EP1409440A4 - A method to inhibit ethylene responses in plants - Google Patents
A method to inhibit ethylene responses in plantsInfo
- Publication number
- EP1409440A4 EP1409440A4 EP02707944A EP02707944A EP1409440A4 EP 1409440 A4 EP1409440 A4 EP 1409440A4 EP 02707944 A EP02707944 A EP 02707944A EP 02707944 A EP02707944 A EP 02707944A EP 1409440 A4 EP1409440 A4 EP 1409440A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- mmol
- added
- cyclopropene
- water
- dried over
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 44
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 239000005977 Ethylene Substances 0.000 title claims abstract description 37
- 230000004044 response Effects 0.000 title claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 112
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 30
- 125000000298 cyclopropenyl group Chemical class [H]C1=C([H])C1([H])* 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- -1 stereoisomers Chemical class 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 71
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 235000013399 edible fruits Nutrition 0.000 claims description 9
- 125000003367 polycyclic group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 230000036253 epinasty Effects 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 235000013311 vegetables Nutrition 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 5
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 5
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 claims description 5
- 150000002690 malonic acid derivatives Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- WFMBDEXRLSHIKH-UHFFFAOYSA-N [O-][N+](=O)Cl(=O)(=O)(N=O)N=[N+]=[N-] Chemical compound [O-][N+](=O)Cl(=O)(=O)(N=O)N=[N+]=[N-] WFMBDEXRLSHIKH-UHFFFAOYSA-N 0.000 claims description 4
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 claims description 4
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 230000006578 abscission Effects 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 230000005070 ripening Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 2
- ZZMRPOAHZITKBV-UHFFFAOYSA-N 3-aminocyclohex-2-en-1-one Chemical class NC1=CC(=O)CCC1 ZZMRPOAHZITKBV-UHFFFAOYSA-N 0.000 claims description 2
- 229930192334 Auxin Natural products 0.000 claims description 2
- 241000233866 Fungi Species 0.000 claims description 2
- 206010000210 abortion Diseases 0.000 claims description 2
- 231100000176 abortion Toxicity 0.000 claims description 2
- 239000002363 auxin Substances 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 230000005059 dormancy Effects 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000017066 negative regulation of growth Effects 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 244000000003 plant pathogen Species 0.000 claims description 2
- 230000017363 positive regulation of growth Effects 0.000 claims description 2
- 230000019649 positive regulation of seed germination Effects 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 230000008117 seed development Effects 0.000 claims description 2
- 230000009758 senescence Effects 0.000 claims description 2
- 238000004904 shortening Methods 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- IMBCELZVGYRYHU-UHFFFAOYSA-N ethyl n-(4-bromo-2-methylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(Br)C=C1C IMBCELZVGYRYHU-UHFFFAOYSA-N 0.000 claims 1
- 230000003054 hormonal effect Effects 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 4
- 230000015556 catabolic process Effects 0.000 abstract description 3
- 238000006731 degradation reaction Methods 0.000 abstract description 3
- 230000035800 maturation Effects 0.000 abstract description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 229910052796 boron Inorganic materials 0.000 abstract 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000010703 silicon Substances 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 426
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 184
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 181
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 171
- 239000012071 phase Substances 0.000 description 145
- 239000000243 solution Substances 0.000 description 134
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 113
- 239000011541 reaction mixture Substances 0.000 description 112
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 104
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 103
- 229960004132 diethyl ether Drugs 0.000 description 94
- 239000012044 organic layer Substances 0.000 description 93
- 235000019341 magnesium sulphate Nutrition 0.000 description 89
- 238000006243 chemical reaction Methods 0.000 description 80
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
- 239000003921 oil Substances 0.000 description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 60
- 238000003756 stirring Methods 0.000 description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
- 239000012267 brine Substances 0.000 description 58
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 58
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- 238000002360 preparation method Methods 0.000 description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- 239000002904 solvent Substances 0.000 description 43
- 241000196324 Embryophyta Species 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 239000000706 filtrate Substances 0.000 description 39
- 229950005228 bromoform Drugs 0.000 description 30
- 239000007788 liquid Substances 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- 239000007787 solid Substances 0.000 description 26
- 238000004440 column chromatography Methods 0.000 description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- 238000010992 reflux Methods 0.000 description 21
- 239000010410 layer Substances 0.000 description 20
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 20
- GNBFLKXPZIUCPH-UHFFFAOYSA-L benzyl-[2-[benzyl(dimethyl)azaniumyl]ethyl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].C=1C=CC=CC=1C[N+](C)(C)CC[N+](C)(C)CC1=CC=CC=C1 GNBFLKXPZIUCPH-UHFFFAOYSA-L 0.000 description 19
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000000746 purification Methods 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- OOXWYYGXTJLWHA-UHFFFAOYSA-N cyclopropene Chemical compound C1C=C1 OOXWYYGXTJLWHA-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000012299 nitrogen atmosphere Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- YMFWYDYJHRGGPF-UHFFFAOYSA-N 2,3-dibromoprop-1-ene Chemical compound BrCC(Br)=C YMFWYDYJHRGGPF-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 239000002002 slurry Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- KPUMBSBAAYTRKG-UHFFFAOYSA-L benzyl-[2-[benzyl(diethyl)azaniumyl]ethyl]-diethylazanium;dibromide Chemical compound [Br-].[Br-].C=1C=CC=CC=1C[N+](CC)(CC)CC[N+](CC)(CC)CC1=CC=CC=C1 KPUMBSBAAYTRKG-UHFFFAOYSA-L 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- DLWPHBBZVHLKLP-UHFFFAOYSA-N 2-bromo-4-(1-ethoxyethoxy)but-1-ene Chemical compound CCOC(C)OCCC(Br)=C DLWPHBBZVHLKLP-UHFFFAOYSA-N 0.000 description 9
- WFIITSVBZDMEFY-UHFFFAOYSA-N 2-bromodec-1-ene Chemical compound CCCCCCCCC(Br)=C WFIITSVBZDMEFY-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000003760 magnetic stirring Methods 0.000 description 9
