Method of insects, mites and nematodes control

专利摘要:
O-alkyl-O-[1,5-disubstituted-1,2,4-triazolyl-(3)]-thiono-phosphoric (phosphonic) acid esters and ester-amides of the formula <IMAGE> (I) in which R is alkyl of 1 to 6 carbon atoms, R' is alkyl, alkoxy or alkylamino of 1 to 6 carbon atoms or phenyl, R'' is alkyl or cyanoalkyl of 1 to 4 carbon atoms or alkenyl of 3 or 4 carbon atoms, R''' is alkyl or cyanoalkyl with 1 to 6 carbon atoms in the alkyl radical, and X is oxygen or sulfur, which possess insecticidal and acaricidal properties.
公开号:SU713527A3
申请号:SU741989776
申请日:1974-01-11
公开日:1980-01-30
发明作者:Хоффманн Гелльмут；Хамманн Ингебогр；Беренц Вольфганг；Хомейер Бернхард；Штендель Вильгельм
申请人:Байер Аг (Фирма)；
IPC主号:

专利说明:

(54) METHOD OF FIGHTING, S WITH N.4 SECOND, CLUSHES AND LIL-MATOLS
The invention relates to chemical methods of fighting time of the farm, agriculture, in particular to the method of fighting nasocynograms and nematodes. The known method of combating agricultural pests by treating them or their biotics with an active principle is based on 0.0 - dimesh1-0-3-methylpyrazole- (5) -yl-tionophosphoric acid 1. However, at low levels of cocy-; its central efficiency is insufficient. The chain of the invention is the search for a new way of combating asecamas, flares and nematodes, which is extremely efficient. heterocyclic nitrogen-containing acidic phosphorus derivatives. This goal is achieved by a technical solution, represented by a new {mi new stusob to combat insects, mites and nematodes, by treating them or x biotope with a heterocyclic nitrogen-containing acid derivative (phosphor of the general formula where R is alkyl Cj-C-,; R is ZTIH -, alkoxy Cj-Ci. isopropushamino, phenyl; R - alkyp Cj-Cj, anmethyl, allyl; ajiKtui Ci-Cz; X - oxygen, sulfur, in a quantity of 0.0001 - 10 weight .. Forms of drug use are usual. CoeziKtJeHHH of formula j is obtained if the halide: zfir or amide ether of gionophosphoric (phosphonic) acid of formula II de R and R have The indicated values, and Hal means halogen, preferably a chlorine atom, are subjected to the reaction of an exchange reaction and with triazolyl hydrogen derivatives of HKR, where X, R and R uNteioT are indicated in the presence of an acid acceptor or in the Bi-uie corresponding salts, and in the mixture, the hychrothers in the presence of an acid acceptor or in the Bi-uie correspond to the alkaline salts, and the ligates are in the presence of an acid acceptor or in the Bi-uie corresponding to the hydrochloric acid, in the presence of an acid acceptor or in the Bi-uie corresponding to the hydrochloric acid in the presence of an acid acceptor or in the Bi-uie corresponding to the hydrochloric acid) ammonium Triazoles of 1P formulas can be obtained in principle by well-known methods: a) in the event that X means a sulfur atom (. To E is estl1-le derivatives of thiosemicrbazidog) ({u mu l1, H, t ...- s -ji -.- HH ,, (lYj - С --н .