Pendimethalin 알아보기

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Title

Continuous Synthesis of Pendimethalin (Agricultural Science Paper ) 합성법

Abstract

Pendimethalin , which was firstly developed by American Cyanamiol Company,Trade names include AC92553,Accotab, Go-Go-San ,Herbadox,Penoxalin,Prowl,Sipaxol,Sovereign, Stomp and Way-Up.Acute oral LD50 technical for rats,1250mg/kg. Acute dermal LD50 for mice,1620mg/kg. Nocarcinogenic,（mutagenic and teratogenic effects at experimental dosage）. High toxic to fish and aquatic organisms. Low toxic to bees and birds,oral LD50 forbees 59.0mg/kg,acute oral LD50 for wigeon 10g/kg?d .Acute oral LD50 of 33% EC for ats2.9g/kg（male） and 2.7g/kg（female）,acute dermal for male rabbits 6.8g/kg,acute inhale for r>475mg/m。Pendimethalin is a selective herbicide used to control most annual grasses and certain broadleaf weeds in field corn, potatoes、rice、cotton、soybeans、tobacco、peanuts and sunflowers. It is used both pre-emergence, that is before weed seeds have sprouted,and early post-emergence. Incorporation into the soil by cultivation or irrigation recommended within 7 days following application. Pendimethalin is available in emulsifiable concentrate,wet table powder,or dispersible granule formulations.In the article,N-（1-ethylpropyl）-3,4-dimethylaniline was used as starting material, we studied on the synthetic process of Nitrification by batch process。We determined the concentration of the nitric acid is 35%,The amount of nitric acid is N-（1-ethylpropyl）-3,4-dimethylaniline1.05 times, the reaction temperature is 40℃, the reaction time was 30min, the reaction was complete in the salifying process; in the nitrification process, We determined the concentration of the nitric acid is 55%,The amount of nitric acid is N-（1-ethylpropyl）-3,4-dimethylaniline 3 times, the reaction temperature is 46-55℃, the reaction time was 2.5h,at the same time ,we carried out a continuous stability test, the average level of Pendimethalin is 96.5%, with an average conversion rate of 79.8%。On this basis,We studied the synthetic process of Nitrification by continuous process,When the total flow is 1.2ml/min,it can be synthesized continuously Pendimethalin TC,the content of Pendimethalin is79.89%,Compared with the intermittent,the Content of product is higher 2%～3%,and the Nitrite content of Pendimethalin was less. In the process of denitrosation,We used FeCl2·4H2O as Scavenger to remove nitrosourea compounds of Pendimethalin TC, after 3h , the concentration of N-nitroso-Pendimethalin below the detection level about 100ppm。

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Order Prowl H2O Herbicide with Pendimethalin

Prowl H2O Herbicide with Pendimethalin

Product Description

Prowl ? H 2 0 Herbicide Prowl ? H 2 0 herbicide is a water-based formulation of pendimethalin. Prowl H 2 0 offers exceptional convenience, performance and crop safety. The innovative, water-based formulation offers additional benefits including no odor, reduced staining, greater storage temperature flexibility and better performance in high surface areas. How Prowl H20 Herbicide Works Thorough, persistent and ravenous — the power of Prowl H 2 O herbicide is yours to unleash. A water-based formulation of pendimethalin, Prowl H 2 O is ideally suited for growers looking for long-lasting, dependable, broad-spectrum residual weed control. The innovative, water-based formulation maximizes herbicide availability for residual weed control through excellent surface stability and reduced binding to field residue. Prowl H 2 O offers exceptional convenience and crop safety benefits, including no odor, reduced staining, greater storage temperature flexibility, a lower use rate than other pendimethalins, no incorporation requirement and better performance in high-surface areas. Combine those features with the staying power to dramatically reduce weed escapes and the need for multiple applications, and it is no wonder that so many growers choose Prowl H 2 O to keep their crops cleaner and higher yielding — right up until harvest. Prowl H 2 0 is registered in over 90 crops, including on corn (field, pop, seed and sweet), cotton, edible beans, garlic, grain sorghum, alfalfa, lentils and peas, bearing grape, bearing fruit and nut trees, , nonbearing fruit and nut crops, nonbearing vineyards, onions and shallots (dry bulb), peanuts, potatoes, rice, soybeans, sugarcane, sunflowers, perennial grasses grown for seed, clover grown for seed, carrots grown for seed, strawberries, mint (peppermint and spearmint), tobacco, and wheat.

