IL41437A - Phenyl and benzyl alkynyl ethers their production and pest-population control compositions containing them - Google Patents

Phenyl and benzyl alkynyl ethers their production and pest-population control compositions containing them

Info

Publication number: IL41437A
Authority: IL; Israel
Prior art keywords: methyl; represents hydrogen; formula; group; chlorine
Prior art date: 1972-02-09

Application number

IL41437A

Other languages

English (en)

Other versions

IL41437A0 (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.)

1972-02-09

Filing date

1973-01-31

Publication date

1977-01-31

1972-02-09 Priority claimed from CH187072A external-priority patent/CH571305A5/de

1973-01-12 Priority claimed from CH43873A external-priority patent/CH584005A5/de

1973-01-31 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1973-03-30 Publication of IL41437A0 publication Critical patent/IL41437A0/xx

1977-01-31 Publication of IL41437A publication Critical patent/IL41437A/en

Links

-1 benzyl alkynyl ethers Chemical class 0.000 title claims description 22
238000004519 manufacturing process Methods 0.000 title claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 6
239000000203 mixture Substances 0.000 title description 13
239000001257 hydrogen Substances 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 41
150000001875 compounds Chemical class 0.000 claims description 36
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
150000002431 hydrogen Chemical class 0.000 claims description 30
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
238000000034 method Methods 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
239000000969 carrier Substances 0.000 claims description 9
241000238631 Hexapoda Species 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
239000000654 additive Substances 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
241000244206 Nematoda Species 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
150000001768 cations Chemical class 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
230000003032 phytopathogenic effect Effects 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 5
241000607479 Yersinia pestis Species 0.000 claims 1
239000013543 active substance Substances 0.000 description 38
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
239000002904 solvent Substances 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
239000003513 alkali Substances 0.000 description 16
239000000243 solution Substances 0.000 description 15
239000008187 granular material Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
229910052784 alkaline earth metal Inorganic materials 0.000 description 7
239000005995 Aluminium silicate Substances 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
235000012211 aluminium silicate Nutrition 0.000 description 6
239000002270 dispersing agent Substances 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
239000007787 solid Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
239000006072 paste Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
239000004202 carbamide Substances 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000002689 soil Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
239000000370 acceptor Substances 0.000 description 3
239000000853 adhesive Substances 0.000 description 3
230000001070 adhesive effect Effects 0.000 description 3
150000004703 alkoxides Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
235000013601 eggs Nutrition 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
150000002191 fatty alcohols Chemical class 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
238000002955 isolation Methods 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
229940031826 phenolate Drugs 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
CDFPXALLOJLBDX-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid;sodium Chemical compound [Na].C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 CDFPXALLOJLBDX-UHFFFAOYSA-N 0.000 description 2
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
241000256118 Aedes aegypti Species 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241001127120 Dysdercus fasciatus Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
241000227653 Lycopersicon Species 0.000 description 2
235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910000095 alkaline earth hydride Inorganic materials 0.000 description 2
239000002518 antifoaming agent Substances 0.000 description 2
229960000892 attapulgite Drugs 0.000 description 2
238000009835 boiling Methods 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
235000019993 champagne Nutrition 0.000 description 2
239000000470 constituent Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000428 dust Substances 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000000499 gel Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
235000012054 meals Nutrition 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
150000002790 naphthalenes Chemical class 0.000 description 2
230000001069 nematicidal effect Effects 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
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 2
229910052625 palygorskite Inorganic materials 0.000 description 2
239000012071 phase Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
235000012217 sodium aluminium silicate Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
JCRNSBKSAQHNIN-UHFFFAOYSA-N 2,4-dibutylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC(CCCC)=C21 JCRNSBKSAQHNIN-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
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
241000534456 Arenaria <Aves> Species 0.000 description 1
241000238660 Blattidae Species 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical class [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
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239000004480 active ingredient Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
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125000000129 anionic group Chemical group 0.000 description 1
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125000003118 aryl group Chemical group 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
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SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000007767 bonding agent Substances 0.000 description 1
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244000038559 crop plants Species 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
COGASMFHJIHQNA-UHFFFAOYSA-N cyclohexanone;3-methylbutan-2-one Chemical compound CC(C)C(C)=O.O=C1CCCCC1 COGASMFHJIHQNA-UHFFFAOYSA-N 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
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239000004491 dispersible concentrate Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000010410 dusting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
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238000011156 evaluation Methods 0.000 description 1
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230000002349 favourable effect Effects 0.000 description 1
239000010433 feldspar Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
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239000005337 ground glass Substances 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
230000000974 larvacidal effect Effects 0.000 description 1
239000004816 latex Substances 0.000 description 1
229920000126 latex Polymers 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000006028 limestone Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
235000012245 magnesium oxide Nutrition 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 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
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([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])[H] 0.000 description 1
230000003151 ovacidal effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
235000012219 potassium aluminium silicate Nutrition 0.000 description 1
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000000429 sodium aluminium silicate Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
238000002336 sorption--desorption measurement Methods 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
229910052717 sulfur Chemical group 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 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 description 1
239000002562 thickening agent Substances 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
238000005292 vacuum distillation Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

