CN1927838A - Compound of N-(substituted pyridyl)amide, preparation and application thereof - Google Patents

Compound of N-(substituted pyridyl)amide, preparation and application thereof Download PDF

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CN1927838A
CN1927838A CN 200510047150 CN200510047150A CN1927838A CN 1927838 A CN1927838 A CN 1927838A CN 200510047150 CN200510047150 CN 200510047150 CN 200510047150 A CN200510047150 A CN 200510047150A CN 1927838 A CN1927838 A CN 1927838A
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alkyl
compound
general formula
alkoxy
alkoxyl group
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CN100467451C (en
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刘长令
迟会伟
李志念
欧阳津
罗艳梅
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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Shenyang Research Institute of Chemical Industry Co Ltd
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Abstract

The present invention belongs to the field of farm germicide, and is especially one kind of N-(substitutional pyridyl) amide compounds with general expression as shown and its preparation and application. The compounds have broad spectrum germicidal activity of preventing rice blast, wheat powdery mildew, cucumber powdery mildew, cucumber gray mold, etc, especially on powdery mildew.

Description

N-(pyridine of replacement) amides and preparation thereof and application
Technical field
The invention belongs to the disinfectant use in agriculture field, relate to a kind of N-(pyridine of replacement) amides and preparation thereof and application particularly.
Background technology
Pyridine is crucial heterocycle in pesticide developing, because pyridine ring has character such as good interior absorption, hydrophobicity, selectivity, so its introducing can make the performance of compound obtain changing.Although the commercialization kind (referring to Clive Tomlin, The Pesticide Manual, 13th ed.2003) that much contains the pyridine group is arranged, still need the compound of novel structure.
Patent US6316632B1 report has the preparation technology of the compound of following general formula, but does not have the biological activity report.
Patent WO9845268A1, WO0023420A1 has also reported relevant pyridyl amine derivative among the EP527016A1 etc., but all with the present invention tangible difference is arranged, and does not influence this patent.
Summary of the invention
The object of the present invention is to provide a kind of new N-(pyridine of replacement) amides, it can be applicable to the disease that agricultural goes up the control crop.
Technical scheme of the present invention is as follows:
The invention provides a kind of N-(pyridine of replacement) amides, shown in general formula (I):
In the formula: R 1, R 2, R 3Can be identical or different, be selected from hydrogen, halogen, cyano group, nitro, C respectively 1-C 12Alkyl, C 2-C 12Thiazolinyl, C 2-C 12Alkynyl, C 1-C 12Haloalkyl, C 1-C 12Alkoxyl group, C 1-C 12Halogenated alkoxy, C 1-C 12Alkylthio, C 1-C 12Alkane alkylsulfonyl, C 1-C 12Alkyl-carbonyl, C 1-C 12Alkoxy C 1-C 12Alkyl, C 1-C 12Alkoxy carbonyl, C 1-C 12Alkoxy carbonyl C 1-C 12Alkyl, C 1-C 12Halogenated alkoxy C 1-C 12Alkyl, replace or one of unsubstituted following radicals arbitrarily: amido C 1-C 12Alkyl, aryl, heteroaryl, aryloxy, aryl C 1-C 12Alkyl, aryl C 1-C 12Alkoxyl group, heteroaryl C 1-C 12Alkyl, heteroaryl C 1-C 12Alkoxyl group; Ar is selected from any replacement or unsubstituted aryl, heteroaryl or aryloxy C 1-C 12Alkyl;
And steric isomer.
Comparatively preferred compound is among the present invention: R in the general formula (I) 1, R 2, R 3Can be identical or different, be selected from hydrogen, halogen, cyano group, nitro, C respectively 1-C 6Alkyl, C 2-C 6Thiazolinyl, C 2-C 6Alkynyl, C 1-C 6Haloalkyl, C 1-C 6Alkoxyl group, C 1-C 6Halogenated alkoxy, C1-C6 alkylthio, C1-C6 alkane alkylsulfonyl, C 1-C 6Alkyl-carbonyl, C 1-C 6Alkoxy C 1-C 6Alkyl, C 1-C 6Alkoxy carbonyl, C 1-C 6Alkoxy carbonyl C 1-C 6Alkyl, C 1-C 6Halogenated alkoxy C 1-C 6Alkyl; That can be replaced by alkyl, alkoxyl group, haloalkyl, halogenated alkoxy, halogen, nitro or cyano group or do not replace one of following radicals: amido C 1-C 6Alkyl, aryl, heteroaryl, aryloxy, aryl C 1-C 6Alkyl, aryl C 1-C 6Alkoxyl group, heteroaryl C 1-C 6Alkyl, heteroaryl C 1-C 6Alkoxyl group; Ar is selected from and replaces or unsubstituted aryl, heteroaryl or aryloxy C 1-C 6Alkyl.
Further preferred compound is: R in the general formula (I) 1, R 2, R 3Can be identical or different, be selected from hydrogen, halogen, cyano group, nitro, C respectively 1-C 6Alkyl, C 2-C 6Thiazolinyl, C 2-C 6Alkynyl, C 1-C 6Haloalkyl, C 1-C 6Alkoxyl group, C 1-C 6Halogenated alkoxy, C 1-C 6Alkylthio, C 1-C 6Alkane alkylsulfonyl, C 1-C 6Alkyl-carbonyl, C 1-C 6Alkoxy C 1-C 6Alkyl, C 1-C 3Alkoxy carbonyl, C 1-C 6Alkoxy carbonyl C 1-C 3Alkyl, C 1-C 3Halogenated alkoxy C 1-C 3Alkyl, substituted amido C 1-C 3Alkyl, replacement or unsubstituted following radicals: phenyl, phenoxy group, benzyl or benzyloxy; Ar is selected from and replaces or unsubstituted phenyl, xenyl, pyridyl, pyrazolyl, thiazolyl or phenoxyalkyl.
