IE47205B1 - Substituted carbamates, preparation and compositions thereof and use thereof as insecticides - Google Patents

Substituted carbamates, preparation and compositions thereof and use thereof as insecticides

Info

Publication number: IE47205B1
Authority: IE; Ireland
Prior art keywords: compound; methyl; chg; insecticidal; bis
Prior art date: 1977-07-01

Application number

IE1324/78A

Other languages

English (en)

Other versions

IE781324L (en

Original Assignee

Du Pont

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.)

1977-07-01

Filing date

1978-06-30

Publication date

1984-01-11

1978-03-10 Priority claimed from US05/885,251 external-priority patent/US4160034A/en

1978-06-30 Application filed by Du Pont filed Critical Du Pont

1979-01-01 Publication of IE781324L publication Critical patent/IE781324L/xx

1984-01-11 Publication of IE47205B1 publication Critical patent/IE47205B1/en

Links

239000000203 mixture Substances 0.000 title claims description 23
239000002917 insecticide Substances 0.000 title abstract description 9
238000002360 preparation method Methods 0.000 title abstract description 5
150000004657 carbamic acid derivatives Chemical class 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 50
241000238631 Hexapoda Species 0.000 claims abstract description 13
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 claims abstract description 13
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims abstract description 4
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims abstract 2
230000000749 insecticidal effect Effects 0.000 claims description 15
238000000034 method Methods 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
239000004094 surface-active agent Substances 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
206010061217 Infestation Diseases 0.000 claims description 2
241000607479 Yersinia pestis Species 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
239000003701 inert diluent Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
-1 methylimino Chemical group 0.000 abstract description 14
125000000446 sulfanediyl group Chemical group *S* 0.000 abstract description 10
241000254173 Coleoptera Species 0.000 abstract description 2
241000255925 Diptera Species 0.000 abstract description 2
241000255777 Lepidoptera Species 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 13
239000004615 ingredient Substances 0.000 description 13
238000009472 formulation Methods 0.000 description 11
239000000243 solution Substances 0.000 description 10
239000003085 diluting agent Substances 0.000 description 8
239000008187 granular material Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
241001521235 Spodoptera eridania Species 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
229940073584 methylene chloride Drugs 0.000 description 6
239000000047 product Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
241000196324 Embryophyta Species 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
239000008188 pellet Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
239000005916 Methomyl Substances 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000000463 material Substances 0.000 description 4
UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 4
239000002245 particle Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000004563 wettable powder Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RAPBNVDSDCTNRC-UHFFFAOYSA-N Chlorobenzilate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OCC)C1=CC=C(Cl)C=C1 RAPBNVDSDCTNRC-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
229960000892 attapulgite Drugs 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
229910052625 palygorskite Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 3
239000007921 spray Substances 0.000 description 3
YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 2
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000462639 Epilachna varivestis Species 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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
231100000674 Phytotoxicity Toxicity 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
241000256247 Spodoptera exigua Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
230000000895 acaricidal effect Effects 0.000 description 2
239000000642 acaricide Substances 0.000 description 2
239000011149 active material Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 2
RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 2
DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
PFIADAMVCJPXSF-UHFFFAOYSA-N chloroneb Chemical compound COC1=CC(Cl)=C(OC)C=C1Cl PFIADAMVCJPXSF-UHFFFAOYSA-N 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 description 2
230000006378 damage Effects 0.000 description 2
UOAMTSKGCBMZTC-UHFFFAOYSA-N dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 description 2
239000000428 dust Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
239000006260 foam Substances 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
238000000227 grinding Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
208000014674 injury Diseases 0.000 description 2
YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 2
UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 2
230000002906 microbiologic effect Effects 0.000 description 2
239000005645 nematicide Substances 0.000 description 2
239000012053 oil suspension Substances 0.000 description 2
KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 2
238000004806 packaging method and process Methods 0.000 description 2
FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
238000005507 spraying Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
229960002447 thiram Drugs 0.000 description 2
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
150000003738 xylenes Chemical class 0.000 description 2
SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 1
LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
XLOPRKKSAJMMEW-SFYZADRCSA-M (R,R)-chrysanthemate Chemical compound CC(C)=C[C@@H]1[C@@H](C([O-])=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-M 0.000 description 1
AQKJHZKWTDKLJH-UHFFFAOYSA-N (propan-2-ylamino)phosphonic acid Chemical compound CC(C)NP(O)(O)=O AQKJHZKWTDKLJH-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WEEMDRWIKYCTQM-UHFFFAOYSA-N 2,6-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=CC(OC)=C1C(N)=S WEEMDRWIKYCTQM-UHFFFAOYSA-N 0.000 description 1
LWGRPXZKPVYNBS-UHFFFAOYSA-N 2-chlorosulfanylethyl thiohypochlorite Chemical compound ClSCCSCl LWGRPXZKPVYNBS-UHFFFAOYSA-N 0.000 description 1
CYEJMVLDXAUOPN-UHFFFAOYSA-N 2-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC=CC=C1O CYEJMVLDXAUOPN-UHFFFAOYSA-N 0.000 description 1
YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000005745 Captan Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 1
239000005766 Dodine Substances 0.000 description 1
239000005958 Fenamiphos (aka phenamiphos) Substances 0.000 description 1
239000005789 Folpet Substances 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
240000002024 Gossypium herbaceum Species 0.000 description 1
235000004341 Gossypium herbaceum Nutrition 0.000 description 1
241001147381 Helicoverpa armigera Species 0.000 description 1
241000255967 Helicoverpa zea Species 0.000 description 1
241000256257 Heliothis Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000005949 Malathion Substances 0.000 description 1
241000257159 Musca domestica Species 0.000 description 1
LVJGHULVGIFLAE-UHFFFAOYSA-N Octachlorocamphene Chemical compound ClC1(Cl)C(Cl)(Cl)C2(Cl)C(C)(C)C(=C)C1(Cl)C2(Cl)Cl LVJGHULVGIFLAE-UHFFFAOYSA-N 0.000 description 1
239000005950 Oxamyl Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
UVWXMTREAOTOLD-UHFFFAOYSA-N S(=O)(=O)(Cl)Cl.C(CSCl)SCl Chemical compound S(=O)(=O)(Cl)Cl.C(CSCl)SCl UVWXMTREAOTOLD-UHFFFAOYSA-N 0.000 description 1
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
239000004965 Silica aerogel Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
241001363650 Thysanoplusia orichalcea Species 0.000 description 1
CRPUJAZIXJMDBK-UHFFFAOYSA-N Toxaphene Natural products C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 1
239000005848 Tribasic copper sulfate Substances 0.000 description 1
241000625014 Vir Species 0.000 description 1
RKZXQQPEDGMHBJ-LIGJGSPWSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentakis[[(z)-octadec-9-enoyl]oxy]hexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC RKZXQQPEDGMHBJ-LIGJGSPWSA-N 0.000 description 1
YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-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
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229940117949 captan Drugs 0.000 description 1
229960005286 carbaryl Drugs 0.000 description 1
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000003889 chemical engineering Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
STUSTWKEFDQFFZ-KPKJPENVSA-N chlordimeform Chemical compound CN(C)\C=N\C1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-KPKJPENVSA-N 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000003599 detergent Substances 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
NAKDJXIEBCHXIZ-UHFFFAOYSA-N dihydroxy-phenyl-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(=S)C1=CC=CC=C1 NAKDJXIEBCHXIZ-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 1
ZCJPOPBZHLUFHF-UHFFFAOYSA-N fenamiphos Chemical compound CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1 ZCJPOPBZHLUFHF-UHFFFAOYSA-N 0.000 description 1
NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229960000453 malathion Drugs 0.000 description 1
231100001225 mammalian toxicity Toxicity 0.000 description 1
229920000940 maneb Polymers 0.000 description 1
NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
YYKXMTXALJYVCN-UHFFFAOYSA-N methyl ethanimidothioate Chemical compound CSC(C)=N YYKXMTXALJYVCN-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
GYGAZRPDUOHMAF-KHPPLWFESA-N oleyl acetate Chemical class CCCCCCCC\C=C/CCCCCCCCOC(C)=O GYGAZRPDUOHMAF-KHPPLWFESA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
235000020030 perry Nutrition 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
229960003536 phenothrin Drugs 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000008654 plant damage Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
DQIGGFPVKGZBQQ-UHFFFAOYSA-N s-carbamoyl carbamothioate Chemical class NC(=O)SC(N)=O DQIGGFPVKGZBQQ-UHFFFAOYSA-N 0.000 description 1
239000004576 sand Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
241000894007 species Species 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229960002385 streptomycin sulfate Drugs 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/58—Derivatives of thiocarboxylic acids, the doubly-bound oxygen atoms being replaced by nitrogen atoms, e.g. imino-thio ethers
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Landscapes

