DD232416A5 - Herbizide mittel - Google Patents
Herbizide mittel Download PDFInfo
- Publication number
- DD232416A5 DD232416A5 DD84267296A DD26729684A DD232416A5 DD 232416 A5 DD232416 A5 DD 232416A5 DD 84267296 A DD84267296 A DD 84267296A DD 26729684 A DD26729684 A DD 26729684A DD 232416 A5 DD232416 A5 DD 232416A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- hydrogen
- alkyl
- methyl
- salts
- chlorine
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 29
- 239000004009 herbicide Substances 0.000 title claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 85
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 85
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 29
- -1 2- (2-substituted benzoyl) -1,3-cyclohexanediones Chemical class 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims description 230
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 35
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 9
- 239000011630 iodine Substances 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000012050 conventional carrier Substances 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 21
- 238000012360 testing method Methods 0.000 description 14
- 238000009472 formulation Methods 0.000 description 11
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- 239000002689 soil Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000001246 bromo group Chemical group Br* 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 244000178993 Brassica juncea Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 231100000208 phytotoxic Toxicity 0.000 description 6
- 230000000885 phytotoxic effect Effects 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
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- 241001148727 Bromus tectorum Species 0.000 description 3
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- 230000000694 effects Effects 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
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- 239000003053 toxin Substances 0.000 description 3
- 231100000765 toxin Toxicity 0.000 description 3
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- 239000000080 wetting agent Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 2
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- 244000062793 Sorghum vulgare Species 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- GJQBHOAJJGIPRH-UHFFFAOYSA-N benzoyl cyanide Chemical class N#CC(=O)C1=CC=CC=C1 GJQBHOAJJGIPRH-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
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- 239000006185 dispersion Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 231100000167 toxic agent Toxicity 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 1
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical class OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- MJJCNUBDKYFMHM-UHFFFAOYSA-N 2,4-dichlorobenzoyl cyanide Chemical compound ClC1=CC=C(C(=O)C#N)C(Cl)=C1 MJJCNUBDKYFMHM-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- NEUXLFCJDNFNOQ-UHFFFAOYSA-N 2-[(2,4-dichlorophenyl)methyl]-4,4-dimethylcyclohexane-1,3-dione Chemical compound O=C1C(C)(C)CCC(=O)C1CC1=CC=C(Cl)C=C1Cl NEUXLFCJDNFNOQ-UHFFFAOYSA-N 0.000 description 1
- OOLBCHYXZDXLDS-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-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
- HABAPWZXRLIZDL-UHFFFAOYSA-N 2-chloro-2-phenoxyacetic acid Chemical compound OC(=O)C(Cl)OC1=CC=CC=C1 HABAPWZXRLIZDL-UHFFFAOYSA-N 0.000 description 1
- ONLWSYXLTSMXII-UHFFFAOYSA-N 2-chloro-n-(2,6-dimethylphenyl)-n-pentan-2-ylacetamide Chemical compound CCCC(C)N(C(=O)CCl)C1=C(C)C=CC=C1C ONLWSYXLTSMXII-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NAOCHJCREOAPOF-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC(Cl)=CC(Cl)=C1 NAOCHJCREOAPOF-UHFFFAOYSA-N 0.000 description 1
- PLGPBTCNKJQJHQ-UHFFFAOYSA-N 4,4-dimethylcyclohexane-1,3-dione Chemical compound CC1(C)CCC(=O)CC1=O PLGPBTCNKJQJHQ-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical class [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000717 retained effect Effects 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical class [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000003419 tautomerization reaction Methods 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
