IL41578A - Haloalkyl silanes their production and plant growth regulating compositions containing them - Google Patents
Haloalkyl silanes their production and plant growth regulating compositions containing themInfo
- Publication number
- IL41578A IL41578A IL7341578A IL4157873A IL41578A IL 41578 A IL41578 A IL 41578A IL 7341578 A IL7341578 A IL 7341578A IL 4157873 A IL4157873 A IL 4157873A IL 41578 A IL41578 A IL 41578A
- Authority
- IL
- Israel
- Prior art keywords
- silane
- radical
- formula
- radicals
- phenyl
- Prior art date
Links
- -1 Haloalkyl silanes Chemical class 0.000 title claims description 103
- 239000000203 mixture Substances 0.000 title claims description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- 230000008635 plant growth Effects 0.000 title claims description 8
- 230000001105 regulatory effect Effects 0.000 title description 2
- 239000013543 active substance Substances 0.000 claims description 47
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 44
- 241000196324 Embryophyta Species 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 229910000077 silane Inorganic materials 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 22
- 235000013399 edible fruits Nutrition 0.000 claims description 21
- 229910052794 bromium Chemical group 0.000 claims description 19
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 230000006578 abscission Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- 230000012010 growth Effects 0.000 claims description 8
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- 230000033228 biological regulation Effects 0.000 claims description 5
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000007517 lewis acids Chemical group 0.000 claims description 4
- 230000005070 ripening Effects 0.000 claims description 4
- 244000043261 Hevea brasiliensis Species 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 239000004816 latex Substances 0.000 claims description 3
- 229920000126 latex Polymers 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 150000004756 silanes Chemical class 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 230000001133 acceleration Effects 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 claims 1
- 239000011347 resin Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 claims 1
- 238000005507 spraying Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- 238000007792 addition Methods 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 150000003254 radicals Chemical class 0.000 description 16
- 230000000694 effects Effects 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 230000009471 action Effects 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- 230000018109 developmental process Effects 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 235000020971 citrus fruits Nutrition 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- SJHZKXBGGHJSQU-UHFFFAOYSA-N 2-bromoethylsilane Chemical class [SiH3]CCBr SJHZKXBGGHJSQU-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- FYBFDYNFIJPJSE-UHFFFAOYSA-N bis(2-bromoethyl)-bis(ethenyl)silane Chemical compound BrCC[Si](C=C)(C=C)CCBr FYBFDYNFIJPJSE-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000006072 paste Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- FLPXNJHYVOVLSD-UHFFFAOYSA-N trichloro(2-chloroethyl)silane Chemical compound ClCC[Si](Cl)(Cl)Cl FLPXNJHYVOVLSD-UHFFFAOYSA-N 0.000 description 4
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 3
- 244000099147 Ananas comosus Species 0.000 description 3
- 235000007119 Ananas comosus Nutrition 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000207836 Olea <angiosperm> Species 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- MIHBEVRKYFBXIK-UHFFFAOYSA-N chloro-(2-chloroethyl)-dimethylsilane Chemical compound C[Si](C)(Cl)CCCl MIHBEVRKYFBXIK-UHFFFAOYSA-N 0.000 description 3
- XSDCTSITJJJDPY-UHFFFAOYSA-N chloro-ethenyl-dimethylsilane Chemical compound C[Si](C)(Cl)C=C XSDCTSITJJJDPY-UHFFFAOYSA-N 0.000 description 3
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 230000028245 fruit abscission Effects 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- 238000003306 harvesting Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 230000028514 leaf abscission Effects 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 125000004079 stearyl 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])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 3
- 238000003756 stirring Methods 0.000 description 3
- RRSDFIVXJVMQTP-UHFFFAOYSA-N tetrakis(2-bromoethyl)silane Chemical compound BrCC[Si](CCBr)(CCBr)CCBr RRSDFIVXJVMQTP-UHFFFAOYSA-N 0.000 description 3
- UFHILTCGAOPTOV-UHFFFAOYSA-N tetrakis(ethenyl)silane Chemical compound C=C[Si](C=C)(C=C)C=C UFHILTCGAOPTOV-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- BIRKEHBNMHSEHT-UHFFFAOYSA-N 2-bromoethyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CCBr BIRKEHBNMHSEHT-UHFFFAOYSA-N 0.000 description 2
- PSPIGWSLGREJFN-UHFFFAOYSA-N 2-bromoethyl-tris(ethenyl)silane Chemical compound BrCC[Si](C=C)(C=C)C=C PSPIGWSLGREJFN-UHFFFAOYSA-N 0.000 description 2
- MGLQRAQKKGYLPA-UHFFFAOYSA-N 2-chloroethyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)CCCl MGLQRAQKKGYLPA-UHFFFAOYSA-N 0.000 description 2
- MAYUMUDTQDNZBD-UHFFFAOYSA-N 2-chloroethylsilane Chemical compound [SiH3]CCCl MAYUMUDTQDNZBD-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 235000002566 Capsicum Nutrition 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 235000019738 Limestone Nutrition 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000006002 Pepper Substances 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 235000016761 Piper aduncum Nutrition 0.000 description 2
- 240000003889 Piper guineense Species 0.000 description 2
- 235000017804 Piper guineense Nutrition 0.000 description 2
- 235000008184 Piper nigrum Nutrition 0.000 description 2
- 244000018633 Prunus armeniaca Species 0.000 description 2
- 235000009827 Prunus armeniaca Nutrition 0.000 description 2
- 240000005809 Prunus persica Species 0.000 description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 244000078534 Vaccinium myrtillus Species 0.000 description 2
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- ZTRQEQWTQBKCSX-UHFFFAOYSA-N bis(2-bromoethyl)-dimethylsilane Chemical compound BrCC[Si](C)(C)CCBr ZTRQEQWTQBKCSX-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000006028 limestone Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
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- 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
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000009105 vegetative growth Effects 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0898—Compounds with a Si-S linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
41578/2
mix** O'JV'O V' Ki n
» ¾ΗΊΛ nio'iiV o»Twain
onin q»V
Novel haloalkyl silanes, their
production and plant growth
regulating compositions containing
them
CIBA-GEIGY A.G.
C. 39739
41578/2
The present invention relates to new agents and
processes for the regulation of plant growth by the use
of new 0-halogenoethyl-silanes as active substances,
also to new -halogenoethyl-silanes and to processes
for the production of these silanes. v
The new 3-halogenoethyl- silanes of the present
invention correspond to formula I
CH2 - CH2 - Si - B (I) .
wherein
A represents a radical -S-R^, -N χ
R3
or -CH2-CH2X,
represents a radical
-CH=CH2'or -CH2CH2 ,
X represents chlorine or bromine,
whereby the radicals R-_, R5 and R? each independently represe
C Cl8 al^yl radicals> CrC18 alkyl radicals substituted by
alkoxycarbonyl, phenyl, furyl,tetrahydrofuryl or pyridyl radicals, alkenyl and cycloalkyl groups; pheny
phenyl radicals
41578/4
mono- or polysubstituted by alkyl- or halogen, monosubs t i uted
by C, -C0 alkoxy and benzyl radicals which may be substituted
1 o
by halogen; represents alkyl which can be substituted
by C^-C^ alkoxy, phenyl, C^-C^ cy.cloalkyl, or by a furyl,tetrahydro uryl
enyl which
hylthio
alkyloxy
and halogen;
represents hydrogen, or the same as ,
and alkyl radicals;
C -C alkyl radicals substituted by halogen, . cyano, C , -C^
1 6 l o
alkoxy, C2-C8 alkanoyloxy, phenyl, C2-C8 alkoxyalkoxy, C^-C^
alkenyloxy , . C2~Cg alkanoylalkox , pherioxy, ^^ ^12 cyc^oa^ ^->
yl or" a"fury1,- -1- substi¬
cycl'";alkyl , ^ ~^12 c cl°alkenyl; phenyl radicals mono- or
polysubstituted b bs tituted
by cyano, formyl,
alkoxycnrbonyl; benzyl radicals mono- or polysubstituted by
halogen, monosubs tituted by alkoxy;
the radical R^ can, however, additionally represent the group
-CORg wherein Rg stands for alkenyl radical,
a C^-Cg halogenoalkyl or C^-C^ halogenoa Ikenyl radical, a ^^'^12
cycloa Iky1 , I
• - . a C -CQ alkoxvalkyl, C -C0 alkoxycarbony lalkyl ,
cyc l°a Ikyla 1 ky1 y a phenoxy or a phenyl radical which can be substituted by halogen, C^-C^ alkyl or C^-C^ alkoxy, and finally, for a - furyl,tetrahydrofuryl or pyridyl iradical; with the proviso, however, that only one of the symbols A and B may represent the respective radical -OR^ or -0R.£ in the case where C represents the methyl group.
