CA2008336C - Agents preservatifs de faible toxicite, sans etain - Google Patents

Agents preservatifs de faible toxicite, sans etain

Info

Publication number: CA2008336C
Authority: CA; Canada
Prior art keywords: dimethyl; chloro; acid; methyl; chlorophenyl
Prior art date: 1988-12-21
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 - Fee Related

Application number

CA002008336A

Other languages

English (en)

Other versions

CA2008336A1 (fr

Inventor

Richard J. Dick

Vincent D. Mcginniss

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.)

Pacific Northwest National Laboratory

Original Assignee

Pacific Northwest National Laboratory

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.)

1988-12-21

Filing date

1990-01-23

Publication date

1999-09-21

1990-01-23 Application filed by Pacific Northwest National Laboratory filed Critical Pacific Northwest National Laboratory

1990-01-23 Priority to CA002008336A priority Critical patent/CA2008336C/fr

1991-07-23 Publication of CA2008336A1 publication Critical patent/CA2008336A1/fr

1999-09-21 Application granted granted Critical

1999-09-21 Publication of CA2008336C publication Critical patent/CA2008336C/fr

2010-01-23 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000002519 antifouling agent Substances 0.000 title claims abstract description 59
231100000053 low toxicity Toxicity 0.000 title description 17
239000000203 mixture Substances 0.000 claims abstract description 38
230000003373 anti-fouling effect Effects 0.000 claims abstract description 27
241000700159 Rattus Species 0.000 claims abstract description 15
239000011230 binding agent Substances 0.000 claims abstract description 10
150000001491 aromatic compounds Chemical class 0.000 claims abstract description 9
239000008199 coating composition Substances 0.000 claims abstract description 8
239000004009 herbicide Substances 0.000 claims abstract description 8
239000000575 pesticide Substances 0.000 claims abstract description 8
229920002554 vinyl polymer Polymers 0.000 claims abstract description 7
239000002904 solvent Substances 0.000 claims abstract description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 6
230000002363 herbicidal effect Effects 0.000 claims abstract description 5
241000699670 Mus sp. Species 0.000 claims abstract description 4
229920001169 thermoplastic Polymers 0.000 claims abstract description 3
229920001187 thermosetting polymer Polymers 0.000 claims abstract description 3
239000004416 thermosoftening plastic Substances 0.000 claims abstract description 3
-1 carbocyclic ketone vinyl ethers Chemical class 0.000 claims description 47
150000001875 compounds Chemical class 0.000 claims description 27
239000007795 chemical reaction product Substances 0.000 claims description 15
RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 8
229920000642 polymer Polymers 0.000 claims description 8
239000007822 coupling agent Substances 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 5
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
239000003822 epoxy resin Substances 0.000 claims description 5
229920000647 polyepoxide Polymers 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 4
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 claims description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
229910052802 copper Inorganic materials 0.000 claims description 4
239000010949 copper Substances 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
DSVOTYIOPGIVPP-UHFFFAOYSA-N (3,4-dichlorophenyl)methyl n-methylcarbamate Chemical compound CNC(=O)OCC1=CC=C(Cl)C(Cl)=C1 DSVOTYIOPGIVPP-UHFFFAOYSA-N 0.000 claims description 3
SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 claims description 3
MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 claims description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
CZGGKXNYNPJFAX-UHFFFAOYSA-N Dimethyldithiophosphate Chemical compound COP(S)(=S)OC CZGGKXNYNPJFAX-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 3
229940092714 benzenesulfonic acid Drugs 0.000 claims description 3
229960001927 cetylpyridinium chloride Drugs 0.000 claims description 3
IRDLUHRVLVEUHA-UHFFFAOYSA-N diethyl dithiophosphate Chemical compound CCOP(S)(=S)OCC IRDLUHRVLVEUHA-UHFFFAOYSA-N 0.000 claims description 3
150000004656 dimethylamines Chemical class 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
229950000688 phenothiazine Drugs 0.000 claims description 3
229920001021 polysulfide Polymers 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
SESJCOBCXSACPH-UHFFFAOYSA-N (2,3-dichlorophenyl)methyl n-methylcarbamate Chemical compound CNC(=O)OCC1=CC=CC(Cl)=C1Cl SESJCOBCXSACPH-UHFFFAOYSA-N 0.000 claims description 2
KPMWGGRSOPMANK-UHFFFAOYSA-N (6-chloro-1,3-benzodioxol-5-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC(C(=C1)Cl)=CC2=C1OCO2 KPMWGGRSOPMANK-UHFFFAOYSA-N 0.000 claims description 2
GNEPLYVYORHREW-UHFFFAOYSA-N 1,1,3,3,6-pentamethyl-7-nitro-2h-inden-5-amine Chemical compound CC1=C(N)C=C2C(C)(C)CC(C)(C)C2=C1[N+]([O-])=O GNEPLYVYORHREW-UHFFFAOYSA-N 0.000 claims description 2
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 claims description 2
AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 claims description 2
OTWBGXPTCSGQEJ-UHFFFAOYSA-N 2-[(dimethylcarbamothioyldisulfanyl)carbothioylamino]ethylcarbamothioylsulfanyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SSC(=S)NCCNC(=S)SSC(=S)N(C)C OTWBGXPTCSGQEJ-UHFFFAOYSA-N 0.000 claims description 2
NCVGSSQICKMAIA-UHFFFAOYSA-N 2-heptadecyl-4,5-dihydro-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NCCN1 NCVGSSQICKMAIA-UHFFFAOYSA-N 0.000 claims description 2
