CN102300455A - 包含农药和uv吸收剂的农业化学组合物 - Google Patents
包含农药和uv吸收剂的农业化学组合物 Download PDFInfo
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- CN102300455A CN102300455A CN2009801558173A CN200980155817A CN102300455A CN 102300455 A CN102300455 A CN 102300455A CN 2009801558173 A CN2009801558173 A CN 2009801558173A CN 200980155817 A CN200980155817 A CN 200980155817A CN 102300455 A CN102300455 A CN 102300455A
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- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
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- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 description 1
- ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
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- 230000004048 modification Effects 0.000 description 1
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- 150000002780 morpholines Chemical class 0.000 description 1
- AEXITZJSLGALNH-UHFFFAOYSA-N n'-hydroxyethanimidamide Chemical class CC(N)=NO AEXITZJSLGALNH-UHFFFAOYSA-N 0.000 description 1
- XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003992 organochlorine insecticide Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001151 peptidyl group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940044654 phenolsulfonic acid Drugs 0.000 description 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 description 1
- 150000008060 phenylpyrroles Chemical class 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000008298 phosphoramidates Chemical class 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 description 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical class CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- QDGHXQFTWKRQTG-UHFFFAOYSA-N pyrimidin-2-ylhydrazine Chemical class NNC1=NC=CC=N1 QDGHXQFTWKRQTG-UHFFFAOYSA-N 0.000 description 1
- 239000002718 pyrimidine nucleoside Substances 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical class CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical class NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004549 water soluble granule Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
-
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及一种包含农药和UV吸收剂的农业化学组合物以及所述UV吸收剂。本发明还涉及所述UV吸收剂在农业化学组合物中的用途。本发明还涉及一种防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长的方法。
Description
本发明涉及一种包含农药和UV吸收剂的农业化学组合物以及上述UV吸收剂。本发明进一步涉及所述UV吸收剂在农业化学组合物中的用途。此外,本发明涉及一种防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长的方法。优选特征与其他优选特征的结合包括在本发明中。
包含农药和UV吸收剂的农业化学组合物通常是已知的:
WO 1992/03926公开了包含合成除虫菊酯类、UV吸收剂和抗氧化剂的杀虫组合物。
EP 0 376 888 A1公开了防治有害昆虫的组合物,其包含一种改变有害昆虫行为的物质和农药活性化合物,这二者均包含在保护该行为改变物质免受UV辐射的可流动基质中。该组合物通常包含51-98重量%的基质,其通常为优选具有1,000-40,000cp的粘度的UV吸收剂。合适的UV吸收剂例如为下列烷氧基化2-(2-羟基苯基)苯并三唑类TinuA和TinuB的混合物:
