CN101562979A - 锐劲特的晶型 - Google Patents
锐劲特的晶型 Download PDFInfo
- Publication number
- CN101562979A CN101562979A CNA2007800417681A CN200780041768A CN101562979A CN 101562979 A CN101562979 A CN 101562979A CN A2007800417681 A CNA2007800417681 A CN A2007800417681A CN 200780041768 A CN200780041768 A CN 200780041768A CN 101562979 A CN101562979 A CN 101562979A
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- Prior art keywords
- crystal formation
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- methyl
- compound
- sharp strength
- Prior art date
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- 230000004048 modification Effects 0.000 title abstract description 6
- 238000012986 modification Methods 0.000 title abstract description 6
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 title abstract description 3
- 239000005899 Fipronil Substances 0.000 title abstract description 3
- 229940013764 fipronil Drugs 0.000 title abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 239
- 238000000034 method Methods 0.000 claims abstract description 61
- 238000002360 preparation method Methods 0.000 claims abstract description 41
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 12
- 244000045947 parasite Species 0.000 claims abstract description 6
- 230000000590 parasiticidal effect Effects 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 226
- 239000013078 crystal Substances 0.000 claims description 172
- 230000015572 biosynthetic process Effects 0.000 claims description 150
- -1 third-1-alcohol Chemical compound 0.000 claims description 90
- 239000002904 solvent Substances 0.000 claims description 59
- 238000002425 crystallisation Methods 0.000 claims description 57
- 230000008025 crystallization Effects 0.000 claims description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
- 241000196324 Embryophyta Species 0.000 claims description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 40
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 39
- 239000007787 solid Substances 0.000 claims description 36
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 35
- 241001465754 Metazoa Species 0.000 claims description 28
- 241000238631 Hexapoda Species 0.000 claims description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 24
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 22
- 239000004546 suspension concentrate Substances 0.000 claims description 22
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 claims description 20
- 239000000843 powder Substances 0.000 claims description 19
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 18
- 150000001555 benzenes Chemical class 0.000 claims description 18
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 17
- 239000002798 polar solvent Substances 0.000 claims description 17
- 239000004562 water dispersible granule Substances 0.000 claims description 16
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 11
- 230000000749 insecticidal effect Effects 0.000 claims description 11
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 10
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 8
- 230000003071 parasitic effect Effects 0.000 claims description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 230000002141 anti-parasite Effects 0.000 claims description 6
- 239000003096 antiparasitic agent Substances 0.000 claims description 6
- 238000009395 breeding Methods 0.000 claims description 6
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 6
- 230000003405 preventing effect Effects 0.000 claims description 6
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 claims description 6
- 230000001488 breeding effect Effects 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 claims description 3
- 241000239290 Araneae Species 0.000 claims description 3
- 239000012752 auxiliary agent Substances 0.000 claims description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical class CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 3
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000002147 killing effect Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 3
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 claims description 3
- OSOUNOBYRMOXQQ-UHFFFAOYSA-N 1-chloro-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1 OSOUNOBYRMOXQQ-UHFFFAOYSA-N 0.000 claims description 2
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 claims description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- 241000244206 Nematoda Species 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 2
- 229940011051 isopropyl acetate Drugs 0.000 claims description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 claims description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims description 2
- 206010061217 Infestation Diseases 0.000 claims 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 230000002195 synergetic effect Effects 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 9
- 230000000361 pesticidal effect Effects 0.000 abstract description 4
- 241000894006 Bacteria Species 0.000 description 175
- 238000005755 formation reaction Methods 0.000 description 126
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 84
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 84
- 150000002148 esters Chemical class 0.000 description 51
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 description 44
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 44
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 44
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 44
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 44
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 description 44
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- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 description 44
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- 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 44
- AMSPWOYQQAWRRM-UHFFFAOYSA-N metrafenone Chemical compound COC1=CC=C(Br)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC AMSPWOYQQAWRRM-UHFFFAOYSA-N 0.000 description 44
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- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 44
- 239000004308 thiabendazole Substances 0.000 description 44
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- NNPRCLUGHFXSOU-UHFFFAOYSA-N 4-chloro-n-[cyano(ethoxy)methyl]benzamide Chemical compound CCOC(C#N)NC(=O)C1=CC=C(Cl)C=C1 NNPRCLUGHFXSOU-UHFFFAOYSA-N 0.000 description 43
- YLJLLELGHSWIDU-UHFFFAOYSA-N 4-cyclododecyl-2,6-dimethylmorpholin-4-ium;acetate Chemical compound CC([O-])=O.C1C(C)OC(C)C[NH+]1C1CCCCCCCCCCC1 YLJLLELGHSWIDU-UHFFFAOYSA-N 0.000 description 43
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- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 43
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- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 41
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- 150000004665 fatty acids Chemical class 0.000 description 30
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- 229910052731 fluorine Inorganic materials 0.000 description 21
- 229920001223 polyethylene glycol Polymers 0.000 description 20
- 239000011737 fluorine Substances 0.000 description 19
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- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 16
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Abstract
本发明涉及一种锐劲特的晶型,一种制备该晶型的方法,包含所述晶型的杀虫和杀寄生虫混合物和组合物及其用于对抗害虫和寄生虫的用途。
Description
本发明涉及一种锐劲特的新晶型,一种制备该晶型的方法,包含所述晶型的杀虫和杀寄生虫混合物和组合物及其用于对抗害虫和寄生虫的用途。
锐劲特(式I)是一种用于防治某些昆虫和螨虫害虫和寄生虫的活性化合物:
用于制备锐劲特的各种方法已广泛并详细地描述。给出详细制备程序的文献例如为EP 295 117;EP 460 940;EP 484 165;EP 668 269;EP 967206;EP 1 331 222;EP 1 374 061;US 5 631 381;CN 1374298;或J.of HeibeiUniversity of Science and Technology,第25卷(2),Sum 69(2004),Dok.Serial No.1008-1542(2004)02-0018-03。
通过现有技术中所述的方法获得的锐劲特材料的表征通常通过1H-NMR分析和/或测量熔点来进行。所述熔点在187-203℃的范围内,主要在195-203℃的范围内。在the Pesticidal Manual,第13版(2003),BritishCrop Protection Council,第433页中,锐劲特被描述为具有200-201℃的熔点的白色固体,其中工业锐劲特具有195.5-203℃的熔点。不同结晶形式的锐劲特的观察还未描述,至于特定晶型的任何表征或用于获得特定晶型的制备程序也没有描述。
对于大规模制备和配制诸如锐劲特的市售化合物,了解是否存在化合物的不同晶型(也经常称为多晶型物),可如何获得它们,及其特征性能如何是至关重要的。一种化合物的各晶型可能具有极不同的性能,例如溶解度、溶解速率、悬浮稳定性、研磨期间的稳定性、蒸气压力、光学和机械性能、吸湿性、晶体尺寸、过滤性能、干燥、密度、熔点、降解稳定性、防止相变为其它晶型的稳定性、颜色和甚至化学反应性。
例如,不同晶型经常自身以不同形式的晶体显示,如针状物或片状物。这例如与制备程序中的过滤步骤有关。在不同晶型的这类混合物中,片状物通常会阻塞过滤器的孔,导致时间和产物的损失和繁重且昂贵的清洁操作。同样,以片状物存在的晶型和以针状物存在的晶型可具有显著不同的涉及储存和包装的堆密度。尤其在杀虫剂的制备中,另一相关方面为晶型是以可产生有害粉尘的细粉末形式存在还是以无尘较大晶体形式存在。锐劲特的不同晶型具有不同堆密度且其不可预测比例的混合物在储存和包装时产生前述问题。
针对该背景,本发明的目的为找到锐劲特的新晶型且对其进行表征。
另一目的为找到该新晶型的制备程序,其可再现地产生晶型I。
本发明的另一目的为找到以高产率产生该新晶型I的制备程序。
本发明的又一目的为找到产生基本上不包括其它晶型(即超过80重量%)的新晶型的制备程序。这确保在制备、运输、储存和使用相应固态形式的所有方面中的再现性和稳定性。
因此,已找到一种锐劲特的新晶型,一种制备该晶型的方法,包含该晶型的杀虫和杀寄生虫混合物和组合物及其用于对抗害虫和寄生虫的用途。在整个本申请中,该锐劲特的新晶型定义为″新晶型I″。
同样,最令人惊讶的是,已找到锐劲特的3种其它晶型,其属于同在申请中的专利申请。尤其令人惊讶的是本发明的锐劲特的晶型I具有与第二晶型V极其类似的熔点,两个熔点均处于现有技术中所给出的熔点范围内(即195-203℃)。此外,同在申请中的专利申请中所述的锐劲特的两种其它晶型II和IV在加热过程中经历相变成为更稳定的形式I和V,因此在典型熔点测量中将得到这些形式I和II的熔点。因此固体形式的锐劲特属于极复杂结晶情况。可推断文献中所给出的熔点决不可能指出分析的是晶型还是晶型混合物。
在T 605/02中,欧洲专利局的技术复审委员会(Technical Board ofAppeal of the European Patent Authority)规定在各自的制备程序不存在的情况下,即使是特定晶型的XRD图案也因不能实现而不能构成现有技术。因此,在申请本申请之前所公开的文献中所给出的熔点不能视作本发明的现有技术,因为其不能使技术人员能够制备锐劲特的新晶型。
锐劲特的新晶型I以具有中心对称空间群C2/c的单斜晶系存在(本文中也称为″晶型I″或″晶型I″或″晶型″)。
(3)d=5.57±0.052θ=15.8±0.2°
(9)d=2.77±0.052θ=32.2±0.2°。
在特别优选实施方案中,该晶型I显示与图1中所示的图案基本相同的粉末X射线衍射图案。
晶型I的单晶的研究已显示基础晶体结构为单斜且具有空间群C2/c。晶型I的晶体结构的特征数据在表1中显示。
表1:晶型I的晶体学数据
a、b、c=晶胞的边长
α、β、γ=晶胞的角
Z=晶胞中分子的数目
锐劲特的晶型I通常具有在180-200℃范围内,尤其在190-200℃范围内,特别在196-198℃范围内的熔点,基本纯的形式为197℃。
锐劲特的晶型I的差示扫描量热法(DSC)热分析图具有194-197℃的起始温度且峰顶点为196-199℃的吸热。其示于图2中。
在另一实施方案中,本发明涉及具有至少92重量%,尤其至少96重量%,特别是至少98重量%的锐劲特含量的晶型I。
本发明还涉及固体锐劲特(锐劲特的组合物),其包含如上文所定义的晶型I和不同于该晶型I的锐劲特的形式(本文中也称为″锐劲特形式″),例如无定型锐劲特或具有不同于晶型I的晶型的锐劲特。优选该固体锐劲特(锐劲特的组合物)包含至少85重量%,优选至少90重量%,更优选至少95重量%,最优选至少98重量%的晶型I。
可通过本发明方法获得的晶型I以片状或薄片形式结晶。与锐劲特的其它晶型相比,其引起较少粉尘,并使制备程序中的过滤和干燥容易进行。该新晶型I进一步提供固体锐劲特组合物的高配制稳定性。
晶型I可使用包括以下步骤的方法来制备:
步骤i)制备不同于晶型I的固体形式的锐劲特在包含至少一种醇A1、乙腈、二甲亚砜(DMSO)或至少一种苯衍生物B1或其混合物的溶剂S中的溶液,该溶剂S可与另一溶剂AS组合;
步骤ii)进行锐劲特的结晶;和
步骤iii)分离所得沉淀。
根据本发明的醇A1为C1-C4链烷醇,即甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、2-丁醇或叔丁醇。
