OA10124A - Pesticidal pyrimidine compounds - Google Patents

Pesticidal pyrimidine compounds Download PDF

Info

Publication number: OA10124A
Authority: OA; OAPI
Prior art keywords: hydrogen; group; atom; alkyl; compound
Prior art date: 1992-07-17

Application number

OA60603A

Other languages

English (en)

Inventor

David Munro

Royston Davis

Janet Anne Day

Jacqueline Ann Wilkin

William Wakefield Wood

Original Assignee

Shell Int Research

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.)

1992-07-17

Filing date

1995-01-12

Publication date

1996-12-18

1995-01-12 Application filed by Shell Int Research filed Critical Shell Int Research

1996-12-18 Publication of OA10124A publication Critical patent/OA10124A/en

Links

230000000361 pesticidal effect Effects 0.000 title claims abstract description 7
150000003230 pyrimidines Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 75
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
239000001257 hydrogen Substances 0.000 claims abstract description 33
125000000217 alkyl group Chemical group 0.000 claims abstract description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 29
-1 haloalkylsulphinyl Chemical group 0.000 claims abstract description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 13
125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 10
239000000460 chlorine Substances 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
125000004994 halo alkoxy alkyl group Chemical group 0.000 claims abstract description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 4
125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 3
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims abstract description 3
125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 3
125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 30
125000005843 halogen group Chemical group 0.000 claims description 18
238000000034 method Methods 0.000 claims description 17
229910052731 fluorine Inorganic materials 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
241000607479 Yersinia pestis Species 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
DRTIDKPIEULFOI-UHFFFAOYSA-N 4,6-diphenoxypyrimidin-2-amine Chemical compound C=1C(OC=2C=CC=CC=2)=NC(N)=NC=1OC1=CC=CC=C1 DRTIDKPIEULFOI-UHFFFAOYSA-N 0.000 claims description 3
244000078703 ectoparasite Species 0.000 claims description 3
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000005675 difluoroethenyl group Chemical group [H]C(*)=C(F)F 0.000 claims description 2
125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 6
DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical group CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 claims 1
CLCYVWGIDJIJLS-UHFFFAOYSA-N 4-n-(3-chlorophenyl)-6-(3-chlorophenyl)imino-5h-pyrimidine-2,4-diamine Chemical compound N1C(N)=NC(=NC=2C=C(Cl)C=CC=2)CC1=NC1=CC=CC(Cl)=C1 CLCYVWGIDJIJLS-UHFFFAOYSA-N 0.000 claims 1
235000005544 Acinos arvensis Nutrition 0.000 claims 1
244000207178 Acinos arvensis Species 0.000 claims 1
125000003342 alkenyl group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 abstract description 9
229910052736 halogen Inorganic materials 0.000 abstract description 5
150000002367 halogens Chemical class 0.000 abstract description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 4
229910052760 oxygen Inorganic materials 0.000 abstract description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
239000001301 oxygen Substances 0.000 abstract 1
238000012360 testing method Methods 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
230000000895 acaricidal effect Effects 0.000 description 15
239000000047 product Substances 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
230000000694 effects Effects 0.000 description 8
235000013601 eggs Nutrition 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000004094 surface-active agent Substances 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 7
239000007787 solid Substances 0.000 description 7
241000238876 Acari Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
239000011734 sodium Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
241001454293 Tetranychus urticae Species 0.000 description 5
239000000969 carrier Substances 0.000 description 5
239000002917 insecticide Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
241000894007 species Species 0.000 description 5
239000000725 suspension Substances 0.000 description 5
230000001988 toxicity Effects 0.000 description 5
231100000419 toxicity Toxicity 0.000 description 5
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
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 4
244000046052 Phaseolus vulgaris Species 0.000 description 4
238000009835 boiling Methods 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
229940093499 ethyl acetate Drugs 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
229940117927 ethylene oxide Drugs 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000642 acaricide Substances 0.000 description 3
239000000654 additive Substances 0.000 description 3
239000003513 alkali Substances 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
229910000323 aluminium silicate Inorganic materials 0.000 description 3
229950005499 carbon tetrachloride Drugs 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
