CA1125533A - Regulateurs de la croissance vegetale contenant des ethers de triazolyle comme ingredients actifs - Google Patents

Regulateurs de la croissance vegetale contenant des ethers de triazolyle comme ingredients actifs

Info

Publication number: CA1125533A
Authority: CA; Canada
Prior art keywords: growth; denotes; plants; weight; parts
Prior art date: 1976-11-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA289,835A

Other languages

English (en)

Inventor

Friedrich Linhart

Bernd Zeeh

Klaus Gutsche

York Hartleben

Johann Jung

Bruno Wuerzer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

1976-11-06

Filing date

1977-10-28

Publication date

1982-06-15

1977-10-28 Application filed by BASF SE filed Critical BASF SE

1982-06-15 Application granted granted Critical

1982-06-15 Publication of CA1125533A publication Critical patent/CA1125533A/fr

Status Expired legal-status Critical Current

Links

-1 triazolyl ethers Chemical class 0.000 title claims abstract description 22
239000004480 active ingredient Substances 0.000 title description 18
239000005648 plant growth regulator Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 42
239000000203 mixture Substances 0.000 claims abstract description 34
239000002253 acid Substances 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
230000008635 plant growth Effects 0.000 claims abstract description 10
239000007788 liquid Substances 0.000 claims abstract description 5
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
239000007787 solid Substances 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
125000004417 unsaturated alkyl group Chemical class 0.000 claims abstract description 4
239000002689 soil Substances 0.000 claims description 14
238000000034 method Methods 0.000 claims description 4
235000006008 Brassica napus var napus Nutrition 0.000 abstract description 5
240000000385 Brassica napus var. napus Species 0.000 abstract description 5
241000219193 Brassicaceae Species 0.000 abstract description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 31
229910017604 nitric acid Inorganic materials 0.000 description 31
241000196324 Embryophyta Species 0.000 description 27
230000012010 growth Effects 0.000 description 25
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 16
125000001309 chloro group Chemical group Cl* 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
125000001246 bromo group Chemical group Br* 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
239000006185 dispersion Substances 0.000 description 8
238000002474 experimental method Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
241000209219 Hordeum Species 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000003630 growth substance Substances 0.000 description 5
241000894007 species Species 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
235000007340 Hordeum vulgare Nutrition 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
239000002585 base Substances 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 4
238000011161 development Methods 0.000 description 4
230000018109 developmental process Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
244000038559 crop plants Species 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
239000006072 paste Substances 0.000 description 3
238000009331 sowing Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
235000007238 Secale cereale Nutrition 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
235000013312 flour Nutrition 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
239000008187 granular material Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
238000005259 measurement Methods 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000012071 phase Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000002028 premature Effects 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000010998 test method Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
230000008511 vegetative development Effects 0.000 description 2
230000009105 vegetative growth Effects 0.000 description 2
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 2
239000002699 waste material Substances 0.000 description 2
KKFBZUNYJMVNFV-UHFFFAOYSA-N 1,2-bis(2-methylpropyl)naphthalene Chemical compound C1=CC=CC2=C(CC(C)C)C(CC(C)C)=CC=C21 KKFBZUNYJMVNFV-UHFFFAOYSA-N 0.000 description 1
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
244000075850 Avena orientalis Species 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
241000219198 Brassica Species 0.000 description 1
235000003351 Brassica cretica Nutrition 0.000 description 1
235000003343 Brassica rupestris Nutrition 0.000 description 1
241000221079 Euphorbia <genus> Species 0.000 description 1
241000209510 Liliopsida Species 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
CQGRLHBOVUGVEA-UHFFFAOYSA-N OOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOO CQGRLHBOVUGVEA-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
235000004443 Ricinus communis Nutrition 0.000 description 1
241000209056 Secale Species 0.000 description 1
244000082988 Secale cereale Species 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
241000209140 Triticum Species 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
239000013066 combination product Substances 0.000 description 1
229940127555 combination product Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
230000006378 damage Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
239000003864 humus Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
CCJHDZZUWZIVJF-UHFFFAOYSA-N iodo nitrate Chemical compound [O-][N+](=O)OI CCJHDZZUWZIVJF-UHFFFAOYSA-N 0.000 description 1
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 1
229920005610 lignin Polymers 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000003921 oil Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003415 peat Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
230000029553 photosynthesis Effects 0.000 description 1
238000010672 photosynthesis Methods 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
101150003625 ribD gene Proteins 0.000 description 1
239000011435 rock Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
230000000007 visual effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CA289,835A 1976-11-06 1977-10-28 Regulateurs de la croissance vegetale contenant des ethers de triazolyle comme ingredients actifs Expired CA1125533A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP2650831.6		1976-11-06
DE19762650831 DE2650831A1 (de)	1976-11-06	1976-11-06	Mittel zur beeinflussung des pflanzenwachstums

