CN1985593A - Pesticide preparation containing saturated guinary heterocyclic compound and its use - Google Patents

Pesticide preparation containing saturated guinary heterocyclic compound and its use Download PDF

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CN1985593A
CN1985593A CN 200510130667 CN200510130667A CN1985593A CN 1985593 A CN1985593 A CN 1985593A CN 200510130667 CN200510130667 CN 200510130667 CN 200510130667 A CN200510130667 A CN 200510130667A CN 1985593 A CN1985593 A CN 1985593A
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saturated
membered heterocycles
formula
missible oil
tween
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任天瑞
张小军
李永红
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Institute of Process Engineering of CAS
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Institute of Process Engineering of CAS
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Abstract

The present invention discloses a kind of pesticide preparation containing saturated quinary heterocyclic compound and its use. The pesticide preparation contains saturated quinary heterocyclic compound as the effective component, solvent and surfactant. It is used for soaking seed of and spraying beet, water melon, tomato, chili, cucumber, etc. It has pesticidal activity, bactericidal activity and plant growth promoting activity, can raise the drought resisting and soline-alkali resisting capacity of plant, and possesses high efficiency, low toxicity, good environment compatibility and low cost.

Description

A kind of pesticidal preparations that contains saturated five-membered heterocycles and uses thereof
Technical field
The present invention relates to a kind of pesticidal preparations that contains saturated five-membered heterocycles and uses thereof.
Background technology
In Agricultural Development and modern production, the environmental problem that use brought of agricultural chemicals has caused people's very big concern.The a data of the World Food Programme shows that world agriculture is faced with annual 7000 ten thousand increasing population and insufficiency that increase, and is limited all the time and plough, so the existing quality of ploughing and the output of unit are are all being appealed to pay attention to more improving in the whole world.The behave that improves agriculture yield per unit area is many-sided, and the use of agricultural chemicals is exactly one of its important measures.The use of agricultural chemicals can be saved the labour, reduces costs of farm produce, increases economic efficiency.Agricultural chemicals all plays important effect in processes such as plant growing, adjusting, results and storage, fresh-keeping, transportation, processing.It is reported, in the world food output due to illness, the loss that causes of worm, crop smothering, wheat accounts for 24.4%, paddy rice is up to 47.1%, and corn and potato are respectively 35.7% and 32.3%.Someone adds up, twentieth century after 50 years whole world agricultural average year units increased in production be preceding 50 years 30 times.Amount to the art contribution in the amplification and account for 73%, wherein chemical fertilizer, agricultural chemicals respectively account for half, and visible agricultural chemicals is to ensure the necessary means of production of agricultural sustainable development.Yet harmful organic solvent and additive can cause secondary pollution to environment in the low and formulation of the unreasonable drug effect that causes of the high toxicity of agricultural chemicals itself and the low biological degradability and the formulations of pesticide.So, prepare rational pesticidal preparations and to the exploitation of the environmental friendliness formulation that matches with it, pesticide efficacy is further improved and the secondary pollution avoiding environment is caused just seems particularly important.
Summary of the invention
The object of the present invention is to provide that a kind of cost is low, efficient, low toxicity, with Environmental compatibility good, be suitable for industrialization contain pesticidal preparations of saturated five-membered heterocycles and uses thereof.
The objective of the invention is to realize by the following technical solutions:
The invention provides a kind of pesticidal preparations that contains saturated five-membered heterocycles, it is characterized in that: contain saturated five-membered heterocycles shown in formula I, formula II or the formula III as effective ingredient.
Formula I
Wherein: X 1=O or S; X 2=O or S; X 3=O or S;
R 1=CH 3Or H; R 2=H, CH 3, CH 2Cl, or CH 2OH;
And: work as X 1, X 2, X 3During=O, R 1=R 2≠ H
Figure A20051013066700052
Formula II
Wherein: X 1=O or S; X 2=O or S; X 3=O or S;
R 1=CH 3R 2=H or CH 3R 3=H, CH 3, CH 2Cl, or CH 2OH
Figure A20051013066700053
Formula III
Wherein: X 2=O or S; X 3=O or S;
R 2=H or CH 3R 3=H, CH 3, CH 2Cl, or CH 2OH
The above-mentioned pesticidal preparations that contains saturated five-membered heterocycles provided by the invention be the mixture of saturated five-membered heterocycles shown in formula I, formula II or the formula III, solvent and surfactant composition, and the ratio of three kinds of components is
Saturated five-membered heterocycles 5～20 weight portions
Solvent 65～90 weight portions
Surfactant 2～7 weight portions
Described solvent comprises: toluene, N, dinethylformamide (DMF), methyl alcohol, ethanol, acetone, soya-bean oil, diesel oil or machine oil etc.;
Described surfactant is APEO (GFC), TritonX (OP)-10, farming breast (0204), Tween-80.
Three kinds of components are at room temperature mixed, can obtain the pesticidal preparations that contains saturated five-membered heterocycles of the present invention.
The above-mentioned pesticidal preparations that contains saturated five-membered heterocycles provided by the invention can be used for desinsection and sterilization aspect and have the plant growing activation, can improve the drought resisting of plant, anti-salt alkali ability.Institute's method of application is seed soaking and foliage-spray.Specific as follows:
1. have insecticidal activity, the working concentration of the saturated five-membered heterocycles shown in active ingredient wherein---formula I, formula II or the formula III is 100～200ppm.
2. have bactericidal activity, be suitable for apple wheel line bacterium, the working concentration of the saturated five-membered heterocycles shown in active ingredient wherein---formula I, formula II or the formula III is 50ppm.
3. has the coordinate plant growth activity, being suitable for using crop is beet, watermelon, tomato, capsicum, cucumber, clover, cotton, asparagus lettuce, wheat, corn, soybean and flowers etc., and the working concentration of the saturated five-membered heterocycles shown in active ingredient wherein---formula I, formula II or the formula III is 10～100ppm.