- 239000003444 phase transfer catalyst Substances 0.000 description 9
- 238000005292 vacuum distillation Methods 0.000 description 9
- 229920000858 Cyclodextrin Polymers 0.000 description 8
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 230000005484 gravity Effects 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 8
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 8
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- DJCOEBLWVMOEJJ-UHFFFAOYSA-N 1,1,2-tribromo-2-octylcyclopropane Chemical compound CCCCCCCCC1(Br)CC1(Br)Br DJCOEBLWVMOEJJ-UHFFFAOYSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- BJCJYXTVNBGEOQ-UHFFFAOYSA-N ethyl 4-bromopent-4-enoate Chemical compound CCOC(=O)CCC(Br)=C BJCJYXTVNBGEOQ-UHFFFAOYSA-N 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 239000005969 1-Methyl-cyclopropene Substances 0.000 description 6
- SHDPRTQPPWIEJG-UHFFFAOYSA-N 1-methylcyclopropene Chemical compound CC1=CC1 SHDPRTQPPWIEJG-UHFFFAOYSA-N 0.000 description 6
- MDENQIAJEXDWMX-UHFFFAOYSA-N 2-bromo-9-(1-ethoxyethoxy)non-1-ene Chemical compound CCOC(C)OCCCCCCCC(Br)=C MDENQIAJEXDWMX-UHFFFAOYSA-N 0.000 description 6
- KPOMMVOUBUBNBV-UHFFFAOYSA-N 4-(1,2,2-tribromocyclopropyl)butan-1-ol Chemical compound OCCCCC1(Br)CC1(Br)Br KPOMMVOUBUBNBV-UHFFFAOYSA-N 0.000 description 6
- QXZAZTDXCREZPW-UHFFFAOYSA-N 4-bromopent-4-enoic acid Chemical compound OC(=O)CCC(Br)=C QXZAZTDXCREZPW-UHFFFAOYSA-N 0.000 description 6
- TWNIHLHLNBGHFF-UHFFFAOYSA-N 5,6-dibromohexan-1-ol Chemical compound OCCCCC(Br)CBr TWNIHLHLNBGHFF-UHFFFAOYSA-N 0.000 description 6
- 241000227653 Lycopersicon Species 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- PLDFKNLQWUBOCK-UHFFFAOYSA-N diethyl 2-(2-bromoprop-2-enyl)propanedioate Chemical compound CCOC(=O)C(CC(Br)=C)C(=O)OCC PLDFKNLQWUBOCK-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 239000012039 electrophile Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 5
- RPBGSGULOHONJZ-UHFFFAOYSA-N 4-(1,2,2-tribromocyclopropyl)butyl 4-methylbenzoate Chemical compound C1=CC(C)=CC=C1C(=O)OCCCCC1(Br)C(Br)(Br)C1 RPBGSGULOHONJZ-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- KZMJASPLZYCVSL-UHFFFAOYSA-N (2-ethylcyclopropen-1-yl)methyl methanesulfonate Chemical compound CCC1=C(COS(C)(=O)=O)C1 KZMJASPLZYCVSL-UHFFFAOYSA-N 0.000 description 4
- KUPYCQADTDVPDX-UHFFFAOYSA-N 1,1,2-tribromo-2-[2-(1-ethoxyethoxy)ethyl]cyclopropane Chemical compound CCOC(C)OCCC1(Br)CC1(Br)Br KUPYCQADTDVPDX-UHFFFAOYSA-N 0.000 description 4
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
- 238000012306 spectroscopic technique Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- A—HUMAN NECESSITIES
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- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
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- 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
- A01N27/00—Biocides, pest repellants or attractants, or plant growth regulators containing hydrocarbons
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- 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
- A01N29/00—Biocides, pest repellants or attractants, or plant growth regulators containing halogenated hydrocarbons
- A01N29/04—Halogen directly attached to a carbocyclic ring system
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- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2632—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving an organo-magnesium compound, e.g. Grignard synthesis
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- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
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- C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
- C07C321/20—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
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- C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
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- C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
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- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/416—Henkel reaction and related reactions, i.e. rearrangement of carboxylate salt groups linked to six-membered aromatic rings, in the absence or in the presence of CO or CO2, (e.g. preparation of terepholates from benzoates); no additional classification for the subsequent hydrolysis of the salt groups has to be given
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- C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms
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- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
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- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
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Definitions
- the present invention generally relates to methods of inhibiting ethylene responses in plants and plant materials, and particularly relates to methods of inhibiting various ethylene responses including plant maturation and degradation, by exposing plants to cyclopropene derivatives and compositions thereof wherein at least one substituent on the cyclopropene ring contains a carbocyclic or heterocyclic ring.
- ethylene can cause the premature death of plants or plant parts including, for example, flowers, leaves, fruits, and vegetables. Ethylene also promotes leaf yellowing and stunted growth as well as premature fruit, flower, and leaf drop. Such activities are understood to be achieved through interaction with a specific ethylene receptor in the plant. Many compounds other than ethylene interact with this receptor: some mimic the action of ethylene; others prevent ethylene from binding and thereby counteract its action. To address these ethylene-induced effects, very active and intense research presently concerns the investigation of ways to prevent or reduce the deleterious effects of ethylene on plants.
- the new compounds will avoid the explosive hazards of 1 -methylcyclopropene and, in addition, provide alternative means of delivery, such as through liquid or solid formulations.
- n is an integer from 1 to 12; ii) each L is independently selected from a member of the group Dl , D2, E, or J wherein: Dl is of the formula:
- D2 is of the formula:
- each X and Y is independently a group of the formula: -(L) m -Z;
- each Z is independently selected from:
- G is an unsubstituted or substituted; unsaturated, partially saturated, or saturated; monocyclic, bicyclic, tricyclic, or fused; 4 to 14 membered carbocyclic or heterocyclic ring system wherein;
- each heteroatom is independently selected from N, O, and S; 4) the number of substituents is from 0 to 5 and each substituent is independently selected from X; b) the total number of non-hydrogen atoms in each compound is 50 or less; and c) the total number of heteroatoms in -(L) n -Z is from 0 to 4; and d) either; i) R' or R contains at least one group G; or ii) at least one L group is an E group; or iii) at least one of R 1 , R 2 , R 3 , and R 4 contains one to four non-hydrogen atoms and at least one of R 1 , R , R , and R 4 contains more than four non-hydrogen atoms; and its enantiomers, stereoisomers, salts, and mixtures thereof; or a composition thereof.
