ZA200505545B - Avermectin monosaccharide derivatives having pesticidal properties - Google Patents
Avermectin monosaccharide derivatives having pesticidal properties Download PDFInfo
- Publication number
- ZA200505545B ZA200505545B ZA200505545A ZA200505545A ZA200505545B ZA 200505545 B ZA200505545 B ZA 200505545B ZA 200505545 A ZA200505545 A ZA 200505545A ZA 200505545 A ZA200505545 A ZA 200505545A ZA 200505545 B ZA200505545 B ZA 200505545B
- Authority
- ZA
- South Africa
- Prior art keywords
- aryl
- heterocyclyl
- mono
- benzyl
- cealkyl
- Prior art date
Links
- -1 Avermectin monosaccharide derivatives Chemical class 0.000 title claims description 38
- 230000000361 pesticidal effect Effects 0.000 title claims description 5
- 239000005660 Abamectin Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 15
- 238000006467 substitution reaction Methods 0.000 claims description 15
- 150000003839 salts Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 241000607479 Yersinia pestis Species 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004468 heterocyclylthio group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 235000019000 fluorine Nutrition 0.000 description 9
- 229940060037 fluorine Drugs 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical class C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241001468227 Streptomyces avermitilis Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001721 carbon Chemical class 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000002771 monosaccharide derivatives Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- ULOIAOPTGWSNHU-UHFFFAOYSA-N 2-butyl radical Chemical compound C[CH]CC ULOIAOPTGWSNHU-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 1
- 241000238631 Hexapoda Species 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000711981 Sais Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000005366 cycloalkylthio group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005347 halocycloalkyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- 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
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- Chemical & Material Sciences (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0302309.0A GB0302309D0 (en) | 2003-01-31 | 2003-01-31 | Avermectin monosaccharide derivatives substituted in the 4 -position having pesticidal properties |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200505545B true ZA200505545B (en) | 2006-04-26 |
Family
ID=9952240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200505545A ZA200505545B (en) | 2003-01-31 | 2005-07-08 | Avermectin monosaccharide derivatives having pesticidal properties |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US20060205595A1 (pt) |
| EP (1) | EP1594878B1 (pt) |
| JP (1) | JP2006518347A (pt) |
| KR (1) | KR20050097524A (pt) |
| CN (1) | CN100410259C (pt) |
| AR (1) | AR042967A1 (pt) |
| AT (1) | ATE397610T1 (pt) |
| AU (1) | AU2004207073B2 (pt) |
| BR (1) | BRPI0406875B1 (pt) |
| CA (1) | CA2513573C (pt) |
| CL (1) | CL2004000147A1 (pt) |
| CY (1) | CY1108295T1 (pt) |
| DE (1) | DE602004014252D1 (pt) |
| DK (1) | DK1594878T3 (pt) |
| ES (1) | ES2308140T3 (pt) |
| GB (1) | GB0302309D0 (pt) |
| IL (1) | IL169598A (pt) |
| MA (1) | MA27587A1 (pt) |
| MX (1) | MXPA05007923A (pt) |
| NZ (1) | NZ541252A (pt) |
| PL (1) | PL218731B1 (pt) |
| PT (1) | PT1594878E (pt) |
| RU (1) | RU2329268C2 (pt) |
| SI (1) | SI1594878T1 (pt) |
| TW (1) | TW200508240A (pt) |
| UA (1) | UA81012C2 (pt) |
| WO (1) | WO2004067534A1 (pt) |
| ZA (1) | ZA200505545B (pt) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EG23124A (en) | 2001-02-27 | 2004-04-28 | Syngenta Participations Ag | Avermectins substituted in the 4-position having pesticidal properties |
| CR6574A (es) | 2001-02-27 | 2004-10-28 | Syngenta Participations Ag | Sales de avermectinas substituidas en la posicion 4 con propiedades plaguicidas |
| AR036486A1 (es) | 2001-08-28 | 2004-09-15 | Syngenta Participations Ag | Derivados 4"-desoxi-4"-(s)-amino avermectina, composicion plaguicida, procedimiento para la preparacion de esa composicion, metodo para controlar plagas, y uso de estos derivados para preparar una composicion |