WO 2006/089747公开了一种保护材料的方法,包括使用包含含有光不稳定农药和UV吸收剂如α-[3-[3-(2H-苯并三唑-2-基)-5-(1,1-二甲基乙基)-4-羟基苯基]-1-氧代丙基]-ω-羟基聚(氧基-1,2-亚乙基)的胶囊的组合物。WO1997/42815公开了一种包含0.1-20%农药、0.01-30%信息素和40-98%UV吸收剂的组合物。例如可以将Tinuvin 1130用作UV吸收剂。
包含烷氧基化基团的肉桂酸衍生物同样也是已知的:
Philippon等(Synthetic Communications,1997,27(15),2651-2682)公开了一种下式化合物:
现有技术的UV吸收剂具有各种缺点:必须加入其他助剂如抗氧化剂。该UV吸收剂必须用于基质中。该UV吸收剂不能足够长时间地稳定光敏性农药。
本发明的目的是提供用于农业化学组合物中的替代UV吸收剂。另一目的是发现稳定UV敏感性农药的UV吸收剂。该稳定化应比现有技术要好,尤其也在较低的UV吸收剂浓度下。此外,目的还在于发现允许更简单地配制农药的UV吸收剂,例如需要更少的助剂,如表面活性剂。
该目的由包含农药和UV吸收剂的农业化学组合物实现,其中该UV吸收剂对应于式I:
其中AO为C2-C4烷氧基或CH2CH2NH;
n为3-50;
若UV表示A或B,则m为1,若UV表示C,则m为3;
X为NH或O;
R1为H或C1-C24烷基;
UV为选自式A-C的基团:
其中R2为H、CN或CO2-(C1-C16烷基);
R3为H、C1-C6烷基、苯基或被C1-C18烷氧基取代的苯基;
R4为H或C1-C18烷氧基;
其中R5为H、C1-C18烷基、OH或C1-C18烷氧基;
R6为C1-C8亚烷基;或
其中R7为H或C1-C12烷基;
该基团经由#键合于I的羰基上。
术语农药表示至少一种选自杀真菌剂、杀虫剂、杀线虫剂、除草剂、安全剂和/或生长调节剂的活性化合物。优选的农药是杀真菌剂、杀虫剂和除草剂,尤其是杀虫剂。还可以使用两种或更多种上述种类农药的混合物。本领域熟练技术人员熟知该类农药,例如可以在Pesticide Manual,第14版(2006),The British Crop Protection Council,London中找到。合适的杀虫剂是选自如下类别的杀虫剂:氨基甲酸酯类、有机磷酸酯类、有机氯杀虫剂、苯基吡唑类、合成除虫菊酯类、新类烟碱类、斯皮诺素类(spinosins)、阿维菌素类(avermectins)、米尔霉素类(milbemycins)、保幼激素类似物、烷基卤、有机锡化合物、沙蚕毒素类似物、苯甲酰脲类、二酰基肼类、METI杀螨剂以及杀虫剂如氯化苦(chloropicrin)、拒嗪酮(pymetrozine)、氟啶虫酰胺(flonicamid)、四螨嗪(clofentezine)、噻螨酮(hexythiazox)、特苯唑(etoxazole)、杀螨硫隆(diafenthiuron)、克螨特(propargite)、三氯杀螨砜(tetradifon)、氟唑虫清(chlorfenapyr)、二硝酚(DNOC)、噻嗪酮(buprofezin)、灭蝇胺(cyromazine)、双甲脒(amitraz)、灭蚁腙(hydramethylnon)、灭螨醌(acequinocyl)、fluacrypyrim、鱼藤酮(rotenone)或其衍生物。合适的杀真菌剂是选自如下类别的杀真菌剂:二硝基苯胺类、烯丙基胺类、苯胺基嘧啶类、抗生素类、芳族烃类、苯磺酰胺类、苯并咪唑类、苯并异噻唑类、二苯甲酮类、苯并噻二唑类、苯并三嗪类、苄基氨基甲酸酯类、氨基甲酸酯类、羧酰胺类、羧酸酰胺类、氯代腈类、氰基乙酰胺肟类、氰基咪唑类、环丙烷羧酰胺类、二羧酰亚胺类、二氢二嗪类、二硝基苯基巴豆酸酯类、二硫代氨基甲酸酯类、二硫戊环类、乙基膦酸酯类、乙基氨基噻唑羧酰胺类、胍类、羟基-(2-氨基-)嘧啶类、羟基酰替苯胺类、咪唑类、咪唑啉酮类、无机化合物、异苯并呋喃酮类、甲氧基丙烯酸酯类、甲氧基氨基甲酸酯类、吗啉类、N-苯基氨基甲酸酯类、唑烷二酮类、肟基乙酸酯类、肟基乙酰胺类、肽基嘧啶核苷、苯基乙酰胺类、苯基酰胺类、苯基吡咯类、苯基脲类、膦酸酯类、硫代磷酸酯类、邻氨甲酰苯甲酸类、苯邻二甲酰亚胺类、哌嗪类、哌啶类、丙酰胺类、哒嗪酮类、吡啶类、吡啶基甲基苯甲酰胺类、嘧啶胺类、嘧啶类、嘧啶酮腙类、吡咯并喹啉酮类、喹唑啉酮类、喹啉类、醌类、磺酰胺类、氨磺酰三唑类、噻唑羧酰胺类、硫代氨基甲酸酯类、托布津类(thiophanates)、噻吩羧酰胺类、甲苯甲酰胺类、三苯基锡化合物、三嗪类、三唑类。合适的除草剂是选自如下类别的除草剂:乙酰胺类、酰胺类、芳氧基苯氧基丙酸酯类、苯甲酰胺类、苯并呋喃、苯甲酸类、苯并噻二嗪酮类、联吡啶氨基甲酸酯类、氯代乙酰胺类、氯代羧酸、环己烷二酮类、二硝基苯胺类、二硝基苯酚类、二苯基醚类、甘氨酸类、咪唑啉酮类、异唑类、异唑烷酮类、腈类、N-苯基苯邻二甲酰亚胺类、二唑类、唑烷二酮类、羟乙酰胺类、苯氧基羧酸类、苯基氨基甲酸酯类、苯基吡唑类、苯基吡唑啉类、苯基哒嗪类、次膦酸类、氨基磷酸酯类、二硫代磷酸酯类、邻氨甲酰苯甲酸酯类、吡唑类、哒嗪酮类、吡啶类、吡啶羧酸类、吡啶羧酰胺类、嘧啶二酮类、嘧啶基(硫代)苯甲酸酯类、喹啉羧酸类、缩氨基脲类、磺酰氨基羰基三唑啉酮类、磺酰脲类、四唑啉酮类、噻二唑类、硫代氨基甲酸酯类、三嗪类、三嗪酮类、三唑类、三唑啉酮类、三唑并羧酰胺类、三唑并嘧啶类、三酮类、尿嘧啶类、脲类。
优选的除草剂是草萘胺(napropamide)、敌稗(propanil)、噻草平(bentazone)、对草快(paraquat dichloride)、噻草酮(cycloxydim)、稀禾定(sethoxydim)、丁氟消草(ethalfluralin)、黄草消(oryzalin)、胺硝草(pendimethalin)、氟乐灵(trifluralin)、氟锁草醚(acifluren)、苯草醚(aclonifen)、氟黄胺草醚(fomesafen)、乙氧氟草醚(oxyfluoren)、碘苯腈(ioxynil)、咪草烟(imazetapyr)、灭草喹(imazaquin)、杀草敏(chloridazon)、达草灭(norflurazon)、噻氟啶草(thiazopyr)、定草酯(triclopyr)、氟硫草定(dithiopyr)、吡氟草胺(diflufenican)、氟吡酰草胺(picolinafen)、磺氨黄隆(amidosulfuron)、草达灭(molinate)、灭草猛(vernolate)、扑灭通(prometon)、赛克津(metribuzin)、唑啶炔草(azafenidin)、氟酮唑草(carfentrazone-ethyl)、磺胺草唑(sulfentrazone)、甲氧隆(metoxuron)、绿谷隆(monolinuron)、氟消草(fluchloralin)和抑草丁(flurenol)。