Publications (1)

Publication Number	Publication Date
CA1125533A true CA1125533A (fr)	1982-06-15

Family

ID=5992573

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA289,835A Expired CA1125533A (fr)	1976-11-06	1977-10-28	Regulateurs de la croissance vegetale contenant des ethers de triazolyle comme ingredients actifs

Country Status (13)

Country	Link
JP (1)	JPS5359031A (fr)
BE (1)	BE860493A (fr)
CA (1)	CA1125533A (fr)
CS (1)	CS194820B2 (fr)
DD (1)	DD131834A5 (fr)
DE (1)	DE2650831A1 (fr)
DK (1)	DK491077A (fr)
FR (1)	FR2369796A1 (fr)
GB (1)	GB1593687A (fr)
NL (1)	NL7711953A (fr)
PL (1)	PL103464B1 (fr)
SE (1)	SE7712332L (fr)
SU (1)	SU685128A3 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL53432A0 (en) *	1976-11-24	1978-01-31	Bayer Ag	Method and compositions containing certain triazole derivatives for regulating plant growth
DE2845254A1 (de)	1978-10-18	1980-05-08	Basf Ag	Gamma -azolylverbindungen
EP0015639A3 (fr) *	1979-02-09	1980-10-01	Imperial Chemical Industries Plc	Enantiomères de composés triazoliques, procédé pour leur préparation, leur utilisation comme fongicides pour plantes et comme agents régulateurs de croissance, et compositions les contenant
DE2921168A1 (de) *	1979-05-25	1980-12-11	Basf Ag	Triazolylderivate und verfahren zu ihrer herstellung sowie diese enthaltende mittel zur beeinflussung des pflanzenwachstums
DE2925687A1 (de) *	1979-06-26	1981-01-22	Basf Ag	Triazolylglykolether enthaltende mittel zur regulierung des pflanzenwachstums
DE3047726A1 (de)	1980-12-18	1982-07-15	Basf Ag, 6700 Ludwigshafen	Wachstumsregulierende (alpha)-azolylglykole, ihre herstellung und verwendung
DE3220183A1 (de) *	1982-05-28	1983-12-01	Basf Ag, 6700 Ludwigshafen	Triazolyl-ketonoxime und -dioxime, verfahren zu ihrer herstellung und ihre verwendung als pflanzenwachstumsregulatoren
DE3233145A1 (de) *	1982-09-07	1984-03-08	Basf Ag, 6700 Ludwigshafen	Neopentyl-phenethyltriazole, verfahren zu ihrer herstellung und diese enthaltende fungizide
EP0126430B1 (fr) *	1983-05-19	1991-08-28	Ciba-Geigy Ag	Procédé pour la préparation de dérivés de 1-triazolyléthyléthers, composés microbicides contenant des dérivés nouveaux de 1-triazolyl-phenoxyphényléthyléther comme ingrédients actifs et leur application
GB2156807A (en) *	1984-04-05	1985-10-16	Ici Plc	Azolyl propanols

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ181916A (en) *	1975-09-10	1979-01-11	Ici Ltd	1-substituted-1,2,4-triazoles and fungicidal compositions
DE2547953A1 (de) *	1975-10-27	1977-04-28	Bayer Ag	(1-phenyl-2-triazolyl-aethyl)-aether- derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE2556319A1 (de) *	1975-12-13	1977-06-23	Basf Ag	Substituierte triazol-aether
IE45765B1 (en) *	1976-08-19	1982-11-17	Ici Ltd	Triazoles and imidazoles useful as plant fungicides and growth regulating agents

1976
- 1976-11-06 DE DE19762650831 patent/DE2650831A1/de not_active Withdrawn
1977
- 1977-10-28 CA CA289,835A patent/CA1125533A/fr not_active Expired
- 1977-10-31 NL NL7711953A patent/NL7711953A/xx not_active Application Discontinuation
- 1977-11-01 SE SE7712332A patent/SE7712332L/xx unknown
- 1977-11-02 JP JP13090877A patent/JPS5359031A/ja active Pending
- 1977-11-03 CS CS777199A patent/CS194820B2/cs unknown
- 1977-11-04 PL PL1977201906A patent/PL103464B1/pl unknown
- 1977-11-04 BE BE182353A patent/BE860493A/fr unknown
- 1977-11-04 GB GB45918/77A patent/GB1593687A/en not_active Expired
- 1977-11-04 DD DD7700201884A patent/DD131834A5/xx unknown
- 1977-11-04 SU SU772543297A patent/SU685128A3/ru active
- 1977-11-04 DK DK491077A patent/DK491077A/da unknown
- 1977-11-04 FR FR7733180A patent/FR2369796A1/fr active Granted

