KR100446912B1 - 살진균성 활성 화합물의 배합물 - Google Patents
살진균성 활성 화합물의 배합물 Download PDFInfo
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- KR100446912B1 KR100446912B1 KR10-2001-7009674A KR20017009674A KR100446912B1 KR 100446912 B1 KR100446912 B1 KR 100446912B1 KR 20017009674 A KR20017009674 A KR 20017009674A KR 100446912 B1 KR100446912 B1 KR 100446912B1
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- active compound
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- active compounds
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- 230000000855 fungicidal effect Effects 0.000 title claims description 11
- 239000013543 active substance Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 241000233866 Fungi Species 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 239000000417 fungicide Substances 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- XDEHMKQLKPZERH-BYPYZUCNSA-N (2s)-2-amino-3-methylbutanamide Chemical class CC(C)[C@H](N)C(N)=O XDEHMKQLKPZERH-BYPYZUCNSA-N 0.000 abstract description 4
- 230000003032 phytopathogenic effect Effects 0.000 abstract description 3
- -1 liquid solvents Chemical class 0.000 description 27
- 230000000694 effects Effects 0.000 description 20
- 241000196324 Embryophyta Species 0.000 description 9
- 238000009472 formulation Methods 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 230000002195 synergetic effect Effects 0.000 description 5
- 239000000969 carrier Substances 0.000 description 4
- 239000010949 copper Chemical class 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000005896 Etofenprox Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 229950005085 etofenprox Drugs 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- BQMRHYBXRAYYQS-UHFFFAOYSA-N 4-dihydroxyphosphinothioyloxy-n,n-diethyl-6-methylpyrimidin-2-amine Chemical compound CCN(CC)C1=NC(C)=CC(OP(O)(O)=S)=N1 BQMRHYBXRAYYQS-UHFFFAOYSA-N 0.000 description 2
- 239000005660 Abamectin Substances 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical class [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEDTXTNSFWUXGQ-UHFFFAOYSA-N Carbophenothion Chemical compound CCOP(=S)(OCC)SCSC1=CC=C(Cl)C=C1 VEDTXTNSFWUXGQ-UHFFFAOYSA-N 0.000 description 2
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000005947 Dimethoate Substances 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000005777 Fenpropidin Substances 0.000 description 2
- 239000005780 Fluazinam Substances 0.000 description 2
- 239000005791 Fuberidazole Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000233626 Plasmopara Species 0.000 description 2
- 241001281803 Plasmopara viticola Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005846 Triadimenol Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- KXRPCFINVWWFHQ-UHFFFAOYSA-N cadusafos Chemical compound CCC(C)SP(=O)(OCC)SC(C)CC KXRPCFINVWWFHQ-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- XFDJMIHUAHSGKG-UHFFFAOYSA-N chlorethoxyfos Chemical compound CCOP(=S)(OCC)OC(Cl)C(Cl)(Cl)Cl XFDJMIHUAHSGKG-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 229960003887 dichlorophen Drugs 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- DLAPIMGBBDILHJ-UHFFFAOYSA-N dimethoxy-(3-methyl-4-methylsulfinylphenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)OC1=CC=C(S(C)=O)C(C)=C1 DLAPIMGBBDILHJ-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 2
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 2
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 2
- ZEYJIQLVKGBLEM-UHFFFAOYSA-N fuberidazole Chemical compound C1=COC(C=2N=C3[CH]C=CC=C3N=2)=C1 ZEYJIQLVKGBLEM-UHFFFAOYSA-N 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 2
- FCOAHACKGGIURQ-UHFFFAOYSA-N iprobenfos Chemical compound CC(C)OP(=O)(OC(C)C)SCC1=CC=CC=C1 FCOAHACKGGIURQ-UHFFFAOYSA-N 0.000 description 2
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 2
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 2
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 description 2
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 2
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- BLCKKNLGFULNRC-UHFFFAOYSA-L n,n-dimethylcarbamodithioate;nickel(2+) Chemical compound [Ni+2].CN(C)C([S-])=S.CN(C)C([S-])=S BLCKKNLGFULNRC-UHFFFAOYSA-L 0.000 description 2
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000004553 water soluble powder for seed treatment Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- 239000011701 zinc Chemical class 0.000 description 1
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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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
본 발명은 화학식 (I)의 발린아미드 유도체와 펜아미돈의 신규한 활성 화합물의 배합물 및 그의 식물병원성 진균을 구제하기 위한 용도에 관한 것이다.
[화학식 1]
상기식에서
R1및 R2는 명세서에 정의된 바와 같다.