优选的杀真菌剂是环丙嘧啶(cyprodinil)、麦穗宁(fuberidazole)、烯酰吗啉(dimethomorph)、丙氯灵(procloraz)、氟菌唑(triflumizole)、克啉菌(tridemorph)、克瘟散(edifenfos)、异嘧菌醇(fenarimol)、氟苯嘧啶醇(nuarimol)、乙菌定(ethirimol)、喹氧灵(q uinoxylen)、二噻农(dithianon)、叉氨苯酰胺(metominostrobin)、肟菌酯(trifloxystrobin)、抑菌灵(dichlofluamid)、糠菌唑(bromuconazole)和腈菌唑(myclobutanil)。优选的杀虫剂是高灭磷(acephate)、乙基谷硫磷(azinphos-ethyl)、谷硫磷(azinphos-methyl)、丙胺磷(isofenphos)、甲基毒死蜱(chlorpyriphos-methyl)、甲基毒虫畏(dimethylvinphos)、甲拌磷(phorate)、辛硫磷(phoxim)、丙硫磷(prothiofos)、三环锡(cyhexatin)、棉铃威(alanycarb)、苯虫威(ethiofencarb)、抗蚜威(pirimicarb)、硫双威(thiodicarb)、锐劲特(fipronil)、反丙烯除虫菊(bioallethrin)、生物苄呋菊酯(bioresmethin)、溴氰菊酯(deltamethrin)、甲氰菊酯(fenpropathin)、氟氰戊菊酯(flucythrinate)、氟胺氰菊酯(taufluvalinate)、甲体氯氰菊酯(alpha-cypermethrin)、氰氟虫胺(metaflumizone)、己体氯氰菊酯(zeta-cypermethrin)、灭虫菊(resmethin)、七氟菊酯(tefluthrin)、氯氟氰菊酯(lambda cyhalothrin)和灭蚁腙。在另一实施方案中,优选的杀虫剂是合成除虫菊酯类或氰氟虫胺,尤其是合成除虫菊酯类。特别优选的农药为甲体氯氰菊酯和氰氟虫胺。
在一个实施方案中,使用UV敏感性农药。该UV敏感性可以简单的初步试验确定。若用UV光,优选波长为300-800nm的UV/VIS光辐照通过干燥25重量%农药在合适溶剂,优选丙酮中的溶液形成的农药薄膜时农药在25℃下在24小时内至少降解20重量%,则认为它们是UV敏感性的。所用照度通常为10000-100000勒克司,优选50000-80000勒克司。当农药(或两种或更多种农药组分的混合物中的一种农药组分)的浓度相应降低时,认为农药发生降解。
合适的UV吸收剂具有如上所定义的式I的结构。合适的基团AO为C2-C4烷氧基或-CH2CH2NH-,优选-CH2CH2NH-,其中C2-C4烷氧基优选为-CH2CH2O-、-CH(CH3)CH2O-或-CH(CH2CH3)CH2O-,尤其是-CH2CH2O-。指数n表示3-50,优选3-30,尤其是3-25,具体为3-15。指数m在UV表示A、B或D时表示1或在UV表示C时表示3。合适的基团X为NH或O,优选O。
合适的基团R1为H或C1-C24烷基,优选C1-C6烷基,尤其是CH3。在另一实施方案中,R1表示H或C1-C24烷基,优选C6-C24烷基,特别优选C6-C24烷基,尤其是C8-C20烷基,具体为C10-C20烷基,非常具体为支化C10-C20烷基。
术语“-CH2CH2NH-”为通用经验式且表示聚乙烯亚胺基团的单体单元。这些聚乙烯亚胺基团可以是线性或支化的并且它们优选是支化的。支化的聚乙烯亚胺基团通常含有伯、仲和叔氨基。伯/仲/叔氨基的摩尔比可以为1/0.5/0.2-1/1.9/1.5,优选1/0.7/0.4-1/1.5/1.1。
合适的基团UV是选自式A-C,优选B或C的基团,其中这些基团经由#与式I的羰基键合。
合适的基团UV具有式A的结构:
其中R2为H、CN或CO2-(C1-C16烷基),优选CN或CO2-(C1-C16烷基),尤其是CN;
R3为H、C1-C6烷基、苯基或被C1-C18烷氧基取代的苯基,优选C1-C6烷基、苯基或被C1-C18烷氧基取代的苯基,尤其是苯基或被C1-C18烷氧基取代的苯基;和
R4为H或C1-C18烷氧基,优选H。
另一合适的基团UV具有式B的结构:
其中R5为H、C1-C18烷基、OH或C1-C18烷氧基,优选H;和
R6为C1-C8亚烷基,优选C1-C2亚烷基,尤其是CH2。
另一合适的基团UV具有式C的结构:
其中R7为H或C1-C12烷基,优选H。
在优选实施方案中,农业化学组合物包含农药和UV吸收剂,其中该UV吸收剂对应于式III的结构:
其中
n为3-50,优选3-25;
R10为H、CN或CO2-(C1-C16烷基),优选H或CN,尤其是H;
R11为H、C1-C6烷基、苯基或被C1-C18烷氧基取代的苯基,优选H、苯基或被C1-C18烷氧基取代的苯基,尤其是H;
R12为H或C1-C18烷氧基,优选H;和
R13为H或C1-C24烷基,优选CH3。
在另一优选实施方案中,R13表示H或C1-C24烷基,优选C6-C24烷基,特别优选C6-C24烷基,尤其是C8-C20烷基,具体为C10-C20烷基,非常具体为支化C10-C20烷基。
在另一优选实施方案中,农业化学组合物包含农药和UV吸收剂,其中该UV吸收剂对应于式IV的结构:
其中
n为3-50,优选3-25;
R14、R15相互独立地为H或C1-C18烷氧基,优选H或甲氧基,尤其是H;和
R16为H或C1-C24烷基,优选C1-C4烷基,特别优选CH3。
在另一优选实施方案中,R16表示H或C1-C24烷基,优选C6-C24烷基,特别优选C6-C24烷基,尤其是C8-C20烷基,具体为C10-C20烷基,非常具体为支化C10-C20烷基。
在另一优选实施方案中,农业化学组合物包含农药和UV吸收剂,其中该UV吸收剂对应于式V的结构:
其中
n为3-50,优选3-25;
R17、R18相互独立地为H或C1-C18烷氧基,优选H或甲氧基,尤其是H。
