Greenhouse and laboratory investigations using four soils were conducted to determine the influence of seven herbicides on symbiotic nitrogen (N2) fixation by soybeans [Glycine max (L.) Merr. ‘Davis’]. Soils were treated with recommended rates of herbicides immediately after planting. After 8 to 10 weeks the nodulated root systems were assayed for nitrogenase activity using the acetylene (C2H2) to ethylene (C2H4) reduction technique, and total numbers and dry weights of nodules were determined. Metribuzin [4-amino-6-tert-butyl-3-(methylthio)-as-triazin-5(4H)-one] (0.3 kg/ha) decreased nodule dry weight and C2H4 production per plant per hour in a Convent sandy loam. Alachlor [2-chloro-2’,6’-diethyl-N-(methoxymethyl) acetanilide] (2.2 kg/ha) and prometryn [2,4-bis(isopropylamino)-6-(methylthio)-s-triazine] (0.6 kg/ha) also decreased C2H4 production per plant per hour in a Convent sandy loam, while metribuzin (0.6 kg/ha) increased C2H4 production per plant per hour and per milligram of nodule dry weight in a Mhoon silt loam. Prometryn (1.7 kg/ha) increased production of C2H4 per plant per hour in a Moreland silt loam. None of the herbicides affected C2H4 production, nodule number, or nodule dry weight in a Commerce silt loam.

Field and laboratory studies were conducted to examine effects of prior butylate use on biodegradation of subsequent applications of butylate and four other carbamothioate herbicides. Bioassays were used to demonstrate reductions of butylate and EPTC activity in four soils preconditioned by annual butylate applications. Combining these herbicides with dietholate, an enzyme inhibitor, prolonged persistence and restored normal herbicidal activity. Expected herbicidal efficacy occurred in adjacent plots with no history of carbamothioate use. Prior applications of butylate resulted in cross-adapted degradation of EPTC but not vernolate, pebulate, or cycloate. When samples of Cecil soil were treated in the laboratory with 14C-butylate, evolution of 14CO2 was significantly higher from soils that had received repeated field applications of butylate. The use of 14C-herbkides could be used to predict problem soils and potential herbicide failure.

Laboratory experiments were conducted to determine the fate of 14C-EPTC in a soil that had a history of vernolate application and exhibited accelerated degradation of carbamothioate herbicides compared to nonhistory soil. A very rapid mineralization of the herbicide to 14CO2 was evident in history soil, compared to nonhistory soil. The two soils did not differ in the amounts of the EPTC lost through volatilization or in the nonextractable radioactive fractions. Except for small quantities of EPTC-sulfoxide and sulfone, no other metabolites were detected. Degradation of 14C-EPTC, as determined by evolution of 14CO2 in history soil, was drastically inhibited following soil sterilization by means of autoclaving or gamma irradiation. Soil disinfestation by solarization, methyl bromide, or metham had a pronounced inhibitory effect during the first 6 days, but was less effective than sterilization. Treatment of a history soil with the fungicide 2-methoxyethylmercury chloride and dietholate strongly inhibited EPTC degradation, while thiram and fentin acetate had only short lasting effects. Cycloheximide, an antifungal antibiotic, had little effect on the degradation of EPTC while chloramphenicol, an antibacterial antibiotic, inhibited the herbicide degradation. These results indicate that accelerated degradation of EPTC is linked to the activity of soil microorganisms, e.g. bacteria, and can be controlled by sterilization and chemical treatments.

Greenhouse and field experiments were conducted to investigate degradation rates and efficacy of EPTC (S-ethyl dipropyl carbamothioate), butylate [S-ethyl bis(2-methylpropyl)carbamothioate], vernolate (S-propyl dipropylcarbamothioate), and cycloate (S-ethyl cyclohexylethylcarbamothioate) in soils with and without prior history of thiocarbamate use. Herbicide persistence was measured by an oat (Avena sativa L.) bioassay, and giant foxtail (Setaria faberi Herrm. # SETFA) control was visually estimated in field studies. Both greenhouse and field studies indicated that enhanced thiocarbamate degradation occurred when the same herbicide (EPTC, butylate, or vernolate) was applied over successive years. Addition of dietholate (O,O-diethyl O-phenyl phosphorothioate) or fonofos (O-ethyl-S-phenylethylphosphonodithioate) increased thiocarbamate persistence and giant foxtail control in soils with prior thiocarbamate exposure. Use of dietholate or fonofos two or three consecutive years with EPTC or butylate again resulted in enhanced degradation. EPTC persistence and giant foxtail control were not affected by prior treatments or tank mixes with carbofuran (2,3-dihydro-2,2-dimethyl-7-benzofuranyl methylcarbamate). Rotation away from successive applications of the same thiocarbamate herbicide (EPTC, butylate, or vernolate) improved herbicide efficacy.