Description
발린아미드 유도체는 살진균적 성질을 가지고 있음이 알려져있다(참조 EP-A 472 996). 이 물질의 활성은 우수하나 낮은 적용 비율에서 종종 만족스럽지 못한 경우가 있다. 또한, 펜아미돈 역시 진균을 구제하는데 이용될 수 있음이 알려져있다(참조 EP-A 0 629 616). 그러나 펜아미돈의 활성은 낮은 적용 비율에서 항상 만족스러운 것은 아니다.
본 발명은 한편으로 발린아미드 유도체와 다른 한편으로 펜아미돈을 포함하며 식물병원성 진균을 구제하는데 매우 적절한 신규한 활성 화합물의 배합물에 관한 것이다.
본 발명에 따라, 화학식 (I)의 발린아미드 유도체와 화학식 (II)의 펜아미돈의 신규한 활성 화합물의 배합물이 매우 우수한 살진균적 성질을 가짐이 밝혀졌다.
상기식에서
R1은 i-프로필 또는 s-부틸을 나타내고,
R2는 염소, 메틸, 에틸 또는 메톡시를 나타낸다.
놀랍게도 본 발명에 따른 활성 화합물의 배합물의 살진균적 활성은 각각의 활성 화합물의 활성의 합보다 훨씬 높다. 이것은 예측될 수 없는 진정한 상승효과이며 단순히 활성의 상보가 아니다.
화학식 (I)의 활성 화합물의 구조적 형태로부터 이 화합물은 두 개의 비대칭적으로 치환된 탄소 원자를 가짐을 알 수 있다. 따라서 생성물은 여러 이성체들의 혼합물이나 각각의 이성체의 형태로 존재할 수 있다.
바람직한 화학식 (I)의 화합물은 아미노산 부분이 i-프로필옥시카보닐-L-발린이나 sec-부틸옥시카보닐-L-발린에 의해 형성되고, 페네틸아민 부분이 라세믹이거나 S-(-)-형태를 가지나, 특히 R-(+)-형태를 가지는 화합물이다.
특히 바람직한 화학식 (I)의 화합물은 R1이 i-프로필을 나타내는 화합물이다.
특히 화학식 (Ia)의 1-메틸에틸[2-메틸-1-[[[-1-(4-클로로페닐)에틸]아미노]카보닐]-프로필]-카바메이트, 화학식 (Ib)의 1-메틸에틸[2-메틸-1-[[[-1-(4-메틸페닐)에틸]아미노]카보닐]-프로필]-카바메이트, 화학식 (Ic)의 1-메틸에틸[2-메틸
-1-[[[-1-(4-에틸페닐)에틸]아미노]카보닐]-프로필]-카바메이트 및 화학식 (Id)의 1-메틸에틸[2-메틸-1-[[[-1-(4-메톡시페닐)에틸]아미노]카보닐]-프로필]-카바메이트 및 상기 언급한 바와 같은 그들의 이성체가 언급될 수 있다.
화학식 (I)의 활성 화합물은 공지되어있다(참조 EP-A 0 472 996).
본 발명에 따른 배합물에 또한 존재하는 살진균성 활성 화합물 펜아미돈 역시 공지되어 있다(참조 EP-A 0 629 616).
화학식 (I)의 적어도 하나의 활성 화합물에 더하여, 본 발명에 따른 활성 화합물의 배합물은 화학식 (II)의 활성 화합물 펜아미돈을 포함한다. 그들은 부가적으로 또한 다른 살진균적 활성 혼합물 성분을 가질 수 있다.
본 발명에 따른 활성 화합물의 배합물에서 활성 화합물이 특정 중량비로 존재할 때 상승 효과가 특히 향상된다. 그러나 활성 화합물의 배합물에서 활성 화합물의 중량비는 비교적 넓은 범위내에서 변화될 수 있다. 일반적으로 화학식 (I)의 활성 화합물의 1 중량부에 대해 화학식 (II)의 활성 화합물이 0.1 내지 10 중량부, 바람직하게는 0.2 내지 2 중량부로 존재한다.
본 발명에 따른 활성 화합물의 배합물은 매우 우수한 살진균적 성질을 가지며 특히 식물병원성 진균, 예를 들면 플라스모디오포로마이시트(Plasmodiophoromyc
etes), 오오마이시트(Oomycetes), 키트리디오마이시트(Chytridiomycetes), 자이고마이시트(Zygomycetes), 아스코마이시트(Ascomycetes), 바시디오마이시트 (Basidiomycetes), 듀테로마이시트(Deuteromycetes)등의 구제에 이용될 수 있다.