Further preferred compound is: R in the general formula (I) 1, R 2, R 3Can be identical or different, be selected from hydrogen, chlorine, bromine, fluorine, cyano group or C respectively 1-C 3Alkyl, C 1-C 3Alkoxyl group, C 1-C 3Halogenated alkoxy, C 1-C 3Alkylthio, C 1-C 3Alkane alkylsulfonyl, C 1-C 3Alkoxy carbonyl, 0-5 the phenyl or the phenoxy group that replace; Ar is selected from Q as follows 1, Q 2, Q 3, Q 4, Q 5, Q 6, Q 7, Q 8, Q 9, Q 10, Q 11, Q 12, Q 13, Q 14, Q 15, Q 16, Q 17, Q 18, Q 19, Q 20, Q 21, Q 22, Q 23, Q 24Or Q 25:
Figure A20051004715000051
Preferred compound is: R in the general formula (I) 1, R 2, R 3Can be identical or different, be selected from hydrogen, chlorine, bromine, fluorine, cyano group or C respectively 1-C 3Alkyl, C 1-C 3Alkoxyl group, C 1-C 3Halogenated alkoxy, 0-3 the phenyl or the phenoxy group that replace; Ar is selected from Q 1, Q 2, Q 3, Q 4, Q 5, Q 6, Q 7, Q 8, Q 9, Q 10, Q 11, Q 12, Q 13, Q 14, Q 15Or Q 16
In the definition of the general formula that provides above (I) compound, compile the following substituting group of used term general proxy:
Substituting group is hydrogen, alkyl, alkoxyl group, haloalkyl, halogenated alkoxy, halogen, nitro, CN or the like in (replacement) phenoxy group, (replacement) benzyloxy, (replacement) phenyl, (replacement) benzyl, and substituent number can be 0～5.
Halogen: refer to fluorine, chlorine, bromine and iodine.
Alkyl: straight or branched alkyl, for example methyl, ethyl, propyl group, sec.-propyl and the tertiary butyl.
Haloalkyl: the straight or branched alkyl, the hydrogen atom on these alkyl can partly or entirely be replaced by halogen atom, for example, haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl.
Alkoxyl group: the straight or branched alkyl is connected on the structure through the Sauerstoffatom key.
Halogenated alkoxy: the straight or branched alkoxyl group, the hydrogen atom on these alkoxyl groups can partly or entirely be replaced by halogen atom.For example, halogenated alkoxy such as chlorine methoxyl group, dichloro methoxyl group, trichlorine methoxyl group, fluorine methoxyl group, difluoro-methoxy, trifluoromethoxy, chlorine fluorine methoxyl group.
Alkenyl: straight or branched also can have two key, for example vinyl, allyl groups on any position.The substituted alkenyl base comprises the aromatic yl alkenyl of any replacement.
Alkynyl: straight or branched also can have triple bond on any position, for example ethynyl, propargyl.Substituted alkynyl comprises the sweet-smelling alkynyl of any replacement.
Aryl moiety in aryl and aralkyl, aromatic yl alkenyl, sweet-smelling alkynyl, aryloxy and the aryloxy alkyl comprises phenyl and Nai Ji.
The indication heteroaryl is to contain one or more N, O, the heteroatomic 5 yuan of rings of S or 6 yuan of rings among the present invention.For example pyridine, furans, pyrimidine, pyrazine, pyridazine, triazine, quinoline, cumarone.
Can the present invention be described with the compound of listing in the following table 1, but not limit the present invention.
Table 1 compound table
Compound number R 1 R 2 R 3 Ar
1 Cl H H Q 1
2 Cl H H Q 2
3 Cl H H Q 3
4 Cl H H Q 7
5 Cl H H Q 8
6 Cl H H Q 9
7 Cl H H Q 5
8 Cl H H Q 6
9 Cl H H Q 16
10 Cl H H Q 10
11 Cl H H Q 11
12 Cl H H Q 12
13 Cl H H Q 13
14 Cl H H Q 14
15 Cl H H Q 15
16 Cl H H Q 17
17 Cl H H Q 18
18 Cl H H Q 19
19 Cl Cl H Q 2
20 Cl H Cl Q 2
21 Cl Cl H Q 1
22 Cl Cl H Q 5
23 Cl Cl H Q 6
24 Cl Cl H Q 7
25 Cl Cl H Q 8
26 Cl Cl H Q 9
27 Cl Cl H Q 10
28 Cl Cl H Q 15
29 Cl Cl H Q 17
30 Cl Cl H Q 18
31 Cl Cl H Q 19
32 OCH 2CF 3 H H Q 1
33 OCH 2CF 3 H H Q 4
34 OCH 2CF 3 H H Q 5
35 OCH 2CF 3 H H Q 6
36 OCH 2CF 3 H H Q 2
37 OCH 2CF 3 H H Q3
38 OCH 2CF 3 H H Q7
40 OCH 2CF 3 H H Q8
41 OCH 2CF 3 H H Q9
42 OCH 2CF 3 H H Q10
43 OCH 2CF 3 H H Q11
44 OCH 2CF 3 H H Q12
45 OCH 2CF 3 H H Q13
46 OCH 2CF 3 H H Q14
47 OCH 2CF 3 H H Q15
48 OCH 2CF 3 H H Q16
49 OCH 2CF 3 H H Q17
50 OCH 2CF 3 H H Q18
51 OCH 2CF 3 H H Q19
52 OCH 2CF 3 H H Q20
53 H H Cl Q 2
54 H H Cl Q 1
55 H Cl Cl Q 15
56 H H CN Q 16
57 H Cl CN Q 1
58 H OCH 3 H Q 2
59 H H OCH 3 Q 1
60 Ph H H Q 5
61 Ph H H Q 8
62 Ph H H Q 6
63 Ph H H Q 9
64 Ph H H Q 10
65 Ph H H Q 4
66 Ph H H Q 1
67 Ph H H Q 2
68 Ph H H Q 3
69 Ph H H Q 7
70 Ph H H Q 11
71 Ph H H Q 12
72 Ph H H Q 13
73 Ph H H Q 14
74 Ph H H Q 15
75 Ph H H Q 16
76 Ph H H Q 17
77 Ph H H Q 18
78 Ph H H Q 19