- each open bond indicates a bond to another L group, a Z group, or the cyclopropene moiety.
- the structural representation - ⁇ — indicates an oxygen atom with bonds to two other atoms; it does not represent a dimethyl ether moiety.
- Typical R 1 , R 2 , R 3 , and R 4 groups include, for example: alkenyl, alkyl, alkynyl, acetylaminoalkenyl, acetylaminoalkyl, acetylaminoalkynyl, alkenoxy, alkoxy, alkynoxy, alkoxyalkoxyalkyl, alkoxyalkenyl, alkoxyalkyl, alkoxyalkynyl, alkoxycarbonylalkenyl, alkoxycarbonylalkyl, alkoxycarbonylalkynyl, alkylcarbonyl, alkylcarbonyloxyalkyl, alkyl(alkoxyimino)alkyl, carboxyalkenyl, carboxyalkyl, carboxyalkynyl, dialkylamino, haloalkoxyalkenyl, haloalkoxyalkyl, haloalkoxyalkynyl, haloalkenyl
- G groups include, for example: saturated or unsaturated cycloalkyl, bicyclic, tricyclic, polycyclic, saturated or unsaturated heterocyclic, unsubstituted or substituted phenyl, naphthyl, or heteroaryl ring systems such as, for example, cyclopropyl, cyclobutyl, cyclopent-3-en-l-yl, 3-methoxycyclohexan-l-yl, phenyl, 4-chlorophenyl, 4-fluorophenyl, 4- bromophenyl, 3-nitrophenyl, 2-mefhoxyphenyl, 2-methylphenyl, 3-methyphenyl, 4- methylphenyl, 4-ethylphenyl, 2-methyl-3-methoxyphenyl, 2,4-dibromophenyl, 3,5- difluorophenyl, 3,5-dimethylphenyl, 2,4,6-trichlorophenyl, 4-methoxyphenyl, naphth
- R 1 , R 2 , R 3 , and R 4 are hydrogen. More preferably, R 1 and R 2 are hydrogen or R and R are hydrogen. Even more preferably, R , R , and R are hydrogen or R 1 , R 2 , and R 3 are hydrogen. Most preferably, R , R , and R 4 are hydrogen.
- n is from 0 to 8. Most preferably, n is from 1 to 7.
- m is 0 to 4. Most preferably, m is from 0 to 2.
- Dl is -CXY-, -CO-, or -CS-. More preferably Dl is -CXY-.
- D2 is -O- or -NX-.
- E is -S-, -SiXY-,, or -S0 2 -.
- X and Y are independently H, halo, OH, SH, -C(0)(C ⁇ -C 4 )alkyl -, -C(0)0(C ⁇ -C 4 )alkyl -, -O- (C ⁇ -C 4 )alkyl, -S-(C ⁇ -C 4 )alkyl, or substituted or unsubstituted (C ⁇ -C 4 )alkyl.
- Z is H, halo, or G. More preferably, Z is H or G.
- each G is independently a substituted or unsubstituted; five, six, or seven membered; aryl, heteroaryl, heterocyclic, or cycloalkyl ring. More preferably, each G is independently a substituted or unsubstituted phenyl, pyridyl, cyclohexyl, cyclopentyl, cycloheptyl, pyrolyl, furyl, thiophenyl, triazolyl, pyrazolyl, 1,3-dioxolanyl, or mo ⁇ holinyl.
- G is unsubstituted or substituted phenyl, cyclopentyl, cycloheptyl, or cyclohexyl. Most preferably, G is cyclopentyl, cycloheptyl, cyclohexyl, phenyl, or substituted phenyl wherein the substituents are independently selected from 1 to 3 of methyl, methoxy, and halo.
- Another aspect of the present invention is a method of blocking ethylene receptors in plants by applying to the plants an effective ethylene receptor-blocking amount of the cyclopropene derivative or a composition thereof.
- the methods described herein may be carried out in a variety of ways, such as by contacting the plant with a cyclopropene derivative or a composition thereof, whether in solid, liquid, or gaseous form, or by exposing the plant, cut flower, picked fruit or picked vegetable in an atmosphere infused with the cyclopropene derivative or a composition thereof.
- contacting means to bring the cyclopropene and a plant into intimate association with each other such that a sufficient number of ethylene receptors are effected by the cyclopropene.
- Agricultural compositions comprising the compounds of this invention are also encompassed by the invention.
- compositions comprise 0.005% to 99%, by weight; preferably 1% to 95%, by weight; more preferably 2% to 90%, by weight; even more preferably 3% to 80%, by weight; or most preferably 4% to 70%, by weight, of the active compounds of the present invention.
- These compositions may comprise one or more adjuvants, such as, for example, carriers, extenders, binders, lubricants, surfactants and/or dispersants, wetting agents, spreading agents, dispersing agents, stickers, adhesives, defoamers, thickeners, and emulsifying agents.
- adjuvants commonly used in the art can be found in the John W. McCutcheon, Inc.
- organic solvents may be used as carriers for the active compounds of the present invention such as, for example, hydrocarbons such as hexane, benzene, toluene, xylene, kerosene, diesel oil, fuel oil and petroleum naphtha, ketones such as acetone, methyl ethyl ketone and cyclohexanone, chlorinated hydrocarbons such as methylene chloride, esters such as ethyl acetate, amyl acetate and butyl acetate, ethers, e.g., ethylene glycol monomethyl ether and diethylene glycol monomethyl ether, alcohols, e.g., ethanol, methanol, isopropanol, amyl alcohol, ethylene glycol, propylene glycol, butyl carbitol acetate and glycerine.
- hydrocarbons such as hexane, benzene, toluene, xylene, kerosene,
- Solid, liquid, and gaseous formulations can be prepared by various conventional procedures.
- the active ingredient, in finely divided form if a solid may be tumbled together with finely divided solid carrier.