The above-mentioned pesticidal preparations that contains saturated five-membered heterocycles provided by the invention has the activity of desinsection, sterilization.And, adopt the seed soaking mode to use the above-mentioned pesticidal preparations that contains saturated five-membered heterocycles provided by the invention can obviously promote the growth of root system of plant, improve plant in arid and the saline and alkaline survival rate that waits under the stress conditions.The foliage-spray mode can promote the growth of crop, improves drought resisting and the resistance against diseases of crop, prolong melon one-tenth current, and can improve physiological function of plants, thereby the one-tenth viability that improves plant under the lack of water condition improves crop yield;
The above-mentioned pesticidal preparations that contains saturated five-membered heterocycles provided by the invention uses saturated five-membered heterocycles as active ingredient, in the toxicity that has overcome crown ether compound, kept the good resistance effect of crown ether compound, it is also advantageous in that:
1. the pesticidal preparations of the saturated five-membered heterocycles of the present invention's preparation is through experiment showed, that such saturated five-membered heterocycles has killing aphids, bactericidal activity effect, respectively shown in table 2 and table 3～6.
2. have anti-saline and alkaline and drought-resistant two kinds of degeneration-resistant biologically actives simultaneously, as the result of table 7～12 as can be seen, pesticidal preparations provided by the invention has the effect that resists saline and alkaline and drought-resistant and plant growth regulating activity.
3. the employed raw material of preparation method of the present invention is easy to get, and used novel solid-phase catalyst, determined that a synthetic route is short, raw material is easy to get, yield height, synthetic route simple to operate, with high content of technology, be suitable for large-scale production, the many factories of China have had the production technology of this product intermediate, and cost low (0.05 yuan/gram), the peasant is acceptant, and technology is promoted easily.
4. the active ingredient in the pesticidal preparations provided by the invention---saturated five-membered heterocycles has the high-efficiency low-toxicity effect, and seed soaking only needs 20% preparation, 2 gram/mus, and spraying only needs every mu 8 gram/mu of 20% preparation, and its scope that is suitable for plant is wide.
5. preparation method of the present invention is simple, technological process easily realizes, easily industrialization, purposes are wide.
Embodiment
The present invention is further illustrated below in conjunction with embodiment, but the present invention is not limited only to these examples.
The used fractional saturation five-membered heterocycles of the present invention can directly be buied, and also can synthesize as follows:
Embodiment 1, (1 α's～1f) is synthetic
250mL two neck round-bottomed flasks are installed on magnetic stirrer, and are furnished with water knockout drum, thermometer.Add furfural 1mol, add the glycol of 1～1.2mol or solvent, the solid catalyst 1～10g of mercaptan or derivatives thereof and 100～150ml again, pour in the reactor after the mixing, install water knockout drum again, with conventional method reflux water-dividing 4～12 hours, remove and desolvate, decompression distillation obtains following (the saturated five-membered heterocycles of 1a～1f).
Figure A20051013066700071
1a：X 1＝X 2＝O，R 1＝CH 3，R 2＝H
1b：X 1＝X 2＝O，R 1＝CH 2Cl，R 2＝H
1c：X 1＝S，X 2＝O，R 1＝R 2＝H
1d：X 1＝S，X 2＝O，R 1＝CH 3，R 2＝CH 3
1e：X 1＝X 2＝S，R 1＝R 2＝H
1f：X 1＝X 2＝O，R 1＝CH 2OH，R 2＝H
Embodiment 2, (2a's～2f) is synthetic
250mL two neck round-bottomed flasks are installed on magnetic stirrer, and are furnished with water knockout drum, thermometer.Add 5 methyl furfural 1mol, add the glycol of 1～1.2mol or solvent, the solid catalyst 1～10g of mercaptan or derivatives thereof and 100～150ml again, pour in the reactor after the mixing, install water knockout drum again, with conventional method reflux water-dividing 4～12 hours, remove and desolvate, decompression distillation obtains following saturated five-membered heterocycles.
Figure A20051013066700081
2a：X 1＝X 2＝O，R 1＝R 2＝H
2b：X 1＝X 2＝O，R 1＝CH 3，R 2＝H
2c：X 1＝X 2＝O，R 1＝CH 2Cl，R 2＝H
2d：X 1＝S，X 2＝O，R 1＝R 2＝H
2e：X 1＝S，X 2＝O，R 1＝R 2＝CH 3
2f：X 1＝X 2＝S，R 1＝R 2＝H
Embodiment 3, (3 α's～3f) is synthetic
250mL two neck round-bottomed flasks are installed on magnetic stirrer, and are furnished with water knockout drum, thermometer.Add 3-ethylmercapto group butyraldehyde 1mol, add the glycol of 1～1.2mol or solvent, the solid catalyst 1～10g of mercaptan or derivatives thereof and 100～150ml again, pour in the reactor after the mixing, install water knockout drum again, with conventional method reflux water-dividing 4～12 hours, remove and desolvate, decompression distillation obtains following saturated five-membered heterocycles.
3a：X 1＝X 2＝O，R 1＝R 2＝H
3b：X 1＝X 2＝O，R 1＝CH 3，R 2＝H
3c：X 1＝X 2＝O，R 1＝CH 2Cl，R 2＝H
3d：X 1＝S，X 2＝O，R 1＝R 2＝H
3e：X 1＝S，X 2＝O，R 1＝R 2＝CH 3
3f：X 1＝X 2＝S，R 1＝R 2＝H
Embodiment 4, (4 α's～4f) is synthetic
250mL two neck round-bottomed flasks are installed on magnetic stirrer, and are furnished with water knockout drum, thermometer.Add 2-aldehyde radical thiophene 1mol, add the glycol of 1～1.2mol or solvent, the solid catalyst 1～10g of mercaptan or derivatives thereof and 100～150ml again, pour in the reactor after the mixing, install water knockout drum again, with conventional method reflux water-dividing 4～12 hours, remove and desolvate, decompression distillation obtains following saturated five-membered heterocycles.
4a：X 1＝X 2＝O，R 1＝R 2＝H
4b：X 1＝X 2＝O，R 1＝CH 3，R 2＝H
4c：X 1＝X 2＝O，R 1＝CH 2Cl，R 2＝H
4d：X 1＝S，X 2＝O，R 1＝R 2＝H
4e：X 1＝S，X 2＝O，R 1＝R 2＝CH 3
4f：X 1＝X 2＝S，R 1＝R 2＝H
Embodiment 5, the preparation cream preparation 1A that contains saturated five-membered heterocycles (1a) of the present invention 1
With the saturated five-membered heterocycles (1a) of preparation among the embodiment 1 of 20 weight portions, the toluene of 75 weight portions, the APEO of 3 weight portions (GFC) adds in the reactor successively, stirring at room is even, obtains the cream preparation 1A that contains saturated five-membered heterocycles (1a) of the present invention 1
Embodiment 6～148, the preparation cream preparation that contains saturated five-membered heterocycles of the present invention
According to the method for embodiment 25, (1a～4f) be mixed with a series of cream preparations that contain saturated five-membered heterocycles of the present invention, its composition is listed in table 1 with the saturated five-membered heterocycles of embodiment 1～4 preparation.