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

IE1324/78A 1977-07-01 1978-06-30 Substituted carbamates, preparation and compositions thereof and use thereof as insecticides IE47205B1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US81231677A	1977-07-01	1977-07-01
US05/885,251 US4160034A (en)	1977-07-01	1978-03-10	Substituted carbamates

Publications (2)

Publication Number	Publication Date
IE781324L IE781324L (en)	1979-01-01
IE47205B1 true IE47205B1 (en)	1984-01-11

Family

ID=27123592

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE1324/78A IE47205B1 (en)	1977-07-01	1978-06-30	Substituted carbamates, preparation and compositions thereof and use thereof as insecticides

Country Status (22)

Country	Link
EP (1)	EP0000283B1 (cs)
JP (1)	JPS5444614A (cs)
AR (1)	AR220138A1 (cs)
AU (1)	AU515983B2 (cs)
BR (1)	BR7804185A (cs)
CA (1)	CA1107292A (cs)
CS (1)	CS199213B2 (cs)
DE (1)	DE2861154D1 (cs)
DK (1)	DK254378A (cs)
EG (1)	EG13741A (cs)
ES (1)	ES471280A1 (cs)
GB (1)	GB2001628B (cs)
GR (1)	GR64548B (cs)
IE (1)	IE47205B1 (cs)
IL (1)	IL55050A (cs)
IT (1)	IT1158872B (cs)
MX (1)	MX5138E (cs)
OA (1)	OA05999A (cs)
PH (1)	PH13803A (cs)
PL (1)	PL114208B1 (cs)
TR (1)	TR19962A (cs)
YU (1)	YU154178A (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR8104086A (pt) *	1980-07-03	1982-03-16	Du Pont	Processo para o controle de carrapatos

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3856972A (en) *	1970-09-24	1974-12-24	M Hirano	Carbamate pesticides

1978
- 1978-06-08 DK DK254378A patent/DK254378A/da not_active Application Discontinuation
- 1978-06-23 PH PH21318A patent/PH13803A/en unknown
- 1978-06-28 TR TR19962A patent/TR19962A/xx unknown
- 1978-06-28 EG EG406/78A patent/EG13741A/xx active
- 1978-06-28 EP EP78300097A patent/EP0000283B1/en not_active Expired
- 1978-06-28 MX MX787191U patent/MX5138E/es unknown
- 1978-06-28 AU AU37526/78A patent/AU515983B2/en not_active Expired
- 1978-06-28 GB GB787828116A patent/GB2001628B/en not_active Expired
- 1978-06-28 DE DE7878300097T patent/DE2861154D1/de not_active Expired
- 1978-06-29 CS CS784303A patent/CS199213B2/cs unknown
- 1978-06-29 JP JP7812978A patent/JPS5444614A/ja active Pending
- 1978-06-29 ES ES471280A patent/ES471280A1/es not_active Expired
- 1978-06-29 YU YU01541/78A patent/YU154178A/xx unknown
- 1978-06-30 OA OA56548A patent/OA05999A/xx unknown
- 1978-06-30 AR AR272767A patent/AR220138A1/es active
- 1978-06-30 IL IL55050A patent/IL55050A/xx unknown
- 1978-06-30 PL PL1978208044A patent/PL114208B1/pl unknown
- 1978-06-30 IT IT25229/78A patent/IT1158872B/it active
- 1978-06-30 CA CA306,631A patent/CA1107292A/en not_active Expired
- 1978-06-30 GR GR56643A patent/GR64548B/el unknown
- 1978-06-30 BR BR7804185A patent/BR7804185A/pt unknown
- 1978-06-30 IE IE1324/78A patent/IE47205B1/en unknown