DPJZYUYVRIVLJB-UHFFFAOYSA-N 2-methyl-n-tritylpropan-1-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(NCC(C)C)C1=CC=CC=C1 DPJZYUYVRIVLJB-UHFFFAOYSA-N 0.000 claims description 2
HOULSWDLZNLUIV-UHFFFAOYSA-N 2-prop-2-enylsulfanyl-4,5-dihydro-1,3-thiazole Chemical compound C=CCSC1=NCCS1 HOULSWDLZNLUIV-UHFFFAOYSA-N 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
MENBKTDEJOJLEK-UHFFFAOYSA-N 3-(4-bromophenyl)-1-methoxy-1-methylurea;1,2-dihydropyridazine-3,6-dione Chemical compound O=C1C=CC(=O)NN1.CON(C)C(=O)NC1=CC=C(Br)C=C1 MENBKTDEJOJLEK-UHFFFAOYSA-N 0.000 claims description 2
IBWJXVVIEGGYGU-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-methyl-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound O=C1C(C)SC(=S)N1C1=CC=C(Cl)C=C1 IBWJXVVIEGGYGU-UHFFFAOYSA-N 0.000 claims description 2
SZYWFOPNFNROQB-UHFFFAOYSA-N 4,5,7-trichloro-2,1,3-benzothiadiazole Chemical compound ClC1=C(Cl)C=C(Cl)C2=NSN=C21 SZYWFOPNFNROQB-UHFFFAOYSA-N 0.000 claims description 2
OPHVSASGPNDWOP-UHFFFAOYSA-N 4-amino-2-(dimethylamino)-4-oxobutanoic acid Chemical compound CN(C)C(C(O)=O)CC(N)=O OPHVSASGPNDWOP-UHFFFAOYSA-N 0.000 claims description 2
UXBUOQYOERKCRY-UHFFFAOYSA-N 4-chloro-n-(4-chlorophenyl)-n-methylbenzenesulfonamide Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N(C)C1=CC=C(Cl)C=C1 UXBUOQYOERKCRY-UHFFFAOYSA-N 0.000 claims description 2
JBVNWTXRFKZNBQ-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-en-1-one Chemical compound C1C(CCCCCC)=CC(=O)CC1C1=CC=C(OCO2)C2=C1 JBVNWTXRFKZNBQ-UHFFFAOYSA-N 0.000 claims description 2
BKAQXYNWONVOAX-UHFFFAOYSA-N Butonate Chemical compound CCCC(=O)OC(C(Cl)(Cl)Cl)P(=O)(OC)OC BKAQXYNWONVOAX-UHFFFAOYSA-N 0.000 claims description 2
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 claims description 2
BCHOBBBWIRHOCU-UHFFFAOYSA-N C(C)OCC(O)(C1=CC=C(C=C1)Cl)C1=CC=C(C=C1)Cl.ClC1=C(OCCOC(C(C)(Cl)Cl)=O)C=C(C(=C1)Cl)Cl Chemical compound C(C)OCC(O)(C1=CC=C(C=C1)Cl)C1=CC=C(C=C1)Cl.ClC1=C(OCCOC(C(C)(Cl)Cl)=O)C=C(C(=C1)Cl)Cl BCHOBBBWIRHOCU-UHFFFAOYSA-N 0.000 claims description 2
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 2
QPGNGYFKDXLBKA-UHFFFAOYSA-N ClC1=C(C(=O)OC)C(=C(C(=C1Cl)C(=O)OC)Cl)Cl.ClC1=C(OCCCC(=O)O)C=CC(=C1)Cl Chemical compound ClC1=C(C(=O)OC)C(=C(C(=C1Cl)C(=O)OC)Cl)Cl.ClC1=C(OCCCC(=O)O)C=CC(=C1)Cl QPGNGYFKDXLBKA-UHFFFAOYSA-N 0.000 claims description 2
JHQZGRPQLCTEHA-UHFFFAOYSA-N ClC1=C(OCC(=O)O)C=CC(=C1)Cl.ClC=1C=C(NC(=O)C2CC2)C=CC1Cl.C1(CCCCCCC1)NC(N(C)C)=O.Cl Chemical compound ClC1=C(OCC(=O)O)C=CC(=C1)Cl.ClC=1C=C(NC(=O)C2CC2)C=CC1Cl.C1(CCCCCCC1)NC(N(C)C)=O.Cl JHQZGRPQLCTEHA-UHFFFAOYSA-N 0.000 claims description 2
HJIUPFPIEBPYIE-UHFFFAOYSA-N Crimidine Chemical compound CN(C)C1=CC(C)=NC(Cl)=N1 HJIUPFPIEBPYIE-UHFFFAOYSA-N 0.000 claims description 2
SPANOECCGNXGNR-UITAMQMPSA-N Diallat Chemical compound CC(C)N(C(C)C)C(=O)SC\C(Cl)=C\Cl SPANOECCGNXGNR-UITAMQMPSA-N 0.000 claims description 2
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 2
GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 claims description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
POUJCTLHZZVQBX-UHFFFAOYSA-N NC1=C(C(=NC(=C1Cl)Cl)C(=O)O)Cl.COP(OC(=CCl)C1=C(C=C(C(=C1)Cl)Cl)Cl)(OC)=O Chemical compound NC1=C(C(=NC(=C1Cl)Cl)C(=O)O)Cl.COP(OC(=CCl)C1=C(C=C(C(=C1)Cl)Cl)Cl)(OC)=O POUJCTLHZZVQBX-UHFFFAOYSA-N 0.000 claims description 2
DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 claims description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 claims description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
XJCLWVXTCRQIDI-UHFFFAOYSA-N Sulfallate Chemical compound CCN(CC)C(=S)SCC(Cl)=C XJCLWVXTCRQIDI-UHFFFAOYSA-N 0.000 claims description 2
239000007983 Tris buffer Substances 0.000 claims description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
150000001241 acetals Chemical class 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims description 2
229940115457 cetyldimethylethylammonium bromide Drugs 0.000 claims description 2
125000000068 chlorophenyl group Chemical group 0.000 claims description 2
CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims description 2
SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims description 2
SCKHCCSZFPSHGR-UHFFFAOYSA-N cyanophos Chemical compound COP(=S)(OC)OC1=CC=C(C#N)C=C1 SCKHCCSZFPSHGR-UHFFFAOYSA-N 0.000 claims 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 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims description 2
FLBJFXNAEMSXGL-UHFFFAOYSA-N het anhydride Chemical compound O=C1OC(=O)C2C1C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl FLBJFXNAEMSXGL-UHFFFAOYSA-N 0.000 claims description 2
150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
150000002429 hydrazines Chemical class 0.000 claims description 2
150000002510 isobutyric acid esters Chemical class 0.000 claims description 2
229910052748 manganese Inorganic materials 0.000 claims description 2
239000011572 manganese Substances 0.000 claims description 2
WJQUPFRYZBSBNG-UHFFFAOYSA-N n-(2,5-dichloro-4-nitrosophenyl)-2-hydroxybenzamide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC(Cl)=C(N=O)C=C1Cl WJQUPFRYZBSBNG-UHFFFAOYSA-N 0.000 claims description 2
BETVNUCOOCCCIO-UHFFFAOYSA-N n-(2-dimethoxyphosphinothioylsulfanylethyl)acetamide Chemical compound COP(=S)(OC)SCCNC(C)=O BETVNUCOOCCCIO-UHFFFAOYSA-N 0.000 claims description 2
XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 claims description 2
229920000847 nonoxynol Polymers 0.000 claims description 2
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 claims description 2