在另一优选实施方案中,该农业化学组合物包含农药和UV吸收剂,其中该UV吸收剂对应于式VI的结构:
其中
n为3-50,优选3-20,尤其是3-10;
R19为C1-C8亚烷基,优选C1-C4亚烷基,尤其是CH2;
R20为H或C1-C24烷基,优选CH3;和
R21为H、C1-C18烷基、OH或C1-C18烷氧基,优选H。
在另一优选实施方案中,R20表示H或C1-C24烷基,优选C6-C24烷基,特别优选C6-C24烷基,尤其是C8-C20烷基,具体为C10-C20烷基,非常具体为支化C10-C20烷基。
在另一优选实施方案中,农业化学组合物包含农药和UV吸收剂,其中该UV吸收剂对应于式VII的结构:
其中
n为3-50,优选3-25,尤其是3-10;
R22为H或C1-C24烷基,优选CH3;和
R23为H或C1-C12烷基,优选H。
在另一优选实施方案中,R22表示H或C1-C24烷基,优选C6-C24烷基,特别优选C6-C24烷基,尤其是C8-C20烷基,具体为C10-C20烷基,非常具体为支化C10-C20烷基。
本发明农业化学组合物通常包含0.01-95重量%,优选0.5-80重量%,特别优选2-50重量%,具体为5-20重量%的农药,在每种情况下基于该组合物。
该UV吸收剂在25℃下在水/空气界面处通常具有至多50mN/m,优选至多46mN/m,特别优选至多44mN/m,具体为至多40mN/m的表面张力。
本发明农业化学组合物通常包含0.1-50重量%,优选0.5-30重量%,特别优选1.0-15重量%的UV吸收剂,在每种情况下基于该组合物。
农药与UV吸收剂的重量比通常为30∶1-1∶2,优选15∶1-2∶1,特别优选8∶1-3∶1。
包含农药和UV吸收剂的农业化学组合物可以呈常用于农业化学配制剂的组合物类型,例如溶液、乳液、悬浮液、粉剂、粉末、糊和颗粒。该类型尤其取决于特定的意欲用途;在所有情况下应确保本发明化合物的精细和均匀分布。组合物类型的实例是悬浮液(SC,OD,FS),糊,锭剂,可湿性粉末或粉剂(WP,SP,SS,WS,DP,DS)或水溶性或水分散性颗粒(GR,FG,GG,MG)以及用于处理植物繁殖材料如种子的凝胶(GF)。用于动物如蚂蚁或大鼠的诱饵可以呈各种上述组合物类型,优选呈粉末、糊、颗粒或凝胶。组合物类型(例如SC,OD,FS,WG,SG,WP,SP,SS,WS,GF)通常以稀释形式使用。组合物类型如DP,DS,GR,FG,GG,MG或诱饵通常以未稀释形式使用。优选的组合物类型是悬浮液。
该农业化学组合物此外还可以包含常用于植物保护组合物的助剂,助剂的选择取决于具体的使用形式或活性化合物。合适助剂的实例是溶剂、固体载体物质、表面活性物质(如其他加溶剂、保护性胶体、润湿剂和粘合剂)、有机和无机增稠剂、杀菌剂、防冻剂、消泡剂、任选还有染料和粘合剂(例如用于种子处理)或用于诱饵配制剂的常规助剂(例如引诱剂、饲料、苦味剂)。
可能的溶剂是水,有机溶剂,如中到高沸点的矿物油馏分,如煤油和柴油,此外还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃如石蜡,四氢化萘,烷基化萘及其衍生物,烷基化苯及其衍生物,醇类如甲醇、乙醇、丙醇、丁醇和环己醇,二醇类,酮类如环己酮、γ-丁内酯,二甲基脂肪酸酰胺类,脂肪酸类和脂肪酸酯类以及强极性溶剂,例如胺类如N-甲基吡咯烷酮。原则上还可以使用溶剂混合物以及上述溶剂与水的混合物。
固体载体物质为矿土如硅石、硅胶、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、陶土、壤土、粘土、白云石、硅藻土、硫酸钙和硫酸镁、氧化镁,磨碎的塑料,肥料如硫酸铵、磷酸铵、硝酸铵和脲类以及植物产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉或其它固体载体物质。
可能的表面活性物质(助剂、润湿剂、粘合剂、分散剂或乳化剂)是芳族磺酸如木素磺酸(例如类型,挪威Borregaard)、苯酚磺酸、萘磺酸类型,Akzo Nobel,USA)和二丁基萘磺酸类型,德国BASF SE)以及脂肪酸的碱金属盐、碱土金属盐和铵盐,烷基-和烷基芳基磺酸盐,烷基硫酸盐,月桂基醚硫酸盐和脂肪醇硫酸盐,以及硫酸化十六-、十七-和十八烷醇的盐,还有脂肪醇乙二醇醚的盐,磺化萘及其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-、辛基-或壬基酚,烷基苯基或三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三烷醇,脂肪醇-氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚或聚氧丙烯烷基醚,月桂醇聚乙二醇醚乙酸酯,山梨糖醇酯,木素亚硫酸盐废液和蛋白质,变性蛋白质,多糖(如甲基纤维素),疏水改性的淀粉,聚乙烯醇类型,瑞士Clariant),聚羧酸盐类类型,德国BASF SE),聚烷氧基化物,聚乙烯胺类型,德国BASF SE),聚乙烯亚胺类型,德国BASF SE),聚乙烯基吡咯烷酮及其共聚物。
增稠剂(即赋予组合物以改性的流动性能,即静止状态下的高粘度和搅动状态下的低粘度的化合物)的实例是多糖以及有机和无机层状矿物,如黄原胶CP Kelco,USA),23(法国Rhodia)或(R.T.Vanderbilt,USA)或(Engelhard Corp.,NJ,USA)。
可以加入杀菌剂以稳定该组合物。杀菌剂实例是基于双氯芬和苄醇半缩甲醛的那些(ICI的或Thor Chemie的RS以及Rohm &Haas的MK),还有异噻唑啉酮衍生物,如烷基异噻唑啉酮类和苯并异噻唑啉酮类(Thor Chemie的MBS)。
合适防冻剂的实例是乙二醇、丙二醇、尿素和甘油。
组合物类型的实例为:
1.用水稀释的组合物类型
i)水溶性浓缩物(SL,LS)
将10重量份农药溶于90重量份水或水溶性溶剂中。或者,加入润湿剂或其他助剂。农药在用水稀释时溶解。以此方式得到活性化合物含量为10重量%的组合物。
ii)分散性浓缩物(DC)
将20重量份农药溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯吡咯烷酮。用水稀释得到分散体。活性化合物含量为20重量%。
iii)可乳化浓缩物(EC)