- the active ingredient in liquid form including mixtures, solutions, dispersions, emulsions and suspensions thereof, may be admixed with a solid carrier in finely divided form.
- the active ingredient in solid form may be admixed with a liquid carrier to form a mixture, solution, dispersion, emulsion, suspension or the like.
- the active compounds of the present invention can be applied to plants by various suitable means.
- an active compound may be applied alone in gaseous, liquid, or solid form by contacting the compound with the plant to be treated. Additionally the active compound may be converted to the salt form, and then applied to the plants.
- compositions containing one or more active compounds of the present invention may be formed. The compositions may be applied in gaseous, liquid, or solid form by contacting the composition with the plant to be treated. Such compositions may include an inert carrier. Similarly, when in gaseous form, the compound may be dispersed in an inert gaseous carrier to provide a gaseous solution.
- the active compound may also be suspended in a liquid solution such as an organic solvent or an aqueous solution that may serve as the inert carrier.
- Solutions containing the active compound may be heterogeneous or homogeneous and may be of various forms including mixtures, dispersions, emulsions, suspensions and the like.
- the cyclopropenes may also be encapsulated into a molecular encapsulation agent.
- Preferred encapsulating agents include cyclodextrins, crown ethers, polysiloxanes, and zeolites. More preferred encapsulating agents include ⁇ -cyclodextrin, ⁇ -cyclodextrin, and ⁇ -cyclodextrin. The most preferred encapsulating agent will vary depending upon the size of the R substituents. However, as one skilled in the art will appreciate, any cyclodextrin or mixture of cyclodextrins, cyclodextrin polymers as well as modified cyclodextrins can also be utilized pursuant to the present invention.
- Cyclodextrins are available from Wacker Biochem Inc., Adrian, MI or Cerestar USA, Hammond, IN, as well as other vendors. When encapsulated, the preferred concentrations of the cyclopropenes will typically be less than in other compositions due to the capacity limitations of molecular encapsulation agents.
- the active compounds and compositions thereof can also be applied as aerosols, e.g., by dispersing them in air using a compressed gas such as, for example, nitrogen, carbon dioxide, dichlorodifluoromethane, trichlorofluoromefhane, or other halocarbons.
- a compressed gas such as, for example, nitrogen, carbon dioxide, dichlorodifluoromethane, trichlorofluoromefhane, or other halocarbons.
- the amount of the cyclopropene needed to inhibit ethylene effects will vary depending upon the particular cyclopropene, the type and amount of plant material present, the cyclopropene composition used, and the volume to be treated. Generally, a gas treatment (measured volume/volume) concentration of the cyclopropene in the treated chamber of from about 0.1 part per billion ("ppb") to 1000 parts per million (“ppm”) provides adequate ethylene inhibition. Likewise, an applied spray treatment (measured weight/weight) concentration of the cyclopropene of from about 0.01 part per billion (“ppb") to 1000 parts per million (“ppm”) provides adequate ethylene inhibition.
- plant is used in a generic sense herein, and includes, for example, woody- stemmed plants such as trees and shrubs; herbs; vegetables, fruits, and agricultural crop;, and ornamental plants. Plants to be treated by the methods described herein include whole plants and any portions thereof, such as field crops, potted plants, seeds, cut flowers (stems and flowers), and harvested fruits and vegetables.
- Plants treated with the compounds and by the methods of the present invention are preferably treated with a non-phytotoxic amount of the active compound.
- the present invention can be employed to modify a variety of different ethylene responses such as, for example, the ripening and/or senescence of flowers, fruits, and vegetables; abscission of foliage, flowers, and fruit; the shortening of life of ornamentals such as potted plants, cut flowers, shrubbery, seeds, and dormant seedlings; in some plants (e.g., pea) the inhibition of growth, the stimulation of growth (e.g., rice), auxin activity, inhibition of terminal growth, control of apical dominance, increase in branching, increase in tillering, changing the mo ⁇ hology of plants, modifying the susceptibility to plant pathogens such as fungi, changing bio-chemical compositions of plants (such as increasing leaf area relative to stem area), abortion or inhibition of flowering and seed development, lodging effects, stimulation of seed germination and breaking of dormancy, and hormone or epinasty effects.
- plants e.g., pea
- the inhibition of growth e.g., the
- Active compounds of the present invention have proven to be unexpectedly potent inhibitors of ethylene action on plants, fruits and vegetables, even when applied at low concentrations.
- compounds of the present invention may result in a longer period of insensitivity to ethylene than compounds found in the prior art. This longer period of insensitivity may occur even when compounds of the present invention are applied at a lower concentration than previous compounds.
- Another embodiment of this invention relates to members of the class of cyclopropenes which are newly discovered compounds. These compounds include compounds of the formula:
- R 1 and R 3 are H and R 2 , R 4 , and the other of R 1 and R 3 are independently selected from H and a group of the formula:
- n is an integer from 1 to 12; ii) each L is independently selected from a member of the group Dl, D2, E, or J wherein:
- Dl is of the formula:
- D2 is of the formula:
- each X and Y is independently a group of the formula: -(L) m -Z;
- each Z is independently selected from:
- G is an unsubstituted or substituted; unsaturated, partially saturated, or saturated; monocyclic, bicyclic, tricyclic, or fused; 4 to 14 membered carbocyclic or heterocyclic ring system wherein;
- each heteroatom is independently selected from N, O, and S; 4) the number of substituents is from 0 to 5 and each substituent is independently selected from X; b) the total number of non-hydrogen atoms in each compound is 50 or less; and c) the total number of heteroatoms in -(L) ⁇ -Z is from 0 to 4; and d) either; i) R 1 or R 3 contains at least one group G; or ii) at least one L group is an E group; or iii) at least one of R 1 , R 2 , R 3 , and R 4 contains one to four non-hydrogen atoms and at least one of R 1 , R 2 , R 3 , and R 4 contains more than four non-hydrogen atoms; andits enantiomers, stereoisomers, salts, and mixtures thereof; or a composition thereof; provided that: a) -(L) n -Z is other than trimethylsilyl, trimethylsilylsulf
- the compounds of this invention can be prepared by a number of methods.