79 Ph H H Q 20
80 Ph-4-Cl H H Q 7
81 Ph-4-Cl H H Q 10
82 Ph-4-Cl H H Q 4
83 Ph-4-Cl H H Q 9
84 Ph-4-Cl H H Q 11
85 Ph-4-Cl H H Q 12
86 Ph-4-Cl H H Q 13
87 Ph-4-Cl H H Q 15
88 Ph-4-Cl H H Q 14
89 Ph-4-Cl H H Q 8
90 Ph-4-Cl H H Q 16
91 Ph-4-Cl H H Q 17
92 Ph-4-Cl H H Q 18
93 Ph-4-Cl H H Q 19
94 Ph-4-Cl H H Q 20
95 OPh-4-Cl H H Q 10
96 OPh-4-Cl H H Q 9
97 OPh-4-Cl H H Q 13
98 OPh-4-Cl H H Q 11
99 OPh-4-Cl H H Q 8
100 OPh-4-Cl H H Q 4
101 OPh-4-Cl H H Q 14
102 OPh-4-Cl H H Q 15
103 OPh-4-Cl H H Q 16
104 OPh-4-Cl H H Q 20
105 SC 3H 7 H H Q 1
106 SC 3H 7 H H Q 2
107 SC 3H 7 H H Q 15
108 SC 3H 7 H H Q 16
109 SC 3H 7 H H Q 3
110 SC 3H 7 H H Q 4
111 SC 3H 7 H H Q 5
112 SC 3H 7 H H Q 6
113 SC 3H 7 H H Q 7
114 SC 3H 7 H H Q 8
115 SC 3H 7 H H Q 9
116 SC 3H 7 H H Q 10
117 SC 3H 7 H H Q 11
118 SC 3H 7 H H Q 12
119 SC 3H 7 H H Q 13
120 SC 3H 7 H H Q 14
121 SC 3H 7 H H Q 17
122 SC 3H 7 H H Q 18
123 SC 3H 7 H H Q 19
124 SC 3H 7 H H Q 20
125 SC 3H 7 Cl H Q 1
126 SC 3H 7 CN Cl Q 1
127 SCH 3 H H Q 17
128 SCH 3 Cl H Q 18
129 SCH 3 Cl Cl Q 7
130 SO 2CH 3 H H Q 1
131 SO 2CH 3 H H Q 7
132 SO 2CH 3 H H Q 17
133 SO 2CH 3 H H Q 2
134 SO 2CH 3 H H Q 3
135 SO 2CH 3 H H Q 4
136 SO 2CH 3 H H Q 5
137 SO 2CH 3 H H Q 6
138 SO 2CH 3 H H Q 13
139 SO 2CH 3 H H Q 8
140 SO 2CH 3 H H Q 9
141 SO 2CH 3 H H Q 10
142 SO 2CH 3 H H Q 11
143 SO 2CH 3 H H Q 12
144 SO 2CH 3 H H Q 14
145 SO 2CH 3 H H Q 15
146 SO 2CH 3 H H Q 16
147 SO 2CH 3 H H Q 18
148 SO 2CH 3 H H Q 19
149 SO 2CH 3 H H Q 20
150 i-C 3H 7 H H Q 1
151 i-C 3H 7 H H Q 2
152 i-C 3H 7 H H Q 3
153 i-C 3H 7 H H Q 4
154 i-C 3H 7 H H Q 5
155 i-C 3H 7 H H Q 6
156 i-C 3H 7 H H Q 7
157 i-C 3H 7 H H Q 8
158 i-C 3H 7 H H Q 9
159 i-C 3H 7 H H Q 10
160 i-C 3H 7 H H Q 11
161 i-C 3H 7 H H Q 12
162 i-C 3H 7 H H Q 13
163 i-C 3H 7 H H Q 14
164 i-C 3H 7 H H Q 15
165 i-C 3H 7 H H Q 16
166 i-C 3H 7 H H Q 17
167 i-C 3H 7 H H Q 18
168 i-C 3H 7 H H Q 19
169 i-C 3H 7 H H Q 20
170 N(CH 3) 2 H H Q 1
171 N(CH 3) 2 H H Q 2
172 N(CH 3) 2 H H Q 3
173 N(CH 3) 2 H H Q 4
174 N(CH 3) 2 H H Q 5
175 N(CH 3) 2 H H Q 6
176 N(CH 3) 2 H H Q 7
177 N(CH 3) 2 H H Q 8
178 N(CH 3) 2 H H Q 9
179 N(CH 3) 2 H H Q 10
180 N(CH 3) 2 H H Q 11
181 N(CH 3) 2 H H Q 12
182 N(CH 3) 2 H H Q 13
183 N(CH 3) 2 H H Q 14
184 N(CH 3) 2 H H Q 15
185 N(CH 3) 2 H H Q 16
186 N(CH 3) 2 H H Q 17
187 N(CH 3) 2 H H Q 18
188 N(CH 3) 2 H H Q 19
189 N(CH 3) 2 H H Q 20
190 OPh H H Q 1
191 OPh H H Q 7
192 OPh H H Q 17
194 OPh H H Q 9
195 OPh-3-CF 3 H H Q1
196 OPh-3-CF 3 H H Q2
197 OPh-3-CF 3 H H Q3
198 OPh-3-CF 3 H H Q4
199 OPh-3-CF 3 H H Q5
200 OPh-3-CF 3 H H Q6
201 OPh-3-CF 3 H H Q7
202 OPh-3-CF 3 H H Q8
203 OPh-3-CF 3 H H Q9
204 OPh-3-CF 3 H H Q10
205 OPh-3-CF 3 H H Q11
206 OPh-3-CF 3 H H Q12
207 OPh-3-CF 3 H H Q13
208 OPh-3-CF 3 H H Q14
209 OPh-3-CF 3 H H Q15
210 OPh-3-CF 3 H H Q16
211 OPh-3-CF 3 H H Q17
212 OPh-3-CF 3 H H Q18
213 OPh-3-CF 3 H H Q19
214 OPh-3-CF 3 H H Q20
215 OPh-4-CF 3 H H Q1
216 OPh-4-CF 3 H H Q7
217 OPh-4-CF 3 H H Q9
218 OPh-4-CF 3 H H Q17
219 OPh-3，4-(OCH 3) 2 H H Q2
220 OPh-3，4-(OCH 3) 2 H H Q5
221 OPh-3，4-(OCH 3) 2 H H Q15
222 OPh-3，4-(OCH 3) 2 H H Q20
223 OPh-2，4-Cl 2 H H Q1
224 OPh-2，4-Cl 2 H H Q6
225 OPh-2，4-Cl 2 H H Q7
226 OPh-2，4-Cl 2 H H Q19
227 Ph-4-CF 3 H H Q4
228 Ph-4-CF 3 H H Q5
229 Ph-4-CF 3 H H Q16
230 Ph-4-CF 3 H H Q20
231 Ph-2，4-Cl 2 H H Q4
231 Ph-2，4-Cl 2 H H Q7
232 Ph-2，4-Cl 2 H H Q8
233 Ph-2，4-Cl 2 H H Q9
234 Ph-2，4-Cl 2 H H Q14
235 Ph-3，4-(OCH 3) 2 H H Q4
236 Ph-3，4-(OCH 3) 2 H H Q7
237 Ph-3，4-(OCH 3) 2 H H Q8
238 Ph-3，4-(OCH 3) 2 H H Q9
239 CO 2CH 3 H H Q1
240 CO 2CH 3 H H Q2
241 CO 2CH 3 H H Q3
242 CO 2CH 3 H H Q4
243 CO 2CH 3 H H Q5
244 CO 2CH 3 H H Q6
245 CO 2CH 3 H H Q7
246 CO 2CH 3 H H Q8
247 CO 2CH 3 H H Q9
248 CO 2CH 3 H H Q10
249 CO 2CH 3 H H Q11
250 CO 2CH 3 H H Q12
251 CO 2CH 3 H H Q13
252 CO 2CH 3 H H Q14
262 CO 2CH 3 H H Q15
263 CO 2CH 3 H H Q16
264 CO 2CH 3 H H Q17
265 CO 2CH 3 H H Q18
266 CO 2CH 3 H H Q19
267 CO 2CH 3 H H Q20
268 CN H H Q1
269 CN H H Q2
270 CN H H Q3
271 CN H H Q4
272 CN H H Q5
273 CN H H Q6
274 CN H H Q7
275 CN H H Q8
276 CN H H Q9
277 CN H H Q10
278 CN H H Q11
279 CN H H Q12
280 CN H H Q13
281 CN H H Q14
282 CN H H Q15
283 CN H H Q16
284 CN H H Q17
285 CN H H Q18
286 CN H H Q19
287 CN H H Q20
288 Cl H H Q21
289 Cl H H Q22
290 Cl H H Q23
291 Cl H H Q24
292 Cl H H Q25
293 OCH 2CF 3 H H Q21
294 OCH 2CF 3 H H Q22
295 OCH 2CF 3 H H Q23
296 OCH 2CF 3 H H Q24
297 OCH 2CF 3 H H Q25
