GB1561695A - Chloroacetyl-phenylamino-acetamides for the regulation of plant growth - Google Patents
Chloroacetyl-phenylamino-acetamides for the regulation of plant growth Download PDFInfo
- Publication number
- GB1561695A GB1561695A GB28489/76A GB2848976A GB1561695A GB 1561695 A GB1561695 A GB 1561695A GB 28489/76 A GB28489/76 A GB 28489/76A GB 2848976 A GB2848976 A GB 2848976A GB 1561695 A GB1561695 A GB 1561695A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- plants
- growth
- formula
- compounds
- 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.)
- Expired
Links
- 230000008635 plant growth Effects 0.000 title claims description 17
- -1 Chloroacetyl-phenylamino-acetamides Chemical class 0.000 title description 19
- 230000033228 biological regulation Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 64
- 239000004480 active ingredient Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 31
- 241000196324 Embryophyta Species 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 14
- 230000000979 retarding effect Effects 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 9
- 244000068988 Glycine max Species 0.000 claims description 7
- 235000013339 cereals Nutrition 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000008247 solid mixture Substances 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- 244000025254 Cannabis sativa Species 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 230000012010 growth Effects 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
- 229940093499 ethyl acetate Drugs 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 241000209504 Poaceae Species 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000002689 soil Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 229940106681 chloroacetic acid Drugs 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- DMOQHEWCUXULLO-UHFFFAOYSA-N 2-(2,6-dimethylanilino)acetic acid Chemical compound CC1=CC=CC(C)=C1NCC(O)=O DMOQHEWCUXULLO-UHFFFAOYSA-N 0.000 description 3
- UGIUIFDIFSBIBH-UHFFFAOYSA-N 2-(n-(2-chloroacetyl)-2,6-dimethylanilino)acetic acid Chemical compound CC1=CC=CC(C)=C1N(CC(O)=O)C(=O)CCl UGIUIFDIFSBIBH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical class OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 239000002253 acid Substances 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JADYRKYZRVLQFB-UHFFFAOYSA-N 2-(2,6-dimethylanilino)-n-propylacetamide Chemical compound CCCNC(=O)CNC1=C(C)C=CC=C1C JADYRKYZRVLQFB-UHFFFAOYSA-N 0.000 description 2
- QRKJNCRCYBKANP-UHFFFAOYSA-N 2-amino-n-phenylacetamide Chemical class NCC(=O)NC1=CC=CC=C1 QRKJNCRCYBKANP-UHFFFAOYSA-N 0.000 description 2
- GXBRYTMUEZNYJT-UHFFFAOYSA-N 2-anilinoacetamide Chemical class NC(=O)CNC1=CC=CC=C1 GXBRYTMUEZNYJT-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 206010053759 Growth retardation Diseases 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 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
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 231100000001 growth retardation Toxicity 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
- 125000006431 methyl cyclopropyl group Chemical group 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003415 peat Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000009105 vegetative growth Effects 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 230000003442 weekly effect Effects 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- MFUUKPXESMFXBH-UHFFFAOYSA-N 2-(n-(2-chloroacetyl)anilino)acetic acid Chemical compound OC(=O)CN(C(=O)CCl)C1=CC=CC=C1 MFUUKPXESMFXBH-UHFFFAOYSA-N 0.000 description 1
- XWKAVQKJQBISOL-UHFFFAOYSA-N 2-(phenylazaniumyl)propanoate Chemical class OC(=O)C(C)NC1=CC=CC=C1 XWKAVQKJQBISOL-UHFFFAOYSA-N 0.000 description 1
- PERLAUCSKSAHSO-UHFFFAOYSA-N 2-anilino-n-(2-chloroacetyl)acetamide Chemical class ClCC(=O)NC(=O)CNC1=CC=CC=C1 PERLAUCSKSAHSO-UHFFFAOYSA-N 0.000 description 1
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
- LKRZCUQFUCYWLZ-UHFFFAOYSA-N 2-chloroacetyl bromide Chemical compound ClCC(Br)=O LKRZCUQFUCYWLZ-UHFFFAOYSA-N 0.000 description 1
- 240000004585 Dactylis glomerata Species 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000410074 Festuca ovina Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000735234 Ligustrum Species 0.000 description 1
- 240000004296 Lolium perenne Species 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 241000209049 Poa pratensis Species 0.000 description 1