229940049964 oleate Drugs 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Chemical group 0.000 claims description 2
229960003540 oxyquinoline Drugs 0.000 claims description 2
229960005235 piperonyl butoxide Drugs 0.000 claims description 2
FHQKDLNFTINTBW-UHFFFAOYSA-N prop-1-ynyl carbamate Chemical compound CC#COC(N)=O FHQKDLNFTINTBW-UHFFFAOYSA-N 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 claims description 2
VEMKTZHHVJILDY-UHFFFAOYSA-N resmethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UHFFFAOYSA-N 0.000 claims description 2
229950000975 salicylanilide Drugs 0.000 claims description 2
IEWKFKOTGJACAI-UHFFFAOYSA-M sodium 2-(2,4-dichlorophenoxy)ethyl sulfate 1-(2-methylcyclohexyl)-3-phenylurea Chemical compound CC1C(CCCC1)NC(=O)NC1=CC=CC=C1.S(=O)(=O)(OCCOC1=C(C=C(C=C1)Cl)Cl)[O-].[Na+] IEWKFKOTGJACAI-UHFFFAOYSA-M 0.000 claims description 2
159000000000 sodium salts Chemical class 0.000 claims description 2
239000001384 succinic acid Substances 0.000 claims description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 claims description 2
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 claims description 2
150000003573 thiols Chemical class 0.000 claims description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 2
ZTHRQJQJODGZHV-UHFFFAOYSA-N n-phenylpropanamide Chemical compound CCC(=O)NC1=CC=CC=C1 ZTHRQJQJODGZHV-UHFFFAOYSA-N 0.000 claims 2
FUZORIOHZSVKAW-WINLOITPSA-N (1R,4S)-1,2,3,4,7,7-hexachloro-5,6-bis(chloromethyl)bicyclo[2.2.1]hept-2-ene Chemical compound ClCC1C(CCl)[C@@]2(Cl)C(Cl)=C(Cl)[C@]1(Cl)C2(Cl)Cl FUZORIOHZSVKAW-WINLOITPSA-N 0.000 claims 1
DAASOABUJRMZAD-NRYKZSQYSA-N (1R,4S,5S)-5-(bromomethyl)-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene Chemical compound BrC[C@H]1C[C@@]2(Cl)C(Cl)=C(Cl)[C@]1(Cl)C2(Cl)Cl DAASOABUJRMZAD-NRYKZSQYSA-N 0.000 claims 1
OZFAFGSSMRRTDW-UHFFFAOYSA-N (2,4-dichlorophenyl) benzenesulfonate Chemical compound ClC1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=CC=C1 OZFAFGSSMRRTDW-UHFFFAOYSA-N 0.000 claims 1
FHNKBSDJERHDHZ-UHFFFAOYSA-N (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(C)C=C1C FHNKBSDJERHDHZ-UHFFFAOYSA-N 0.000 claims 1
RRCXOIBMSKRASZ-UHFFFAOYSA-N (2-prop-2-enoxyphenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1OCC=C RRCXOIBMSKRASZ-UHFFFAOYSA-N 0.000 claims 1
YJXNJQHBVKTWCC-UHFFFAOYSA-N (3-cyclopent-2-en-1-yl-2-methyl-4-oxocyclopent-2-en-1-yl) 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC1C(C)=C(C2C=CCC2)C(=O)C1 YJXNJQHBVKTWCC-UHFFFAOYSA-N 0.000 claims 1
LHTOXQCYXYXXEZ-UHFFFAOYSA-N (3-pentan-2-ylphenyl) n-methylcarbamate Chemical compound CCCC(C)C1=CC=CC(OC(=O)NC)=C1 LHTOXQCYXYXXEZ-UHFFFAOYSA-N 0.000 claims 1
YSOLKQMMAWJIMJ-UHFFFAOYSA-N 1,1-bis(4-chlorophenyl)ethanol 1-chloro-4-[1-(4-chlorophenyl)ethyl]benzene Chemical compound ClC1=CC=C(C=C1)C(C)(O)C1=CC=C(C=C1)Cl.ClC1=CC=C(C=C1)C(C)C1=CC=C(C=C1)Cl YSOLKQMMAWJIMJ-UHFFFAOYSA-N 0.000 claims 1
SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims 1
XRONASRTKCDKMP-UHFFFAOYSA-N 2,6-dichloro-n-(hydroxymethyl)benzenecarbothioamide Chemical compound OCNC(=S)C1=C(Cl)C=CC=C1Cl XRONASRTKCDKMP-UHFFFAOYSA-N 0.000 claims 1
WGEUSFXLHJRECP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)-1-(3,5-dimethylpyrazol-1-yl)ethanone Chemical compound N1=C(C)C=C(C)N1C(=O)COC1=CC=C(Cl)C=C1Cl WGEUSFXLHJRECP-UHFFFAOYSA-N 0.000 claims 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
OQMPNMGXNJHPJP-UHFFFAOYSA-N 2-diethoxyphosphinothioyloxybenzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(N(OP(=S)(OCC)OCC)C2=O)=O)=C3C2=CC=CC3=C1 OQMPNMGXNJHPJP-UHFFFAOYSA-N 0.000 claims 1
FCUBTKFQDYNIIC-UHFFFAOYSA-N 2-dimethoxyphosphinothioylsulfanyl-n-(methoxymethyl)acetamide Chemical compound COCNC(=O)CSP(=S)(OC)OC FCUBTKFQDYNIIC-UHFFFAOYSA-N 0.000 claims 1
OQHXZZGZASQSOB-UHFFFAOYSA-N 3,4,5,6-tetrachlorobenzene-1,2-dicarbonitrile Chemical compound ClC1=C(Cl)C(Cl)=C(C#N)C(C#N)=C1Cl OQHXZZGZASQSOB-UHFFFAOYSA-N 0.000 claims 1
XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 claims 1
XNYGOEGATLFFOX-UHFFFAOYSA-N 4,5a,6,9,9a,9b-hexahydro-1h-dibenzofuran-4a-carbaldehyde Chemical compound C12CC=CCC2OC2(C=O)C1CC=CC2 XNYGOEGATLFFOX-UHFFFAOYSA-N 0.000 claims 1
LDMMYYWIJJTTHG-UHFFFAOYSA-M 9-(4-hexoxyphenyl)-10-methylacridin-10-ium;chloride Chemical compound [Cl-].C1=CC(OCCCCCC)=CC=C1C1=C(C=CC=C2)C2=[N+](C)C2=CC=CC=C12 LDMMYYWIJJTTHG-UHFFFAOYSA-M 0.000 claims 1
RYGQTDWKDQPSHS-UHFFFAOYSA-N C(C1=C(C(=CC(=C1Cl)Cl)Cl)O)C1=C(C(=CC(=C1Cl)Cl)Cl)O.C(C=1C(OC2=CC=CC=C2C1O)=O)C=1C(OC2=CC=CC=C2C1O)=O Chemical compound C(C1=C(C(=CC(=C1Cl)Cl)Cl)O)C1=C(C(=CC(=C1Cl)Cl)Cl)O.C(C=1C(OC2=CC=CC=C2C1O)=O)C=1C(OC2=CC=CC=C2C1O)=O RYGQTDWKDQPSHS-UHFFFAOYSA-N 0.000 claims 1
GUSWVGNMILUXQM-UHFFFAOYSA-N C(CC)OC(=O)C1=NC=C(C=C1)C(=O)OCCC.[N+](=O)([O-])C1=C(N(CCC)CCC)C(=CC(=C1)C)[N+](=O)[O-].C1(=CC=CC=C1)NC1=CC=CC=C1.C1(=CC=CC=C1)C(C#N)C1=CC=CC=C1.CN(C(C(C1=CC=CC=C1)C1=CC=CC=C1)=O)C Chemical compound C(CC)OC(=O)C1=NC=C(C=C1)C(=O)OCCC.[N+](=O)([O-])C1=C(N(CCC)CCC)C(=CC(=C1)C)[N+](=O)[O-].C1(=CC=CC=C1)NC1=CC=CC=C1.C1(=CC=CC=C1)C(C#N)C1=CC=CC=C1.CN(C(C(C1=CC=CC=C1)C1=CC=CC=C1)=O)C GUSWVGNMILUXQM-UHFFFAOYSA-N 0.000 claims 1
ZWMDFIDZLSVUMF-UHFFFAOYSA-M C(O)CN.ClC1=CC=C(C(C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])Cl)=C1)O.ClC1=C(C(=O)[O-])C=C(C=C1[N+](=O)[O-])Cl.ClC1=C(N)C(=CC(=C1)[N+](=O)[O-])Cl.[Na+].ClC(C(=O)O)(CCl)C Chemical compound C(O)CN.ClC1=CC=C(C(C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])Cl)=C1)O.ClC1=C(C(=O)[O-])C=C(C=C1[N+](=O)[O-])Cl.ClC1=C(N)C(=CC(=C1)[N+](=O)[O-])Cl.[Na+].ClC(C(=O)O)(CCl)C ZWMDFIDZLSVUMF-UHFFFAOYSA-M 0.000 claims 1