By alkyl radicals are meant straight-chain or branched radicals having 1 to 18 carbon atoms, such as, e.g.
methyl, ethyl, n- propyl, isopropyl, n-butyl, sec-butyl,
n-hexyl, n-octyl, n-dodecyl, n-octadecyl, and so forth. It is particularly the straight-chain and branched alkyl radicals having 1 to 8 carbon atoms vihich form the alkyl moiety
of alkoxy, alkylthio or alkoxycarbony1 substituents of
an alkyl radical or of a phenyl radical . In the case of
halogenoalkyl radicals, these are alkyl radicals having
1 to 6 carbon atoms, which can be substituted by fluorine, chlorine and/or bromine, such as, e.g. trifluoromethyl ,
2-chloroethyl, 6-chlorohexyl, etc.. Alkenyl radicals are straight-chain or branched radicals having 3 to 18 carbon
atoms, e.g. propenyl, butenyl, octenyl, decenyl or
heptadecenyl radicals .
These alkenyl radicals can be mono- or polysubstituted by halogen, such as fluorine, chlorine, bromine and/or iodine. Alkenyl radicals having 3 to 6 carbon atoms, form the alkenyl moiety of alkenyloxy radicals . Alkynyl
preferably
radicals proforably contain 3 to 8 carbon atoms/ in a
straight chain, such as, e.g. 2-propynyl, 2-butynyl or
3-hexyn3'l. By cycloalkyl and cycloalkenyl radicals are meant such radicals having 3 to 12 carbon atoms, such as, e.g. cyclopropyl, cyclopentyl, cyclopentenyl , cyclohexyl or cyclohexenyl , etc.
The β-halogenoethyl-silanes of formula I affect
in a varying manner the growth of parts of plants above and below the soil, and have a low toxicity towards warmblooded animals. The active substances cause no morphological changes or damage which would result in the withering of the plant. The compounds are not mutagenic. Their action differs from that of a herbicidal active substance and of a fertiliser. The action corresponds more to the effects which can be observed on application of ethylene to various parts of plants. It is known that the plant itself produces, in various stages of development, ethylene to a varying degree, particularly before and during the ripening process of the fruits, and at the end of the vegetation period with the occurring abscission of fruit and leaves. Since the
regulation of ripening and of fruit and leaf abscission by application of chemical substances is of the greatest
such as commercial importance in the cultivation of f uit , /citrus fruit, pineapples and cotton, efforts have been directed towards the discovery of compounds with which such
effects might be obtained, without the treated plants suffering any kind of damage in the process. Thus, various classes of substances have meanwhile become known with which it has been possible to obtain some of the growth-regulating effects referred to; however, the extent of the range of action of these substances corresponds in no way to that of ethylene. Compounds which under certain conditions release ethylene are known. Such compounds have the disadvantage either in that they are relatively unstable under the influences of weather, because they are very susceptible to hydrolysis, or in that they are phytotoxic. In the South African Patent Specification
No. 68/1036, β-halogenoethyl- phos phonic acid derivatives are described as active substances which regulate plant growth. These compounds decompose in and on the plant with the release of ethylene, and are therefore similar in action and range of action to ethylene. By virtue of their very low stability, phosphonic acid derivatives are not able, however, to satisfy the demands made on them. As they are stable only in an acid medium, more precisely in a pH-range below 5, the active-substance concentrates have to be stabilised by the addition of acids . This addition of acid
however, limits the range of application of these active
substances in view of the resulting phytotoxic effects.
Furthermore, the storage of such sensitive concentrates of active substance presents difficulties.
Further compounds known as herbicidally active substances are halogenoalkyl-xnethyl-silanes cf» US-Patent Specifications Nos. 3,390,976 and 3,390,977, and J.E. Leasure et al. ,
J.Med. Chem. J3 , 949 (1966)7'. $-Chloroethylmethyl-dimethoxy~ silane was produced by J.K. Leasure et al. (loc.cit) , but has no herbicidal action. The US-Patent Specification
No.3,183,076 describes a-chloroethylmethyl-dialkoxy-silanes of the formula
CH,
R - Si - (OR* )2
wherein R i3 methyl, chloromethy1, ethyl or o-chlorethyl R' is hydrogen, lower alkyl or chloro lower alk l. The activity is given as growth altering in plants e.g. suppression and control of the growth of germinant seeds, emerging seedlings and
established plants and for promoting the maturing of crops and facilitate their harvest.
The compounds of the present invention must contain a β-halogeno-ethyl group (not an -chloroethyl ) group, which the plant can split off and use the ethylene thus liberated for its own purpose e.g. weakening of the tissue in the stem
which connects a fruit to the branch. (Citrus fruit and olives are the crop wherein use of such compounds is most meaningful because they adhere rather strongly. In citrus fruit it is thus possible to harvest ripe fruit while leaving not ripe fruit and flowers unharmed on the tree by this method.
The compounds of the present invention are structurally different from the known compounds and it has been found that a chloromethyl- or a a-chlorethyl silane does not act in the
same manner as the compounds of the present application.
For example, while the compounds of the present
invention are very effective in fruit abscission of olives, the known compounds have no effect at all.
The present invention relates to new agents containing as active substances β-halogenoethyl-silanes , which
have a stimulating or retarding action on plant growth in the various stages of development of the plants. These agents can contain the usual carrier substances, distributin; agents, and stabilisers protecting against the effects of light and of oxidation. The action of the new agents is to regulate vegetative plant growth and germination power, and to promote the formation of blossoms, the development of fruit and the growth of abscission layers. In the case of monocotyledons, an increase in tillering and branching was observed with a simultaneous reduction of growth in height. There was moreover a strengthening of the support tissues of
the stalks in the case of the treated plants. The formation of undesirable side shoots on various types of plants
is very greatly reduced; for example, the vegetative
growth of grape vines is inhibited. The new compounds also have a secretion- promoting action; for example, the latex discharge in the case of Hevea brasiliensis is promoted, an effect which is of great commercial importance. As tests have shown, the rooting of seedlings and cuttings, as well as the development of tubers in the case of potatoes, is promoted. In addition, there occurs a simultaneous sprouting of dormant rhizomes, a factor which is particularly important concerning the various perennial weeds, such as couchgrass, Johnson grass and cyperus, for these can. then be easily
destroyed or suppressed by herbicides. The germination
capacity of seeds, such as, e.g. seed potatoes and legumes, is promoted with low concentrations, and inhibited with
higher concentrations. Both the one effect and the other can be commercially important. A regulation of the blossoming time and of the number of blossoms is possible in the case
of many ornamental and cultivated plants. This effect is
a particularly important factor in the growing of pineapples . If all the trees or shrubs blossom at the same time, then the crops can be gathered within a comparatively short space of time. With regard to cucurbitaceae, there occurs a
displacement of the blossom sex differentiation in favour of pistillate flowers .
Tests have shown that in the case of fruit trees there occurs a thinning of blossomsand fruit. Furthermore,
fruit ripening and fruit colouration are accelerated and improved, e.g. with oranges, melons, apricots, peaches,
tomatoes, bananas, bilberries, figs, coffee, pepper,
o
tobacco and pineapples . As a result of the development
of abscission layers, the abscission of fruit and
leaves is rendered appreciably more easy. This factor
has great commercial significance with regard to mechanical harvesting, e.g. of citrus fruits, such as oranges,
grapefruits and olives; or stone fruit such as cherries, damsons, peaches, plums and apricots; or pomaceous ifruit such as apples and pears; or soft fruit such as currants, rasberries and bilberries; or nuts such as walnuts
and pecan nuts; or sub-tropical fruits such as coffee,
figs and pepper, or cotton. With high concentrations,
the defoliation of ornamental plants, such as chrysanthemums, rhododendrons, carnations and roses, is also obtained.
The extent and the nature of the action are dependent on the most diverse factors; they are dependent particularly on the time of application with regard to the stage of
development of the plant, and on the application concentration. These factors vary, however, depending on the type of
plant and on the effect desired. Thus, for example, lawns are treated during the entire growth period; ornamental
plants, of which, e.g. the intensity and number of ,the
blossoms are to be increased, before development of the
blossom setting; plants of which the fruit is to be sold, or in some other way utilised, immediately after blossoming,
or at an appropriate interval of time before the gathering of the crop. Application of the active substances is effected by the use of solid or liquid agents, these being applied to parts of plants above the soil, to the surface of the soil, as well as into the soil itself.
The preferred method is the application to the parts of plants above the soil, for which purpose solutions or aqueous suspensions are most suitable. In addition to solutions and dispersions for the treatment of the growth substrate (soil), dusts, granulates and
scattering agents are also suitable.
The essential promotion of the abscission of citrus fruits and bean leaves with the use of agents according to the invention was demonstrated by the following tests.
