DD255729A5 - Verfahren zur herstellung von neuen phenoxy-benzoyl-malonsaeureester-derivaten - Google Patents

Verfahren zur herstellung von neuen phenoxy-benzoyl-malonsaeureester-derivaten Download PDF

Info

Publication number: DD255729A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; nitro; trifluoromethyl; halogen; phenoxy
Prior art date: 1985-10-01

Application number

DD86301113A

Other languages

German (de)

English (en)

Inventor

Tamas Koemives

Ferenc Dutka

Istvan Barta

Istvan Jablonkai

Agnes Hulesch

Ferenc Bihari

Gyuly Eifert

Peter Bohus

Mihaly Nagy

Mihaly Barabas

Istvan Kueronya

Original Assignee

��@��k��

��@��@��@��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-10-01

Filing date

1986-09-25

Publication date

1988-04-13

1986-09-25 Application filed by ��@��k��, ��@��@��@��@��k�� filed Critical ��@��k��

1988-04-13 Publication of DD255729A5 publication Critical patent/DD255729A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 17
-1 PHENOXY-BENZOYL Chemical class 0.000 title claims abstract description 12
150000001875 compounds Chemical class 0.000 claims abstract description 32
229910052736 halogen Inorganic materials 0.000 claims abstract description 13
150000002367 halogens Chemical class 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 9
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
150000002431 hydrogen Chemical class 0.000 claims abstract 6
239000000460 chlorine Substances 0.000 claims description 26
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 claims description 5
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims description 3
PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000002736 metal compounds Chemical class 0.000 claims description 3
YMJTZXQTOOCDHU-UHFFFAOYSA-N 2-benzoyl-2-phenoxypropanedioic acid Chemical class O(C1=CC=CC=C1)C(C(=O)O)(C(=O)O)C(C1=CC=CC=C1)=O YMJTZXQTOOCDHU-UHFFFAOYSA-N 0.000 claims description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
229910001629 magnesium chloride Inorganic materials 0.000 claims description 2
230000002363 herbicidal effect Effects 0.000 abstract description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
FXMOZZSVIOBEGU-UHFFFAOYSA-N 2-[2-chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoyl]propanedioic acid Chemical compound C1=C(Cl)C(C(=O)C(C(O)=O)C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 FXMOZZSVIOBEGU-UHFFFAOYSA-N 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 4
241000196324 Embryophyta Species 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
239000012071 phase Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 2
235000005822 corn Nutrition 0.000 description 2
OAQIJHWWDSEJDY-UHFFFAOYSA-N diethyl 2-(4-fluoro-2-nitrobenzoyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)C1=CC=C(F)C=C1[N+]([O-])=O OAQIJHWWDSEJDY-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000284 extract Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
230000035484 reaction time Effects 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
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
YNWKEXMSQQUMEL-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1Cl YNWKEXMSQQUMEL-UHFFFAOYSA-N 0.000 description 1
WUDKZVAHDRZANM-UHFFFAOYSA-N 2-nitro-5-(2,4,6-trichlorophenoxy)benzoyl chloride Chemical compound C1=C(C(Cl)=O)C([N+](=O)[O-])=CC=C1OC1=C(Cl)C=C(Cl)C=C1Cl WUDKZVAHDRZANM-UHFFFAOYSA-N 0.000 description 1
PVMWXQADECJYQC-UHFFFAOYSA-N 5-[2,6-dichloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl bromide Chemical compound C1=C(C(Br)=O)C([N+](=O)[O-])=CC=C1OC1=C(Cl)C=C(C(F)(F)F)C=C1Cl PVMWXQADECJYQC-UHFFFAOYSA-N 0.000 description 1
KGPHNHSAYAXSOW-UHFFFAOYSA-N 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chloride Chemical compound C1=C(C(Cl)=O)C([N+](=O)[O-])=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl KGPHNHSAYAXSOW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
241000219317 Amaranthaceae Species 0.000 description 1
240000001592 Amaranthus caudatus Species 0.000 description 1
235000009328 Amaranthus caudatus Nutrition 0.000 description 1
NZQXQEOVVJNTPV-UHFFFAOYSA-N C(C)OC(C(C(=O)OCC)C(C1=C(C=CC(=C1)OC1=C(C=C(C=C1Cl)Cl)Cl)[N+](=O)[O-])=O)=O Chemical compound C(C)OC(C(C(=O)OCC)C(C1=C(C=CC(=C1)OC1=C(C=C(C=C1Cl)Cl)Cl)[N+](=O)[O-])=O)=O NZQXQEOVVJNTPV-UHFFFAOYSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
244000020551 Helianthus annuus Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
240000004713 Pisum sativum Species 0.000 description 1
235000010582 Pisum sativum Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
235000005775 Setaria Nutrition 0.000 description 1
241000232088 Setaria <nematode> Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001341 alkaline earth metal compounds Chemical class 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
239000008346 aqueous phase Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
244000038559 crop plants Species 0.000 description 1
239000013078 crystal Substances 0.000 description 1
XEGSQSORQFTDJF-UHFFFAOYSA-N diethyl 2-[2-chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoyl]propanedioate Chemical compound C(C)OC(C(C(=O)OCC)C(C1=C(C=CC(=C1)OC1=C(C=C(C=C1)C(F)(F)F)Cl)Cl)=O)=O XEGSQSORQFTDJF-UHFFFAOYSA-N 0.000 description 1
LSALYRLFFRBENA-UHFFFAOYSA-N diethyl 2-[5-[2,6-dichloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl]propanedioate Chemical compound C(C)OC(C(C(=O)OCC)C(C1=C(C=CC(=C1)OC1=C(C=C(C=C1Cl)C(F)(F)F)Cl)[N+](=O)[O-])=O)=O LSALYRLFFRBENA-UHFFFAOYSA-N 0.000 description 1
KDIFRLZXBPGPJS-UHFFFAOYSA-N diethyl 2-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl]propanedioate Chemical compound C(C)OC(C(C(=O)OCC)C(C1=C(C=CC(=C1)OC1=C(C=C(C=C1)C(F)(F)F)Cl)[N+](=O)[O-])=O)=O KDIFRLZXBPGPJS-UHFFFAOYSA-N 0.000 description 1
HCDITHVDEPPNIL-UHFFFAOYSA-L dipotassium;propanedioate Chemical compound [K+].[K+].[O-]C(=O)CC([O-])=O HCDITHVDEPPNIL-UHFFFAOYSA-L 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
239000008241 heterogeneous mixture Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
235000021374 legumes Nutrition 0.000 description 1
150000002680 magnesium Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
150000002690 malonic acid derivatives Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000002496 methyl group Chemical group [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
150000002825 nitriles Chemical class 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000012429 reaction media Substances 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
238000009331 sowing Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 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
- 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
- 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
- A01N37/44—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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DD86301113A 1985-10-01 1986-09-25 Verfahren zur herstellung von neuen phenoxy-benzoyl-malonsaeureester-derivaten DD255729A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU853797A HU196884B (en)	1985-10-01	1985-10-01	Herbicides comprising phenoxy-benzoyl-malon ester derivatives as active ingredient and process for producing the active ingredients