- 238000010998 test method Methods 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005303 weighing 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/303—Saturated compounds containing keto groups bound to rings to a six-membered ring
-
- 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
- A01N37/42—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 within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53288283A | 1983-09-16 | 1983-09-16 | |
| US56607783A | 1983-12-27 | 1983-12-27 | |
| US64079184A | 1984-08-17 | 1984-08-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD232416A5 true DD232416A5 (de) | 1986-01-29 |
Family
ID=27415107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84267296A DD232416A5 (de) | 1983-09-16 | 1984-09-14 | Herbizide mittel |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0135191B1 (da) |
| KR (1) | KR890000193B1 (da) |
| AR (1) | AR240669A1 (da) |
| BG (1) | BG43683A3 (da) |
| BR (1) | BR8404641A (da) |
| CA (1) | CA1231962A (da) |
| DD (1) | DD232416A5 (da) |
| DE (1) | DE3474814D1 (da) |
| DK (1) | DK436484A (da) |
| ES (1) | ES535946A0 (da) |
| HU (1) | HU192442B (da) |
| MX (1) | MX156956A (da) |
| NZ (1) | NZ209558A (da) |
| PH (1) | PH21446A (da) |
| PL (1) | PL145926B1 (da) |
| PT (1) | PT79210B (da) |
| RO (1) | RO89372A2 (da) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5006162A (en) * | 1982-03-25 | 1991-04-09 | Ici Americas Inc. | Certain 2-(2-substituted benzoyl)-1,3,5-cyclohexanetriones |
| US4797150A (en) * | 1986-06-09 | 1989-01-10 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-1,3,5-cyclohexanetriones |
| IL77349A (en) * | 1984-12-20 | 1990-07-12 | Stauffer Chemical Co | 2-(2'-nitrobenzoyl)-1,3-cyclohexanediones,their preparation and their use as herbicides |
| TR22585A (tr) * | 1984-12-20 | 1987-12-07 | Stauffer Chemical Co | Bazi 2-(2'-alkilbenzoil)-1,3-sikloheksandion'lar |
| US4957540A (en) * | 1986-06-09 | 1990-09-18 | Ici Americas Inc. | Certain substituted 3-(substituted oxy)-2-benzoyl-cyclohex-2-enones |
| US4918236A (en) * | 1986-06-09 | 1990-04-17 | Ici Americas Inc. | Certain substituted 3-(substituted oxy)-2-benzoyl-cyclohex-2-enones |
| US4837352A (en) * | 1986-06-09 | 1989-06-06 | Stauffer Chemical Company | 3-chloro-2-(2'-substituted benzoyl)-cyclohex-2-enone intermediate compounds |
| KR890003680A (ko) * | 1986-10-16 | 1989-04-17 | 죤 알.페넬 | 2-(2-치환 벤조일)-4-(치환)-1,3-시클로헥산디온 및 그 제조방법과 이를 이용한 조성물 및 식물체의 억제방법 |
| US4781751A (en) * | 1987-08-20 | 1988-11-01 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-4-(substituted)-1,3-cyclohexanediones |
| US4783213A (en) * | 1986-10-16 | 1988-11-08 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-4-(substituted oxy or substituted thio)-1,3-cyclohexanediones |
| GB8706557D0 (en) * | 1987-03-19 | 1987-04-23 | Ici Plc | Herbicidal compounds |
| EP0316491A1 (en) * | 1987-11-19 | 1989-05-24 | Stauffer Agricultural Chemicals Company, Inc. | Herbicidal 2-pyridyl and 2-pyrimidine carbonyl 1,3-cyclohexanediones |
| DE3743695A1 (de) * | 1987-12-18 | 1989-06-29 | Schering Ag | 4-benzoyl-3-hydroxy-5-oxo-3-cyclohexencarbonsaeurederivate, verfahren zur herstellung dieser verbindungen und ihre verwendung als mittel mit pflanzenwachstumsregulierender wirkung |
| HUT50312A (en) * | 1988-02-01 | 1990-01-29 | Sandoz Ag | Herbicide composition containing new dion-compounds and process for producing these compounds |
| HU202851B (en) * | 1988-04-04 | 1991-04-29 | Sandoz Ag | Herbicidal or acaricidal compositions and process for producing the active ingredient aryldione derivatives |
| US5089046A (en) * | 1988-04-04 | 1992-02-18 | Sandoz Ltd. | Aryl and heteroaryl diones |
| AU616956B2 (en) * | 1988-04-18 | 1991-11-14 | Sandoz Ltd. | Substituted phenyl or pyrimidine bicyclodiones |
| IL91083A (en) * | 1988-07-25 | 1993-04-04 | Ciba Geigy | Cyclohexanedione derivatives, their preparation and their use as herbicides |