The active substances are sprayed, in the form of solutions in concentrations of 0.2% and 0.4%, respectively, onto branches, well hung with fruit, of various orange trees. The tests are evaluated after 14 days according to the method developed by W.C. Wilson and C.H. Hendershott [Proc. Am. Soc. Hort . Sc. 90, 123 - 129 (1967)]. The test consists in the measuring of the force in kilograms required to effect the abscission of the f uit.
41578/3
In the case of bean-leaf abscission tests-, segments of bean leaves of the type "Tempo" are immersed in a solution of 0.0027c of active substance; for each active substance, 4-8 segments are left for 6 days in the active substance solution under controlled conditions. On specific days after commencement of the treatment, the number of resulting abscissions (contraction or necking of the stalk in the abscission zone on the leaf-side) is
assessed.
Tests with agents containing the following active
substances produced excellent results:
2-chloroethyl-bis (benzylthio) -hexyloxy-silane,
2-chloroethyl- (benzylthio) -bis (hexyloxy) -silane ,
2-chloroethyl-methyl-benzylthio-benzyloxy-silane ,
2-chloroethyl-methyl-bis (benzylamino) -silane ,
2-chloroethyl-methyl-bis (octadecylainino) -silane,
bis- ( β-bromoethyl) -divinyl-silane ,
tris- ( β-bromoethyl) -vinyl-silane,
tetrakis- ( β-bromoethyl) -silane ,
2-chloroethyl-dimethyl-ethoxy-silane,
2-chloroe hyl-dimethyl-octyloxy-silane ,
2-bromoe hyl-dimethyl-octyloxy-silane ,
2-chloroethyl-dimethyl-benzoxy-silane,
41578/3
-bromoethyl-dimethyl-benzyloxy-silane ,
-chloroethyl-dimethyl- (propynyl- (2 * ) -oxy) -silane , -chloroethyl-dimethyl- (butenyl- (21 ) -oxy) -silane , -chloroethyl-dimethyl- (4 ' -methoxybenzyloxy) -silane, -chloroethyl-dimethyl-acetoxy-silane ,
-chloroethyl-dimethyl- (41 -chlorobenzyloxy) -silane , -chloroethyl-dimethyl- ( 2-chloroethoxy) -silane, -chloroethyl-dimethyl- (hexynyl- (3 ' ) -oxy) -silane, -chloroethyl-dimethy.l- (benzylthio) -silane ,
-chloroethyl-dimethyl- (octylthio) -silane ,
-chloroethyl-dimethyl- (benzylamino) -silane ,
-chloroethyl-dimethyl- (octadecylamino) -silane .
Agents according to the invention arc produced in a manner known per se by the intimate mixing and grinding of active substances of the general formula I with
suitable carriers, optionally -with the addition of
dispersing agents or solvents which are inert to the
active substances.
VJater-dispersible concentrates of active substance, i.e. wettable powders, pastes and emulsion concentrates, are active substance concentrates which can be diluted with water to obtain any desired concentration. They
consist of active substance, carrier, optionally
additives which stabilise the active substance,
surface-active substances, and anti-foam agents and,
optionally, solvents. The concentration of active
substance in these agents is 0.5 - 80%.
The wettable powders and pastes are obtained by
the mixing and grinding of the active substances with dispersing agents and pulverulent carriers, in suitable devices, until homogeneity is attained. Suitable
carriers are, e.g. the following:
kaolin, talcum, bole, loess, chalk, limestone, gT-ou-t - sinter Attapulgite
limestone -Vfe-fe-qclay , dolomite, diatomaceous earth,
precipitated silicic acid, alkaline-earth metal silicates, sodium and potassium aluminium silicates . (feldspar and mica) calcium and magnesium sulphates, magnesium oxide, ground synthetic materials, fertilisers such as ammonium -sulphate, ammonium phosphate, ammonium nitrate, urea, ground
vegetable products such as bran, bark dust, sawdust,
ground nutshells, cellulose powder, residues of plant
extractions, active charcoal, etc., alone or in
admixture with each other,
Suitable dispersing agents are, e.g. the following:
condensation products of sulphonated naphthalene and
sulphonated naphthalene derivatives with formaldehyde,
condensation products of naphthalene or of naphthalene-sulphonic acids with phenol and formaldehyde, as well as alkali, ammonium and alkaline-earth metal salts of
ligninsulphonic acid, also alkylarylsulphonates ,
alkali metal salts and alkaline-earth metal salts of
dibutylnaphthalenesulphonic acid, fatty alcohol sulphates such as salts of sulphated hexadecanols, heptadecanols ,
octadecanols , and salts of sulphated fatty alcohol
glycol ether, the sodium salt of oleyl methyl tauride, dialkyl-dilaurylammonium chloride and fatty acid alkali metal and
alkaline-earth metal salts.
Suitable anti-foam agents are for example silicones.
To these mixtures may also be added additives-stabilising the active substance, and/or non-ionic,
anion-active and cation-active substances, which, for
example, improve the adhesiveness of the active substances on plants and on parts of plants (adhesives and
agglutinants) , and/or ensure a better wettability (wetting agents). Suitable adhesives are, for example, the following:
olein/lime mixture, cellulose derivatives (methyl cellulose, carboxymethyl cellulose), hydroxyethylene glycol ethers of mono- and dialkylphenols having 5 - 15 ethylene, oxide radicals per molecule and 8 - 9 carbon atoms in the
alkyl radical, ligninsulphonic acid, alkali metal and alkaline-earth metal salts thereof, polyethylene glycol ethers (carbowaxes) , fatty alcohol polyglvcol ethers
having 5 - 20 ethylene oxide radicals per molecule av^d
8 to 18 carbon atoms in the fatty alcohol moiety,
condensation products of ethylene oxide, propylene oxide, polyvinylpyrrolidones , polyvinyl alcohols, condensation products of urea/formaldehyde, as well as latex products. • The active substances are so mixed, ground, sieved
and strained with the above mentioned additives that
the solid constituen in the case of wettable powders has a particle size not exceeding 0.02 to 0.04 mm, and in the case of pastes not exceeding 0.03 mm.
Emulsion concentrates and pastes are prepared by
application of the dispersing agents such as those
mentioned in the preceding paragraphs, organic solvents and water. Suitable solvents are, e.g. the following:
ketones, benzene, xylenes, toluene, dimethyljsulphoxide , and mineral oil fractions boiling in the range of 120° to 350°. The solvents must be practically odourless,
non- hytotoxic, and inert to the active substances.
Furthermore, the agents according to the invention
can be employed in the form of solutions. For this
purpose, the active substance (or several active
substances) of the general formula I is (or are) dissolved in suitable organic solvents, solvent mixtures, or
water. The followin -can be used as organic solvents:
aliphatic and aromatic hydrocarbons, chlorinated
derivatives thereof, alkylnaphthalenes , or mineral oils on their own or in admixture with each other. The
solutions should contain the active substances in a
concentration range of from 1 to 20%.
The solid preparations, such as dusts, scattering
agents and granulates, contain solid carriers such as
those mentioned in the foregoing, and, optionally,
additives stabilising the active substance. The particle size of the carriers is for dusts advantageously up to
about 0.1 mm; for scattering agents from about 0.075 mm
to 0.2 mm; and for granulates 0.2 mm or coarser. The
concentrations of active substance in the solid
preparations are from 0.5 to 807o.
All the mentioned active substance concentrates may
also contain agents stabilising against the effects of
light, and antioxidants.
In the following are described several types of preparations containing active substances usable according to the invention.. Where not otherwise stated, the term 'parts' denotes parts by weight .
Grnnnl a e
The following substances are used for the preparation of a 57o granulate:
parts of 2-chloroethyl- dimethyl- (21 -chloroethoxy) - silane,
0.25 parts of epichlorohydrin,
0.25 parts of cetyl polyglycol ether,
3.50 parts of polyethylene glycol ( "Carbowax" ) ,
91 parts of kaolin (particle size 0.2 - 0.8 mm).
The active substance is mixed with epichlorohydrin and the mixture dissolved in o parts of acetone; to the solution are then added polyethylene glycol and cetyl polyglycol ether. The thus obtained solution is sprayed on to kaolin, and the acetone subsequently evaporated
in vacuo .
Instead of 5 parts of■ the above active substance, it is also possible to use the following:
parts of 2-chloroethyl- (benzylthio) -bis- (hexyloxy) -silane, or
parts of bis (2-bromoethyl) -divinyl-silane . .