YMWAEUVISMTDQH-UHFFFAOYSA-N 4,6-bis[3-(trifluoromethyl)phenoxy]-1h-pyrimidin-2-one Chemical compound FC(F)(F)C1=CC=CC(OC2=NC(=O)NC(OC=3C=C(C=CC=3)C(F)(F)F)=C2)=C1 YMWAEUVISMTDQH-UHFFFAOYSA-N 0.000 description 2
CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
241000258937 Hemiptera Species 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241001454294 Tetranychus Species 0.000 description 2
241000018137 Trialeurodes vaporariorum Species 0.000 description 2
239000011149 active material Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
230000009969 flowable effect Effects 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
238000013101 initial test Methods 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
OPXLLQIJSORQAM-UHFFFAOYSA-N mebendazole Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1C(=O)C1=CC=CC=C1 OPXLLQIJSORQAM-UHFFFAOYSA-N 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
239000012085 test solution Substances 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DPVIABCMTHHTGB-UHFFFAOYSA-N 2,4,6-trichloropyrimidine Chemical compound ClC1=CC(Cl)=NC(Cl)=N1 DPVIABCMTHHTGB-UHFFFAOYSA-N 0.000 description 1
BOTNFCTYKJBUMU-UHFFFAOYSA-N 2-[4-(2-methylpropyl)piperazin-4-ium-1-yl]-2-oxoacetate Chemical compound CC(C)C[NH+]1CCN(C(=O)C([O-])=O)CC1 BOTNFCTYKJBUMU-UHFFFAOYSA-N 0.000 description 1
IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
WMHSWGPTVOZBRT-UHFFFAOYSA-N 2-bromo-4,6-bis[3-(trifluoromethyl)phenoxy]pyrimidine Chemical compound FC(F)(F)C1=CC=CC(OC=2N=C(Br)N=C(OC=3C=C(C=CC=3)C(F)(F)F)C=2)=C1 WMHSWGPTVOZBRT-UHFFFAOYSA-N 0.000 description 1
DGXRGGUNBXNJRI-UHFFFAOYSA-N 2-methyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(C)=C1 DGXRGGUNBXNJRI-UHFFFAOYSA-N 0.000 description 1
UGEJOEBBMPOJMT-UHFFFAOYSA-N 3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1 UGEJOEBBMPOJMT-UHFFFAOYSA-N 0.000 description 1
VHQANZSFKIKHCO-UHFFFAOYSA-N 4,6-bis[4-chloro-3-(trifluoromethyl)phenoxy]pyrimidine 4-chloro-3-(trifluoromethyl)phenol Chemical compound ClC1=C(C=C(C=C1)O)C(F)(F)F.ClC1=C(C=C(OC2=NC=NC(=C2)OC2=CC(=C(C=C2)Cl)C(F)(F)F)C=C1)C(F)(F)F VHQANZSFKIKHCO-UHFFFAOYSA-N 0.000 description 1
YFUDLRFOGLVNNA-UHFFFAOYSA-N 4,6-dichloro-1h-pyrimidin-2-one Chemical compound ClC=1C=C(Cl)NC(=O)N=1 YFUDLRFOGLVNNA-UHFFFAOYSA-N 0.000 description 1
QFWVAJQVYBRTCL-UHFFFAOYSA-N 4,6-dichloro-2-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=NC(Cl)=CC(Cl)=N1 QFWVAJQVYBRTCL-UHFFFAOYSA-N 0.000 description 1
MCLDVUCSDZGNRR-UHFFFAOYSA-N 4,6-difluoropyrimidine Chemical compound FC1=CC(F)=NC=N1 MCLDVUCSDZGNRR-UHFFFAOYSA-N 0.000 description 1
CPYSKABWRUCXBU-UHFFFAOYSA-N 4-[6-[4-fluoro-3-(trifluoromethyl)phenoxy]pyrimidin-4-yl]oxybenzonitrile Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1OC1=CC(OC=2C=CC(=CC=2)C#N)=NC=N1 CPYSKABWRUCXBU-UHFFFAOYSA-N 0.000 description 1
YGNISOAUPSJDJE-UHFFFAOYSA-N 4-bromo-3-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Br)C(C(F)(F)F)=C1 YGNISOAUPSJDJE-UHFFFAOYSA-N 0.000 description 1
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005874 Bifenthrin Substances 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
101100340271 Caenorhabditis elegans ida-1 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000283707 Capra Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
102100036372 Carbonic anhydrase 5A, mitochondrial Human genes 0.000 description 1
101710133954 Carbonic anhydrase 5A, mitochondrial Proteins 0.000 description 1
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XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000001984 ectoparasiticidal effect Effects 0.000 description 1
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229910052618 mica group Inorganic materials 0.000 description 1
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238000007254 oxidation reaction Methods 0.000 description 1
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WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
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YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
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239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
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LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
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QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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235000011152 sodium sulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000012414 tert-butyl nitrite Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/58—Two sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Environmental Sciences (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Pest Control & Pesticides (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Agronomy & Crop Science (AREA)
Plant Pathology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Tropical Medicine & Parasitology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

OA60603A 1992-07-17 1995-01-12 Pesticidal pyrimidine compounds OA10124A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP92306600		1992-07-17

Publications (1)

Publication Number	Publication Date
OA10124A true OA10124A (en)	1996-12-18

Family

ID=8211436

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA60603A OA10124A (en)	1992-07-17	1995-01-12	Pesticidal pyrimidine compounds

