DE1695840A1 - Process for the preparation of new pyridazone derivatives - Google Patents
Process for the preparation of new pyridazone derivativesInfo
- Publication number
- DE1695840A1 DE1695840A1 DE1968S0114601 DES0114601A DE1695840A1 DE 1695840 A1 DE1695840 A1 DE 1695840A1 DE 1968S0114601 DE1968S0114601 DE 1968S0114601 DE S0114601 A DES0114601 A DE S0114601A DE 1695840 A1 DE1695840 A1 DE 1695840A1
- Authority
- DE
- Germany
- Prior art keywords
- trifluoromethylphenyl
- methyl
- hydrogen
- formula
- dimethylamino
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 3-Trifluoromethylphenyl Chemical group 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000004480 active ingredient Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000004009 herbicide Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 230000002363 herbicidal effect Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 8
- 241000219146 Gossypium Species 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 244000000626 Daucus carota Species 0.000 description 6
- 235000002767 Daucus carota Nutrition 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 244000046052 Phaseolus vulgaris Species 0.000 description 5
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- JXIVRSULRMSHRL-UHFFFAOYSA-N 4,5-dichloro-2-[3-(trifluoromethyl)phenyl]-1,5-dihydropyridazin-6-one Chemical compound FC(C=1C=C(C=CC1)N1NC(C(C(=C1)Cl)Cl)=O)(F)F JXIVRSULRMSHRL-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000010633 broth Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003415 peat Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000004576 sand Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 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 3
- 239000011707 mineral Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000011305 Capsella bursa pastoris Nutrition 0.000 description 2
- 240000008867 Capsella bursa-pastoris Species 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 108010073771 Soybean Proteins Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- JSWQDLBFVSTSIW-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=CC=C1C(F)(F)F JSWQDLBFVSTSIW-UHFFFAOYSA-N 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000019710 soybean protein Nutrition 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- NCNYEGJDGNOYJX-NSCUHMNNSA-N (e)-2,3-dibromo-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Br)=C(/Br)C=O NCNYEGJDGNOYJX-NSCUHMNNSA-N 0.000 description 1
- LUMLZKVIXLWTCI-NSCUHMNNSA-N (e)-2,3-dichloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(/Cl)C=O LUMLZKVIXLWTCI-NSCUHMNNSA-N 0.000 description 1
- LXILAQXSFLCWDQ-UHFFFAOYSA-N 5-amino-4-chloro-2-phenyl-1,5-dihydropyridazin-6-one Chemical compound C1=C(Cl)C(N)C(=O)NN1C1=CC=CC=C1 LXILAQXSFLCWDQ-UHFFFAOYSA-N 0.000 description 1
- 241001073386 Acanthospermum hispidum Species 0.000 description 1
- 241001630332 Adonis dentata Species 0.000 description 1
- 244000296912 Ageratum conyzoides Species 0.000 description 1
- 235000004405 Ageratum conyzoides Nutrition 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 241000743987 Alopecurus pratensis Species 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 244000237958 Amaranthus spinosus Species 0.000 description 1
- 235000013480 Amaranthus spinosus Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000404031 Anacyclus Species 0.000 description 1
- 241000404028 Anthemis Species 0.000 description 1
- 241001282784 Atractylis carduus Species 0.000 description 1
- 241000143476 Bidens Species 0.000 description 1
- 244000296619 Cakile maritima Species 0.000 description 1
- 235000015890 Cakile maritima Nutrition 0.000 description 1
- 241001563787 Calopogonium Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000718035 Cenchrus echinatus Species 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 244000191502 Chenopodium murale Species 0.000 description 1
- 235000000751 Chenopodium murale Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 244000227271 Cleome gynandra Species 0.000 description 1
- 235000012469 Cleome gynandra Nutrition 0.000 description 1
- 241000208296 Datura Species 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- 235000011804 Dioscorea sp Nutrition 0.000 description 1
- 244000157519 Dioscorea sp Species 0.000 description 1
- 241000967566 Diplotaxis harra Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 241000400638 Echinochloa crus-pavonis Species 0.000 description 1
- 240000001837 Euphorbia peplus Species 0.000 description 1
- 244000084800 Euphorbia prunifolia Species 0.000 description 1
- NVKGMAKXUDHHBI-UHFFFAOYSA-N FC(C=1C=C(C=CC=1)N1NC(C(C(=C1)Br)Br)=O)(F)F Chemical compound FC(C=1C=C(C=CC=1)N1NC(C(C(=C1)Br)Br)=O)(F)F NVKGMAKXUDHHBI-UHFFFAOYSA-N 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 244000010922 Plantago major Species 0.000 description 1
- 235000015266 Plantago major Nutrition 0.000 description 1