The following constituents are used for the preparation of a) a 407,, b) a 50%, c) a 25%, and d) a 10%
wettable pov^der:
a) O pa ts of 2-chloroethyl-- dimethyl- (octyloxy) -silane ,
pa ts of sodium ligninsulphonate ,
1 pa t of sodium dibutyl-naphthalenesulphonate ,
54 parts of silicic acid;
b) 50 parts of 2-chloroethyl- dimethyl- (dodecyloxy) -silane ,
parts of alkylaryl sulphonate ("Tinovetin B"),
parts of calcium ligninsulphonate, ,
1 part of Champagne chalk/hydr oxyethyl cellulose
mixture (1 : 1) ,
parts of silicic acid,
14 pa ts of kaolin;
c) 25 parts of 2-chloroethyl- dimethyl- (4 ' -methoxy-benzoxy)- silane,
.'5 parts of the sodium salt of oleylmethyl tauride,
2. 5 parts of naphthalenesulphonic acid/formaldehyde
condensate,
0. 5 parts of carboxymethyl cellulose,
par s of neutral potassium aluminium silicate,
62 parts of kaolin;
d) 10 pa ts of 2-chloroethyl- dimethyl- (4 ' -chloroben¾xy) -si: parts of a mixture of the sodium salts of saturated
fatty alcohol sulphates,
parts of naphthalenesulphonic acid/formaldehyde
condensate,
82 parts of kaolin.
The active, substances are intimately mixed, in suitable mixers, with the additives; the mixture is subsequently ground in suitable mills and rollers . Wettable powders are thus obtained which can be diluted with water
to give suspensions of any desired conce ration. Such suspensions are employed, e.g. for the removal of
undesired side shoots, for the tillering of lavms, and for the rooting of seedlings and cuttings.- etc...
Equally good wettable powders can be obtained if the active substance under a) is replaced by 40 parts of 2-chloro-ethyl-bis (benzylthio) - (hexyloxy) -silane ; or by 40 parts of tris- ( 2-bromoethyl ) -vinyl-silane ; or if the active substance under b) is replaced by 50 parts of 2-chloroethyl-methyl-bis (octadecylamino) -silane , or by bis ( 2-bromoethyl ) -divinyl-silane; or if the active substance under c) is replaced by
parts of 2-chloroethyl-methyl-benzylthio-benzyloxy-silane , or by bis (2-bromoethyl) -methyl-vinyl-silane or, finally, if the active subance under d) is replaced by 10 parts of
2-chloroethyl- (benzylthio) -bis (hexyloxy) -silane , or by 10 parts of bis (2-bromoethyl) -dimethyl-silane.
Ernul s ion con con (;r at:e
The following cons t tuents are mixed together to
produce 2570 emulsion concentrates:
a) 25 parts of 2-chloroethyl- dimethyl-benz-bxy -silane,
parts of a mixture of nonylpbenolpolyoxyethylene
and calcium dodecylbenzenesulphonate,
70 parts of xylene;
b) 25 parts of 2-chloroethyl- dimethyl-ethoxy -silane, 10 parts of a mixture of non lphenolpolyoxyethylene
and calcium dodecylbenzenesulphonate,
65 parts of cyclohexanone .
This concentrate can be diluted v;ith water to obtain emulsions of any desired concentration. Such emulsions are suitable for the thinning out of blossom and fruit, for the accelerated ripening of fruits, and for the
promotion of fruit and leaf abscission.
Equally good emulsion concentrates are obtained if the active substance under a) is replaced by 25 parts of 2-chloroethyl- methyl-benzylthio-benzyloxy -silane, or by tetrakis(2-bromoethyl) -silane; or if the. active substance under b) is replaced by 25 parts of 2-chloroethyl bis (benzyl-thio)- (hexyloxy) -silane, or by 2-bromoethyl-trivinyl-silane .
All β-halogenoethyl-silanes embraced by formula I are new compounds. The new β-halogenoethyl-silanes of formula I wherein A, B and C do not denote hydrocarbon radicals are produced according to the present invention by the reaction of a β-halogenoethyl- trichloro-silane of formula II
X - CH2 - CH2 - Si - Cl3 (II)
independently
with three equivalents -iiree+y chosen from one or more of the following types of mercaptans, amines or alcohols of formulae III, IV, V, VI, VII or VIII:
RjSH (III) R5SH (IV) . RySH (V)
R2R3 H (VI) R^OH (VII) R OK (VIII)
The new β-halogenoethyl-silanes of formula I where A does not stand for a hydrocarbon radical, and methyl is denoted by C alone or by both B and C, are produced in an analogous manner by the reaction of a β-halogenoethyl-methyl-chlorosilane of formula IX
' CI D
X - CH2 - CH2 - Si (IX)
wherein D is methyl or chlorine,
with one or two equivalents of one of the mercaptans, amines or alcohols of the formulae III, IV, V, VI, VII or VIII/ respectively.
In the formulae II and IX of the starting materials
X represents chlorine or bromine, and R, , R , R~, R
4'
R^, and R-, have the meanings given under formula I.
The β-halogenoethyl-dimethyl-silanes of formula I
are
produced according to the present invention by the reaction of a β-halogenoethyl-dimethyl-chlorosilane of the formula
CH
3
CH
3
with one equivalent of an acid of the formula
0
or of a carboxylic acid anhydride of the formula
R - C - 0 - C - Rp
o I I i t 8
0 0
to give a compound of the formula
CH„
I
- CH2 - CH2 - Si - 0 - C - R8
C1I3
and, optionally, the exchange of the radical
- 0 - C - R0
I t o
0
for the radical of an alcohol of formula VII
R 0H
The symbols R^, Rg and X have the earlier defined meanings .
The process is preferably carried out in the presence of solvents and/or diluents which are inert to the
reactants . Aprotic solvents are particularly suitable, such as, e.g. aliphatic and aromatic hydrocarbons, e.g. hexane, cyclohexane, benzene, toluene, xylene,
halogenated hydrocarbons such as chlorinated ethylene, carbon tetrachloride, chloroform, chlorobeiizene , also ethers and ethereal compounds such as diethyl ether, tetrahydrofuran, etc..
A complete reaction is obtained moreover where the alcohols, mercaptans or amines employed as reactants are used in excess to serve as solvents or diluents.
Furthermore, the addition of an acid-binding agent to the reaction mixture may be necessary in some cases.
Suitable acid-binding agents for this purpose are, in particular, tertiary amines such as trialkylamines , e.g. triethylamine , pyridine and pyridine bases, dialkyl-anilines , etc ..
The reaction temperatures are in the range of 0 to 100°C; the reaction duration can vary from a few minutes to several days, and depends to a great extent on the reactivity of the mercaptans, amines or alcohols employed.
The two starting materials of formula II wherein X represents chlorine or bromine are known. β-Chloroethyl-trichloro-silane can be produced, for example, by reaction
f
of ethyl-trichloro-silane with chlorine (c^>. L.H. Sommer
et al., J.Am. Chem. Soc. 68, 1881 (1946); and β-bromoethyl-trichloro-silane by reaction of ethyl-trichloro-silane with bromine (K.W. Michael, J.Org. Chem. 34, 2832 (1969); or by HBr-addition to vinyl-trichloro- silane according to the method of A.I. Bourne (J. Chem. Soc, Sect. C.
1970, 1740) . Catalysts which can be used for this
addition reaction are UV-light, peroxides and radical initiators.
Of the starting materials of formula IX, the chlorine compound wherein X and D represent chlorine is known, and can be produced, for example, by reaction of ethyl- nethyl-dichloro/silane with chlorine (c^. J.K. Leasure et al . , loc . cit .) .
The starting materials of formula IX wherein X
represents bromine, and wherein X represents chlorine and D methyl, have not hitherto been described in the literature .
β-Bromoethyl-methyl-dichloro-silane is produced by methods known per se by reaction of ethyl-/methyl-dichloro/ silane with bromine, corresponding to the process described by K.W. Michael (loc. cit.) for the production of β-bromo-ethyl-trichloro-silane; or by HBr-addition to vinyl-methyl-dichloro-silane analogously to the mode of reaction describ by A.I. Bourne (loc . cit .) . For these addition reactions the catalyst can be UV-light, peroxides and radical, initiators.
The US-Patent Specification No. 3,183,076 describe a-chloroethyl-methyl-dialkoxy-silanes , which can be used for the promotion of germination and leaf-abscission , etc. β-Chloroethyl-dimethyl-chloro-silane is produced by methods known per se by reaction of ethyl-dimethyl-chloro-silane with chlorine, corresponding to the process described by A.D.Petrov (Doklady Akad.Nauk S.S.S.R.
100, 1107 (1955) for the production of 3-chloroethyl- o
diethyl-chloro-silane or by HCl-addition o- vinyl-dimethyl-chloro-silane analogously to a mode of reaction described by G.H.Wagner et al . , (Ind. Eng.Chem., 45 ,
367 (1953) .
There is obtained in a similar manner g-bromoethyl dimethyl-chloro-silane by a method known per se (cf.