Table 1, cream preparation provided by the invention
Embodiment Saturated five-membered heterocycles Solvent Surfactant Numbering
Kind Weight (g) Kind Weight (g) Kind Weight (g)
5 1a 20 Toluene 75 GFC 3 1A 1
6 1a 20 DMF 65 Tween-80 2 1A 2
7 1a 15 Methyl alcohol 80 Farming breast (0204) 7 1A 3
8 1a 15 Toluene 75 Tween-80 5 1A 4
9 1a 5 DMF 85 OP-10 4 1A 5
10 1a 5 Methyl alcohol 90 Tween-80 6 1A 6
11 1b 20 Toluene 75 GFC 3 1B 1
12 1b 20 DMF 65 Tween-80 2 1B 2
13 1b 15 Methyl alcohol 80 Farming breast (0204) 7 1B 3
14 1b 15 Toluene 75 Tween-80 5 1B 4
15 1b 5 DMF 85 OP-10 4 1B 5
16 1b 5 Methyl alcohol 90 Tween-80 6 1B 6
17 1c 20 Toluene 75 GFC 3 1C 1
18 1c 20 DMF 65 Tween-80 2 1C 2
19 1c 15 Methyl alcohol 80 Farming breast (0204) 7 1C 3
20 1c 15 Toluene 75 Tween-80 5 1C 4
21 1c 5 DMF 85 OP-10 4 1C 5
22 1c 5 Methyl alcohol 90 Tween-80 6 1C 6
23 1d 20 Toluene 75 GFC 3 1D 1
24 1d 20 DMF 65 Tween-80 2 1D 2
25 1d 15 Methyl alcohol 80 Farming breast (0204) 7 1D 3
26 1d 15 Toluene 75 Tween-80 5 1D 4
27 1d 5 DMF 85 OP-10 4 1D 5
28 1d 5 Methyl alcohol 90 Tween-80 6 1D 6
29 1e 20 Toluene 75 GFC 3 1E 1
30 1e 20 DMF 65 Tween-80 2 1E 2
31 1e 15 Methyl alcohol 80 Farming breast (0204) 7 1E 3
32 1e 15 Toluene 75 Tween-80 5 1E 4
33 1e 5 DMF 85 OP-10 4 1E 5
34 1e 5 Methyl alcohol 90 Tween-80 6 1E 6
35 1f 20 Toluene 75 GFC 3 1F 1
36 1f 20 DMF 65 Tween-80 2 1F 2
37 1f 15 Methyl alcohol 80 Farming breast (0204) 7 1F 3
38 1f 15 Toluene 75 Tween-80 5 1F 4
39 1f 5 DMF 85 OP-10 4 1F 5
40 1f 5 Methyl alcohol 90 Tween-80 6 1F 6
41 2a 20 Toluene 75 GFC 3 2A 1
42 2a 20 DMF 65 Tween-80 2 2A 2
43 2a 15 Methyl alcohol 80 Farming breast (0204) 7 2A 3
44 2a 15 Toluene 75 Tween-80 5 2A 4
45 2a 5 DMF 85 OP-10 4 2A 5
46 2a 5 Methyl alcohol 90 Tween-80 6 2A 6
47 2b 20 Toluene 75 GFC 3 2B 1
48 2b 20 DMF 65 Tween-80 2 2B 2
49 2b 15 Methyl alcohol 80 Farming breast (0204) 7 2B 3
50 2b 15 Toluene 75 Tween-80 5 2B 4
51 2b 5 DMF 85 OP-10 4 2B 5
52 2b 5 Methyl alcohol 90 Tween-80 6 2B 6
53 2c 20 Toluene 75 GFC 3 2C 1
54 2c 20 DMF 65 Tween-80 2 2C 2
55 2c 15 Methyl alcohol 80 Farming breast (0204) 7 2C 3
56 2c 15 Toluene 75 Tween-80 5 2C 4
57 2c 5 DMF 85 OP-10 4 2C 5
58 2c 5 Methyl alcohol 90 Tween-80 6 2C 6
59 2d 20 Toluene 75 GFC 3 2D 1
60 2d 20 DMF 65 Tween-80 2 2D 2
61 2d 15 Methyl alcohol 80 Farming breast (0204) 7 2D 3
62 2d 15 Toluene 75 Tween-80 5 2D 4
63 2d 5 DMF 85 OP-10 4 2D 5
64 2d 5 Methyl alcohol 90 Tween-80 6 2D 6
65 2e 20 Toluene 75 GFC 3 2E 1
66 2e 20 DMF 65 Tween-80 2 2E 2
67 2e 15 Methyl alcohol 80 Farming breast (0204) 7 2E 3
68 2e 15 Toluene 75 Tween-80 5 2E 4
69 2e 5 DMF 85 OP-10 4 2E 5
70 2e 5 Methyl alcohol 90 Tween-80 6 2E 6
71 2f 20 Toluene 75 GFC 3 2F 1
72 2f 20 DMF 65 Tween-80 2 2F 2
73 2f 15 Methyl alcohol 80 Farming breast (0204) 7 2F 3
74 2f 15 Toluene 75 Tween-80 5 2F 4
75 2f 5 DMF 85 OP-10 4 2F 5
76 2f 5 Methyl alcohol 90 Tween-80 6 2F 6
77 3a 20 Toluene 75 GFC 3 3A 1
78 3a 20 DMF 65 Tween-80 2 3A 2
79 3a 15 Methyl alcohol 80 Farming breast (0204) 7 3A 3
80 3a 15 Toluene 75 Tween-80 5 3A 4
81 3a 5 DMF 85 OP-10 4 3A 5
82 3a 5 Methyl alcohol 90 Tween-80 6 3A 6
83 3b 20 Toluene 75 GFC 3 3B 1
84 3b 20 DMF 65 Tween-80 2 3B 2
85 3b 15 Methyl alcohol 80 Farming breast (0204) 7 3B 3
86 3b 15 Toluene 75 Tween-80 5 3B 4
87 3b 5 DMF 85 OP-10 4 3B 5
88 3b 5 Methyl alcohol 90 Tween-80 6 3B 6
89 3c 20 Toluene 75 GFC 3 3C 1
90 3c 20 DMF 65 Tween-80 2 3C 2
91 3c 15 Methyl alcohol 80 Farming breast (0204) 7 3C 3
92 3c 15 Toluene 75 Tween-80 5 3C 4
93 3c 5 DMF 85 OP-10 4 3C 5
94 3c 5 Methyl alcohol 90 Tween-80 6 3C 6
95 3d 20 Toluene 75 GFC 3 3D 1
96 3d 20 DMF 65 Tween-80 2 3D 2
97 3d 15 Methyl alcohol 80 Farming breast (0204) 7 3D 3
98 3d 15 Toluene 75 Tween-80 5 3D 4
99 3d 5 DMF 85 OP-10 4 3D 5
100 3d 5 Methyl alcohol 90 Tween-80 6 3D 6
101 3e 20 Toluene 75 GFC 3 3E 1
102 3e 20 DMF 65 Tween-80 2 3E 2
103 3e 15 Methyl alcohol 80 Farming breast (0204) 7 3E 3
104 3e 15 Toluene 75 Tween-80 5 3E 4
105 3e 5 DMF 85 OP-10 4 3E 5
