CS199733B2 - Herbicide and method of producing active ingredient - Google Patents
Herbicide and method of producing active ingredient Download PDFInfo
- Publication number
- CS199733B2 CS199733B2 CS784058A CS405878A CS199733B2 CS 199733 B2 CS199733 B2 CS 199733B2 CS 784058 A CS784058 A CS 784058A CS 405878 A CS405878 A CS 405878A CS 199733 B2 CS199733 B2 CS 199733B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- compound
- formula
- hydrogen
- methyl
- chloro
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 6
- 230000002363 herbicidal effect Effects 0.000 title claims description 19
- 239000004480 active ingredient Substances 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- -1 cyclopropylmethoxy anilides Chemical class 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 29
- 150000001408 amides Chemical class 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 2
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract description 2
- 125000001589 carboacyl group Chemical group 0.000 abstract description 2
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002689 soil Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000007921 spray Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241001148683 Zostera marina Species 0.000 description 6
- 235000013877 carbamide Nutrition 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 241000209504 Poaceae Species 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 231100000208 phytotoxic Toxicity 0.000 description 3
- 230000000885 phytotoxic effect Effects 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 230000001629 suppression Effects 0.000 description 3
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 3
- QAXCUSLWCKLHIJ-UHFFFAOYSA-N 1-[(2,2-dichloro-1-methylcyclopropyl)methoxy]-3-isocyanatobenzene Chemical compound C=1C=CC(N=C=O)=CC=1OCC1(C)CC1(Cl)Cl QAXCUSLWCKLHIJ-UHFFFAOYSA-N 0.000 description 2
- 241000219318 Amaranthus Species 0.000 description 2
- 235000007558 Avena sp Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000289659 Erinaceidae Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 240000004153 Hibiscus sabdariffa Species 0.000 description 2
- 235000001018 Hibiscus sabdariffa Nutrition 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 235000005291 Rumex acetosa Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 230000000051 modifying effect Effects 0.000 description 2
- 238000003359 percent control normalization Methods 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 235000003513 sheep sorrel Nutrition 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- FOWRHXQSCVDBKQ-UHFFFAOYSA-N 1,1-dichloro-2-(chloromethyl)-2-methylcyclopropane Chemical compound ClCC1(C)CC1(Cl)Cl FOWRHXQSCVDBKQ-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- LOODICROWGFYED-UHFFFAOYSA-N 3-[(2,2-dichloro-1-methylcyclopropyl)methoxy]aniline Chemical compound C=1C=CC(N)=CC=1OCC1(C)CC1(Cl)Cl LOODICROWGFYED-UHFFFAOYSA-N 0.000 description 1
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 244000178993 Brassica juncea Species 0.000 description 1
- 235000011332 Brassica juncea Nutrition 0.000 description 1
- 235000014700 Brassica juncea var napiformis Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YGPSAUARDPSITI-UHFFFAOYSA-N ClC1(C(C1)(C)C=1C=C(NOC)C=CC1)Cl Chemical compound ClC1(C(C1)(C)C=1C=C(NOC)C=CC1)Cl YGPSAUARDPSITI-UHFFFAOYSA-N 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 244000088461 Panicum crus-galli Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 244000115721 Pennisetum typhoides Species 0.000 description 1
- 235000007195 Pennisetum typhoides Nutrition 0.000 description 1
- 101100062394 Picea mariana DAD1 gene Proteins 0.000 description 1