K.W.Michael, J. Org. Chem. , 34_, 2832 (1969)) by reaction of ethyl-dimethyl-chloro-silane with bromine, or by addition of HBr to vinyl-dimethyl-chloro-silane (cf.
A. I. Bourne, J.Chem.Soc. , Sect . C , 1970 , 1740).
The catalysts for the addition of HCl to vinyl-dimethyl-chloro-silane can be zinc chloride and other Lewis acids.
41578/2
The addition of HBr to vinyl-dimethyl-chloro-silane
is catalytically promoted by UV-light, peroxides and
radical initiators.
β-Halogenoethyl-silanes wherein all the symbols
A, B and C are hydrocarbon radicals can be.
produced by methods known per se; for example, by reaction of corresponding ethyl-silanes with chlorine or bromine
according to the process described by A.D. Petrov et al.,
[Doklady Akad.Nauk. S.S.S.R. 100, (1955) ]; or by the
process described by K.W. Michael, [J.Org.Chem. 34, 2832
(L969) 1 for the production of β-chloroethyldiethyl-chloro- silane or β-bromoethyl-dimethyl-chloro-silane . Preferably, however, these new β-halogenoethyl-silanes are produced
by addition of HBr or HC1 to vinyl-silanes , that is, to produce -bromoethyl-silanes of formula lb
wherein
Y2 represents -CH=CH2 or -CH2-CH2-Br, and
X and Z2 each independently represent -CH^, -CH=CH2 or
-CH2-CH2-Br,
the addition being effected by reaction of hydrogen bromide with the appropriate vinyl-silane derivative of formula lib
41578/2
wherein
Y3 represents -CH=CH2 , and
X3 and Z3 each independently represent -CH^ or -CH=CH2 ,
in a molar ratio of at least 1:1; and to produce
/3-chloroethyl-silanes of formula Ic
Cl-CH2-
wherein
represents -CH=CH2 or -CH2-CH2-C1, and
and each independently represent "CH^, -CH=CH2 or
the addition being effected by reaction of hydrogen chloride with the appropriate vinyl-silane derivative of formula lib in molar ration of at least 1:1.
The reaction of a vinylrsilane_of_formula lib..with hydrogen bromide is advantageously performed by
irradiation with UV-light and/or in the presence of a
catalyst, such as organic peroxides or radical initiators.
Suitable -catalysts are, for example: dibenzoyl peroxide, diacetyl peroxide, di-tert-butyl peroxide, cumene hydroperoxide, dialkoxyazo compounds and azobisisobutyronitrile.
The reaction temperatures can vary, depending on the nature of the final product desired, within wide limits;
they are however advantageously between -10°C and +150°C,
'particularly between -10°C and +35°C. Since the reaction
is intensely exothermic, it is generally performed with initial cooling of the reaction mixture. It is also
possible to carry out the reaction under elevated
pressure .
The reaction of a vinyl-silane of formula lib with hydrogen chloride is advantageously performed in the
presence of a Lewis acid, and optionally under elevated pressure .
The Lewis acids employed can be the compounds known from the literature: for example, aluminium chloride,
ί
aluminium bromide, iron(III)fchloride, antimony pentachloride, antimony pentafluoride, tin tetrachloride, zinc chloride and boron trifluoride. The reaction is preferably performed in the presence of aluminium chloride.
In general, it is advisable to carry out the reaction at a pressure of at least 5 bars, and at a temperature of between 0°C and 60°C. It is also possible in certain cases, however, to operate at normal pressure; e.g.,
for the production of the β-chloroethyltrimethyl-silane known per se (c^. Sommer and Baugham, J .Am.Chem.Soc. 83 , 3346 (1961).
wherein the
various "Hal" meanings are not identical can be obtained, for example, by reaction of vinyl-silanes of formula lib with a mixture of hydrogen chloride and hydrogen bromide, preferably with UV-light irradiation; or by reaction of
-chloroethyl-silanes of formula Ic wherein at least
one of the symbols X^, and represents -CHXHH^
with hydrogen bromide in the above described manner.
The vinyl- silanes of formula lib and the hydrogen bromide or hydrogen chloride are used, as defined, in a molar
ratio of at least 1:1; preferably, however, the hydrogen bromide or hydrogen chloride is used in a ca . 5 - 60% excess
above the stoichiometrically required amount.
The vinyl-silanes of formula lib used as starting
products are known; they can be produced, for example,
by the action of Grignard compounds on corresponding
chlorosilanes .
The following examples serve to further illustrate
the process according to the invention. I the attached
table there are listed further β-halogenoethyl- silanes
of formula I produced by the methods described in
the examples .
The temperatures are expressed in degrees Centigrade.
Example 1 (Production of an intermediate)
An amount of 59.4 g of 2-chloroethyl- trichloro-silane is dissolved in 750 ml of absolute diethyl ether an addition is then made in the course of one hour at
-5° to -10° of a mixture of 34.9 g of he.xan-(l)-ol and
23.7 g of absolute pyridine dissolved in 250 ml of
absolute ether. The mixture is afterwards stirred for
12 hours at room temperature; filtration, is then performed and the filtrate concentrated in vacuo. After fractional distillation there is obtained 39.2 g of 2-chloroethyl- hexyloxy-dichloro/-silane ;
B.P. : 69 - 72°/0.1 Torr .
Calculated: C 36.5 H 6.5 Si 10.7%
Found: C 36.5 H 6.5 Si 11.0%
Example 2 (Production of an intermediate)
An amount of 59.4 g of 2-chloroethyl-trichloro-silane is dissolved in 750 ml of absolute diethyl ether;
an addition is then made in the course of one hour at -5° to -10° of a mixture of 69.7 g of hexan-(l)-ol and 47.5 g of absolute pyridine dissolved in 250 ml of absolute
ether. The mixture is subsequently stirred for 12 hours at room temperature; filtration is then performed and the filtrate concentrated in vacuo. After fractional distillation there is obtained 32.5 g of 2-chloroethyl-
chloro/-silane ;
B.P.: 97 - 102°/0.001 Torr, n?n = 1.4423.
Example 3 (Production of an intermediate)
An amount of 35.5 g of 2-chloroethyl-methyl-dichloro-silane is dissolved in 300 ml of absolute diethyl ether; an addition is made in the course of one hour at -5° to -10° of a mixture of 2.6 g of benzyl alcohol and 15.8 g of absolute pyridine dissolved in 100 ml of absolute ether,
The mixture is stirred for 12 hours at room temperature; filtration is subsequently performed and the filtrate concentrated in vacuo. There is obtained 53.3 g of
2-chloroethyl- methyl-benzyloxy-chloro -silane ;
n!^ = 1.5123.
Example 4
A mixture of 30.3 g of triethylamine and 32.1 g of benzylamine is dissolved in 400 ml of absolute diethyl ether; an addition is made at -5° to -10° in the course of 1 1/2 to 2 hours of 19.8 g of 2-chloroethyl-trichloro-silane dissolved in 100 ml of absolute ether. The mixture is stirred for 24 hours at 0° and for 12 hours at room temperature; filtration is then performed and the filtrate concentrated in vacuo. There is obtained 37 g of
tria
2-chloroethyl- j -a(benzylamino) -silane;
n?n = 1.5730
U Calculated: Si 6.970
Found: Si 7.1%
Example 5
An amount of 13.2 g of 2-chloroethyl-
silane is dissolved in 100 ml of absolute diethyl ether; additions are then made at -10°, in the course of 30 minutes, firstly of 12.4 g of benzylinercaptan and then of 7.9 g of absolute pyridine dissolved in 50 ml of absolute ether. The mixture is subsequently stirred for
2 hours at 0° and for 2 hours at room temperature and afterwards refluxed for 36 hours. Filtration is performed; the filtrate is quickly washed with ice cold water, dried, and concentrated in vacuo to obtain 23 g of 2-chloroethyl- "bis
(hexyloxy)-di(benzylthio) -silane ;
n^Q = 1.5215
Calculated: Si 6.4%
Found: Si 6.3%
Example 6 (Production of a starting material)
42.3 g of vinyl-methyl-dichlorosilane is cooled to -5° to 0°. Hydrogen bromide is then introduced at this temperature, with UV-irradiation, for a period of 30 to 40 minutes. After completion of the HBr-absorption, the Solution is allowed to stand overnight in a nitrogen
atmosphere at room temperature. There is obtained an amount of 61.6 g of the new compound 2-bromoethyl- jmethyl-dichloro/ silane; B.P.: 94° - 96°/57 Torr.
Calculated: Si 12.6%
Found: Si 13.0%
Example 7 (Production of a starting material)
A mixture of 142.3 g of vinyl-methyl-dichlorosilane and 1 g of anhydrous AlCl^ is cooled to -5° to 0° .
