IE48789B1 - Algicidal composition and method of preventing or controlling algae with said composition - Google Patents

Algicidal composition and method of preventing or controlling algae with said composition

Info

Publication number: IE48789B1
Authority: IE; Ireland
Prior art keywords: group; diethyl; compound; diamine; composition
Prior art date: 1978-07-26

Application number

IE1504/79A

Other languages

English (en)

Other versions

IE791504L (en

Original Assignee

Duphar Int Res

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.)

1978-07-26

Filing date

1979-08-08

Publication date

1985-05-15

1979-08-08 Application filed by Duphar Int Res filed Critical Duphar Int Res

1979-08-08 Priority to IE122283A priority Critical patent/IE48790B1/en

1980-01-26 Publication of IE791504L publication Critical patent/IE791504L/xx

1985-05-15 Publication of IE48789B1 publication Critical patent/IE48789B1/en

Links

239000000203 mixture Substances 0.000 title claims abstract description 39
241000195493 Cryptophyta Species 0.000 title claims description 26
230000002353 algacidal effect Effects 0.000 title claims description 13
150000001875 compounds Chemical class 0.000 claims abstract description 78
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
239000013543 active substance Substances 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 20
150000004985 diamines Chemical class 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
-1 fluoromethyl-substituted phenyl group Chemical group 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 6
239000002352 surface water Substances 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
239000012876 carrier material Substances 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
239000003755 preservative agent Substances 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
230000000855 fungicidal effect Effects 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
239000000470 constituent Substances 0.000 claims 3
125000004429 atom Chemical group 0.000 claims 2
125000004807 2-methylethylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
150000002367 halogens Chemical group 0.000 claims 1
239000000463 material Substances 0.000 claims 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
230000002335 preservative effect Effects 0.000 claims 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
239000003619 algicide Substances 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 15
239000000243 solution Substances 0.000 description 12
150000001412 amines Chemical class 0.000 description 11
230000000694 effects Effects 0.000 description 10
238000011282 treatment Methods 0.000 description 10
239000000047 product Substances 0.000 description 9
230000002829 reductive effect Effects 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
101100356682 Caenorhabditis elegans rho-1 gene Proteins 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
241000251468 Actinopterygii Species 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
231100000419 toxicity Toxicity 0.000 description 5
230000001988 toxicity Effects 0.000 description 5
241001478778 Cladophora Species 0.000 description 4
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000238571 Cladocera Species 0.000 description 3
241001494246 Daphnia magna Species 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
CJKRXEBLWJVYJD-UHFFFAOYSA-N N,N'-diethylethylenediamine Chemical compound CCNCCNCC CJKRXEBLWJVYJD-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241000196294 Spirogyra Species 0.000 description 3
241000200212 Vaucheria Species 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 3
RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000276427 Poecilia reticulata Species 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
241001098657 Pterois Species 0.000 description 2
235000003846 Ricinus Nutrition 0.000 description 2
241000322381 Ricinus <louse> Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
101150052863 THY1 gene Proteins 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000003480 eluent Substances 0.000 description 2
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 2
150000003840 hydrochlorides Chemical class 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
239000010410 layer Substances 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
239000008188 pellet Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
241000894007 species Species 0.000 description 2
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000008399 tap water Substances 0.000 description 2
235000020679 tap water Nutrition 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
NZUXRGMXFCTGBV-UHFFFAOYSA-N 2-(1,1,2,2-tetrachloroethylsulfanyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)C21 NZUXRGMXFCTGBV-UHFFFAOYSA-N 0.000 description 1
MZDWLSFMKPXWGO-UHFFFAOYSA-N 2-n-(3,4-dichlorophenyl)-1-n,1-n-diethylpropane-1,2-diamine Chemical compound CCN(CC)CC(C)NC1=CC=C(Cl)C(Cl)=C1 MZDWLSFMKPXWGO-UHFFFAOYSA-N 0.000 description 1
QPHOEINJOPAVDB-UHFFFAOYSA-N 2-n-(4-chlorophenyl)-1-n,1-n-diethylpropane-1,2-diamine Chemical compound CCN(CC)CC(C)NC1=CC=C(Cl)C=C1 QPHOEINJOPAVDB-UHFFFAOYSA-N 0.000 description 1
DUSNCFKVMGTTFK-UHFFFAOYSA-N 3,4-dichloro-n-methylaniline Chemical compound CNC1=CC=C(Cl)C(Cl)=C1 DUSNCFKVMGTTFK-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
INGWZEYBHANKIQ-UHFFFAOYSA-N 4-chloro-n-(2-chloroethyl)aniline Chemical compound ClCCNC1=CC=C(Cl)C=C1 INGWZEYBHANKIQ-UHFFFAOYSA-N 0.000 description 1
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
GXEKYRXVRROBEV-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1CC2C(C(O)=O)C(C(=O)O)C1O2 GXEKYRXVRROBEV-UHFFFAOYSA-N 0.000 description 1
101100515516 Arabidopsis thaliana XI-H gene Proteins 0.000 description 1
241000195585 Chlamydomonas Species 0.000 description 1
101000713575 Homo sapiens Tubulin beta-3 chain Proteins 0.000 description 1
241001491711 Melosira Species 0.000 description 1
241000721605 Mougeotia Species 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
241000786363 Rhampholeon spectrum Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
102100036790 Tubulin beta-3 chain Human genes 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910001516 alkali metal iodide Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000003373 anti-fouling effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical class S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
150000005332 diethylamines Chemical class 0.000 description 1
238000007865 diluting Methods 0.000 description 1
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230000007613 environmental effect Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
QUYFJBLQAWHMEK-UHFFFAOYSA-N n',n'-diethyl-n-[4-(trifluoromethoxy)phenyl]ethane-1,2-diamine Chemical compound CCN(CC)CCNC1=CC=C(OC(F)(F)F)C=C1 QUYFJBLQAWHMEK-UHFFFAOYSA-N 0.000 description 1
AMZRCWDZLLMPBU-UHFFFAOYSA-N n',n'-diethyl-n-naphthalen-1-ylethane-1,2-diamine Chemical compound C1=CC=C2C(NCCN(CC)CC)=CC=CC2=C1 AMZRCWDZLLMPBU-UHFFFAOYSA-N 0.000 description 1
SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
231100000956 nontoxicity Toxicity 0.000 description 1
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239000003973 paint Substances 0.000 description 1
230000000361 pesticidal effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
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229920000136 polysorbate Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
239000013535 sea water Substances 0.000 description 1
238000007873 sieving Methods 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
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239000003381 stabilizer Substances 0.000 description 1
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239000010409 thin film Substances 0.000 description 1
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125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
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229910052727 yttrium Inorganic materials 0.000 description 1
AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
- A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/06—Nitrogen directly attached to an aromatic ring system
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom

