IL116562A - 1,2,3,4-substituted naphthalene compounds for use as pesticides, their preparation and use - Google Patents

1,2,3,4-substituted naphthalene compounds for use as pesticides, their preparation and use

Info

Publication number: IL116562A
Authority: IL; Israel
Prior art keywords: group; formula; compound; alkyl; alkenyl
Prior art date: 1995-01-10

Application number

IL11656295A

Other languages

English (en)

Other versions

IL116562A0 (en

Original Assignee

British Tech Group

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.)

1995-01-10

Filing date

1995-12-26

Publication date

2001-08-08

1995-01-10 Priority claimed from GBGB9500394.3A external-priority patent/GB9500394D0/en

1995-01-10 Priority claimed from GBGB9500389.3A external-priority patent/GB9500389D0/en

1995-12-26 Application filed by British Tech Group filed Critical British Tech Group

1996-03-31 Publication of IL116562A0 publication Critical patent/IL116562A0/xx

2001-08-08 Publication of IL116562A publication Critical patent/IL116562A/en

Links

238000002360 preparation method Methods 0.000 title claims description 18
239000000575 pesticide Substances 0.000 title description 7
150000002790 naphthalenes Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 156
238000000034 method Methods 0.000 claims description 48
125000000217 alkyl group Chemical group 0.000 claims description 41
125000003342 alkenyl group Chemical group 0.000 claims description 27
-1 cyano, hydroxy Chemical group 0.000 claims description 27
125000001188 haloalkyl group Chemical group 0.000 claims description 27
241000607479 Yersinia pestis Species 0.000 claims description 22
125000000753 cycloalkyl group Chemical group 0.000 claims description 22
125000000262 haloalkenyl group Chemical group 0.000 claims description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
230000000694 effects Effects 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
241000233866 Fungi Species 0.000 claims description 16
150000001721 carbon Chemical group 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
125000000547 substituted alkyl group Chemical group 0.000 claims description 11
125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
241000813090 Rhizoctonia solani Species 0.000 claims description 8
125000001624 naphthyl group Chemical group 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
241000228245 Aspergillus niger Species 0.000 claims description 7
241001330975 Magnaporthe oryzae Species 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
238000001727 in vivo Methods 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
230000002538 fungal effect Effects 0.000 claims description 6
125000004438 haloalkoxy group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
241000254127 Bemisia tabaci Species 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
150000003254 radicals Chemical class 0.000 claims description 5
125000005415 substituted alkoxy group Chemical group 0.000 claims description 5
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
241000228212 Aspergillus Species 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
241000231139 Pyricularia Species 0.000 claims description 4
241001361634 Rhizoctonia Species 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
238000010516 chain-walking reaction Methods 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
239000003999 initiator Substances 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
241000255777 Lepidoptera Species 0.000 claims description 2
241000256248 Spodoptera Species 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims 1
241000254123 Bemisia Species 0.000 claims 1
GQZIHDBCHUMFSW-UHFFFAOYSA-N C1CC(C)CCC1C1=C(O)C(=O)C2=CC=CC=C2C1=O Chemical compound C1CC(C)CCC1C1=C(O)C(=O)C2=CC=CC=C2C1=O GQZIHDBCHUMFSW-UHFFFAOYSA-N 0.000 claims 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
125000003172 aldehyde group Chemical group 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 claims 1
230000008030 elimination Effects 0.000 claims 1
238000003379 elimination reaction Methods 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
239000012454 non-polar solvent Substances 0.000 claims 1
239000003495 polar organic solvent Substances 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
239000000203 mixture Substances 0.000 description 26
241000258937 Hemiptera Species 0.000 description 23
238000012360 testing method Methods 0.000 description 18
239000000243 solution Substances 0.000 description 16
241000238876 Acari Species 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
241000238631 Hexapoda Species 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
239000002904 solvent Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
231100000111 LD50 Toxicity 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000011282 treatment Methods 0.000 description 9
241000196324 Embryophyta Species 0.000 description 8
230000000361 pesticidal effect Effects 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
229920001817 Agar Polymers 0.000 description 5
229930192627 Naphthoquinone Natural products 0.000 description 5
241001608567 Phaedon cochleariae Species 0.000 description 5
230000000895 acaricidal effect Effects 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
230000000855 fungicidal effect Effects 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
150000002791 naphthoquinones Chemical class 0.000 description 5
241000255925 Diptera Species 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241000257226 Muscidae Species 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000008272 agar Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
238000001914 filtration Methods 0.000 description 4
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
241000894007 species Species 0.000 description 4
241001124076 Aphididae Species 0.000 description 3
