IL96113A - Insecticidal miticidal and nematocidal compositions containing pyrimidinyl benzoic acids and esters processes for the preparation thereof and some novel pyrimidinyl benzoic acids and esters - Google Patents

Insecticidal miticidal and nematocidal compositions containing pyrimidinyl benzoic acids and esters processes for the preparation thereof and some novel pyrimidinyl benzoic acids and esters

Info

Publication number: IL96113A
Authority: IL; Israel
Prior art keywords: hydrogen; alkyl; hydrocarbyl; halogen; independently
Prior art date: 1989-11-17

Application number

IL9611390A

Other languages

English (en)

Other versions

IL96113A0 (en

Original Assignee

Uniroyal Chemical Ltd

Uniroyal Chem Co Inc

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.)

1989-11-17

Filing date

1990-10-25

Publication date

1995-08-31

1990-10-25 Application filed by Uniroyal Chemical Ltd, Uniroyal Chem Co Inc filed Critical Uniroyal Chemical Ltd

1991-07-18 Publication of IL96113A0 publication Critical patent/IL96113A0/xx

1995-08-31 Publication of IL96113A publication Critical patent/IL96113A/en

Links

239000000203 mixture Substances 0.000 title claims abstract description 22
238000000034 method Methods 0.000 title claims abstract description 12
230000000749 insecticidal effect Effects 0.000 title claims abstract description 9
230000001069 nematicidal effect Effects 0.000 title claims abstract description 7
230000003129 miticidal effect Effects 0.000 title claims abstract description 5
150000002148 esters Chemical class 0.000 title description 7
238000002360 preparation method Methods 0.000 title description 6
BCLGTIBYZQQFJW-UHFFFAOYSA-N 2-pyrimidin-2-ylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1C1=NC=CC=N1 BCLGTIBYZQQFJW-UHFFFAOYSA-N 0.000 title 2
150000001875 compounds Chemical class 0.000 claims abstract description 45
-1 class of aryl pyrimidine derivatives Chemical class 0.000 claims abstract description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 70
239000001257 hydrogen Substances 0.000 claims description 70
125000001183 hydrocarbyl group Chemical group 0.000 claims description 51
125000000217 alkyl group Chemical group 0.000 claims description 41
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
150000002431 hydrogen Chemical group 0.000 claims description 25
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
229910052736 halogen Inorganic materials 0.000 claims description 22
150000002367 halogens Chemical group 0.000 claims description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
239000003513 alkali Chemical group 0.000 claims description 12
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
241000238876 Acari Species 0.000 claims description 9
241000238631 Hexapoda Species 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
241000244206 Nematoda Species 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
150000001342 alkaline earth metals Chemical group 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
229910052717 sulfur Chemical group 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 5
229910052700 potassium Inorganic materials 0.000 claims 5
239000011591 potassium Substances 0.000 claims 5
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
125000004001 thioalkyl group Chemical group 0.000 claims 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
241000607479 Yersinia pestis Species 0.000 abstract description 4
230000000361 pesticidal effect Effects 0.000 abstract description 4
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000002904 solvent Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
241000209094 Oryza Species 0.000 description 12
235000007164 Oryza sativa Nutrition 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
235000009566 rice Nutrition 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
238000012360 testing method Methods 0.000 description 11
241000196324 Embryophyta Species 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
241001466042 Fulgoromorpha Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
239000002689 soil Substances 0.000 description 5
241001498622 Cixius wagneri Species 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
239000002917 insecticide Substances 0.000 description 4
238000003359 percent control normalization Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
241000721621 Myzus persicae Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
241000722027 Schizaphis graminum Species 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
239000000642 acaricide Substances 0.000 description 3
150000004982 aromatic amines Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
XXXSCJQGBPSJMJ-UHFFFAOYSA-N propan-2-yl 5-isocyanato-2-methylbenzoate Chemical compound CC(C)OC(=O)C1=CC(N=C=O)=CC=C1C XXXSCJQGBPSJMJ-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
239000011550 stock solution Substances 0.000 description 3
XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical class CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
206010061217 Infestation Diseases 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
241000722272 Schizaphis Species 0.000 description 2
240000003768 Solanum lycopersicum Species 0.000 description 2
241000194622 Tagosodes orizicolus Species 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
239000000969 carrier Substances 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
239000012043 crude product Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
150000002081 enamines Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000002363 herbicidal effect Effects 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
VENXSELNXQXCNT-IJYXXVHRSA-N metaraminol bitartrate Chemical compound [H+].[H+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O.C[C@H](N)[C@H](O)C1=CC=CC(O)=C1 VENXSELNXQXCNT-IJYXXVHRSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
238000005580 one pot reaction Methods 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DJRFJAVPROZZFL-UHFFFAOYSA-N 1975-52-6 Chemical compound CC1=CC=C([N+]([O-])=O)C=C1C(O)=O DJRFJAVPROZZFL-UHFFFAOYSA-N 0.000 description 1
OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
SHVCSCWHWMSGTE-UHFFFAOYSA-N 6-methyluracil Chemical compound CC1=CC(=O)NC(=O)N1 SHVCSCWHWMSGTE-UHFFFAOYSA-N 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
241001414720 Cicadellidae Species 0.000 description 1
241000256113 Culicidae Species 0.000 description 1
241000255925 Diptera Species 0.000 description 1
241000995023 Empoasca Species 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
241000243785 Meloidogyne javanica Species 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
241000526145 Psylla Species 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
240000006394 Sorghum bicolor Species 0.000 description 1
235000011684 Sorghum saccharatum Nutrition 0.000 description 1
241000368303 Unaspis citri Species 0.000 description 1
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
235000010726 Vigna sinensis Nutrition 0.000 description 1
244000042314 Vigna unguiculata Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
238000000160 carbon, hydrogen and nitrogen elemental analysis Methods 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000013078 crystal Substances 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000000428 dust Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
239000000469 ethanolic extract Substances 0.000 description 1
JQGQFCBRPKXRHM-UHFFFAOYSA-N ethyl 2,4,4,4-tetrafluoro-3-oxobutanoate Chemical compound CCOC(=O)C(F)C(=O)C(F)(F)F JQGQFCBRPKXRHM-UHFFFAOYSA-N 0.000 description 1
CTIIDKOCCAZEDV-UHFFFAOYSA-N ethyl 3-amino-2,4,4,4-tetrafluorobut-2-enoate Chemical compound CCOC(=O)C(F)=C(N)C(F)(F)F CTIIDKOCCAZEDV-UHFFFAOYSA-N 0.000 description 1
NXVKRKUGIINGHD-UHFFFAOYSA-N ethyl 3-amino-4,4,4-trifluorobut-2-enoate Chemical class CCOC(=O)C=C(N)C(F)(F)F NXVKRKUGIINGHD-UHFFFAOYSA-N 0.000 description 1
OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 description 1
239000000835 fiber Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
239000008263 liquid aerosol Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
FEMGFJFVGWMKRG-UHFFFAOYSA-N propan-2-yl 5-amino-2-methylbenzoate Chemical compound CC(C)OC(=O)C1=CC(N)=CC=C1C FEMGFJFVGWMKRG-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000002352 surface water Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000012085 test solution Substances 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene 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
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- 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
- 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
- C07D239/56—One oxygen atom and one sulfur atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