Landscapes

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

IE1504/79A 1978-07-26 1979-08-08 Algicidal composition and method of preventing or controlling algae with said composition IE48789B1 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
IE122283A IE48790B1 (en)	1978-07-26	1979-08-08	Algicidal n-(substituted phenyl)-n',n'-diethyl ethylene diamines

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL7807908		1978-07-26

Publications (2)

Publication Number	Publication Date
IE791504L IE791504L (en)	1980-01-26
IE48789B1 true IE48789B1 (en)	1985-05-15

Family

ID=19831300

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE1504/79A IE48789B1 (en)	1978-07-26	1979-08-08	Algicidal composition and method of preventing or controlling algae with said composition

Country Status (16)

Country	Link
US (3)	US4286983A ( )
JP (1)	JPS5519300A ( )
AU (1)	AU526440B2 ( )
BE (1)	BE877867A ( )
DD (1)	DD145049A5 ( )
DE (1)	DE2929181A1 ( )
DK (1)	DK309179A ( )
ES (2)	ES482799A1 ( )
FR (1)	FR2437785A1 ( )
GB (2)	GB2026867B ( )
IE (1)	IE48789B1 ( )
IL (1)	IL57868A ( )
IT (1)	IT1193208B ( )
PH (1)	PH15779A ( )
SE (1)	SE7906293L ( )
ZA (1)	ZA793568B ( )