-- т- со, с, 11 fv) (, ... S. shis residue, iianpHMepj ha, W “g,, -,. ,, aikpizayii, -Ljli5 II- P, -HZ / 6) in the event that X means oxygen, ethyl chloroformate ester acts to react with rolling, 1 cal, and then with the removal of the mixture, the formula PS 11.1 С jHjO - С -1Ш - С - ОБ, {- Where R has been indicated with a value of 1. And these are interstitial products of gyvergathot and f3 n C} t: stBSH n oizvodn111h TTI) el azine niklizatsii eduyuschey with xe e: OS IIn OR + n, 1t- and c-to -WI - C N-l-l-R nolucheni new substances according to the invention is carried out using nredpochtitelno sootvetstvuyun1ih solvents and diluents. Almost all inert orthanic solvents are used as solvents. These include especially hyphagic and aromatic. if necessary, chlorinated hydrocarbons, for example.) benzene, toluene, xylene, gasoline, methylene chloride, chloroform, carbon tetrachloride, i, chlorobenzene, etc., such ethers as cystic and dkbutyl, daoxane, further ketones, for example, adeton, .metilati.lovy, mettigzzonroniiyuv1 and methi.isobutyl gy keyuI m, in addition, W Trilles, for example, aceto-and droshyunitril. As acid acceptors, common acid binding agents, preferably alkali metal carbonates and alkoxides, sodium nitrates, carbonates, methylates or ethesates of sodium and potassium, then ali ()) atic are used. aromatic or tetrocyclic amines, for example, triztilamine,; timethyl min, lime1T lanilin, dimethylbenzylamine, and pyridi) {. The first one is the reactions of the GYUYNYA BA Girovat in pppyukh prelelah. The process is carried out at a temperature of 0 ° C and 20 ° C, preferably at 20 ° C to 70 ° C, and the reaction of decomposition is usually carried out at normal temperature. Ll of the propellant process, the waste materials are berl / g, usually about squimol p1) 1x quantities, the reaction about the exchange decomposition of ved; rm is preferably in one of the specified form 0 l those; 1, in the case of the need. in the presence of an ACID acceptor}, with the indicated gelp1sra; urah, Pos, le (and during the last few hours, in most cases), with additional gemrachures, the reaction mixture is cooled, poured into oxen and absorbed in an organic solvent, for example benzene. The mixture is then separated by the usual method of extruding orgapichex. F | a3i, i. 11 dissolve dissolve; and, if necessary, distillation of the residue, iioBr. soybeans are recovered in the bulk of oil: iL4i i, in the form of oils, kuray not partly distilled without decomposition, but by means of hack called initial distillation, t, s, 1p . -Large heating with reduced lavage up to slightly noiibiHicHHi.ix, te.impractors, have been freed from P (x; second, blinding combiOirjHTOB and thus cleared), and they are previously sterilized with tacceral syndrome.
Example 1
.СНз
(CHZO) rR-o- {f
N-G-SNT
to a mixture of 159 g (0.1 mol) of 1-methyl-3-hydroxy-5-methylmercaptotriazole- (1,2,4) and
15 g of potassium carbonate in 250 ml of acetohydrogryl add 16 g (0.1 mol) of 0,0-dimethylthionophosphoric acid diester chloride dropwise, while the internal temperature rises slowly to 22-30 ° C. After stirring for 4 hours at room temperature and subsequently heated during
(CjHgO
.Р-0
 I K-lT-CTj
(C, H50 P-0-4 I
1 - YAG-SNZ
(SNSO) - OR - I
N - And - With Shch-from
SzN7-T N Y
h
- ° H I
X
Cjhso
 Schj
// v I
/ P-0-l CjHgO H-1-CzH7-of
, t-CjH50) (
N-
.SCHj

