CS197326B2 - Herbicide means and method of making the active components - Google Patents
Herbicide means and method of making the active components Download PDFInfo
- Publication number
- CS197326B2 CS197326B2 CS784415A CS441578A CS197326B2 CS 197326 B2 CS197326 B2 CS 197326B2 CS 784415 A CS784415 A CS 784415A CS 441578 A CS441578 A CS 441578A CS 197326 B2 CS197326 B2 CS 197326B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- phenyl
- ester
- acid
- substituted
- cyanomethyl
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 8
- 239000004009 herbicide Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- -1 cyanomethyl Chemical group 0.000 claims description 92
- 239000002253 acid Substances 0.000 claims description 45
- 239000004480 active ingredient Substances 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims 1
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- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 25
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- NVDLOQJYFKNQON-UHFFFAOYSA-N [3-(dimethylcarbamoylamino)phenyl] n-(cyanomethyl)-n-phenylcarbamate Chemical compound CN(C)C(=O)NC1=CC=CC(OC(=O)N(CC#N)C=2C=CC=CC=2)=C1 NVDLOQJYFKNQON-UHFFFAOYSA-N 0.000 description 3
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- RVPIJUCNCBVJKR-UHFFFAOYSA-N [3-(methylcarbamoylamino)phenyl] n-(2-cyanoethyl)-n-(3-methylphenyl)carbamate Chemical compound CNC(=O)NC1=CC=CC(OC(=O)N(CCC#N)C=2C=C(C)C=CC=2)=C1 RVPIJUCNCBVJKR-UHFFFAOYSA-N 0.000 description 1
- OLRRXMVYJRCYLE-UHFFFAOYSA-N [3-(methylcarbamoylamino)phenyl] n-(3-chloro-4-methylphenyl)-n-(cyanomethyl)carbamate Chemical compound CNC(=O)NC1=CC=CC(OC(=O)N(CC#N)C=2C=C(Cl)C(C)=CC=2)=C1 OLRRXMVYJRCYLE-UHFFFAOYSA-N 0.000 description 1
- XMESENFMLOUKQE-UHFFFAOYSA-N [3-(methylcarbamoylamino)phenyl] n-(cyanomethyl)-n-phenylcarbamate Chemical compound CNC(=O)NC1=CC=CC(OC(=O)N(CC#N)C=2C=CC=CC=2)=C1 XMESENFMLOUKQE-UHFFFAOYSA-N 0.000 description 1
- LLSPWQCZWKOCRJ-UHFFFAOYSA-N [3-(propan-2-ylcarbamoylamino)phenyl] n-(cyanomethyl)-n-(3-methylphenyl)carbamate Chemical compound CC(C)NC(=O)NC1=CC=CC(OC(=O)N(CC#N)C=2C=C(C)C=CC=2)=C1 LLSPWQCZWKOCRJ-UHFFFAOYSA-N 0.000 description 1
- JPPYQDQRORVLJM-UHFFFAOYSA-N [3-(propylcarbamoylamino)phenyl] n-(2-cyanoethyl)-n-(3-methylphenyl)carbamate Chemical compound CCCNC(=O)NC1=CC=CC(OC(=O)N(CCC#N)C=2C=C(C)C=CC=2)=C1 JPPYQDQRORVLJM-UHFFFAOYSA-N 0.000 description 1
- FLPPZQHRJCKMAH-UHFFFAOYSA-N [3-(propylcarbamoylamino)phenyl] n-(cyanomethyl)-n-(3-methylphenyl)carbamate Chemical compound CCCNC(=O)NC1=CC=CC(OC(=O)N(CC#N)C=2C=C(C)C=CC=2)=C1 FLPPZQHRJCKMAH-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004848 alkoxyethyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- BUSBFZWLPXDYIC-UHFFFAOYSA-N arsonic acid Chemical class O[AsH](O)=O BUSBFZWLPXDYIC-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 150000005130 benzoxazines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- QWLOTCHRKCKVMO-UHFFFAOYSA-N cyanomethyl-(3,4-dimethylphenyl)carbamic acid Chemical compound C(#N)CN(C(O)=O)C1=CC(=C(C=C1)C)C QWLOTCHRKCKVMO-UHFFFAOYSA-N 0.000 description 1
- YGEUHYSUEAKPNK-UHFFFAOYSA-N cyanomethyl-(3,5-dimethylphenyl)carbamic acid Chemical compound C(#N)CN(C(O)=O)C1=CC(=CC(=C1)C)C YGEUHYSUEAKPNK-UHFFFAOYSA-N 0.000 description 1
- KWLWUXHVJLRMCK-UHFFFAOYSA-N cyanomethyl-(3-methoxyphenyl)carbamic acid Chemical compound C(#N)CN(C(O)=O)C1=CC(=CC=C1)OC KWLWUXHVJLRMCK-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- QQSGDKKFXBGYON-UHFFFAOYSA-N ethoxy-methylperoxy-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxy-sulfanylidene-$l^{5}-phosphane Chemical class CCOP(=S)(OOC)OC1=CC(C)=NC(C(C)C)=N1 QQSGDKKFXBGYON-UHFFFAOYSA-N 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 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
