Herbicide antidotes—A review

The history of herbicide antidotes is reviewed, beginning with the exploration of compounds to protect wheat (Triticum aestivum L.) against barban in the early 1960s, and the later introduction of naphthalic anhydride (NA, naphthalene-1, 8-dicarboxy-licanhydride) as a seed dressing for protecting maize (Zea mays L.) against EPTC. This compound was largely replaced by Stauffer's R-25788 (N, N-diallyl-2, 2-dichloroacetamide) which has continued to be widely used in conjunction with EPTC and butylate in maize. This compound is highly specific to maize and can thus be applied in admixture with the herbicide, but has not proved of practical value on other crop species. NA on the other hand is less specific and is of potential value on sorghum [Sorghum bicolor (L.) Moench] and rice (Oryza sativa L.); experimental work continues on these crops. The only other antidote to be marketed so far is cyometrinil as a seed dressing for protecting sorghum against metolachlor and related herbicides. Other compounds are under development. Mode of action and structure-activity relations are discussed, as well as the current and future potential for antidotes in respect of the control of weed species in closely related crops, the increased options for herbicide use in minor crops and the possibility of reduced costs for broad spectrum weed control in major crops.     

Dichloroacetamide antidotes enhance thiocarbamate sulfoxide detoxification by elevating corn root glutathione content and glutathione S-transferase activity

Glutathione (GSH) content and GSH S-transferase activity are consistently increased in corn roots on 24-hr exposure of corn seedlings to part per million levels of N,N-diallyl-2,2-dichloroacetamide (R-25788) and related antidotes for thiocarbamate herbicide injury in susceptible corn varieties. This combined enhancement of enzyme activity and cofactor level leads to rapid detoxification of thiocarbamate sulfoxides, which are proposed to be the active herbicidal compounds formed on metabolic sulfoxidation. S-(N,N-Dipropylcarbamyl)-GSH is formed by this enzyme-catalyzed detoxification of EPTC sulfoxide. This hypothesis on antidote mode of action is supported by studies on 32 dichloroacetamides and related compounds and on the concentration- and time-dependent relationships of R-25788 action. The liver GSH content is normal in mice injected with high doses of R-25788, but the content is reduced when EPTC or EPTC sulfoxide is administered. EPTC sulfoxide also carbamoylates the thiol group of coenzyme A in neutral aqueous medium.     

Potential safeners for protecting sorghum (Sorghum bicolor (L.) Moench) against chlorsulfuron,fluazifop-butyl and sethoxydim*

In greenhouse studies, the efficacy of the herbicide safeners NA(1,8-naphthalic anhydride), R-25788 (N,N-diallyl-2,2-dichloroacetamide), cyometrinil and CGA-92194 [N-(1,3-dioxolan-2-yl-methoxy)imino-benzeneaceto-nitrile] in protecting grain sorghum (Sorghum bicolor (L.) Moench, cv. ‘Funk G623’) against injury from pre-emergence or early post-emergence applications of the herbicides chlorsulfuron, fluazifop-butyl and sethoxydim was examined. NA as a seed dressing at 0·5 or 1·0% (w/w) was the most effective of the four safeners and offered partial to good protection to sorghum against injury from the lower rates of pre-emergence applications of all three herbicides. R-25788 was totally ineffective as a sorghum protectant against fluazifop-butyl injury but it did antagonize partially the injurious effects of the lower rates of sethoxydim and chlorsulfuron on sorghum. Cyometrinil and CGA-92194 offered partial protection to sorghum against injury from the lowest rate of all herbicides but their efficacy against higher rates of the three herbicides was very limited. None of the four safeners was effective in protecting grain sorghum against injury from post-emergence applications of the three herbicides tested.     

Biochemical response of inbred and hybrid corn (Zea mays L.) to R-25788 and its distribution with EPTC in corn seedlings

The average endogenous GSH content of eight lines of inbred corn was almost twofold greater than ten varieties of hybrid corn. When inbred and hybrid corn lines were treated with R-25788, the average GSH content increased by 56 and 95%, respectively. R-25788 protected two special inbred corn lines, GT 112 (atrazine susceptible) and GT 112 RfRf (atrazine resistant) from EPTC injury by increasing the GSH content and GSH S-transferase activity in roots. Most of the radiolabel from [¹⁴C]R-25788-treated plants remained in the root tissues whereas the radiolabel in [¹⁴C]EPTC-treated plants was evenly distributed between foliar and root tissues. From radiolabel experiments, hybrid corn seedlings were found to absorb more R-25788 from soil than EPTC. There was no difference between inbred and hybrid corn in the amounts of R-25788 or EPTC taken up or in the enhancement of GSH S-transferase activity caused by R-25788.     