N (СНзО) гР-0-
2 hours to 55-60 ° C, the reaction mixture is cooled, poured into water and this mixture is absorbed in benzene. The organic phase is washed, dried, the solvent is evaporated under reduced pressure and the residue is subjected to an initial distillation.
 19 g (71% of Teopmi) of 0.0-dimethyl-and-G1 -methyl-5 -methyl ltercaptotriazole (1,2,4) -yl- (3) thionophosphoric acid ester with
the refractive index of p is 1.5311.
The following compounds, presented in Table 1, can be prepared by analogy.
15
Table
15
R8

ze
64
.5114
at
Sch,
74
.5159
D
k - n-j-u3a
28
76
1.551:
T)
80
1.5125
T)
n D
1.5224
2
S-CHj.-CH CHi
i
ICpHjOJ P-o-x
Nn-CjHg
-S-CH -CN
STT
(C, H50), - 0- (I
-Y-iTC KS
OSSN
(X
- / P - 0 -Dh; With HgO
It-CHj S11- / °
(c 2,1150) 77-0-k -B cHj
Zshz
Sn
(CjHsOj P-O

 -UJ0,
with;, /
 S V-1I - C, H5
KSS
-tj .30-СзН70 И у
city yy I
Bn-CjHy-uji)
of.-szn,
CH-jO- l i G. “
5 - - from
Trnazolyl derivatives of CT, used as starting materials, half a dozen, for example, in the following way:
ASO- -Siz
(17) I NO
Continued gab. 1 C 14
24
1.5160
86
l
1.5184
71
1E
, 28
1.5576
58
B
24
75
1,4887
B
74
1.5089
B
68
1.5278
2 1
71
, 5045
D
68
1.5090
D
sns
35.4 g (0.2 mol) of HjN-CS-N-NH-CO-OQf (obtained from megylthiosemicarbazide and hafaronic acid diethyl ester (tlsh. 17CfC) and 0.2 mol of sodium methoxide, dissolved in 100 ml of methanol, are heated within 5 hours under reflux, then evaporated at {pressurized pressure, the residue is dissolved in water and precipitated again with hydrochloric acid. IlojryTjaroT 17 g (65% of theory) COCJIHH of formula 17 with a melting point of 250 ° C. Similar can be from NgM-SB-M-MH-CO-OSSNd (from the p-id of ethyl ester of N-goo-propyltolic acid and potassium rhodanide, Tll. 168 ° C) or HjN-CS-N-NHCO-OCjHjCnoJ yreH from ethyl ether N-ztilutolnoy acid and potassium thiocyanate, t.gt. 133 ° C) to obtain guides soedinenush: HH H-SPP-j -iso -kn mp.. 228 ° C; yield 60% of theory. 13.1 g (0.1 mol) of the compound obtained by the described method A (1) and 6 g of potassium hydroxide are dissolved in 50 ml of water and mixed with 12.6 g of dimethyl sulphate. This mixture is stirred for 2 hours at 25 ° C, the reaction solution is taken up in methylene chloride and separated in the usual way. Obtain 143 g (98% of theory) of 1 -met, -3-hydroxy-5-methylmercaptotriazole- (1,2,4) with so pl. 130 ° C. Similarly, you can SCllj n-СзН7-sha BUT output from the theory of scacj T.PL. 91-93 ° C; yield 33% of theory. .g-C "-" P I IT-HC Hg A solution of 73 g (0.5 mol) of 1-ethyl-3-c-triazolthion- (5) in 300 ml of methanol change - 10 first with 0.5 a mole of sodium methane; gpiom with 38 g of chloroacetonitrile, the reaction mixture having a temperature of from 30 to 40 ° C. After exchanging for c}, the precipitate formed is sucked off, the filtrate is concentrated under reduced pressure, the residue is triturated with water, sucked off and dried. recrystallization from acetonitrile gives 19 g (20.6% of theory) -ethyl-3-oxy-5-dianmethylmercaptopirazole (1,2,4) with tll. 127 ° C. The reaction of interaction with an allybro ID can be done in an analogous manner by a creep, K.ZSNg-CH-Syag t. G. 76-77 yield 35% of theory. B (1) C.HgO-C-NH-C-OCH (25) to a solution or from 300 g (3 mol) of potassium rhodanide to a solution in SOO ml of dry acetone; 1, 327 g of SUPRECT chloroform acid ester. yy} eichsm the temperature of the mixture rises to 30-40 ° C. the latter is stirred for 3 hours and then at 50-60 ° C, 200 ml of methanol is added with perspersptvani. After over-stirring overnight, the OTcacbrBaJOT is solid, KONfflOHCHTbi, the filtrate is evaporated under reduced pressure and the residue is mixed with a small amount of water. After suction and drying, half of 314 g (64% of the theoretical yield) of L-carbethoxythiomethyl fetan with m.p. 48 C. By reacting with ethyl chloroformate ACID, it is possible to likewise crawl O5 O-C-NH-C-OC H yield 61. 46 C; from theory. h B (2) OCHN N --- N - CH To 163 g (1 moshl N-carbl- (1k-ciio, mc1n.11 retan. dissolved in 500 ml of methanol, add 46 g of meatsp-ilrassh1a. and the reaction solution rises to 0--30 ° C. Then this mixture is cleansed at about 80 ° C and then boiled for 2 hours with an M condenser. After cooling, the precipitate is sucked off and lepekp l: i 1iz () T from methanol, 1 fi this get 44 i (34. from eoria) - 1-metal-3 - hydroxy - 5 - labels-sy11ira-.i) L (1,2,4) with t, pl. 216 ° C. By using N-carbethoxythioethylurethane, the following compound can be obtained in an anapogated manner: t ir-CH, tlsh. 162 ° C; Zykhod 55% of theory. Example A. Ogalt with horseradish larvae larvae - Phaedon. Solvent: 3 weight.h. acetone. Emulsifier: 1 weight.h. alkyl aryl polypolycoleum j ifipa. For ps) .1 | uchs P syschivayut it with the specified kolichestest (Experience with Phaedon larvae)
Active substance
sns
//
0-1
to - and
1 of & eu pio
and (smgr-h
-N-
,
II0
7T-11G,
-ZSNz