LCPVJFRBFXAZCB-UHFFFAOYSA-N C1(=CC(=CC=C1)NC(C=1C(C(=O)O)=CC=CC1)=O)C.CN(C(SSC(N(C)C)=S)=S)C Chemical compound C1(=CC(=CC=C1)NC(C=1C(C(=O)O)=CC=CC1)=O)C.CN(C(SSC(N(C)C)=S)=S)C LCPVJFRBFXAZCB-UHFFFAOYSA-N 0.000 claims 1
WTQSCAOSLZVNQF-UHFFFAOYSA-M CCCN(CCC)C([O-])=[S+]CCC.CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1C(N)=O.CN(C)C([S-])=S.NC(SCCSC(N)=S)=S.[Zn+2].[Zn+2] Chemical compound CCCN(CCC)C([O-])=[S+]CCC.CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1C(N)=O.CN(C)C([S-])=S.NC(SCCSC(N)=S)=S.[Zn+2].[Zn+2] WTQSCAOSLZVNQF-UHFFFAOYSA-M 0.000 claims 1
JNFRQNCKPOWXQD-UHFFFAOYSA-N CN(C(NC(C=C1)=CC(Cl)=C1Br)=O)OC.COCCCNC1=NC(NCCCOC)=NC(SC)=N1.OB(OC(C(Cl)=C1Cl)(C(Cl)=C1Cl)Cl)OC(C(Cl)=C1Cl)(C(Cl)=C1Cl)Cl.Cl.Cl Chemical compound CN(C(NC(C=C1)=CC(Cl)=C1Br)=O)OC.COCCCNC1=NC(NCCCOC)=NC(SC)=N1.OB(OC(C(Cl)=C1Cl)(C(Cl)=C1Cl)Cl)OC(C(Cl)=C1Cl)(C(Cl)=C1Cl)Cl.Cl.Cl JNFRQNCKPOWXQD-UHFFFAOYSA-N 0.000 claims 1
SYLVSDVDIZDCTA-UHFFFAOYSA-N CNC(OC1=CC=CC=2CCCCC12)=O.ClC1=C(C=C(C(=C1)Cl)Cl)S(=O)(=O)C1=CC=C(C=C1)Cl.ClC1=C(C(=C(C(=C1)Cl)Cl)[N+](=O)[O-])Cl Chemical compound CNC(OC1=CC=CC=2CCCCC12)=O.ClC1=C(C=C(C(=C1)Cl)Cl)S(=O)(=O)C1=CC=C(C=C1)Cl.ClC1=C(C(=C(C(=C1)Cl)Cl)[N+](=O)[O-])Cl SYLVSDVDIZDCTA-UHFFFAOYSA-N 0.000 claims 1
VCBRBUKGTWLJOB-UHFFFAOYSA-N Chloranocryl Chemical compound CC(=C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 VCBRBUKGTWLJOB-UHFFFAOYSA-N 0.000 claims 1
ULBXWWGWDPVHAO-UHFFFAOYSA-N Chlorbufam Chemical compound C#CC(C)OC(=O)NC1=CC=CC(Cl)=C1 ULBXWWGWDPVHAO-UHFFFAOYSA-N 0.000 claims 1
RXRAXOVRXYVXFP-UHFFFAOYSA-N ClC(C(=NC1=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)Cl)(Cl)Cl.ClC(SN1C(OC2=C1C=CC=C2)=O)(Cl)Cl.ClC(SN2CS(C1=C2C=CC=C1)=O)(Cl)Cl.ClC1=C(COC(CC)O)C(=CC=C1Cl)Cl Chemical compound ClC(C(=NC1=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)Cl)(Cl)Cl.ClC(SN1C(OC2=C1C=CC=C2)=O)(Cl)Cl.ClC(SN2CS(C1=C2C=CC=C1)=O)(Cl)Cl.ClC1=C(COC(CC)O)C(=CC=C1Cl)Cl RXRAXOVRXYVXFP-UHFFFAOYSA-N 0.000 claims 1
GZWRXGQVJPNDDR-UHFFFAOYSA-N ClC1=C(C#N)C(=CC=C1)Cl.P(OC1=C(C=C(C=C1)[N+](=O)[O-])Cl)(OC)(OC)=S.ClC1=C(C(C(=O)O)=C(C=C1)Cl)OC.C(CCC)N(S(=O)(=O)C1=CC=C(C=C1)Cl)CCCC.N1C=NC=C1 Chemical compound ClC1=C(C#N)C(=CC=C1)Cl.P(OC1=C(C=C(C=C1)[N+](=O)[O-])Cl)(OC)(OC)=S.ClC1=C(C(C(=O)O)=C(C=C1)Cl)OC.C(CCC)N(S(=O)(=O)C1=CC=C(C=C1)Cl)CCCC.N1C=NC=C1 GZWRXGQVJPNDDR-UHFFFAOYSA-N 0.000 claims 1
CODRATWCUPVPQH-UHFFFAOYSA-N ClC1=C(C(=C(C=C1)CC(=O)O)Cl)Cl.C(C)(=O)O.C(CCCCCCCCCCC)NC(=N)N Chemical compound ClC1=C(C(=C(C=C1)CC(=O)O)Cl)Cl.C(C)(=O)O.C(CCCCCCCCCCC)NC(=N)N CODRATWCUPVPQH-UHFFFAOYSA-N 0.000 claims 1
SNCWTTKMLZYKQF-UHFFFAOYSA-N ClC1=C(C(=O)O)C=C(C=C1N)Cl.CC1C(C1(C(=O)O)C=CC)C Chemical compound ClC1=C(C(=O)O)C=C(C=C1N)Cl.CC1C(C1(C(=O)O)C=CC)C SNCWTTKMLZYKQF-UHFFFAOYSA-N 0.000 claims 1
NGFVUZRVEAGNMN-UHFFFAOYSA-N ClC1=C(N)C(=CC(=C1)[N+](=O)[O-])Cl.C(C=CC1=CC=CC=C1)(=O)O Chemical compound ClC1=C(N)C(=CC(=C1)[N+](=O)[O-])Cl.C(C=CC1=CC=CC=C1)(=O)O NGFVUZRVEAGNMN-UHFFFAOYSA-N 0.000 claims 1
VLHJUNNTOYVULW-UHFFFAOYSA-N ClC1=CC=C(C=C1)C(C(Cl)Cl)C1=CC=C(C=C1)Cl.ClC1=C(C(Cl)(Cl)Cl)C=CC=C1 Chemical compound ClC1=CC=C(C=C1)C(C(Cl)Cl)C1=CC=C(C=C1)Cl.ClC1=C(C(Cl)(Cl)Cl)C=CC=C1 VLHJUNNTOYVULW-UHFFFAOYSA-N 0.000 claims 1
GXDNDFXAUOSNBT-UHFFFAOYSA-N ClC1=CC=C(C=C1)SSC1=CC=C(C=C1)Cl.ClC1=CC=C(OCOC2=CC=C(C=C2)Cl)C=C1.C(C1=CC=CC=C1)=NN1C(SC=C1C1=CC=CC=C1)=S.C(C1=CC=CC=C1)NCC(=O)O.C1(=CC=CC=C1)S(=O)(=O)NCCS Chemical compound ClC1=CC=C(C=C1)SSC1=CC=C(C=C1)Cl.ClC1=CC=C(OCOC2=CC=C(C=C2)Cl)C=C1.C(C1=CC=CC=C1)=NN1C(SC=C1C1=CC=CC=C1)=S.C(C1=CC=CC=C1)NCC(=O)O.C1(=CC=CC=C1)S(=O)(=O)NCCS GXDNDFXAUOSNBT-UHFFFAOYSA-N 0.000 claims 1
DVJYPKOPYOGFSL-UHFFFAOYSA-N ClC1=NC(=NC(=N1)Cl)NC1=C(C=CC=C1)Cl.ClC(C(C1=CC=C(C=C1)CC)C1=CC=C(C=C1)CC)Cl Chemical compound ClC1=NC(=NC(=N1)Cl)NC1=C(C=CC=C1)Cl.ClC(C(C1=CC=C(C=C1)CC)C1=CC=C(C=C1)CC)Cl DVJYPKOPYOGFSL-UHFFFAOYSA-N 0.000 claims 1
AVDBCJOXKXDXLX-UHFFFAOYSA-N ClCC(=O)N(C1=CC=CC=C1)C(C)C.CC1N(C(=NC(=N1)NC(C)C)NC(C)C)S.C(C)(C)NC1=NC(=NC(=N1)NC(C)C)OC.CNC Chemical compound ClCC(=O)N(C1=CC=CC=C1)C(C)C.CC1N(C(=NC(=N1)NC(C)C)NC(C)C)S.C(C)(C)NC1=NC(=NC(=N1)NC(C)C)OC.CNC AVDBCJOXKXDXLX-UHFFFAOYSA-N 0.000 claims 1
XXXSILNSXNPGKG-ZHACJKMWSA-N Crotoxyphos Chemical compound COP(=O)(OC)O\C(C)=C\C(=O)OC(C)C1=CC=CC=C1 XXXSILNSXNPGKG-ZHACJKMWSA-N 0.000 claims 1
WTDSSEJBZWKFCC-UHFFFAOYSA-N FC1=CC=C(C=C1)SCC1=CC=C(C=C1)Cl.[Zn].ClC=1C=CC2=C(N=C(S2)S)C1 Chemical compound FC1=CC=C(C=C1)SCC1=CC=C(C=C1)Cl.[Zn].ClC=1C=CC2=C(N=C(S2)S)C1 WTDSSEJBZWKFCC-UHFFFAOYSA-N 0.000 claims 1
PSYBGEADHLUXCS-UHFFFAOYSA-N Isocil Chemical compound CC(C)N1C(=O)NC(C)=C(Br)C1=O PSYBGEADHLUXCS-UHFFFAOYSA-N 0.000 claims 1
FPMIAGPUNXEUCZ-UHFFFAOYSA-N Lythidathion Chemical compound CCOC1=NN(CSP(=S)(OC)OC)C(=O)S1 FPMIAGPUNXEUCZ-UHFFFAOYSA-N 0.000 claims 1
ZDSHFUXEMODBLN-UHFFFAOYSA-N N-ethyl-N-[[methoxy-(trihydroxy-lambda5-phosphanylidene)-lambda4-sulfanyl]oxymethyl]ethanamine Chemical class CCN(CC)COS(=P(O)(O)O)OC ZDSHFUXEMODBLN-UHFFFAOYSA-N 0.000 claims 1
RVWUIBIEVIEHKD-UHFFFAOYSA-N N1C=C(C2=CC=CC=C12)CC(=O)O.OC1=C(C(=C(C(=O)O)C=C1)O)O.OCC#N Chemical compound N1C=C(C2=CC=CC=C12)CC(=O)O.OC1=C(C(=C(C(=O)O)C=C1)O)O.OCC#N RVWUIBIEVIEHKD-UHFFFAOYSA-N 0.000 claims 1
GIYKTZPOJRZOHU-UHFFFAOYSA-L OC1=C(C=CC(=C1)O)C1=C(CCCC1)C(=O)O.N1=CC=CC2=CC=CC(=C12)[O-].[Cu+2].N1=CC=CC2=CC=CC(=C12)[O-] Chemical compound OC1=C(C=CC(=C1)O)C1=C(CCCC1)C(=O)O.N1=CC=CC2=CC=CC(=C12)[O-].[Cu+2].N1=CC=CC2=CC=CC(=C12)[O-] GIYKTZPOJRZOHU-UHFFFAOYSA-L 0.000 claims 1
NBQCNZYJJMBDKY-UHFFFAOYSA-N Terbacil Chemical compound CC=1NC(=O)N(C(C)(C)C)C(=O)C=1Cl NBQCNZYJJMBDKY-UHFFFAOYSA-N 0.000 claims 1