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HORTSCIENCE 25(1):84-86. 1990.
Root and Rhizome Growth of Kentucky Bluegrass Following Application of Pendimethalin
R.J. Cooper, P.C. Bhowmik, and L.A. Spokas
Department of Plant and Soil Sciences, University of Massachusetts,
Amherst, MA 01003
Additional index words. Poa pratensis, preemergence, herbicide, turfgrass

Abstract. Field experiments were conducted to determine the response of five widely
used Kentucky bluegrass (Poa pratensis L.) cultivars (Adelphi, Baron, Bensun, Merion,
and Touchdown) to preemergence applications of the herbicide pendimethalin. Pendimethalin applied during 2 years at 1.7 or 3.4 kg·ha-1 (a.i.) controlled smooth crabgrass
[Digitaria ischaemum (Schreb. ex Schweig.) Schreb. ex Muhl.] effectively without injury
to turf. Pendimethalin at 3.4 kg·ha-1 resulted in a short-term suppression of root
growth immediately following application in the first year of the study. The reduction
was transitory and subsequent rooting and rhizome growth were unaffected by pendimethalin.
Cultivar × pendimethalin level interactions were not significant during
the study. Thus, the herbicide appears to be a safe, effective preemergence material
for crabgrass control in Kentucky bluegrass turf. Chemical name used: N-(1-ethylpropyl)-
3,4-dimethyl-2,6 -dinitrobenzenamine (pendimethalin).
Preemergence herbicides are applied routinely
to turfgrass for control of annual grassy weeds. Although the benefits of annual grass
control are well known, concerns exist as to
whether preemergence herbicides may adversely
affect the growth of desirable turf
species. Many of the commonly used preemergence
herbicides have been shown to have inhibitory effects on the growth of certain
cool-season turfgrasses (Bhowmik, 1988; Christians, 1984 Shearman et al., 1979). In
addition, cultivars within a particular species may vary in their ability to tolerate preemergence
herbicides without injury (Christians, 1982; Dernoeden et al., 1988; Hurto
and Turgeon, 1979; Shearman et al., 1979).
Pendimethalin is used widely for preemergence control of annual grassy weeds in
turf. Although its efficacy and lack of phytotoxicity have been demonstrated (Bhowmik,
1988; Demoeden et al., 1988; Watschke, 1983), research results concerning its effects
on turfgrass rooting and rhizome growth have indicated potential for injury. Jagschitz (1986)
eval‎uated pendimethalin applied to immature (7.5-month-old) Kentucky bluegrass sod and
noted that applications of 1.7 and 3.4 kg·ha-1 inhibited tillering for up to 22 weeks after
treatment (WAT). In addition, sod strength was significantly reduced 22 WAT by pendimethalin applied at 3.4 kg·ha-1. In experimentsconducted on both seedling and mature Kentucky bluegrass, Reicher and Christians Received for publication 9 Nov. 1988. Contribution from the Massachusetts Agr. Expt. Sta., Amherst,
Journal Article no. 2910. This work was supported in part by state and Hatch Act funds
(Project 526) allocated to the Massachusetts Agr.Expt. Sta. The cost of publishing this paper wasdefrayed in part by the payment of page charges.
Under postal regulations, this paper therefore must be hereby marked advertisement solely to indicate this fact. (1986, 1988) reported that recommended rates
(1.7 to 3.4 kg·ha-1) of pendimethalin significantly inhibited rooting. Dernoeden et al.
(1988) found that pendimethalin at 3.4 kg-ha-’ restricted perennial ryegrass (Lolium
perenne L.) rooting to 54% and 22% of untreated turf at 4 and 15 WAT, respectively.
Despite significantly reduced rooting, decreased visual quality was not observed.
Since annual grassy weed problems are often greatest in low-density, poor-quality
turf, it is important that preemergence herbicides not impair the growth of desirable
grasses into areas previously occupied by weeds. Published work indicates that the potential may exist for inhibition of turfgrass growth following pendimethalin application.
The purpose of this study was to eval‎uate the rooting, rhizome production, and quality
of five widely used cultivars of Kentucky bluegrass in response to annual applications
of pendimethalin.
Pendimethalin (60 WDG) was applied on 3 May 1986 and 16 Apr. 1987 at 0, 1.7, and
3.4 kg a.i./ha to 0.9 × 1.8-m field plots of 5-year-old ‘Adelphi’, ‘Baron’, ‘Bensun’,
‘Merion’, and ‘Touchdown’ Kentucky bluegrass growing on a Hadley silt loam soil (coarse, silty, mixed, nonacid, mesic Typic Udifluvent). These cultivars, with the exception of ‘Merion’, were chosen because of their widespread use in seed and sod mixtures.
‘Merion’, although not currently recommended for new seedings or sod, remains a common component of many existing turf areas. The experimental design was a randomized complete-block with three replications.
Treatments were applied using a CO2-powered backpack sprayer at 207 kPa of
pressure delivering 1390 liters·ha-1. All turf (field plots and plugs used for rooting and
rhizome determinations) was maintained at a mowing height of 5 cm, with irrigation
applied as necessary to prevent drought stress.
Nitrogen was applied at 49 kg·ha-1 during May and September of each year. The fungicides tetrachloroisophthalonitrile (chlorothalonil)
and 3-(3,5 -dichlorophenyl)-N-(1-methylethyl)-2,4-dioxo-1-imidazolidinecarboxamide (iprodione) were applied on a curativebasis at recommended rates for controlof dollar spot (Sclerotinia homoeocarpa).
Turfgrass quality and crabgrass control.Visual ratings of quality were made several times during each growing season using a scale of 1 to 9, where 1 = brown, lowquality turf; 6 = acceptable; and 9 = dark
green, high-quality turf. Smooth crabgrass control was assessed visually on field plots
using a scale of O to 100, with O representing no crabgrass and 100 indicating complete
crabgrass ground coverage. Percent control was expressed as a percentage of mean
crabgrass cover in untreated plots. Crabgrass density in turfgrass plugs used for root and
rhizome study was determined twice during 1986 and once during 1987 and was expressed as plants/dm2.
Root and rhizome development. On 6 May 1986, 10.8-cm-diameter × 2.5-cm-deep
plugs were removed from each pendimethalin level/cultivar plot and transplanted into a sand bed in the field using three replications
in a split-plot design with cultivars as main plots and pendimethalin levels as subplots.
Sufficient plugs were transplanted to allow for the harvest and destructive sampling of separate plugs on each harvest date.
To eval‎uate rooting depth and mass, as well as rhizome production, length, and mass,
plugs were harvested 30, 61, 131, and 209 days after treatment (DAT) during 1986.
Harvesting consisted of excavating each plug, along with associated sand within a 15-
cm radius, to a depth of 25 cm. Sand was

