CA1241966A - 1-methylamino-cyclopropane-1-carboxylic acid derivatives - Google Patents
1-methylamino-cyclopropane-1-carboxylic acid derivativesInfo
- Publication number
- CA1241966A CA1241966A CA000464252A CA464252A CA1241966A CA 1241966 A CA1241966 A CA 1241966A CA 000464252 A CA000464252 A CA 000464252A CA 464252 A CA464252 A CA 464252A CA 1241966 A CA1241966 A CA 1241966A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- cyclopropane
- methylamino
- compound
- formyl
- 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
- ZCLBLSZZIRMCLZ-UHFFFAOYSA-N 1-(methylamino)cyclopropane-1-carboxylic acid Chemical class CNC1(C(O)=O)CC1 ZCLBLSZZIRMCLZ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 108
- 230000008569 process Effects 0.000 claims abstract description 89
- 150000001875 compounds Chemical class 0.000 claims abstract description 82
- -1 alkinyloxy Chemical group 0.000 claims abstract description 70
- 239000002253 acid Substances 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 239000003795 chemical substances by application Substances 0.000 claims description 36
- 239000003085 diluting agent Substances 0.000 claims description 25
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 230000008635 plant growth Effects 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 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 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 3
- PYZWRNNLMUMWQG-UHFFFAOYSA-N methyl 1-(methylamino)cyclopropane-1-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1(NC)CC1 PYZWRNNLMUMWQG-UHFFFAOYSA-N 0.000 claims 3
- CNGPSWCUPLOVEK-UHFFFAOYSA-N octyl 1-[formyl(methyl)amino]cyclopropane-1-carboxylate Chemical compound CCCCCCCCOC(=O)C1(N(C)C=O)CC1 CNGPSWCUPLOVEK-UHFFFAOYSA-N 0.000 claims 3
- CTKHKRHTEBZLNY-UHFFFAOYSA-N methyl 1-[formyl(methyl)amino]cyclopropane-1-carboxylate Chemical compound COC(=O)C1(N(C)C=O)CC1 CTKHKRHTEBZLNY-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 5
- 239000005648 plant growth regulator Substances 0.000 abstract description 3
- 125000003302 alkenyloxy group Chemical group 0.000 abstract description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract description 2
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 abstract 1
- 235000013350 formula milk Nutrition 0.000 description 112
- 241000196324 Embryophyta Species 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000003630 growth substance Substances 0.000 description 18
- 230000012010 growth Effects 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- 239000007858 starting material Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000011230 binding agent Substances 0.000 description 10
- 238000003306 harvesting Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- 210000000056 organ Anatomy 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 235000013399 edible fruits Nutrition 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000003213 activating effect Effects 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 230000009105 vegetative growth Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 244000061176 Nicotiana tabacum Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
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- 239000008096 xylene Substances 0.000 description 3
- DJMUYABFXCIYSC-UHFFFAOYSA-N 1H-phosphole Chemical compound C=1C=CPC=1 DJMUYABFXCIYSC-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 244000099147 Ananas comosus Species 0.000 description 2
- 235000007119 Ananas comosus Nutrition 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- 240000005979 Hordeum vulgare Species 0.000 description 2
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- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- 150000001768 cations Chemical class 0.000 description 2
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- HMDASTWKBIFUGF-UHFFFAOYSA-N ethyl 1-[acetyl(methyl)amino]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1(N(C)C(C)=O)CC1 HMDASTWKBIFUGF-UHFFFAOYSA-N 0.000 description 2
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- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
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- 230000001035 methylating effect Effects 0.000 description 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