298 Ph-4-Cl H H Q21
299 Ph-4-Cl H H Q22
300 Ph-4-Cl H H Q23
301 Ph-4-Cl H H Q24
302 OPh-4-Cl H H Q25
The present invention also comprises the preparation method of general formula (I) compound: reacted under alkaline condition, in organic solvent by the pyridyl amine compound of the replacement shown in the general formula (II) and the carboxylic acid halides shown in the general formula (III) and make.
In the formula, R 1, R 2, R 3With the definition of each group of Ar as mentioned above.
The reaction formula of preparation general formula (I) compound is as follows:
Figure A20051004715000132
React the optional methylene dichloride freely of used appropriate solvent, ethylene dichloride, tetrahydrofuran (THF), acetonitrile, toluene, dimethylbenzene or benzene etc.
The optional potassium hydroxide freely of suitable alkali, sodium hydroxide, yellow soda ash, salt of wormwood, sodium bicarbonate, triethylamine or pyridine etc.
Suitable temperature refers to room temperature to the solvent boiling point temperature, is generally 20～100 ℃.
Reaction times is 30 minutes to 10 hours, common 1～5 hour.
The pyridyl amine compound of the replacement shown in the general formula (II) partly has commercially available, also can be made by currently known methods, for example referring to Tetrahedron Letters, 1987,28,5093-5096; US6316632, US6511995, WO9845268A1 etc.; Perhaps also can utilize hoffman degradation reaction to obtain corresponding amine again by the carboxylic acid of correspondence through amidation.
Compound shown in the general formula (III) partly has commercially available, also can prepare by currently known methods, and for example referring to US4618366, US5438070, US5330995, US5589493, WO9845268A1 etc.; Also can make acyl chlorides according to ordinary method by corresponding carboxylic acid.
General formula of the present invention (I) compound has broad spectrum of activity---can be used for control on various crops by multiple germ diseases such as Oomycete, Basidiomycetes, ascomycetes and imperfect fungis, and because these compounds have very high biological activity makes just can obtain good effect under very low dosage.This compounds all has good preventive effect to diseases such as rice sheath blight disease, rice blast, wheat powdery mildew, powdery mildew of cucumber, cucumber downy mildew, gray molds of cucumber, especially Powdery Mildew is had excellent activity.Therefore technical scheme of the present invention also comprises the application of general formula (I) compound disease on the control crop.
The present invention also provides a kind of fungicidal composition, contains general formula (I) compound in the said composition, and the weight percentage of active ingredient is 0.1-99% in the composition.
Active ingredient in the composition of the present invention can be the simplification compound in general formula (I) compound or the mixture of several compounds.Also contain carrier in the composition.
Carrier system in the present composition satisfies the material of following condition: being convenient to be applied to pending site after it and activeconstituents are prepared, for example can be plant, seed or soil; Perhaps help storing, transport or operation.Carrier can be solid or liquid, comprises the material that is generally gas but has been compressed into liquid, and used carrier all can use in the preparation fungicidal composition usually.
Suitable solid carrier comprises natural and synthetic clay and silicate, for example diatomite, talcum, attapulgite, pure aluminium silicate (kaolin), montmorillonite and mica; Lime carbonate; Calcium sulfate; Ammonium sulfate; Synthetic silicon oxide and synthetic calcium silicate or pure aluminium silicate; Element such as carbon and sulphur; Natural and synthetic resin such as coumarone resin, polyvinyl chloride and styrene polymer and multipolymer; Solid polystream phenol; Pitch; Wax such as beeswax, paraffin.
Suitable liquid vehicle comprises water; Alcohol is as Virahol and ethanol; Ketone such as acetone, methyl ethyl ketone, methyl isopropyl Ketone, cyclohexyl ketone; Ether; Aromatic hydrocarbons such as benzene,toluene,xylene; Petroleum fractions such as kerosene and mineral oil; Hydrochloric ether such as tetracol phenixin, tetrachloroethylene and trieline.Usually, these mixtures of liquids also are suitable.