在工艺条件下苯衍生物B1为惰性的,且优选由苯组成,其可由一个或多个选自卤素、氰基、C1-C6烷基、C1-C6烷氧基、卤代甲基和硝基的基团取代,如氟苯、苄腈、苯甲醚、对二甲苯、邻二甲苯、间二甲苯、CF3-苯、异丙基苯、正丙基苯、正丁基苯、叔丁基苯、仲丁基苯、异丁基苯、氯苯、2-氯甲苯、4-氯甲苯、1,2-二氯苯、1,3-二氯苯、1,4-二氯苯、1,4-二异丙基苯、1,3,5-三甲基苯、硝基苯、2-硝基甲苯、3-硝基甲苯、4-硝基甲苯、正丙基苯和甲苯,更优选选自可被卤化的单(C1-C6烷基)苯、二(C1-C6烷基)苯或三(C1-C6烷基)苯。
在一个实施方案中,该另一溶剂AS可为非极性溶剂N,其降低锐劲特在溶剂S中的溶解度,该溶剂AS例如为烃类,优选C5-C14链烷烃,例如戊烷、己烷、庚烷、辛烷、壬烷、癸烷、十一烷或十二烷或其混合物。
在另一实施方案中,该另一溶剂AS可为极性溶剂P。添加溶剂P可有助于晶型I从溶液中结晶。
极性溶剂P优选选自:甲醇、乙醇、丙-1-醇、丙-2-醇(异丙醇)、丁-1-醇(正丁醇)、丁-2-醇、叔丁醇、2-甲基-丙-1-醇(异丁醇)、2-甲基-丙-2-醇、戊-3-醇、2-甲基丁-1-醇、3-甲基丁-1-醇、1,2-乙二醇、1,3-丙二醇、1,2-丙二醇、环己醇、乙腈、丙腈、丙酮、丁酮(甲基乙基酮)、戊-2-酮(甲基丙基酮)、戊-3-酮(二乙基酮)、4-甲基-2-戊酮(异丁基-甲基-酮)、3-甲基-丁-2-酮(异丙基-甲基-酮)、3,3-二甲基-2-丁酮(叔丁基-甲基-酮)、环己酮、乙酸甲酯、乙酸乙酯、乙酸异丙酯、乙酸正丁基酯、乙酸异丁酯、碳酸二乙酯、乙酸2-丁氧基乙酯、二噁烷、四氢呋喃(THF)、乙醚、2-甲基-THF、甲基-叔丁基醚、二甲基甲酰胺、二甲基乙酰胺、二甲亚砜(DMSO)、硝基甲烷和硝基乙烷。
在本发明方法中通常C2-C4链烷醇、酮和乙酸酯优选作为极性溶剂P。
在一个实施方案中,溶剂P在步骤i)开始时存在,其可为所用溶剂的至多50体积%,优选至多20体积%,最优选5-15体积%。
在另一实施方案中,溶剂P在步骤i)完成后加入。
这些步骤的详细说明如下:
步骤i)
不同于晶型I的适用于步骤i)的锐劲特形式例如选自无定型锐劲特或结晶锐劲特,如具有空间群P-1的三斜晶锐劲特,以及锐劲特的晶型的混合物。
用作步骤i)中的原料的锐劲特形式优选具有至少85重量%,尤其至少90重量%,特别是至少95重量%的纯度。″纯度″指不存在除锐劲特外的化合物。
用于步骤i)的溶剂S包含至少一种醇A1。溶剂S可额外含有水。
在另一实施方案中,S可为乙腈或DMSO,其可额外含有水或极性溶剂P。在另一实施方案中,S可为至少一种苯衍生物B1,其任选与极性溶剂P组合。该极性溶剂P通常以总溶剂体积的至少5体积%且至多20体积%,优选至多15体积%的比例应用。
溶剂S优选选自:
(a)纯的醇A1,
(b)不同醇A1的混合物,
(c)一种或多种醇A1与水的混合物,
(d)纯乙腈,
(e)乙腈与水和/或一种或多种额外溶剂AS的混合物,额外溶剂AS优选由极性溶剂P组成,
(f)纯DMSO,
(g)DMSO与水和/或一种或多种额外溶剂AS的混合物,额外溶剂AS优选由极性溶剂P组成,
(h)纯苯衍生物B1,
(i)一种或多种苯衍生物B1与一种或多种醇A1的混合物,和
(j)一种或多种苯衍生物B1与一种或多种额外溶剂AS的混合物,额外溶剂AS优选由极性溶剂P组成。
特别优选的醇A1为甲醇、乙醇和异丙醇。
在优选实施方案中,用于步骤i)的溶剂S由甲醇、乙醇或异丙醇组成,优选甲醇。
在另一实施方案中,用于步骤i)的溶剂S由如上文所定义的醇A1与水的混合物组成。水的比例基于溶剂S的总量优选不超过约25重量%。
根据本发明的苯衍生物B1为可被卤化的单(C1-C6烷基)苯、二(C1-C6烷基)苯或三(C1-C6烷基)苯,优选乙苯、正丙基苯、异丙基苯、二异丙基苯、正丁基苯、叔丁基苯、仲丁基苯、异丁基苯、CF3-苯、2-氯甲苯、3-氯甲苯和1,3,5-三甲基苯。
特别优选的苯衍生物B1为乙苯、二异丙基苯、正丁基苯和CF3-苯。
在优选实施方案中,用于步骤i)的溶剂S由优选选自乙苯、二异丙基苯、正丁基苯和CF3-苯的苯衍生物B1与至少一种选自丙酮、乙酸酯、酮或醇A1的溶剂的混合物组成,该醇A1优选选自乙醇或异丙醇。
在另一优选实施方案中,用于步骤i)的溶剂S由优选选自乙苯、二异丙基苯、正丁基苯和CF3-苯的苯衍生物B1与上文所定义且优选的极性溶剂P的混合物组成。
在溶剂S为乙腈的情况下,结晶步骤ii)优选通过在低温,如低于40℃的温度,优选20-25℃,最优选0-20℃下蒸发溶剂来进行。
在溶剂S为DMSO的情况下,结晶步骤ii)优选在低于80℃,优选低于50℃的温度,如在20-25℃,优选0-20℃的温度下进行。沉淀优选通过添加极性溶剂P或水,优选水来产生。
在步骤i)中,不同于晶型I的锐劲特形式通常以固体形式掺入溶剂S中,其中在溶剂S能够完全溶解锐劲特形式的浓度和温度下混合。
在本发明的优选实施方案中,在升高温度,优选30-60℃,特别优选在40-50℃下溶解锐劲特形式。溶解于溶剂S中的锐劲特形式的量取决于溶剂S的性质和溶解温度。本领域熟练技术人员可通过标准实验确定合适的条件。
在溶剂S由甲醇组成的情况下,用于溶解锐劲特形式的温度范围为20-60℃,尤其是40-50℃。
在溶剂S由苯衍生物B1,尤其乙苯、二异丙基苯、正丁基苯和CF3-苯组成的情况下,用于溶解锐劲特形式的温度范围通常高于90℃,优选100-140℃,尤其110-120℃。
步骤ii)
在本发明的方法步骤ii)中,然后使锐劲特结晶。结晶可以常规方式进行,例如通过使步骤i)中获得的溶液冷却,通过加入降低溶解度的溶剂,尤其通过加入水,或通过浓缩溶液,或通过上文所提及的措施的组合来进行。
在上述方法步骤的一个实施方案中,降低溶解度所加入的溶剂由极性溶剂P组成。
在一个优选实施方案中,步骤ii)在晶型I的种晶存在下进行。
为尽可能完全转化为晶型I,该结晶进行至少1h,尤其至少3h的时间(结晶持续时间)。对本领域熟练技术人员而言,将结晶持续时间理解为指在引发结晶的措施开始与通过从母液分离结晶材料来分离锐劲特之间的时间。
通常而言,使结晶进行其中已结晶出至少60重量%,优选至少70重量%,尤其至少90重量%(例如80-90重量%)的所用锐劲特的点。
溶液的冷却通常以每小时5-20K的冷却速率进行,优选在接近溶剂S的沸点,优选不超过90℃,更优选不超过80℃的升高温度下开始。例如,在溶剂S由乙醇组成的情况下,在60℃下开始并以每小时10K的速率进行冷却。通常将冷却速率调节在5-20K/h,优选至多10K/h的范围内。
通过逐渐移除溶剂S,如通过在真空中在低温下或在约20-25℃下,或在升高温度下和/或在诸如氮气或氩气的惰性气体流动存在下蒸发来进行溶液的浓缩。当然,″低温″和″升高温度″的值取决于溶剂S的性质,并由本领域熟练技术人员容易地确定。例如,在溶剂S由甲醇组成的情况下,优选在18-27℃下在空气中或在40-50℃下在氮气流动下进行蒸发。
优选在0-25℃的温度下由锐劲特的溶液获得晶型I。
特别优选通过将水加入步骤i)中获得的锐劲特溶液中来进行锐劲特的结晶,水的量基于用于溶解锐劲特形式的溶剂S的重量例如为20-130重量%,尤其50-130重量%,特别是100-130重量%。优选经较长时间,例如经15分钟至4小时,尤其是0.5-2小时加入水。优选在加入水后继续搅拌所得混合物。本领域熟练技术人员能够确定进行结晶所需的水量。
在另一优选实施方案中,通过依次加入第一量的降低溶解度的溶剂(优选水),然后加入晶型I的种晶来进行锐劲特的结晶。
通常而言,结晶的产率可进一步通过冷却至低于20℃的温度,优选冷却至0-10℃的温度来提高。
在优选实施方案中,通过浓缩溶液来进行结晶。
可通过将热溶液冷却至至少75℃,且将沉淀在至多100℃,优选至多95℃,更优选至多90℃下热调理使锐劲特从某些溶剂,如甲苯、氟苯、二甲苯、MCB或DCB中结晶。该热调理通常进行约12-48小时直至完成转化为晶型I。热调理的时间也取决于施加压力。
结晶可在减压下,如小于100巴,优选5-40毫巴下进行。
当冷却溶液时,在60-100℃,优选70-90℃的温度范围内开始结晶,这取决于溶液的饱和度。本领域熟练技术人员能够通过调节浓度、冷却速率和在结晶溶液中加入种晶的组合来影响结晶温度。
步骤iii)
在本发明的方法的步骤iii)中,使用从液体中分离固体组份的常规技术,例如通过过滤、离心或滗析来分离晶型I。通常而言,例如使用用于结晶的溶剂S洗涤所分离的沉淀。该洗涤可以一个或多个步骤进行。通常在低于30℃,特别是低于25℃的温度下进行洗涤,以使有价值产物的损失尽可能低。然后可将所得结晶锐劲特或晶型I干燥并经受进一步加工。
晶型I的分离也可通过在20-35℃下从乙腈蒸发来完成。
或者,晶型I的分离也可通过用水从乙腈或DMSO中沉淀来完成。
可重复由步骤i)至步骤iii)组成的制备方法以获得更高纯度的锐劲特。
晶型I尤其适用于有效对抗如下害虫:
千足虫(倍足纲(Diplopoda)),如Blaniulus或山蛩属(Narceus)
昆虫(昆虫纲(insecta))如:
蚂蚁、蜜蜂、黄蜂、锯蝇(膜翅目(Hymenoptera)),Atta capiguara、切叶蚁(Atta cephalotes)、Atta laevigata、Atta robusta、Atta sexdens、Attatexana、举腹蚁属(Crematogaster)、Hoplocampa minuta、Hoplocampatestudinea、小黄家蚁(Monomorium pharaonis)、热带火蚁(Solenopsisgeminate)、红火蚁(Solenopsis invicta)、黑火蚁(Solenopsis richteri)、南方火蚁(Solenopsis xyloni)、Pheidole megacephala,Pogonomyrmex属,如红蚂蚁(Pogonomyrmex barbatus)和Pogonomyrmex californicus,天鹅绒蚂蚁(Dasymutilla occidentalis)、熊蜂属(Bombus)、大黄蜂(Vespulasquamosa)、Paravespula vulgaris、Paravespula pennsylvanica、Paravespulagermanica、姬胡蜂(Dolichovespula maculata)、黄边胡蜂(Vespa crabro)、胡蜂(Polistes rubiginosa)、Campodontus floridanus和阿根廷蚁(Linepithema humile),
甲虫(鞘翅目(Coleoptera)),例如梨窄吉丁(Agrilus sinuatus)、直条叩头虫(Agriotes lineatus)、暗色叩头虫(Agriotes obscurus)和其他叩甲属(Agriotes)、Amphimallus solstitialis、Anisandrus dispar、墨西哥棉铃象(Anthonomus grandis)、苹花象(Anthonomus pomorum)、Aracanthusmorei、甜菜隐食甲(Atomaria linearis)、拟步甲属(Blapstinus)、纵坑切梢小蠹(Blastophagus piniperda)、Blitophaga undata、Bothynoderespunciventris、蚕豆象(Bruchus rufimanus)、豌豆象(Bruchus pisorum)、欧洲兵豆象(Bruchus lentis)、苹卷象(Byctiscus betulae)、甜菜大龟甲(Cassidanebulosa)、Cerotoma trifurcata、白菜籽龟象(Ceuthorrhynchus assimilis)、芫菁龟象(Ceuthorrhynchus napi)、甜菜胫跳甲(Chaetocnema tibialis)、Conoderus vespertinus和其他金针虫属(Conoderus)、Conorhynchusmendicus、石刁柏负泥虫(Crioceris asparagi)、Cylindrocopturusadspersus、Diabrotica(longicornis)barberi、Diabrotica semi-punctata、南美叶甲(Diabrotica speciosa)、黄瓜十一星叶甲(Diabroticaundecimpunctata)、玉米根叶甲(Diabrotica virgifera)和其他叶甲属(Diabrotica)、Eleodes属、墨西哥豆瓢虫(Epilachna varivestis)、烟草跳甲(Epitrix hirtipennis)、棉灰蒙象变种(Eutinobothrus brasiliensis)、欧洲松树皮象(Hylobius abietis)、埃及苜蓿叶象(Hypera brunneipennis)、紫苜蓿叶象(Hypera postica)、云杉八齿小蠹(Ips typographus)、烟草负泥虫(Lemabilineata)、黑角负泥虫(Lema melanopus)、马铃薯叶甲(Leptinotarsadecemlineata)、Limonius californicus和其他金针虫属(Limonius)、稻水象甲(Lissorhoptrus oryzophilus)、阿根廷茎象甲(Listronotus bonariensis)、玉米叩甲(Melanotus communis)和其他叩甲属(Melanotus)、油菜露尾甲(Meligethes aeneus)、大栗鳃金龟(Melolontha hippocastani)、五月鳃金龟(Melolontha melolontha)、水稻负泥虫(Oulema oryzae)、葡萄黑耳喙象(Ortiorrhynchus sulcatus)、Oryazophagus oryzae、草莓根象甲(Otiorrhynchus ovatus)、稻叶甲(Oulema oryzae)、辣根猿叶甲(Phaedoncochleariae)、Phyllotreta chrysocephala、Phyllophaga cuyabana和其他食叶鳃金龟属(Phyllophaga)、庭园发丽金龟(Phyllopertha horticola)、大豆淡足跳甲(Phyllotreta nemorum)、黄曲条菜跳甲(Phyllotreta striolata)和其他跳甲属(Phyllotreta)、日本金龟子(Popillia japonica)、Promecopscarinicollis、Premnotrypes voraz、兰跳甲属(Psylliodes)、豌豆叶象(Sitonalineatus)、谷象(Sitophilus granaria)、Sternechus pinguis、Sternechussubsignatus以及Tanymechus palliatus和其他Tanymechus属,
百足虫(唇足纲(Chilopoda)),例如Scutigera coleoptrata,
蟑螂(蜚蠊目(Blattaria-Blattodea),例如德国小蠊(Blattellagermanica)、Blattella asahinae、美洲大蠊(Periplaneta americana)、日本大蠊(Periplaneta japonica)、棕色蜚蠊(Periplaneta brunnea)、Periplanetafuligginosa、澳洲蜚蠊(Periplaneta australasiae)和东方蜚蠊(Blattaorientalis),
蟋蟀、蚱蜢、蝗虫(直翅目(Orthoptera)),例如居屋艾蟋(Achetadomestica)、蝼蛄(Gryllotalpa gryllotalpa)、飞蝗(Locusta migratoria)、双纹黑蝗(Melanoplus bivittatus)、红足黑蝗(Melanoplus femurrubrum)、墨西哥黑蝗(Melanoplus mexicanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplus spretus)、条纹红蝗(Nomadacris septemfasciata)、美洲沙漠蝗(Schistocerca americana)、沙漠蝗(Schistocerca gregaria)、摩洛哥戟纹蝗(Dociostaurus maroccanus)、庭疾灶螽(Tachycines asynamorus)、塞纳加尔小车蝗(Oedaleus senegalensis)、Zonozerus variegatus、非洲蔗蝗(Hieroglyphus daganensis)、Kraussaria angulifera、意大利蝗(Calliptamusitalicus)、澳洲草栖蝗(Chortoicetes terminifera)和褐色拟飞蝗(Locustanapardalina),
跳蚤(蚤目(Siphonaptera)),例如猫跳蚤(Ctenocephalides felis)、狗跳蚤(Ctenocephalides canis)、印鼠客蚤(Xenopsylla cheopis)、致痒蚤(Pulexirritans)、穿皮潜蚤(Tunga penetrans)和具带病蚤(Nosopsyllus fasciatus),
蝇、蚊(双翅目(Diptera)),例如埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedes albopictus)、剌扰伊蚊(Aedes vexans)、Agromyza oryzea、墨西哥果蝇(Anastrepha ludens)、五斑按蚊(Anopheles maculipennis)、Anophelescrucians、白足按蚊(Anopheles albimanus)、冈比亚按蚊(Anophelesgambiae)、Anopheles freeborni、海南岛白踝按蚊(Anopheles leucosphyrus)、云南微小按蚊(Anopheles minimus)、四斑按蚊(Anophelesquadrimaculatus)、红头丽蝇(Calliphora vicina)、蛆症金蝇(Chrysomyabezziana)、Chrysomya hominivorax、Chrysomya macellaria、鹿蝇(Chrysops discalis)、Chrysops silacea、Chrysops atlanticus、螺旋蝇(Cochliomyia hominivorax)、嗜人瘤蝇蛆(Cordylobia anthropophaga)、狂怒库蠓(Culicoides furens)、尖音库蚊(Culex pipiens)、致倦库蚊(Culexquinquefasciatus)、媒斑蚊(Culex tarsalis)、Culiseta inornata、Culisetamelanura、瓜实蝇(Dacus cucurbitae)、油橄榄实蝇(Dacus oleae)、油菜叶瘿蚊(Dasineura brassicae)、Delia antique、麦地种蝇(Delia coarctata)、灰地种蝇(Delia platura)、甘蓝地种蝇(Delia radicum)、Dermatobia hominis、小毛厕蝇(Fannia canicularis)、马蝇(Gasterophilus intestinalis)、GeomyzaTripunctata、刺舌蝇(Glossina morsitans)、须舌蝇(Glossina palpalis)、Glossina fuscipes、胶舌蝇(Glossina tachinoides)、Haematobia irritans、Haplodiplosis equestris、潜蝇属(Hippelates spp.)、纹皮蝇(Hypodermalineata)、Leptoconops torrens、蔬菜斑潜蝇(Liriomyza sativae)、美国潜叶蝇(Liriomyza trifolii)、Lucilia caprina、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Lucilia sericata)、Lycoria pectoralis、Mansonia属、麦瘿蚊(Mayetioladestructor)、家蝇(Musca domestica)、厩腐蝇(Muscina stabulans)、羊狂蝇(Oestrus ovis)、Opomyza florum、欧洲麦秆蝇(Oscinella frit)、天仙子泉蝇(Pegomya hysocyami)、银足白蛉(Phlebotomus argentipes)、葱蝇(Phorbiaantiqua)、萝卜蝇(Phorbia brassicae)、麦地种蝇(Phorbia coarctata)、progonya leyoscianii、胡萝卜茎蝇(Psila rosae)、Psorophora columbiae、Psorophora discolor、Prosimulium mixtum、樱桃实蝇(Rhagoletiscerasi)、苹果实蝇(Rhagoletis pomonella)、赤尾麻蝇(Sarcophagahaemorrhoidalis)、肉蝇属(Sarcophaga)、Simulium vittatum、厩螫蝇(Stomoxys calcitrans)、牛虻(Tabanus bovinus)、Tabanus atratus、红色原虻(Tabanus lineola)和Tabanus similis、Tetanops myopaeformis、Tipulaoleracea和欧洲大蚊(Tipula paludosa)
异翅目昆虫(异翅目(Heteroptera)),例如拟绿蝽(Acrosternum hilare)、玉米长蝽(Blissus leucopterus)、大叶蝉科(Cicadellidae)如蚕豆微叶蝉(Empoasca fabae)、叶甲科(Chrysomelidae)、黑斑烟盲蝽(Cyrtopeltisnotatus)、飞虱科(Delpahcidae)、棉红蝽(Dysdercus cingulatus)、Dysdercusintermedius、麦扁盾蝽(Eurygaster integriceps)、Euschistus impictiventris、棉红铃喙缘蝽(Leptoglossus phyllopus)、美洲牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lygus pratensis)、黑尾叶蝉属(Nephotettix)、稻绿蝽(Nezaraviridula)、蝽科(Pentatomidae)、甜菜拟网蝽(Piesma quadrata)、Solubeainsularis和Thyanta perditor,