Interactions between barban and protectants on maize, oats and barley

In glasshouse experiments 1,8-naphthalic anhydride (NA) as a seed dressing, and N,N-diallyl-2,2-dichloroacetamide (R25788), either as a seed dressing or mixed in the spray tank with the herbicide, protected maize (Zea mays L.) from subsequent barban damage. When applied after maize emergence, R25788 was not effective through the foliage but had to reach the soil to provide protection. Soil drench treatments of R25788 countered barban damage successfully if applied up to 7 days prior to spraying or up to one day after. Delay of application to 2 or 3 days after barban resulted in only partial protection. Neither NA nor R25788 completely protected barley (Hordeum vulgare L.) or oats (Avena saliva L.) from a subsequent barban spray. Interactions entre le barbane et des produils protecteurs sur le maïs, l'avoine el l'orge Dans des expériences faites en serre, I'anhydride 1,8-naphtalique (AN) employé pour l'enrobage des semences et le N,N-dial-lyl-2,2-dichloroacetamide (R 25788) egalement en enrobage oumélangé dans le réservoir du pulvérisateur avec I'herbicide, ont protégé le maïs (Zea mays L.) des dommages résultant d'un traitement au barbane. Lorsqu'il a été appliqué après la levée du maïs, le R 25788 ne s'est pas montré efficace par voie foliaire: il doit atteindre le sol pour assurer une protection. Les traitements du sol en pluie abondante avec le R 25788 ont supprime efficacement les dégCts du barbane s'ils ont été effectues au plus 7 jours avant le traitement ou 1 jour au plus apres. Lorsque l'application a été faite 2 ou 3 jours apres le traitement au barbane, la protection n'a été que partielle. Ni l'AN ni le R 25788 n'ont complètement protégé I'orge (Hordeum vulgare L.) ou I'avoine (Avena sativa L.) d'un traitement ultériéur avec le barbane. Interaktionen zwischen Barban und Schutzstoffen (Antidote) bei Mais. Hafer und Gerste In Gewächshausversuchen wurde Mais (Zea mays L.) vor einer Schädigung durch Barban geschützt, wenn 1,8-Naphthylsäure-anhydrid (NA) als Saatgutbeize und N,N-Diallyl-2,2-dichlor-acetamid (R 25788) entweder als Saatgutbeize oder als Tankmischung mit dem Herbizid angewendet wurden. Wenn R 25788 nach dem Auflaufen des Maises appliziert wurde, musste es um wirksam zu werden, auf den Boden gelangen; eine Wir-kung über die Blätter konnte nicht festgestellt werden. Durch die Anwendung von R 25788 im Giessverfahren trat kein Barbanschaden auf, vorausgesetzt, dass die Anwendung bis zu 7 Tage vor oder bis zu einen Tag nach der Spritzung erfolgte. Wurde die Applikation erst 2 oder 3 Tage nach der Barbansprit-zung durchgeführt, dann wurde nur ein teilweiser Schutz erzielt. Gerste (Hordeum vulgare L.) und Hafer (Avena saliva L.) wurden weder durch NA noch durch R 25788 völlig vor der schädigenden Wirkung einer darauffolgenden Barbanspritzung geschützt.     