- the cyclopropenyllithium can be reacted with electrophiles to give derivatived cyclopropenes. Examples of such electrophiles include alkylating agents, trisubstituted chlorosilanes, borates, dialkyl or diaryl disulfides, ketones, aldehydes, esters, amides and nitriles.
- the bromo-olefins can be prepared by standard methods. Chloro-olefins can be used in place of bromo-olefins.
- the tribrominated cyclopropanes can also be converted to mono-brominated cyclopropanes with reducing agents such as diethylphosphite. Other reducing agents could be used.
- a 1 , 1 -disubstituted olefin can also react with dibromocarbene to give a dibrominated intermediate. This can be reduced with zinc to the mono-brominated cyclopropane. Elimination of the bromide with base gives the cyclopropene (reference Binger, P. Synthesis 1974, 190).
- Cyclopropene can be deprotonated with a strong base such as sodium amide in liquid ammonia and reacted with an alkyl halide or other electrophiles to give a substituted cyclopropene (reference: Schipperijn, A. J.; Smael, P.; Reel Trav. Chim. Pays-Bas, 1973, 92, 1159).
- Substituted cyclopropenes can be deprotonated with alkyllithium reagents and reacted with electrophiles.
- Tribromocyclopropanes or cyclopropenes containing an alcohol can be converted to a good leaving group such as a sulfonate derivative.
- the leaving group can be displaced with nucleophiles to give other substituted cyclopropenes.
- a l-trialkylsilyl-2-hydroxycyclopropane, generated from vinyltrialkylsilane, can serve as a precursor to a cyclopropene (Mizojiri, R.; Urabe, H.; Sato, F. J. Org Chem. 2000, 65, 6217).
- l-Trialkylsilyl-2-halocyclopropanes also undergo a fluoride catalyzed elimination to give cyclopropenes (Billups, W. E.; Lee, G-A; Arney, B. E.; Whitmire, K. H. J. Am. Chem. Soc, 1991, 775, 7980. and Banwell, M. G.; Corbett, M.; Gulbis, J.; Mackay, M.F.; Reum, M. E. J. Chem. Soc. Perkin Trans. 1, 1993, 945).
- the esters can be hydrolyzed to the carboxylic acid.
- dihalocarbenes can be added to acetylenes to give l-alkyl-3,3- dihalocyclopropenes (Bessard, Y.; Schlosser, M.; Tetrahedron, 1991, 47, 7323).
- a solution of 8 ml (0.0622 mol) of 2,3-dibromopropene in 50 ml diethyl ether was placed under a nitrogen atmosphere by use of a Firestone valve. While cooling in an ice water bath, a solution of 62 ml (0.062 mol) of IM 4-chlorophenylmagnesium bromide in diethyl ether was added slowly via addition funnel. After stirring for 2 hours while warming to room temperature, the reaction was recooled in an ice bath and 50 ml of 1 N hydrochloric acid was then added via syringe. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgS0 4 and filtered.
- the Grignard reagent of 2-bromothiophene was prepared, and converted to 1 -( 2- thienyl)methyl-cyclopropene by the same reaction sequence as was used for the preparation of compound 1.
- EXAMPLE 3 Preparation of 2-(3-Cvcloprop-l-enyl-propyl)- l ,31dioxane (Compound 3) The Grignard reagent of 2-(2-bromoethyl)-l,3-dioxane was prepared, and converted to 2-(3-cycloprop-l-enyl-propyl)-[l,3]dioxane by the same reaction sequence as was used for the preparation of compound 1.
- EXAMPLE 4 Preparation of l-(6-(Phenyldimethylsilyl)-hexyl)-cvclopropene (Compound 3)
- N,N'-dibenzyl-N,N,N',N'-tetramethylethylenediammonium dibromide and N,N'- dibenzyl-N,N,N',N'-tetraethylethylenediammonium dibromide Phase transfer catalysts
- N,N,N',N'-tetraethylethylenediamine one obtains N,N'- dibenzyl-N,N,N',N'-tetraethylethylenediammonium dibromide, a white solid mp 190-193°C, decomposes.
- EXAMPLE 5 Preparation of l-( ⁇ , ⁇ -dimethylbenzyl)-cvclopropene (Compound 5) a. ⁇ , ⁇ -dimefhylbenzylcyanide Into a 1000 ml 3 necked flask with mechanical stirring, an external water bath, an internal thermometer, a condenser and an addition funnel was added 250 g of dimethyl sulfoxide, 59 g (504 mmol) of benzyl cyanide, and 160 g (1127 mmol) of methyl iodide. The internal temperature was raised to +45 °C and then 83 g of 50% aqueous NaOH was added at 0.7 drops per second. After two hours the addition was complete.
- the thick slurry was cooled, diluted with 1000 ml of water and 500 ml of diethyl ether and 500 ml of hexane.
- the organic layer was separated and concentrated. It contained mono and dimethylated compounds.
- To this concentrate was further added 250 g of dimethyl sulfoxide, 60 g of methyl iodide, and 37 g of 50% aqueous NaOH for two hours as above.
- Extractive workup with diethyl ether gave a mixture of l-( ⁇ , ⁇ -dimethylbenzyl)-l-chloroethylene and l-( ⁇ , ⁇ - dimethylbenzyl)-l,l-dichloroethane.
- Vacuum distillation gave purified l-( ⁇ , ⁇ - dimethylbenzyl)-l-chloroethylene bp (23 torr) 110-120 °C. d.
- reaction was quenched with 0.5 ml of methanol, rapidly evaporated in vacuo with a bath temperature of +25 °C, partitioned between diethyl ether and dilute aqueous hydrochloric acid, dried with anhydrous magnesium sulfate and re- evaporated in vacuo yielding 1.3 g of l-methyl-2- benzylcyclopropene.
- EXAMPLE 10 2-(2-Benzenesulfonyloxyethyl)-cvclopropene (Compound 10) A solution of 0.745 g (0.00150 mol) of l,l,2-tribromo-2-(2- benzenesulfonyloxyethyl)-cyclopropane in 4 ml of diethyl ether was placed under a nitrogen atmosphere by use of a Firestone valve.