| AR040073A1 (es) | 2002-05-07 | 2005-03-16 | Syngenta Participations Ag | Derivados de 4''-desoxi-4''-(s)-amido avermectina y su uso como plaguicidas |
| GB0302310D0 (en) * | 2003-01-31 | 2003-03-05 | Syngenta Participations Ag | Avermectin- and avermectin monosaccharide derivatives substituted in the 4"- or 4' - positionhaving pesticidal properties |
| GB0302308D0 (en) | 2003-01-31 | 2003-03-05 | Syngenta Participations Ag | Avermectin and avermectin monosaccharide derivatives substituted in the 4"- or 4'-position having pesticidal properties |
| GB0302547D0 (en) * | 2003-02-04 | 2003-03-12 | Syngenta Participations Ag | Avermectins and avermectin monosaccharide substituted in the 4'- and 4" position having pesticidal properties |
| GB0320176D0 (en) | 2003-08-28 | 2003-10-01 | Syngenta Participations Ag | Avermectins and avermectin monosaccharides substitued in the 4'-and 4"-positionhaving pesticidal properties |
| TW200538461A (en) * | 2004-04-07 | 2005-12-01 | Syngenta Participations Ag | Avermectin and avermectin monosaccharide substituted in the 4"-and 4'-position respectively |
| US8551914B2 (en) * | 2010-08-26 | 2013-10-08 | Dow Agrosciences, Llc. | Pesticidal compositions |
| CN103214532B (zh) * | 2013-02-28 | 2018-07-06 | 河北威远生物化工有限公司 | 阿维菌素B2a/2b胺基衍生物、衍生物盐和阿维菌素B2a/2b胺基衍生物盐的制备方法及用途 |
| CN103613625B (zh) * | 2013-12-02 | 2016-03-02 | 兰州大学 | 一种阿维菌素类化合物及其制备方法和在农药中的用途 |
| CN104402954A (zh) * | 2014-11-28 | 2015-03-11 | 大庆志飞生物化工有限公司 | 甲胺基阿维菌素单糖化合物及其制备方法和用途 |
| CN104402953B (zh) * | 2014-11-28 | 2017-07-28 | 大庆志飞生物化工有限公司 | 阿维菌素单糖化合物及其制备方法和用途 |
| CN107501368B (zh) * | 2017-09-30 | 2020-02-21 | 中国科学院成都生物研究所 | 一种多拉菌素衍生物的合成及其杀虫应用 |
| CN108690108B (zh) * | 2018-07-27 | 2022-03-11 | 河北威远生物化工有限公司 | 一种磺酰胺基取代的阿维菌素B2a/B2b衍生物及其制备方法与应用 |
| CN113150053A (zh) * | 2020-01-22 | 2021-07-23 | 华东理工大学 | 偶氮苯类阿维菌素衍生物及其制备方法和应用 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4206205A (en) * | 1977-10-03 | 1980-06-03 | Merck & Co., Inc. | Monosaccharide and aglycone derivatives of C-076 |
| US4203976A (en) * | 1978-08-02 | 1980-05-20 | Merck & Co., Inc. | Sugar derivatives of C-076 compounds |
| US4427663A (en) * | 1982-03-16 | 1984-01-24 | Merck & Co., Inc. | 4"-Keto-and 4"-amino-4"-deoxy avermectin compounds and substituted amino derivatives thereof |
| US4622313A (en) * | 1985-08-01 | 1986-11-11 | Merck & Co., Inc. | O-sulfate derivatives of avermectins and milbemycins having improved water solubility |
| US4886828A (en) * | 1986-09-12 | 1989-12-12 | American Cyanamid Company | Δ22 -derivatives of LL-F28249 compounds |
| US4831016A (en) * | 1986-10-31 | 1989-05-16 | Merck & Co., Inc. | Reduced avermectin derivatives |
| US4895837A (en) * | 1988-01-29 | 1990-01-23 | Merck & Co., Inc. | Avermectin derivatives |
| NZ228866A (en) * | 1988-05-02 | 1991-10-25 | Merck & Co Inc | Fluoro-substituted milbemycins and avermectins for combatting parasites and insects |
| US5008250A (en) * | 1988-05-25 | 1991-04-16 | Merck & Co., Inc. | Avermectins with a cleaved furan ring and an 8a hydroxy group |
| GB2220856A (en) * | 1988-07-18 | 1990-01-24 | Merck & Co Inc | Novel synergistic agricultural insecticidal and acaricidal combinations containing avermectin derivatives |
| NZ231773A (en) * | 1988-12-23 | 1992-09-25 | Merck & Co Inc | Avermectin derivatives, preparation and parasiticidal pharmaceutical compositions thereof |
| FR2646237B1 (fr) * | 1989-04-21 | 1994-01-07 | Fabrication Instruments Mesure | Dispositif de jaugeage de gaz haute pression, en particulier pour la reserve d'oxygene gazeux embarquee a bord d'un avion |
| US5057499A (en) * | 1989-06-02 | 1991-10-15 | Merck & Co. Inc. | Avermectin derivatives |
| US5023241A (en) * | 1989-07-31 | 1991-06-11 | Merck & Co., Inc. | Avermectin derivatives |
| US5169839A (en) * | 1990-05-11 | 1992-12-08 | Merck & Co., Inc. | Derivatives of 3'- and 3"-o-desmethyl avermectin compounds, compositions and methods of treating melmintic and parasitic infections |
| US5192546A (en) * | 1991-01-15 | 1993-03-09 | Mycogen Corporation | Synergistic pesticidal compositions |
| US5346698A (en) * | 1991-01-15 | 1994-09-13 | Mycogen Corporation | Synergistic pesticidal compositions |
