DD149996A5 - SELECTIVE HERBICIDES MEDIUM - Google Patents
SELECTIVE HERBICIDES MEDIUM Download PDFInfo
- Publication number
- DD149996A5 DD149996A5 DD80220215A DD22021580A DD149996A5 DD 149996 A5 DD149996 A5 DD 149996A5 DD 80220215 A DD80220215 A DD 80220215A DD 22021580 A DD22021580 A DD 22021580A DD 149996 A5 DD149996 A5 DD 149996A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- propynyl
- ester
- compounds
- acid
- carbanilic acid
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 239000011593 sulfur Substances 0.000 claims abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 2
- FPCVKACKGOHVAO-UHFFFAOYSA-N phenyl(prop-2-ynyl)carbamic acid Chemical compound C(C#C)N(C(O)=O)C1=CC=CC=C1 FPCVKACKGOHVAO-UHFFFAOYSA-N 0.000 claims description 9
- 230000002363 herbicidal effect Effects 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 15
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 230000006378 damage Effects 0.000 abstract description 8
- 239000000969 carrier Substances 0.000 abstract description 5
- QJUUGNSQLMIUAJ-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] N-phenyl-N-prop-2-ynylcarbamate Chemical class COC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC#C)=O QJUUGNSQLMIUAJ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003139 biocide Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 26
- -1 aminophenyl Chemical group 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000011331 Brassica Nutrition 0.000 description 2
- 241000219198 Brassica Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- 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
- 235000002634 Solanum Nutrition 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- IZKIWEYIOKPHLF-UHFFFAOYSA-N n-prop-2-ynylaniline Chemical compound C#CCNC1=CC=CC=C1 IZKIWEYIOKPHLF-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 1
- GIRGFOHZHDGCJA-UHFFFAOYSA-N 2-[(2,3,6-trichlorophenyl)methoxy]propan-2-ol Chemical compound CC(C)(O)OCC1=C(Cl)C=CC(Cl)=C1Cl GIRGFOHZHDGCJA-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
- KKAHGSQLSTUDAV-UHFFFAOYSA-N 3-butynoic acid Chemical compound OC(=O)CC#C KKAHGSQLSTUDAV-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 240000004385 Centaurea cyanus Species 0.000 description 1
- 235000005940 Centaurea cyanus Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 244000303225 Lamium amplexicaule Species 0.000 description 1
- 235000009198 Lamium amplexicaule Nutrition 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 240000005498 Setaria italica Species 0.000 description 1
- 235000007226 Setaria italica Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- MNBOFGKALCNRMG-UHFFFAOYSA-N [3-(ethoxycarbonylamino)phenyl] N-phenyl-N-prop-2-ynylcarbamate Chemical compound C(C)OC(=O)NC=1C=C(C=CC1)OC(N(C1=CC=CC=C1)CC#C)=O MNBOFGKALCNRMG-UHFFFAOYSA-N 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 235000012735 amaranth Nutrition 0.000 description 1
- 239000004178 amaranth Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 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
- 229920005551 calcium lignosulfonate Polymers 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
- 235000013877 carbamide Nutrition 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 150000004891 diazines Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003560 thiocarbamic acids Chemical class 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Erfindungsaufgabe ist die Bereitstellung eines Unkrautbekaempfungsmittels, das keine Schaedigung der Kulturpflanzen hervorruft aber auch bei schwer bekaempfbaren Unkraeutern einzusetzen ist. Erfindungsgemaesz sind die neuen Mittel dadurch gekennzeichnet, dasz sie einen Gehalt an einem oder mehreren N-(2-Propinyl)-carbanilsaeure-(3-methoxycarbonylaminophenyl)-estern der allgemeinen Formel, in der R C&ind1!-C&ind4!-Alkyl, C&ind3!-C&ind4!-Alkenyl oder C&ind3!-C&ind4!-Alkinyl und X Sauerstoff oder Schwefel darstellen in Mischung mit Traeger- und/oder Hilfsstoffen aufweisen.The object of the invention is the provision of a weed-killing agent which does not cause damage to crops but can also be used in the case of weeds which are difficult to catch. According to the invention, the novel agents are characterized as having a content of one or more N- (2-propynyl) -carbanilic acid (3-methoxycarbonylaminophenyl) esters of the general formula in which R is C 1 -C 4 -alkyl, C & ind 3! -C & ind4! -Alkenyl or C & ind3! -C & ind4! Alkynyl and X are oxygen or sulfur in mixture with carriers and / or auxiliaries.