蚜虫及其他同翅目昆虫(同翅目(Homoptera)),例如Acyrthosiphononobrychis、落叶松球蚜(Adelges laricis)、Aphidula nasturtii、甜菜蚜(Aphisfabae)、草莓根蚜(Aphis forbesi)、大豆蚜(Aphis glycines)、棉蚜(Aphisgossypii)、北美茶簏子蚜(Aphis grossulariae)、苹果蚜(Aphis pomi)、Aphisschneideri、卷叶蚜(Aphis spiraecola)、Aphis sambuci、豌豆蚜(Acyrthosiphon pisum)、马铃薯蚜(Aulacorthum solani)、Brachycauduscardui、杏圆尾蚜(Brachycaudus helichrysi)、Brachycaudus persicae、Brachycaudus prunicola、甘蓝蚜(Brevicoryne brassicae)、Capitophorushorni、Cerosipha gossypii、Chaetosiphon fragaefolii、Cryptomyzus ribis、高加索冷杉椎球蚜(Dreyfusia nordmannianae)、云杉椎球蚜(Dreyfusiapiceae)、居根西圆尾蚜(Dysaphis radicola)、Dysaulacorthum pseudosolani、Dysaphis plantaginea、Dysaphis pyri、蚕豆微叶蝉(Empoasca fabae)、桃大尾蚜(Hyalopterus pruni)、Hyperomyzus lactucae、麦长管蚜(Macrosiphum avenae)、大戟长管蚜(Macrosiphum euphorbiae)、蔷薇管蚜(Macrosiphon rosae)、Megoura viciae、巢莱修尾蚜(Melanaphis pyrarius)、麦无网蚜(Metopolophium dirhodum)、Myzodes(Myzus)persicae、冬葱瘤额蚜(Myzus ascalonicus)、Myzus cerasi、李瘤蚜(Myzus varians)、Nasonoviaribis-nigri、稻飞虱(Nilaparvata lugens)、囊柄瘿绵蚜(Pemphigusbursarius)、杨脉瘿绵蚜(Pemphigus populivenae)及其他瘿绵蚜属(Pemphigus)、蔗飞虱(Perkinsiella saccharicida)、忽布疣蚜(Phorodonhumuli)、木虱科(Psyllidae)如苹木虱(Psylla mali)、梨木虱(Psylla piri)及其他木虱属(Psylla)、冬葱瘤蛾蚜(Rhopalomyzus ascalonicus)、玉米蚜(Rhopalosiphum maidis)、禾谷溢管蚜(Rhopalosiphum padi)、Rhopalosiphum insertum、Sappaphis mala、Sappaphis mali、麦二叉蚜(Schizaphis graminum)、Schizoneura lanuginosa、麦长管蚜(Sitobionavenae)、白粉虱(Trialeurodes vaporariorum)、Toxoptera aurantiiand和葡萄根瘤蚜(Viteus vitifolii);
鳞翅目(Lepidoptera),例如小地老虎(Agrotis ypsilon)、黄地老虎(Agrotis segetum)及其他地虎属(Agrotis),木棉虫(Alabama argillacea)、黎豆夜蛾(Anticarsia gemmatalis)、Argyresthia conjugella、叉纹夜蛾(Autographa gamma)、树尺蠖(Bupalus piniarius)、Cacoecia murinana、Capua reticulana、Cheimatobia brumata、二化螟(Chilo suppresalis)及其他禾草螟属(Chilo),云杉色卷蛾(Choristoneura fumiferana)、Choristoneura occidentalis、二化螟(Cirphis unipuncta)、稻纵卷叶虫(Cnaphlocrocis medinalis)、苹果小卷蛾(Cydia pomonella)、松毛虫(Dendrolimus pini)、Diaphania nitidalis、西南玉米杆草螟(Diatraeagrandiosella)、埃和钻夜蛾(Earias insulana)、南美玉米苗斑螟(Elasmopalpus lignosellus)、女贞细卷蛾(Eupoecilia ambiguella)、切夜蛾属(Euxoa)、Evetria bouliana、Feltia subterranea、蜡螟(Galleria mellonella)、李小食心虫(Grapholitha funebrana)、梨小食心虫(Grapholitha molesta)、棉铃虫(Heliothis armigera)、烟芽夜蛾(Heliothis virescens)、玉米穗虫(Heliothis zea)、菜螟(Hellula undalis)、Hibernia defoliaria、美国白蛾(Hyphantria cunea)、苹果巢蛾(Hyponomeuta malinellus)、番茄虫蛾(Keiferia lycopersicella)、Lambdina fiscellaria、甜菜夜蛾(Laphygmaexigua)、Lerodea eufala、咖啡潜叶蛾(Leucoptera coffeella)、旋纹潜蛾(Leu coptera scitella)、Lithocolletis blancardella、葡萄浆果小卷蛾(Lobesiabotrana)、甜菜网螟(Loxostege sticticalis)、舞毒蛾(Lymantria dispar)、模毒蛾(Lymantria monacha)、桃潜蛾(Lyonetia clerkella)、黄褐天幕毛虫(Malacosoma neustria)、甘蓝夜蛾(Mamestra brassicae)、织蛾科(Momphidae)、黄杉毒蛾(Orgyia pseudotsugata)、玉米螟(Ostrinianubilalis)、小眼夜蛾(Panolis flammea)、棉花红铃虫(Pectinophoragossypiella)、疆夜蛾(Peridroma saucia)、圆掌舟蛾(Phalera bucephala)、马铃薯麦蛾(Phthorimaea operculella)、柑桔潜叶蛾(Phyllocnistis citrella)、欧洲粉蝶(Pieris brassicae)、苜蓿绿夜蛾(Plathypena scabra)、菜蛾(Plutellaxylostella)、大豆夜蛾(Pseudoplusia includens)、Rhyacionia frustrana、Scrobipalpula absoluta、Sesamia nonagrioides及其他蛀茎夜蛾属(Sesamia),麦蛾(Sitotroga cerealella)、葡萄卷叶蛾(Sparganothispilleriana)、草地夜蛾(Spodoptera frugiperda)、海灰翅夜蛾(Spodopteralittoralis)、斜纹夜蛾(Spodoptera litura)、Thaumatopoea pityocampa、绿色橡木飞蛾(Tortrix viridana)、粉纹夜蛾(Trichoplusia ni)和Zeirapheracanadensis;
虱(毛虱目(Phthiraptera)),例如人头虱(Pediculus humanus capitis)、人体虱(Pediculus humanus corporis)、阴虱(Pthirus pubis)、牛血虱(Haematopinus eurysternus)、猪血虱(Haematopinus suis)、牛颚虱(Linognathus vituli)、Bovicola bovis、鸡虱(Menopon gallinae)、Menacanthus stramineus和Solenopotes capillatus。
直翅目(Orthoptera),例如珍蝶科(Acrididae)、居屋艾蟋(Achetadomestica)、欧洲球螋(Forficula auricularia)、蝼蛄(Gryllotalpagryllotalpa)、飞蝗(Locusta migratoria)、双纹黑蝗(Melanoplus bivittatus)、红足黑蝗(Melanoplus femur-rubrum)、墨西哥黑蝗(Melanoplusmexicanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplusspretus)、条纹红蝗(Nomadacris septemfasciata)、美洲沙漠蝗(Schistocercaamericana)、Schistocerca peregrina、Stauronotus maroccanus和庭疾灶螽(Tachycines asynamorus);
衣鱼、家衣鱼(缨尾目(Thysanura)),例如西洋衣鱼(Lepisma saccharina)和斑衣鱼(Thermobia domestica),
白蚁(等翅目(Isoptera)),例如Calotermes flavicollis、乳白蚁属(Coptotermes)、玉米叶蝉(Dalbulus maidis)、金黄异白蚁(Heterotermesaureus)、Leucotermes flavipes、暗黄大白蚁(Macrotermes gilvus)、黑胸散白蚁属(Reticulitermes)、和Termes natalensis、台湾乳白蚁(Coptotermesformosanus);
蓟马(缨翅目(Thysanoptera)),例如烟褐蓟马(Frankliniella fusca)、苜蓿花蓟马(Frankliniella occidentalis)、东方花蓟马(Frankliniella tritici)及其他花蓟马属(Frankliniella),桔硬蓟马(Scirtothrips citri)、稻蓟马(Thripsoryzae)、棕榈蓟马(Thrips palmi)、菖蒲蓟马(Thrips simplex)和烟蓟马(Thrips tabaci),
蜱科和小鼠寄生螨虫(parasitic mites)(Parasitiformes):硬蜱科(Ixodidae),例如黑脚硬蜱(Ixodes scapularis)、全环硬蜱(Ixodes holocyclus)、太平洋硬蜱(Ixodes pacificus)、Rhiphicephalus sanguineus、安氏革蜱(Dermacentor andersoni)、美洲大革蜱(Dermacentor variabilis)、长星形壁虱(Amblyomma americanum)、Ambryomma maculatum、Ornithodorushermsi、Ornithodorus turicata和小鼠寄生螨虫(Mesostigmata),例如柏氏禽刺螨(Ornithonyssus bacoti)和鸡皮刺螨(Dermanyssus gallinae),
真正臭虫(半翅目(Hemiptera))如温带臭虫(Cimex lectularius)、热带臭虫(Cimex hemipterus)、Reduvius senilis、Triatoma属、Rhodniusprolixus和Arilus critatus,
蛛形纲,如蜘蛛(蜱螨目(Acarina)),例如软蜱科(Argasidae)、硬蜱科(Ixodidae)和疥螨科(Sarcoptidae),如长星形壁虱(Amblyommaamericanum)、热带花蜱(Amblyomma variegatum)、波斯锐缘蜱(Argaspersicus)、牛壁虱(Boophilus annulatus)、Boophilus decoloratus、微小牛蜱(Boophilus microplus)、Dermacentor silvarum、Hyalomma truncatum、蓖子硬蜱(Ixodes ricinus)、Ixodes rubicundus、毒蜘蛛(Latrodectus mactans)和褐丝蛛(Loxosceles reclusa)、Ornithodorus moubata、Otobius megnini、鸡皮刺螨(Dermanyssus gallinae)、绵羊疥病(Psoroptes ovis)、Rhipicephalusappendiculatus、Rhipicephalus evertsi、人疥螨(Sarcoptes scabiei)和瘿螨属(Eriophyidae),如苹果刺锈螨(Aculus schlechtendali)、Phyllocoptrataoleivora和Eriophyes sheldoni;细螨属(Tarsonemidae),如Phytonemuspallidus和侧多食跗线螨(polyphagotarsonemus latus);细须螨属(Tenuipalpidae),如紫红短须螨(Brevipalpus phoenicis);叶螨属(tetranychidae),如朱砂叶螨(tetranychus cinnabarinus)、神泽叶螨(tetranychus kanzawai)、太平洋叶螨(tetranychus pacificus)、棉叶螨(tetranychus telarius)和二点叶螨(tetranychus urticae),苹果叶螨(Panonychus ulmi)、柑椐叶螨(Panonychus citri)和Oligonychus pratensis;
蠼蛸(革翅目(Dermaptera)),例如欧洲球螋(forficula auricularia),
此外,晶型I尤其适用于防治作物害虫,尤其是鞘翅目、鳞翅目和蜱螨目。
此外,晶型I尤其适用于防治非作物害虫(庭院、草皮、观赏植物)。非作物害虫为唇足纲(Chilopoda)和倍足纲(Diplopoda)和等翅目(Isoptera)、Diptera(双翅目)、蜚蠊目(Blattaria)(Blattodea)、革翅目(Dermaptera)、半翅目(Hemiptera)、膜翅目(Hymenoptera)、直翅目(Orthoptera)、蚤目(Siphonaptera)、缨尾目(Thysanura)、毛虱目(Phthiraptera)和蜱螨目(Acarina)的害虫。
对本发明用途而言,可以将晶型I转化成常规配制剂,例如溶液、乳液、悬浮液、粉剂、粉末、糊和颗粒。使用形式取决于特定的意欲目的;在每种情况下应确保本发明化合物精细和均匀地分布。
配制剂以已知方式制备,例如通过将活性化合物与如下物质混合:适合配制农用化学品的助剂如溶剂和/或载体,需要的话表面活性剂(如辅助剂或分散剂),防腐剂,消泡剂,防冻剂,对于种子处理配制剂还任选着色剂和/或粘合剂和/或胶凝剂,(例如参见综述US 3,060,084、EP-A 707 445(对于液体浓缩物),Browning,“Agglomeration”,Chemical Engineering,1967年12月4日,147-48,Perry’s Chemical Engineer’s Handbook,第4版,McGraw-Hill,New York,1963,第8-57页及随后各页。WO 91/13546、US 4,172,714、US 4,144,050、US 3,920,442、US 5,180,587、US 5,232,701、US 5,208,030、GB 2,095,558、US 3,299,566,Klingman,Weed Control asa Science(杂草防治科学),John Wiley and Sons,Inc.,New York,1961,Hance等,Weed Control Handbook(杂草防治手册),第8版,BlackwellScientific Publications,Oxford,1989和Mollet,H.,Grubemann,A.,Formulation technology(配制技术),Wiley VCH Verlag GmbH,Weinheim(德国),2001,2.D.A.Knowles,Chemistry and Technology of AgrochemicalFormulations(农业化学配制剂化学和技术),Kluwer Academic Publishers,Dordrecht,1998(ISBN 0-7514-0443-8)。
合适的溶剂实例为水、芳族溶剂(如Solvesso产品、二甲苯)、石蜡(如矿物油馏分)、醇类(如甲醇、丁醇、戊醇、苄醇)、酮类(如环己酮、γ-丁内酯)、吡咯烷酮(NMP、NOP)、乙酸酯(乙二醇二乙酸酯)、二元醇、脂肪酸二甲基酰胺、脂肪酸及脂肪酸酯。原则上还可以使用溶剂混合物。
合适的载体的实例为磨碎的天然矿物(如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(如高度分散的硅石、硅酸盐)。
适用的表面活性剂是木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,烷基芳基磺酸盐,烷基硫酸盐,烷基磺酸盐,脂肪醇硫酸盐,脂肪酸和硫酸化脂肪醇乙二醇醚,还有磺化萘和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基酚醚,乙氧基化异辛基酚、辛基酚、壬基酚,烷基酚聚乙二醇醚,三丁基苯基聚乙二醇醚,三硬脂基苯基聚乙二醇醚,烷基芳基聚醚醇,醇和脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸盐废液和甲基纤维素。
适于制备可直接喷雾溶液、乳液、糊或油分散体的物质是中沸点到高沸点的矿物油馏分,如煤油或柴油,此外还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃,例如甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物、甲醇、乙醇、丙醇、丁醇、环己醇、环己酮、异佛尔酮,强极性溶剂,例如二甲亚砜、N-甲基吡咯烷酮或水。
防冻剂如甘油、乙二醇、丙二醇以及杀菌剂也可加入配制剂。
合适的消泡剂例如为基于硅或硬脂酸镁的消泡剂。
合适的防腐剂例如为双氯酚(Dichlorophen)和苯甲醇半缩甲醛(enzylalkoholhemiformal)。
种子处理配制剂可额外包含粘合剂和任选着色剂。
添加粘合剂以改进活性材料在处理后对于种子的粘附。合适粘合剂为嵌段共聚物EO/PO表面活性剂,以及聚乙烯醇、聚乙烯吡咯烷酮、聚丙烯酸酯、聚甲基丙烯酸酯、聚丁烯、聚异丁烯、聚苯乙烯、聚乙烯胺、聚乙烯酰胺、聚乙烯亚胺聚醚、聚氨酯、聚乙烯基乙酸酯、纤基乙酸钠和衍生自这些聚合物的共聚物。
任选在配制剂中也包含着色剂。适用于种子处理配制剂的着色剂或染料为若丹明B、C.I.颜料红112、C.I.溶剂红1、颜料蓝15:4、颜料蓝15:3、颜料蓝15:2、颜料蓝15:1、颜料蓝80、颜料黄1、颜料黄13、颜料红112、颜料红48:2、颜料红48:1、颜料红57:1、颜料红53:1、颜料橙43、颜料橙34、颜料橙5、颜料绿36、颜料绿7、颜料白6、颜料棕25、碱性紫10、碱性紫49、酸性红51、酸性红52、酸性红14、酸性蓝9、酸性黄23、碱性红10、碱性红108。
粉末、撒播用材料和可撒粉产品可以通过将活性物质与固体载体混合或同时研磨而制备。
颗粒如涂覆颗粒、浸渍颗粒和均质颗粒可以通过将活性化合物与固体载体粘附而制备。固体载体的实例是矿土如硅胶、硅酸盐、滑石、高岭土、活性粘土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵、尿素,以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其它固体载体。
配制剂通常包含0.01-95重量%,优选0.1-90重量%的活性化合物。此时,活性化合物以90-100重量%,优选95-100重量%的纯度(根据NMR谱)使用。
对于种子处理,各种配制剂可在稀释2-10倍后得到活性化合物在即用制剂中的0.01-60重量%,优选0.1-40重量%的浓度。
晶型I可以直接、以其配制剂形式或由其制备的使用形式,如可直接喷雾溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播用材料或颗粒,借助喷雾、雾化、撒粉、撒播或浇灌来使用。使用形式完全取决于意欲的目的;意欲在每种情况下确保本发明活性化合物的最佳可能分布。
含水使用形式可通过加入水由乳液浓缩物、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助湿润剂、增粘剂、分散剂或乳化剂将该物质直接或溶于油或溶剂中后在水中均化。然而还可以制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂以及合适的话溶剂或油组成的浓缩物且该浓缩物适于用水稀释。
即用制剂中的活性化合物浓度可在较宽范围内变化。其通常为0.0001-10重量%,优选0.01-1重量%。
活性化合物还可成功地以超低容量法(ULV)使用,其中可以施用包含超过95重量%活性化合物的配制剂或甚至可以在没有添加剂的情况下施用活性化合物。
下列为配制剂实例:
1.用水稀释的叶面施用产品
对于种子处理,这些产品可稀释或不经稀释而施用于种子。
A水溶性浓缩物(SL、LS)
将10重量份活性化合物溶于90重量份水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性化合物经水稀释溶解,以此方式得到活性化合物含量为10重量%的配制剂。
B分散性浓缩物(DC)
将20重量份活性化合物溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体,由此得到活性化合物含量为20重量%的配制剂。
C乳油(EC)
将15重量份活性化合物溶于80重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。用水稀释得到乳液,由此得到活性化合物含量为15重量%的配制剂。
D乳液(EW、EO、ES)
将25重量份活性化合物溶于35重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。借助乳化机(如Ultraturrax)将该混合物加入30重量份水中并制成均相乳液。用水稀释得到乳液,由此得到活性化合物含量为25重量%的配制剂。
E悬浮液(SC、OD、FS)
在搅拌的球磨机中,将20重量份活性化合物粉碎并加入10重量份分散剂和湿润剂以及70重量份水或有机溶剂,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液,由此得到活性化合物含量为20重量%的配制剂。
F水分散性颗粒和水溶性颗粒(WG、SG)
将50重量份活性化合物细碎研磨并加入50重量份分散剂和湿润剂,借助工业装置(如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性化合物分散体或溶液,由此得到活性化合物含量为50重量%的配制剂。
G水分散性粉末和水溶性粉末(WP、SP、SS、WS)
将75重量份活性化合物在转子-定子磨机中研磨并加入25重量份分散剂、湿润剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液,由此得到活性化合物含量为75重量%的配制剂。
H凝胶配制剂(GF)(仅用于种子处理)
在搅拌的球磨机中,将20重量份活性化合物在添加10重量份分散剂,1重量份胶凝剂/润湿剂以及70重量份水或有机溶剂下研磨,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液,由此得到活性化合物含量为20重量%的配制剂。
2.不经稀释而叶面施用的产品。对于种子处理,这些产品可经稀释而施用于种子。