- 241000295650 Plagiobothrys arizonicus Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 235000021501 Rumex crispus Nutrition 0.000 description 1
- 244000207667 Rumex vesicarius Species 0.000 description 1
- 235000008515 Setaria glauca Nutrition 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical group NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 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
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 239000003621 irrigation water Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- YMPKWMGLBHVDBS-UHFFFAOYSA-N n-(3-hydroxyphenyl)-2,2-dimethylpentanamide Chemical compound CCCC(C)(C)C(=O)NC1=CC=CC(O)=C1 YMPKWMGLBHVDBS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 231100000241 scar Toxicity 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000009736 wetting Methods 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- A01N37/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
-
- 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
- A01N47/20—N-Aryl derivatives thereof
-
- 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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/807,940 US4149874A (en) | 1977-06-21 | 1977-06-21 | Substituted cyclopropylmethoxy anilides and their use as herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199733B2 true CS199733B2 (en) | 1980-07-31 |
Family
ID=25197489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS784058A CS199733B2 (en) | 1977-06-21 | 1978-06-20 | Herbicide and method of producing active ingredient |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4149874A (fr) |
| EP (1) | EP0000324B1 (fr) |
| JP (2) | JPS5838422B2 (fr) |
| AR (1) | AR220713A1 (fr) |
| AU (1) | AU515316B2 (fr) |
| BG (1) | BG30613A3 (fr) |
| BR (1) | BR7803787A (fr) |
| CA (1) | CA1232287A (fr) |
| CS (1) | CS199733B2 (fr) |
| DD (1) | DD137318A5 (fr) |
| DE (1) | DE2860186D1 (fr) |
| DK (1) | DK266578A (fr) |
| HU (1) | HU184675B (fr) |
| IL (1) | IL54783A (fr) |
| IT (1) | IT1105426B (fr) |
| PH (1) | PH13812A (fr) |
| PL (1) | PL110841B1 (fr) |
| RO (1) | RO83446B (fr) |
| YU (2) | YU143678A (fr) |
| ZA (1) | ZA783180B (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4230483A (en) * | 1977-06-21 | 1980-10-28 | Stauffer Chemical Company | Substituted cyclopropylmethoxy phenyl carbamates and thiocarbamates and their use as herbicides |
| US4356026A (en) | 1977-06-21 | 1982-10-26 | Stauffer Chemical Company | Substituted cyclopropylmethoxy phenyl ureas and their use as herbicides |
| US4336062A (en) * | 1977-09-19 | 1982-06-22 | Stauffer Chemical Company | Herbicidal cyclohexenone derivatives |
| DE2804739A1 (de) * | 1978-02-02 | 1979-08-09 | Schering Ag | Phenylharnstoff-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes selektives herbizides mittel |
| US4165976A (en) * | 1978-04-21 | 1979-08-28 | Stauffer Chemical Company | Synergistic herbicidal compositions |
| JPS55102553A (en) * | 1979-01-30 | 1980-08-05 | Sumitomo Chem Co Ltd | Substituted phenylurea derivative, its preparation, herbicide and fungicide comprising it as active constituent |
| DE2913976A1 (de) * | 1979-04-05 | 1980-10-23 | Schering Ag | Substituierte carbanilsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
| JPS56135456A (en) * | 1980-03-27 | 1981-10-22 | Sumitomo Chem Co Ltd | Substituted phenylurea derivative, its preparation and herbicide containing the same as active constituent |
| US4361438A (en) * | 1981-01-21 | 1982-11-30 | Stauffer Chemical Company | Substituted cyclopropyl methoxy phenyl ureas and the herbicidal use thereof |
| BR112015023829B1 (pt) * | 2013-03-25 | 2020-05-12 | Sumitomo Chemical Company, Limited | Composto de amidina e seu uso |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1219947B (de) * | 1963-05-22 | 1966-06-30 | Bayer Ag | Verfahren zur Herstellung von Carbonsaeureaniliden |