- 239000006028 limestone Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- XMCWHSNPPQIPQX-UHFFFAOYSA-N n-(2-cyanoethyl)-n-phenylcarbamoyl chloride Chemical compound N#CCCN(C(=O)Cl)C1=CC=CC=C1 XMCWHSNPPQIPQX-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- IBIKVXOGGWLTSG-UHFFFAOYSA-N phenyl(2-propoxyethyl)carbamic acid Chemical compound C(CC)OCCN(C(O)=O)C1=CC=CC=C1 IBIKVXOGGWLTSG-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N phenyldimethylamine Natural products CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical class P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- BFZYLUGEHGYJKJ-UHFFFAOYSA-N pyrazolidine-3-thione Chemical class S=C1CCNN1 BFZYLUGEHGYJKJ-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000005299 pyridinones Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000008318 pyrimidones Chemical class 0.000 description 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- OLPRIZQBWZMBAS-UHFFFAOYSA-N thiadiazolidine 1,1-dioxide Chemical class O=S1(=O)CCNN1 OLPRIZQBWZMBAS-UHFFFAOYSA-N 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 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
- 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<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772730325 DE2730325A1 (de) | 1977-07-01 | 1977-07-01 | Carbanilsaeure-(3-ureido-phenyl)- ester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS197326B2 true CS197326B2 (en) | 1980-04-30 |
Family
ID=6013198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS784415A CS197326B2 (en) | 1977-07-01 | 1978-07-03 | Herbicide means and method of making the active components |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4378318A (pl) |
| JP (1) | JPS5416450A (pl) |
| AU (1) | AU518443B2 (pl) |
| BE (1) | BE868642A (pl) |
| CA (1) | CA1100986A (pl) |
| CH (1) | CH637634A5 (pl) |
| CS (1) | CS197326B2 (pl) |
| DD (1) | DD135440A5 (pl) |
| DE (1) | DE2730325A1 (pl) |
| DK (1) | DK294878A (pl) |
| ES (1) | ES471311A1 (pl) |
| FR (1) | FR2395986A1 (pl) |
| GB (1) | GB2000500B (pl) |
| HU (1) | HU182600B (pl) |
| IE (1) | IE47008B1 (pl) |
| IL (1) | IL55039A (pl) |
| IT (1) | IT1096866B (pl) |
| LU (1) | LU79899A1 (pl) |
| NL (1) | NL7806766A (pl) |
| PL (1) | PL110791B1 (pl) |
| PT (1) | PT68240A (pl) |
| SU (1) | SU797574A3 (pl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3126909A1 (de) * | 1981-07-08 | 1983-02-10 | Hoechst Ag, 6000 Frankfurt | "kupferkomplex-monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe" |
| DE10257080A1 (de) * | 2002-12-06 | 2004-06-24 | Bayer Cropscience Ag | Substituierte Pyrazolincarboxanilide |
| EP2061844B1 (en) * | 2006-11-09 | 2017-03-15 | Huntsman Advanced Materials (Switzerland) GmbH | Mixtures of reactive dyes and their use in a method for trichromatic dyeing or printing |
| WO2014011133A1 (en) | 2012-07-12 | 2014-01-16 | Mke Silah Fabrikasi Mudurlugu | Buttstock assembly whose length can be adjusted, having a rotating mechanism and fit lock |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133808A (en) * | 1959-03-16 | 1964-05-19 | Monsanto Chemicals | Herbicide composition |
| DE1156780B (de) * | 1961-08-29 | 1963-11-07 | Bayer Ag | Verfahren zur Herstellung von Carbaminsaeureestern |
| US3404975A (en) * | 1964-12-18 | 1968-10-08 | Fmc Corp | m-(carbamoyloxy)-carbanilates as herbicides |