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA793568B (en) *	1978-07-26	1981-02-25	Duphar Int Res	Algicidal composition
DE3000441A1 (de) *	1980-01-08	1981-07-09	Merck Patent Gmbh, 6100 Darmstadt	Anilinderivate,,diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung
JPS6132451Y2 ( ) *	1980-03-08	1986-09-20
HU184392B (en) *	1981-03-04	1984-08-28	Gyogyszerkutato Intezet	Process for producing new alkylene-diamine derivatives
US4435425A (en)	1982-04-09	1984-03-06	Merrell Toraude Et Compagnie	Fluorinated diaminobutane derivatives
US5071569A (en) *	1990-03-22	1991-12-10	Coral International, Inc.	Method and composition for water treatment
US5334389A (en) *	1992-10-15	1994-08-02	Duke University	Antifouling coating and method for using same
US7951989B2 (en) *	1998-02-23	2011-05-31	Phylonix Pharmaceuticals, Inc.	Methods of screening agents for activity using teleosts
EP1066402B1 (en) *	1998-02-23	2005-05-18	Phylonix Pharmaceuticals Inc.	Methods of screening agents for activity using teleosts
US6656449B1 (en)	1998-02-23	2003-12-02	Phylonix Pharmaceuticals, Inc.	Methods of screening agents for activity using teleosts
US5958836A (en) *	1998-09-26	1999-09-28	Triquest, Lp	Algistats
ES2286908T3 (es)	1998-12-01	2007-12-01	Phylonix Pharmaceuticals Inc.	Metodos para introducir celulas heterologas en peces.
KR101819190B1 (ko) *	2015-10-14	2018-01-16	주식회사 큐얼스	미세조류 파괴용 조성물

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2830056A (en) *		1958-04-08		Chj oh
US2634293A (en) *	1946-10-04	1953-04-07	Monsanto Chemicals	Process of preparing a monobasic salt of a secondary amine
US2739981A (en) *	1952-08-26	1956-03-27	American Home Prod	Diamines and salts thereof
US3173917A (en) *	1960-11-25	1965-03-16	American Cyanamid Co	Method of preparing substituted phenylpiperazines
GB1016071A (en) *	1961-02-15	1966-01-05	Smith Kline French Lab	New guanidine derivatives and process for preparing the same
US3532749A (en) *	1965-05-11	1970-10-06	Aldrich Chem Co Inc	N'-propargyl-n**2-cyclopropyl-ethylenediamines and the salts thereof
US3394137A (en) *	1966-12-05	1968-07-23	Dow Chemical Co	Nu-pentachlorophenyl piperazine derivatives
DE1643384A1 (de)	1967-12-27	1971-06-09	Bayer Ag	Algizide Mittel
US3928603A (en) *	1970-10-28	1975-12-23	Fuveau Sa	New derivatives of alpha-methyl benzylamine in treating inflammation
US3871861A (en) *	1971-04-02	1975-03-18	Millmaster Onyx Corp	Method of inhibiting algae utilizing trimethylbenzylaminoethylamine
US3871862A (en) *	1972-09-25	1975-03-18	Millmaster Onyx Corp	Amino derivatives of tetrasubstituted benzene compounds
US4104383A (en) *	1973-11-02	1978-08-01	C M Industries	Derivatives of phenylpropenylamine
US4060630A (en) *	1975-12-22	1977-11-29	Richardson-Merrell Inc.	Ethylenediamine derivatives useful in treating sickle cell anemia
DE2742174A1 (de) *	1977-09-20	1979-03-29	Bayer Ag	Verfahren zur herstellung von aminen
ZA793568B (en) *	1978-07-26	1981-02-25	Duphar Int Res	Algicidal composition

