IE53231B1 - Herbicide composition containing a mixture of two active agents - Google Patents

Herbicide composition containing a mixture of two active agents

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Publication number
IE53231B1
IE53231B1 IE1642/82A IE164282A IE53231B1 IE 53231 B1 IE53231 B1 IE 53231B1 IE 1642/82 A IE1642/82 A IE 1642/82A IE 164282 A IE164282 A IE 164282A IE 53231 B1 IE53231 B1 IE 53231B1
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radical
ethyl
propyl
weight
percent
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IE1642/82A
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IE821642L (en
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Eszakmagyar Vegyimuevek
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Publication of IE821642L publication Critical patent/IE821642L/en
Publication of IE53231B1 publication Critical patent/IE53231B1/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention relates to a herbicide composition comprising altogether 10 to 80 percent by weight of a compound of formula (I> and of general formula (II> further 14 to 80 percent by weight of at least one liquid hydrocarbon with a boiling point of 150 to 320 DEG C as well as 6 to 15 percent by weight of an additive or additives generally used in the formulation of agrochemical compositions. In general formula (II) R1 stands for an ethyl, n-propyl, isobutyl or cyclohexyl radical, R2 stands for an ethyl, n-propyl, n-butyl or isobutyl radical; or R1 and R2 together represent a hexamethylene radical; further R3 is an ethyl or n-propyl radical with the proviso that R1 and R2 cannot simultaneously represent an n-propyl radical if R3 is an ethyl radical. The composition of the invention can be successfully used for controlling both monocotyledonous and dicotyledonous weeds.