106 3e 5 Methyl alcohol 90 Tween-80 6 3E 6
107 3f 20 Toluene 75 GFC 3 3F 1
108 3f 20 DMF 65 Tween-80 2 3F 2
109 3f 15 Methyl alcohol 80 Farming breast (0204) 7 3F 3
110 3f 15 Toluene 75 Tween-80 5 3F 4
111 3f 5 DMF 85 OP-10 4 3F 5
112 3f 5 Methyl alcohol 90 Tween-80 6 3F 6
113 4a 20 Toluene 75 GFC 3 4A 1
114 4a 20 DMF 65 Tween-80 2 4A 2
115 4a 15 Methyl alcohol 80 Farming breast (0204) 7 4A 3
116 4a 15 Toluene 75 Tween-80 5 4A 4
117 4a 5 DMF 85 OP-10 4 4A 5
118 4a 5 Methyl alcohol 90 Tween-80 6 4A 6
119 4b 20 Toluene 75 GFC 3 4B 1
120 4b 20 DMF 65 Tween-80 2 4B 2
121 4b 15 Methyl alcohol 80 Farming breast (0204) 7 4B 3
122 4b 15 Toluene 75 Tween-80 5 4B 4
123 4b 5 DMF 85 OP-10 4 4B 5
124 4b 5 Methyl alcohol 90 Tween-80 6 4B 6
125 4c 20 Toluene 75 GFC 3 4C 1
126 4c 20 DMF 65 Tween-80 2 4C 2
127 4c 15 Methyl alcohol 80 Farming breast (0204) 7 4C 3
128 4c 15 Toluene 75 Tween-80 5 4C 4
129 4c 5 DMF 85 OP-10 4 4C 5
130 4c 5 Methyl alcohol 90 Tween-80 6 4C 6
131 4d 20 Toluene 75 GFC 3 4D 1
132 4d 20 DMF 65 Tween-80 2 4D 2
133 4d 15 Methyl alcohol 80 Farming breast (0204) 7 4D 3
134 4d 15 Toluene 75 Tween-80 5 4D 4
135 4d 5 DMF 85 OP-10 4 4D 5
136 4d 5 Methyl alcohol 90 Tween-80 6 4D 6
137 4e 20 Toluene 75 GFC 3 4E 1
138 4e 20 DMF 65 Tween-80 2 4E 2
139 4e 15 Methyl alcohol 80 Farming breast (0204) 7 4E 3
140 4e 15 Toluene 75 Tween-80 5 4E 4
141 4e 5 DMF 85 OP-10 4 4E 5
142 4e 5 Methyl alcohol 90 Tween-80 6 4E 6
143 4f 20 Toluene 75 GFC 3 4F 1
144 4f 20 DMF 65 Tween-80 2 4F 2
145 4f 15 Methyl alcohol 80 Farming breast (0204) 7 4F 3
146 4f 15 Toluene 75 Tween-80 5 4F 4
147 4f 5 DMF 85 OP-10 4 4F 5
148 4f 5 Methyl alcohol 90 Tween-80 6 4F 6
Embodiment 149, aphid screening test result
1.1 for trying aphid: black bean aphid (Aphis laburni Kaltenbach)
1.2 reagent agent: saturated five-membered ring compounds
1.3 the preparation of medicament
To above-mentioned 1A 2～4F 2Add distilled water in the cream preparation, and stir, compound concentration is the soup of 200mg/L.During use, get this soup of 200mg/L, become the soup of 100mg/L, 50mg/L and 25mg/L again with an amount of distilled water diluting, with standby with pipette.
1.4 toxicity test method
Adopt infusion process, to have from basin, cutting of at least 60 black bean aphids for examination broad bean plant, in each soup to be measured, flooded for 5 seconds, take out and get rid of unnecessary soup gently, be inserted in and preserved moisture on the water saturated sponge, treat that the dried back of soup is with on the cloche cover, the opening of cloche upper end seals with gauze in case aphid escapes, check the aphid death state after raising placement 24h, standard is: can creep with the examination worm and maybe can stand or six legs can strenuous exercises is worm alive, with the clear water is contrast, and with the mean value calculation corrected mortality, each concentration of each medicament repeats respectively 3 times.
Biologicall test the results are shown in Table 2, the part compound when 200mg/L, show reasonable biologically active.
Table 2,1A 2～4F 2Missible oil is to the toxicity test result (test concentrations 200ppm) of aphid
Sample CK 1A 2Missible oil 1B 2Missible oil 1C 2Missible oil 1D 2Missible oil 1E 2Missible oil 1F 2Missible oil
Corrected mortality 0 0 0 0 0 21 100
Sample CK 2A 2Missible oil 2B 2Missible oil 2C 2Missible oil 2D 2Missible oil 2E 2Missible oil 2F 2Missible oil
Corrected mortality 0 0 0 0 0 0 93
Sample CK 3A 2Missible oil 3B 2Missible oil 3C 2Missible oil 3D 2Missible oil 3E 2Missible oil 3F 2Missible oil
Corrected mortality 0 0 30 60 41 100 72
Sample CK 4A 2Missible oil 4B 2Missible oil 4C 2Missible oil 4D 2Missible oil 4E 2Missible oil 4F 2Missible oil
Corrected mortality 0 23 24 25 20 24 16
Found through experiments, under 200mg/L concentration, 1F 2, 2F 2, 3C 2, 3E 2, 3F 2Missible oil has good active to aphid, wherein is 100, and 2f is 93, and 3c is 60, and 3e is 100, and 3f is 72.