The relationship between herbicide injury and soybean [Glycine max (L.) Merr. ‘Amsoy 71’] yield response was studied under weed free conditions at three locations. Reduced crop vigor at early growth stages was not an adequate indicator of yield response. Yield reduction was greater when soybean stand was reduced by herbicides than when stand was reduced to the same level by hand thinning. Yield response was a function of the degree and persistence of crop vigor reduction in a reduced stand of soybeans.

Laboratory experiments were conducted to evaluate the biodegradation of 14C-labeled butylate, cycloate, EPTC, pebulate, and vernolate in three butylate-history soils that had received three to eight applications of butylate under field conditions. After 20 days, biodegradation of butylate and EPTC was accelerated and had no lag phase in all three butylate-history soils. Butylate-adapted microorganisms were cross-adapted for EPTC and degraded EPTC as readily as butylate. Biodegradation of butylate and EPTC in Dothan soil without a butylate history exhibited a lag phase of 6 days after which 14CO2 was evolved at an exponential rate. This indicated that enhanced biodegradation was induced after one application of butylate or EPTC. Butylate-adapted microorganisms were cross-adapted for vernolate and pebulate in Dothan and pebulate in Wagram soils with a butylate history. Biodegradation of vernolate and pebulate was not enhanced in Varina butylate-history soil. After 20 days, there was no cross-adaptation for cycloate in any soil. These findings indicated that biodegradation of carbamothioates was influenced by soil type and previous carbamothioate use and that caution should be exercised in use of EPTC on fields of previous butylate use.

Greenhouse and on-farm tests were conducted in North Carolina in 1979 and 1980 to evaluate sicklepod (Cassia obtusifolia L. # CASOB) management in soybeans [Glycine max (L.) Merr.]. All postemergence herbicide applications gave better sicklepod control when applied following vernolate [S-dipropylthiocarbamate) preplant incorporated than when applied following alachlor [2-chloro-2,6-diethyl-N-(methoxymethyl)acetanilide] preemergence. This resulted from decreased fatty alcohols and hydrocarbons in the epicuticle of vernolate-treated sicklepod. When applied sequentially to vernolate, toxaphene (chlorinated camphene, 67 to 69% chlorine) plus an oil concentrate and acifluorfen {5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoic acid} applied postemergence to the first true-leaf stage of sicklepod resulted in 95 and 90% control, respectively. Linuron [3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea] and metribuzin [4-amino-6-tert-butyl-3-(methylthio)-as-triazin-5(4H)-one] applied alone or as tank mixes with 2,4-DB [4-(2,4-dichlorophenoxy)butyric acid] provided greater than 90% sicklepod control when applied postemergence-directed to soybeans. Metribuzin was more injurious to soybeans than linuron.

An increased rate of butylate (S-ethyl diisobutylthiocarbamate) degradation occurred on a Kennebec silt loam (sil) exhibiting rapid EPTC (S-ethyl dipropylthiocarbamate) breakdown in the field. Butylate degradation was not as rapid as EPTC degradation on field soils previously treated with EPTC. Addition of R-33865 (O, O-diethyl-O-phenol phosphorothioate) to butylate extended its persistence in field soils with and without prior EPTC application. Although microbial degradation of butylate, EPTC, and vernolate (S-propyl dipropylthiocarbamate) was increased on EPTC-pretreated soils, EPTC and vernolate degradation was much more rapid than butylate degradation. Addition of R-33865 to butylate, EPTC, or vernolate extended their soil persistence on soils pretreated with EPTC. In a laboratory experiment, a maximum rate of EPTC degradation resulted from one prior application. The rate of butylate degradation increased with each successive butylate application, but the degradation rate was not as high as those observed for EPTC on EPTC-pretreated soil.