Dichloroacetamide herbicide antidotes enhance sulfate metabolism in corn roots

The herbicide antidotes N,N-diallyl-2,2-dichloroacetamide (R25788) and 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R29148) at ppm levels slightly enhance the uptake of [³⁵S]sulfate in corn roots and greatly increase its metabolism to “bound sulfide”, cysteine, and glutathione (GSH). The decrease in free sulfate content of the roots with R25788 is closely associated with an increase in GSH level. The sulfate content is decreased with an 8-hr exposure to R25788 and R29148 at 3 ppm and its decline continues through 48 hr to about 5% of the control level. Effects on sulfate content are evident at 24 hr even with 0.3–1 ppm of these antidotes. Several other mono- or dichloroacetamide antidotes at 30 ppm also decrease the free sulfate content of corn roots to about 34–60% of control levels within 24 hr. R25788 at 30 ppm has little or no effect at 24 hr on sulfate levels in corn leaves whether the plants are grown in the light or in the dark. R25788 and R29148 decrease sulfate levels in the leaves of milo and in whole pigweed plants, but not in barley, lambsquarters, water grass, wheat, or wild mustard. In increasing GSH biosynthesis, the antidote acts in corn prior to the reduction step to form bound sulfide; in fact, R25788 increases the specific activity of ATP sulfurylase, the first enzyme involved in sulfate assimilation. Thus, dichloroacetamides such as R25788 and R29148 provide a means to experimentally, and perhaps even practically, manipulate sulfate utilization in corn and some other plants.     

The effect of CDAA (N,N,-diallyl-2-chloroacetamide) pretreatments on subsequent CDAA injury to corn (Zea mays L.)

The effects of CDAA (N,N-diallyl-2-chloroacetamide) pretreatment on subsequent CDAA injury to corn were examined and compared with the effects of the herbicide protectant R-25788 (N,N,-diallyl-2,2-dichloroacetamide). In addition, the effects of CDAA pretreatment on subsequent CDAA metabolism were determined. It was found that 5μM CDAA protected corn from injury by 200 μM CDAA when given as a 2.5- or 1-day pretreatment. R-25788 at similar concentrations did not protect corn from subsequent R-25788 injury. Pretreatment with CDAA increased GSH levels of corn roots by 61% within 1 day, and these levels did not increase with a longer 2.5-day pretreatment with CDAA. GSH-S-transferase activity was assayed spectrophotometrically using CDNB (1-chloro-2,4-dinitrobenzene). A 1-day pretreatment with CDAA increased the root GSH-S-transferase activity by 35%, but did not affect shoot GSH-S-transferase activity. A 2.5-day pretreatment resulted in a 50% increase in root GSH-S-transferase activity but no response of the shoot enzyme was observed. Even longer pretreatments with CDAA did not result in any further increases in enzyme activity. When corn roots pretreated with CDAA for 2.5 days were excised and incubated with radiolabeled CDAA, they exhibited greater rates of uptake and metabolism than did nonpretreated roots. With in vitro studies, a fairly high rate of nonenzymatic degradation of CDAA was observed. However, the enzymatic rate was always double that of the nonenzymatic rate under the experimental conditions used. It is concluded that elevations in the GSH levels and GSH-S-transferase activities of corn roots following CDAA pretreatments may be involved in the protection of corn from subsequent CDAA injury.     