HFBWPRKWDIRYNX-UHFFFAOYSA-N Trietazine Chemical compound CCNC1=NC(Cl)=NC(N(CC)CC)=N1 HFBWPRKWDIRYNX-UHFFFAOYSA-N 0.000 claims 1
OWNAXTAAAQTBSP-UHFFFAOYSA-N [3-(dimethylcarbamoylamino)phenyl] n-tert-butylcarbamate Chemical compound CN(C)C(=O)NC1=CC=CC(OC(=O)NC(C)(C)C)=C1 OWNAXTAAAQTBSP-UHFFFAOYSA-N 0.000 claims 1
UCLSMRUQRKTEHR-UHFFFAOYSA-N ac1lcm5e Chemical compound ClC1=C(Cl)C2C3C(Cl)C(Cl)C(Cl)C3C1(Cl)C2(Cl)Cl UCLSMRUQRKTEHR-UHFFFAOYSA-N 0.000 claims 1
150000003931 anilides Chemical class 0.000 claims 1
FMYOAHVUBRCRTI-UHFFFAOYSA-N bis[2-(2,4-dichlorophenoxy)ethyl] hydrogen phosphite Chemical compound C=1C=C(Cl)C=C(Cl)C=1OCCOP(O)OCCOC1=CC=C(Cl)C=C1Cl FMYOAHVUBRCRTI-UHFFFAOYSA-N 0.000 claims 1
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclo-pentanone Natural products O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims 1
BAFCBDVCYCRYPM-UHFFFAOYSA-N di(propan-2-yloxy)phosphinothioyl n,n-diethylcarbamodithioate Chemical compound CCN(CC)C(=S)SP(=S)(OC(C)C)OC(C)C BAFCBDVCYCRYPM-UHFFFAOYSA-N 0.000 claims 1
WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 claims 1
ZRCQYAQOWIQUBA-UHFFFAOYSA-N ethyl 2-diethoxyphosphorylsulfanylacetate Chemical compound CCOC(=O)CSP(=O)(OCC)OCC ZRCQYAQOWIQUBA-UHFFFAOYSA-N 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
CWOBGOXHYZMVNY-UHFFFAOYSA-N methyl 2,3,5,6-tetrachloro-4-[methoxy(methyl)carbamoyl]benzoate Chemical compound CON(C)C(=O)C1=C(Cl)C(Cl)=C(C(=O)OC)C(Cl)=C1Cl CWOBGOXHYZMVNY-UHFFFAOYSA-N 0.000 claims 1
IHCHKPCNDMQWGF-UHFFFAOYSA-N methyl phenkapton Chemical compound COP(=S)(OC)SCSC1=CC(Cl)=CC=C1Cl IHCHKPCNDMQWGF-UHFFFAOYSA-N 0.000 claims 1
XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 claims 1
ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 claims 1
VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 claims 1
WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical compound OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 claims 1
NTOCDDPMRUNYHP-UHFFFAOYSA-M sodium;2-(2,4,5-trichlorophenoxy)ethyl sulfate Chemical compound [Na+].[O-]S(=O)(=O)OCCOC1=CC(Cl)=C(Cl)C=C1Cl NTOCDDPMRUNYHP-UHFFFAOYSA-M 0.000 claims 1
NMGNJWORLGLLHQ-UHFFFAOYSA-M sulcofuron-sodium Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 NMGNJWORLGLLHQ-UHFFFAOYSA-M 0.000 claims 1
ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 claims 1
NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 claims 1
238000000576 coating method Methods 0.000 description 20
239000000460 chlorine Substances 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
239000011248 coating agent Substances 0.000 description 9
238000009472 formulation Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 7
238000007654 immersion Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000011347 resin Substances 0.000 description 6
229920005989 resin Polymers 0.000 description 6
231100000167 toxic agent Toxicity 0.000 description 6
239000003440 toxic substance Substances 0.000 description 6
230000008901 benefit Effects 0.000 description 5
239000000178 monomer Substances 0.000 description 5
239000003973 paint Substances 0.000 description 5
239000002245 particle Substances 0.000 description 5
241000282412 Homo Species 0.000 description 4
238000002386 leaching Methods 0.000 description 4
239000004033 plastic Substances 0.000 description 4
229920003023 plastic Polymers 0.000 description 4
239000013535 sea water Substances 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
102100021570 B-cell lymphoma 3 protein Human genes 0.000 description 3
NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
239000005770 Eugenol Substances 0.000 description 3
101000971179 Mus musculus B-cell lymphoma 3 protein homolog Proteins 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 3
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
239000004327 boric acid Substances 0.000 description 3
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
229960002217 eugenol Drugs 0.000 description 3
239000011159 matrix material Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
239000000049 pigment Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
231100000331 toxic Toxicity 0.000 description 3
230000002588 toxic effect Effects 0.000 description 3
239000003053 toxin Substances 0.000 description 3
231100000765 toxin Toxicity 0.000 description 3
108700012359 toxins Proteins 0.000 description 3
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 3
ZQIXMFWBDHBJMJ-UHFFFAOYSA-N (dimethoxy-lambda4-sulfanylidene)-trihydroxy-lambda5-phosphane Chemical class COS(OC)=P(O)(O)O ZQIXMFWBDHBJMJ-UHFFFAOYSA-N 0.000 description 2
FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
NEBPTMCRLHKPOB-UHFFFAOYSA-N 2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C#N)C1=CC=CC=C1 NEBPTMCRLHKPOB-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
102100032481 B-cell CLL/lymphoma 9 protein Human genes 0.000 description 2
101710165244 B-cell CLL/lymphoma 9 protein Proteins 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241000238586 Cirripedia Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000003619 algicide Substances 0.000 description 2
SZXAQBAUDGBVLT-UHFFFAOYSA-H antimony(3+);2,3-dihydroxybutanedioate Chemical compound [Sb+3].[Sb+3].[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O SZXAQBAUDGBVLT-UHFFFAOYSA-H 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
SVOAENZIOKPANY-UHFFFAOYSA-L copper;octadec-9-enoate Chemical compound [Cu+2].CCCCCCCCC=CCCCCCCCC([O-])=O.CCCCCCCCC=CCCCCCCCC([O-])=O SVOAENZIOKPANY-UHFFFAOYSA-L 0.000 description 2
PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Chemical compound CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 2
230000002500 effect on skin Effects 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
238000011068 loading method Methods 0.000 description 2
239000000025 natural resin Substances 0.000 description 2
238000012856 packing Methods 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000002986 polymer concrete Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000000565 sealant Substances 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 2
ZCVAOQKBXKSDMS-PVAVHDDUSA-N (+)-trans-(S)-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-PVAVHDDUSA-N 0.000 description 1
WOVDLAVTRWJPBY-UHFFFAOYSA-N (4-tert-butyl-2-chlorophenyl)methoxy-N-methylphosphonamidous acid Chemical compound CNP(O)OCC1=CC=C(C(C)(C)C)C=C1Cl WOVDLAVTRWJPBY-UHFFFAOYSA-N 0.000 description 1
DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
DMYOHQBLOZMDLP-UHFFFAOYSA-N 1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1CCCCN1CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 DMYOHQBLOZMDLP-UHFFFAOYSA-N 0.000 description 1
FHUZHGVZUUHRIO-UHFFFAOYSA-N 1-chloro-4-[(4-chlorophenoxy)methoxy]benzene;1-chloro-4-[(4-chlorophenyl)disulfanyl]benzene Chemical compound C1=CC(Cl)=CC=C1SSC1=CC=C(Cl)C=C1.C1=CC(Cl)=CC=C1OCOC1=CC=C(Cl)C=C1 FHUZHGVZUUHRIO-UHFFFAOYSA-N 0.000 description 1
YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
KPLDRYODCDLNHB-UHFFFAOYSA-N 1-ethylpyrimidine-2,4-dione Chemical compound CCN1C=CC(=O)NC1=O KPLDRYODCDLNHB-UHFFFAOYSA-N 0.000 description 1
WHRZCXAVMTUTDD-UHFFFAOYSA-N 1h-furo[2,3-d]pyrimidin-2-one Chemical compound N1C(=O)N=C2OC=CC2=C1 WHRZCXAVMTUTDD-UHFFFAOYSA-N 0.000 description 1
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
BRRSNXCXLSVPFC-UHFFFAOYSA-N 2,3,4-Trihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1O BRRSNXCXLSVPFC-UHFFFAOYSA-N 0.000 description 1
ALLSOOQIDPLIER-UHFFFAOYSA-N 2,3,4-trichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(Cl)=C1Cl ALLSOOQIDPLIER-UHFFFAOYSA-N 0.000 description 1
239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
HCGXLLKTPOWTFZ-UHFFFAOYSA-N 2-(2,3,4-trichlorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(Cl)C(Cl)=C1Cl HCGXLLKTPOWTFZ-UHFFFAOYSA-N 0.000 description 1
WYHZRJFGAZCCCB-UHFFFAOYSA-N 2-(2,4-dihydroxyphenyl)cyclohexene-1-carboxylic acid Chemical compound C1CCCC(C(=O)O)=C1C1=CC=C(O)C=C1O WYHZRJFGAZCCCB-UHFFFAOYSA-N 0.000 description 1
NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
RZCJYMOBWVJQGV-UHFFFAOYSA-N 2-naphthyloxyacetic acid Chemical compound C1=CC=CC2=CC(OCC(=O)O)=CC=C21 RZCJYMOBWVJQGV-UHFFFAOYSA-N 0.000 description 1
BIAGXFVBJBNHOR-GZTJUZNOSA-N 3-[(e)-benzylideneamino]-4-phenyl-1,3-thiazole-2-thione Chemical compound C=1C=CC=CC=1/C=N/N1C(=S)SC=C1C1=CC=CC=C1 BIAGXFVBJBNHOR-GZTJUZNOSA-N 0.000 description 1
ZCDNZGUTDLSWLU-UHFFFAOYSA-N 4,6-dichloro-n-(2-chlorophenyl)-1,3,5-triazin-2-amine;1,4-diethylbenzene Chemical compound CCC1=CC=C(CC)C=C1.ClC1=NC(Cl)=NC(NC=2C(=CC=CC=2)Cl)=N1 ZCDNZGUTDLSWLU-UHFFFAOYSA-N 0.000 description 1
YVSOHSORZSKWNS-UHFFFAOYSA-N 4-n-ethyl-6-methylsulfanyl-2-n-propan-2-yl-1,3,5-triazine-2,4-diamine;1,2,3,4,7,7-hexachloro-5,6-bis(chloromethyl)bicyclo[2.2.1]hept-2-ene Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1.ClC1=C(Cl)C2(Cl)C(CCl)C(CCl)C1(Cl)C2(Cl)Cl YVSOHSORZSKWNS-UHFFFAOYSA-N 0.000 description 1
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
102100021569 Apoptosis regulator Bcl-2 Human genes 0.000 description 1
102100021631 B-cell lymphoma 6 protein Human genes 0.000 description 1
FRTZXXQJMFWTPY-UHFFFAOYSA-N C(C)(C)(C)C1=C(C(=CC(=C1)CNC(O)=O)C(C)(C)C)C.C(C)(C)(C)N1C(NC(=C(C1=O)Cl)C)=O Chemical compound C(C)(C)(C)C1=C(C(=CC(=C1)CNC(O)=O)C(C)(C)C)C.C(C)(C)(C)N1C(NC(=C(C1=O)Cl)C)=O FRTZXXQJMFWTPY-UHFFFAOYSA-N 0.000 description 1
XDCAWJQLADJFDX-UHFFFAOYSA-N C(C)(C)NN1NC(=CC(=N1)Cl)NCC Chemical compound C(C)(C)NN1NC(=CC(=N1)Cl)NCC XDCAWJQLADJFDX-UHFFFAOYSA-N 0.000 description 1
HNKLISGSBIDDLP-UHFFFAOYSA-N C(C1=CC=CC=C1)NCC(=O)O.C1(=CC=CC=C1)S(=O)(=O)N Chemical compound C(C1=CC=CC=C1)NCC(=O)O.C1(=CC=CC=C1)S(=O)(=O)N HNKLISGSBIDDLP-UHFFFAOYSA-N 0.000 description 1
MNGWWGKSZTUTQI-UHFFFAOYSA-L C(N)(SCCSC(N)=S)=S.[Na+].[Na+].ClC(C(=O)[O-])(Cl)Cl.ClC(C(=O)[O-])(Cl)Cl Chemical compound C(N)(SCCSC(N)=S)=S.[Na+].[Na+].ClC(C(=O)[O-])(Cl)Cl.ClC(C(=O)[O-])(Cl)Cl MNGWWGKSZTUTQI-UHFFFAOYSA-L 0.000 description 1
229910014033 C-OH Inorganic materials 0.000 description 1
ZGUNSNUZEDVBNT-UHFFFAOYSA-N CC1C(C1(C(=O)O)C=CC)C Chemical compound CC1C(C1(C(=O)O)C=CC)C ZGUNSNUZEDVBNT-UHFFFAOYSA-N 0.000 description 1
JOGGFKCGFJQLID-UHFFFAOYSA-N CN(C)P(N)(N)=O.N.N Chemical compound CN(C)P(N)(N)=O.N.N JOGGFKCGFJQLID-UHFFFAOYSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
229920013683 Celanese Polymers 0.000 description 1
HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
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 1
XQZLLLHIAQOEAI-UHFFFAOYSA-N ClC(SN1CS(C2=C1C=CC=C2)=O)(Cl)Cl.ClC2=C(COC(CC)O)C(=CC=C2Cl)Cl Chemical compound ClC(SN1CS(C2=C1C=CC=C2)=O)(Cl)Cl.ClC2=C(COC(CC)O)C(=CC=C2Cl)Cl XQZLLLHIAQOEAI-UHFFFAOYSA-N 0.000 description 1
229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
229910014570 C—OH Inorganic materials 0.000 description 1
239000004287 Dehydroacetic acid Substances 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
102100024165 G1/S-specific cyclin-D1 Human genes 0.000 description 1
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical class NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
101000971171 Homo sapiens Apoptosis regulator Bcl-2 Proteins 0.000 description 1