본 발명에 따른 활성 화합물의 배합물은 특히 토마토 및 감자상의 피토프쏘라 인페스탄트(Phytophthorainfestants) 및 알테나리아 종(Alternaria spp.), 및 포도나무상의 플라스모파라 비티콜라(Plasmopara viticola)의 보호적 구제에 적절하다.
식물의 병을 구제하는데 요구되는 농도에서 식물이 활성 화합물의 배합물에 잘 견딜 수 있다는 사실은 상기한 식물의 지상부, 번식 줄기와 종자, 및 토양에의 처리를 허용한다.
본 발명에 따른 활성 화합물의 배합물은 통상적인 제제, 예를 들면 용액제, 유제, 현탁제, 분말, 폼(foam), 페이스트(pastes), 과립, 에어로졸 및 고분자성 물질과 시드(seed)에 대한 코팅 조성물의 미세캡슐, 및 ULV 제제로 전환될 수 있다.
이러한 제제는 공지된 방법, 예를 들면 활성 화합물 또는 활성 화합물의 배합물과 증량제, 즉 액체 용매, 가압 액화 가스, 및/또는 고체 담체를, 임의적으로 계면활성제, 즉 유화제 및/또는 분산제, 및/또는 발포제를 사용하여 혼합하여 생산된다. 사용된 증량제가 물인 경우, 예로서 보조 용매로서 유기 용매를 이용하는 것도 가능하다. 필수적으로, 적당한 액체 용매는 방향족, 예를 들면 자일렌, 톨루엔 또는 알킬나프탈렌; 염소화된 방향족 또는 염소화된 지방족 탄화수소, 예를 들면 클로로벤젠, 클로로에틸렌 또는 메틸렌 클로라이드; 지방족 탄화수소, 예를 들면 사이클로헥산 혹은 파라핀, 예로서 석유 분획물, 알콜, 예를 들면 부탄올 혹은 글리콜 및 그들의 에테르 및 에스테르, 케톤, 예를 들면 아세톤, 메틸 에틸 케톤, 메틸 이소부틸 케톤 또는 사이클로헥사논; 강한 극성 용매, 예를 들면 디메틸포름아미드 및 디메틸 설폭사이드, 또는 물이다. 액화된 가스상의 증량제 혹은 담체는 실온과 대기압에서 기체상인 액체를 의미하는 것으로, 예로서 에어로졸 분무제, 예를 들면 부탄, 프로판, 질소 및 이산화탄소가 있다. 적당한 고체 담체는 예로서 토양의 천연 미네랄, 예를 들면 고령토, 진흙, 활석, 초크, 석영, 아타펄지트(attapulgite), 몬트모릴로나이트(montmorillonite) 또는 규조토, 및 토양의 합성 미네랄, 예를 들면 미세하게 분할된 실리카, 알루미나 및 실리케이트가 있다. 과립에 적당한 고체 담체는 예로서 분쇄되고 분류된 자연석, 예를 들면 방해석, 대리석, 경석(pumice), 해포석(sepiolite), 및 백운암(dolomite) 또는 무기 및 유기 곡식의 합성 과립, 및 유기 물질의 과립, 예를 들면 톱밥, 코코넛 껍질, 옥수수 속, 및 담배 줄기가 있다. 적당한 유화제 및/또는 발포제는 예로서 비이온성 및 음이온성 유화제, 예를 들면 폴리옥시에틸렌 지방산 에스테르, 폴리옥시에틸렌 지방 알콜 에테르, 예로서 알킬아릴 폴리글리콜 에테르, 알킬설포네이트, 알킬 설페이트, 아릴설포네이트, 또는 단백질 가수분해물이 있다. 적당한 분산제는 예로서 리그닌-설파이트 페출액과 메틸셀룰로오스가 있다.
증점제(tackifiers), 예를 들면 카복실메틸셀룰로오스 및 분말, 과립 또는 유액(latices) 형태의 천연 및 합성 고분자, 예를 들면 아라비아 고무, 폴리비닐 알콜 및 폴리비닐 아세테이트 또는 천연 포스포리피드, 예를 들면 세파린 및 레시틴(lecithins) 및 합성 포스포리피드가 제제에 이용될 수 있다. 다른 첨가제는 미네랄 및 식물성 오일이 가능하다.
발색제, 예를 들면 무기 색소, 예로서 산화철, 산화 타이타늄 및 프러시안블루, 및 유기 염료, 예를 들면 알리자린(alizarin) 염료, 아조(azo) 염료 및 금속 프탈로시아나이드 염료, 및 미량 영양소, 예를 들면 철, 마그네슘, 보론, 구리, 코발트, 몰리브덴 및 아연의 염을 사용하는 것이 가능하다.