Fungicidal composition is processed into the form of enriched material usually and is used for transportation with this, by the user it is diluted before using.Having of a spot of supporting surfactant helps dilution.Like this, according to having preferably tensio-active agent of a kind of carrier in the composition of the present invention at least.For example composition can contain at least two kinds of carriers, and wherein at least a is tensio-active agent.
Tensio-active agent can be emulsifying agent, dispersion agent or wetting agent; It can be non-ionic or the ionic tensio-active agent.The example of suitable tensio-active agent comprises the sodium salt or the calcium salt of polyacrylic acid and lignosulfonic acid; Contain the lipid acid of at least 12 carbon atoms or the condenses of aliphatic amide or acid amides and oxyethane and/or propylene oxide in the molecule.The condenses of glycol, sorbyl alcohol, sucrose or pentaerythritol fatty ester and these esters and oxyethane and/or propylene oxide; Fatty Alcohol(C12-C14 and C12-C18) or alkylphenol such as paraoctyl phenol or to the condenses of octyl group cresylol and oxyethane and/or propylene oxide; The vitriol of these condensation products and sulfonate; In molecule, contain the sulfuric acid of 10 carbon atoms or the basic metal or the alkaline earth salt of sulphonate at least, particular certain cancers, sulfuric acid laurate sodium for example, the secondary alkyl ester sodium of sulfuric acid, the sulfonated castor oil sodium salt, alkyl aryl sulfonic acid ester sodium is as pelopon A.
Composition of the present invention can be processed into various formulations according to ordinary method, for example wettable powder, pulvis, granule or liquor, emulsible enriching agent, emulsion, suspension enriching agent, aerosol or smoke substance.Wettable powder contains 25,50 or 75% weight activeconstituents usually, and usually except that solid inert carrier, also contains the dispersion agent of 3-10% weight, and if needs to add stablizer and/or other additive such as the permeate agent or the tackiness agent of 0-10% weight.Pulvis may be molded to the pulvis enriching agent that has the composition similar to wettable powder but do not have dispersion agent usually, further with the solid carrier dilution, is contained the composition of 0.5-10% weight active ingredient usually again.Granula is prepared into usually has 10 to 100 order (1.676-0.152mm) sizes, and available agglomerating or implantttion technique preparation.Usually granula contains the activeconstituents of 0.5-75% weight and 0-10% weight additive such as stablizer, tensio-active agent, slowly-releasing modifying agent.So-called " dry powder can flow " is by the relatively little granulometric composition with relative high density activeconstituents.Outside but emulsion concentrate desolventizes, when needs, contain cosolvent usually, 1-50%W/V activeconstituents, other additives of 2-20%W/V emulsifying agent and 0-20%W/V such as stablizer, permeate agent and corrosion inhibitor.The suspension enriching agent contains the activeconstituents of 10-75% weight, the dispersion agent of 0.5-15% weight, other additive such as defoamer, corrosion inhibitor, stablizer, permeate agent and the tackiness agent of 0.1-10% weight usually.
Water dispersant and emulsion, for example by dilute with water according to the composition that wettable powder of the present invention or enriched material obtain, also list the scope of the invention in.Said emulsion can have water-in-oil or two types of oil-in-water.
By in composition, adding other one or more sterilant, make it have the more activity of wide spectrum than independent general formula (I) compound.In addition, but the fungicidal activity of other sterilant mutual-through type (I) compounds has synergism.
Embodiment
Below concrete example be used for further specifying the present invention, but do not limit the present invention.
Synthetic embodiment
Example 1: the preparation of compound 1
Under the room temperature, in 20 milliliters of dichloromethane solutions that contain 0.6 gram triethylamine, 0.64 gram (II-1), drip 1.1 grams (III-1), stirring reaction 5 hours.With the reaction mixture concentrating under reduced pressure, in resistates, add saturated sodium bicarbonate aqueous solution, ethyl acetate extraction 3 times, combining extraction liquid, saturated common salt washing 3 times, drying is filtered, concentrating under reduced pressure, getting faint yellow solid is thick product.Mixed solution (1: 4) column chromatography with ethyl acetate and sherwood oil obtains title compound 0.98 gram, fusing point 82-84 ℃.Yield 70.5%.
Nuclear magnetic data ( 1HNMR, 300MHz, interior mark TMS, solvent C DCl 3) as follows: δ ppm 7.22 (1H, m), 7.40 (2H, d), 7.45 (3H, m), 7.55 (4H, m), 7.86 (1H, d), 8.02 (1H, d), 8.83 (1H, d).
Example 2: the preparation of compound 32
Figure A20051004715000161
Under the room temperature, in 20 milliliters of dichloromethane solutions that contain 0.6 gram triethylamine, 0.96 gram (II-32), drip 1.1 grams (III-1), stirring reaction 6 hours.With the reaction mixture concentrating under reduced pressure, in resistates, add saturated sodium bicarbonate aqueous solution, ethyl acetate extraction 3 times, combining extraction liquid, saturated common salt washing 3 times, drying is filtered, concentrating under reduced pressure, getting faint yellow solid is thick product.Mixed solution (1: 4) column chromatography with ethyl acetate and sherwood oil obtains title compound 1.28 grams, fusing point 69-71 ℃.Yield 68.5%.
Nuclear magnetic data ( 1HNMR, 300MHz, interior mark TMS, solvent C DCl 3) as follows: δ ppm 4.61 (2H, m), 6.96 (1H, m), 7.36 (2H, t), 7.42 (3H, m), 7.56 (4H, m), 7.76 (1H, dd), 7.83 (1H, dd), 8.75 (1H, d).
Example 3: the preparation of compound 96
Under the room temperature, in 20 milliliters of dichloromethane solutions that contain 0.6 gram triethylamine, 1.11 grams (II-96), drip 0.9 gram (III-96), stirring reaction 8 hours.With the reaction mixture concentrating under reduced pressure, in resistates, add saturated sodium bicarbonate aqueous solution, ethyl acetate extraction 3 times, combining extraction liquid, saturated common salt washing 3 times, drying is filtered, concentrating under reduced pressure, getting faint yellow solid is thick product.Mixed solution (1: 3) column chromatography with ethyl acetate and sherwood oil obtains title compound 1.19 grams, fusing point 112-114 ℃.Yield 66.2%.