- 240000006597 Poa trivialis Species 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 241000220263 Sisymbrium Species 0.000 description 1
- 235000002594 Solanum nigrum Nutrition 0.000 description 1
- 244000061457 Solanum nigrum Species 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
- RSESUCWJKLHXEZ-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=CC(C(F)(F)F)=C1 RSESUCWJKLHXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229940071162 caseinate Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PKDBSOOYVOEUQR-UHFFFAOYSA-N mucobromic acid Natural products OC1OC(=O)C(Br)=C1Br PKDBSOOYVOEUQR-UHFFFAOYSA-N 0.000 description 1
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/22—Nitrogen and oxygen atoms
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F03—MACHINES OR ENGINES FOR LIQUIDS; WIND, SPRING, OR WEIGHT MOTORS; PRODUCING MECHANICAL POWER OR A REACTIVE PROPULSIVE THRUST, NOT OTHERWISE PROVIDED FOR
- F03B—MACHINES OR ENGINES FOR LIQUIDS
- F03B13/00—Adaptations of machines or engines for special use; Combinations of machines or engines with driving or driven apparatus; Power stations or aggregates
- F03B13/02—Adaptations for drilling wells
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung neuer Pyridazon-Derivate Die vorliegende Erfindung betrifft neue Pyridazon-Derivate der Formel I, worin X Chlor oder Brom, R1 Wasserstoff oder Methyl bedeuten und R2 für Methylsteht, oder, falls R1 Wasserstoff Ist, auch Aethyl bedeuten kann, die herbizide Eigenschaften besitzen, sowie ein Verfahren zur Herstellung dieser Verbindungen. Process for the preparation of new pyridazone derivatives The present invention relates to new pyridazone derivatives of the formula I, where X is chlorine or bromine, R1 is hydrogen or methyl and R2 is methyl, or, if R 1 is hydrogen, can also be ethyl, which have herbicidal properties, and a process for the preparation of these compounds.
Erfindungsgemäss gelangt man zu den Pyridazon-Derivaten der Formel I, indem man eine Verbindung der Formel II worin X die obige Bedeutung besitzt, mit einer Verbindung der Formel III worin R1 und R2 die oben angegebenen Bedeutungen besitzen, umsetzt.According to the invention, the pyridazone derivatives of the formula I are obtained by adding a compound of the formula II wherein X has the above meaning with a compound of the formula III in which R1 and R2 have the meanings given above.
Die Herstellung der Verbindungen der Formel I kann wie folgt durchgeführt werden: Man erhitzt eine Verbindung der Forme. II mit-einer Lösung einer Verbindung der Formel III,beispielsweise in Aethanol, während 2 bis 24 Stunden auf etwa 70 bis 120°, vorzugsweise auf 85°, unter normalem oder erhöhtem Druck und arbeitet die Reaktionsmischung nach bekannten Methoden auf. Die Verbindungen der Formel I können durch Umkristallisation gereinigt werden.The compounds of the formula I can be prepared as follows be: One heats a connection of the form. II with-a solution of a compound of formula III, for example in ethanol, for 2 to 24 hours to about 70 to 120 °, preferably to 85 °, under normal or elevated pressure and works the reaction mixture according to known methods. The compounds of formula I. can be purified by recrystallization.
Die Verbindungen der Formel II können auf folgende Weise erhalten werden: 3-Trifluormethyl-phenylhydrazin wird mit einer Säure der Formel IV worin X die oben bezeichnete Bedeutung besitzt, vorzugsweise bei Raumtemperatur, in Gegenwart eines Lösungsmittels, z. B. einer mineralsauren wässrigen Lösung oder einem wasserhaltigen oder wasserfreien, -inerten organischen Lösungsmittel, wie Aethanol, das nach Beendigung der Reaktion abgedampft wird, zu dem entsprechenden Dihalogensäuresemicarbazon umgesetzt und dieses, ohne es zu isolieren, durch Kochen in Eisessig und/oder Essigsäureanhydrid oder durch Erwärmen in wässriger Mineralsäure, wie z.B. Salzsäure, bei Temperaturen von 70 bis ea. lOuu oder durch Rühren in konz. Mineralsäure, wie z.B. Schwefelsäure, bei Raumtemperatur zu der entsprechenden Verbindung der Formel II cyclisiert.The compounds of the formula II can be obtained in the following manner: 3-Trifluoromethylphenylhydrazine is treated with an acid of the formula IV wherein X has the meaning given above, preferably at room temperature, in the presence of a solvent, e.g. B. a mineral acid aqueous solution or an aqueous or anhydrous, inert organic solvent, such as ethanol, which is evaporated after the reaction has ended, converted to the corresponding dihalo semicarbazone and this, without isolating it, by boiling in glacial acetic acid and / or acetic anhydride or by heating in aqueous mineral acid, such as hydrochloric acid, at temperatures of 70 to ea. 10uu or by stirring in conc. Mineral acid, such as, for example, sulfuric acid, is cyclized at room temperature to give the corresponding compound of the formula II.