제제는 일반적으로 0.1 내지 95중량%, 바람직하게는 0.5 내지 90중량%의 활성 화합물을 포함한다.
제제에서 본 발명에 따른 활성 화합물의 배합물은 다른 활성 화합물, 예를 들면 살진균제, 살충제, 살진드기제 및 제초제와의 혼합물, 및 비료 혹은 식물 성장 조절제와의 혼합물로 존재할 수 있다.
그러한 혼합물들의 혼합 파트너의 예는 하기와 같다.
살진균제:
2-아미노부탄; 2-아닐리노-4-메틸-6-사이클로프로필-피리미딘; 2', 6'-디브로모-2-메틸-4'-트리플루오로메톡시-4'-트리플루오로-메틸-1,3-티아졸-5-카복산일라이드; 2,6-디클로로-N-(4-트리플루오로메틸벤질)-벤즈아미드; (E)-2-메톡시이미노-N-메틸-2-(2-페녹시페닐)-아세트아미드; 8-하이드록시퀴놀린 설페이트; 메틸 (E)-2-{2-[6-(2-시아노페녹시)-피리미딘-4-일옥시]-페닐}-3-메톡시아크릴레이트; 메틸 (E)-메톡스이미노-[알파-(o-톨릴옥시)-o-톨릴]-아세테이트; 2-페닐페놀 (OPP), 알디모르프(aldimorph), 암프로필포스(ampropylfos), 아닐아진(anilazine), 아자코나졸(azaconazole), 베날락실(benalaxyl), 베노다닐(benodanil), 베노밀(benomyl), 비나파크릴(binapacryl), 비페닐, 비테르타놀(bitertanol), 블라스티시딘-S(blasticidin-S), 브로머코나졸(bromuconazole), 부피리메이트(bupirima
te), 부티오베이트(buthiobate), 칼슘 폴리설파이드, 캡타폴(captafol), 캡탄(captan), 카벤다짐(carbendazim), 카복신, 퀴노메티오네이트, 클로로넵(chloroneb), 클로로피크린(chloropicrin), 클로로탈로닐(chlorothaloni
l), 클로졸리네이트(chlorozolinate), 쿠프라넵(cufraneb), 시모크사닐(cymoxani
l), 사이프로코나졸(cyproconazole), 사이프로푸람(cyprofuram), 디클로로펜, 디클로부트라졸(diclobutrazol), 디클로플루아니드(diclofluanid), 디클로메진(diclome
zin), 디클로란(dicloran), 디에토펜카브(diethofencarb), 디페노코나졸(difenoco
nazole), 디메티리몰(dimethirimol), 디메토모르프(dimethomorph), 디니코나졸
(diniconazole), 디노캡(dinocap), 디페닐아민, 디피리티온(dipyrithion), 디탈림포스(ditalimfos), 디티아논(dithianon), 도다인(dodine), 드라즈옥솔론(drazo
xolon), 에디펜포스, 에폭시코나졸, 에티리몰(ethirimol), 에트리디아졸(etridiazo
le), 페나리몰(fenarimol), 펜부코나졸(fenbuconazole), 펜푸람(fenfuram), 페니트로판(fenitropan), 펜피클로닐(fenpiclonil), 펜프로피딘(fenpropidin), 펜프로피모르프(fenpropimorph), 펜틴 아세테이트, 펜틴 하이드록사이드, 퍼밤(ferbam), 페림존(ferimzone), 플루아지남(fluazinam), 플루디옥소닐, 플루오로마이드, 플루퀸코나졸(fluquinconazole), 플루실라졸, 플루설파미드, 플루톨아닐, 플루트리아폴, 폴펫(folpet), 포세틸(fosetyl)-알루미늄, 프탈라이드(fthalide), 푸베리다졸
(fuberidazole), 푸랄락실(furalaxyl), 퍼메사이클록스(furmecyclox), 구아자틴
(guazatine), 헥사클로로벤젠, 헥사코나졸, 하이멕사졸(hymexazole), 이마자릴
(imazalil), 이미벤코나졸, 이미녹타딘(iminoctadine), 이프로벤포스(iprobenfos)
(IBP), 이프로디온, 이소프로티올란(isoprothiolane), 카수가마이신(kasugamycin), 구리 제제, 예를 들면 수산화 구리, 구리 나프테네이트, 구리 옥시클로라이드, 구리 설페이트, 산화구리, 옥신-구리 및 보독스(Bordeaux) 혼합물, 맨카파(manco
pper), 맨코제브(mancozeb), 매네브(maneb), 메파니피림(mepanipyrim), 메프로닐
(mepronil), 메타락실(metalaxyl), 메트코나졸(metconazole), 메타설포카브(meth
asulfocarb), 메스푸록삼(methfuroxam), 메티람(metiram), 메트설포박스(metsul
fovax), 마이클로부타닐(myclobutanil), 니켈 디메틸디티오카바메이트, 니트로탈-이소프로필, 누아리몰(nuarimol), 오푸레이스(ofurace), 옥사딕실(oxadixyl), 옥사모카브(oxamocarb), 옥시카복신, 페푸라조에이트(pefurazoate), 펜코나졸(pencon
