CN113651718B - 一种1, 1-二氰基肟醚类化合物及其应用 - Google Patents
一种1, 1-二氰基肟醚类化合物及其应用 Download PDFInfo
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- CN113651718B CN113651718B CN202110508837.7A CN202110508837A CN113651718B CN 113651718 B CN113651718 B CN 113651718B CN 202110508837 A CN202110508837 A CN 202110508837A CN 113651718 B CN113651718 B CN 113651718B
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 36
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
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- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
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- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
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- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
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- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 238000010998 test method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
- C07C255/64—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to oxygen atoms
-
- A—HUMAN NECESSITIES
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Abstract
本发明公开了一种1,1‑二氰基肟醚类化合物,结构如通式I所示,式中各取代基的定义见说明书。
Description
技术领域
本发明属农用杀菌剂领域,具体涉及一种1, 1-二氰基肟醚类化合物及其应用。
背景技术
细菌性病害已成为我国农业生产中仅次于真菌性病害的第二大常发性病害,据不完全统计,我国细菌性病害目前发生面积在1.2亿亩次,细菌性病害防治市场容量超过20亿元。目前农业生产中,防治细菌性病害药剂主要包括用量较大的铜制剂(包括有机或无机铜制剂)和抗生素类产品;其中,铜制剂的防效较低并且大量的重金属喷施到环境中,对土壤、水体和食品形成污染,引发环境及食品的安全担忧;而另一方面,抗生素的大量使用,可能引起人体病原菌对医用抗生素产生抗药性。其它能用于农业细菌治疗的仅有少量品种,实际生产中受到抗性及防效的双重限制,推广面积较小。因此,研发新型、高效、低毒、环境友好型细菌性病害防治药剂是非常必要而迫切的。
发明内容
本发明的目的是提供一种可以控制多种植物细菌性病害和真菌性病害的1, 1-二氰基肟醚类化合物,及其用于制备农业和其它领域中防治病菌的药物。
为实现上述目的,本发明的技术方案如下:
一种1, 1-二氰基肟醚类化合物,其特征在于,化合物如通式I所示:
式中:
W选自W1-W4所示基团之一:
;
X1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15、X16、X17各自独立地选自氢、卤素、氰基、硝基、羟基、巯基、氨基、羧基、-ON=C(CN)2、(3-氯-5-(三氟甲基)吡啶-2-基)氨基、C1-C8烷基、C3-C8环烷基、卤代C1-C8烷基、C1-C8烷氧基、卤代C1-C8烷氧基、C1-C8烷硫基、卤代C1-C8烷硫基、C1-C8烷基氨基、C1-C8二烷基氨基、C1-C8烷基羰基、C1-C8烷氧基羰基、氨基羰基、C1-C8烷基氨基羰基、C1-C8二烷基氨基羰基、C1-C8烷基磺酰基、C1-C8烷基磺酰基氧基或者任意取代的芳氨基或杂芳基氨基;但,当X2、X4、X5选自氢时,X1、X3不选自硝基;
或者,W选自W1,X1、X2、X4选自氢,X3、X5选自硝基;
或通式I化合物的盐。
本发明中较优选的化合物为:通式I中,
W选自W1-W4所示基团之一;
X1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15、X16、X17各自独立地选自氢、卤素、氰基、硝基、羟基、巯基、氨基、羧基、-ON=C(CN)2、(3-氯-5-(三氟甲基)吡啶-2-基)氨基、C1-C4烷基、C3-C4环烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C1-C4烷硫基、卤代C1-C4烷硫基、C1-C4烷基氨基、C1-C4二烷基氨基、C1-C4烷基羰基、C1-C4烷氧基羰基、氨基羰基、C1-C4烷基氨基羰基、C1-C4二烷基氨基羰基、C1-C4烷基磺酰基、C1-C4烷基磺酰基氧基、未取代的或被1-3个如下基团进一步取代的苯氨基或(吡啶-2-基)氨基:卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C4烷基、C3-C4环烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C1-C4烷硫基或卤代C1-C4烷硫基;但,当X2、X4、X5选自氢时,X1、X3不选自硝基;