Potential antidotes against acetanilide herbicide injury to corn (Zea mays)*

R-25788 (2,2-Dichloro-N,N-diallylacetamide) was the most effective of six potential antidotes evaluated to counter corn (Zea mays L.) injury from the acetanilide herbicides alachlor, metolachlor, acetochlor, H-22234 (N-chloroacetyl-N-(2,6-diethylphenyl)glycine ethyl ester), and H-26910 (N-chloroacetyl-N-(2-methyl-6-cthylphenyl)glycine isopropyl ester). The other potential antidotes in order of decreasing effectiveness were: R-29148 (2,2-dimethyl-5-methyl-dichloroacetyloxazolidine), NA (1,8-naphthalic anhydride), CDAA (2-chloro-N,N-diallylacetamide), Carboxin (2,3-dihydro-5-carboxanilido-6-methyl-l,4-oxathiin), and gibberellin (GA₃). GA₃ only partly relieved the stunting of corn caused by EPTC and metolachlor and did not prevent other herbicide injury symptoms, suggesting that the mode of action of EPTC and metolachlor is not to simply block GA₃ synthesis. R-25788 protected corn equally well from acetanilide or EPTC injury. Produits protecteurs du maïs (Zea mays) contre les dommages provoqués par les acétanilides herbicides Le R-25788 (2,2-dichloro-N.N-diallylacétamide) s'est révéléêtre le plus efficace de six produits protecteurs essayés pour préserver le maïs (Zeas mays L.) des dégâts provoqués par des acétanilides herbicides: alachlore, métolachlore, acétochlore, H-22234 (ester éthylique de la N-chloracétyl-N-(2,6-diéthylphényl) glycine) et H-26910 (ester isopropylique de la N-chloroacétyl-N-(2-méthyl-6-éthylphényl) glycine. Les autres produits protecteurs potentiels ont été, dans l'ordre d'efficacité décroissante: le R-29148 (2,2-diméthyl-5-méthyl-dichloroacéthyloxazolidine), l'AN (anhydride 1.8-naphtalique), le CDAA (2-chloro-N-N-diallylacétamide), la carboxyne (2,3-dihydro-5-carboxanilido-6-méthyl-l,4-oxathiine) et la gibbérelline (A₃ G). Cette dernière a seulement atténué le rabou-grissement provoqué par l.EPTC et le métolachlore chez le maïs. Elle n'a pas supprimé les symptômes de dommages provoqués par les autres herbicides, ce qui suggère que le mode d'action de I'EPTC et du métolachlore ne consiste pas seulement en un blocage de la synthèse de la gibbérelline. Le R-25788 a protégé le maïs des dommages provoqués par l'acétanilide ainsi que par I'EPTC. Potentielle Antidots zur Vermeidung von Acetanilid-Herbizid-schäden an Mais (Zea mays) Von sechs potentiellen Antidots, die geprüft wurden, um Schäden an Mais (Zea mays L.) durch Acetanilid-Herbizide zu vermeiden, war R-25788 (2,2-Dichlor-N,N-diallylacetamid) am wirksamsten. Die verwendeten Herbizide waren: Alachlor, Metolachlor, Acetochlor, H-22234 [N-Chloracetyl-N-(2,6- diäthylphenyl) glycin Älhylester] und H-26910 [N-Chloracelyl-N-(2-méthyl-6-äthylphenyl)glycin lsopropylester]. Die weiteren möglichen Antidots, in der Reihenfolge abnehmender Wirksamkeit, waren: R-29148 (2,2-Dimethyl-5-methyldichlorace-toxazolidin), NA (1,8-Naphthalsäureanhydrid), CDAA (2-Chlor-N,N-diallylacetamid), Carboxin (2,3-Dihydro-5-car- boxanilido-6-methyl-l,4-oxathiin) und Gibberellin (GA₃). durch GA₃ wurde die dureh EPTC und Metolachlor verursachte Stauchung des Mais nur teilweise vermieden. Die durch andere Herbizide verusachten Symptome liessen sich durch GA₃ nicht vermeiden, was darauf schliessen lässt, dass die Wirkungsweise von EPTC und Metolachlor nicht einfach mit einer Blockierung der GA₃ -Synthese zu erklären ist. R-25788 schützte Mais gleichermassen vor Acetanilid-, wie vor EPTC-Schäden.     

Comparative metabolism of atrazine and EPTC in proso millet (Panicum miliaceum L.) and corn

The purpose of this study was to examine the differential activities of proso millet (Panicum miliaceum L.) and corn (Zea mays L.) with respect to atrazine [2-chloro-4-(ethylamino)-6-(isopropylamino)-S-triazine] and EPTC (S-ethyldipropyl thiocarbamate) metabolism. GSH-S-transferase was isolated from proso millet shoots and roots. When assayed spectrophotometrically using CDNB (1-chloro 2,4-dinitrobenzene) as a substrate, the shoot enzyme had only 10% of the activity of corn shoot enzyme while the root enzyme had 33% the activity of corn root enzyme. However, when proso millet shoot GSH-S-transferase was assayed in vitro using ¹⁴C-ring-labeled atrazine, it degraded the atrazine to water-soluble products at the same rate as the corn shoot enzyme. Incubation of excised proso millet and corn roots with [¹⁴C]EPTC indicated that uptake of EPTC was similar in both plants. However, proso millet metabolized the EPTC to water-soluble products at only half the rate of corn. Glutathione levels of proso millet roots were 35.9 μg GSH/g fresh wt, compared with 65.4 μg GSH/g fresh wt for corn. However, a 2.5-day pretreatment with R-25788 (N,N-diallyl-2-2-dichloroacetamide) elevated proso millet GSH levels to 62.7 μg GSH/g fresh wt. R-25788 did not elevate the activity of proso millet GSH-S-transferase, in contrast to its effects on corn. We conclude that differences in response to atrazine and EPTC in proso millet and corn are a result of their differential metabolism.     