Description
Die Erfindung betrifft neue selektive herbizide Mittel·The invention relates to novel selective herbicidal compositions
Die herbizide Wirkung von Carbanilsäure-(3-alkoxycarbonylaminophenyl)-estern bzw. Diurethanen ist bereits bekannt (DE-PS 1 567 115).The herbicidal action of carbanilic acid (3-alkoxycarbonylaminophenyl) esters or diurethanes is already known (DE-PS 1 567 115).
Eine ausreichende Selektivität besitzen diese Verbindungen jjedoch nur in Beta-Eüben. Darüber hinaus weisen die Verbindungen große Wirkungslücken auf.However, these compounds have sufficient selectivity only in beta-turnovers. In addition, the compounds have large gaps in their effectiveness.
Es ist Ziel der Erfindung, diese Nachteile zu beseitigen.It is an object of the invention to eliminate these disadvantages.
Aufgabe der vorliegenden Erfindung ist es, ein Unkrautbekämpfungsmittel zu schaffen, das auch Wirkung gegen schwer bekämpfbare Unkräuter besitzt, insbesondere bei voller Verträglichkeit für wichtige landwirtschaftliche Kulturen. Diese Aufgabe wird erfindungsgemäß durch ein Mittel gelöst, das gekennzeichnet ist durch einen Gehalt an einem oder mehreren N-(2-Propinyl)-carbanilsäure-(3-methoxycarbonyl~ aminophenyl)-estern der allgemeinen FormelThe object of the present invention is to provide a weed control agent which also has activity against hard-to-control weeds, especially with full compatibility for important agricultural crops. This object is achieved by an agent which is characterized by a content of one or more N- (2-propynyl) -carbanilsäure- (3-methoxycarbonyl ~ aminophenyl) esters of the general formula
220215220215
57 W 1257 W 12
CH2-C=CHCH 2 -C = CH
in der E Cj-C^-Alkyl, C^-C^-Alkenyl oder Co-C^-Alkinyl und X Sauerstoff oder Schwefel darstellen·in which E represents C 1 -C 4 -alkyl, C 1 -C 4 -alkenyl or C 1 -C 4 -alkynyl and X represents oxygen or sulfur ·
Die erfindungsgemäßen Verbindungen zeigen überraschenderweise eine größere selektive herbizide Wirkung als die bekannten konstitutionsanalogen Verbindungen gleicher Wirkungsrichtung,The compounds according to the invention surprisingly show a greater selective herbicidal action than the known constitution-analogous compounds of the same direction of action,
Ein weiterer technisch viichtiger Vorteil der erfindungsgemäßen Verbindungen liegt in ihrer praktischen Anwendung, indem sie als neue Herbizide gegen solche resistente Unkräuter und eine Sekundärflora eingesetzt werden können, die von den praxisbekannten Herbiziden wegen Resistenzbildung der Unkräuter nicht mehr ausreichend bekämpft werden»Another technically viichtiger advantage of the compounds of the invention lies in their practical application by they can be used as new herbicides against such resistant weeds and a secondary flora that are no longer sufficiently controlled by the known herbicides because of resistance of the weeds »
Die erfindungsgemäßen Verbindungen zeichnen sich durch eine breite blattherbizide Wirkung aus. Sie können zur Bekämpfung dikotyler Unkräuter verwendet werden. Bei den Verbindungen werden im Nachauf laufverfahren Ackerunkräuter, wie Stellaria media, Matricaria chamomilla, Lamium amplexicaule, Centaurea cyanus, Amarant us retroflexus, Solanum saccharoides, Eschholtzia californica, Impomoea purpursa, Setaria italica und anders Unkräuter bekämpft.The compounds according to the invention are distinguished by a broad foliar herbicidal action. They can be used to control dicotyledonous weeds. The compounds are Nachauf running process field weeds such as Stellaria media, Matricaria chamomilla, Lamium amplexicaule, Centaurea cyanus, amaranth us retroflexus, Solanum saccharoides, Eschholtzia californica, Impomoea purpursa, Setaria italica and other weeds combated.
220215220215
- 3 - 57 W 12- 3 - 57 W 12
Zelt Bekämpfung von Samen-Unkräutern werden in der Regel Aufwandmengen von 1 kg bis 5 kg Wirkst off/ha verwendet. Dabei erweisen sich die gekennzeichneten Wirkstoffe überraschenderweise selektiv in Nutzpflanzenkulturen, "wie Baumwolle, Kartoffel, Mais, Weizen und Eeis.Tent control of seed weeds are usually used rates of 1 kg to 5 kg Wirkst off / ha. Surprisingly, the labeled compounds are found to be selective in crops such as cotton, potato, corn, wheat and ice.