241000283690 Bos taurus Species 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
206010061217 Infestation Diseases 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
230000002824 aphicidal effect Effects 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000000969 carrier Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
239000000417 fungicide Substances 0.000 description 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
OPKFWRVRCVCMJH-UHFFFAOYSA-N 6-methylnaphthalene-1,4-dione Chemical compound O=C1C=CC(=O)C2=CC(C)=CC=C21 OPKFWRVRCVCMJH-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
238000007792 addition Methods 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Chemical group 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
125000002993 cycloalkylene group Chemical group 0.000 description 2
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
238000001212 derivatisation Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
229910001961 silver nitrate Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 1
229940005561 1,4-benzoquinone Drugs 0.000 description 1
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
LZCBWTIQIXZAKZ-UHFFFAOYSA-N 2-(aminomethyl)naphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(CN)=CC(=O)C2=C1 LZCBWTIQIXZAKZ-UHFFFAOYSA-N 0.000 description 1
WVCHIGAIXREVNS-UHFFFAOYSA-N 2-hydroxy-1,4-naphthoquinone Chemical compound C1=CC=C2C(O)=CC(=O)C(=O)C2=C1 WVCHIGAIXREVNS-UHFFFAOYSA-N 0.000 description 1
XBGHCDVBZZNDBY-UHFFFAOYSA-N 3-cyclohexyl-4-hydroxynaphthalene-1,2-dione Chemical compound O=C1C(=O)C2=CC=CC=C2C(O)=C1C1CCCCC1 XBGHCDVBZZNDBY-UHFFFAOYSA-N 0.000 description 1
FFZMMBKGTNDVRX-UHFFFAOYSA-N 4,4,4-trifluoro-3-methylbutanoic acid Chemical compound FC(F)(F)C(C)CC(O)=O FFZMMBKGTNDVRX-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
QTDXSEZXAPHVBI-UHFFFAOYSA-N 4-methylcyclohexane-1-carboxylic acid Chemical compound CC1CCC(C(O)=O)CC1 QTDXSEZXAPHVBI-UHFFFAOYSA-N 0.000 description 1
QRDZSRWEULKVNW-UHFFFAOYSA-N 6-hydroxy-2-oxo-1h-quinoline-4-carboxylic acid Chemical group C1=C(O)C=C2C(C(=O)O)=CC(=O)NC2=C1 QRDZSRWEULKVNW-UHFFFAOYSA-N 0.000 description 1
239000004160 Ammonium persulphate Substances 0.000 description 1
241001480061 Blumeria graminis Species 0.000 description 1
241001465180 Botrytis Species 0.000 description 1
241000123650 Botrytis cinerea Species 0.000 description 1
241001065413 Botrytis fabae Species 0.000 description 1
241001101608 Bouvardia Species 0.000 description 1
239000005885 Buprofezin Substances 0.000 description 1
TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
239000005946 Cypermethrin Substances 0.000 description 1
241000489975 Diabrotica Species 0.000 description 1
241000489947 Diabrotica virgifera virgifera Species 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
238000005698 Diels-Alder reaction Methods 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
241000221787 Erysiphe Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000735332 Gerbera Species 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
241001344131 Magnaporthe grisea Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000257159 Musca domestica Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
241001494479 Pecora Species 0.000 description 1
239000005820 Prochloraz Substances 0.000 description 1
208000010362 Protozoan Infections Diseases 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
QDRXWCAVUNHOGA-UHFFFAOYSA-N acequinocyl Chemical compound C1=CC=C2C(=O)C(CCCCCCCCCCCC)=C(OC(C)=O)C(=O)C2=C1 QDRXWCAVUNHOGA-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
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239000007864 aqueous solution Substances 0.000 description 1
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000004181 carboxyalkyl group Chemical group 0.000 description 1
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238000006555 catalytic reaction Methods 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
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GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
238000004040 coloring Methods 0.000 description 1
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229940125797 compound 12 Drugs 0.000 description 1
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239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
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VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
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239000012024 dehydrating agents‎ Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
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238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
235000021186 dishes Nutrition 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
238000007429 general method Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
125000004969 haloethyl group Chemical group 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
230000036541 health Effects 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
CSFWPUWCSPOLJW-UHFFFAOYSA-N hydroxynaphthoquinone Natural products C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000003137 locomotive effect Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
201000004792 malaria Diseases 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
230000003129 miticidal effect Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
239000003986 organophosphate insecticide Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000003544 oxime group Chemical group 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000002304 perfume Substances 0.000 description 1
230000002688 persistence Effects 0.000 description 1
239000001965 potato dextrose agar Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000011514 reflex Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000003252 repetitive effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