101000971234 Homo sapiens B-cell lymphoma 6 protein Proteins 0.000 description 1
101000980756 Homo sapiens G1/S-specific cyclin-D1 Proteins 0.000 description 1
206010061217 Infestation Diseases 0.000 description 1
244000073231 Larrea tridentata Species 0.000 description 1
235000006173 Larrea tridentata Nutrition 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
240000007930 Oxalis acetosella Species 0.000 description 1
235000008098 Oxalis acetosella Nutrition 0.000 description 1
USUVUUDTYRMYMV-UHFFFAOYSA-N P(OC)(OC)(OC1=CC(=C(C=C1)[N+](=O)[O-])Cl)=S.P(O)(O)(O)=S Chemical compound P(OC)(OC)(OC1=CC(=C(C=C1)[N+](=O)[O-])Cl)=S.P(O)(O)(O)=S USUVUUDTYRMYMV-UHFFFAOYSA-N 0.000 description 1
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
241000237908 Riftia pachyptila Species 0.000 description 1
IVAIOFLFEOYWLX-UHFFFAOYSA-N S1C=NC(=C1)C=1NC2=C(N1)C=CC=C2.[N+](=O)([O-])C2=CC(=CC=1C3=CC(=CC(=C3NC21)[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-] Chemical compound S1C=NC(=C1)C=1NC2=C(N1)C=CC=C2.[N+](=O)([O-])C2=CC(=CC=1C3=CC(=CC(=C3NC21)[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-] IVAIOFLFEOYWLX-UHFFFAOYSA-N 0.000 description 1
KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
229920001079 Thiokol (polymer) Polymers 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
GVWHWWZFJPCSCV-UHFFFAOYSA-N [1-(4,4-dimethylcyclohexyl)-3-phenoxypent-1-yn-3-yl] hydrogen sulfite Chemical compound CCC(C#CC1CCC(CC1)(C)C)(OC2=CC=CC=C2)OS(=O)O GVWHWWZFJPCSCV-UHFFFAOYSA-N 0.000 description 1
UZRKASNXDXMTMC-UHFFFAOYSA-N [N+](=O)([O-])C1=C(N(CCC)CCC)C(=CC(=C1)C)[N+](=O)[O-].C1(=CC=CC=C1)NC1=CC=CC=C1.C1(=CC=CC=C1)C(C#N)C1=CC=CC=C1 Chemical compound [N+](=O)([O-])C1=C(N(CCC)CCC)C(=CC(=C1)C)[N+](=O)[O-].C1(=CC=CC=C1)NC1=CC=CC=C1.C1(=CC=CC=C1)C(C#N)C1=CC=CC=C1 UZRKASNXDXMTMC-UHFFFAOYSA-N 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
150000001260 acyclic compounds Chemical class 0.000 description 1
150000007824 aliphatic compounds Chemical class 0.000 description 1
230000002547 anomalous effect Effects 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
230000015572 biosynthetic process Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
239000004841 bisphenol A epoxy resin Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001717 carbocyclic compounds Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
AXGUBXVWZBFQGA-UHFFFAOYSA-N chloropropylate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OC(C)C)C1=CC=C(Cl)C=C1 AXGUBXVWZBFQGA-UHFFFAOYSA-N 0.000 description 1
CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
230000001010 compromised effect Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
229960002126 creosote Drugs 0.000 description 1
229940008203 d-transallethrin Drugs 0.000 description 1
QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 description 1
230000002950 deficient Effects 0.000 description 1
235000019258 dehydroacetic acid Nutrition 0.000 description 1
229940061632 dehydroacetic acid Drugs 0.000 description 1
BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 1
IITCWRFYJWUUPC-UHFFFAOYSA-N dipropyl pyridine-2,5-dicarboxylate Chemical compound CCCOC(=O)C1=CC=C(C(=O)OCCC)N=C1 IITCWRFYJWUUPC-UHFFFAOYSA-N 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
229940075933 dithionate Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
230000003628 erosive effect Effects 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
VUFOSBDICLTFMS-UHFFFAOYSA-M ethyl-hexadecyl-dimethylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)CC VUFOSBDICLTFMS-UHFFFAOYSA-M 0.000 description 1
235000010985 glycerol esters of wood rosin Nutrition 0.000 description 1
LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 1
239000011440 grout Substances 0.000 description 1
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
ACGUYXCXAPNIKK-UHFFFAOYSA-N hexachlorophene Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1CC1=C(O)C(Cl)=CC(Cl)=C1Cl ACGUYXCXAPNIKK-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
231100001225 mammalian toxicity Toxicity 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
150000002731 mercury compounds Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
KNDXZFMNQKSIHU-UHFFFAOYSA-N methyl 2,3,5,6-tetrachloro-4-methylsulfanylcarbonylbenzoate Chemical compound COC(=O)C1=C(Cl)C(Cl)=C(C(=O)SC)C(Cl)=C1Cl KNDXZFMNQKSIHU-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
230000008450 motivation Effects 0.000 description 1
WMIPWRSVIZFVQB-UHFFFAOYSA-N n,n-dimethyl-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)N(C)C)C1=CC=CC=C1.C=1C=CC=CC=1C(C(=O)N(C)C)C1=CC=CC=C1 WMIPWRSVIZFVQB-UHFFFAOYSA-N 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000010292 orthophenyl phenol Nutrition 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
239000002574 poison Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
KZTXOHMYUXADBN-UHFFFAOYSA-N propan-2-yl 2-dimethoxyphosphinothioylsulfanyl-2-phenylacetate Chemical compound COP(=S)(OC)SC(C(=O)OC(C)C)C1=CC=CC=C1 KZTXOHMYUXADBN-UHFFFAOYSA-N 0.000 description 1
PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000005060 rubber Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
229960002447 thiram Drugs 0.000 description 1
CVNKFOIOZXAFBO-UHFFFAOYSA-J tin(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Sn+4] CVNKFOIOZXAFBO-UHFFFAOYSA-J 0.000 description 1
229940066528 trichloroacetate Drugs 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
239000012989 trithiocarbonate Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Paints Or Removers (AREA)

