CN1009417B - Method for control of soil-borne insects - Google Patents
Method for control of soil-borne insectsInfo
- Publication number
- CN1009417B CN1009417B CN85107462A CN85107462A CN1009417B CN 1009417 B CN1009417 B CN 1009417B CN 85107462 A CN85107462 A CN 85107462A CN 85107462 A CN85107462 A CN 85107462A CN 1009417 B CN1009417 B CN 1009417B
- Authority
- CN
- China
- Prior art keywords
- compound
- soil
- chloro
- cis
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for controlling soil-borne insects such as southern corn rootworm is disclosed and exemplified in which a pyrethroid selected from mono- and di-fluorophenylmethyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-diemethylcyclopropanecarbo xylates is applied to the soil for insect control.
Description
The present invention relates to the general field of insecticide, in soil, add 3-(2-chloro-3 specifically, 3,3-three fluoro-1-acrylic)-2, certain benzyl esters of fluoridizing of 2-dimethyl cyclopropane carboxylic acid control geophilous insect particularly the main time of its larva life such as the southern corn rootworm the insect of in soil, spending.
United States Patent (USP) 4,332,813 have revealed the perhaloalkyl radical vinyl cyclopropanecarboxylcompound of multiclass, being called as for Lepidoptera and homopteran has the excellent insecticidal effect.This patent description these compounds best contact and blade effect are arranged, but to eliminate geophilous insect role then be record not to relevant these compounds.
Its publication number of european patent application is that 10879A1 revealed once that certain crossed the benzyl esters of fluoridizing of alkylhalide group vinyl cyclopropane-carboxylic acid, and particularly its four halogen phenylester and phenyl-pentahalide base ester can be made fumigating insecticide.The use of the compound of control soil insect has been revealed in this application, and shows the effect of four halobenzene methyl and phenyl-pentahalide methyl compound.Yet relevant of the present invention one or the report data of difluoro benzylated title compound represent that a kind of scored cucumber beetle (Diabrotica balteata) that these compounds spend for its young life is inoperative basically in soil.
The serial number of application on March 14th, 1984 is 589 simultaneously, 622 U.S. Patent application was once revealed and was used 2,4,6-trifluoro-benzene methyl 3-(2-chloro-3,3,3-three fluoro-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester is controlled at geophilous insect, this reveal content that content and the european patent application of pointing out above reveal not the professional in this technical field propose of the present invention one or the difluoro benzyl esters geophilous insect is had bigger significantly effect.
Have now found that certain cis-3-(2-chloro-3,3,3-three chloro-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester, 2-fluorobenzene methyl and 2 particularly, 6-difluoro benzyl esters (at United States Patent (USP) 4,332, comprised in 815 the claim and in above-mentioned european patent application concrete illustrational compound) to showing surprising effect such as southern corn rootworm (Diabrotica undecimpunctata howardi).
According to above-mentioned situation, the invention provides a kind of method of preventing and treating geophilous insect, this method is included in and plants one or more compounds of the present invention that add about 0.2～8 weight portion in plant or the soil with plant species in per 1,000,000 weight portion soil, 2-fluorobenzene methyl or 2 particularly, 6-difluoro benzyl 3-(2-chloro-3,3,3-three fluoro-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester.
These compounds have at the general structure shown in the molecular formula I, wherein n=1 or 2
Used compound and certain intermediate thereby exist with cis and trans geometric isomer among the present invention are cis or trans on the vinyl group correlation of 1 and 3 locational carboxyl of cyclopropane ring and replacement.Otherwise the preparation of this compounds provides the mixture (naming to suitable, anti-) of cis and transisomer usually wherein can change on wide wide scope along ratio.
Because position of cyclopropane ring 1 and position 3 are asymmetric carbon atoms, four optical isomers are also arranged, they can name and be 1R, cis; 1S, cis; 1R, trans; And 1S, trans.
Compound of the present invention can be used as E or Z isomer or as E and the existence of Z mixture of isomers, this depends on the substituent relation spatially on substituent on the alpha-carbon atom of vinyl group and the beta carbon at vinyl group.