Dégradation catalytique de carbamates herbicides deposés sur bentonites homoioniques. I. Cas du barbane

Surface catalysed degradation of carbamate herbicides on bentonites. I. Barban The chemical degradation of barban on various monotonic bentonites (Cu²⁺; Ag⁺) was investigated at room temperature. Interesting results were obtained with bentonite Ag⁺, because they clarified the first phase of the degradation. A chemical degradation pathway for barban was proposed.     

Gibberellin precursor biosynthesis inhibition by EPTC and reversal by R-25788

S-ethyl dipropylthiocarbamate (EPTC) inhibited gibberellic acid (GA) precursor biosynthesis in a cell-free enzyme preparation from unruptured, etiolated sorghum (Sorghum bicolor L. cv. G522 DR) coleoptiles. EPTC, 1 μM, inhibited incorporation of [¹⁴C]mevalonic acid into kaurene 60%, while 10 μM EPTC inhibited ¹⁴C incorporation into kaurene 90%. The precursor of kaurene cyclization (GGPP) increased in ¹⁴C content at both EPTC concentrations. R-25788 reversed the EPTC inhibition of kaurene synthesis. Kaurene oxidation was modified by both EPTC and R-25788. Hypothesized modes of action for EPTC and R-25788 are (a) inhibition of GA synthesis, (b) increased peroxidase activity resulting in increased lignification, (c) increased detoxification by sulfoxidation and carbamoylation, and (d) inhibition of fatty acid synthesis and/or desaturation. These hypotheses are discussed with three of them being incorporated into one working unit which correlates with EPTC and R-25788 symptom phenology. The fourth hypothesis could also fit into this general pattern.     

The role of coleoptile on barban sensitivity between wild oat and wheat

Differential sensitivity of wild oat (Avena fatua L.) and wheat (Triticum aestivum L.) to barban (4-chloro-2-butynyl-m-chlorocarbanilate) was highest when barban was applied to the coleoptile. The coleoptile acts as a physical and physiological barrier to reduce the concentration of free barban in the stem section where the sensitive meristematic sites are located. Metabolism of barban was higher ïn the coleoptile of tolerant wheat than in that of susceptible wild oat. Free barban concentration was higher in the stem of wild oat than in the stem of wheat after 24 hr, but after 48 hr, concentrations were similar. The coleoptile appears to enhance the differential sensitivity to barban between wild oat and wheat.     

Control of Avena fatua and Fagopyrum tataricum with tank mixtures of linuron or linuron + MCPA and sequential applications of linuron, and post-emergence A. fatua herbicides

Linuron (0.21 and 0.28 kg/ha) and linuron + MCPA (0.21+0.56 kg/ha) in a tank mixture with field rates of barban, difenzoquat and flamprop-methyl reduced the phytotoxicity of these herbicides to Avena fatua. When linuron was applied immediately following or 6 days after the A. fatua herbicides no reduction in phytotoxicity to A. fatua occurred, suggesting that the antagonism may be occurring as a result of physical or chemical incompatability when the herbicides are mixed together. The possibility of obtaining broad-spectrum weed control with one trip over the field by applying linuron and one of these wild oat herbicides separately but at the same time using a double-boom, double-tank system deserves evaluation. When linuron was applied in a tank mixture (0.21 and 0.28 kg/ha), immediately after, or 6 days after diclofop-methyl (0.70 kg/ha), there was no reduction of A. fatua control, and wheat tolerance to the tank mixture was good. This tank mixture offers potential for control under field conditions of A. fatua and some broad-leaved weeds in one spray operation. Linuron + MCPA (0.21+0.56 kg/ha) in a tank mixture severely reduced A. fatua control with diclofop-methyl. No loss of phytotoxicity to Fagopyrum tataricum occurred when the A. fatua herbicides tested were tank mixed with linuron or linuron + MCPA. Lutte contre Avena fatua et Fagopyrum tataricum avec des mélanges extemporanés de linuron ou de linuron + MCPA et des applications successives de linuron et d'herbicides de postlevée actifs contre A. fatua     

Effets de divers herbicides sur la croissance mycélienne de souches de Botrytis cinerea pers et de Penicillium expansum Link, sensibles ou résistantes à certains fongicides