I可撒粉粉末(DP、DS)
将5重量份活性化合物细碎研磨并与95重量份细碎高岭土充分混合。这得到活性化合物含量为5重量%的可撒粉产品。
J颗粒(GR、FG、GG、MG)
将0.5重量份活性化合物细碎研磨并结合99.5重量份载体,由此得到活性化合物含量为0.5重量%的配制剂。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而叶面施用的颗粒。
K ULV溶液(UL)
将10重量份活性化合物溶于90重量份有机溶剂如二甲苯中。这得到不经稀释而叶面施用的活性化合物含量为10重量%的产品。
常规的种子处理配制剂例如包括可流动浓缩物FS、溶液LS、干处理用粉末DS、淤浆处理用水分散性粉末WS、水溶性粉末SS以及乳液ES和EC以及凝胶配制剂GF。这些配制剂可以稀释或不经稀释的形式施用于种子。施用于种子可在播种之前进行或直接对种子进行。
在优选实施方案中,将FS配制剂用于种子处理。FS配制剂通常可包含1-800g/l活性成分、1-200g/l表面活性剂、0-200g/l防冻剂、0-400g/l粘合剂、0-200g/l颜料和至多1升溶剂,优选水。
本发明尤其涉及呈含水悬浮液浓缩物(SC)形式的杀虫或杀寄生虫组合物。这类悬浮液浓缩物包含呈细碎颗粒状形式的晶型I,其中晶型I的颗粒悬浮于含水介质中。活性化合物颗粒的尺寸(即90重量%活性化合物颗粒不超过的尺寸)通常低于30μm,尤其低于20μm。有利的是本发明SC中至少40重量%,特别是至少60重量%的颗粒具有低于2μm的直径。
除活性化合物外,悬浮液浓缩物通常包含表面活性剂,以及合适的话消泡剂、增稠剂、防冻剂、稳定剂(生物杀伤剂)、pH调节剂和抗结块剂。
在这类SC中,活性化合物的量,晶型I以及合适的话其它活性化合物的总量基于悬浮液浓缩物的总重量通常为10-70重量%,尤其是20-50重量%。
优选表面活性剂为阴离子和非离子表面活性剂。表面活性剂的量基于本发明含水SC的总重量通常为0.5-20重量%,尤其是1-15重量%,特别优选1-10重量%。优选表面活性剂包含至少一种阴离子表面活性剂和至少一种非离子表面活性剂,其中阴离子表面活性剂与非离子表面活性剂的重量比通常为10∶1-1∶10。
阴离子表面活性剂的实例包括烷基芳基磺酸盐、苯基磺酸盐、烷基硫酸盐、烷基磺酸盐、烷基醚硫酸盐、烷基芳基醚硫酸盐、烷基聚乙二醇醚磷酸盐、聚芳基苯基醚磷酸盐,烷基磺基琥珀酸酯、烯烃磺酸盐、链烷磺酸盐、石油醚磺酸盐、氨基乙磺酸盐、肌氨酸盐、脂肪酸、烷基萘磺酸、萘磺酸、木素磺酸、磺化萘与甲醛或与甲醛和苯酚以及合适的话尿素的缩合物,以及苯酚磺酸、甲醛和尿素的缩合物,木素-亚硫酸盐废液和木素磺酸盐,烷基磷酸盐,烷基芳基磷酸盐,如三苯乙烯基磷酸盐,以及聚羧酸盐如聚丙烯酸盐,马来酸酐/烯烃共聚物(如CP9,BASF),包括上述物质的碱金属盐、碱土金属盐、铵盐和胺盐。优选阴离子表面活性剂为含有至少一个磺酸根基团那些,尤其是它们的碱金属盐及其铵盐。
非离子表面活性剂的实例包括烷基酚烷氧基化物、醇烷氧基化物、脂肪胺烷氧基化物、聚氧乙烯甘油脂肪酸酯、蓖麻油烷氧基化物、脂肪酸烷氧基化物、脂肪酸酰胺烷氧基化物、脂肪酸聚二乙醇酰胺、羊毛脂乙氧基化物、脂肪酸聚乙二醇酯、异十三烷醇、脂肪酰胺、甲基纤维素、脂肪酸酯、烷基聚糖苷、甘油脂肪酸酯、聚乙二醇、聚丙二醇、聚乙二醇/聚丙二醇嵌段共聚物、聚乙二醇烷基醚、聚丙二醇烷基醚、聚乙二醇/聚丙二醇醚嵌段共聚物(聚氧乙烯/聚氧丙烯嵌段共聚物)及其混合物。优选非离子表面活性剂为脂肪醇乙氧基化物、烷基聚糖苷、甘油脂肪酸酯、蓖麻油烷氧基化物、脂肪酸烷氧基化物、脂肪酸酰胺烷氧基化物、羊毛脂乙氧基化物、脂肪酸聚乙二醇酯和氧化乙烯/氧化丙烯嵌段共聚物及其混合物。
本发明SC尤其包含至少一种改进由含水施用形式润湿植物部分的表面活性剂(湿润剂)和至少一种稳定活性化合物颗粒在SC中的分散体的表面活性剂(分散剂)。湿润剂的量基于SC的总重量通常为0.5-10重量%,尤其是0.5-5重量%,特别是0.5-3重量%。分散剂的量基于SC的总重量通常为0.5-10重量%,特别是0.5-5重量%。
优选湿润剂具有阴离子或非离子性质且例如选自萘磺酸,包括其碱金属盐、碱土金属盐、铵盐和胺盐,还有脂肪醇乙氧基化物、烷基聚糖苷、甘油脂肪酸酯、蓖麻油烷氧基化物、脂肪酸烷氧基化物、脂肪酰胺烷氧基化物、脂肪聚二乙醇酰胺、羊毛脂乙氧基化物和脂肪酸聚乙二醇酯。
优选分散剂具有阴离子或非离子性质且例如选自聚乙二醇/聚丙二醇嵌段共聚物、聚乙二醇烷基醚、聚丙二醇烷基醚、聚乙二醇/聚丙二醇醚嵌段共聚物、烷基芳基磷酸盐(例如三苯乙烯基磷酸盐)、木素磺酸、磺化萘与甲醛或与甲醛和苯酚以及合适的话尿素的缩合物,以及苯酚磺酸、甲醛和尿素的缩合物、木素亚硫酸盐废液和木素磺酸盐、聚羧酸盐,如聚丙烯酸盐、马来酸酐/烯烃共聚物(例如CP9、BASF),包括上文所提及物质的碱金属盐、碱土金属盐、铵盐和胺盐。
适用于本发明含水SC的粘度改性添加剂(增稠剂)尤其为赋予配制剂假塑性流动行为如静止状态下高粘度和运动状态下低粘度的化合物。合适的化合物原则上是为此用于悬浮浓缩物所有那些。可提及的物质例如为无机物质,如膨润土或硅镁土(例如购自Engelhardt的),和有机物质如多糖和杂多糖如黄原胶(如Kelco的),23(RhonePoulenc)或(购自R.T.Vanderbilt),优选使用黄原胶。粘度改性添加剂的量基于SC的总重量通常为0.1-5重量%。
适用于本发明含水SC的消泡剂实例是为此已知的聚硅氧烷乳液(如Wacker的SRE,或Rhodia的),长链醇,脂肪酸,蜡水分散体类型的消泡剂,固体消泡剂(所谓的配混物),有机氟化合物及其混合物。消泡剂的量基于SC的总重量通常为0.1-1重量%。
也可将杀菌剂加入本发明悬浮液浓缩物中以稳定它们。合适的杀菌剂为基于异噻唑啉酮(isothiazolone)的那些,例如购自ICI的或购自Thor chemie的RS或购自Rohm&Haas的MK。杀菌剂的量基于SC的总重量通常为0.05-0.5重量%。
合适的防冻剂为液体多元醇,例如乙二醇、丙二醇或甘油。防冻剂量基于含水悬浮液浓缩物的总重量通常为1-20重量%,尤其是5-10重量%。
合适的话,本发明含水SC可包含缓冲剂以调节pH。缓冲剂的实例为无机或有机弱酸如磷酸、硼酸、乙酸、丙酸、柠檬酸、富马酸、酒石酸、草酸和琥珀酸的碱金属盐。
本发明尤其涉及水分散性颗粒(WG)或水分散性粉末(WP)形式的杀虫或杀寄生虫组合物。这类配制剂包含细碎颗粒形式的晶型I,其中晶型I的颗粒以固体或粉末形式均化。活性化合物颗粒的尺寸(即90重量%的活性化合物颗粒不超过的尺寸)通常低于30μm,尤其是低于20μm。有利的是在本发明WG或WP中至少40重量%,尤其是至少60重量%的颗粒具有低于5μm的直径。
除了活性化合物之外,水分散性粉末和水分散性颗粒通常包含表面活性剂以及合适的话消泡剂、填料、粘合剂和抗结块剂。
在这类WG和WP中,活性物质的量,即晶型I以及合适的话其它活性化合物的总量基于WG/WP的总重量通常为10-90重量%,尤其是20-75重量%。
优选表面活性剂为阴离子和非离子表面活性剂。通常而言,表面活性剂的量基于本发明WG或WP的总重量为0.5-20重量%,尤其是1-15重量%,特别优选1-10重量%。优选表面活性剂包含至少一种阴离子表面活性剂和至少一种非离子表面活性剂,其中阴离子表面活性剂与非离子表面活性剂的重量比通常为10∶1-1∶10。
阴离子表面活性剂的实例包括烷基芳基磺酸盐、苯基磺酸盐、烷基硫酸盐、烷基磺酸盐、烷基醚硫酸盐、烷基芳基醚硫酸盐、烷基聚乙二醇醚磷酸盐、聚芳基苯基醚磷酸盐,烷基磺基琥珀酸酯、烯烃磺酸盐、链烷磺酸盐、石油醚磺酸盐、氨基乙磺酸盐、肌氨酸盐、脂肪酸、烷基萘磺酸、萘磺酸、木素磺酸、磺化萘与甲醛或与甲醛和苯酚以及合适的话尿素的缩合物,以及苯酚磺酸、甲醛和尿素的缩合物,木素-亚硫酸盐废液和木素磺酸盐,烷基磷酸盐,烷基芳基磷酸盐,如三苯乙烯基磷酸盐,以及聚羧酸盐如聚丙烯酸盐,马来酸酐/烯烃共聚物(如CP9,BASF),包括上述物质的碱金属盐、碱土金属盐、铵盐和胺盐。优选阴离子表面活性剂为含有至少一个磺酸根基团那些,尤其是它们的碱金属盐及其铵盐。
非离子表面活性剂的实例包括烷基酚烷氧基化物、醇烷氧基化物、脂肪胺烷氧基化物、聚氧乙烯甘油脂肪酸酯、蓖麻油烷氧基化物、脂肪酸烷氧基化物、脂肪酸酰胺烷氧基化物、脂肪酸聚二乙醇酰胺、羊毛脂乙氧基化物、脂肪酸聚乙二醇酯、异十三烷醇、脂肪酰胺、甲基纤维素、脂肪酸酯、烷基聚糖苷、甘油脂肪酸酯、聚乙二醇、聚丙二醇、聚乙二醇/聚丙二醇嵌段共聚物、聚乙二醇烷基醚、聚丙二醇烷基醚、聚乙二醇/聚丙二醇醚嵌段共聚物(聚氧乙烯/聚氧丙烯嵌段共聚物)及其混合物。优选非离子表面活性剂为脂肪醇乙氧基化物、烷基聚糖苷、甘油脂肪酸酯、蓖麻油烷氧基化物、脂肪酸烷氧基化物、脂肪酸酰胺烷氧基化物、羊毛脂乙氧基化物、脂肪酸聚乙二醇酯和氧化乙烯/氧化丙烯嵌段共聚物及其混合物。
本发明WG或WP尤其包含至少一种改进由含水施用形式润湿配制剂的表面活性剂(湿润剂)和至少一种使活性化合物颗粒在水稀释液中分散的表面活性剂。湿润剂的量基于WG/WP的总重量通常为0.5-10重量%,尤其是0.5-5重量%,特别是0.5-3重量%。分散剂的量基于WG/WP的总重量通常为0.5-10重量%,特别是2.0-8重量%。
优选湿润剂具有阴离子或非离子性质且例如选自萘磺酸,包括其碱金属盐、碱土金属盐、铵盐和胺盐,还有脂肪醇乙氧基化物、烷基聚糖苷、甘油脂肪酸酯、蓖麻油烷氧基化物、脂肪酸烷氧基化物、脂肪酰胺烷氧基化物、脂肪聚二乙醇酰胺、羊毛脂乙氧基化物和脂肪酸聚乙二醇酯。
优选分散剂具有阴离子或非离子性质且例如选自聚乙二醇/聚丙二醇嵌段共聚物、聚乙二醇烷基醚、聚丙二醇烷基醚、聚乙二醇/聚丙二醇醚嵌段共聚物、烷基芳基磷酸盐(例如三苯乙烯基磷酸盐)、磷酸钠、月桂基硫酸钠、改性纤维素胶、聚乙烯基吡咯烷酮、木素磺酸、磺化萘与甲醛或与甲醛和苯酚以及合适的话尿素的缩合物,以及苯酚磺酸、甲醛和尿素的缩合物、木素亚硫酸盐废液和木素磺酸盐、聚羧酸盐,如聚丙烯酸盐、马来酸酐/烯烃共聚物(例如CP9、BASF),包括上文所提及物质的碱金属盐、碱土金属盐、铵盐和胺盐。
适用于本发明WG或WP的消泡剂实例是为此已知的牛脂皂(AgniqueSoap L、Foamaster Soap L),长链醇,脂肪酸,有机氟化合物及其混合物。消泡剂的量基于WG/WP的总重量通常为0.1-1重量%。
适合于本发明WG和WP的填料、粘合剂或其它分散助剂通常组成配制剂的剩余部分。这些物质通常例如为高岭土或硅镁土、热解或沉淀硅石、硅藻土、硫酸铵或硅酸钙。
晶型I经由接触和进食而起作用。
根据本发明的优选实施方案,经由土壤施用来使用晶型I。土壤施用尤其有利于对抗蚂蚁、白蚁、蟋蟀或蟑螂。
根据本发明的另一优选实施方案,为了用于对抗非作物害虫如蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀、蝗虫或蟑螂,将晶型I制备成诱饵制剂。
诱饵可以是液体、固体或半固体制剂(例如凝胶)。固体诱饵可以制成各种适合相应用途的形状和形式,如颗粒、块、棒、片。液体诱饵可以填充到各种装置中以确保适当施用,例如敞开容器、喷雾装置、液滴供应源或蒸发源。凝胶可以基于含水基质或油性基质且可以按照粘性、水分保留或老化特性根据特定要求配制。
用于组合物中的诱饵是具有足够的吸引力以刺激诸如蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀等的昆虫或蟑螂食用它的产品。该吸引剂可以选自进食刺激剂或伪和/或性信息素。合适的食物刺激剂例如选自动物和/或植物蛋白质(肉-、鱼-或血液膳食,昆虫部分、蟋蟀粉末、蛋黄)、动物和/或植物来源的脂肪和油或单-、低聚-或聚有机糖类,尤其是蔗糖、乳糖、果糖、右旋糖、葡萄糖、淀粉、果胶或甚至糖蜜或蜂蜜,或选自盐如硫酸铵、碳酸铵或乙酸铵。水果、作物、植物、动物、昆虫的新鲜或腐败部分或其特定部分也可以用作进食刺激剂。已知信息素更具昆虫特异性。特殊信息素描述于文献中且对本领域熟练技术人员是已知的。
我们发现杀虫混合物解决降低剂量率和/或改进杀虫活性谱和/或组合击倒活性与长期防治和/或抗性管理和/或促进植物的健康的问题。
本发明的组合物还可以含有其他活性成分,例如其他农药,杀虫剂,杀真菌剂,除草剂,肥料如硝酸铵、尿素、钾碱和过磷酸盐,植物毒素和植物生长调节剂和安全剂和杀线虫剂。这些额外成分可以与上述组合物依次或结合使用,合适的话还在紧临使用前加入(桶混合)。例如可以在用其他活性成分处理之前或之后用本发明组合物喷雾植物。
已发现晶型I与至少一种下文所定义的杀虫或杀真菌化合物的混合物当施用于植物、植物部分、种子或其生长场所时与用单个化合物可能获得的防治率相比获得显著增强的对抗害虫和/或真菌的作用和/或适合于改善植物的健康。
下列可与本发明晶型I一起使用的杀虫或杀寄生虫化合物意欲说明可能的组合,而非施加任何限制:
A.1.有机(硫代)磷酸酯类:高灭磷(Acephate)、唑啶磷(azamethiphos)、谷硫磷(Azinphos-methyl)、毒死蜱(Chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、毒虫畏(Chlorfenvinphos)、二嗪农(Diazinon)、敌敌畏(Dichlorvos)、百治磷(Dicrotophos)、乐果(Dimethoate)、乙拌磷(Disulfoton)、乙硫磷(Ethion)、杀螟松(Fenitrothion)、倍硫磷(Fenthion)、异噁唑磷(Isoxathion)、马拉硫磷(Malathion)、甲胺磷(Methamidophos)、杀扑磷(Methidathion)、甲基一六零五(Methyl-Parathion)、速灭磷(Mevinphos)、久效磷(Monocrotophos)、砜吸磷(Oxydemeton-methyl)、对氧磷(Paraoxon)、一六零五(Parathion)、稻丰散(Phenthoate)、伏杀磷(Phosalone)、亚胺硫磷(Phosmet)、磷胺(Phosphamidon)、甲拌磷(Phorate)、辛硫磷(Phoxim)、虫螨磷(Pirimiphos-methyl)、丙溴磷(Profenofos)、丙硫磷(Prothiofos)、乙丙硫磷(Sulprophos)、杀虫畏(tetrachlorvinphos)、特丁磷(terbufos)、三唑磷(Triazophos)、敌百虫(Trichlorfon);
A.2.氨基甲酸酯:棉铃威(alanycarb)、涕灭威(aldicarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、双氧威(fenoxycarb)、呋线威(furathiocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、唑蚜威(triazamate);
A.3.合成除虫菊酯:氟锁草醚丙烯除虫菊(allethrin)、氟氯菊酯(bifenthrin)、乙氰菊脂(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、氯氰菊酯(cypermethrin)、甲体氯氰菊酯(alpha-cypermethrin)、乙体氯氰菊酯(beta-cypermethrin)、己体氯氰菊酯(zeta-cypermethrin)、溴氰菊酯(deltamethrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、咪炔菊酯(imiprothrin)、氯氟氰菊酯(Lambda-Cyhalothrin)、氯菊酯(permethrin)、炔酮菊酯(prallethrin)、除虫菊酯I和II、灭虫菊(resmethrin)、灭虫硅醚(silafluofen)、氟胺氰菊酯(Tau-Fluvalinate)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)和丙氟菊酯(profluthrin)、四氟甲醚菊酯(dimefluthrin);
A.4.生长调节剂:a)几丁质合成抑制剂:苯甲酰基脲类:定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、伏虫隆(teflubenzuron)、杀虫隆(triflumuron);噻嗪酮(Buprofezin)、噁茂醚(Diofenolan)、噻螨酮(Hexythiazox)、特苯噁唑(Etoxazole)、四螨嗪(Clofentazine);b)蜕皮激素拮抗剂:特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide)、艾扎丁(Azadirachtin);c)保幼激素类似物:蚊蝇醚(pyriproxyfen)、蒙五一五(methoprene)、双氧威(fenoxycarb);d)类脂生物合成抑制剂:螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat);
A.5.烟碱受体激动剂/拮抗剂化合物:噻虫胺(Clothianidin)、呋虫胺(dinotefuran)、吡虫啉(Imidacloprid)、噻虫嗪(Thiamethoxam)、硝胺烯啶(Nitenpyram)、吡虫清(acetamiprid)、噻虫啉(Thiacloprid);式Γ1的噻唑化合物:
A.6.GABA拮抗剂化合物:氯丹(acetoprole)、硫丹(endosulfan)、乙虫清(ethiprole)、锐劲特(fipronil)、氟吡唑虫(vaniliprole)、pyrafluprole、pyriprole、式Γ2的5-氨基-1-(2,6-二氯-4-三氟甲基-苯基)-4-三氟甲烷亚磺酰基-1H-吡唑-3-硫代甲酸酰胺:
A.7.大环内酯杀虫剂:齐墩螨素(abamectin)、甲氨基阿维菌素(emamectin)、米尔螨素(milbemectin)、lepimectin、艾克敌105(spinosad);
A.8.METI I化合物:喹螨醚(fenazaquin)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)、flufenerim;
A.9.METI II和III化合物:灭螨醌(acequinocyl)、fluacyprim、灭蚁腙(hydramethylnon);
A.10.分离剂化合物:氟唑虫清(chlorfenapyr);
A.11.氧化磷酸化抑制剂化合物:三环锡(cyhexatin)、杀螨硫隆(diafenthiuron)、杀螨锡(fenbutatin oxide)、克螨特(propargite);
A.12.蜕皮干扰剂(Moulting disruptor)化合物:cryomazine;
A.13.混合功能氧化酶抑制剂化合物:增效醚(piperonyl butoxide);
A.14.钠通道阻断剂化合物:噁二唑虫(indoxacarb)、氰氟虫胺(metaflumizone);
A.15.下列各种化合物:benclothiaz、联苯肼酯(bifenazate)、杀螟丹(cartap)、氟啶虫酰胺(flonicamid)、啶虫丙醚(pyridalyl)、拒嗪酮(pymetrozine)、硫、硫环杀(thiocyclam)、氟虫酰胺(flubendiamide)、cyenopyrafen、吡氟硫磷(flupyrazofos)、丁氟螨酯(cyflumetofen)、amidoflumet、式Γ3的邻氨基苯甲酰胺(anthranilamide)化合物:
其中A1为CH3、Cl、Br、I,X为C-H、C-Cl、C-F或N,Y′为F、Cl或Br,Y″为氢、F、Cl、CF3,B1为氢、Cl、Br、I、CN,B2为Cl、Br、CF3、OCH2CF3、OCF2H,且RB为氢、CH3或CH(CH3)2,和如JP 2002 284608、WO02/89579、WO 02/90320、WO 02/90321、WO 04/06677、WO 04/20399、JP 2004 99597、WO 05/68423、WO 05/68432或WO 05/63694中所述的丙二腈化合物,尤其为丙二腈化合物CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF3(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)5CF2H(2-(2,2,3,3,4,4,5,5,6,6,7,7-十二氟庚基)-2-(3,3,3-三氟丙基)-丙二腈)、CF3(CH2)2C(CN)2(CH2)2C(CF3)2F(2-(3,4,4,4-四氟-3-三氟甲基-丁基)-2-(3,3,3-三氟丙基)-丙二腈)、CF3(CH2)2C(CN)2(CH2)2(CF2)3CF3(2-(3,3,4,4,5,5,6,6,6-九氟己基)-2-(3,3,3-三氟丙基)-丙二腈)、CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF2H(2,2-双-(2,2,3,3,4,4,5,5-八氟戊基)-丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)3CF3(2-(2,2,3,3,4,4,5,5,5-九氟戊基)-2-(3,3,3-三氟丙基)-丙二腈)、CF3(CF2)2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,4-七氟丁基)-2-(2,2,3,3,4,4,5,5-八氟戊基)-丙二腈)和CF3CF2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(2,2,3,3,3-五氟丙基)-丙二腈)。
组A的市售化合物可在The Pesticide Manual,第13版,British CropProtection Council(2003)和其它出版物中找到。式Γ2的硫酰胺及其制备描述于WO 98/28279中。Lepimectin由Agro Project,PJB Publications Ltd,2004年11月已知。Benclothiaz及其制备描述于EP-A1 454621中。杀扑磷和对氧磷及其制备描述于Farm Chemicals Handbook,第88卷,MeisterPublishing Company,2001中。Acetoprole及其制备描述于WO 98/28277中。氰氟虫胺及其制备描述于EP-A1 462 456中。吡氟硫磷描述于PesticideScience 54,1988,第237-243页和US 4822779中。Pyrafluprole及其制备描述于JP 2002193709和WO 01/00614中。Pyriprole及其制备描述于WO98/45274和US 6335357中。Amidoflumet及其制备描述于US 6221890和JP 21010907中。Flufenerim及其制备描述于WO 03/007717和WO 03/007718中。Cyflumetofen及其制备描述于WO 04/080180中。式Γ3的邻氨基苯甲酰胺描述于WO 01/70671;WO 02/48137;WO 03/24222;WO03/15518;WO 04/67528;WO 04/33468;和WO 05/118552中。这类丙二腈化合物CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF3(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,3-三氟丙基)丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)5CF2H(2-(2,2,3,3,4,4,5,5,6,6,7,7-十二氟庚基)-2-(3,3,3-三氟丙基)-丙二腈)、CF3(CH2)2C(CN)2(CH2)2C(CF3)2F(2-(3,4,4,4-四氟-3-三氟甲基-丁基)-2-(3,3,3-三氟丙基)-丙二腈)、CF3(CH2)2C(CN)2(CH2)2(CF2)3CF3(2-(3,3,4,4,5,5,6,6,6-九氟己基)-2-(3,3,3-三氟丙基)-丙二腈)、CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF2H(2,2-双-(2,2,3,3,4,4,5,5-八氟戊基)-丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)3CF3(2-(2,2,3,3,4,4,5,5,5-九氟戊基)-2-(3,3,3-三氟丙基)-丙二腈)、CF3(CF2)2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,4-七氟丁基)-2-(2,2,3,3,4,4,5,5-八氟戊基)-丙二腈)和CF3CF2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(2,2,3,3,3-五氟丙基)-丙二腈)描述于WO 05/63694中。