或者,W选自W1,X1、X2、X4选自氢,X3、X5选自硝基;
或通式I化合物与盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸形成的盐。
本发明中进一步优选的化合物为:通式I中,
W选自W1-W4所示基团之一;
X1、X2、X3、X4、X5、X6、X7、X8、X9、X10、X11、X12、X13、X14、X15、X16、X17各自独立地选自氢、氟、氯、溴、氰基、硝基、羟基、巯基、氨基、羧基、-ON=C(CN)2、(3-氯-5-(三氟甲基)吡啶-2-基)氨基、甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基、一氯甲基、二氯甲基、三氯甲基、一溴甲基、二溴甲基、三溴甲基、一氟甲基、二氟甲基、三氟甲基、2, 2,2-三氟乙基、七氟异丙基、甲氧基、乙氧基、正丙氧基、异丙氧基、二氟甲氧基、三氟甲氧基、甲硫基、乙硫基、三氟甲硫基、2, 2,2-三氟乙硫基、甲氨基、乙氨基、N, N-二甲基氨基、甲基羰基、乙基羰基、甲氧基羰基、乙氧基羰基、氨基羰基、N-甲基氨基羰基、N-乙基氨基羰基、N,N-二甲基氨基羰基、甲基磺酰基、乙基磺酰基、甲基磺酰基氧基、乙基磺酰基氧基、未取代的或被1-2个如下基团进一步取代的苯氨基或(吡啶-2-基)氨基:氟、氯、溴、氰基、硝基、羟基、巯基、氨基、羧基、甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、仲丁基、叔丁基、一氯甲基、二氯甲基、三氯甲基、一溴甲基、二溴甲基、三溴甲基、一氟甲基、二氟甲基、三氟甲基、2, 2, 2-三氟乙基、七氟异丙基、甲氧基、乙氧基、正丙氧基、异丙氧基、二氟甲氧基、三氟甲氧基、甲硫基、乙硫基、三氟甲硫基或2, 2, 2-三氟乙硫基;但,当X2、X4、X5选自氢时,X1、X3不选自硝基;
或者,W选自W1,X1、X2、X4选自氢,X3、X5选自硝基;
或通式I化合物与盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸形成的盐。
本发明中更进一步优选的化合物为:通式I中,
W选自W1,X1选自氰基或硝基,X2、X3、X4、X5选自氢;
或者,W选自W1,X2选自氰基或硝基,X1、X3、X4、X5选自氢;
或者,W选自W1,X3选自氰基或硝基,X1、X2、X4、X5选自氢;
或者,W选自W1,X1选自氰基,X3选自氰基或硝基,X2、X4、X5选自氢;
或者,W选自W1,X1选自硝基,X3选自氰基,X2、X4、X5选自氢;
或者,W选自W1,X2选自氰基,X3选自氰基或硝基,X1、X4、X5选自氢;
或者,W选自W1,X2选自硝基,X3选自氰基或硝基,X1、X4、X5选自氢;
或者,W选自W1,X2选自氰基,X4选自氰基或硝基,X1、X3、X5选自氢;
或者,W选自W1,X2选自硝基,X4选自氰基或硝基,X1、X3、X5选自氢;
或者,W选自W1,X2选自氯,X3选自氰基或硝基,X1、X4、X5选自氢;
或者,W选自W1,X1、X3选自硝基,X4选自氯,X2、X5选自氢;
或者,W选自W1,X1、X3选自硝基,X4选自-ON=C(CN)2,X2、X5选自氢;
或者,W选自W1,X1、X3选自硝基,X2选自(3-氯-5-(三氟甲基)吡啶-2-基)氨基,X5选自三氟甲基,X4选自氢;
或者,W选自W1,X1、X2、X4选自氢,X3、X5选自硝基;
或通式I化合物与盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸形成的盐。
上面给出的通式化合物的定义中,汇集所用术语一般代表如下取代基:
卤素:指氟、氯、溴或碘。
烷基:直链或支链烷基,例如甲基、乙基、正丙基、异丙基或不同的丁基、戊基或己基异构体等。
环烷基:取代或未取代的环状烷基,例如环丙基、环戊基或环己基等;取代基如甲基、卤素等。
卤代烷基:直链或支链烷基,在这些烷基上的氢原子可部分或全部被卤素所取代,例如一氯甲基、二氯甲基、三氯甲基、一溴甲基、二溴甲基、三溴甲基、一氟甲基、二氟甲基、三氟甲基、2, 2, 2-三氟乙基、七氟异丙基等。
烷氧基:直链或支链烷基,经氧原子键连接到结构上,例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、叔丁氧基等。
卤代烷氧基:直链或支链烷氧基,在这些烷氧基上的氢原子可部分或全部被卤素所取代,例如氯甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、2, 2, 2-三氟乙氧基等。
烷硫基:直链或支链烷基,经硫原子键连接到结构上,例如甲硫基、乙硫基等。
卤代烷硫基:直链或支链烷硫基,在这些烷硫基上的氢原子可部分或全部被卤素所取代,例如二氟甲硫基、三氟甲硫基、2, 2, 2-三氟乙硫基等。
烷基氨基:直链或支链烷基,经氮原子键连接到结构上,例如甲氨基、乙氨基、正丙基氨基、异丙基氨基或同分异构的丁基胺等。
二烷基氨基:两个相同或不同的直链或支链烷基,经氮原子键连接到结构上,例如N, N-二甲基氨基、N-甲基-N-乙基氨基等。
烷基羰基:烷基经羰基连接到结构上,例如甲基羰基(CH3CO-),乙基羰基(CH3CH2CO-)等。
烷氧基羰基:烷基-O-CO-,例如甲氧基羰基(CH3OCO-)、乙氧基羰基(CH3CH2OCO-)、正丙氧基羰基(CH3CH2CH2OCO-)、正丁氧基羰基(CH3CH2CH2CH2OCO-)等。
氨基羰基:即NH2-CO-。
烷基氨基羰基:烷基-NH-CO-,例如N-甲基氨基羰基(CH3NHCO-),N-乙基氨基羰基(CH3CH2NHCO-)等。
二烷基氨基羰基:例如N,N-二甲基氨基羰基((CH3)2NCO-),N, N-二乙基氨基羰基((CH3CH2)2NCO-)等。
烷基磺酰基:烷基-S(O)2-,例如甲基磺酰基(CH3S(O)2-)、乙基磺酰基(CH3CH2S(O)2-)等。
烷基磺酰基氧基:烷基-S(O)2-O-,例如甲基磺酰基氧基(CH3S(O)2-O-)、乙基磺酰基氧基(CH3CH2S(O)2-O-)等。