IL9611390A 1989-11-17 1990-10-25 Insecticidal miticidal and nematocidal compositions containing pyrimidinyl benzoic acids and esters processes for the preparation thereof and some novel pyrimidinyl benzoic acids and esters IL96113A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/438,913 US5134145A (en)	1989-11-17	1989-11-17	Pesticidal pyrimidinyl benzoic acids and esters

Publications (2)

Publication Number	Publication Date
IL96113A0 IL96113A0 (en)	1991-07-18
IL96113A true IL96113A (en)	1995-08-31

Family

ID=23742546

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9611390A IL96113A (en)	1989-11-17	1990-10-25	Insecticidal miticidal and nematocidal compositions containing pyrimidinyl benzoic acids and esters processes for the preparation thereof and some novel pyrimidinyl benzoic acids and esters

Country Status (8)

Country	Link
US (1)	US5134145A (ja)
JP (1)	JPH0699407B2 (ja)
KR (1)	KR927003546A (ja)
AU (1)	AU6874591A (ja)
BR (1)	BR9007846A (ja)
IL (1)	IL96113A (ja)
WO (1)	WO1991007392A1 (ja)
ZA (1)	ZA908757B (ja)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
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US6680323B2 (en) *	1998-12-23	2004-01-20	Synaptic Pharmaceutical Corporation	Dihydropyrimidines and uses thereof
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1989
- 1989-11-17 US US07/438,913 patent/US5134145A/en not_active Expired - Fee Related
1990
- 1990-10-17 WO PCT/US1990/005956 patent/WO1991007392A1/en not_active Ceased
- 1990-10-17 JP JP3500404A patent/JPH0699407B2/ja not_active Expired - Lifetime
- 1990-10-17 BR BR909007846A patent/BR9007846A/pt unknown
- 1990-10-17 AU AU68745/91A patent/AU6874591A/en not_active Abandoned
- 1990-10-17 KR KR1019920701137A patent/KR927003546A/ko not_active Abandoned
- 1990-10-25 IL IL9611390A patent/IL96113A/en not_active IP Right Cessation
- 1990-10-31 ZA ZA908757A patent/ZA908757B/xx unknown

