NL8900087A - Synergistische fungicide- en acaricidepreparaten met twee of drie werkzame bestanddelen erin. - Google Patents

Synergistische fungicide- en acaricidepreparaten met twee of drie werkzame bestanddelen erin. Download PDF

Info

Publication number: NL8900087A
Authority: NL; Netherlands
Prior art keywords: carbon atoms; alkyl; triforine; ethyl; compound
Prior art date: 1988-01-14

Application number

NL8900087A

Other languages

English (en)

Dutch (nl)

Original Assignee

Eszakmagyar Vegyimuevek

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.)

1988-01-14

Filing date

1989-01-13

Publication date

1989-08-01

1989-01-13 Application filed by Eszakmagyar Vegyimuevek filed Critical Eszakmagyar Vegyimuevek

1989-08-01 Publication of NL8900087A publication Critical patent/NL8900087A/nl

Links

239000004480 active ingredient Substances 0.000 title claims description 133
238000002360 preparation method Methods 0.000 title claims description 92
230000000855 fungicidal effect Effects 0.000 title claims description 52
230000002195 synergetic effect Effects 0.000 title claims description 23
230000000895 acaricidal effect Effects 0.000 title claims description 19
239000000417 fungicide Substances 0.000 title description 18
239000000642 acaricide Substances 0.000 title description 3
RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 claims description 130
-1 alkyl radicals Chemical class 0.000 claims description 116
TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 63
125000004432 carbon atom Chemical group C* 0.000 claims description 53
239000000203 mixture Substances 0.000 claims description 47
239000006013 carbendazim Substances 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 23
125000005843 halogen group Chemical group 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 claims description 12
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
125000000304 alkynyl group Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
229960000988 nystatin Drugs 0.000 claims description 5
VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
150000001556 benzimidazoles Chemical class 0.000 claims description 4
JHRWWRDRBPCWTF-UHFFFAOYSA-N captafol Chemical compound C1C=CCC2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)C21 JHRWWRDRBPCWTF-UHFFFAOYSA-N 0.000 claims description 4
BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical class NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000005802 Mancozeb Substances 0.000 claims description 2
125000005108 alkenylthio group Chemical group 0.000 claims description 2
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000005133 alkynyloxy group Chemical group 0.000 claims description 2
125000005109 alkynylthio group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000004069 aziridinyl group Chemical group 0.000 claims description 2
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
125000005936 piperidyl group Chemical group 0.000 claims description 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims description 2
125000001166 thiolanyl group Chemical group 0.000 claims description 2
125000004953 trihalomethyl group Chemical group 0.000 claims description 2
YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 claims 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical group C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 claims 1
125000003302 alkenyloxy group Chemical group 0.000 claims 1
125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
BWOVZCWSJFYBRM-UHFFFAOYSA-N carbononitridic isocyanate Chemical class O=C=NC#N BWOVZCWSJFYBRM-UHFFFAOYSA-N 0.000 claims 1
150000002540 isothiocyanates Chemical class 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
150000003567 thiocyanates Chemical class 0.000 claims 1
229940126657 Compound 17 Drugs 0.000 description 69
229940126062 Compound A Drugs 0.000 description 68
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 68
238000000034 method Methods 0.000 description 39
239000004495 emulsifiable concentrate Substances 0.000 description 38
230000000694 effects Effects 0.000 description 37
239000004563 wettable powder Substances 0.000 description 25
OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 description 21
230000005764 inhibitory process Effects 0.000 description 16
239000007788 liquid Substances 0.000 description 16
WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 16
238000011282 treatment Methods 0.000 description 16
241000238876 Acari Species 0.000 description 15
241000221785 Erysiphales Species 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
KRZUZYJEQBXUIN-UHFFFAOYSA-N Cyprofuram Chemical compound ClC1=CC=CC(N(C2C(OCC2)=O)C(=O)C2CC2)=C1 KRZUZYJEQBXUIN-UHFFFAOYSA-N 0.000 description 14
239000003995 emulsifying agent Substances 0.000 description 14
239000000843 powder Substances 0.000 description 14
239000004308 thiabendazole Substances 0.000 description 14
229960004546 thiabendazole Drugs 0.000 description 14
235000010296 thiabendazole Nutrition 0.000 description 14
241000196324 Embryophyta Species 0.000 description 13
241001223281 Peronospora Species 0.000 description 13
ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 13