芳氨基:芳基-NH2-,例如苯氨基(Ph-NH2-);芳氨基的芳基部分包括苯基或萘基等。
杂芳基氨基:杂芳基-NH2-,例如(吡啶-2-基)氨基()、(3-氯-5-(三氟甲基)吡啶-2-基)氨基()等;杂芳基氨基的杂芳基部分是指具有1-20个碳原子、1-4个选自N、S、O杂原子的单环或多环杂芳族基团,例如吡咯基、呋喃基、噻吩基、咪唑基、吡唑基、噁唑基、噻唑基、异噁唑基、异噻唑基、吡啶基、嘧啶基、哒嗪基、哒嗪酮基、吲哚基、苯并呋喃基、苯并噁唑基、苯并噻吩基、苯并噻唑基、苯并异噁唑基、苯并异噻唑基、苯并咪唑基、苯并吡唑基、喹喔啉基等。
本发明部分通式I化合物如表1~表4所示,但本发明绝非仅限于这些化合物。
通式I中,当W=W1时,通式I可以通式I-W1表示(为便于叙述,W1的取代基X1、X2、X3、X4、X5以R表示;另外,通式I-W1中的数字1、2、3、4、5、6表示苯环上取代基的取代位置)。
表1:通式I-W1中,R为不同的取代基见表1,代表化合物编号为1.1-1.387。
表1
通式I中,当W=W2时,通式I可以通式I-W2表示(为便于叙述,W2的取代基X6、X7、X8、X9以R表示;另外,通式I-W2中的数字1、2、3、4、5表示吡啶环上取代基的取代位置)。
表2:通式I-W2中,R为不同的取代基见表2,代表化合物编号为2.1-2.285。
表2
通式I中,当W=W3时,通式I可以通式I-W3表示(为便于叙述,W3的取代基X10、X11、X12、X13以R表示;另外,通式I-W3中的数字1、2、3、4、5表示吡啶环上取代基的取代位置)。
表3:通式I-W3中,R为不同的取代基与表2一致,依次对应表2中2.1-2.285记载的取代基,代表化合物编号为3.1-3.285。
通式I中,当W=W4时,通式I可以通式I-W4表示(为便于叙述,W4的取代基X14、X15、X16、X17以R表示;另外,通式I-W4中的数字1、2、3、4、5表示吡啶环上取代基的取代位置)。
表4:通式I-W4中,R为不同的取代基与表2一致,依次对应表2中2.1-2.285记载的取代基,代表化合物编号为4.1-4.285。
本发明部分化合物的物化性质、核磁数据及质谱数据如表5所示:
表5
本发明的通式I化合物,可按照以下方法制备(式中各基团除另有说明外定义同前,Halo代表卤素,例如F, Cl, Br或I; M表示阳离子,例如Na+, K+, CS+, Ag+或NH4 +等):
通式II化合物与通式III化合物在适宜的溶剂中,在温度从-10°C到溶剂沸点下反应0.5-48小时可制得通式I化合物。适宜的溶剂可相同或不同选自为醇类(如,甲醇、乙醇等)、芳烃类(如,苯、甲苯、二甲苯等)、酮类(如,丙酮、甲乙酮、甲基异丁基酮等)、卤代烃类(如,二氯甲烷等、氯仿、四氯化碳等)、酯类(如,乙酸甲酯、乙酸乙酯等)、醚类(如,四氢呋喃、二噁烷、二乙醚、1, 2-二甲氧基乙烷等)、极性溶剂类(如,水、乙腈、二氧六环、N, N-二甲基甲酰胺、N-甲基吡咯烷酮、二甲基亚砜等)或上述溶剂的混合溶剂。
通式II化合物通常有市售,也可按常规方法自制。
通式III化合物可以按公知方法(例如CN103804321、WO2008139481、US20130096098或Journal of the Chemical Society of Pakistan, 33(3), 324-332,2011等报道的方法)制备。
本发明通式I所示的化合物用于控制植物细菌性病害的用途,可用于防治多种植物细菌性病害,例如果斑病(如甜瓜果斑病等)、叶斑病(如番茄细菌性叶斑病等)、青枯病(如番茄青枯病、马铃薯青枯病等)、细菌性疫病、溃疡病(如柑橘溃疡病、猕猴桃溃疡病等)、软腐病(如大白菜软腐病等)、细菌性角斑病(如黄瓜细菌性角斑病等)、细菌性条斑病(如水稻细菌性条斑病等)、叶枯病、白叶枯病(如水稻白叶枯病等)、野火病和细菌性疮痂病等。
本发明的化合物也可用于防治在多种作物上由卵菌纲、担子菌纲、子囊菌和半知菌类等多种真菌引起的病害,例如在较低剂量下对黄瓜霜霉病、黄瓜灰霉病、黄瓜炭疽病、黄瓜白粉病、番茄早疫病、番茄晚疫病、辣椒疫病、葡萄霜霉病、葡萄白腐病、苹果轮纹病、苹果斑点落叶病、水稻纹枯病、水稻稻瘟病、小麦锈病、小麦叶斑病、小麦白粉病、油菜菌核病、玉米小斑病等病害都有着很好的防效。
由于其积极的特性,上述化合物可有利地用于保护农业和园艺业重要的作物、家畜和种畜,以及人类常去的环境免于病菌的伤害。
为获得理想效果,化合物的用量因各种因素而改变,例如所用化合物、预保护的作物、有害生物的类型、感染程度、气候条件、施药方法、采用的剂型等。
每公顷5克-5公斤的化合物剂量能提供充分的防治。
本发明还包括以通式I化合物作为活性组分的杀菌剂。该杀菌剂中活性组分的重量百分含量在0.1-99%之间。该杀菌剂中还包括农业、林业、卫生上可接受的载体和助剂。
本发明的杀菌剂可以制剂的形式施用。通式I化合物作为活性组分溶解或分散于载体和/或助剂中或配制成制剂以便作为杀菌使用时更易于分散。
本发明以通式I化合物为活性组分,可依照本领域所熟知的方式将通式I化合物制备成多种制剂类型,包括水剂、可溶性液剂、乳油、微乳剂、水乳剂、悬浮剂、悬浮种衣剂、可分散油悬浮剂、超低容量剂、粉剂、可湿性粉剂、可溶性粉剂、可乳化粉剂、颗粒剂、水分散粒剂、可溶性粒剂、可乳化粒剂、干悬浮剂、泡腾粒剂、漂浮粒剂、片剂、可溶性片剂、泡腾片剂、微胶囊粉剂、微胶囊悬浮剂,在任何情况下,制剂类型的选取取决于通式I化合物的物理、化学和生物学特性。
本发明通式I化合物的杀菌制剂可由通常的加工方法制备,即将活性物质与液体载体或固体载体混合后,加入一种或几种表面活性剂如乳化剂、分散剂、润湿剂、增稠剂、稳定剂和消泡剂等。通常组合物中含有至少一种载体和至少一种表面活性剂。在各种情况下,应确保本发明组合物活性组分均匀分布。
水剂是将通式I化合物、表面活性剂、水混合均匀,形成均一透明的液体。通常含有5~50%的活性成分,5~20%乳化剂,0~10%的其他添加剂如渗透剂,以及水余量。
可溶性液剂将通式I化合物、表面活性剂、非水极性溶剂混合均匀,形成均一透明液体。可溶性液剂中通常含有5~60%的活性成分,5~20%乳化剂,0~10%的其他添加剂如渗透剂,以及液体载体余量。