| GB1093121A (en) * | 1963-05-31 | 1967-11-29 | Wellcome Found | Etherified ªÐ-hydroxyanilines |
| DE1189312B (de) * | 1963-12-06 | 1965-03-18 | Schering Ag | Mittel mit selektiver herbizider Wirkung |
| US3362992A (en) * | 1965-05-27 | 1968-01-09 | Schwartz Herbert | Novel cycloalkenecarboxanilides |
| FR1507886A (fr) * | 1967-01-13 | 1967-12-29 | J Berthier Sa Lab | Nouveaux dérivés du dipropylacétylanilide |
| US3761592A (en) * | 1969-03-18 | 1973-09-25 | R Mizzoni | Quinoline derivatives exhibiting growth promoting and anticoccidial effects |
| CH536594A (de) * | 1970-07-31 | 1973-05-15 | Ciba Geigy Ag | Mittel zur Regulierung der Fruchtabszission |
| US3839446A (en) * | 1970-11-18 | 1974-10-01 | Stauffer Chemical Co | Ether and sulfide meta-substituted anilides |
| US3786090A (en) * | 1971-09-29 | 1974-01-15 | Interx Research Corp | Alkoxyacetanilide compounds |
| US3875229A (en) * | 1972-11-24 | 1975-04-01 | Schering Corp | Substituted carboxanilides |
| US3885948A (en) * | 1973-01-04 | 1975-05-27 | Stauffer Chemical Co | Meta-substituted ether anilides as algicidal agents |
| US3987059A (en) * | 1974-06-10 | 1976-10-19 | Sandoz, Inc. | 2-substituted indoles and process for their preparation |
-
1977
- 1977-06-21 US US05/807,940 patent/US4149874A/en not_active Expired - Lifetime
-
1978
- 1978-05-25 IL IL54783A patent/IL54783A/xx unknown
- 1978-05-30 AU AU36640/78A patent/AU515316B2/en not_active Expired
- 1978-06-01 EP EP78100019A patent/EP0000324B1/fr not_active Expired
- 1978-06-01 DE DE7878100019T patent/DE2860186D1/de not_active Expired
- 1978-06-02 ZA ZA00783180A patent/ZA783180B/xx unknown
- 1978-06-09 CA CA000305144A patent/CA1232287A/fr not_active Expired
- 1978-06-13 BR BR787803787A patent/BR7803787A/pt unknown
- 1978-06-14 DK DK266578A patent/DK266578A/da not_active Application Discontinuation
- 1978-06-14 RO RO94359A patent/RO83446B/ro unknown
- 1978-06-15 PH PH21266A patent/PH13812A/en unknown
- 1978-06-16 YU YU01436/78A patent/YU143678A/xx unknown
- 1978-06-16 JP JP53072288A patent/JPS5838422B2/ja not_active Expired
- 1978-06-19 DD DD78206108A patent/DD137318A5/xx unknown
- 1978-06-19 AR AR272661A patent/AR220713A1/es active
- 1978-06-19 IT IT49918/78A patent/IT1105426B/it active
- 1978-06-19 BG BG040140A patent/BG30613A3/xx unknown
- 1978-06-20 CS CS784058A patent/CS199733B2/cs unknown
- 1978-06-20 HU HU78SA3116A patent/HU184675B/hu unknown
- 1978-06-20 PL PL1978207767A patent/PL110841B1/pl not_active IP Right Cessation
-
1982
- 1982-06-14 JP JP57100820A patent/JPS6059901B2/ja not_active Expired
- 1982-10-07 YU YU02263/82A patent/YU226382A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0000324A1 (fr) | 1979-01-24 |
| AU515316B2 (en) | 1981-03-26 |
| DK266578A (da) | 1978-12-22 |
| IT1105426B (it) | 1985-11-04 |
| AR220713A1 (es) | 1980-11-28 |
| JPS584757A (ja) | 1983-01-11 |
| ZA783180B (en) | 1979-06-27 |
| JPS549246A (en) | 1979-01-24 |
| YU143678A (en) | 1983-02-28 |
| RO83446A (fr) | 1984-02-21 |
| PL207767A1 (pl) | 1979-04-09 |
| YU226382A (en) | 1983-02-28 |
| PH13812A (en) | 1980-10-03 |
| CA1232287A (fr) | 1988-02-02 |
| IL54783A (en) | 1981-07-31 |
| DE2860186D1 (en) | 1981-01-08 |
| DD137318A5 (de) | 1979-08-29 |
| IT7849918A0 (it) | 1978-06-19 |
| BG30613A3 (en) | 1981-07-15 |
| PL110841B1 (en) | 1980-08-30 |
| HU184675B (en) | 1984-09-28 |
| EP0000324B1 (fr) | 1980-10-01 |
| AU3664078A (en) | 1979-12-06 |
| JPS6059901B2 (ja) | 1985-12-27 |
| IL54783A0 (en) | 1978-07-31 |
| US4149874A (en) | 1979-04-17 |
| JPS5838422B2 (ja) | 1983-08-23 |
| RO83446B (ro) | 1984-02-28 |
| BR7803787A (pt) | 1979-01-16 |
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