Also Published As

Publication number	Publication date
KR927003546A (ko)	1992-12-18
ZA908757B (en)	1991-08-28
JPH0699407B2 (ja)	1994-12-07
IL96113A0 (en)	1991-07-18
WO1991007392A1 (en)	1991-05-30
BR9007846A (pt)	1992-09-22
US5134145A (en)	1992-07-28
JPH05502862A (ja)	1993-05-20
AU6874591A (en)	1991-06-13

Legal Events

Date	Code	Title	Description
1997-08-14	RH	Patent void

Publication	Publication Date	Title
IL96113A (en)	1995-08-31	Insecticidal miticidal and nematocidal compositions containing pyrimidinyl benzoic acids and esters processes for the preparation thereof and some novel pyrimidinyl benzoic acids and esters
KR920002112B1 (ko)	1992-03-12	니트로메틸렌 유도체의 제조방법
CA1077048A (en)	1980-05-06	Pyrazole derivatives
JPH02235881A (ja)	1990-09-18	新規ヘテロ環式化合物及び殺虫剤
HUP0002729A2 (hu)	2000-11-28	4-(Halogén-alkil)-3-heterociklusos-piridin- és 4-(halogén-alkil)-5-heterociklusos-pirimidin-származékok, eljárás előállításukra, ezeket tartalmazó készítmények és kártevőírtó szerként történő alkalmazásuk
US5178663A (en)	1993-01-12	3-alkoxyalkanoic acid derivative, process for preparing the same and herbicide using the same
JPH02223564A (ja)	1990-09-05	アミノピリミジン誘導体、その製法及び殺虫・殺菌剤
US5134144A (en)	1992-07-28	Pesticidal 3-arylpyrimidinyl ethers and thioethers
JPH04316559A (ja)	1992-11-06	ピラゾールカルボキサニリド誘導体及び殺菌剤
JPH0327360A (ja)	1991-02-05	フェノキシアルキルアミン誘導体並びに殺虫剤・殺ダニ剤及び殺菌剤
JP3047447B2 (ja)	2000-05-29	ピラゾール誘導体、その製造法およびそれを有効成分とする除草剤
JPH04217968A (ja)	1992-08-07	イミノチアゾリン誘導体、その製造法、それを有効成分とする除草剤およびその製造中間体
FR2834288A1 (fr)	2003-07-04	Procede de preparation de nouveaux derives n-substitues de 5-amino-phenylpyrazole, nouveaux derives n-substitues de 5-amino-phenylpyrazole et leur utilisation comme agents parasiticides et/ou insecticides
JP3711581B2 (ja)	2005-11-02	セミカルバゾン誘導体及び有害生物防除剤
JPS6281382A (ja)	1987-04-14	新規複素環式化合物
JPH0363266A (ja)	1991-03-19	アラルキルアミン誘導体、その製法及び殺菌、殺虫剤
JPH01275554A (ja)	1989-11-06	スルホニルヒドラジン化合物及び殺虫剤
JP3498331B2 (ja)	2004-02-16	セミカルバゾン誘導体
JP3066536B2 (ja)	2000-07-17	縮合ヘテロ環誘導体及び除草剤
US5252596A (en)	1993-10-12	Phenoxyalkylamine derivative and method for controlling noxious organisms containing the same
KR960012181B1 (ko)	1996-09-16	신규 6-클로로-2-(4,6-디메톡시피리미딘-2-일)옥시벤조익산의 헤테로아릴이미노 에스테르 유도체 및 그의 제조방법
KR0128544B1 (ko)	1998-04-04	2,3-디히드로-3-메틸렌-2-치환된 페닐-1h-이소인돌-1-온 유도체
KR960012180B1 (ko)	1996-09-16	신규 6-클로로-2-(4,6-디메톡시피리미딘-2-일)옥시벤조익산의 페닐이미노 에스테르 유도체 및 그의 제조방법
KR960012179B1 (ko)	1996-09-16	신규 6-클로로-2-(4,6-디메톡시피리미딘-2-일)옥시벤조익산의 페닐이미노 에스테르 유도체 및 그의 제조방법
JPH0535147B2 (ja)	1993-05-25