Description

The invention relates to a herbicide composition comprising 10 to 80 percent by weight in total of a compound of formula (I) V N - C - S - C„He « 5 (I) HC3H7 and a compound of general formula (II) to 80 percent by weight of at least one liquid hydrocarbon with a boiling point of 150 to 320 °C as well as 5 to 15 percent by weight of an additive or additives generally used in the formulation of agrochemical compositions, - In general formula (li) stands for an ethyl, n-propyl, isobutyl or cyelohexyl radical; R2 stand for an ethyl, n-propyl, n-butyl or isobutyl radical; or and Rg together represent a hexamethylene radical; Rg is an ethyl or n-propyl radical with the proviso· that R^ and Rg cannot simultaneously represent an n-propyl radical if R3 is an ethyl radical, and R^ and Rg cannot represent ethyl and nbutyl respectively if Rg represents n-propyl.
The Ν', N-dialkyl-thiocarbamic acid S-alkylesters have been known from the literature for nearly twenty years (see e.g. the Ό.S. patent specification Nos. 2,913,327, 3,087,853, 3175,897, 3.185.720, 3,198,786 and 3,582,314). The herbicides called generally thiocarbamates, are used successfully primarily for the protection against monocotyledonous weeds.
The derivatives developed up to now, i.e.
N,N-di-isobutyl thiocarbamic acid S-ethylester (Butylate), Ν,Ν-di-n-propyl thiocarhamic acid S-ethylester (EPTC),· Ν,Ν-di-n-propyl thiocarbamic acid S-n-propyl-ester (Vernolate, N-ethyl-N-cyclohexyl thiocarbamic acid S-ethylester (Cycloate) and Ν,Ν-hexamethylene thiocarbamic acid S-ethylester (Molinate), can be used in different plant cultures; they show different selectivity for the cultivated plants and the weeds and their physico-chemical characteristics influencing their effect are considerably different (water-solubility, vapour tension, and so on).
Thus e.g. the water-solubility of Butylate amounts only to twelve percent of that of EPTC (at 20°C (45 mg/1 as opposed to 370 mg/1) while its vapour tension is somewhat less than half of the latter at 25°C (1.73 Pa as opposed to 4.53 Pa) . -·4 The use of the N/N-disubstituted thiocarbamic acid S-alkyl-esters in plant protection depends, due to their different physico-chemical chai'acteristics, to a considerable degree on the weather conditions (tem5 perature, rainfall) and this fact restricts the scope of their use. Their disadvantage is that they control dicotyledonous weeds to a smaller degree and, when used in a dose necessary for an efficacious weed control, they exert from time to time a phytotoxic effect on the cultivated plants to be protected. In order to improve the controlling action against dicotyledonous weeds it was proposed to use the thiocarbamio acid derivatives combined with s-triazine derivatives, while in order to reduce their phytotoxicity they were combined with compounds of so-called antidotal effect (see e.g, the Hungarian patent specification No, 165.73^).
In the course of our research work carried out in connection with the examination of the herbicidal effect of thiocarbamio acid S-esters it was realized that all these disadvantages can be reduced considerably or eliminated, if a combination of two thiocarbamio acid derivatives in a determined ratio is used so that one of the derivatives is always N,N-di-n-propyl thiocarbamio acid S-ethyl-ester (EPTC) of formula (l), while the other one is one of the derivatives of a thiocarbamio acid of general formula (II) , e.g. Butylate, Vemolate, -Cycloate or Molinate. - 5 Our experiments proved that a herbicide composition containing the mixture of said two derivatives can be used not only independent of the weather but it shows synergism at definite ratios in relation to weeds.
On the basis of these recognitions the invention relates to a herbicide composition containing a mixture of two active agents; in said composition one agent is always Ν,Ν-di-n-propyl-thiocarbamic acid S-ethylester (EPTC) of formula (I), while the other one is one of the thio10 carbamic acid derivatives of the general formula (II).
- In general formula (II) R^ stands for an ethyl, n-propyl, isobutyl or cyclohexyl radical; Rg stands for an ethyl, n-propyl, n-butyl or isobutyl radical; or Rj and Rg together represent a hexamethylene radical; stands for an ethyl or n-propyl radical; with tbe proviso that R^ and Rg cannot simultaneously represent an £-propyl radical if Rg la an ethyl radical and R^ and R^ cannot stand for ethyl and n-butyl respectively if Rg represents n-propyl.
