (de)	1994-12-07
DE58908721D1 (de)	1995-01-19
IL91198A (en)	1994-02-27

Legal Events

Date	Code	Title	Description
1995-06-08	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0342569B1 (de)	1994-06-22	Heterocyclische 2-Alkoxyphenoxysulfonylharnstoffe und ihre Verwendung als Herbizide oder Pflanzenwachstumsregulatoren
EP0131258A2 (de)	1985-01-16	Neue N-Alkoxy- N-Alkylsulfonylaminosulfonylharnstoffe, und neue (Pyrimido) Triazino-thiatriazinoxide als Vorprodukte
EP0510032B1 (de)	1996-11-13	Pyridylsulfonylharnstoffe als herbizide und pflanzenwachstumsregulatoren, verfahren zu ihrer herstellung und ihre verwendung
EP0521500A1 (de)	1993-01-07	Salze von Pyridylsulfonylharnstoffen als Herbizide und Pflanzenwachstumsregulatoren, Verfahren zu ihrer Herstellung und ihre Verwendung
EP0353641B1 (de)	1994-12-07	Heterozyklisch substituierte Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide oder Pflanzenwachstumsregulatoren
DD202615A5 (de)	1983-09-28	Herbizide und wachstumsregulierende mittel
EP0347788B1 (de)	1994-08-10	Substituierte Sulfonyldiamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DD202378A5 (de)	1983-09-14	Herbizide und wachstumsregulierende mittel
EP0336354B1 (de)	1994-11-02	Heterocyclisch substituierte Alkyl- und Alkenylsulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide oder Pflanzenwachstumsregulatoren
DD212643A5 (de)	1984-08-22	Herbizide und wachstumsregulierende mittel
EP0342568B1 (de)	1994-02-02	Heterocyclisch substituierte Phenoxysulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide oder Pflanzenwachstumsregulatoren
EP0409114B1 (de)	1994-11-09	Heterocyclisch substituierte Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide oder Pflanzenwachstumsregulatoren
EP0319689B1 (de)	1993-12-15	Heterocyclisch substituierte N-Sultam-sulfonamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
EP0303114B1 (de)	1994-08-24	Heterocyclisch substituierte Sulfamidsäurephenylester, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
EP0388771B1 (de)	1995-06-28	Phenoxysulfonylharnstoffe auf Basis von 3-substituierten Salicylsäurealkylestern, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
EP0464838B1 (de)	1998-10-07	Substituierte Sulfonylalkylsulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE3807532A1 (de)	1989-09-21	Pyrimidin-carbonsaeuren, verfahren zur herstellung und ihre verwendung als herbizide
DE3709340A1 (de)	1988-09-29	Neue heterocyclisch substituierte benzylsulfonamide, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren
DE4022934A1 (de)	1991-01-24	Heterocyclisch substituierte sulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide oder pflanzenwachstumsregulatoren
DE3725939A1 (de)	1989-02-16	Heterocylisch substituierte sulfamidsaeurephenylester, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren
DE3806323A1 (de)	1989-09-07	Heterocyclisch substituierte sulfamidsaeurephenylester, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren
DD283910A5 (de)	1990-10-31	Herbizide und pflanzenwachstumsregulierende mittel
DE4122905A1 (de)	1993-01-21	Pyridylsulfonylharnstoffe als herbizide und pflanzenwachstumsregulatoren, verfahren zu ihrer herstellung und ihre verwendung