The mensuration of embodiment 150, the bactericidal activity that exsomatizes
1.1 reagent agent and collocation method thereof
To above-mentioned 1A 2～4F 2Add distilled water in the cream preparation, and stir, compound concentration is the soup of 200mg/L.During use, get this soup of 200mg/L, become the soup of 100mg/L, 50mg/L and 25mg/L again with an amount of distilled water diluting, with standby with pipette.
1.2 for examination pathogen and cultivation
Chinese Latin name Chinese Latin name
Sugar beet leaf spot bacteria Cercosporabeticola Asparagus stem wilt bacteria Phomaasparagi
Fusarium moniliforme Gibberellafuj ikuroi Tomato early blight bacterium Alternariasolani
Cucumber fusarium axysporum Fusariumoxysporum Fusarium graminearum Gibberellazeae
Peanut Cercospora bacteria Cercosporarachidicola The root rotof flax bacterium olarissorokiniana
The ring rot of apple bacterium Physalosporapiricola The miliary damping-off germ Rhizoctoniasolani
Botrytis cinerea pers B otrytiscinerea Exserohilum turcicum Setosphaeriaturcica
The fruit white rot of grape bacterium Coniothyriumlodiella Sclerotinia sclerotiorum clerotiniasclerotiorum
Apple zonate spot bacterium Alternariamali The pears alternaria Alternariakikuchiana
Valsa mali Valsamali Glorosprium musarum Cookeet Mass Glomerellacingulata
Rhizoctonia solani Kuhn Pelliculariasasakii Apple anthrax bacteria Glomerellacingulata
Above-mentionedly be this institute and preserve bacterial strain, all adopt the PSA medium for the examination bacterium, standby after activated for the examination bacterium.
1.3 test method
Adopt thalli growth rate determination method.Detailed process is, reagent agent is respectively drawn under aseptic condition in 1 milliliter of injection culture dish, adds 9 milliliters of medium more respectively, makes 50ug/ml pastille flat board after shaking up, and does blank with the flat board that adds 1 milliliter of aqua sterilisa.Card punch with 4 millimeters of diameters cuts the bacterium dish along the mycelia outer rim, moves on the pastille flat board, is equilateral triangle and puts.Every processing triplicate.Culture dish is placed on cultivation in 24 ± 1 ℃ of constant incubators." Invest, Then Investigate " was respectively handled bacterium dish expansion diameter in 48 hours, averaged, and relatively calculated relative bacteriostasis rate with blank.
Bacteriostasis rate (%)=(the thick bacterium expansion of control group bacterium dish expansion average diameter-processing average diameter)/control group bacterium expands average diameter * 100% relatively.
Experimental result (Plating exsomatizes) is listed in table 3～6.
Table 3,1A 2～1F 2The missible oil bactericidal activity result (test concentrations is 50ppm) that exsomatizes
Tested object (disease) Gibberella saubinetii Tomato is epidemic disease early The asparagus stem is withered Apple wheel line The peanut foxiness
1A 2Missible oil Active (%) 15.0 24.6 24.4 16.9 0
Rank - - - - -
1B 2Missible oil Active (%) 0 10.5 0 9.8 0
Rank - - - - -
1C 2Missible oil Active (%) 20.0 0 34.2 16.9 0
Rank - - - - -
1D 2Missible oil Active (%) 0 17.5 0 22.5 0
Rank - - - - -
1E 2Missible oil Active (%) 9.1 35.7 0 29.3 0
Rank - - - - -
1F 2Missible oil Active (%) 30.42 28.2 0 26.2 0
Rank - - - - -
Table 4,2A 2～2F 2The missible oil bactericidal activity result (test concentrations is 50ppm) that exsomatizes
Tested object (disease) Gibberella saubinetii Tomato is epidemic disease early The asparagus stem is withered Apple wheel line The peanut foxiness
2A 2Missible oil Active (%) 15.2 0 0 24.2 0
Rank - - - - -
2B 2Missible oil Active (%) 15.0 12.3 0 16.9 0
Rank - - - - -
2C 2Missible oil Active (%) 10.0 17.5 24.4 29.6 0
Rank - - - - -
2D 2Missible oil Active (%) 10.0 17.5 17.1 29.6 0
Rank - - - - -
2E 2Missible oil Active (%) 11.7 10.5 0 29.6 0
Rank - - - - -
2F 2Missible oil Active (%) 15.2 17.9 0 31.7 0
Rank - - - - -
Table 5,3A 2～3F 2The missible oil bactericidal activity result (test concentrations is 50ppm) that exsomatizes
Tested object (disease) Gibberella saubinetii Tomato is epidemic disease early The asparagus stem is withered Apple wheel line The peanut foxiness
3A 2Missible oil Active (%) 12.1 0 0 31.7 0
Rank - - - - -
3B 2Missible oil Active (%) 12.1 14.3 0 39.0 0
Rank - - - - -
3C 2Missible oil Active (%) 9.1 17.9 0 21.9 0
Rank - - - - -
3D 2Missible oil Active (%) 30.4 23.1 0 16.7 0
Rank - - - - -
3E 2Missible oil Active (%) 24.2 0 0 29.3 0
Rank - - - - -
3F 2Missible oil Active (%) 24.2 21.4 0 60.9 0
Rank - - - + -
Table 6,4A 2～4F 2The missible oil bactericidal activity result (test concentrations is 50ppm) that exsomatizes
Tested object (disease) Gibberella saubinetii Tomato is epidemic disease early The asparagus stem is withered Apple wheel line The peanut foxiness
4A 2Missible oil Active (%) 27.5 39.5 0 51.3 28.0
Rank - - - + -
4B 2Missible oil Active (%) 17.5 42.1 0 58.9 24.0
Rank - - - + -
4C 2Missible oil Active (%) 10.0 23.7 15.6 56.4 16.0
Rank - - - + -
4D 2Missible oil Active (%) 15.0 34.2 15.6 57.6 20.0
Rank - - - + -
4E 2Missible oil Active (%) 27.5 34.2 15.6 73.0 36.0
Rank - - - ++ -
4F 2Missible oil Active (%) 27.5 26.3 34.4 62.8 44.0
Rank - - - + -
Found through experiments, under 50mg/L concentration, 3F 2, 4A 2, 4B 2, 4C 2, 4D 2, 4E 2, 4F 2Missible oil has certain activity to apple wheel line bacterium, wherein 3F 2Missible oil is 60.9,4E 2Missible oil is 73.0.