azole), 펜사이쿠론(pencycuron), 포스디펜(phosdiphen), 피마리신(pimaricin), 피페라린, 폴리옥신, 프로베나졸(probenazole), 프로클로라즈(prochloraz), 프로사이미돈(procymidone), 프로파모카브(propamocarb), 프로피코나졸(propiconazole), 프로피네브(propineb), 피라조포스(pyrazophos), 피리페녹스(pyrifenox), 피리메타닐
(pyrimethanil), 피로퀼론(pyroquilon), 퀸토젠(quintozene)(PCNB), 황 및 황 제제, 테부카노졸(tebucanozole), 테클로프탈람(tecloftalam), 테크나진(tecnazene), 테트라코나졸(tetraconazole), 티아벤다졸(thiabendazole), 티사이오펜(thicyo
fen), 티오파네이트(thiophanate)-메틸, 티람(thiram), 톨클로포스(tolclophos)-메틸, 톨릴플루아니드(tolylfluanid), 트리아디메폰(triadimefon), 트리아디메놀
(triadimenol), 트리아즈옥사이드(triazoxide), 트리클아미드(trichlamid), 트리사이클라졸(tricyclazole), 트리데모르프(tridemorph), 트리플루미졸(triflumizole),트리포린(triforin), 트리티코나졸(triticonazole), 발리다마이신 A(validamycin A), 빈클로졸린(vinclozolin), 지네브(zineb), 지람(ziram).
살박테리아제:
브로노폴(bronopol), 디클로로펜, 니트라피린(nitrapyrin), 니켈 디메틸디티오카바메이트. 카수가마이신(kasugamycin), 옥틸리논(octhilinone), 푸란카복실산, 옥시테트라사이클린, 프로베나졸, 스트렙토마이신(streptomycin), 테클로프탈람 (tecloftalam), 구리 설페이트 및 다른 구리 제제.
살충제/살진드기제/네마티시드(Nematicides):
아바멕틴(abamectin), AC 303 630, 아세페이트(acephate), 아크리나트린(ac
rinathrin), 알라니카브(alanycarb), 알디카브(aldicarb), 알파메트린(alphamethri
n), 아미트라즈(amitraz), 아버멕틴(avermectin), AZ 60541, 아자디라크틴(azadira
chtin), 아진포스 A(azinphos A), 아진포스 M, 아조사이클로틴, 바실러스 투린지엔시스(Bacillus thuringiensis), 벤디오카브(bendiocarb), 벤푸라카브(benfuracarb
), 벤설탭(bensultap), 베타사이플루트린(betacyfluthrin), 비펜트린(bifentrin), BPMC, 브로펜프록스(brofenprox), 브로모포스 A(bromophos A), 부펜카브(bufencar
b), 부프로페진(buprofezin), 부토카복신(butocarboxin), 부틸피리다벤(butylpyri
daben), 카두사포스(cadusafos), 카바릴(carbaryl), 카보푸란(carbofuran), 카보페노티온(carbophenothion), 카보설판, 카탑(cartap), CGA 157 419, CGA 184699, 클로에토카브(chloethocarb), 클로에톡시포스(chlorethoxyfos), 클로에톡시포스(chlo
retoxyfos), 클로펜빈포스(chlorfenvinphos), 클로플루아주론(chlorfluazuron), 클로메포스(chlormephos), 클로피리포스(chlorpyrifos), 클로피리포스 M, 시스-레스메트린(cis-resmethrin), 클로사이트린(clocythrin), 클로펜테진(clofentezine), 시아노포스, 사이클로프로트린(cycloprothrin), 사이플루트린(cyfluthrin), 사이할로트린(cyhalothrin), 사이헥사틴(cyhexatin), 사이퍼메트린(cypermethrin), 사이로마진(cyromazine), 델타메트린(deltamethrin), 데메톤 M(demeton M), 데메톤 S, 데메톤-S-메틸, 디아펜티우론(diafenthiuron), 디아지논(diazinon), 디클로펜티온
(dichlofenthion), 디클로보스(dichlorvos), 디클리포스(dicliphos), 디크로토포스
(dicrotophos), 디에티온(diethion), 디플루벤주론(diflubenzuron), 디메토에이트
(dimethoate), 디메틸빈포스(dimethylvinphos), 디옥사티온(dioxathion), 디설포톤
(disulfoton), 에디펜포스(edifenphos), 에마멕틴(emamectin), 에스펜발레레이트
(esfenvalerate), 에티오펜카브(ethiofencarb), 에티온(ethion), 에토펜프록스