Nuclear magnetic data ( 1HNMR, 300MHz, interior mark TMS, solvent C DCl 3) as follows: δ ppm 7.12 (1H, dd), 7.18 (2H, d), 7.21 (2H, m), 7.44 (2H, d), 7.58 (1H, m), 7.90 (1H, dd), 8.80 (1H, dd).
Other compounds are synthetic with reference to aforesaid method.
The rerum natura of the general formula shown in the part table 1 (I) compound and nuclear magnetic data ( 1HNMR, 300MHz, interior mark TMS, solvent C DCl 3) as follows:
Compound 2: fusing point 132-134 ℃.δppm 7.26(1H，t)，7.42(5H，m)，7.57(3H，m)，7.84(1H，dd)，8.08(1H，dd)，8.82(1H，d)。
Compound 3: fusing point 118-120 ℃.δppm 7.20(1H，t)，7.22(1H，t)，7.32(2H，d)，7.36(1H，m)，7.57(2H，d)。
Compound 4: fusing point 108-110 ℃.δppm 5.16(2H，m)，7.26(1H，t)，7.34(1H，m)，8.19(1H，d)，8.36(1H，s)，8.64(1H，d)，8.93(1H，d)，10.00(1H，s)。
Compound 19: fusing point 160-162 ℃.δppm 7.34(3H，m)，7.44(1H，dd)，7.54(2H，t)，7.60(1H，m)，7.84(1H，dd)，8.04(1H，d)，8.93(1H，d)，10.20(1H，s)。
Compound 20: fusing point 120-122 ℃.δppm 7.26(1H，d)，7.38(3H，t)，7.44(1H，d)，7.54(2H，d)，7.60(1H，t)，7.86(1H，dd)，8.83(1H，d)，10.20(1H，s)。
Compound 33: fusing point 102-104 ℃.δppm 4.87(2H，m)，7.08(1H，dd)，7.46(1H，dd)，7.92(1H，dd)，8.38(1H，dd)，8.56(1H，dd)，8.83(1H，dd)，9.15(1H，s)。
Compound 34: fusing point 140-141 ℃.δppm 4.75(2H，m)，7.07(1H，dd)，7.13(1H，m)，7.25(2H，m)，7.33(1H，dd)，7.41(1H，t)，7.88(1H，dd)，8.29(1H，dd)，8.70(1H，dd)，8.95(1H，dd)，10.21(1H，s)。
Compound 35: fusing point 127-129 ℃.δppm 4.74(2H，m)，7.07(1H，dd)，7.16(2H，d)，7.23(1H，dd)，7.44(2H，d)，7.88(1H，dd)，8.27(1H，dd)，8.70(1H，dd)，8.94(1H，dd)，10.23(1H，s)。
Compound 36: fusing point 102-103 ℃.δppm 4.70(2H，m)，6.98(1H，m)，7.36(4H，m)，7.40(1H，d)，7.44(1H，d)，7.52(1H，dd)，7.58(1H，dd)，7.82(2H，m)，10.00(1H，s)。
Compound 53: fusing point 170-172 ℃.δppm 6.98(1H，s)，7.42(5H，m)，7.62(2H，m)，7.86(1H，d)，7.96(2H，d)，10.00(1H，s)。
Compound 58: fusing point 142-144 ℃.δppm 3.92(3H，s)，6.72(1H，d)，6.95(1H，s)，7.42(4H，d)，7.56(2H，m)，7.74(1H，dd)，7.82(2H，d)，10.00(1H，s)。
Compound 60: fusing point 120-122 ℃.δppm 6.88(2H，d)，7.12(1H，t)，7.38(2H，m)，7.40(8H，m)，8.18(1H，dd)，8.60(2H，m)，9.27(1H，s)。
Compound 61: fusing point 163-165 ℃.δppm 2.71(3H，s)，7.40(4H，m)，7.62(2H，d)，8.20(1H，d)，8.58(1H，d)，9.78(1H，s)。
Compound 62: fusing point 109-112 ℃.δppm 6.92(2H，m)，7.14(1H，m)，7.24(2H，t)，7.34(2H，m)，7.46(2H，m)，7.58(2H，m)，8.22(1H，dd)，8.44(1H，dd)，8.62(1H，dd)，8.92(1H，dd)，9.80(1H，s)。
Compound 63: fusing point 98-100 ℃.δppm 6.78(1H，t)，6.98(3H，m)，7.48(4H，m)，7.90(1H，s)，8.45(1H，dd)，8.86(1H，dd)，9.86(1H，s)。
Compound 64: fusing point 130-134 ℃.δppm 7.48(5H，m)，7.60(4H，d)，7.75(1H，d)，8.50(1H，d)，8.82(1H，d)，9.88(1H，s)。
Compound 65: fusing point 161-163 ℃.δppm 7.41(5H，m)，7.62(2H，m)，7.94(1H，dd)，8.37(1H，dd)，8.45(2H，m)，9.92(1H，s)。
Compound 80: fusing point 116-118 ℃.δppm 4.64(2H，m)，7.04(1H，m)，7.26(2H，d)，7.38(2H，m)，7.56(4H，m)，7.76(1H，dd)，7.83(1H，dd)，9.58(1H，s)。
Compound 81: fusing point 159-161 ℃.δppm 7.50(3H，m)，7.72(6H，m)，8.24(1H，d)，8.58(1H，d)，9.60(1H，s)。
Compound 82: fusing point 160-164 ℃.δppm 7.36(2H，m)，7.62(4H，d)，8.36(1H，d)，8.40(2H，m)，8.68(1H，d)，9.92(1H，s)。
Compound 83: fusing point 138-140 ℃.δppm 7.08(2H，m)，7.52(4H，m)，7.76(2H，d)，8.38(1H，d)，8.60(1H，d)，9.96(1H，s)。
Compound 84: fusing point 158-160 ℃.δppm 7.42(2H，dd)，7.46(1H，s)，7.54(1H，d)，7.70(2H，d)，8.14(1H，dd)，8.24(1H，dd)，8.54(1H，dd)，8.82(1H，d)，10.02(1H，s)。
Compound 85: fusing point 197-200 ℃.δppm 7.42(2H，d)，7.56(1H，d)，7.80(2H，d)，8.18(2H，d)，8.22(1H，d)，8.38(2H，d)，8.62(1H，d)，9.88(1H，s)。
Compound 86: fusing point 159-162 ℃.δppm 4.80(2H，s)，7.17(1H，d)，7.35(1H，dd)，7.45(2H，m)，7.52(2H，d)，7.68(2H，d)，8.52(1H，dd)，8.60(1H，dd)，10.21(1H，s)。
Compound 87: fusing point 175-176 ℃.δppm 2.75(3H，s)，7.50(3H，m)，7.70(2H，d)，8.25(1H，d)，8.60(1H，d)，9.68(1H，s)。
Compound 88: fusing point 166-170 ℃.δppm 7.43(1H，m)，7.51(2H，d)，7.82(2H，d)，8.54(1H，d)，8.71(1H，d)，9.96(1H，s)。
Compound 89: fusing point 138-142 ℃.δppm 2.76(3H，s)，7.52(4H，m)，7.86(1H，s)，8.60(1H，d)，8.82(1H，d)，10.21(1H，s)。
Compound 90: fusing point 156-159 ℃.δppm 4.09(3H，s)，7.42(1H，m)，7.48(2H，d)，7.72(2H，d)，8.18(1H，dd)，8.27(1H，s)，8.55(1H，dd)，8.80(1H，s)。