|
h
-74
and
N
SzN7-ize
Sch3
V -
/ about-
13th
SNS 5
Table
The degree of killing,%, after 3 days
3
2
0.1
0.1
100 00 0.01
100
0.1 100 0.01
100 100
100
100
0.1 100 0.01 V of a solvent containing the indicated amount of emulsifier and dilute the concentrate with water to the desired concentration. Prepared active substance is sprayed to the formation of cabbage leaves (Brassica oleracea) and droplets of horseradish leaf beetles are planted on them (Phaedon cochlea). After these periods, the degree of killing (%) is determined. none of the larvae was euthanized.The active substances, their concentrations, the timing of determination and the results are shown in Table 2.
Continued gab.2
Schj

,,,,,,
 with jH - i / ao G p and m er B. Opgt with qaggustnor) moule P lute Na. The receiver: 3 pes.m. acetone. Emulsifier: 1 weight.h. alkyl aryl polyglycol ether. In order to obtain lrenarate active veiijecTBa 1 (v. H. It is mixed with the specified amount of solvent containing my specified amount of emulsifier and diluted with water concentrate 1O of the desired concentration. FBrassica oleracea leaves are sprayed with the active substance (Ogalt
(SNZO) rR (usSscmtJosJ
, -8СНз
PTS
1 y
N
Continuation of the file.2
3
100
100 100
100 100 100
100
100
100
0.1
| (K) 0.01 to moisture content of dew and rycetmu of the cabbage moth (Pluteila grass ipennis) is planted on them. after a specified period, a wall is determined after slaughtering} Eu (%). At the same time, 100% means that all the caterpillars have been killed, 0% means that no caterpillar has been killed. The substances derived from the concentration, determination dates and results are given in Table 3, Table tetla)
Continued gab., Pr. And V. Mer. With MS / ZUS (contact action). FacTBOpjnCJib: 3 weight. H. anetone. E l} shy O: 1 wt. H, alkylarylgoliglycol ether. To pound the current weight of 1 weight.4. it is mixed with pokazh-PzGM with a quantity of solvent, which is indicated by the solvent, and diluted with water to the desired concentration. Prepared active ingredient is sprayed with cabbage plants (Brass ica oleracea), fatally infected with tobacco aphids (Myzus persicae), until it is formed {1 drop. The degree of sacrifice (%) is determined after the passage of the indicated periods. At the same time, 100% means that all aphids are euthanized, and 0% means that not one tl is killed. The active substances, their concentrations, the timing of determination and the results obtained are shown in Table 4.
(Experience with Myzus)
Active substance
sn.
R
(snzo) rR-o- /
(u3iecmHoe)
sn
(WITH )
N
(u SecmHoe)
.SCH,
TO
ABOUT
and-to
sn,
.SCHi
TO.
W
0)

B - K

Cjhs
(snzo) rR-o- /
i-
SzN7-izs
.ZSNz
o
1 to

sns
jj / sch3
/ 1 o- |
TJ-K- CrH5
The degree of umerichlsii.
Concentration. DeutBVK-iiuero substances% 7 jrhi C.1 flow
OD
23
Sch-,
W
O- / I
SzNt-iso
S (C, H50),
SNS
oed
, 7- () 2P- О
-B