将15重量份农药溶于75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5重量份)。用水稀释得到乳液。该组合物的活性化合物含量为15重量%。
iv)乳液(EW,EO,ES)
将25重量份农药溶于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5重量份)。借助乳化机(例如Ultra-Turrax)将该混合物加入30重量份水中并转化成均相乳液。用水稀释得到乳液。该组合物的活性化合物含量为25重量%。
v)悬浮液(SC,OD,FS)
在搅拌的球磨机中将20重量份农药粉碎并加入10重量份分散剂和润湿剂以及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。该组合物的活性化合物含量为20重量%。
vi)水分散性颗粒和水溶性颗粒(WG,SG)
将50重量份农药细碎研磨并加入50重量份分散剂和润湿剂,借助工业装置(例如挤出机、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。该组合物的活性化合物含量为50重量%。
vii)水分散性粉末和水溶性粉末(WP,SP,SS,WS)
将75重量份农药在转子-定子磨机中研磨并加入25重量份分散剂、润湿剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液。该组合物的活性化合物含量为75重量%。
viii)凝胶(GF)
在球磨机中研磨20重量份农药、10重量份分散剂、1重量份溶胀剂(“胶凝剂”)和70重量份水或有机溶剂而得到精细悬浮液。用水稀释得到活性化合物含量为20重量%的稳定悬浮液。
2.直接施用的组合物类型
ix)粉剂(DP,DS)
将5重量份农药细碎研磨并与95重量份细碎高岭土充分混合。由此得到活性化合物含量为5重量%的粉剂组合物。
x)颗粒(GR,FG,GG,MG)
将0.5重量份农药细碎研磨并结合99.5重量份载体物质。常见方法是挤出、喷雾干燥或流化床方法。由此得到活性化合物含量为0.5重量%的直接施用的颗粒。
xi)ULV溶液(UL)
将10重量份农药溶于90重量份有机溶剂如二甲苯中。由此得到活性化合物含量为10重量%的直接施用组合物。
化合物可以直接或以其组合物形式(例如以可直接喷雾溶液、粉末、悬浮液、分散体、乳液、油分散体、糊、粉剂组合物、撒播组合物或颗粒形式)通过喷雾、雾化、撒粉、撒播、诱饵展开、刷涂、浸渍或浇灌来使用。
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(喷雾粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助润湿剂、粘合剂、分散剂或乳化剂将该物质直接或作为在油或溶剂中的溶液在水中均化。然而,还可以由活性物质制备包含润湿剂、粘合剂、分散剂或乳化剂以及可能的话溶剂或油的浓缩物且该类浓缩物适于用水稀释。
活性化合物在即用配制剂中的浓度可以在较宽范围内变化。它们通常为0.0001-10%,优选0.01-1%。在植物保护中使用的施用量为0.01-2.0kg活性化合物/ha,这取决于所需效果的性质。在植物繁殖材料如种子的处理中,通常使用的活性化合物量为1-1,000g/100kg,优选5-100g/100kg繁殖材料或种子。为了用于保护材料或储存产品,活性化合物的施用量取决于使用领域和所需效果的性质。在材料保护中施用的常规量例如为0.001g-2kg,优选0.005-1kg活性化合物/m3被处理材料。
此外,本发明涉及上式I的UV吸收剂,其中若R2和R3均表示H,则AO表示CH2CH2NH。优选UV表示选自式B和C结构的基团。优选AO表示CH2CH2NH。
在优选实施方案中,本发明涉及一种UV吸收剂,其中该UV吸收剂对应于式Ⅸ的结构:
其中n为3-50,优选3-25,以及R10、R11、R12和R13如上所定义。
在另一优选实施方案中,本发明涉及一种UV吸收剂,其中该UV吸收剂对应于式X的结构:
其中n为3-50,优选3-25,以及R14、R15和R16如上所定义。
在另一优选实施方案中,本发明涉及一种UV吸收剂,其中该UV吸收剂对应于式XI的结构:
其中n为3-50,优选3-25,以及R17和R18如上所定义。
在另一优选实施方案中,本发明涉及一种UV吸收剂,其中该UV吸收剂对应于式XII的结构:
其中n为3-50,优选3-25,尤其是3-10,以及R19、R20和R21如上所定义。
在另一优选实施方案中,本发明涉及一种UV吸收剂,其中该UV吸收剂对应于式XIII的结构:
其中n为3-50,优选3-25,尤其是3-10,以及R22和R23如上所定义。
本发明UV吸收剂在25℃下在水/空气界面处通常具有至多50mN/m,优选至多46mN/m,特别优选至多44mN/m,具体为至多40mN/m的表面张力。
本发明进一步涉及本发明UV吸收剂在农业化学组合物中的用途。优选在农业化学组合物中的用途。特别优选稳定UV敏感性农药以尤其防阳光的用途。优选的UV吸收剂是式III-XIV的那些,尤其是式IX-XIII的那些。合适的农业化学组合物如上所述。
本发明进一步涉及一种防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长的方法,其中使本发明组合物作用于特定害虫、其栖息地或要防止特定害虫的植物、土壤和/或不希望的植物和/或农作物和/或其生长场所。
本发明的优点是它们稳定UV敏感性农药,尤其是已经在低浓度的UV吸收剂下。另一优点是需要使用更少的表面活性剂以获得活性化合物分散体,尤其是活性化合物悬浮液的高稳定性。该UV吸收剂易溶于农业化学配制剂中或非常容易与农业化学配制剂如水乳液和含水悬浮液相容。例如,为了将该UV吸收剂掺入配制剂中也无需额外乳化剂。
下列实施例说明但不限制本发明。
实施例
A350E:聚亚烷氧基二醇单甲醚(Polyalkoxylene glycolmonomethyl ether),OH数为约160mg KOH/g,摩尔质量为约350g/mol,借助OH数测定,以A350E由BASF市购。
A500PE:丁基聚乙二醇/丙二醇共聚物,OH数为约115mg KOH/g,摩尔质量为约500g/mol,借助OH数测定,以A500PE由BASFSE市购。