CA002008336A 1988-12-21 1990-01-23 Agents preservatifs de faible toxicite, sans etain Expired - Fee Related CA2008336C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002008336A CA2008336C (fr)	1988-12-21	1990-01-23	Agents preservatifs de faible toxicite, sans etain

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US28789988A	1988-12-21	1988-12-21
CA002008336A CA2008336C (fr)	1988-12-21	1990-01-23	Agents preservatifs de faible toxicite, sans etain

Publications (2)

Publication Number	Publication Date
CA2008336A1 CA2008336A1 (fr)	1991-07-23
CA2008336C true CA2008336C (fr)	1999-09-21

Family

ID=25673900

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002008336A Expired - Fee Related CA2008336C (fr)	1988-12-21	1990-01-23	Agents preservatifs de faible toxicite, sans etain

Country Status (1)

Country	Link
CA (1)	CA2008336C (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN112375090B (zh) *	2020-11-25	2022-04-15	广西民族师范学院	一种一维梯形链状结构铜配合物的制备方法及用途

1990
- 1990-01-23 CA CA002008336A patent/CA2008336C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2008336A1 (fr)	1991-07-23

Legal Events

Date	Code	Title	Description
1996-09-19	EEER	Examination request
2001-01-23	MKLA	Lapsed

Publication	Publication Date	Title
AU2004271873B2 (en)	2009-12-17	Capsaicin derivates and the production and use thereof
EP0449975B1 (fr)	1997-04-23	Agents antisalissures non stanniferes de faible toxicite
AU660030B2 (en)	1995-06-08	Marine compositions bearing preferentially concentrated domains of non-tin, organo or inorganic anti-fouling agents
US5441743A (en)	1995-08-15	Marine compositions bearing preferentially concentrated domains of non-tin, organo anti-fouling agents
AU2001275527B2 (en)	2005-01-13	Non-toxic coating composition, methods of use thereof and articles protected from attachment of biofouling organisms
DE69632936T2 (de)	2004-12-16	Verwendung von Pyrrolverbindungen als Antifouling-Wirkstoff
CA2008336C (fr)	1999-09-21	Agents preservatifs de faible toxicite, sans etain
US3912519A (en)	1975-10-14	Anti-fouling ship bottom paint
KR100363364B1 (ko)	2004-02-05	수생부착성유기물의정착방지방법
Phillip	1973	Modern trends in marine antifouling paints research
US5833742A (en)	1998-11-10	Phenylamides as marine antifouling agents
GB2140299A (en)	1984-11-28	Use of haloalkynyl carbamates in treating micro-organisms
DE68907952T2 (de)	1994-03-10	Überzugsmassen und Verfahren, um die Haftung von Unterwasserorganismen zu verhindern.
JPH0769815A (ja)	1995-03-14	水中防汚剤
US3765933A (en)	1973-10-16	Method for the protection against aquatic parasites
US5507862A (en)	1996-04-16	Anti-fouling compositions or fouling control of harmful aquatic organisms
EP0266738B1 (fr)	1993-07-21	Utilisation de la composition de revêtement
EP0890310A1 (fr)	1999-01-13	Agent marin anti-salissure
CA1079455A (fr)	1980-06-17	Enduit
CN111826033A (zh)	2020-10-27	一种水性船舶生物防污工业涂料及其制备方法
JPH06340504A (ja)	1994-12-13	水中防汚剤
CA1258227A (fr)	1989-08-08	Repulsifs et toxiques pour invertebres aquatiques, obtenus a partir d'urethanes de derives de substitution d'alcynes halogenes en 1; compositions renfermant ces produits et leur utilisation
Anton et al.	0	ANTIFOULING ACTIVITY OF NATURAL ACTIVE COMPOUNDS THROUGH BIOASSAYS AND FIELD IMMERSION TESTS
DE2510330A1 (de)	1975-10-23	Gegen mikroorganismen bestaendige ueberzugsmassen
JPH06305908A (ja)	1994-11-01	水中防汚剤