Die Verbindungen der Formel 1 sind Herbizide, die vor dem Auflaufen der Unkäuter oder spätestens im Keimstadium angewendet werden. Sie eignen sich inroige ihrer überraschend geringen Phytotoxizität gegen Baumwolle besonders gut für die Anwendung in BaumwollKulturen. Sie können aber auch in gewissen Fällen in Karotten- und Kartoffelkulturen angewendet werden.The compounds of formula 1 are herbicides that pre-emerge the weeds or at the latest in the germination stage. They are suitable inroige their surprisingly low phytotoxicity to cotton is particularly good for that Use in cotton crops. But in certain cases you can also use carrot and potato crops can be used.
Die Verbindungen der Formel 1 sind bei Vorauflaufanwendung bezüglich der herbiziden Wirkung der als Herbizia angewandten Verbindung 1=Yhenyl-4-amino-5-chlor-pyridazon-(b) überlegen und sind im Gegensatz zu 1-Phenyl-4-amino-5-chlor-pyridazon-(,b) selektiv in Bezug auf Baumwolle. Sie sind hinsichtlich der herbiziden Wirkung auch Verbindungen überlegen, die sich von Verbindungen der Formel I dadurch unterscheiden, dass sie an Stelle einer alkylierten Aminogruppe eine nicht alkylierte Aminogruppe enthalten.The compounds of formula 1 are with respect to pre-emergence application the herbicidal effect of the compound used as herbicide 1 = yhenyl-4-amino-5-chloro-pyridazon- (b) superior and, in contrast to 1-phenyl-4-amino-5-chloropyridazon - (, b), are selective in relation to cotton. They are also compounds in terms of herbicidal activity consider that differ from compounds of the formula I in that they instead of an alkylated amino group contain a non-alkylated amino group.
Die hervorragende herbizide Wirkung der Verbindungen der Formel I ist überraschend, da aus der Literatur bekannt war, dass beim Ersatz der Aminogruppe beim 1-Phenyl-4-amino -5-chlor-pyridazon-(6) durch eine Alkylamino-, bzw. Dialkylaminogruppe die herbizide Wirkung stark abnimmt bzw. verschwindet.The excellent herbicidal action of the compounds of the formula I. is surprising because it was known from the literature that when the amino group was replaced for 1-phenyl-4-amino -5-chloro-pyridazon- (6) by an alkylamino-, or dialkylamino group the herbicidal effect decreases or disappears.
Die nachfolgenden Beispiele dienen zur Erläuterung der Herstellung der erfindungsgemässen Verbindungen, sollen die Erfindung aber in keiner Weise einschränken. Die Temperaturangaben erfolgen in Celsiusgraden. Beispiel 1: 1=(3_Trifluormethylphen@l)_4=meth@lamino=5= chlor=pyridazon_(6) 20 g 1-(3-Trifluormethylphenyl)-4,5-dichlorpyridazon-(6) werden mit einer Lösung von 15 g Methylamin in 175 ml Alkohol versetzt und 24 Stunden auf 85° erhitzt. Danach wird mit Wasser gefällt, der Niederschlag abfiltriert und getrocknet. Durch Umkristallisierencus Alkohol erhält man 1-(3-Trifluormethylphenyl)-4-methylamino-5-chlor-pyridazon-(6) vom Smp. 183-185o.The following examples serve to explain the preparation of the compounds according to the invention, are not intended to restrict the invention in any way. The temperatures are given in degrees Celsius. Example 1: 1 = (3_trifluoromethylphen @ l) _4 = meth @ lamino = 5 = chlorine = pyridazon_ (6) 20 g of 1- (3-trifluoromethylphenyl) -4,5-dichloropyridazon- (6) mixed with a solution of 15 g of methylamine in 175 ml of alcohol and 24 hours Heated to 85 °. Then it is precipitated with water, the precipitate is filtered off and dried. Recrystallization of alcohol gives 1- (3-trifluoromethylphenyl) -4-methylamino-5-chloro-pyridazon- (6) from m.p. 183-185o.