SNS
f
/ I
оN-Wx
..S-CHj-CH-CHj
o- (I
IT-
CiHs
.SCHj
L
N: -B

CjH -U39
SCH
N
SzNt-MN n,
P - 0 -4
Cjhgo
B -N
N
With jH-j-iso
Schj
djHg
B - K
CrH5
713527
24 Continuation of table 4
100
100 100
100 100
97,100
100
45,100
100
100 100
100 99
100
100
99
100
100
9
00 100 100
Example g. Experience on limiting concentration (HaceKONtbie, living in the ground).
Experimental insect; Tenebrio moLitor.
Solvent: 3 weight. H. acetone.
Emulsifier: 1 weight. H. alkyl aryl polyglycol ether.
To obtain the preparation of the active substance 1 wt. H. it is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
The prepared active ingredient is thoroughly mixed with the earth. At the same time, the concentration of the active substance in the preparation practically does not play any role, which
Experience in limiting concentration (insects living in the ground) (Tenebrio molitor)
(known)
CzHsO n
P-0-r
CiHsO- 1 I
(usIecfTJHoe) shnz
is the weight amount of active ingredient per unit volume of earth, which is given in parts per million (e.g., mg / l). Fill the hillsides with earth; left mouth to stand at room temperature.
For the most demanding days in the cultivated land
The experimental insects are administered, and the effectiveness of the active substance is calculated by counting the dead and live under-ground insects (%) for a period of 48 hours. Efficiency is 1007s, if all podpygnye insects are euthanized; and 09g, if as many experimental insects live as with the control.
Active substances, their concentration and
received rezu. are given in table.5.
Table 5
27
N -B - C jH 5
 „
50. Y
e.Kso-
. f
CKjO /
- "- 713527
28 Continuation of table 5
100
100
100
50
100
50
100 Example D. Experience with Tetranychus. Solvent: 3 weight.h. acetone. Emulsifier: 1 weight.h. alkyl aryl polyglycol ether. To obtain the preparation of the active substance 1 wt.h. it is mixed with the indicated amount of solvent containing the indicated amount of emulsifier, and the concentrate is diluted with water to the desired concentration. Bean plants (Phaseol.us vulgar is) about 10-30 cm in height are sprayed with the prepared active ingredient before dropping. These bean plants are strong (Tetranych Experience
(CHZO) 2P-0
(usSectrtHoe) IT-
SNS
(C.HsOJ P-O- /
(izestnoe) TI-tg
S (i
Bk-.
CHj
 ZSNz

and-it.

with
/ /
(snzo) rR-o- 1
SzN.
about j
k14
sn,
50
0.1
about 0.01
0.1
98 0.01 95
100 100
100
100
95
100 98 95
0.1
0.01
0.001 730 are affected by spider webs n (Tetranychus urticae) of all stations of development. The effectiveness of the active ingredient calculated by counting dead ticks is determined by the existence of these periods. The killing degree is indicated in%. means that all spider mites are killed, and 0% means that not one spider mite has been killed. The active substances, their concentrations, the timing of determination and the results obtained are given in Table. 6. T-face 6
STT.
; CjK50) jP
(YLZO) ,, P
S
one
, P-0CjHsO
о30-СзН5-№1ч
caijO
-n

C, H5
Forg) izhe 1abl.6
100
0.1
90
OL1
90
0.001
Example E.
LD5ooo - experience.
Test insects: Sitophilus dhzpa-rijis.
Solvent: acetone.
2 weight parts the active substance is absorbed in 1000 vol.4. solvent. The solution thus obtained is diluted by further adding the solvent to obtain the desired concentration.
2.5 ml of the solution of the active substance is placed with a pipette into the Petri string. At the bottom of the Petri dish there is a filter (Experiment on LD Syophilus granartus)
.СНз
if / -g
(C, H50) 2-P-0-I
l uiSecmHffe) V-K
.sn,
Mr.- (
1shn, I
/ known)
H
OCjHs
S V F-O I
and-n
H
CHi
Continued gabl.B
on paper with a diameter of about 9.5 cm. The Petri dish remains open until the solvent has evaporated completely. Depending on the concentration of the active substance in the solution
its quantity on 1 m of filter paper is various. Then about 25 experts are planted in a Petri dish) 1x in a shch and covered with itx glass krppkoy.
The condition of the experimental insects is monitored 3 days after the start of the experiment. Killing is defined in%.
Active substances, their concentrations, experimental insects and the results are shown in Table 7.
Table 7
100
about
I fX /
then n
Example J. LTuo-experiment with two wings
№1.
Experimental insect: Mizsz jdomestica house fly.
Continuation of table 7
Solvent: acetone.
2 weight parts the active substance is absorbed in the 1000 region. solvent. The solution thus obtained is diluted with further colo3771352738
honest solvent to the desired insignificant paper. Then, a concentration of about 45 experimental animals is planted in a Petri dish and covered
2.5 MP solution of the active substance in their glass by me. Pipette into the Petri dish using a pipette. A filter paper with a diameter of about 9.5 cm is located at the bottom of the Petri bag. The Petri dish remains open until the solution evaporates completely. Depending on the concentration of the active substance solution, its amount per 1 m of filter is different in the table. eight.
(Experience with Diptera / Musca domesticai)
well-known) n-h
SNL
1 / -G
(CHZO) Mr. P-o-I I (known) V
OS2K5
(C, H50) i-P-0-4
SNS
ZSNz
() Mr. P
SJY7-UZO
Sch3