Well-known in the cyclopropanecarboxylcompound technology have sizable difference aspect insecticidal action horizontal between cis and transisomer.As between the cis and transisomer of known synthetic cyclopropanecarboxylcompound, cis-isomer is usually than transisomer better effects if, and also better than the mixture effect of cis and transisomer, although such was the case with.About E and Z isomer similar difference is being arranged also aspect the effect.
Unless have opposite purpose to represent, embodiments of the invention and comprise that wherein at 1 and 3 the locational carboxyl of cyclopropane ring and the vinyl group of replacement be cis or all trans compounds, or the relevant mutually cis and the mixture of anti-configuration; Cis-isomer is especially with 1R, and cis-isomer is generally the best.It also is that the present invention is desired also within the scope of the present invention that analogue has other E and Z isomer and composition thereof.
The preparation of compound can be used the whole bag of tricks known to the ordinary skill in the relevant technologies field, is included in this United States Patent (USP) of classifying reference as 4,332,815 described those methods.The method easily for preparing this compound is the compound by the structural formula II
Wherein R is a carboxyl, and lower alkoxy or halogen and comprise 2-luorobenzyl alcohol or 2, and 6-difluorobenzyl alcohol residue reacts, and for example itself reacts with pure when II is acid chloride.
The compound 2-fluorobenzene methyl that obtains is suitable-3-(2-chloro-3,3, and 3-three fluoro-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester (compd A) is a kind of oil.
NMR (Nuclear Magnetic Resonance) spectrum and specified structure: δ (CDCl
3, TMS) 1.32(S, 6E), 2.08(t, 2H), 5.21(S, 2H), 6.83-7.63(m, 5H) consistent.
C
16H
15ClF
4O
2The computational analysis value: C54.81, H4.82
Discovery value: C55.06, H4.53
The compound 2 that obtains, 6-difluoro benzyl is suitable-3-(2-chloro-3,3,3-three fluoro-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester (compd B) is a kind of oil.
NMR (Nuclear Magnetic Resonance) spectrum and specified structure: (CDCl
3, TMS) 1.28(S, 6H), 2.04(t, 2H), 5.24(S, 2H), 6.73-7.56(m, 4H) consistent.
C
16H
14ClF
5O
2The computational analysis value: C52.12; H3.83
Discovery value: C52.76; H4.10
In the method for the invention by will be wherein composition combine and maybe will plant the soil of crops (being the worm place of infesting) and apply reactive compound planting crops.This can be finished by laxative remedy, promptly sows this composition on the zone that maybe will plant in the zone of having planted or in conjunction with the root that is applied to plant maybe plantation place.The quantity that is added to the composition in root district when clearly, using back one method must be enough so that the concentration of the active component of being supplied with in soil is very effective to desinsection.The proper proportion of the active component of using to about 5 kilograms, and is the best with 0.2～1.5 kilogram/hectare as per hectare 0.1 for this purpose.
Employed in the method for the invention typical prescription comprises that active component goes up acceptable carrier with agricultural or replenishers combine, and is the best to be used in combination surfactant, and can chooses other active components wantonly.The formulation that is suitable for comprises different big or small particles, powder, wettable powder, emulsible concentrate, solution, dispersion etc., and its selection can be decided according to haunt in the insect pest environmental factor at place and selected application method.Because the difference of the different and desired application mode of used additive and carrier, representative formula may alter a great deal on the concentration of active component.Thereby the concentration that active component presents counts 0.1% to 99.5% by the weight of formulation.On the agricultural acceptable carrier can account for formulation weight about 99.5% to being low to moderate 0.5%.The surfactant that is suitable for, as be used for filling a prescription and can present different concentration, be advisable to 30% with 1% by its scope of weight of formulation.
When using formulation, can be diluted to the concentration that to use with being convenient to the diluent or carrier that active component disperses to be suitable for.When diluting for the ease of using, the concentration range of active component is about 0.0001 to about 10% on weight, and low concentration is particularly useful when thinner is water.