Das als Ausgangsprodukt benötigte 1-(3-Trifluormethylphenyl)-4,5-dichlorpyridazon-(6) kann auf folgende Weise hergestellt werden: 57,5 g Mucochlorsäure werden in 100 ml abs. Alkohol gelöst und mit 60 g m-Trifluormethylphenylhydrazin versetzt. Dann wird die Lösung unter vermindertem Druck zur Trockne eingedampft und unter Zusatz von 120 ml Eisessig und 120 ml Essigsäureanhydrid 40 Minuten unter Rückfluss erhitzt. Anschliessend wird wieder unter vermindertem Druck zur Trockne eingedampft, worauf beim Umkristallisieren aus 90%igem wässrigem Alkohol farblose Kristalle vom Smp. 92-94° erhalten werden. Die Ausbeute an 1-(3-Trifluormethylphenyl)-4,5-dichlorpyridazon-(6) beträgt 94 g.The 1- (3-trifluoromethylphenyl) -4,5-dichloropyridazon- (6) required as the starting product can be prepared in the following way: 57.5 g of mucochloric acid are in 100 ml abs. Dissolved alcohol and mixed with 60 g of m-trifluoromethylphenylhydrazine. then the solution is evaporated to dryness under reduced pressure and with addition heated under reflux for 40 minutes by 120 ml of glacial acetic acid and 120 ml of acetic anhydride. It is then again evaporated to dryness under reduced pressure, whereupon on recrystallization from 90% aqueous alcohol, colorless crystals of mp. 92-94 ° can be obtained. The yield of 1- (3-trifluoromethylphenyl) -4,5-dichloropyridazon- (6) is 94 g.
Beispiel 2: 1-(3-Trifluormeth 1 henyl)-4-äthylamino-5-chlor ridazon-(6) 20 g 1-(3-Trifluormethylphenyl)-4,5-dichlorpyridazon-(6) und 20 g Aethylamin werden in 200 ml Alkohol 24 Stunden auf 85° erhitzt. Danach wird mit Wasser gefällt, der Niederschlag abfiltriert und getrocknet. Durch Umkristallisation aus Alkohol erhält man das l-(3-Trifluormethylphenyl)-4-äthylamino-5-chlor-pyridazon-(6) vom Smp. 1.320. Example 2: 1- (3-Trifluorometh 1 henyl) -4-ethylamino-5-chloro ridazon- (6) 20 g of 1- (3-trifluoromethylphenyl) -4,5-dichloropyridazone (6) and 20 g of ethylamine are in 200 ml of alcohol heated to 85 ° for 24 hours. Then it is precipitated with water, the precipitate is filtered off and dried. Recrystallization from alcohol gives 1- (3-trifluoromethylphenyl) -4-ethylamino-5-chloro-pyridazon- (6) with a melting point of 1,320.
Beispiel 3: 1-(3-Trifluormethylphen 1)-4-dimeth lamino--- -------------------- x-----------y-5-chlor-pyridazon-(6) 50 g 1-(3-Trifluormethylphenyl)-4,5-dichlorpyridazon-(6) werden mit einer Lösung aus 36,5 g Dimethylamin in 200 ml Alkohol versetzt und 24 Stunden bei 85° gerührt. Danach wird mit Wasser gefällt, der Niederschlag abfiltriert und getrocknet. Durch Umkristallisieren aus Alkohol erhält man das 1-(3-Trifluormethylphenyl)-4-dimethylamino-5-chlorpyridazon-(6) vom Smp. 153°. Example 3: 1- (3-trifluoromethylphen 1) -4-dimeth lamino --- -------------------- x ---------- -y-5-chloropyridazon- (6) 50 g of 1- (3-trifluoromethylphenyl) -4,5-dichloropyridazon- (6) are mixed with a solution of 36.5 g of dimethylamine in 200 ml of alcohol and 24 hours at 85 ° stirred. Then it is precipitated with water, the precipitate is filtered off and dried. Recrystallization from alcohol gives 1- (3-trifluoromethylphenyl) -4-dimethylamino-5-chloropyridazon- (6) with a melting point of 153 °.
Beispie 1 4: 1-(3=Trifluormethylphenyl)-4=methylamino=5= brom-pyridazon-(6) .Example 1 4: 1- (3 = trifluoromethylphenyl) -4 = methylamino = 5 = bromopyridazon- (6).
10 g 1-(3-Trifluormethylphenyl)-4,5-dibrom-pyridazon-(6) und 4 g Methylamin in 50 ml Alkohol werden 24 Stunden auf 85° erhitzt. Bei gleicher Aufarbeitung wie in den obigen Beispielen erhält man das 1-(3-Trifluormethylphenyl)-4-methylamino-5-brom-pyridazon-(6) vom Smp. 156-158a-.10 g of 1- (3-trifluoromethylphenyl) -4,5-dibromopyridazon- (6) and 4 g of methylamine in 50 ml of alcohol are heated to 85 ° for 24 hours. With the same processing as in the above examples, 1- (3-trifluoromethylphenyl) -4-methylamino-5-bromo-pyridazon- (6) is obtained of m.p. 156-158a-.