Table 1. Pendimethalin influence on Kentucky bluegrass maximum root length. Values represent the mean of 15 observations.
zTreatments applied 3 May 1986 and 16 Apr. 1987.
ySampled 15 Apr., 1 day before treatment. NS,*Nonsignificant or significant at P = 0.05, respectively.
84 HORTSCIENCE, VOL. 25(1), JANUARY 1990

Table 2. Rhizome growth of Kentucky bluegrass cultivars during 1986.z
zValues represent an average of nine observations across all pendimethalin levels (cultivar-pendimethalin
level interaction is NS). yTreatments applied 3 May 1986.
xMean separation within columns by Duncan’s multiple range test, P = 0.05.
wSamples insufficient for analysis.
NS,*,**Nonsignificant or significant at P = 0.05 or 0.01, respectively.
Fig. 1. Mean maximum root length of Kentucky
bluegrass turf 30 days after pendimethalin application,
1986.

The plot is a significant (P =
0.05) linear regression. Values represent the mean of 15 observations.
carefully washed from the roots before determining mean maximum root length. Roots
were then clipped from each plug to determine root mass. Root mass represents the
difference between oven dry weight (70C for
48 hr) and ash weight (600C for 24 hr). Rhizome production was determined by counting
the number of rhizomes that originated from a given turfgrass plug and secondary
rhizomes branching from those primary rhizomes.
Both types were measured to determine average length and were then ovendried at 70C for 48 hr to determine rhizome mass per plug.
To assess the effect of a second annual application on rooting and rhizome development,
pendimethalin was reapplied, using the procedure previously described, on 16 Apr. 1987 to the remaining Kentucky bluegrass plugs growing in the sand bed. During
1987, root growth and rhizome development were eval‎uated 1 day before application and
at 40 and 110 DAT.
Statistical analysis. AH values were subjected to an analysis of variance (ANOVA)
using the Statistical Analysis System (SAS,1982). Significant pendimethalin application
level effects were eval‎uated using stepwise polynomial regression (SAS, 1982). Duncan’s
multiple range test was employed far mean separation when the ANOVA F test
indicated that cultivar effects were significant. Turfgrass quality and crabgrass control.
During 1986 and 1987, pendimethalin applied at 1.7 and 3.4 kg·ha-1 provided excellent,
season-long control of smooth crabgrass (97% and 99%, respectively) in field plots of all Kentucky bluegrass cultivars.
The lack of crabgrass encroachment in pendimethalin-treated turf plugs maintained
for rooting and rhizome eval‎uation confirm‎s effective control. Untreated turf averaged 4.0
and 6.4 crabgrass plants/dm2 during 1986 and 1987, respectively. Crabgrass encroachment in response to pendimethalin at either level
averaged less than one plant/dm2 in 1986 and none in 1987. As in the field plot eval‎uation,
the 3.4-kg application did not provide significantly better control than pendimethalin
applied at 1.7 kg·ha-1. Kentucky bluegrass field plots showed no injury from pendimethlin application at either level throughout the study. Visual quality,
averaged for all cultivars, in response to pendimethalin
applied at 0, 1.7, or 3.4 kg·ha-l rated 7.6, 7.5, and 7.7 during 1986 and 6.8,
6.8, and 6.9 during 1987. The cultivar ×
pendimethalin level interaction for turfgrass quality was not significant at any time during
the study, indicating a lack of cultivar-specific sensitivity to pendimethalin.
Root and rhizome development: pendimethalin effects. Pendimethalin at either level
had no effect on mean maximum root length throughout the study, except when eval‎uated
30 DAT in 1986 (Table 1). The relationshipof maximum root length to pendimethalin
level 30 DAT during 1986 was linear and is described by the equation Y= 4.4 – 0.5(X)
(Fig. 1). Inhibition of root length 30 DAT (1986) was transitory and was not evident
when plants were sampled 61 DAT in 1986.
In addition, restricted root length was not observed in response to a repeat application
of pendimethalin in 1987.
The short-term inhibition of root length during 1986, as well as the lack of restricted
