CA1053232A - Salts of phenylpyridazines and the preparation thereof - Google Patents
Salts of phenylpyridazines and the preparation thereofInfo
- Publication number
- CA1053232A CA1053232A CA241,581A CA241581A CA1053232A CA 1053232 A CA1053232 A CA 1053232A CA 241581 A CA241581 A CA 241581A CA 1053232 A CA1053232 A CA 1053232A
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- general formula
- chlorine
- chloro
- salt
- 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.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 150000003839 salts Chemical class 0.000 title claims description 5
- XWSSUYOEOWLFEI-UHFFFAOYSA-N 3-phenylpyridazine Chemical class C1=CC=CC=C1C1=CC=CN=N1 XWSSUYOEOWLFEI-UHFFFAOYSA-N 0.000 title description 4
- 239000000460 chlorine Substances 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 17
- -1 Amine salts Chemical class 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000002560 nitrile group Chemical group 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- ZUSHSDOEVHPTCU-UHFFFAOYSA-N 6-chloro-3-phenyl-1h-pyridazin-4-one Chemical compound N1C(Cl)=CC(=O)C(C=2C=CC=CC=2)=N1 ZUSHSDOEVHPTCU-UHFFFAOYSA-N 0.000 claims description 21
- 150000001412 amines Chemical group 0.000 claims description 9
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical class CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 claims description 3
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical class CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 3
- BUEAACVLKZAVFX-UHFFFAOYSA-N 3-(2-methylpropylamino)propanenitrile Chemical class CC(C)CNCCC#N BUEAACVLKZAVFX-UHFFFAOYSA-N 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- IWSZDQRGNFLMJS-UHFFFAOYSA-N 2-(dibutylamino)ethanol Chemical class CCCCN(CCO)CCCC IWSZDQRGNFLMJS-UHFFFAOYSA-N 0.000 claims 1
- DVFGEIYOLIFSRX-UHFFFAOYSA-N 3-(2-ethylhexoxy)propan-1-amine Chemical class CCCCC(CC)COCCCN DVFGEIYOLIFSRX-UHFFFAOYSA-N 0.000 claims 1
- RUVUQOOKKGVDNN-UHFFFAOYSA-N 3-(ethylamino)propanenitrile Chemical class CCNCCC#N RUVUQOOKKGVDNN-UHFFFAOYSA-N 0.000 claims 1
- UNIJBMUBHBAUET-UHFFFAOYSA-N 3-(methylamino)propanenitrile Chemical class CNCCC#N UNIJBMUBHBAUET-UHFFFAOYSA-N 0.000 claims 1
- AFXXFNVAHYRPIZ-UHFFFAOYSA-N 3-(octylamino)propanenitrile Chemical class CCCCCCCCNCCC#N AFXXFNVAHYRPIZ-UHFFFAOYSA-N 0.000 claims 1
- MZQXEAUWIMFFCG-UHFFFAOYSA-N 3-(propylamino)propanenitrile Chemical class CCCNCCC#N MZQXEAUWIMFFCG-UHFFFAOYSA-N 0.000 claims 1
- JZOZZDCUSWCAAJ-UHFFFAOYSA-N 6-bromo-3-phenyl-1h-pyridazin-4-one Chemical compound OC1=CC(Br)=NN=C1C1=CC=CC=C1 JZOZZDCUSWCAAJ-UHFFFAOYSA-N 0.000 claims 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical class CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical class C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 abstract description 14
- 239000000203 mixture Substances 0.000 abstract description 8
- 241000196324 Embryophyta Species 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000011833 salt mixture Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 150000002440 hydroxy compounds Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 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 2
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 2
- 239000002794 2,4-DB Substances 0.000 description 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000132570 Centaurea Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 241000520028 Lamium Species 0.000 description 2
- 239000005574 MCPA Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 229920005610 lignin Polymers 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
- XBAXAJAODIQLCI-UHFFFAOYSA-N 3-(propan-2-ylamino)propanenitrile Chemical class CC(C)NCCC#N XBAXAJAODIQLCI-UHFFFAOYSA-N 0.000 description 1
- YICPBKWYZXFJNB-UHFFFAOYSA-N 3-chloro-1h-pyridazin-6-one Chemical compound OC1=CC=C(Cl)N=N1 YICPBKWYZXFJNB-UHFFFAOYSA-N 0.000 description 1
- IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical compound ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 description 1
- 241000602336 Anthemis arvensis Species 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 240000003759 Erodium cicutarium Species 0.000 description 1
- ZLSWBLPERHFHIS-UHFFFAOYSA-N Fenoprop Chemical compound OC(=O)C(C)OC1=CC(Cl)=C(Cl)C=C1Cl ZLSWBLPERHFHIS-UHFFFAOYSA-N 0.000 description 1
- 240000005702 Galium aparine Species 0.000 description 1
- 235000014820 Galium aparine Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241001513371 Knautia arvensis Species 0.000 description 1
- 240000002702 Lapsana communis Species 0.000 description 1
