DE1567213A1 - Mittel zur Regulierung des Pflanzenwuchses - Google Patents
Mittel zur Regulierung des PflanzenwuchsesInfo
- Publication number
- DE1567213A1 DE1567213A1 DE19661567213 DE1567213A DE1567213A1 DE 1567213 A1 DE1567213 A1 DE 1567213A1 DE 19661567213 DE19661567213 DE 19661567213 DE 1567213 A DE1567213 A DE 1567213A DE 1567213 A1 DE1567213 A1 DE 1567213A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- derivative
- active ingredient
- dimethylaminofumaramic
- fumaramic
- 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.)
- Pending
Links
- 230000008635 plant growth Effects 0.000 title claims description 9
- 230000001105 regulatory effect Effects 0.000 title claims description 9
- 239000002253 acid Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 26
- -1 C1-4 alkyl fumaramic acid Chemical compound 0.000 claims description 18
- 241000196324 Embryophyta Species 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- ACVHHVCLERJENS-ONEGZZNKSA-N (e)-4-(2,2-dimethylhydrazinyl)-4-oxobut-2-enoic acid Chemical compound CN(C)NC(=O)\C=C\C(O)=O ACVHHVCLERJENS-ONEGZZNKSA-N 0.000 claims description 12
- FSQQTNAZHBEJLS-UHFFFAOYSA-N Monoamide-Fumaric acid Natural products NC(=O)C=CC(O)=O FSQQTNAZHBEJLS-UHFFFAOYSA-N 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 10
- FSQQTNAZHBEJLS-OWOJBTEDSA-N (e)-4-amino-4-oxobut-2-enoic acid Chemical compound NC(=O)\C=C\C(O)=O FSQQTNAZHBEJLS-OWOJBTEDSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 230000012010 growth Effects 0.000 claims description 6
- 241001553178 Arachis glabrata Species 0.000 claims description 4
- 150000004702 methyl esters Chemical class 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- IOCOIVLEHVKVJC-BJILWQEISA-N (E)-4-(2,2-dimethylhydrazinyl)-4-oxobut-2-enoic acid hydrochloride Chemical compound Cl.CN(NC(/C=C/C(=O)O)=O)C IOCOIVLEHVKVJC-BJILWQEISA-N 0.000 claims description 2
- NRMACYVLTHGFLA-SNAWJCMRSA-N (e)-4-oxo-4-(piperidin-1-ylamino)but-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)NN1CCCCC1 NRMACYVLTHGFLA-SNAWJCMRSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 18
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 2
- UUDQEAHYPKZNCP-OWOJBTEDSA-N (e)-4-(morpholin-4-ylamino)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)NN1CCOCC1 UUDQEAHYPKZNCP-OWOJBTEDSA-N 0.000 claims 1
- CJAVUPWGLVWWAS-AATRIKPKSA-N C(C)OC(\C=C\C(=O)NN(C)C)=O Chemical compound C(C)OC(\C=C\C(=O)NN(C)C)=O CJAVUPWGLVWWAS-AATRIKPKSA-N 0.000 claims 1
- ZTBIUCKICOOFBG-UHFFFAOYSA-N Cl.C(C)OC(C=CC(=O)NN(C)C)=O Chemical compound Cl.C(C)OC(C=CC(=O)NN(C)C)=O ZTBIUCKICOOFBG-UHFFFAOYSA-N 0.000 claims 1
- 159000000007 calcium salts Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000002689 soil Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- FOWAVPREFGTTQS-OWOJBTEDSA-N (e)-4-hydrazinyl-4-oxobut-2-enoic acid Chemical class NNC(=O)\C=C\C(O)=O FOWAVPREFGTTQS-OWOJBTEDSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000979 retarding effect Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- SPQIOSNDBKICOH-OWOJBTEDSA-N (e)-2,4-diamino-4-oxobut-2-enoic acid Chemical compound NC(=O)\C=C(\N)C(O)=O SPQIOSNDBKICOH-OWOJBTEDSA-N 0.000 description 1
- BSSNZUFKXJJCBG-OWOJBTEDSA-N (e)-but-2-enediamide Chemical compound NC(=O)\C=C\C(N)=O BSSNZUFKXJJCBG-OWOJBTEDSA-N 0.000 description 1