Die erfindungsgemäßen Verbindungen können entweder allein in Mischung miteinander oder mit anderen Wirkstoffen angewendet werden. Gegebenenfalls können andere Pflanzenschutzoder Schädlingsbekämpfungsmittel je nach dem gewünschten Zweck zugesetzt werden.The compounds of the invention can be used either alone in admixture with each other or with other active ingredients. Optionally, other crop protection or pest control agents may be added according to the desired purpose.
Sofern eine Verbreiterung des Wirkungsspektrums beabsichtigt ist, können auch andere Herbizide zugesetzt werden. Beispielsweise eignen sich als herbizid wirksame Mischungspaxtner Wirkstoffe aus den Gruppen der Triazine, Aminotriazole, Anilide, Diazine, Uracile, aliphatischen Carbonsäuren und Aryloxycarbonsäuren, Hydrazide, Amide, Nitrile, Ester solcher Carbonsäuren, Carbamidsäure- und Thiocarbaminsäureester, Harnstoffe, 2,3,6-Trichlorbenzyloxyisopropanol und rhodanhaltigen Mitteln u,a,. Unter anderen Zusätzen sind z, B, auch nicht phytotoxische Zusätze zu verstehen, die bei Herbiziden eine Synergist isehe Wirkungssteigerung ergeben, wie Netzmittel, Emulgatoren, Lösungsmittel und ölige Zusätze,If a widening of the spectrum of action is intended, other herbicides can be added. Examples of suitable herbicidally active compounding agents are active compounds from the groups of the triazines, aminotriazoles, anilides, diazines, uracils, aliphatic carboxylic acids and aryloxycarboxylic acids, hydrazides, amides, nitriles, esters of such carboxylic acids, carbamic acid and thiocarbamic acid esters, ureas, 2,3,6- Trichlorobenzyloxyisopropanol and rhodan-containing agents u, a ,. Among other additives, z, B are also non-phytotoxic additives which, in the case of herbicides, produce a synergistic increase in activity, such as wetting agents, emulsifiers, solvents and oily additives,
Zweckmäßig werden die gekennzeichneten Wirkstoffe oder deren Mischungen in Form von Zubereitungen, wie Pulvern, Streumitteln, Granulaten, Lösungen, Emulsionen oder Suspensionen, unter Zusatz.von flüssigen und/oder festen Trägerstoffen bzw, Verdünnungsmitteln und gegebenenfalls vonThe labeled active substances or mixtures thereof are expediently used in the form of preparations, such as powders, scattering agents, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and optionally of
220215220215
- 4 - 57 147 12- 4 - 57 147 12
Hetz-, Haft-, Emulgier- und/oder Dispergierhilfsmitteln, angewandt, ·Hetz-, Haft-, emulsifying and / or dispersing aids, applied, ·
Geeignete flüssige Trägerstoffe sind z. B, Wasser, aliphatische und aromatische Kohlenwasserstoffe, wie Benzol, Toluol, Xylol, Cyclohexanon, Isophoron, Dimethylsulfoxyd, Dimethylformamid, weiterhin Mineralölfraktionen·Suitable liquid carriers are, for. B, water, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide, furthermore mineral oil fractions
Als feste Trägerstoffe eignen sich Mineralerden, z, B, Tonsil, Silicagel, Talkum, Kaolin, Attaclay, Kalkstein, Kieselsäure und pflanzliche Produkte, z» B. Mehle,Suitable solid carriers are mineral earths, z, B, tonsil, silica gel, talc, kaolin, attaclay, limestone, silicic acid and vegetable products, for example flours,
An oberflächenaktiven Stoffen sind zu nennen z« B. CaIciumligninsulfonat, Polyoxyäthylen-alkylphenolather, Naphthalinsulfonsäuren und deren Salze, Phenolsulfonsäuren und deren Salze, Formaldehydkondensate, Fettalkoholsulfate, sowie substituierte Benzolsulfonsäuren und deren Salze«Surfactants include, for example, calcium lignosulfonate, polyoxyethylene alkylphenol ether, naphthalenesulfonic acids and their salts, phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates, and substituted benzenesulfonic acids and their salts.