消泡剂:基于聚硅氧烷,活性物含量为20重量%(以Silikon SRE-PFL由Wacker市购)
异十三烷醇N:通过丁烯三聚以及随后加氢甲酰化和氢化得到的支化脂族C13伯醇(以N由BASF SE市购)。
实施例1A:合成2-氰基-3,3-二苯基丙烯酸(5)
将205g(0.74mol)Uvinol 3035(4)悬浮于2L 50%浓度的甲醇中并加入71.2g(0.89mol)50%浓度的氢氧化钠溶液。将该混合物在20℃下搅拌过夜。然后用102g(0.89mol)32%浓度的盐酸使该混合物呈酸性。将沉淀滤出并洗涤2次,每次使用0.5L水。干燥后得到170g黄色粉末(5)(产率=92%)。
实施例1B:合成2-氰基-3,3-二苯基丙烯酰氯(6)
首先在20℃下将140g(0.56mol)(5)与在0.5L二氯甲烷中的3滴二甲基甲酰胺一起引入反应容器中。在60分钟内在20℃下滴加179g(1.41mol)草酰氯(1.41mol)。将该混合物在回流下搅拌24小时,然后在旋转蒸发器上浓缩至干。得到149g黄色固体(6)(产率=99%)。
实施例2A:合成2-氰基-3,3-二苯基丙烯酸[Pluriol A350E]酯(27)
在150℃下将63.4g(189mmol)Pluriol A350E(26)搅拌3分钟,在整个反应过程中通过浸入而通入氮气。然后加入50.0g(180mmol)Uvinol 3035(4)和0.58g(2mmol)异丙醇钛(IV)。将反应混合物在155℃下搅拌24小时。蒸除形成的乙醇。将该混合物溶于200ml二氯甲烷中,加入350mg(3mmol)85%磷酸并将该溶液在20℃下静置24小时。通过用1kg硅胶60快速层析而提纯产物。为此,将该溶液引入快速柱上并用二氯甲烷由该柱洗脱离析物(4),然后用甲醇洗脱产物(27)。在旋转蒸发器上浓缩甲醇溶液至干。得到94g橙色粘稠液体(27)(产率=95%)。
实施例2B:合成2-氰基-3,3-二苯基丙烯酸[Pluriol A500E]酯(29)
在整个反应过程通过浸入而通入氮气。首先在20℃下将83.3g(180mmol)Pluriol A500E(28)和50.0g Uvinul 3035(4)引入反应容器中,然后将该混合物在150℃下搅拌30分钟。然后加入0.58g(2mmol)异丙醇钛(IV)。将反应混合物在155℃下搅拌24小时。在反应过程中蒸除形成的乙醇。得到118g棕色粘稠液体(29)(产率=95%)。
实施例2C:合成2-氰基-3,3-二苯基丙烯酸[Pluriol A500PE]酯(31)
在整个反应过程通过浸入而通入氮气。首先在20℃下将77.4g(189mmol)Pluriol A500PE(30)和50.0g(180mmol)Uvinul 3035(4)引入反应容器中,然后将该混合物在155℃下搅拌30分钟。然后加入0.58g(2mmol)异丙醇钛(IV)并将反应混合物在155℃下搅拌21小时。蒸除形成的乙醇。将0.5ml水加入该混合物中并将该混合物搅拌10分钟,然后溶于200ml二氯甲烷中。通过用1kg硅胶60快速层析而提纯该产物。为此,将该溶液引入快速柱上并用二氯甲烷由该柱洗脱离析物(4),然后用甲醇洗脱产物(31)。在旋转蒸发器上浓缩甲醇溶液至干。得到110g橙色粘稠液体(31)(产率=83%)。
实施例2D:合成2-氰基-3,3-二苯基丙烯酸[EO-十三烷醇]酯(14)
在高压釜中将粉状KOH(2g,0.036mol)加入异十三烷醇(160g,0.8mol)中,然后在95℃和20毫巴下脱水1小时。然后用氮气使该混合物惰性化并加热到100℃。然后在8小时内计量加入氧化乙烯(634g,14.4mol)直到最大压力为6巴,然后在加料结束之后将该混合物再搅拌3小时。最后向该化合物中加入合成硅酸镁(3重量%)并过滤该混合物。得到十三烷基十八氧乙烯二醇(13)(794g;OH数为69mg KOH/g)。在搅拌下将化合物(13)(49.6g,0.05mol)溶于甲苯(100ml),并加入三乙胺(5.06g,0.05mol)。在25℃下将化合物(6)(13.4g,0.05mol)在二氯甲烷(50ml)中的溶液滴加到该溶液中以使得温度不超过30℃。在25℃下搅拌12小时之后,借助N2气流除去该溶液中的二氯甲烷。然后通过用饱和NaCl溶液振摇3次而萃取有机相,在硫酸钠上干燥并真空除去溶剂。以58g的产率得到目标化合物(14)。(14)的结构由1H-NMR光谱法证实。
实施例3A:合成(4-苯甲酰基-3-羟基苯氧基)乙酸甲酯(9)
首先在20℃下将107g(0.5mol)2,4-二羟基二苯甲酮99%(7)和69g(0.5mol)碳酸钾引入0.65L甲醇中。在20℃下在1小时内向该混合物中滴加98g(0.5mol)溴乙酸乙酯(8)。将该悬浮液在回流下搅拌24小时。滤出固体并用300ml甲醇洗涤。将粗产物溶于1L二氯甲烷中,然后加入30g硫酸钠和15g活性炭。将该混合物在20℃下搅拌15分钟,然后在100g硅胶60上吸滤。在旋转蒸发器上浓缩该溶液。得到70g白色针状物(9)(产率=49%)。
实施例3B:合成(4-苯甲酰基-3-羟基苯氧基)乙酸[Pluriol A350E]酯(34)
在整个反应过程通过浸入而通入氮气。首先在室温下将61.4g(192mmol)Pluriol A350E(26)和50.0g(175mmol)(9)引入反应容器中,然后将该混合物在155℃下搅拌30分钟。然后加入0.58g(2mmol)异丙醇钛(IV)并将反应混合物在155℃下搅拌18小时。蒸除形成的甲醇。将该混合物溶于200ml二氯甲烷中,加入350mg(3mmol)85%磷酸并将该溶液在20℃下静置24小时。通过用1kg硅胶60快速层析而提纯该产物。为此,将该溶液引入快速柱上并用二氯甲烷由该柱洗脱离析物(9),然后用甲醇洗脱产物(34)。在旋转蒸发器上浓缩甲醇溶液至干。得到99g橙色粘稠液体(34)(产率=99%)。
实施例3C:合成(4-苯甲酰基-3-羟基苯氧基)乙酸[Pluriol A500E]酯(35)
在整个反应过程通过浸入而通入氮气。将44.4g(96.0mmol)PluriolA500E(28)和25.0g(87.3mmol)(9)混合,然后将该混合物在155℃下搅拌30分钟。在加入0.29g(1mmol)异丙醇钛(IV)之后,将反应混合物在155℃下搅拌20小时。蒸除形成的甲醇。将该混合物溶于100ml二氯甲烷中。通过用435g硅胶60快速层析而提纯该产物。为此,将该溶液引入快速柱上并用二氯甲烷由该柱洗脱离析物(9),然后用甲醇洗脱产物(35)。在旋转蒸发器上浓缩甲醇溶液至干。得到54g橙色粘稠液体(35)(产率=86%)。