乳油将通式I化合物、表面活性剂、有机溶剂混合均匀,形成均相油状液体。乳油中通常含有1~70%的活性成分,5~20%乳化剂,0~10%的其他添加剂如渗透剂、稳定剂,以及液体载体余量。
微乳剂将通式I化合物、表面活性剂、水、有机溶剂混合均匀,形成均一透明液体。微乳剂中通常含有1~50%的活性成分,5~30%乳化剂,2~10%防冻剂,0~10%的其他添加剂如渗透剂、稳定剂,以及液体载体余量。
水乳剂将通式I化合物、表面活性剂、有机溶剂混合均匀,制成油相;将水、防冻剂混合在一起,制成水相。用高剪切乳化机高速剪切油相,同时慢慢将水相加入油相,即可得到分散均匀的水乳剂。通常含有5~50%的活性成分,5~20%乳化剂,2~5%防冻剂,以及液体载体余量。
悬浮剂将通式I化合物、分散剂、润湿剂、防冻剂、水混合均匀后,经砂磨机砂磨,获得稳定的非沉积可流动的液体。悬浮剂中通常含有5~50%的活性成分,2~10%分散剂,2~5%润湿剂,2~5%防冻剂,0~10%其他添加剂如消泡剂、增稠剂、防腐剂,以及液体载体余量。
悬浮种衣剂将通式I化合物、分散剂、润湿剂、成膜剂、水混合均匀后,经砂磨机砂磨,获得稳定的非沉积可流动的液体。悬浮种衣剂中通常含有1~50%的活性成分,2~10%分散剂,2~5%润湿剂,2~5%防冻剂,2~10%成膜剂,0~10%其他添加剂如消泡剂、增稠剂、防腐剂、警戒色,以及液体载体余量。
可分散油悬浮剂将通式I化合物、表面活性剂、油基载体混合均匀后,经砂磨机砂磨,获得稳定的非沉积可流动的液体。可分散油悬浮剂中通常含有5~50%的活性成分,5~30%表面活性剂,0~10%其他添加剂如增稠剂、稳定剂,以及液体载体余量。
超低容量剂将通式I化合物、表面活性剂、有机溶剂混合均匀,加工成均一透明油相。通常含有1~30%的活性成分,5~30%乳化剂,0~10%的其他添加剂如稳定剂,以及液体载体余量。
粉剂将通式I化合物、助剂、载体混合,经粉碎得到粉体物。粉剂通常含有5~85%的活性成分,5~10%分散剂,0~10%的其他添加剂如稳定剂,以及固体载体余量。
可湿性粉剂将通式I化合物、分散剂、润湿剂、载体混合,经粉碎得到粉体物。可湿性粉剂通常含有5~85%的活性成分,5~10%分散剂,1~10%润湿剂,0~10%的其他添加剂如稳定剂,以及固体载体余量。
可溶性粉剂将通式I化合物、分散剂、润湿剂、载体混合,经粉碎得到粉体物。可溶性粉剂通常含有5~80%的活性成分,5~10%分散剂,1~10%润湿剂,0~10%的其他添加剂如稳定剂,以及固体载体余量。
可乳化粉剂将通式I化合物、表面活性剂、有机溶剂混合,制成均一透明油相,然后将上述油相均匀喷洒在预先粉碎好的载体上。可乳化粉剂通常含有5~50%的活性成分,5~30%乳化剂,5~10%润湿分散剂,0~15%的有机溶剂,以及固体载体余量。
颗粒剂将通式I化合物、助剂、载体混合,然后捏合、造粒、干燥、包衣。颗粒剂通常含有0.5~20%的活性成分,0.1~10%粘结剂,0~10%的其他添加剂如稳定剂,以及固体载体余量。
水分散粒剂将通式I化合物、分散剂、润湿剂、崩解剂、载体混合,然后捏合、造粒、干燥。水分散粒剂通常含有5~85%的活性成分,1~10%分散剂,1~10%润湿剂,0.1~10%粘结剂,0~10%的其他添加剂如崩解剂、稳定剂,以及固体载体余量。
可溶性粒剂将通式I化合物、分散剂、润湿剂、崩解剂、载体混合,然后捏合、造粒、干燥。可溶性粒剂通常含有5~85%的活性成分,1~10%分散剂,1~10%润湿剂,0.1~10%粘结剂,0~10%的其他添加剂如崩解剂、稳定剂,以及固体载体余量。
可乳化粒剂将通式I化合物、表面活性剂、有机溶剂混合,制成均一透明油相,然后将上述油相均匀喷洒在预先粉碎好的载体上,捏合、造粒、干燥。可乳化粒剂通常含有5~50%的活性成分,5~30%乳化剂,5~10%润湿分散剂,0~15%的有机溶剂,0~10%的其他添加剂如崩解剂、稳定剂、粘结剂,以及固体载体余量。
干悬浮剂将通式I化合物、分散剂、润湿剂、载体、水混合均匀后,经砂磨机砂磨,砂磨后进行喷雾干燥。干悬浮剂中通常含有5~80%的活性成分,2~20%分散剂,2~10%润湿剂,0~10%其他添加剂如消泡剂、增稠剂、以及固体载体余量。
泡腾粒剂将通式I化合物、润湿分散剂、泡腾崩解剂、载体混合,然后捏合、造粒。泡腾颗粒剂通常含有0.5~30%的活性成分,2~20%润湿分散剂,2~20%泡腾崩解剂,0~10%的其他添加剂如稳定剂、粘结剂,以及固体载体余量。
漂浮粒剂将通式I化合物、润湿分散剂、漂珠、载体混合,然后捏合、造粒。漂浮颗粒剂通常含有0.5~30%的活性成分,2~20%润湿分散剂,5~20%漂珠,0~10%的其他添加剂如稳定剂、粘结剂、崩解剂,以及固体载体余量。
片剂将通式I化合物、分散剂、润湿剂、崩解剂、载体混合,然后捏合、压片、干燥。片剂通常含有5~50%的活性成分,1~10%分散剂,1~10%润湿剂,0.1~10%粘结剂,0~10%的其他添加剂如崩解剂、稳定剂,以及固体载体余量。
可溶性片剂将通式I化合物、分散剂、润湿剂、崩解剂、载体混合,然后捏合、压片、干燥。可溶性片剂通常含有5~50%的活性成分,1~10%分散剂,1~10%润湿剂,0.1~10%粘结剂,0~10%的其他添加剂如崩解剂、稳定剂,以及固体载体余量。
泡腾片剂将通式I化合物、润湿分散剂、泡腾崩解剂、载体混合,然后捏合、压片。泡腾片剂通常含有0.5~30%的活性成分,2~20%润湿分散剂,2~20%泡腾崩解剂,0~10%的其他添加剂如稳定剂、粘结剂,以及固体载体余量。
微胶囊粉剂将通式I化合物溶于溶剂中,向其中加入乳化剂和壁材,搅拌均匀,得到油相;水中加入分散剂得到水相;在高速搅拌下,将油相加入水相中,形成水包油型乳状液;在搅拌条件下,向乳状液中加入固化剂,加热保温成囊,然后过滤、干燥。微胶囊粉剂通常含有0.5~30%的活性成分,2~10%乳化剂,2~10%润湿分散剂,5~30%的其他添加剂如壁材、消泡剂、固化剂、稳定剂,以及固体载体余量。