(s, H5o) Mr.
SNS
. $ CHS
S y
{
P-oii-i
SNS
The condition of the experimental insects is continuously monitored. The time required for 100% killing is determined.
Experimental insects, active substances, their concentrations and periods at which 100% killing is achieved are given
T a b c a 8
8 h. 70%
- 35
75
6 h. 90%
50 210
6 h. 40%
75
0.2 6 hours 80% 0.02
65 110
6 h. 60%
39
Example 3. Experience with Ixodon and mites.
The painter: 35 weight.h. monomethyl ether
Em ly-ator: 35 weight.h. ionphenol polyglycol ether.
 the preparation of preshrat mix 3 weight.h. active ingredient with 7 weight.h. said mixture of solvent and ethugulgator and the thus obtained emulsion concentrate is diluted with water to the desired concentration.
In this preparation, containing the active substance, adults are immersed for 1 min by pumping blood of females ixodid ticks of Boophilus micropLLus (sensitive and resistant) 11 X HOSA blood. After immersion
(Experience with Ixodes ticks / Boophilus microplus)
. $ CHS
-W
0-h,
B-TG
With Shch-from S-CHj-CN
T
/ |
0 h i
ft-n
713527
40 Continued table.
10 females of each of the different types of Ixodes ticks are placed in Petri dishes, at the bottom of which are lined with circles of filter paper of the appropriate size.
After 10 days, the efficacy of the drug acting on its substance is determined, the delay of the egg laying is established in comparison with the non-immersed control ticks. Efficiency is expressed in%, and 100% means that no more eggs have been laid, and 0% means that ticks have set aside a normal amount of eggs.
The tested active substances, applied grounds, experimental parasites and the obtained results are shown in Table. 9.
Table 9
100
100 50
100
100 100 Example I. Experience with the fly repellent traps. Solvent: 35 weight.h. ethyleneglycol monomethylated ester. Emulsifier: 35 weight.h. nonylphenol polyglycol ether. To obtain the preparation of the active substance 30 wt.h. it is mixed with the indicated amount of solvent containing the indicated amount of emulsifier, and diluted (Experience with parasitizing individuals
Active substance
Sch,
() rR-0
SzN7-iZO
S-CHj rR- ° I
()
iJ-S

Cjhs
s-dH,
o) rR-o- (I
(CrH5
vv

Continuation gabl.9
The degree of killing,%
(Lucilia cuprina / resistant)
100 100 100 100 100
about
100 100 50 100 100 100 the concentrate thus obtained with water to the desired concentration. About 20 fly larvae (Lucilia cuprina) are placed in a test tube containing about 2 cm of horse muscle tissue. 0.5 ml of the prepared active ingredient is applied to this horse meat. After one day, the degree of killing is determined in%. At the same time, 100% means that all the larvae are euthanized, and 0% means that no larvae are euthanized. The results of the experiment are given in table.10. Table 10 mi flies / Luc ilia cuprina) 4371 Example K. Experience on the maximum concentration, the experimental nematode: Meloidogyne incognita .. Solvent: 3 weight.h. acetone. Emulsifier: 1 weight.h. apkylrippolyglycolic ether. To obtain the preparation of the active substance 1 wt.h. it is mixed with the indicated amount of solvent, the indicated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration. The prepared active ingredient is thoroughly mixed with the ground, strongly infected by predualous nematodes. At the same time, the coicenter of the active ingredient in the preparation is practical (Experience with Meloidogyne incognita)
Active substance
HsOx,
p „0
(known}
SNSO I
SNZO (from natural
S it
MN
p
14-N-C3H7 ujo
$ SNS
g u-un II
p-0-4 I
/ I
Cjhso
and --N-SzNg-UZO
The degree of killing,%, at a concentration
active substance, h / mpn.
1 10 T 5 I 2, 1.25 I 0.6 lo I 10 I5 1 2,, 25 I 0.625
1.j1.-4.L.
100100100100 1009 "
100
100
100
9999
100
75 does not play any role; It is only the amount of active ingredient per unit volume of earth that is indicated in parts per million. Pots are filled with earth, lettuce seeds are sown and seeds are kept at a greenhouse temperature of 27 ° C. After four weeks, the infestation of the roots of lettuce by nematodes is determined and the effectiveness of the active substance (%) is determined. Efficacy is 100% if no damage has occurred, and 0% if the impact is as high as that of the control plants in untreated, but in the same way contaminated land. The active ingredients, the doses used and the results obtained are shown in the table below. 11. Table 11
S1I C "1-CN
iV-f