下列可与本发明晶型I一起使用的杀真菌化合物意欲说明可能的组合,而非施加任何限制:
优选含有作为化合物I的晶型I的二元混合物。
优选含有作为化合物I的晶型I、化合物IIA和化合物IIB的三元混合物。
优选含有作为化合物I的晶型I、化合物IIA和两种分别为化合物IIB1和IIB2的四元混合物。
特别优选含有作为化合物I的晶型I和选自包含唑类一列的杀真菌化合物IIA的二元混合物:环唑醇(cyproconazole)、噁醚唑(difenoconazole)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、环戊唑醇(ipconazole)、环戊唑菌(metconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、唑菌醇(triadimenol)、三唑酮(triadimefon)、戊叉唑菌(triticonazole)、氰霜唑(cyazofamid)、烯菌灵(imazalil)、丙氯灵(prochloraz)、氟菌唑(triflumizole)、苯菌灵(benomyl)、多菌灵(carbendazim)、涕必灵(thiabendazole)、噻唑菌胺(ethaboxam)和土菌消(hymexazole)。
特别优选含有作为化合物I的晶型I和选自包含嗜球果伞素(strobilurin)列的杀真菌化合物IIA的二元混合物:腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、烯肟菌酯(enestroburin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、啶氧菌酯(picoxystrobin)、唑菌胺酯(pyraclostrobin)、肟菌酯(trifloxystrobin)、(2-氯-5-[1-(3-甲基苄氧基-亚氨基)乙基]苄基)胺基甲酸甲酯、(2-氯-5-[1-(6-甲基吡啶-2-基甲氧基-亚氨基)乙基]苄基)胺基甲酸甲酯和2-(邻-((2,5-二甲基苯氧基-亚甲基)苯基)-3-甲氧基丙烯酸甲酯。
特别优选含有作为化合物I的晶型I和选自包含羧酰胺列的杀真菌化合物IIA的二元混合物:啶酰菌胺(boscalid)、萎锈灵(carboxin)、苯霜灵(benalaxyl)、环酰菌胺(fenhexamid)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、甲霜灵(metalaxyl)、精甲霜灵(mefenoxam)、甲呋酰胺(ofurace)、噁霜灵(oxadixyl)、氧化萎锈灵(oxycarboxin)、吡噻菌胺(penthiopyrad)、溴氟唑菌(thifluzamide)、噻酰菌胺(tiadinil)、氟吡菌胺(fluopicolide)(picobenzamid)、双氯氰菌胺(diclocymet)、N-(4′-溴联苯-2-基)-4-二氟甲基-2-甲基噻唑-5-甲酰胺、N-(4′-三氟甲基联苯-2-基)-4-二氟甲基-2-甲基噻唑-5-甲酰胺、N-(4′-氯-3′-氟联苯-2-基)-4-二氟甲基-2-甲基噻唑-5-甲酰胺、N-(3′,4′-二氯-4-氟联苯-2-基)-3-二氟甲基-1-甲基吡唑-4-甲酰胺、N-(3′,4′-二氯-5-氟联苯-2-基)-3-二氟甲基-1-甲基吡唑-4-甲酰胺;3,4-二氯-N-(2-氰基苯基)异噻唑-5-甲酰胺;N-(2′,4′-二氟联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;N-(2′,4′-二氯联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;N-(2′,4′-二氟联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;N-(2′,4′-二氯-联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;N-(2′,5′-二氟联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;N-(2′,5′-二氯联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;N-(2′,5′-二氟联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;N-(2′,5′-二氯联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;N-(3′,5′-二氟-联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;N-(3′,5′-二氯联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺、N-(3′,5′-二氟联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;N-(3′,5′-二氯联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;N-(3′-氟联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺、N-(3′-氯联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;N-(3′-氟联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-(3′-氯联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;N-(2′-氟联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;N-(2′-氯联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;N-(2′-氟联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;N-(2′-氯联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;N-(2′-氟-4′-氯-5′-甲基联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;N-(3′,4′,5′-三氟联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;N-(3′,4′,5′-三氟联苯-2-基)-1-甲基-3-二氟甲基-1H-吡唑-4-甲酰胺;N-(2′,4′,5′-三氟联苯-2-基)-1-甲基-3-二氟甲基-1H-吡唑-4-甲酰胺;N-(3′,4′,5′-三氟联苯-2-基)-3-氯氟甲基-1-甲基-1H-吡唑-4-甲酰胺;N-[2-(1,1,2,3,3,3-六氟丙氧基)苯基]-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;N-[2-(1,1,2,3,3,3-六氟丙氧基)-苯基]-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-[2-(2-氯-1,1,2-三氟乙氧基)苯基]-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;N-[2-(2-氯-1,1,2-三氟乙氧基)苯基]-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;N-[2-(1,1,2,2-四氟乙氧基)苯基]-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;N-[2-(1,1,2,2-四氟-乙氧基)苯基]-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;N-(4′-(三氟甲基硫基)联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;N-(4′-(三氟甲硫基)联苯-2-基)-1-甲基-3-三氟甲基-1H-吡唑-4-甲酰胺;和5-氟-1,3-二甲基-1H-吡唑-4-甲酸[2-(1,2-二甲基-丙基)-苯基]-酰胺。
特别优选含有作为化合物I的晶型I和选自包含杂环化合物列的杀真菌化合物IIA的二元混合物:二甲嘧菌胺(pyrimethanil)、拌种咯(fenpiclonil)、氟噁菌(fludioxonil)、4-十二烷基-2,6-二甲基吗啉(aldimorph)、吗菌灵(dodemorph)、丁苯吗啉(fenpropimorph)、克啉菌(tridemorph)、异丙定(iprodione)、杀菌利(procymidone)、噁唑酮菌(famoixadone)、咪唑菌酮(fenamidone)、异噻菌酮(octhilinone)、噻菌灵(probenazole)、哒菌清(diclomezine)、咯喹酮(pyroquilon)、丙氧喹啉(proquinazid)、三环唑(tricyclazole)、敌菌丹(captafol)、克菌丹(captan)、棉隆(dazomet)、氰菌胺(fenoxanil)、喹氧灵(quinoxyfen)、5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶、6-(3,4-二氯-苯基)-5-甲基-[1,2,4]三唑并[1,5-a]嘧啶-7-基-胺、6-(4-叔丁基苯基)-5-甲基-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺、5-甲基-6-(3,5,5-三甲基-己基)-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺、5-甲基-6-辛基-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺、6-甲基-5-辛基-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺、6-乙基-5-辛基-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺、5-乙基-6-辛基-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺、5-乙基-6-(3,5,5-三甲基-己基)-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺、6-辛基-5-丙基-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺、5-甲氧基甲基-6-辛基-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺、6-辛基-5-三氟甲基-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺和5-三氟甲基-6-(3,5,5-三甲基-己基)-[1,2,4]三唑并[1,5-a]嘧啶-7-基胺。
特别优选为含有作为化合物I的晶型I和选自包含氨基甲酸盐列的杀真菌化合物IIA的二元混合物:代森锰锌(mancozeb)、代森锰(maneb)、威百亩(metam)、代森联(metiram)、福美铁(ferbam)、甲基代森锌(propineb)、福美双(thiram)、代森锌(zineb)、福美锌(ziram)、乙霉威(diethofencarb)、异丙菌胺(iprovalicarb)、百维灵(propamocarb)和3-(4-氯苯基)-3-(2-异丙氧羰基氨基-3-甲基丁酰氨基)丙酸甲酯。
特别优选含有作为化合物I的晶型I和选自包含下列的杀真菌化合物IIA的二元混合物:双胍盐(guazatine)、链霉素(streptomycin)、井冈霉素(validamycin A);乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton);二噻农(dithianon)、稻瘟灵(isoprothiolane);三苯锡基盐如薯瘟锡;克瘟散(edifenphos)、异稻瘟净(iprobenfos)、藻菌磷(fosetyl)、定菌磷(pyrazophos);百菌清(chlorothalonil)、抑菌灵(dichlofluanid)、磺菌胺(flusulfamide)、四氯苯酞(phthalide)、五氯硝基苯(quintozene)、甲基托布津(thiophanate-methyl)、对甲抑菌灵(tolylfluanid);醋酸铜、氢氧化铜、王铜、碱式硫酸铜、硫;环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、甲菌定(dimethirimol)、乙菌定(ethirimol)、呋氨丙灵(furalaxyl)、苯菌酮(metrafenone)和螺噁茂胺(spiroxamine)
上文所提及的活性化合物IIA、其制备及其对有害真菌的作用通常已知(参见:http://www.hclrss.demon.co.uk/index.html);其可市购。根据IUPAC命名的化合物、其制备及其杀真菌活性同样由以下专利已知:EP-A12 01 648;EP-A 226 917;WO 98/46608;WO 99/24413;WO 2004/049804;WO 2003/066609;WO 2003/053145;WO 2003/14103;EP-A 10 35 122;EP-A 10 28 125;EP-A 71 792;EP-A 141 317;WO 2003/009687;WO05/087771;WO 2005/087772;WO 2005/087773;WO 2006/087325;WO2006/087325;WO 2006/092428;WO 2006/092428;WO 2006/087343;WO 2001/42223;WO 2005/34628;WO 2005/123689;WO 2005/123690;WO 2006/120219;PCT/EP2006/064991;WO 2007/017450和欧洲申请第06123463.9号。
关于它们的意欲用途,特别优选以下作为化合物I的晶型I的三元和四元混合物:
表1
其中化合物IIA为肟菌酯且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表2
其中化合物IIA为腈嘧菌酯且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表3
其中化合物IIA为唑菌胺酯且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表4
其中化合物IIA为啶酰菌胺且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表5
其中化合物IIA为甲霜灵且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表6
其中化合物IIA为精甲霜灵且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表7
其中化合物IIA为环唑醇且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表8
其中化合物IIA为氧唑菌且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表9
其中化合物IIA为腈苯唑且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表10
其中化合物IIA为喹唑菌酮且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表11
其中化合物IIA为粉唑醇且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表12
其中化合物IIA为环戊唑醇且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表13
其中化合物IIA为环戊唑菌且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表14
其中化合物IIA为丙环唑且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表15
其中化合物IIA为丙硫菌唑且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表16
其中化合物IIA为戊唑醇且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表17
其中化合物IIA为唑菌醇且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表18
其中化合物IIA为戊叉唑菌且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表19
其中化合物IIA为烯菌灵且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表20
其中化合物IIA为丙氯灵且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表21
其中化合物IIA为多菌灵且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表22
其中化合物IIA为涕必灵且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表23
其中化合物IIA为噻唑菌胺且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表24
其中化合物IIA为土菌消且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表25
其中化合物IIA为二甲嘧菌胺且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表26
其中化合物IIA为氟噁菌且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表27
其中化合物IIA为4-十二烷基-2,6-二甲基吗啉且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表28
其中化合物IIA为吗菌灵且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表29
其中化合物IIA为丁苯吗啉且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表30
其中化合物IIA为异丙定且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表31
其中化合物IIA为克菌丹且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表32
其中化合物IIA为氰菌胺且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表33
其中化合物IIA为噻菌灵且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表34
其中化合物IIA为代森锰锌且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表35
其中化合物IIA为代森联且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表36
其中化合物IIA为福美双且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表37
其中化合物IIA为福美锌且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表38
其中化合物IIA为双胍盐且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表39
其中化合物IIA为甲基托布津且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表40
其中化合物IIA为百菌清且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表41
其中化合物IIA为苯菌酮且化合物IIB1和IIB2的组合在每种情况下对应于表Q的一行的混合物。
表Q
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-1 | 腈嘧菌酯 | - |
M-2 | 腈嘧菌酯 | 啶酰菌胺 |
M-3 | 腈嘧菌酯 | 甲霜灵 |
M-4 | 腈嘧菌酯 | 环唑醇 |
M-5 | 腈嘧菌酯 | 氧唑菌 |
M-6 | 腈嘧菌酯 | 腈苯唑 |
M-7 | 腈嘧菌酯 | 喹唑菌酮 |
M-8 | 腈嘧菌酯 | 粉唑醇 |
M-9 | 腈嘧菌酯 | 环戊唑醇 |
M-10 | 腈嘧菌酯 | 环戊唑菌 |
M-11 | 腈嘧菌酯 | 丙环唑 |
M-12 | 腈嘧菌酯 | 丙硫菌唑 |