- EXAMPLE 12 Preparation of 7-(l -Imidazole)- 1-heptylcvclopropene (Compound 12) a. 1 -( 1 -Ethoxyethoxy)-6-bromohexane
- N,N'-dibenzyl-N,N,N',N'-tetraethylethylenediammonium dibromide 42 g of 45% potassium hydroxide (337 mmol), 93 g of bromoform (368 mmol) and 280 g of methylene chloride were rapidly stirred at room temperature for two days.
- the reaction mixture was transferred to a separatory funnel and washed with water.
- the methylene chloride phase was transferred to a flask and treated with the same amount of the phase transfer catalyst and 45% potassium hydroxide as above, then stirred at room temperature for an additional 3 days.
- the reaction mixture was washed with water, the methylene chloride phase was dried with magnesium sulfate, and then stripped.
- the product was treated with 320 ml of methanol and 40 ml of IN HCI for 1 hour at room temperature. The methanol was stripped, ethyl acetate was added. The organic phase was washed with water and brine, then treated with 200 ml of silica gel. Filtration followed by a strip gave 38 g of black product. This was chromatographed on silica gel to give 19.0 g of l,l,2-tribromo-2-(7- hydroxyheptyl)cyclopropane as a pale yellow liquid. d.
- EXAMPLE 14 Preparation of 1 -Cyclohexylcyclopropene (Compound 14) l-Cyclohexyl-2-(trimethylsilyl)cyclopropanol was prepared from methyl cyclohexylcarboxylate and vinyltrimethylsilane as described in Mizojiri, R.; Urabe, H.; Sato, F. J. Org Chem. 2000, 65, 6217. This material was converted to the cyclopropene in an analogous manner to that described in the same reference.
- EXAMPLE 15 Preparation of l-((2-Carboxy-N-mo ⁇ holino)ethyl)-cyclopropene a. 2-(2-Bromo-allyl)-malonic acid diethyl ester
- EXAMPLE 17 Preparation of l-(3-trifluoromethylphenoxymethyl)-2- ethylcvclopropene (Compound 37) a. 1,1 ,2-Tribromo-2-efhylcyclopropane l,l,2-Tribromo-2-ethylcyclopropane was prepared from 2-bromo-l-butene by the same method used in example 4 c. b. 1 -(Hydroxymethyl)-2-ethylcyclopropene
- Example 2Q l-PhenyI-2,3.3-trichlorocvclopropene (Compound 41) l-Phenyl-2,3,3-trichlorocyclopropene was prepared by the method described in Eicher, theophil; Huch, VolkerJ Schneider, VolkerJ Veith, Michael.
- Example 21 l-(4-Methylphenylcarbonyloxybutyl)-cvclopropene (Compound 44) a. 5,6-Dibromo-hexan-l-ol To an ice bath cooled solution of 5-hexen-l-ol (ll.23g, 112.3mmol) in about
- the reaction was heated to 60 °C for about 2 hours then cooled to room temperature. After about 15 hours, 50% aqueous potassium carbonate (30 g, 107 mmol) and 30 g water were added and the reaction was heated to 60 °C for about 2 hours then cooled to room temperature. The reaction mixture was concentrated in vacuo, then the resulting residue was extracted with diethyl ether. The organic layer was washed with basified water (pHlO.) The phases were separated and the organic phase was dried over magnesium sulfate then dried in vacuo.
- Example 23 l-Benzyl-2-chlorocyclopropene (Compound 46) a. l-(2-Bromo-allyl)-benzene l-(2-Bromo-ally ⁇ )-benzene was prepared from 2,3-dibromopropene and phenylmagnesium bromide by the method shown in Example la. b. l-Benzyl-l-bromo-2,2-dichlorocyclopropane
- the methylene chloride phase was transferred to a flask and treated with the same amount of the phase transfer catalyst and 45% potassium hydroxide as before, then stirred at room temperature for an additional 3 days.
- the reaction mixture was washed with water, the methylene chloride phase was dried with magnesium sulfate, and then stripped.
- the product was treated with 320 ml of methanol and 40 ml of IN HCI for 1 hour at room temperature. The methanol was stripped, ethyl acetate was added.
- the organic phase was washed with water and brine, then treated with 200 ml of silica gel. Filtration followed by a strip gave 38 g of black product.
- Ethyl 4-bromopent-4-enoate was prepared by the method described in Mori, M.; et al. Journal of Organic Chemistry, 1983, 48, 4058-4067. b. 3-(l,2,2-Tribromo-cyclopropyl)-propionic acid ethyl ester
- Example 27 l-(8-Benzenesulfonyloxyoctyl)-cvclopropene (Compound 56) a. 9,10-Dibromo-decan-l-ol
- Example 28 l-(4-Methylphenylthiooctyl)-cvclopropene (Compound 57) a.
- l-(Benzenesulfonyloxyoctyl)-cyclopropene l-(Benzenesulfonyloxyoctyl)-cyclopropene is prepared from 1- (benzenesulfonyloxyoctyl)- 1,2,2-tribromo-cyclopropane by the method shown in Example 27. b. l-(4-Methylphenylthiooctyl)-cyclopropene
- Example 29 l-(lH-1.2.4-triazol-2-ylthiooctyl)-cvclopropene (Compound 58) a. l-(Benzenesulfonyloxyoctyl)-cyclopropene l-(Benzenesulfonyloxyoctyl)-cyclopropene is prepared from 1-
- 3-(4-Chlorophenyl)-pyridaz-6-one can be prepared as described in Example 3 of DE Pat. No. 2435244 (1976.)
- b. l-(Methanesulfonyloxymethyl)-2-ethylcyclopropene
- l-(Methanesulfonyloxymethyl)-2-ethylcyclopropene is prepared from by the method shown in Example 17c.
- N,N'-dibenzyl-N,N,N',N'-tetramethylethylenediammonium dibromide and N,N'- dibenzyl-N,N,N',N'-tetraethylethylenediammonium dibromide Phase transfer catalysts.
- N,N,N',N'-tetraethylethylenediamine one obtains N,N'- dibenzyl-N,N,N',N'-tetraethylethylenediammonium dibromide, a white solid mp 190-193°C, decomposes.