Country Status (27)

Country	Link
US (1)	US5707995A (pl)
EP (1)	EP0650482B1 (pl)
JP (1)	JP3353895B2 (pl)
KR (1)	KR950702541A (pl)
CN (1)	CN1087085A (pl)
AT (1)	ATE206404T1 (pl)
AU (1)	AU671845B2 (pl)
CA (1)	CA2140346A1 (pl)
CZ (1)	CZ282275B6 (pl)
DE (1)	DE69330882T2 (pl)
DK (1)	DK0650482T3 (pl)
EG (1)	EG20267A (pl)
ES (1)	ES2164666T3 (pl)
GE (1)	GEP19981224B (pl)
HU (1)	HUT70086A (pl)
IL (1)	IL106324A (pl)
MD (1)	MD1154F2 (pl)
OA (1)	OA10124A (pl)
PL (6)	PL173021B1 (pl)
PT (1)	PT650482E (pl)
RU (1)	RU95105445A (pl)
SG (1)	SG49712A1 (pl)
SK (1)	SK279516B6 (pl)
TR (1)	TR26781A (pl)
TW (1)	TW234077B (pl)
WO (1)	WO1994002470A1 (pl)
ZA (1)	ZA935155B (pl)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE53930B1 (en)	1982-04-07	1989-04-12	Nat Res Dev	Endoprosthetic bone joint devices
US6235887B1 (en)	1991-11-26	2001-05-22	Isis Pharmaceuticals, Inc.	Enhanced triple-helix and double-helix formation directed by oligonucleotides containing modified pyrimidines
GB9325217D0 (en) *	1993-12-09	1994-02-09	Zeneca Ltd	Pyrimidine derivatives
EP0723960B1 (en) *	1995-01-26	2003-04-02	Basf Aktiengesellschaft	Herbicidal 2,6-disubstituted pyridines and 2,4-disubstituted pyrimidines
US5849758A (en) *	1995-05-30	1998-12-15	American Cyanamid Company	Herbicidal 2, 6-disubstituted pyridines and 2, 4-disubstituted pyrimidines
CZ290330B6 (cs) *	1995-01-26	2002-07-17	American Cyanamid Company	2,6-Disubstituované pyridinové a 2,4-disubstituované pyrimidinové deriváty, způsob a meziprodukty pro jejich výrobu, jejich pouľití a herbicidní prostředky na jejich bázi a způsob potlačování růstu neľádoucích rostlin
ATE251141T1 (de)	1995-03-10	2003-10-15	Berlex Lab	Benzamidin-derivate, deren herstellung und deren verwendung als anti-koagulantien
US5994375A (en) *	1996-02-12	1999-11-30	Berlex Laboratories, Inc.	Benzamidine derivatives substituted by amino acid and hydroxy acid derivatives and their use as anti-coagulants
UA53611C2 (uk) *	1996-03-07	2003-02-17	Амерікан Ціанамід Компані	Спосіб одержання несиметричних 4,6-біс(арилокси)піримідинових сполук
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1993
- 1993-07-13 IL IL10632493A patent/IL106324A/en unknown
- 1993-07-13 TW TW082105581A patent/TW234077B/zh active
- 1993-07-15 HU HU9500127A patent/HUT70086A/hu unknown
- 1993-07-15 AT AT93915936T patent/ATE206404T1/de not_active IP Right Cessation
- 1993-07-15 KR KR1019950700201A patent/KR950702541A/ko not_active Application Discontinuation
- 1993-07-15 SK SK32-95A patent/SK279516B6/sk unknown
- 1993-07-15 SG SG1996004295A patent/SG49712A1/en unknown
- 1993-07-15 PL PL93307131A patent/PL173021B1/pl unknown
- 1993-07-15 AU AU45700/93A patent/AU671845B2/en not_active Ceased
- 1993-07-15 PL PL93317717A patent/PL173717B1/pl unknown
- 1993-07-15 PL PL93317719A patent/PL173056B1/pl unknown
- 1993-07-15 US US08/351,477 patent/US5707995A/en not_active Expired - Fee Related
- 1993-07-15 PL PL93317720A patent/PL173467B1/pl unknown
- 1993-07-15 MD MD95-0235A patent/MD1154F2/ro unknown
- 1993-07-15 DK DK93915936T patent/DK0650482T3/da active
- 1993-07-15 EG EG44493A patent/EG20267A/xx active
- 1993-07-15 CA CA002140346A patent/CA2140346A1/en not_active Abandoned
- 1993-07-15 RU RU95105445/04A patent/RU95105445A/ru unknown
- 1993-07-15 ES ES93915936T patent/ES2164666T3/es not_active Expired - Lifetime
- 1993-07-15 WO PCT/EP1993/001880 patent/WO1994002470A1/en active IP Right Grant
- 1993-07-15 PL PL93317716A patent/PL173066B1/pl unknown
- 1993-07-15 CZ CZ9530A patent/CZ282275B6/cs unknown
- 1993-07-15 GE GEAP19932333A patent/GEP19981224B/en unknown
- 1993-07-15 PT PT93915936T patent/PT650482E/pt unknown
- 1993-07-15 DE DE69330882T patent/DE69330882T2/de not_active Expired - Fee Related
- 1993-07-15 EP EP93915936A patent/EP0650482B1/en not_active Expired - Lifetime
- 1993-07-15 JP JP50413894A patent/JP3353895B2/ja not_active Expired - Fee Related
- 1993-07-15 PL PL93317718A patent/PL173091B1/pl unknown
- 1993-07-16 ZA ZA935155A patent/ZA935155B/xx unknown
- 1993-07-16 CN CN93116763A patent/CN1087085A/zh active Pending
- 1993-07-19 TR TR93/0604A patent/TR26781A/xx unknown
1995
- 1995-01-12 OA OA60603A patent/OA10124A/en unknown