M-13 | 腈嘧菌酯 | 戊唑醇 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-14 | 腈嘧菌酯 | 唑菌醇 |
M-15 | 腈嘧菌酯 | 戊叉唑菌 |
M-16 | 腈嘧菌酯 | 烯菌灵 |
M-17 | 腈嘧菌酯 | 丙氯灵 |
M-18 | 腈嘧菌酯 | 多菌灵 |
M-19 | 腈嘧菌酯 | 涕必灵 |
M-20 | 腈嘧菌酯 | 噻唑菌胺 |
M-21 | 腈嘧菌酯 | 土菌消 |
M-22 | 腈嘧菌酯 | 二甲嘧菌胺 |
M-23 | 腈嘧菌酯 | 氟噁菌 |
M-24 | 腈嘧菌酯 | 4-十二烷基-2,6-二甲基吗啉 |
M-25 | 腈嘧菌酯 | 吗菌灵 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-26 | 腈嘧菌酯 | 丁苯吗啉 |
M-27 | 腈嘧菌酯 | 异丙定 |
M-28 | 腈嘧菌酯 | 克菌丹 |
M-29 | 腈嘧菌酯 | 氰菌胺 |
M-30 | 腈嘧菌酯 | 噻菌灵 |
M-31 | 腈嘧菌酯 | 代森锰锌 |
M-32 | 腈嘧菌酯 | 代森联 |
M-33M-34 | 腈嘧菌酯 | 福美双 |
腈嘧菌酯 | 福美锌 | |
M-35 | 腈嘧菌酯 | 双胍盐 |
M-36 | 腈嘧菌酯 | 甲基托布津 |
M-37 | 腈嘧菌酯 | 百菌清 |
M-38 | 腈嘧菌酯 | 苯菌酮 |
M-39 | 肟菌酯 | - |
M-40 | 肟菌酯 | 啶酰菌胺 |
M-41 | 肟菌酯 | 甲霜灵 |
M-42 | 肟菌酯 | 环唑醇 |
M-43 | 肟菌酯 | 氧唑菌 |
M-44 | 肟菌酯 | 腈苯唑 |
M-45 | 肟菌酯 | 喹唑菌酮 |
M-46 | 肟菌酯 | 粉唑醇 |
M-47 | 肟菌酯 | 环戊唑醇 |
M-48 | 肟菌酯 | 环戊唑菌 |
M-49 | 肟菌酯 | 丙环唑 |
M-50 | 肟菌酯 | 丙硫菌唑 |
M-51 | 肟菌酯 | 戊唑醇 |
M-52 | 肟菌酯 | 唑菌醇 |
M-53 | 肟菌酯 | 戊叉唑菌 |
M-54 | 肟菌酯 | 烯菌灵 |
M-55 | 肟菌酯 | 丙氯灵 |
M-56 | 肟菌酯 | 多菌灵 |
M-57 | 肟菌酯 | 涕必灵 |
M-58 | 肟菌酯 | 噻唑菌胺 |
M-59 | 肟菌酯 | 土菌消 |
M-60 | 肟菌酯 | 二甲嘧菌胺 |
M-61 | 肟菌酯 | 氟噁菌 |
M-62 | 肟菌酯 | 4-十二烷基-2,6-二甲基吗啉 |
M-63 | 肟菌酯 | 吗菌灵 |
M-64 | 肟菌酯 | 丁苯吗啉 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-65 | 肟菌酯 | 异丙定 |
M-66 | 肟菌酯 | 克菌丹 |
M-67 | 肟菌酯 | 氰菌胺 |
M-68 | 肟菌酯 | 噻菌灵 |
M-69 | 肟菌酯 | 代森锰锌 |
M-70 | 肟菌酯 | 代森联 |
M-71 | 肟菌酯 | 福美双 |
M-72 | 肟菌酯 | 福美锌 |
M-73 | 肟菌酯 | 双胍盐 |
M-74 | 肟菌酯 | 甲基托布津 |
M-75 | 肟菌酯 | 百菌清 |
M-76 | 肟菌酯 | 苯菌酮 |
M-77 | 肟醚菌胺 | - |
M-78 | 肟醚菌胺 | 啶酰菌胺 |
M-79 | 肟醚菌胺 | 甲霜灵 |
M-80 | 肟醚菌胺 | 环唑醇 |
M-81 | 肟醚菌胺 | 氧唑菌 |
M-82 | 肟醚菌胺 | 腈苯唑 |
M-83 | 肟醚菌胺 | 喹唑菌酮 |
M-84 | 肟醚菌胺 | 粉唑醇 |
M-85 | 肟醚菌胺 | 环戊唑醇 |
M-86 | 肟醚菌胺 | 环戊唑菌 |
M-87 | 肟醚菌胺 | 丙环唑 |
M-88 | 肟醚菌胺 | 丙硫菌唑 |
M-89 | 肟醚菌胺 | 戊唑醇 |
M-90 | 肟醚菌胺 | 唑菌醇 |
M-91 | 肟醚菌胺 | 戊叉唑菌 |
M-92 | 肟醚菌胺 | 烯菌灵 |
M-93 | 肟醚菌胺 | 丙氯灵 |
M-94 | 肟醚菌胺 | 多菌灵 |
M-95 | 肟醚菌胺 | 涕必灵 |
M-96 | 肟醚菌胺 | 噻唑菌胺 |
M-97 | 肟醚菌胺 | 土菌消 |
M-98 | 肟醚菌胺 | 二甲嘧菌胺 |
M-99 | 肟醚菌胺 | 氟噁菌 |
M-100 | 肟醚菌胺 | 4-十二烷基-2,6-二甲基吗啉 |
M-101 | 肟醚菌胺 | 吗菌灵 |
M-102 | 肟醚菌胺 | 丁苯吗啉 |
M-103 | 肟醚菌胺 | 异丙定 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-104 | 肟醚菌胺 | 克菌丹 |
M-105 | 肟醚菌胺 | 氰菌胺 |
M-106 | 肟醚菌胺 | 噻菌灵 |
M-107 | 肟醚菌胺 | 代森锰锌 |
M-108 | 肟醚菌胺 | 代森联 |
M-109 | 肟醚菌胺 | 福美双 |
M-110 | 肟醚菌胺 | 福美锌 |
M-111 | 肟醚菌胺 | 双胍盐 |
M-112 | 肟醚菌胺 | 甲基托布津 |
M-113 | 肟醚菌胺 | 百菌清 |
M-114 | 肟醚菌胺 | 苯菌酮 |
M-115 | 唑菌胺酯 | - |
M-116 | 唑菌胺酯 | 啶酰菌胺 |
M-117 | 唑菌胺酯 | 甲霜灵 |
M-118 | 唑菌胺酯 | 环唑醇 |
M-119 | 唑菌胺酯 | 氧唑菌 |
M-120 | 唑菌胺酯 | 腈苯唑 |
M-121 | 唑菌胺酯 | 喹唑菌酮 |
M-122 | 唑菌胺酯 | 粉唑醇 |
M-123 | 唑菌胺酯 | 环戊唑醇 |
M-124 | 唑菌胺酯 | 环戊唑菌 |
M-125 | 唑菌胺酯 | 丙环唑 |
M-126 | 唑菌胺酯 | 丙硫菌唑 |
M-127 | 唑菌胺酯 | 戊唑醇 |
M-128 | 唑菌胺酯 | 唑菌醇 |
M-129 | 唑菌胺酯 | 戊叉唑菌 |
M-130 | 唑菌胺酯 | 烯菌灵 |
M-131 | 唑菌胺酯 | 丙氯灵 |
M-132 | 唑菌胺酯 | 多菌灵 |
M-133 | 唑菌胺酯 | 涕必灵 |
M-134 | 唑菌胺酯 | 噻唑菌胺 |
M-135 | 唑菌胺酯 | 土菌消 |
M-136 | 唑菌胺酯 | 二甲嘧菌胺 |
M-137 | 唑菌胺酯 | 氟噁菌 |
M-138 | 唑菌胺酯 | 4-十二烷基-2,6-二甲基吗啉 |
M-139 | 唑菌胺酯 | 吗菌灵 |
M-140 | 唑菌胺酯 | 丁苯吗啉 |
M-141 | 唑菌胺酯 | 异丙定 |
M-142 | 唑菌胺酯 | 克菌丹 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-143 | 唑菌胺酯 | 氰菌胺 |
M-144 | 唑菌胺酯 | 噻菌灵 |
M-145 | 唑菌胺酯 | 代森锰锌 |
M-146 | 唑菌胺酯 | 代森联 |
M-147 | 唑菌胺酯 | 福美双 |
M-148 | 唑菌胺酯 | 福美锌 |
M-149 | 唑菌胺酯 | 双胍盐 |
M-150 | 唑菌胺酯 | 甲基托布津 |
M-151 | 唑菌胺酯 | 百菌清 |
M-152 | 唑菌胺酯 | 苯菌酮 |
M-153 | 啶酰菌胺 | - |
M-154 | 啶酰菌胺 | 甲霜灵 |
M-155 | 啶酰菌胺 | 环唑醇 |
M-156 | 啶酰菌胺 | 氧唑菌 |
M-157 | 啶酰菌胺 | 腈苯唑 |
M-158 | 啶酰菌胺 | 喹唑菌酮 |
M-159 | 啶酰菌胺 | 粉唑醇 |
M-160 | 啶酰菌胺 | 环戊唑醇 |
M-161 | 啶酰菌胺 | 环戊唑菌 |
M-162 | 啶酰菌胺 | 丙环唑 |
M-163 | 啶酰菌胺 | 丙硫菌唑 |
M-164 | 啶酰菌胺 | 戊唑醇 |
M-165 | 啶酰菌胺 | 唑菌醇 |
M-166 | 啶酰菌胺 | 戊叉唑菌 |
M-167 | 啶酰菌胺 | 烯菌灵 |
M-168 | 啶酰菌胺 | 丙氯灵 |
M-169 | 啶酰菌胺 | 多菌灵 |
M-170 | 啶酰菌胺 | 涕必灵 |
M-171 | 啶酰菌胺 | 噻唑菌胺 |
M-172 | 啶酰菌胺 | 土菌消 |
M-173 | 啶酰菌胺 | 二甲嘧菌胺 |
M-174 | 啶酰菌胺 | 氟噁菌 |
M-175 | 啶酰菌胺 | 4-十二烷基-2,6-二甲基吗啉 |
M-176 | 啶酰菌胺 | 吗菌灵 |
M-177 | 啶酰菌胺 | 丁苯吗啉 |
M-178 | 啶酰菌胺 | 异丙定 |
M-179 | 啶酰菌胺 | 克菌丹 |
M-180 | 啶酰菌胺 | 氰菌胺 |
M-181 | 啶酰菌胺 | 噻菌灵 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-182 | 啶酰菌胺 | 代森锰锌 |
M-183 | 啶酰菌胺 | 代森联 |
M-184 | 啶酰菌胺 | 福美双 |
M-185 | 啶酰菌胺 | 福美锌 |
M-186 | 啶酰菌胺 | 双胍盐 |
M-187 | 啶酰菌胺 | 甲基托布津 |
M-188 | 啶酰菌胺 | 百菌清 |
M-189 | 啶酰菌胺 | 苯菌酮 |
M-190 | 甲霜灵 | - |
M-191 | 甲霜灵 | 环唑醇 |
M-192 | 甲霜灵 | 氧唑菌 |
M-193 | 甲霜灵 | 腈苯唑 |
M-194 | 甲霜灵 | 喹唑菌酮 |
M-195 | 甲霜灵 | 粉唑醇 |
M-196 | 甲霜灵 | 环戊唑醇 |
M-197 | 甲霜灵 | 环戊唑菌 |
M-198 | 甲霜灵 | 丙环唑 |
M-199 | 甲霜灵 | 丙硫菌唑 |
M-200 | 甲霜灵 | 戊唑醇 |
M-201 | 甲霜灵 | 唑菌醇 |
M-202 | 甲霜灵 | 戊叉唑菌 |
M-203 | 甲霜灵 | 烯菌灵 |
M-204 | 甲霜灵 | 丙氯灵 |
M-205 | 甲霜灵 | 多菌灵 |
M-206 | 甲霜灵 | 涕必灵 |
M-207 | 甲霜灵 | 噻唑菌胺 |
M-208 | 甲霜灵 | 土菌消 |
M-209 | 甲霜灵 | 二甲嘧菌胺 |
M-210 | 甲霜灵 | 氟噁菌 |
M-211 | 甲霜灵 | 4-十二烷基-2,6-二甲基吗啉 |
M-212 | 甲霜灵 | 吗菌灵 |
M-213 | 甲霜灵 | 丁苯吗啉 |
M-214 | 甲霜灵 | 异丙定 |
M-215 | 甲霜灵 | 克菌丹 |
M-216 | 甲霜灵 | 氰菌胺 |
M-217 | 甲霜灵 | 噻菌灵 |
M-218 | 甲霜灵 | 代森锰锌 |
M-219M-220 | 甲霜灵 | 代森联 |
甲霜灵 | 福美双 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-221 | 甲霜灵 | 福美锌 |
M-222 | 甲霜灵 | 双胍盐 |
M-223 | 甲霜灵 | 甲基托布津 |
M-224 | 甲霜灵 | 百菌清 |
M-225 | 甲霜灵 | 苯菌酮 |
M-226 | 环唑醇 | - |
M-227 | 环唑醇 | 氧唑菌 |
M-228 | 环唑醇 | 腈苯唑 |
M-229 | 环唑醇 | 喹唑菌酮 |
M-230 | 环唑醇 | 粉唑醇 |
M-231 | 环唑醇 | 环戊唑醇 |
M-232 | 环唑醇 | 环戊唑菌 |
M-233 | 环唑醇 | 丙环唑 |
M-234 | 环唑醇 | 丙硫菌唑 |
M-235 | 环唑醇 | 戊唑醇 |
M-236 | 环唑醇 | 唑菌醇 |
M-237 | 环唑醇 | 戊叉唑菌 |
M-238 | 环唑醇 | 烯菌灵 |
M-239 | 环唑醇 | 丙氯灵 |
M-240 | 环唑醇 | 多菌灵 |
M-241 | 环唑醇 | 涕必灵 |
M-242 | 环唑醇 | 噻唑菌胺 |
M-243 | 环唑醇 | 土菌消 |
M-244 | 环唑醇 | 二甲嘧菌胺 |
M-245 | 环唑醇 | 氟噁菌 |
M-246 | 环唑醇 | 4-十二烷基-2,6-二甲基吗啉 |
M-247 | 环唑醇 | 吗菌灵 |
M-248 | 环唑醇 | 丁苯吗啉 |
M-249 | 环唑醇 | 异丙定 |
M-250 | 环唑醇 | 克菌丹 |
M-251 | 环唑醇 | 氰菌胺 |
M-252 | 环唑醇 | 噻菌灵 |
M-253 | 环唑醇 | 代森锰锌 |
M-254 | 环唑醇 | 代森联 |
M-255 | 环唑醇 | 福美双 |
M-256 | 环唑醇 | 福美锌 |
M-257 | 环唑醇 | 双胍盐 |
M-258 | 环唑醇 | 甲基托布津 |
M-259 | 环唑醇 | 百菌清 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-260 | 环唑醇 | 苯菌酮 |
M-261 | 氧唑菌 | - |
M-262 | 氧唑菌 | 腈苯唑 |
M-263 | 氧唑菌 | 喹唑菌酮 |
M-264 | 氧唑菌 | 粉唑醇 |
M-265 | 氧唑菌 | 环戊唑醇 |
M-266 | 氧唑菌 | 环戊唑菌 |
M-267 | 氧唑菌 | 丙环唑 |
M-268 | 氧唑菌 | 丙硫菌唑 |
M-269 | 氧唑菌 | 戊唑醇 |
M-270 | 氧唑菌 | 唑菌醇 |
M-271 | 氧唑菌 | 戊叉唑菌 |
M-272 | 氧唑菌 | 烯菌灵 |
M-273 | 氧唑菌 | 丙氯灵 |
M-274 | 氧唑菌 | 多菌灵 |
M-275 | 氧唑菌 | 涕必灵 |
M-276 | 氧唑菌 | 噻唑菌胺 |
M-277 | 氧唑菌 | 土菌消 |
M-278 | 氧唑菌 | 二甲嘧菌胺 |
M-279 | 氧唑菌 | 氟噁菌 |
M-280 | 氧唑菌 | 4-十二烷基-2,6-二甲基吗啉 |
M-281 | 氧唑菌 | 吗菌灵 |
M-282 | 氧唑菌 | 丁苯吗啉 |
M-283 | 氧唑菌 | 异丙定 |
M-284 | 氧唑菌 | 克菌丹 |
M-285 | 氧唑菌 | 氰菌胺 |
M-286 | 氧唑菌 | 噻菌灵 |
M-287 | 氧唑菌 | 代森锰锌 |
M-288 | 氧唑菌 | 代森联 |
M-289 | 氧唑菌 | 福美双 |
M-290 | 氧唑菌 | 福美锌 |
M-291 | 氧唑菌 | 双胍盐 |
M-292 | 氧唑菌 | 甲基托布津 |
M-293 | 氧唑菌 | 百菌清 |
M-294 | 氧唑菌 | 苯菌酮 |
M-295 | 腈苯唑 | - |
M-296 | 腈苯唑 | 喹唑菌酮 |
M-297 | 腈苯唑 | 粉唑醇 |
M-298 | 腈苯唑 | 环戊唑醇 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-299 | 腈苯唑 | 环戊唑菌 |
M-300 | 腈苯唑 | 丙环唑 |
M-301 | 腈苯唑 | 丙硫菌唑 |
M-302 | 腈苯唑 | 戊唑醇 |
M-303 | 腈苯唑 | 唑菌醇 |
M-304 | 腈苯唑 | 戊叉唑菌 |
M-305 | 腈苯唑 | 烯菌灵 |
M-306 | 腈苯唑 | 丙氯灵 |
M-307 | 腈苯唑 | 多菌灵 |
M-308 | 腈苯唑 | 涕必灵 |
M-309 | 腈苯唑 | 噻唑菌胺 |
M-310 | 腈苯唑 | 土菌消 |
M-311 | 腈苯唑 | 二甲嘧菌胺 |
M-312 | 腈苯唑 | 氟噁菌 |
M-313 | 腈苯唑 | 4-十二烷基-2,6-二甲基吗啉 |
M-314 | 腈苯唑 | 吗菌灵 |
M-315 | 腈苯唑 | 丁苯吗啉 |
M-316 | 腈苯唑 | 异丙定 |
M-317 | 腈苯唑 | 克菌丹 |
M-318 | 腈苯唑 | 氰菌胺 |
M-319 | 腈苯唑 | 噻菌灵 |
M-320 | 腈苯唑 | 代森锰锌 |
M-321 | 腈苯唑 | 代森联 |
M-322 | 腈苯唑 | 福美双 |
M-323 | 腈苯唑 | 福美锌 |
M-324 | 腈苯唑 | 双胍盐 |
M-325 | 腈苯唑 | 甲基托布津 |
M-326 | 腈苯唑 | 百菌清 |
M-327 | 腈苯唑 | 苯菌酮 |
M-328 | 喹唑菌酮 | - |
M-329 | 喹唑菌酮 | 粉唑醇 |
M-330 | 喹唑菌酮 | 环戊唑醇 |
M-331 | 喹唑菌酮 | 环戊唑菌 |
M-332 | 喹唑菌酮 | 丙环唑 |
M-333 | 喹唑菌酮 | 丙硫菌唑 |
M-334 | 喹唑菌酮 | 戊唑醇 |
M-335 | 喹唑菌酮 | 唑菌醇 |
M-336 | 喹唑菌酮 | 戊叉唑菌 |
M-337 | 喹唑菌酮 | 烯菌灵 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-338 | 喹唑菌酮 | 丙氯灵 |
M-339 | 喹唑菌酮 | 多菌灵 |
M-340 | 喹唑菌酮 | 涕必灵 |
M-341 | 喹唑菌酮 | 噻唑菌胺 |
M-342 | 喹唑菌酮 | 土菌消 |
M-343 | 喹唑菌酮 | 二甲嘧菌胺 |
M-344 | 喹唑菌酮 | 氟噁菌 |
M-345 | 喹唑菌酮 | 4-十二烷基-2,6-二甲基吗啉 |
M-346 | 喹唑菌酮 | 吗菌灵 |
M-347 | 喹唑菌酮 | 丁苯吗啉 |
M-348 | 喹唑菌酮 | 异丙定 |
M-349 | 喹唑菌酮 | 克菌丹 |
M-350 | 喹唑菌酮 | 氰菌胺 |
M-351 | 喹唑菌酮 | 噻菌灵 |
M-352 | 喹唑菌酮 | 代森锰锌 |
M-353 | 喹唑菌酮 | 代森联 |
M-354 | 喹唑菌酮 | 福美双 |
M-355 | 喹唑菌酮 | 福美锌 |
M-356 | 喹唑菌酮 | 双胍盐 |
M-357 | 喹唑菌酮 | 甲基托布津 |
M-358 | 喹唑菌酮 | 百菌清 |
M-359 | 喹唑菌酮 | 苯菌酮 |
M-360 | 粉唑醇 | - |
M-361 | 粉唑醇 | 环戊唑醇 |
M-362 | 粉唑醇 | 环戊唑菌 |
M-363 | 粉唑醇 | 丙环唑 |
M-364 | 粉唑醇 | 丙硫菌唑 |
M-365 | 粉唑醇 | 戊唑醇 |
M-366 | 粉唑醇 | 唑菌醇 |
M-367 | 粉唑醇 | 戊叉唑菌 |
M-368 | 粉唑醇 | 烯菌灵 |
M-369 | 粉唑醇 | 丙氯灵 |
M-370 | 粉唑醇 | 多菌灵 |
M-371 | 粉唑醇 | 涕必灵 |
M-372 | 粉唑醇 | 噻唑菌胺 |
M-373 | 粉唑醇 | 土菌消 |
M-374 | 粉唑醇 | 二甲嘧菌胺 |
M-375 | 粉唑醇 | 氟噁菌 |
M-376 | 粉唑醇 | 4-十二烷基-2,6-二 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
甲基吗啉 | ||
M-377 | 粉唑醇 | 吗菌灵 |
M-378 | 粉唑醇 | 丁苯吗啉 |
M-379 | 粉唑醇 | 异丙定 |
M-380 | 粉唑醇 | 克菌丹 |
M-381 | 粉唑醇 | 氰菌胺 |
M-382 | 粉唑醇 | 噻菌灵 |
M-383 | 粉唑醇 | 代森锰锌 |
M-384 | 粉唑醇 | 代森联 |
M-385 | 粉唑醇 | 福美双 |
M-386 | 粉唑醇 | 福美锌 |
M-387 | 粉唑醇 | 双胍盐 |
M-388 | 粉唑醇 | 甲基托布津 |
M-389 | 粉唑醇 | 百菌清 |
M-390 | 粉唑醇 | 苯菌酮 |
M-391 | 环戊唑醇 | - |
M-392 | 环戊唑醇 | 环戊唑菌 |
M-393 | 环戊唑醇 | 丙环唑 |
M-394 | 环戊唑醇 | 丙硫菌唑 |
M-395 | 环戊唑醇 | 戊唑醇 |
M-396 | 环戊唑醇 | 唑菌醇 |
M-397 | 环戊唑醇 | 戊叉唑菌 |
M-398 | 环戊唑醇 | 烯菌灵 |
M-399 | 环戊唑醇 | 丙氯灵 |
M-400 | 环戊唑醇 | 多菌灵 |
M-401 | 环戊唑醇 | 涕必灵 |
M-402 | 环戊唑醇 | 噻唑菌胺 |
M-403 | 环戊唑醇 | 土菌消 |
M-404 | 环戊唑醇 | 二甲嘧菌胺 |
M-405 | 环戊唑醇 | 氟噁菌 |
M-406 | 环戊唑醇 | 4-十二烷基-2,6-二甲基吗啉 |
M-407 | 环戊唑醇 | 吗菌灵 |
M-408 | 环戊唑醇 | 丁苯吗啉 |
M-409 | 环戊唑醇 | 异丙定 |
M-410 | 环戊唑醇 | 克菌丹 |
M-411 | 环戊唑醇 | 氰菌胺 |
M-412 | 环戊唑醇 | 噻菌灵 |
M-413 | 环戊唑醇 | 代森锰锌 |
M-414 | 环戊唑醇 | 代森联 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-415 | 环戊唑醇 | 福美双 |
M-416 | 环戊唑醇 | 福美锌 |
M-417 | 环戊唑醇 | 双胍盐 |
M-418 | 环戊唑醇 | 甲基托布津 |
M-419 | 环戊唑醇 | 百菌清 |
M-420 | 环戊唑醇 | 苯菌酮 |
M-421 | 环戊唑菌 | - |
M-422 | 环戊唑菌 | 丙环唑 |
M-423 | 环戊唑菌 | 丙硫菌唑 |
M-424 | 环戊唑菌 | 戊唑醇 |
M-425 | 环戊唑菌 | 唑菌醇 |
M-426 | 环戊唑菌 | 戊叉唑菌 |
M-427 | 环戊唑菌 | 烯菌灵 |
M-428 | 环戊唑菌 | 丙氯灵 |
M-429 | 环戊唑菌 | 多菌灵 |
M-430 | 环戊唑菌 | 涕必灵 |
M-431 | 环戊唑菌 | 噻唑菌胺 |
M-432 | 环戊唑菌 | 土菌消 |
M-433 | 环戊唑菌 | 二甲嘧菌胺 |
M-434 | 环戊唑菌 | 氟噁菌 |
M-435 | 环戊唑菌 | 4-十二烷基-2,6-二甲基吗啉 |
M-436 | 环戊唑菌 | 吗菌灵 |
M-437 | 环戊唑菌 | 丁苯吗啉 |
M-438 | 环戊唑菌 | 异丙定 |
M-439 | 环戊唑菌 | 克菌丹 |
M-440 | 环戊唑菌 | 氰菌胺 |
M-441 | 环戊唑菌 | 噻菌灵 |
M-442 | 环戊唑菌 | 代森锰锌 |
M-443 | 环戊唑菌 | 代森联 |
M-444 | 环戊唑菌 | 福美双 |
M-445 | 环戊唑菌 | 福美锌 |
M-446 | 环戊唑菌 | 双胍盐 |
M-447 | 环戊唑菌 | 甲基托布津 |
M-448 | 环戊唑菌 | 百菌清 |
M-449 | 环戊唑菌 | 苯菌酮 |
M-450 | 丙环唑 | - |
M-451 | 丙环唑 | 丙硫菌唑 |
M-452 | 丙环唑 | 戊唑醇 |
M-453 | 丙环唑 | 唑菌醇 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-454 | 丙环唑 | 戊叉唑菌 |
M-455 | 丙环唑 | 烯菌灵 |
M-456 | 丙环唑 | 丙氯灵 |
M-457 | 丙环唑 | 多菌灵 |
M-458 | 丙环唑 | 涕必灵 |
M-459 | 丙环唑 | 噻唑菌胺 |
M-460 | 丙环唑 | 土菌消 |
M-461 | 丙环唑 | 二甲嘧菌胺 |
M-462 | 丙环唑 | 氟噁菌 |
M-463 | 丙环唑 | 4-十二烷基-2,6-二甲基吗啉 |
M-464 | 丙环唑 | 吗菌灵 |
M-465 | 丙环唑 | 丁苯吗啉 |