微胶囊悬浮剂将通式I化合物溶于溶剂中,向其中加入乳化剂和壁材,搅拌均匀,得到油相;水中加入分散剂得到水相;在高速搅拌下,将油相加入水相中,形成水包油型乳状液;在搅拌条件下,向乳状液中加入固化剂,加热保温成囊,形成微囊悬浮剂。微胶囊悬浮剂通常含有0.5~30%的活性成分,2~10%乳化剂,2~10%润湿分散剂,5~30%的其他添加剂如壁材、消泡剂、防腐剂、增稠剂、固化剂、稳定剂,以及液体载体余量。
本发明通式I化合物的杀菌制剂的配制可以采用本领域的技术人员公知的(液体或固体)载体和各种助剂。例如包括但不限于下述各类物质。
本发明通式I化合物的杀菌制剂中适宜的表面活性剂,可以是乳化剂、分散剂或湿润剂;可以是非离子型或离子型中的一种或几种。离子型表面活性剂选自磺酸盐类、硫酸盐类、羧酸盐类、磷酸酯盐类、琥珀酸酯盐类、木质素磺酸盐类、丙烯酰胺丙烯酸共聚物类等。非离子表面活性剂选自脂肪醇聚氧乙烯醚、烷基酚聚氧乙烯醚、脂肪胺聚氧乙烯醚、脂肪酸聚氧乙烯醚、酸醇酯及其聚氧乙烯醚、烷基聚乙二醇醚、烷基苯基聚乙二醇醚、脂肪酰胺及其聚氧乙烯醚、烷醇酰胺及其聚氧乙烯醚、聚氧乙烯聚氧丙烯醚嵌段共聚物、烷基萘磺酸钠脂肪醇聚氧乙烯基醚、失水山梨醇脂肪酸酯聚氧乙烯基醚等。
上述表面活性剂可选自所示表面活性剂中的一种或几种,如:木质素磺酸钠盐或钙盐、聚氧乙烯(n20)苯乙基酚基醚油酸酯、烷基芳基聚氧乙烯聚氧丙烯醚、三苯乙烯基酚聚氧乙烯(n20)醚磷酸化三乙醇胺盐、农乳0201B、农乳0203B、农乳100#、农乳600#、农乳700#、农乳1601#、农乳AEO-3、农乳AEO-5、农乳AEO-7、农乳T-20、农乳T-80、农乳T-85、农乳S-80、农乳S-85、农乳NP-7、农乳NP-10、农乳NP-15、农乳OX-2681、农乳OX-8686、农乳OX-690、农乳2201#、聚羧酸盐分散剂GY-D800、聚羧酸盐分散剂GY-D04、聚羧酸盐分散剂GY-D02、烷基萘磺酸盐甲醛缩合物(NNO)、萘酚磺酸甲醛缩合物钠盐、烷基酚聚氧乙烯聚氧丙烯醚、苯乙烯马来酸酐、甲基萘磺酸甲醛缩合物、蓖麻油环氧乙烷加成物、烷基酚聚氧乙烯聚氧丙烯醚、烷基-二乙二醇醚-磺酸钠、N-甲基-油酰基-牛磺酸钠、净洗剂LS、亚甲基萘磺酸钠、油酸甲基氨基乙基磺酸钠、分散剂SP-28F、分散剂SP-SC3、达润分散剂D909S、烷基芳基聚氧乙烯醚、十二烷基聚氧乙烯醚磷酸酯、烷基酚聚氧乙烯醚甲醛缩合物、二丁基萘磺酸钠(拉开粉BX)、二丁基萘磺酸甲醛缩合物、分散剂SD-811、分散剂SD815、分散剂SK-24、分散剂SK-20TX、分散剂SK-5218、分散剂SK-33H、分散剂SK-10LX、分散剂SK-551、分散剂Atlox4913、分散剂EL-20、分散剂EL-40、分散剂EL-90、分散剂YUS-NV1203、分散剂YUS-NV1420、分散剂YUS-WG4、分散剂YUS-TG285、分散剂YUS-WP1、分散剂YUS-110、分散剂YUS-EP60P、分散剂YUS-CH1100、分散剂SP-OF3468、分散剂SP-OF3472、分散剂SP-2728、分散剂SP-SC29、分散剂Supragil MNS/90、分散剂Soprophor FD、分散剂YUS-FS1、分散剂YUS-PQ100、分散剂YUS-WG5、YUS-D935、辛基酚聚氧乙烯基醚硫酸盐、Morwet EFW、润湿剂Igepal BC/10、润湿剂GEROPONL-WET/P、润湿剂Rhodasurf 860/p、润湿剂SP-SC3266、润湿剂PICO-SW2、润湿剂PICO-SW3、润湿剂YUS-LXC、润湿剂YUS-204、烷基醇聚氧乙烯基醚硫酸钠、烷基酚聚氧乙烯基醚甲醛缩合物硫酸盐、烷基丁二酸磺酸盐、十二烷基苯磺酸钠、十二烷基硫酸钠、十二烷基苯磺酸钙等。
本发明通式I化合物的杀菌制剂中适宜的液体载体可以是水、有机溶剂、油性介质中的一种或几种。适宜的有机溶剂选自芳烃、氯代芳烃、脂族烃、氯代脂族烃、醇类以及它们的醚和酯、酮类等,例如苯、二甲苯、甲苯、烷基苯、烷基萘、氯代苯、氯乙烯、三氯乙烷、二氯甲烷、氯仿、四氯化碳、多氯乙烷、石油馏分、环己烷、甲醇、乙醇、异丙醇、丁醇、乙二醇、丙二醇、丙三醇、山梨醇、苯甲醇、糠醇、环己醇、丙酮、甲乙酮、甲基异丁基酮、环己酮、N-甲基-吡咯烷酮、磷酸三丁酯、二甲基甲酰胺和二甲基亚砜等。适宜的油性介质选自大豆油、油酸甲酯、轻质矿物油、液体石蜡、煤油、松节油等。
本发明通式I化合物的杀菌制剂中适宜的固体载体包括天然的或合成的。可选自但不限于粘土、岩石粉末、白垩、石英、粘土、蒙脱土、硫酸钠、二氧化硅、硅藻土、浮石、石膏、滑石、膨润土、高岭土、凹凸棒土、轻质碳酸钙、陶土、蒙脱土、硅酸铝镁、活性白土、白碳黑、硫酸铵、苯并呋喃树脂、过磷酸盐、氧化铝、方解石、大理石、浮石等,合适的颗粒载体包括破碎的和分级的天然岩石例如海泡石和白云石和由有机和无机的粉末制成的合成颗粒。
适宜的粘合剂、增稠剂包括合成的或天然的水溶性聚合物。可选自但不限于羰甲基醇、聚乙烯醇、聚乙酸乙烯酯、黄原胶、明胶、阿拉伯树胶、聚乙烯吡咯烷酮、硅酸镁铝、聚乙烯醇、聚乙二醇、酚醛树脂、虫胶、甲基纤维素、可溶性淀粉、羧甲基纤维素和海藻酸钠等,以粉末、颗粒或胶乳形式加入制剂中。
适宜的消泡剂可选自但不限于消泡剂SAG1522、硅酮类、C8~10脂肪醇、磷酸酯类、
C10~20饱和脂肪酸类(如癸酸)及酰胺等。
适宜的防冻剂可选自但不限于乙醇、异丙醇、乙二醇、丙二醇、丙三醇、二甘醇、乙二醇丁醚、丙二醇丁醚、乙二醇丁醚乙酸酯、尿素等。
适宜的渗透剂可选自但不限于有机硅、渗透剂T、渗透剂JFC等。
适宜的成膜剂包括天然产物及其改性物和人工合成高分子。可选自但不限于羧甲基淀粉钠、可溶性淀粉、磷酸化淀粉、氧化淀粉、壳聚糖及其衍生物、聚丙烯接枝共聚物、黄原胶、海藻酸钠、琼脂、明胶、阿拉伯胶、聚乙二醇、聚乙烯醇、聚醋酸乙烯酯、聚丙烯酰胺、聚乙烯吡咯烷酮、聚丙烯酸等。
适宜的防腐剂可选自但不限于苯甲酸钠、卡松、山梨酸钾等。
适宜的崩解剂可选自但不限于羧甲基淀粉钠、交联羧甲基淀粉钠、交联羧甲基纤维素钠、改性淀粉、交联聚乙烯吡咯烷酮、硫酸铵、硫酸钠、氯化钠、氯化铵等。
泡腾崩解剂可为酸性组分和/或碱性组分,其中酸性组分可选自有机酸、无机酸,例