- the methylene chloride phase was placed in a reaction flask and treated with an additional 0.47 g of 45% aqueous potassium hydroxide solution (3.8 mmol) and 75 mg N,N'-dibenzyl- N,N,N',N'-tetraethylethylenediammonium dibromide.
- the reaction mixture was stirred overnight, then water and additional methylene chloride were added and the phases were separated.
- the methylene chloride phase was dried over magnesium sulfate, and stripped. A small amount of heptane was added during the strip to help remove remaining bromoform.
- Column chromatography gave 390 mg of 2-triethylsilylmethyl- 1 , 1 ,2-tribromocyclopropane as a colorless liquid, e) 1 -Triethylsilylmethylcyclopropene
- EXAMPLE 33 Preparation of l-Trimethylsilylmethylcyclopropene (Compound 64) Commercially available 3-trimethylsilyl-2-bromopropene was converted to 1- trimethylsilylmethylcyclopropene in a similar manner as described for Example 1.
- EXAMPLE 34 Preparation of 6-(Trimethylsilyl)-hexylcycloprop-2-ene (Compound 65) a. 2-Bromo-8-(trimethylsilyl)-oct-l-ene
- 2-Bromodec-l-ene Into a 500 ml 3 necked flask equipped with magnetic stirring, an addition funnel, and a reflux condenser was added 17 g (700 mmol) of magnesium turnings. The atmosphere was exchanged for dry nitrogen and the turnings were covered with 20 ml of diethyl ether. 2 g of 1 ,2-dibromoethane was added whereon a reaction occurred as evidenced by some bubbling and cloudiness. After 5 minutes, 200 ml of diethyl ether was added and the mixture brought to reflux. Slow addition of 90 g (503 mmol) of 1-bromoheptane in 100 ml of diethyl ether at a rate sufficient to maintain reflux took 50 minutes. The reaction was further refluxed for 30 minutes yielding a solution of heptyl magnesium bromide.
- the methylene chloride phase was transferred to a flask and treated with the same amount of the phase transfer catalyst and 45% potassium hydroxide as before, then stirred at room temperature for an additional 3 days.
- the reaction mixture was washed with water, the methylene chloride phase was dried with magnesium sulfate, and then stripped.
- the product was treated with 320 ml of methanol and 40 ml of IN HCI for 1 hour at room temperature. The methanol was stripped, ethyl acetate was added.
- the organic phase was washed with water and brine, then treated with 200 ml of silica gel. Filtration followed by a strip gave 38 g of black product.
- 2-Octyl- 1 , 1 ,2-tribromocyclopropane Into a 125 ml single necked flask with magnetic stirring was added 20 g (91 mmol) of 2-bromodec-l-ene, 75 g (297 mmol) of bromoform, 200 g of methylene chloride, 2.2 g of N,N'-dibenzyl-N,N,N',N'-tetramethylethylenediammonium dibromide, and 20 g (161 mmol) of 45% aqueous potassium hydroxide.
- This compound was prepared in a similar manner to compound 2. It was obtained as a mixture of 40% 3-methyl-3-nonyl-cyclopropene, 30% 1 -methyl- 1-nonyl- cyclopropane and 20% l-methyl-l-nonyl-2-bromocyclopropane.
- EXAMPLE 43 Preparation of 1 -Heptyl-2-methyl-cyclopropene (Compound 74) A solution of 1 mg of 1,10-phenanthroline, 1.74 ml of tetramethylethylenediamine, and 20 ml of tetrahydrofuran was placed under a nitrogen atmosphere via use of a Firestone valve.
- 1,1 ,2-Tribromo-2-(2-(carbo(acetoxylmethyl))ethyl-cyclopropene To a solution of 0.800 g (0.00228 mol) of 3-1,1, 2-tribromo -2-(2-(carboxy))ethyl- cyclopropene in about 2 ml anhydrous N,N-dimefhylformamide was added 0.224 ml (0.00228 mol) of bromomethyl acetate then 0.396 ml (0.00228 mol) of diisopropylethylamine. After heating to 60 °C for 2 hours, water and diethyl ether were added.
- EXAMPLE 45 Preparation of l-Bromo-2-(2-(carboethoxy)-ethyl-cvclopropene (Compound 76) l-Bromo-2-(2-(carboethoxy)-ethyl-cyclopropene was prepared from 1,1,2- tribromo-2-(2-(carboethoxy)-ethyl-cyclopropene in a manner similar to the preparation 1- bromo-2-(2-(carbo(acetoxylmethyl))-ethyl-cyclopropene from 1 , 1 ,2-tribromo-2-(2- (carbo(acetoxylmethyl))-efhyl-cyclopropene (Example 5).
- EXAMPLE 46 Preparation of l-Bromo-2-(2-(carboxy)-ethyl-cvclopropene (Compound 77) To a solution of 200 mg (0.913 mmol) of l-bromo-2-(2-(carboethoxy)-ethyl- cyclopropene in 2 ml of absolute ethanol was added 0.0768 g (1.37 mmol) of potassium hydroxide. After stirring for 1 hour, diethyl ether and water were added. The resulting mixture was transferred to a separatory funnel and the phases were separated. After the isolated aqueous layer was acidified by addition of 1 N hydrochloric acid, diethyl ether was added.
- EXAMPLE 47 Preparation of l-Octyl-3-carboxy-cvclopropene (Compound 78): a. 1 -Octyl-3-(carboxyethoxy)-cyclopropene l-Octyl-3-(carboxyethoxy)-cyclopropene was prepared from 1-decyne and ethyl diazoacetate by the method of Mueller, P.; Pautex, N. Helv. Chim Acta 1990, 73, 1233. b.
- l-Octyl-3-carboxy-cyclopropene l-Octyl-3-(carboxyethoxy)-cyclopropene (1.12g, 5 mmol) and 100 ml of 0.2 N potassium hydroxide were stirred at room temperature for one week. Ether was added and the phases were separated. The aqueous phase was acidified and extracted with methylene chloride. The organic phase was dried over magnesium sulfate and stripped to give 0.8 g of l-octyl-3-carboxy-cyclopropene.