Compound of the present invention stood filter paper test and having added use in the soil by G.R. Sai Teer (Sutter) (J.Econ.Entom.) roll up 75(3 at " economic entomology magazine "), the test of the conventional method that proposed in 489-91 page or leaf (1982) one literary compositions kill the 3rd age southern corn rootworm larva, this method is listed as for referencial use herein.
Example 1
Filter paper test
When filter paper test, with compound dissolution of the present invention in ketone/water so that obtain comprising the testing liquid of the specific concentrations of test compound.With diameter is that 100 millimeters filter paper is placed in 100mm easy disposal, plastics * 15mm Petri dish, and 2.5 milliliters testing liquid is poured on above the filter paper.In excessive water evaporation back (evaporate 1-1.5 hour), ten the 3rd or four-age larva be placed on the filter paper that wets and with Petri dish cover.Each compound carries out twice same test.24 hourages go out in heaven and dying larva number after infecting insect.And obtain the percentage that kills.Report the result and see Table 1.
Table 1
Filter paper test under 1ppm concentration
Kill the percentage phenyl
Compound number southern corn rootworm
aStriped cucumber beetle
bSubstitute
A 90 100 2F
B 100 100 2F，6F
C 90 95 3F
D 65 30 4F
E 100 100 2F，4F
F 100 100 2F，5F
G 95 100 3F，4F
H
c95 100 2F，4F，6F
Annotate a: southern corn rootworm (Diabrotica undecimpunctata howardi)
B: striped cucumber beetle (Diabrotica balteata)
C: compound H is 2,4, and 6-trifluoro-benzene methyl is suitable-3-(2-chloro-3,3,3-three fluoro-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester is application on March 14th, 1984, U. S. application number is 589,622 compound.
Table 1 expression compound of the present invention is effective with the larva that kills two kinds of different insects kinds spending its larva life in soil under the millionth low concentration.In view of being that killing with higher substantially concentration of being reported in the european patent application of 10879A1 lacks validity aspect a kind of insect in these kinds at publication number, so these results are beyond thought especially.
Adding the pilot scale of burying tests
The preparation method of the liquid storage of each test compound is dissolving this compound of 4.8mg and with the ketone of 90ml/water dilution (1: 9) in the acetone of 10ml.This liquid storage 5ml is added to is placed in the air-dry viscosity loam of 30 in 3 ounce plastic cups grams, the concentration that makes the test compound in the soil is 8/1000000ths to be 8ppm.Use the liquid storage of a series of dilutions so that obtaining the concentration of the test compound in the soil is 4,2,1,0,5,0.25 and the various soil of 0.125ppm.All be that the 5ml solution that will have required concentration is added in the soil of 30 grams in all cases.Allow treated soil not add a cover to be placed in the fume hood 0.5 hour so that with acetone evaporated.Before soil is put the southern corn rootworm into, that soil is thoroughly mixed.With two grow three days corn bud and ten early the southern corn rootworm larvas of the third phases (growing 9～10 days) be put in the cup, cover vinyl cover then and remain in the airtight plastic sack.After storing 48 hours under 74-78 the temperature, cup is taken out from plastic sack, remove lid and each wine is placed on the lethality of obtaining larva in improved Bai Erlaisi (Berlese) the polyethylene funnel that 18 order mesh screens are housed.Again funnel is placed on the solution container that contains washing agent above.Incandescent lamp (100 watts) is placed on 36cm place above the soil specimen.Slowly make antecedent soil moisture from the heat that these bulbs produced, the feasible larva that is not subjected to the test compound effect gets out soil and falls in the detergent solution.The larva that does not get out soil can be judged dead.Try to achieve the per cent death loss of every kind of concentration in this way.Under each concentration, carry out twice test equally.
Because it is all different every day to add the possibility of result that the pilot scale of burying tests, this is owing to there is uncontrollable factor, the accurate development and the state that for example are used to the health of the larva tested, the reference compound (but inactive component) that can effectively kill insect in the soil when adding the pilot scale of burying each time and test is included, and it is invalid for insect.The initial data of each compound is deposited in the calculator that is composed of program to proofread and correct LC blank and calculating this used compound in this test
50Value.Underproof then compound can be compared with the normative reference in same test and be obtained relative effectivenes.Relative effectivenes (RP) is defined as LC
50Reference compound/LC
50Test compound.Can carry out more accurate comparison with the compound of evaluating at different time after this mode.Table 2 is represented the effect of some compound of the present invention and has been illustrated the method for asking of relative effectivenes.