Publications (1)

Publication Number	Publication Date
DD255729A5 true DD255729A5 (de)	1988-04-13

Family

ID=10965547

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DD86301113A DD255729A5 (de)	1985-10-01	1986-09-25	Verfahren zur herstellung von neuen phenoxy-benzoyl-malonsaeureester-derivaten
DD86294689A DD249840A5 (de)	1985-10-01	1986-09-25	Herbizide mittel und verfahren zur bekaempfung von unkraeutern

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DD86294689A DD249840A5 (de)	1985-10-01	1986-09-25	Herbizide mittel und verfahren zur bekaempfung von unkraeutern

Country Status (14)

Country	Link
JP (1)	JPS6281353A (fr)
AU (1)	AU595834B2 (fr)
BE (1)	BE905534A (fr)
CH (1)	CH676595A5 (fr)
CS (1)	CS273620B2 (fr)
DD (2)	DD255729A5 (fr)
DE (1)	DE3632492A1 (fr)
FR (1)	FR2587998B1 (fr)
GB (1)	GB2181133B (fr)
HU (1)	HU196884B (fr)
IL (1)	IL79974A (fr)
NL (1)	NL8602481A (fr)
SE (1)	SE8604148L (fr)
SU (1)	SU1676435A3 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5925795A (en) *	1996-09-16	1999-07-20	Zeneca Limited	Processes for the preparation of aryl-β-diketones, arylpyrimidine ketones and crop protection intermediates

1985
- 1985-10-01 HU HU853797A patent/HU196884B/hu not_active IP Right Cessation
1986
- 1986-09-08 IL IL79974A patent/IL79974A/xx unknown
- 1986-09-18 CH CH3682/86A patent/CH676595A5/de not_active IP Right Cessation
- 1986-09-24 DE DE19863632492 patent/DE3632492A1/de not_active Withdrawn
- 1986-09-25 DD DD86301113A patent/DD255729A5/de not_active IP Right Cessation
- 1986-09-25 DD DD86294689A patent/DD249840A5/de not_active IP Right Cessation
- 1986-09-30 SU SU864028283A patent/SU1676435A3/ru active
- 1986-09-30 JP JP61230188A patent/JPS6281353A/ja active Pending
- 1986-09-30 SE SE8604148A patent/SE8604148L/ not_active Application Discontinuation
- 1986-09-30 AU AU63266/86A patent/AU595834B2/en not_active Ceased
- 1986-09-30 GB GB8623486A patent/GB2181133B/en not_active Expired
- 1986-09-30 FR FR8613597A patent/FR2587998B1/fr not_active Expired
- 1986-10-01 BE BE0/217241A patent/BE905534A/fr not_active IP Right Cessation
- 1986-10-01 NL NL8602481A patent/NL8602481A/nl not_active Application Discontinuation
- 1986-10-01 CS CS705886A patent/CS273620B2/cs unknown