Hydrogen chloride is introduced at this temperature, with UV-irradiation, for a period of 90 minutes. After completion of the HCl-abso ption, the product is distilled at 0.1 Torr and at a bath temperature of at most 15° into a flask cooled with dry ice. There is obtained 177.5 g of the known 2-chloroethyl-jfaiethyl-dichloro -silane ;
B.P. : 82 - 84°/68 Torr.
Calculated: Si 15.8
Found: Si 16.4
Example 8 (Production of a starting material)
A 300 ml steel autoclave fitted with magnetic stirrer, thermocouple element and cooling device is charged with 60 g (0.5 mole) of vinyl-dimethyl-chlorosilarte and
0.3 g of anhydrous zinc chloride. The apparatus is flushed twice with nitrogen, and hydrogen chloride then injected portionwise, with stirring, until an internal pressure of 34 bars is obtained. The temperature is raised to 40° and maintained by repeated cooling at 40 - 50° for one hour, during which time the consumed amount of hydrogen chloride is continuously replenished to maintain a
constant pressure of 34 bars.
After cooling, the reaction product is distilled over at room temperature and 0.1 Torr, to effect the removal of the ZnC^-catalyst , into a cooling trap cooled to
-70°; and subsequently fractionated at 60 Torr through a 10 cm Vigreux-column to obtain 7.1 g of 2-chloroethyl-(,/dimethyl-chloro -silanej B.P.: 70 - 72°/60 Torr.
Example 9 (Production of a starting material)
An amount of 725 g of vinyl-dimethyl- chlorosilane is cooled to -5° to 0°; hydrogen bromide is then fed in at this temperature, with UV-irradiation, for 45 to 60 minutes. After completion of the HBr-abso ption, the unreacted hydrogen bromide is expelled with nitrogen, and the solution fractionated through a 20 cm Vigreux-column .
There is obtained 1080 g of 2-bromoethyl- ^dimethyl-chloro^-silane; B.P.: 65 - 66° /13 Torr .
Calculated : Found :
Si 13.39 13.56
Example 10
An amount of 60.4 g of 2-bromoethyl-^dimethyl-chloro^-silane is dissolved in 36 g of acetic acid anhydride, and the solution allowed to stand in a closed vessel for
48 hours at room temperature. The solution is fractionated through a 10 cm Vigreux column.
There is obtained 19.6 g of 2-bromoethyl- /dimethyl-acetyloxy -silane; B.P.: 43° - 44°/0.6 Torr .
Calculated ; Found :
Si 12.5 12.4
Example 11
An amount of 30.2 g of 2-bromoethyl~dimethyl-chloro-silane is dissolved in 350 ml of absolute diethyl ether; an addition is then made at -5° to -10° within 5 to 10 minutes of 6.9 g of ethyl alcohol and 11.9 g of absolute pyridine, both constituents dissolved together in 100 ml of absolute ether. Stirring is carried out for a further hour at 0°, and refluxing then performed for 18 hours.
The reaction mixture is filtered, and the filtrate concentrated in vacuo to obtain 13.1 g of 2-bromoethyl-
B.P.: 67 - 69°/14 Torr.
Calculated : Found :
Si 14.6 14.1
Example 12
A mixture of 10.1 g of triethylamiiie and 10.7 g of benzylamine is dissolved in 150 ml of absolute diethyl ether; an addition is then made at -5° to -10° within one hour of 15.7 g of 2-chloroethyl-dimethyl-chlorosilane dissolved in 50 ml of absolute ether. The mixture, is stirred for 24 hours at 0° and for 12 hours at room temperature. It is then filtered and the filtrate
concentrated in vacuo.
There is obtained 16.8 g of 2-chloroethyl- ^dimethyl-(benzylamino) -silane .
Example 13
An amount of 15.7 g of 2-chloroethyl-dimethyl-chloro- silane is dissolved in 200 ml of absolute diethyl ether; additions are ; then made at -10° within 30 minutes
firstly of 12.4 g of benzylmercaptan, and then of absolute pyridine dissolved in 50 ml of absolute ether. The mixture is stirred for 2 hours at 0° and for 2 hours at room temperature, and then refluxed for 18 hours. It is
subsequently filtered and the filtrate concentrated in vacuo .
There is obtained 19.8 g of 2-chloroethyl-^dimethyl- (benzylthio) -silane .
Example 14
CH--CH,
2
or
Br-CH2-CH2-Si-CH2-CH2-Br .kw. Br-CH2 -CH2 ·- Si -CH2 - CH2 ■
CH-CIL CH=CH,
A vigorous flow of dry hydrogen bromide is fed at a temperature of -5°, with UV-irradiation, into 17.5 g (0.13 mole) of tetravinyl-silane . After commencement of the exothermic reaction, hydrogen bromide is further introduced with cooling (-5 to 0°) until the absorption of hydrogen bromide is ca . 25 g. The reaction mixture is subsequently fractionated under 0.001 Torr through a Vigreux column to obtain 15.3 g (40% of theory) of bis- (β-bromoethyl) -divinyl-silane and 13.4 g (27% of theory) of tris- (β-bromoethyl) -vinyl-silane .
Analyses :
bis- (β-bromoethy1) -divinyl-silane; B.P.Q QQ-^ = 78°
Calculated: C 32.2% H 4.7% Si 9.4% Br 53.7% Found: C 32.4% H 4.7% Si 9.8% Br 53.4%
tris- (ft-bromoethyl) -vinyl-silane; B-P-Q Q1 = ^6°
Calculated: C 25.3% H 4.0% Si 7.4% Br 63.3% Found: C 25.6% H 3.9% Si 7.8% Br 62.4%
Example 15
Br-CII2 -CH2- Si-CH2 -CHΊ -Br
CH2-CIl2-Br
Dry hydrogen bromide is introduced, with UV-irradiation, into 20.4 g (0.15 mole) of tetravinyl-silane, with the
temperature being raised from 0° to 140°. After 5-6 hours the hydrogen bromide absorption has attained a level of
93%; the reaction mixture is cooled, whereupon tetrakis-(β-bromoethyl) -silane crystallises out. After recrystallisation from carbon tetrachloride with the addition of active
charcoal, there is obtained 45 g (65% of theory) of
tetrakis- (jB-bromoethyl) -silane, M'.P. 90 - 91°.
Analysis :
Calculated: C 20.9% H 3.5% Si 6.1% Br 69.5%
Found: C 20.9% H 3.5% Si 6.0% Br 69.8%
Example 16
Br-ClJ 29 --cuill2-- CH2-CH2-Br
CH3
Dry hydrogen bromide is introduced, with UV-irradiation at -5° to 0° into 17.0 g (0.151 mole) of dimethyl-divinyl-silane; the reaction occurring is intensely exothermic, and the hydrogen bromide absorption after 30 minutes is already 99%. The reaction product is fractionated at 10 Tor through a Vigreux column to obtain 31.4 g (7670 of theory) of bis- (β-bromoethyl) -dimethyl-silane; B.P.-^ = 117°.
Analysis :
Calculated: C 26.3% H 5.1% Si 10.2% Br 58.4% Found: C 26.5% H 5.1% Si 10.4% Br 58.0%
Example 17
Br ~C11
B -CH
At a temperature of -5° to 0° and with exposure to
UV-radiation, hydrogen bromide is fed into 54.4 g (0.4 mole) of tetravinyl-silane ; the supply of hydrogen bromide is
continued for ca. 90 minutes, with continuous cooling
and stirring of the reaction mixture, until ca . 68 g of
hydrogen bromide has been absorbed. The following β-bromoethyl-silanes are obtained after f actionating of
the reaction mixture through a 10 cm Vigreux. column:
β-bromoethyl-trivinyl-silane, B.P.Q OO5 = 38-40°
yield: 3 g (3.5% of theory);
bis- ( -bromoethyl) -divinyl-silane, B.P.Q QQ^ ~ 76-78°,
yield: 37.2 g (31.5% of theory);
theory).
It is possible to obtain from7 the distillation residue, by recrystallisation from cyclohexane or from n-hexane, a further 4 g (2.2% of theory) of tetrakis- (β-bromoethyl) -silane; M.P. 91.
A separation of the β-bromoethyl-silanes obtained is in most cases not necessary for their use in agents according to the invention.
Example 18
At a temperature of -10° to +35° and with exposure to
UV-radiation, hydrogen bromide is fed for 4 hours into 50
(0.4 mole) of methyl-trivinyl-silane , until an increase
in weight of 79 g is recorded. The reaction mixture is
fractionated through a 10 cm Vigreux-column to obtain
the following β-bromoethyl-silanes :
β-bromoethyl-methyl-divinyl-silane, B.P.„ „- _ 34-37°,
yield: 3.3 g (4% of theory);
bis- (β-bromoethyl) -methyl- inyl-silane , B . P . = 79-80°,
0.01
yield: 49.7 g (44% of theory)
tris- (β-bromoethyD-methyl-silane, B.P.n n!- = 134-135°,
yield: 47.7 g (33% of theory)
If the tris- (β-bromoethyl) -methyl-silane is recrystallised from n-hexane, then a white crystalline product, M.P. 64°, is obtained.