VTWVWXZKYDDACW-UHFFFAOYSA-M copper(1+);quinolin-8-ol;quinolin-8-olate Chemical compound [Cu+].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 VTWVWXZKYDDACW-UHFFFAOYSA-M 0.000 description 12
239000002270 dispersing agent Substances 0.000 description 12
239000005807 Metalaxyl Substances 0.000 description 11
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
239000008096 xylene Substances 0.000 description 11
239000007864 aqueous solution Substances 0.000 description 10
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 10
238000009472 formulation Methods 0.000 description 10
CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 10
239000005734 Benalaxyl Substances 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
244000070406 Malus silvestris Species 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000002699 waste material Substances 0.000 description 9
239000000080 wetting agent Substances 0.000 description 9
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 8
HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 8
238000012360 testing method Methods 0.000 description 8
241000219094 Vitaceae Species 0.000 description 7
235000021021 grapes Nutrition 0.000 description 7
UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
244000020551 Helianthus annuus Species 0.000 description 6
235000011430 Malus pumila Nutrition 0.000 description 6
235000015103 Malus silvestris Nutrition 0.000 description 6
238000011156 evaluation Methods 0.000 description 6
239000005789 Folpet Substances 0.000 description 5
241000233866 Fungi Species 0.000 description 5
235000010469 Glycine max Nutrition 0.000 description 5
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
230000001586 eradicative effect Effects 0.000 description 5
230000003631 expected effect Effects 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
229910052710 silicon Inorganic materials 0.000 description 5
239000010703 silicon Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
240000006497 Dianthus caryophyllus Species 0.000 description 4
235000009355 Dianthus caryophyllus Nutrition 0.000 description 4
235000009754 Vitis X bourquina Nutrition 0.000 description 4
235000012333 Vitis X labruscana Nutrition 0.000 description 4
240000006365 Vitis vinifera Species 0.000 description 4
235000014787 Vitis vinifera Nutrition 0.000 description 4
235000021016 apples Nutrition 0.000 description 4
239000000969 carrier Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000001963 growth medium Substances 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000007787 solid Substances 0.000 description 4
208000024891 symptom Diseases 0.000 description 4
229920001817 Agar Polymers 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
240000008067 Cucumis sativus Species 0.000 description 3
235000010799 Cucumis sativus var sativus Nutrition 0.000 description 3
235000003222 Helianthus annuus Nutrition 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
241001454295 Tetranychidae Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
244000098338 Triticum aestivum Species 0.000 description 3
239000013543 active substance Substances 0.000 description 3
239000008272 agar Substances 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
239000010949 copper Substances 0.000 description 3
238000011161 development Methods 0.000 description 3
230000018109 developmental process Effects 0.000 description 3
235000013399 edible fruits Nutrition 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
238000005507 spraying Methods 0.000 description 3
235000013311 vegetables Nutrition 0.000 description 3
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
241001465180 Botrytis Species 0.000 description 2
241001123534 Colletotrichum coccodes Species 0.000 description 2
241000654919 Cytospora cincta Species 0.000 description 2
241000223218 Fusarium Species 0.000 description 2
241000208818 Helianthus Species 0.000 description 2
208000031888 Mycoses Diseases 0.000 description 2
241000233610 Plasmopara halstedii Species 0.000 description 2
244000018633 Prunus armeniaca Species 0.000 description 2
235000009827 Prunus armeniaca Nutrition 0.000 description 2
241000220324 Pyrus Species 0.000 description 2
241001361634 Rhizoctonia Species 0.000 description 2
244000061456 Solanum tuberosum Species 0.000 description 2
235000002595 Solanum tuberosum Nutrition 0.000 description 2
241000344246 Tetranychus cinnabarinus Species 0.000 description 2
241000607479 Yersinia pestis Species 0.000 description 2
239000000654 additive Substances 0.000 description 2
229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000013256 coordination polymer Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
230000002538 fungal effect Effects 0.000 description 2
238000003898 horticulture Methods 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 2
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
239000002609 medium Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 2
230000004487 negative regulation of sporulation resulting in formation of a cellular spore Effects 0.000 description 2
239000000575 pesticide Substances 0.000 description 2
231100000208 phytotoxic Toxicity 0.000 description 2
230000000885 phytotoxic effect Effects 0.000 description 2