The herbicide composition of the invention contains the two active agents, which together are present In a SO quantity of 10 to SO percent by weight, at least one liquid hydrocarbon with a boiling point of 150 to 320°C present in a quantity of 14 to 80 percent by weight, and 5 to 15 percent by weight of an additive or additives generally used in the preparation of agrochemical compositions. The weight ratio of the compound of formula (I) to a compound of general formula (II) preferably amounts to 9.5 : 0.5 to 4 : 6.
It is advantageous to use petroleum or kerosine as liquid hydrocarbon while it is preferred to use surface-active agents and optionally antidotal compounds as additives.
The following examples illustrate the invention without restricting the scope claimed.
Example 1 Into a round-bottomed flask provided with a mixer different quantities of EPTC and Butylate as set forth in Table 1 are weighed so that their total quantity amounts to 80 parts by weight, then under stirring Imparts by weight of kerosine as well as 6 parts by weight of a surface-active substance are added. The stirring is continued until the mixture becomes homogeneous, then it is filtered. Thus an emulsifying concentrate contain15 ing 80 percent by weight of active agent is obtained, as set out in Table 1: Table 1 Substances Amount s (in parts by weight) EPTC 72.0 64.0 56.0 48.0 4o.o 32.0 Butylate 8.0 16.0 24.0 32.0 4o.o 48.0 Kerosine l4.0 14.0 14.0 14.0 14.0 14.0 Tensiofix AS 3.8 3.9 4.0 4.1 4.2 4.3 Tensiofix IS 2.2 2.1 2.0 1.9 1.8 1.7 Example 2 One proceeds similarly as in Example 1 with the difference that by changing the weight ratio of the components an emulsifying concentrate containing 10 percent by weight of active ingredient is prepared, as set out in Table 2: Table 2 Substances Amounts (in parts bj r weight) EPTC 9.0 8.0 7.0 6.0 5.0 4.0 Butylate 1.0 2.0 3.0 4.0 5.0 6.0 Kerosine 80.0 80.0 80.0 80.0 80.0 80.0 Tensiofix AS 5.3 5.6 5.9 6.2 6.5 6.8 Tensiofix IS 4.7 4.4 4.1 3.8 3.5 3.2 Example 3 One proceeds as in Example I with the difference that the EPTC is combined with Vemolate and an emulsifying concentrate containing 50 percent by weight of active agent is prepared, as set out in Table 3: Table 3 Substance Amo u n t s (in parts by weight) EPTC 45.0 40.0 35.0 30.0 25.0 Vemolate 5.0 10.0 15.0 20.0 25.0 AD-6 7 7.0 7.0 7.0 7.0 7.0 Kerosine 37.0 37.0 37.0 37.0 37.0 Tensiofix AS 4.0 3.5 3.0 2.5 2.0 Tensiofix IS 2.0 2.5 3.0 3.5 4.0 5333 a Example- 4 One proceeds as in Example 1 with the difference that by combining EPTC with Cycloate an emulsifying concentrate containing 60 percent by weight of active agent is prepared., as set out in Table 4: Table 4 Substances A m o u n t s (in parts by weight) EPTC 54.0 48.0 42.0 36.0 30.0 24.0 Cycloate 6.0 12.0 18.0 24.0 30.0 36.0 Petroleum 34.0 34.0 34.0 34.0 34.0 34.0 Evamul A 2.0 2.2 2.4 2.6 2.8 3.0 Evamul B 4.0 3,8 3.6 3.4 3.2 3.0 Example 5 One proceeds as in Example 1 with the difference 15 that by combining EPTC with Molinate an emulsifying concentrate containing 70 percent by weight of active agent is prepared, as set out in Table 5: Table 5 Substances A m 0 u n t s (in parts by weight) EPTC 63.0 56.0 49.0 42.0 28.0 Molinate 7-0 14.0 21.0 28.0 42.0 Petroleum 22.0 22.0 22.0 22.0 22.0 Evamul A 3.2 2.8 2.4 2.0 0.8 Evamul B 4.8 5.2 5.6 6.0 7.2 5323 - 9 Example 6 One proceeds as in Example 1 with the difference that antidote AD-67 is added to a mixture of EPTC and Butylate and petroleum is used as liquid hydrocarbon.
Thus an emulsifying concentrate containing 46-48 percent by weight of active agent is prepared, as set out in Table 6 Table 6 Substances Amount s (in parts by weight) EPTC 40.0 35.0 30.0 25.0 20.0 Butylate 6.0 11.5 17.0 22.5 28.0 AD-67 4.0 3.5 3.0 2.5 2.0 Petroleum 42.0 42.0 42.0 42.0 42.0 Evamul A 3.0 3.3 3.6 3.9 4.2 Evamul B 5.0 4.7 4.4 4.1 3.8 The surface -active agents used in Examples 1 to 6 are as follows : Tensiofix AS: octylphenol polyglycolether (product of the firm Tensia AG) Tensiofix IS: nonylphenol polyglycolether (product of 20 the firm Tensia AG) Evamul A: the mixture of a fatty alcohol ethoxylate and dodecylbenzene sulfonic acid in a ratio of 20 ; 80 (product of the firm Hoechst AG) Evamul B: the mixture of a fatty alcohol ethoxylate and dodecylbenzene sulfonic acid in a ratio of 30 : 70 ( product of the firm Hoechst AG).
The antidote AD-67 is produced by Nitrok6mia Xpartelepek, a Hungarian enterprise of Balatonfiizf0, Hungary.
Example 7 In the course of our experiments the herbicidal activity of emulsifying concentrates containing only one thiocarbamic acid derivative each (EPTC and Butylate, respectively) as well as of emulsifying concentrates containing the mixture of these two compounds was studied.