1979
- 1979-07-16 ZA ZA00793568A patent/ZA793568B/xx unknown
- 1979-07-19 DE DE19792929181 patent/DE2929181A1/de not_active Withdrawn
- 1979-07-20 US US06/059,420 patent/US4286983A/en not_active Expired - Lifetime
- 1979-07-23 GB GB7925573A patent/GB2026867B/en not_active Expired
- 1979-07-23 GB GB8109842A patent/GB2072188B/en not_active Expired
- 1979-07-23 DK DK309179A patent/DK309179A/da not_active Application Discontinuation
- 1979-07-23 IL IL57868A patent/IL57868A/xx unknown
- 1979-07-23 SE SE7906293A patent/SE7906293L/ not_active Application Discontinuation
- 1979-07-23 IT IT24582/79A patent/IT1193208B/it active
- 1979-07-24 ES ES482799A patent/ES482799A1/es not_active Expired
- 1979-07-24 BE BE0/196436A patent/BE877867A/fr not_active IP Right Cessation
- 1979-07-24 PH PH22809A patent/PH15779A/en unknown
- 1979-07-25 DD DD79214604A patent/DD145049A5/de unknown
- 1979-07-26 FR FR7919298A patent/FR2437785A1/fr active Granted
- 1979-07-26 JP JP9556579A patent/JPS5519300A/ja active Granted
- 1979-08-08 IE IE1504/79A patent/IE48789B1/en unknown
- 1979-08-08 AU AU49687/79A patent/AU526440B2/en not_active Ceased
1980
- 1980-04-22 ES ES490775A patent/ES490775A0/es active Granted
- 1980-11-20 US US06/208,791 patent/US4596891A/en not_active Expired - Lifetime
1981
- 1981-06-05 US US06/270,826 patent/US4341548A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
US4341548A (en)	1982-07-27
IT1193208B (it)	1988-06-15
JPS5519300A (en)	1980-02-09
FR2437785A1 (fr)	1980-04-30
IE791504L (en)	1980-01-26
AU4968779A (en)	1980-05-01
JPS6320801B2 ( )	1988-04-30
DD145049A5 (de)	1980-11-19
DE2929181A1 (de)	1980-02-14
PH15779A (en)	1983-03-24
GB2026867B (en)	1982-09-08
AU526440B2 (en)	1983-01-13
ES8107001A1 (es)	1980-12-01
DK309179A (da)	1980-01-27
GB2026867A (en)	1980-02-13
US4286983A (en)	1981-09-01
ES490775A0 (es)	1980-12-01
IT7924582A0 (it)	1979-07-23
ES482799A1 (es)	1980-09-01
US4596891A (en)	1986-06-24
IL57868A (en)	1982-08-31
SE7906293L (sv)	1980-01-28
IL57868A0 (en)	1979-11-30
GB2072188A (en)	1981-09-30
BE877867A (fr)	1980-01-24
FR2437785B1 ( )	1984-06-29
GB2072188B (en)	1983-03-16
ZA793568B (en)	1981-02-25

Publication	Publication Date	Title
JP2793956B2 (ja)	1998-09-03	トリアジン誘導体およびそれを有効成分とする除草剤
IE48789B1 (en)	1985-05-15	Algicidal composition and method of preventing or controlling algae with said composition
DE3013162A1 (de)	1980-10-30	N-substituierte tetrahydrophthalimide und herbizide mittel mit einem gehalt derselben
DE2531643A1 (de)	1976-01-29	Herbizide verbindungen, unkrautvertilgungsmittel, worin diese enthalten sind, und verfahren zu ihrer anwendung
PL154960B1 (en)	1991-10-31	Agent for combating or preventing attack by insects or microorganisms
CS247096B2 (en)	1986-11-13	Fungicide agent for using in agriculature and production method of its effective compound
JPH0242003A (ja)	1990-02-13	工業用殺菌剤
PL139504B1 (en)	1987-01-31	Pesticide and method of obtaining novel derivatives of benzoilurea
JPS6141353B2 ( )	1986-09-13
PL93536B1 ( )	1977-06-30
US3978091A (en)	1976-08-31	2,4-Dimethyl-3-carboxyanilidofuran compounds
CA1117961A (en)	1982-02-09	N-cyano-and n-alkynyl-2-(substituted phenoxy) butyramides and their use as mildewicides
EP0146047B1 (de)	1991-05-22	Mittel zur Beeinflussung des Pflanzenwachstums
US4496559A (en)	1985-01-29	2-Selenopyridine-N-oxide derivatives and their use as fungicides and bactericides
DD219103A5 (de)	1985-02-27	Gegen milben, weisse fliege und thrips wirksame zusammensetzung
CA1282419C (en)	1991-04-02	Imidazoles, their preparation and their use as fungicides
DE2365677C3 (de)	1982-05-06	Verwendung von N-(3,5-Dichlorphenyl)-7-oxabicyclo [2.2.1] heptan-2,3-dicarboximid zur Bekämpfung von Pilzen der Gattung Sclerotinia und Botrytis
DE2637886A1 (de)	1977-03-10	3-pyridyl-oxy-alkancarbonsaeureamide
EA011609B1 (ru)	2009-04-28	Фунгицидные феноксифенилгидразиновые производные
PL135177B1 (en)	1985-10-31	Pesticide and method of manufacture of iodopropargylammonium salts
JPS62205063A (ja)	1987-09-09	新規な２−シアノベンゾイミダゾ−ル誘導体、その製造方法および殺菌剤としてのその使用、並びに他の殺菌剤との組合せ物
DE2643476A1 (de)	1977-04-07	Schaedlingsbekaempfungsmittel
US4315846A (en)	1982-02-16	Metal salt of N-substituted alkylenebisdithiocarbamic acid
PL84075B1 ( )	1976-02-28
DD262025A5 (de)	1988-11-16	Imidazol-derivate