Embodiment 151, in aqueous medium, promote the indoor bioassay of winter wheat root growth
Add distilled water in above-mentioned cream preparation, and stir, compound concentration is the soup of 200mg/L.During use, get this soup of 200mg/L, become the soup of 100mg/L, 50mg/L and 25mg/L again with an amount of distilled water diluting, with standby with pipette.
Adopt seed-soaking method, winter wheat (No. 2, north farming) seed is carried out immersion treatment respectively reach 12 hours in the variable concentrations of the missible oil of embodiment 5～148 preparations, and be contrast with the winter wheat of water logging bubble.Winter wheat seed soaked after 12 hours, the climatic cabinate that winter wheat seed is put into 20～25 ℃ is sprouted, 5 days " Invest, Then Investigate "s and seed vitality relevant index in close relations, as radical, root length, radical bud fresh weight, dry weight and related content, test result is listed in table 7～10 respectively.
Table 7,1A 2～1F 2Missible oil promotes wheat taking root in aqueous medium, germination experimental result
Concentration Radical (bar) Root long (cm) Bud long (cm) Radical bud fresh weight (g) Radical bud dry weight (g)
CK - 3.5 5.53 5.72 0.07640 0.01628
1A 2Missible oil 100ppm 4.3 3.72 3.71 0.05887 0.01488
50ppm 4.3 5.80 6.49 0.1217 0.02288
25ppm 5.0 5.58 7.02 0.1150 0.02368
1B 2Missible oil 100ppm 5.0 6.18 7.57 0.1329 0.23330
50ppm 5.0 5.16 6.22 0.1336 0.02352
25ppm 5.0 5.63 7.48 0.1415 0.02372
1C 2Missible oil 100ppm 3.0 3.82 4.15 0.04300 0.01563
50ppm 5.0 5.79 6.78 0.08142 0.02002
25ppm 4.8 6.60 6.20 0.07230 0.02112
1D 2Missible oil 100ppm 4.3 5.50 6.50 0.13540 0.02318
50ppm 5.3 5.28 6.94 0.14190 0.02414
25ppm 4.8 6.33 6.47 0.11900 0.01788
1E 2Missible oil 100ppm 4.3 5.16 4.53 0.05544 0.01364
50ppm 4.8 6.53 5.80 0.06860 0.01520
25ppm 4.0 4.95 4.43 0.08960 0.02024
1F 2Missible oil 100ppm 4.0 7.41 5.73 0.08100 0.01948
50ppm 4.8 6.93 6.85 0.09060 0.01966
25ppm 5.0 6.57 6.73 0.09460 0.02176
Table 8,2A 2～2F 2Missible oil promotes wheat taking root in aqueous medium, germination experimental result
Concentration Radical (bar) Root long (cm) Bud long (cm) Radical bud fresh weight (g) Radical bud dry weight (g)
CK - 3.6 5.43 5.56 0.07726 0.01792
2A 2Missible oil 100ppm 3.0 3.05 3.28 0.02680 0.01348
50ppm 4.0 4.99 5.25 0.04720 0.01624
25ppm 5.0 5.90 6.65 0.0880 0.01916
2B 2Missible oil 100ppm 4.8 6.13 6.90 0.13670 0.02404
50ppm 4.8 6.57 7.55 0.14180 0.02448
25ppm 4.8 6.67 6.13 0.11760 0.02126
2C 2Missible oil 100ppm 4.3 4.13 4.85 0.07820 0.01734
50ppm 4.8 5.93 6.35 0.10860 0.02168
25ppm 4.3 3.31 4.44 0.08652 0.01682
2D 2Missible oil 100ppm 5.0 7.05 7.65 0.07240 0.01690
50ppm 4.5 5.65 6.33 0.08240 0.02032
25ppm 4.5 5.94 6.33 0.07864 0.02040
2E 2Missible oil 100ppm 5.0 5.62 5.96 0.11380 0.02000
50ppm 4.5 5.05 6.40 0.10900 0.02076
25ppm 4.0 6.36 5.59 0.11100 0.02040
2F 2Missible oil 100ppm 4.3 4.26 5.10 0.05675 0.01264
50ppm 4.5 6.15 7.03 0.06894 0.01608
25ppm 4.3 6.69 6.88 0.07640 0.01848
Table 9,3A 2～3F 2Missible oil promotes wheat taking root in aqueous medium, germination experimental result
Concentration Radical (bar) Root long (cm) Bud long (cm) Radical bud fresh weight (g) Radical bud dry weight (g)
CK - 4.8 6.78 6.36 0.0956 0.01035
3A 2Missible oil 100ppm 4.8 5.55 4.60 0.07994 0.00813
50ppm 4.6 5.67 4.86 0.06552 0.00591
25ppm 5.0 6.66 6.60 0.07860 0.00896
3B 2Missible oil 100ppm 5.24 4.2 4.80 0.06542 0.00804
50ppm 4.4 5.60 5.12 0.06123 0.07251
25ppm 4.6 5.18 5.84 0.07015 0.07245
3C 2Missible oil 100ppm 4.2 5.21 4.50 0.05920 0.01426
50ppm 5.0 6.75 6.00 0.06800 0.01060
25ppm 4.4 5.44 6.3 0.06900 0.0857
3D 2Missible oil 100ppm 4.2 6.05 5.18 0.06070 0.00900
50ppm 4.6 6.17 6.20 0.06940 0.00992
25ppm 4.0 6.47 5.96 0.08720 0.00936
3E 2Missible oil 100ppm 4.8 6.21 5.52 0.08920 0.00926
50ppm 5.2 7.25 6.20 0.09800 0.01020
25ppm 5.0 7.14 6.35 0.08900 0.00957
3F 2Missible oil 100ppm 4.4 6.15 5.20 0.08070 0.00903
50ppm 4.8 5.76 5.96 0.08940 0.00892
25ppm 5.0 6.17 6.06 0.08720 0.00975
Table 10,4A 2～4F 2Missible oil promotes wheat taking root in aqueous medium, germination experimental result
Concentration Radical (bar) Root long (cm) Bud long (cm) Radical bud fresh weight (g) Radical bud dry weight (g)
CK - 4.8 6.78 6.36 0.0956 0.01035
4A 2Missible oil 100ppm 4.8 6.27 5.74 0.08720 0.01044
50ppm 4.8 5.78 5.06 0.09760 0.01072
25ppm 3.6 3.20 2.70 0.07270 0.00548
4B 2Missible oil 100ppm 4.6 6.32 6.74 0.08822 0.01022
50ppm 4.8 6.68 6.16 0.09862 0.00952
25ppm 5.0 5.27 6.71 0.08542 0.00924
4C 2Missible oil 100ppm 3.6 5.28 4.86 0.05667 0.00941
50ppm 4.4 6.37 5.74 0.06140 0.00985
25ppm 3.8 6.21 6.0 0.05818 0.00886
4D 2Missible oil 100ppm 4.4 6.00 5.42 0.09020 0.01166
50ppm 4.0 6.50 5.66 0.09884 0.01135
25ppm 4.6 6.90 6.10 0.08940 0.01006
4E 2Missible oil 100ppm 4.6 5.48 5.43 0.08620 0.00952
50ppm 5.0 6.85 6.08 0.09100 0.00895
25ppm 5.0 7.02 6.25 0.08200 0.00986
4F 2Missible oil 100ppm 4.8 6.55 5.25 0.08570 0.01016
50ppm 4.6 6.86 5.78 0.09140 0.09530
25ppm 5.2 6.22 6.01 0.08920 0.09956