The experiments were carried out in plastic 2 jars having a surface of 1.2 dm in the following way: 400 g· of laminar soil [see its definition e.g, in Biologiai Lexikon, volume 3, page 301, Akademiai Kiado, Budapest, 1977] were weighed into each of the jars, then the seeds of weeds Linum usitatissimus and Sinapsis alba were sown and the seeds were covered with 200 g. of soil each. Then different doses of the three different emulsifying concentrates containing (a) EPTC as the sole active agent, Butylate as the sole active agent and (c) EPTC and Butylate together, were sprayed ento the soil and a further 100 g. of soil each were put into the jars. Hie weeds were cultivated with 12 hour lighting periods (under 400 W daylight supplemental lamps of - 11 typo HgMi/D). Water was supplemented up to 65 % of the maximum water capacity daily.
In the course of the cultivation the average temperature of the glass-house was 24.3 °C (maximum 26,8 °C, minimum 21.8 °C) while the average relative humidity was 57.8 %.
The evaluation of the experiments was carried out on the 12th day after the treatments so that the part of the weeds above the soil was out off and the total green mass of these parts was weighed.
The calculated effect for the evaluation of the probable effect of'the treatment carried out with the ' combination containing the two thioearbamie acid derivatives was determined with the help of the formula elabo15 rated by Colby S.R. [Weeds, 15, p. 20-22 (1967)]: X. . Y. x E. = x 100 In the formula X.^ represents the growth measured at the application level p in kg/ha of herbicide A expressed in percents of the control, Y^ represents the growth measured at the application level q kg/ha of herbicide B expressed in percents of the control, while E^ is - 12 the probable growth - the additive effect - at the use of the application level p + q kg/ha of the herbicides A and B expressed in percent of the control (calculated value ).
The results of the experiments, the measured and calculated values, are shown in Table 7' from which it appears that .the actually measured weed weight is significantly lower at treatments 2,3, 4, 5, 6 and 7 then the probable calculated value, thus when using the two active agents EPTC and Butylate together in a ratio of 9.5 : 0.5 to 4 : 6a synergistic effect can he observed, - 13 Table OK J· in o cn m 00 cn 00 rl • a • • • « • a Φ 0 m H 04 cn cn r* o H -0· Ok K0 £-- CO 00 00 oo oo 00 O o r-l Ok 5 o rl H r-l 3 w 3 0 -P a λ Q 60 Τί *rl 1 0 Φ 3 H 3 0 Ok -tf o KO cn 00 04 J· • K h H *0 • • • • • • • • Σ'- • r-i *p dΦ m t'· cn o Ok cn 04 o Ok KO a 0 0 *P r· H Ok Ok o o Ok Ok KO 0 3 rl rl K H Ok 3 B Φ > •rl -P 0 +> 3 ε 3 a λ ec © O o o o o o © © o © Φ \ + • • • • • • a 0 H 60 6D Οι H H rl rl rl rl rl rt rl rl H 3 3 = 0 -P 0 •ri «Ρ P d Φ 0 p d d p s o H 04 cn m © 4S 00 Ok o Η \ O1 a • • • • • • • • a a S 6B = o O o o o o o O © o rl •P 3 pq E 0 + © d ©is o Ok 00 t- Ό m 4· cn 04 rl o A \ ft • • * • « • « • • • a Pl a : H o o o o o o o © o o a a 1 vs. Φ Q) >> m +> o Ό 04 o cn o KO 00 Ok 04 rl +3 +> a £ • • • • • • • • « a * 0 0 3 60 -rl o 04 m Ok oo o cn © cn KO o a ο τΐ sh o m rl o o 04 o Ok Ok Ok Ok •rl 0 Φ Φ rl rl rl rl rl rl H •P 0 3 3 > > II £ = o rl 04 cn J· m KO 00 ok o • • • • • • • • • a a m ep o o o o o o o o o o rl 1 KS. Φ S to -P O\ Ok 4S H Ok 00 KO Ol 04 O -p 3 • • • • • • • • • a a 0 0 3 60 Tl m KO o cn o ©1 00 m C cn o © 0 a Φ -rl X n- 00 00 o rl Ok OK o o o P •ri 0 Φ Φ rl rl K rl rl ε 3 3 > Ϊ $ II d i = o Ok 00 r- KO m cn 04 H o — \ ft • • • • • • • • • a a 3.- rl o o o o o o o o o o •P Φ » H 04 cn J- in Ό Γ- oo Ok o rl 0 H rl 0 -P -P 2 31 3 231 - 14 Example 8 Similarly as in Example 7 the herbicidal effect of the emulsifying concentrates containing only EPTC and Vernolate, respectively, as well as the mixture of these two active agents was examined. The experiments were carried out in plastic jars with a surface of o 1.2 dm in the following way: 400 g. of layered soil were weighed into the jars, then the seeds of the weed Echinoclos crus-galli (barnyard grass) were sown into the soil and the seeds were covered with 200 g. of soil. Then different doses of the three different emulsifying concentrates containing EPTC, Vernolate as well as EPTC and Vernolate together were sprayed onto the soil and a further 100 g. of soil each were put into the jars.
The weeds were cultivated with 12 hour lighting periods (under 400 W- daylight supplementing lamps of type HgMi/D). Water was supplemented up to 65 % of the maximum water capacity daily.
In the course of the cultivation the average temperature of the glass-house was 24.3 °C (maximum 26.8 °C, minimum 21.8 °C) while the average relative humidity was 57.8 %.
The evaluation of the experiments was carried out on the 12th day after the treatments so that the - 15 part of the weeds above the soil was cut off and the total green mass of these parts was weighed.