M-466 | 丙环唑 | 异丙定 |
M-467 | 丙环唑 | 克菌丹 |
M-468 | 丙环唑 | 氰菌胺 |
M-469 | 丙环唑 | 噻菌灵 |
M-470 | 丙环唑 | 代森锰锌 |
M-471 | 丙环唑 | 代森联 |
M-472 | 丙环唑 | 福美双 |
M-473 | 丙环唑 | 福美锌 |
M-474 | 丙环唑 | 双胍盐 |
M-475 | 丙环唑 | 甲基托布津 |
M-476 | 丙环唑 | 百菌清 |
M-477 | 丙环唑 | 苯菌酮 |
M-478 | 丙硫菌唑 | - |
M-479 | 丙硫菌唑 | 戊唑醇 |
M-480 | 丙硫菌唑 | 唑菌醇 |
M-481 | 丙硫菌唑 | 戊叉唑菌 |
M-482 | 丙硫菌唑 | 烯菌灵 |
M-483 | 丙硫菌唑 | 丙氯灵 |
M-484 | 丙硫菌唑 | 多菌灵 |
M-485 | 丙硫菌唑 | 涕必灵 |
M-486 | 丙硫菌唑 | 噻唑菌胺 |
M-487 | 丙硫菌唑 | 土菌消 |
M-488 | 丙硫菌唑 | 二甲嘧菌胺 |
M-489 | 丙硫菌唑 | 氟噁菌 |
M-490 | 丙硫菌唑 | 4-十二烷基-2,6-二甲基吗啉 |
M-491 | 丙硫菌唑 | 吗菌灵 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-492 | 丙硫菌唑 | 丁苯吗啉 |
M-493 | 丙硫菌唑 | 异丙定 |
M-494 | 丙硫菌唑 | 克菌丹 |
M-495 | 丙硫菌唑 | 氰菌胺 |
M-496 | 丙硫菌唑 | 噻菌灵 |
M-497 | 丙硫菌唑 | 代森锰锌 |
M-498 | 丙硫菌唑 | 代森联 |
M-499 | 丙硫菌唑 | 福美双 |
M-500 | 丙硫菌唑 | 福美锌 |
M-501 | 丙硫菌唑 | 双胍盐 |
M-502 | 丙硫菌唑 | 甲基托布津 |
M-503 | 丙硫菌唑 | 百菌清 |
M-504 | 丙硫菌唑 | 苯菌酮 |
M-505 | 戊唑醇 | - |
M-506 | 戊唑醇 | 唑菌醇 |
M-507 | 戊唑醇 | 戊叉唑菌 |
M-508 | 戊唑醇 | 烯菌灵 |
M-509 | 戊唑醇 | 丙氯灵 |
M-510 | 戊唑醇 | 多菌灵 |
M-511 | 戊唑醇 | 涕必灵 |
M-512 | 戊唑醇 | 噻唑菌胺 |
M-513 | 戊唑醇 | 土菌消 |
M-514 | 戊唑醇 | 二甲嘧菌胺 |
M-515 | 戊唑醇 | 氟噁菌 |
M-516 | 戊唑醇 | 4-十二烷基-2,6-二甲基吗啉 |
M-517 | 戊唑醇 | 吗菌灵 |
M-518 | 戊唑醇 | 丁苯吗啉 |
M-519 | 戊唑醇 | 异丙定 |
M-520 | 戊唑醇 | 克菌丹 |
M-521 | 戊唑醇 | 氰菌胺 |
M-522 | 戊唑醇 | 噻菌灵 |
M-523 | 戊唑醇 | 代森锰锌 |
M-524 | 戊唑醇 | 代森联 |
M-525 | 戊唑醇 | 福美双 |
M-526 | 戊唑醇 | 福美锌 |
M-527 | 戊唑醇 | 双胍盐 |
M-528 | 戊唑醇 | 甲基托布津 |
M-529 | 戊唑醇 | 百菌清 |
M-530 | 戊唑醇 | 苯菌酮 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-531 | 唑菌醇 | - |
M-532 | 唑菌醇 | 戊叉唑菌 |
M-533 | 唑菌醇 | 烯菌灵 |
M-534 | 唑菌醇 | 丙氯灵 |
M-535 | 唑菌醇 | 多菌灵 |
M-536 | 唑菌醇 | 涕必灵 |
M-537 | 唑菌醇 | 噻唑菌胺 |
M-538 | 唑菌醇 | 土菌消 |
M-539 | 唑菌醇 | 二甲嘧菌胺 |
M-540 | 唑菌醇 | 氟噁菌 |
M-541 | 唑菌醇 | 4-十二烷基-2,6-二甲基吗啉 |
M-542 | 唑菌醇 | 吗菌灵 |
M-543 | 唑菌醇 | 丁苯吗啉 |
M-544 | 唑菌醇 | 异丙定 |
M-545 | 唑菌醇 | 克菌丹 |
M-546 | 唑菌醇 | 氰菌胺 |
M-547 | 唑菌醇 | 噻菌灵 |
M-548 | 唑菌醇 | 代森锰锌 |
M-549 | 唑菌醇 | 代森联 |
M-550 | 唑菌醇 | 福美双 |
M-551 | 唑菌醇 | 福美锌 |
M-552 | 唑菌醇 | 双胍盐 |
M-553 | 唑菌醇 | 甲基托布津 |
M-554 | 唑菌醇 | 百菌清 |
M-555 | 唑菌醇 | 苯菌酮 |
M-556 | 戊叉唑菌 | - |
M-557 | 戊叉唑菌 | 烯菌灵 |
M-558 | 戊叉唑菌 | 丙氯灵 |
M-559 | 戊叉唑菌 | 多菌灵 |
M-560 | 戊叉唑菌 | 涕必灵 |
M-561 | 戊叉唑菌 | 塞唑菌胺 |
M-562 | 戊叉唑菌 | 土菌消 |
M-563 | 戊叉唑菌 | 二甲嘧菌胺 |
M-564 | 戊叉唑菌 | 氟噁菌 |
M-565 | 戊叉唑菌 | 4-十二烷基-2,6-二甲基吗啉 |
M-566 | 戊叉唑菌 | 吗菌灵 |
M-567 | 戊叉唑菌 | 丁苯吗啉 |
M-568 | 戊叉唑菌 | 异丙定 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-569 | 戊叉唑菌 | 克菌丹 |
M-570 | 戊叉唑菌 | 氰菌胺 |
M-571 | 戊叉唑菌 | 噻菌灵 |
M-572 | 戊叉唑菌 | 代森锰锌 |
M-573 | 戊叉唑菌 | 代森联 |
M-574 | 戊叉唑菌 | 福美双 |
M-575 | 戊叉唑菌 | 福美锌 |
M-576 | 戊叉唑菌 | 双胍盐 |
M-577 | 戊叉唑菌 | 甲基托布津 |
M-578 | 戊叉唑菌 | 百菌清 |
M-579 | 戊叉唑菌 | 苯菌酮 |
M-580 | 烯菌灵 | - |
M-581 | 烯菌灵 | 丙氯灵 |
M-582 | 烯菌灵 | 多菌灵 |
M-583 | 烯菌灵 | 涕必灵 |
M-584 | 烯菌灵 | 噻唑菌胺 |
M-585 | 烯菌灵 | 土菌消 |
M-586 | 烯菌灵 | 二甲嘧菌胺 |
M-587 | 烯菌灵 | 氟噁菌 |
M-588 | 烯菌灵 | 4-十二烷基-2,6-二甲基吗啉 |
M-589 | 烯菌灵 | 吗菌灵 |
M-590 | 烯菌灵 | 丁苯吗啉 |
M-591 | 烯菌灵 | 异丙定 |
M-592 | 烯菌灵 | 克菌丹 |
M-593 | 烯菌灵 | 氰菌胺 |
M-594 | 烯菌灵 | 噻菌灵 |
M-595 | 烯菌灵 | 代森锰锌 |
M-596 | 烯菌灵 | 代森联 |
M-597 | 烯菌灵 | 福美双 |
M-598 | 烯菌灵 | 福美锌 |
M-599 | 烯菌灵 | 双胍盐 |
M-600 | 烯菌灵 | 甲基托布津 |
M-601 | 烯菌灵 | 百菌清 |
M-602 | 烯菌灵 | 苯菌酮 |
M-603 | 丙氯灵 | - |
M-604 | 丙氯灵 | 多菌灵 |
M-605 | 丙氯灵 | 涕必灵 |
M-606 | 丙氯灵 | 噻唑菌胺 |
M-607 | 丙氯灵 | 土菌消 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-608 | 丙氯灵 | 二甲嘧菌胺 |
M-609 | 丙氯灵 | 氟噁菌 |
M-610 | 丙氯灵 | 4-十二烷基-2,6-二甲基吗啉 |
M-611 | 丙氯灵 | 吗菌灵 |
M-612 | 丙氯灵 | 丁苯吗啉 |
M-613 | 丙氯灵 | 异丙定 |
M-614 | 丙氯灵 | 克菌丹 |
M-615 | 丙氯灵 | 氰菌胺 |
M-616 | 丙氯灵 | 噻菌灵 |
M-617 | 丙氯灵 | 代森锰锌 |
M-618 | 丙氯灵 | 代森联 |
M-619 | 丙氯灵 | 福美双 |
M-620 | 丙氯灵 | 福美锌 |
M-621 | 丙氯灵 | 双胍盐 |
M-622 | 丙氯灵 | 甲基托布津 |
M-623 | 丙氯灵 | 百菌清 |
M-624 | 丙氯灵 | 苯菌酮 |
M-625 | 多菌灵 | - |
M-626 | 多菌灵 | 涕必灵 |
M-627 | 多菌灵 | 噻唑菌胺 |
M-628 | 多菌灵 | 土菌消 |
M-629 | 多菌灵 | 二甲嘧菌胺 |
M-630 | 多菌灵 | 氟噁菌 |
M-631 | 多菌灵 | 4-十二烷基-2,6-二甲基吗啉 |
M-632 | 多菌灵 | 吗菌灵 |
M-633 | 多菌灵 | 丁苯吗啉 |
M-634 | 多菌灵 | 异丙定 |
M-635 | 多菌灵 | 克菌丹 |
M-636 | 多菌灵 | 氰菌胺 |
M-637 | 多菌灵 | 噻菌灵 |
M-638 | 多菌灵 | 代森锰锌 |
M-639 | 多菌灵 | 代森联 |
M-640 | 多菌灵 | 福美双 |
M-641 | 多菌灵 | 福美锌 |
M-642 | 多菌灵 | 双胍盐 |
M-643 | 多菌灵 | 甲基托布津 |
M-644 | 多菌灵 | 百菌清 |
M-645 | 多菌灵 | 苯菌酮 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-646 | 涕必灵 | - |
M-647 | 涕必灵 | 噻唑菌胺 |
M-648 | 涕必灵 | 土菌消 |
M-649 | 涕必灵 | 二甲嘧菌胺 |
M-650 | 涕必灵 | 氟噁菌 |
M-651 | 涕必灵 | 4-十二烷基-2,6-二甲基吗啉 |
M-652 | 涕必灵 | 吗菌灵 |
M-653 | 涕必灵 | 丁苯吗啉 |
M-654 | 涕必灵 | 异丙定 |
M-655 | 涕必灵 | 克菌丹 |
M-656 | 涕必灵 | 氰菌胺 |
M-657 | 涕必灵 | 噻菌灵 |
M-658 | 涕必灵 | 代森锰锌 |
M-659 | 涕必灵 | 代森联 |
M-660 | 涕必灵 | 福美双 |
M-661 | 涕必灵 | 福美锌 |
M-662 | 涕必灵 | 双胍盐 |
M-663 | 涕必灵 | 甲基托布津 |
M-664 | 涕必灵 | 百菌清 |
M-665 | 涕必灵 | 苯菌酮 |
M-666 | 噻唑菌胺 | - |
M-667M-668 | 噻唑菌胺 | 土菌消 |
噻唑菌胺 | 二甲嘧菌胺 | |
M-669 | 噻唑菌胺 | 氟噁菌 |
M-670 | 噻唑菌胺 | 4-十二烷基-2,6-二甲基吗啉 |
M-671 | 噻唑菌胺 | 吗菌灵 |
M-672 | 噻唑菌胺 | 丁苯吗啉 |
M-673 | 噻唑菌胺 | 异丙定 |
M-674 | 噻唑菌胺 | 克菌丹 |
M-675 | 噻唑菌胺 | 氰菌胺 |
M-676 | 噻唑菌胺 | 噻菌灵 |
M-677 | 噻唑菌胺 | 代森锰锌 |
M-678 | 噻唑菌胺 | 代森联 |
M-679 | 噻唑菌胺 | 福美双 |
M-680 | 噻唑菌胺 | 福美锌 |
M-681 | 噻唑菌胺 | 双胍盐 |
M-682 | 噻唑菌胺 | 甲基托布津 |
M-683 | 噻唑菌胺 | 百菌清 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-684 | 噻唑菌胺 | 苯菌酮 |
M-685 | 土菌消 | - |
M-686 | 土菌消 | 二甲嘧菌胺 |
M-687 | 土菌消 | 氟噁菌 |
M-688 | 土菌消 | 4-十二烷基-2,6-二甲基吗啉 |
M-689 | 土菌消 | 吗菌灵 |
M-690 | 土菌消 | 丁苯吗啉 |
M-691 | 土菌消 | 异丙定 |
M-692 | 土菌消 | 克菌丹 |
M-693 | 土菌消 | 氰菌胺 |
M-694 | 土菌消 | 噻菌灵 |
M-695 | 土菌消 | 代森锰锌 |
M-696 | 土菌消 | 代森联 |
M-697 | 土菌消 | 福美双 |
M-698 | 土菌消 | 福美锌 |
M-699 | 土菌消 | 双胍盐 |
M-700 | 土菌消 | 甲基托布津 |
M-701 | 土菌消 | 百菌清 |
M-702 | 土菌消 | 苯菌酮 |
M-703 | 二甲嘧菌胺 | - |
M-704 | 二甲嘧菌胺 | 氟噁菌 |
M-705 | 二甲嘧菌胺 | 4-十二烷基-2,6-二甲基吗啉 |
M-706 | 二甲嘧菌胺 | 吗菌灵 |
M-707 | 二甲嘧菌胺 | 丁苯吗啉 |
M-708 | 二甲嘧菌胺 | 异丙定 |
M-709 | 二甲嘧菌胺 | 克菌丹 |
M-710 | 二甲嘧菌胺 | 氰菌胺 |
M-711 | 二甲嘧菌胺 | 噻菌灵 |
M-712 | 二甲嘧菌胺 | 代森锰锌 |
M-713 | 二甲嘧菌胺 | 代森联 |
M-714 | 二甲嘧菌胺 | 福美双 |
M-715 | 二甲嘧菌胺 | 福美锌 |
M-716 | 二甲嘧菌胺 | 双胍盐 |
M-717 | 二甲嘧菌胺 | 甲基托布津 |
M-718 | 二甲嘧菌胺 | 百菌清 |
M-719 | 二甲嘧菌胺 | 苯菌酮 |
M-720 | 氟噁菌 | - |
M-721 | 氟噁菌 | 4-十二烷基-2,6-二 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
甲基吗啉 | ||
M-722 | 氟噁菌 | 吗菌灵 |
M-723 | 氟噁菌 | 丁苯吗啉 |
M-724 | 氟噁菌 | 异丙定 |
M-725 | 氟噁菌 | 克菌丹 |
M-726 | 氟噁菌 | 氰菌胺 |
M-727 | 氟噁菌 | 噻菌灵 |
M-728 | 氟噁菌 | 代森锰锌 |
M-729 | 氟噁菌 | 代森联 |
M-730 | 氟噁菌 | 福美双 |
M-731 | 氟噁菌 | 福美锌 |
M-732 | 氟噁菌 | 双胍盐 |
M-733 | 氟噁菌 | 甲基托布津 |
M-734 | 氟噁菌 | 百菌清 |
M-735 | 氟噁菌 | 苯菌酮 |
M-736 | 4-十二烷基-2,6-二甲基吗啉 | - |
M-737 | 4-十二烷基-2,6-二甲基吗啉 | 吗菌灵 |
M-738 | 4-十二烷基-2,6-二甲基吗啉 | 丁苯吗啉 |
M-739 | 4-十二烷基-2,6-二甲基吗啉 | 异丙定 |
M-740 | 4-十二烷基-2,6-二甲基吗啉 | 克菌丹 |
M-741 | 4-十二烷基-2,6-二甲基吗啉 | 氰菌胺 |
M-742 | 4-十二烷基-2,6-二甲基吗啉 | 噻菌灵 |
M-743 | 4-十二烷基-2,6-二甲基吗啉 | 代森锰锌 |
M-744 | 4-十二烷基-2,6-二甲基吗啉 | 代森联 |
M-745 | 4-十二烷基-2,6-二甲基吗啉 | 福美双 |
M-746 | 4-十二烷基-2,6-二甲基吗啉 | 福美锌 |
M-747 | 4-十二烷基-2,6-二甲基吗啉 | 双胍盐 |
M-748 | 4-十二烷基-2,6- | 甲基托布津 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
二甲基吗啉 | ||
M-749 | 4-十二烷基-2,6-二甲基吗啉 | 百菌清 |
M-750 | 4-十二烷基-2,6-二甲基吗啉 | 苯菌酮 |
M-751 | 吗菌灵 | - |
M-752 | 吗菌灵 | 丁苯吗啉 |
M-753 | 吗菌灵 | 异丙定 |
M-754 | 吗菌灵 | 克菌丹 |
M-755 | 吗菌灵 | 氰菌胺 |
M-756 | 吗菌灵 | 噻菌灵 |
M-757 | 吗菌灵 | 代森锰锌 |
M-758 | 吗菌灵 | 代森联 |
M-759 | 吗菌灵 | 福美双 |
M-760 | 吗菌灵 | 福美锌 |
M-761 | 吗菌灵 | 双胍盐 |
M-762 | 吗菌灵 | 甲基托布津 |
M-763 | 吗菌灵 | 百菌清 |
M-764 | 吗菌灵 | 苯菌酮 |
M-765 | 丁苯吗啉 | - |
M-766 | 丁苯吗啉 | 异丙定 |
M-767 | 丁苯吗啉 | 克菌丹 |
M-768 | 丁苯吗啉 | 氰菌胺 |
M-769 | 丁苯吗啉 | 噻菌灵 |
M-770 | 丁苯吗啉 | 代森锰锌 |
M-771 | 丁苯吗啉 | 代森联 |
M-772 | 丁苯吗啉 | 福美双 |
M-773 | 丁苯吗啉 | 福美锌 |
M-774 | 丁苯吗啉 | 双胍盐 |
M-775 | 丁苯吗啉 | 甲基托布津 |
M-776 | 丁苯吗啉 | 百菌清 |
M-777 | 丁苯吗啉 | 苯菌酮 |
M-778 | 异丙定 | - |
M-779 | 异丙定 | 克菌丹 |
M-780 | 异丙定 | 氰菌胺 |
M-781 | 异丙定 | 噻菌灵 |
M-782 | 异丙定 | 代森锰锌 |
M-783 | 异丙定 | 代森联 |
M-784 | 异丙定 | 福美双 |
M-785 | 异丙定 | 福美锌 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-786 | 异丙定 | 双胍盐 |
M-787 | 异丙定 | 甲基托布津 |
M-788 | 异丙定 | 百菌清 |
M-789 | 异丙定 | 苯菌酮 |
M-790 | 克菌丹 | - |
M-791 | 克菌丹 | 氰菌胺 |
M-792 | 克菌丹 | 噻菌灵 |
M-793 | 克菌丹 | 代森锰锌 |
M-794 | 克菌丹 | 代森联 |
M-795 | 克菌丹 | 福美双 |
M-796 | 克菌丹 | 福美锌 |
M-797 | 克菌丹 | 双胍盐 |
M-798 | 克菌丹 | 甲基托布津 |
M-799 | 克菌丹 | 百菌清 |
M-800 | 克菌丹 | 苯菌酮 |
M-801 | 氰菌胺 | - |
M-802 | 氰菌胺 | 噻菌灵 |
M-803 | 氰菌胺 | 代森锰锌 |
M-804 | 氰菌胺 | 代森联 |
M-805 | 氰菌胺 | 福美双 |
M-806 | 氰菌胺 | 福美锌 |
M-807 | 氰菌胺 | 双胍盐 |
M-808 | 氰菌胺 | 甲基托布津 |
M-809 | 氰菌胺 | 百菌清 |
M-810 | 氰菌胺 | 苯菌酮 |
M-811 | 噻菌灵 | - |
M-812 | 噻菌灵 | 代森锰锌 |
M-813 | 噻菌灵 | 代森联 |
M-814 | 噻菌灵 | 福美双 |
M-815 | 噻菌灵 | 福美锌 |
M-816 | 噻菌灵 | 双胍盐 |
M-817 | 噻菌灵 | 甲基托布津 |
M-818 | 噻菌灵 | 百菌清 |
M-819 | 噻菌灵 | 苯菌酮 |
M-820 | 代森锰锌 | - |
M-821 | 代森锰锌 | 代森联 |
M-822 | 代森锰锌 | 福美双 |
M-823 | 代森锰锌 | 福美锌 |
M-824 | 代森锰锌 | 双胍盐 |
M-825 | 代森锰锌 | 甲基托布津 |
混合物号 | 化合物IIB1 | 化合物IIB2 |
M-826 | 代森锰锌 | 百菌清 |
M-827 | 代森锰锌 | 苯菌酮 |
M-828 | 代森联 | - |
M-829 | 代森联 | 福美双 |
M-830 | 代森联 | 福美锌 |
M-831 | 代森联 | 双胍盐 |
M-832 | 代森联 | 甲基托布津 |
M-833 | 代森联 | 百菌清 |
M-834 | 代森联 | 苯菌酮 |
M-835 | 福美双 | - |
M-836 | 福美双 | 福美锌 |
M-837 | 福美双 | 双胍盐 |
M-838 | 福美双 | 甲基托布津 |
M-839 | 福美双 | 百菌清 |
M-840 | 福美双 | 苯菌酮 |
M-841 | 福美锌 | - |
M-842 | 福美锌 | 双胍盐 |
M-843 | 福美锌 | 甲基托布津 |
M-844 | 福美锌 | 百菌清 |
M-845 | 福美锌 | 苯菌酮 |
M-846 | 双胍盐 | - |
M-847 | 双胍盐 | 甲基托布津 |
M-848 | 双胍盐 | 百菌清 |
M-849 | 双胍盐 | 苯菌酮 |
M-850 | 甲基托布津 | - |
M-851 | 甲基托布津 | 百菌清 |
M-852 | 甲基托布津 | 苯菌酮 |
M-853 | 百菌清 | - |
M-854 | 百菌清 | 苯菌酮 |
M-855 | 苯菌酮 | - |
晶型I和A.1-A.15组的一种或多种化合物通常以500∶1-1∶100,优选20∶1-1∶50,尤其是5∶1-1∶20的重量比来施用。
同样优选混合物比例也适用于晶型I与杀真菌化合物IIA的组合的比例。化合物IIB通常以100∶1-1∶100的比例与晶型I组合。
取决于所需的效果,本发明混合物的施用率为5-2000g/ha,优选50-1500g/ha,尤其是50-750g/ha。
本发明晶型I、混合物和组合物可施用于任何和所有发育阶段,如卵、幼虫、蛹和成虫。可通过使目标害虫、其食物源、栖息地、繁殖地或其场所与杀虫有效量的本发明晶型I、混合物和组合物接触来防治害虫。
“场所”是指其中害虫或寄生虫生长或会生长的植物、种子、土壤、区域、材料或环境。
“杀虫有效量”通常指对生长获得可观察到的效果所需要的本发明晶型I、混合物和组合物的量,所述效果包括坏死、死亡、阻滞、预防和去除效果,破坏效果或减少目标生物体的出现和活动的效果。对于在本发明中使用的各种混合物/组合物,杀虫有效量可以变化。混合物/组合物的杀虫有效量也会根据主要条件如所需杀虫效果及持续时间、天气、目标物种、场所、施用方式等而变化。
本发明晶型I、混合物和组合物也可用于保护植物免受昆虫、螨虫或线虫的侵袭或侵染,其包括与植物或植物生长的土壤或水接触。
在本发明上下文中,术语植物是指完整植物、植物的一部分或植物的繁殖材料,即种子或秧苗。
可用本发明晶型l、混合物和组合物处理的植物包括所有基因改进植物或转基因植物,例如由于包括基因工程方法的育种而对除草剂或杀真菌剂或杀虫剂具有耐受性的作物,或与现有植物相比具有改性特征的植物,其可例如通过传统育种方法和/或产生突变体来产生,或通过重组程序来产生。
本发明的混合物和组合物中的一些具有内吸作用并因此可用于保护植物枝抵抗叶面害虫以及用于处理种子和根以抵抗土壤害虫。术语种子处理包括本领域已知的所有合适的种子处理技术,例如包括但不限于拌种、种子包衣、种子撒粉、种子浸泡、种子包膜、种子多层包衣、种子包壳、种子湿淋和种子造粒。
本发明也包括涂有或含有本发明晶型I或混合物或组合物的种子。
术语种子包括种子和各种植物繁殖体,包括但不限于真正种子、种子块、根出条、球茎、鳞茎、果实、块茎、谷粒、插条、伐条等且在优选实施方案中意指真正种子。
合适的种子为禾谷类、根用作物、油料作物、蔬菜、香料、观赏植物的种子,例如以下植物的种子:硬粒小麦及其它小麦、大麦、燕麦、黑麦、玉米(饲料玉米和甜玉米/甜玉米和大田玉米)、大豆、油料作物、十字花科植物、棉花、向日葵、香蕉、水稻、油菜、球茎甘蓝、糖用甜菜、饲料甜菜、茄子、土豆、草、草坪、草皮、牧草、西红柿、韮菜、南瓜、卷心菜、卷心莴苣、胡椒、黄瓜、甜瓜、芸苔(Brassica)属、甜瓜、菜豆、豌豆、大蒜、洋葱、胡萝卜、块茎类植物(如土豆)、糖用甘蔗、烟草、葡萄、矮牵牛、天竺葵、三色堇和凤仙花。
另外,本发明晶型I、混合物和组合物也可用于处理由于育种、突变和/或基因工程方法而对除草剂或杀真菌剂或杀虫剂或杀线虫剂具有耐受性的植物种子。