如:酒石酸、柠檬酸、水杨酸、磷酸等;碱性组分可选自碱式碳酸盐、碳酸盐,例如:碳酸氢钠、碳酸钠、碳酸氢钾、碳酸钾、碳酸氢铵等。
适宜的警戒色可选自但不限于无机颜料,如氧化铁、氧化钛或普鲁士兰;有机染料,如阿利札林、酸性大红G、碱性玫瑰精、偶氮染料、金属酞菁等。
适宜的壁材包括天然高分子材料、半合成高分子材料和全合成高分子材料中的一种或几种。天然高分子材料可选自但不限于明胶、阿拉伯胶、琼脂、海藻酸盐、壳聚糖、纤维蛋白、玉米蛋白等;半合成高分子材料可选自但不限于甲(乙)基纤维素、羧甲基纤维素(钠)、醋酸纤维素及其酯类和部分甘油酯等;全合成高分子材料可选自但不限于聚丙烯酸树酯、脲醛树脂、聚酰胺、聚酯、聚甲基丙烯酸甲酯、聚脲、聚氨酯等。
适宜的固化剂包括多元醇、多元胺中的一种或几种。多元醇可选自但不限于乙二醇、丙三醇、1,2-丙二醇、1,4-丁二醇、二乙二醇、聚乙二醇200、聚乙二醇400、聚乙二醇600等;多元胺可选自但不限于乙二胺、丙二胺、己二胺、二乙烯三胺、三乙烯四胺、乙醇胺、二乙醇胺、三乙醇胺、六亚甲基四胺、异佛尔酮二胺等。
下面为制剂制备实例:
微囊悬浮剂:将5份活性化合物、5份600#、10份二甲苯、1份二苯基甲烷二异氰酸酯搅拌均匀制成油相,然后将其加入到由1份乙二胺、5份丙三醇、3份Atlox 4913、2份EFW和1份SAG1522、水余量组成的水相中,经高速搅拌、固化、保温即可制得5%活性化合物微囊悬浮剂。
乳油:将10份活性化合物、5份0201B、7份0203B、溶剂油150补足至100%加入混合釜中,搅拌混合均匀,必要时用热水浴加热溶解,即可得到10%活性化合物乳油。
水乳剂:将15份活性化合物、8份T-20、4份农乳S-85、5份磷酸三丁酯、5份溶剂油200加入混合釜中,搅拌混合,使溶解成均匀油相,在高速搅拌下,将余量水(补足至100%)加入到油相,即可得到分散性良好的15%活性化合物水乳剂。
可分散油悬浮剂:将25份活性化合物、6份分散剂SP-OF3468、6份分散剂SP-OF3472、2份农乳1601#、2份有机膨润土、油酸甲酯补足至100%依次加入到混合罐中混合,先经过高剪切进行粗粉碎、匀化,然后抽入到砂磨机中进行细磨,用粒度分布仪检测砂磨物料的粒度,当粒径达到标准要求后,过滤,即可得到25%活性化合物可分散油悬浮剂。
水分散粒剂:将60份活性化合物、2份Morwet EFW、4份分散剂D425、4份烷基萘磺酸盐甲醛缩合物、10份可溶性淀粉、8份硫酸胺、硅藻土补足至100%加在一起,进行混合粉碎,再经加水捏合后,加入装有一定规格筛网的造粒机中进行造粒。然后再经干燥、筛分(按筛网范围),即可得到60%活性化合物水分散粒剂。
可湿性粉剂:将50份活性化合物、3份十二烷基硫酸钠、4份烷基萘磺酸缩聚物的钠盐、4份亚甲基萘磺酸钠、4份木质素磺酸钠、5份白碳黑、硅藻土补足至100%充分混合,经超细粉碎机粉碎后,即得到50%活性化合物可湿性粉剂。
微乳剂:将10份活性化合物、6份农乳0201B、2份NP-15、8份YUS-A51G、5份甲醇、
5份环己酮加在一起,使其溶解成均匀油相,余量用水补足至100%,在高速搅拌下,将水相加入到油相或将油相加入到水相,形成分散性良好的10%活性化合物微乳剂。
可溶液剂:将10份活性化合物、6份三苯乙烯基酚聚氧乙烯(n20)醚磷酸化三乙醇胺盐、3份农乳T-20、2份农乳0201B、3份N-甲基吡咯烷酮、环己酮补足至100%混合均匀,必要时用热水浴加热溶解,可制得10%活性化合物可溶液剂。
可乳化粉剂:将15份活性化合物、2份农乳1601#、3份500#、5份农乳0201B、5份N-甲基吡咯烷酮、5份Armid FMPC加入混合釜中,搅拌混合均匀,必要时用热水浴加热溶解,在搅拌条件下,将上述油基均匀喷雾到由20份白炭黑、膨润土补足至100%组成的混合物上,经超细粉碎机粉碎后,即得到15%活性化合物可乳化粉剂。
悬浮剂:将20份活性化合物、2份分散剂4913、2份润湿剂TXC、2份农乳1601#、2份白炭黑、0.2份黄原胶、1份SAG1522、5份乙二醇、水补足至100%依次加入到混合罐中混合,先经过高剪切进行粗粉碎、匀化,然后抽入到砂磨机中进行细磨,用粒度分布仪检测砂磨物料的粒度,当粒径达到标准要求后,过滤,即可得到20%活性化合物悬浮剂。
干悬浮剂:将50份活性化合物、20份木质素磺酸钠、2份润湿剂TXC、2份白炭黑、高岭土补足至100%依次加入到混合罐中与水混合,先经过高剪切进行粗粉碎、匀化,然后抽入到砂磨机中进行细磨,用粒度分布仪检测砂磨物料的粒度,喷雾造粒,干燥,即可得到50%活性化合物干悬浮剂。
超低容量剂:将10份活性化合物、5份Armid FMPC、2份农乳0201B、1份S-80、溶剂油补足至100%加入混合釜中,搅拌混合均匀,必要时用热水浴加热溶解,即可得到10%活性化合物超低容量剂。
悬浮种衣剂:将10份活性化合物、2份分散剂FS3000、2份润湿剂TXC、2份SK-92FS1、2份白炭黑、0.2份黄原胶、10份10%聚乙烯醇溶液、0.2份碱性玫瑰精、1份SAG1522、5份乙二醇、水补足至100%依次加入到混合罐中混合,先经过高剪切进行粗粉碎、匀化,然后抽入到砂磨机中进行细磨,用粒度分布仪检测砂磨物料的粒度,当粒径达到标准要求后,过滤,即可得到10%活性化合物悬浮种衣剂。
粉剂:将30份活性化合物、5份亚甲基萘磺酸钠、6份木质素磺酸钠、8份白碳黑、硅藻土补足至100%充分混合,经超细粉碎机粉碎后,即得到30%活性化合物粉剂。
可溶性粉剂:将50份活性化合物、3份十二烷基硫酸钠、4份烷基萘磺酸缩聚物的钠盐、4份EFW、5份羟丙基纤维素、硫酸铵补足至100%充分混合,经超细粉碎机粉碎后,即得到50%活性化合物可溶性粉剂。
片剂:将10份活性化合物、2份甲基萘磺酸钠甲醛缩合物、1份十二烷基硫酸
钠、15份可溶性淀粉、8份硫酸钠、5份白碳黑、硅藻土补足至100%充分混合,经超细粉
碎机粉碎后,压片,即可得到10%活性化合物片剂。
颗粒剂:将10份活性化合物、3份甲基萘磺酸钠甲醛缩合物、2份烷基萘磺酸缩聚物的钠盐、10份硫酸钠、硅藻土补足至100%加在一起,进行混合粉碎,再经加水捏合后,加入装有一定规格筛网的造粒机中进行造粒。然后再经干燥、筛分(按筛网范围),即可得到10%活性化合物颗粒剂。