The calculated effect for the evaluation of the probable effect of the treatment carried out with the combination containing the two thiocarbamic acid derivatives was determined with the help of the formula elaborated by Colby as indicated in Example 7. φ Η Ρ d Η Wt P - 16 - 31 to •rl Φ Η CM r* »4 cn O H -d 2± CM O\ m -d £ ©ν « • • • • • • • • • « 3 Ο Η 00 in -d o F* in m «4 00 «4 cn Ό P Η Η i4 r4 CM t4 K «4 Φ o Φ © & 3 0 d *3 Q Φ τί P © 3 ι4 CM cn o o F*· O o 00 cn ao -d o * • • • • • • • • « • • 0 Ο cn £» σ» «4 -d- F* -d cn M3 .d Os en o © Η t4 Η CM cn H r4 »4 i4 i4 t4 «4 0 0 d 0 •H B a d Q Ρ _ Ο Ο Ο ο o o O O O O O o o © •ri β σ* M3 Ό νο VO M3 M3 M3 Ό M3 M3 M3 M3 M3 p P © + • • • • • • • • • • • • • 0 0 δη ft Η Η Η «4 <4 r4 H »4 »4 «4 »4 «4 H P P © © © Φ d P © © *ri £ _ Ο co Ό CM -d ¢3 M3 CO «d CM M3 O o X. σ* Ο Ο ο γ4 on M3 00 OS CM -d in in M3 fi £* hO • J? Ο ο ο Ο o o O O f4 i4 »4 •4 •4 B © > o © ο νο CM -d oo M3 o -d CM M3 oo •st· o o Λ - νο m ιη -d CM Os 00 M3 en »4 O O o H \ ft • • « • « • • « • • « • • - ft sn Η Η «4 «4 «4 o o O o o o o o H Φ P r» (0 •st H 0 0 Ρ Ο -d ο -d CM in M3 CM en CM -d M3 -d 0 0 d 31 • « « • « • • • • • • • • β 0 o *0 δα Ο Σ'* ο Ο co M3 -d- OS F* oo in Os cn p β *rt © •4 ίΗ Ο Ο ο os f> cn cn «4 H <4 r4 «4 © 0 © Φ Φ Η «4 »4 !> B r-l & II © Ο -d οη M3 CM -d o M3 OO J· CM M3 o ra Λ Ο ο ο «4 cn M> 00 OS CM -d in m M3 σ* « • • • « • * * • « « • • «η ο ο ο Ο o o o o «4 «4 »4 »4 »4 1 }>. w 0 0 Ρ Η cn cn Σ'- M3 cn H H o cn o- OS o 0 β Λ • • « • • « • • • • • « • Q 0 0 δα •Η Ο CM ο CM Os oo »4 cn in CM cn i4 o £ d «3 © •Η Μ Η «4 Η cn en cn m fr- OS O\ O o ft 0 Φ © Φ «4 r4 a S Η 11 © Ο <Ο CM -d· oo M3 o 2d CM M> oo -d O — Λ M3 ιη in -d CM Os 00 M3 cn H o O o \ ft « « * • • • • • • • « • • en Η «4 Η Η H o o o o o o o o A! +» Φ (0 Λ © Ρ Ρ Ο <Η a q The results of the examinations, the measured and calculated values are included in Table 8 from which it appears that, on the one hand, EPTC and Vornolato used separately exert a weaker herbicidal effect than the herbicide composition containing both together in an identical dose and, on the other hand, the actually measured weed weight is significantly lower at treatments 2, 3, 4, 5, 6 and 7 than the probable calculated value, thus when using the two active agents EPTC and Vernolate together in a ratio of 97·5 : 2.5-50 : 50 a synergistic effect can be observed.
Example 9 Using the same methods and conditions as in Example 8 the herbicidal effect of EPTC and Cycloate was examined by using them separately and together, in a mixture, respectively, on the weed Echinocloa crus-galli.
The course and evaluation of the examination 2o is identical with that of Example 8, the results are included in Table 9. Η Φ ri Η 1Π * ri cn j· cn • i4 in • o • cn • ri • OS ·- 0 3 Ο Ι> 01 in Os m co vO H 00 vo cn φ μ Η ri ri ri O| Ol Ol 01 cn 01 CM CM £ 0 Φ σ) 3 0 a «μ Ό 0 Λ Φ Ό 60 μ φ •Η Φ Φ Η Η Η. Ο Os o m -d“ ri ri cm m OS £ φ • • • • • « « • » » • • • -μ 0 Ο cn Os cn o o vo ri m in 00 cn 0 ri Η Η Η 01 cn cn cn cn 01 CM 01 0 Φ 0 0 a 0 •ri Β W a 0 Φ > μ φ =- Ο Ο ο o o o o o o o o O o •ri Φ •ri β Λ σ VO VO VO VO VO vo VO vo vO vo vo VO vo -μ μ /1) \ + * * • • • » • • • • • • • -P 0 0 ω 60 ft Η rl Η ri ri ri H ri rl rl H ri ri -μ Φ Φ Φ β φ -μ Φ Ο .4 οη VO 01 -d· O VO CO -d· Ol VO O •Η Φ Λ - ο ο ο ri cn vo 00 Os 01 -4 in in VO 0 X σ* • • • • * • • • • « • • • fi 60 ο ο ο O o O o o rl rl ri ri ri 0 Λ Ε >. ο ο Φ ο Ό οι J- oo vo o -d· 01 Ό CO O ρ Λ χ Ό m m 01 os oo vo cn ri o o O ρ X ft • • • • • • • • • « • • • ft 60 Η Η ri H ri o o o o o o o o α X 1 ΰ φ φ φ 0 ϊ>. fcS. μ μ Ο Κ cn 01 VO o ri 01 o ri o Os β ο φ μ • • « « • • • - · • • • « • 0 0 3 Λ Ο Ό oo ri cn OS Os cn 01 00 Z> oo cn 0 0 to •ri ο ο Os OS 00 zs vo J- cn Ol CM CM 0 a a •ri Η Η μ, !►> 0 0 Φ Ο Ε τ3 Is It Φ Ο -d· OO VO CM -d* o VO 00 CM vO o — Λ Ο Ο O ri cn VO 00 Os 01 -d· in m vo β S. ο* • « • • • • • • « « » • • to Ο Ο o o o o o o rl H ri ri rl Λ! , ’d Φ φ φ V- -μ Η cn cn VO cn ri H o cn o Os o 0 (0 μ • • * • • • • * • • • « • 0 3 Λ ο οι r* 01 Os oo ri cn in 01 cn ri o 0 0 60 •ri Η Η ri cn cn cn in IS Os OS o o Q a a •ri κ ri ri Η 0 0 Φ ft ε Ό is Η II Φ Ο Ό 01 -d· 00 VO o -d· 01 vo 00 •4· O 4?! VO ιη in -d· CM Os 00 VO cn ri o o o — \ ft • • • • • • « • .· • • « • 60 Η Η ri H ri o o O o O o o o Λ! μ • Φ 01 Η οι cn -4 m VO 00 Os o ri CM cn 0 <Η Λ φ rl ri ri K 3 C -μ μ From the data of Table 9 it appears on the one hand that EPTC and Cycloate used separately exert a weaker herbicidal effect than the herbicide composition containing them together in an identical dose and on the other hand that the actually measured weed weight was significantly lower at treatments 2, 3» , 6, 7, 8, 9 and 10 than the probable calculated value, thus using the two agents EPTC and Cycloate together in a ratio of 97·5 : 2.5 - 10 : 90 a synergistic effect can be observed,