A separation of the β-bromoethyl-silanes obtained is
in most cases not necessary for their use in agents according to the invention.
Example 19
Cl-CH2-CH2- 2-C1 or
CI] .,
Cl-CH2 -CH2-Si-CH2 -CH2 -C l
CH 2 - CH ? -C 1
Ari amount of 62.1 g (0.5 mole) of methyl-trivinyl-silane is placed into a 300 ml steel autoclave fitted
with magnetic stirrer, thermocouple element and cooling device and containing a nitrogen atmosphere. At a
temperature of -5 to 0°, hydrogen chloride is injected
portionwise until an internal pressure of 30 bars is obtained, The reaction mixture is subsequently stirred for 2 1/2 hours at 0 to 20°, while the amount of hydrogen chloride is
continuously replenished to maintain a constant pressure of 30 bars . A total amount of 90 g of hydrogen chloride is injected. Fractionating of the reaction mixture through a 10 cm Vigreux column yields the following β-chloroethyl-silanes:
β-chloroethyl-methyl-divinyl-silane, = 62-65°,
yield: 19 g (23.7% of theory);
bis- (/3-chloroethyl) -methyl-vinyl-silane, B.P.Q Q-^ = 64-67°,
yield: 20.7 g (21% of theory);
tris- (jS-chloroethyl)-methyl-silane, B.P.Q 0QL = 98-103°,
yield: 4.0 g (3.5% of 'theory) .
Compounds of formula I
CH - CH„ - X
I
B
B
R^S R?S R5S
R2R3 R2R3N
R2R3N
R.O
6
CH,
Table 1
Table 2
Table 3
41578/2
Table 4
A = R- -S B - R.O C X
o Physical data ^ is: R6 is:
Ethyl Ethyl CH3 CI
II Bu yl CI
II Octyl CI
II Dodecyl CI
Octadecy1 CI
Butyl 6- Chlorohexyl CI
II 2- Butyloxyethyl CI
2-Ethylthioethyl CI
II Benzyl CI n20 = 1.4466
II 2- Allyloxyethyl Br
Octyl 2- Phenoxyethyl CI
II 2-Buteny1 CI
II 2- Propynyl CI
3-Hexynyl Br
Benzyl Cyclohexylme thy1 CI
11 Cyclohexyl CI
II 3-Phenyl-2-propenyl CI
II Benzyl CI 1.5353
Phenyl Br
Butyl 3- Chiorophenyl CI
4-Chlorobenzyl Octyl CI
- romophenyl 4-Bromophenyl CI
Cyclohexyl Cyclohexyl It Br
4-liethoxypheny1 3·, 4-DimethyIphenyl II CI
3-Methylphenyl Octyl CI
2-Propenyl Octyl CI
' Table 5
41578/4
Compounds of formula I
CH.
X - CH _ C1L Si - A
I
CH,
Table 7; Λ = O-R^
X Physical data
130 Ethyl CI
131 Ethyl Br' B.P. 67 - 69° /U Torr
132 n-Butyl CI
133 Isobutyl CI
134 sec. Butyl CI
135 Isopropyl CI
136 Hexyl Br B.P. 131° /O , Torr
137 2-MethyIbutyl CI
138 3-Methylbutyl ' CI
139 1,3-DimethyIbutyl CI
140 Octyl CI
141 1-Methylheptyl CI
142 Decyl Br
143 Undecyl CI
144 Dodecyl CI
145 Hexadecyl CI
146 Octadecyl CI
147 2-Chloroethyl CI
6-Chlorohexyl CI
6-Chlorohexyl Br
2 -Methoxyethyl CI
2-Ethoxyethyl CI
2-Isopropyloxyeth l CI
2-Propyloxyethyl CI
2-Butyloxyethyl . CI
2-lIexyloxyethyl Br
2- (2-Ethoxyethoxy) ethyl CI
2- (2-Me thoxyethoxy) ethy1 CI
2- (2-Butyloxyethoxy) ethyl Br
2-Allyloxyethyl CI
2-Aethylthioethyl CI
2-Octylthioethyl CI
3-Phenylpropyl Br
2-Phenylethyl CI
•2-Phenoxyethyl CI
2-Propenyl CI
2-Bu enyl CI
2-Butenyl Br B.P. 80 - 82°/0.15
3 , 7-Dimethyl-2-octenyl CI
-Undecenyl CI
9-Octadecenyl CI
3 , 7-Dimethyl-7-octenyl CI
.
3 , 7-Diwethyl-2 , 6-octadienyl ;Br nD - 1 4748
2-Propynyl CI
2-Propynyl Br
l-P):opyl-2 -propinyl CI
3-Hexynyl CI
Physical data
177 3- Chloro-2-butenyl CI
178 3-Phenyl-2-propcnyl CI
179 3 -Phany1- 2 -prope.ny1 Br n = 1. 5A 90
180 2- (l-Methylethenyl)ethyl C
181 2- Cyanoethyl CI
182 Ethoxycarbonylmetliyl CI
183 1-Ethoxycarbonylethyl) - Br
184 Butoxycarbony1 IV!ethy1 CI
185 Cyclohexyl CI
186 Cyclohexylmethyl CI
187 3-Cyclobex lpropyl Br
"189 Benzyl CI B.P. 90 - 95°/0.3 190 Benzyl Br. B.P. 85 - 87°/0.08 191 A - Chlorobenzyl CI
192 A - Chlorobenzyl Br
193 A -Me hoxybenzyl CI
194 2 , -Dichlorbenzyl CI
195 A-Methylbenzyl CI
196 Phenyl CI
197 A-Chlorophenyl CI
198 3-Chlorophenyl CI
199 3, A-Dichlorophenyl CI
200 3 ,5-Dichlorophenyl CI
201 A-Bromophenyl CI
202 -Me hoxypheny1 CI
203 A-Me hoxyphenyl Br n^ = 1..A708
41578/2
41578/3
Table 8 Λ - 0-R,; V, ■■= -CO-
X Physical data
i
217 Methyl CI
218 Methyl Br A3 - AA°/0.6 Torr
219 Ethyl Cl
220 Ethyl Br
221 Isopropyl CI
222 l-But 1 propyl CI.
223 Pen yl' CI
224 Octyl CI
225 Heptyl CI
226 llndecyl CI
227 Pentadecyl CI
228 Heptadecyl CI
229 2-Propenyl CI
230 2-Propenyl Br
231 1-P open l CI
232 9-Decenyl CI
233 1 , 3~Pentadienyl CI
234 8 j 11-Heptadecadie.nyl CI
235 2-Chloroethyl CI
236 2-Bromoeth}7l CI
237 l-Bromopentyl CI
238 10-Bromodecyl CI
239 10-Bromodecyl Br
240 cis -2-Chloroethenyl CI
241 cis- 2-Chloroethenyl Br
242 Phenylmethy1 CI
243 2-Phenyl ethyl CI
244 k -Ch lorophenylmethyl CI
245 3-Me hyl henyl CI
- ' -
41578/3
41578/2
A = -N /R2
Table 9
N
R.