实施例4A:合成2,4,6-三苯胺基-对-(羧乙基)-1,3,5-三嗪(12)
首先在氮气气氛和室温下将30.0g(0.163mol)氰脲酰氯(10)和33.7g(0.244mol)碳酸钾引入1L 1,4-二烷中。向该混合物中分批加入82.3g(0.488mol)4-氨基苯甲酸乙酯98%(11)。将该混合物在回流下搅拌1小时。吸滤该混合物并将吸滤滤饼用400ml 80℃热水和250ml冷水洗涤。在真空干燥箱中干燥之后,得到87g白色固体(12)(产率=94%)。
实施例4B:合成2,4,6-三苯胺基-对-(羧基-[Pluriol A500E]-基)-1,3,5-三嗪
(36)
在整个反应过程通过浸入而通入氮气。将53.7g(116mmol)PluriolA500E(28)和20.0g(35.1mmol)(12)混合,然后将该混合物在150℃下搅拌30分钟。在加入0.85g(3mmol)异丙醇钛(IV)之后,将反应混合物在155℃下搅拌17小时。蒸除形成的乙醇。得到63g橙色粘稠液体(36)(产率=99%)。
实施例5A:合成Uvinul 3035-Lupasol FG-酰胺(38)
在整个反应过程通过浸入而通入氮气。在室温下将17g(61.6mmol;5mol%)Uvinul 3035(4)和75g(1.23mol)Lupasol FG(37)(胺值=16.34mmol/g)混合并将该混合物在110℃下搅拌2小时。蒸除形成的乙醇。得到82g琥珀色粘稠液体(38)。
实施例5B:合成Uvinul 3035-Lupasol FG-酰胺(39):
在整个反应过程通过浸入而通入氮气。在20℃下将34g(123mmol;10mol%)Uvinul 3035(4)和75g(1.23mol)Lupasol FG(37)(AN=16.34mmol/g)混合并将该混合物在110℃下搅拌2小时。蒸除形成的乙醇。得到84g琥珀色粘稠液体(39)。
实施例6A:合成3,6,9,12-四氧杂十三烷基肉桂酸酰胺(42):
首先在0-5℃下将37.9g(182mmol)(41)和9.5g(90mmol)碳酸钠引入50ml二氯甲烷中。在1小时内向该混合物中滴加30g(180mmol)(40)在50ml二氯甲烷中的溶液。将该混合物在20℃下搅拌过夜。再向该悬浮液中加入100ml二氯甲烷,然后通过振摇3次而萃取,每次使用200ml盐酸饱和的氯化钠溶液。有机相用硫酸钠干燥,然后过滤并在旋转蒸发器上于50℃下浓缩。得到60g琥珀色液体(42)(产率=98%)。
实施例6B:合成肉桂酸3,6,9,12-四氧杂十三烷基酯(44):
首先在20℃下将36.8g(180mmol)(43)和18.2g(180mmol)三乙胺引入50ml二氯甲烷中。在2小时内在室温下向该混合物中加入30g(180mmol)(40)在50ml二氯甲烷中的溶液。将该混合物在20℃下搅拌过夜。通过振摇3次萃取该悬浮液,每次使用75ml饱和氯化钠溶液。有机相用硫酸钠干燥,然后过滤并在旋转蒸发器上于50℃下浓缩。得到55g黄色部分结晶液体(44)(产率=89%)。
实施例7:研究稳定剂的作用
通过两种不同方法制备包含100g/l氰氟虫胺和40g/l UV吸收剂的配制剂:
a)湿研磨并随后加入如实施例9的UV吸收剂。
b)用如实施例8的UV吸收剂湿研磨。
将约20mg以此方式制备的混合物施用于显微镜载玻片上,干燥30分钟并连续暴露于光7天(Atlas Suntest CRT plus,“室外”设置,暴露于光对应于与夏日正午的正常阳光相同的光谱和强度)。在暴露时间之后,将样品溶于二甲亚砜中。借助定量UPLC(柱BEH C18 1.7μm 2.1×100;用由5/95增加到95/5的乙腈/0.1%H3PO4梯度液洗脱)测定氰氟虫胺的残留含量。为了对比,在每一暴露系列中还试验不含UV吸收剂的样品(参照)。
评价:在干燥之后立即将2个不暴露于光的样品再次溶解作为空白样,并测定氰氟虫胺的含量。将所得平均值设定为100%并针对此将其余样品统一。结果汇总于表1中:
表1
a)非本发明
实施例8:悬浮浓缩物的稳定性-用UV吸收剂湿研磨
通过湿研磨(1小时,3,000rpm,Dispermat)表2中所提到的组分以及105g氰氟虫胺(95重量%纯度)和70g 1,2-丙二醇而制备悬浮浓缩物A1-A6和C1。得到其中至少90%固体颗粒具有的粒度小于5μm且D(4,3)为1.0μm的均匀稳定悬浮液。在每种情况下将20g Wettol D1、5.0g消泡剂、3.0g黄原胶和2.0g杀菌剂加入这些悬浮液中,用水配成1.0L。在54℃下储存两周之后,粒度和颗粒分布均没有变化。
在每种情况下将来自所有试验的样品用CIPAC水D(包含342ppmCa/Mg离子)稀释至浓度为0.1重量%和1重量%的悬浮液。在储存6小时后实际上没有发现沉降。
该试验表明与没有UV吸收剂的SC相比,加入本发明UV吸收剂没有降低悬浮浓缩物(SC)的稳定性。A1和A2的稳定性与A4和A5相当表明该SC配制剂甚至使用更少分散剂,即111g/l而不是222g/l也没有问题。
表2
混合物 | A1 | A2 | A4 | A5 | C1a) |
Pluronic 10500[g/l] | 111 | 111 | 222 | 222 | 167 |
UV吸收剂实施例2A[g/l] | 40 | - | 80 | - | - |
UV吸收剂实施例3B[g/l] | - | 40 | - | 80 | - |
a)非本发明
实施例9:悬浮浓缩物的稳定性-随后加入UV吸收剂
通过湿研磨(1小时,3,000rpm,Dispermat)105g氰氟虫胺(95重量%纯度)、70g 1,2-丙二醇和111g Pluronic 10500而制备悬浮浓缩物A7-A17。得到其中至少90%固体颗粒具有的粒度小于5μm且D(4,3)为1.0μm的均匀稳定悬浮液。在每种情况下将40g UV吸收剂(见表3;试验C1例外)、20g Wettol D1、5.0g消泡剂、3.0g黄原胶和2.0g杀菌剂加入这些悬浮液中,用水配成1.0L。在54℃下储存两周之后,活性化合物的粒度和颗粒分布均没有变化。
在每种情况下将来自所有试验的样品用CIPAC水D(包含342ppmCa/Mg离子)稀释至浓度为0.1重量%和1重量%的活性化合物悬浮液。在储存6小时后实际上没有发现活性化合物的沉降。