Der Anteil des bzw. der Wirkstoffe(s) in den verschiedenen Zubereitungen kann in weiten Grenzen variieren. Beispielsweise enthalten die Mittel etwa 5 bis 95 Gewe~% Wirkstoffe, 95 bis 5 Gew«-% flüssige oder feste TrägerstoffeThe proportion of the active ingredient (s) in the various preparations can vary within wide limits. For example, contain an average of about 5 to 95 wt% active e ~, 95 to 5 weight "-% liquid or solid carriers
gegebenenfalls bis zu 20 Gew»-% oberflächenaktive Stoffe.optionally up to 20% by weight of surface-active substances.
Die Ausbringung der Mittel kann in üblicher Weise erfolgen, z. B· mit Wasser als.Träger in Spritzbrühmengen von etwa 50 bis 1000 Liter/ha. Eine Anwendung der Mittel im sogenannten Low-Volume- und Ultra-Low-Volume-Verfahren ist ebenso möglich wie ihre Applikation in Form von sogenannten Mikrogranulaten.The application of the funds can be done in the usual way, for. B with Wasser als.Träger in Spritzbrühmengen of about 50 to 1000 liters / ha. An application of the funds in the so-called low-volume and ultra-low-volume method is just as possible as their application in the form of so-called microgranules.
220215220215
- 5 - 57 W 12- 5 - 57 W 12
Von den erfindungsgemäßen Verbindungen zeichnen sich durch eine herausragende selektive herbizide Wirkung insbesondere diejenigen aus, bei denen in der oben angeführten allgemeinen Formel.R Methyl, Äthyl, Isopropyl, Allyl, Propinyl, Isobutyl, sec,-Butyl, sec.-Butenyl oder sec.-Butinyl und X Sauerstoff oder Schwefel darstellen·Of the compounds according to the invention are distinguished by an outstanding selective herbicidal action in particular those in which in the abovementioned general formula.R methyl, ethyl, isopropyl, allyl, propynyl, isobutyl, sec, butyl, sec-butenyl or sec. -Butinyl and X represent oxygen or sulfur ·
Die neuen erfindungsgemäßen Verbindungen lassen sich z, B, herstellen, indem manThe novel compounds of the invention can be prepared z, B, by
a) Verbindungen der allgemeinen Formel O - COOla) compounds of the general formula O - COOl
NH-C-Z-RNH-C-Z-R
mit N-(2-Propinyl)-anilinwith N- (2-propynyl) -aniline
CH2 - C Ξ CHCH 2 - CΞCH
H-NH-N
in Gegenwart eines Säureakzeptors, z, B. unter Zusatz von überschüssigem Amin, oder einer anorganischen Base, wie z. B. Natronlauge, Natriumcarbonat, Kaliumcarbonat oder einer tertiären organischen Base, wie z, B, Triäthylamin, umsetzt oderin the presence of an acid acceptor, for example, with the addition of excess amine, or an inorganic base, such as. As sodium hydroxide, sodium carbonate, potassium carbonate or a tertiary organic base, such as, B, triethylamine, or
220215220215
- 6 - 57 14-7 12- 6 - 57 14-7 12
b) Verbindungen der allgemeinen Formel OHb) compounds of the general formula OH
HH-C-X-E Il 0HH-C-X-E Il 0
in Gegnewart einer tertiären organischen Base, wie z. B· Triäthylamin oder Pyridin, oder als Alkalisalze mit H-Phenyl-N-(2-propinyl)-carbamoylchlorid der Formelin Gegnewart a tertiary organic base such. B · triethylamine or pyridine, or as alkali metal salts with H-phenyl-N- (2-propynyl) -carbamoyl chloride of the formula
CH a C - CH2 CH a C - CH 2
bei Temperaturen von 0° bis 1000C reagieren läßt und die Verfahrensprodukte in üblicher Weise isoliert,, wobei E und X die obige Bedeutung haben·react at temperatures of 0 ° to 100 0 C and the process products isolated in a conventional manner, wherein E and X have the above meaning ·
Ausführungsbeispiel Exemplary embodiment
Das folgende Beispiel erläutert die Herstellung der erfindungsgemäßen Verbindungen. ·The following example illustrates the preparation of the compounds of the invention. ·