Das als Ausgangsmaterial verwendete 1-(3-Trifluormethylphenyl)-4,5-dibrom-pyridazon-(6) kann auf folgende Weise hergestellt werden: ' 100 g Mucobromsäure werden in 200 ml abs. Alkohol gelöst und mit 62 g m-Trifluormethylphenylhydrazin versetzt. Dann wird die Lösung unter vermindertem Druck zur Trockne eingedampft und unter Zusatz von 130 ml Eisessig und 13C ml Essigsäureanhydrid 4 Stunden unter Rückfluss erhitzt. Anschliessend wird wieder unter vermindertem Druck zur Trockne eingedampft, worauf beim Umkristallisieren aus 90%igem wässrigem Alkohol Kristalle vom Smp.103-1050 erhalten werden. Die Ausbeute an 1-(3-Trifluormethylphenyl)-4,5-dibrompyridazon-(6) beträgt 104 g.The 1- (3-trifluoromethylphenyl) -4,5-dibromopyridazon- (6) used as starting material can be prepared in the following way: 100 g of mucobromic acid are dissolved in 200 ml of abs. Dissolved alcohol and mixed with 62 g of m-trifluoromethylphenylhydrazine. The solution is then evaporated to dryness under reduced pressure and heated under reflux for 4 hours with the addition of 130 ml of glacial acetic acid and 13C ml of acetic anhydride. It is then again evaporated to dryness under reduced pressure, whereupon crystals of melting point 103-1050 are obtained on recrystallization from 90% aqueous alcohol. The yield of 1- (3-trifluoromethylphenyl) -4,5-dibromopyridazon- (6) is 104 g.
Beis iel 5: 1-(_3-Trifluormeth 1 @2nyl)-4-äthylamino-5-brom-pyridazon-(6) 10 g 1-(3-Trifluormethylphenyl)-4,5-dibrom-pyridazon-(6) und 6 g Aethylamin in 60 ml Alkohol werden 24 Stunden auf 850 erhitzt. Bei gleicher Aufarbeitung wie in den obigen Beispielen erhält man nach dem Umkristallisieren aus Alkohol das 1-(3-Trifluormethylphenyl)-4-äthylamino-5-brom-pyridazon-(6) vom Smp. 138-140°.B ice iel 5: 1 - (_ 3-Trifluormeth 1 @ 2nyl) -4-ethylamino-5-bromo-pyridazone (6) 10 g of 1- (3-trifluoromethylphenyl) -4,5-dibromo-pyridazone (6) and 6 g of ethylamine in 60 ml of alcohol are heated to 850 for 24 hours. With the same work-up as in the above examples, 1- (3-trifluoromethylphenyl) -4-ethylamino-5-bromopyridazon- (6) with a melting point of 138-140 ° is obtained after recrystallization from alcohol.
Beispiel 6: 1_(3=Trifluormethylphenyl)=4=dimethylamino= 5_bromlpyridazon=(#6) 25,8 g 1-(3-Trifluormethylphenyl)-4,5-dibrom-pyridazon-(6), und 30 g Dimethylamin in 200 ml Alkohol werden 24 Stunden auf 850 erhitzt. Bei gleicher Aufarbeitung wie in den obigen Beispielen erhält man das 1-(3-Trifluormethylphenyl)-4-dimethylamino-5-brom-pyridazon-%6) vom Smp. 1590. Example 6: 1_ (3 = trifluoromethylphenyl) = 4 = dimethylamino = 5_bromlpyridazon = (# 6) 25.8 g of 1- (3-trifluoromethylphenyl) -4,5-dibromopyridazon- (6), and 30 g of dimethylamine in 200 ml of alcohol are heated to 850 for 24 hours. With the same work-up as in the above examples, 1- (3-trifluoromethylphenyl) -4-dimethylamino-5-bromopyridazone% 6) with a melting point of 1590 is obtained.
Die Verbindungen können in Mischung mit den bei Herbiziden üblichen Verdünnungsmitteln und Trägerstoffen zur Anwendung gelangen.The compounds can be mixed with those customary for herbicides Thinners and carriers are used.