238000012545 processing Methods 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000003944 tolyl group Chemical group 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
GDURTYCKMYLVRL-UHFFFAOYSA-N (3,4-diethoxyphenyl)-propan-2-ylcarbamic acid Chemical compound CCOC1=CC=C(N(C(C)C)C(O)=O)C=C1OCC GDURTYCKMYLVRL-UHFFFAOYSA-N 0.000 description 1
YJTOVUWIAQQJJT-UHFFFAOYSA-N 2-(furan-2-yl)acetamide Chemical compound NC(=O)CC1=CC=CO1 YJTOVUWIAQQJJT-UHFFFAOYSA-N 0.000 description 1
QRNATDQRFAUDKF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate Chemical compound NC(=S)SCCSC(N)=S QRNATDQRFAUDKF-UHFFFAOYSA-N 0.000 description 1
MUHFRORXWCGZGE-KTKRTIGZSA-N 2-hydroxyethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCO MUHFRORXWCGZGE-KTKRTIGZSA-N 0.000 description 1
DEQFYOHXOZHJRC-UHFFFAOYSA-N 2-methoxy-n-(2-oxo-1,3-oxazolidin-3-yl)acetamide Chemical compound COCC(=O)NN1CCOC1=O DEQFYOHXOZHJRC-UHFFFAOYSA-N 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 description 1
QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
244000291564 Allium cepa Species 0.000 description 1
235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
244000144730 Amygdalus persica Species 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
241000228439 Bipolaris zeicola Species 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
241001480061 Blumeria graminis Species 0.000 description 1
241000167854 Bourreria succulenta Species 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000011293 Brassica napus Nutrition 0.000 description 1
235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
229920000298 Cellophane Polymers 0.000 description 1
241001157813 Cercospora Species 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
241000222199 Colletotrichum Species 0.000 description 1
241000588698 Erwinia Species 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
241000735332 Gerbera Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
235000008694 Humulus lupulus Nutrition 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-M L-alaninate Chemical compound C[C@H](N)C([O-])=O QNAYBMKLOCPYGJ-REOHCLBHSA-M 0.000 description 1
244000081841 Malus domestica Species 0.000 description 1
206010027146 Melanoderma Diseases 0.000 description 1
241001363490 Monilia Species 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
OZBZONOEYUBXTD-UHFFFAOYSA-N OOOOOOOOO Chemical compound OOOOOOOOO OZBZONOEYUBXTD-UHFFFAOYSA-N 0.000 description 1
HFEFMUSTGZNOPY-UHFFFAOYSA-N OOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOO HFEFMUSTGZNOPY-UHFFFAOYSA-N 0.000 description 1
241000488583 Panonychus ulmi Species 0.000 description 1
241000233679 Peronosporaceae Species 0.000 description 1
206010035148 Plague Diseases 0.000 description 1
241000896242 Podosphaera Species 0.000 description 1
241000317981 Podosphaera fuliginea Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
235000006040 Prunus persica var persica Nutrition 0.000 description 1
244000046095 Psophocarpus tetragonolobus Species 0.000 description 1
235000014443 Pyrus communis Nutrition 0.000 description 1
244000181025 Rosa gallica Species 0.000 description 1
241001558929 Sclerotium <basidiomycota> Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
244000107946 Spondias cytherea Species 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
150000003869 acetamides Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229940053202 antiepileptics carboxamide derivative Drugs 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000011324 bead Substances 0.000 description 1
RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
230000034303 cell budding Effects 0.000 description 1
235000019693 cherries Nutrition 0.000 description 1
235000013330 chicken meat Nutrition 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
230000018842 conidium formation Effects 0.000 description 1
150000004699 copper complex Chemical class 0.000 description 1
229940118056 cresol / formaldehyde Drugs 0.000 description 1
238000009109 curative therapy Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
235000021186 dishes Nutrition 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
244000053095 fungal pathogen Species 0.000 description 1
244000000004 fungal plant pathogen Species 0.000 description 1
229940095098 glycol oleate Drugs 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000003906 humectant Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000002932 luster Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
239000002420 orchard Substances 0.000 description 1
235000021017 pears Nutrition 0.000 description 1
231100000760 phototoxic Toxicity 0.000 description 1
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
230000008659 phytopathology Effects 0.000 description 1
KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
ZEVCJZRMCOYJSP-UHFFFAOYSA-N sodium;2-(dithiocarboxyamino)ethylcarbamodithioic acid Chemical compound [Na+].SC(=S)NCCNC(S)=S ZEVCJZRMCOYJSP-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000004546 suspension concentrate 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
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing acyclic or cycloaliphatic radicals

