CA1139770A - Sulfure de carbamoyle a proprietes insecticides - Google Patents

Sulfure de carbamoyle a proprietes insecticides

Info

Publication number: CA1139770A
Authority: CA; Canada
Prior art keywords: alkyl; compound; methylimino; phenyl; dimethyl
Prior art date: 1979-03-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000359521A

Other languages

English (en)

Inventor

Jiin-Duey Cheng

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

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

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.)

1979-03-06

Filing date

1980-09-04

Publication date

1983-01-18

1980-04-24 Priority claimed from US06/139,836 external-priority patent/US4254141A/en

1980-09-04 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1983-01-18 Application granted granted Critical

1983-01-18 Publication of CA1139770A publication Critical patent/CA1139770A/fr

Status Expired legal-status Critical Current

Links

230000000749 insecticidal effect Effects 0.000 title description 5
DQIGGFPVKGZBQQ-UHFFFAOYSA-N s-carbamoyl carbamothioate Chemical class NC(=O)SC(N)=O DQIGGFPVKGZBQQ-UHFFFAOYSA-N 0.000 title description 2
241000244206 Nematoda Species 0.000 claims abstract description 17
241000238631 Hexapoda Species 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims description 59
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
241000238876 Acari Species 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 12
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 abstract description 32
-1 dimethyl N Chemical class 0.000 abstract description 30
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract description 26
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 abstract description 22
150000003568 thioethers Chemical class 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 106
239000000203 mixture Substances 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
125000000446 sulfanediyl group Chemical group *S* 0.000 description 20
239000000243 solution Substances 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
239000004615 ingredient Substances 0.000 description 10
PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical compound NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 0.000 description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
238000009472 formulation Methods 0.000 description 8
239000008187 granular material Substances 0.000 description 7
239000003085 diluting agent Substances 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
238000001914 filtration Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000008188 pellet Substances 0.000 description 6
241000196324 Embryophyta Species 0.000 description 5
125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 description 5
239000002917 insecticide Substances 0.000 description 5
150000002923 oximes Chemical class 0.000 description 5
239000002689 soil Substances 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 4
241000238421 Arthropoda Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000005916 Methomyl Substances 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000000428 dust Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000000463 material Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal 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
238000002156 mixing Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000004563 wettable powder Substances 0.000 description 4
JGUQDUKBUKFFRO-GGWOSOGESA-N (NE)-N-[(3E)-3-hydroxyiminobutan-2-ylidene]hydroxylamine Chemical compound O\N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-GGWOSOGESA-N 0.000 description 3
241000722666 Camponotus Species 0.000 description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
241000256244 Heliothis virescens Species 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
241001481696 Rhipicephalus sanguineus Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241001521235 Spodoptera eridania Species 0.000 description 3
241000607479 Yersinia pestis Species 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000417 fungicide Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
230000000361 pesticidal effect Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
241000894007 species Species 0.000 description 3
239000007921 spray Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 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
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
241001367803 Chrysodeixis includens 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
206010061217 Infestation Diseases 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
241001465754 Metazoa Species 0.000 description 2
241000257159 Musca domestica Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
230000000895 acaricidal effect Effects 0.000 description 2
239000000642 acaricide Substances 0.000 description 2
238000005054 agglomeration Methods 0.000 description 2
230000002776 aggregation Effects 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
229960000892 attapulgite Drugs 0.000 description 2
239000003899 bactericide agent Substances 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
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
BIWJNBZANLAXMG-YQELWRJZSA-N chloordaan Chemical compound ClC1=C(Cl)[C@@]2(Cl)C3CC(Cl)C(Cl)C3[C@]1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-YQELWRJZSA-N 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 2
OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 2