(ethofenprox), 에토프로포스(ethoprophos), 에토펜프록스(etofenprox), 에트림포스(etrimphos), 펜아미포스(fenamiphos), 펜아자퀸(fenazaquin), 산화 펜부타틴
(fenbutatin), 페니트로티온(fenitrothion), 페노부카브(fenobucarb), 페노티오카브(fenothiocarb), 페녹시카브(fenoxycarb), 펜프로파트린(fenpropathrin), 펜피라드(fenpyrad), 펜피록시메이트(fenpyroximate), 펜티온(fenthion), 펜발레레이트
(fenvalerate), 피프로닐(fipronil), 플루아지남(fluazinam), 플루사이클록수론
(flucycloxuron), 플루사이트리네이트(flucythrinate), 플루페녹수론(flufenoxu
ron), 플루펜프록스(flufenprox), 플루발리네이트(fluvalinate), 포노포스(fono
phos), 포모티온(formothion), 포스티아제이트(fosthiazate), 퍼브펜프록스(fubfen
prox), 푸라티오카브(furathiocarb), HCH, 헵테노포스(heptenophos), 헥사플루머론
(hexaflumuron), 헥시티아족스(hexythiazox), 이미다클로프리드(imidacloprid), 이프로벤포스(iprobenfos), 이사조포스(isazophos), 이소펜포스(isofenphos), 이소프로카브(isoprocarb), 이속사티온(isoxathion), 이베멕틴(ivemectin), 람다-사이할로트린(lamda-cyhlothrin), 루페누론(lufenuron), 말라티온(malathion), 메카밤(mecarbam), 메르빈포스(mervinphos), 메설펜포스(mesulfenphos), 메트알데히드, 메타크리포스(methacrifos), 메타미도포스(methamidophos), 메티다티온(meth
idathion), 메티오카브(methiocarb), 메토밀(methomyl), 메톨카브(metolcarb), 밀베멕틴(milbemectin), 모노크로토포스(monocrotophos), 목시덱틴(moxidectin), 날드(naled), NC 184, NI 25, 니텐피람(nitenpyram), 오메토에이트(omethoate),옥사밀(oxamyl), 옥시데메톤 M(oxydemethon M), 옥시데프로포스(oxydeprofos), 파라티온 A(parathion A), 파라티온 M, 퍼메트린(permethrin), 펜토에이트(phenthoate), 포레이트(phorate), 포살론(phosalone), 포스메트(phosmet), 포스팜돈(phospham
don), 폭심(phoxim), 피리미카브(pirimicarb), 피리미포스 M(pirimiphos M), 피리미포스 A, 프로페노포스(profenofos), 프로페노포스(profenophos), 프로메카브(pro
mecarb), 프로파포스(propaphos), 프로폭서(propoxur), 프로티오포스(prothiofos), 프로티오포스(prothiophos), 프로토에이트(prothoate), 피메트로진(pymetrozin), 피라클로포스(pyrachlophos), 피라클로포스(pyraclofos), 피라클로포스(pyracloph
os), 피라다펜티온(pyradaphenthion), 피레스메트린(pyresmethrin), 피레트럼(pyrethrum), 피리다벤(pyridaben), 피리미디펜(pyrimidifen), 피리프록시펜(pyriproxifen), 퀴날포스(quinalphos), RH 5992, 살리티온(salithion), 세부포스(sebufos), 실라플루오펜(silafluofen), 설포텝(sulfotep), 설프로포스(sulpro
fos), 테부페노지드(tebufenozid), 테부펜피라드(tebufenpyrad), 테부피림포스
(tebupirimphos), 테플루벤주론(teflubenzuron), 테플루트린(tefluthrin), 테메포스(temephos), 터밤(terbam), 터부포스(terbufos), 테트라클로빈포스(tetrachlor
vinphos), 티아페녹스(thiafenox), 티오디카브(thiodicarb), 티오파녹스(thiofan
ox), 티오메톤(thiomethon), 티오나진(thionazin), 투린지엔신(thuringiensin), 트랄로메트린(tralomethrin), 트리아라텐(triarathen), 트리아조포스(triazophos), 트리아주론(triazuron), 트리클로폰(trichlorfon), 트리플루머론(triflumuron), 트리메타카브(trimethacarb), 바미도티온(vamidothion), XMC, 자일릴카브(xylylcarb)
, YI 5301/5302, 제타메트린(zetamethrin).