Also Published As

Publication number	Publication date
FR2587998A1 (fr)	1987-04-03
GB8623486D0 (en)	1986-11-05
AU595834B2 (en)	1990-04-12
HU196884B (en)	1989-02-28
CS273620B2 (en)	1991-03-12
NL8602481A (nl)	1987-05-04
SU1676435A3 (ru)	1991-09-07
GB2181133A (en)	1987-04-15
CS705886A2 (en)	1990-08-14
SE8604148D0 (sv)	1986-09-30
HUT41590A (en)	1987-05-28
DD249840A5 (de)	1987-09-23
BE905534A (fr)	1987-02-02
CH676595A5 (fr)	1991-02-15
GB2181133B (en)	1989-03-22
FR2587998B1 (fr)	1988-08-05
JPS6281353A (ja)	1987-04-14
IL79974A0 (en)	1986-12-31
SE8604148L (sv)	1987-04-02
DE3632492A1 (de)	1987-04-16
IL79974A (en)	1990-09-17
AU6326686A (en)	1987-04-09

Legal Events

Date	Code	Title	Description
1995-07-06	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE2612731C2 (de)	1986-06-26	Verfahren zur Herstellung von N-substituierten Halogen-2-pyrrolidinonen
EP0014684A2 (fr)	1980-08-20	Dérivés substitués en position 2 d'acides phénoxy-5 phénylphosphoniques, procédé pour leur préparation et leur utilisation comme herbicides
EP0053321A2 (fr)	1982-06-09	Dérivés substitués de l'acide cinnamique, leur procédé de préparation et leur application comme herbicides
DD209718A5 (de)	1984-05-23	Schaedlingsbekaempfungsmittel
EP0008624A1 (fr)	1980-03-19	Esters d'acides O-(pyridyloxy-phényl)-lactiques, leur procédé de préparation et leur utilisation comme herbicides et régulateurs de croissance de plantes
US4429146A (en)	1984-01-31	Substituted diphenyl ether herbicides and process for use
EP0050097B1 (fr)	1984-12-05	Dérivés de l'acide alpha-(pyridyl-2-oxy-phénoxy)-propionique, procédé pour leur préparation et leur utilisation comme herbicide et/ou régulateurs de croissance de plantes
EP0144895B1 (fr)	1988-01-20	Thiolan-2,4-dion-3-carboxamides
EP0086375B1 (fr)	1986-04-09	Dérivés de la pyridine, leur préparation et utilisation
EP0007089A1 (fr)	1980-01-23	Acylanilides à activité herbicide et fungicide, procédé pour leur préparation et leur utilisation
DD255730A5 (de)	1988-04-13	Verfahren zur herstellung von neuen aryloxy-phenoxyacyl-malonsaeureester-derivaten
EP0019858B1 (fr)	1983-06-22	N-Oximinoalcoyl-anilides, procédés pour leur préparation et leur utilisation comme fongicides
DD255729A5 (de)	1988-04-13	Verfahren zur herstellung von neuen phenoxy-benzoyl-malonsaeureester-derivaten
EP0010692A1 (fr)	1980-05-14	N-m-Anilidocarbamates, herbicides les contenant et procédé pour leur préparation ainsi que procédé pour contrôler la croissance de plantes indésirables
EP0001641A1 (fr)	1979-05-02	Ester methoxyethylique de l'acide 2(2'-Nitro-5-(2"-chloro-4" trifluoromethylphenoxy)-phenoxy) propionique, une composition contenant cet ester comme substance active, et son utilisation comme herbicide.
DE3625460A1 (de)	1988-02-04	N-(2-cyan-2-oximinoacetyl)-aminonitrile
EP0030702A1 (fr)	1981-06-24	Esters de l'acide propionique, leur préparation, composés herbicides contenant ces dérivés comme agents actifs et l'utilisation de ces composés et agents herbicides
EP0024747A1 (fr)	1981-03-11	Ethers d'anilinométhyloxime et procédés pour leur préparation
EP0299313B1 (fr)	1991-07-03	Pesticide à base de dérivés du nitrile de l'acide 2,3-diaminomaléique
EP0160962B1 (fr)	1989-09-13	Esters iodopropargyliques d'acides phénylacétiques substitués, leur préparation et utilisation comme agents biocides
DE3805059A1 (de)	1989-08-31	Heterocyclisch substituierte acrylsaeureester
EP0066771B1 (fr)	1984-10-03	1-Iodo-1-propyn-3-ols, procédé pour leur préparation et leur utilisation comme agent de protection des plantes
EP0387499B1 (fr)	1993-12-22	Ethers d'oxime substitués et leur application comme pesticides
DE4427997A1 (de)	1996-02-15	5-Hydroxypyrazol-4-yl-carbonyl-substituierte Saccharinderivate
EP0028609B1 (fr)	1983-07-27	Utilisation de dérivés de chloronitrophényle comme herbicides sélectifs et nouveaux dérivés de chloronitrophényle