N-(2-Propinyl)-carbanilsäure-(3-methoxycarbonylaminophenyl)-ester N- (2-propynyl) -carbanilic acid (3-methoxycarbonylamino- phenyl) ester
In eine Lösung von 39,4 g (0,3 Mol) N-(2-Propinyl)-anilin in 75 ml Essigsäureäthylester'wird unter Bahren'und Kühlung auf 8 bis 12 0C eine Lösung von 68,7 g (0,3 Mol) Chlor-In a solution of 39.4 g (0.3 mol) of N- (2-propynyl) -aniline in 75 ml Essigsäureäthylester'wird Bahren'und under cooling to 8 to 12 0 C a solution of 68.7 g (0, 3 moles) of chlorine
220215220215
- 7 - 57 W 12- 7 - 57 W 12
ame iserLSäure-(3-methoxycarbonylaminophenyl)-ester in 150 ml Essigsäureafchylester und gleichzeitig eine Lösung von 41,4· g (0,3 Mol) Kaliumcarbonat in 15O ml Wasser eingetropft. 30 Minuten wird bei 10 0C nachgerührt, dann die organische Phase abgetrennt und unter Biszugabe mit verdünnter Salzsäure und Wasser gewaschen. Nach dem Trocknen mit Magnesiumsulfat wird unter vermindertem Druck eingedampft und mit 500 ml Isopropyläther versetzt, worauf das Umsetzungsprodukt auskristallisiert. Ausbeute: 67,9 g = 69,8 % der Theorie Fp.: 104 0CAme iserLSäure- (3-methoxycarbonylaminophenyl) ester in 150 ml of acetic acid acetate and at the same time a solution of 41.4 x g (0.3 mol) of potassium carbonate in 15O ml of water was added dropwise. Stirred for 30 minutes at 10 0 C, then the organic phase separated and washed with bis addition with dilute hydrochloric acid and water. After drying with magnesium sulfate is evaporated under reduced pressure and treated with 500 ml of isopropyl ether, whereupon the reaction product crystallized out. Yield: 67.9 g = 69.8% of theory mp: 104 ° C.
In analoger Weise lassen sich die folgenden erfindungsgemäßen Verbindungen herstellen.In an analogous manner, the following compounds according to the invention can be prepared.
Käme der Verbindung PhysikalischeWould the connection physical
Konstanteconstant
N-(2-Propinyl)-carbanilsäure-^J-Cmethylthio-carbonylamino)-phenyl7_ester Fp,: 130 0CN- (2-propynyl) -carbanilsäure- ^ J-Cmethylthio-carbonylamino) -phenyl7_ester ,: mp 130 0 C.
N-(2-Propinyl)-carbanilsäure-iiJ-(äthylthio-carbonylamino)-phenyi7-ester Fp.: 99 0CN- (2-propynyl) -carbanilsäure- i IJ (ethylthio-carbonylamino) -phenyi7 ester M.p .: 99 0 C
N-(2-Propinyl)-carbanilsäure-i/J-(2-pröpinyloxycarbonylamino)-phenylT-N- (2-propynyl) -carbanilic acid i / J- (2-propinyloxycarbonylamino) -phenylT-
ester Fp.: 118 0Cester mp: 118 ° C.
N-(2-Propinyl)-carbanilsäure-i/J-(2-me t hylpropoxycarbonylamino) -phenyl7-N- (2-propynyl) -carbanilic acid i / J- (2-methylpropoxycarbonylamino) -phenyl7-
ester Fp.: 108 0Cester mp .: 108 ° C.
- 8 - 57 147 12- 8 - 57 147 12
Physikalische Harne der Verbindung Eonstante Physical urine of the compound Eonstante
N-(2-Propinyl) «-carbanilsäure-(3-äthoxycarbonylaminophenyl)-ester Fp,: 101 - 103 0CN- (2-Propynyl) N -carbanilic acid (3-ethoxycarbonylaminophenyl) ester Fp, 101-103 0 C
N~(2-Propinyl)-carbeüiilsäure~/3"-(1-nie t hylät hoxycarb onylamino) -phenylT-ester Fp.: 78 - 79 0GN ~ (2-propynyl) -carboxylic acid ~ / 3 "- (1-n-butylethoxycarbonylamino) -phenylT-ester M.p .: 78-79 0 G
N-(2-Propinyl)-carbanilsäure-^J-(1-nie thy 1-2-propenyloxycarb onylamino) -N- (2-propynyl) -carbanilic acid ^ J- (1-never thy 1-2-propenyloxycarbylamino) -
Fp.: 96 - 97 0CMp .: 96-97 0 C
Die erfindungsgemäßen Verbindungen sind löslich in Isophoron, Cyclohexanon, Aceton, Tetrahydrofuran, Dimethylformamid, DimethyIsulfoxyd und anderen Lösungsmitteln, schwer löslich in Wasser, Benzol, Toluol u.a..The compounds of the invention are soluble in isophorone, cyclohexanone, acetone, tetrahydrofuran, dimethylformamide, dimethylsulfoxide and other solvents, sparingly soluble in water, benzene, toluene and the like.