Also Published As

Publication number	Publication date
GB2001628A (en)	1979-02-07
CA1107292A (en)	1981-08-18
IT1158872B (it)	1987-02-25
PL114208B1 (en)	1981-01-31
DE2861154D1 (en)	1981-12-24
AU3752678A (en)	1980-01-03
TR19962A (tr)	1980-05-16
AU515983B2 (en)	1981-05-14
PH13803A (en)	1980-10-01
OA05999A (fr)	1981-06-30
ES471280A1 (es)	1979-10-01
BR7804185A (pt)	1979-03-20
PL208044A1 (cs)	1979-12-03
IE781324L (en)	1979-01-01
IT7825229A0 (it)	1978-06-30
IL55050A (en)	1983-03-31
JPS5444614A (en)	1979-04-09
GB2001628B (en)	1982-01-13
MX5138E (es)	1983-03-28
IL55050A0 (en)	1978-08-31
YU154178A (en)	1983-01-21
GR64548B (en)	1980-04-12
EP0000283A1 (en)	1979-01-10
CS199213B2 (en)	1980-07-31
EG13741A (en)	1982-09-30
EP0000283B1 (en)	1981-10-14
AR220138A1 (es)	1980-10-15
DK254378A (da)	1979-01-02

Publication	Publication Date	Title
US4830661A (en)	1989-05-16	Substituted tetrazolinones and herbicidal compositions thereof
US5019152A (en)	1991-05-28	Substituted tetrazolinones and their use as herbicides
US5003075A (en)	1991-03-26	Preparation of substituted tetrazolinones
CA1137496A (en)	1982-12-14	1-n,n-dimethylcarbamoyl-3(5)-alkyl-5(3)- alkylthioalkylthio-1,2,4-triazoles, a process for their manufacture, compositions which contain them and their use in pest control
US4225615A (en)	1980-09-30	Insecticidal and nematicidal carbamates
US4160034A (en)	1979-07-03	Substituted carbamates
US4626273A (en)	1986-12-02	Herbicidal novel 2-alkoxyaminosulfonyl-benzene-sulfonylureas
IE47205B1 (en)	1984-01-11	Substituted carbamates, preparation and compositions thereof and use thereof as insecticides
US4619688A (en)	1986-10-28	Herbicidal sulfonylguanidine derivatives
US4268520A (en)	1981-05-19	Insecticidal and nematicidal carbamates
US5120346A (en)	1992-06-09	Substituted tetrazolinones for plant growth inhibition
US4291054A (en)	1981-09-22	Insecticidal carbamoyl sulfides
US4150122A (en)	1979-04-17	Substituted carbamates
US4210668A (en)	1980-07-01	Insecticidal carbamates
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EP0015745B1 (en)	1983-06-22	Pesticidal carbamoyl sulfides, and preparation and use thereof
US5856478A (en)	1999-01-05	Anellated (oxa)hydantoins and their use as herbicides
US4335140A (en)	1982-06-15	Insecticidal trifluoroethanimidothioate disulfides
US5922647A (en)	1999-07-13	Anellated (oxa)hydantoins and their use as herbicides
US4146618A (en)	1979-03-27	Substituted carbamates
EP0007156B1 (en)	1982-07-21	Carbamates, compositions containing them, their insecticidal and nematocidal use, and a method for their preparation
US4330674A (en)	1982-05-18	Carbamoyl sulfide fluorides
US4254141A (en)	1981-03-03	Insecticidal carbamoyl sulfides
US4316911A (en)	1982-02-23	Ureidosulfenyl carbamate nematicides
US3910877A (en)	1975-10-07	Bis(cyanophenyl)-3-formazancarbonitrile compounds