rooting following 1987 application to transplanted plugs, might be explained by the nature
of dinitroaniline herbicide activity, which is characterized by low water volubility and
a mode of action involving inhibition of both cell division and elongation of lateral roots
(Ashton and Crafts, 1981);
In 1986, newly transplanted plugs had root systems predominantly within the upper 2.5 cm of soil, where they likely would be subject to the inhibitory effects of pendimethalin.
As the 1986 season progressed, and by the time of reapplication during Spring
1987, the plugs had developed notably longer roots (Table 1). Thus, given the low water
volubility of pendimethalin, it is plausible that much of the root system was then below
the herbicide layer and unaffected by the application.
This reasoning may explain other research nating only a short-term inhibition of Kentucky
bluegrass rooting following pendimethalin application. Reicher and Christians
(1986) reported a decrease in root mass 50days after application of pendimethalin at 1.7
or 3.4 kg·ha-1 on mature, low-maintenance Kentucky bluegrass, while no inhibition was
evident 100 DAT. Bingham et al. (1988) also reported inhibited rooting of Kentucky bluegrass
(42 DAT) in response to pendimethalin  applied at 3.4 kg·ha-1 in Virginia.
Since the 3.4-kg·ha-1 level provided no improvement in crabgrass control over 1.7
kg·ha-1 in this study, no justification exists for applying the higher level for crabgrass
control in the northeastern United States.
Thus, the turf would not be subject to the significant decline in root length observed
with the 3.4 kg·ha-1 application.
Throughout the study, root mass remained unaffected by pendimethalin application at
either level. Root mass during 1986 averaged across all treatments ranged from 0.34
g/plug 30 DAT to 1.3 g/plug 209 DAT. During 1987, average root mass increased from
2.2 g/plug 1 day before treatment to 2.7 g/ plug 110 DAT.
Rhizome production per transplanted plug, as well as rhizome length and mass, were
not affected by pendimethalin application during the study. During 1986, rhizome production
averaged across all treatments reached a maximum of 56 rhizomes/plug 209 DAT.
Rhizome length and mass averaged for all cultivars increased to 13.2 cm and 5.5 g/
plug, respectively, as determined 209 DAT.
Rhizome growth during 1987 continued to be vigorous and unaffected by pendimethalin application.
Cultivar effects. Throughout the study, the cultivar × pendimethalin level interaction
remained nonsignificant for all measures of root and rhizome growth, indicating no cultivar- specific response to pendimethalin. Mean
HORTSCIENCE, VOL. 25(1), JANUARY 1990 85 maximum root length did not vary significantly
among cultivars during either year, and increased from 3.7 cm 30 DAT in 1986
to 9.9 cm 110 DAT in 1987. Root mass was similar for all cultivars, ranging from an average
low of 0.35 g/plug 30 DAT in 1986 to
3.44 g/plug 40 DAT in 1987. Unlike root production, differences were noted in the
number and mass of rhizomes produced by Kentucky bluegrass cultivars during 1986
(Table 2). In particular ‘Adelphi’ produced more rhizomes and a greater mass than other
cultivars on two of the first three observations.
Although ‘Adelphi’ exhibited superior rhizome production capacity through the 131
DAT (1986) observation date, rhizome production
and growth of other cultivars increased with time, so that no significant
differences among cultivars were observed 209 DAT in 1986 or during 1987 (data not
presented). Our results indicate that pendimethalin can be used on these cultivars without
concern for foliar injury or restricted root and rhizome production. Concurrent work by
Bhowmik (1988) revealed that pendimethalin applied to ‘Baron’ Kentucky bluegrass
at 1.7 or 3.4 kg·ha-1 did not inhibit either
rhizome growth or tiller formation when measured 4, 8, and 12 WAT. Although some
root length inhibition occurred immediately after the 1986 pendimethalin application in
this study, it was short-lived and did not affect quality or subsequent root growth.