Compound 95: fusing point 137-139 ℃.δppm 7.12(3H，m)，7.38(2H，d)，7.70(3H，m)，7.80(1H，d)，7.90(1H，d)，8.18(1H，s)，8.90(1H，d)，9.92(1H，s)。
Compound 96: fusing point 112-114 ℃.δppm 7.14(1H，m)，7.20(4H，m)，7.44(2H，d)，7.58(1H，m)，7.90(1H，dd)，8.82(1H，dd)，9.62(1H，s)。
Compound 97: fusing point 181-183 ℃.δppm 4.66(2H，s)，6.86(1H，d)，7.06(1H，dd)，7.12(2H，d)，7.26(1H，d)，7.39(3H，m)，7.88(1H，dd)，8.81(1H，dd)，9.38(1H，s)。
Compound 98: fusing point 110-112 ℃.δppm 7.06(1H，m)，7.12(1H，d)，7.41(2H，d)，7.50(1H，d)，7.90(1H，dd)，8.19(1H，dd)，8.44(1H，s)，8.83(1H，dd)，8.93(1H，d)。
Compound 99: fusing point 136-138 ℃.δppm 2.78(3H，s)，7.07(1H，dd)，7.13(2H，d)，7.40(2H，d)，7.91(1H，dd)，8.58(1H，s)，8.77(1H，dd)。
Compound 100: fusing point 93-95 ℃.δppm 7.16(1H，m)，7.20(2H，d)，7.44(2H，d)，7.54(1H，dd)，7.90(1H，dd)，8.13(1H，dd)，8.50(1H，dd)，8.78(1H，dd)。
Example of formulations
(be metered into behind the active ingredient folding hundred in the prescription, shown in percentage composition be weight percentage)
Example 4 60% wettable powders
Compound 1 (content 97.2%) 60%
Dodecyl sodium naphthalene sulfonate 2%
Sodium lignosulfonate 9%
Kaolin complements to 100%
Compound 1, dodecyl sodium naphthalene sulfonate, sodium lignosulfonate and kaolin (being solid) are mixed, in pulverizer, pulverize, reach standard up to particle.
Example 5 35% missible oil
Compound 4 (content 98.4%) 35%
Phosphorous acid 10%
Ethoxylated glycerol three acid esters 15%
Pimelinketone complements to 100%
Phosphorous acid is dissolved in the pimelinketone, adds compound 4 and ethoxylated glycerol three acid esters then, obtains transparent solution.
Example 6 30% aq suspensions
Compound 7 (content 96.4%) 30%
Dodecyl sodium naphthalene sulfonate 4%
Hemicellulose 2%
Propylene oxide 8%
Water complements to 100%
Compound 7 is pulverized in (1mm pearl) in ball mill with 80% and the dodecyl sodium naphthalene sulfonate of answering amount of water.Hemicellulose and propylene oxide are dissolved in all the other water of 20%, stir then to add said components.
Example 7 25% suspension-emulsion enriched materials
Compound 10 (content 96.2%) 25%
Dodecyl alcohol polyoxyethylene glycol phosphoric acid ester 4%
Oxyethyl group tri-glyceride 2%
Calcium dodecylbenzene sulphonate 1.5%
The epoxy first and second alkane epoxy propane copolymers 2.5%
Pimelinketone 30%
The alkylaryl cut complements to 100%
With compound 10 be dissolved in 80% should add (pimelinketone and alkylaryl cut) in the quantity of solvent, add emulsifying agent (dodecyl alcohol polyoxyethylene glycol phosphoric acid ester, oxyethyl group tri-glyceride and calcium dodecylbenzene sulphonate) and dispersion agent (2.5 parts of epoxy first and second alkane epoxy propane copolymers) then, mixture is thoroughly stirred.Mixture is pulverized in ball mill (1mm pearl), and then adds all the other solvents of 20%.
Biological activity determination
Example 8 fungicidal activities are measured
With The compounds of this invention the multiple fungal disease of plant has been carried out the fungicidal activity test.The method of test is as follows:
Adopt the potted plant measuring method of live body.The former medicinal acetone solution of testing compound (acetone consumption be liquid to be measured 10%) is diluted to required concentration with the water that contains 0.1% tween 80.Spray pesticide carries out the disease inoculation after 24 hours to plant examination material.After the inoculation, plant is placed in the fixed temperature and humidity incubator, makes it susceptible, wait to contrast abundant morbidity back (being generally week age) and carry out assessment surveys.
Partial test result following (all dosage are all in effective constituent):
During 400mg/L, be 100% compound 1,32,33,34,63,64,81,84,96 etc. to be arranged to the wheat powdery mildew preventive effect; Preventive effect greater than 90% compound 61,86,87,99 etc. are arranged.
During 400mg/L, to the gray mold of cucumber preventive effect be 90% compound 34 etc. arranged; Preventive effect be 85% compound 62,82,83,85,86,100 etc. are arranged.