Die nachfolgenden Beispiele a) bis i) dienen zur Erläuterung der Anwendungsformen der Verbindungen@der Formel I, ohne die Erfindung einzuschränken. a) 70 g 1-(3-Trifluormethylphenyl)-4-dimethylamino-5-chlor-pyridazon-(6) werden zusammen mit 30 g eines inerten festen Trägers, der aus einem Gemisch von 15 g Kaolin, 7 g Diatomeenerde, 7 g Talkum besteht, und 1 g eines Haftmittels in einer Kugelmühle zu einem feinen Pulver vermahlen, welches als Stäubemittel dient.The following examples a) to i) serve to explain the application forms of the compounds @ of the formula I, without restricting the invention. a) 70 g of 1- (3-trifluoromethylphenyl) -4-dimethylamino-5-chloro-pyridazon- (6) are combined with 30 g of an inert solid carrier, which consists of a mixture of 15 g of kaolin, 7 g of diatomaceous earth, 7 g of talc, and 1 g of an adhesive in a ball mill Grind to a fine powder, which serves as a dusting agent.
b) 20 g 1-(3-Trifluormethylphenyl)-4-methylamino-5-chlorpyridazon-(6) werden mit 72 g eines inerten festen Trägerstoffgemisches, welches aus 2/3 Diatomeenerde und 1/3 Kaolin besteht, 6 g Isooctylphenyloctaglykoläther und 2 g eines Schutzkolloids, z.B. Sufitablauge, in einer Stiftenmühle zu einem feinen Fulver vermahlen, das in Wasser suspendierbar ist.b) 20 g of 1- (3-trifluoromethylphenyl) -4-methylamino-5-chloropyridazon- (6) with 72 g of an inert solid carrier mixture, which consists of 2/3 diatomaceous earth and 1/3 consists of kaolin, 6 g of isooctylphenyloctaglycol ether and 2 g of a protective colloid, E.g. Sufitablauge, ground in a pin mill to a fine fulver, which in Water is suspendable.
c) Ein pulverförmiges, in Wasser gut suspendierbares Mittel wird erhalten, wenn man 25 g einer Verbindung der Formel I mit 3 g tert. Dodecylmercaptanundecaglykoläther, 7 g pulverförmigem Kieselsäuregel und 65 g Kaolin vermischt und mahlt.c) A powdery agent which can be easily suspended in water is obtained, if you tert 25 g of a compound of formula I with 3 g. Dodecyl mercaptan undecaglycol ether, 7 g of powdered silica gel and 65 g of kaolin are mixed and ground.
d) 50 g 1-(3-Trifluormethylphenyl)-4-äthylamino-5-chlorpyridazon-(6), 15 g pulvriger Sojabohneneiweissextrakt (Spray Soy), 5 g Dextrin, 18 g eines sulfonierten Kondensationsproduktes aus Naphthalin und Formaldehyd, 4 g Natriumalkylbenzolsulfonat, 2 g Ammoniumkaseinat und 6 g kolloide Kieselsäure werden zusammen in einer Kugelmühle zu einem feinen lockeren Pulver vermahlen.d) 50 g of 1- (3-trifluoromethylphenyl) -4-ethylamino-5-chloropyridazon- (6), 15 g of powdered soybean protein extract (Spray Soy), 5 g of dextrin, 18 g of a sulfonated one Condensation product of naphthalene and formaldehyde, 4 g sodium alkylbenzenesulfonate, 2 g ammonium caseinate and 6 g colloidal silica are put together in a ball mill Grind to a fine, fluffy powder.
e) 80 g 1-(3-Trifluormethylphenyl)-4-methylamino-5-brompyridazon-.(6), 5 g Sulfitcellulosepulver (Ca-salz), 5 g eines aus 3/4 Sojabohneneiweissextrakt (Spray Soy) und 1/4 Dextrin bestehenden, pulvrigen Gemisches, und 10 g kolloide Kieselsäure werden zusammen mit 200 ml Wasser in einer Kugelmühle fein vermahlen. e) 80 g of 1- (3-trifluoromethylphenyl) -4-methylamino-5-bromopyridazone -. (6), 5 g of sulfite cellulose powder (Ca salt), 5 g of a 3/4 soybean protein extract (Spray Soy) and 1/4 Powdery mixture consisting of dextrin and 10 g of colloidal silica are finely ground together with 200 ml of water in a ball mill.
f) Wird die gemäss e) erhaltene Suspension, ohne Zusatz eines Verdickungsmittels, im Vakuum sorgfältig zur Trockne eingedampft und anschliessend in einer Kugelmühle vermahlen, so erhält man ein feines lockeres Spritzpulver, welches beim Einrühren in WasserAriwendungsbrühen von hervorragenden Suspensionseigenschaften ergibt und einen Wirkstoffgehalt von 80 % besitzt.f) If the suspension obtained according to e), without the addition of a thickener, Carefully evaporated to dryness in vacuo and then in a ball mill ground, a fine, loose spray powder is obtained, which when stirred in in water application broths with excellent suspension properties and has an active ingredient content of 80%.