IL41437A 1972-02-09 1973-01-31 Phenyl and benzyl alkynyl ethers their production and pest-population control compositions containing them IL41437A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH187072A CH571305A5 (en)	1972-02-09	1972-02-09	Phenyl-or benzyl-alkynyl ethers - prepd from phenol and alkinylhalides used as insecticides, nematocides
CH43873A CH584005A5 (en)	1973-01-12	1973-01-12	Phenyl-or benzyl-alkynyl ethers - prepd from phenol and alkinylhalides used as insecticides, nematocides

Publications (2)

Publication Number	Publication Date
IL41437A0 IL41437A0 (en)	1973-03-30
IL41437A true IL41437A (en)	1977-01-31

Family

ID=25684580

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL41437A IL41437A (en)	1972-02-09	1973-01-31	Phenyl and benzyl alkynyl ethers their production and pest-population control compositions containing them

Country Status (13)

Country	Link
JP (1)	JPS4887018A (it)
AT (1)	AT324043B (it)
BE (1)	BE795129A (it)
CA (1)	CA996553A (it)
DD (1)	DD107849A5 (it)
DE (1)	DE2305698A1 (it)
FR (1)	FR2171303B1 (it)
GB (1)	GB1418824A (it)
HU (1)	HU165798B (it)
IL (1)	IL41437A (it)
IT (1)	IT987010B (it)
NL (1)	NL7301604A (it)
SU (1)	SU670198A3 (it)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4141921A (en)	1972-02-09	1979-02-27	Ciba-Geigy Corporation	Phenoxyphenyl- and phenoxybenzyl-alkynyl ethers
DE2404951A1 (de) *	1973-02-05	1974-08-08	Ciba Geigy Ag	1-phenyl-1-p-propargyloxyphenyl-2nitro-aethan-derivate, verfahren zu ihrer herstellung und ihre verwendung
EP0363308B1 (de) *	1988-09-15	1994-06-01	Ciba-Geigy Ag	Neue Aether
EP1770089A1 (en) *	2005-10-03	2007-04-04	Institut Pasteur	Pyranodibenzofuran derivatives with antifungal and antibacterial activity
KR20190104348A (ko) *	2017-01-18	2019-09-09	미쯔비시 가스 케미칼 컴파니, 인코포레이티드	화합물, 수지, 조성물 및 패턴 형성방법