- FOWAVPREFGTTQS-UPHRSURJSA-N (z)-4-hydrazinyl-4-oxobut-2-enoic acid Chemical class NNC(=O)\C=C/C(O)=O FOWAVPREFGTTQS-UPHRSURJSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cultivation Of Plants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53527066A | 1966-01-28 | 1966-01-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1567213A1 true DE1567213A1 (de) | 1970-05-21 |
Family
ID=24133517
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661567213 Pending DE1567213A1 (de) | 1966-01-28 | 1966-09-16 | Mittel zur Regulierung des Pflanzenwuchses |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3458304A (en, 2012) |
| BE (1) | BE688275A (en, 2012) |
| BR (1) | BR6682672D0 (en, 2012) |
| DE (1) | DE1567213A1 (en, 2012) |
| GB (1) | GB1117036A (en, 2012) |
| IL (1) | IL26285A (en, 2012) |
| LU (1) | LU52196A1 (en, 2012) |
| NL (1) | NL6700635A (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5146812B1 (en, 2012) * | 1971-04-15 | 1976-12-11 | ||
| US3775089A (en) * | 1971-11-02 | 1973-11-27 | A Donnell | Methylated muconic acid hydrazides |
| US4125398A (en) * | 1975-11-07 | 1978-11-14 | Ciba-Geigy Corporation | N-Phenyl-maleic acid amides for regulating the growth and development of plants |
| US4216238A (en) * | 1979-02-13 | 1980-08-05 | Stauffer Chemical Company | Dialkyl amino ethyl amides, their salts and their use as anti-ripening agents |
| US5214196A (en) * | 1987-09-04 | 1993-05-25 | Dexter Chemical Corporation | Diethyl ester of di-glycyl fumaramide |
| US5242905A (en) * | 1987-09-04 | 1993-09-07 | Dexter Chemical Corporation | Pharmaceutical compositions for the treatment of psoriasis |
| US4906280A (en) * | 1987-10-14 | 1990-03-06 | Pennwalt Corporation | Tertiary butylhydrazides as plant growth regulators |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2835703A (en) * | 1956-04-18 | 1958-05-20 | Eastman Kodak Co | Hydrazides of allyloxamic acid |
| US3084036A (en) * | 1959-02-05 | 1963-04-02 | Dow Chemical Co | Herbicidal composition and method employing allyl hydrazine |
| US3240799A (en) * | 1961-02-16 | 1966-03-15 | Us Rubber Co | N-disubstituted amino amic acids |
| US3318677A (en) * | 1961-02-16 | 1967-05-09 | Us Rubber Co | Plant dwarfing composition and method |
| US3278597A (en) * | 1963-05-08 | 1966-10-11 | Gulf Oil Corp | Substituted tiglanilide herbicides |
| US3305347A (en) * | 1964-11-12 | 1967-02-21 | Tenneco Chem | Benzylidene hydrazine pesticides |
-
1966
- 1966-01-28 US US535270A patent/US3458304A/en not_active Expired - Lifetime
- 1966-08-07 IL IL26285A patent/IL26285A/en unknown
- 1966-08-12 GB GB36112/66A patent/GB1117036A/en not_active Expired
- 1966-09-06 BR BR182672/66A patent/BR6682672D0/pt unknown
- 1966-09-16 DE DE19661567213 patent/DE1567213A1/de active Pending
- 1966-10-14 BE BE688275D patent/BE688275A/xx unknown
- 1966-10-18 LU LU52196A patent/LU52196A1/xx unknown
-
1967
- 1967-01-16 NL NL6700635A patent/NL6700635A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU52196A1 (en, 2012) | 1966-12-19 |
| IL26285A (en) | 1970-07-19 |
| US3458304A (en) | 1969-07-29 |
| BE688275A (en, 2012) | 1967-03-16 |
| GB1117036A (en) | 1968-06-12 |
| NL6700635A (en, 2012) | 1967-07-31 |
| BR6682672D0 (pt) | 1973-08-09 |
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