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토양중 Pendimethalin의 흡착 및 이동특성

The Adsorptionand Movement Characteristics of Pendimethalin in Soils
	라덕관, 김영규 저
	pp.17~23 (7pages)

간행물명 : 지하수토양환경

권/호 : 한국토양환경학회지 제5권 제3호 / 2001

발행기관 : 한국지하수토양환경학회

간행물유형 : 학술저널

주제분류 : 환경공학

파일형식 : PDF

한국어초록

토양중 pendimethalin의 흡착과 이동특성을 파악하기 위하여 사양토, 미사질토 및 양토를 대상으로 회분식 및 칼럼식 실험을 통하여 얻어진 결과는 다음과 같다. Pendimethalin은 진탕 6시간에서 사양토의 경우 59.6%, 미사질토의 경우 77.3%, 양토의 경우 64.0%가 흡착되어 평형흡착에 근접하는 경향을 나타냈으며, 흡착등온식은 Freundlich식에 잘 일치하였으나, Langmuir식에는 적합하지 않았다. 사양토, 미사질토 및 양토에 대한 pendimethalin의 흡착계수는 각각 8.0, 16.1, 9.5로 나타났다. 흡착칼럼 배출구에서 pendimethalin이 처음 검출된 시간 및 유출량은 사양토의 경우 112min, 700ml, 미사질토의 경우 630min, 2100ml, 양토의 경우 189min, 900ml이었다. 0.05Co를 파과점으로 할 경우 각 토양의 파과점에 도달되는 시간은 각각 256min, 810min, 420min이었다.