Solar heating (SH) of the soil by mulching it with transparent polyethylene (PE) during the hot season elevated the soil temperature by 10 to 18 C above that of the non-mulched soil. SH for 4 to 5 weeks resulted in effective control of most summer and winter annual weeds, the effect lasting for more than 5 months after PE removal. Melilotus sulcatus Desf., Astragalus boeticus L. and bull mallow (Malva nicaeensis All. # MALNI) were not controlled by SH. Perennial weeds which propagate from vegetative parts were only partially controlled with short SH, but mulching for 8 to 10 weeks improved control. Mulching the soil with perforated or shaded transparent PE or black PE resulted in a smaller increase of soil temperature and thus less efficient weed control. A combination of SH with soil-incorporated EPTC (S-ethyl dipropylthiocarbamate) or vernolate (S-propyl dipropylthiocarbamate) did not improve the weed control over SH alone, but significantly enhanced the disappearance of the herbicides from the soil. SH inhibited the disappearance of fluridone {1-methyl-3-phenyl-5-[3-(trifluoromethyl) phenyl]-4(1H)-pyridinone} but did not change the residual phytotoxicity of bromacil (5-bromo-3-sec-butyl-6-methyluracil). SH treatment improved plant growth and increased the yield of wheat (Triticum aestivum L. ‘895′) and turnip (Brassica rapa L. ‘Purple top’), but not of parsley (Petroselinum sativum Hoffm.).

Field studies were conducted in 1978 and 1979 on broadleaf signalgrass [Brachiaria platyphylla (Griseb.) Nash] management in peanuts [Arachis hypogaea (L.) ‘Florigiant′]. In both years, preplant incorporated applications of benefin (N-butyl-N-ethyl-α,α,α-trifluoro-2,6-dinitro-p-toluidine), alachlor [2-chloro-2′,6′-diethyl-N-(methoxymethyl)acetanilide], and metolachlor [2-chloro-N-(2-ethyl-6-methylphenyl)-N-(2-methoxy-1-methylethyl)acetamide] provided better than 75% initial control of broadleaf signalgrass. Preemergence applications of alachlor and metolachlor provided 90% or better initial control. Vernolate (S-propyl dipropylthiocarbamate) and diphenamid (N,N-dimethyl-2,2-diphenylacetamide) provided less than 45% initial control. An at-cracking application of dinoseb (2-sec-butyl-4,6-dinitrophenol) plus naptalam (N-1-naphthylphthalamic acid) plus either alachlor or metolachlor increased control over that provided by at-planting herbicides alone and maximum yields were obtained. No at-planting herbicide alone provided better than 60% control at harvest and consequently yields were lower. In three of four experiments, sequential applications of at-planting and at-cracking herbicides provided better than 75% control at harvest. In the fourth experiment, only benefin and metolachlor followed by at-cracking applications provided better than 70% control at harvest.

Efficacy of EPTC (S-ethyl dipropylcarbamothioate), butylate [S-ethyl bis(2-methylpropyl)carbamothioate], vernolate (S-propyl dipropylcarbamothioate), and cycloate (S-ethyl cyclohexylethylcarbamothioate) applied with dichlormid (N,N-diallyl-2,2-dichloroacetamide), and the former three herbicides applied with dichlormid and dietholate (O,O-diethyl-O-phenol phosphorothioate) for wild proso millet (Panicum miliaceum L. ssp. ruderale (Kitagawa) Tzevelev. # PANMI) control in corn (Zea mays L.) was evaluated in fields previously treated with EPTC + dichlormid or EPTC + dichlormid + dietholate. Cycloate + dichlormid usually controlled millet regardless of prior herbicide use. But EPTC + dichlormid was less effective than on soils not previously treated with the herbicides, suggesting enhanced soil biodegradation. The use of EPTC + dichlormid with row cultivation or applications of selected herbicides improved millet control. Following prior use of EPTC + dichlormid, wild proso millet control was improved by the addition of dietholate to EPTC + dichlormid and vernolate + dichlormid but not butylate + dichlormid. In dissipation studies using soils previously treated with EPTC + dichlormid, the relative order of herbicide persistence was EPTC + dichlormid < vernolate + dichlormid < butylate + dichlormid < EPTC + dichlormid + dietholate < vernolate + dichlormid + dietholate = butylate + dichlormid + dietholate < cycloate + dichlormid. When EPTC + dichlormid + dietholate was applied to soils previously treated with that mixture, wild proso millet control was again reduced. Dissipation studies confirmed that dietholate slowed biodegradation of EPTC in soils previously treated with EPTC + dichlormid but not with EPTC + dichlormid + dietholate.