Landscapes

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)

NL8900087A 1988-01-14 1989-01-13 Synergistische fungicide- en acaricidepreparaten met twee of drie werkzame bestanddelen erin. NL8900087A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU12988		1988-01-14
HU88129A HU202728B (en)	1988-01-14	1988-01-14	Synergetic fungicide and acaricide compositions containing two or three active components

Publications (1)

Publication Number	Publication Date
NL8900087A true NL8900087A (nl)	1989-08-01

Family

ID=10948065

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8900087A NL8900087A (nl)	1988-01-14	1989-01-13	Synergistische fungicide- en acaricidepreparaten met twee of drie werkzame bestanddelen erin.

Country Status (15)

Country	Link
US (1)	US4980346A (de)
JP (1)	JPH02701A (de)
CN (1)	CN1037067A (de)
AT (1)	ATA319088A (de)
BE (1)	BE1002744A4 (de)
BR (1)	BR8900164A (de)
DE (1)	DE3900892A1 (de)
ES (1)	ES2012223A6 (de)
FR (1)	FR2625870A1 (de)
GB (1)	GB2213727A (de)
GR (1)	GR1000272B (de)
HU (1)	HU202728B (de)
NL (1)	NL8900087A (de)
PT (1)	PT89449B (de)
ZA (1)	ZA89306B (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5191305A (en) *	1991-07-02	1993-03-02	Interstate Electronics Corporation	Multiple bandpass filter
ES2065284B1 (es) *	1993-07-14	1995-11-16	Agriplan S A	Un producto fungicida para el tratamiento postcosecha de frutas destinadas a frigoconservacion.
DE4342621A1 (de) *	1993-12-14	1995-06-22	Bayer Ag	Phosphorsäure-Derivate
NZ513639A (en) *	1999-04-15	2004-02-27	Bristol Myers Squibb Co	Cyclic protein tyrosine kinase inhibitors
US7125875B2 (en) *	1999-04-15	2006-10-24	Bristol-Myers Squibb Company	Cyclic protein tyrosine kinase inhibitors
WO2002041891A2 (en) *	2000-11-01	2002-05-30	The Procter & Gamble Company	Hiv treatment with benzimidazoles
FR2836999B1 (fr) *	2002-03-08	2004-05-28	Thales Sa	Dispositif audiophonique panoramique pour sonar passif
WO2003082273A1 (en) *	2002-03-26	2003-10-09	Arizona Board Of Regents On Behalf Of The University Of Arizona	Solubilization of weak bases
DE602004008658T2 (de) *	2003-09-05	2008-06-12	Cellzome Ag	Behandlung neurodegenerativer krankheiten
DK1926370T3 (da)	2005-09-13	2013-03-25	Isagro Spa	Fremgangsmåde til beskyttelse mod fytopatogener med kiralaxyl, tilsvarende anvendelse og middel dertil
KR100779986B1 (ko) *	2006-12-30	2007-11-28	한양대학교 산학협력단	폴리다이아세틸렌 함유 초미세섬유의 제조방법
KR100914149B1 (ko) *	2008-01-24	2009-08-28	한국과학기술원	컷아웃 주위에 이중 적층 전자기 밴드갭 구조를 가지는반도체 패키지 기판
KR100888250B1 (ko) *	2008-09-18	2009-03-10	현대엔지니어링 주식회사	조력발전소 최적발전량 및 운영상태 예측 방법
WO2010043553A1 (en) *	2008-10-16	2010-04-22	Basf Se	Pesticidal mixtures comprising metaflumizone and a fungicidal compound
WO2012117055A1 (en)	2011-03-03	2012-09-07	Dsm Ip Assets B.V.	New antifungal compositions