Be recorded in result of the test in the table 2 and express compd A and compd B each has all shown the unexpected high base level that kills the effect of southern corn rootworm, and each compound kill aspect the southern corn rootworm more effective significantly than the trifluoro base analog of prior art.
Table 2
Kill aspect the southern corn rootworm fluorobenzene methyl suitable-3-(2-chloro-3,3,3-three chloro-1-acrylic)-2, the insecticidal action of 2-dimethyl cyclopropane carboxylic acid ester in soil.
Use percentage and kill percentage
The reference of compound reference compound reference compound
A compd B compound H compound
4.0ppm 100 - 95 - 100 -
2.0 85 90 95 100 85 85
1.0 75 80 90 95 85 75
0.5 70 75 85 60 70 70
0.25 65 45 65 40 25 40
0.125 - 35 - 10 - 35
LC
50（ppm） 0.27 0.38 0.14 0.45 0.4 0.3
Rp 1.4 1 3.2 1 0.75 1
Reference compound is (2-methyl [1,1 '-phenylbenzene]-3-yl) methyl cis-3-(2-chloro-3,3,3-three fluoro-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester.
The relative effectivenes of phenyl-monofluoride methyl ester of the present invention and difluoro benzyl esters is listed in the table 3.
Table 3
Relative effectivenes when adding the pilot scale of burying and testing
Relative effectivenes
Compound is to soil
bIn the southern corn rootworm
a
A 1.5
B 3.4
B′ 2.05
C 1.08
D 1
E 0.78
F 0.72
G 0.62
H 0.75
Reference compound 1
Annotate a:Diabrotica undecimpunctata howardi
B: at the middle 3-(2-chloro-3,3 of B ', 3-three fluoro-1-acrylic)-2, the ratio of the cis/trans of 2-dimethyl cyclopropane carboxylic acid ester is 75/25.B comprises the cis-isomer greater than 98%.
The present invention can prevent and treat other comprise geophilous insect: Japanese beetle (Popillia japonica Newman), black cutworm (Agrotis ipsilon), Oregon wireworm (Melanotus oregonensis), corn wireworm (Melanotus communis), bay wireworm (Conoderus amplicollis), southern potato wireworm (Conoderus falli) and prairie cereal wireworm (Ctenicera aeripenni destructor).
Claims (8)
1, a kind of southern corn rootworm in the soil and method of striped cucumber beetle of preventing and treating, it is characterized in that it comprises to kind plant being arranged or want to add in the soil of plant species the comprising from by single and difluoro benzyl 3-(2-chloro-3 of insecticidal effective dose, 3,3-three fluoro-1-acrylic)-2, one or more compounds of selecting in one group of compound that 2-dimethyl cyclopropane carboxylic acid ester is formed and one or more agriculturals go up acceptable carrier, the composition of replenishers or adjuvant.
2, the method for claim 1 is characterized in that carboxylate is fluorophenyl methyl alcohol or 2, the ester of 6-difluorophenyl methyl alcohol.
3, method as claimed in claim 2 is characterized in that compound is a 2-fluorobenzene methyl 3-(2-chloro-3,3,3-three fluoro-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester.
4, the method for claim 1 is characterized in that active component is 2,6-difluoro benzyl 3-(2-chloro-3,3,3-three fluoro-1-acrylic)-2,2-dimethyl cyclopropane carboxylic acid ester.
5, the method for claim 1 is characterized in that wherein used active component mainly is cis or mainly is 1R, cis-isomer or its mixture.
6, the method for claim 1 is characterized in that the consumption of the active component used is 0.1 to 5 kilogram of a per hectare.
7, the method for claim 1 is characterized in that it is surfactant that agricultural goes up acceptable carrier, replenishers or adjuvant.