表3
试验 | 如下实施例的UV吸收剂 |
C1a) | 无 |
A7 | 6A |
A8 | 6B |
A9 | 2A |
A10 | 2B |
A13 | 5A |
A14 | 5B |
A15 | 3B |
A16 | 3C |
A17 | 4B |
a)非本发明,制备见实施例9。
该试验表明加入本发明UV吸收剂没有降低悬浮浓缩物的稳定性。该高稳定性正如实施例8一样又在低浓度的分散剂(111g/l)下实现。
实施例10:悬浮浓缩物的稳定性-随后加入UV吸收剂
如实施例10制备悬浮浓缩物A21-A31,不同的是Pluronic 10500的浓度为222g/l且UV吸收剂的浓度为80g/l(表4)。在54℃下储存两周之后,粒度和颗粒分布均没有变化。
在每种情况下将来自所有试验的样品用CIPAC水D(包含342ppmCa/Mg离子)稀释至浓度为0.1重量%和1重量%的悬浮液。在储存6小时后实际上没有发现沉降。
表4
试验 | 如下实施例的UV吸收剂 |
C1a) | 无 |
A21 | 6A |
A22 | 6B |
A23 | 2A |
A24 | 2B |
A27 | 5A |
A28 | 5B |
A29 | 3B |
A30 | 3C |
A31 | 4B |
a)非本发明,制备见实施例9。
该试验表明加入本发明UV吸收剂没有降低悬浮浓缩物的稳定性。
实施例11:测试甲体氯氰菊酯的UV稳定性
制备20mg甲体氯氰菊酯和5或10mg(即相对于活性化合物分别为25或50重量%)UV吸收剂在丙酮中的溶液。将几滴置于玻璃板上,干燥1小时,然后用波长为300-800nm的UV/VIS光辐照24小时。然后将辐照后的混合物溶于四氢呋喃中并借助HPLC色谱法测定甲体氯氰菊酯的含量(即回收率)。作为对比研究在黑暗中储存24小时的相同样品。该试验表明该UV吸收剂显著提高UV敏感性活性化合物如甲体氯氰菊酯的稳定性(表5)。
表5
试验 | 如下实施例的UV吸收剂 | UV吸收剂[重量%] | 回收率[%] |
A | - | 0 | 48 |
B | - | 0 | 46 |
C | 2A | 25 | 99 |
D | 2B | 25 | 91 |
E | 3B | 25 | 92 |
F | 3C | 25 | 92 |
G | 4B | 25 | 99 |
H | 5A | 25 | 99 |
I | 6A | 25 | 80 |
J | 6B | 25 | 67 |
K | 2A | 50 | 95 |
L | 2B | 50 | 94 |
M | 3B | 50 | 93 |
N | 3C | 50 | 94 |
O | 4B | 50 | 95 |
P | 5A | 50 | 95 |
实施例12:使用氰氟虫胺的生物学试验
在生长室中于26℃下将植物(青豆,金甲豆(Phaseolus lunatus))用UV光每天恒定辐照24小时。在300-400nm的UV范围内测量辐照强度,结果为39瓦/m2。
在两叶阶段用包含来自实施例9-11的悬浮浓缩物(SC)A7-A31或C1的含水喷雾液以10g/ha氰氟虫胺的施用率处理植物。在处理之后第7和10天(DAT)对Spodoptera eridania(南方灰翅夜蛾)的幼虫进行生物评价以测定残留的活性化合物活性。为此,使幼虫与植物接触并在3天后测定死亡率(表6)。
该试验表明该杀虫剂在包含所测试的UV吸收剂的配制剂中比在不含UV吸收剂的配制剂中对UV光更稳定。
表6
a)对比试验,非本发明
实施例13:测定表面张力
该UV吸收剂的表面张力(ST)在25℃下于UV吸收剂浓度为约1-5,000mg/l下测定。用于对比的水/空气的ST为72.4mN/m,市售表面活性剂的ST为约30-35mN/m。结果总结于表7中,其表明本发明UV吸收剂可以显著降低表面张力,即它们具有表面活性。
表7
如下实施例的UV吸收剂 | ST[mN/m] |
2A | 43.1 |
3B | 45.7 |
2D | 33.9 |
Claims (10)
2.如权利要求1所要求的组合物,其中UV表示选自式B或C的基团。
3.如权利要求1或2所要求的组合物,其中所述农药是UV敏感性的。
4.如权利要求1-3中任一项所要求的组合物,其中农药与UV吸收剂的重量比为30∶1-1∶2。
5.如权利要求1-4中任一项所要求的组合物,其中所述农药为合成除虫菊酯类。
6.一种如权利要求1所要求的式I的UV吸收剂,其中若R2和R3均表示H,则AO表示CH2CH2NH。
7.如权利要求6所要求的UV吸收剂,其中UV表示选自式B和C的结构的游离基团。
8.如权利要求6或7所要求的UV吸收剂,其中AO表示CH2CH2NH。
9.如权利要求6-8中任一项所要求的UV吸收剂在农业化学组合物中的用途。
10.一种防治植物病原性真菌和/或不希望的植物生长和/或不希望的昆虫或螨虫侵染和/或调节植物生长的方法,其中使如权利要求1-5中任一项所要求的组合物作用于特定害虫、其栖息地或要防止特定害虫的植物、土壤和/或不希望的植物和/或农作物和/或其生长场所。
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WO2010130752A2 (de) | 2009-05-15 | 2010-11-18 | Basf Se | Hochmolekulare unpolare benztriazole |
US9125411B2 (en) | 2010-04-15 | 2015-09-08 | Basf Se | UV absorbers for reducing the E/Z isomerization of pesticides |
US8765753B2 (en) * | 2011-03-23 | 2014-07-01 | Basf Se | Process for the preparation of s-triazine compounds |
WO2017157678A1 (en) * | 2016-03-17 | 2017-09-21 | Basf Se | Reduced photodegradation by co-dissolving pyraclostrobin and uv absorber |
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