Claims (6)

CLAIMS:
1. A herbicide composition characterized in that it includes 10 to 80 percent by weight in total of a compound of formula (I) 0 II N - C - S - C 2 H 5 (X) and a compound of general formula (II) wherein R^ stands for an ethyl, n-propyl, isobutyl or cyclohexyl radical; Rg stands for an ethyl, n-propyl, 10 n-butyl or isobutyl radical; or R^ and Rg together represent a hexamethylene radical; R^ is an ethyl or n-propyl radical with the proviso that R^ and Rg cannot represent simultaneously an n-propyl radical if Rj is an ethyl radical and that R^ and Rg cannot represent . 15 ethyl and n-butyl respectively when R^ represents n-propyl; 14 to 80 percent by weight of at least one liquid hydrocarbon with a boiling point of 150 to 320°C and 5-15 percent by weight of an additive or additives generally used in agrochemical compositions. - 21
2. A herbicide composition as claimed in claim 1, wherein the liquid hydrocarbon is kerosine.
3. A herbicide composition as claimed in claim 1 or claim 2, characterized in that the weight ratio of the 5 compound of formula (I) to compound of general formula (II) is between 9.5:0.5 and 4:6.
4. A herbicide composition as claimed in any one of claims 1 to 3, wherein the compound of the general formula (II) is N,N-di-isobutyl thiocarbamic acid S-ethylester. 10
5. A herbicide composition as claimed in claim 1 or claim 2, wherein the compound of the general formula (II) is N-ethyl-N-cyclohexyl thiocarbamic acid S-ethylester.
6. A herbicide composition as claimed in claim 5, wherein the ratio by weight of N,N-di-n-propyl thiocarbamic 15 acid S-ethylester to N-ethyl-N-cyclohexyl thiocarbamic acid S-ethylester is in the range of from 97.5:2.5 to 10:90.
IE1642/82A 1981-07-08 1982-07-07 Herbicide composition containing a mixture of two active agents IE53231B1 (en)