Also Published As

Publication number	Publication date
RU95105445A (ru)	1996-10-27
PL173717B1 (pl)	1998-04-30
JP3353895B2 (ja)	2002-12-03
PL307131A1 (en)	1995-05-02
PT650482E (pt)	2002-03-28
IL106324A0 (en)	1993-11-15
CZ282275B6 (cs)	1997-06-11
MD1154F2 (ro)	1999-02-28
DK0650482T3 (da)	2001-12-03
TR26781A (tr)	1995-05-15
CA2140346A1 (en)	1994-02-03
KR950702541A (ko)	1995-07-29
EP0650482A1 (en)	1995-05-03
EP0650482B1 (en)	2001-10-04
DE69330882T2 (de)	2002-04-11
AU671845B2 (en)	1996-09-12
HUT70086A (en)	1995-09-28
SK3295A3 (en)	1995-05-10
ZA935155B (en)	1994-06-20
WO1994002470A1 (en)	1994-02-03
JPH07508999A (ja)	1995-10-05
US5707995A (en)	1998-01-13
IL106324A (en)	1998-09-24
ES2164666T3 (es)	2002-03-01
PL173056B1 (pl)	1998-01-30
GEP19981224B (en)	1998-02-11
PL173467B1 (pl)	1998-03-31
DE69330882D1 (de)	2001-11-08
EG20267A (en)	1998-05-31
CN1087085A (zh)	1994-05-25
PL173091B1 (pl)	1998-01-30
PL173066B1 (pl)	1998-01-30
CZ3095A3 (en)	1995-09-13
SK279516B6 (sk)	1998-12-02
TW234077B (pl)	1994-11-11
SG49712A1 (en)	1998-06-15
MD950235A (ro)	1997-10-31
ATE206404T1 (de)	2001-10-15
PL173021B1 (pl)	1998-01-30
AU4570093A (en)	1994-02-14

Publication	Publication Date	Title
OA10124A (en)	1996-12-18	Pesticidal pyrimidine compounds
EP0369526B1 (en)	1995-07-26	Nitromethylene compounds, their preparation and their use as pesticides
JPS62263162A (ja)	1987-11-16	置換２，４−ジアミノ−５−シアノピリミジン及び該化合物を含有する有害生物防除剤
US5134144A (en)	1992-07-28	Pesticidal 3-arylpyrimidinyl ethers and thioethers
US5225423A (en)	1993-07-06	Butenone compounds, their preparation and their use as pesticides
EP0411706B1 (en)	1994-12-07	Sulphonamide herbicides
EP0103918B1 (en)	1987-07-29	Pesticidal benzoylurea compounds
JPS6368559A (ja)	1988-03-28	置換チオ尿素、イソチオ尿素及びカルボジイミド化合物、それらの製法、有害生物防除剤としてのそれらの使用及び該化合物製造用中間体
EP0375069B1 (en)	1994-03-09	Benzamide compounds, their preparation and their use as pesticides
KR960010344B1 (ko)	1996-07-30	치환된 2,4-디아미노-5-시아노피리미딘 및 이들 화합물의 제조방법
EP0605059A1 (en)	1994-07-06	Nitromethylene compounds and their use as pesticides
CA2122178A1 (en)	1994-10-31	Biocidal compounds
GB2181125A (en)	1987-04-15	Pesticidal benzoylurea compounds
JPS6178759A (ja)	1986-04-22	置換カルボジイミド及びその製造方法並びに殺虫・殺ダニ組成物
JPS62230768A (ja)	1987-10-09	Ｎ−ピリジルオキシフエニルイソチオ尿素、その製造方法及び該化合物を含有する有害生物防除用組成物