Die folgenden Beispiele dienen zur Erläuterung der Anwendungsmöglichkeiten der erfindungsgemäßen Verbindungen, die in Form ihrer Zubereitungen erfolgt.The following examples serve to illustrate the possible applications of the compounds according to the invention, which take place in the form of their preparations.
Im Gewächshaus wurden die in der Tabelle aufgeführten erfindungsgemäßen Verbindungen als wäßrige Emulsionen bzw· Suspensionen in einer Aufwandmenge von 5 kg Wirkstoff/ha in 500 Liter Wasser/ha auf die Pflanzen im Nachauflaufverfahren gespritzt.In the greenhouse, the compounds according to the invention listed in the table were sprayed as aqueous emulsions or suspensions at a rate of 5 kg of active ingredient / ha in 500 liters of water / ha on the plants postemergence.
220215 _9_220215 _ 9 _
Drei Wochen nach der Behandlung wurde das Behandlungsergebnis bonitiert, wobei nach dem Schema 0, 1, 2, 3, 4 0 α keine Wirkung und 4 = Vernichtung der Pflanzen bedeuten·Three weeks after the treatment, the treatment result was scored, with 0, 1, 2, 3, 4 0 α meaning no effect and 4 = destruction of the plants.
Das Ergebnis zeigt, daß.in der Kegel eine Vernichtung der Pflanzen erreicht wurde«The result shows that a destruction of the plants was achieved in the cones. "
Erfindungsgemäße Verbindung Solanum BrassicaCompound of the invention Solanum Brassica
N-(2-Propiny1)-carbanilsäure- _^J-(methylthio-carbonalamino)-N- (2-propyne-1) -carbanilic acid -> - J- (methylthio-carbonalamino) -
phenyl7-ester 4 4phenyl 7-ester 4 4
N-(2-Propiny1)-carbanilsäure- ^J-(äthylthio-carbonylamino)-phenyl7~ester 4 4N- (2-Propiny1) -carbanilic acid ^ J- (ethylthio-carbonylamino) -phenyl ester 4 4
N-(2-Propinyl)-carbanilsäure- ^-(2-propinyloxycarbonylamino)-N- (2-propynyl) -carbanilic acid ^ - (2-propynyloxycarbonylamino) -
pheny].7-ester 4 4phenyl] .7-ester 4 4
N-(2-Prop inyl)-carb anils äure-/$-(2-met hylpropoxycarb onyl-N- (2-propynyl) carbanilic acid / $ - (2-methylpropoxycarbonyl)
amino)-pheny3.7-ester 4 4amino) -pheny3.7-ester 4 4
N-(2-Propinyl)-carbanilsäure-(3-äthoxycarbonylaminophenyl)-N- (2-propynyl) -carbanilsäure- (3-äthoxycarbonylaminophenyl) -
ester 4 4ester 4 4
2 20 215 - ίο- 57147122 20 215 - ίo- 5714712
gemäße Verbindung Solanom Brassicaproper compound Solanom Brassica
N-(2-Propinyl)-carbanilsäure-N- (2-propynyl) -carbanilsäure-
$~ (1-me t hylät hoxy carb ony 1- $ ~ (1-me t hylät hoxy carb ony 1
amino)-phenyl7-ester 4 4amino) -phenyl-7-ester 4 4
N-(2-Propinyl) -carbanilsäure-N- (2-propynyl) -carbanilic acid
£$-(1-methyl-2-propenyloxycarbonyl- £ $ - (1-methyl-2-propenyloxycarbonyl-
amino)-phenyl7-ester 4 4amino) -phenyl-7-ester 4 4
Unbehandelt 0 OUntreated 0 O
O = keine WirkungO = no effect
4 = Vernichtung der Pflanzen4 = destruction of the plants
Im Gewächshaus wurden die in der Tabelle aufgeführten Pflanzen nach dem Auflaufen mit der erfindungsgemäßen Verbindung und der bekannten Verbindung als wäßrige Emulsion in einer Aufwandmenge von 1 kg Wirkstoff/ha behandelt, indem die Zubereitungen gleichmäßig über die Pflanzen gesprüht wurden·In the greenhouse, the plants listed in the table were treated after emergence with the compound of the invention and the known compound as an aqueous emulsion in an application rate of 1 kg / ha, by spraying the preparations evenly over the plants.