| DE1593520C3 (de) * | 1966-09-05 | 1974-07-11 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 3-(Carbamoyloxyphenyl)-harnstoffe bzw. -thioharnstoffe, diese enthaltende Mittel mit selektiver herbizider Wirkung sowie Verfahren zu deren Herstellung |
| DE1618169A1 (de) * | 1967-05-31 | 1970-12-10 | Basf Ag | Substituierte Phenylcarbaminsaeureureidophenylester |
| US3867426A (en) * | 1970-10-02 | 1975-02-18 | Monsanto Co | Herbicidal meta-bifunctional benzenes |
| US3780104A (en) * | 1971-03-15 | 1973-12-18 | Stauffer Chemical Co | Phenoxy acetals |
| US3778473A (en) * | 1971-05-19 | 1973-12-11 | Upjohn Co | Organic compounds and process |
| EG10699A (en) * | 1971-06-23 | 1976-07-31 | Bayer Ag | Novel n.carbamic aryl acid esters method for preparation and their use for controlling plant growth |
| BE793176A (fr) * | 1971-12-22 | 1973-06-22 | Scm Corp | Composition herbicide |
| US3823178A (en) * | 1972-05-08 | 1974-07-09 | K Szabo | Novel m-(3,3-disubstitutedureido)phenyl(alpha-cyanoalkyl)carbamates and method for the control of undesirable plant species therewith |
| DE2423536A1 (de) * | 1974-05-15 | 1975-11-27 | Bayer Ag | 3-amino-phenylessigsaeure-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
-
1977
- 1977-07-01 DE DE19772730325 patent/DE2730325A1/de not_active Withdrawn
-
1978
- 1978-06-22 NL NL7806766A patent/NL7806766A/xx not_active Application Discontinuation
- 1978-06-23 IE IE1258/78A patent/IE47008B1/en unknown
- 1978-06-28 AU AU37539/78A patent/AU518443B2/en not_active Expired
- 1978-06-29 IT IT25104/78A patent/IT1096866B/it active
- 1978-06-29 DD DD78206383A patent/DD135440A5/xx unknown
- 1978-06-29 IL IL7855039A patent/IL55039A/xx unknown
- 1978-06-29 PT PT68240A patent/PT68240A/pt unknown
- 1978-06-29 PL PL1978208013A patent/PL110791B1/pl unknown
- 1978-06-29 LU LU79899A patent/LU79899A1/xx unknown
- 1978-06-29 DK DK294878A patent/DK294878A/da not_active Application Discontinuation
- 1978-06-30 CH CH718878A patent/CH637634A5/de not_active IP Right Cessation
- 1978-06-30 BE BE188992A patent/BE868642A/xx not_active IP Right Cessation
- 1978-06-30 ES ES471311A patent/ES471311A1/es not_active Expired
- 1978-06-30 HU HU78SCHE650A patent/HU182600B/hu unknown
- 1978-06-30 GB GB7828440A patent/GB2000500B/en not_active Expired
- 1978-06-30 SU SU782631495A patent/SU797574A3/ru active
- 1978-06-30 JP JP7969578A patent/JPS5416450A/ja active Granted
- 1978-06-30 CA CA306,587A patent/CA1100986A/en not_active Expired
- 1978-07-03 FR FR7819777A patent/FR2395986A1/fr active Granted
- 1978-07-03 CS CS784415A patent/CS197326B2/cs unknown
-
1981
- 1981-07-15 US US06/283,667 patent/US4378318A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU3753978A (en) | 1980-01-03 |
| IE47008B1 (en) | 1983-11-30 |
| DK294878A (da) | 1979-01-02 |
| LU79899A1 (pl) | 1978-12-07 |
| IL55039A (en) | 1982-07-30 |
| PT68240A (de) | 1978-07-01 |
| IL55039A0 (en) | 1978-08-31 |
| ES471311A1 (es) | 1979-09-01 |
| GB2000500A (en) | 1979-01-10 |
| US4378318A (en) | 1983-03-29 |
| JPS5416450A (en) | 1979-02-07 |
| IE781258L (en) | 1979-01-01 |
| DD135440A5 (de) | 1979-05-09 |
| CH637634A5 (de) | 1983-08-15 |
| GB2000500B (en) | 1982-02-24 |
| FR2395986A1 (fr) | 1979-01-26 |
| FR2395986B1 (pl) | 1984-04-20 |
| DE2730325A1 (de) | 1979-01-11 |
| BE868642A (fr) | 1979-01-02 |
| AU518443B2 (en) | 1981-10-01 |
| SU797574A3 (ru) | 1981-01-15 |
| IT1096866B (it) | 1985-08-26 |
| JPS5630343B2 (pl) | 1981-07-14 |
| PL110791B1 (en) | 1980-07-31 |
| IT7825104A0 (it) | 1978-06-29 |
| NL7806766A (nl) | 1979-01-03 |
| HU182600B (en) | 1984-02-28 |
| PL208013A1 (pl) | 1979-04-09 |
| CA1100986A (en) | 1981-05-12 |
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