활성 화합물의 배합물은 그 자체로, 그의 제제 형태로, 또는 그로부터 제조된 사용 형태, 예를 들면, 사용직전(ready-to-use)의 용액, 유화 가능한 농축액, 유제, 현탁액, 습윤성 분말, 가용성 분말 및 과립으로 사용될 수 있다. 이들은 통상의 방법, 예로서 끼얹기, 스프레이, 분무, 스캐터링, 살포, 및 건조 종자 처리를 위한 분말, 종자 처리를 위한 용액, 종자 처리를 위한 수용성 분말, 슬러리 처리를 위한 수용성 분말, 또는 외피 형성으로 사용될 수 있다.
식물의 부분의 처리에 있어서, 사용 형태에서의 활성 화합물 농도는 비교적으로 넓은 범위내에서 변화 가능하다. 일반적으로 그것은 1 내지 0.0001중량%, 바람직하게는 0.5 내지 0.001중량% 이다.
종자의 처리에 있어서 활성 화합물의 양은 일반적으로 종자 1kg당 0.001 내지 50g, 바람직하게는 0.01 내지 10g이 요구된다.
토양의 처리에 있어서 작용 부위당 0.00001 내지 0.1중량%, 바람직하게는 0.0001 내지 0.02중량%의 활성 화합물의 농도가 요구된다.
본 발명에 따른 활성 화합물의 배합물의 우수한 살진균적 활성은 하기의 실험으로 증명된다. 각각의 활성 화합물은 살진균적 활성에 있어서 열등하지만, 배합물은 단순한 활성의 합을 초과하는 활성을 나타낸다.
살진균제의 상승적 효과는 활성 화합물의 배합물의 살진균적 활성이 개별적으로 적용되는 활성 화합물의 활성의 총합을 초과할 때 항상 나타난다.
두 활성 화합물의 주어진 배합에 대해 예측되는 활성은 하기와 같은 방법으로 계산될 수 있다. (참조. Colby, S.R., "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds15, 20-22 쪽, 1967):
상기식에서,
X 는 활성 화합물 A를 mg/ha의 농도로 적용하였을 때, 비처리 대조군에 대해 %로 표현되는 효과이고,
Y 는 활성 화합물 B를 ng/ha의 농도로 적용하였을 때, 비처리 대조군에 대해 %로 표현되는 효과이며,
E 는 활성 화합물 A와 B를 m 및 ng/ha의 농도로 적용하였을 때, 비처리 대조군에 대해 %로 표현되는 효과이다.
실질적인 살진균적 활성이 계산된 값을 초과한다면, 그 배합의 활성은 초부가적, 즉 상승적 효과가 존재한다. 이러한 경우에, 실질적으로 관찰되는 효과는 상기 언급한 식으로부터 계산되는 예측되는 효과(E)의 값보다 커야한다.
플라스모파라 테스트(
Plasmopara
test) (포도나무) / 예방적
활성 화합물의 적당한 제제를 제조하기 위해서 시판 활성 화합물 제제(개개의 활성 화합물 또는 활성 화합물의 배합물) 또는 활성 화합물 1 중량부를 용매(아세톤) 4.7 중량부 및 유화제(알킬-아릴 폴리글리콜 에테르) 0.3 중량부와 혼합하고, 이 혼합물을 목적하는 특정의 농도로 될 때까지 물로 희석한다.
예방적 활성을 시험하기 위하여 어린 식물에 언급된 적용 비율로 활성 화합물의 배합물로 스프레이한다. 스프레이 코팅이 건조되면 식물을 플라스모파라 비티콜라(Plasmopara viticola)의 수성 포자 현탁액으로 접종하고, 약 20℃ 및 100% 상대 습도의 배양실 내에 하루동안 방치한다. 곧이어 식물을 약 21℃ 및 약 90% 상대습도의 온실에 5일간 방치한다. 다음으로 식물은 적셔지고 배양실 내에 하루동안 방치한다.
평가는 접종 후 6일째 날에 수행한다. 0%는 대조군에 상응하는 효과이고, 100%의 효과란 어떠한 감염도 관찰되지 않는다는 것을 의미한다.
본 발명에 따른 활성 화합물의 배합에서 관찰된 활성은 계산된 활성 보다 크다. 즉, 상승적 효과를 나타낸다. 1:1의 혼합비 및 5 g/ha의 적용 비율에서 이프로발리카브(iprovalicarb)와 페나미돈(fenamidone)의 배합은 실질적으로 98%의 효과를 나타낸다. 콜비의 식에 의해 계산되는 예측치는 45%으로 매우 낮다.