Drei Wochen nach der Behandlung wrde das Behandlungsergebnis nach dem Schema O bis 10 bonitiert, wobei 0 s totale Vernicht und 10 = keine Schädigung bedeuten.Three weeks after the treatment, the treatment result would be scored according to scheme O to 10, where 0 s means total destruction and 10 = no damage.
Die erfindungsgemäße Verbindung zeigte eine herausragende selektive herbizide Wirkung, die bekannte Verbindung jedoch nicht·The compound according to the invention showed an outstanding selective herbicidal action, but the known compound was not
Erf ind ungs ge mäße Ve rb ind ungInventive industry
H OH O
cdCD
•Hi•Hi
SiSi
tata
•rl• rl
H-HT OOH-HT OO
co aco a
M s ©M s ©
1010
ro ο ro jp (4 R £>© cö+» R feOro ο ro jp (4 R £> © cö + »R feO
^ H O 03^ H O 03
etet
CQCQ
CQCQ
•η m• η m
O Ct5 © bO Örj © 3 CO >O Ct5 © bO Örj © 3 CO>
N~(2-Propinyl)-carbanilsäure-(3-äthoxycarbonylaminophenyl)-ester 10 10 10N ~ (2-propynyl) -carbanilic acid (3-ethoxycarbonylaminophenyl) ester 10 10 10
Vergleichsmittel gemäß DE-PS 1 567 151 Comparative agent according to DE-PS 1 567 151
3-Me t hoxycarb onylaminophenyl-N« (3'-methylphenyl)-carbamat3-methoxycarbonylaminophenyl-N "(3'-methylphenyl) carbamate
Unbehandeltuntreated
ti cdti cd
•Hi O• Hi O
COrH ·*=· CtJ O4» CO ·ΗCOrH · * = · CtJ O4 »CO · Η
5 8 42 8 5 10 10 10 10 10 10 10 105 8 42 8 5 10 10 10 10 10 10 10 10
O β totale Vernichtung 10 rs keine SchädigungO β total destruction 10 rs no damage
Claims (1)
X Sauerstoff oder Schwefel darstellen in Mischung mit
Träger- und/oder Hilfsstoffen aufweisen·in the EC ^ -C ^ alkyl, C ^ -C ^ alkenyl or C ^ -C ^ alkynyl and
X oxygen or sulfur are in mixture with
Carrier and / or auxiliary materials have ·
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792913975 DE2913975A1 (en) | 1979-04-05 | 1979-04-05 | N- (2-PROPINYL) -CARBANILIC ACID- (3-ALKOXY- AND ALKYLTHIOCARBONYLAMINO-PHENYL) -ESTERS, METHOD FOR PRODUCING THESE COMPOUNDS AND THE SELECTIVE HERBICIDES CONTAINING THEM |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD149996A5 true DD149996A5 (en) | 1981-08-12 |
Family
ID=6067686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80220215A DD149996A5 (en) | 1979-04-05 | 1980-04-03 | SELECTIVE HERBICIDES MEDIUM |
Country Status (35)
| Country | Link |
|---|---|
| JP (1) | JPS5819672B2 (en) |
| AR (1) | AR224521A1 (en) |
| AT (1) | AT365896B (en) |
| AU (1) | AU535374B2 (en) |
| BE (1) | BE882627A (en) |
| BG (1) | BG34897A3 (en) |
| BR (1) | BR8002009A (en) |
| CA (1) | CA1125301A (en) |
| CH (1) | CH645344A5 (en) |
| CS (1) | CS209949B2 (en) |
| DD (1) | DD149996A5 (en) |
| DE (1) | DE2913975A1 (en) |
| EG (1) | EG14317A (en) |
| ES (1) | ES8107172A1 (en) |
| FI (1) | FI800832A7 (en) |
| FR (1) | FR2453142A1 (en) |
| GB (1) | GB2049672B (en) |
| GR (1) | GR67206B (en) |
| HU (1) | HU181764B (en) |
| IL (1) | IL59736A (en) |
| IN (1) | IN154011B (en) |
| IT (1) | IT1148780B (en) |
| MA (1) | MA18803A1 (en) |
| MX (1) | MX6017E (en) |
| NL (1) | NL8001638A (en) |
| PH (1) | PH17275A (en) |
| PL (1) | PL123694B1 (en) |
| PT (1) | PT71032A (en) |
| RO (1) | RO79220A (en) |
| SE (1) | SE8002183L (en) |
| SU (1) | SU925248A3 (en) |
| TR (1) | TR20575A (en) |