泡腾粒剂:将20份活性化合物、4份烷基萘磺酸缩聚物的钠盐、2份甲基萘磺酸钠甲醛缩合物、2份十二烷基硫酸钠、20份可溶性淀粉、15份柠檬酸钠、15份碳酸氢钠、10份硫酸钠、硅藻土补足至100%充分混合,经超细粉碎机粉碎后,再经捏合、造粒,即可得到20%活性化合物泡腾粒剂。
可乳化粒剂:将20份活性化合物、1份农乳EL-40、3份OX-2681、4份农乳0201B、2份农乳700#、3份N-甲基吡咯烷酮、3份Armid FMPC加入混合釜中,搅拌混合均匀,必要时用热水浴加热溶解,在搅拌条件下,将上述油基均匀喷雾到由25份白炭黑、轻质碳酸钙补足至100%组成的混合物上,经超细粉碎机粉碎后,再经加水捏合后,加入装有一定规格筛网的造粒机中进行造粒。然后再经干燥、筛分(按筛网范围),即可得到20%活性化合物可乳化粒剂。
可溶性片剂:将20份活性化合物、3份润湿剂TXC、4份烷基萘磺酸缩聚物的钠盐、4份EFW、5份羟丙基纤维素、硫酸铵补足至100%充分混合,经超细粉碎机粉碎后,压片,即得到20%活性化合物可溶性片剂。
微囊粒剂:在1000毫升塑料(带挡板)瓶中,加入600毫升的0 .5%聚乙烯醇水溶液,用四氟乙烯搅拌器,在高速搅拌下加入40份活性化合物、9克环氧乙烷环氧丙烷嵌段共聚物、6克环氧化大豆油、3克二苯基甲烷-4 ,4-二异氰酸酯、1.5克乙二胺、5克碳酸钠和150毫升水,加料完毕后,减慢速度继续搅拌1小时,静置1小时,过滤,真空干燥,即得40%活性化合物微囊粒剂。
泡腾片剂:将10份活性化合物、4份木质素磺酸钠、4份NNO、2份十二烷基硫酸钠、20份可溶性淀粉、20份柠檬酸钠、20份碳酸氢钠、10份硫酸钠、煅烧高岭土补足至100%充分混合,经超细粉碎机粉碎后,再经捏合、压片,即可得到10%活性化合物泡腾片剂。
漂浮粒剂:将15份活性化合物、4份D425、2份EFW、2份十二烷基硫酸钠、20份玉米淀粉、20份漂珠、5份白炭黑、10份硫酸钠、硅藻土补足至100%充分混合,经超细粉碎机粉碎后,再经捏合、造粒,即可得到15%活性化合物漂浮粒剂。
可溶性粒剂:将30份活性化合物、3份润湿剂TXC、4份烷基萘磺酸缩聚物的钠盐、4份十二烷基硫酸钠、5份羧甲基纤维素、5份葡萄糖、硫酸铵补足至100%充分混合,经超细粉碎机粉碎后,捏合、造粒,即得到30%活性化合物可溶性粒剂。
本发明通式I化合物的杀菌制剂在使用前可以由使用者经稀释或直接兑水喷雾,也可以直接使用。
本发明的技术方案还包括防治病菌的方法:将本发明的杀菌剂施于所述的病菌或其生长介质上。通常选择的较为适宜有效量为每公顷10克到1000克,优选有效量为每公顷10克到500克。
应明确的是,在本发明的权利要求所限定的范围内,可进行各种变换和改动。
具体实施方式
以下具体实施例用来进一步说明本发明,但本发明绝非限于这些例子。(除另有注明外,所用原料均有市售)
合成实施例
按照上述记载的合成路线,采用不同的原料化合物,即可分别制备获得本发明通式I所示化合物,进一步具体描述如下:
实施例1:化合物1.17的制备
50毫升反应瓶中加入对氯苯腈(0.35克, 2.55毫摩尔)、丙二腈肟醚钠盐(0.34克,2.91毫摩尔)和20毫升N-甲基吡咯烷酮,升温回流搅拌反应。TLC监测,待反应完成后,加入适量乙酸乙酯和水进行萃取,有机层减压浓缩、干燥、柱层析纯化后得白色固体0.31克。
实施例2:化合物1.149的制备
50毫升反应瓶中加入1-氯-2, 4-二硝基苯(0.41克,2.03毫摩尔)、丙二腈肟醚钠盐(0.26克, 2.22毫摩尔)和20毫升乙腈,室温下搅拌反应。TLC监测,待反应完成后,减压蒸除乙腈,残余物柱层析纯化后得白色固体0.38克。
实施例3:化合物1.237的制备
50毫升反应瓶中加入2-氯-5-硝基苯腈(0.29克, 1.59毫摩尔)、丙二腈肟醚钠盐(0.20克, 1.71毫摩尔)和20毫升乙腈,升温回流搅拌反应。TLC监测,待反应完成后,减压蒸除乙腈,残余物柱层析纯化后得黄色固体0.25克。
实施例4:化合物1.387的制备
50毫升反应瓶中加入3-氯-N-(3-氯-2,6-二硝基-4-三氟甲基苯基)-5-三氟甲基-2-吡啶胺(0.84克,1.80毫摩尔)、丙二腈肟醚钠盐(0.25克,2.14毫摩尔)和20毫升乙腈,室温搅拌反应。TLC监测,待反应完成后,减压蒸除乙腈,残余物柱层析纯化后得白色固体0.81克。
参照以上具体实施例以及发明内容中记载的方法可以制备本发明通式I中其它化合物。
生物活性测定
实施例5:对稻瘟病或灰霉病生物活性测定
离体杀菌活性测定:采用高通量筛选方法,即将通式I化合物样品用适合的溶剂(溶剂的种类如丙酮、甲醇、DMF等,并且依据其对样品的溶解能力而选择)溶解,配制成所需浓度待测液。在超净工作环境下,将待测液加入到96孔培养板的微孔中,再将病原菌繁殖体悬浮液加入其中,处理后的培养板放置在恒温培养箱中培养。24小时后进行调查,调查时目测病原菌繁殖体萌发或生长情况,并根据对照处理的萌发或生长情况,评价化合物抑菌活性。
测试结果如下:
25 mg/L时,化合物1.149、1.237、1.240对稻瘟病菌孢子萌发抑制率为100%。
25 mg/L时,化合物1.387对蔬菜灰霉病孢子萌发抑制率为100%。
实施例6:对甜瓜果斑病、大白菜软腐病、黄瓜细菌性角斑病、番茄细菌性叶斑病、水稻细菌性条斑病、水稻白叶枯病及柑橘溃疡病防治效果的测定
用本发明的化合物对多种植物细菌性病害进行了防效测定,针对不同的细菌性病害,试验程序如下:
甜瓜果斑病:将待测化合物用少量N, N二甲基甲酰胺溶解,用水稀释至所需要的浓度。将培养至稳定生长期的病原细菌与定量化合物溶液混合均匀,将经过催芽的甜瓜种子放入菌液与化合物的混合液中浸泡半小时,再将种子播种于蚯蚓土培养杯中,放入温室中保湿培养,一般培养两周时间,待对照充分发病后进行防效调查。
大白菜软腐病:切取2厘米见方的白菜叶片,放入垫有双层滤纸的玻璃培养皿中。将用N, N二甲基甲酰胺溶解,并用水稀释至所需浓度的化合物喷雾于白菜叶片表面,于通风橱内晾干白菜叶片表面药液后,使用接种针在白菜叶片表面针刺造成伤口,将培养至稳定生长期的大白菜软腐病菌取5微升加入伤口内,进行接种。最后将试材放入培养箱中避光培养48小时,待对照充分发病后进行防效调查。