Physical data
R i R3
κ j
270 j Ethyl ! Ethyl CI
271 ! H ! Butyl CI
1
272 j H 1 Butyl Br
273 ' Octyl
1 H CI
274 j H Dodecyl CI
275 j H Dodecyl Br
276 j H Octadecyl CI
ί
277 j H 2-Propenyl CI
278 j H 9-Octadccenyl Br 1.4664
1
279 ; H 2-Propynyl CI
280 i H 1 , 2 , 2 , -Trimethylpropyl CI
281 H l-Methylhexyl CI
282 H Pentyl CI
283 H Decyl CI
284 H 2-.ethylhexyl CI
285 H Hexa decyl CI
286 H Cyclohexyl CI
287 H Cyclohexylmethyl CI
288 H 2-Methoxyethyl CI
2 89 H 3-1 sopropy1oxypropy1 ci
290 H . 2,2-Diphenylethyl CI
291 H Benzyl CI
292 H Benzyl Br
293 H -Chlorobenzyl CI
294 H 3-Chlorobenzyl CI
295 H 3 } 4 -Dichlorobenzyl CI
296 H 4-Methoxybenzyl CI
297 H Phenyl CI
298 H - Bromopheny 1 CI
299 11 -Methoxypheny1 CI
300 4-Me hylthiophenyl Br 1.5826
H
301 H 3-Me hylphenyl CI
302 Meth l Benz l CI
41578/2'
Table 10 A - s -R
X Physical data
307 Ethyl CI
308 Butyl CI
309 Octyl CI
310 Octyl Br
311 Dodecyl CI
312 Octadecyl CI
313 Methox carbonylethyl CI
314 3-Phen 1propy1 CI
315 Cyclohexyl CI
316 2-Propenyl CI
317 Phe yl CI
318 Phenyl Br
319 4-Bromophenyl CI
320 A-Chlorophenyl ci
321 A-te t . Butylphenyl CI
322 A-Bromo-3-methylphenyl CI
323 A-MeLhoxyphenyl CI
324 A -Methoxypheny1 Br
325 3-Me hylphenyl CI
326 Benzyl CI
327 Benzyl Br
328 A-Chlorobenzyl CI
329 -Chlorobenzyl Br
330 3 , A-Dimethylpheny1 CI
1
Claims (5)
- L.) Composition for the regulation of plant -growth for the purpose of increasing and facilitating the production of useful parts of plants, containing as active substance at least one /S-halogenoethyl-silane of formula I A X - CH2 - CH2 - Si - B j (I) wherein A represents a radical -S-R1} or -CH -CH R2 B represents a radical -SR,-, -N*^ , -OR^, -CH^ R. ■CH=CH2or -CH2CH2X, C represents a radical -SR.,, -N^ , -CH=CH2 -CH3 or -CH2-CH2X, and R3 X represents chlorine or bromine, whereby the radicals R^, R^ and R^ each independen ly represent alkyl radicals substituted by alkoxycarbonyl , phenyl, furyl,tetrahydrofuryl or pyridyl radicals, cycloalkyl groups; phenyl » phenyl radicals 41578/3 mono- or polysubstituted by alkyl or halogen, monosubstituted | by C, -C0 alkoxy and benzyl radicals which may be substituted J 1 o by halogen; R^ represents- c^_c13 alkyl which can be substituted alky rad ca s substituted by halogen, cyano, alkoxy, C2~cQ alkanoyloxy, phenyl, C2-C8 alkoxyalkoxy , C^-C^ alkenyloxy, > alkylthio and'C2~Cg alkoxycarbonyl orafuryl,, tetrahyo^furyl or pyridyl radical- C„-C, Q alkenyl , C-,-C-0 alkenyl substi- ' J Io J 1o tuted b/ phenyl, C^-C^ halogenoalkenyl , C3-Cg alkynyl, C ~C12 cycloalkyl, alkenyl; phenyl radicals mono- or polysubstitu alkyl or halogen, phenyl monosubstituted by cyano, fo alkoxy, C2~Cg alkanoyl and C2~Cg alkoxycarbonyl; benzyl radicals mono- or polysubs ituted by halogen, monosubstituted by alkoxy; the radical R^ can, however, additionally represent the group -CORg wherein Rg stands for C]^~c^ alkyl or C2~ciQ alkenyl radical, a cycloalkyl, : . a (-'2~^8 a ^ ^oxya Iky1 , ^2_<½ a lkoxycarbony la Iky1 , Iky1 a phenoxy or a phenyl radical which can be substituted by halogen, C^-C^ alkyl or C^-C^ alkoxy, and finally, for a - furyl,terahydrofuryl or pyridyl .radical; with the proviso, however , that only one of the symbols A and B may represent the respective radical -OR^ or -ORg in the case where C represents the methyl group.
- 2. )conposition according to Claim 1, containing as active substance a β-halogenoethyl-silane of formula I wherein A represents a radical B represents a radical anc* C represents a radical -SR-,, > °': methyl group, 3 wherein the radicals to R^ are defined as in Claim 1, except that R4 does not represent the group -CORy> and only one of the symbols A and B may represent the respective radical. -OR, or -OR-' in the case here C represents the methyl group.
- 3. )composition according to Claim 1, containing as active substance a β-halogenoethyl-dimethyl-silane of the formula A I X - CH, CH, Si CH. CH. wherein X represents chlorine or bromine, and R2 A represents a radical -OR^, , or -SR-^, 41578/2 wherein to are defined as in Claim 1, with inclusion of the meaning "CORg for R^ .
- 4. ) Composition according to Claim 1, containing as active substance a /3-halogenoethyl-silane of formula I wherein B and C each independently represent "CH^, -CH=CH2 or -CH2-CH-X, and A represents -CH=CH2 or -CH2-CH2-X.
- 5. ) Process for the regulation of plant growth, wherein plants and parts of plants, or the growth substrate of plants, are treated with β-halogenoethyl-silanes of formula I of Claim 1. 6.) A method for the acceleration of the ripening of fruit and facilitation of their abscission as well as for the promotion of the resinous exudation in trees, particularly of the latex flow in rubber trees (Hevea) which consists in spraying fruit bearing or resin producing trees with an effective amount of a compound of formula I, of Claim 1 or a composition contaiing it. 7.) New β-halogenoethyl-silanes of formula I A X - CH2 - CH2 - Si - B (I) C wherein X, A, B and C have the same meanings as in formula I of- Claim 1. 41578/3 8.) Process for the production of β-halogenoethyl· silanes of formula Ϊ2 CH2 - CH2 - St - ½ (lb) Z2 wherein * Y2 represents -CH=CH2 or -CK2-CH2-X, and X2 and Z2 each independently represent -CH^ -CII-CH7 or -CH2-CH2-X, which comprises reacting hydrogen chloride or hydrogen bromide with the appropriate vinyl-silane derivative of the formula CH9 « CH - Si - X3 . (IIb) wherein represents -CH=CH2? and X and each independently represent -Cll or -CD^CIU, in a molar ratio of at least 1:1. 9.) Process according to Claim 8, wherein the reaction is performed by irradiation with UV-light, and/or in the presence of a catalyst I \ r 10.) Process according to Claim 9, wherein the employed catalyst is a Lewis acid, particularly aluminium chloride.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH304872A CH566103A5 (en) | 1972-03-02 | 1972-03-02 | |
CH473372A CH566105A5 (en) | 1972-03-29 | 1972-03-29 | 2-haloethylsilanes - plant growth regulators |
CH467172A CH566104A5 (en) | 1972-03-29 | 1972-03-29 | 2-haloethylsilanes - plant growth regulators |
Publications (2)
Publication Number | Publication Date |
---|---|
IL41578A0 IL41578A0 (en) | 1973-04-30 |
IL41578A true IL41578A (en) | 1978-04-30 |
Family
ID=27174098
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL7341578A IL41578A (en) | 1972-03-02 | 1973-02-19 | Haloalkyl silanes their production and plant growth regulating compositions containing them |
Country Status (13)
Country | Link |
---|---|
JP (1) | JPS4899344A (en) |
AT (1) | AT324367B (en) |
BG (1) | BG21236A3 (en) |
CA (1) | CA1016364A (en) |
DD (1) | DD103125A5 (en) |
EG (1) | EG10981A (en) |
GB (1) | GB1429072A (en) |
HU (1) | HU165899B (en) |
IL (1) | IL41578A (en) |
IT (1) | IT979608B (en) |
NL (1) | NL7303004A (en) |
OA (1) | OA04341A (en) |
SU (1) | SU584736A3 (en) |
-
1973
- 1973-02-19 IL IL7341578A patent/IL41578A/en unknown
- 1973-02-23 CA CA164,419A patent/CA1016364A/en not_active Expired
- 1973-02-28 OA OA54845A patent/OA04341A/en unknown
- 1973-02-28 IT IT7321023A patent/IT979608B/en active
- 1973-02-28 BG BG022855A patent/BG21236A3/en unknown
- 1973-02-28 SU SU7301888351A patent/SU584736A3/en active
- 1973-03-01 GB GB998573A patent/GB1429072A/en not_active Expired
- 1973-03-01 DD DD169147A patent/DD103125A5/xx unknown
- 1973-03-01 EG EG78/73A patent/EG10981A/en active
- 1973-03-01 AT AT181873A patent/AT324367B/en not_active IP Right Cessation
- 1973-03-01 HU HUCI1347A patent/HU165899B/hu unknown
- 1973-03-02 NL NL7303004A patent/NL7303004A/xx not_active Application Discontinuation
- 1973-03-02 JP JP48024999A patent/JPS4899344A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
BG21236A3 (en) | 1976-03-20 |
IT979608B (en) | 1974-09-30 |
HU165899B (en) | 1974-12-28 |
GB1429072A (en) | 1976-03-24 |
AU5248873A (en) | 1974-08-22 |
SU584736A3 (en) | 1977-12-15 |
DD103125A5 (en) | 1974-01-12 |
EG10981A (en) | 1976-08-31 |
IL41578A0 (en) | 1973-04-30 |
JPS4899344A (en) | 1973-12-15 |
OA04341A (en) | 1980-01-31 |
CA1016364A (en) | 1977-08-30 |
AT324367B (en) | 1975-08-25 |
NL7303004A (en) | 1973-09-04 |
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