Effects of various herbicides on mycelial growth of strains of Botrytis cinerea. Pers. and Pénicillium expansum Link, sensitive or resistant to certain fungicides Of seventy herbicides tested, thirty-eight were slightly toxic to B. cinerea (CI50, concentration giving 50% inhibition of the speed of mycelial growth, exceeding or equal to 100g of herbicide/ml of nutrient solution) and, of those, ten had no effect even at 1000 g/ml. The most active products (CI50 less than 10 g/ml) were Chlorthiamid, dichlobénil, nitrofen, propyzamide and phenolic derivatives (DNOC, ioxynil, PCP). In most cases P. expansum was less sensitive than B. cinerea except to endothal, propachlor, prynachlor and certain substituted ureas. Strains resistant to the benzimidazole fungicides (carbendazim, thiabendazole etc.) show increased sensitivity to certain carbamade herbicides (barban, chlorbufam etc.), this indicates the existence of a negative cross resistance between these groups of antimitotic pesticides. Strains resistant to the cyclic-imide fungicides (iprodionc, procymidone, vinclozolin) and to various aromatic compounds (biphenyl. chloroneb, dicloran etc.) may also be resistant to bipyridilium, dinitroanilinc and diphenylethcr herbicides, to chlorthamid. dichlobénil and oxadiazon. This cross resistance between pesticides with different biochemical modes of action has yet to be explained.     

Interaction between difenzoquat and other herbicides for wild oat and broadleaved weed control in barley