8, method as claimed in claim 7 is characterized in that agricultural goes up the 0.5-99.5%(weight that acceptable carrier, replenishers or adjuvant account for the composition gross weight).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US65938484A | 1984-10-10 | 1984-10-10 | |
| US659,384 | 1984-10-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN85107462A CN85107462A (en) | 1986-06-10 |
| CN1009417B true CN1009417B (en) | 1990-09-05 |
Family
ID=24645184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN85107462A Expired CN1009417B (en) | 1984-10-10 | 1985-10-08 | Method for control of soil-borne insects |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0197115A4 (en) |
| JP (1) | JPS61501709A (en) |
| KR (1) | KR870700285A (en) |
| CN (1) | CN1009417B (en) |
| AR (1) | AR247656A1 (en) |
| AU (1) | AU564889B2 (en) |
| BG (1) | BG51231A3 (en) |
| BR (1) | BR8506967A (en) |
| DK (1) | DK269286D0 (en) |
| GR (1) | GR852434B (en) |
| HU (1) | HUT41236A (en) |
| IL (1) | IL76595A (en) |
| WO (1) | WO1986002238A1 (en) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2831193A1 (en) * | 1978-07-15 | 1980-01-24 | Bayer Ag | FLUORALKENYL-SUBSTITUTED CYCLOPROPANCARBONIC ACID ESTERS AND THEIR USE AS INSECTICIDES |
| ZA795532B (en) * | 1978-10-27 | 1980-09-24 | Ici Ltd | Halogenated esters of cyclopropane acids,their preparation compositions and use as pesticides |
| DE2965291D1 (en) * | 1978-10-27 | 1983-06-01 | Ici Plc | Halogenated esters of cyclopropane acids, their preparation, compositions and use as pesticides |
| US4332815A (en) * | 1979-06-25 | 1982-06-01 | Fmc Corporation | Insecticidal perhaloalkylvinylcyclopropanecarboxylates |
| EP0031199B1 (en) * | 1979-12-21 | 1983-12-14 | Imperial Chemical Industries Plc | Substituted benzyl esters of cyclopropane carboxylic acids and their preparation, compositions containing them and methods of combating insect pests therewith, and substituted benzyl alcohols |
-
1985
- 1985-10-01 BR BR8506967A patent/BR8506967A/en unknown
- 1985-10-01 EP EP19850905156 patent/EP0197115A4/en not_active Withdrawn
- 1985-10-01 WO PCT/US1985/001898 patent/WO1986002238A1/en not_active Application Discontinuation
- 1985-10-01 JP JP60504542A patent/JPS61501709A/en active Pending
- 1985-10-01 HU HU855033A patent/HUT41236A/en unknown
- 1985-10-01 AU AU49525/85A patent/AU564889B2/en not_active Ceased
- 1985-10-06 IL IL76595A patent/IL76595A/en unknown
- 1985-10-08 CN CN85107462A patent/CN1009417B/en not_active Expired
- 1985-10-08 GR GR852434A patent/GR852434B/el unknown
- 1985-10-08 AR AR85301877A patent/AR247656A1/en active
-
1986
- 1986-06-09 BG BG075271A patent/BG51231A3/en unknown
- 1986-06-09 DK DK269286A patent/DK269286D0/en not_active Application Discontinuation
- 1986-06-10 KR KR1019860700343A patent/KR870700285A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HUT41236A (en) | 1987-04-28 |
| AR247656A1 (en) | 1995-03-31 |
| GR852434B (en) | 1986-02-10 |
| AU564889B2 (en) | 1987-08-27 |
| EP0197115A1 (en) | 1986-10-15 |
| BG51231A3 (en) | 1993-03-30 |
| JPS61501709A (en) | 1986-08-14 |
| BR8506967A (en) | 1986-12-23 |
| AU4952585A (en) | 1986-05-02 |
| DK269286A (en) | 1986-06-09 |
| IL76595A (en) | 1988-11-30 |
| WO1986002238A1 (en) | 1986-04-24 |
| DK269286D0 (en) | 1986-06-09 |
| EP0197115A4 (en) | 1989-08-29 |
| KR870700285A (en) | 1987-12-28 |
| CN85107462A (en) | 1986-06-10 |
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