IE44291B1 - 3,4-diphenyl-1.2.5.6-tetrahydrobenzoic acid derivatives - Google Patents

3,4-diphenyl-1.2.5.6-tetrahydrobenzoic acid derivatives

Info

Publication number: IE44291B1
Authority: IE; Ireland
Prior art keywords: formula; compound; alkyl; radical; unsubstituted
Prior art date: 1975-08-15

Application number

IE1795/76A

Other languages

English (en)

Other versions

IE44291L (en

Original Assignee

Ciba Geigy Ag

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.)

1975-08-15

Filing date

1976-08-13

Publication date

1981-10-07

1975-08-15 Priority claimed from CH1066575A external-priority patent/CH617421A5/de

1975-08-15 Priority claimed from CH1066675A external-priority patent/CH617423A5/de

1975-08-15 Priority claimed from CH1066475A external-priority patent/CH617418A5/de

1976-08-13 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1977-02-15 Publication of IE44291L publication Critical patent/IE44291L/xx

1981-10-07 Publication of IE44291B1 publication Critical patent/IE44291B1/en

Links

KRNZHMDBIHOWMH-UHFFFAOYSA-N 3,4-diphenylcyclohex-3-ene-1-carboxylic acid Chemical class C1C(C(=O)O)CCC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 KRNZHMDBIHOWMH-UHFFFAOYSA-N 0.000 title claims 2
241000196324 Embryophyta Species 0.000 claims abstract description 43
239000002253 acid Substances 0.000 claims abstract description 19
235000007320 Avena fatua Nutrition 0.000 claims abstract description 7
244000075850 Avena orientalis Species 0.000 claims abstract description 5
235000005373 Uvularia sessilifolia Nutrition 0.000 claims abstract description 5
-1 methylthio, ethylthio Chemical group 0.000 claims description 86
150000001875 compounds Chemical class 0.000 claims description 81
239000000203 mixture Substances 0.000 claims description 39
238000000034 method Methods 0.000 claims description 35
229910052736 halogen Inorganic materials 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 28
150000002367 halogens Chemical group 0.000 claims description 27
125000003545 alkoxy group Chemical group 0.000 claims description 21
229910052720 vanadium Inorganic materials 0.000 claims description 17
239000004480 active ingredient Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
230000008635 plant growth Effects 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
125000005842 heteroatom Chemical group 0.000 claims description 13
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 12
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
230000008569 process Effects 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 8
230000002401 inhibitory effect Effects 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
150000001768 cations Chemical class 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
150000004702 methyl esters Chemical class 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Chemical group 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
239000004606 Fillers/Extenders Substances 0.000 claims description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
150000001993 dienes Chemical class 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
239000004094 surface-active agent Substances 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
125000002560 nitrile group Chemical group 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
239000011701 zinc Substances 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
239000003513 alkali Substances 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
125000005210 alkyl ammonium group Chemical group 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
150000002009 diols Chemical class 0.000 claims description 2
230000008030 elimination Effects 0.000 claims description 2
238000003379 elimination reaction Methods 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
239000004615 ingredient Substances 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
229910052759 nickel Inorganic materials 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 claims 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 1
239000004305 biphenyl Substances 0.000 claims 1
229910052748 manganese Inorganic materials 0.000 claims 1
239000011572 manganese Substances 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
230000012010 growth Effects 0.000 abstract description 16
239000003795 chemical substances by application Substances 0.000 abstract description 7
150000002148 esters Chemical class 0.000 abstract description 7
150000003839 salts Chemical class 0.000 abstract description 6
241000252254 Catostomidae Species 0.000 abstract description 5
244000061176 Nicotiana tabacum Species 0.000 abstract description 5
235000002637 Nicotiana tabacum Nutrition 0.000 abstract description 4
239000013543 active substance Substances 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
230000000694 effects Effects 0.000 description 14
239000003921 oil Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 9
238000002360 preparation method Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
238000012360 testing method Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
235000013399 edible fruits Nutrition 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
241000209504 Poaceae Species 0.000 description 5
239000004495 emulsifiable concentrate Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
230000009036 growth inhibition Effects 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
150000007970 thio esters Chemical class 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
239000005995 Aluminium silicate Substances 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
238000005698 Diels-Alder reaction Methods 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
229910006069 SO3H Inorganic materials 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
239000002585 base Substances 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000011575 calcium Substances 0.000 description 3
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 3
239000000839 emulsion Substances 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
230000002363 herbicidal effect Effects 0.000 description 3
239000004009 herbicide Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
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 3
239000011777 magnesium Substances 0.000 description 3
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 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000009467 reduction Effects 0.000 description 3
230000005070 ripening Effects 0.000 description 3
230000032678 sex differentiation Effects 0.000 description 3
244000045561 useful plants Species 0.000 description 3
230000009105 vegetative growth Effects 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 2
125000006227 2-n-butoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
244000099147 Ananas comosus Species 0.000 description 2
235000007119 Ananas comosus Nutrition 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000209764 Avena fatua Species 0.000 description 2
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
244000025254 Cannabis sativa Species 0.000 description 2
XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000219112 Cucumis Species 0.000 description 2
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 2
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
241001101998 Galium Species 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
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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
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
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150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 2
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229910052791 calcium Inorganic materials 0.000 description 2
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125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
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125000002704 decyl group Chemical class [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
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239000011734 sodium Substances 0.000 description 2
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 1
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 description 1
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238000009331 sowing Methods 0.000 description 1
241000894007 species Species 0.000 description 1
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 1
239000004575 stone Substances 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
RLTPJVKHGBFGQA-UHFFFAOYSA-N thiadiazolidine Chemical compound C1CSNN1 RLTPJVKHGBFGQA-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
125000002889 tridecyl group Chemical class [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])[H] 0.000 description 1
PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
125000002948 undecyl group Chemical class [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
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/39—Unsaturated compounds containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/34—Unsaturated compounds containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/06—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal 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
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