The interaction between barban and difenzoquat was additive upon application at the two-or four-leaf stage of wild oat. Wild oat control with a mixture of barban and difenzoquat at 0.14 + 0.42kg/applied at the two-or four-leaf stage was as effective as the recommended field rate of barban alone (0.28 kg/ha) at the two-leaf or difenzoquat alone (0.84 kg/ha) at the four-leaf stage. Barley yield increases with the mixture were comparable to those obtained with the full rates of the herbicides used alone their correct leaf stages This mixture offers the farmer excellent wild oat control, an extended Leaf-stage latitude (two-to four-leaf), excellent barley yield increases and the possibility of reduced operating costs. The herbicidal activity of difenzoquat or a barban + difenzoquat mixture was reduced on addition of amine formulations but not ester formulations of herbicides for broadleaved weeds. MCPA ester and bromoxynil plus MCPA were the most compatible broadleaf herbicides when mixed with difenzoquat Difenzoquat or difenzoquat + barban significantly stimulated the activity of various herbicides on Tartary buckwheat. A mixture of burban + difenzoquat + bromoxynil-MCPA or MCPA ester provided effective wild oat and Tartary buckwheat control The latter mixtures enable a farmer to eliminate one spray operation. The interaction between difenzoquat and diclofop methyl [4-(2,4-dichlorophenoxy) phenoxy propionic acid methyl ester was additive. Wild oat control with the mixtures was good and barley yield was increased over that obtained with a recommended field rate of diclofop methyl. Interaction entre le difenzoquat et d'autres herbicides pour la lutte contre la folle acoine et les mauvaises herbes dicotylédones dans l'orge L'interaction entre le barbane et le difenzonzoquat a été additive en ce qui concerne l'application aux stades 2- et 4- feuilles de la folle-avoine. L'efficacité contre la folle avoine avec un mèlange de barbane et de difenzoquat à difenzoquat à 0.14 + 0.42 kg/ha appliqué aux stades 2 ou 4 feuilles a été aussi bonne que la dose recommandée au champ de barbane seul (0.28 kg/ha) au stade 2 feuilles ou que le difenzoquat seul (0.84 kg ha) au stade 4 feuitles. Les augmentations de rendement de l'orge avec le mélange ont été comparables employès seuls au stade correct de développement foltaire. Ce folle-avoine. une latitude de stades plus grande (2 á 4 feuilles). de substantielles augmentations de rendement pour l'orge et la possibilité de réduire le prix de revient de l'opération. L'activité herbicide du difenzoquai ou d'un mèlange barbane + difenzoquat a été réduite par l'addition de formulat ions amine mais pas avec les formulations ester des herbicides pour les mauvaises herbes dicotylédones L'ester de MCPA et le bromoxynile plus MCPA ont été les plus compatibles parmi les herbicides anti-dicotylédones lorsqu'ils ont été mélangés avec le difenzoquat. Le difenzoquat ou le mélange difenzoquat + barbane ont significativement stimulé l'activité de divers herbicides vis-à-vis du Fagopyrum tartaricum. Un mèlange de barbane + difenzoquat + bromoxynil-MCPA ou MCPA ester s'est montré efficace contre la folle-avoine et F tartaricum Ces derniers mélanges permettent au cultivateur de faire l'èconomie d'un traitement. L'interaction entre le difenzoquat et le diclofop mèthyle (ester méthylique de l'acide 4(2,4 dichtorophénoxy)phénoxy propionique) a été additive. L'efficacite contre la folle-avorne avec les mèlanges a été bonne et le rendement de l'orge a été meilleur que celui obtenu avec la dose recommandée de diclofop méthyle. Wechselwirkungen zwischen Difenzoquat und anderen Herbiziden zur Bekämpfung von Flughafer und dikotylen Unkräutern in Gerste Wenn Barban und difenzoquat im 2-oder 4-Blattstadium des Flughafers appliziert wurden, konnte etne additive Wirkung zwischen den beiden Herbiziden beobachtet werden. Die Flug-haferbekampfung war mit einer Mischung von Barban und Difenzoquat bei Aufwandmengen von 0.14 + 0.42 kg/ha und Anwendung im 2- Oder 4-Blattstadium genauso gut wie bei alleiniger Anwendung von Barban mit der empfohlenen Aufwandmenge von 0.28 kg/ha im 2-Blattstadium. oder von Difenzoquat mit O.84 kg/ha im 4-Blattadium. Die Mehrerträge an Gerste die mit der Mischung erzielt wurden. entsprachen den Mehrerträgen bei alleibuger Anwendung der Herbizide im empfohlenen Entwicklungsstadium Diese Mischung beitet dem Landwirt eine ausgezeichnete Bekämpfung des Flughafers bei erweitertem Anwndungsbereich (2- bis 4-Blattstadium). deutlich Mehrerträge bei Gerste und die Möglichkeit geringerer Anwendungskosten. Die Wirkung von Difenzoquat oder der Barban + Difenzoquat-Mischung war schlechter. wenn Amin-formulierungen von Herbiziden zur Bekämpfung dikotlyer Unkräuter zugesetzt wurden, jedoch nicht bei Zusatz von Ester-formulierungen. MCPA-Ester und Bromoxynil plus MCPA waren die geeignetsten Mischungspartner für Difenzoquat gegen dikotyle Arten. Difenzoquat oder Difenzoquat + Barban steigerten signifikant die Wirkung verschiedener Herbizide gegenüber Fagoyprum tataricum. Die Mischung von Barban +Difenzoquat + Bromoxynil-MCPA oder MCPA-Ester ergab eine gute Bekàmpfung des Flughafers und von F. tataricum. Mit diesen Mischungen kann eine Spritzung emgespart werden Für Difenzoquat und Diclofop-methyl [2-[4-(2′,4′-Dichlorphenoxy)-phenoxy]-propionsäuremethylester wurde eine additive Wirkung festgestellt. Die Flughaferbekämpfung mit diesen Mischungen war gut und der Gersteertrag war höher als bei Anwendung der empfohlenen Aufwandmenge von Diclofop-methyl.     

Glasshouse trials with controlled drop application of some foliage-applied herbicides

MCPA, mecoprop, dichlorprop, dicamba, 2,3,6-TBA, bentazone, ioxynil/bromoxynil (a mixture), barban, difenzoquat and chlorfenprop-methyl were applied by spinning disc in controlled drop sizes from 150-350μm and at very low volume rates (5–45 1/ha), to the foliage of some dicotyledonous weed species or wild oats (Avena fatua L.). The same herbicides were also applied by means of conventional hydraulic nozzles at volume rates of about 200 1/ha. Most of these herbicides performed as well at very low volume rates as with the conventional application, the major exceptions being bentazone, ioxynil/bromoxynil (both of which have distinct contact effects) and dichlorprop. Comparisons between oil and water as the diluent at a very low volume rates suggest that there may be situations when oil is preferable and others when water is.     

