CA1046935A - Carbamates iodoalkynyles a effets fongicides - Google Patents

Carbamates iodoalkynyles a effets fongicides

Info

Publication number: CA1046935A
Authority: CA; Canada
Prior art keywords: compounds; urethanes; compound; carbon atoms; ether
Prior art date: 1973-07-11
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

CA291,724A

Other languages

English (en)

Inventor

William Singer

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.)

Troy Chemical Corp

Original Assignee

Troy Chemical Corp

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.)

1973-07-11

Filing date

1977-11-25

Publication date

1979-01-23

1973-07-11 Priority claimed from US378089A external-priority patent/US3923870A/en

1977-11-25 Application filed by Troy Chemical Corp filed Critical Troy Chemical Corp

1979-01-23 Application granted granted Critical

1979-01-23 Publication of CA1046935A publication Critical patent/CA1046935A/fr

Status Expired legal-status Critical Current

Links

230000000855 fungicidal effect Effects 0.000 title claims abstract description 12
150000004657 carbamic acid derivatives Chemical class 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 38
239000000203 mixture Substances 0.000 claims abstract description 16
239000003973 paint Substances 0.000 claims abstract description 14
241000233866 Fungi Species 0.000 claims abstract description 12
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
239000000463 material Substances 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
239000011149 active material Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
150000003673 urethanes Chemical class 0.000 description 25
239000007787 solid Substances 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
239000000417 fungicide Substances 0.000 description 13
239000012948 isocyanate Substances 0.000 description 11
150000002513 isocyanates Chemical class 0.000 description 11
238000012360 testing method Methods 0.000 description 11
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
230000012010 growth Effects 0.000 description 7
239000004816 latex Substances 0.000 description 7
229920000126 latex Polymers 0.000 description 7
239000007788 liquid Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
125000002346 iodo group Chemical group I* 0.000 description 6
239000002904 solvent Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
125000001246 bromo group Chemical group Br* 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
230000002538 fungal effect Effects 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 4
238000000576 coating method Methods 0.000 description 4
235000021388 linseed oil Nutrition 0.000 description 4
239000000944 linseed oil Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
150000001345 alkine derivatives Chemical class 0.000 description 3
238000004166 bioassay Methods 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
239000013530 defoamer Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
241001558165 Alternaria sp. Species 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
230000001680 brushing effect Effects 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000008199 coating composition Substances 0.000 description 2
230000001276 controlling effect Effects 0.000 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 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
125000003438 dodecyl group Chemical group [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])* 0.000 description 2
230000000694 effects Effects 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
238000011534 incubation Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
239000000787 lecithin Substances 0.000 description 2
229940067606 lecithin Drugs 0.000 description 2
235000010445 lecithin Nutrition 0.000 description 2
125000002347 octyl 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])[H] 0.000 description 2
239000000123 paper Substances 0.000 description 2
239000000049 pigment Substances 0.000 description 2
235000019422 polyvinyl alcohol Nutrition 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000004408 titanium dioxide Substances 0.000 description 2
-1 urethane compound Chemical class 0.000 description 2
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
JYQJMGROXSSXDR-UHFFFAOYSA-N 3-iodoprop-2-yn-1-ol Chemical compound OCC#CI JYQJMGROXSSXDR-UHFFFAOYSA-N 0.000 description 1
PCIPCEOKFBAUNM-UHFFFAOYSA-N 4-bromo-2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#CBr PCIPCEOKFBAUNM-UHFFFAOYSA-N 0.000 description 1
ZUKWNSZNXJADAY-UHFFFAOYSA-N 4-bromobut-3-yn-1-ol Chemical compound OCCC#CBr ZUKWNSZNXJADAY-UHFFFAOYSA-N 0.000 description 1
NKFIBMOQAPEKNZ-UHFFFAOYSA-N 5-amino-1h-indole-2-carboxylic acid Chemical compound NC1=CC=C2NC(C(O)=O)=CC2=C1 NKFIBMOQAPEKNZ-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical class C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
241000228245 Aspergillus niger Species 0.000 description 1
241000223678 Aureobasidium pullulans Species 0.000 description 1
239000005745 Captan Substances 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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 1
BGZLICMDVPAAHL-UHFFFAOYSA-N NC(=O)OCC.OCCC#CI Chemical class NC(=O)OCC.OCCC#CI BGZLICMDVPAAHL-UHFFFAOYSA-N 0.000 description 1
235000004443 Ricinus communis Nutrition 0.000 description 1
206010040880 Skin irritation Diseases 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
239000005708 Sodium hypochlorite Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001516 alkali metal iodide Inorganic materials 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000013096 assay test Methods 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229940117949 captan Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
NMCCNOZOBBWFMN-UHFFFAOYSA-N davicil Chemical compound CS(=O)(=O)C1=C(Cl)C(Cl)=NC(Cl)=C1Cl NMCCNOZOBBWFMN-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007682 dermal toxicity Effects 0.000 description 1
AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
XPQBPGDCDTYGHL-UHFFFAOYSA-N diiodomethylsulfonylbenzene Chemical compound IC(I)S(=O)(=O)C1=CC=CC=C1 XPQBPGDCDTYGHL-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
VHYIGGDXWYKOMG-UHFFFAOYSA-N ethyl n-bromocarbamate Chemical class CCOC(=O)NBr VHYIGGDXWYKOMG-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000002083 iodinating effect Effects 0.000 description 1
230000026045 iodination Effects 0.000 description 1
238000006192 iodination reaction Methods 0.000 description 1
239000002085 irritant Substances 0.000 description 1
231100000021 irritant Toxicity 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000010985 leather Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000003340 mental effect Effects 0.000 description 1
150000002731 mercury compounds Chemical class 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000005609 naphthenate group Chemical group 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
229940096825 phenylmercury Drugs 0.000 description 1
DCNLOVYDMCVNRZ-UHFFFAOYSA-N phenylmercury(.) Chemical compound [Hg]C1=CC=CC=C1 DCNLOVYDMCVNRZ-UHFFFAOYSA-N 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
238000007747 plating Methods 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000036556 skin irritation Effects 0.000 description 1
231100000475 skin irritation Toxicity 0.000 description 1
231100000438 skin toxicity Toxicity 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000004383 yellowing Methods 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA291,724A 1973-07-11 1977-11-25 Carbamates iodoalkynyles a effets fongicides Expired CA1046935A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US378089A US3923870A (en)	1973-07-11	1973-07-11	Urethanes of 1-halogen substituted alkynes
CA203,714A CA1047046A (fr)	1973-07-11	1974-06-28	Fongicides a base de carbamates d'indoalkynyle

Publications (1)

Publication Number	Publication Date
CA1046935A true CA1046935A (fr)	1979-01-23

Family

ID=25667614

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA291,724A Expired CA1046935A (fr)	1973-07-11	1977-11-25	Carbamates iodoalkynyles a effets fongicides

Country Status (1)

Country	Link
CA (1)	CA1046935A (fr)

1977
- 1977-11-25 CA CA291,724A patent/CA1046935A/fr not_active Expired

Publication	Publication Date	Title
CA1047046A (fr)	1979-01-23	Fongicides a base de carbamates d'indoalkynyle
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AU619257B2 (en)	1992-01-23	Improvments in or relating to biocidal quaternary salts of tertrafluoroborate and hexafluorophosphate
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