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- 239000002689 soil Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- NNOGOOFZLBJDDQ-ZETCQYMHSA-N (2s)-2-[acetyl(methyl)amino]-4-methylsulfanylbutanoic acid Chemical compound CSCC[C@@H](C(O)=O)N(C)C(C)=O NNOGOOFZLBJDDQ-ZETCQYMHSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3335514.2 | 1983-09-30 | ||
| DE19833335514 DE3335514A1 (de) | 1983-09-30 | 1983-09-30 | 1-methylamino-cyclopropan-1-carbonsaeure-derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1241966A true CA1241966A (en) | 1988-09-13 |
Family
ID=6210573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000464252A Expired CA1241966A (en) | 1983-09-30 | 1984-09-28 | 1-methylamino-cyclopropane-1-carboxylic acid derivatives |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5041612A (enExample) |
| EP (1) | EP0136615B1 (enExample) |
| JP (1) | JPS6092251A (enExample) |
| AT (1) | ATE33634T1 (enExample) |
| CA (1) | CA1241966A (enExample) |
| DE (2) | DE3335514A1 (enExample) |
| HU (1) | HU199064B (enExample) |
| IL (1) | IL73093A (enExample) |
| ZA (1) | ZA847650B (enExample) |
Families Citing this family (71)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3539307A1 (de) * | 1985-11-06 | 1987-05-07 | Bayer Ag | Substituierte 1-amino-cyclopropancarbonsaeurederivate |
| DE3820528A1 (de) * | 1988-06-16 | 1989-12-21 | Bayer Ag | Mittel zur insekten- und milbenabwehr |
| PL345692A1 (en) * | 1998-07-30 | 2002-01-02 | Aventis Cropscience Sa | Method of preventing premature fruit drop from apple trees |
| US8247352B2 (en) * | 2005-03-11 | 2012-08-21 | The Regents Of The University Of California | Method of inhibiting ethylene production in plants |
| AR080443A1 (es) | 2010-03-04 | 2012-04-11 | Bayer Cropscience Ag | 2-amidobencimidazoles sustituidos con fluruoalquilo |
| BR112012025714A2 (pt) | 2010-04-06 | 2015-09-08 | Bayer Ip Gmbh | uso de ácido 4-fenilbutírico e/ou sais do mesmo para aumentar a tolerância a estresse de plantas |
| WO2011124553A2 (de) | 2010-04-09 | 2011-10-13 | Bayer Cropscience Ag | Verwendung von derivaten der (1-cyancyclopropyl)phenylphosphinsäure, deren ester und/oder deren salze zur steigerung der toleranz in pflanzen gegenüber abiotischem stress |
| AU2011281679B2 (en) | 2010-07-20 | 2015-09-03 | Bayer Intellectual Property Gmbh | Use of anthranilic acid amide derivatives for controlling insects and spider mites by watering, mixing with soil, drench treatment, droplet application, injection into the soil, stems or blossoms, in hydroponic systems, by treating the planting hole or immersion application, floating or seed box application or by the treatment of seeds, and for increasing the stress tolerance in plants to abiotic stress |
| AU2011298423B2 (en) | 2010-09-03 | 2015-11-05 | Bayer Intellectual Property Gmbh | Substituted fused pyrimidinones and dihydropyrimidinones |
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Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4554017A (en) * | 1978-06-03 | 1985-11-19 | Bayer Aktiengesellschaft | Method and compositions for regulating plant growth using cycloalkane-carboxylic acid compounds |
| DE2948024A1 (de) * | 1979-11-29 | 1981-08-27 | Bayer Ag, 5090 Leverkusen | 1-amino-cyclopropancarbonsaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren |
-
1983
- 1983-09-30 DE DE19833335514 patent/DE3335514A1/de not_active Withdrawn
-
1984
- 1984-09-18 EP EP84111095A patent/EP0136615B1/de not_active Expired
- 1984-09-18 DE DE8484111095T patent/DE3470533D1/de not_active Expired
- 1984-09-18 AT AT84111095T patent/ATE33634T1/de not_active IP Right Cessation
- 1984-09-26 IL IL73093A patent/IL73093A/xx unknown
- 1984-09-28 ZA ZA847650A patent/ZA847650B/xx unknown
- 1984-09-28 CA CA000464252A patent/CA1241966A/en not_active Expired
- 1984-09-28 HU HU843687A patent/HU199064B/hu not_active IP Right Cessation
- 1984-09-29 JP JP59205460A patent/JPS6092251A/ja active Pending
-
1987
- 1987-03-03 US US07/021,292 patent/US5041612A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6092251A (ja) | 1985-05-23 |
| EP0136615A2 (de) | 1985-04-10 |
| IL73093A0 (en) | 1984-12-31 |
| ATE33634T1 (de) | 1988-05-15 |
| US5041612A (en) | 1991-08-20 |
| HU199064B (en) | 1990-01-29 |
| DE3470533D1 (de) | 1988-05-26 |
| IL73093A (en) | 1988-06-30 |
| EP0136615B1 (de) | 1988-04-20 |
| ZA847650B (en) | 1985-05-29 |
| DE3335514A1 (de) | 1985-04-18 |
| EP0136615A3 (enExample) | 1985-05-15 |
| HUT35629A (en) | 1985-07-29 |
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