Claims (6)
- 적어도 하나의 화학식 (I)의 발리나미드 유도체와 화학식 (II)의 펜아미돈을 포함하는 활성 화합물의 배합물 :[화학식 I][화학식 II]상기식에서R1은 i-프로필 또는 s-부틸을 나타내고,R2는 염소, 메틸, 에틸 또는 메톡시를 나타낸다.
- 제 1 항에 있어서, 화학식 (1)의 활성 화합물과 화학식(2)의 활성 화합물의 중량비가 1: 0.1 내지 1: 10임을 특징으로 하는 활성 화합물의 배합물.
- 제 1 항에 따른 활성 화합물의 배합물을 진균 및/또는 그의 서식지에 적용함을 특징으로 하여 진균을 구제하는 방법.
- 제 1 항에 따른 활성 화합물의 배합물을 포함하는 살진균제 조성물.
- 삭제
- 제 1 항에 따른 활성 화합물의 배합물을 증량제 및/또는 계면활성제와 혼합함을 특징으로 하여 살진균제 조성물을 제조하는 방법.
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DE19904081A DE19904081A1 (de) | 1999-02-02 | 1999-02-02 | Fungizide Wirkstoffkombinationen |
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EP (1) | EP1150568B1 (ko) |
JP (1) | JP3841264B2 (ko) |
KR (1) | KR100446912B1 (ko) |
CN (1) | CN1204811C (ko) |
AR (1) | AR022294A1 (ko) |
AT (1) | ATE276659T1 (ko) |
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FR2789551B1 (fr) | 1999-02-12 | 2002-06-21 | Aventis Cropscience Sa | Compositions fongicides pour la protection des fruits |
MXPA03006033A (es) | 2001-01-22 | 2003-09-10 | Basf Ag | Mezclas fungicidas. |
DE10141618A1 (de) * | 2001-08-24 | 2003-03-06 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
FR2832031A1 (fr) * | 2001-11-14 | 2003-05-16 | Aventis Cropscience Sa | Composition fongicide a base d'au moins un derive de pyridylmethylbenzamide et d'au moins un derive de type valinamide |
ITMI20012430A1 (it) * | 2001-11-19 | 2003-05-19 | Isagro Spa | Composizioni a base di sali rameici sali rameici e loro utilizzo per il controllo di fitopatogeni |
DE602008003921D1 (de) | 2007-04-25 | 2011-01-20 | Syngenta Participations Ag | Fungizidzusammensetzungen |
EP2292094A1 (en) * | 2009-09-02 | 2011-03-09 | Bayer CropScience AG | Active compound combinations |
BR112013002081A2 (pt) | 2010-07-27 | 2018-01-30 | S Ginn Richard | sistema para estabilização sacro-ilíaca |
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UA61064C2 (uk) * | 1997-12-02 | 2003-11-17 | Рон-Пуленк Агро | Синергічна фунгіцидна композиція, що містить 2-інідазолін-5-он та спосіб боротьби з фітопатогенними грибками культур |
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ATE276659T1 (de) | 2004-10-15 |
EP1150568A1 (de) | 2001-11-07 |
TR200102212T2 (tr) | 2001-12-21 |
KR20010104336A (ko) | 2001-11-24 |
CN1204811C (zh) | 2005-06-08 |
HU228792B1 (en) | 2013-05-28 |
BR0007910A (pt) | 2001-11-06 |
ZA200105255B (en) | 2002-06-26 |
CN1338897A (zh) | 2002-03-06 |
HUP0105229A2 (hu) | 2002-04-29 |
RU2237996C2 (ru) | 2004-10-20 |
AU2543600A (en) | 2000-08-25 |
EP1150568B1 (de) | 2004-09-22 |
PL349862A1 (en) | 2002-09-23 |
JP3841264B2 (ja) | 2006-11-01 |
CO5210898A1 (es) | 2002-10-30 |
HUP0105229A3 (en) | 2004-06-28 |
ES2226778T3 (es) | 2005-04-01 |
PL195817B1 (pl) | 2007-10-31 |
ID30023A (id) | 2001-11-01 |
DE50007895D1 (de) | 2004-10-28 |
WO2000045638A1 (de) | 2000-08-10 |
HK1042827A1 (zh) | 2002-08-30 |
JP2002536303A (ja) | 2002-10-29 |
US6444693B1 (en) | 2002-09-03 |
PT1150568E (pt) | 2005-02-28 |
DE19904081A1 (de) | 2000-08-03 |
AR022294A1 (es) | 2002-09-04 |
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