Laboratory studies were conducted to evaluate the degradation of butylate (S-ethyl diisobutylthiocarbamate), EPTC (S-ethyl dipropylthiocarbamate), cycloate (S-ethyl N-ethylthiocyclohexanecarbamate), and vernolate (S-propyldipropylthiocarbamate) in soil with prior thiocarbamate herbicide exposure. EPTC degradation was accelerated in soil which had previously been treated with butylate, vernolate, or EPTC in 1979, 1980, and 1981. The evolution rate of 14CO2 from 14C-labeled vernolate was increased in soil which had previously been treated with vernolate or EPTC in 1979, 1980, and 1981. Cycloate degradation was not enhanced in soil with prior exposure to butylate, EPTC, or vernolate. Butylate breakdown was enhanced to the greatest extent in soil with previous exposure to butylate.

Wild poinsettia control in peanut was evaluated following various preplant-incorporated and postemergence herbicide applications. The addition of vernolate or alachlor to a preplant-incorporated treatment of benefin improved wild poinsettia control obtained with treatments of lactofen or paraquat plus alachlor applied at the time of peanut emergence. Lactofen applied postemergence following lactofen plus alachlor applied at the time of peanut emergence provided ≥92% wild poinsettia control and peanut yields equivalent to the handweeded control. Treatments of paraquat plus alachlor applied at the time of peanut emergence followed by acifluorfen (applied once or twice) or paraquat followed by acifluorfen provided good (74 to 100%) wild poinsettia control for up to 12 weeks after planting and peanut yields not different from the handweeded plots. Treatments that did not provide at least 92% wild poinsettia control when evaluated 5 weeks after planting resulted in significant peanut yield reduction compared to the handweeded control.

Experiments were conducted to investigate enhanced biodegradation of carbamothioates and to evaluate the effect of microbial inhibitors on the efficacy of butylate [S-ethyl bis(2-methylpropyl)carbamothioate], EPTC (S-ethyl dipropylcarbamothioate), and vernolate (S-propyl dipropylcarbamothioate) in soils that had received butylate treatment in previous years (butylate-history soils). Inhibitors used were fonofos (O-ethyl-S-phenylether phosphonodithioate) and R-33865 (O,O-diethyl-O-phenylphosphorothioate). R-33865 and fonofos significantly improved control of large crabgrass [Digitaria sanguinalis (L.) Scop. # DIGSA] with butylate and EPTC in corn (Zea mays L. ‘Coker 21’). Bioassay data reflected more residual phytotoxicity from butylate and EPTC when these herbicides were combined with the microbial inhibitors. In butylate-history soils planted to soybeans [Glycine max (L.) Merr. ‘Wright’], R-33865 did not improve the efficacy of vernolate. These results indicated some cross-adaptation of the butylate-adapted microorganisms for EPTC, but no cross-adaptation was detected for vernolate. Under laboratory conditions, 14C-butylate was degraded more rapidly to 14CO2 in butylate-history soils than in non-butylate-history soils.

Laboratory studies enumerated butylate-, EPTC-, vernolate-, pebulate-, and cycloate-utilizing bacteria and actinomycetes in a Dothan loamy sand following repeated use of butylate, EPTC, or vernolate. Herbicide utilizers were isolated on a defined medium composed of minimal salts plus 200 mg/L herbicide as the primary carbon source plus 25 mg/L TTC as an indicator of organisms capable of metabolizing the herbicide substrates. Media inoculated with a butylate-history soil developed more TTC-red actinomycetes on the butylate-indicator agar than did media inoculated with a non-herbicide-history soil. Similarly, media inoculated with a vernolate-history soil developed more TTC-red bacteria on the vernolate-indicator agar. Cross-adaptation from vernolate to butylate and cycloate was evident, with inoculant from the vernolate-history soil exhibiting an increase in bacterial counts when butylate or cycloate was present as the primary carbon source. Likewise, previous butylate exposure corresponded with an increase in the number of vernolate- and pebulate-utilizing actinomycetes. Previous exposure to EPTC resulted in an increased population of butylate- and pebulate-utilizing actinomycetes.