- 244000172730 Rubus fruticosus Species 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229940059260 amidate Drugs 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- QKZIVVMOMKTVIK-UHFFFAOYSA-N anilinomethanesulfonic acid Chemical compound OS(=O)(=O)CNC1=CC=CC=C1 QKZIVVMOMKTVIK-UHFFFAOYSA-N 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000019993 champagne Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007596 consolidation process Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000004491 dispersible concentrate Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- WKARXCUFHCJKRA-UHFFFAOYSA-N methyl 2-(2,6-dimethylanilino)acetate Chemical compound COC(=O)CNC1=C(C)C=CC=C1C WKARXCUFHCJKRA-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000026267 regulation of growth Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
Classifications
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH896075A CH593606A5 (en) | 1975-07-09 | 1975-07-09 | Substd. chloro acetyl phenyl amino acetamides - having plant growth inhibiting activity without phytotoxic effect |
| CH429876A CH604492A5 (en) | 1976-04-06 | 1976-04-06 | Substd. chloro acetyl phenyl amino acetamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1561695A true GB1561695A (en) | 1980-02-27 |
Family
ID=25695148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28489/76A Expired GB1561695A (en) | 1975-07-09 | 1976-07-08 | Chloroacetyl-phenylamino-acetamides for the regulation of plant growth |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5210225A (enExample) |
| DE (1) | DE2630373A1 (enExample) |
| FR (1) | FR2317279A1 (enExample) |
| GB (1) | GB1561695A (enExample) |
| IL (1) | IL49992A (enExample) |
| LU (1) | LU75335A1 (enExample) |
| NL (1) | NL7607588A (enExample) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK140082B (da) * | 1972-03-10 | 1979-06-18 | Hercules Inc | Herbicid indeholdende som aktiv bestanddel en aromatisk aminforbindelse. |
| DE2416213A1 (de) * | 1974-04-03 | 1975-10-16 | Ciba Geigy Ag | Phenylaminoacetamide zur beeinflussung des pflanzenwachstums |
-
1976
- 1976-07-06 DE DE19762630373 patent/DE2630373A1/de not_active Withdrawn
- 1976-07-07 FR FR7620730A patent/FR2317279A1/fr active Granted
- 1976-07-07 IL IL49992A patent/IL49992A/xx unknown
- 1976-07-08 GB GB28489/76A patent/GB1561695A/en not_active Expired
- 1976-07-08 NL NL7607588A patent/NL7607588A/xx not_active Application Discontinuation
- 1976-07-08 LU LU75335A patent/LU75335A1/xx unknown
- 1976-07-09 JP JP51081853A patent/JPS5210225A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2317279A1 (fr) | 1977-02-04 |
| JPS5210225A (en) | 1977-01-26 |
| IL49992A0 (en) | 1976-09-30 |
| FR2317279B1 (enExample) | 1978-04-14 |
| IL49992A (en) | 1983-10-31 |
| LU75335A1 (enExample) | 1977-04-01 |
| NL7607588A (nl) | 1977-01-11 |
| DE2630373A1 (de) | 1977-01-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4270948A (en) | Herbicidal compound, herbicidal composition containing the same, and method of use thereof | |
| JPS6230184B2 (enExample) | ||
| DE2657728C2 (enExample) | ||
| CA1140122A (en) | SALTS OF .alpha.-AMINOACETANILIDES, THE MANUFACTURE THEREOF, AND THEIR USE AS PLANT GROWTH REGULATORS | |
| DE2548231A1 (de) | 1-(bis-trifluormethylphenyl)-2-oxo- pyrrolidin-4-carbonsaeurederivate, deren herstellung und verwendung als pflanzenwachstumsregulatoren und herbizide | |
| EP0382463B1 (en) | Maleimide compounds and fungicides containing them | |
| EP0027019B1 (en) | 2-chloro-4,5-disubstituted-thiazoles, process for their preparation, use as antidotes against damage caused by herbicides and mixtures containing them | |
| US4243406A (en) | 5-Aryl-4-isoxazolecarboxylate-safening agents | |
| US4126440A (en) | Hydroxamic acid derivatives for regulating plant growth | |
| EP0115470B1 (de) | Optisch aktives N-(1'-Methyl-2'-methoxyethyl)-N-chloracetyl-2,6-di-methylanilin als Herbizid | |
| US4298375A (en) | 2-Substituted-5-phenyl-4-thiazolecarboxylic acids and their derivatives as safening agents | |
| KR830001039B1 (ko) | 2-이미노-1, 3-디티오 및 1, 3-옥사티오 복소환 화합물 함유 제초제 조성물 | |
| GB1561695A (en) | Chloroacetyl-phenylamino-acetamides for the regulation of plant growth | |
| KR860002107B1 (ko) | α, α-디메틸페닐초산 아닐리드 유도체의 제조방법 | |
| US4063921A (en) | Method for the cultivation of plants employing α-cyano-α-hydroxyimino-acetamide derivatives | |
| US4334909A (en) | N-(Alkoxymethyl)-2'-nitro-6'-substituted-2-haloacetanilides and their use as herbicides and plant growth regulants | |
| CA1120034A (en) | Phenoxy-phenoxy-propionic acid amides, process for their manufacture and their use as herbicides | |
| US4685962A (en) | Phenylacetanilide derivatives | |
| CS214799B2 (cs) | Prostředek k regulaci růstu rostlin a způsob výroby účinných látek | |
| EP0044201A1 (en) | 2-Chloro-4-trifluoromethyl-thiazolecarbothioic acids useful as herbicidal safeners | |
| US3988328A (en) | 5-Amino-2,3,7,8-tetrathiaalkane-1,9-dioic acids, esters and salts | |
| KR830000743B1 (ko) | 치환페닐 요소의 제조법 | |
| US4486222A (en) | Herbicide composition and process for the preparation of the active ingredients herbicidal phenyl carbonates | |
| JPS6143160A (ja) | シクロヘキセンジカルボン酸ジアミド類およびこれを有効成分とする除草剤 | |
| CA1129882A (en) | Benzamide derivatives and their use as herbicides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |