DE2109755A1 - Substituierte Thiadiazolidindione - Google Patents
Substituierte ThiadiazolidindioneInfo
- Publication number
- DE2109755A1 DE2109755A1 DE19712109755 DE2109755A DE2109755A1 DE 2109755 A1 DE2109755 A1 DE 2109755A1 DE 19712109755 DE19712109755 DE 19712109755 DE 2109755 A DE2109755 A DE 2109755A DE 2109755 A1 DE2109755 A1 DE 2109755A1
- Authority
- DE
- Germany
- Prior art keywords
- dione
- methyl
- weight
- thiadiazolidine
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- PZWGPRQVKJVQSE-UHFFFAOYSA-N thiadiazolidine-4,5-dione Chemical class O=C1NNSC1=O PZWGPRQVKJVQSE-UHFFFAOYSA-N 0.000 title claims description 9
- -1 alkylniercapto Chemical group 0.000 claims description 19
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 240000006694 Stellaria media Species 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 235000008427 Brassica arvensis Nutrition 0.000 description 4
- 244000024671 Brassica kaber Species 0.000 description 4
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 4
- 244000088461 Panicum crus-galli Species 0.000 description 4
- 235000011999 Panicum crusgalli Nutrition 0.000 description 4
- 244000292693 Poa annua Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 240000006597 Poa trivialis Species 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000007244 Zea mays Nutrition 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 3
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical class S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- LSXPXEJAKMFTTI-UHFFFAOYSA-N 2-methyl-4-phenyl-1,2,4-thiadiazolidine-3,5-dione Chemical compound O=C1N(C)SC(=O)N1C1=CC=CC=C1 LSXPXEJAKMFTTI-UHFFFAOYSA-N 0.000 description 2
- 241001621841 Alopecurus myosuroides Species 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
- 241000209048 Poa Species 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229940117953 phenylisothiocyanate Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RLRBTMWAHQDDPE-UHFFFAOYSA-N (3-isothiocyanatophenyl) N-methylcarbamate Chemical compound CNC(=O)OC=1C=C(C=CC1)N=C=S RLRBTMWAHQDDPE-UHFFFAOYSA-N 0.000 description 1
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical class O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 description 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- BOQXXVXKZLDLAT-UHFFFAOYSA-N 2-methyl-4-phenyl-1,2,4-oxadiazolidine-3,5-dione Chemical compound O=C1N(C)OC(=O)N1C1=CC=CC=C1 BOQXXVXKZLDLAT-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
- BWZDLMGVEVSNBI-UHFFFAOYSA-N 3-isothiocyanatophenol Chemical compound OC1=CC=CC(N=C=S)=C1 BWZDLMGVEVSNBI-UHFFFAOYSA-N 0.000 description 1
- XPFLDDSMNQTKFF-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-methyl-1,2,4-thiadiazolidine-3,5-dione Chemical compound O=C1N(C)SC(=O)N1C1=CC=C(Cl)C=C1 XPFLDDSMNQTKFF-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 241000192043 Echinochloa Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 241000862632 Soja Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical class O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712109755 DE2109755A1 (de) | 1971-03-02 | 1971-03-02 | Substituierte Thiadiazolidindione |
| NL7201510A NL7201510A (enExample) | 1971-03-02 | 1972-02-04 | |
| JP47017318A JPS4844432A (enExample) | 1971-03-02 | 1972-02-21 | |
| IT48521/72A IT951068B (it) | 1971-03-02 | 1972-02-23 | Tiadiazolidindioni sostituiti |
| IL38846A IL38846A0 (en) | 1971-03-02 | 1972-02-28 | Substituted thiadiazolidinediones and their use as herbicides |
| BR1171/72A BR7201171D0 (pt) | 1971-03-02 | 1972-02-29 | Composicoes herbicidas baseadas em novas tiadiazolidinadionas |
| ZA721359A ZA721359B (en) | 1971-03-02 | 1972-03-01 | Substituted thiadiazolidine-diones |
| DD161225A DD95149A5 (enExample) | 1971-03-02 | 1972-03-01 | |
| BE780047A BE780047A (fr) | 1971-03-02 | 1972-03-01 | Thiadiazolidines-diones substituees |
| FR7207225A FR2127929A5 (en) | 1971-03-02 | 1972-03-02 | 4-phenyl-1,2,4-thiadiazolidin-3,5-diones - useful as selective herbicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712109755 DE2109755A1 (de) | 1971-03-02 | 1971-03-02 | Substituierte Thiadiazolidindione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2109755A1 true DE2109755A1 (de) | 1972-09-07 |
Family
ID=5800224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712109755 Pending DE2109755A1 (de) | 1971-03-02 | 1971-03-02 | Substituierte Thiadiazolidindione |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS4844432A (enExample) |
| BE (1) | BE780047A (enExample) |
| BR (1) | BR7201171D0 (enExample) |
| DD (1) | DD95149A5 (enExample) |
| DE (1) | DE2109755A1 (enExample) |
| FR (1) | FR2127929A5 (enExample) |
| IL (1) | IL38846A0 (enExample) |
| IT (1) | IT951068B (enExample) |
| NL (1) | NL7201510A (enExample) |
| ZA (1) | ZA721359B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4309209A (en) | 1977-08-15 | 1982-01-05 | Chevron Research | Herbicidal method and composition |
| US4474598A (en) * | 1983-06-27 | 1984-10-02 | Shell Oil Company | Oxazolyl-substituted thiadiazolidinediones |
| US7666885B2 (en) | 2000-05-11 | 2010-02-23 | Consejo Superior De Investigaciones Cientificas | Enzyme inhibitors |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5161301U (enExample) * | 1974-11-06 | 1976-05-14 | ||
| JPS54147779U (enExample) * | 1978-04-06 | 1979-10-15 | ||
| ES2166328B1 (es) * | 2000-05-11 | 2003-09-16 | Consejo Superior Investigacion | Inhibidores heterociclicos del enzima gsk 3 utiles en el tratamiento de procesos neurodegenerativos e hiperproliferativos |
| WO2006001443A1 (ja) | 2004-06-28 | 2006-01-05 | Mitsubishi Chemical Corporation | ビフェニルテトラカルボン酸二無水物及びその製造方法、並びにこれを用いたポリイミド及びその製造方法 |
| JP4436822B2 (ja) * | 2006-10-25 | 2010-03-24 | 株式会社奈良機械製作所 | 粉粒体の熱交換装置及びその製造方法 |
-
1971
- 1971-03-02 DE DE19712109755 patent/DE2109755A1/de active Pending
-
1972
- 1972-02-04 NL NL7201510A patent/NL7201510A/xx unknown
- 1972-02-21 JP JP47017318A patent/JPS4844432A/ja active Pending
- 1972-02-23 IT IT48521/72A patent/IT951068B/it active
- 1972-02-28 IL IL38846A patent/IL38846A0/xx unknown
- 1972-02-29 BR BR1171/72A patent/BR7201171D0/pt unknown
- 1972-03-01 DD DD161225A patent/DD95149A5/xx unknown
- 1972-03-01 ZA ZA721359A patent/ZA721359B/xx unknown
- 1972-03-01 BE BE780047A patent/BE780047A/xx unknown
- 1972-03-02 FR FR7207225A patent/FR2127929A5/fr not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4309209A (en) | 1977-08-15 | 1982-01-05 | Chevron Research | Herbicidal method and composition |
| US4474598A (en) * | 1983-06-27 | 1984-10-02 | Shell Oil Company | Oxazolyl-substituted thiadiazolidinediones |
| US7666885B2 (en) | 2000-05-11 | 2010-02-23 | Consejo Superior De Investigaciones Cientificas | Enzyme inhibitors |
| US7781463B2 (en) | 2000-05-11 | 2010-08-24 | Consejo Superior De Investigaciones Cientificas | Enzyme inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2127929A5 (en) | 1972-10-13 |
| ZA721359B (en) | 1972-12-27 |
| BE780047A (fr) | 1972-09-01 |
| BR7201171D0 (pt) | 1973-04-26 |
| DD95149A5 (enExample) | 1973-01-12 |
| JPS4844432A (enExample) | 1973-06-26 |
| IL38846A0 (en) | 1972-04-27 |
| IT951068B (it) | 1973-06-30 |
| NL7201510A (enExample) | 1972-09-05 |
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