0
- BE BE795129D patent/BE795129A/xx unknown
1973
- 1973-01-31 IL IL41437A patent/IL41437A/en unknown
- 1973-02-02 CA CA162,827A patent/CA996553A/en not_active Expired
- 1973-02-05 NL NL7301604A patent/NL7301604A/xx not_active Application Discontinuation
- 1973-02-06 DE DE2305698A patent/DE2305698A1/de not_active Ceased
- 1973-02-08 HU HUCI1339A patent/HU165798B/hu unknown
- 1973-02-08 JP JP48016070A patent/JPS4887018A/ja active Pending
- 1973-02-08 DD DD168756A patent/DD107849A5/xx unknown
- 1973-02-08 FR FR7304487A patent/FR2171303B1/fr not_active Expired
- 1973-02-08 GB GB630273A patent/GB1418824A/en not_active Expired
- 1973-02-08 IT IT20170/73A patent/IT987010B/it active
- 1973-02-08 AT AT112173A patent/AT324043B/de not_active IP Right Cessation
- 1973-02-08 SU SU731879889A patent/SU670198A3/ru active

Also Published As

Publication number	Publication date
DE2305698A1 (de)	1973-08-16
GB1418824A (en)	1975-12-24
AT324043B (de)	1975-08-11
IT987010B (it)	1975-02-20
HU165798B (it)	1974-11-28
DD107849A5 (it)	1974-08-20
SU670198A3 (ru)	1979-06-25
JPS4887018A (it)	1973-11-16
CA996553A (en)	1976-09-07
BE795129A (fr)	1973-08-08
NL7301604A (it)	1973-08-13
IL41437A0 (en)	1973-03-30
FR2171303B1 (it)	1979-10-12
FR2171303A1 (it)	1973-09-21

Publication	Publication Date	Title
US4097581A (en)	1978-06-27	Dioxolane derivatives
US3957885A (en)	1976-05-18	Ether derivatives of diphenylmethanes
US4048235A (en)	1977-09-13	Propenyloxy benzene compounds
US4141921A (en)	1979-02-27	Phenoxyphenyl- and phenoxybenzyl-alkynyl ethers
US3839509A (en)	1974-10-01	O-alkyl-s-alkyl-o-substituted phenylthiophosphoric acid esters
IL41437A (en)	1977-01-31	Phenyl and benzyl alkynyl ethers their production and pest-population control compositions containing them
CA1100991A (en)	1981-05-12	Esters
US3845171A (en)	1974-10-29	O-ethyl-s-n propyl-s-carbamoylalkyl dithiophosphates
US3992533A (en)	1976-11-16	O-ethyl-S-N-propyl-O-(2-chloro-4-bromophenyl)-thiophosphate
GB1570928A (en)	1980-07-09	Pesticidal cyclopropane carboxylic acid esters
US3998972A (en)	1976-12-21	Diphenyl derivatives
CA1142541A (en)	1983-03-08	Esters
US4100296A (en)	1978-07-11	Dioxolane derivatives
HU199652B (en)	1990-03-28	Insecticide and nematocide composition containing s,s'-di/terc-alkyl/-thiophosphonate derivatives as active component and process for producing the active component
CA1080743A (en)	1980-07-01	Spiroheptenyl carboxylate
IL45454A (en)	1977-06-30	3-methyl-4-(p-phenoxy(or benzyl)-phenoxy)-2-butene derivatives their preparation and pest-population contaol compositions containing them
CA1048515A (en)	1979-02-13	S'-(imidomethylene)-s-alkyl-o-alkyl-dithiophosphoric esters
US4051240A (en)	1977-09-27	O,s-dialkyl-o-(4-phenylazophenyl)-thiophosphates and pesticidal compositions thereof
US4064263A (en)	1977-12-20	4,5-Benzospiro(2,4)-heptane (and hepta-4,6-diene)-1-carboxylic acid esters and compositions containing same
US4104378A (en)	1978-08-01	Combatting pests with O,S-dialkyl-O-(4-phenylazophenyl)-thiophosphates
US3911122A (en)	1975-10-07	Insecticidal and acarididal substituted phenyl thiophosphoric acid esters
CA1048048A (en)	1979-02-06	Esters
US4048327A (en)	1977-09-13	(4-Phenoxyphenoxy)alkyl cyclopropanecarboxylates
US3998890A (en)	1976-12-21	Ether derivatives of phenylthiobenzenes
CA1092145A (en)	1980-12-23	Pesticidal metaphenoxybenzylcyclopropane carboxylate derivatives