| US5208222A (en) * | 1991-03-28 | 1993-05-04 | Merck & Co., Inc. | 4"-and 4'-alkylthio avermectin derivatives |
| GB9201505D0 (en) * | 1992-01-24 | 1992-03-11 | Pfizer Ltd | Antiparasitic agents |
| US5229415A (en) * | 1992-03-24 | 1993-07-20 | Merck & Co., Inc. | Alkylthio alkyl avermectins are active antiparasitic agents |
| US5362863A (en) * | 1993-09-29 | 1994-11-08 | Merck & Co., Inc. | Process for the preparation of 4"-amino avermectin compounds |
| US5981500A (en) * | 1994-01-12 | 1999-11-09 | Pfizer Inc. | Antiparasitic agents related to the milbemycins and avermectins |
| US5436355A (en) * | 1994-02-03 | 1995-07-25 | Merck & Co., Inc. | Process for making avermectin/zein compositions |
| TW327125B (en) * | 1994-02-07 | 1998-02-21 | Merck & Co Inc | Composition and method for protecting against pine exhausted |
| US6875727B2 (en) * | 1997-12-23 | 2005-04-05 | Syngenta Crop Protection, Inc. | Use of macrolides in pest control |
| KR20010101819A (ko) * | 1999-02-09 | 2001-11-14 | 오무라 사토시 | 에바멕틴 유도체 |
| US20040087519A1 (en) * | 2000-08-09 | 2004-05-06 | Satoshi Omura | Avermectin derivatives |
| EG23124A (en) * | 2001-02-27 | 2004-04-28 | Syngenta Participations Ag | Avermectins substituted in the 4-position having pesticidal properties |
| CR6574A (es) * | 2001-02-27 | 2004-10-28 | Syngenta Participations Ag | Sales de avermectinas substituidas en la posicion 4 con propiedades plaguicidas |
| AR037938A1 (es) * | 2001-12-21 | 2004-12-22 | Syngenta Participations Ag | Derivados de avermectina b1 que tienen un substituyente de aminosulfoniloxilo en la posicion 4'' |
| GB0302308D0 (en) * | 2003-01-31 | 2003-03-05 | Syngenta Participations Ag | Avermectin and avermectin monosaccharide derivatives substituted in the 4"- or 4'-position having pesticidal properties |
| GB0302548D0 (en) * | 2003-02-04 | 2003-03-12 | Syngenta Participations Ag | Avermectins substituted in the 4"- and 4' -positions having pesticidal properties |
| TW200538461A (en) * | 2004-04-07 | 2005-12-01 | Syngenta Participations Ag | Avermectin and avermectin monosaccharide substituted in the 4"-and 4'-position respectively |
-
2003
- 2003-01-31 GB GBGB0302309.0A patent/GB0302309D0/en not_active Ceased
-
2004
- 2004-01-29 AR ARP040100268A patent/AR042967A1/es active IP Right Grant
- 2004-01-29 TW TW093102006A patent/TW200508240A/zh unknown
- 2004-01-29 CL CL200400147A patent/CL2004000147A1/es unknown
- 2004-01-30 PT PT04706630T patent/PT1594878E/pt unknown
- 2004-01-30 AU AU2004207073A patent/AU2004207073B2/en not_active Ceased
- 2004-01-30 BR BRPI0406875-0A patent/BRPI0406875B1/pt not_active IP Right Cessation
- 2004-01-30 ES ES04706630T patent/ES2308140T3/es not_active Expired - Lifetime
- 2004-01-30 WO PCT/EP2004/000899 patent/WO2004067534A1/en active IP Right Grant
- 2004-01-30 CA CA2513573A patent/CA2513573C/en not_active Expired - Fee Related
- 2004-01-30 JP JP2006501692A patent/JP2006518347A/ja active Pending
- 2004-01-30 AT AT04706630T patent/ATE397610T1/de active
- 2004-01-30 MX MXPA05007923A patent/MXPA05007923A/es active IP Right Grant
- 2004-01-30 SI SI200430826T patent/SI1594878T1/sl unknown
- 2004-01-30 DK DK04706630T patent/DK1594878T3/da active
- 2004-01-30 DE DE602004014252T patent/DE602004014252D1/de not_active Expired - Lifetime
- 2004-01-30 US US10/543,643 patent/US20060205595A1/en not_active Abandoned
- 2004-01-30 PL PL378024A patent/PL218731B1/pl unknown
- 2004-01-30 CN CNB2004800043694A patent/CN100410259C/zh not_active Expired - Fee Related
- 2004-01-30 RU RU2005127321/04A patent/RU2329268C2/ru active
- 2004-01-30 KR KR1020057014004A patent/KR20050097524A/ko not_active Application Discontinuation
- 2004-01-30 NZ NZ541252A patent/NZ541252A/en not_active IP Right Cessation
- 2004-01-30 EP EP04706630A patent/EP1594878B1/en not_active Expired - Lifetime
- 2004-01-30 UA UAA200508413A patent/UA81012C2/uk unknown
-
2005
- 2005-07-07 IL IL169598A patent/IL169598A/en active IP Right Grant
- 2005-07-08 ZA ZA200505545A patent/ZA200505545B/en unknown
- 2005-08-30 MA MA28474A patent/MA27587A1/fr unknown
-
2008
- 2008-08-25 CY CY20081100913T patent/CY1108295T1/el unknown
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