g) 800 g 1-(3-Trifluormethylphenyl)-4-dimethylamino-5-chlor-pyridazon-(6) werden in einer Stiftenmühle gemahlen, wobei die Feinheit des Pulvers mindestens 90 p pro 0,045 mm beträgt, und dann in einen Horizontalmischer gebracht,- worin sie mit 185 g einer aus 84 g sulfoniertem Kondensationsprodukt aus Naphthalin und Formaldehyd, 84 g Sulfiteellulosepulver (Ca-salz) und 17 g Natriumalkylbenzolsulfonat bestehenden Mischung 1/2 Stunde lang vermischt werden. Nach Zugabe von 15 g Carboxymethylcellulosepulver wird anschliessend noch 1 Stunde lang gemischt und das Gemisch in einer Kolloidmühle fein vermahlen. Man erhält ein Spritzpulver mit 80 % Wirkstoffgehalt, welches in Wasser hervorragend suspendierbar ist. g) 800 g of 1- (3-trifluoromethylphenyl) -4-dimethylamino-5-chloro-pyridazon- (6) are ground in a pin mill, the fineness of the powder being at least 90 p per 0.045 mm, and then placed in a horizontal mixer In which they are mixed for 1/2 hour with 185 g of a mixture consisting of 84 g of sulfonated condensation product of naphthalene and formaldehyde, 84 g of sulfite cellulose powder (Ca salt) and 17 g of sodium alkylbenzenesulfonate. After adding 15 g of carboxymethyl cellulose powder, the mixture is then mixed for a further hour and the mixture is finely ground in a colloid mill. A wettable powder with an active ingredient content of 80% is obtained, which can be excellently suspended in water.
h) 50 g 1-(3-Trifluormethylphenyl)-4-dimethylamino-5-ehlor-pyridazon-(6) und 850 g Bentonit werden in einen Mischer gegeben und 100 g Diglykol unter fortwährendem Mischen aufgespritzt. Die erhaltene Mischung wird in einem Kneter durchgeknetet und dann auf eine Korngrösse von 0,5 bis l mnr granuliert. Das erhaltene Granulat wird als Herbizid appliziert.h) 50 g of 1- (3-trifluoromethylphenyl) -4-dimethylamino-5-chloro-pyridazon- (6) and 850 g of bentonite are added to a mixer and 100 g of diglycol while continuing Mixing sprayed on. The mixture obtained is kneaded in a kneader and then to a grain size granulated from 0.5 to 1 mnr. That Granules obtained are applied as a herbicide.
i) Eine Acetonlösung von 20 g 1-(3-Trifluormethylphenyl)-4-dimethylamino-5-chlor-pyridazon-(6) wird auf 180 g Himsgranulat, das eine Korngrösse von 0,3 bis 1 mm besitzt, aufgespritzt und hierauf das Lösungsmittel im Wasserstrahlvakuum bei 40-60° entfernt. Man erhält ein sehr gut fliessendes körniges Granulat.i) An acetone solution of 20 g of 1- (3-trifluoromethylphenyl) -4-dimethylamino-5-chloro-pyridazon- (6) is sprayed onto 180 g Himsgranulat, which has a grain size of 0.3 to 1 mm and then the solvent is removed in a water jet vacuum at 40-60 °. You get a very good flowing granular granulate.
Nachfolgend wird die herbizide Wirkung der Verbindungen der Formel
-I beschrieben. Die in den Tabellen mit Nr. 1 -6 bezeichneten Wirkstoffe bedeuten:
Nr. 1: 1-(3-Trifluormethylphenyl)-4-methylamino-5-chlorpyridazon-(6)
Nr. 2: 1-(3-Trifluormethylphenyl)-4-äthylamino-5-chlorpyridazon-(6) Nr. 1-(3-Trifluormethylphenyl)-4-dimethylamino-5-chlorpyridazon-(6)
Nr. 4: 1-(3-Trifluormethylphenyl)-4-methylamino-5-brompyridazon-(6) . Nr.