| US4957538A (en) * | 1988-11-18 | 1990-09-18 | Ici Americas Inc. | Certain 2-(2',3',4'-trisubstituted benzoyl)-1,3-cyclohexanediones |
| ZA904951B (en) | 1989-07-04 | 1991-05-29 | Nippon Soda Co Limited | Substituted bicycloheptandione derivatives |
| US4997473A (en) * | 1989-08-24 | 1991-03-05 | Ici Americas Inc. | Certain 2-(2'-substituted benzoyl)-4-proparoyl-1,3-cyclohexanedione herbicides |
| DE59010829D1 (de) * | 1989-10-18 | 1998-07-16 | Hoechst Schering Agrevo Gmbh | Herbizide wirkstoffkombinationen |
| US5306695A (en) * | 1991-03-06 | 1994-04-26 | Hoechst Aktiengesellschaft | Haloalkoxy-substituted benzoylcyclohexanediones as herbicides and plant growth regulators |
| GEP20001970B (en) * | 1995-02-24 | 2000-03-05 | Basf Ag | Herbicidal Benzoyl Derivatives |
| DE19532311A1 (de) * | 1995-09-01 | 1997-03-06 | Basf Ag | Benzoylderivate |
| EA002923B1 (ru) | 1997-05-07 | 2002-10-31 | Басф Акциенгезельшафт | Замещенные 2-(3-алкенилбензоил)циклогексан-1,3-дионы |
| ATE288900T1 (de) | 1998-07-24 | 2005-02-15 | Bayer Cropscience Ag | Substituierte benzoylcyclohexandione |
| DE19962923A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Benzoylcyclohexandione |
| AR027575A1 (es) | 2000-03-06 | 2003-04-02 | Bayer Ag | Benzoilciclohexenonas substituidas |
| CN111072548B (zh) * | 2019-12-19 | 2022-07-26 | 南开大学 | 2-(2,3,4,9-四氢-1h-咔唑-6-羰基)环己烷-1,3-二酮类化合物及除草活性 |
| TW202543611A (zh) * | 2024-03-27 | 2025-11-16 | 美商費斯製藥有限公司 | Hpd抑制劑組成物及使用方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4175135A (en) * | 1978-07-18 | 1979-11-20 | Union Carbide Corporation | Method of controlling acarina ectoparasites on warmblooded animals by orally administering to the animal an ectoparasitically effective amount of a 2-aryl-1,3-cyclohexanedione compound, and alkali metal salts, ammonium salts and enol esters thereof |
| US4350705A (en) * | 1979-03-31 | 1982-09-21 | Eisai Co., Ltd. | Cyclohexane derivatives, process for preparation thereof and medicines containing these cyclohexane derivatives |
| EP0090262B1 (en) * | 1982-03-25 | 1992-08-05 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
-
1982
- 1982-09-14 PH PH31212A patent/PH21446A/en unknown
-
1984
- 1984-09-05 AR AR29784484A patent/AR240669A1/es active
- 1984-09-11 MX MX202664A patent/MX156956A/es unknown
- 1984-09-12 DK DK436484A patent/DK436484A/da not_active Application Discontinuation
- 1984-09-12 EP EP84110916A patent/EP0135191B1/en not_active Expired
- 1984-09-12 DE DE8484110916T patent/DE3474814D1/de not_active Expired
- 1984-09-13 BG BG066847A patent/BG43683A3/xx unknown
- 1984-09-14 HU HU843470A patent/HU192442B/hu not_active IP Right Cessation
- 1984-09-14 PT PT79210A patent/PT79210B/pt unknown
- 1984-09-14 ES ES535946A patent/ES535946A0/es active Granted
- 1984-09-14 DD DD84267296A patent/DD232416A5/de unknown
- 1984-09-14 KR KR1019840005585A patent/KR890000193B1/ko not_active Expired
- 1984-09-14 PL PL1984249588A patent/PL145926B1/pl unknown
- 1984-09-14 NZ NZ209558A patent/NZ209558A/en unknown
- 1984-09-17 BR BR8404641A patent/BR8404641A/pt not_active IP Right Cessation
- 1984-09-17 CA CA000463343A patent/CA1231962A/en not_active Expired
- 1984-09-17 RO RO84115724A patent/RO89372A2/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR850002827A (ko) | 1985-05-20 |
| PT79210A (en) | 1984-10-01 |
| BG43683A3 (en) | 1988-07-15 |
| EP0135191A2 (en) | 1985-03-27 |
| PL249588A1 (en) | 1985-07-02 |
| CA1231962A (en) | 1988-01-26 |
| DE3474814D1 (en) | 1988-12-01 |
| RO89372A2 (ro) | 1986-05-30 |
| MX156956A (es) | 1988-10-17 |
| ES8600191A1 (es) | 1985-10-01 |
| ES535946A0 (es) | 1985-10-01 |
| EP0135191B1 (en) | 1988-10-26 |
| KR890000193B1 (ko) | 1989-03-10 |
| NZ209558A (en) | 1988-05-30 |
| DK436484A (da) | 1985-03-17 |
| EP0135191A3 (en) | 1985-12-27 |
| PT79210B (en) | 1986-08-22 |
| PH21446A (en) | 1987-10-20 |
| PL145926B1 (en) | 1988-11-30 |
| HUT35150A (en) | 1985-06-28 |
| HU192442B (en) | 1987-06-29 |
| BR8404641A (pt) | 1985-08-06 |
| AR240669A1 (es) | 1990-08-31 |
| DK436484D0 (da) | 1984-09-12 |
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