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3657443A (en) *	1969-09-29	1972-04-18	Du Pont	2-benzimidazolecarbamic acid alkyl esters as foliar fungicides
DD219098A1 (de) *	1983-10-24	1985-02-27	Adl Inst Pflanzenschutz	Schaedlingsbekaempfungsmittel
HU194258B (en) *	1984-09-26	1988-01-28	Eszakmagyar Vegyimuevek	Acaricide, insecticide, fungicide compositions and process for producing new n-alkyl-/ene/-n-/0,0-disubstituted-thiophosphoryl/-n-comma above-n-comma above-disubstituted-glycin-amides as active components
AT387577B (de) *	1984-09-26	1989-02-10	Eszakmagyar Vegyimuevek	Verfahren zur herstellung von n-alkyl/en/-n-/o,o- disubstituierten thiophosphoryl/-n'n'disubstituierten-glycinamiden und diese verbindungen enthaltende akarizide, insektizide und fungizide mittel

1988
- 1988-01-14 HU HU88129A patent/HU202728B/hu not_active IP Right Cessation
- 1988-12-29 AT AT883190A patent/ATA319088A/de not_active Application Discontinuation
1989
- 1989-01-11 US US07/296,451 patent/US4980346A/en not_active Expired - Fee Related
- 1989-01-12 BE BE8900025A patent/BE1002744A4/fr not_active IP Right Cessation
- 1989-01-13 BR BR898900164A patent/BR8900164A/pt unknown
- 1989-01-13 DE DE3900892A patent/DE3900892A1/de not_active Withdrawn
- 1989-01-13 ES ES8900122A patent/ES2012223A6/es not_active Expired - Fee Related
- 1989-01-13 JP JP895048A patent/JPH02701A/ja active Pending
- 1989-01-13 PT PT89449A patent/PT89449B/pt not_active IP Right Cessation
- 1989-01-13 NL NL8900087A patent/NL8900087A/nl not_active Application Discontinuation
- 1989-01-13 CN CN89100188A patent/CN1037067A/zh active Pending
- 1989-01-13 FR FR8900370A patent/FR2625870A1/fr not_active Withdrawn
- 1989-01-13 GR GR890100020A patent/GR1000272B/el unknown
- 1989-01-13 GB GB8900760A patent/GB2213727A/en not_active Withdrawn
- 1989-01-13 ZA ZA89306A patent/ZA89306B/xx unknown