Unkrautbekämpfung in Lupinen – Erkenntnisse aus 10 Jahren Lückenindikation

In Germany, cultivation of lupines traditionally takes place only in few federal states at sites with light/sandy soil conditions. Due to this fact, there only exist a small number of field trials to close gaps in chemical weed control via herbicides. The existing pre-emergence herbicides are not able to control all of the most common weed species sufficiently-they all show efficiency gaps against single weed species. Not any of the pre-emergence herbicides tested could achieve high efficiencies against Polygonum convolvulus. The best efficiency against P. convolvulus can be achieved after a sequence of a pre-emergence spray of 0,8–1,0 l/ha Fenikan and a post-emergence spray of 0,2 l/ha Tacco. Since Fenikan and Tacco are not approved for lupine, after approval the application only in lupine stocks for seed production is possible. By taking into account only the currently legal permitted herbicides, Gardo Gold and the tank mix Boxer?+?Stomp Aqua show the best broad effects. Benefits resulting from Gardo Gold can be obtained against Chenopodium album, Viola arvensis, Centaurea cyanus, while the tank mixes Boxer?+?Stomp Aqua show advantages against Galium aparine. From the pre-emergence herbicides tested, Successor T could be applied as an addition to improve the broad effect. In tank mixes with Gardo Gold, the most common weed species can be controlled well. However, with permission also this tank mix can currently only be applied in lupine seed stock production. In the near future weed control will only be possible with the currently existing and approved herbicides, because there are no new herbicides to expect that are compatible with corn, grain and lupine. Under suboptimal application conditions of soil herbicides, weeded lupine stocks can only be harvested after siccation.     

THE HERBICIDAL EFFECT OF SOME α-HYDROXY-β,β,β-TRICHLOROETHYLAMINO-1,2,4-TRIAZOLES

Summary. Four α-hydroxy-β,β,β-trichloroethylamino-1,2,4-triazoles were prepared by the reaction of chloral hydrate with the corresponding aminotriazole and tested for herbicidal activity.
The introduction of the α-hydroxy-β,β,β-trichloroethyl group into the aminotriazole molecule increased the activity of the parent compound. The increase in activity was slight with the highly active 3-amino-1,2,4-triazole but was more marked with amino 1,2,4-triazoles of low activity. The symptoms resembled those of the simultaneous action of 3-amino-l,2,4-triazole with chloral hydrate or trichloroacetic acid.     

Root growth profiles of Aveneae and Poeae plants in optically active α-methylbenzyl-3-p-tolylurea media

Using a root growth inhibition assay, we studied the diverse chiral responses of plants in the tribes, Aveneae and Poeae, to the optically active compounds, R- and S- 1-α-methylbenzyl-3- p -tolylurea (MBTU). We specifically examined the responses of grasses belonging to the Poeae tribe ( Lolium , Briza , Poa , Dactylis , and Festuca ) and the Aveneae tribe ( Avena , Holcus , Agrostis , Alopecurus , Beckmannia , and Phleum ). These plants include companion weeds of wheat and barley, and turf grass. The companion weeds of cereal crops, such as Poa annua , Poa pratensis , Dactylis glomerata , Avena fatua , Avena sativa , Holcus lanatus , Agrostis stolonifera , Alopecurus myosuroides , Al. aequalis , and Beckmannia syzigachne , showed significantly inhibited root growth in response to 20 µmol L⁻¹ R- MBTU, whereas the root growth of Triticum aestivum was not inhibited at this concentration. Like Oryza sativa , almost all the Poeae and Aveneae plants tested here preferentially responded to R -MBTU, but the four grasses, Lolium multiflorum , D. glomerata , Alopecurus species, and Phleum pratense , preferentially responded to S -MBTU. Among them, the Agrostis species were highly sensitive to R -MBTU and the Alopecurus species were highly sensitive to S -MBTU. All the plants among the genera, Poa , Avena , and Alopecurus , showed a homogeneous chiral preference.     

Systematic approach to the wild oat problem

A five-year study in consecutive cereal cropping under commercial conditions has indicated that a dense population of wild oat, Avena fatua, can be reduced to a practical roguing level by annual efficient use of the currently available herbicides, barban or tri-allate, over a four-year period. Alternative year application of these herbicides was also studied. Problems arising during the conduct of a National Wild Oat Advisory Programme are also spotlighted.