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Pendimethalin

From Wikipedia, the free encyclopedia

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Pendimethalin[1]
IUPAC name[hide] 3,4-Dimethyl-2,6-dinitro-N-pentan-3-yl-aniline
Identifiers
CAS number	40487-42-1 Y
PubChem	38479
UNII	VL6L14C06U Y
KEGG	C11019 Y
Jmol-3D images	Image 1
SMILES [show] CCC(CC)NC1=C(C=C(C(=C1[N+](=O)[O-])C)C)[N+](=O)[O-]
Properties
Molecular formula	C13H19N3O4
Molar mass	281.31 g mol−1
Density	1.17 g/cm³
Melting point	47-58 °C
Boiling point	330 °C, 603 K, 626 °F
Solubility in water	0.275 ppm
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Pendimethalin is an herbicide used in premergence and postemergence applications to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation. Pendimethalin is listed in the K1-group according to the HRAC classification and is approved in Europe, North America, South America, Africa, Asia and Oceania for different crops including cereals (wheat, barley, rye, triticale), corn, soybeans, rice, potato, legumes, fruits, vegetables, nuts as well as lawns and ornamental plants.

Contents

[hide]

• 1 Use
• 2 Mode of Action
• 3 Resistance
• 4 Registrative status
• 5 Tradenames
• 6 References

[edit] Use

Pendimethalin protects crops like wheat, corn, soybeans potatoes, cabbage, peas, carrots and asparagus. It is used to control annual grasses and certain broadleaf weeds which interfere with growth, development, yield and quality of agricultural and horticultural crops by competing on nutrients, water and light.

In areas where weed infestation is particularly high, yield losses can render wheat production economically unviable.^[2] In addition to wheat, a large number of crops are grown in Europe that are a relatively small percentage of total agricultural output. Herbicide options are limited for these minor crops, with few effective herbicides available in the vegetable sector.^[3] Long-term field studies performed in Germany by governmental research and advisory institutes together with farmers rank Pendimethalin as an efficient herbicide to control blackgrass, regarding to weed control efficacy, crop yield, treatment costs and environmental impact.^[4][5][6]

[edit] Mode of Action

Pendimethalin acts both pre-emergence, that is before weed seedlings have emerged, and early post-emergence. Pendimethalin inhibits root and shoot growth. It controls the weed population and prevents weeds from emerging, particularly during the crucial development phase of the crop. Its primary mode of action is to prevent plant cell division and elongation in susceptible species. In the HRAC classification of herbicides according their mode of action, pendimethalin is listed in group K1.

[edit] Resistance

Herbicide resistance typically increases production costs and limits options for herbicide selection, cultivations and rotations. Up to now Pendimethalin does not show resistance. It is not cross-resistant with other grass weed herbicides. This means that Pendimethalin supports the effects of other supplementary grass weed herbicides that use a different mode of action.^[7]

[edit] Registrative status

Pendimethalin is registered globally for a wide range of crops, according to human and environmental safety standards by the European Commission, US-EPA, Canada-PMRA, Japan, Brazil-ANVISA and others.

[edit] Tradenames

Tradenames include Prowl, Stomp, Stealth and Pendulum.

[edit] References

1. ^ EXTOXNET
2. ^ Clarke, Wynn, Twinning, Berry, Cook, Ellis and Gladders Pesticide availability for cereals and oilseeds following revision of Directive 91/414/EEC; effects of losses and new research priorities. In: HGCA Research Review. Nr. 70, 2009.
3. ^ Little J.: EU´s pesticide regulation must be challenged. In: FarmBusiness. 2009 S. 26–27.
4. ^ Gehring, K. and S. Thyssen: Unkrautmanagement im Getreidebau – Herbizid-Leistungszahl – eine mehrfaktorielle Bewertung von Herbizidbehandlungen. LFL Pflanzenschutz. Institut für Pflanzenschutz der Bayerischen Landesanstalt für Landwirtschaft. In: Freising-Weihestephan, Deutschland. 2004.
5. ^ Gehring, K. and S. Thyssen: Unkrautmanagement im Getreidebau – Herbizid-Leistungszahl – eine mehrfaktorielle Bewertung von Herbizidbehandlungen. LFL Pflanzenschutz. Institut für Pflanzenschutz der Bayerischen Landesanstalt für Landwirtschaft. In: Freising-Weihestephan, Deutschland. 2007.
6. ^ Gehring, K.: Ackerfuchschwanz und Windhalm – die zwei bedeutendsten Ungräser im Getreidebau. In: Getreide Magazin. Nr. 1, 2009, S. 20-25.
7. ^ Moss, S. R. and R. Hull: The value of pre-emergence herbicides for combating herbicide-resistant Alopecurus myosuroides (blackgrass). In: Aspects of Applied Biology. Nr. 91, 2009