Also Published As

Publication number	Publication date
GB8900760D0 (en)	1989-03-08
US4980346A (en)	1990-12-25
BE1002744A4 (fr)	1991-05-28
CN1037067A (zh)	1989-11-15
GR1000272B (el)	1992-05-12
ZA89306B (en)	1989-10-25
PT89449A (pt)	1990-02-08
ES2012223A6 (es)	1990-03-01
HU202728B (en)	1991-04-29
PT89449B (pt)	1993-12-31
FR2625870A1 (fr)	1989-07-21
GB2213727A (en)	1989-08-23
BR8900164A (pt)	1989-09-12
JPH02701A (ja)	1990-01-05
DE3900892A1 (de)	1989-07-27
ATA319088A (de)	1992-06-15

Legal Events

Date	Code	Title	Description
1992-09-01	BV	The patent application has lapsed

Publication	Publication Date	Title
KR0169476B1 (ko)	1999-01-15	살균 조성물 및 이를 사용한 살균방법
DE60202132T2 (de)	2005-11-10	Fungizide Zusammensetzungen suf der Basis von Pyridylmethylbenzamid-Derivaten und mindestens einer den Komplex III hemmenden Verbindung
UA119672C2 (uk)	2019-07-25	Пестицидні композиції
EA015804B1 (ru)	2011-12-30	Синергически действующие и хорошо переносимые культурными растениями гербицидные средства, которые содержат гербициды из группы бензоилпиразолов
EA015243B1 (ru)	2011-06-30	Способ повышения урожайности кукурузы
Tisdale et al.	1942	Derivatives of dithiocarbamic acid as pesticides
RU2265331C2 (ru)	2005-12-10	Фунгицидная композиция
EA026738B1 (ru)	2017-05-31	Пестицидные смеси, содержащие спирогетероциклические пирролидиндионы
AU2003233306A1 (en)	2003-12-02	Novel vegetal reinforcing agent based on phytohormones for use in the cultivation of plants or agriculture, preferably in the cultivation of fruit or in wine growing
FR2625870A1 (fr)	1989-07-21	Compositions synergiques fongicides et acaricides contenant deux ou trois ingredients actifs
KR100703913B1 (ko)	2007-04-05	상승효과적인 살충 조성물
JP2010275205A (ja)	2010-12-09	除草剤組成物又は植物成長調節剤組成物及びその使用方法
AU2021202169A1 (en)	2021-05-06	Pre- and post-emergence broad spectrum herbicidal formulation containing triazolinones in association with urea pesticides and methods for controlling weeds and increasing crop yield
TW201717762A (zh)	2017-06-01	協同性殺蟲組合物
EP3871501B1 (de)	2023-03-08	Verfahren zur herstellung von thiocyclamhydrochlorid
CA3225280A1 (en)	2023-01-12	Fungicidal use
BG63027B1 (bg)	2001-02-28	Метод за унищожаване яйцата на вредни насекоми и приложение на овоцидни състави за целта
US11653650B2 (en)	2023-05-23	Fungicide composition and method for controlling disease of crop
CN107306981A (zh)	2017-11-03	含有绿僵菌素和螺虫乙酯的杀虫组合物
RU2245033C1 (ru)	2005-01-27	Способ борьбы с колорадским жуком
BR102019028250A2 (pt)	2020-07-14	Misturas fungicidas, composição pesticida, uso da mistura e método para controlar pragas fitopatogênicas
EA014917B1 (ru)	2011-02-28	Пестицидные смеси, включающие фенилсемикарбазон
CN112674107A (zh)	2021-04-20	一种防治果蔬病害的杀菌组合物及应用
BG64721B1 (bg)	2006-01-31	Фунгицидни състави
WO2024105626A1 (en)	2024-05-23	Synergistic fungicidal composition comprising picoxystrobin and thiophanate methyl and method related thereto