黄瓜细菌性角斑病、番茄细菌性叶斑病、水稻细菌性条斑病、水稻白叶枯病:将待测化合物用少量N, N二甲基甲酰胺溶解,用水稀释至所需要的浓度。将化合物其喷雾于植物试材表面,于阴凉处风干表面药液后,将培养至稳定生长期的病原细菌菌液喷雾接种于植物试材表面,然后将植物试材放入温室中保湿培养。通常培养十天左右,待对照充分发病后,进行防效调查。
柑桔溃疡病:试验设处理和对照,每个处理10次重复,每个重复1张叶片,使用接种针在柑橘离体叶片上造成8-10个针刺点;用无菌水将药剂原液(即将待测化合物用少量N,N二甲基甲酰胺溶解)稀释至所需浓度后对柑橘离体叶片进行叶面喷施,再接种病原菌,处理完成后置于90mm培养皿中(用适量无菌水润湿吸水纸,置于培养皿底部进行保湿),于28℃恒温箱内培养,7天后观察并记录柑橘溃疡病的离体发病情况,进行防效调查。防治效果(%)=(对照针刺发病点数-处理针刺发病点数)/对照针刺发病点数×100%。
测试结果如下:
600 mg/L时,化合物1.17、1.18、1.149、1.237、1.240、1.274、1.276、1.369、1.386、1.387对甜瓜果斑病的防效为100%。
400mg/L时,化合物1.17、1.18、1.149、1.237、1.240、1.274、1.276、1.369、1.386、1.387对黄瓜细菌性角斑病、水稻细菌性条斑病、水稻白叶枯病、大白菜软腐病和番茄细菌性叶斑病的防效为100%。
100mg/L时,化合物1.17、1.18、1.149、1.237、1.240、1.274、1.276、1.369、1.386、1.387对柑橘溃疡病的防效为100%。
Claims (10)
1.一种1,1-二氰基肟醚类化合物,其特征在于,化合物如通式I所示:
式中:
W选自W1;
X1、X2、X3、X4、X5各自独立地选自氢、卤素、氰基、硝基、-ON=C(CN)2、(3-氯-5-(三氟甲基)吡啶-2-基)氨基、C1-C8烷基、卤代C1-C8烷基、C1-C8烷氧基、卤代C1-C8烷氧基;但,当X2、X4、X5选自氢时,X1、X3不选自硝基;
或通式I化合物的盐。
2.根据权利要求1所述的化合物,其特征在于,通式I中,
W选自W1;
X1、X2、X3、X4、X5各自独立地选自氢、卤素、氰基、硝基、-ON=C(CN)2、(3-氯-5-(三氟甲基)吡啶-2-基)氨基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基;但,当X2、X4、X5选自氢时,X1、X3不选自硝基;
或通式I化合物与盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸形成的盐。
3.根据权利要求2所述的化合物,其特征在于,通式I中,
W选自W1;
X1、X2、X3、X4、X5各自独立地选自氢、氟、氯、溴、氰基、硝基、-ON=C(CN)2、(3-氯-5-(三氟甲基)吡啶-2-基)氨基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、一氯甲基、二氯甲基、三氯甲基、一溴甲基、二溴甲基、三溴甲基、一氟甲基、二氟甲基、三氟甲基、2,2,2-三氟乙基、七氟异丙基、甲氧基、乙氧基、正丙氧基、异丙氧基、二氟甲氧基、三氟甲氧基;但,当X2、X4、X5选自氢时,X1、X3不选自硝基;
或通式I化合物与盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸形成的盐。
4.根据权利要求3所述的化合物,其特征在于,通式I中,
W选自W1,X1选自氰基或硝基,X2、X3、X4、X5选自氢;
或者,W选自W1,X2选自氰基或硝基,X1、X3、X4、X5选自氢;
或者,W选自W1,X3选自氰基或硝基,X1、X2、X4、X5选自氢;
或者,W选自W1,X1选自氰基,X3选自氰基或硝基,X2、X4、X5选自氢;
或者,W选自W1,X1选自硝基,X3选自氰基,X2、X4、X5选自氢;
或者,W选自W1,X2选自氰基,X3选自氰基或硝基,X1、X4、X5选自氢;
或者,W选自W1,X2选自硝基,X3选自氰基或硝基,X1、X4、X5选自氢;
或者,W选自W1,X2选自氰基,X4选自氰基或硝基,X1、X3、X5选自氢;
或者,W选自W1,X2选自硝基,X4选自氰基或硝基,X1、X3、X5选自氢;
或者,W选自W1,X2选自氯,X3选自氰基或硝基,X1、X4、X5选自氢;
或者,W选自W1,X1、X3选自硝基,X4选自氯,X2、X5选自氢;
或者,W选自W1,X1、X3选自硝基,X4选自-ON=C(CN)2,X2、X5选自氢;
或者,W选自W1,X1、X3选自硝基,X2选自(3-氯-5-(三氟甲基)吡啶-2-基)氨基,X5选自三氟甲基,X4选自氢;
或通式I化合物与盐酸、氢溴酸、硫酸、磷酸、甲酸、乙酸、丙酸、丁酸、戊酸、三氟乙酸、草酸、丙二酸、甲磺酸、4-甲苯磺酸、苹果酸、富马酸、乳酸、马来酸、水杨酸、酒石酸或柠檬酸形成的盐。
5.根据权利要求1所述的化合物,其特征在于,所述化合物通式I化合物选自如下化合物:
6.一种按照权利要求1所述的通式I化合物在农业、林业或卫生领域中作为杀真菌剂或杀细菌剂的用途。
7.一种按照权利要求1所述的通式I化合物用于控制植物细菌性病害的用途。
8.根据权利要求7所述的通式I化合物用于控制植物细菌性病害的用途,其特征在于:所述植物细菌性病害为果斑病、叶斑病、青枯病、细菌性疫病、溃疡病、软腐病、细菌性角斑病、细菌性条斑病、叶枯病、白叶枯病、野火病或细菌性疮痂病。
9.一种杀菌组合物,其特征在于:组合物中含有权利要求1所述的通式I化合物和农业上可接受的载体,组合物中活性组分的重量百分含量为0.1-99%。
10.一种防治病菌的方法,其特征在于:向作物或作物的生长介质或地点上施用杀菌有效剂量的如权利要求9所述的杀菌组合物。
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