238000007865 diluting Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
239000007788 liquid Substances 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
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
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 2
229920000609 methyl cellulose Polymers 0.000 description 2
UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
DCAMNZNIQSVBSR-UHFFFAOYSA-N n-[carbonofluoridoyl(methyl)amino]sulfanyl-n-methylcarbamoyl fluoride Chemical compound FC(=O)N(C)SN(C)C(F)=O DCAMNZNIQSVBSR-UHFFFAOYSA-N 0.000 description 2
239000005645 nematicide Substances 0.000 description 2
238000004806 packaging method and process Methods 0.000 description 2
229910052625 palygorskite Inorganic materials 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
229910052903 pyrophyllite Inorganic materials 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 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
229960002447 thiram Drugs 0.000 description 2
ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-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
FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
KFTHGQZJWAXFGG-ZUVMSYQZSA-N (NE)-N-[(1E)-1-hydroxyiminopropan-2-ylidene]hydroxylamine Chemical compound C\C(\C=N\O)=N/O KFTHGQZJWAXFGG-ZUVMSYQZSA-N 0.000 description 1
LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical compound O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 description 1
LNTHQBNSXNQPPZ-UXBLZVDNSA-N (ne)-n-[[4-(methoxymethyl)cyclohexa-1,4-dien-1-yl]methylidene]hydroxylamine Chemical compound COCC1=CCC(\C=N\O)=CC1 LNTHQBNSXNQPPZ-UXBLZVDNSA-N 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
DBGSRZSKGVSXRK-UHFFFAOYSA-N 1-[2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]acetyl]-3,6-dihydro-2H-pyridine-4-carboxylic acid Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CCC(=CC1)C(=O)O DBGSRZSKGVSXRK-UHFFFAOYSA-N 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 description 1
UPTVJAJPBGIRLZ-UHFFFAOYSA-N 2-(trichloromethylsulfanyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 UPTVJAJPBGIRLZ-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
CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 description 1
HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
FZLSDZZNPXXBBB-KDURUIRLSA-N 5-chloro-N-[3-cyclopropyl-5-[[(3R,5S)-3,5-dimethylpiperazin-1-yl]methyl]phenyl]-4-(6-methyl-1H-indol-3-yl)pyrimidin-2-amine Chemical compound C[C@H]1CN(Cc2cc(Nc3ncc(Cl)c(n3)-c3c[nH]c4cc(C)ccc34)cc(c2)C2CC2)C[C@@H](C)N1 FZLSDZZNPXXBBB-KDURUIRLSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
OENCGGPNQKWBEF-UHFFFAOYSA-N COC=1[ClH]C=CC=1 Chemical compound COC=1[ClH]C=CC=1 OENCGGPNQKWBEF-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241001489688 Camponotus herculeanus Species 0.000 description 1
239000005745 Captan Substances 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
240000008067 Cucumis sativus Species 0.000 description 1
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
241000255925 Diptera Species 0.000 description 1
239000005766 Dodine Substances 0.000 description 1
101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
241000462639 Epilachna varivestis Species 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
JHJOOSLFWRRSGU-UHFFFAOYSA-N Fenchlorphos Chemical compound COP(=S)(OC)OC1=CC(Cl)=C(Cl)C=C1Cl JHJOOSLFWRRSGU-UHFFFAOYSA-N 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
241000255967 Helicoverpa zea Species 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
241000256602 Isoptera Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000255682 Malacosoma americanum Species 0.000 description 1
241000255685 Malacosoma neustria Species 0.000 description 1
241000243785 Meloidogyne javanica Species 0.000 description 1
241001024304 Mino Species 0.000 description 1
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AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
XDOTVMNBCQVZKG-OXAWKVHCSA-N methyl (1z)-n-[methyl-[methyl-[(z)-1-methylsulfanylethylideneamino]oxycarbonylamino]sulfanylcarbamoyl]oxyethanimidothioate Chemical compound CS\C(C)=N/OC(=O)N(C)SN(C)C(=O)O\N=C(\C)SC XDOTVMNBCQVZKG-OXAWKVHCSA-N 0.000 description 1
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FOAMDPDTDULKHA-UHFFFAOYSA-N methyl-[methyl-[(2-methyl-2-methylsulfanylpropylidene)amino]oxycarbonylamino]sulfanylcarbamic acid Chemical compound CSC(C)(C)C=NOC(=O)N(C)SN(C)C(O)=O FOAMDPDTDULKHA-UHFFFAOYSA-N 0.000 description 1
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KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 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
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HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000011541 reaction mixture 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
238000005507 spraying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
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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
NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-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
238000012546 transfer Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000359521A 1979-03-06 1980-09-04 Sulfure de carbamoyle a proprietes insecticides Expired CA1139770A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US1829379A	1979-03-06	1979-03-06
US018,293		1979-03-06
US06/139,836 US4254141A (en)	1980-04-24	1980-04-24	Insecticidal carbamoyl sulfides
US139,836		1980-04-24