-41
-K-cjhj
S-jj SCH2-CH CH2

Kn i
PH-NC HS
sz-ss
K
° H I
KNH;
CH-.
 SzN7
, Sch3
 7
sso -K SzN7
Sch3
fV
(sno) rr-och (
Mv
ZSNz
 4 - 4 I
Ss
Continuation gabl.11
1009750
100100 989750
100100100100
100 98
100,100
100,100
100,100
100,100
CrH5o) rR-o- (
 I
tg-w
SNS
Thus, the proposed method of combating insects, mites and nematodes has increased efficiency.

权利要求:
Claims (1)
[1]
1. US patent No. 2754244, cl. 424-200, published. 07/10/56.

类似技术:

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同族专利:

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引用文献:

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公开号 | 申请日 | 公开日 | 申请人 | 专利标题

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DE2200467A1|1971-01-19|1972-08-03|Agripat Sa|New esters|

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BE792452A|1971-12-10|1973-06-08|Ciba Geigy|TRIAZOLYL ESTERS OF PHOSPHORUS ACIDS AND PESTICIDE PRODUCTS CONTAINING|

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BE792449A|1971-12-10|1973-06-08|Ciba Geigy|TRIAZOLYL ESTERS OF OXYGENIC ACIDS OF PHOSPHORUS AND PESTICIDE PRODUCTS THAT CONTAIN|

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US4044124A|1971-12-10|1977-08-23|Ciba-Geigy Corporation|Triazolylphosphorus compounds|

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BE792451A|1971-12-10|1973-06-08|Ciba Geigy|TRIAZOLYL ESTERS OF PHOSPHORIC ACIDS AND PESTICIDE PRODUCTS WHICH CONTAIN|

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NL7316468A|1972-12-08|1974-06-11|

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ZA75514B|1974-01-26|1976-01-28|Bayer Ag|Novel thionophosphoric acid esters and their use as insecticides and acaricides|

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DE2423683C2|1974-05-15|1982-10-21|Bayer Ag, 5090 Leverkusen|0-Triazolyl phosphorus acid esters and ester amides, processes for their preparation and their use as insecticides, acaricides and nematicides|

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DE2423765C2|1974-05-16|1982-10-14|Bayer Ag, 5090 Leverkusen|0-Triazolylphosphoric acid esters and ester amides, process for their preparation and their use as insecticides and acaricides|DE2423683C2|1974-05-15|1982-10-21|Bayer Ag, 5090 Leverkusen|0-Triazolylphosphorusacid esters and ester amides, processes for their preparation and their use as insecticides, acaricides and nematicides|

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DE2423765C2|1974-05-16|1982-10-14|Bayer Ag, 5090 Leverkusen|0-Triazolylphosphoric acid esters and ester amides, process for their preparation and their use as insecticides and acaricides|

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CH601266A5|1974-08-29|1978-06-30|Ciba Geigy Ag|

---

GB2163068B|1984-08-17|1988-09-28|American Cyanamid Co|Neutral circuit sulfide collectors|

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DE3440913A1|1984-11-09|1986-05-15|Bayer Ag, 5090 Leverkusen|TRIAZOLYL THIONOPHOSPHORIC ACID ESTER|

法律状态:

优先权:

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申请号 | 申请日 | 专利标题

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DE2301400A|DE2301400C2|1973-01-12|1973-01-12|0-Triazolyl-thionophosphorusacid esters and ester amides, process for their preparation and their use as insecticides and acaricides|

---