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HU811975A HU184467B (en) 1981-07-08 1981-07-08 Herbicide composition containing the mixture of two active agents

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IE821642L IE821642L (en) 1983-01-08
IE53231B1 true IE53231B1 (en) 1988-09-14

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AT (1) AT381208B (en)
BE (1) BE893739A (en)
BG (1) BG41474A3 (en)
CA (1) CA1182656A (en)
CH (1) CH653214A5 (en)
CS (1) CS232728B2 (en)
DE (1) DE3225624A1 (en)
DK (1) DK305782A (en)
FR (1) FR2509136B1 (en)
GB (1) GB2101889B (en)
GR (1) GR76523B (en)
HU (1) HU184467B (en)
IE (1) IE53231B1 (en)
IT (1) IT1156106B (en)
NL (1) NL8202720A (en)
PL (1) PL130154B1 (en)
PT (1) PT75200B (en)
SU (1) SU1494851A3 (en)

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Publication number Priority date Publication date Assignee Title
EP0175332B1 (en) * 1984-09-19 1992-03-18 Stauffer Chemical Company Herbicide compositions of extended soil life
USD926637S1 (en) * 2018-08-23 2021-08-03 Pexco Gmbh Cycle or motorcycle frame component

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Publication number Priority date Publication date Assignee Title
NL232065A (en) * 1956-01-17
US3175897A (en) * 1962-08-21 1965-03-30 Stauffer Chemical Co Asymmetric thiolcarbamates as herbicides
JPS52128221A (en) * 1976-04-20 1977-10-27 Mitsubishi Petrochem Co Ltd Herbicidal accelerators
DE2909158A1 (en) * 1979-03-08 1980-09-11 Basf Ag HERBICIDAL MIXTURES

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HU184467B (en) 1984-08-28
FR2509136B1 (en) 1986-08-22
NL8202720A (en) 1983-02-01
GR76523B (en) 1984-08-10
DK305782A (en) 1983-01-09
CS232728B2 (en) 1985-02-14
FR2509136A1 (en) 1983-01-14
IE821642L (en) 1983-01-08
GB2101889A (en) 1983-01-26
DE3225624A1 (en) 1983-02-03
PT75200A (en) 1982-08-01
CS520282A2 (en) 1984-02-13
SU1494851A3 (en) 1989-07-15
IT8222291A0 (en) 1982-07-07
IT8222291A1 (en) 1984-01-07
PL237300A1 (en) 1983-02-14
AT381208B (en) 1986-09-10
CA1182656A (en) 1985-02-19
BG41474A3 (en) 1987-06-15
PT75200B (en) 1984-06-27
CH653214A5 (en) 1985-12-31
GB2101889B (en) 1985-05-01
ATA231782A (en) 1986-02-15
PL130154B1 (en) 1984-07-31
BE893739A (en) 1982-11-03
IT1156106B (en) 1987-01-28

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