Publications (1)

Publication Number	Publication Date
CA1139770A true CA1139770A (fr)	1983-01-18

Family

ID=26690942

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000359521A Expired CA1139770A (fr)	1979-03-06	1980-09-04	Sulfure de carbamoyle a proprietes insecticides

Country Status (1)

Country	Link
CA (1)	CA1139770A (fr)

1980
- 1980-09-04 CA CA000359521A patent/CA1139770A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-01-18	MKEX	Expiry

Publication	Publication Date	Title
US4072751A (en)	1978-02-07	Pesticidal N-substituted bis-carbamoyl sulfide compounds
CA1139770A (fr)	1983-01-18	Sulfure de carbamoyle a proprietes insecticides
CA1069127A (fr)	1980-01-01	Composes de type fluorure de carbamate-sulfenyle-carbamoyle
KR890000369B1 (ko)	1989-03-14	S-메틸 n-[{n-메틸-n-(n, n-이치환된 아미노설페닐)카바모일}옥시]티오아세트아미데이트 유도체의 제조방법
GB2121687A (en)	1984-01-04	Insecticidal compositions having high concentration of active ingredients
US4479002A (en)	1984-10-23	Carbamate-carbamoyl fluoride compounds
US4210668A (en)	1980-07-01	Insecticidal carbamates
CA1139769A (fr)	1983-01-18	Sulfure de carbamoyles insecticides
US4254141A (en)	1981-03-03	Insecticidal carbamoyl sulfides
US3288673A (en)	1966-11-29	Control of pests with benzothienyl carbamates
US4335140A (en)	1982-06-15	Insecticidal trifluoroethanimidothioate disulfides
US4330674A (en)	1982-05-18	Carbamoyl sulfide fluorides
US3476490A (en)	1969-11-04	Methods of using particular carbamic acid esters for insecticidal and acaricidal purposes
US4150122A (en)	1979-04-17	Substituted carbamates
US4268520A (en)	1981-05-19	Insecticidal and nematicidal carbamates
US4291054A (en)	1981-09-22	Insecticidal carbamoyl sulfides
EP0005338A1 (fr)	1979-11-14	Carbamates possédant des propriétés insecticides et nématocides; leur préparation et leur usage
CA1139771A (fr)	1983-01-18	Derives du (n-methylcarbamoyl-phenoxy)-n',n'',n''- trialkyl-uree)-n-n'-sulfure, procede de production, compose les contenant a titre d'ingredients actifs et utilisation pour larepression des insectes nuisibles
EP0007156B1 (fr)	1982-07-21	Carbamates, compositions les contenant, leur utilisation comme insècticides et nématocides ainsi qu'un procédé de leur préparation
CA1087621A (fr)	1980-10-14	Produits a base de thiosulfenylcarbamoylfluorure de carbamate
US4473580A (en)	1984-09-25	N-Imidoylthio(methyl)carbamates and methods for controlling insects
CA1107292A (fr)	1981-08-18	Carbamates substitues
US4216147A (en)	1980-08-05	N-methyl-N-(substituted carbonylaminothio)carbamates
US4454134A (en)	1984-06-12	Amide carbamates and amide oxime compounds
US4288455A (en)	1981-09-08	Method of controlling mollusc pest