By indoor bioassay experiment, by data in table 2～5 as seen, in aqueous medium, most compounds can promote taking root and germinateing of wheat, wherein 1B under 50mg/L and 25mg/L concentration 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2These several compounds of missible oil can obviously promote taking root of wheat and germinate, and all are better than contrast (CK), illustrate that these several compounds have certain plant growth regulating activity, and best at the working concentration of 50mg/L and 25mg/L.Embodiment 152, under the drought stress condition, promote the indoor bioassay of winter wheat drought resistance root growth
To above-mentioned 1B 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2Add distilled water in the cream preparation, and stir, compound concentration is the soup of 200mg/L.During use, get this soup of 200mg/L, become the soup of 100mg/L, 50mg/L and 25mg/L again with an amount of distilled water diluting, with standby with pipette.
Vertically sprout the winter wheat experiment in the adverse circumstance simulated conditions, (add 210.6g sucrose in the 1000ml water, according to ψ with-15 sucrose solutions that cling to n=-icRT) is as the drought stress condition.At first, with winter wheat (north farming No. 2) seed respectively at 1B 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2In the variable concentrations of missible oil, carry out immersion treatment and reach 12 hours, 1B 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2The concentration of missible oil is got 25ppm and 50ppm respectively, is contrast with the winter wheat of water logging.Seed soaked after 10 hours, put in order on glass plate, utilized the capillary water absorption principle vertically to sprout again, and glass plate is vertically put into the container of the sucrose solution that-15 crust are housed, and adds a cover the climatic cabinate of putting into 20 ℃ again and sprouts.Sprout and investigate after 10 days, measure the fresh weight and the dry weight of radicle bar number, radicle length, radicle and plumule, the results are shown in table 11.
Table 11,1B 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2Missible oil improves winter wheat drought resistance test experimental result
Concentration Radical (bar) Root long (cm) Radical bud fresh weight (g) Radical bud dry weight (g) Moisture (g) Tissue water content (%)
CK - 2.3 1.5 0.06424 0.00814 0.0561 87.3
1B 2Missible oil 50ppm 3.5 2.0 0.09000 0.01125 0.0788 87.6
25ppm 3.8 2.5 0.09201 0.01230 0.0797 86.6
1D 2Missible oil 50ppm 3.1 2.0 0.08214 0.00992 0.0722 87.9
25ppm 3.3 1.9 0.07852 0.01002 0.0685 87.2
1F 2Missible oil 50ppm 3.7 2.4 0.09320 0.01236 0.0808 86.7
25ppm 3.5 2.6 0.09265 0.01302 0.0796 86.0
2B 2Missible oil 50ppm 3.4 2.2 0.08400 0.01025 0.0738 87.8
25ppm 3.6 2.4 0.08501 0.01130 0.0737 86.7
2D 2Missible oil 50ppm 3.3 2.4 0.08024 0.01102 0.0692 86.3
25ppm 3.0 2.6 0.07878 0.01011 0.0687 87.2
2E 2Missible oil 50ppm 3.0 2.0 0.08812 0.00994 0.0782 88.7
25ppm 3.2 2.4 0.09065 0.01002 0.0806 88.9
Annotate: data are the mean value of 10 strains in the table 6; Contrast (CK) sample root length when investigation in the 5th day is 0 with bud length.
The biological activity test test result of indoor drought resisting, by table 6 result as can be seen, 1B 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2No matter missible oil is 25mg/L, or 50mg/L, and under the water stress condition of-15 crust, wheat root amount (bar number and length) all is better than contrast (CK) significantly.Analyzing with the size of tissue water content numerical value, also is 1B again 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2The water content of missible oil is higher.As everyone knows, under the water stress condition, be that the size that how much reaches tissue water content of the root amount of seedling or plant all is the important indicator of its drought resistance of reaction.For this reason, we confirm 1B 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2Missible oil is the preferable formulation that winter wheat is improved drought resisting, the drought-resisting biological activity of doing well, and 25mg/L and 50mg/L are optium concentration in the indoor model experiment.
Promote the indoor bioassay of winter wheat salt-resistance root growth under embodiment 153, the condition of salt stress
To above-mentioned 1B 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2Add distilled water in the cream preparation, and stir, compound concentration is the soup of 200mg/L.During use, get this soup of 200mg/L, become the soup of 100mg/L, 50mg/L and 25mg/L again with an amount of distilled water diluting, with standby with pipette.
Vertically sprout the winter wheat experiment in the adverse circumstance simulated conditions, the NaCl solution with 2% is as condition of salt stress.At first, with winter wheat (north farming No. 2) seed respectively at 1B 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2After (concentration of 50ppm and 100ppm) soaked seed 12 hours in the variable concentrations of missible oil, winter wheat pendulum after will soaking seed in order is on glass plate, utilize the capillary water absorption principle vertically to sprout again, glass plate is vertically put into the solution container that 2%NaCl is housed, and adds a cover the climatic cabinate of putting into 20 ℃ again and sprouts.Sprout and investigate after 10 days, measure the fresh weight and the dry weight of radicle bar number, radicle length, radicle and plumule, the results are shown in table 12.
