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Articles 17 and 18 of the United Nations (UN) Framework Convention on Tobacco Control address the environmental sustainability of tobacco as a contested agricultural crop. They require regulatory land-use policies to be introduced and designed to enhance a sustainability transition to diversified farming practices and/or alternative livelihoods. Related activities of the UN Study/Working Group on Economically Sustainable Alternatives to Tobacco Growing are reviewed to assess and monitor the crop’s impact on natural resources with a focus on methods to identify tobacco-attributable deforestation (remote sensing, proxy values, secondary statistics, natural valuation, ecological/social surveys). It is posited that since 2007 no advances have been achieved in framing woody biomass destruction/degradation due to land extension and curing (i.e., drying green leaf using wood). Building on support by digital technologies and land surface monitoring systems, a novel post-2020 strategy is proposed to mainstream an extended set of indicators integratively, i.e., addressing biodiversity losses, soil carbon reservoirs and land degradation neutrality of tobacco as an agricultural crop. Thus, the point is emphasized that land stewardship requires political priority setting that makes the framing of land-use sustainability metrics more than a purely technical matter.