- EXAMPLE 48 Preparation of l-Trimethylsilyl-2,3,3-trimethylcyclopropene (Compound 79) Compound 79 was prepared as a 36% solution in ether from 2-bromo-3-mefhyl-2-butene by the same method used to prepare Compound 5 from 2-bromodec-l-ene.
- EXAMPLE 49 Preparation of l-(Butyldimethylsilyl)-2-methylcvclopropene (Compound 80)
- Compound 80 was prepared from 2-bromopropene by the same method used to prepare Compound 5 from 2-bromodec-l-ene.
- EXAMPLE 50 Preparation of l-Triethylsilyl-2 -methylcyclopropene (Compound 81)
- Compound 81 was prepared from 2-bromopropene by the same method used to prepare Compound 5 from 2-bromodec-l-ene.
- EXAMPLE 51 Preparation of 1 -(7-T-butyldimethylsilyloxyheptyl)-cyclopropene (Compound 82) a. 1 -(7-Hydroxyheptyl)-cyclopropene l-(7-Hydroxyheptyl)-cyclopropene was prepared by the same method already described in example 7. b. 1 -(7-T-butyldimethylsilyloxyheptyl)-cyclopropene
- EXAMPLE 52 Preparation of 1 -(Methanesulfonyloxymethyl)-2-ethylcvclopropene (Compound 83) a. 1,1 ,2-Tribromo-2-efhylcyclopropane l,l,2-Tribromo-2-ethylcyclopropane was prepared from 2-bromo-l-butene by the same method used in example 5. b. l-(Hydroxymethyl)-2-ethylcyclopropene
- EXAMPLE 53 Preparation of l-(Diethoxy-thiophosphorylthiomethyl)-2- ethylcvclopropene (Compound 84) a. l-(Methanesulfonyloxymethyl)-2-ethylcyclopropene l-(Methanesulfonyloxymethyl)-2-ethylcyclopropene was prepared from 1- (hydroxymethyl)-2-ethyl cyclopropene by the same method used in example 13. b.
- Tomato Epinasty Test Objective The test procedure is designed to determine the ability of an experimental compound to block the epinastic growth response induced by ethylene in tomato plants when the experimental compound is administered either as a volatile gas or as a component of a spray solution.
- Treatment chambers are of an appropriate size for the test plants and are airtight. Each is fitted with a reusable septum to be used for injection of ethylene.
- Test plants are Patio variety tomato seedlings planted two plants per three inch square plastic pot.
- Volatile gas treatment entails placing two pots of Patio var. tomatoes into a polystyrene 4.8L volume treatment chamber along with one-half (upper or lower section) of a 50 X 9 mm plastic Petri dish containing a Gelman filter pad.
- the appropriate amount of experimental compound, dissolved in 1.0 ml acetone, is pipetted onto the filter pad and the chamber immediately sealed. Four hours later ethylene gas equal to 10 ppm v/v final concentration is injected into the sealed chamber.
- Spray application treatment entails using a DeVilbiss atomizer to completely cover all foliage and stems of two pots of Patio var. tomato plants with the appropriate amount of experimental compound dissolved in 10% acetone / 90% water with 0.05%> Silwett L-77 surfactant. Plants are air-dried in a drying hood for four hours then transferred to a 4.8L polystyrene chamber which is sealed.
- Ethylene gas equal to 10 ppm v/v final concentration is injected into the sealed chamber. Sixteen hours later the chambers are opened in an exhaust hood, allowed to air and the plants scored visually for the degree of protection against ethylene-induced epinasty conferred by the experimental compound when compared to ethylene treated and untreated controls on a scale of 0 to 10. A rating of 10 means complete protection. A rating of 0 means no protection from the effects of ethylene.
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US7041625B2 (en) | 2003-08-21 | 2006-05-09 | Rohm And Haas Company | Method to inhibit ethylene responses in plants |
UA85690C2 (en) | 2003-11-07 | 2009-02-25 | Басф Акциенгезелльшафт | Mixture for use in agriculture, comprising strobilurin and ethylene modulator, method for treatment and controlling infections in legume crops |
EP1609359A3 (en) * | 2004-06-24 | 2011-10-05 | Rohm and Haas Company | A method for treating plants or plant parts |
AU2005242218A1 (en) * | 2005-01-14 | 2006-08-03 | Rohm And Haas Company | Plant growth regulation |
US20070117720A1 (en) * | 2005-11-18 | 2007-05-24 | Jacobson Richard M | Compositions with cyclopropenes |
CN101784508B (en) * | 2007-06-22 | 2014-06-04 | 北卡罗莱纳州立大学 | Methods of inhibiting ethylene responses in plants using cyclopropene amine compounds |
IL184729A0 (en) * | 2007-07-19 | 2008-01-20 | Yissum Res Dev Co | Compositions and methods for blocking ethylene response in plants using 3-cyclopropyl-1-enyl-propanoic acid salt |
KR101429554B1 (en) | 2010-04-22 | 2014-08-14 | (주)이룸바이오테크놀러지 | Cyclopropenes and Method for Applying Cyclopropenes to Agricultural Products or Crops |
CN103524434B (en) * | 2013-09-29 | 2015-08-12 | 北京大学 | The micromolecular inhibitor pyrazinoic acid amide of Plant Ethylene route of synthesis and application thereof |
US20180325106A1 (en) * | 2015-11-03 | 2018-11-15 | Curtin University Of Technology | Method of retarding an ethylene response |
CN106478507A (en) * | 2016-09-28 | 2017-03-08 | 重庆大学 | A kind of 2(1,3,5 triaryl, 1 H pyrazoles 4 base)The preparation method of Cyanoacetyl-Cyacetazid |
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US5100462A (en) | 1991-04-01 | 1992-03-31 | North Carolina State University | Method of counteracting ethylene response by treating plants with diazocyclopentadiene and derivatives thereof |
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CHEMICAL ABSTRACTS, vol. 89, no. 5, 1978, Columbus, Ohio, US; abstract no. 42600p, L.S. SURMINA ET AL.: "skeletal rearrangement during the dehydrochlorination of 1,1-dichloro-2-benzylcyclopropane." page 558; column 1; XP002335566 * |
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