IE1795/76A 1975-08-15 1976-08-13 3,4-diphenyl-1.2.5.6-tetrahydrobenzoic acid derivatives IE44291B1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH1066575A CH617421A5 (en)	1975-08-15	1975-08-15	Plant growth-regulating composition
CH1066675A CH617423A5 (en)	1975-08-15	1975-08-15	Plant growth regulator.
CH1066475A CH617418A5 (en)	1975-08-15	1975-08-15	Plant growth regulators.

Publications (2)

Publication Number	Publication Date
IE44291L IE44291L (en)	1977-02-15
IE44291B1 true IE44291B1 (en)	1981-10-07

Family

ID=27176486

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE1795/76A IE44291B1 (en)	1975-08-15	1976-08-13	3,4-diphenyl-1.2.5.6-tetrahydrobenzoic acid derivatives

Country Status (19)

Country	Link
JP (1)	JPS5223050A (es)
AT (1)	AT344752B (es)
AU (1)	AU507074B2 (es)
BG (1)	BG27357A3 (es)
BR (1)	BR7605355A (es)
CA (1)	CA1069913A (es)
CS (1)	CS189595B2 (es)
DD (1)	DD127675A5 (es)
DE (1)	DE2636389A1 (es)
DK (1)	DK367976A (es)
ES (1)	ES450723A1 (es)
FR (1)	FR2320700A1 (es)
GB (1)	GB1539091A (es)
GR (1)	GR60796B (es)
IE (1)	IE44291B1 (es)
IL (1)	IL50231A (es)
LU (1)	LU75586A1 (es)
NL (1)	NL7609063A (es)
TR (1)	TR19118A (es)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5557007A (en) *	1990-09-28	1996-09-17	Union Carbide Chemicals & Plastics Technology Corporation	Unsaturated polylactone acrylates and derivatives thereof

1976
- 1976-08-10 IL IL50231A patent/IL50231A/xx unknown
- 1976-08-12 LU LU75586A patent/LU75586A1/xx unknown
- 1976-08-12 DE DE19762636389 patent/DE2636389A1/de not_active Withdrawn
- 1976-08-12 TR TR19118A patent/TR19118A/xx unknown
- 1976-08-13 AU AU16834/76A patent/AU507074B2/en not_active Expired
- 1976-08-13 DK DK367976A patent/DK367976A/da unknown
- 1976-08-13 IE IE1795/76A patent/IE44291B1/en unknown
- 1976-08-13 GR GR51473A patent/GR60796B/el unknown
- 1976-08-13 BG BG033986A patent/BG27357A3/xx unknown
- 1976-08-13 DD DD194323A patent/DD127675A5/xx unknown
- 1976-08-13 AT AT603676A patent/AT344752B/de not_active IP Right Cessation
- 1976-08-13 CA CA259,036A patent/CA1069913A/en not_active Expired
- 1976-08-13 FR FR7624739A patent/FR2320700A1/fr active Granted
- 1976-08-13 CS CS765290A patent/CS189595B2/cs unknown
- 1976-08-13 NL NL7609063A patent/NL7609063A/xx not_active Application Discontinuation
- 1976-08-13 GB GB33819/76A patent/GB1539091A/en not_active Expired
- 1976-08-14 ES ES450723A patent/ES450723A1/es not_active Expired
- 1976-08-16 JP JP51097632A patent/JPS5223050A/ja active Pending
- 1976-08-16 BR BR7605355A patent/BR7605355A/pt unknown