例如,本发明晶型I、混合物和组合物可用于转基因作物,该转基因作物耐受选自磺酰脲类(EP-A-0257993、US 5,013,659)、咪唑啉酮类(例如参见US 6,222,100、WO 01/82685、WO 00/26390、WO 97/41218、WO98/02526、WO 98/02527、WO 04/106529、WO 05/20673、WO 03/14357、WO 03/13225、WO 03/14356、WO 04/16073)、草铵膦类(例如参见EP-A-0242236、EP-A-242246)或草甘膦类(例如参见WO 92/00377)的除草剂,或可用于耐受选自环己二烯酮/芳氧基苯氧基丙酸除草剂的除草剂的植物(US 5,162,602、US 5,290,696、US 5,498,544、US 5,428,001、US 6,069,298、US 6,268,550、US 6,146,867、US 6,222,099、US 6,414,222)或可用于能够产生使植物抵抗某些害虫的芽孢杆菌(Bacillus thuringiensis)毒素(Bt毒素)的转基因作物植物如棉花(EP-A-0142924、EP-A-0193259)。
此外,本发明晶型I、混合物和组合物还可以用于处理与现有植物相比具有改性特征的植物的种子,这些植物可以例如通过传统的育种方法和/或突变体的产生而产生,或通过重组程序产生。例如,已描述了作物植物重组改性以改变植物中合成的淀粉(如WO 92/11376、WO 92/14827、WO91/19806)或具有改变的脂肪酸组成的转基因作物植物(WO 91/13972)的许多实例。
本发明晶型I、混合物和组合物的种子处理施用通过在植物播种之前和植物出苗之前对种子喷雾或撒粉而进行。
在处理种子中,通过用有效量的本发明晶型I、混合物或组合物处理种子来施用相应配制剂。本文中,晶型I的施用率通常为每100kg种子0.1g至10kg,优选每100kg种子1g至5kg,尤其是每100kg种子1g至2.5kg。对于诸如莴苣和洋葱的特定作物而言,施用率可更高。
本发明混合物和组合物通过接触(经由土壤、玻璃、墙壁、床网、地毯、植物部分或动物部分)和进食(诱饵或植物部分)以及通过交哺和转移起作用。
优选施用方法为施入水体,经由土壤、裂缝和裂隙、牧场、粪肥堆、下水道施入水中,施用于地板、墙壁上,或通过周围喷雾施用和诱饵施用。
根据本发明的另一优选实施方案,为了用于对抗非作物害虫如蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀、蝗虫或蟑螂,将本发明混合物和组合物制备成诱饵制剂。
诱饵可以是液体、固体或半固体制剂(例如凝胶)。用于混合物/组合物中的诱饵是具有足够的吸引力以刺激诸如蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀等的昆虫或蟑螂食用它的产品。该吸引剂可以选自本领域易于知道的进食刺激剂或伪和/或性信息素。
用本发明混合物及其各自的组合物防治由昆虫传播的传染病(例如疟疾、登革热和黄热病、淋巴丝虫病和利什曼病(leishmaniasis))的方法也包括处理房屋表面、空气喷雾和浸渍窗帘、帐篷、衣物、床网、舌蝇捕捉器或类似物。施用于纤维、织物、针织品、非织造物、网状材料或箔片和防水布的杀虫组合物优选包含包括本发明混合物、任选驱除剂和至少一种粘合剂的组合物。
本发明晶型I、混合物和组合物可用于保护木质材料如树木、护栏、枕木等,以及建筑物如房子、附属建筑物、工厂,还有建筑材料、家具、皮革、纤维、聚氯乙烯制品、电线和电缆等以防蚂蚁和/或白蚁,并防止蚂蚁和白蚁损害作物或人类(例如当害虫侵入房子和公共设施时)。
在土壤处理或施用于害虫栖息地或巢穴的情况下,活性成分的施用量为0.0001-500g/100m2,优选0.001-20g/100m2。
材料保护中的通常施用率例如为每平方米处理材料0.01-1000g活性化合物,理想的是每平方米0.1-50g活性化合物。
用于材料浸渍的杀虫组合物通常含有0.001-95重量%,优选0.1-45重量%,更优选1-25重量%至少一种驱除剂和/或杀虫剂。
用于诱饵组合物的活性成分的典型含量为0.0001-15重量%,理想的是0.001-5重量%活性化合物。所用组合物还可以包含其它添加剂如活性材料的溶剂、调味剂、防腐剂、染料或苦味剂。其吸引力还可以通过特殊颜色、形状或结构而增强。
用于喷雾组合物的活性成分含量为0.001-80重量%,优选0.01-50重量%,最优选0.01-15重量%。
用于处理作物植物的活性成分的施用率可为每公顷0.1-4000g,理想的是每公顷25-600g,更理想的是每公顷50-500g。
本发明的目的还为提供适用于处理、防治、预防和保护,包括人在内的温血动物和鱼对抗害虫侵袭和侵染的混合物。在动物和/或人身上或体内的害虫防治中可能遇到的问题类似于开头所述的那些,即需要降低剂量率和/或改进的活性谱和/或结合了击倒活性和长期防治和/或耐药性管理。
本发明还提供了一种处理、防治、预防和保护包括人的温血动物和鱼对抗蚤目、膜翅目、半翅目、直翅目、蜱螨目、毛虱目和双翅目的害虫侵袭和侵染的方法,其包括将杀虫有效量的本发明晶型I、混合物和组合物口服、局部或肠胃外给药或施用于所述动物。
本发明还提供了一种制备用于处理、防治、预防或保护温血动物或鱼对抗蚤目、膜翅目、半翅目、直翅目、蜱螨目、毛虱目和双翅目害虫侵袭和侵染的组合物的方法,该组合物包含杀虫有效量的本发明晶型I、混合物和组合物。
上述方法尤其用于防治和预防在温血动物如牛、绵羊、猪、骆驼、鹿、马、家禽、山羊、狗和猫以及人中的侵袭和侵染。
在温血动物和鱼中的侵袭包括但不限于虱、叮咬虱、蜱、鼻蝇、羊蜱蝇(keds)、叮咬蝇、家蝇(muscoid flies)、蝇、蝇蛆幼虫、恙螨、蚋、蚊子和跳蚤,其可由本发明晶型I、混合物和组合物防治、预防或消除。
对于温血动物的口服给药,可将本发明晶型I、混合物和组合物配制成动物饲料、动物饲料预混物、动物饲料浓缩物、丸剂、溶液、糊、悬浮液、浸液、凝胶、片剂、大丸剂和胶囊。此外,本发明晶型I、混合物和组合物可在其饮用水中给药于动物。对于口服给药,所选剂型应给动物提供0.01-100mg/kg动物体重/天的本发明晶型I、混合物和组合物。
或者,本发明晶型I、混合物和组合物可以肠胃外给药于动物,例如通过腔内(intraruminal)、肌内、静脉内或皮下注射。本发明晶型I、混合物和组合物可以分散或溶于对于皮下注射而言生理上可接受的载体中。或者,可以将本发明晶型I、混合物和组合物配制成皮下给药用植入物。此外,本发明晶型I、混合物和组合物可以透皮(transdermally)给药于动物。对于肠胃外给药,所选剂型应给动物提供0.01-100mg/kg动物体重/天的本发明晶型I、混合物和组合物。
本发明晶型I、混合物和组合物还可以浸洗液、粉剂、粉末、项圈、挂牌(medallions)、喷雾剂、蘸点(spot-on)和喷淋配制剂形式局部施用于动物。对于局部施用,浸洗液和喷雾剂通常含有0.5-5000ppm,优选1-3000ppm晶型I。此外,本发明晶型I可以配制成动物,尤其是四足动物如牛和绵羊用耳贴。
以下图和实施例用于说明本发明而不应理解为限制本发明。
图1:晶型I的X-射线粉末衍射图
图2:晶型I的差示扫描量热法热分析图
图3:晶型I和V的两种混合物的X-射线粉末衍射图
制备实施例
以下所有制备程序均用根据WO 01/30760中所述的程序获得的固体锐劲特的两种样品作为原料来进行,其中最后在70-35℃的温度下使产物从氯苯/乙醇的溶剂混合物(结晶时乙醇的重量%:13%)中结晶。在X射线粉末衍射图研究中证实该固体形式为数种晶型混合物的结晶锐劲特。如在申请中的申请中第一次鉴别和描述,该混合物已经表征由晶型I和晶型V组成。对形式I和形式V的单晶数据的模拟X射线粉末衍射图图案的Topas程序的最小二乘方修正显示在这两种实施例样品中,形式I的百分比在30-70%内变化。两种样品的X射线粉末衍射图示于图3。
与用作原料的固体锐劲特的样品无关,下文给出的实施例中给出的结晶程序产生相同的本发明的晶型I。
实施例1:通过从甲醇中结晶来制备晶型I
将1g具有约96重量%的化学纯度的结晶锐劲特在48-52℃下在圆底烧瓶中溶解于25ml甲醇中。将溶液保持在该温度下,同时用缓慢流动的惰性N2气体使溶剂缓慢蒸发。使溶剂蒸发过夜,之后将结晶锐劲特的干燥产物冷却至20-25℃并进行分析。结晶产率>95%,熔点:195℃。所获得的材料具有图1中所示的X射线粉末衍射图,其中反射列于下表2中。
实施例2:通过从异丙醇中结晶来制备晶型I
在65-70℃和回流下将1g具有约96重量%的化学纯度的结晶锐劲特溶解于25g异丙醇中。在65-70℃下搅拌混合物直至所有材料完全溶解,之后停止搅拌。移除加热并以1-5K/min的速率将溶液冷却至20-25℃,并将烧瓶打开,在20-25℃下使溶剂缓慢蒸发一周,在此之后溶剂完全蒸发。结晶产率>95%,熔点:194℃。所获得的材料具有图1中所示的X射线粉末衍射图,其中反射列于下表2中。
实施例3:通过从乙醇中结晶来制备晶型I
在65-70℃和回流下将1g具有约96重量%的化学纯度的结晶锐劲特溶解于25g乙醇中。在65-70℃下搅拌混合物直至所有材料完全溶解,之后停止搅拌。移除加热并以1-5K/min的速率将溶液冷却至20-25℃,并将烧瓶打开,在20-25℃下使溶剂缓慢蒸发。结晶产率>95%,熔点:196℃。所获得的材料具有图1中所示的X射线粉末衍射图,其中反射列于下表2中。
实施例4:通过从乙苯中结晶来制备晶型I
将0.61g具有>98重量%的化学纯度的锐劲特悬浮于15ml乙苯中。施加搅拌并将悬浮液加热至140℃,产生清澈溶液。移除加热并以-1K/min的冷却速率将溶液冷却至25℃。在整个冷却相的过程中施加搅拌(700rpm)。检测到结晶在76-70℃时开始。将固体产物过滤并在滤纸上干燥过夜,然后通过PXRD分析以产生图1中所示的X射线粉末衍射图。
实施例5:通过从二异丙基苯(间二异丙基苯与对二异丙基苯的混合物,比例2∶1)中结晶来制备晶型I
将1.0g具有>98重量%的化学纯度的锐劲特悬浮于10ml二异丙基苯中。施加搅拌并将悬浮液加热至150℃,产生清澈溶液。移除加热并以-1K/min的冷却速率将溶液冷却至25℃。在整个冷却相的过程中施加搅拌(700rpm)。检测到结晶在138-130℃时开始。将固态产物过滤并在滤纸上干燥过夜,然后通过PXRD分析以产生图1中所示的X射线粉末衍射图。
实施例6:通过从正丁基苯中结晶来制备晶型I
将1.0g具有>98重量%的化学纯度的锐劲特悬浮于10ml正丁基苯中。施加搅拌并将悬浮液加热至150℃,产生清澈溶液。移除加热且以-1K/min的冷却速率将溶液冷却至25℃。在整个冷却相的过程中施加搅拌(700rpm)。检测到结晶在138-130℃时开始。将固态产物过滤并在滤纸上干燥过夜,然后通过PXRD分析以产生图1中所示的X射线粉末衍射图。
实施例7:通过从CF3-苯中结晶来制备晶型I
将1.0g具有>98重量%的化学纯度的锐劲特悬浮于8ml CF3-苯中。施加搅拌并将悬浮液加热至130℃,产生清澈溶液。移除加热且以-1K/min的冷却速率将溶液冷却至25℃。在整个冷却相的过程中施加搅拌(700rpm)。检测到结晶在105-95℃时开始。将固态产物过滤并在滤纸上干燥过夜,然后通过PXRD分析以产生图1中所示的X射线粉末衍射图。
实施例8:通过从乙腈中结晶来制备晶型I
在20-25℃下将1g具有约96重量%的化学纯度的结晶锐劲特溶解于15ml异丙醇中以产生清澈溶液。在打开的烧瓶中使溶液蒸发10天。使所得结晶固体在滤纸上干燥过夜。所获得的材料具有图1中所示的X射线粉末衍射图,其中反射列于下表2中。
实施例9:通过加入水而从DMSO中结晶来制备晶型I
在20-25℃下在10ml试管中将0.6g具有>98重量%的化学纯度的锐劲特溶解于2ml DMSO中。搅拌溶液并立即加入4ml水。在加入水后产物立即结晶。在20-25℃下将溶液搅拌1小时。过滤固体并使其在滤纸上干燥过夜。通过PXRD分析固体以产生图1中所示的X射线粉末衍射图。
表2:晶型I的2θ和d值
分析:
在25℃下使用Siemens D-5000衍射仪(制造商:Bruker AXS)记录图1中显示的X射线粉末衍射图,反射几何范围为2θ=2°-60°,增量为0.02°并且使用Cu-Kα辐射在25℃下进行。将测量的2θ值用于计算所述晶面间距d。在图1中,绘制峰值强度(y轴:线性强度,以计数表示)与2θ角(x轴,以度2θ表示)的关系图。
使用石墨CuKα辐射在Bruker AXS CCD检测器上收集单晶X射线衍射数据。使用直接法来解释结构,以及使用傅里叶(Fourier)技术以SHELX软件包进行改进和扩展(G.M.Sheldrick,SHELX-97, 1997)。用SADABS软件进行吸收校正。
本文中所示的熔点是指在Mettler热载台上结合光学显微镜所测定的值并表示平衡熔点。
在Mettler Toledo DSC 822e型号上进行DSC。将取自母液的晶体在滤纸上吸干并置于卷边但开孔的铝样品盘中以用于DCS实验。样品量在每种情况下为4-6mg。温度范围通常为30-250℃,加热速率为5℃/min。用以150ml/min流动的氮气流吹扫样品以用于DSC实验。
成核和结晶开始的温度对结晶最终产物的晶型的影响的研究用HELLtd的Polyblock进行。多反应器结晶系统允许用HEL的特殊反射率混浊度探针监测结晶过程和混浊度变化。用PC控制加热/冷却套和恒温器″Julabo FP 50″以及混浊度探针。
Claims (37)
1.一种以具有中心对称空间群C2/c的单斜晶系存在的晶型I的锐劲特。
3.根据权利要求1或2的晶型I,其具有在196-198℃范围内的熔点。
4.根据权利要求1-3中任一项的晶型I,其具有至少98重量%的锐劲特含量。
5.一种固体锐劲特,其包含如权利要求1-4中任一项所定义的晶型I和不同于晶型I的锐劲特的形式。
6.根据权利要求5的固体锐劲特,其包含至少85重量%的如权利要求1-4中任一项所定义的晶型I。
7.一种制备如权利要求1-4中任一项所定义的晶型I的方法,其包括以下步骤:
步骤i)制备不同于晶型I的固体形式的锐劲特在包含至少一种醇A1、乙腈、二甲亚砜(DMSO)或至少一种苯衍生物B1的溶剂S中的溶液;
步骤ii)进行锐劲特的结晶;和
步骤iii)分离所得沉淀,
其中醇A1选自甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、2-丁醇或叔丁醇,且苯衍生物B1选自苯,其可被一个或多个选自卤素、氰基、C1-C6烷基、C1-C6烷氧基、卤代甲基和硝基的基团取代。
8.根据权利要求7的方法,其中在步骤i)中,溶剂S选自异丙醇、正丁醇、异丁醇、2-丁醇或叔丁醇。
9.根据权利要求7的方法,其中在步骤i)中,溶剂S选自乙苯、正丙基苯、异丙基苯、二异丙基苯、正丁基苯、叔丁基苯、仲丁基苯、异丁基苯、CF3-苯、2-氯甲苯、3-氯甲苯和1,3,5-三甲基苯。
10.根据权利要求7或8的方法,其中在步骤i)中,溶剂S选自:
(a)纯的醇A1,
(b)不同醇A1的混合物,和
(c)一种或多种醇A1与水的混合物。
11.根据权利要求7或9的方法,其中在步骤i)中,溶剂S选自:
(d)纯乙腈,
(e)乙腈与水和/或一种或多种极性溶剂P的混合物,
(f)纯DMSO,
(g)DMSO与水和/或一种或多种极性溶剂P的混合物,
(h)纯苯衍生物B1,
(i)一种或多种苯衍生物B1与一种或多种醇A1的混合物,和
(j)一种或多种苯衍生物B1与一种或多种极性溶剂P的混合物;
其中极性溶剂P选自甲醇、乙醇、丙-1-醇、丙-2-醇、丁-1-醇、丁-2-醇、叔丁醇、2-甲基-丙-1-醇、2-甲基-丙-2-醇、戊-3-醇、2-甲基丁-1-醇、3-甲基丁-1-醇、1,2-乙二醇、1,3-丙二醇、1,2-丙二醇、环己醇、乙腈、丙腈、丙酮、丁酮、戊-2-酮、戊-3-酮、4-甲基-2-戊酮、3-甲基-丁-2-酮、3,3-二甲基-2-丁酮、环己酮、乙酸甲酯、乙酸乙酯、乙酸异丙酯、乙酸正丁酯、乙酸异丁酯、碳酸二乙酯、乙酸2-丁氧基乙酯、二噁烷、四氢呋喃、乙醚、2-甲基-四氢呋喃、甲基-叔丁基醚、二甲基甲酰胺、二甲基乙酰胺、二甲亚砜、硝基甲烷和硝基乙烷。
12.根据权利要求7、8或10的方法,其中醇A1为甲醇。
13.根据权利要求7、8或10的方法,其中醇A1为乙醇。
14.根据权利要求7、8或10的方法,其中醇A1为异丙醇。
15.根据权利要求7、8或10的方法,其中溶剂S为甲醇与水的混合物,其中水的含量不超过25重量%。
16.根据权利要求7、9或11的方法,其中苯衍生物B1为乙苯。
17.根据权利要求7、8或11的方法,其中苯衍生物B1为丙基苯。
18.根据权利要求7、9或11的方法,其中苯衍生物B1为丁基苯。
19.根据权利要求7、9或11的方法,其中苯衍生物B1为CF3-苯。
20.根据权利要求7-19中任一项的方法,其中在步骤ii)中,锐劲特的结晶通过浓缩步骤i)中获得的溶液而进行。
21.根据权利要求7-20中任一项的方法,其中步骤ii)在如权利要求1-4中任一项所定义的晶型I的种晶存在下进行。
22.一种协同增效的杀虫或杀寄生虫混合物,其包含作为活性组份的如权利要求1-4中任一项所定义的晶型I和一种或多种杀虫或杀寄生虫化合物。
23.一种杀虫或杀寄生虫组合物,其包含如权利要求1-4中任一项所定义的晶型I或如权利要求15所定义的混合物和杀虫或杀寄生虫可接受的载体和/或助剂。
24.根据权利要求23的组合物,其呈含水悬浮液浓缩物的形式。
25.根据权利要求23的组合物,其呈水分散性颗粒的形式。
26.根据权利要求23的组合物,其呈水分散性粉末的形式。
27.如权利要求1-4中任一项所定义的晶型I或如权利要求5或6所定义的固体锐劲特或如权利要求22所定义的混合物或如权利要求23-26中任一项所定义的组合物在防治害虫中的用途。
28.一种防治害虫的方法,其包括使害虫或其食物源、栖息地、繁殖地或其场所与杀虫有效量的如权利要求1-4中任一项所定义的晶型I或如权利要求5或6所定义的固体锐劲特或如权利要求22所定义的混合物或如权利要求23-26中任一项所定义的组合物接触。
29.一种保护植物免受害虫侵染和侵袭的方法,其包括向所述植物的叶或茎施用杀虫有效量的如权利要求1-4中任一项所定义的晶型I或如权利要求5或6所定义的固体锐劲特或如权利要求22所定义的混合物或如权利要求23-26中任一项所定义的组合物。
30.根据权利要求21或22的方法,其中以5-2000g/ha的量施用如权利要求1-4中任一项所定义的晶型I或如权利要求5或6所定义的固体锐劲特或如权利要求22所定义的混合物或如权利要求23-26中任一项所定义的组合物。
31.根据权利要求27的用途或根据权利要求28-30中任一项的方法,其中所述害虫为昆虫、蜘蛛或植物线虫。
32.一种保护种子的方法,其包括使种子与杀虫有效量的如权利要求1-4中任一项所定义的晶型I或如权利要求5或6所定义的固体锐劲特或如权利要求22所定义的混合物或如权利要求23-26中任一项所定义的组合物接触。
33.根据权利要求32的方法,其中以每100kg种子0.1g至10kg的量施用如权利要求1-4中任一项所定义的晶型I或如权利要求5或6所定义的固体锐劲特或如权利要求22所定义的混合物或如权利要求23-26中任一项所定义的组合物。
34.种子,其以每100kg种子0.1g至10kg量包含如权利要求1-4中任一项所定义的晶型I或如权利要求5或6所定义的固体锐劲特或如权利要求22所定义的混合物。
35.如权利要求1-4中任一项所定义的晶型I或如权利要求5或6所定义的固体锐劲特或如权利要求22所定义的混合物或如权利要求23-26中任一项所定义的组合物在对抗动物体内或身上的寄生虫中的用途。
36.一种处理、防治、预防或保护动物免受寄生虫侵袭或侵染的方法,其包括将杀寄生虫有效量的如权利要求1-4中任一项所定义的晶型I或如权利要求5或6所定义的固体锐劲特或如权利要求22所定义的混合物或如权利要求23-26中任一项所定义的组合物口服、局部或肠胃外给药或施用于所述动物。
37.一种制备用于处理、防治、预防或保护动物免受寄生虫侵袭或侵染的组合物的方法,该组合物包含杀寄生虫有效量的如权利要求1-4中任一项所定义的晶型I或如权利要求5或6所定义的固体锐劲特或如权利要求22所定义的混合物或如权利要求23-26中任一项所定义的组合物。
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103313604A (zh) * | 2011-01-14 | 2013-09-18 | K·H·伽达 | [5-氨基-1-(2,6-二氯-4-三氟甲苯基)-3-腈-4-三氟甲基亚磺酰基吡唑]中的多晶体 |
CN103313604B (zh) * | 2011-01-14 | 2016-03-02 | K·H·伽达 | [5-氨基-1-(2,6-二氯-4-三氟甲苯基)-3-腈-4-三氟甲基亚磺酰基吡唑]中的多晶体 |
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US9451772B2 (en) | 2016-09-27 |
JP2010509274A (ja) | 2010-03-25 |
CA2667713A1 (en) | 2008-05-15 |
IL198262A0 (en) | 2009-12-24 |
JP2016136940A (ja) | 2016-08-04 |
BRPI0718771A2 (pt) | 2013-11-26 |
US20100081698A1 (en) | 2010-04-01 |
NZ576639A (en) | 2012-03-30 |
BR122019011580B1 (pt) | 2020-10-13 |
JP6147371B2 (ja) | 2017-06-14 |
JP2014141494A (ja) | 2014-08-07 |
UA110598C2 (uk) | 2016-01-25 |
MX2009004264A (es) | 2009-05-05 |
EA201300338A1 (ru) | 2013-12-30 |
CN101562979B (zh) | 2013-08-21 |
BR122019020541B1 (pt) | 2022-04-19 |
EA024053B1 (ru) | 2016-08-31 |
EP2083626A1 (en) | 2009-08-05 |
KR101475537B1 (ko) | 2014-12-23 |
ZA200903970B (en) | 2016-08-31 |
EA200900641A1 (ru) | 2009-12-30 |
KR20090082474A (ko) | 2009-07-30 |
WO2008055881A1 (en) | 2008-05-15 |
EA019304B1 (ru) | 2014-02-28 |
JP5931321B2 (ja) | 2016-06-08 |
TW200826842A (en) | 2008-07-01 |
US20130137571A1 (en) | 2013-05-30 |
US8383664B2 (en) | 2013-02-26 |
AU2007316638B2 (en) | 2013-03-07 |
MA30929B1 (fr) | 2009-11-02 |
TWI473567B (zh) | 2015-02-21 |
AR063652A1 (es) | 2009-02-04 |
AU2007316638A1 (en) | 2008-05-15 |
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