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

IL11656295A 1995-01-10 1995-12-26 1,2,3,4-substituted naphthalene compounds for use as pesticides, their preparation and use IL116562A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GBGB9500394.3A GB9500394D0 (en)	1995-01-10	1995-01-10	Pesticidal compounds
GBGB9500389.3A GB9500389D0 (en)	1995-01-10	1995-01-10	Pesticidal compounds
GBGB9513584.4A GB9513584D0 (en)	1995-01-10	1995-07-04	Pesticidal compounds
GBGB9513594.3A GB9513594D0 (en)	1995-01-10	1995-07-04	Pesticidal compounds

Publications (2)

Publication Number	Publication Date
IL116562A0 IL116562A0 (en)	1996-03-31
IL116562A true IL116562A (en)	2001-08-08

Family

ID=27451248

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL11656295A IL116562A (en)	1995-01-10	1995-12-26	1,2,3,4-substituted naphthalene compounds for use as pesticides, their preparation and use

Country Status (3)

Country	Link
AR (1)	AR001788A1 (es)
BR (1)	BR9606742A (es)
IL (1)	IL116562A (es)

1995
- 1995-12-26 IL IL11656295A patent/IL116562A/en not_active IP Right Cessation
1996
- 1996-01-09 AR AR33496296A patent/AR001788A1/es unknown
- 1996-01-10 BR BR9606742A patent/BR9606742A/pt not_active IP Right Cessation

Also Published As

Publication number	Publication date
IL116562A0 (en)	1996-03-31
AR001788A1 (es)	1997-12-10
BR9606742A (pt)	1997-12-30

Publication	Publication Date	Title
JP3279818B2 (ja)	2002-04-30	殺虫・殺ダニ剤
EP0802730B1 (en)	1999-06-23	Pesticidal compounds
EP0802729A1 (en)	1997-10-29	Pesticidal compounds
AU699685C (en)	2000-02-24	Pesticidal compounds
US6162799A (en)	2000-12-19	Pesticidal compounds
US6043286A (en)	2000-03-28	Pesticidal compounds
IL116562A (en)	2001-08-08	1,2,3,4-substituted naphthalene compounds for use as pesticides, their preparation and use
JP3625012B2 (ja)	2005-03-02	殺虫殺菌組成物
EP0759898B1 (en)	1999-07-14	Naphthoquinone derivatives
RU2173049C2 (ru)	2001-09-10	Замещенные нафталин-1,4-дионы, обладающие пестицидными свойствами, способ их получения, их применение в качестве пестицидов, способ борьбы с вредителями с применением таких соединений и содержащие их пестицидные композиции
US5962002A (en)	1999-10-05	Pesticidal compounds
RU2180330C2 (ru)	2002-03-10	1,2,3,4-замещенные нафталиновые соединения, способ их получения, способ борьбы с вредителями, пестицидная композиция
RU2174981C2 (ru)	2001-10-20	Производные нафтохинона, инсектицидноакарицидная и/или фунгицидная композиция, способ борьбы с грибками, и/или насекомыми, и/или акаридами
CA2209906A1 (en)	1996-07-18	Pesticidal compounds
JPH0761923B2 (ja)	1995-07-05	殺菌剤
JPH02288852A (ja)	1990-11-28	殺虫性化合物
KR19980701324A (ko)	1998-05-15	해충구제용 화합물(pesticidal compounds)
JPS63502272A (ja)	1988-09-01	Ｎ−（ビニルオキシエチル）ジチオカルバミン酸塩、その製造方法およびその塩に基づく農薬
MXPA98000140A (es)	1998-10-15	Compuestos plaguicidas
JPS58118533A (ja)	1983-07-14	３−フエノキシ−４−フルオロベンジル２−（４−エトキシフエニル）−２−メチルプロピルエ−テル、その製造法および殺虫、殺ダニ剤
CN1177907A (zh)	1998-04-01	农药化合物
FR2490930A1 (fr)	1982-04-02	Composition pesticide a base d'un derive phosphorothiolate et d'un compose pyrethroide pour la destruction des insectes

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2002-02-10	FF	Patent granted
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2006-09-05	MM9K	Patent not in force due to non-payment of renewal fees