1-(3-Trifluormethylphenyl)-4-äthylamino-5-brompyridazon-(6) N r. 6: 1-.(3-Trifluormethylphenyl)-4-dimethylamino-5-brompyridazon-(6)
Unkrautvernichtun im Yorauflauf-Verfahren: 30 x 40 cm grosse Saatschalen wurden
6 cm hoch mit einer Mischung, bestehtend aus TKS (Torf-Kultur-Substrat
Nr. 1)
und Sand gefüllt. Hierauf wurde mit einer 0,04 %
bzw. 0,2 % Wirkstoff enthaltenden wässrigen Suspension, und zwar entsprechend einer
Aufwandmenge von 1500 1 Brühe pro Hektar, besprüht. Danach wurden Samen folgender
Unkräuter in die so vorbereiteten Schalen ausgesät: Alopecurus pratensis (Al.p.)
Alopecurus myosuroides (Alm.) Amaranthus retroflexus (Am.) Capsella bursa-pastoris
(Ca.) Chenopodium albuni (Ch.) Echinochloa crus-galli (Ech.) Plantago major (P1.)
Poa trivialis (PO.)
Senecio vulgaris (Se.) Stellaria media (St.) Nach der
Aussaat wurde etwa 1 cm hoch mit Erde gedeckt und 28 Tage lang unter normalen Gewächshausbedingungen
gehalten. Die Beurteilung der herbiziden Wirkung ergab die in der Tabelle -1 wiedergegebenen
Resultate.
Nach der Aussaat wurde etwa 1 cm hoch mit Erde gedeckt und 28 Tage
lang unter normalen Gewächshausbedingungen gehalten. Die Versuchsauswertung ergab
hinsichtlich der Selektivität die in der Tabelle 2 angegebenen Resultate.
Danach wurden Samen von Baumwolle (Gossypium herbaceum) sowie von
den in Tabelle 1 genannten Unkrautpflanzen in die so vorbehandelten Schalen
ausgesät.
Nach der Aussaat wurde etwa 1 cm hoch mit Erde gedeckt
und 28 Tage lang unter normalen Gewächshausbedingungen gehalten. Die Versuchsauswertung
ergab für die Selektivität in Baumwolle die in der Tabelle 3 gezeigten Resultate.
Die Substanz A bedeutet 1-Phenyl-4-amino-5-chlorpyridazon-(6).
Unkrautvernichtung im Vorauflauf-Verfahren - Tropen: ---------------
2,4
kg 1-(3-Trifluormethylphenyl)-4-dimethylamino-5-chlorpyridazon-(6) pro Hektar wurden
vor dem Auflaufen der Unkräuter ausgebracht. Dabei wurden ca. 80 bis 100 % der folgenden
Unkräuter vernichtet:
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1968S0114601 DE1695840B2 (en) | 1968-03-18 | 1968-03-18 | 1- (3-TRIFLOROMETHYLPHENYL) -4-ALKYLAMINO-5-HALOGEN-PYRIDAZONE (6) DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND HERBICIDALS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1968S0114601 DE1695840B2 (en) | 1968-03-18 | 1968-03-18 | 1- (3-TRIFLOROMETHYLPHENYL) -4-ALKYLAMINO-5-HALOGEN-PYRIDAZONE (6) DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND HERBICIDALS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1695840A1 true DE1695840A1 (en) | 1971-05-13 |
| DE1695840B2 DE1695840B2 (en) | 1976-08-05 |
Family
ID=7533298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1968S0114601 Granted DE1695840B2 (en) | 1968-03-18 | 1968-03-18 | 1- (3-TRIFLOROMETHYLPHENYL) -4-ALKYLAMINO-5-HALOGEN-PYRIDAZONE (6) DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND HERBICIDALS |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1695840B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0410238A3 (en) * | 1989-07-28 | 1991-07-24 | Bayer Ag | Pyridazinone derivatives |
| EP0352638A3 (en) * | 1988-07-27 | 1991-07-31 | BASF Aktiengesellschaft | 5-amino-6-pyridazinon-derivatives, process for their preparation and herbicidal agent containing them |
| EP2052612A1 (en) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbicide combination |
| DE102008037629A1 (en) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides |
-
1968
- 1968-03-18 DE DE1968S0114601 patent/DE1695840B2/en active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0352638A3 (en) * | 1988-07-27 | 1991-07-31 | BASF Aktiengesellschaft | 5-amino-6-pyridazinon-derivatives, process for their preparation and herbicidal agent containing them |
| EP0410238A3 (en) * | 1989-07-28 | 1991-07-24 | Bayer Ag | Pyridazinone derivatives |
| US5097028A (en) * | 1989-07-28 | 1992-03-17 | Bayer Aktiengesellschaft | 2-substituted-4-substituted-5-amino-2h-pyridazin-3-ones |
| EP2052612A1 (en) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbicide combination |
| DE102008037629A1 (en) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbicide combination with dimethoxytriazinyl-substituted difluoromethanesulfonylanilides |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1695840B2 (en) | 1976-08-05 |
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