Table 12,1B 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2Missible oil improves winter wheat salt-resistance result of the test
Concentration Radical (bar) Root long (cm) Radical bud fresh weight (g) Radical bud dry weight (g) Moisture (g) Tissue water content (%)
CK - 3.0 4.5 0.242 0.043 0.199 82.2
1B 2Missible oil 50ppm 3.8 4.3 0.323 0.044 0.279 86.4
25ppm 4.0 4.5 0.349 0.046 0.303 86.8
1D 2Missible oil 50ppm 3.8 4.0 0.229 0.039 0.190 83.0
25ppm 3.6 4.6 0.280 0.042 0.238 85.0
1F 2Missible oil 50ppm 3.6 4.6 0.358 0.047 0.311 86.9
25ppm 4.2 4.8 0.372 0.048 0.324 87.1
2B 2Missible oil 50ppm 3.6 4.4 0.302 0.045 0.257 85.1
25ppm 3.8 4.6 0.329 0.051 0.278 84.5
2D 2Missible oil 50ppm 3.4 4.0 0.249 0.038 0.211 84.7
25ppm 3.5 4.5 0.268 0.042 0.226 84.3
2E 2Missible oil 50ppm 3.9 4.8 0.340 0.050 0.290 85.3
25ppm 4.2 4.8 0.376 0.053 0.323 85.9
Annotate: data are the mean value of 10 strains in the table 7.
The biological activity test test result of indoor anti-salt is by table 7 interpretation of result, from the bar number of root, 1B 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2Missible oil all is better than contrast (CK), promptly shows 1B 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2Missible oil all has short root effect.But from the length of root, its short root effect also has certain difference, 1B 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2The long part of the root of two concentration of missible oil is less than contrast (CK).Under condition of salt stress, root system is the organ that at first is hurt, and the length of root amount, particularly root is one of important indicator of crop salt-resistance.Size 1B from tissue water content 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2Missible oil has more tissue water content, can keep water supply preferably, also can keep the normal physiological function of long period, to alleviate the degree of salt damage.By above root amount and two indexs of tissue water content, 1B 2, 1D 2, 1F 2, 2B 2, 2D 2, 2E 2Missible oil is the preferable formulation of raising winter wheat salt-resistance, the anti-salt biologically active of doing well, and 25mg/L and 50mg/L are optium concentration in the indoor model experiment.

Claims (8)

1, a kind of pesticidal preparations that contains saturated five-membered heterocycles is characterized in that: contain saturated five-membered heterocycles shown in formula I, formula II or the formula III as effective ingredient
Figure A2005101306670002C1
Formula I
Wherein: X 1=O or S; X 2=O or S; X 3=O or S;
R 1=CH 3Or H; R 2=H, CH 3, CH 2Cl, or CH 2OH;
And: work as X 1, X 2, X 3During=O, R 1: R 2≠ H
Figure A2005101306670002C2
Formula II
Wherein: X 1=O or S; X 2=O or S; X 3: O or S;
R 1=CH 3R 2=H or CH 3R 3=H, CH 3, CH 2Cl, or CH 2OH
Formula III
Wherein: X 2=O or S; X 3=O or S;
R 2=H or CH 3: R 3=H, CH 3, CH 2Cl, or CH 2OH
2, the pesticidal preparations that contains saturated five-membered heterocycles as claimed in claim 1 is characterized in that: also comprise solvent and surfactant, and the ratio of three kinds of components is
Saturated five-membered heterocycles 5～20 weight portions
Solvent 65～90 weight portions
Surfactant 2～7 weight portions.
3, the pesticidal preparations that contains saturated five-membered heterocycles as claimed in claim 2 is characterized in that: described solvent is toluene, N, dinethylformamide, methyl alcohol, ethanol, acetone, soya-bean oil, diesel oil or machine oil.
4, the pesticidal preparations that contains saturated five-membered heterocycles as claimed in claim 2 is characterized in that: described surfactant is APEO, TritonX, farming breast, Tween-80.
5, the described pesticidal preparations that contains saturated five-membered heterocycles of one of claim 1～4 is being used for desinsection, sterilization, is reaching plant growing activation, the drought resisting that improves plant, the application aspect the anti-salt alkali ability, and institute's method of application is seed soaking and foliage-spray.
6, the purposes that contains the pesticidal preparations of saturated five-membered heterocycles as claimed in claim 5, it is characterized in that: when being used for desinsection, the working concentration of the saturated five-membered heterocycles shown in active ingredient wherein---formula I, formula II or the formula III is 100～200ppm.
7, the purposes that contains the pesticidal preparations of saturated five-membered heterocycles as claimed in claim 5, it is characterized in that: when being used for sterilization, be suitable for apple wheel line bacterium, the working concentration of the saturated five-membered heterocycles shown in active ingredient wherein---formula I, formula II or the formula III is 50ppm.
8, the purposes that contains the pesticidal preparations of saturated five-membered heterocycles as claimed in claim 5, it is characterized in that: when being used for the coordinate plant growth activity, being suitable for using crop is beet, watermelon, tomato, capsicum, cucumber, clover, cotton, asparagus lettuce, wheat, corn, soybean and flowers, and the working concentration of the saturated five-membered heterocycles shown in active ingredient wherein---formula I, formula II or the formula III is 10～100ppm.
CN 200510130667 2005-12-20 2005-12-20 Pesticide preparation containing saturated guinary heterocyclic compound and its use Pending CN1985593A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102933083A (en) * 2010-04-09 2013-02-13 拜耳知识产权有限责任公司 Use of derivatives of the (1-cyanocyclopropyl)phenylphosphinic acid, the esters thereof and/or the salts thereof for enhancing the tolerance of plants to abiotic stress

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102933083A (en) * 2010-04-09 2013-02-13 拜耳知识产权有限责任公司 Use of derivatives of the (1-cyanocyclopropyl)phenylphosphinic acid, the esters thereof and/or the salts thereof for enhancing the tolerance of plants to abiotic stress
CN102933083B (en) * 2010-04-09 2015-08-12 拜耳知识产权有限责任公司 The derivative of (1-anocy clopropyl) phenyl phosphinic acid or its ester and/or its salt improve the purposes of plants against abiotic stress tolerance

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