- 239000005575 MCPB Substances 0.000 description 1
- 101150039283 MCPB gene Proteins 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000286177 Raphanus raphanistrum Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 235000005545 Veronica americana Nutrition 0.000 description 1
- 241001166549 Veronica hederifolia Species 0.000 description 1
- 240000005592 Veronica officinalis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000080 wetting agent 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
- C07D237/14—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT1007374A AT334133B (de) | 1974-12-17 | 1974-12-17 | Herbizides mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1053232A true CA1053232A (en) | 1979-04-24 |
Family
ID=3619675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA241,581A Expired CA1053232A (en) | 1974-12-17 | 1975-12-08 | Salts of phenylpyridazines and the preparation thereof |
Country Status (21)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2741260A1 (de) * | 1977-09-14 | 1979-03-22 | Bayer Ag | Neue 1,4-dihydropyridazine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2745496A1 (de) * | 1977-10-10 | 1979-05-17 | Bayer Ag | Neue 1-n-substituierte 1.4-dihydropyridazine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| US4187097A (en) * | 1977-12-16 | 1980-02-05 | Monsanto Company | N-hydrazides of 2-benzothiazolinone as plant growth regulants |
| AT397598B (de) * | 1990-04-05 | 1994-05-25 | Agrolinz Agrarchemikalien | Herbizides mittel |
| AT397085B (de) * | 1992-02-17 | 1994-01-25 | Agrolinz Agrarchemikalien | Herbizide n-cyanopyridazinone |
| CN110128352A (zh) * | 2018-02-02 | 2019-08-16 | 青岛清原化合物有限公司 | 哒嗪醇类化合物及其衍生物、制备方法、除草组合物和应用 |
| CN111820224B (zh) * | 2019-04-22 | 2022-04-05 | 江苏清原农冠杂草防治有限公司 | 包含三氟甲基哒嗪醇类化合物的除草组合物及其应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2805926A (en) * | 1956-04-11 | 1957-09-10 | Us Rubber Co | Plant growth regulants |
| DE2129109C3 (de) * | 1971-06-11 | 1979-06-07 | Lentia Gmbh | Phenylpyridazine, ihre Herstellung und sie enthaltende herbizide Mittel |
| DE2341629A1 (de) * | 1973-08-17 | 1975-02-27 | Basf Ag | Herbizid |
| DE2351553A1 (de) * | 1973-10-13 | 1975-04-24 | Basf Ag | Herbizid |
-
1974
- 1974-12-17 AT AT1007374A patent/AT334133B/de not_active IP Right Cessation
-
1975
- 1975-11-19 DE DE19752551975 patent/DE2551975A1/de not_active Withdrawn
- 1975-11-24 CS CS757944A patent/CS195717B2/cs unknown
- 1975-11-28 DK DK537475A patent/DK537475A/da unknown
- 1975-12-08 GB GB5028475A patent/GB1474896A/en not_active Expired
- 1975-12-08 CA CA241,581A patent/CA1053232A/en not_active Expired
- 1975-12-08 ZA ZA757673A patent/ZA757673B/xx unknown
- 1975-12-09 IL IL48636A patent/IL48636A/xx unknown
- 1975-12-09 HU HU75CE1071A patent/HU173972B/hu unknown
- 1975-12-10 FR FR7537757A patent/FR2295028A1/fr active Granted
- 1975-12-15 PL PL1975185576A patent/PL97265B1/pl unknown
- 1975-12-15 LU LU74020A patent/LU74020A1/xx unknown
- 1975-12-15 DD DD190157A patent/DD122470A1/xx unknown
- 1975-12-16 BE BE162786A patent/BE836691A/xx unknown
- 1975-12-16 NL NL7514641A patent/NL7514641A/xx not_active Application Discontinuation
- 1975-12-16 US US05/641,588 patent/US4058390A/en not_active Expired - Lifetime
- 1975-12-16 ES ES443536A patent/ES443536A1/es not_active Expired
- 1975-12-17 SU SU752199208A patent/SU625576A3/ru active
- 1975-12-17 JP JP50149641A patent/JPS5186131A/ja active Pending
- 1975-12-17 BR BR7508389*A patent/BR7508389A/pt unknown
- 1975-12-17 CH CH1634775A patent/CH595043A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE836691A (fr) | 1976-06-16 |
| IL48636A (en) | 1978-12-17 |
| FR2295028B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-06-29 |
| NL7514641A (nl) | 1976-06-21 |
| AU8741375A (en) | 1977-06-16 |
| CH595043A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-01-31 |
| FR2295028A1 (fr) | 1976-07-16 |
| ES443536A1 (es) | 1977-05-01 |
| DK537475A (da) | 1976-06-18 |
| AT334133B (de) | 1976-12-27 |
| DD122470A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-10-12 |
| DE2551975A1 (de) | 1976-07-01 |
| LU74020A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-07-20 |
| HU173972B (hu) | 1979-10-28 |
| ZA757673B (en) | 1976-11-24 |
| PL97265B1 (pl) | 1978-02-28 |
| US4058390A (en) | 1977-11-15 |
| CS195717B2 (en) | 1980-02-29 |
| IL48636A0 (en) | 1976-02-29 |
| ATA1007374A (de) | 1976-04-15 |
| BR7508389A (pt) | 1976-08-24 |
| SU625576A3 (ru) | 1978-09-25 |
| JPS5186131A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-07-28 |
| GB1474896A (en) | 1977-05-25 |
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