| YU (1) | YU76180A (en) |
| ZA (1) | ZA802032B (en) |
| ZW (1) | ZW7980A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6014760U (en) * | 1983-07-09 | 1985-01-31 | フランスベッド株式会社 | Pine tress device |
| JPS6074668U (en) * | 1983-10-28 | 1985-05-25 | フランスベッド株式会社 | pine tress |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2413933A1 (en) * | 1974-03-20 | 1975-09-25 | Schering Ag | DIURETHANE WITH SELECTIVE HERBICIDAL EFFECT |
| DE2557552C2 (en) * | 1975-12-18 | 1984-12-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | Diurethanes and herbicidal agents containing these compounds as active ingredients |
| DE2650796A1 (en) * | 1976-11-03 | 1978-05-11 | Schering Ag | DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND THE SELECTIVE HERBICIDAL PRODUCT CONTAINING THEM |
| DE2651526A1 (en) * | 1976-11-09 | 1978-05-18 | Schering Ag | DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND THE SELECTIVE HERBICIDAL PRODUCT CONTAINING THEM |
-
1979
- 1979-04-05 DE DE19792913975 patent/DE2913975A1/en not_active Withdrawn
-
1980
- 1980-03-18 FI FI800832A patent/FI800832A7/en not_active Application Discontinuation
- 1980-03-19 NL NL8001638A patent/NL8001638A/en not_active Application Discontinuation
- 1980-03-19 YU YU00761/80A patent/YU76180A/en unknown
- 1980-03-20 SE SE8002183A patent/SE8002183L/en not_active Application Discontinuation
- 1980-03-25 IN IN217/DEL/80A patent/IN154011B/en unknown
- 1980-03-26 CH CH238480A patent/CH645344A5/en not_active IP Right Cessation
- 1980-03-27 CS CS802160A patent/CS209949B2/en unknown
- 1980-03-28 PT PT71032A patent/PT71032A/en unknown
- 1980-03-28 SU SU802901453A patent/SU925248A3/en active
- 1980-03-31 GB GB8010810A patent/GB2049672B/en not_active Expired
- 1980-03-31 IL IL59736A patent/IL59736A/en unknown
- 1980-03-31 MX MX808729U patent/MX6017E/en unknown
- 1980-04-01 CA CA348,942A patent/CA1125301A/en not_active Expired
- 1980-04-01 BR BR8002009A patent/BR8002009A/en unknown
- 1980-04-02 ES ES490256A patent/ES8107172A1/en not_active Expired
- 1980-04-02 AR AR280534A patent/AR224521A1/en active
- 1980-04-02 BG BG047214A patent/BG34897A3/en unknown
- 1980-04-02 GR GR61616A patent/GR67206B/el unknown
- 1980-04-02 AT AT0180680A patent/AT365896B/en not_active IP Right Cessation
- 1980-04-03 DD DD80220215A patent/DD149996A5/en unknown
- 1980-04-03 BE BE0/200112A patent/BE882627A/en not_active IP Right Cessation
- 1980-04-03 PL PL1980223231A patent/PL123694B1/en unknown
- 1980-04-03 HU HU80818A patent/HU181764B/en unknown
- 1980-04-03 TR TR20575A patent/TR20575A/en unknown
- 1980-04-03 ZA ZA00802032A patent/ZA802032B/en unknown
- 1980-04-03 ZW ZW79/80A patent/ZW7980A1/en unknown
- 1980-04-03 IT IT21168/80A patent/IT1148780B/en active
- 1980-04-03 AU AU57150/80A patent/AU535374B2/en not_active Ceased
- 1980-04-04 MA MA18998A patent/MA18803A1/en unknown
- 1980-04-04 JP JP55043644A patent/JPS5819672B2/en not_active Expired
- 1980-04-04 RO RO80100727A patent/RO79220A/en unknown
- 1980-04-04 FR FR8007670A patent/FR2453142A1/en active Granted
- 1980-04-05 EG EG207/80A patent/EG14317A/en active
- 1980-04-07 PH PH23863A patent/PH17275A/en unknown
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