Also Published As

Publication number	Publication date
ATA603676A (de)	1977-12-15
AT344752B (de)	1978-08-10
FR2320700A1 (fr)	1977-03-11
DE2636389A1 (de)	1977-02-24
GR60796B (en)	1978-08-30
GB1539091A (en)	1979-01-24
JPS5223050A (en)	1977-02-21
BG27357A3 (en)	1979-10-12
IE44291L (en)	1977-02-15
FR2320700B1 (es)	1979-09-28
TR19118A (tr)	1978-07-01
IL50231A (en)	1981-02-27
ES450723A1 (es)	1977-12-01
DK367976A (da)	1977-02-16
BR7605355A (pt)	1977-08-16
AU507074B2 (en)	1980-01-31
IL50231A0 (en)	1976-10-31
CS189595B2 (en)	1979-04-30
CA1069913A (en)	1980-01-15
AU1683476A (en)	1978-02-16
DD127675A5 (es)	1977-10-05
NL7609063A (nl)	1977-02-17
LU75586A1 (es)	1977-04-22

Publication	Publication Date	Title
US4518600A (en)	1985-05-21	Combating fungi with 1-phenoxy-2-pyrimidinyl alkanols
US4605747A (en)	1986-08-12	α-Benzyl-α-triazolyl pinacolone compounds
DK142360B (da)	1980-10-20	Fungicide N-acyl-anilinoeddikesyrederivater til anvendelse ved plantebeskyttelse.
JPS6254103B2 (es)	1987-11-13
JPH0655692B2 (ja)	1994-07-27	シクロヘキサンジオンカルボン酸誘導体、その製法及びそれを含有する組成物
US4570014A (en)	1986-02-11	Cycloalkanecarboxylic acid compounds
JPS6215548B2 (es)	1987-04-08
DE2548231A1 (de)	1976-05-06	1-(bis-trifluormethylphenyl)-2-oxo- pyrrolidin-4-carbonsaeurederivate, deren herstellung und verwendung als pflanzenwachstumsregulatoren und herbizide
CS195314B2 (en)	1980-01-31	Fungicide and method of preparing active components therrefor
JPS6187642A (ja)	1986-05-06	除草及び植物生長調節特性を有するシクロヘキサンジオンカルボン酸誘導体の製法及び生成物並びに該誘導体を含有する組成物
US4229207A (en)	1980-10-21	Esters of 1,2-diphenyl-cyclohex-1-ene-4-carboxylic acid
US4171214A (en)	1979-10-16	Pyrazine-2-ylmethyl-ketones and their fungicidal use
US4227918A (en)	1980-10-14	Novel halogenoethyl sulphones and their use as plant growth regulators
US4075349A (en)	1978-02-21	Microbicidal compositions
US4875922A (en)	1989-10-24	Pyrimidine derivatives
IE44291B1 (en)	1981-10-07	3,4-diphenyl-1.2.5.6-tetrahydrobenzoic acid derivatives
US4319911A (en)	1982-03-16	Triazolyl derivatives, their manufacture, and agents containing them for influencing plant growth
EP0193270B1 (en)	1991-09-11	Heterocyclic compounds
IE49101B1 (en)	1985-07-24	Substituted n-propargyl-anilines,processes for their preparation,and their use as fungicides
EP0032879A1 (de)	1981-07-29	Neue Benzthiazolyl-harnstoffderivate, deren Herstellung, sie enthaltende Mittel und deren Verwendung als Herbizide
US4895589A (en)	1990-01-23	Heterocyclic compounds
CA1080746A (en)	1980-07-01	Hydroxamic acid derivatives for regulating plant growth
US4190433A (en)	1980-02-26	Thioester of 1,2-diphenyl-cyclohex-1-ene-4-carboxylic-acid
US4340415A (en)	1982-07-20	Esters of 1,2-diphenyl-cyclohex-1-ene-4-carboxylic-acid
US4340747A (en)	1982-07-20	Esters of 1,2-diphenyl-cyclohex-1-ene-4-carboxylic-acid