During 400mg/L, to the cucumber downy mildew preventive effect be 90% compound 89 etc. arranged.
During 400mg/L, to the rice blast preventive effect be 98% compound 61 etc. arranged.
During 200mg/L, to the wheat powdery mildew preventive effect be 100% compound 32,33,84 etc. are arranged; Preventive effect greater than 90% compound 1,86,96 etc. are arranged.
During 200mg/L, to the rice blast preventive effect be 85% compound 61 etc. arranged.

Claims (8)

1, a kind of N-(pyridine of replacement) amides, shown in general formula (I):
Figure A2005100471500002C1
In the formula: R 1, R 2, R 3Can be identical or different, be selected from hydrogen, halogen, cyano group, nitro, C respectively 1-C 12Alkyl, C 2-C 12Thiazolinyl, C 2-C 12Alkynyl, C 1-C 12Haloalkyl, C 1-C 12Alkoxyl group, C 1-C 12Halogenated alkoxy, C 1-C 12Alkylthio, C 1-C 12Alkane alkylsulfonyl, C 1-C 12Alkyl-carbonyl, C 1-C 12Alkoxy C 1-C 12Alkyl, C 1-C 12Alkoxy carbonyl, C 1-C 12Alkoxy carbonyl C 1-C 12Alkyl, C 1-C 12Halogenated alkoxy C 1-C 12Alkyl, replace or one of unsubstituted following radicals arbitrarily: amido C 1-C 12Alkyl, aryl, heteroaryl, aryloxy, aryl C 1-C 12Alkyl, aryl C 1-C 12Alkoxyl group, heteroaryl C 1-C 12Alkyl, heteroaryl C 1-C 12Alkoxyl group; Ar is selected from any replacement or unsubstituted aryl, heteroaryl or aryloxy C 1-C 12Alkyl;
And steric isomer.
2, compound according to claim 1 is characterized in that: R in the general formula (I) 1, R 2, R 3Can be identical or different, be selected from hydrogen, halogen, cyano group, nitro, C respectively 1-C 6Alkyl, C 2-C 6Thiazolinyl, C 2-C 6Alkynyl, C 1-C 6Haloalkyl, C 1-C 6Alkoxyl group, C 1-C 6Halogenated alkoxy, C 1-C 6Alkylthio, C 1-C 6Alkane alkylsulfonyl, C 1-C 6Alkyl-carbonyl, C 1-C 6Alkoxy C 1-C 6Alkyl, C 1-C 6Alkoxy carbonyl, C 1-C 6Alkoxy carbonyl C 1-C 6Alkyl, C 1-C 6Halogenated alkoxy C 1-C 6Alkyl; That can be replaced by alkyl, alkoxyl group, haloalkyl, halogenated alkoxy, halogen, nitro or cyano group or do not replace one of following radicals: amido C 1-C 6Alkyl, aryl, heteroaryl, aryloxy, aryl C 1-C 6Alkyl, aryl C 1-C 6Alkoxyl group, heteroaryl C 1-C 6Alkyl, heteroaryl C 1-C 6Alkoxyl group; Ar is selected from and replaces or unsubstituted aryl, heteroaryl or aryloxy C 1-C 6Alkyl.
3, compound according to claim 2 is characterized in that: R in the general formula (I) 1, R 2, R 3Can be identical or different, be selected from hydrogen, halogen, cyano group, nitro, C respectively 1-C 6Alkyl, C 2-C 6Thiazolinyl, C 2-C 6Alkynyl, C 1-C 6Haloalkyl, C 1-C 6Alkoxyl group, C 1-C 6Halogenated alkoxy, C 1-C 6Alkylthio, C 1-C 6Alkane alkylsulfonyl, C 1-C 6Alkyl-carbonyl, C 1-C 6Alkoxy C 1-C 6Alkyl, C 1-C 3Alkoxy carbonyl, C 1-C 6Alkoxy carbonyl C 1-C 3Alkyl, C 1-C 3Halogenated alkoxy C 1-C 3Alkyl, substituted amido C 1-C 3Alkyl, replacement or unsubstituted following radicals: phenyl, phenoxy group, benzyl or benzyloxy; Ar is selected from and replaces or unsubstituted phenyl, xenyl, pyridyl, pyrazolyl, thiazolyl or phenoxyalkyl.
4, compound according to claim 3 is characterized in that: R in the general formula (I) 1, R 2, R 3Can be identical or different, be selected from hydrogen, chlorine, bromine, fluorine, cyano group or C respectively 1-C 3Alkyl, C 1-C 3Alkoxyl group, C 1-C 3Halogenated alkoxy, C 1-C 3Alkylthio, C 1-C 3Alkane alkylsulfonyl, C 1-C 3Alkoxy carbonyl, 0-5 the phenyl or the phenoxy group that replace; Ar is selected from Q as follows 1, Q 2, Q 3, Q 4, Q 5, Q 6, Q 7, Q 8, Q 9, Q 10, Q 11, Q 12, Q 13, Q 14, Q 15, Q 16, Q 17, Q 18, Q 19, Q 20, Q 21, Q 22, Q 23, Q 24Or Q 25:
5, compound according to claim 4 is characterized in that: R in the general formula (I) 1, R 2, R 3Can be identical or different, be selected from hydrogen, chlorine, bromine, fluorine, cyano group or C respectively 1-C 3Alkyl, C 1-C 3Alkoxyl group, C 1-C 3Halogenated alkoxy, 0-3 the phenyl or the phenoxy group that replace; Ar is selected from Q 1, Q 2, Q 3, Q 4, Q 5, Q 6, Q 7, Q 8, Q 9, Q 10, Q 11, Q 12, Q 13, Q 14, Q 15Or Q 16
6, the preparation method of any described compound among the claim 1-5 is characterized in that: general formula (I) compound is reacted under alkaline condition, in organic solvent by the pyridyl amine compound of the replacement shown in the general formula (II) and the carboxylic acid halides shown in the general formula (III) and makes:
Figure A2005100471500003C2
In the formula, R 1, R 2, R 3The same with the definition of Ar group.
7, the application of the described general formula of claim 1 (I) compound disease on the control crop.
8, a kind of fungicidal composition is characterized in that: contain the described general formula of claim 1 (I) compound in the composition, the weight percentage of active ingredient is 0.1-99%.
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