Also Published As

Publication number	Publication date
SU685128A3 (ru)	1979-09-05
PL103464B1 (pl)	1979-06-30
NL7711953A (nl)	1978-05-09
DE2650831A1 (de)	1978-05-11
DK491077A (da)	1978-05-07
FR2369796B1 (fr)	1982-02-19
GB1593687A (en)	1981-07-22
BE860493A (fr)	1978-05-05
DD131834A5 (de)	1978-07-26
FR2369796A1 (fr)	1978-06-02
SE7712332L (sv)	1978-05-07
CS194820B2 (en)	1979-12-31
PL201906A1 (pl)	1978-06-19
JPS5359031A (en)	1978-05-27

Legal Events

Date	Code	Title	Description
1999-06-15	MKEX	Expiry

Publication	Publication Date	Title
US4070176A (en)	1978-01-24	Method for controlling the growth of plants
CA1111429A (fr)	1981-10-27	Alcools gamma-azolyliques et regulateurs de croissance pour les plantes
US5240951A (en)	1993-08-31	Isothiazolecarboxylic acid derivatives, rice blast control agents containing the same as active ingredients, and rice blast control method applying the control agents
PL88780B1 (fr)	1976-09-30
CA1100988A (fr)	1981-05-12	Traduction non-disponible
US4232033A (en)	1980-11-04	Combating fungi with diastereomeric form A of 1-phenoxy-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ols
CA1125533A (fr)	1982-06-15	Regulateurs de la croissance vegetale contenant des ethers de triazolyle comme ingredients actifs
US4889551A (en)	1989-12-26	Isoxazoline derivatives and plant growth regulators
EP0010298B1 (fr)	1981-12-09	Dérivés 1,2,4-triazol-1-yliques, leur préparation, fongicides, procédé de préparation de fongicides et méthode de lutte contre les champignons
GB1601877A (en)	1981-11-04	Azolyl-acetophenone-oxime ethers and their use as fungicides
EP0075377A2 (fr)	1983-03-30	Composés de diphényléthers, leur utilisation comme herbicide et compositions herbicides les contenant
KR890001547B1 (ko)	1989-05-08	치환된 아졸린-페녹시 유도체의 제조방법
CA1144167A (fr)	1983-04-05	Sels de naphtyloxy- et naphtylthio- alkylammonium substitues; preparation, et utilisation comme agents regulateurs de la croissance des plantes
JPS58967A (ja)	1983-01-06	菌・カビ防除組成物
CA1144922A (fr)	1983-04-19	Sels d'alkylammonium substitues, leur preparation et leur utilisation comme regulateurs de la croissance des plantes
EP0001721A2 (fr)	1979-05-02	N-Cyano et N-alkynyle-2(phénoxy substitué)-butyramides et leur utilisation comme agents antioidium
PL100897B1 (pl)	1978-11-30	Srodek grzybobojczy
HU181646B (en)	1983-10-28	Herbicide composition containing acetanilide as active substance and dichloro-acetamide as antidote
EP0010270B1 (fr)	1981-11-04	Dérivés de l'acide alpha-azolyl-alpha-phénylacétique, leur fabrication, fongicides les contenant, méthode de lutte contre les champignons et procédé pour la préparation de fongicides
US4319911A (en)	1982-03-16	Triazolyl derivatives, their manufacture, and agents containing them for influencing plant growth
EP0102163B1 (fr)	1987-04-01	Dérivés de triazole et compositions les contenant
US3985799A (en)	1976-10-12	2-Fluoro-6-trifluoromethylbenzoic acid
KR900005678B1 (ko)	1990-08-06	살균활성을 갖는 알파-(1-트리아졸일-)-케토-유도체의 제조방법
CA2042660A1 (fr)	1991-11-18	Derives de la sulfonyluree comme herbicides
JPS58167575A (ja)	1983-10-03	フエノキシプロピルトリアゾリル−ケトン及びカルビノ−ル、その製法並びに利用